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I don't like the pro-con list thing because it's never
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a complete list. A lot of people are nervous about
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making decisions because they feel final. I'm after the statistics.
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I'm after the feeling.
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I tend not to set goals.
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I set directions. I don't think putting a target in
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front of you makes you do better work. What makes
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you do better work is being proud of the work itself.
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Earlier in your career, you caught the eye of Jeff Bezos.
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What's cool about Jeff, he wasn't looking for control. He
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was looking to support.
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I'd love to hear more about the importance of writing
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from a leadership perspective.
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I hated writing growing up. I hated it until I
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got to write. What's in my head? There's no way
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in hell I could ever run a company where I
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couldn't speak for myself. It's sort of been ingrained in
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us to think about writing. I'm just trying to think
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about communicating.
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Welcome to the Learning Leader Show presented by Insight Global.
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I am your host, Ryan Hawke. Thank you so much
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for being here. Text HAWK to 66866 to become part
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of Mindful Monday.
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You, along with tens.
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Of thousands of other learning leaders from all over the world,
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will receive a carefully curated email from me each Monday
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morning to help you start your week off right. You'll
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also receive details about how my book, The Score That Matters,
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will help you become a more effective leader. Text HAWK.
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To 66866.
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Now on to tonight's featured leader. Jason Freed is the
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co-founder and CEO at 37signals. 37signals is a privately held
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company committed to building the best web-based tools possible with
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the least number of features necessary. Jason is an amazing writer,
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one of my favorites. He's a co-author of Getting Real, Rework, remote,
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and it doesn't have to be crazy at work. During
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this conversation, we discussed Jason's framework for making hard decisions.
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He also told me why he doesn't set goals as
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well as why he doesn't think they're needed to accomplish
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what they want to do at his company. And it
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may make you rethink your goal setting framework. And then
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We talked about the importance of leaders having a writing practice.
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He shares how he's maintained an excellent relationship with his
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co-founder for the past 25 years. And I think the
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advice Jason shares applies really to all relationships. And then
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an amazingly cool story about Jeff Bezos sitting in the
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front row during one of Jason's keynotes in 2005 and
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how that led led to Jeff investing in 37 singles.
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So cool.
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Jason, as I said before, is one of my favorite writers.
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I love his books as well as the essays he
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publishes online. I highly encourage you read his work. Please
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enjoy my conversation with Jason Freed. Jason, hey man, it's
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awesome to have you back on The Learning Leader Show.
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Welcome.
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Good to be here, Ryan.
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I want to talk about decision-making.
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I've seen you write about this because I think decision-making
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can paralyze some people. And you've written that decisions aren't hard.
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It's the moments after that are. Whenever I make decisions,
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I don't think about now. I think about eventually. How
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will this feel then, maybe a year from now, when
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it's not real, not raw, when the complications around the
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concern have cleared and distance has done its job? As
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a leader of a company, as a founder, as somebody
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who's creating new products and You have to make decisions
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all the time. What is your overall philosophy on making
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the right decisions long-term?
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Yeah, I do.
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It's kind of, it is basically my job is to
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make calls or decisions, not calls. I don't, I'm not
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on the phone most of the time. First of all,
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it's not to try to make the
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right one because
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I don't know what the right one is. And I
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don't want to worry that I'm making the wrong one. Right.
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So yeah, The opposite of right is wrong in that sense.
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And then that's where people get nervous. Like, oh my God,
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what if I make the wrong decision? I'm basically trying
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to place a bet, essentially. And the bet is never
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going to be 100% right. It could be sometimes, I suppose.
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But really, it's about probability. It's like, how close to
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right can we get? Like, how does this feel? How
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do we feel about it? What are the things we're considering?
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How important is this really? Because, I mean, if it's
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not that important, let's not like deliberate forever on it.
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And let me not like beat myself up over it.
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And also, what's the likelihood that we could make a
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different decision about the same thing in two weeks if
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we need to? I'm trying to always reduce the criticality
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and seriousness of the decision so it's not as big
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of a deal. That way we don't get paralyzed and
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not wanting to make it. So those are the things.
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But really, I'm trying to feel... my way through what
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seems to be the best possible choice out of, out
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of the things that I, that I, that I can
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choose versus trying to be right.
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Is, is there a framework you use? Let's, let's, let's
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use a different example when it comes to decision-making. One
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of the ones is, okay, you know, I'm thinking about
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taking this job or leaving my company and going over there.
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Let's make a pros and cons list, right? You've heard
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this before.
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I'm curious.
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When let's say you're advising somebody and they come to
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you with a question like that, or maybe it's somebody
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who works for you, because I know you guys are
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so open with everything. I'm sure those types of conversations
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probably actually happen when they probably wouldn't in most companies.
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What's an overall framework somebody could use, you think, to
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help them make decisions? Yeah.
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So I don't like the pro-con list thing, because I
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think that here's why I don't like it personally. I'm
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sure it works for some people, but It's never a
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complete list. It's nowhere near a complete list. It's just
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the things you can come up with. But there's probably
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hundreds of other things that are at play that you
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may be aware of or may not be aware of.
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And so I'm not, it's not like balancing the list
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because you're just balancing the things you can come up with.
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What I would usually think or feel is like, what
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does it matter? That's honestly like, what does it matter
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which one you choose? And because oftentimes, like both are
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probably OK, like there's different outcomes probably or maybe the
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outcome might be the same. But but but both branches
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can lead you somewhere interesting. So I just try to
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get away from the right and wrong thing in terms
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of I mean, there are, of course, like a moral
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right and wrongs. Perhaps you might argue that's a philosophical conversation.
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But in most of these sort of business decisions, you're
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just making a call one way or the other. And
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unless it's highly, highly, highly critical, like something that we
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call internally concrete. If you're pouring concrete, you better make
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sure you're putting it in the right place and pouring
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it the right way because it's going to be very,
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very painful to bust up. So recognizing like, are we
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dealing with a concrete conversation here or a decision or
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mostly just like, are we moving dirt around? If we're
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moving dirt around, like you can move it around a
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bunch of different ways and the outcome might be fine
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either way. So I just, again, try to reduce the criticality.
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so people don't get too caught up in how serious
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this is when it isn't. That's basically my framework because
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I'm trying to get to the point where I can
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tell someone, I don't know, like, what do you think
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makes sense? And they're like, well, I think this makes sense.
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I go, that sounds pretty good. Why don't you try that?
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You know, it's more of a try than it is
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like a, I'm going down this branch no matter what. Now,
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to your point, like there are times in life where
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you're like, do I move to New York or do
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I go to LA? Or like, there's some big things,
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but still, even in those things, which are big things,
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you could say like, you could pick either one. You're
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just going to have a different, the life, your life
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might be different, but they both might be great outcomes.
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So pick the one you feel is right versus like
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New York would be wrong for you. How do you know?
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You know?
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So I guess I'm not... I know I'm not like
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in some ways giving people actionable advice in a sense,
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but the only thing that would be actionable about this
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is try to reduce the severity and criticality of these
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decisions so they're easier to make and you don't feel
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regret if you pick one and not the other.
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Well, speaking of a decision that you've made, I saw
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the dream home you built for yourself and your family
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in Chicago.
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Looked through the listing a few times. Amazing pictures. It's just...
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It's unique. It's different.
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It looks like almost a commercial building, but then it's beautiful.
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It's amazing, but you're, you're selling it, right? So, uh,
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and I know you decided to move. That's a huge decision, right?
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A guy with a family, you, you built a dream home.
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It's very expensive for most people and you decide to move.
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What went into that decision?
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It's so funny that you mentioned this because it is
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like the way you mentioned it, it is a pretty
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big decision, but strangely we didn't treat it that way.
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So this is like during COVID. So I don't, I
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built the house 10 years prior. Love the house. House
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is great. During COVID, we're like, we don't want to
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be locked in Chicago because it's really cold. Winter's going
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to be bad. We're all going to be stuck inside.
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And a few years before that, we bought this place
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we had to renovate in California. It was an old
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house built in the 50s, and it needed some renovation.
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So we were working on that kind of slowly on
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the side. And it turned out that it was sort
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of kind of ready to go, like right in the
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middle of COVID. I guess maybe it was 2020. July
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of 2020 or so, or August, something like that. And
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we're looking forward, like winter's coming in Chicago in a
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few months. Maybe we'll just go out to California for
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a bit and figure it out and see what happens.
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No one kind of knew what was happening at this time.
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You know, now you can look back on that. But
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back then it was like, who knows what's the future?
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Is this going to be a 10-year thing? Like no
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one knew anything. Like are people going to be dropping
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like flies everywhere? We don't know. So let's go to
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California and be outside at least, you know, and not
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feel cooped up inside. And so we did that. Now,
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We had a place, but we could have rented a place.
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There could have been other ways to deal with this, perhaps,
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but we had a place to go. And as we
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were just we're here, we just decided never to go
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back to Chicago. It wasn't like there was a moment
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where we decided to move. It was just this transition
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between like, we kind of like it here. Let's keep staying.
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And even now I'm like, do we live here? I mean,
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we're living here now. Does this mean we're going to
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be here forever? I don't need to make that choice.
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I mean, we have kids in school, but they're in school.
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That's fine. I can work remotely. My wife does what
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she does. She can do that remotely. And it's like,
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we'll just keep doing this. So strangely, in my mind,
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it didn't feel like a decision as much as it
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felt like, let's try something, which I guess is a decision,
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but it didn't feel final. I think maybe this is
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sort of what, as we dig into this, a lot
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of people are nervous about making decisions because they feel final.
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Yeah.
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And it could have been that like we stayed here
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for a year or six months and decided to go
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back to Chicago and that would have been fine too.
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We could have done that. Could have done all the
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different things. There were different outcomes that were possible. We
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just felt like this one made the most sense for
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us right now. And here we are, we're still here.
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So I know it's, yes, now I'm selling the house.
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So that means we're like, now at this point, we're like,
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we're leaving Chicago and we're making that decision if the
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house sells. If the house doesn't sell, I still have it.
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But now that a few years have passed, we can
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sort of stretch the decision out over a few years
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in this case, because we didn't know what we were
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going to do. And now we feel comfortable that we
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can make this decision versus like freaking out about leaving
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home and going somewhere else where it would feel so final.
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Like we are saying goodbye to Chicago like three years ago.
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We didn't say it that way. We're like, we're just
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going to go out here for a while and see
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what happens. Is that helpful?
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I don't know.
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It's, It's kind of amorphous, but it really is how
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I think about it.
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You know what it is, Jason, is the fact that
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most of the elements of life are very nuanced and gray.
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They're not black and white. And I think sometimes we
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try to bifurcate everything.
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It's either a pro or a con. It's a yes
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or a no.
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But in reality, with most things, including even a decision
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to move or whatever, it's not a.
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yes or a no, it's, it's just, we're going to
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go try this. We're just going to go do it.
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We want to be outside, you know, like we don't
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need to overcomplicate the thing. And it's almost like in
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alignment with how you run your business as well. Like
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we don't need to overcomplicate this thing. We're just going
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to go do it and then kind of figure it out.
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And that feels because let's transition to goal setting, because
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I feel like you guys, I loved reading about your
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process when it I'll pause and I want you to
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describe your overall philosophy both personally for yourself as well
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as now running a company when it comes to the
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idea of goal setting.
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Yeah, so I'm not a goal-driven person. I tend not
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to set goals. I set directions. So like I'll go
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in a direction. We'll take an idea in a direction.
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We have an idea for where we want to head
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with this thing. And I mean, the goal of course
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is implicit in a sense, like we want to ship
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this thing and make it great, but that's not like a,
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it's not like we need to do it and measure
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it based on revenue or number of customers we signed
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up in the first three weeks or any of these
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sort of numbers that really, frankly, most people are making up.
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And then you've got to hit these targets and you
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set these targets out for you that are so precise
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that you either hit them and you feel good, or
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maybe you should have had a more ambitious target, or
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now you just set another target. Like you just keep
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setting target after target after target after target versus like,
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how about just doing the best you can and seeing
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where things end up. That's kind of how I've always
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approached these things. And this whole thing kind of came
288
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to me through running actually. So I was trying to
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like run a six minute mile or something, whenever this was.
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And I remember like aiming for this time and then
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I'd run and I'd run on, what it was, 605
292
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or whatever, 606 or something. And it kind of dawned
293
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on me that like, I was actually upset. I was upset.
294
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Like why, why I didn't get my, I didn't hit
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my goal. Now you could say, well, that's more motivation
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to hit it next time. But like, okay, so let's
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say I hit it, but then what? So what I
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realized was that hitting the goal is for me, the
299
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wrong thing to aim for. The real questions I should
300
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be asking at that point is not, did I run
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a six-minute mile? It's like, did I enjoy the run?
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How do I feel? Did I get some fresh air?
303
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Is my heart pumping? Is my heart rate up? Did
304
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I get some good exercise today? It's all of that.
305
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And that is true at 6.04, and it's true at 6,
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and it's true at 5.57, and whatever. Those are the
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kind of questions, and those are not goal-based things. Those are, again,
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result-feeling-based directional things that are amorphous to some degree, but
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also very specific. I can answer those questions. Yeah, I
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feel pretty good. I'm glad I did this today. Like,
311
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I feel like I got a good workout in. Yeah.
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How do I measure if I got a good workout in?
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I mean, some people would measure with their Fitbit or
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their Garmin or their Apple Watch. Like, I just like, yeah,
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I feel like I worked out pretty well today. That's
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good enough for me. So I don't wear the things
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that give me the statistics because I'm not after the statistics.
318
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I'm after the feeling. Again, same as business, same as decisions.
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I'm after a feeling. And I know when something feels
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right or when something doesn't feel right. I think we
321
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all actually do. But for some
reason, when things are
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easy to measure or easy to set a target on,
323
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we tend to want to do that and aim for
324
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this degree of precision that I think is unnecessary and
325
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perhaps not even helpful.
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So the real question we should be asking ourselves, I think,
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it feels like from what you're saying is, what are
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you optimizing for?
329
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Yeah.
330
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Right? When you think about running, the question is, what
331
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are you optimizing for? And you can answer that question.
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And that becomes the goal, so to speak, right? Of
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heart rate or how you feel or getting exercise as
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opposed to a six minute mile. Yeah.
335
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And so you could say that the goal is to
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have a good workout, right? I wouldn't call that a
337
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goal though. Like to me, a goal, typically most people
338
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think of it as like a six minute mile. Like
339
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I'm aiming for something a singularity. I'm aiming for this point.
340
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I need to get to this point and hit it exactly.
341
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That's a goal. That's how most people, I think, think
342
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of goals. I think like, did I have a good workout? Now,
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I can still push myself harder if I want to.
344
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I'll go, yeah, I had a good workout, but I
345
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think I got some left. And if I push myself
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and I ended up, if I did time it and
347
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I was under six, that'd be great too. But it
348
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wouldn't feel any better to me. It would just feel like,
349
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Because the time and the precision isn't the feeling. It's
350
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like the action, the act of the thing, doing the
351
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work or the workout in this case is the result.
352
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It's not the time or the number. Now, if I'm
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training professionally for, which I'm not, but like for like
354
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a marathon or a race, And there's targets you got
355
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to hit that other people set or you set for yourself.
356
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I can totally see how that would be very, very,
357
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very useful. So if someone's like, I'm running a triathlon,
358
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I want to finish in the top quartile. I got
359
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to get past this number. I'm going to train a
360
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certain way to get past this number. Totally understand that.
361
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I don't do that. So for me, I don't want
362
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to act as if I do that. I'd rather just
363
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do the workout and push harder if I feel like
364
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I have some left.
365
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What type of impact or effect, I guess I should say,
366
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do you think it would have on your company if
367
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all of a sudden, January 2nd, you have a town
368
00:17:31.230 --> 00:17:34.309
hall or whatever, you gather everybody together and you say, okay.
