WEBVTT
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I just think that writing is the best way to
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expose gaps in your thinking and where your thinking is
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falling short. It is impossible to write down everything you
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know about an idea and not immediately see the gaps
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in what you know about that concept. And so as
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a leader, it's one of the most important things you
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can do for clarifying your thinking on any given topic.
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I recently found an exciting new investment opportunity.
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high entry cost. But one startup is making it available
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for everyone. Masterworks.io lets you invest in multi-million dollar works
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by artists like Banksy and Monet. Contemporary art prices outperformed
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trillion and is growing by another trillion over the next
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five years. Now, demand is high, but I've worked with
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Masterworks to let you skip their wait list by going
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to masterworks.io slash learning. That's masterworks.io slash learning. Also, please
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see important disclosures at masterworks.io slash disclaimer. Welcome to the
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Learning Leader Show presented by Insight Global.
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I am your host, Ryan Hawk. Thank you so much
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for being here.
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Text LEARNERS to 44222 to become part.
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Of Mindful Monday. You, along with tens of thousands of
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other learning leaders from all over.
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The world, will receive a carefully curated email from me
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each Monday morning.
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To help you start your week off right.
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You'll also receive details about how my book, Welcome to Management,
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will help you become.
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A more effective leader. Text LEARNERS to 44222.
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Now on to tonight's featured leader. This was a fun one.
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It's Sahil Bloom, writer and angel investor. He publishes work
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on the Curiosity Chronicle.
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Love the name.
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He demystifies complex topics and makes them simple. Previously, he
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was a pitcher for Stanford's baseball team. A few of
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the topics we discuss, the must-have qualities of a leader
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he chooses to invest in, and then what makes a
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great coach, both.
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On the field and online. in the business world.
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What he learned from giving up a grand slam in
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a pivotal game broadcasted on ESPN.
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And why you should write.
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I've been beating this drum for a while, but Sahil
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shares some great examples of how it's made his life better.
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Ladies and gentlemen, this is a great one. It's Sahil Bloom.
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You first piqued my curiosity. I saw a thread you've
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written on Twitter and then I looked at your bio
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and it said a couple of things that I really liked. One,
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writing threads to demystify the world, investor, advisor, and creator.
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And then this next part really got me. Gave up
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a grand slam on ESPN in 2012 and still waiting
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for it to land. So I was like, okay, this guy,
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I like this guy and I don't know him yet.
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Could you share more?
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About a little of your backstories, I guess, going to
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Stanford and being a baseball pitcher and why you thought,
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let me just jab myself a little bit with my
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Twitter bio.
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Yeah. Yeah.
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Well, I appreciate you having me on. This is awesome.
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Been a big fan of the content you're putting out.
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So I'm excited to be a part of it now.
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But no, I mean, the genesis of all of that
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was like, I generally think that people take themselves too seriously.
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And we all have a tendency to do it, right? Like,
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especially while you are pursuing something that you think is meaningful.
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You're achieving things that you think are meaningful. There's just
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a tendency to get really buttoned up and serious along
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the way and stop having the ability to make fun
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of yourself. And so I have this great group of friends,
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a lot of my baseball teammates from back in the
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day who no matter how far any of us make
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it in life, the exclusive purpose of when we get
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together is making fun of each other. And so I
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sort of just like have adopted that ethos in my
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own life that I just can't take myself too seriously ever.
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And so the bio is kind of a, you know,
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a jab in that direction of like, you know, I
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was accomplishing something that I thought was great. I was
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playing on this, you know, big stage and at this
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great level. And, you know, I had this horrible moment.
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I gave up a grand slam on national television, lost us,
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you know, a chance at playing in the College World Series.
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It was like one of the worst moments of my
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life at the time. But being able to laugh at
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yourself kind of on the back end of that stuff,
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I think is such a powerful thing. You know, and
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there's also a lesson there in like never getting too high,
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never getting too low. The week before that, I mean,
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the context to it is like the week before that
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we had played in the regional championships and I had
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closed the regional championship game, got a got a save
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in the regional championship game, like 10,000 people in the stands.
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you know, the highest moment of my baseball career to date.
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And I remember coming away from it being like, man,
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I am so good. Like I really thought, you know,
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it's like the Giannis quote from a few weeks ago.
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Like when you think about the past, that's all about
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your ego. And that was how it was. I was like, man,
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I did this. I did this. Like, look, I'm coming.
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I'm getting better.
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I'm going to get drafted.
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And then the next week I gave up this absolutely
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massive grand slam to lose my team, a chance at
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going to the college world series. And it was that
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exact example of like, you get too far ahead of yourself.
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You get too high. you get knocked down. It's just
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what happens. And so you need to be able to
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focus on the present and never get too high, never
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get too low. So that's always just really resonated with me.
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How do you, so I have a somewhat similar college story.
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I coming out of high school, I went to Miami
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of Ohio here in Ohio, obviously the Mid-American Conference. And
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I happened to go at the exact same time and
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play the same position as Ben Roethlisberger. And a bunch
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of people, college coaches, others called me back after, because
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Ben committed about a week after I did. And they said, hey, dude,
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you don't want to go there. It's not going to
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work out for you. And of course, I'm sure you're
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the same way when you're 18. You're like, you guys
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have no idea what you're talking about.
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I'll beat them out.
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And I think, though, the great lesson that I learned
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from that experience of battling it out for two years
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and maybe having this this belief in myself that I
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somehow could win this job, even though I like from
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the first day, I probably was never going to win
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that job, but I thought I was, but I think
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it's that you, you know, you do everything you can
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to make it happen. And the world doesn't necessarily care
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because the coach is going to play the guy who
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gives the team the best chance to win. And in
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this case, the late great Terry Heppner made the, obviously
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the right decision when he named him starter during our
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second year at Miami. And I think there's, those are
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awesome lessons. Like, and so I'm curious from, giving up
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that grand slam. It sounds like one of the toughest
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moments of your life at up to that point, at least, but,
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but especially in your formative years, having to bounce back
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from things like that, like what have you learned from
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that grand slam that has made you better in what
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you do today?
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Yeah. You know, it's interesting. It's like you hear about
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those big public failures and those moments, right? Like I
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talk about that one because it was a big moment.
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It was on TV. It was, you know, big game, whatever.
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I actually think the like private failures are even more
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impactful in terms of how they, how they kind of
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create you and shape you. Um, I think about one
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of the most impactful ones for myself was like the
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day I showed up at Stanford campus as a freshman 2009. And, um,
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you know, I'd grown up in a small town in Massachusetts.
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I was like the ultimate big fish, small pond syndrome. Like,
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you know, I thought I was hot shit, man. I mean, like,
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excuse my language, but Like I, you know, I thought
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I was really smart. I thought I was a great
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baseball player. I, you know, got a scholarship to go
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to this great school and I got to campus the
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first day and just got like kicked in the gut, um, academically, athletically,
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I mean, everything, right? Like I went to class and
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realized I wasn't that smart. Um, you know, I went
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to baseball practice and realized I wasn't that good at baseball. Um,
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and so I remember like freshman year was such a
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grind because it was like the first time in my
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life that I had really had to experience on a
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daily basis failures. Um, and in hindsight, you realize that
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that kind of stuff is crucial to forming and shaping
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who you are as a person later. The fact that
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you were able to like, just keep pounding your head
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into a wall, keep pounding your head into a wall,
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keep pounding your head until finally you break through. And
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you didn't really know when it was going to happen.
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There was no end in sight. It might've never happened. Um,
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it's like that idea of, are you willing to sprint
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when the distance is unknown? Um, which I've always loved.
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It's resonated with me. It gives me chills even when
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I like see people talk about that or quotes because
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it's so powerful. Like how much are you willing to
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just keep running when you have no idea how far
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you're going to be running? And those were the moments.
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I mean, none of it was public. It was like
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practices or going to class on a daily basis and
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just like being willing to just get knocked down every
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day and get back up. There's nothing more powerful than
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that in the long run than if you can kind
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of like form your character around that type of ethos.
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Has anything like that happened now?
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Because I think sports and especially going to a school
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like Stanford for you probably were great learning tools, but
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as then you transitioned to post-athletic you're into the business
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world you're investing you're you have a job you're doing
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things on the side can you think of like a
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moment how where you drew from that and it made
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you better in this more professional world that most of
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us are in now since we can't play sports forever.
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Yeah i mean every day it's like Your career, your life,
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it's all about how you bounce back from failures. No
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one has the privilege of only succeeding. If anyone tells
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you they do, they're lying or they're in such rare
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air that I can't even relate to them. I remember
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my first job, all of the failures that came with it.
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You screw stuff up.
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What was your first job after playing baseball?
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I went straight into the investing world. I got hurt
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my last year at school and thought I was going
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to go play professionally. It got taken away from me.
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probably for the better because I wasn't all that good
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in the grand scheme of things. But I went and
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took this job in the investing world, didn't know a
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lick about investing. And so I knew I was just
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going to have to do the same thing, like pick
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up and just start grinding with it. And I just
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remember like every day there was something I was screwing up.
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I'd forget to do something or make the same mistake twice.
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And the ability to actually like take those pieces of
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feedback in and not crumble from them is such a
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massive advantage in life. Like so many people that I
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saw and still see a lot of young people entering
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the work world, they can't take critical feedback. You like
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give them one piece of constructive feedback, not even critical, constructive, like, Hey,
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I want to make you better. Here's one, two, three
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things that you could do to make your performance better.
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And it's like they crumble almost because their whole life
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they've been only succeeding at things and they've only gotten
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straight A's and they've been at the top of their
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class and they went to X school or whatever it was.
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They never had to deal with that. Like, I'm bad
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at something. How do I pull up and get better?
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And so I just think that like those moments, especially
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as a parent, I think about it for, you know,
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when I eventually, God willing, have children and I'm raising them,
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what do I want to instill in them? And that's
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one of the biggest things to me is like, let
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them fail. let them fall on their face. And it's
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terrifying as a parent, I imagine, easier said than done.
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But those moments of failure and those things that I
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had to get smoked by are now the greatest experiences,
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the things that I wouldn't trade for the world in
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terms of forming my day-to-day perspective and character.
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You are an active angel investor. So first, for those
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who Don't know anything about that. I'll ask you to
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kind of define that for a second. But the second
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part of the question, which I'm going to ask you
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at the same time, is when you're looking to make
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an investment, what are some of the must-have qualities and
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or behaviors in a person that you're going to invest in?
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I know the idea is probably important or their product
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or whatever it is that they're doing, product, market, fit,
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or if you're so early, you might not even have
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that yet. But I'm really, because I think of the
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best investors when I hear what they say, they usually
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say something like, I invest in the person first before
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whatever it is.
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That they're doing.
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I believe in that person regardless of what they're doing.
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So I'm curious, C.O., from your perspective, what are some
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of those must-have qualities in a person to back?
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Yeah.
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Yeah.
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So, I mean, first off to your first question, angel investing,
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I think it's like this term that people start throwing
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around a lot.
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It's like....
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You know, effectively it's just that you are an individual,
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not a investment fund and you are providing money to startups, um,
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is the right way to think about it. And I
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don't know where the term angel officially got coined, but
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you know, you're like supposed to be like, they're saving grace.
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It's far from that. You know, you're, you're just, you're
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buying into a person and an idea and you're providing
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capital for them to go and execute in the very
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early days, generally before they can go get a venture
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fund to back them or whatever private, private fund. Um,
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And then to your question on what you're looking for,
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I mean, I think the resilience and grit is probably
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the number one thing. And the reason I say that
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is because startups and entrepreneurship and small business and all
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of these areas, you're just going to get knocked around.
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It's just the reality of life is that nothing is
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ever up and to the right in a straight line.
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And so if you're investing in a person, you're investing
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in their idea, The idea can be as good as
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you want, but it's going to have struggles along the way.
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Jeff Bezos, the struggles along the way of Amazon, when
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you look at how much wealth he's accumulated, it's because
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he was literally the only person that has held Amazon
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stock for that entire time. No one else could stomach
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those 60% drops that the stock had because of massive
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business issues over time. it was resilience. It was like,
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you stick with it and you continue to find a
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way to win in the long run. You like zoom
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out of the short-term issues and are able to kind
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of see the vision and see where it's headed and
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what I'm supposed to be doing. And when you find
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that in an entrepreneur, it's really hard to like ask
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the question that makes you figure out that they have
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it or not, but you can feel it. Like when
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you talk to someone, you can really feel it. And
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I'm by no means some expert. There are legendary investors
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who I'm sure have this like sixth sense figuring out
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whether an entrepreneur has that it factor. Um, but I
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think that is just like the most critical thing. Like,
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is this person just willing to die before they fail
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at this business? Um, and there are just people out
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there that have that, that are just like that. And
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you just know, um, that's not even an option for them.
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Like the business, this business that you're backing could completely
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collapse and they will somehow find a way to like
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Phoenix out of the ashes and start something else that
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ends up being even more impressive. So yeah, that a
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long way of answering your question, but I think resilience
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and grit are the two.
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You've done this more than 25 times from what I've read.
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So when you think, think to each of those 25
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plus decisions, like.
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Can you take us inside the room?
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Like, I don't know, or, or the zoom or the
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calls or like, how do you go from, Oh, okay.
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This is an opportunity to, all right, I'm giving them money.
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Like, can you, can you, I'm fascinated by that process.
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Like, how does it work? Yeah.
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I think it depends on like, first off, it depends
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on if you're in the COVID, you know, pre COVID
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or post COVID world, because a lot of the, okay.
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Maybe sure.
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Both.
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Yeah.
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Yeah. I mean, pre COVID, a lot of this stuff
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is driven by relationships and, and, in a sense, it
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was easier as an investor then because you got to
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spend time building relationship with these individuals that you were
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going to eventually back. And so you had more data points.
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You saw how they interacted with other people. You saw
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how they responded to different questions, challenges, things that were
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happening over just a longer duration. In the post-COVID era,
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a lot of this has been done via Zoom. It's
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like this, you're on a Zoom with someone. And so
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they have their like, you know, an entrepreneur that's really
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seasoned has their pitch and they know how to run
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through it. And so I've personally found like, if I'm
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doing a call with someone, I already understand the idea.
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I'm interested in the idea in the business. I believe
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in the long-term vision of it. So I personally try
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to take it more towards like, I want to get
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to know you, you know, tell me about a time
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you got your ass kicked type thing. But the other
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reality to it is like, I'm not an investment fund.
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I don't have, you know, limited partners, LPs that have
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given me their money to invest on their behalf. It's
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my money. And so, you know, when I do it,
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I want to get comfortable and the burden of that
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is different. And I reached that kind of burden of
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proof in different amounts of time, depending on the person.
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I've gotten on a call with someone in like two
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minutes in said to myself, holy crap, I got to
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back this person. I don't care what the idea is
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almost because like I need to back this person and
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they're going to figure it out. I had that with a,
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with an entrepreneur recently and And I actually didn't even
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think the idea is that good, what he's working on.
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But I just want to invest in him because I
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think that he's such a killer in the long run.
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But it just depends. It just depends what the circumstances
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are around it, how long it actually takes you to
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go develop that comfort around an idea. The other thing
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to mention, which people have probably seen in the news,
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is the market is so frothy and hot right now.
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And there's so much capital out there that these things
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like the timeframes around them have just compressed and compressed
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and compressed to the point where, you know, most of them,
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if you can't make a decision quickly, you're just, you're
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not going to have an opportunity to invest in the thing.
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You know, the like investors that are stealing everyone's lunch
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right now are the ones that can just move really quickly,
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you know, and send a.
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Check and say, let's go totally.
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Like they've done the work, they've done the prep in
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advance and, they know the industry, they know the market,
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they know the business, they know the competitive landscape. And
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so they're basically just like check the box on a
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couple of things that they really want to figure out
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and then they can just.
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Roll and make a move on it. So how about
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let's make it personal.
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So my current kind of investing strategy is I have
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set amount of money that goes to my financial advisor
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every month and it's kind of automated and I don't
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really think about it. And then I just let compounding
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go to work, right? The best way to get wealthy, right,
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is just don't interrupt it as Charlie Munger or Warren
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Buffett might say. And I'll continue to do that no
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matter what, but I am curious about this and I
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think other people are too.
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So let's say, Sahil, I called you and I'm like, dude,
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I want to do this.
399
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I have this set amount of disposable money that If
400
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I lose it, I lose it.
401
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It's okay. How can I get started?
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So what advice would you give to me if I'm like,
403
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I want to do this part of what you do?
404
00:19:46.039 --> 00:19:49.970
Yeah. I mean, look, my first advice would be don't.
405
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Do it.
406
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Just keep compounding. Because the reality of most of this,
407
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most people want to say they are an angel investor
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and it's become this like, it's like a flex almost.
409
00:20:03.019 --> 00:20:05.690
It's like a LinkedIn flex where you're like, you want
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to say that you're an angel investor. The reality is like,
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the vast majority of those investments go to zero because
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they're startups and they're like really risky. And so for
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most people, probably myself included, the like value maximizing thing
414
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to do over the long run would be to take
415
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all that money that you were going to angel invest
416
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and just put it into the S & P 500
417
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and let it just go up over the next 40
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years of your life. And you'll probably like on an
419
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expected value basis, that'll leave you the best off. My
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personal opinion on it always and why I do a
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lot of it is I learned so much from these conversations,
422
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from the people that I get to associate with because
423
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of it, from being around these businesses, from helping them.
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I mean, for me, I could lose all the money
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that I've invested in all this stuff, every single dollar.
426
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And I think it would be a net positive return
427
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to me because of the actual intellectual returns that I've
428
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gotten on that capital that I've put out beyond the
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financial returns. But on a purely financial basis... I think
430
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it's like the burden of wanting to get into that
431
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is very high. The challenge, so if you said, okay,
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I understand that and I want to do it, it's
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all about deal flow. What are you actually seeing? And
434
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so therefore, what can you execute against? The challenge with
435
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the venture world and with angel investing in general is
436
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that it is the ultimate game of adverse selection. The
437
00:21:29.039 --> 00:21:32.559
deals that want you to invest in them are typically
438
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not the ones you want to be investing in because
439
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they're the ones that no one else has backed, right?
440
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Like if there's some unbelievably hot company that can raise
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money from anyone in the world, like five years ago,
442
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maybe not now, but five years ago, if they had
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come to me and said like, Sahil, we want you
444
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to put in some money into this. My first reaction
445
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would have been like, why? Like, why do you want
446
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me to, I'm like some random analyst at a fund
447
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at the time. Like what about what is making you
448
00:22:00.680 --> 00:22:02.759
want me to invest? And that would almost like set
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off alarm bells. Now it's a little different because I
450
00:22:05.460 --> 00:22:07.099
can help them with a bunch of things. You know,
451
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I have a platform. I can talk about them publicly.
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I can get them exposure. And so now it's like,
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I'm in more of a real position to add value
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to them. And so I might be able to get
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into things that way. But like for a new person
456
00:22:19.190 --> 00:22:22.269
starting angel investing, every deal that you see, you almost
457
00:22:22.329 --> 00:22:24.990
have to have your initial reaction be like, why am
458
00:22:25.069 --> 00:22:28.130
I so lucky? Is this actually a really good opportunity
459
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or are they just showing it to me because they
460
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can't get the money from anyone else?
461
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Interesting.
462
00:22:32.829 --> 00:22:36.039
Yeah. It's like, uh, the very beginning of when people
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started asking me to come give talks, I would talk
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to other more experienced speakers.
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And I would say, hey, you have a speaking agent.
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Should I get one of those?
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And they said, trust me, the speaking agents will start
468
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reaching out to you the moment you don't need a
469
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speaking agent anymore, meaning like the book you kick. So
470
00:22:56.130 --> 00:22:59.190
it's just weird how the things work. And that's exactly
471
00:22:59.250 --> 00:23:01.869
how this has worked now that multiple years have passed
472
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where I don't need the inbound person or the person
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out there doing it.
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00:23:06.799 --> 00:23:08.660
It'd be just kind of like an admin person. It's
475
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not worth giving all that percentage for that. So I
476
00:23:10.660 --> 00:23:13.099
handle it myself. It's kind of interesting how the world
477
00:23:13.140 --> 00:23:14.039
kind of works that way.
478
00:23:14.480 --> 00:23:17.359
Totally. Yeah. I mean, that's a great analog, but there's
479
00:23:17.380 --> 00:23:18.799
so many analogs like that, right?
480
00:23:18.880 --> 00:23:19.500
Actually a lot.
481
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I mean, it's funny because the common adage within the
482
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financial world is that dentists have made the best marks
483
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for some of these funds to go and try to
484
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raise money from because they had they met the accredited
485
00:23:33.960 --> 00:23:37.140
investor thresholds, which are what require, you know, you're required
486
00:23:37.160 --> 00:23:39.359
to meet in order to invest in these private placements,
487
00:23:39.839 --> 00:23:43.259
but they weren't particularly knowledgeable about financial things because they
488
00:23:43.279 --> 00:23:46.809
had pursued a life of science and medicine. Um, and
489
00:23:46.849 --> 00:23:49.069
so those were the people that were like typically falling
490
00:23:49.119 --> 00:23:51.650
victim to, and it was obviously generalized, but that was
491
00:23:51.690 --> 00:23:53.910
like the, the thing that everyone would talk about were
492
00:23:53.950 --> 00:23:56.829
like dentists were the most prone to falling victim to
493
00:23:56.869 --> 00:23:59.250
these like random scams that were coming up within the
494
00:23:59.289 --> 00:23:59.910
finance world.
495
00:24:01.750 --> 00:24:04.190
Uh, Shifting gears a bit, and I want to talk
496
00:24:04.210 --> 00:24:04.950
about writing.
497
00:24:06.150 --> 00:24:10.150
There's a great Boston Globe story that talks about this,
498
00:24:10.390 --> 00:24:12.670
written about you, great picture with you and Tim Cook.
