WEBVTT
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00:00:47.899Hey, welcome to the show, everyone.
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00:00:49.579Today we have Adam Spector with us.
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00:00:54.219Adam is currently running uh Chor, founder and CEO.
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00:00:55.579So, Adam, welcome to the show.
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00:00:56.299Thanks for joining me.
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00:00:57.979James, it's definitely a pleasure.
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00:00:58.699Great to see you again.
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00:00:59.420Yeah, it's great.
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00:00:59.979Great to see you.
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00:01:00.939It was actually, it was nice.
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00:01:06.780We got to um everybody tuning in, we were able to meet in person to go through the prep conversation.
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00:01:07.659So that was pretty cool.
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00:01:09.579We don't always don't always get to do that.
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00:01:17.420Yeah, no, it's rare and arguably um those sorts of in-person meetings are the most important ones we're all gonna have going forward in the world of AI.
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00:01:19.180So um, I'm glad we were able to do it.
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00:01:26.060And let's do it again when you either make it out to San Francisco, which is where I live, or if I make it when not if, but when I make it back to DC.
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00:01:27.659Yeah, uh definitely.
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00:01:30.620If I remember correctly, you're from the DC area, right?
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00:01:35.099I am, born and raised just outside in in a little place called Trevy Chase, Maryland.
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00:01:35.900Yeah, yeah.
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00:01:39.579Were you there like throughout your entire childhood or did you Yeah, I was really lucky.
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00:01:44.699Um, my parents were able to create a pretty stable place for us, and my my brother and myself to grow up.
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00:01:50.460Uh grew up in the same house, I guess, from almost the day I was born, maybe not quite that early, but maybe I was like a few years old.
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00:01:57.740But from what I remember from my whole life, uh up through gosh, my parents sold that house sometime after I graduated college.
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00:01:59.740So um for my whole life.
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00:02:00.699Yeah, yeah.
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00:02:02.620What were you like as a kid?
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00:02:05.740Um, I I think I like that question.
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00:02:10.939Uh I I I bet I was a com I was kind of a combination of nerdy and dorky and kind of cool.
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00:02:18.460So like it was a weird combo of like I was friends with all the cool kids who were doing all the partying and fun stuff, and I'd get invited to the parties and everything else.
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00:02:24.379But I would also be the kid who would like be playing video games and reading a ton in those sorts of pizzas.
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00:02:26.859So it was a sort of, I think a pretty good combo.
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00:02:28.620I mean, I'd I I'm certainly happy with it.
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00:02:30.139I don't, I don't mind where I ended up.
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00:02:34.539Um, and I I never felt like anything was problematic.
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00:02:35.419That's good.
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00:02:35.900That's good.
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00:02:37.900Yeah, you uh you're a big reader, right?
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00:02:38.539I am.
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00:02:39.819I I read a ton.
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00:02:46.300Uh I track a large majority of pretty much everything I read and have for the past, I don't know, probably 20 years.
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00:02:51.740Um, everything, not every article, but like every article I find interesting, I save it at the article.
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00:02:55.900Um, I read on a Kindles, and I've been doing that literally since like the Kindle one almost.
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00:03:04.060Um, and so like all my highlights and notes from all my books are stored, which by the way makes for a great fodder for AI to help understand yourself to some extent.
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00:03:08.219But like, yeah, I know, reading a ton um on a wide variety of topics.
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00:03:15.340Although I've actually did an analysis on this, and a lot of my topics are over the past three years to become more and more AI related.
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00:03:21.500Um not shocking to some extent, but it's like everybody's uh seems like everybody's obsession currently, right?
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00:03:22.539Correct, for sure.
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00:03:23.980And we'll get more into that.
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00:03:24.860It's interesting.
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00:03:36.300We were, you know, during our prep, and then earlier before we hit record, we were talking through maybe some of the more influential uh chapters uh growing up for you that really shaped who you are today.
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00:03:41.180And one of the first things you brought up is uh going to boarding school and high school.
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00:03:46.939And I'm just curious to get a sense for how that possibly shaped the person you've become.
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00:03:55.099Yeah, look, I so I I was going to the same school in DC for had gone there for almost 10 years, um, from pre-kind kindergarten all the way through eighth grade.
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00:03:57.980Um, and I had met some people who were going to boarding school.
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00:03:59.099It was not a thing in DC.
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00:04:04.060It probably still isn't a thing in DC, whereas in the Northeast, it's like a big lot of kids go to boarding school.
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00:04:07.180Um, and my parents were like, hey, these schools are amazing.
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00:04:08.780Yeah, you should think about going.
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00:04:10.460And so we applied.
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00:04:17.740Um, I only applied to four schools and got into two out of the four, and ended up being my parents like, look, you need to go for a year.