369
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Here's what I want us to accomplish by the end
370
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of the year.
371
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And you have a revenue number and you have a
372
00:17:39.589 --> 00:17:42.359
profit number and you have some other things about how
373
00:17:42.390 --> 00:17:44.880
you're doing in the market against competitors, whatever, the stuff
374
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that most CEOs do. What type of impact or effect
375
00:17:48.700 --> 00:17:50.359
would that have on your company if you did that?
376
00:17:51.279 --> 00:17:51.579
I don't know.
377
00:17:51.660 --> 00:17:55.059
I mean, it could work. We could perform better. Why
378
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don't you choose to do that? I wouldn't enjoy it, frankly. Like, honestly,
379
00:18:00.079 --> 00:18:03.829
I wouldn't enjoy working for that.
380
00:18:04.410 --> 00:18:04.589
Yeah.
381
00:18:04.910 --> 00:18:09.549
Like, I just, it doesn't matter in a sense to me. Like,
382
00:18:09.690 --> 00:18:11.809
what I want to get to and where I think
383
00:18:11.849 --> 00:18:14.250
we are and where I hope we stay is that
384
00:18:14.289 --> 00:18:15.859
we just want to do the best work we can.
385
00:18:16.500 --> 00:18:17.519
Yeah.
386
00:18:17.920 --> 00:18:21.529
And I don't think putting a target in front of
387
00:18:21.589 --> 00:18:25.039
you makes you do better work. I think what makes
388
00:18:25.059 --> 00:18:28.920
you do better work is the inherent motivation of caring
389
00:18:28.940 --> 00:18:31.259
about your craft, caring about the people you're working with,
390
00:18:31.339 --> 00:18:33.920
understanding what you're making, being proud of the work itself.
391
00:18:34.460 --> 00:18:36.680
And you're going to take that as far as you can.
392
00:18:36.700 --> 00:18:40.029
And we're going to end up in a place and
393
00:18:40.069 --> 00:18:42.029
the market is going to tell the truth. Like, did
394
00:18:42.069 --> 00:18:43.150
we do good enough?
395
00:18:44.630 --> 00:18:45.000
Yes or no.
396
00:18:46.200 --> 00:18:50.079
Again, it's not to beat the competition because the competition
397
00:18:50.099 --> 00:18:51.940
can have their business and we can have our business.
398
00:18:51.980 --> 00:18:53.859
I don't need to beat anybody. I'm not out for
399
00:18:53.900 --> 00:18:58.259
domination or taking market share. There's enough for us. There's
400
00:18:58.279 --> 00:19:01.279
enough for them. Of course, there are zero-sum game businesses.
401
00:19:01.559 --> 00:19:03.589
We're not in one of those. There's lots and lots
402
00:19:03.609 --> 00:19:06.430
of tools in our world that people use that are
403
00:19:06.470 --> 00:19:08.730
not ours. We can build a great business. They can
404
00:19:08.750 --> 00:19:11.930
build a great business. It's very insular in a sense.
405
00:19:11.990 --> 00:19:15.319
What do we need to do to function well, to
406
00:19:15.359 --> 00:19:18.940
sustain our business, to be profitable. That is the one
407
00:19:19.000 --> 00:19:20.700
goal I would say that we have, but there's not
408
00:19:20.740 --> 00:19:23.029
a number attached to it. It's not like we need
409
00:19:23.049 --> 00:19:26.269
to be this profitable or have this exact margin, but
410
00:19:26.289 --> 00:19:28.309
we want to be profitable and have healthy margins.
411
00:19:28.509 --> 00:19:29.609
Again, range.
412
00:19:29.809 --> 00:19:33.049
It's about a range. And we've been doing that for
413
00:19:33.049 --> 00:19:36.460
25 years straight, every year for 25 years, doing it
414
00:19:36.519 --> 00:19:42.190
without targets, without specifics to aim for, but instead kind
415
00:19:42.210 --> 00:19:44.109
of going inside and going, let's just do the best
416
00:19:44.150 --> 00:19:48.089
work we can together. Now, there are moments where I'm like,
417
00:19:48.109 --> 00:19:49.990
we need to ship this. So we're going to ship
418
00:19:50.029 --> 00:19:53.150
this by January 1st. And so is that a goal?
419
00:19:53.170 --> 00:19:55.450
It's more of a deadline, really. We are going to
420
00:19:55.490 --> 00:19:57.200
do this. And we're going to take some things out
421
00:19:57.240 --> 00:19:58.420
if we can't get it done because we need to
422
00:19:58.440 --> 00:20:01.460
get this thing out the door. So it's not like this...
423
00:20:02.000 --> 00:20:03.819
as long as it takes kind of mentality. It's certainly
424
00:20:03.880 --> 00:20:06.759
not that there's more discipline here, but fundamentally it is
425
00:20:06.799 --> 00:20:09.599
about doing good work that we're proud of and letting
426
00:20:09.619 --> 00:20:10.460
the chips fall where they may.
427
00:20:11.400 --> 00:20:13.319
At one point earlier in your career, you caught the
428
00:20:13.460 --> 00:20:16.940
eye of Jeff Bezos and I believe he came to
429
00:20:16.960 --> 00:20:19.380
you and said he wanted to invest. Can you take
430
00:20:19.400 --> 00:20:22.039
me back to that moment? What caught his eye and
431
00:20:22.079 --> 00:20:24.259
what was it like working with him when he decided
432
00:20:24.299 --> 00:20:25.319
to invest in your
company?
433
00:20:26.400 --> 00:20:30.220
Yeah. So historically we had, um, uh, been approached by
434
00:20:30.240 --> 00:20:33.000
a lot of different investors and it was never interesting
435
00:20:33.039 --> 00:20:35.259
to us and still isn't today. To this day, we
436
00:20:35.279 --> 00:20:38.160
still get approached all the time. I was speaking in
437
00:20:38.220 --> 00:20:42.119
San Diego at this conference called E-Tech in 2005 and
438
00:20:42.289 --> 00:20:44.970
Jeff was speaking there also. And what was cool about Jeff,
439
00:20:44.990 --> 00:20:46.150
I don't know if he still does this, but when
440
00:20:46.170 --> 00:20:47.890
he goes to a conference, he actually attends the conference,
441
00:20:48.289 --> 00:20:50.269
which is cool. A lot of people kind of come
442
00:20:50.309 --> 00:20:52.809
in and leave, especially like someone like him, you think
443
00:20:52.849 --> 00:20:54.190
he's in and out, but he was sitting in the
444
00:20:54.210 --> 00:20:56.809
front row, listening to all the speakers. And I think
445
00:20:56.829 --> 00:20:58.690
he liked what I had to say. And I think
446
00:20:58.730 --> 00:21:01.509
a few of his companies that he'd invested in were
447
00:21:01.569 --> 00:21:03.589
using Basecamp at the time. Basecamp was only a year
448
00:21:03.650 --> 00:21:06.230
old at the time, basically, when I was giving this talk.
449
00:21:06.809 --> 00:21:09.670
And I think he just kind of liked our irreverent
450
00:21:09.730 --> 00:21:11.490
point of view, which is kind of sort of how
451
00:21:11.539 --> 00:21:14.420
he is in general. And so he has people reach
452
00:21:14.480 --> 00:21:16.420
out to us, say, you know, Jeff wants to catch
453
00:21:16.519 --> 00:21:18.640
up and kind of had an inkling this was about
454
00:21:18.660 --> 00:21:20.660
investment of some sort. Otherwise, like, why would you want
455
00:21:20.680 --> 00:21:23.440
to do that? And I was hesitant, but it's like,
456
00:21:23.460 --> 00:21:27.029
it was Jeff Bezos, it was 2005. I mean, yeah, sure.
457
00:21:27.769 --> 00:21:30.150
Let's get together. I'd love to. Oh my God, I'd
458
00:21:30.170 --> 00:21:32.599
be honored to do that. So flew out to Seattle.
459
00:21:33.380 --> 00:21:35.539
We had a conversation and really going into it, I'm like,
460
00:21:35.880 --> 00:21:37.440
in my head, I'm like, we're not taking anyone's money.
461
00:21:38.920 --> 00:21:42.240
Not even his money. Not even his money. I didn't
462
00:21:42.319 --> 00:21:44.799
want the money. I don't need the money. And I
463
00:21:44.940 --> 00:21:47.740
don't want what the money costs. Right.
464
00:21:47.849 --> 00:21:49.450
Having to answer to somebody else, right?
465
00:21:49.529 --> 00:21:52.150
Yeah. There you go. So people think like you get money. Well,
466
00:21:52.170 --> 00:21:54.269
guess what? You pay for that. You pay for that
467
00:21:54.329 --> 00:21:57.690
money in other ways. You lose your independence. You're on
468
00:21:57.730 --> 00:22:00.309
someone else's schedule in a sense to sell the company
469
00:22:00.769 --> 00:22:03.900
or go IPO or whatever. Like, Funds need their money back.
470
00:22:03.940 --> 00:22:06.240
Investors need their money back, understandably so. So I went
471
00:22:06.279 --> 00:22:08.059
in not wanting to do this, but we just had
472
00:22:08.099 --> 00:22:10.759
some really good conversations. And what became clear was like,
473
00:22:10.779 --> 00:22:13.859
he was just interested in supporting a handful of entrepreneurs
474
00:22:14.160 --> 00:22:17.809
that he thought were doing interesting things. He was not
475
00:22:17.829 --> 00:22:20.849
looking for an exit. We don't have a board. He
476
00:22:21.029 --> 00:22:22.910
didn't want a seat. We don't even have one, right?
477
00:22:23.029 --> 00:22:25.190
And he didn't want to create one. So he wasn't
478
00:22:25.210 --> 00:22:29.069
looking for control. He was looking to support some people.
479
00:22:29.130 --> 00:22:33.099
And part of the support was liquidity. So- Jeff didn't
480
00:22:33.180 --> 00:22:35.480
really invest in our business. What he did was he
481
00:22:35.579 --> 00:22:39.119
bought secondaries. He bought some shares from me and from David.
482
00:22:39.660 --> 00:22:42.130
And we put that money in our own personal bank accounts.
483
00:22:42.190 --> 00:22:44.509
So we took some risk off the table early on.
484
00:22:45.109 --> 00:22:47.150
But none of his money ever went into our business.
485
00:22:47.210 --> 00:22:50.470
Our business is 100% always has been funded by customer revenues.
486
00:22:51.509 --> 00:22:53.660
So it was kind of this ideal situation where he
487
00:22:53.680 --> 00:22:55.440
didn't have a board seat, didn't really have any controls,
488
00:22:55.480 --> 00:22:57.809
a very straightforward, simple thing. We got to take a
489
00:22:57.809 --> 00:22:59.710
little bit of money off the table early on when
490
00:22:59.730 --> 00:23:01.450
we're like, this thing could be a fluke. This base
491
00:23:01.470 --> 00:23:04.190
camp thing has taken off sort of, but like, I mean,
492
00:23:04.210 --> 00:23:06.109
I don't know what's going to happen. Like we could
493
00:23:06.130 --> 00:23:08.589
get crushed in a year. I'd like to have something
494
00:23:08.609 --> 00:23:11.930
to show for the effort we made. And it all
495
00:23:11.970 --> 00:23:15.650
just kind of like magically came together in a way
496
00:23:15.710 --> 00:23:18.809
where he was sort of the ideal partner. And what's
497
00:23:18.849 --> 00:23:21.930
interesting is, so he still owns a piece, the same piece,
498
00:23:22.619 --> 00:23:26.619
although he had to split it up with his ex-wife, like,
499
00:23:27.250 --> 00:23:30.150
There's just that, those are the rules. So, but anyway,
500
00:23:30.170 --> 00:23:35.069
still owns a slice and she does. And we're an LLC.
501
00:23:35.250 --> 00:23:38.630
So we make distributions every year to member unit holders.
502
00:23:39.190 -->
00:23:41.529
He is one, she's one. So he gets paid every
503
00:23:41.569 --> 00:23:43.710
year on this investment without having to exit the company.
504
00:23:44.029 --> 00:23:46.869
So he's made his money many, many, many, many times over,
505
00:23:46.950 --> 00:23:49.910
still has all of his equity. And it turned out
506
00:23:49.930 --> 00:23:52.390
to be a pretty good deal for him. So that's great.
507
00:23:52.410 --> 00:23:57.190
But he's, to your other point, he is... The most
508
00:23:57.230 --> 00:23:59.319
positive person I've ever met in my life, like by
509
00:23:59.359 --> 00:24:02.839
a long shot. And that really made an impression on me.
510
00:24:03.740 --> 00:24:07.660
I've never been around someone so optimistic, ever. And I've
511
00:24:07.680 --> 00:24:09.880
been around a number of optimistic people. He just has
512
00:24:09.980 --> 00:24:14.880
a can-do optimistic spirit about him that it's always sort
513
00:24:14.900 --> 00:24:19.369
of anchored in like humor and like the silliest ideas
514
00:24:19.410 --> 00:24:22.170
are the most interesting. And I just loved that about him.
515
00:24:22.230 --> 00:24:23.829
We really got along in that way. So we went
516
00:24:23.849 --> 00:24:24.069
for it.
517
00:24:24.569 --> 00:24:27.789
Most positive person ever. How did that come out in
518
00:24:27.809 --> 00:24:30.930
the meetings and your conversation? How did you sense this overwhelm?
519
00:24:30.950 --> 00:24:32.460
I mean, what a great trait, by the way. But
520
00:24:32.519 --> 00:24:35.920
how did you sense it in him through your conversations?
521
00:24:36.460 --> 00:24:38.920
Yeah. And I wish I had that because I'm not...
522
00:24:39.220 --> 00:24:42.720
Maybe inwardly, I feel optimistic and confident about things, but
523
00:24:42.960 --> 00:24:45.880
I don't have that cheerleader spirit that he has, in
524
00:24:46.000 --> 00:24:49.019
a sense. First of all, if you've ever seen any
525
00:24:49.039 --> 00:24:51.019
interviews with him or met him, I don't know, but
526
00:24:51.599 --> 00:24:58.400
massive laugh. Like just... deep, fun, fun laugh. His laugh
527
00:24:58.460 --> 00:25:01.099
is fun and it's never faked. You can tell it's
528
00:25:01.240 --> 00:25:03.500
super genuine when he does it because it's so deep.
529
00:25:04.700 --> 00:25:07.490
You could imagine a fake version of it, but when
530
00:25:07.509 --> 00:25:10.069
you hear the real version of that, that's real. That's
531
00:25:10.230 --> 00:25:14.009
all in. And every time we asked him a question
532
00:25:14.049 --> 00:25:17.049
about like, what would you do or whatever? He's always like,
533
00:25:17.069 --> 00:25:18.650
what would you do? Well, what would you do? And
534
00:25:18.670 --> 00:25:20.269
we'd sort of get in this conversation. He's like, I
535
00:25:20.269 --> 00:25:22.299
love that. You should do that. Because if you guys
536
00:25:22.319 --> 00:25:25.859
think that that's good, you should do that. Like he's very, now,
537
00:25:25.880 --> 00:25:27.200
I don't know what it's like to work for him
538
00:25:27.259 --> 00:25:29.920
in his own company. So I can't comment on that.
539
00:25:30.019 --> 00:25:31.920
I heard he can be quite tough as you'd expect.