499
00:24:13.490 --> 00:24:15.990
But a lot of, I feel like, I mean, I
500
00:24:16.269 --> 00:24:18.750
became aware of you because of your willingness to ship
501
00:24:18.809 --> 00:24:21.470
work publicly, to learn in public, to share what you're learning,
502
00:24:21.519 --> 00:24:25.319
and to be a fantastic storyteller, whether it's through tweet
503
00:24:25.819 --> 00:24:30.849
threads or your sub stack. Can you first, from a
504
00:24:30.990 --> 00:24:36.329
leadership perspective, let's talk about from a leadership perspective, why
505
00:24:36.450 --> 00:24:41.210
should every leader have some form of a writing practice,
506
00:24:41.250 --> 00:24:42.710
whether they decide to publish it or not?
507
00:24:44.190 --> 00:24:50.539
Great question. Simple answer. When you write, you think better.
508
00:24:52.119 --> 00:24:54.579
I just think that writing is the best way to
509
00:24:54.640 --> 00:24:57.319
expose gaps in your thinking and where your thinking is
510
00:24:57.339 --> 00:25:06.049
falling short. It is impossible, virtually impossible to write down
511
00:25:06.390 --> 00:25:09.890
everything you know about an idea and not immediately see
512
00:25:09.930 --> 00:25:13.349
the gaps in what you know about that concept. And
513
00:25:13.390 --> 00:25:15.829
so for me, I mean, to make it real, like
514
00:25:15.849 --> 00:25:17.670
when I want to go write a thread or write
515
00:25:17.710 --> 00:25:22.079
a newsletter piece about some new topic, say inversion, it's
516
00:25:22.099 --> 00:25:24.119
like this mental model that I use quite a bit.
517
00:25:24.940 --> 00:25:27.619
I can go and write down a piece about it
518
00:25:28.180 --> 00:25:31.619
and then I'll read it. and realize, oh my God,
519
00:25:31.660 --> 00:25:34.559
there's like these massive gaps in how I'm understanding this.
520
00:25:35.059 --> 00:25:36.500
And I wouldn't have known that. I would have thought
521
00:25:36.539 --> 00:25:39.259
I understood inversion. Like, yeah, I understand it. Because your
522
00:25:39.299 --> 00:25:41.319
mind tells you that. You're just like, oh, I get it.
523
00:25:41.400 --> 00:25:43.200
I don't need to read more about this. And when
524
00:25:43.220 --> 00:25:45.849
you write it down, suddenly it becomes very clear to
525
00:25:45.890 --> 00:25:48.730
you where those gaps exist and how you can go
526
00:25:48.789 --> 00:25:52.549
fill them in. And so as a leader, I just
527
00:25:52.589 --> 00:25:55.230
think it's one of the most important things you can
528
00:25:55.289 --> 00:25:58.519
do for clarifying your thinking on any given topic. The
529
00:25:58.579 --> 00:26:01.380
other piece is it makes you better at everything you do.
530
00:26:01.559 --> 00:26:05.440
When you write clearly, you communicate more clearly. You're able
531
00:26:05.500 --> 00:26:09.059
to be more succinct in everything that you're putting together.
532
00:26:09.160 --> 00:26:12.519
I mean, my Twitter writing habit started with Twitter. It's
533
00:26:12.559 --> 00:26:15.220
become a newsletter writing habit has made me a better investor.
534
00:26:16.160 --> 00:26:19.829
It's made me a better husband. It's made me a
535
00:26:19.849 --> 00:26:22.269
better friend. I just, because I think more clearly and
536
00:26:22.309 --> 00:26:26.089
I think in more concise terms, I have more value
537
00:26:26.230 --> 00:26:28.710
add and conversations that I have with people because I'm
538
00:26:28.789 --> 00:26:30.950
able to just like draw upon these things that I've
539
00:26:31.019 --> 00:26:34.519
written about. And so I've learned them more effectively. It
540
00:26:34.559 --> 00:26:37.740
just has this massive spillover effect across all these realms
541
00:26:37.779 --> 00:26:38.279
of your life.
542
00:26:39.099 --> 00:26:45.819
I sold a book deal on management to my publisher
543
00:26:45.859 --> 00:26:48.579
McGraw Hill. I remember in the book proposal, you know,
544
00:26:48.599 --> 00:26:51.180
you write like a sample chapter, but a lot of
545
00:26:51.220 --> 00:26:54.039
it's kind of the mark. That's how a proposal sells.
546
00:26:54.059 --> 00:26:55.880
They're like, can this dude sell books? And we're going
547
00:26:55.900 --> 00:26:58.319
to say yes or no. The idea, yeah, they want
548
00:26:58.339 --> 00:27:01.059
it to be good enough. But then you get the deal,
549
00:27:01.559 --> 00:27:04.440
and then you have to actually write the book. And
550
00:27:05.160 --> 00:27:10.089
I didn't fully realize how little I actually knew about
551
00:27:10.140 --> 00:27:13.049
the topic that I had just sold a book deal
552
00:27:13.150 --> 00:27:16.849
until I was forced to go really deep. And so
553
00:27:17.170 --> 00:27:19.420
this is why I push all leaders to That was
554
00:27:19.460 --> 00:27:21.420
one of the greatest learning tools in the world. And
555
00:27:21.559 --> 00:27:25.390
so I push all leaders, write. I mean, I like
556
00:27:25.430 --> 00:27:27.430
if you're going to publish, but even if you're not,
557
00:27:27.450 --> 00:27:30.549
you should still write. And second, put yourself in the
558
00:27:30.589 --> 00:27:34.450
position of being a teacher. So anytime you're going to
559
00:27:34.470 --> 00:27:36.529
give a speech or you're going to meet with a
560
00:27:36.609 --> 00:27:38.970
mentee or you're going to try to help, let's say,
561
00:27:39.009 --> 00:27:41.819
a founder in your case, you're not going to want
562
00:27:41.839 --> 00:27:44.940
to not be a value add. So leading up to
563
00:27:44.980 --> 00:27:47.359
that meeting, you're probably going to really like, wait, what
564
00:27:47.380 --> 00:27:48.259
do I think about this?
565
00:27:48.319 --> 00:27:50.039
How am I going to help this person? What can
566
00:27:50.119 --> 00:27:50.420
I do?
567
00:27:50.779 --> 00:27:55.039
That process of preparing so much learning happens. Then you
568
00:27:55.140 --> 00:27:58.259
share the advice and you get immediate feedback if it
569
00:27:58.299 --> 00:28:00.900
was useful or not. And you can adjust moving forward.
570
00:28:01.180 --> 00:28:03.859
I feel like you seem to always be in the
571
00:28:03.880 --> 00:28:05.759
mode of being a teacher. And that seems to be
572
00:28:05.779 --> 00:28:08.400
a great learning tool for you, I gather.
573
00:28:09.180 --> 00:28:12.240
One hundred percent. I mean, it's funny, like people have
574
00:28:13.569 --> 00:28:15.210
told me over the course of the last year that
575
00:28:15.230 --> 00:28:16.849
they've learned a lot from the things that I've put
576
00:28:16.910 --> 00:28:19.250
out in the writing. And I like I think that's amazing.
577
00:28:19.730 --> 00:28:22.650
First off, I'm absolutely like I have so much gratitude
578
00:28:23.849 --> 00:28:26.519
for the era that we live in that I can
579
00:28:26.559 --> 00:28:28.880
like put things out there and that globally it can
580
00:28:28.900 --> 00:28:31.140
have an impact on people. I mean, like the responses
581
00:28:31.200 --> 00:28:33.819
I get from people in India and in Africa and
582
00:28:33.900 --> 00:28:36.019
all these places, like it's just incredible to me and
583
00:28:36.059 --> 00:28:38.460
I am still blown away by it every day. the
584
00:28:38.480 --> 00:28:41.200
thing I always say back is like, I'm actually learning
585
00:28:41.269 --> 00:28:46.089
alongside you about all of these things because I can't
586
00:28:46.109 --> 00:28:48.670
even describe how much smarter I have gotten in the
587
00:28:48.710 --> 00:28:51.549
last year from doing all of this writing that was
588
00:28:51.950 --> 00:28:54.420
from the outside looking in, looked like me teaching. It
589
00:28:54.440 --> 00:28:57.740
was actually me learning. And it's the most selfish thing
590
00:28:57.759 --> 00:29:01.019
I've ever done, candidly, because I've done all this writing
591
00:29:01.099 --> 00:29:03.660
and people view it as all this time that I've
592
00:29:03.839 --> 00:29:06.680
put out to help others. And that was a huge
593
00:29:06.720 --> 00:29:10.119
inspiration and motivation around it. But I've learned so much
594
00:29:10.180 --> 00:29:12.920
from doing it that like the downside to me of
595
00:29:13.000 --> 00:29:14.799
writing all of these pieces and doing all of this
596
00:29:14.839 --> 00:29:17.640
was that I learned a lot and the upside was limitless.
597
00:29:17.700 --> 00:29:19.549
And so it always just felt like that's a pretty
598
00:29:19.569 --> 00:29:21.829
good asymmetric trade I can make there.
599
00:29:22.990 --> 00:29:25.609
One of the things that you're really good at is
600
00:29:25.630 --> 00:29:28.130
writing great threads. So those who are, I guess not
601
00:29:28.170 --> 00:29:29.769
everyone's on Twitter. I find Twitter to be one of
602
00:29:29.789 --> 00:29:32.230
the greatest learning tools in the world. It's also been
603
00:29:32.250 --> 00:29:34.549
a great networking tool for me to meet people. That's
604
00:29:34.569 --> 00:29:38.809
how we met. And part of what makes your thread
605
00:29:38.849 --> 00:29:43.029
so good is that you're, become a phenomenal storyteller. So
606
00:29:43.049 --> 00:29:45.970
I do want to get specific on the threads thing,
607
00:29:45.990 --> 00:29:47.819
but I know not everybody cares about that. I do,
608
00:29:47.880 --> 00:29:50.359
but I know not everybody does. So let's start with
609
00:29:50.380 --> 00:29:54.640
the storytelling aspect of it. How have you worked on
610
00:29:55.079 --> 00:29:57.160
and what is the makings of someone who is a
611
00:29:57.259 --> 00:29:58.259
great storyteller?
612
00:29:58.319 --> 00:29:59.859
How can we do this? Yeah.
613
00:30:00.579 --> 00:30:06.269
I mean, for me, storytelling is a kind of built skill. Um,
614
00:30:06.710 --> 00:30:08.009
a lot of people think that you're either a good
615
00:30:08.049 --> 00:30:11.490
storyteller or you're not. And I just push back on that. Um,
616
00:30:12.589 --> 00:30:14.710
I read, I just spent a lot of time reading
617
00:30:15.039 --> 00:30:17.680
all of these different pieces on the principles of great
618
00:30:17.720 --> 00:30:21.859
storytelling from Disney and Pixar and the, these places that
619
00:30:21.900 --> 00:30:28.140
I consider to be, um, foundational storytellers. And I think, honestly,
620
00:30:28.480 --> 00:30:32.259
you can study that. I don't write about fantasy worlds
621
00:30:32.339 --> 00:30:38.049
and different realities, but those principles run through every area
622
00:30:38.069 --> 00:30:41.150
of your life. If you're an entrepreneur and you're running
623
00:30:41.170 --> 00:30:44.390
a business and you're constantly telling stories, you're doing it
624
00:30:44.410 --> 00:30:46.089
to your investors to tell them to give you money.
625
00:30:46.109 --> 00:30:47.910
You're doing it to your employees to give them that
626
00:30:48.009 --> 00:30:50.380
vision of what you're building and why it's so exciting.
627
00:30:50.730 --> 00:30:53.799
And so it's just a foundational skill on a day-to-day basis.
628
00:30:54.710 --> 00:30:56.509
And I just focused on how can I just keep
629
00:30:56.529 --> 00:31:00.059
getting better at it? My mom is an incredible storyteller.
630
00:31:01.099 --> 00:31:03.079
Everyone that knows her will say that about her. She
631
00:31:03.119 --> 00:31:06.440
just has this like air about her where she just
632
00:31:06.460 --> 00:31:09.579
kind of captivates a room. And I think maybe I
633
00:31:09.599 --> 00:31:11.710
had a little bit of that from her naturally. Like
634
00:31:11.750 --> 00:31:13.329
I was always the guy in the locker room that
635
00:31:13.349 --> 00:31:16.049
was telling stories and like, you know, had people laughing.
636
00:31:16.089 --> 00:31:18.309
I wasn't like a clown, but always had some story
637
00:31:18.349 --> 00:31:20.720
that I would like to be telling. And so I've
638
00:31:20.779 --> 00:31:22.779
kind of tried to take that and put it into
639
00:31:22.819 --> 00:31:25.380
my writing. When I'm writing about a topic, how can
640
00:31:25.420 --> 00:31:29.220
I infuse a degree of personality, of emotion, of novelty,
641
00:31:29.940 --> 00:31:32.960
something that just makes it more than a dry educational piece?
642
00:31:32.980 --> 00:31:36.410
Because you think about as a child, you have all
643
00:31:36.430 --> 00:31:38.710
these textbooks and these things that they're making you read,
644
00:31:38.730 --> 00:31:43.029
and it's really hard to absorb stuff that feels that dry, mundane.
645
00:31:43.950 --> 00:31:46.490
It's much easier to absorb something when it feels relatable.
646
00:31:46.529 --> 00:31:49.170
It feels like it has... wit. It feels like it
647
00:31:49.210 --> 00:31:52.269
has novelty or emotion and it's grabbing you in some
648
00:31:52.349 --> 00:31:55.380
different way. Um, and so I think it's just so
649
00:31:55.430 --> 00:31:58.880
important to develop that, to hone that skill, um, and
650
00:31:58.920 --> 00:32:01.359
really to just keep improving upon it. I mean, I
651
00:32:01.400 --> 00:32:03.000
started this a year and a half, not even a
652
00:32:03.019 --> 00:32:07.299
year and a half ago. I started it. I'm 12th
653
00:32:07.640 --> 00:32:10.269
of 2020, I started writing publicly. That was when I
654
00:32:10.289 --> 00:32:11.910
started my Twitter writing.
655
00:32:12.190 --> 00:32:12.450
Wow.
656
00:32:12.529 --> 00:32:14.430
Really? It's only been that amount of time?
657
00:32:14.450 --> 00:32:14.769
Yeah.
658
00:32:15.250 --> 00:32:15.529
Yeah.
659
00:32:15.529 --> 00:32:17.390
14 months or 15 months, whatever that is. I had
660
00:32:17.390 --> 00:32:23.210
500 Twitter followers, started putting stuff out. And I objectively
661
00:32:23.250 --> 00:32:26.210
think my early stuff was pretty bad. It was well-researched
662
00:32:26.279 --> 00:32:29.420
and well thought through, but it didn't have that extra
663
00:32:29.480 --> 00:32:32.640
kind of it factor. And that just comes from storytelling.
664
00:32:33.279 --> 00:32:36.519
So let's go a step further then. Let's break it down.
665
00:32:37.000 --> 00:32:40.859
Someone who says, I'm not a good storyteller, how can
666
00:32:40.880 --> 00:32:43.599
I get better? What are some of the practical applications
667
00:32:43.640 --> 00:32:45.839
or practical things they could take away from this conversation
668
00:32:46.240 --> 00:32:48.930
to implement immediately to become a better storyteller?
669
00:32:49.349 --> 00:32:53.789
Yeah. I think the three biggest ones for me, maybe
670
00:32:53.829 --> 00:32:55.569
I'm going to end up running over on that, but
671
00:32:56.089 --> 00:33:00.069
I think something that elicits an emotional response from the
672
00:33:00.130 --> 00:33:04.430
audience is You need emotion woven into the fabric of
673
00:33:04.470 --> 00:33:07.900
what you are writing, saying, speaking, whatever it might be.
674
00:33:07.920 --> 00:33:10.279
It needs to grab people in some way. And so
675
00:33:10.619 --> 00:33:12.359
when you're writing it or when you're sketching out your
676
00:33:12.400 --> 00:33:15.420
notes for something that you're going to publicly say and
677
00:33:15.440 --> 00:33:18.779
the storytelling aspect of it, you need to know what
678
00:33:18.819 --> 00:33:21.109
that emotion is going to be. What are you trying
679
00:33:21.140 --> 00:33:24.309
to elicit? Is it happiness? Is it hope? Is it inspiration?
680
00:33:24.329 --> 00:33:28.599
And the best writers do that naturally. I wasn't one
681
00:33:28.619 --> 00:33:30.549
of those like best writers. I had to force it.
682
00:33:30.619 --> 00:33:33.359
I would have to think before I wrote something. What
683
00:33:33.440 --> 00:33:35.279
is the emotion that I'm going for here and how
684
00:33:35.299 --> 00:33:37.059
do I weave that in and make sure that it's
685
00:33:37.369 --> 00:33:40.660
kind of creating that reaction and creating that response? The
686
00:33:40.680 --> 00:33:44.410
other piece is novelty to me. It's what is like
687
00:33:44.430 --> 00:33:47.170
the oh, wow moment that I'm triggering in my audience
688
00:33:48.190 --> 00:33:50.859
that's kind of taking them out of their. normal, just
689
00:33:50.900 --> 00:33:55.140
like humdrum life that I'm hitting them with. Because that's
690
00:33:55.160 --> 00:33:57.109
when you grab someone and then they remember it. Then
691
00:33:57.150 --> 00:33:59.470
they're telling that story and they're sharing it with somebody.
692
00:33:59.509 --> 00:34:02.250
And now you're bigger than just your one-to-one of you
693
00:34:02.269 --> 00:34:04.910
telling a story to someone else. It becomes like you
694
00:34:04.930 --> 00:34:07.559
have this K factor of like shareability of the things
695
00:34:07.579 --> 00:34:10.360
that you're putting out there. So I think those are
696
00:34:10.380 --> 00:34:12.420
the two biggest. I mean, the other one, which is
697
00:34:12.460 --> 00:34:15.619
just like table stakes for all writing and speaking is
698
00:34:16.340 --> 00:34:19.550
you need to be punchy and concise about how you
699
00:34:19.590 --> 00:34:22.630
tell a story. Telling a great story isn't about writing
700
00:34:22.670 --> 00:34:26.130
a million words and winding it in 40 directions and
701
00:34:26.210 --> 00:34:30.030
making it complicated and using big words. It's actually the opposite.
702
00:34:30.150 --> 00:34:31.650
It's like the Mark Twain quote. It's one of my
703
00:34:31.670 --> 00:34:35.030
favorite quotes. I didn't have time to write a short letter,
704
00:34:35.110 --> 00:34:38.070
so I wrote a long one instead. And I just
705
00:34:38.159 --> 00:34:40.920
love that quote because it's so true. It's much harder
706
00:34:41.019 --> 00:34:44.409
to simplify and write something very clear and short than
707
00:34:44.449 --> 00:34:49.710
it is to write some long winding verbose piece. And
708
00:34:49.750 --> 00:34:51.969
that plays through to storytelling. The best storytellers in the
709
00:34:52.010 --> 00:34:56.530
world are the most concise. Every single word is considered.
710
00:34:56.909 --> 00:35:00.449
It's thoughtful. And that's, I mean, I think that is
711
00:35:00.510 --> 00:35:02.389
just table stakes. If you want to be a great
712
00:35:02.429 --> 00:35:04.309
storyteller and you want to improve your storytelling.
713
00:35:04.329 --> 00:35:08.590
It's like a standup comedians talk about the economy of words,
714
00:35:09.090 --> 00:35:10.949
the best of the best. They make it feel like
715
00:35:10.989 --> 00:35:13.739
they just kind of just kind of stumble out on
716
00:35:13.880 --> 00:35:18.519
stage and start talking and yet the great ones have
717
00:35:19.119 --> 00:35:24.039
handcrafted every single word they say when they get on
718
00:35:24.079 --> 00:35:29.000
that stage so i want may may 9th 2020 is
719
00:35:29.019 --> 00:35:31.539
this the first thread that helped you blow up and
720
00:35:31.840 --> 00:35:33.320
and this is i just want to give an example
721
00:35:33.360 --> 00:35:35.380
for people who haven't read this or heard of your
722
00:35:35.420 --> 00:35:37.460
stuff yet and this is how it starts and it
723
00:35:37.539 --> 00:35:41.590
piqued my curiosity you A thread on markets. It is
724
00:35:41.630 --> 00:35:45.010
the year 1500 and you enter a market in Renaissance
725
00:35:45.070 --> 00:35:49.090
era Italy. There are buyers and there are sellers. Prices
726
00:35:49.230 --> 00:35:52.599
of the various goods are determined by the interaction by
727
00:35:52.639 --> 00:35:57.320
and among these individuals. Now in walks Mr. Federico, a
728
00:35:57.380 --> 00:35:58.980
man of endless means.
729
00:35:59.739 --> 00:36:00.800
Tweet two. Mr.
730
00:36:00.840 --> 00:36:03.159
Federico climbs a tower in the center of the market
731
00:36:03.199 --> 00:36:05.989
and proclaims, quote, I am a buyer of any and
732
00:36:06.030 --> 00:36:09.650
all goods in this market regardless of their price. He
733
00:36:09.710 --> 00:36:12.389
climbs down off the tower and exits the market to
734
00:36:12.429 --> 00:36:16.170
return to his mansion. What happens in the market when
735
00:36:16.210 --> 00:36:18.989
he leaves? And then the thread continues. So this is
736
00:36:19.010 --> 00:36:21.449
what I'm talking about. Like, I'm like, wait, it's like
737
00:36:21.489 --> 00:36:24.110
in a book where the good authors make you turn
738
00:36:24.179 --> 00:36:25.860
the page. I got to go to the next one
739
00:36:25.900 --> 00:36:27.380
and the next one and the next one, you can't
740
00:36:27.400 --> 00:36:30.719
put it down. So this is at the beginning of you,
741
00:36:30.800 --> 00:36:33.199
you probably had no followers at this point. And now
742
00:36:33.219 --> 00:36:38.130
you have 242,000 plus, um, So what's going through your
743
00:36:38.150 --> 00:36:40.530
head as you're putting this together now that I shared
744
00:36:40.570 --> 00:36:41.260
a real example?