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00:04:19.180It's an amazing opportunity.
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00:04:20.219The school's amazing.
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00:04:27.180And these in some of these boarding schools, for those who don't know, people think of boarding school as like a remedial place that kids go because they're really bad or something.
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00:04:28.779This is not that sort of boarding school.
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00:04:30.779This is this school is one of the, it's called the Lawrenceville School.
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00:04:33.339It's one of the top 10, probably high schools in the country.
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00:04:39.819And my parents like, look, the the facilities they have, the resources they have, the opportunity for you is really big.
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00:04:40.620You should go.
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00:04:48.060Um, and and I remember like first being excited, and then I actually got in and realized, oh my God, I might leave all my friends who I'd been friends with for 10 years at that point.
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00:04:49.819And I went and I'm so glad I went.
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00:04:56.300In the end, what it did is it gave me a much wider perspective and lens on the world because the kids at Lawrenceville were from all over the world.
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00:05:00.139Whereas the kids I was going to school with in DC were just from the DC area.
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00:05:03.019Um in were pretty similar to me, right?
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00:05:07.340The kids in DC were all pretty similar to me, versus the kids from at Lawrenceville were really from everywhere.
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00:05:09.500And so that changed my perspective in a big way.
00:05:09.579 -->
00:05:11.740I was lucky enough I was able to keep kind of my DC connects.
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00:05:13.579I would come home for parties and do all that stuff.
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00:05:15.980I'd but I would, but I'm a high school kid, right?
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00:05:29.420I'm taking the train from basically Princeton slash like Trenton, New Jersey area down to DC to Union Station, and then taking the subway home to Chevy Chase, like by myself.
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00:05:31.980That's kind of a big deal as like a 16-year-old to be doing that.
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00:05:35.500And my parents, like, yeah, like if you want to come home, you can come home and just gotta figure it out and get it done.
00:05:35.660 -->
00:05:42.139And and that all led to I think me having a higher level of certainly independence, but also being much more ready for college.
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00:05:45.259Like most kids go to college and like I've never lived away from home in my life.
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00:05:48.060And your parents drop you off and they're like, peace, I'm out.
00:05:48.540 -->
00:05:49.740My my dad literally did that.
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00:05:54.220He literally was like, dropped me off, he uh helped me unpack and he was like, I gotta go.
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00:06:01.019My flights in a few in an hour, and took that rental car, drove right back to the airport and left.
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00:06:03.500He's like, This is easy for you though, you've done this before.
00:06:03.740 -->
00:06:04.540And he's right.
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00:06:07.420I was like, Cool, just like another year of high school.
00:06:07.660 -->
00:06:08.620Oh, that's awesome.
00:06:08.780 -->
00:06:11.019And you ended up going to uh Vanderbilt, right?
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00:06:12.379I did, yeah, loved it.
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00:06:14.540Early applied early decision.
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00:06:19.500Um, it was a really good school at the time, but not very sexy for people in the Northeast.
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00:06:23.819Um, and I was just, I don't know, I guess I've always been a little bit of a mildly contrarian thinker.
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00:06:25.500But I was like, this school is great.
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00:06:27.100Like it's what everything I wanted.
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00:06:31.180There's a reason I applied early, like location is in the city, but had its own little campus.
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00:06:36.540The education was great, um, great athletics, had like all the different pieces that I was like, this is the dope place to go.
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00:06:37.579So I applied early.
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00:06:39.180Lucky enough I got in.
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00:06:46.620Um, but I mean, like, I was student body president when I was there, like all the other things, and it really just it gave me all the opportunities um to do more.
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00:06:47.420So it was great.
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00:06:51.740Yeah, you uh so you had double major and a minor.
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00:06:53.899You studied uh philosophy.
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00:06:56.300Minor philosophy, minor, minor philosophy.
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00:06:56.780Okay.
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00:07:02.780So I dabble, I dabble in things when I can tell you some philosophical argument that I don't know that much about anymore.
00:07:03.019 -->
00:07:03.819Okay, got it.
00:07:03.980 -->
00:07:04.860Yeah, that's cool.
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00:07:06.620I love uh I love philosophy.
00:07:06.699 -->
00:07:09.579So do you still read any philosophy or I don't really.
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00:07:12.939I every once in a while I do, but but not a ton, um, unfortunately.
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00:07:14.139I probably should get back into it.
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00:07:14.939It's one of those things.
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00:07:17.259Like when I have more time, I will do this.
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00:07:18.699Yeah, yeah, I hear you.
00:07:18.860 -->
00:07:22.459And so that you do did you you also went to law school, right?
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00:07:22.939I did.
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00:07:24.939I after so after I finished Bainer Belt.