540
00:25:32.480 --> 00:25:35.220
But with us, he's always been very supportive and positive
541
00:25:35.329 --> 00:25:42.529
and like encouraging and an extraordinarily good listener. Um, and this, again,
542
00:25:42.569 --> 00:25:44.140
one of these people who are, when you're talking to me,
543
00:25:44.150 --> 00:25:45.619
I feel like you only, you're the only person in
544
00:25:45.640 --> 00:25:48.880
the room and he just has that quality, but it's,
545
00:25:49.279 --> 00:25:51.480
it's always like, it feels to me always rooted in
546
00:25:51.880 --> 00:25:59.329
genuine curiosity and excitement for novelty and, uh, cleverness and,
547
00:25:59.569 --> 00:26:03.210
and fun ideas. And, um, We were kind of spinning
548
00:26:03.250 --> 00:26:05.670
those kinds of things out early on, and we still
549
00:26:06.150 --> 00:26:08.509
do that. But back then, especially, we were kind of
550
00:26:08.569 --> 00:26:11.990
new on the scene. We were very irreverent, doing things
551
00:26:12.069 --> 00:26:14.329
totally different than everybody else. And I think he just
552
00:26:14.349 --> 00:26:18.250
kind of came into that and loved that. And we
553
00:26:18.309 --> 00:26:19.609
felt that vibe from him.
554
00:26:20.789 --> 00:26:22.529
It's also got to feel good, I would imagine, to
555
00:26:22.609 --> 00:26:25.039
prove that. early supporters. Right.
556
00:26:25.119 --> 00:26:25.299
Yeah.
557
00:26:25.319 --> 00:26:26.480
That was early in the game.
558
00:26:26.799 --> 00:26:29.619
Yes. You give a speech, he supports you. And what
559
00:26:29.640 --> 00:26:32.960
a great feeling, especially now what he's become too, but
560
00:26:33.099 --> 00:26:35.140
proving early supporters.
561
00:26:35.220 --> 00:26:35.440
Right.
562
00:26:35.619 --> 00:26:38.420
I think is, is just a really amazing.
563
00:26:38.460 --> 00:26:40.099
Cause like now he's made all of this, not that
564
00:26:40.119 --> 00:26:41.740
he needs the money, but he's made it all back
565
00:26:41.799 --> 00:26:45.599
in a lot more. And you prove that person, right.
566
00:26:45.640 --> 00:26:47.900
As opposed to, I think that's more fulfilling than proving
567
00:26:47.960 --> 00:26:51.509
haters wrong or proving doubters wrong is proving supporters.
568
00:26:51.690 --> 00:26:51.950
Right.
569
00:26:51.970 --> 00:26:54.559
You know, That's a good way of thinking about it.
570
00:26:54.599 --> 00:26:58.380
I mean, I've always been fueled by people who don't
571
00:26:58.400 --> 00:27:00.460
think I can do something for a reason like that.
572
00:27:00.500 --> 00:27:00.640
Yeah.
573
00:27:00.680 --> 00:27:02.380
That has always kind of been a bit of a
574
00:27:02.980 --> 00:27:05.980
chip my shoulder kind of feeling around that. It started
575
00:27:06.009 --> 00:27:07.980
out when I was a web designer way back when
576
00:27:08.029 --> 00:27:11.769
I first started my career, I'd submitted some, some work
577
00:27:11.809 --> 00:27:15.049
to this award thing that was like kind of the preeminent,
578
00:27:15.089 --> 00:27:17.990
like web design award guy at the time, David Siegel
579
00:27:18.009 --> 00:27:20.710
was his name. I forget what, what the award was
580
00:27:20.769 --> 00:27:24.160
called at the time, but Anyway, I submitted some work
581
00:27:24.200 --> 00:27:26.740
to him and he wrote me back. He's like, you suck.
582
00:27:27.259 --> 00:27:29.819
He's like, you should get a new job. Like, this
583
00:27:29.880 --> 00:27:32.059
is not your career. He's like kind of a real,
584
00:27:32.140 --> 00:27:36.000
you know, chippy guy. And I loved it. I honestly
585
00:27:36.039 --> 00:27:39.390
just loved it. Like, I'm like, okay, all right, let's go.
586
00:27:39.410 --> 00:27:41.990
And I think this comes from like, I'm five foot seven,
587
00:27:42.029 --> 00:27:45.210
so I'm not a tall person. And I've always been
588
00:27:45.230 --> 00:27:47.210
good at basketball and I can jump. And I used
589
00:27:47.230 --> 00:27:48.759
to be able to like touch the rim and I
590
00:27:48.779 --> 00:27:50.039
can't do it anymore, but I used to be able to.
591
00:27:50.259 --> 00:27:52.140
And so like, I love this sort of notion, like
592
00:27:52.420 --> 00:27:54.140
someone looking at me thinking I can't do something and
593
00:27:54.160 --> 00:27:58.440
then doing it always has fueled me. But so haters,
594
00:27:58.480 --> 00:27:59.990
like I kind of don't.
595
00:28:03.009 --> 00:28:03.509
A hater.
596
00:28:04.539 --> 00:28:07.279
It's kind of fueling when a bunch of people gather
597
00:28:07.400 --> 00:28:09.779
or pile on, like, I don't really pay attention to that.
598
00:28:10.200 --> 00:28:10.480
Yeah.
599
00:28:10.559 --> 00:28:12.859
But I do agree with you though, that it's nice
600
00:28:12.900 --> 00:28:15.549
to people who are really by your side in the
601
00:28:15.650 --> 00:28:19.250
early days who believed in you, who saw something others didn't.
602
00:28:19.509 --> 00:28:23.730
It is very rewarding to, um, to your point, prove
603
00:28:23.750 --> 00:28:27.039
them right. Or, or more so like, Find a deep
604
00:28:27.079 --> 00:28:30.960
satisfaction in making them feel good about their decision. So
605
00:28:30.980 --> 00:28:32.609
I'm with you on both sides here.
606
00:28:32.630 --> 00:28:34.150
I agree.
607
00:28:34.309 --> 00:28:38.609
And as you know, there are so many great, great
608
00:28:38.730 --> 00:28:42.690
examples of the Michael Jordans of the world and very
609
00:28:42.769 --> 00:28:47.819
Tom Brady's where. they, Aaron Rodgers have this permanent chip
610
00:28:47.900 --> 00:28:50.839
on their shoulder. And if there isn't a person there
611
00:28:50.900 --> 00:28:52.740
to put it there, they'll create it.
612
00:28:52.759 --> 00:28:55.400
They'll make it up. And so I do think, I mean,
613
00:28:55.440 --> 00:28:57.869
we're humans, like we're human beings. We're not perfect. Like
614
00:28:58.329 --> 00:29:00.269
I think there is something real.
615
00:29:00.289 --> 00:29:02.329
Like I still think about people when I was in college,
616
00:29:02.369 --> 00:29:05.069
I played a quarterback and I got beat out for
617
00:29:05.089 --> 00:29:07.329
a starting quarterback job by a guy who ended up
618
00:29:07.349 --> 00:29:07.990
being really good.
619
00:29:08.049 --> 00:29:09.970
Played for the Steelers named Ben Roethlisberger.
620
00:29:10.029 --> 00:29:12.730
And I remember people from my hometown when I transferred,
621
00:29:12.750 --> 00:29:14.819
because after I got beat out for that job, saying
622
00:29:15.220 --> 00:29:16.900
yeah he's a really good high school player just not
623
00:29:16.980 --> 00:29:19.019
not good enough to start in division one college football
624
00:29:19.380 --> 00:29:21.460
i still remember the actual names of some of those
625
00:29:21.500 --> 00:29:23.799
people that said that to me when i transferred and
626
00:29:23.819 --> 00:29:25.440
yeah i thought about it when i was not only
627
00:29:25.460 --> 00:29:27.220
the starter but team captain and had a chance to
628
00:29:27.269 --> 00:29:28.930
play after college like i thought of some of those
629
00:29:28.950 --> 00:29:30.450
people i want to prove my.
630
00:29:30.390 --> 00:29:32.470
Parents right right my supporters.
631
00:29:32.089 --> 00:29:35.130
Who love me but yeah dude like there's a little
632
00:29:35.150 --> 00:29:37.170
bit i'm thinking of those that saying like yeah good
633
00:29:37.210 --> 00:29:38.730
high school not good at playing college.
634
00:29:38.769 --> 00:29:41.059
I was like, well, what's up now? You know, like
635
00:29:41.099 --> 00:29:43.160
there is a little bit of that that happens, you know?
636
00:29:43.819 --> 00:29:46.079
I think it's healthy on both sides. And I've always been,
637
00:29:46.099 --> 00:29:47.920
you know, I grew up in Chicago. So Jordan was
638
00:29:47.960 --> 00:29:49.859
like kind of, you know, my idol kind of guy.
639
00:29:49.940 --> 00:29:52.480
And he is like all the way at the end
640
00:29:52.539 --> 00:29:54.880
of insane when it comes to chips on your shoulder.
641
00:29:54.900 --> 00:29:57.500
I mean, which is amazing for someone who's so accomplished,
642
00:29:57.539 --> 00:30:01.769
of course, to remember that Every single slight ever that
643
00:30:02.009 --> 00:30:06.970
anyone ever slighted him, talked shit, whatever it was, anything,
644
00:30:07.150 --> 00:30:10.009
like a little shove, a little, what, like, and you,
645
00:30:10.130 --> 00:30:12.009
you know, if you, if you've paid attention to him,
646
00:30:12.109 --> 00:30:14.119
he'll always talk about the, I remember that one thing.
647
00:30:14.130 --> 00:30:15.480
And that one guy said this thing to me and
648
00:30:15.500 --> 00:30:18.880
I dropped 60 on
him. Like, that's how I've always felt.
649
00:30:18.980 --> 00:30:21.680
I couldn't drop 60 on someone like in that way.
650
00:30:21.960 --> 00:30:24.410
But I do, I do look for those things. Uh,
651
00:30:24.519 --> 00:30:27.039
and they do give me some momentum and some, some
652
00:30:27.279 --> 00:30:29.710
sort of purpose in a sense that Kind of, not
653
00:30:29.750 --> 00:30:34.539
really purpose, but enjoyment, frankly. And we've done, you know,
654
00:30:34.839 --> 00:30:37.259
I think this manifests itself in our business in that
655
00:30:37.500 --> 00:30:39.500
we've been very early on a lot of things. So
656
00:30:39.539 --> 00:30:41.420
we were very early on remote work. We were very
657
00:30:41.539 --> 00:30:44.339
early on four-day work weeks. We were very early on
658
00:30:45.079 --> 00:30:47.420
small teams. We were very early on bootstrapping, although, of course,
659
00:30:47.440 --> 00:30:49.759
many companies have bootstrapped over the years. But in our industry,
660
00:30:49.799 --> 00:30:52.970
like pitching, bootstrapping, and talking about it seriously, we were
661
00:30:52.990 --> 00:30:56.039
very early on SaaS. Now we're very early on this
662
00:30:56.079 --> 00:30:58.859
thing called ONCE, which we're doing, which is one-time payment software,
663
00:30:58.900 --> 00:31:01.720
not subscription-based anymore. And people are like, but that's stupid.
664
00:31:01.759 --> 00:31:04.579
And I go, yeah, it is stupid. It is stupid.
665
00:31:05.339 --> 00:31:06.819
Right now it is, but let's see where it is
666
00:31:06.880 --> 00:31:08.460
in five years or whatever. And we're going to put
667
00:31:08.480 --> 00:31:12.309
some products out and see what happens. So I do
668
00:31:12.349 --> 00:31:15.549
like that. But yeah, I mean... I also think about
669
00:31:15.670 --> 00:31:18.029
like my parents being at every track meet I ran track.
670
00:31:18.049 --> 00:31:20.609
So every track meet I was ever at and my
671
00:31:20.650 --> 00:31:22.650
dad yelling at me in a positive way about get
672
00:31:22.670 --> 00:31:24.450
your knees up and all the things he would teach
673
00:31:24.490 --> 00:31:27.390
me about running speed, you know, I was a sprinter and,
674
00:31:27.569 --> 00:31:30.369
and finally being really damn good at that. And like
675
00:31:30.390 --> 00:31:33.299
being really happy to, to, I know how happy he
676
00:31:33.359 --> 00:31:37.119
was that I got really good. And so you can
677
00:31:37.140 --> 00:31:38.980
play both sides of it. I think it's, look, you
678
00:31:39.000 --> 00:31:43.309
gotta look for motivation. anywhere you can sometimes, you know?
679
00:31:43.339 --> 00:31:43.970
Yeah, no, no, 100%.
680
00:31:43.970 --> 00:31:48.059
Being early, I think, feels to me like a skill,
681
00:31:49.319 --> 00:31:53.380
something you've developed. How does one, this is a tough one,
682
00:31:53.539 --> 00:31:56.339
how does one develop the skill of being early?
683
00:31:57.359 --> 00:32:04.700
Well, I think part of it is not second-guessing yourself
684
00:32:04.759 --> 00:32:06.529
when you have an idea that you want to pursue.
685
00:32:06.549 --> 00:32:10.309
I think it's, I'm not suggesting we're the first ones
686
00:32:10.349 --> 00:32:11.849
to think of any of the things that we were,
687
00:32:11.869 --> 00:32:14.009
let's say early on, and we weren't the only ones,
688
00:32:14.150 --> 00:32:16.410
but there was, you know, a collection of companies that
689
00:32:16.430 --> 00:32:18.849
were early. And I think those are the ones that
690
00:32:18.890 --> 00:32:21.630
just do the thing and not like worry about what
691
00:32:21.650 --> 00:32:23.930
everyone else thinks they're going to do or be or
692
00:32:24.009 --> 00:32:26.029
how it's going to work out. But they're like, we
693
00:32:26.049 --> 00:32:27.930
believe in this, we're going to go for it. So
694
00:32:27.950 --> 00:32:29.750
I think a lot of it is just like allowing
695
00:32:29.769 --> 00:32:33.660
yourself to do the thing. Um, and sometimes you're really
696
00:32:33.720 --> 00:32:36.140
early and it doesn't work. I mean, for example, we
697
00:32:36.180 --> 00:32:39.160
made this, this product, this group chat tool back in
698
00:32:39.160 --> 00:32:44.009
2007 called, or six called campfire, um, which we've since
699
00:32:44.049 --> 00:32:47.430
re-released as this under this once umbrella. But back in 2006,
700
00:32:47.430 --> 00:32:51.289
I couldn't shove the idea of group chat down people's throats.
701
00:32:51.390 --> 00:32:54.210
Nobody understood it. Um, they're like, why would we chat
702
00:32:54.309 --> 00:32:56.430
like at a company? Like what? I don't, I don't,
703
00:32:56.470 --> 00:32:57.970
we can just talk to each other. Like, why would,
704
00:32:58.309 --> 00:33:00.680
so no one understood this at all. We couldn't sell it.
705
00:33:00.750 --> 00:33:07.019
It was like, Our least worst selling product we've ever made, essentially.
706
00:33:07.700 --> 00:33:10.839
And then along comes Slack, I don't know, it was
707
00:33:10.880 --> 00:33:13.529
eight years later or whatever it was. And we'd sort
708
00:33:13.549 --> 00:33:15.299
of given up on it because we just couldn't move it.
709
00:33:15.730 --> 00:33:20.109
And they just crushed it, right? Now, essentially, the products
710
00:33:20.130 --> 00:33:22.869
were the same. They did a few things really, really
711
00:33:22.930 --> 00:33:25.250
well that really, really mattered. They deserve all the credit
712
00:33:25.269 --> 00:33:28.980
in the world. But that idea, literally, if Slack had
713
00:33:29.039 --> 00:33:31.900
launched Campfire in 2006, it would have died on the
714
00:33:31.940 --> 00:33:34.519
vine too, essentially. It just was too early. So you
715
00:33:34.559 --> 00:33:37.420
can be wrong. Sometimes it takes a while for something
716
00:33:37.460 --> 00:33:39.950
to make sense. And sometimes it never makes sense. But
717
00:33:39.970 --> 00:33:43.150
I do think it's
not being afraid to just try
718
00:33:43.230 --> 00:33:46.390
something because I think most people talk themselves out of
719
00:33:46.450 --> 00:33:49.430
the early ideas they do have. Like it's not, we're
720
00:33:49.450 --> 00:33:50.950
not ready for prime time or no one's going to
721
00:33:50.970 --> 00:33:52.369
buy it or it's not going to work. And so
722
00:33:52.390 --> 00:33:55.289
they just don't. So I think we just do. That's
723
00:33:55.630 --> 00:33:57.769
kind of maybe how you are early with things.