745
00:36:41.639 --> 00:36:43.780
Yeah, that was my first one. So it's near and
746
00:36:43.800 --> 00:36:50.119
dear to my heart. So it's May 2020. Markets are
747
00:36:50.239 --> 00:36:53.269
soaring while the economy is still shut down. Everyone's stuck
748
00:36:53.289 --> 00:36:57.269
at home. And basically everyone in the world, myself included,
749
00:36:57.329 --> 00:36:59.210
was like, what the hell is going on?
750
00:36:59.650 --> 00:37:00.030
How is the.
751
00:37:00.010 --> 00:37:03.650
Market ripping right now while everyone's stuck at home and
752
00:37:03.690 --> 00:37:06.730
no one's spending money? And I was trying to find
753
00:37:06.769 --> 00:37:09.789
a way to explain the concept that like what the
754
00:37:09.849 --> 00:37:11.949
Federal Reserve is doing, which is they're going into the
755
00:37:11.989 --> 00:37:14.250
market and basically just buying a bunch of stuff and
756
00:37:14.469 --> 00:37:17.820
the impact that has on prices in a market. And
757
00:37:17.840 --> 00:37:19.139
I was like, how can I do this in a
758
00:37:19.159 --> 00:37:20.980
way that is going to make it digestible? It's not
759
00:37:21.000 --> 00:37:23.539
going to be technical things about buying bonds and what
760
00:37:23.559 --> 00:37:26.119
they're doing. And it's going to be accessible to anybody.
761
00:37:26.539 --> 00:37:29.260
And so I basically, I sat down, I had a
762
00:37:29.280 --> 00:37:31.519
few friends from my baseball days texting me, asking me
763
00:37:31.559 --> 00:37:33.159
these questions. And I was like, I need to figure
764
00:37:33.199 --> 00:37:35.219
out something that I can just send them And I
765
00:37:35.239 --> 00:37:37.309
can just be like, here, this explains it. You'll get it.
766
00:37:38.260 --> 00:37:40.010
And that was how that came to life. And I
767
00:37:40.070 --> 00:37:45.670
created that fictional character, Mr. Federico, which is admittedly not
768
00:37:45.690 --> 00:37:48.190
my best humor, but it got the point across that
769
00:37:48.210 --> 00:37:51.730
that's what I was talking about. And I wrote that
770
00:37:52.050 --> 00:37:53.690
on the floor of my garage just because I had
771
00:37:53.730 --> 00:37:55.739
an idea right then. I wanted to write it down.
772
00:37:56.340 --> 00:37:59.440
And I posted it. First off, I called my shot
773
00:37:59.500 --> 00:38:00.980
because I told my wife that it was going to
774
00:38:01.000 --> 00:38:02.820
go viral. And she rolled her eyes at me and
775
00:38:02.840 --> 00:38:06.110
walked away. I had 500 followers at the time, so
776
00:38:06.130 --> 00:38:09.269
there was no reason to think so. You really believed
777
00:38:09.309 --> 00:38:09.690
that though.
778
00:38:09.829 --> 00:38:11.570
What's that? You really believed that.
779
00:38:11.650 --> 00:38:13.289
I did. Yeah. I wrote it and I was like,
780
00:38:13.309 --> 00:38:15.739
I basically just wrote it and I was like, this
781
00:38:15.800 --> 00:38:19.380
is really good. If this is a meritocracy, which I
782
00:38:19.420 --> 00:38:23.679
believe Twitter effectively is, this should go viral. This is
783
00:38:23.760 --> 00:38:26.019
really good. It's thoughtful. It gets the point across. I
784
00:38:26.059 --> 00:38:28.699
think it's really good. And so I tweeted it and
785
00:38:29.340 --> 00:38:30.820
I didn't have many followers, so it didn't really get
786
00:38:30.860 --> 00:38:33.260
much traction at first. And then I sort of hustled
787
00:38:33.300 --> 00:38:35.610
a little bit. I commented it under a couple of
788
00:38:35.670 --> 00:38:39.610
big accounts posts. And Chamath, who has this massive following,
789
00:38:39.690 --> 00:38:43.010
saw it and retweeted it and said, this is good
790
00:38:43.070 --> 00:38:45.369
and retweeted it. And so all of a sudden, my
791
00:38:45.429 --> 00:38:48.690
phone just went bananas. I went from having 500 followers
792
00:38:48.730 --> 00:38:52.969
to 2000 or something that day. And that was kind
793
00:38:53.010 --> 00:38:54.829
of the start of it. I realized like, oh, there's
794
00:38:54.869 --> 00:38:59.389
something to this concept of breaking these concepts down in
795
00:38:59.469 --> 00:39:02.769
an easy, digestible way for people. And that it wasn't
796
00:39:02.809 --> 00:39:04.869
out there. Like in general, I had this perception that
797
00:39:04.909 --> 00:39:08.110
the market had split where in the world of finance,
798
00:39:08.130 --> 00:39:10.650
in the world of business, you have like the really
799
00:39:10.690 --> 00:39:14.050
low end, like the TikTokers that are giving you nonsense
800
00:39:14.090 --> 00:39:16.699
advice about buying options and like all of that stuff.
801
00:39:16.840 --> 00:39:18.679
And then you had the like really high end of
802
00:39:18.739 --> 00:39:20.820
people who are just talking over your head. They're like,
803
00:39:21.360 --> 00:39:23.940
you know, basically trying to make you feel dumb because
804
00:39:23.980 --> 00:39:25.900
they want you to pay them to manage their money,
805
00:39:25.960 --> 00:39:29.170
whatever it might be. And so my decided was like, if,
806
00:39:29.469 --> 00:39:32.269
if this end, is the like really crappy like you
807
00:39:32.289 --> 00:39:34.690
know bicycle and this end is the like ferrari i
808
00:39:34.710 --> 00:39:37.380
was like i'm gonna be the like toyota camry just
809
00:39:37.409 --> 00:39:39.420
like good old faithful gets you from point a to
810
00:39:39.440 --> 00:39:42.559
point b sell tons of those cars because they're just
811
00:39:42.599 --> 00:39:46.059
very you know they're like a good price point quote-unquote Um,
812
00:39:46.280 --> 00:39:47.659
and that's what I wanted to be. I wanted it
813
00:39:47.719 --> 00:39:50.300
to be accessible, digestible. I wanted anyone to be able
814
00:39:50.320 --> 00:39:52.809
to share it and get value out of it. Um,
815
00:39:53.110 --> 00:39:55.150
and I think I've generally met that, you know, met
816
00:39:55.170 --> 00:39:56.690
that burden that I tried to set out for.
817
00:39:57.289 --> 00:39:59.070
Reminds me a little bit of Tim Urban. He's been
818
00:39:59.090 --> 00:40:01.789
on the show. He writes at weight, but Wyatt.com takes
819
00:40:01.809 --> 00:40:03.090
a huge fan of Tim. Yeah.
820
00:40:03.130 --> 00:40:05.949
I think everyone who writes loves Tim because he takes
821
00:40:06.429 --> 00:40:11.679
the super complex, makes it simple and is funny. And, um,
822
00:40:13.599 --> 00:40:18.019
I think the best writers have that ability to take
823
00:40:18.039 --> 00:40:21.389
the complex, they then digest it and synthesize it and
824
00:40:21.489 --> 00:40:23.469
retell it in the form of a story. They add
825
00:40:23.510 --> 00:40:28.230
some humor and they make the reader feel smarter after
826
00:40:28.289 --> 00:40:30.889
having read them, not dumber because they speak like, listen
827
00:40:30.909 --> 00:40:34.000
to my big words. And that is what I strive for.
828
00:40:34.019 --> 00:40:36.699
I think that's what leaders in general should strive for,
829
00:40:36.760 --> 00:40:40.690
regardless of your title, regardless of your job. And one
830
00:40:40.710 --> 00:40:42.760
of the best ways, I think, to get better at this, one,
831
00:40:42.989 --> 00:40:44.739
first and foremost, like anything else, you just got to
832
00:40:44.780 --> 00:40:46.619
do it, right? You got to get the reps. But
833
00:40:46.639 --> 00:40:49.260
then two, and I think a close second is you
834
00:40:49.280 --> 00:40:51.300
got to be reading this stuff constantly. And that's why
835
00:40:51.440 --> 00:40:53.679
Twitter has been a great learning tool for me. And
836
00:40:53.699 --> 00:40:55.880
I push people towards it because there are some negative
837
00:40:55.900 --> 00:40:58.480
things just like anything else in life, but there's so
838
00:40:58.539 --> 00:40:59.980
much positive that comes from it.
839
00:40:59.980 --> 00:41:02.159
And there's so much out there to learn.
840
00:41:02.179 --> 00:41:04.239
And I feel like this is something you've really, it's
841
00:41:04.300 --> 00:41:05.320
become part of you.
842
00:41:05.699 --> 00:41:05.980
Yeah.
843
00:41:06.360 --> 00:41:06.539
Yeah.
844
00:41:06.639 --> 00:41:08.679
I mean, to me, it's just about being positive some.
845
00:41:09.500 --> 00:41:13.199
you clearly have that mentality, but the world in my
846
00:41:13.260 --> 00:41:17.360
view is positive, is a positive sum game when other
847
00:41:17.409 --> 00:41:20.690
people win and we have a rising tide and a
848
00:41:20.750 --> 00:41:24.489
groundswell of people getting smarter and feeling empowered and inspired
849
00:41:24.550 --> 00:41:27.289
by things I'm putting out there. That makes me better off.
850
00:41:27.329 --> 00:41:30.530
Like the economy starts getting better. People are making better decisions.
851
00:41:30.570 --> 00:41:34.010
They're spending money on things. They're investing in things. And, um,
852
00:41:35.219 --> 00:41:37.199
And when that happens, we all win. And so like,
853
00:41:37.469 --> 00:41:40.110
I just have this general positive, some mentality around this stuff,
854
00:41:40.170 --> 00:41:42.289
or if I can empower people, and if I can
855
00:41:42.329 --> 00:41:45.050
spend a few hours writing something that I don't know,
856
00:41:45.070 --> 00:41:47.250
I mean, the recent things I'm putting out there, like
857
00:41:47.429 --> 00:41:50.400
it's 2 million, 3 million impressions in 24 hours. It's like,
858
00:41:50.659 --> 00:41:53.280
that's an unbelievable number of people that I can reach.
859
00:41:53.340 --> 00:41:57.480
And if 1% of those people feel empowered and inspired
860
00:41:57.539 --> 00:42:02.150
or learn one thing, that's the best university teacher in
861
00:42:02.170 --> 00:42:04.130
the world. You can't reach that many people. And so
862
00:42:04.150 --> 00:42:05.809
we live in this era where I can do that.
863
00:42:06.349 --> 00:42:08.670
And I just am blown away by that fact. And
864
00:42:08.730 --> 00:42:11.809
so that's kind of what inspires me to continue doing
865
00:42:11.889 --> 00:42:16.269
it is just this general positive sum mentality that I
866
00:42:16.389 --> 00:42:20.590
feel around all of it. I tweeted something about starting
867
00:42:20.610 --> 00:42:23.969
to genuinely root for others to succeed is this massive
868
00:42:24.050 --> 00:42:26.809
unlock in life. And I really believe it. The people
869
00:42:26.909 --> 00:42:30.139
who I look at who have helped me along the
870
00:42:30.179 --> 00:42:32.780
way who had no reason, like I was giving them
871
00:42:32.880 --> 00:42:36.219
no benefit. Um, and I may never give them a benefit,
872
00:42:36.539 --> 00:42:38.670
but they still just rooted for me along the way. Um,
873
00:42:40.050 --> 00:42:41.730
that just blows me away. And I want to be
874
00:42:41.769 --> 00:42:45.929
that person to tens, hundreds, thousands of others, you know,
875
00:42:45.949 --> 00:42:47.809
in their lives so that they feel that same way.
876
00:42:47.829 --> 00:42:48.670
Yeah.
877
00:42:49.250 --> 00:42:50.889
One of the things I wanted to talk to you about,
878
00:42:50.949 --> 00:42:54.010
since we have the similar background of playing, um, a
879
00:42:54.110 --> 00:42:58.579
sport in college, is that we've had experiences with coaches,
880
00:42:59.159 --> 00:43:02.940
both on the field and maybe a boss can play
881
00:43:02.980 --> 00:43:05.559
the role of a coach as well. I'm curious from
882
00:43:05.619 --> 00:43:09.199
your perspective, what have you found when you compare and
883
00:43:09.219 --> 00:43:13.219
contrast the excellent coaches who have made your life better
884
00:43:13.260 --> 00:43:15.539
in more ways than just maybe throwing the ball harder
885
00:43:16.360 --> 00:43:20.510
or more accurate, but they've made you better? What's the
886
00:43:20.679 --> 00:43:24.989
makeup of a great coach, um, both sports wise and
887
00:43:25.010 --> 00:43:27.110
maybe outside of the sporting world too, in your mind.
888
00:43:27.130 --> 00:43:30.659
Yeah. I think the two things for me are in
889
00:43:30.699 --> 00:43:34.760
the trenches with the team. Um, that's a common thread
890
00:43:34.780 --> 00:43:38.099
in everything, whether that's sports or life, the best leaders,
891
00:43:38.139 --> 00:43:40.860
the best coaches, they're in the trenches with their guys.
892
00:43:40.880 --> 00:43:43.820
Like they're never, it's, um, I think it's the New
893
00:43:43.880 --> 00:43:48.239
Zealand all blacks, like the, the, um, the concept of like,
894
00:43:48.380 --> 00:43:50.880
never be too big to do the small things. And
895
00:43:51.440 --> 00:43:53.480
the team, the captains of the team are the ones
896
00:43:53.519 --> 00:43:55.389
that have to sweep out the locker room at the
897
00:43:55.409 --> 00:43:57.610
end of a game. And I was always taken with
898
00:43:57.650 --> 00:44:00.909
that concept and it's, it's it's really powerful. And I
899
00:44:00.949 --> 00:44:04.010
think the best coaches do it naturally. You can learn that,
900
00:44:04.190 --> 00:44:06.949
but it's just being in the trenches with, with the
901
00:44:06.989 --> 00:44:09.820
guys or girls on the team and, and you know,
902
00:44:09.840 --> 00:44:13.199
feeling like you're fighting alongside them. You just do so
903
00:44:13.260 --> 00:44:15.219
much and you want to work for that coach that's
904
00:44:15.239 --> 00:44:17.719
there with you. And then the other one is someone
905
00:44:17.739 --> 00:44:18.719
that's willing to challenge you.
906
00:44:18.739 --> 00:44:19.619
Yeah.
907
00:44:20.110 --> 00:44:22.610
Call you out when you're wrong on something, tell you
908
00:44:22.650 --> 00:44:24.909
that you're, you know, what you did is not good enough.
909
00:44:25.630 --> 00:44:26.949
Um, because otherwise you're.
910
00:44:26.829 --> 00:44:28.829
Just never going to get better. I mean, I had,
911
00:44:28.989 --> 00:44:32.050
I've had coaches in my life that were, you know,
912
00:44:32.130 --> 00:44:35.769
sort of just, um, sort of just there and like,
913
00:44:36.050 --> 00:44:38.130
you know, not going to call you out if you
914
00:44:38.170 --> 00:44:40.530
didn't put in the effort you should have because you
915
00:44:40.550 --> 00:44:42.449
were the star or whatever. They don't want to call
916
00:44:42.510 --> 00:44:45.170
out the star. The best coaches I found were the
917
00:44:45.250 --> 00:44:48.219
ones that were like, literally just say to your face,
918
00:44:48.500 --> 00:44:50.460
that's not good enough. You know, it's not good enough
919
00:44:50.519 --> 00:44:52.900
as well as I do. And if you're okay with
920
00:44:52.920 --> 00:44:55.019
that as your level of effort, there's, I don't know.
921
00:44:55.039 --> 00:44:57.219
I don't know who you are as a person. Um,
922
00:44:57.550 --> 00:44:59.789
those kinds of things, you're just like, Whoa, it kind
923
00:44:59.829 --> 00:45:01.690
of like knocks you back when someone calls you out
924
00:45:01.730 --> 00:45:03.750
like that. But those are the moments where you get,
925
00:45:03.889 --> 00:45:05.429
you might get pissed and you might be like, how
926
00:45:05.489 --> 00:45:08.369
dare they say that to me. But if it triggers
927
00:45:08.409 --> 00:45:10.250
that response and you kind of jump in and you're
928
00:45:10.289 --> 00:45:13.539
working harder because of it, I mean, man, the impact
929
00:45:13.559 --> 00:45:16.039
that can have on a full team when you're doing that. Um,
930
00:45:16.760 --> 00:45:18.679
And I always found that. I mean, I've had some
931
00:45:18.699 --> 00:45:21.599
amazing coaches and been privileged to have some amazing mentors,
932
00:45:22.420 --> 00:45:23.980
people that have been around me in my life. And
933
00:45:24.280 --> 00:45:26.239
the common thread among the most amazing ones is they
934
00:45:26.260 --> 00:45:29.300
just push my thinking. They just push me and push me.
935
00:45:29.320 --> 00:45:32.400
And if I say something that's unfounded, they're like, oh,
936
00:45:32.440 --> 00:45:34.199
do you really believe that? You think you've done the
937
00:45:34.239 --> 00:45:37.380
work to really believe that or to make that assertion
938
00:45:37.440 --> 00:45:40.789
in that confident of a manner? And normally you realize
939
00:45:40.809 --> 00:45:44.110
that you have it and you're like, oh crap, they're right.
940
00:45:44.230 --> 00:45:46.300
I need to dig in further. I need to spend
941
00:45:46.340 --> 00:45:48.820
more time on that. But I think it's those two.
942
00:45:48.860 --> 00:45:51.559
It's being in the trenches and then it's just being
943
00:45:51.619 --> 00:45:54.079
willing to challenge the people that are under you.
944
00:45:55.420 --> 00:45:55.960
I like that.
945
00:45:57.260 --> 00:45:59.820
I know for me, from a coaching perspective, they're the
946
00:45:59.880 --> 00:46:02.739
ones who pushed me to levels that I didn't even
947
00:46:02.800 --> 00:46:05.900
realize I was capable of. And that's because they weren't
948
00:46:05.980 --> 00:46:10.550
afraid for me to temporarily dislike them. Um, I, I,
949
00:46:10.730 --> 00:46:14.880
I grew to love them deeply sometimes after the fact,
950
00:46:15.360 --> 00:46:18.300
but I love the fact that they cared so much
951
00:46:18.860 --> 00:46:21.860
that they were willing to upset me because they knew
952
00:46:21.880 --> 00:46:24.280
that's what it took to get me to perform at
953
00:46:24.300 --> 00:46:26.610
a level. And I would say, I don't think I
954
00:46:26.650 --> 00:46:29.309
get a college scholarship without my two of my high
955
00:46:29.329 --> 00:46:29.789
school coaches.
956
00:46:29.849 --> 00:46:32.130
I'm in the exact same boat. My, um, my high
957
00:46:32.150 --> 00:46:36.090
school baseball coach who I'm still extremely close with to
958
00:46:36.110 --> 00:46:40.590
this day. I was just Coach John Beverly, small public
959
00:46:40.630 --> 00:46:44.469
high school in Massachusetts. And I remember like my freshman
960
00:46:44.489 --> 00:46:46.730
and sophomore year of high school, I had two great seasons,
961
00:46:47.630 --> 00:46:50.389
but I was throwing, I don't know, 78, 80 miles
962
00:46:50.429 --> 00:46:52.090
an hour, but I was good. I was like, you know,
963
00:46:52.150 --> 00:46:54.550
Dyson guys, a little, little breaking ball. Yeah. I was,
964
00:46:54.650 --> 00:46:57.110
I was doing the whole dance. And I remember at
965
00:46:57.139 --> 00:46:58.980
the end of that sophomore season, he called me in
966
00:46:59.000 --> 00:47:00.920
and he was like, what do you want to do? Like, well,
967
00:47:00.940 --> 00:47:03.320
what's your vision for baseball? Do you want to play
968
00:47:03.360 --> 00:47:05.780
in college? And I said like, yeah, I think maybe
969
00:47:05.820 --> 00:47:08.400
I could play in an Ivy league and, Um, you know,
970
00:47:08.420 --> 00:47:10.219
that's kind of lower end D one baseball. I think
971
00:47:10.260 --> 00:47:12.119
I could go do that. And he looked me straight
972
00:47:12.139 --> 00:47:14.800
in the face and he was like, how about Stanford?
973
00:47:15.460 --> 00:47:19.199
How about rice? And I remember thinking like this dude crazy.
974
00:47:19.360 --> 00:47:20.840
I mean, that was like the first thought that went
975
00:47:20.860 --> 00:47:23.210
through my mind was just like, this guy's nuts. I'm
976
00:47:23.250 --> 00:47:27.289
like a five, 10, 165 pound right-hander from Massachusetts public
977
00:47:27.309 --> 00:47:29.110
high school in Massachusetts. I'm throwing 80 miles an hour.