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00:07:30.939Um, actually, funny, I got an opportunity to stay in Nashville, and like there's some things that could have been really cool for me to do there.
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00:07:37.500But I was like, I'm a good son, my dad's a lawyer, I'm gonna follow in his footsteps, the usual sort of thing.
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00:07:38.939So follow in his footsteps.
00:07:39.019 -->
00:07:39.899I went to law school.
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00:07:44.939And I remember my dad saying, he's like, hey, look, when you get a law degree, you'll never be without a job.
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00:07:47.660And so I give it felt like the right, smart thing to do.
00:07:47.819 -->
00:07:50.060Um, but I wasn't that into law.
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00:07:52.379Uh, and so I also got my MBA at the same time.
00:07:52.459 -->
00:07:54.699So did a JD MBA combined.
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00:07:57.579Um, and when I finished, I took the bar.
00:07:57.740 -->
00:07:59.259I managed all four years of that.
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00:08:01.180So combined, you know, combined degree was four years.
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00:08:03.259If I did it separately, it would have been five.
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00:08:09.980Um, and when I graduated, I took the Maryland bar, thankfully passed it and went straight into business actually.
00:08:10.060 -->
00:08:19.100So I got a this is literally got a job um at a mid-sized sort of publicly traded tech company in the DC area right before the 2008 crash.
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00:08:20.300And I got really lucky.
00:08:20.379 -->
00:08:23.899I had a bunch of friends who didn't get jobs and it I think it kind of messed up their careers.
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00:08:24.699Yeah.
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00:08:25.500Yeah.
00:08:25.819 -->
00:08:27.899When did you decide you want to get into tech?
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00:08:28.139Right.
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00:08:32.059Because I know you so you start off as an attorney, but I wasn't practicing, right?
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00:08:33.740So the department I went to law school because I'm not sure.
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00:08:34.059Right.
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00:08:42.699You started like you said, so you thought you were gonna be an attorney, but during that time, had you already sort of decided, were you also considering getting into tech, or what was your Yeah, no, 100%.
00:08:42.939 -->
00:08:46.620I mean, like I was a kid, like with my grandfather bought us the first computer I ever had.
00:08:46.699 -->
00:08:53.340It was like I think a like HP 486 computer with the dial-up modem, like 288 baud dial-up modem.
00:08:53.659 -->
00:08:58.939And we were, you know, getting online and and going on AOL and all these other things, and like very cool.
00:08:59.019 -->
00:09:02.939And then I was that guy at boarding school reading Wired magazine all the time.
00:09:03.019 -->
00:09:05.579I still get Wired Magazine as a paper copy to my house.
00:09:05.659 -->
00:09:11.179I'm probably like the longest ever subscriber to it, but it's the only paper magazine I get nowadays.
00:09:11.419 -->
00:09:16.059Um, but uh, but but yeah, I'd always wanted to be in tech, like just reading about those things.
00:09:16.139 -->
00:09:18.700And like, you know, I graduate college and man, I kind of regret this.
00:09:18.779 -->
00:09:23.100Like Vanderbilt was one of the first 20 schools to get Facebook.
00:09:23.500 -->
00:09:25.899My senior year of my senior year of college.
00:09:26.060 -->
00:09:33.500It was 2004, which kind of dates me, I suppose, but like senior year of college, um got got Facebook, and I remember reading about it.
00:09:33.580 -->
00:09:42.700Like, this is like a bunch of like kids who dropped out of Harvard and rented a house in Silicon Valley and just started building this thing.
00:09:42.779 -->
00:09:47.419Like, I know Mark Zuckerberg started it, of course, at Harvard, but like they moved to Silicon Valley and started going.
00:09:47.740 -->
00:09:52.620And like I should have, I remember thinking at the time like I should like screw law school.
00:09:52.700 -->
00:09:55.259I should just go out to Silicon Valley and get started.
00:09:55.419 -->
00:09:57.340And I didn't, and I kind of regret that a little bit.
00:09:57.419 -->
00:10:03.340Like, no, I don't have real regrets, I don't really believe in regrets, speaking of philosophical philosophy, but like, but I sort of regret that a little bit.
00:10:03.419 -->
00:10:07.740Like, God, why wasn't I just gung-ho enough and just like what's the worst that could happen if I don't go to law school?
00:10:07.820 -->
00:10:09.100I'd go back to law school.
00:10:09.659 -->
00:10:14.860I should have just gone out of Silicon Valley and like just sat in front of their front porch and be like, I will do whatever you need me to do.
00:10:15.019 -->
00:10:16.379Well, your building's freaking awesome.
00:10:16.460 -->
00:10:17.340Let me get started.
00:10:18.860 -->
00:10:21.899I've done fine, but like that would have been a different trajectory.