724
00:33:57.789 --> 00:34:00.309
One of the other unique parts about your story, I
725
00:34:00.329 --> 00:34:04.559
feel like, Jason, is your relationship with David. You mentioned
726
00:34:04.579 --> 00:34:07.500
David earlier. To some, he's known as DHH. I've had
727
00:34:07.539 --> 00:34:11.139
him on the show. Super interesting dude. What's been the
728
00:34:11.300 --> 00:34:15.400
key to you guys having a good partnership?
729
00:34:15.699 --> 00:34:20.369
So a few things, probably. Luck, number one. The fact
730
00:34:20.389 --> 00:34:22.130
that we even met. He was in Denmark. I was
731
00:34:22.190 --> 00:34:24.699
in Chicago. We met on the internet. because I had
732
00:34:24.739 --> 00:34:26.619
a programming issue I didn't know how to solve. He
733
00:34:26.820 --> 00:34:29.139
wasn't a programmer, but I was trying to learn PHP,
734
00:34:29.179 --> 00:34:31.550
and he happened to read our blog somehow and happened
735
00:34:31.570 --> 00:34:35.170
to see my question, and that's how it all happened.
736
00:34:35.849 --> 00:34:40.690
So that was super unusual. Shouldn't have happened, but it did.
737
00:34:42.130 --> 00:34:44.650
So let's say the connection was made, then what, right? Well,
738
00:34:45.030 --> 00:34:48.070
first of all, he's on the technical side. I'm on
739
00:34:48.090 --> 00:34:51.239
the design side. So we are primarily doing very, very
740
00:34:51.420 --> 00:34:55.059
different things. So we're not... stepping over each other and
741
00:34:55.539 --> 00:34:59.380
constantly headbutting over the same thing. We'll headbutt over other
742
00:34:59.440 --> 00:35:02.260
things that are on the business side or product side
743
00:35:02.280 --> 00:35:06.849
because we both kind of share that. We're about 90%
744
00:35:06.849 --> 00:35:09.050
aligned on many of these things, but there's some differences
745
00:35:09.090 --> 00:35:10.869
there and we both have to make some of these decisions.
746
00:35:11.730 --> 00:35:14.789
So sometimes we'll argue there, which is totally healthy and good,
747
00:35:15.349 --> 00:35:17.820
but the majority of the work we do is different work.
748
00:35:18.010 --> 00:35:22.320
So we compliment each other rather than get tripped up.
749
00:35:22.400 --> 00:35:23.960
So that's number one. Or number two, I don't know
750
00:35:23.980 --> 00:35:26.159
what number this is. But the other thing is like,
751
00:35:26.920 --> 00:35:28.949
and I'll speak for myself, you'd have to ask him,
752
00:35:28.989 --> 00:35:32.409
but I just admire David's abilities. I admire him as
753
00:35:32.449 --> 00:35:35.760
a person, his skills, his writing ability, his technical ability,
754
00:35:35.800 --> 00:35:38.239
his ability to make decisions. his ability to see things
755
00:35:38.280 --> 00:35:40.219
other people don't see, his ability to be early on
756
00:35:40.280 --> 00:35:43.920
technical stuff, his willingness to just go for it and
757
00:35:43.940 --> 00:35:47.119
just be able to simplify. I admire that. And I
758
00:35:47.159 --> 00:35:51.639
think in any partnership, you must admire your partner. You
759
00:35:51.659 --> 00:35:53.559
should like them, but you should also admire them and
760
00:35:53.599 --> 00:35:56.119
be like, wow, they're good. They're really good at what
761
00:35:56.159 --> 00:35:59.409
they do. I admire their skill. I'll never have that ability.
762
00:35:59.449 --> 00:36:02.610
I'm not that. They are, and I admire that. So
763
00:36:02.630 --> 00:36:05.670
I think there's this admiration, different skillset, but then we
764
00:36:05.730 --> 00:36:09.760
see enough eye to eye on the core business side
765
00:36:09.780 --> 00:36:11.860
of things and how to run a business. So we're
766
00:36:11.880 --> 00:36:14.940
not constantly arguing about that either. Neither of us want
767
00:36:14.960 --> 00:36:16.760
to raise money from the outside world. Both of us
768
00:36:16.780 --> 00:36:18.440
want to keep the company as small as possible. Both
769
00:36:18.480 --> 00:36:21.010
of us believe in profitability. You know, both of us
770
00:36:21.030 --> 00:36:22.789
don't think growth is the be all end all. So
771
00:36:22.809 --> 00:36:25.369
like all the real things that matter that founders often
772
00:36:25.409 --> 00:36:27.929
hit their head over or butt heads over in a
773
00:36:27.989 --> 00:36:30.349
painful way. We don't, we don't have those, those interactions.
774
00:36:30.369 --> 00:36:33.989
We'll argue about the execution of something or the quality
775
00:36:34.030 --> 00:36:36.929
of something, whatever, but that makes it better. We never
776
00:36:36.969 --> 00:36:39.289
come away from that feeling like hurt and injured. Like
777
00:36:39.489 --> 00:36:41.190
I know a lot of founders do, and they just
778
00:36:41.409 --> 00:36:44.090
radically disagree about fundamentals in their business.
779
00:36:45.050 --> 00:36:49.190
Most people out there want to scale and grow at
780
00:36:49.250 --> 00:36:51.989
all costs, do whatever it takes. And so it's interesting
781
00:36:52.010 --> 00:36:54.829
that both of you are fully aligned when at the
782
00:36:54.869 --> 00:36:57.579
beginning you there couldn't have been any way of knowing
783
00:36:57.659 --> 00:37:00.320
that you would have been both against like growth at
784
00:37:00.360 --> 00:37:03.320
all costs or not, or, or both so focused on
785
00:37:03.409 --> 00:37:06.070
profitability and building a company that's going to do
that
786
00:37:06.230 --> 00:37:09.070
every single year and not just try to raise money and.
787
00:37:09.510 --> 00:37:11.929
Build, build, build, build, build big exit. Right.
788
00:37:12.010 --> 00:37:14.070
So is that part of the luck or have you
789
00:37:14.110 --> 00:37:17.349
influenced him more about that? Has he influenced you more
790
00:37:17.389 --> 00:37:20.110
about that? Or were you guys just, just perfectly aligned
791
00:37:20.150 --> 00:37:20.789
from the beginning?
792
00:37:21.849 --> 00:37:25.639
Well, I'm sure we've influenced each other. Yeah. Many, In
793
00:37:25.659 --> 00:37:29.300
many different ways, clearly. So David was a fan of
794
00:37:29.360 --> 00:37:32.000
our company in the early days. And our company was
795
00:37:32.119 --> 00:37:34.260
based on ideas. So if you were to look at
796
00:37:34.300 --> 00:37:39.449
our early website, if you actually go to 37signals. com slash manifesto,
797
00:37:39.750 --> 00:37:43.090
I think is the original site that's still available. You
798
00:37:43.110 --> 00:37:44.469
have to double check that. I'll get you the right
799
00:37:44.489 --> 00:37:46.409
link if that's not exactly that. I think it is
800
00:37:46.449 --> 00:37:48.570
that though. That was the original site. And we were
801
00:37:48.590 --> 00:37:51.260
a web design company. And the site was black and white.
802
00:37:51.469 --> 00:37:55.289
And it was text only. And it was 37signals. weird
803
00:37:55.349 --> 00:37:59.630
ideas about stuff. So if you're a fan of the
804
00:37:59.670 --> 00:38:02.869
company after looking at that, like all that stuff was
805
00:38:02.909 --> 00:38:09.340
about being small, focusing on quality, the value of design,
806
00:38:09.420 --> 00:38:12.679
people who inspired us, good writing, all these things. And
807
00:38:12.719 --> 00:38:15.139
David fell in and liked that stuff. So I think
808
00:38:15.179 --> 00:38:19.059
we had this shared understanding of what we thought was
809
00:38:19.099 --> 00:38:21.739
good to begin with, which was helpful. But yeah, we
810
00:38:21.760 --> 00:38:25.440
didn't like talk about profitability or any of these things
811
00:38:25.559 --> 00:38:28.019
early on. But I think like the sensibilities were there
812
00:38:28.119 --> 00:38:34.809
because the foundational, our foundational interests were aligned. And then
813
00:38:34.849 --> 00:38:38.199
I think, I mean, it's pretty hard to probably be
814
00:38:38.219 --> 00:38:41.139
in a business that is profitable and throwing off cash
815
00:38:41.460 --> 00:38:44.619
to the owners and think it's a bad direction. So
816
00:38:44.639 --> 00:38:47.250
I think like, you kind of ultimately fall in behind
817
00:38:47.289 --> 00:38:49.030
each other in a sense. And then you, you push
818
00:38:49.050 --> 00:38:51.150
and pull each other in different ways. And we've been
819
00:38:51.170 --> 00:38:52.849
influenced by one another in a lot of different ways.
820
00:38:53.469 --> 00:38:55.489
But yeah, I, like if he would have come from
821
00:38:55.530 --> 00:38:57.800
a world also, I would say he had similar experiences.
822
00:38:57.900 --> 00:39:01.000
So he'd worked for a VC backed company. I think
823
00:39:01.039 --> 00:39:02.699
it was in video games or something like that. And
824
00:39:02.739 --> 00:39:06.000
just saw like the sort of the, the tragedy that
825
00:39:06.039 --> 00:39:08.469
that was. And I had done the same thing. I'd
826
00:39:08.510 --> 00:39:11.510
worked on a contract basis for a company called Quokka
827
00:39:11.530 --> 00:39:14.739
sports in San Francisco and, And I was only there
828
00:39:14.780 --> 00:39:16.519
for a few months. And in those few months, I
829
00:39:16.539 --> 00:39:18.920
think they doubled or tripled their head count. Like they
830
00:39:18.940 --> 00:39:20.659
had ended up having hundreds of people that raised a
831
00:39:20.699 --> 00:39:23.690
bunch of money. And I could just see waste everywhere.
832
00:39:24.570 --> 00:39:26.769
And like, this doesn't make any sense. And everyone's like, no,
833
00:39:26.789 --> 00:39:28.150
this is the future. And like, they went out of
834
00:39:28.170 --> 00:39:29.969
business in a handful of years. It was like so obvious.
835
00:39:30.219 --> 00:39:32.539
to me that was going to happen. And David, so
836
00:39:32.559 --> 00:39:34.239
David has similar experience. I had a similar experience. We
837
00:39:34.280 --> 00:39:36.380
came to this, he saw the kind of our point
838
00:39:36.400 --> 00:39:38.760
of view that was very clear and, and, and out front.
839
00:39:39.420 --> 00:39:41.719
And so I think we had enough in common early
840
00:39:41.800 --> 00:39:44.039
on to make it all kind of coalesce.
841
00:39:44.639 --> 00:39:47.539
You mentioned one of the important things was good writing.
842
00:39:48.329 --> 00:39:50.449
I read everything you write. You're one of my favorite writers,
843
00:39:50.590 --> 00:39:55.849
both online and books too. And that, I think great
844
00:39:55.909 --> 00:39:58.300
writers make it look easy. I think you make it
845
00:39:58.320 --> 00:40:00.340
look really, I read them like, yeah, that's easy.
846
00:40:00.380 --> 00:40:01.579
I could do that. And then you go try to
847
00:40:01.619 --> 00:40:03.719
do it. You're like, that doesn't look the same.
848
00:40:04.539 --> 00:40:07.559
I love to hear more about one, the importance of
849
00:40:07.639 --> 00:40:11.179
writing from a leadership perspective, right? And how you view
850
00:40:11.219 --> 00:40:16.530
that as well as beyond repetition, how you've gotten so
851
00:40:16.610 --> 00:40:17.050
good at it.
852
00:40:18.579 --> 00:40:20.380
Well, first of all, I'll take the second part first
853
00:40:20.400 --> 00:40:23.800
because I hated writing growing up. I hated it. Absolutely
854
00:40:23.820 --> 00:40:25.539
hated it. And I hate it because I was asked
855
00:40:25.559 --> 00:40:27.800
to write things I didn't care about. Like I had
856
00:40:27.820 --> 00:40:29.320
to write a report on, you know, I don't know,
857
00:40:29.880 --> 00:40:32.800
Rome or something. I mean, Rome's cool now, but when
858
00:40:32.840 --> 00:40:35.260
I was 15, I could care less, right? You know,
859
00:40:35.280 --> 00:40:37.119
all the things, whatever, right? You're asked to write these
860
00:40:37.159 --> 00:40:39.699
reports and they have to be 10 pages. And it's
861
00:40:39.719 --> 00:40:41.800
like all about page count and subject you don't care about.
862
00:40:41.880 --> 00:40:43.420
Or maybe you get to pick a subject, but what
863
00:40:43.440 --> 00:40:45.159
do you know when you're that age and you just, whatever.
864
00:40:46.099 --> 00:40:47.820
I just hated it. I hated the formality of it.
865
00:40:47.820 --> 00:40:51.619
I hated the, the process around it, the length requirements,
866
00:40:51.659 --> 00:40:54.300
like the whole thing, the way it was supposed to
867
00:40:54.340 --> 00:40:55.880
be done, which is like you write a draft and
868
00:40:55.900 --> 00:40:57.519
you hand a draft and the teacher gives you feedback
869
00:40:57.579 --> 00:40:59.500
and you're doing other, I don't write that way. I
870
00:40:59.500 --> 00:41:01.840
don't like that. So anyway, hated writing until I got
871
00:41:01.880 --> 00:41:07.500
to write what's in my head. You, you and I
872
00:41:07.980 --> 00:41:10.699
are having a conversation right now. We're not struggling to
873
00:41:10.719 --> 00:41:13.969
have this conversation. You're asking great questions. Hopefully I'm providing
874
00:41:14.030 --> 00:41:18.929
decent answers. Um, If you could just write what you
875
00:41:18.969 --> 00:41:23.269
want to say, then writing isn't that hard. What's hard
876
00:41:23.309 --> 00:41:26.269
is when you think about having to write something. So
877
00:41:26.309 --> 00:41:27.789
the way I do is I just think about what
878
00:41:27.829 --> 00:41:31.150
I want to say. Instead of saying it, I write it.
879
00:41:31.840 --> 00:41:36.260
And so my writing is very conversational. And my head
880
00:41:36.300 --> 00:41:37.800
is always like, write it like you'd say it, write
881
00:41:37.820 --> 00:41:39.519
it like you'd say it. And this is true in
882
00:41:39.599 --> 00:41:41.139
business writing too. Like when I'm trying to come up
883
00:41:41.159 --> 00:41:43.380
with a marketing, like I write all of our marketing sites,
884
00:41:43.780 --> 00:41:46.039
all the copy on our pages and the headlines and everything.
885
00:41:47.150 --> 00:41:49.889
And I can find myself sometimes falling into that trap
886
00:41:49.929 --> 00:41:52.539
of trying to like write a marketing-y headline or something
887
00:41:53.280 --> 00:41:57.219
or describing the product in a way that like, you know,
888
00:41:57.300 --> 00:41:59.199
is it like a marketing description of the product?