978
00:47:29.409 --> 00:47:31.110
What do you mean Stanford? Like Stanford's one of the
979
00:47:31.130 --> 00:47:34.079
best baseball programs in the country. Um, And he was
980
00:47:34.139 --> 00:47:35.980
dead serious. He looked, I mean, like I kind of
981
00:47:36.039 --> 00:47:37.460
laughed and I looked at him and he was just
982
00:47:37.500 --> 00:47:39.409
staring at me. And he's like, if you were willing
983
00:47:39.429 --> 00:47:40.949
to put in the work, you have the talent to
984
00:47:40.989 --> 00:47:43.750
do this. It's going to be hard, but that's what
985
00:47:43.789 --> 00:47:45.969
I expect from you is doing that. And all of
986
00:47:46.010 --> 00:47:48.829
a sudden it was like, oh, wow. Someone believes in
987
00:47:48.869 --> 00:47:51.110
me at that level. Like this guy who is an
988
00:47:51.170 --> 00:47:54.480
informed individual and credible believes in me at that level.
989
00:47:55.559 --> 00:47:58.099
And a year later, I had a scholarship offer from
990
00:47:58.119 --> 00:48:00.500
Stanford and I was signing a letter of intent to
991
00:48:00.539 --> 00:48:03.010
go to Stanford. And I attribute so much of that
992
00:48:03.050 --> 00:48:05.329
to just that one moment where he kind of challenged
993
00:48:05.369 --> 00:48:07.670
me and he was like, what about Stanford? What about Rice?
994
00:48:09.050 --> 00:48:11.349
It still blows me away to think about it. I mean,
995
00:48:11.429 --> 00:48:13.150
one of the most impactful moments in my whole life,
996
00:48:13.230 --> 00:48:15.079
I mean, in terms of setting a trajectory. And I
997
00:48:15.239 --> 00:48:20.340
owe him a massive debt of gratitude. But it's just amazing.
998
00:48:20.380 --> 00:48:22.940
There's like one person that believes in you on some
999
00:48:23.000 --> 00:48:24.920
level like that and is willing to challenge you and
1000
00:48:24.940 --> 00:48:27.550
kind of push you to that level can totally change
1001
00:48:27.590 --> 00:48:29.550
the trajectory and your path.
1002
00:48:30.139 --> 00:48:32.250
Doesn't that make you want to do that for other people?
1003
00:48:33.130 --> 00:48:36.570
Totally. I mean, it's what I try to do every
1004
00:48:36.610 --> 00:48:38.570
single day. I want to mentor people. I want to
1005
00:48:38.590 --> 00:48:42.110
be that person that had that impact. It's why I
1006
00:48:42.150 --> 00:48:45.730
think coaches, teachers, we're some of the most underpaid people
1007
00:48:45.769 --> 00:48:49.679
in the world. Everyone has that one high school teacher
1008
00:48:49.739 --> 00:48:54.019
or some person that, again, for no benefit, for no
1009
00:48:54.059 --> 00:48:57.719
monetary benefit, helped you and completely changed the course of
1010
00:48:57.739 --> 00:49:01.030
your life. And we pay our teachers like crap. We
1011
00:49:01.050 --> 00:49:03.690
pay these high school coaches like crap. And the impact
1012
00:49:03.730 --> 00:49:05.719
they have on young men and women and the course
1013
00:49:05.739 --> 00:49:08.539
of their life, it's truly remarkable.
1014
00:49:09.440 --> 00:49:13.199
I think it's got to be such a fulfilling and
1015
00:49:13.239 --> 00:49:16.019
rewarding feeling for them to do it. Uh, and I've,
1016
00:49:16.199 --> 00:49:18.480
I've gone back and interviewed some even had, had, had
1017
00:49:19.039 --> 00:49:21.159
a couple on this podcast because as a, as a
1018
00:49:21.199 --> 00:49:21.900
way to say thank you.
1019
00:49:21.940 --> 00:49:23.920
And just to deconstruct how their mind works.
1020
00:49:24.639 --> 00:49:28.070
And, um, to me, I love the thought of like
1021
00:49:28.170 --> 00:49:32.650
seeing something in someone who they believe in themselves, but they,
1022
00:49:33.050 --> 00:49:36.389
maybe their level of expectations are just right. Like here,
1023
00:49:36.670 --> 00:49:40.760
you know, they're, kind of realistic, but they've got like
1024
00:49:40.780 --> 00:49:43.739
a ceiling that they've put that it's not intentional. There's
1025
00:49:43.800 --> 00:49:49.449
nothing bad. They just don't really think bigger. And for
1026
00:49:49.489 --> 00:49:55.789
you or me or anyone to say, actually, Stanford, Rice,
1027
00:49:57.309 --> 00:50:00.309
that is realistic for you. I know it is. And
1028
00:50:00.369 --> 00:50:03.829
here's some things to do to do it. But it's
1029
00:50:03.909 --> 00:50:06.550
actually in play. And all of a sudden, your mind changes.
1030
00:50:06.590 --> 00:50:11.659
Your mind shifts. your expectation level changed. And to me,
1031
00:50:11.719 --> 00:50:14.480
like he set a standard of excellence for you that
1032
00:50:14.539 --> 00:50:16.900
we can do. We can do this for people if
1033
00:50:16.960 --> 00:50:19.920
we care, but that's hard. Like it's much easier for
1034
00:50:19.940 --> 00:50:21.530
your coach to be like, wow, I'm glad you're on
1035
00:50:21.590 --> 00:50:24.250
our team. Don't transfer. Don't go somewhere else.
1036
00:50:24.769 --> 00:50:25.289
I love you.
1037
00:50:25.389 --> 00:50:27.809
I'm here for you instead. He's like, no, I'm going
1038
00:50:27.829 --> 00:50:30.730
to push you and raise your level of expectations. Like
1039
00:50:30.769 --> 00:50:33.070
what an awesome moment of leadership.
1040
00:50:33.619 --> 00:50:36.039
Yeah. Insane. I mean, it's like the Pygmalion effect. I
1041
00:50:36.079 --> 00:50:38.179
just wrote about this. It's a cognitive bias. It's like
1042
00:50:38.219 --> 00:50:43.400
high expectations lead to improved and higher performance. Someone vocalizing
1043
00:50:43.719 --> 00:50:47.579
that they have these amazing high expectations for you has
1044
00:50:47.599 --> 00:50:49.780
this impact where you just want to live up to
1045
00:50:49.820 --> 00:50:51.960
those expectations that the person has set for you. You
1046
00:50:51.980 --> 00:50:54.460
want to work hard and achieve those things.
1047
00:50:54.800 --> 00:50:55.179
I don't know.
1048
00:50:55.239 --> 00:50:57.840
It's funny. We go through life and we don't necessarily
1049
00:50:57.929 --> 00:51:03.130
vocalize our thanks for the people that that gave us
1050
00:51:03.170 --> 00:51:04.989
those moments. I mean, I'm like, I'm going to send
1051
00:51:05.010 --> 00:51:07.780
my coach this, this podcast. Cause I want him, I
1052
00:51:07.820 --> 00:51:10.019
want him to hear it and, you know, like publicly
1053
00:51:10.039 --> 00:51:12.659
kind of hear the word of thanks, but you know,
1054
00:51:12.699 --> 00:51:14.199
maybe I've said it to him over the years, but
1055
00:51:14.239 --> 00:51:16.960
it's just funny to think about like how impactful one moment.
1056
00:51:17.019 --> 00:51:18.869
I don't even know if he remembers that moment, but
1057
00:51:18.909 --> 00:51:20.949
it's so impactful for me. Yeah.
1058
00:51:21.030 --> 00:51:23.110
He probably doesn't, you know, he probably doesn't. I've, I've
1059
00:51:23.150 --> 00:51:25.510
said those things to my coach was like, Oh, cause
1060
00:51:25.570 --> 00:51:26.289
it's just the way they are.
1061
00:51:26.559 --> 00:51:27.760
Yeah. You know, like the great ones.
1062
00:51:28.199 --> 00:51:31.159
And they've done it for other people, too, because that's
1063
00:51:31.179 --> 00:51:33.539
just their standard mode of operation. And I think that
1064
00:51:33.679 --> 00:51:35.860
I'm glad you said that this is a good kind
1065
00:51:35.900 --> 00:51:39.099
of signal for people. If there is somebody like that
1066
00:51:39.159 --> 00:51:41.800
in your life and hopefully there is or hopefully there's
1067
00:51:41.840 --> 00:51:44.300
more than one, I would urge you to tell them,
1068
00:51:44.639 --> 00:51:47.800
call them, email them, try to see them if possible.
1069
00:51:47.820 --> 00:51:49.099
I would urge you.
1070
00:51:49.199 --> 00:51:52.389
I did this recently with my high school offensive coordinator
1071
00:51:52.429 --> 00:51:54.670
who became a head coach. I asked him to go
1072
00:51:54.690 --> 00:51:58.139
to dinner. This was months ago. And, uh, we went
1073
00:51:58.219 --> 00:51:59.659
out to eat and I just wanted to look him
1074
00:51:59.679 --> 00:52:00.820
in the eye. He was with his wife and I
1075
00:52:00.860 --> 00:52:02.900
wanted his wife to hear it too. I wanted her
1076
00:52:02.920 --> 00:52:05.010
to hear like the impact he had on me. And
1077
00:52:05.050 --> 00:52:07.550
I just was like, honestly told him exactly how I felt.
1078
00:52:07.590 --> 00:52:09.289
And he had this like look in his eye. It's
1079
00:52:09.309 --> 00:52:11.409
like emotional. Even thinking about this, this look in his
1080
00:52:11.570 --> 00:52:15.150
eye of like, okay, like good. Like I still want
1081
00:52:15.170 --> 00:52:16.690
to do impress him though. You know how weird those
1082
00:52:16.730 --> 00:52:18.610
coaches were. You still want to impress him, but I
1083
00:52:18.630 --> 00:52:19.989
just want to make sure he knew it. And then
1084
00:52:20.030 --> 00:52:23.710
we had like hours and hours of conversation, storytelling, a
1085
00:52:23.809 --> 00:52:25.269
follow-up meeting afterwards.
1086
00:52:25.570 --> 00:52:27.409
It just, I urge people to do that.
1087
00:52:27.449 --> 00:52:30.840
Like to call somebody, see them, tell them, even text them, whatever,
1088
00:52:30.880 --> 00:52:33.619
maybe to let them know, like, thank you for what
1089
00:52:33.639 --> 00:52:35.119
you've done for me. Like, I don't know if you
1090
00:52:35.179 --> 00:52:37.480
fully realize how much you've impacted me and that can
1091
00:52:37.519 --> 00:52:38.340
be really powerful.
1092
00:52:38.659 --> 00:52:40.130
Yeah, absolutely.
1093
00:52:40.329 --> 00:52:40.710
I love it.
1094
00:52:41.010 --> 00:52:42.190
I love it.
1095
00:52:42.929 --> 00:52:43.449
One more thing.
1096
00:52:43.469 --> 00:52:46.539
I know we have to run, but, I want to
1097
00:52:46.559 --> 00:52:48.639
talk about the power of learning circles. Could you briefly
1098
00:52:48.699 --> 00:52:52.480
describe the power of learning circles? Because you're a lifelong learner.
1099
00:52:52.639 --> 00:52:55.800
I'm a lifelong learner. I'm fans of leaders who are
1100
00:52:56.159 --> 00:53:00.679
learning leaders. And you've written about learning circles. And I
1101
00:53:00.699 --> 00:53:03.699
get to do this too in my daily life. Can
1102
00:53:03.900 --> 00:53:05.739
you talk about the power of learning circles?
1103
00:53:05.760 --> 00:53:05.980
Yeah.
1104
00:53:06.320 --> 00:53:08.079
Maybe I need to write more about this too, because
1105
00:53:08.119 --> 00:53:09.880
it's something a lot of people ask me about.
1106
00:53:11.119 --> 00:53:11.400
My.
1107
00:53:13.010 --> 00:53:16.269
my hypothesis is that the best learning is communal. It's
1108
00:53:16.309 --> 00:53:19.429
not an individual activity. And what I mean by that
1109
00:53:19.670 --> 00:53:23.329
is when you read something new, you read a new concept,
1110
00:53:23.909 --> 00:53:26.070
you can sit there and think about it and it's
1111
00:53:26.090 --> 00:53:28.139
in your head and you've learned something a little bit,
1112
00:53:28.659 --> 00:53:32.219
but it gets really cemented. It gets much more dynamic
1113
00:53:32.300 --> 00:53:34.519
and usable when you go talk about it with a
1114
00:53:37.539 --> 00:53:40.099
push and pull it in different directions, this idea becomes
1115
00:53:40.199 --> 00:53:42.559
much more than just a concept that you've read about
1116
00:53:42.579 --> 00:53:45.019
and you've only heard it one way. And so one
1117
00:53:45.039 --> 00:53:46.820
thing that I always encourage people to do and that
1118
00:53:46.860 --> 00:53:49.860
I've adopted in my own life is develop these circles
1119
00:53:49.940 --> 00:53:53.510
of friends, whether it's a group chat or a hangout
1120
00:53:53.610 --> 00:53:56.389
every now and then in person, groups of people that
1121
00:53:56.429 --> 00:53:59.989
you can collectively learn with about these things and bring
1122
00:54:00.030 --> 00:54:02.010
up these ideas. It doesn't have to be formal and
1123
00:54:02.030 --> 00:54:04.849
you're saying, hey, this is my learning circle. But groups
1124
00:54:04.889 --> 00:54:07.610
of friends that push your thinking on things where you
1125
00:54:07.630 --> 00:54:09.969
can throw out an idea and say, hey, I'm really
1126
00:54:10.010 --> 00:54:13.110
thinking about the future of work. What does it look like?
1127
00:54:13.159 --> 00:54:15.409
I read this cool article about X, Y, or Z.
1128
00:54:15.449 --> 00:54:17.699
And what do you think about that? And they totally disagree.
1129
00:54:17.739 --> 00:54:19.840
And then you kind of go at it a little
1130
00:54:19.880 --> 00:54:22.360
bit and push in different directions. And suddenly you're just like,
1131
00:54:22.780 --> 00:54:25.519
you have this unbelievably dynamic set of thoughts about a
1132
00:54:25.559 --> 00:54:27.739
concept that you never would have had if you had
1133
00:54:27.760 --> 00:54:29.579
just read the article and then said, oh, yeah, I
1134
00:54:29.619 --> 00:54:32.000
know about the future of work now. It's just a
1135
00:54:32.039 --> 00:54:34.179
different degree. You were here and now you're up here.
1136
00:54:35.019 --> 00:54:37.960
And that's brought about by that collective learning. And so
1137
00:54:38.000 --> 00:54:41.059
I always encourage people like find your learning circle, find
1138
00:54:41.159 --> 00:54:44.139
people that you can kind of collectively come together with
1139
00:54:45.000 --> 00:54:47.019
and learn together, learn in that same way.
1140
00:54:47.579 --> 00:54:47.969
I love it.
1141
00:54:49.360 --> 00:54:53.500
Thanks so much, man, for being here. There's so much
1142
00:54:53.659 --> 00:54:55.530
out there to learn more about you.
1143
00:54:55.550 --> 00:54:57.760
Where would you send people online?
1144
00:54:58.349 --> 00:55:01.409
Yeah. I mean, my Twitter is at sawhillbloom. Just my name.
1145
00:55:01.570 --> 00:55:05.070
It's the benefit of having a weird name. So it's
1146
00:55:05.139 --> 00:55:11.780
at sawhillbloom. And then my newsletter is, I don't know, sawhillbloom.substack.com,
1147
00:55:11.820 --> 00:55:12.099
I think.
1148
00:55:12.119 --> 00:55:14.460
The Curiosity Chronicle. I love the name.
1149
00:55:14.780 --> 00:55:18.639
Yeah. Just exploring my own curiosity and sharing it with others.
1150
00:55:18.800 --> 00:55:22.860
So I highly recommend people checking it out because both
1151
00:55:22.909 --> 00:55:26.280
your threads and your um, your sub stack, because I've,
1152
00:55:26.420 --> 00:55:28.880
I've learned a ton from it personally. So every time
1153
00:55:28.920 --> 00:55:31.219
like a new thread comes, I am ready. Um, so
1154
00:55:31.260 --> 00:55:33.840
I really, and, and your, uh, sub stack, I really
1155
00:55:33.860 --> 00:55:35.400
appreciate it, man. And thanks so much for being here.
1156
00:55:35.420 --> 00:55:37.900
I'd love to continue our dialogue as we both progress.
1157
00:55:38.280 --> 00:55:40.150
Would love to appreciate it. Thanks so much.
1158
00:55:40.429 --> 00:55:40.789
Thanks, man.
1159
00:55:41.949 --> 00:55:45.289
Now that is a conversation I love to have continued
1160
00:55:45.349 --> 00:55:48.789
for hours. And we both intend to do that after
1161
00:55:48.829 --> 00:55:50.590
we got to recording. So he'll say, Hey, you got,
1162
00:55:50.610 --> 00:55:52.489
you have to come to New York city so we
1163
00:55:52.510 --> 00:55:56.070
can keep this, uh, going, maybe over a meal and
1164
00:55:56.090 --> 00:55:58.760
a few drinks, and I fully intend to do that.
1165
00:56:00.139 --> 00:56:03.039
I really appreciate the way his mind works and how
1166
00:56:03.679 --> 00:56:08.119
deep of a thinker Sahil is. A few takeaways from
1167
00:56:08.159 --> 00:56:11.579
my notes. Learning circles. Develop a circle of people to
1168
00:56:11.699 --> 00:56:15.969
collectively learn with. Push your thinking. This is something I
1169
00:56:16.010 --> 00:56:18.889
do with my learning leader circles, and it's some of
1170
00:56:18.929 --> 00:56:22.869
the most rewarding and fulfilling work I do where I'm
1171
00:56:23.070 --> 00:56:28.760
able to facilitate conversations, ask questions, ask even better follow-up
1172
00:56:28.800 --> 00:56:31.840
questions so that we all can learn together. Then the
1173
00:56:31.920 --> 00:56:36.119
makeup of a great coach. They're never too big to
1174
00:56:36.159 --> 00:56:39.039
do the small things. They push you beyond what you
1175
00:56:39.139 --> 00:56:45.420
think you're capable of. They lift expectations for you. As
1176
00:56:45.480 --> 00:56:48.510
his coach said to him, how about Stanford when that
1177
00:56:48.570 --> 00:56:51.929
wasn't even in Sahil's mind? And I'd like for you
1178
00:56:51.969 --> 00:56:55.550
to take a moment and say thank you to someone
1179
00:56:55.570 --> 00:56:58.420
who has done this for you. Maybe text them, call them,
1180
00:56:58.500 --> 00:57:00.599
meet with them, send them an email, write them a letter.
1181
00:57:01.099 --> 00:57:03.920
I'd love to see you do this and hear about
1182
00:57:03.940 --> 00:57:07.800
the response from that person when you do. And then
1183
00:57:08.500 --> 00:57:12.960
why writing makes you better at everything you do. That
1184
00:57:13.000 --> 00:57:16.869
was a fun part of the conversation when Sahil said
1185
00:57:16.949 --> 00:57:21.829
writing is the best way to expose gaps in your thinking.
1186
00:57:22.309 --> 00:57:25.480
When you write, you think better, and it makes you
1187
00:57:25.519 --> 00:57:26.949
better at every.
1188
00:57:26.889 --> 00:57:31.949
Aspect of your life. All leaders should be writers.
1189
00:57:32.510 --> 00:57:34.110
I want to say once again, thank you so much
1190
00:57:34.150 --> 00:57:37.250
for continuing to spread the message and telling a friend
1191
00:57:37.429 --> 00:57:40.260
or two, hey, you should listen to this episode of
1192
00:57:40.300 --> 00:57:43.199
The Learning Leader Show with Sahil Bloom. It will make
1193
00:57:43.260 --> 00:57:46.659
you a more effective leader. And because you continue to
1194
00:57:46.679 --> 00:57:49.480
do that, and because you continue to write reviews and
1195
00:57:49.559 --> 00:57:53.110
rate the show, hopefully five stars on Apple Podcasts, you
1196
00:57:53.599 --> 00:57:56.530
are giving me the opportunity to do what I love
1197
00:57:56.730 --> 00:58:00.489
on a daily basis. And for that, I will forever
1198
00:58:00.909 --> 00:58:03.250
be grateful. Thank you so much.
1199
00:58:03.610 --> 00:58:07.969
Talk to you soon. Can't wait.
1200
00:58:07.989 --> 00:58:13.619
I recently found an exciting new investment opportunity, Blue Chip Art. Now,
1201
00:58:13.699 --> 00:58:17.199
it's traditionally only open to billionaires because of the high
1202
00:58:17.380 --> 00:58:25.940
entry cost. But one startup is making it available for everyone. Masterworks.io
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00:58:26.039 --> 00:58:29.159
lets you invest in multi-million dollar works by artists like
1204
00:58:29.280 --> 00:58:34.739
Banksy and Monet. Contemporary art prices outperformed S & P
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00:58:34.739 --> 00:58:40.699
500 returns by 174% from 1995 to 2020. The total
1206
00:58:40.840 --> 00:58:45.789
art asset class is currently estimated at $ 1. 7 trillion and
1207
00:58:45.849 --> 00:58:49.110
is growing by another trillion over the next five years. Now,
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00:58:49.170 --> 00:58:51.929
demand is high, but I've worked with Masterworks to let
1209
00:58:51.949 --> 00:58:58.190
you skip their waitlist. by going to masterworks.io slash learning.
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00:58:58.210 --> 00:59:06.110
That's masterworks.io slash learning. Also, please see important disclosures at masterworks.io
1211
00:59:06.230 --> 00:59:07.269
slash disclaimer.
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00:00:01.870 --> 00:00:04.330
I just think that writing is the best way to
2
00:00:04.389 --> 00:00:07.070
expose gaps in your thinking and where your thinking is
3
00:00:07.089 --> 00:00:11.650
falling short. It is impossible to write down everything you
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know about an idea and not immediately see the gaps
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00:00:15.550 --> 00:00:18.120
in what you know about that concept. And so as
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a leader, it's one of the most important things you
7
00:00:20.399 --> 00:00:23.320
can do for clarifying your thinking on any given topic.
8
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I recently found an exciting new investment opportunity.
9
00:00:29.329 --> 00:00:30.390
Blue Chip Art.
10
00:00:30.809 --> 00:00:34.170
Now, it's traditionally only open to billionaires because of the
11
00:00:34.250 --> 00:00:39.329
high entry cost. But one startup is making it available
12
00:00:39.609 --> 00:00:45.789
for everyone. Masterworks.io lets you invest in multi-million dollar works
13
00:00:45.850 --> 00:00:51.289
by artists like Banksy and Monet. Contemporary art prices outperformed
14
00:00:51.509 --> 00:00:54.630
S & P 500 returns by 174% from 1995 to 2020.
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00:00:57.700 --> 00:01:05.500
The total art asset class is currently estimated at $ 1. 7
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00:01:02.219 --> 00:01:05.700
trillion and is growing by another trillion over the next
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00:01:05.760 --> 00:01:08.379
five years. Now, demand is high, but I've worked with
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Masterworks to let you skip their wait list by going
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to masterworks.io slash learning. That's masterworks.io slash learning. Also, please
20
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see important disclosures at masterworks.io slash disclaimer. Welcome to the
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Learning Leader Show presented by Insight Global.
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I am your host, Ryan Hawk. Thank you so much
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for being here.
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Text LEARNERS to 44222 to become part.
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Of Mindful Monday. You, along with tens of thousands of
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other learning leaders from all over.
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The world, will receive a carefully curated email from me
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each Monday morning.
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To help you start your week off right.
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You'll also receive details about how my book, Welcome to Management,
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will help you become.
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A more effective leader. Text LEARNERS to 44222.
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Now on to tonight's featured leader. This was a fun one.
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It's Sahil Bloom, writer and angel investor. He publishes work
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on the Curiosity Chronicle.
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Love the name.
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He demystifies complex topics and makes them simple. Previously, he
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was a pitcher for Stanford's baseball team. A few of
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the topics we discuss, the must-have qualities of a leader
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he chooses to invest in, and then what makes a
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great coach, both.
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On the field and online. in the business world.
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What he learned from giving up a grand slam in
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a pivotal game broadcasted on ESPN.
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And why you should write.
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I've been beating this drum for a while, but Sahil
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shares some great examples of how it's made his life better.
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Ladies and gentlemen, this is a great one. It's Sahil Bloom.
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You first piqued my curiosity. I saw a thread you've
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written on Twitter and then I looked at your bio
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and it said a couple of things that I really liked. One,
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writing threads to demystify the world, investor, advisor, and creator.
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And then this next part really got me. Gave up
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a grand slam on ESPN in 2012 and still waiting
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for it to land. So I was like, okay, this guy,
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I like this guy and I don't know him yet.
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Could you share more?
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About a little of your backstories, I guess, going to
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Stanford and being a baseball pitcher and why you thought,
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let me just jab myself a little bit with my
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Twitter bio.
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Yeah. Yeah.
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Well, I appreciate you having me on. This is awesome.
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Been a big fan of the content you're putting out.
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So I'm excited to be a part of it now.
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But no, I mean, the genesis of all of that
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was like, I generally think that people take themselves too seriously.
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And we all have a tendency to do it, right? Like,
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especially while you are pursuing something that you think is meaningful.
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You're achieving things that you think are meaningful. There's just
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a tendency to get really buttoned up and serious along
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the way and stop having the ability to make fun
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of yourself. And so I have this great group of friends,
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a lot of my baseball teammates from back in the
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day who no matter how far any of us make
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it in life, the exclusive purpose of when we get
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together is making fun of each other. And so I
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sort of just like have adopted that ethos in my
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own life that I just can't take myself too seriously ever.
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And so the bio is kind of a, you know,
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a jab in that direction of like, you know, I
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was accomplishing something that I thought was great. I was
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playing on this, you know, big stage and at this
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great level. And, you know, I had this horrible moment.
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I gave up a grand slam on national television, lost us,
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you know, a chance at playing in the College World Series.
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It was like one of the worst moments of my
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life at the time. But being able to laugh at
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yourself kind of on the back end of that stuff,
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I think is such a powerful thing. You know, and
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there's also a lesson there in like never getting too high,
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never getting too low. The week before that, I mean,
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the context to it is like the week before that
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we had played in the regional championships and I had
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closed the regional championship game, got a got a save
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in the regional championship game, like 10,000 people in the stands.
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you know, the highest moment of my baseball career to date.
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And I remember coming away from it being like, man,
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I am so good. Like I really thought, you know,
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it's like the Giannis quote from a few weeks ago.
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Like when you think about the past, that's all about
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your ego. And that was how it was. I was like, man,
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I did this. I did this. Like, look, I'm coming.
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I'm getting better.
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I'm going to get drafted.
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And then the next week I gave up this absolutely
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massive grand slam to lose my team, a chance at
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going to the college world series. And it was that
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exact example of like, you get too far ahead of yourself.
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You get too high. you get knocked down. It's just
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what happens. And so you need to be able to
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focus on the present and never get too high, never
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get too low. So that's always just really resonated with me.
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How do you, so I have a somewhat similar college story.
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I coming out of high school, I went to Miami
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of Ohio here in Ohio, obviously the Mid-American Conference. And
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I happened to go at the exact same time and
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play the same position as Ben Roethlisberger. And a bunch
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of people, college coaches, others called me back after, because
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Ben committed about a week after I did. And they said, hey, dude,
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you don't want to go there. It's not going to
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work out for you. And of course, I'm sure you're
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the same way when you're 18. You're like, you guys
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have no idea what you're talking about.
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I'll beat them out.
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And I think, though, the great lesson that I learned
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from that experience of battling it out for two years
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and maybe having this this belief in myself that I
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somehow could win this job, even though I like from
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the first day, I probably was never going to win
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that job, but I thought I was, but I think
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it's that you, you know, you do everything you can
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to make it happen. And the world doesn't necessarily care
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because the coach is going to play the guy who
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gives the team the best chance to win. And in
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this case, the late great Terry Heppner made the, obviously
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the right decision when he named him starter during our
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second year at Miami. And I think there's, those are
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awesome lessons. Like, and so I'm curious from, giving up
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that grand slam. It sounds like one of the toughest
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moments of your life at up to that point, at least, but,
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but especially in your formative years, having to bounce back
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from things like that, like what have you learned from
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that grand slam that has made you better in what
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you do today?
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Yeah. You know, it's interesting. It's like you hear about
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those big public failures and those moments, right? Like I
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talk about that one because it was a big moment.
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It was on TV. It was, you know, big game, whatever.
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I actually think the like private failures are even more
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impactful in terms of how they, how they kind of
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create you and shape you. Um, I think about one
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of the most impactful ones for myself was like the
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day I showed up at Stanford campus as a freshman 2009. And, um,
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you know, I'd grown up in a small town in Massachusetts.
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I was like the ultimate big fish, small pond syndrome. Like,
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you know, I thought I was hot shit, man. I mean, like,
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excuse my language, but Like I, you know, I thought
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I was really smart. I thought I was a great
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baseball player. I, you know, got a scholarship to go
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to this great school and I got to campus the
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first day and just got like kicked in the gut, um, academically, athletically,
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I mean, everything, right? Like I went to class and
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realized I wasn't that smart. Um, you know, I went
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to baseball practice and realized I wasn't that good at baseball. Um,
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and so I remember like freshman year was such a
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grind because it was like the first time in my
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life that I had really had to experience on a
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daily basis failures. Um, and in hindsight, you realize that
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that kind of stuff is crucial to forming and shaping
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who you are as a person later. The fact that
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you were able to like, just keep pounding your head
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into a wall, keep pounding your head into a wall,
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keep pounding your head until finally you break through. And
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you didn't really know when it was going to happen.
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There was no end in sight. It might've never happened. Um,
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it's like that idea of, are you willing to sprint
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when the distance is unknown? Um, which I've always loved.
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It's resonated with me. It gives me chills even when
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I like see people talk about that or quotes because
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it's so powerful. Like how much are you willing to
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just keep running when you have no idea how far
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you're going to be running? And those were the moments.
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I mean, none of it was public. It was like
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practices or going to class on a daily basis and
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just like being willing to just get knocked down every
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day and get back up. There's nothing more powerful than
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that in the long run than if you can kind
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of like form your character around that type of ethos.
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Has anything like that happened now?
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Because I think sports and especially going to a school
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like Stanford for you probably were great learning tools, but
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as then you transitioned to post-athletic you're into the business
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world you're investing you're you have a job you're doing
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things on the side can you think of like a
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moment how where you drew from that and it made
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you better in this more professional world that most of
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us are in now since we can't play sports forever.
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Yeah i mean every day it's like Your career, your life,
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it's all about how you bounce back from failures. No
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one has the privilege of only succeeding. If anyone tells
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you they do, they're lying or they're in such rare
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air that I can't even relate to them. I remember
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my first job, all of the failures that came with it.
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You screw stuff up.
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What was your first job after playing baseball?
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I went straight into the investing world. I got hurt
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my last year at school and thought I was going
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to go play professionally. It got taken away from me.
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probably for the better because I wasn't all that good
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in the grand scheme of things. But I went and
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took this job in the investing world, didn't know a
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lick about investing. And so I knew I was just
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going to have to do the same thing, like pick
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up and just start grinding with it. And I just
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remember like every day there was something I was screwing up.
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I'd forget to do something or make the same mistake twice.
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And the ability to actually like take those pieces of
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feedback in and not crumble from them is such a
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massive advantage in life. Like so many people that I
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saw and still see a lot of young people entering
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the work world, they can't take critical feedback. You like
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give them one piece of constructive feedback, not even critical, constructive, like, Hey,
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I want to make you better. Here's one, two, three
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things that you could do to make your performance better.
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And it's like they crumble almost because their whole life
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they've been only succeeding at things and they've only gotten
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straight A's and they've been at the top of their
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class and they went to X school or whatever it was.
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They never had to deal with that. Like, I'm bad
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at something. How do I pull up and get better?
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And so I just think that like those moments, especially
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as a parent, I think about it for, you know,
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when I eventually, God willing, have children and I'm raising them,
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what do I want to instill in them? And that's
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one of the biggest things to me is like, let
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them fail. let them fall on their face. And it's
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terrifying as a parent, I imagine, easier said than done.
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But those moments of failure and those things that I
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had to get smoked by are now the greatest experiences,
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the things that I wouldn't trade for the world in
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terms of forming my day-to-day perspective and character.
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You are an active angel investor. So first, for those
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who Don't know anything about that. I'll ask you to
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kind of define that for a second. But the second
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part of the question, which I'm going to ask you
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at the same time, is when you're looking to make
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an investment, what are some of the must-have qualities and
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or behaviors in a person that you're going to invest in?
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I know the idea is probably important or their product
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or whatever it is that they're doing, product, market, fit,
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or if you're so early, you might not even have
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that yet. But I'm really, because I think of the
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best investors when I hear what they say, they usually
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say something like, I invest in the person first before
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whatever it is.
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That they're doing.
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I believe in that person regardless of what they're doing.
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So I'm curious, C.O., from your perspective, what are some
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of those must-have qualities in a person to back?
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Yeah.
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Yeah.
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So, I mean, first off to your first question, angel investing,
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I think it's like this term that people start throwing
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around a lot.
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It's like....
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You know, effectively it's just that you are an individual,
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not a investment fund and you are providing money to startups, um,
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is the right way to think about it. And I
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don't know where the term angel officially got coined, but
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you know, you're like supposed to be like, they're saving grace.
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It's far from that. You know, you're, you're just, you're
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buying into a person and an idea and you're providing
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capital for them to go and execute in the very
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early days, generally before they can go get a venture
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fund to back them or whatever private, private fund. Um,
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And then to your question on what you're looking for,
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I mean, I think the resilience and grit is probably
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the number one thing. And the reason I say that
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is because startups and entrepreneurship and small business and all
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of these areas, you're just going to get knocked around.
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It's just the reality of life is that nothing is
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ever up and to the right in a straight line.
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And so if you're investing in a person, you're investing
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in their idea, The idea can be as good as
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you want, but it's going to have struggles along the way.
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Jeff Bezos, the struggles along the way of Amazon, when
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you look at how much wealth he's accumulated, it's because
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he was literally the only person that has held Amazon
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stock for that entire time. No one else could stomach
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those 60% drops that the stock had because of massive
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business issues over time. it was resilience. It was like,
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you stick with it and you continue to find a
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way to win in the long run. You like zoom
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out of the short-term issues and are able to kind
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of see the vision and see where it's headed and
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what I'm supposed to be doing. And when you find
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that in an entrepreneur, it's really hard to like ask
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the question that makes you figure out that they have
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it or not, but you can feel it. Like when
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you talk to someone, you can really feel it. And
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I'm by no means some expert. There are legendary investors
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who I'm sure have this like sixth sense figuring out
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whether an entrepreneur has that it factor. Um, but I
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think that is just like the most critical thing. Like,
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is this person just willing to die before they fail
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at this business? Um, and there are just people out
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there that have that, that are just like that. And
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you just know, um, that's not even an option for them.
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Like the business, this business that you're backing could completely
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collapse and they will somehow find a way to like
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Phoenix out of the ashes and start something else that
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ends up being even more impressive. So yeah, that a
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long way of answering your question, but I think resilience
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and grit are the two.
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You've done this more than 25 times from what I've read.
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So when you think, think to each of those 25
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plus decisions, like.
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Can you take us inside the room?
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Like, I don't know, or, or the zoom or the
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calls or like, how do you go from, Oh, okay.
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This is an opportunity to, all right, I'm giving them money.
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Like, can you, can you, I'm fascinated by that process.
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Like, how does it work? Yeah.
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I think it depends on like, first off, it depends
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on if you're in the COVID, you know, pre COVID
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or post COVID world, because a lot of the, okay.
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Maybe sure.
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Both.
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Yeah.
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Yeah. I mean, pre COVID, a lot of this stuff
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is driven by relationships and, and, in a sense, it
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was easier as an investor then because you got to
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spend time building relationship with these individuals that you were
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going to eventually back. And so you had more data points.
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You saw how they interacted with other people. You saw
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how they responded to different questions, challenges, things that were
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happening over just a longer duration. In the post-COVID era,
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a lot of this has been done via Zoom. It's
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like this, you're on a Zoom with someone. And so
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they have their like, you know, an entrepreneur that's really
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seasoned has their pitch and they know how to run
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through it. And so I've personally found like, if I'm
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doing a call with someone, I already understand the idea.
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I'm interested in the idea in the business. I believe
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in the long-term vision of it. So I personally try
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to take it more towards like, I want to get
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to know you, you know, tell me about a time
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you got your ass kicked type thing. But the other
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reality to it is like, I'm not an investment fund.
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I don't have, you know, limited partners, LPs that have
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given me their money to invest on their behalf. It's
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my money. And so, you know, when I do it,
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I want to get comfortable and the burden of that
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is different. And I reached that kind of burden of
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proof in different amounts of time, depending on the person.
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I've gotten on a call with someone in like two
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minutes in said to myself, holy crap, I got to
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back this person. I don't care what the idea is
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almost because like I need to back this person and
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they're going to figure it out. I had that with a,
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with an entrepreneur recently and And I actually didn't even
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think the idea is that good, what he's working on.
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But I just want to invest in him because I
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think that he's such a killer in the long run.
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But it just depends. It just depends what the circumstances
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are around it, how long it actually takes you to
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go develop that comfort around an idea. The other thing
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to mention, which people have probably seen in the news,
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is the market is so frothy and hot right now.
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And there's so much capital out there that these things
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like the timeframes around them have just compressed and compressed
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and compressed to the point where, you know, most of them,
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if you can't make a decision quickly, you're just, you're
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not going to have an opportunity to invest in the thing.
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You know, the like investors that are stealing everyone's lunch
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right now are the ones that can just move really quickly,
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you know, and send a.
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Check and say, let's go totally.
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Like they've done the work, they've done the prep in
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advance and, they know the industry, they know the market,
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they know the business, they know the competitive landscape. And
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so they're basically just like check the box on a
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couple of things that they really want to figure out
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and then they can just.
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Roll and make a move on it. So how about
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let's make it personal.
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So my current kind of investing strategy is I have
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set amount of money that goes to my financial advisor
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every month and it's kind of automated and I don't
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really think about it. And then I just let compounding
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go to work, right? The best way to get wealthy, right,
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is just don't interrupt it as Charlie Munger or Warren
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Buffett might say. And I'll continue to do that no
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matter what, but I am curious about this and I
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think other people are too.
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So let's say, Sahil, I called you and I'm like, dude,
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I want to do this.
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I have this set amount of disposable money that If
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I lose it, I lose it.
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It's okay. How can I get started?
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So what advice would you give to me if I'm like,
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I want to do this part of what you do?
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Yeah. I mean, look, my first advice would be don't.
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Do it.
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Just keep compounding. Because the reality of most of this,
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most people want to say they are an angel investor
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and it's become this like, it's like a flex almost.
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It's like a LinkedIn flex where you're like, you want
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to say that you're an angel investor. The reality is like,
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the vast majority of those investments go to zero because
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they're startups and they're like really risky. And so for
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most people, probably myself included, the like value maximizing thing
414
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to do over the long run would be to take
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all that money that you were going to angel invest
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and just put it into the S & P 500
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and let it just go up over the next 40
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years of your life. And you'll probably like on an
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expected value basis, that'll leave you the best off. My
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personal opinion on it always and why I do a
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lot of it is I learned so much from these conversations,
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from the people that I get to associate with because
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of it, from being around these businesses, from helping them.
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I mean, for me, I could lose all the money
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that I've invested in all this stuff, every single dollar.
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And I think it would be a net positive return
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to me because of the actual intellectual returns that I've
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gotten on that capital that I've put out beyond the
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financial returns. But on a purely financial basis... I think
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it's like the burden of wanting to get into that
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is very high. The challenge, so if you said, okay,
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I understand that and I want to do it, it's
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all about deal flow. What are you actually seeing? And
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so therefore, what can you execute against? The challenge with
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the venture world and with angel investing in general is
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that it is the ultimate game of adverse selection. The
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deals that want you to invest in them are typically
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not the ones you want to be investing in because
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they're the ones that no one else has backed, right?
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Like if there's some unbelievably hot company that can raise
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money from anyone in the world, like five years ago,
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maybe not now, but five years ago, if they had
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come to me and said like, Sahil, we want you
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to put in some money into this. My first reaction
445
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would have been like, why? Like, why do you want
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me to, I'm like some random analyst at a fund
447
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at the time. Like what about what is making you
448
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want me to invest? And that would almost like set
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off alarm bells. Now it's a little different because I
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can help them with a bunch of things. You know,
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I have a platform. I can talk about them publicly.
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I can get them exposure. And so now it's like,
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I'm in more of a real position to add value
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to them. And so I might be able to get
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into things that way. But like for a new person
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starting angel investing, every deal that you see, you almost
457
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have to have your initial reaction be like, why am
458
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I so lucky? Is this actually a really good opportunity
459
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or are they just showing it to me because they
460
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can't get the money from anyone else?
461
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Interesting.
462
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Yeah. It's like, uh, the very beginning of when people
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started asking me to come give talks, I would talk
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to other more experienced speakers.
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And I would say, hey, you have a speaking agent.
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Should I get one of those?
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And they said, trust me, the speaking agents will start
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reaching out to you the moment you don't need a
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speaking agent anymore, meaning like the book you kick. So
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it's just weird how the things work. And that's exactly
471
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how this has worked now that multiple years have passed
472
00:23:01.930 --> 00:23:05.319
where I don't need the inbound person or the person
473
00:23:05.400 --> 00:23:06.059
out there doing it.
474
00:23:06.799 --> 00:23:08.660
It'd be just kind of like an admin person. It's
475
00:23:08.680 --> 00:23:10.640
not worth giving all that percentage for that. So I
476
00:23:10.660 --> 00:23:13.099
handle it myself. It's kind of interesting how the world
477
00:23:13.140 --> 00:23:14.039
kind of works that way.
478
00:23:14.480 --> 00:23:17.359
Totally. Yeah. I mean, that's a great analog, but there's
479
00:23:17.380 --> 00:23:18.799
so many analogs like that, right?
480
00:23:18.880 --> 00:23:19.500
Actually a lot.
481
00:23:19.539 --> 00:23:25.140
I mean, it's funny because the common adage within the
482
00:23:25.160 --> 00:23:28.759
financial world is that dentists have made the best marks
483
00:23:29.000 --> 00:23:31.089
for some of these funds to go and try to
484
00:23:31.140 --> 00:23:33.900
raise money from because they had they met the accredited
485
00:23:33.960 --> 00:23:37.140
investor thresholds, which are what require, you know, you're required
486
00:23:37.160 --> 00:23:39.359
to meet in order to invest in these private placements,
487
00:23:39.839 --> 00:23:43.259
but they weren't particularly knowledgeable about financial things because they
488
00:23:43.279 --> 00:23:46.809
had pursued a life of science and medicine. Um, and
489
00:23:46.849 --> 00:23:49.069
so those were the people that were like typically falling
490
00:23:49.119 --> 00:23:51.650
victim to, and it was obviously generalized, but that was
491
00:23:51.690 --> 00:23:53.910
like the, the thing that everyone would talk about were
492
00:23:53.950 --> 00:23:56.829
like dentists were the most prone to falling victim to
493
00:23:56.869 --> 00:23:59.250
these like random scams that were coming up within the
494
00:23:59.289 --> 00:23:59.910
finance world.