889
00:41:59.219 --> 00:42:01.769
I feel like you should say for like this grand
890
00:42:01.829 --> 00:42:04.530
audience when it's like, actually, that probably doesn't work as
891
00:42:04.570 --> 00:42:05.989
well as me just saying like what I think.
892
00:42:06.429 --> 00:42:09.329
Yeah. And also like, One thing I always catch myself
893
00:42:09.369 --> 00:42:11.230
doing when I'm in this rut is being like, would
894
00:42:11.250 --> 00:42:13.730
I ever say that? Would I ever say that out loud?
895
00:42:14.130 --> 00:42:17.030
Would I ever say Basecamp is a project management tool
896
00:42:17.070 --> 00:42:21.579
that's apt for... I would never talk that way. So
897
00:42:21.840 --> 00:42:23.519
I try to make sure I'm writing the way I
898
00:42:23.559 --> 00:42:26.320
would actually literally speak to a human being if I
899
00:42:26.360 --> 00:42:29.099
was talking about our product or if I was talking
900
00:42:29.119 --> 00:42:30.900
about an idea or like I am right now with
901
00:42:30.980 --> 00:42:35.179
answering your questions. My writing would sound just like I'm talking.
902
00:42:36.090 --> 00:42:37.909
And I just know, I know this because I've talked
903
00:42:37.929 --> 00:42:39.809
to so many writers about this who struggle with this.
904
00:42:40.929 --> 00:42:44.650
They can't quite, and I'll get, they'll send me a
905
00:42:44.659 --> 00:42:46.699
draft of a blog post or something like, what do
906
00:42:46.719 --> 00:42:48.679
you think? And I'm like, would you ever say this
907
00:42:48.719 --> 00:42:50.179
out loud? If you were to read this out loud,
908
00:42:50.219 --> 00:42:52.139
would this sound like you? And they're always like, no.
909
00:42:52.280 --> 00:42:54.059
I'm like, well, then why are you writing it like that?
910
00:42:55.619 --> 00:42:58.639
And I know why. It's sort of been ingrained in
911
00:42:58.699 --> 00:43:02.460
us to think about writing. I'm just trying to think
912
00:43:02.480 --> 00:43:05.300
about communicating And I don't care if it's verbal or written,
913
00:43:05.340 --> 00:43:07.139
it's going to be the same for me. So that's
914
00:43:07.360 --> 00:43:09.079
kind of, I'm not going to call it a secret.
915
00:43:09.159 --> 00:43:11.159
It's certainly not a secret, but that's like my approach
916
00:43:11.199 --> 00:43:13.019
that I think works well for me. At least other
917
00:43:13.039 --> 00:43:14.679
people are going to write in different ways, but that
918
00:43:14.719 --> 00:43:15.389
works well for me.
919
00:43:16.289 --> 00:43:19.510
Do you ever actually speak and then just have like
920
00:43:19.550 --> 00:43:22.789
transcripts written out and then you like edit the transcripts?
921
00:43:22.809 --> 00:43:24.369
So it's literally you speaking?
922
00:43:24.989 --> 00:43:27.639
Yeah. I don't do that. But what I will do
923
00:43:27.760 --> 00:43:30.219
sometimes is I'll use like the voice memo app on
924
00:43:30.239 --> 00:43:32.699
my phone to just, if I have an idea that
925
00:43:32.739 --> 00:43:35.420
I think is interesting, I'll just like speak it and
926
00:43:35.440 --> 00:43:39.840
just
record that. So I don't forget the idea. And then,
927
00:43:40.000 --> 00:43:42.380
and I want to say it versus writing it because
928
00:43:42.400 --> 00:43:45.820
I can just kind of like free wheel and just
929
00:43:45.860 --> 00:43:48.659
kind of go free associate for a little bit and
930
00:43:48.699 --> 00:43:50.860
not like worry about grammar and all this stuff. And
931
00:43:50.880 --> 00:43:53.019
it's just faster to talk it out loud. So I'm like,
932
00:43:53.489 --> 00:43:56.929
I might talk for 45 seconds into the mic just
933
00:43:56.969 --> 00:43:59.070
to record something and then I'll come back to it
934
00:43:59.090 --> 00:44:01.119
and I'll write it. But I've never tried to dictate
935
00:44:01.179 --> 00:44:06.280
an entire piece. I think I would probably be, spend
936
00:44:06.300 --> 00:44:08.920
more time editing out the ums and the ahs and
937
00:44:08.940 --> 00:44:13.400
the ands and the weird structure because speaking is still
938
00:44:13.420 --> 00:44:16.219
a little bit different than writing in a sense that
939
00:44:16.260 --> 00:44:17.739
it just, it's easier for me to just write the thing.
940
00:44:17.880 --> 00:44:19.840
And I also, by the way, I don't write in drafts.
941
00:44:20.119 --> 00:44:23.409
So I don't, I don't write a whole thing and
942
00:44:23.449 --> 00:44:25.750
then go back and revise the whole thing and then
943
00:44:25.789 --> 00:44:28.210
go back and revise the whole thing. I'm writing and
944
00:44:28.349 --> 00:44:32.050
editing as I go. So it's, I will finish a
945
00:44:32.090 --> 00:44:34.239
thing and then read it and go, I don't like this.
946
00:44:34.510 --> 00:44:36.960
And like, where can I tweak it? But I'll write
947
00:44:36.980 --> 00:44:39.260
a sentence or two and I'll come back and quickly
948
00:44:39.320 --> 00:44:41.920
modify that without moving on. So it's not a whole
949
00:44:42.019 --> 00:44:44.280
complete draft thing. I think that I found that that
950
00:44:44.519 --> 00:44:46.380
is a waste of my time to do it in
951
00:44:46.420 --> 00:44:48.159
that way. I'd rather just kind of edit as I
952
00:44:48.179 --> 00:44:51.210
go and get, get somewhere good as I'm going. And then, um,
953
00:44:51.869 --> 00:44:55.320
you know, proofread at the end and maybe revise it
954
00:44:55.340 --> 00:44:57.340
a bit more or usually cutting it down a little
955
00:44:57.360 --> 00:44:59.719
bit can be a bit wordy sometimes that way. So
956
00:44:59.980 --> 00:45:00.500
that's my.
957
00:45:00.920 --> 00:45:03.670
The Morgan Housel style of, of his writing. That's what
958
00:45:03.690 --> 00:45:03.969
he said.
959
00:45:04.010 --> 00:45:06.789
Sometimes he won't even, he won't even read the thing
960
00:45:06.869 --> 00:45:10.639
he'll he'll edit as he goes, press publish. And he's like,
961
00:45:10.659 --> 00:45:12.460
the quickest way you'll find a typo is just hit
962
00:45:12.519 --> 00:45:14.619
publish because all your readers will tell you, they'll tell you.
963
00:45:14.980 --> 00:45:16.199
And then you just clean it up. He's like, and
964
00:45:16.219 --> 00:45:18.340
I just fixed it afterwards. And I'm like, he's a
965
00:45:18.340 --> 00:45:20.519
really good writer, but I read all of his stuff too.
966
00:45:20.639 --> 00:45:23.139
I've done that too. And it's funny because that is
967
00:45:23.239 --> 00:45:27.409
really how software works as well. So just briefly, there
968
00:45:27.469 --> 00:45:31.199
is nothing better than shipping something to figure out if
969
00:45:31.219 --> 00:45:33.489
something's working or not. You just ship it. And like,
970
00:45:34.230 --> 00:45:36.710
at that moment, you actually figure out what's really worth
971
00:45:36.829 --> 00:45:39.880
fixing and what really isn't worth fixing versus like, laboring
972
00:45:39.920 --> 00:45:42.539
over for three weeks to get it just right before shipping.
973
00:45:42.579 --> 00:45:44.260
I feel like you're better off shipping it and spending
974
00:45:44.280 --> 00:45:47.010
those three weeks, if there is even work to do
975
00:45:47.030 --> 00:45:49.530
over the next three weeks, refining and fixing the things
976
00:45:49.550 --> 00:45:51.989
that really needed fixing and refining, and not just fixing
977
00:45:52.010 --> 00:45:54.030
and refining things that didn't actually need it. And shipping
978
00:45:54.070 --> 00:45:55.550
is the best way, just like publishing.
979
00:45:56.070 --> 00:45:57.690
That goes for life.
980
00:45:58.329 --> 00:45:59.590
Yeah, 100% agree.
981
00:45:59.659 --> 00:46:02.599
If you just ship it, you'll... I mean, we learn
982
00:46:02.619 --> 00:46:04.260
who we are in practice, not in theory, right? The
983
00:46:04.300 --> 00:46:07.809
Herminia Barqua, but it's so true. for pretty much everything.
984
00:46:07.829 --> 00:46:11.090
Like we learn by doing, we learn by that one, one,
985
00:46:11.199 --> 00:46:13.360
one more point on writing from a leadership perspective, Jason,
986
00:46:13.420 --> 00:46:13.840
is that.
987
00:46:15.380 --> 00:46:17.079
Some leaders that I work with, they.
988
00:46:16.940 --> 00:46:20.420
Have like comms teams and, you know, like they're, they, they,
989
00:46:20.579 --> 00:46:22.119
they have something they want to say, then they got
990
00:46:22.139 --> 00:46:23.639
to go with the team and they go through it.
991
00:46:23.659 --> 00:46:25.579
And by the time the draft gets back out and
992
00:46:25.639 --> 00:46:27.860
it's sent to the whole company, it's like, what is this?
993
00:46:27.940 --> 00:46:31.210
Like it's plain and boring and generic. And it's obviously
994
00:46:31.269 --> 00:46:33.210
not from the voice of the leader.
995
00:46:34.260 --> 00:46:34.679
Two things.
996
00:46:34.889 --> 00:46:37.449
One, I think writing is the ultimate tool for clarity.
997
00:46:37.489 --> 00:46:39.429
You don't fully know what you think until you get
998
00:46:39.449 --> 00:46:41.300
it out of your head onto the page. And then two,
999
00:46:41.389 --> 00:46:43.780
for the reader, especially if you're leading a company like
1000
00:46:43.820 --> 00:46:48.300
you are, if they sense it's not your voice... you
1001
00:46:48.360 --> 00:46:50.500
might as well just delete it. It actually has a
1002
00:46:50.880 --> 00:46:54.260
negative effect, I think, because it's inauthentic. It's not real.
1003
00:46:54.280 --> 00:46:56.900
And they're like, well, what is he actually thinking? As
1004
00:46:56.960 --> 00:46:59.699
opposed to when they read your stuff, you're like, oh,
1005
00:46:59.900 --> 00:47:02.389
I can hear Jason saying this stuff.
1006
00:47:02.760 --> 00:47:04.429
So now I know exactly what he's thinking.
1007
00:47:04.469 --> 00:47:06.469
So I know there's two parts to that when it
1008
00:47:06.530 --> 00:47:08.989
comes to getting clarity of thought as the writer. But
1009
00:47:09.030 --> 00:47:12.269
then from a reader's perspective, it's actually getting your real
1010
00:47:12.309 --> 00:47:17.090
thoughts as opposed to some comms team edited draft that
1011
00:47:18.260 --> 00:47:21.409
I think could have negative consequences for a leader. Yes.
1012
00:47:21.610 --> 00:47:22.010
Oh my God.
1013
00:47:22.070 --> 00:47:25.010
I mean, so David and I will often talk about
1014
00:47:25.050 --> 00:47:26.630
how like the worst thing in the world would be
1015
00:47:26.650 --> 00:47:30.389
to have like a ghostwriter or, or a comms team or,
1016
00:47:30.550 --> 00:47:32.909
or anyone that has to filter our words and write
1017
00:47:32.949 --> 00:47:36.059
something for, you know, for our behalf and put our
1018
00:47:36.099 --> 00:47:38.199
name on it. Like there's no way in hell ever,
1019
00:47:38.800 --> 00:47:40.480
anything that comes out of this company with my name
1020
00:47:40.559 --> 00:47:42.119
on it is not written a hundred percent by me.
1021
00:47:42.880 --> 00:47:45.059
Or like, I might run it by somebody that I
1022
00:47:45.139 --> 00:47:47.429
choose to like, David can give me some feedback, whatever,
1023
00:47:47.469 --> 00:47:50.159
but like, No one's writing this for me. Absolutely not.
1024
00:47:50.199 --> 00:47:51.489
Same thing is true for David. Same thing is true
1025
00:47:51.510 --> 00:47:54.380
for anyone. There is no one writing things for anybody here.
1026
00:47:54.880 --> 00:47:58.340
And there's no filtering through legal or we don't have
1027
00:47:58.360 --> 00:47:59.840
a PR team. We don't have a PR. We don't
1028
00:47:59.860 --> 00:48:02.099
have a comms person. We don't have a lawyer on staff.
1029
00:48:02.119 --> 00:48:04.119
We don't have any of those things. We write what
1030
00:48:04.139 --> 00:48:08.860
we write. And that's what we do for us. Now,
1031
00:48:09.239 --> 00:48:12.139
can you do that at a company with 60,000 people?
1032
00:48:12.219 --> 00:48:14.179
I don't know. In your public company, maybe you can't.
1033
00:48:14.260 --> 00:48:16.199
Maybe you're not allowed to. But I'll tell you what's
1034
00:48:16.219 -->
00:48:19.599
very interesting is like Mark Zuckerberg's sort of transformation, I
1035
00:48:19.639 --> 00:48:22.289
think recently, like he's doing a lot more first person
1036
00:48:23.070 --> 00:48:28.190
sort of rough cut stuff. I find it really endearing.
1037
00:48:29.900 --> 00:48:33.300
And I can imagine maybe there's somebody at the company
1038
00:48:33.320 --> 00:48:36.800
who's nervous about that. I don't know, whatever, but. He's not.
1039
00:48:37.000 --> 00:48:39.300
And I think he realizes that like he needs to
1040
00:48:39.420 --> 00:48:41.000
connect with people. And the best way to connect with
1041
00:48:41.019 --> 00:48:43.980
people is to communicate directly to people in your own style,
1042
00:48:44.019 --> 00:48:46.159
in your own way. That is so a hundred percent
1043
00:48:46.260 --> 00:48:49.150
your words out of your mouth. Uh, so I, I'm
1044
00:48:49.170 --> 00:48:51.170
a big fan of that. And, and if that was
1045
00:48:51.230 --> 00:48:53.570
ever to change here, like I wouldn't be here. There's
1046
00:48:53.630 --> 00:48:55.110
no way in hell I could ever run a company
1047
00:48:55.130 --> 00:48:56.210
where I couldn't speak for myself.
1048
00:48:57.469 --> 00:49:01.329
Speaking of Zuckerberg, I mean, talk about a transformation I
1049
00:49:01.369 --> 00:49:04.800
mean I think a big part of why he's gone
1050
00:49:04.840 --> 00:49:06.179
from a guy that a lot of people did not
1051
00:49:06.219 --> 00:49:08.559
like and hated to now I think a lot of
1052
00:49:08.599 --> 00:49:11.460
people respect and like is because he's like yeah I'm
1053
00:49:11.500 --> 00:49:13.280
just gonna say it it's like the end of Kobe's
1054
00:49:13.340 --> 00:49:15.250
career you remember when Kobe kind of made that shift
1055
00:49:15.269 --> 00:49:17.670
where he's just going to tell the truth all the time.
1056
00:49:17.829 --> 00:49:20.019
And we all like, I just wanted to hear every
1057
00:49:20.119 --> 00:49:22.159
single time a microphone was in front of his face
1058
00:49:22.219 --> 00:49:25.199
because he kind of got comfortable enough to just say
1059
00:49:25.280 --> 00:49:25.880
what he thinks.
1060
00:49:26.380 --> 00:49:27.679
I feel like that's where Zuckerberg is.