495
00:24:01.750 --> 00:24:04.190
Uh, Shifting gears a bit, and I want to talk
496
00:24:04.210 --> 00:24:04.950
about writing.
497
00:24:06.150 --> 00:24:10.150
There's a great Boston Globe story that talks about this,
498
00:24:10.390 --> 00:24:12.670
written about you, great picture with you and Tim Cook.
499
00:24:13.490 --> 00:24:15.990
But a lot of, I feel like, I mean, I
500
00:24:16.269 --> 00:24:18.750
became aware of you because of your willingness to ship
501
00:24:18.809 --> 00:24:21.470
work publicly, to learn in public, to share what you're learning,
502
00:24:21.519 --> 00:24:25.319
and to be a fantastic storyteller, whether it's through tweet
503
00:24:25.819 --> 00:24:30.849
threads or your sub stack. Can you first, from a
504
00:24:30.990 --> 00:24:36.329
leadership perspective, let's talk about from a leadership perspective, why
505
00:24:36.450 --> 00:24:41.210
should every leader have some form of a writing practice,
506
00:24:41.250 --> 00:24:42.710
whether they decide to publish it or not?
507
00:24:44.190 --> 00:24:50.539
Great question. Simple answer. When you write, you think better.
508
00:24:52.119 --> 00:24:54.579
I just think that writing is the best way to
509
00:24:54.640 --> 00:24:57.319
expose gaps in your thinking and where your thinking is
510
00:24:57.339 --> 00:25:06.049
falling short. It is impossible, virtually impossible to write down
511
00:25:06.390 --> 00:25:09.890
everything you know about an idea and not immediately see
512
00:25:09.930 --> 00:25:13.349
the gaps in what you know about that concept. And
513
00:25:13.390 --> 00:25:15.829
so for me, I mean, to make it real, like
514
00:25:15.849 --> 00:25:17.670
when I want to go write a thread or write
515
00:25:17.710 --> 00:25:22.079
a newsletter piece about some new topic, say inversion, it's
516
00:25:22.099 --> 00:25:24.119
like this mental model that I use quite a bit.
517
00:25:24.940 --> 00:25:27.619
I can go and write down a piece about it
518
00:25:28.180 --> 00:25:31.619
and then I'll read it. and realize, oh my God,
519
00:25:31.660 --> 00:25:34.559
there's like these massive gaps in how I'm understanding this.
520
00:25:35.059 --> 00:25:36.500
And I wouldn't have known that. I would have thought
521
00:25:36.539 --> 00:25:39.259
I understood inversion. Like, yeah, I understand it. Because your
522
00:25:39.299 --> 00:25:41.319
mind tells you that. You're just like, oh, I get it.
523
00:25:41.400 --> 00:25:43.200
I don't need to read more about this. And when
524
00:25:43.220 --> 00:25:45.849
you write it down, suddenly it becomes very clear to
525
00:25:45.890 --> 00:25:48.730
you where those gaps exist and how you can go
526
00:25:48.789 --> 00:25:52.549
fill them in. And so as a leader, I just
527
00:25:52.589 --> 00:25:55.230
think it's one of the most important things you can
528
00:25:55.289 --> 00:25:58.519
do for clarifying your thinking on any given topic. The
529
00:25:58.579 --> 00:26:01.380
other piece is it makes you better at everything you do.
530
00:26:01.559 --> 00:26:05.440
When you write clearly, you communicate more clearly. You're able
531
00:26:05.500 --> 00:26:09.059
to be more succinct in everything that you're putting together.
532
00:26:09.160 --> 00:26:12.519
I mean, my Twitter writing habit started with Twitter. It's
533
00:26:12.559 --> 00:26:15.220
become a newsletter writing habit has made me a better investor.
534
00:26:16.160 --> 00:26:19.829
It's made me a better husband. It's made me a
535
00:26:19.849 --> 00:26:22.269
better friend. I just, because I think more clearly and
536
00:26:22.309 --> 00:26:26.089
I think in more concise terms, I have more value
537
00:26:26.230 --> 00:26:28.710
add and conversations that I have with people because I'm
538
00:26:28.789 --> 00:26:30.950
able to just like draw upon these things that I've
539
00:26:31.019 --> 00:26:34.519
written about. And so I've learned them more effectively. It
540
00:26:34.559 --> 00:26:37.740
just has this massive spillover effect across all these realms
541
00:26:37.779 --> 00:26:38.279
of your life.
542
00:26:39.099 --> 00:26:45.819
I sold a book deal on management to my publisher
543
00:26:45.859 --> 00:26:48.579
McGraw Hill. I remember in the book proposal, you know,
544
00:26:48.599 --> 00:26:51.180
you write like a sample chapter, but a lot of
545
00:26:51.220 --> 00:26:54.039
it's kind of the mark. That's how a proposal sells.
546
00:26:54.059 --> 00:26:55.880
They're like, can this dude sell books? And we're going
547
00:26:55.900 --> 00:26:58.319
to say yes or no. The idea, yeah, they want
548
00:26:58.339 --> 00:27:01.059
it to be good enough. But then you get the deal,
549
00:27:01.559 --> 00:27:04.440
and then you have to actually write the book. And
550
00:27:05.160 --> 00:27:10.089
I didn't fully realize how little I actually knew about
551
00:27:10.140 --> 00:27:13.049
the topic that I had just sold a book deal
552
00:27:13.150 --> 00:27:16.849
until I was forced to go really deep. And so
553
00:27:17.170 --> 00:27:19.420
this is why I push all leaders to That was
554
00:27:19.460 --> 00:27:21.420
one of the greatest learning tools in the world. And
555
00:27:21.559 --> 00:27:25.390
so I push all leaders, write. I mean, I like
556
00:27:25.430 --> 00:27:27.430
if you're going to publish, but even if you're not,
557
00:27:27.450 --> 00:27:30.549
you should still write. And second, put yourself in the
558
00:27:30.589 --> 00:27:34.450
position of being a teacher. So anytime you're going to
559
00:27:34.470 --> 00:27:36.529
give a speech or you're going to meet with a
560
00:27:36.609 --> 00:27:38.970
mentee or you're going to try to help, let's say,
561
00:27:39.009 --> 00:27:41.819
a founder in your case, you're not going to want
562
00:27:41.839 --> 00:27:44.940
to not be a value add. So leading up to
563
00:27:44.980 --> 00:27:47.359
that meeting, you're probably going to really like, wait, what
564
00:27:47.380 --> 00:27:48.259
do I think about this?
565
00:27:48.319 --> 00:27:50.039
How am I going to help this person? What can
566
00:27:50.119 --> 00:27:50.420
I do?
567
00:27:50.779 --> 00:27:55.039
That process of preparing so much learning happens. Then you
568
00:27:55.140 --> 00:27:58.259
share the advice and you get immediate feedback if it
569
00:27:58.299 --> 00:28:00.900
was useful or not. And you can adjust moving forward.
570
00:28:01.180 --> 00:28:03.859
I feel like you seem to always be in the
571
00:28:03.880 --> 00:28:05.759
mode of being a teacher. And that seems to be
572
00:28:05.779 --> 00:28:08.400
a great learning tool for you, I gather.
573
00:28:09.180 --> 00:28:12.240
One hundred percent. I mean, it's funny, like people have
574
00:28:13.569 --> 00:28:15.210
told me over the course of the last year that
575
00:28:15.230 --> 00:28:16.849
they've learned a lot from the things that I've put
576
00:28:16.910 --> 00:28:19.250
out in the writing. And I like I think that's amazing.
577
00:28:19.730 --> 00:28:22.650
First off, I'm absolutely like I have so much gratitude
578
00:28:23.849 --> 00:28:26.519
for the era that we live in that I can
579
00:28:26.559 --> 00:28:28.880
like put things out there and that globally it can
580
00:28:28.900 --> 00:28:31.140
have an impact on people. I mean, like the responses
581
00:28:31.200 --> 00:28:33.819
I get from people in India and in Africa and
582
00:28:33.900 --> 00:28:36.019
all these places, like it's just incredible to me and
583
00:28:36.059 --> 00:28:38.460
I am still blown away by it every day. the
584
00:28:38.480 --> 00:28:41.200
thing I always say back is like, I'm actually learning
585
00:28:41.269 --> 00:28:46.089
alongside you about all of these things because I can't
586
00:28:46.109 --> 00:28:48.670
even describe how much smarter I have gotten in the
587
00:28:48.710 --> 00:28:51.549
last year from doing all of this writing that was
588
00:28:51.950 --> 00:28:54.420
from the outside looking in, looked like me teaching. It
589
00:28:54.440 --> 00:28:57.740
was actually me learning. And it's the most selfish thing
590
00:28:57.759 --> 00:29:01.019
I've ever done, candidly, because I've done all this writing
591
00:29:01.099 --> 00:29:03.660
and people view it as all this time that I've
592
00:29:03.839 --> 00:29:06.680
put out to help others. And that was a huge
593
00:29:06.720 --> 00:29:10.119
inspiration and motivation around it. But I've learned so much
594
00:29:10.180 --> 00:29:12.920
from doing it that like the downside to me of
595
00:29:13.000 --> 00:29:14.799
writing all of these pieces and doing all of this
596
00:29:14.839 --> 00:29:17.640
was that I learned a lot and the upside was limitless.
597
00:29:17.700 --> 00:29:19.549
And so it always just felt like that's a pretty
598
00:29:19.569 --> 00:29:21.829
good asymmetric trade I can make there.
599
00:29:22.990 --> 00:29:25.609
One of the things that you're really good at is
600
00:29:25.630 --> 00:29:28.130
writing great threads. So those who are, I guess not
601
00:29:28.170 --> 00:29:29.769
everyone's on Twitter. I find Twitter to be one of
602
00:29:29.789 --> 00:29:32.230
the greatest learning tools in the world. It's also been
603
00:29:32.250 --> 00:29:34.549
a great networking tool for me to meet people. That's
604
00:29:34.569 --> 00:29:38.809
how we met. And part of what makes your thread
605
00:29:38.849 --> 00:29:43.029
so good is that you're, become a phenomenal storyteller. So
606
00:29:43.049 --> 00:29:45.970
I do want to get specific on the threads thing,
607
00:29:45.990 --> 00:29:47.819
but I know not everybody cares about that. I do,
608
00:29:47.880 --> 00:29:50.359
but I know not everybody does. So let's start with
609
00:29:50.380 --> 00:29:54.640
the storytelling aspect of it. How have you worked on
610
00:29:55.079 --> 00:29:57.160
and what is the makings of someone who is a
611
00:29:57.259 --> 00:29:58.259
great storyteller?
612
00:29:58.319 --> 00:29:59.859
How can we do this? Yeah.
613
00:30:00.579 --> 00:30:06.269
I mean, for me, storytelling is a kind of built skill. Um,
614
00:30:06.710 --> 00:30:08.009
a lot of people think that you're either a good
615
00:30:08.049 --> 00:30:11.490
storyteller or you're not. And I just push back on that. Um,
616
00:30:12.589 --> 00:30:14.710
I read, I just spent a lot of time reading
617
00:30:15.039 --> 00:30:17.680
all of these different pieces on the principles of great
618
00:30:17.720 --> 00:30:21.859
storytelling from Disney and Pixar and the, these places that
619
00:30:21.900 --> 00:30:28.140
I consider to be, um, foundational storytellers. And I think, honestly,
620
00:30:28.480 --> 00:30:32.259
you can study that. I don't write about fantasy worlds
621
00:30:32.339 --> 00:30:38.049
and different realities, but those principles run through every area
622
00:30:38.069 --> 00:30:41.150
of your life. If you're an entrepreneur and you're running
623
00:30:41.170 --> 00:30:44.390
a business and you're constantly telling stories, you're doing it
624
00:30:44.410 --> 00:30:46.089
to your investors to tell them to give you money.
625
00:30:46.109 --> 00:30:47.910
You're doing it to your employees to give them that
626
00:30:48.009 --> 00:30:50.380
vision of what you're building and why it's so exciting.
627
00:30:50.730 --> 00:30:53.799
And so it's just a foundational skill on a day-to-day basis.
628
00:30:54.710 --> 00:30:56.509
And I just focused on how can I just keep
629
00:30:56.529 --> 00:31:00.059
getting better at it? My mom is an incredible storyteller.
630
00:31:01.099 --> 00:31:03.079
Everyone that knows her will say that about her. She
631
00:31:03.119 --> 00:31:06.440
just has this like air about her where she just
632
00:31:06.460 --> 00:31:09.579
kind of captivates a room. And I think maybe I
633
00:31:09.599 --> 00:31:11.710
had a little bit of that from her naturally. Like
634
00:31:11.750 --> 00:31:13.329
I was always the guy in the locker room that
635
00:31:13.349 --> 00:31:16.049
was telling stories and like, you know, had people laughing.
636
00:31:16.089 --> 00:31:18.309
I wasn't like a clown, but always had some story
637
00:31:18.349 --> 00:31:20.720
that I would like to be telling. And so I've
638
00:31:20.779 --> 00:31:22.779
kind of tried to take that and put it into
639
00:31:22.819 --> 00:31:25.380
my writing. When I'm writing about a topic, how can
640
00:31:25.420 --> 00:31:29.220
I infuse a degree of personality, of emotion, of novelty,
641
00:31:29.940 --> 00:31:32.960
something that just makes it more than a dry educational piece?
642
00:31:32.980 --> 00:31:36.410
Because you think about as a child, you have all
643
00:31:36.430 --> 00:31:38.710
these textbooks and these things that they're making you read,
644
00:31:38.730 --> 00:31:43.029
and it's really hard to absorb stuff that feels that dry, mundane.
645
00:31:43.950 --> 00:31:46.490
It's much easier to absorb something when it feels relatable.
646
00:31:46.529 --> 00:31:49.170
It feels like it has... wit. It feels like it
647
00:31:49.210 --> 00:31:52.269
has novelty or emotion and it's grabbing you in some
648
00:31:52.349 --> 00:31:55.380
different way. Um, and so I think it's just so
649
00:31:55.430 --> 00:31:58.880
important to develop that, to hone that skill, um, and
650
00:31:58.920 --> 00:32:01.359
really to just keep improving upon it. I mean, I
651
00:32:01.400 --> 00:32:03.000
started this a year and a half, not even a
652
00:32:03.019 --> 00:32:07.299
year and a half ago. I started it. I'm 12th
653
00:32:07.640 --> 00:32:10.269
of 2020, I started writing publicly. That was when I
654
00:32:10.289 --> 00:32:11.910
started my Twitter writing.
655
00:32:12.190 --> 00:32:12.450
Wow.
656
00:32:12.529 --> 00:32:14.430
Really? It's only been that amount of time?
657
00:32:14.450 --> 00:32:14.769
Yeah.
658
00:32:15.250 --> 00:32:15.529
Yeah.
659
00:32:15.529 --> 00:32:17.390
14 months or 15 months, whatever that is. I had
660
00:32:17.390 --> 00:32:23.210
500 Twitter followers, started putting stuff out. And I objectively
661
00:32:23.250 --> 00:32:26.210
think my early stuff was pretty bad. It was well-researched
662
00:32:26.279 --> 00:32:29.420
and well thought through, but it didn't have that extra
663
00:32:29.480 --> 00:32:32.640
kind of it factor. And that just comes from storytelling.
664
00:32:33.279 --> 00:32:36.519
So let's go a step further then. Let's break it down.
665
00:32:37.000 --> 00:32:40.859
Someone who says, I'm not a good storyteller, how can
666
00:32:40.880 --> 00:32:43.599
I get better? What are some of the practical applications
667
00:32:43.640 --> 00:32:45.839
or practical things they could take away from this conversation
668
00:32:46.240 --> 00:32:48.930
to implement immediately to become a better storyteller?
669
00:32:49.349 --> 00:32:53.789
Yeah. I think the three biggest ones for me, maybe
670
00:32:53.829 --> 00:32:55.569
I'm going to end up running over on that, but
671
00:32:56.089 --> 00:33:00.069
I think something that elicits an emotional response from the
672
00:33:00.130 --> 00:33:04.430
audience is You need emotion woven into the fabric of
673
00:33:04.470 --> 00:33:07.900
what you are writing, saying, speaking, whatever it might be.
674
00:33:07.920 --> 00:33:10.279
It needs to grab people in some way. And so
675
00:33:10.619 --> 00:33:12.359
when you're writing it or when you're sketching out your
676
00:33:12.400 --> 00:33:15.420
notes for something that you're going to publicly say and
677
00:33:15.440 --> 00:33:18.779
the storytelling aspect of it, you need to know what
678
00:33:18.819 --> 00:33:21.109
that emotion is going to be. What are you trying
679
00:33:21.140 --> 00:33:24.309
to elicit? Is it happiness? Is it hope? Is it inspiration?
680
00:33:24.329 --> 00:33:28.599
And the best writers do that naturally. I wasn't one
681
00:33:28.619 --> 00:33:30.549
of those like best writers. I had to force it.
682
00:33:30.619 --> 00:33:33.359
I would have to think before I wrote something. What
683
00:33:33.440 --> 00:33:35.279
is the emotion that I'm going for here and how
684
00:33:35.299 --> 00:33:37.059
do I weave that in and make sure that it's
685
00:33:37.369 --> 00:33:40.660
kind of creating that reaction and creating that response? The
686
00:33:40.680 --> 00:33:44.410
other piece is novelty to me. It's what is like
687
00:33:44.430 --> 00:33:47.170
the oh, wow moment that I'm triggering in my audience
688
00:33:48.190 --> 00:33:50.859
that's kind of taking them out of their. normal, just
689
00:33:50.900 --> 00:33:55.140
like humdrum life that I'm hitting them with. Because that's
690
00:33:55.160 --> 00:33:57.109
when you grab someone and then they remember it. Then
691
00:33:57.150 --> 00:33:59.470
they're telling that story and they're sharing it with somebody.
692
00:33:59.509 --> 00:34:02.250
And now you're bigger than just your one-to-one of you
693
00:34:02.269 --> 00:34:04.910
telling a story to someone else. It becomes like you
694
00:34:04.930 --> 00:34:07.559
have this K factor of like shareability of the things
695
00:34:07.579 --> 00:34:10.360
that you're putting out there. So I think those are
696
00:34:10.380 --> 00:34:12.420
the two biggest. I mean, the other one, which is
697
00:34:12.460 --> 00:34:15.619
just like table stakes for all writing and speaking is
698
00:34:16.340 --> 00:34:19.550
you need to be punchy and concise about how you
699
00:34:19.590 --> 00:34:22.630
tell a story. Telling a great story isn't about writing
700
00:34:22.670 --> 00:34:26.130
a million words and winding it in 40 directions and
701
00:34:26.210 --> 00:34:30.030
making it complicated and using big words. It's actually the opposite.
702
00:34:30.150 --> 00:34:31.650
It's like the Mark Twain quote. It's one of my
703
00:34:31.670 --> 00:34:35.030
favorite quotes. I didn't have time to write a short letter,
704
00:34:35.110 --> 00:34:38.070
so I wrote a long one instead. And I just
705
00:34:38.159 --> 00:34:40.920
love that quote because it's so true. It's much harder
706
00:34:41.019 --> 00:34:44.409
to simplify and write something very clear and short than
707
00:34:44.449 --> 00:34:49.710
it is to write some long winding verbose piece. And
708
00:34:49.750 --> 00:34:51.969
that plays through to storytelling. The best storytellers in the
709
00:34:52.010 --> 00:34:56.530
world are the most concise. Every single word is considered.
710
00:34:56.909 --> 00:35:00.449
It's thoughtful. And that's, I mean, I think that is
711
00:35:00.510 --> 00:35:02.389
just table stakes. If you want to be a great
712
00:35:02.429 --> 00:35:04.309
storyteller and you want to improve your storytelling.
713
00:35:04.329 --> 00:35:08.590
It's like a standup comedians talk about the economy of words,
714
00:35:09.090 --> 00:35:10.949
the best of the best. They make it feel like
715
00:35:10.989 --> 00:35:13.739
they just kind of just kind of stumble out on
716
00:35:13.880 --> 00:35:18.519
stage and start talking and yet the great ones have
717
00:35:19.119 --> 00:35:24.039
handcrafted every single word they say when they get on
718
00:35:24.079 --> 00:35:29.000
that stage so i want may may 9th 2020 is
719
00:35:29.019 --> 00:35:31.539
this the first thread that helped you blow up and
720
00:35:31.840 --> 00:35:33.320
and this is i just want to give an example
721
00:35:33.360 --> 00:35:35.380
for people who haven't read this or heard of your
722
00:35:35.420 --> 00:35:37.460
stuff yet and this is how it starts and it
723
00:35:37.539 --> 00:35:41.590
piqued my curiosity you A thread on markets. It is
724
00:35:41.630 --> 00:35:45.010
the year 1500 and you enter a market in Renaissance
725
00:35:45.070 --> 00:35:49.090
era Italy. There are buyers and there are sellers. Prices
726
00:35:49.230 --> 00:35:52.599
of the various goods are determined by the interaction by
727
00:35:52.639 --> 00:35:57.320
and among these individuals. Now in walks Mr. Federico, a
728
00:35:57.380 --> 00:35:58.980
man of endless means.
729
00:35:59.739 --> 00:36:00.800
Tweet two. Mr.
730
00:36:00.840 --> 00:36:03.159
Federico climbs a tower in the center of the market
731
00:36:03.199 --> 00:36:05.989
and proclaims, quote, I am a buyer of any and
732
00:36:06.030 --> 00:36:09.650
all goods in this market regardless of their price. He
733
00:36:09.710 --> 00:36:12.389
climbs down off the tower and exits the market to
734
00:36:12.429 --> 00:36:16.170
return to his mansion. What happens in the market when
735
00:36:16.210 --> 00:36:18.989
he leaves? And then the thread continues. So this is
736
00:36:19.010 --> 00:36:21.449
what I'm talking about. Like, I'm like, wait, it's like
737
00:36:21.489 --> 00:36:24.110
in a book where the good authors make you turn
738
00:36:24.179 --> 00:36:25.860
the page. I got to go to the next one
739
00:36:25.900 --> 00:36:27.380
and the next one and the next one, you can't
740
00:36:27.400 --> 00:36:30.719
put it down. So this is at the beginning of you,
741
00:36:30.800 --> 00:36:33.199
you probably had no followers at this point. And now
742
00:36:33.219 --> 00:36:38.130
you have 242,000 plus, um, So what's going through your
743
00:36:38.150 --> 00:36:40.530
head as you're putting this together now that I shared
744
00:36:40.570 --> 00:36:41.260
a real example?
745
00:36:41.639 --> 00:36:43.780
Yeah, that was my first one. So it's near and
746
00:36:43.800 --> 00:36:50.119
dear to my heart. So it's May 2020. Markets are
747
00:36:50.239 --> 00:36:53.269
soaring while the economy is still shut down. Everyone's stuck
748
00:36:53.289 --> 00:36:57.269
at home. And basically everyone in the world, myself included,
749
00:36:57.329 --> 00:36:59.210
was like, what the hell is going on?
750
00:36:59.650 --> 00:37:00.030
How is the.
751
00:37:00.010 --> 00:37:03.650
Market ripping right now while everyone's stuck at home and
752
00:37:03.690 --> 00:37:06.730
no one's spending money? And I was trying to find
753
00:37:06.769 --> 00:37:09.789
a way to explain the concept that like what the
754
00:37:09.849 --> 00:37:11.949
Federal Reserve is doing, which is they're going into the
755
00:37:11.989 --> 00:37:14.250
market and basically just buying a bunch of stuff and
756
00:37:14.469 --> 00:37:17.820
the impact that has on prices in a market. And
757
00:37:17.840 --> 00:37:19.139
I was like, how can I do this in a
758
00:37:19.159 --> 00:37:20.980
way that is going to make it digestible? It's not
759
00:37:21.000 --> 00:37:23.539
going to be technical things about buying bonds and what
760
00:37:23.559 --> 00:37:26.119
they're doing. And it's going to be accessible to anybody.
761
00:37:26.539 --> 00:37:29.260
And so I basically, I sat down, I had a
762
00:37:29.280 --> 00:37:31.519
few friends from my baseball days texting me, asking me
763
00:37:31.559 --> 00:37:33.159
these questions. And I was like, I need to figure
764
00:37:33.199 --> 00:37:35.219
out something that I can just send them And I
765
00:37:35.239 --> 00:37:37.309
can just be like, here, this explains it. You'll get it.
766
00:37:38.260 --> 00:37:40.010
And that was how that came to life. And I
767
00:37:40.070 --> 00:37:45.670
created that fictional character, Mr. Federico, which is admittedly not
768
00:37:45.690 --> 00:37:48.190
my best humor, but it got the point across that
769
00:37:48.210 --> 00:37:51.730
that's what I was talking about. And I wrote that
770
00:37:52.050 --> 00:37:53.690
on the floor of my garage just because I had
771
00:37:53.730 --> 00:37:55.739
an idea right then. I wanted to write it down.
772
00:37:56.340 --> 00:37:59.440
And I posted it. First off, I called my shot
773
00:37:59.500 --> 00:38:00.980
because I told my wife that it was going to
774
00:38:01.000 --> 00:38:02.820
go viral. And she rolled her eyes at me and
775
00:38:02.840 --> 00:38:06.110
walked away. I had 500 followers at the time, so
776
00:38:06.130 --> 00:38:09.269
there was no reason to think so. You really believed
777
00:38:09.309 --> 00:38:09.690
that though.
778
00:38:09.829 --> 00:38:11.570
What's that? You really believed that.
779
00:38:11.650 --> 00:38:13.289
I did. Yeah. I wrote it and I was like,
780
00:38:13.309 --> 00:38:15.739
I basically just wrote it and I was like, this
781
00:38:15.800 --> 00:38:19.380
is really good. If this is a meritocracy, which I
782
00:38:19.420 --> 00:38:23.679
believe Twitter effectively is, this should go viral. This is
783
00:38:23.760 --> 00:38:26.019
really good. It's thoughtful. It gets the point across. I
784
00:38:26.059 --> 00:38:28.699
think it's really good. And so I tweeted it and
785
00:38:29.340 --> 00:38:30.820
I didn't have many followers, so it didn't really get
786
00:38:30.860 --> 00:38:33.260
much traction at first. And then I sort of hustled
787
00:38:33.300 --> 00:38:35.610
a little bit. I commented it under a couple of
788
00:38:35.670 --> 00:38:39.610
big accounts posts. And Chamath, who has this massive following,
789
00:38:39.690 --> 00:38:43.010
saw it and retweeted it and said, this is good
790
00:38:43.070 --> 00:38:45.369
and retweeted it. And so all of a sudden, my
791
00:38:45.429 --> 00:38:48.690
phone just went bananas. I went from having 500 followers
792
00:38:48.730 --> 00:38:52.969
to 2000 or something that day. And that was kind
793
00:38:53.010 --> 00:38:54.829
of the start of it. I realized like, oh, there's
794
00:38:54.869 --> 00:38:59.389
something to this concept of breaking these concepts down in
795
00:38:59.469 --> 00:39:02.769
an easy, digestible way for people. And that it wasn't
796
00:39:02.809 --> 00:39:04.869
out there. Like in general, I had this perception that
797
00:39:04.909 --> 00:39:08.110
the market had split where in the world of finance,
798
00:39:08.130 --> 00:39:10.650
in the world of business, you have like the really
799
00:39:10.690 --> 00:39:14.050
low end, like the TikTokers that are giving you nonsense
800
00:39:14.090 --> 00:39:16.699
advice about buying options and like all of that stuff.
801
00:39:16.840 --> 00:39:18.679
And then you had the like really high end of
802
00:39:18.739 --> 00:39:20.820
people who are just talking over your head. They're like,
803
00:39:21.360 --> 00:39:23.940
you know, basically trying to make you feel dumb because
804
00:39:23.980 --> 00:39:25.900
they want you to pay them to manage their money,
805
00:39:25.960 --> 00:39:29.170
whatever it might be. And so my decided was like, if,
806
00:39:29.469 --> 00:39:32.269
if this end, is the like really crappy like you
807
00:39:32.289 --> 00:39:34.690
know bicycle and this end is the like ferrari i
808
00:39:34.710 --> 00:39:37.380
was like i'm gonna be the like toyota camry just
809
00:39:37.409 --> 00:39:39.420
like good old faithful gets you from point a to
810
00:39:39.440 --> 00:39:42.559
point b sell tons of those cars because they're just
811
00:39:42.599 --> 00:39:46.059
very you know they're like a good price point quote-unquote Um,
812
00:39:46.280 --> 00:39:47.659
and that's what I wanted to be. I wanted it
813
00:39:47.719 --> 00:39:50.300
to be accessible, digestible. I wanted anyone to be able
814
00:39:50.320 --> 00:39:52.809
to share it and get value out of it. Um,
815
00:39:53.110 --> 00:39:55.150
and I think I've generally met that, you know, met
816
00:39:55.170 --> 00:39:56.690
that burden that I tried to set out for.
817
00:39:57.289 --> 00:39:59.070
Reminds me a little bit of Tim Urban. He's been
818
00:39:59.090 --> 00:40:01.789
on the show. He writes at weight, but Wyatt.com takes
819
00:40:01.809 --> 00:40:03.090
a huge fan of Tim. Yeah.
820
00:40:03.130 --> 00:40:05.949
I think everyone who writes loves Tim because he takes
821
00:40:06.429 --> 00:40:11.679
the super complex, makes it simple and is funny. And, um,
822
00:40:13.599 --> 00:40:18.019
I think the best writers have that ability to take
823
00:40:18.039 --> 00:40:21.389
the complex, they then digest it and synthesize it and
824
00:40:21.489 --> 00:40:23.469
retell it in the form of a story. They add
825
00:40:23.510 --> 00:40:28.230
some humor and they make the reader feel smarter after
826
00:40:28.289 --> 00:40:30.889
having read them, not dumber because they speak like, listen
827
00:40:30.909 --> 00:40:34.000
to my big words. And that is what I strive for.
828
00:40:34.019 --> 00:40:36.699
I think that's what leaders in general should strive for,
829
00:40:36.760 --> 00:40:40.690
regardless of your title, regardless of your job. And one
830
00:40:40.710 --> 00:40:42.760
of the best ways, I think, to get better at this, one,
831
00:40:42.989 --> 00:40:44.739
first and foremost, like anything else, you just got to
832
00:40:44.780 --> 00:40:46.619
do it, right? You got to get the reps. But
833
00:40:46.639 --> 00:40:49.260
then two, and I think a close second is you
834
00:40:49.280 --> 00:40:51.300
got to be reading this stuff constantly. And that's why
835
00:40:51.440 --> 00:40:53.679
Twitter has been a great learning tool for me. And
836
00:40:53.699 --> 00:40:55.880
I push people towards it because there are some negative
837
00:40:55.900 --> 00:40:58.480
things just like anything else in life, but there's so
838
00:40:58.539 --> 00:40:59.980
much positive that comes from it.
839
00:40:59.980 --> 00:41:02.159
And there's so much out there to learn.
840
00:41:02.179 --> 00:41:04.239
And I feel like this is something you've really, it's
841
00:41:04.300 --> 00:41:05.320
become part of you.
842
00:41:05.699 --> 00:41:05.980
Yeah.
843
00:41:06.360 --> 00:41:06.539
Yeah.
844
00:41:06.639 --> 00:41:08.679
I mean, to me, it's just about being positive some.
845
00:41:09.500 --> 00:41:13.199
you clearly have that mentality, but the world in my
846
00:41:13.260 --> 00:41:17.360
view is positive, is a positive sum game when other
847
00:41:17.409 --> 00:41:20.690
people win and we have a rising tide and a
848
00:41:20.750 --> 00:41:24.489
groundswell of people getting smarter and feeling empowered and inspired
849
00:41:24.550 --> 00:41:27.289
by things I'm putting out there. That makes me better off.
850
00:41:27.329 --> 00:41:30.530
Like the economy starts getting better. People are making better decisions.
851
00:41:30.570 --> 00:41:34.010
They're spending money on things. They're investing in things. And, um,
852
00:41:35.219 --> 00:41:37.199
And when that happens, we all win. And so like,
853
00:41:37.469 --> 00:41:40.110
I just have this general positive, some mentality around this stuff,
854
00:41:40.170 --> 00:41:42.289
or if I can empower people, and if I can
855
00:41:42.329 --> 00:41:45.050
spend a few hours writing something that I don't know,
856
00:41:45.070 --> 00:41:47.250
I mean, the recent things I'm putting out there, like
857
00:41:47.429 --> 00:41:50.400
it's 2 million, 3 million impressions in 24 hours. It's like,
858
00:41:50.659 --> 00:41:53.280
that's an unbelievable number of people that I can reach.
859
00:41:53.340 --> 00:41:57.480
And if 1% of those people feel empowered and inspired
860
00:41:57.539 --> 00:42:02.150
or learn one thing, that's the best university teacher in
861
00:42:02.170 --> 00:42:04.130
the world. You can't reach that many people. And so
862
00:42:04.150 --> 00:42:05.809
we live in this era where I can do that.
863
00:42:06.349 --> 00:42:08.670
And I just am blown away by that fact. And
864
00:42:08.730 --> 00:42:11.809
so that's kind of what inspires me to continue doing
865
00:42:11.889 --> 00:42:16.269
it is just this general positive sum mentality that I
866
00:42:16.389 --> 00:42:20.590
feel around all of it. I tweeted something about starting
867
00:42:20.610 --> 00:42:23.969
to genuinely root for others to succeed is this massive
868
00:42:24.050 --> 00:42:26.809
unlock in life. And I really believe it. The people
869
00:42:26.909 --> 00:42:30.139
who I look at who have helped me along the
870
00:42:30.179 --> 00:42:32.780
way who had no reason, like I was giving them
871
00:42:32.880 --> 00:42:36.219
no benefit. Um, and I may never give them a benefit,
872
00:42:36.539 --> 00:42:38.670
but they still just rooted for me along the way. Um,
873
00:42:40.050 --> 00:42:41.730
that just blows me away. And I want to be
874
00:42:41.769 --> 00:42:45.929
that person to tens, hundreds, thousands of others, you know,
875
00:42:45.949 --> 00:42:47.809
in their lives so that they feel that same way.
876
00:42:47.829 --> 00:42:48.670
Yeah.
877
00:42:49.250 --> 00:42:50.889
One of the things I wanted to talk to you about,
878
00:42:50.949 --> 00:42:54.010
since we have the similar background of playing, um, a
879
00:42:54.110 --> 00:42:58.579
sport in college, is that we've had experiences with coaches,
880
00:42:59.159 --> 00:43:02.940
both on the field and maybe a boss can play
881
00:43:02.980 --> 00:43:05.559
the role of a coach as well. I'm curious from
882
00:43:05.619 --> 00:43:09.199
your perspective, what have you found when you compare and
883
00:43:09.219 --> 00:43:13.219
contrast the excellent coaches who have made your life better
884
00:43:13.260 --> 00:43:15.539
in more ways than just maybe throwing the ball harder
885
00:43:16.360 --> 00:43:20.510
or more accurate, but they've made you better? What's the
886
00:43:20.679 --> 00:43:24.989
makeup of a great coach, um, both sports wise and
887
00:43:25.010 --> 00:43:27.110
maybe outside of the sporting world too, in your mind.
888
00:43:27.130 --> 00:43:30.659
Yeah. I think the two things for me are in
889
00:43:30.699 --> 00:43:34.760
the trenches with the team. Um, that's a common thread
890
00:43:34.780 --> 00:43:38.099
in everything, whether that's sports or life, the best leaders,
891
00:43:38.139 --> 00:43:40.860
the best coaches, they're in the trenches with their guys.
892
00:43:40.880 --> 00:43:43.820
Like they're never, it's, um, I think it's the New
893
00:43:43.880 --> 00:43:48.239
Zealand all blacks, like the, the, um, the concept of like,
894
00:43:48.380 --> 00:43:50.880
never be too big to do the small things. And
895
00:43:51.440 --> 00:43:53.480
the team, the captains of the team are the ones
896
00:43:53.519 --> 00:43:55.389
that have to sweep out the locker room at the
897
00:43:55.409 --> 00:43:57.610
end of a game. And I was always taken with
898
00:43:57.650 --> 00:44:00.909
that concept and it's, it's it's really powerful. And I
899
00:44:00.949 --> 00:44:04.010
think the best coaches do it naturally. You can learn that,
900
00:44:04.190 --> 00:44:06.949
but it's just being in the trenches with, with the
901
00:44:06.989 --> 00:44:09.820
guys or girls on the team and, and you know,
902
00:44:09.840 --> 00:44:13.199
feeling like you're fighting alongside them. You just do so
903
00:44:13.260 --> 00:44:15.219
much and you want to work for that coach that's
904
00:44:15.239 --> 00:44:17.719
there with you. And then the other one is someone
905
00:44:17.739 --> 00:44:18.719
that's willing to challenge you.
906
00:44:18.739 --> 00:44:19.619
Yeah.
907
00:44:20.110 --> 00:44:22.610
Call you out when you're wrong on something, tell you
908
00:44:22.650 --> 00:44:24.909
that you're, you know, what you did is not good enough.
909
00:44:25.630 --> 00:44:26.949
Um, because otherwise you're.
910
00:44:26.829 --> 00:44:28.829
Just never going to get better. I mean, I had,
911
00:44:28.989 --> 00:44:32.050
I've had coaches in my life that were, you know,
912
00:44:32.130 --> 00:44:35.769
sort of just, um, sort of just there and like,
913
00:44:36.050 --> 00:44:38.130
you know, not going to call you out if you
914
00:44:38.170 --> 00:44:40.530
didn't put in the effort you should have because you
915
00:44:40.550 --> 00:44:42.449
were the star or whatever. They don't want to call
916
00:44:42.510 --> 00:44:45.170
out the star. The best coaches I found were the
917
00:44:45.250 --> 00:44:48.219
ones that were like, literally just say to your face,
918
00:44:48.500 --> 00:44:50.460
that's not good enough. You know, it's not good enough
919
00:44:50.519 --> 00:44:52.900
as well as I do. And if you're okay with
920
00:44:52.920 --> 00:44:55.019
that as your level of effort, there's, I don't know.
921
00:44:55.039 --> 00:44:57.219
I don't know who you are as a person. Um,
922
00:44:57.550 --> 00:44:59.789
those kinds of things, you're just like, Whoa, it kind
923
00:44:59.829 --> 00:45:01.690
of like knocks you back when someone calls you out
924
00:45:01.730 --> 00:45:03.750
like that. But those are the moments where you get,
925
00:45:03.889 --> 00:45:05.429
you might get pissed and you might be like, how
926
00:45:05.489 --> 00:45:08.369
dare they say that to me. But if it triggers
927
00:45:08.409 --> 00:45:10.250
that response and you kind of jump in and you're
928
00:45:10.289 --> 00:45:13.539
working harder because of it, I mean, man, the impact
929
00:45:13.559 --> 00:45:16.039
that can have on a full team when you're doing that. Um,
930
00:45:16.760 --> 00:45:18.679
And I always found that. I mean, I've had some
931
00:45:18.699 --> 00:45:21.599
amazing coaches and been privileged to have some amazing mentors,
932
00:45:22.420 --> 00:45:23.980
people that have been around me in my life. And
933
00:45:24.280 --> 00:45:26.239
the common thread among the most amazing ones is they
934
00:45:26.260 --> 00:45:29.300
just push my thinking. They just push me and push me.
935
00:45:29.320 --> 00:45:32.400
And if I say something that's unfounded, they're like, oh,
936
00:45:32.440 --> 00:45:34.199
do you really believe that? You think you've done the
937
00:45:34.239 --> 00:45:37.380
work to really believe that or to make that assertion
938
00:45:37.440 --> 00:45:40.789
in that confident of a manner? And normally you realize
939
00:45:40.809 --> 00:45:44.110
that you have it and you're like, oh crap, they're right.
940
00:45:44.230 --> 00:45:46.300
I need to dig in further. I need to spend
941
00:45:46.340 --> 00:45:48.820
more time on that. But I think it's those two.
942
00:45:48.860 --> 00:45:51.559
It's being in the trenches and then it's just being
943
00:45:51.619 --> 00:45:54.079
willing to challenge the people that are under you.
944
00:45:55.420 --> 00:45:55.960
I like that.
945
00:45:57.260 --> 00:45:59.820
I know for me, from a coaching perspective, they're the
946
00:45:59.880 --> 00:46:02.739
ones who pushed me to levels that I didn't even
947
00:46:02.800 --> 00:46:05.900
realize I was capable of. And that's because they weren't
948
00:46:05.980 --> 00:46:10.550
afraid for me to temporarily dislike them. Um, I, I,
949
00:46:10.730 --> 00:46:14.880
I grew to love them deeply sometimes after the fact,
950
00:46:15.360 --> 00:46:18.300
but I love the fact that they cared so much
951
00:46:18.860 --> 00:46:21.860
that they were willing to upset me because they knew
952
00:46:21.880 --> 00:46:24.280
that's what it took to get me to perform at
953
00:46:24.300 --> 00:46:26.610
a level. And I would say, I don't think I
954
00:46:26.650 --> 00:46:29.309
get a college scholarship without my two of my high
955
00:46:29.329 --> 00:46:29.789
school coaches.
956
00:46:29.849 --> 00:46:32.130
I'm in the exact same boat. My, um, my high
957
00:46:32.150 --> 00:46:36.090
school baseball coach who I'm still extremely close with to
958
00:46:36.110 --> 00:46:40.590
this day. I was just Coach John Beverly, small public
959
00:46:40.630 --> 00:46:44.469
high school in Massachusetts. And I remember like my freshman
960
00:46:44.489 --> 00:46:46.730
and sophomore year of high school, I had two great seasons,
961
00:46:47.630 --> 00:46:50.389
but I was throwing, I don't know, 78, 80 miles
962
00:46:50.429 --> 00:46:52.090
an hour, but I was good. I was like, you know,
963
00:46:52.150 --> 00:46:54.550
Dyson guys, a little, little breaking ball. Yeah. I was,
964
00:46:54.650 --> 00:46:57.110
I was doing the whole dance. And I remember at
965
00:46:57.139 --> 00:46:58.980
the end of that sophomore season, he called me in
966
00:46:59.000 --> 00:47:00.920
and he was like, what do you want to do? Like, well,
967
00:47:00.940 --> 00:47:03.320
what's your vision for baseball? Do you want to play
968
00:47:03.360 --> 00:47:05.780
in college? And I said like, yeah, I think maybe
969
00:47:05.820 --> 00:47:08.400
I could play in an Ivy league and, Um, you know,
970
00:47:08.420 --> 00:47:10.219
that's kind of lower end D one baseball. I think
971
00:47:10.260 --> 00:47:12.119
I could go do that. And he looked me straight
972
00:47:12.139 --> 00:47:14.800
in the face and he was like, how about Stanford?
973
00:47:15.460 --> 00:47:19.199
How about rice? And I remember thinking like this dude crazy.
974
00:47:19.360 --> 00:47:20.840
I mean, that was like the first thought that went
975
00:47:20.860 --> 00:47:23.210
through my mind was just like, this guy's nuts. I'm
976
00:47:23.250 --> 00:47:27.289
like a five, 10, 165 pound right-hander from Massachusetts public
977
00:47:27.309 --> 00:47:29.110
high school in Massachusetts. I'm throwing 80 miles an hour.