1061
00:49:27.699 --> 00:49:30.019
And when he has his buddy with the goggles on
1062
00:49:30.119 --> 00:49:33.039
filming him and he just speaking directly to camera and
1063
00:49:33.099 --> 00:49:36.210
it's like, he's MK, a BHD, you know, where he's
1064
00:49:36.230 --> 00:49:38.989
just doing like the YouTube reviews, but he's doing it
1065
00:49:39.010 --> 00:49:41.570
of his own product versus Apple. I mean, you were like,
1066
00:49:42.210 --> 00:49:44.349
This is wild. I mean, this is wild that this
1067
00:49:44.369 --> 00:49:47.710
guy's doing it. And it's so connected with people. Like,
1068
00:49:47.730 --> 00:49:50.889
I think it's so worked because we felt this is genuinely,
1069
00:49:51.070 --> 00:49:54.449
he's really smart, but
this is genuinely what he thinks.
1070
00:49:54.510 --> 00:49:56.329
And it's a little bit raw and yeah, it's, there's
1071
00:49:56.349 --> 00:49:58.840
a little editing, but not much. It's pretty much just
1072
00:49:59.239 --> 00:50:02.500
him to camera giving you a product review. And I
1073
00:50:02.539 --> 00:50:06.829
found it super compelling. Yeah, and he's doing more of that.
1074
00:50:06.949 --> 00:50:08.309
I think he's coming into his own right now.
1075
00:50:08.369 --> 00:50:10.090
It's interesting. He's been doing this for a long time,
1076
00:50:10.110 --> 00:50:12.030
but I feel like he's having a resurgence and a
1077
00:50:12.070 --> 00:50:15.260
second wind in a sense. And partially because like the
1078
00:50:15.300 --> 00:50:17.820
industry is in the place that it is and he's
1079
00:50:17.880 --> 00:50:20.360
finding himself as an, I mean, there's nothing wrong with
1080
00:50:20.380 --> 00:50:21.880
being an opportunist. I feel like he's a bit of
1081
00:50:21.900 --> 00:50:25.929
an opportunist right now. Like Google or Apple is sort
1082
00:50:25.969 --> 00:50:29.110
of maybe fading a bit in some ways and clearly
1083
00:50:29.150 --> 00:50:31.929
like huge, powerful company making great stuff. But like their
1084
00:50:31.969 --> 00:50:35.039
reputation has sort of taken a hit. Um, Google's reputation
1085
00:50:35.059 --> 00:50:37.619
has taken a hit. Uh, all those companies are trying
1086
00:50:37.639 --> 00:50:39.900
to do like a lot of closed stuff and he's like, well,
1087
00:50:39.920 --> 00:50:42.360
I'll take the open road. I'll go the open route. And, uh,
1088
00:50:42.400 --> 00:50:45.900
which has not historically been actually their approach, but, uh,
1089
00:50:46.340 --> 00:50:47.710
I think you kind of want to root for that
1090
00:50:47.809 --> 00:50:51.170
and you're kind of glad that he exists. And, um, uh,
1091
00:50:51.409 --> 00:50:53.429
I think, I think it's great. I think he wasn't
1092
00:50:53.510 --> 00:50:56.409
the most comfortable communicator like early in his career. I
1093
00:50:56.449 --> 00:50:58.989
think he was pretty stiff and, and maybe not comfortable
1094
00:50:59.010 --> 00:51:01.079
in front of a camera. But he's been working on
1095
00:51:01.099 --> 00:51:03.079
that clearly. And I think when he's at his best,
1096
00:51:03.119 --> 00:51:05.980
when he's just not scripted. And when you see him
1097
00:51:06.039 --> 00:51:08.599
do scripted stuff, it's still cringeworthy, in my opinion. And
1098
00:51:09.260 --> 00:51:12.969
you're like, dude, just talk. Don't read a script. You
1099
00:51:13.010 --> 00:51:15.150
know your stuff. You know your product. You know your pitch.
1100
00:51:15.190 --> 00:51:17.630
You know how this goes. Just be yourself. You can
1101
00:51:17.710 --> 00:51:20.010
really feel when someone is just going off the cuff
1102
00:51:20.030 --> 00:51:23.429
versus reading a teleprompter, as good as they might be
1103
00:51:23.449 --> 00:51:27.420
at reading a teleprompter. It's the cadence, the tone, the timing. Yeah.
1104
00:51:28.139 --> 00:51:29.460
You can tell when someone's reading and you can tell
1105
00:51:29.480 --> 00:51:32.280
when someone's speaking. And he'd be better off. And I
1106
00:51:32.420 --> 00:51:34.960
think it's proving true that he's better off just speaking,
1107
00:51:35.219 --> 00:51:39.739
just being himself. Tim Cook would never do this. Or
1108
00:51:39.760 --> 00:51:44.590
maybe he would, but he's too disconnected from the product
1109
00:51:44.630 --> 00:51:46.889
in a way that Zuckerberg is very connected.
1110
00:51:46.610 --> 00:51:48.010
To the product. I don't know him that well, but
1111
00:51:48.070 --> 00:51:49.710
you think so?
1112
00:51:51.030 --> 00:51:54.230
My sense is that Cook is definitely, I mean, probably
1113
00:51:54.250 --> 00:51:58.550
an outstripper. not even probably, is an outstanding operator, but
1114
00:51:58.590 --> 00:52:01.309
he's not a product person in the way that Zuckerberg
1115
00:52:01.989 --> 00:52:05.050
understands his product. He uses his product through and through
1116
00:52:05.090 --> 00:52:07.610
and through and through. I really feel like he's in
1117
00:52:07.650 --> 00:52:10.980
there with the teams working this stuff out and has
1118
00:52:11.019 --> 00:52:13.739
great product instinct. And I think that comes from just
1119
00:52:13.760 --> 00:52:16.659
starting a company that was a product company. Tim Cook
1120
00:52:16.860 --> 00:52:20.599
was an operator, a COO, an extraordinary supply chain genius.
1121
00:52:21.730 --> 00:52:23.809
And it's clearly run Apple really, really well in a
1122
00:52:23.829 --> 00:52:27.820
lot of ways, obviously. But he doesn't have the product,
1123
00:52:28.340 --> 00:52:31.340
in my opinion, for whatever it's worth, which is not much,
1124
00:52:31.420 --> 00:52:33.739
but it's just my observation. Like he just doesn't have
1125
00:52:33.780 --> 00:52:36.480
that product gene in him. So when he talks about
1126
00:52:36.500 --> 00:52:41.019
the products, it's like there's a translator in the middle somewhere.
1127
00:52:41.420 --> 00:52:41.599
Yeah.
1128
00:52:41.860 --> 00:52:43.400
And I think you can, even if he was to
1129
00:52:43.480 --> 00:52:45.469
go off the cuff, it still feels like there's a translator.
1130
00:52:46.909 --> 00:52:49.409
Also, back to Zuckerberg, and I think some people think
1131
00:52:49.449 --> 00:52:51.909
this is really stupid, what I'm about to say, but
1132
00:52:53.170 --> 00:52:57.530
I would not discount the fact of this dude's working
1133
00:52:57.670 --> 00:53:01.309
out hard in the gym, and he's fighting, and I
1134
00:53:01.369 --> 00:53:04.849
think it's built confidence. And you can build confidence in
1135
00:53:04.929 --> 00:53:08.949
certain areas of your life that then show up in
1136
00:53:09.110 --> 00:53:10.409
other areas of your life.
1137
00:53:10.489 --> 00:53:13.210
I'm a big workout guy, athlete, right? You're
running and
1138
00:53:13.230 --> 00:53:15.150
all this. I think that stuff.
1139
00:53:16.380 --> 00:53:18.780
will help you in way more ways than just being
1140
00:53:18.840 --> 00:53:22.949
a healthier person because you're exercising. And I don't know
1141
00:53:22.989 --> 00:53:25.969
if that's enough of the story. I think you see
1142
00:53:25.989 --> 00:53:27.610
this guy with a shirt off and he's kind of jacked,
1143
00:53:27.690 --> 00:53:29.989
you know, and he's at UFC fights. I think that
1144
00:53:30.030 --> 00:53:32.539
plays a role in the guy showing up more confident
1145
00:53:32.559 --> 00:53:34.739
for these podcast interviews that he's doing, as well as
1146
00:53:34.800 --> 00:53:35.820
the straight to camera stuff.
1147
00:53:36.179 --> 00:53:37.880
That is a part of leading.
1148
00:53:38.219 --> 00:53:40.539
And we have to find ways to build confidence so
1149
00:53:40.559 --> 00:53:44.010
that it kind of inspires people to say, yeah, I
1150
00:53:44.030 --> 00:53:45.730
can get behind this guy, you know, and I feel
1151
00:53:45.750 --> 00:53:46.909
like that's, that's part of his story.
1152
00:53:46.929 --> 00:53:49.250
A hundred percent. I think it's a great observation and
1153
00:53:49.309 --> 00:53:51.449
I don't think it's stupid at all. I think it's probably,
1154
00:53:51.809 --> 00:53:54.409
we're guessing here, but probably very true. If I had
1155
00:53:54.429 --> 00:53:56.610
to wager, if I had to place a bet, I
1156
00:53:56.650 --> 00:53:58.889
think so. Mind and body are connected. You know, you
1157
00:53:58.909 --> 00:54:01.440
feel good about your body. You feel good about your strength, yourself.
1158
00:54:02.199 --> 00:54:06.119
He's been very high achieved person in, in, in, in,
1159
00:54:06.239 --> 00:54:08.920
in the software world. And now clearly he's like a legitimate,
1160
00:54:08.940 --> 00:54:10.320
what is he black belt now or something? And a
1161
00:54:10.360 --> 00:54:12.380
few things I don't even know, but like he's all, he's,
1162
00:54:12.679 --> 00:54:16.980
Clearly worked hard and is committed and disciplined and pushing himself.
1163
00:54:17.179 --> 00:54:19.800
And of course, why wouldn't you feel good about walking
1164
00:54:19.840 --> 00:54:23.079
through the space, walking through the world that way? It's
1165
00:54:23.139 --> 00:54:26.199
going to show up in some other way. I know
1166
00:54:26.260 --> 00:54:29.400
like for me, I've been doing CrossFit for like a
1167
00:54:29.420 --> 00:54:32.539
few years now. And I feel better in every way
1168
00:54:32.599 --> 00:54:34.840
because of it. I've always been an athlete. I've always
1169
00:54:34.860 --> 00:54:37.050
been in shape. But I've been pushing myself a lot
1170
00:54:37.070 --> 00:54:39.409
harder over the last few years in ways that kind
1171
00:54:39.429 --> 00:54:44.750
of surprised me. And I feel incredibly strong and solid
1172
00:54:44.829 --> 00:54:47.550
in a way where I feel like foundationally I have
1173
00:54:48.230 --> 00:54:53.070
more stability mentally as well. And so I'm not surprised
1174
00:54:53.110 --> 00:54:54.760
at all if that's the case with him. And it's
1175
00:54:54.780 --> 00:54:55.969
cool to see. It's really cool to see.
1176
00:54:56.019 --> 00:54:59.159
It feels good. It feels good to feel strong. It
1177
00:54:59.199 --> 00:55:01.400
feels good. It shows up everywhere. It feels good. It
1178
00:55:01.420 --> 00:55:04.699
feels strong. One of the things, not to pivot too much,
1179
00:55:04.760 --> 00:55:08.099
but I think that's also a part of like the
1180
00:55:08.139 --> 00:55:13.619
word culture is used constantly now. And in your work rework,
1181
00:55:14.079 --> 00:55:16.079
you write about a culture and you said you don't
1182
00:55:16.179 --> 00:55:17.219
create culture.
1183
00:55:17.800 --> 00:55:18.559
It happens.
1184
00:55:19.639 --> 00:55:22.860
And so I would love to hear more about how
1185
00:55:22.920 --> 00:55:25.059
you think about the culture at your.
1186
00:55:24.940 --> 00:55:29.150
Company and how it has happened over time. My feeling
1187
00:55:29.170 --> 00:55:32.840
basically is that culture is essentially a moving average. It's
1188
00:55:32.900 --> 00:55:36.320
not something you create, actually. It's something that creates itself.
1189
00:55:37.579 --> 00:55:41.340
It is the result of consistent behavior in an organization.
1190
00:55:42.639 --> 00:55:44.380
So it's how you treat each other, how you treat
1191
00:55:44.400 --> 00:55:47.219
your customers, the focus you have or the focus you
1192
00:55:47.260 --> 00:55:49.260
don't have, the decisions you make or the decisions you
1193
00:55:49.280 --> 00:55:52.280
don't make, or how you're making decisions, how you speak
1194
00:55:52.300 --> 00:55:54.460
to the public, how you show up in all these
1195
00:55:54.500 --> 00:55:58.309
different ways. And it's just the result of all of
1196
00:55:58.369 --> 00:56:02.199
those things. So you can decide to want a certain
1197
00:56:02.219 --> 00:56:05.679
culture in a company. You can say that, like, we're
1198
00:56:05.699 --> 00:56:07.480
going to be honest and we're going to be open
1199
00:56:07.500 --> 00:56:09.480
and we're going to be transparent or we're going to
1200
00:56:09.539 --> 00:56:12.300
really care for each other or whatever it is, whatever
1201
00:56:12.360 --> 00:56:13.280
your things are. Right.
1202
00:56:14.030 --> 00:56:14.670
It doesn't matter.
1203
00:56:14.690 --> 00:56:17.590
I mean, it can matter that you want to go
1204
00:56:17.630 --> 00:56:19.409
in that direction. You're going to make efforts to go
1205
00:56:19.449 --> 00:56:23.449
in that direction. But ultimately, it's what are you actually doing?
1206
00:56:23.989 --> 00:56:27.460
Actions speak louder than words, essentially, in the most basic
1207
00:56:27.500 --> 00:56:30.179
form here. And I would take the last 50 days.
1208
00:56:30.199 --> 00:56:33.179
I always think of a 50-day moving average. That's the culture.
1209
00:56:33.780 --> 00:56:35.739
And the good news there is like, It can get
1210
00:56:35.780 --> 00:56:38.300
better and it can get worse quickly. So it's good
1211
00:56:38.320 --> 00:56:41.260
and bad. But it's relatively easy to correct if things
1212
00:56:41.300 --> 00:56:43.699
aren't going well. And you also can't rest on your
1213
00:56:43.719 --> 00:56:45.219
laurels because if things are going well, they can go
1214
00:56:45.260 --> 00:56:47.579
bad too. If you just start to be, you know,
1215
00:56:48.420 --> 00:56:51.469
terse with each other or, you know, you're not helpful, whatever,
1216
00:56:51.489 --> 00:56:54.289
like pretty quickly, people recognize that very, very fast. And
1217
00:56:54.329 --> 00:56:56.909
it's going to take your trend line down. So I
1218
00:56:56.949 --> 00:56:59.190
think of it as, yeah, as a moving average of
1219
00:56:59.469 --> 00:57:03.809
results and not financial results, but like all the results
1220
00:57:03.849 --> 00:57:07.739
of what a team does to and with one another.
1221
00:57:09.659 --> 00:57:13.889
Would you and DHH ever consider selling?
1222
00:57:15.469 --> 00:57:19.670
Well, so right now, no, but the truth is like
1223
00:57:20.469 --> 00:57:21.650
businesses don't last forever.
1224
00:57:22.130 --> 00:57:22.929
Yeah.
1225
00:57:22.989 --> 00:57:25.429
So what happens to a business? It either goes out
1226
00:57:25.469 --> 00:57:28.460
of business. It sort of either goes out of business
1227
00:57:28.559 --> 00:57:31.800
rapidly because something goes terribly wrong. It sort of fades
1228
00:57:31.860 --> 00:57:35.300
away because it's irrelevant or you just mismanage it. It
1229
00:57:35.320 --> 00:57:38.599
gets acquired or it can go public or whatever, right?