978
00:47:29.409 --> 00:47:31.110
What do you mean Stanford? Like Stanford's one of the
979
00:47:31.130 --> 00:47:34.079
best baseball programs in the country. Um, And he was
980
00:47:34.139 --> 00:47:35.980
dead serious. He looked, I mean, like I kind of
981
00:47:36.039 --> 00:47:37.460
laughed and I looked at him and he was just
982
00:47:37.500 --> 00:47:39.409
staring at me. And he's like, if you were willing
983
00:47:39.429 --> 00:47:40.949
to put in the work, you have the talent to
984
00:47:40.989 --> 00:47:43.750
do this. It's going to be hard, but that's what
985
00:47:43.789 --> 00:47:45.969
I expect from you is doing that. And all of
986
00:47:46.010 --> 00:47:48.829
a sudden it was like, oh, wow. Someone believes in
987
00:47:48.869 --> 00:47:51.110
me at that level. Like this guy who is an
988
00:47:51.170 --> 00:47:54.480
informed individual and credible believes in me at that level.
989
00:47:55.559 --> 00:47:58.099
And a year later, I had a scholarship offer from
990
00:47:58.119 --> 00:48:00.500
Stanford and I was signing a letter of intent to
991
00:48:00.539 --> 00:48:03.010
go to Stanford. And I attribute so much of that
992
00:48:03.050 --> 00:48:05.329
to just that one moment where he kind of challenged
993
00:48:05.369 --> 00:48:07.670
me and he was like, what about Stanford? What about Rice?
994
00:48:09.050 --> 00:48:11.349
It still blows me away to think about it. I mean,
995
00:48:11.429 --> 00:48:13.150
one of the most impactful moments in my whole life,
996
00:48:13.230 --> 00:48:15.079
I mean, in terms of setting a trajectory. And I
997
00:48:15.239 --> 00:48:20.340
owe him a massive debt of gratitude. But it's just amazing.
998
00:48:20.380 --> 00:48:22.940
There's like one person that believes in you on some
999
00:48:23.000 --> 00:48:24.920
level like that and is willing to challenge you and
1000
00:48:24.940 --> 00:48:27.550
kind of push you to that level can totally change
1001
00:48:27.590 --> 00:48:29.550
the trajectory and your path.
1002
00:48:30.139 --> 00:48:32.250
Doesn't that make you want to do that for other people?
1003
00:48:33.130 --> 00:48:36.570
Totally. I mean, it's what I try to do every
1004
00:48:36.610 --> 00:48:38.570
single day. I want to mentor people. I want to
1005
00:48:38.590 --> 00:48:42.110
be that person that had that impact. It's why I
1006
00:48:42.150 --> 00:48:45.730
think coaches, teachers, we're some of the most underpaid people
1007
00:48:45.769 --> 00:48:49.679
in the world. Everyone has that one high school teacher
1008
00:48:49.739 --> 00:48:54.019
or some person that, again, for no benefit, for no
1009
00:48:54.059 --> 00:48:57.719
monetary benefit, helped you and completely changed the course of
1010
00:48:57.739 --> 00:49:01.030
your life. And we pay our teachers like crap. We
1011
00:49:01.050 --> 00:49:03.690
pay these high school coaches like crap. And the impact
1012
00:49:03.730 --> 00:49:05.719
they have on young men and women and the course
1013
00:49:05.739 --> 00:49:08.539
of their life, it's truly remarkable.
1014
00:49:09.440 --> 00:49:13.199
I think it's got to be such a fulfilling and
1015
00:49:13.239 --> 00:49:16.019
rewarding feeling for them to do it. Uh, and I've,
1016
00:49:16.199 --> 00:49:18.480
I've gone back and interviewed some even had, had, had
1017
00:49:19.039 --> 00:49:21.159
a couple on this podcast because as a, as a
1018
00:49:21.199 --> 00:49:21.900
way to say thank you.
1019
00:49:21.940 --> 00:49:23.920
And just to deconstruct how their mind works.
1020
00:49:24.639 --> 00:49:28.070
And, um, to me, I love the thought of like
1021
00:49:28.170 --> 00:49:32.650
seeing something in someone who they believe in themselves, but they,
1022
00:49:33.050 --> 00:49:36.389
maybe their level of expectations are just right. Like here,
1023
00:49:36.670 --> 00:49:40.760
you know, they're, kind of realistic, but they've got like
1024
00:49:40.780 --> 00:49:43.739
a ceiling that they've put that it's not intentional. There's
1025
00:49:43.800 --> 00:49:49.449
nothing bad. They just don't really think bigger. And for
1026
00:49:49.489 --> 00:49:55.789
you or me or anyone to say, actually, Stanford, Rice,
1027
00:49:57.309 --> 00:50:00.309
that is realistic for you. I know it is. And
1028
00:50:00.369 --> 00:50:03.829
here's some things to do to do it. But it's
1029
00:50:03.909 --> 00:50:06.550
actually in play. And all of a sudden, your mind changes.
1030
00:50:06.590 --> 00:50:11.659
Your mind shifts. your expectation level changed. And to me,
1031
00:50:11.719 --> 00:50:14.480
like he set a standard of excellence for you that
1032
00:50:14.539 --> 00:50:16.900
we can do. We can do this for people if
1033
00:50:16.960 --> 00:50:19.920
we care, but that's hard. Like it's much easier for
1034
00:50:19.940 --> 00:50:21.530
your coach to be like, wow, I'm glad you're on
1035
00:50:21.590 --> 00:50:24.250
our team. Don't transfer. Don't go somewhere else.
1036
00:50:24.769 --> 00:50:25.289
I love you.
1037
00:50:25.389 --> 00:50:27.809
I'm here for you instead. He's like, no, I'm going
1038
00:50:27.829 --> 00:50:30.730
to push you and raise your level of expectations. Like
1039
00:50:30.769 --> 00:50:33.070
what an awesome moment of leadership.
1040
00:50:33.619 --> 00:50:36.039
Yeah. Insane. I mean, it's like the Pygmalion effect. I
1041
00:50:36.079 --> 00:50:38.179
just wrote about this. It's a cognitive bias. It's like
1042
00:50:38.219 --> 00:50:43.400
high expectations lead to improved and higher performance. Someone vocalizing
1043
00:50:43.719 --> 00:50:47.579
that they have these amazing high expectations for you has
1044
00:50:47.599 --> 00:50:49.780
this impact where you just want to live up to
1045
00:50:49.820 --> 00:50:51.960
those expectations that the person has set for you. You
1046
00:50:51.980 --> 00:50:54.460
want to work hard and achieve those things.
1047
00:50:54.800 --> 00:50:55.179
I don't know.
1048
00:50:55.239 --> 00:50:57.840
It's funny. We go through life and we don't necessarily
1049
00:50:57.929 --> 00:51:03.130
vocalize our thanks for the people that that gave us
1050
00:51:03.170 --> 00:51:04.989
those moments. I mean, I'm like, I'm going to send
1051
00:51:05.010 --> 00:51:07.780
my coach this, this podcast. Cause I want him, I
1052
00:51:07.820 --> 00:51:10.019
want him to hear it and, you know, like publicly
1053
00:51:10.039 --> 00:51:12.659
kind of hear the word of thanks, but you know,
1054
00:51:12.699 --> 00:51:14.199
maybe I've said it to him over the years, but
1055
00:51:14.239 --> 00:51:16.960
it's just funny to think about like how impactful one moment.
1056
00:51:17.019 --> 00:51:18.869
I don't even know if he remembers that moment, but
1057
00:51:18.909 --> 00:51:20.949
it's so impactful for me. Yeah.
1058
00:51:21.030 --> 00:51:23.110
He probably doesn't, you know, he probably doesn't. I've, I've
1059
00:51:23.150 --> 00:51:25.510
said those things to my coach was like, Oh, cause
1060
00:51:25.570 --> 00:51:26.289
it's just the way they are.
1061
00:51:26.559 --> 00:51:27.760
Yeah. You know, like the great ones.
1062
00:51:28.199 --> 00:51:31.159
And they've done it for other people, too, because that's
1063
00:51:31.179 --> 00:51:33.539
just their standard mode of operation. And I think that
1064
00:51:33.679 --> 00:51:35.860
I'm glad you said that this is a good kind
1065
00:51:35.900 --> 00:51:39.099
of signal for people. If there is somebody like that
1066
00:51:39.159 --> 00:51:41.800
in your life and hopefully there is or hopefully there's
1067
00:51:41.840 --> 00:51:44.300
more than one, I would urge you to tell them,
1068
00:51:44.639 --> 00:51:47.800
call them, email them, try to see them if possible.
1069
00:51:47.820 --> 00:51:49.099
I would urge you.
1070
00:51:49.199 --> 00:51:52.389
I did this recently with my high school offensive coordinator
1071
00:51:52.429 --> 00:51:54.670
who became a head coach. I asked him to go
1072
00:51:54.690 --> 00:51:58.139
to dinner. This was months ago. And, uh, we went
1073
00:51:58.219 --> 00:51:59.659
out to eat and I just wanted to look him
1074
00:51:59.679 --> 00:52:00.820
in the eye. He was with his wife and I
1075
00:52:00.860 --> 00:52:02.900
wanted his wife to hear it too. I wanted her
1076
00:52:02.920 --> 00:52:05.010
to hear like the impact he had on me. And
1077
00:52:05.050 --> 00:52:07.550
I just was like, honestly told him exactly how I felt.
1078
00:52:07.590 --> 00:52:09.289
And he had this like look in his eye. It's
1079
00:52:09.309 --> 00:52:11.409
like emotional. Even thinking about this, this look in his
1080
00:52:11.570 --> 00:52:15.150
eye of like, okay, like good. Like I still want
1081
00:52:15.170 --> 00:52:16.690
to do impress him though. You know how weird those
1082
00:52:16.730 --> 00:52:18.610
coaches were. You still want to impress him, but I
1083
00:52:18.630 --> 00:52:19.989
just want to make sure he knew it. And then
1084
00:52:20.030 --> 00:52:23.710
we had like hours and hours of conversation, storytelling, a
1085
00:52:23.809 --> 00:52:25.269
follow-up meeting afterwards.
1086
00:52:25.570 --> 00:52:27.409
It just, I urge people to do that.
1087
00:52:27.449 --> 00:52:30.840
Like to call somebody, see them, tell them, even text them, whatever,
1088
00:52:30.880 --> 00:52:33.619
maybe to let them know, like, thank you for what
1089
00:52:33.639 --> 00:52:35.119
you've done for me. Like, I don't know if you
1090
00:52:35.179 --> 00:52:37.480
fully realize how much you've impacted me and that can
1091
00:52:37.519 --> 00:52:38.340
be really powerful.
1092
00:52:38.659 --> 00:52:40.130
Yeah, absolutely.
1093
00:52:40.329 --> 00:52:40.710
I love it.
1094
00:52:41.010 --> 00:52:42.190
I love it.
1095
00:52:42.929 --> 00:52:43.449
One more thing.
1096
00:52:43.469 --> 00:52:46.539
I know we have to run, but, I want to
1097
00:52:46.559 --> 00:52:48.639
talk about the power of learning circles. Could you briefly
1098
00:52:48.699 --> 00:52:52.480
describe the power of learning circles? Because you're a lifelong learner.
1099
00:52:52.639 --> 00:52:55.800
I'm a lifelong learner. I'm fans of leaders who are
1100
00:52:56.159 --> 00:53:00.679
learning leaders. And you've written about learning circles. And I
1101
00:53:00.699 --> 00:53:03.699
get to do this too in my daily life. Can
1102
00:53:03.900 --> 00:53:05.739
you talk about the power of learning circles?
1103
00:53:05.760 --> 00:53:05.980
Yeah.
1104
00:53:06.320 --> 00:53:08.079
Maybe I need to write more about this too, because
1105
00:53:08.119 --> 00:53:09.880
it's something a lot of people ask me about.
1106
00:53:11.119 --> 00:53:11.400
My.
1107
00:53:13.010 --> 00:53:16.269
my hypothesis is that the best learning is communal. It's
1108
00:53:16.309 --> 00:53:19.429
not an individual activity. And what I mean by that
1109
00:53:19.670 --> 00:53:23.329
is when you read something new, you read a new concept,
1110
00:53:23.909 --> 00:53:26.070
you can sit there and think about it and it's
1111
00:53:26.090 --> 00:53:28.139
in your head and you've learned something a little bit,
1112
00:53:28.659 --> 00:53:32.219
but it gets really cemented. It gets much more dynamic
1113
00:53:32.300 --> 00:53:34.519
and usable when you go talk about it with a
1114
00:53:37.539 --> 00:53:40.099
push and pull it in different directions, this idea becomes
1115
00:53:40.199 --> 00:53:42.559
much more than just a concept that you've read about
1116
00:53:42.579 --> 00:53:45.019
and you've only heard it one way. And so one
1117
00:53:45.039 --> 00:53:46.820
thing that I always encourage people to do and that
1118
00:53:46.860 --> 00:53:49.860
I've adopted in my own life is develop these circles
1119
00:53:49.940 --> 00:53:53.510
of friends, whether it's a group chat or a hangout
1120
00:53:53.610 --> 00:53:56.389
every now and then in person, groups of people that
1121
00:53:56.429 --> 00:53:59.989
you can collectively learn with about these things and bring
1122
00:54:00.030 --> 00:54:02.010
up these ideas. It doesn't have to be formal and
1123
00:54:02.030 --> 00:54:04.849
you're saying, hey, this is my learning circle. But groups
1124
00:54:04.889 --> 00:54:07.610
of friends that push your thinking on things where you
1125
00:54:07.630 --> 00:54:09.969
can throw out an idea and say, hey, I'm really
1126
00:54:10.010 --> 00:54:13.110
thinking about the future of work. What does it look like?
1127
00:54:13.159 --> 00:54:15.409
I read this cool article about X, Y, or Z.
1128
00:54:15.449 --> 00:54:17.699
And what do you think about that? And they totally disagree.
1129
00:54:17.739 --> 00:54:19.840
And then you kind of go at it a little
1130
00:54:19.880 --> 00:54:22.360
bit and push in different directions. And suddenly you're just like,
1131
00:54:22.780 --> 00:54:25.519
you have this unbelievably dynamic set of thoughts about a
1132
00:54:25.559 --> 00:54:27.739
concept that you never would have had if you had
1133
00:54:27.760 --> 00:54:29.579
just read the article and then said, oh, yeah, I
1134
00:54:29.619 --> 00:54:32.000
know about the future of work now. It's just a
1135
00:54:32.039 --> 00:54:34.179
different degree. You were here and now you're up here.
1136
00:54:35.019 --> 00:54:37.960
And that's brought about by that collective learning. And so
1137
00:54:38.000 --> 00:54:41.059
I always encourage people like find your learning circle, find
1138
00:54:41.159 --> 00:54:44.139
people that you can kind of collectively come together with
1139
00:54:45.000 --> 00:54:47.019
and learn together, learn in that same way.
1140
00:54:47.579 --> 00:54:47.969
I love it.
1141
00:54:49.360 --> 00:54:53.500
Thanks so much, man, for being here. There's so much
1142
00:54:53.659 --> 00:54:55.530
out there to learn more about you.
1143
00:54:55.550 --> 00:54:57.760
Where would you send people online?
1144
00:54:58.349 --> 00:55:01.409
Yeah. I mean, my Twitter is at sawhillbloom. Just my name.
1145
00:55:01.570 --> 00:55:05.070
It's the benefit of having a weird name. So it's
1146
00:55:05.139 --> 00:55:11.780
at sawhillbloom. And then my newsletter is, I don't know, sawhillbloom.substack.com,
1147
00:55:11.820 --> 00:55:12.099
I think.
1148
00:55:12.119 --> 00:55:14.460
The Curiosity Chronicle. I love the name.
1149
00:55:14.780 --> 00:55:18.639
Yeah. Just exploring my own curiosity and sharing it with others.
1150
00:55:18.800 --> 00:55:22.860
So I highly recommend people checking it out because both
1151
00:55:22.909 --> 00:55:26.280
your threads and your um, your sub stack, because I've,
1152
00:55:26.420 --> 00:55:28.880
I've learned a ton from it personally. So every time
1153
00:55:28.920 --> 00:55:31.219
like a new thread comes, I am ready. Um, so
1154
00:55:31.260 --> 00:55:33.840
I really, and, and your, uh, sub stack, I really
1155
00:55:33.860 --> 00:55:35.400
appreciate it, man. And thanks so much for being here.
1156
00:55:35.420 --> 00:55:37.900
I'd love to continue our dialogue as we both progress.
1157
00:55:38.280 --> 00:55:40.150
Would love to appreciate it. Thanks so much.
1158
00:55:40.429 --> 00:55:40.789
Thanks, man.
1159
00:55:41.949 --> 00:55:45.289
Now that is a conversation I love to have continued
1160
00:55:45.349 --> 00:55:48.789
for hours. And we both intend to do that after
1161
00:55:48.829 --> 00:55:50.590
we got to recording. So he'll say, Hey, you got,
1162
00:55:50.610 --> 00:55:52.489
you have to come to New York city so we
1163
00:55:52.510 --> 00:55:56.070
can keep this, uh, going, maybe over a meal and
1164
00:55:56.090 --> 00:55:58.760
a few drinks, and I fully intend to do that.
1165
00:56:00.139 --> 00:56:03.039
I really appreciate the way his mind works and how
1166
00:56:03.679 --> 00:56:08.119
deep of a thinker Sahil is. A few takeaways from
1167
00:56:08.159 --> 00:56:11.579
my notes. Learning circles. Develop a circle of people to
1168
00:56:11.699 --> 00:56:15.969
collectively learn with. Push your thinking. This is something I
1169
00:56:16.010 --> 00:56:18.889
do with my learning leader circles, and it's some of
1170
00:56:18.929 --> 00:56:22.869
the most rewarding and fulfilling work I do where I'm
1171
00:56:23.070 --> 00:56:28.760
able to facilitate conversations, ask questions, ask even better follow-up
1172
00:56:28.800 --> 00:56:31.840
questions so that we all can learn together. Then the
1173
00:56:31.920 --> 00:56:36.119
makeup of a great coach. They're never too big to
1174
00:56:36.159 --> 00:56:39.039
do the small things. They push you beyond what you
1175
00:56:39.139 --> 00:56:45.420
think you're capable of. They lift expectations for you. As
1176
00:56:45.480 --> 00:56:48.510
his coach said to him, how about Stanford when that
1177
00:56:48.570 --> 00:56:51.929
wasn't even in Sahil's mind? And I'd like for you
1178
00:56:51.969 --> 00:56:55.550
to take a moment and say thank you to someone
1179
00:56:55.570 --> 00:56:58.420
who has done this for you. Maybe text them, call them,
1180
00:56:58.500 --> 00:57:00.599
meet with them, send them an email, write them a letter.
1181
00:57:01.099 --> 00:57:03.920
I'd love to see you do this and hear about
1182
00:57:03.940 --> 00:57:07.800
the response from that person when you do. And then
1183
00:57:08.500 --> 00:57:12.960
why writing makes you better at everything you do. That
1184
00:57:13.000 --> 00:57:16.869
was a fun part of the conversation when Sahil said
1185
00:57:16.949 --> 00:57:21.829
writing is the best way to expose gaps in your thinking.
1186
00:57:22.309 --> 00:57:25.480
When you write, you think better, and it makes you
1187
00:57:25.519 --> 00:57:26.949
better at every.
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00:57:26.889 --> 00:57:31.949
Aspect of your life. All leaders should be writers.
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00:57:32.510 --> 00:57:34.110
I want to say once again, thank you so much
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00:57:34.150 --> 00:57:37.250
for continuing to spread the message and telling a friend
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00:57:37.429 --> 00:57:40.260
or two, hey, you should listen to this episode of
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00:57:40.300 --> 00:57:43.199
The Learning Leader Show with Sahil Bloom. It will make
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00:57:43.260 --> 00:57:46.659
you a more effective leader. And because you continue to
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00:57:46.679 --> 00:57:49.480
do that, and because you continue to write reviews and
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00:57:49.559 --> 00:57:53.110
rate the show, hopefully five stars on Apple Podcasts, you
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00:57:53.599 --> 00:57:56.530
are giving me the opportunity to do what I love
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00:57:56.730 --> 00:58:00.489
on a daily basis. And for that, I will forever
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00:58:00.909 --> 00:58:03.250
be grateful. Thank you so much.
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Talk to you soon. Can't wait.
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00:58:07.989 --> 00:58:13.619
I recently found an exciting new investment opportunity, Blue Chip Art. Now,
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00:58:13.699 --> 00:58:17.199
it's traditionally only open to billionaires because of the high
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00:58:17.380 --> 00:58:25.940
entry cost. But one startup is making it available for everyone. Masterworks.io
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00:58:26.039 --> 00:58:29.159
lets you invest in multi-million dollar works by artists like
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00:58:29.280 --> 00:58:34.739
Banksy and Monet. Contemporary art prices outperformed S & P
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00:58:34.739 --> 00:58:40.699
500 returns by 174% from 1995 to 2020. The total
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00:58:40.840 --> 00:58:45.789
art asset class is currently estimated at $ 1. 7 trillion and
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00:58:45.849 --> 00:58:49.110
is growing by another trillion over the next five years. Now,
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00:58:49.170 --> 00:58:51.929
demand is high, but I've worked with Masterworks to let
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00:58:51.949 --> 00:58:58.190
you skip their waitlist. by going to masterworks.io slash learning.
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That's masterworks.io slash learning. Also, please see important disclosures at masterworks.io
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slash disclaimer.