1230
00:57:38.679 --> 00:57:40.739
It can merge with another company. There's like a handful
1231
00:57:40.780 --> 00:57:46.019
of outcomes eventually, right? And I can tell you like
1232
00:57:46.099 --> 00:57:49.840
going public would be a no. I'm not interested in that, right?
1233
00:57:50.300 --> 00:57:54.230
Hopefully we don't crash and burn because we really screw
1234
00:57:54.250 --> 00:57:57.829
something terribly bad up, you know, out of nowhere. I mean,
1235
00:57:57.889 --> 00:57:59.469
it can happen, but hopefully that doesn't happen or a
1236
00:57:59.510 --> 00:58:02.289
competition come in and crush us in some way, whatever,
1237
00:58:02.429 --> 00:58:05.269
all possible, right? But we'd like to probably have control
1238
00:58:05.329 --> 00:58:10.269
over our demise, in a sense. And I do think
1239
00:58:10.329 --> 00:58:13.289
selling the business would be a bit of a demise, actually.
1240
00:58:15.010 --> 00:58:17.929
It'd be the end of something. Not that that's a
1241
00:58:17.949 --> 00:58:21.179
bad thing, by the way. Things end and... everything does.
1242
00:58:21.420 --> 00:58:23.730
And I don't think it's bad. So I'm using the
1243
00:58:23.750 --> 00:58:26.530
word
demise, which sounds like a negative, but it's really
1244
00:58:26.590 --> 00:58:30.730
just like the end of something essentially. Um, so most likely, um,
1245
00:58:32.530 --> 00:58:35.519
when that happens, it'll probably be a sale because that's
1246
00:58:36.059 --> 00:58:39.659
hopefully we're still doing well at that point. And that's
1247
00:58:39.780 --> 00:58:42.519
sort of the, the natural, that'd be the natural end.
1248
00:58:43.079 --> 00:58:46.400
I think that, um, Another end could be like David
1249
00:58:46.420 --> 00:58:48.860
and I could decide to leave and bring in a
1250
00:58:48.900 --> 00:58:52.579
whole new team to run the place. But I don't
1251
00:58:52.599 --> 00:58:54.579
think we'd want to do it that way. I think
1252
00:58:54.599 --> 00:58:56.719
we'd probably want to sell the business. But yeah, right
1253
00:58:56.760 --> 00:58:59.610
now we're really thrilled to run the business still. We're
1254
00:58:59.650 --> 00:59:02.309
about to kick off some pretty ambitious stuff, things we've
1255
00:59:02.329 --> 00:59:04.670
never done before. And I think this next year is
1256
00:59:04.710 --> 00:59:07.590
going to be pretty spectacular and really, really fun and hard.
1257
00:59:08.429 --> 00:59:10.380
And so you know, I don't think much more than
1258
00:59:10.760 --> 00:59:14.519
beyond that anyway. But yeah, realistically, that's probably what would happen.
1259
00:59:14.820 --> 00:59:16.880
What are some of the things that you've never done
1260
00:59:16.900 --> 00:59:18.659
before that you're like going to do?
1261
00:59:18.960 --> 00:59:20.059
You're going to get this out of me, aren't you?
1262
00:59:20.480 --> 00:59:22.280
Well, I don't know. I'm not going to try.
1263
00:59:22.920 --> 00:59:24.440
Well, I will tell you, one of the things we
1264
00:59:24.460 --> 00:59:26.179
want to do is we have more product ideas that
1265
00:59:26.199 --> 00:59:28.269
we want to do. Sure. And we want to try
1266
00:59:28.329 --> 00:59:33.250
to do two of them simultaneously, which we've never done before.
1267
00:59:33.389 --> 00:59:35.320
We've only like built one product at a time, which
1268
00:59:35.380 --> 00:59:37.619
is how, you know, we only have 75 or so people.
1269
00:59:37.679 --> 00:59:40.760
So like it's a tall order to build, to build
1270
00:59:40.780 --> 00:59:43.800
a product anyway, from scratch, do it well in the way,
1271
00:59:43.840 --> 00:59:45.320
in the way we like to do it. So we'd
1272
00:59:45.340 --> 00:59:47.699
like to do two at once. And that would be
1273
00:59:47.880 --> 00:59:49.920
pretty amazing. And like to be able to launch them
1274
00:59:49.960 --> 00:59:52.840
at the same time would be pretty amazing, pretty fun.
1275
00:59:52.860 --> 00:59:55.320
And then we have, you know, might want to offer
1276
00:59:55.340 --> 00:59:58.659
them multiple different business models. There's just a bunch of
1277
00:59:58.699 --> 01:00:00.400
stuff we're going to play with and see what we
1278
01:00:00.440 --> 01:00:02.179
come up with. But I think we want to make
1279
01:00:02.239 --> 01:00:05.260
two things at once. We've never done that before and
1280
01:00:05.300 --> 01:00:07.280
launch two things at the same time. We've never done
1281
01:00:07.300 --> 01:00:09.849
that before. So that would be pretty spectacular if we
1282
01:00:09.869 --> 01:00:11.570
can pull that off in a relatively short period of
1283
01:00:11.610 --> 01:00:12.969
time as well as what we want to do. So
1284
01:00:13.889 --> 01:00:16.750
that's something we haven't done before. These also would be
1285
01:00:17.710 --> 01:00:21.349
categories we haven't we've sort of we're they're adjacent to
1286
01:00:21.389 --> 01:00:24.750
what we're doing but not we've never done these kinds
1287
01:00:24.789 --> 01:00:27.090
of products before but they're adjacent so it wouldn't be
1288
01:00:27.170 --> 01:00:30.320
a stretch to do these and uh i would say
1289
01:00:30.340 --> 01:00:32.199
that and then we might want to write another book
1290
01:00:32.280 --> 01:00:33.699
this year at the same time so we kind of
1291
01:00:33.719 --> 01:00:35.400
want to take on a lot of work we're actually
1292
01:00:35.440 --> 01:00:38.239
feeling right now like creative uh we've got a good
1293
01:00:38.280 --> 01:00:42.929
momentum got a wonderful extraordinarily good team good size and Like,
1294
01:00:43.070 --> 01:00:46.110
let's make sure we take advantage of this moment. And also,
1295
01:00:46.230 --> 01:00:48.730
this is our 25th year in business. Like, why not?
1296
01:00:49.010 --> 01:00:52.849
If we destroy it because we do too much or whatever, like,
1297
01:00:52.909 --> 01:00:54.750
not a bad run. I mean, that's hopefully not going
1298
01:00:54.769 --> 01:00:56.519
to happen. But like, if you're not willing to do
1299
01:00:56.559 --> 01:00:59.619
this now, especially after we have this incredible history behind us, like,
1300
01:00:59.639 --> 01:01:01.579
when are you going to do it? Let's do it now.
1301
01:01:01.639 --> 01:01:04.639
Let's just get extra ambitious, like 25 years in and
1302
01:01:04.679 --> 01:01:05.820
have some fun and see what happens.
1303
01:01:05.820 --> 01:01:09.300
25 years in, 75 people, fully remote. How often do
1304
01:01:09.340 --> 01:01:10.380
you guys get together in person?
1305
01:01:11.429 --> 01:01:13.699
Twice a year. So we just got together a couple
1306
01:01:13.719 --> 01:01:18.420
weeks ago, actually, in Atlanta. So we pick usually a
1307
01:01:18.460 --> 01:01:21.619
city in the U.S. and a city in Europe. And
1308
01:01:21.960 --> 01:01:23.519
in the spring, we do one. In the fall, we
1309
01:01:23.539 --> 01:01:26.610
do another. It's not always the case. Sometimes there's two
1310
01:01:26.670 --> 01:01:29.889
North American cities or whatever. So we were in Atlanta.
1311
01:01:29.929 --> 01:01:31.590
Before that, we were in Barcelona. Before that, we were
1312
01:01:31.610 --> 01:01:33.969
in New Orleans. Before that, we were in Amsterdam. We
1313
01:01:33.989 --> 01:01:35.489
kind of go back and forth. We have half our
1314
01:01:35.929 --> 01:01:37.389
companies outside of the US. We kind of want to
1315
01:01:37.429 --> 01:01:40.190
make it travel fairly easy on one half and hard
1316
01:01:40.230 --> 01:01:43.269
on the other and then the opposite. These get-togethers are
1317
01:01:43.349 --> 01:01:46.610
one week and it's basically four days. So everyone kind
1318
01:01:46.639 --> 01:01:49.440
of comes in on Sunday. We meet Monday through Thursday
1319
01:01:49.460 --> 01:01:52.139
and we all leave Friday. And the first day or
1320
01:01:52.199 --> 01:01:55.059
first day and a half is pretty much like Business
1321
01:01:55.099 --> 01:01:58.670
stuff like state of the company, big picture ideas, Q
1322
01:01:58.670 --> 01:02:00.820
& A, a little bit of a town hall kind
1323
01:02:00.840 --> 01:02:04.239
of style, you know, all hands sort of thing. And
1324
01:02:04.260 --> 01:02:07.440
then the rest of the time is primarily social. People
1325
01:02:07.480 --> 01:02:09.420
get together in small groups. They have small meals. We
1326
01:02:09.440 --> 01:02:12.300
also have a big company meal, but small meals, outings,
1327
01:02:12.380 --> 01:02:14.679
you know, to do this or that or hang out
1328
01:02:14.719 --> 01:02:16.539
as teams or just hang out, you know, and just
1329
01:02:16.579 --> 01:02:18.320
kind of hang out in a city or a place
1330
01:02:18.340 --> 01:02:25.059
or whatever. It's very replenishing. It's very refreshing. It's wonderful
1331
01:02:25.099 --> 01:02:28.219
to see everybody. And surprisingly, twice a year for a
1332
01:02:28.239 --> 01:02:29.199
week at a time is enough.
1333
01:02:30.219 --> 01:02:30.619
It's enough.
1334
01:02:31.400 --> 01:02:33.440
We look forward to doing it. And then when it's over,
1335
01:02:33.480 --> 01:02:35.579
we look forward to getting home because we're a bunch
1336
01:02:35.599 --> 01:02:41.539
of introverts. And there's always like this post-meetup exhaustion just
1337
01:02:41.559 --> 01:02:43.420
because everyone has to see each other for a lot.
1338
01:02:43.929 --> 01:02:46.320
But it really fuels us. And during COVID, we didn't
1339
01:02:46.360 --> 01:02:48.369
do this for a few years. And it really hurt
1340
01:02:48.469 --> 01:02:50.750
the company, I think. Not being able to see anyone
1341
01:02:50.869 --> 01:02:53.190
at all, literally, for a couple of years, which is
1342
01:02:53.230 --> 01:02:55.889
not unique for us. But We really rely on these
1343
01:02:55.929 --> 01:02:58.349
just simply two weeks a year. And when we didn't
1344
01:02:58.389 --> 01:02:58.869
have them, it hurt.
1345
01:02:59.389 --> 01:03:01.849
How much involvement do you have in designing like the
1346
01:03:01.909 --> 01:03:04.289
entire experience when you're at these off sites together?
1347
01:03:04.849 --> 01:03:05.710
None anymore.
1348
01:03:06.190 --> 01:03:07.690
No. So you have like a team of
people that
1349
01:03:07.730 --> 01:03:10.070
are pros at that or you hire somebody or what?
1350
01:03:10.329 --> 01:03:14.650
Two people. So Andrea and Bethany internally, they book all
1351
01:03:14.670 --> 01:03:18.869
the venues, handle all the flights, all the catering, all
1352
01:03:18.909 --> 01:03:20.590
the dinners, all the events.
1353
01:03:21.429 --> 01:03:21.940
And you show up?
1354
01:03:22.710 --> 01:03:24.690
I just show up. Everyone just shows up. They are
1355
01:03:24.909 --> 01:03:27.219
magical at this. This is not their full-time job. They
1356
01:03:27.239 --> 01:03:29.039
do other things in the company, but they do these
1357
01:03:29.300 --> 01:03:32.739
and they're super good at them. Everything goes off perfectly.
1358
01:03:32.780 --> 01:03:35.820
It's sort of an extraordinary thing to like coordinate, literally
1359
01:03:35.900 --> 01:03:39.059
flying in, you know, 70 some odd people. Not everyone
1360
01:03:39.079 --> 01:03:42.219
shows up at these 60 to 70, let's say, from
1361
01:03:42.219 --> 01:03:44.800
60 to 70 different cities around the world, essentially kind
1362
01:03:44.840 --> 01:03:46.679
of not. And there's some people live in the same city,
1363
01:03:46.719 --> 01:03:48.559
but it's a lot of flights, a lot of coordination.
1364
01:03:48.599 --> 01:03:50.019
Everyone shows up at the same time. All the rooms
1365
01:03:50.059 --> 01:03:53.159
are booked, food's there, everything's set up. AV, the whole thing.
1366
01:03:53.199 --> 01:03:56.980
So it's, it's great. I used to be more involved
1367
01:03:57.059 --> 01:04:00.219
in where we would go, but I don't want that responsibility.
1368
01:04:00.280 --> 01:04:01.710
I'd like it to be a surprise. I mean, I
1369
01:04:01.750 --> 01:04:04.750
have suggestions, like I didn't suggest the last two and
1370
01:04:04.809 --> 01:04:08.079
I'm glad we went to those. I suggested the next one.
1371
01:04:08.110 --> 01:04:08.789
We'll see where we go.
1372
01:04:08.809 --> 01:04:09.130
I don't know.
1373
01:04:09.610 --> 01:04:12.750
The reason I asked is because with the, the, the
1374
01:04:12.909 --> 01:04:17.760
changing setup of how people work, a lot of hybrid stuff,
1375
01:04:18.699 --> 01:04:21.539
a lot more remote stuff, especially with sales organizations, which
1376
01:04:21.579 --> 01:04:23.719
is I've worked with a lot of sales leaders. And
1377
01:04:23.739 --> 01:04:25.460
so their people are all over. They don't see each
1378
01:04:25.500 --> 01:04:28.760
other very much. I think it is really important to
1379
01:04:28.820 --> 01:04:32.559
be intentional about getting together and to have a team
1380
01:04:32.599 --> 01:04:34.659
of people who think about that a lot about how
1381
01:04:34.699 --> 01:04:37.139
do we design a really good experience for us to
1382
01:04:37.179 --> 01:04:40.239
be together if we're remote or if we're hybrid where
1383
01:04:40.260 --> 01:04:42.869
we're not together very much. And that's changed a lot
1384
01:04:42.949 --> 01:04:44.210
over the last few years. You guys have been doing
1385
01:04:44.230 --> 01:04:46.130
it for 25 years, but that's changed a lot for
1386
01:04:46.230 --> 01:04:49.449
most companies over the last few years. So it's worth
1387
01:04:49.489 --> 01:04:51.750
it as leaders to be, to be thinking about this
1388
01:04:51.789 --> 01:04:52.909
and to be really intentional.
1389
01:04:53.369 --> 01:04:57.869
A hundred percent. I agree. And it's, it's, it's really immeasurable.
1390
01:04:57.949 --> 01:05:00.230
Like the, the, the, the value is there. I mean, it's,
1391
01:05:00.250 --> 01:05:02.329
first of all, it's very expensive for us to do this,
1392
01:05:02.510 --> 01:05:05.070
but we don't pay rent because we don't have offices anymore.
1393
01:05:05.130 --> 01:05:07.179
So basically all the rent money we'd be spending goes
1394
01:05:07.219 --> 01:05:10.110
into these two events and they're very well thought out
1395
01:05:10.860 --> 01:05:14.110
and we, we adjust them. Um, We've been now inviting
1396
01:05:14.150 --> 01:05:16.320
a customer usually to each one to sort of talk
1397
01:05:16.360 --> 01:05:18.780
about how they use Basecamp, for example, or Hay or
1398
01:05:18.820 --> 01:05:20.599
something like that. So that's kind of nice to see.
1399
01:05:21.280 --> 01:05:22.840
And sometimes they're a little bit, some of them are
1400
01:05:22.860 --> 01:05:25.179
a little bit too booked up with events and things.
1401
01:05:25.260 --> 01:05:27.079
So like we loosen up the next one. So people
1402
01:05:27.099 --> 01:05:28.960
have more free time. And then sometimes there's too much
1403
01:05:29.019 --> 01:05:31.860
free time and enough structure. And so we're very much
1404
01:05:31.920 --> 01:05:34.360
paying attention to this. They're not formulaic, except for like
1405
01:05:34.400 --> 01:05:36.960
a couple things. There's a company-wide dinner. There's an all
1406
01:05:36.980 --> 01:05:39.480
hands thing on the first day, usually, or sometimes a
1407
01:05:39.519 --> 01:05:41.780
second day instead, depending on some people can't make it
1408
01:05:41.820 --> 01:05:45.670
in on the first day. And there's suggested events and
1409
01:05:45.730 --> 01:05:48.269
group things that you can sign up for, small group dinners,
1410
01:05:48.949 --> 01:05:51.070
small group events. There's a sign-up sheet and there's like
1411
01:05:51.130 --> 01:05:53.030
six slots for this one and four slots for that one.
1412
01:05:53.090 --> 01:05:54.469
And sign up if you want or if you don't
1413
01:05:54.510 --> 01:05:56.949
want to, that's fine. So there are things available and
1414
01:05:56.969 --> 01:05:58.969
there are things to do and they're very thoughtful things.
1415
01:05:59.710 --> 01:06:03.010
And I just can't recommend doing this highly enough. It
1416
01:06:03.170 --> 01:06:05.550
is expensive and it's going to seem like a huge
1417
01:06:06.769 --> 01:06:09.329
lift up. just to get people together. You're
like, why
1418
01:06:09.349 --> 01:06:11.650
can't we just sit over Zoom? It's just not the same.
1419
01:06:11.849 --> 01:06:13.070
You got to share a meal with people. You got
1420
01:06:13.090 --> 01:06:15.690
to smile. You got to see everyone's humanity, breathe the
1421
01:06:15.730 --> 01:06:17.250
same air. It does matter.
1422
01:06:18.090 --> 01:06:19.179
Yeah. Love it.
1423
01:06:19.289 --> 01:06:20.840
Jason, man, thank you so much for doing this. We
1424
01:06:20.880 --> 01:06:23.960
didn't come here to promote anything. I just, again, you're
1425
01:06:23.980 --> 01:06:26.840
one of my favorite thinkers and writers. So any opportunity
1426
01:06:27.099 --> 01:06:29.019
to talk to you, to me, I treasure it, man.
1427
01:06:29.340 --> 01:06:32.280
Where would you send viewers, listeners to learn more about
1428
01:06:32.300 --> 01:06:32.760
you online?
1429
01:06:33.360 --> 01:06:34.579
Well, first of all, it's very kind and I'm glad
1430
01:06:34.619 --> 01:06:36.960
we could line this up. I know scheduling was challenging
1431
01:06:37.099 --> 01:06:39.610
on my side, not on yours. So I'm glad we
1432
01:06:39.619 --> 01:06:42.369
could do this. So primarily a couple of places. So
1433
01:06:42.409 --> 01:06:46.610
I'm on Twitter, just or X at Jason Freed, F-R-I-E-D.
1434
01:06:47.110 --> 01:06:49.469
I'm on LinkedIn. Also, you can find me there. I
1435
01:06:49.510 --> 01:06:51.389
write stuff there too. And then I have my own
1436
01:06:51.409 --> 01:06:57.030
little newsletter. So if you go to world.hey.com slash Jason,
1437
01:06:57.880 --> 01:07:00.900
it's my little email newsletter and personal blog thing. You know,
1438
01:07:00.920 --> 01:07:02.940
that's kind of me. And then of course, check out
1439
01:07:02.980 --> 01:07:07.639
our stuff, 37signals, Basecamp, heyonce.com. You know, we've got a
1440
01:07:07.639 --> 01:07:09.280
lot of stuff going on these days and we've written
1441
01:07:09.300 --> 01:07:10.679
a bunch of books. You can check those out too.
1442
01:07:10.719 --> 01:07:13.780
I'm sure you'll link those up. So yeah. And you
1443
01:07:13.800 --> 01:07:20.630
can also email me. My email address is publicjasonat37signals. com or jasonatbasecamp.com
1444
01:07:20.670 --> 01:07:23.550
or jasonathey.com. You can hit me up. If you email me,
1445
01:07:23.590 --> 01:07:25.710
I will write you back. Sometimes it might take a while.
1446
01:07:25.909 --> 01:07:28.130
I would say if you want a response sooner, keep
1447
01:07:28.150 --> 01:07:31.530
the email shorter. hardest emails to respond to are like,
1448
01:07:32.130 --> 01:07:34.889
you're like, God, this person put like an hour into this.
1449
01:07:34.909 --> 01:07:37.780
I can't be flippant and write a quick response. I
1450
01:07:37.780 --> 01:07:39.099
have to really take time. And then it's hard to
1451
01:07:39.159 --> 01:07:42.820
find the time. So my general suggestion, if you want
1452
01:07:42.840 --> 01:07:45.559
to write someone and you want to
get a response,
1453
01:07:45.960 --> 01:07:47.840
short emails will almost always get a response.
1454
01:07:48.460 --> 01:07:52.829
So you probably don't remember this, but you had posted
1455
01:07:52.869 --> 01:07:55.110
on Twitter, this might've been two years ago, year and
1456
01:07:55.130 --> 01:07:55.389
a half ago.
1457
01:07:55.409 --> 01:07:56.329
I don't remember how long ago it was.
1458
01:07:57.070 --> 01:07:59.469
And you said, man, I wish people would just say, Hey,
1459
01:08:00.099 --> 01:08:02.780
do you want to record a podcast right now? As
1460
01:08:02.820 --> 01:08:04.940
opposed to like having to schedule it. So I remember
1461
01:08:05.000 --> 01:08:07.920
I waited like a week, did a lot of research,
1462
01:08:07.980 --> 01:08:10.699
you know, got my outline ready to go. And then
1463
01:08:10.739 --> 01:08:11.940
I emailed you and I'm like, do you want to
1464
01:08:11.960 --> 01:08:15.400
record a podcast right now? And then you couldn't. And
1465
01:08:15.420 --> 01:08:18.199
then I did it like again and again and again.
1466
01:08:18.239 --> 01:08:19.439
And then I was like, would you just want to
1467
01:08:19.500 --> 01:08:23.229
schedule it? So we eventually scheduled it because I'm with you.
1468
01:08:23.310 --> 01:08:25.869
Like there are some times where I would say, you know,
1469
01:08:25.930 --> 01:08:27.890
someone wants to say, hey, can I get some time
1470
01:08:27.909 --> 01:08:28.430
to do whatever?
1471
01:08:28.470 --> 01:08:31.989
And I'm like, yeah, now. Right now. Right now. Let's
1472
01:08:32.029 --> 01:08:32.210
do it.
1473
01:08:32.229 --> 01:08:33.210
I don't want to put it on my calendar. I
1474
01:08:33.229 --> 01:08:34.890
hate putting it on my calendar. I want my calendar
1475
01:08:34.909 --> 01:08:36.399
to stay clean. I got to think and I got
1476
01:08:36.409 --> 01:08:37.479
to write and I got to prepare.
1477
01:08:38.300 --> 01:08:39.319
Yes, right now. Right now.
1478
01:08:39.380 --> 01:08:41.260
I almost do that every time. I'll wait to respond
1479
01:08:41.300 --> 01:08:43.380
and say, yeah, now. And I guess that's, I don't know,
1480
01:08:43.399 --> 01:08:47.100
that's a little power imbalance. But to me, I'll say yes,
1481
01:08:47.319 --> 01:08:50.859
but I would rather just be now. It's funny how
1482
01:08:50.899 --> 01:08:54.050
many times I tried to actually record this podcast by
1483
01:08:54.090 --> 01:08:55.649
just saying, dude, you want to do it right now?
1484
01:08:57.069 --> 01:08:59.090
It's funny because I happen to be in a weird
1485
01:08:59.170 --> 01:09:02.289
time where my schedule is really messed up. I had
1486
01:09:02.350 --> 01:09:04.729
like taking the kids to school and there's some other
1487
01:09:04.750 --> 01:09:07.289
things we're working on. So like the right now's weren't working,
1488
01:09:07.649 --> 01:09:10.100
but usually they totally do work, but my schedule has
1489
01:09:10.109 --> 01:09:11.979
been scattered. So I'm glad we could line this up.
1490
01:09:12.180 --> 01:09:14.020
And I think you sent me a note a few
1491
01:09:14.060 --> 01:09:16.000
days ago and like, yeah, how about Friday? So like
1492
01:09:16.060 --> 01:09:19.060
it was close to now. It's more like, I hate
1493
01:09:19.119 --> 01:09:22.159
scheduling things like, like let's say right now we're in April.
1494
01:09:22.229 --> 01:09:24.729
Like someone's like, can you do a interview on June 9th?
1495
01:09:24.750 --> 01:09:26.949
I'm like, no, it's too far away. I don't know
1496
01:09:26.970 --> 01:09:29.420
what I'll be doing in June. So. I appreciate the
1497
01:09:29.439 --> 01:09:31.939
persistence and, and, and, uh, thanks. It was really fun
1498
01:09:31.960 --> 01:09:32.260
to chat.
1499
01:09:32.399 --> 01:09:34.359
No, I appreciate it, man. Thank you so much again
1500
01:09:34.380 --> 01:09:36.439
for doing this. And I would love to continue our
1501
01:09:36.479 --> 01:09:37.779
dialogue as we both progress, man.
1502
01:09:38.289 --> 01:09:38.369
Yeah.
1503
01:09:38.409 --> 01:09:38.670
Let me know.
1504
01:09:38.949 --> 01:09:40.109
Happy to come back on and chat.
1505
01:09:40.609 --> 01:09:41.289
Thanks so much, man.
1506
01:09:44.550 --> 01:09:47.489
It is the end of the podcast club. Thank you
1507
01:09:47.510 --> 01:09:49.710
for being a member of the end of the podcast club.
1508
01:09:49.750 --> 01:09:52.590
If you are sending me a note, Ryan at learning leader.com.
1509
01:09:52.630 --> 01:09:55.100
Let me know what you learned from this great conversation
1510
01:09:55.180 --> 01:09:58.039
with Jason Freed. A few takeaways from my notes, uh,
1511
01:09:58.479 --> 01:10:00.539
You don't create culture.
1512
01:10:00.939 --> 01:10:01.739
It happens.
1513
01:10:01.920 --> 01:10:06.220
A company's culture is a 50-day moving average. It's what
1514
01:10:06.260 --> 01:10:09.859
you've been collectively doing as a company over the last
1515
01:10:09.859 --> 01:10:10.439
50 days.
1516
01:10:10.479 --> 01:10:12.890
How do you treat people? Who have you hired or fired?
1517
01:10:13.090 --> 01:10:17.689
And why? Thinking of culture as a moving average is
1518
01:10:17.750 --> 01:10:21.449
a much more useful way as opposed to putting words
1519
01:10:21.630 --> 01:10:25.020
up on a wall. Culture is about what you actually do.
1520
01:10:25.140 --> 01:10:29.399
It's what's happening. Then, how about that Jeff Bezos story
1521
01:10:29.439 --> 01:10:34.060
you never know who is watching Jeff sat in the
1522
01:10:34.199 --> 01:10:37.420
front row for one of Jason's keynotes and was so
1523
01:10:37.500 --> 01:10:41.619
impressed that he asked to invest in his company when
1524
01:10:41.640 --> 01:10:45.079
you have the guts to put your thoughts and beliefs
1525
01:10:45.300 --> 01:10:48.199
out into the world it can work as a magnetic
1526
01:10:48.260 --> 01:10:52.399
effect to attract people to you. And it's just so
1527
01:10:52.460 --> 01:10:55.239
refreshing also to hear Jason
talk about one of the
1528
01:10:55.300 --> 01:10:58.260
core qualities that he loves so much about Jeff is
1529
01:10:58.319 --> 01:11:05.000
that he is overwhelmingly optimistic. The world is built by optimists.
1530
01:11:05.720 --> 01:11:09.890
And then, I will beat this drum forever, all leaders
1531
01:11:09.930 --> 01:11:12.829
should have a writing practice. This is how I became
1532
01:11:12.890 --> 01:11:15.949
aware of Jason. If he wasn't publicly writing, I would
1533
01:11:15.989 --> 01:11:19.859
not know that he exists. But, He ships work on
1534
01:11:19.899 --> 01:11:24.119
his website, on Twitter. He writes books. And I think
1535
01:11:24.819 --> 01:11:28.550
it's another reminder of when you hear a clear thinker,
1536
01:11:28.710 --> 01:11:32.569
it's probably because they have a writing practice. They're regularly
1537
01:11:32.609 --> 01:11:34.829
getting the thoughts out of their head onto the page.
1538
01:11:35.989 --> 01:11:39.189
And in his case, he's regularly sharing this with his company.
1539
01:11:39.210 --> 01:11:42.529
And I think if you're leading a company, hopefully you're
1540
01:11:42.590 --> 01:11:45.949
writing a lot. And hopefully you don't feel the need
1541
01:11:46.500 --> 01:11:49.520
to send your writing to a comms team or a
1542
01:11:49.659 --> 01:11:53.890
lawyer before sharing it. Now, I know there's different situations
1543
01:11:54.100 --> 01:11:56.329
depending on the size of your company, but we even
1544
01:11:56.390 --> 01:11:59.829
talked about Mark Zuckerberg doing this right now, and he's
1545
01:11:59.890 --> 01:12:03.729
leading a massive company, and it's working. It's working really
1546
01:12:03.770 --> 01:12:06.880
well because it's genuine and it's authentic, and I think
1547
01:12:06.949 --> 01:12:10.319
that's what people want. So write like you talk, write
1548
01:12:10.340 --> 01:12:12.600
what's in your head, think about what you want to say,
1549
01:12:12.819 --> 01:12:15.569
and then say it. Once again, I would say thank
1550
01:12:15.609 --> 01:12:17.909
you so much for continuing to spread the message and
1551
01:12:17.930 --> 01:12:19.930
telling a friend or two, hey, you should listen to
1552
01:12:19.970 --> 01:12:22.510
this episode of The Learning Leader Show with Jason Freed.
1553
01:12:22.729 --> 01:12:25.689
I think it will help you become a more effective leader.
1554
01:12:25.729 --> 01:12:27.720
And because you continue to do that, and you also
1555
01:12:27.729 --> 01:12:31.000
go to Apple Podcasts and Spotify, and you subscribe to
1556
01:12:31.039 --> 01:12:33.420
the show, and you rate it, hopefully five stars, and
1557
01:12:33.439 --> 01:12:35.840
you write a thoughtful review. And by doing all of that,
1558
01:12:36.380 --> 01:12:40.079
you are continually giving me the opportunity to do what
1559
01:12:40.119 --> 01:12:42.060
I love on a daily basis. And for that, I
1560
01:12:42.640 --> 01:12:45.420
will forever be grateful. Thank you so, so much. Talk
1561
01:12:45.439 --> 01:12:46.100
to you soon. Can't wait.