00:10:22.220 -->
00:10:22.539All right.
00:10:22.620 -->
00:10:26.539So when did you uh and so you decided uh you had a mentor, right?
00:10:26.620 -->
00:10:32.539That gave you some advice that ultimately that's how you decided to move to uh to SF.
00:10:32.700 -->
00:10:33.259Is that right?
00:10:33.500 -->
00:10:45.580Yes, meant mentor is a long strong term, but um when I when I was so after grad school, uh I you know this is after grad school, I um was uh dating someone seriously.
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00:10:53.820She engaged at the time, um, and we uh called it off and I was working at this mid-sized tech company.
00:10:53.980 -->
00:11:02.779Um and I had always I would have moved out to San Francisco right off the bat, except she was someone who was from the DC area, and I was from the DC area, so of course it made sense.
00:11:02.860 -->
00:11:05.419We had family there to like move back to the DC area.
00:11:05.580 -->
00:11:09.340But once we called things off, I was like, why am I still here?
00:11:09.580 -->
00:11:12.299Like I've always wanted to be in Silicon Valley.
00:11:12.460 -->
00:11:16.060That is the the people that I sort of worship, like most people worship like celebrities.
00:11:16.220 -->
00:11:21.179Like, oh, I see Beyonce or or Taylor Swift or whatever, um, and they would know who they are.
00:11:21.419 -->
00:11:25.019I actually would know who Taylor Swift and Beyonce were, but like most people I really wouldn't.
00:11:25.179 -->
00:11:29.340Like, truthfully, if I met most celebrities, but like I don't, you're just a random person.
00:11:29.580 -->
00:11:35.580My celebrities were like Mark Zuckerberg or Elon Musk or like Jeff Bezos.
00:11:35.740 -->
00:11:38.620Um, like truly, like my my goal was to go work at Microsoft.
00:11:38.700 -->
00:11:47.019Like, I want to go work at Microsoft because I thought Microsoft and like Bill Gates were like the jam, which once again chose like how Dorky and Nerdia was, but like those companies are changing the world.
00:11:47.179 -->
00:11:47.980I want to go there.
00:11:48.139 -->
00:11:49.820Um, so anyways, called it off.
00:11:49.899 -->
00:11:56.940Uh, and I wanted the I took the conversation with this sort of mentor, and I was like, he was like, Look, you have to make a choice in life.
00:11:57.019 -->
00:12:02.620Like you you who you surround yourself with are the what you become to it to a large extent.
00:12:03.019 -->
00:12:10.940Um, and this by the way, this this guy was he was a Sequoia-backed, so top-tier venture capital fund, sequoia-backed funder, founder, CEO, based in DC.
00:12:11.820 -->
00:12:18.539Um, and he literally was like, Look, you if you want to be in tech, or sorry, if you want to be in politics, stay in DC.
00:12:20.139 -->
00:12:21.980If you want to be in finance, go up to New York.
00:12:22.379 -->
00:12:24.220If you want to be in media, go to LA.
00:12:24.379 -->
00:12:26.620And if you want to be in tech, like go to San Francisco.
00:12:27.419 -->
00:12:28.539And the reason is pretty simple.
00:12:28.620 -->
00:12:30.700And I think this advice, by the way, still holds for most companies.
00:12:30.779 -->
00:12:38.779And I know no offense to you being James, you know, you being in the DC area, but the the simple fact is like, yes, you can build amazing technology anywhere, right?
00:12:38.860 -->
00:12:43.740All you need is a laptop and an internet connection, and you can be anywhere on the planet Earth and build great stuff.
00:12:44.539 -->
00:12:56.220However, there's something to be said for the community that you surround yourself with, the questions they're asking, the discussions they're having, and essentially just even listening in, the osmosis effect of being part of that.
00:12:56.539 -->
00:12:59.340And that's what he meant by going to San Francisco, right?
00:12:59.419 -->
00:13:05.179If you want to be one of the best in the world, you need to compete with the best and be surrounded by the best and see what they're doing.
00:13:05.340 -->
00:13:07.899And so I was like, Yeah, like this is already always something I wanted to do.
00:13:08.060 -->
00:13:09.259So he kind of gave me permission.
00:13:09.500 -->
00:13:13.340And I applied to some jobs, got flown out here by a company.
00:13:13.580 -->
00:13:16.060Uh, they hired me literally, they made me an offer.
00:13:16.139 -->
00:13:24.700They were like, by the time I so they flew me back, I was boarding the plane at San Francisco Airport, SFO International, um, to fly back to DC.
00:13:24.860 -->
00:13:28.220And they were like, you will have an offer in your inbox by the time you land, right?
00:13:28.299 -->
00:13:30.060We didn't have internet on the airplane at the time.
00:13:30.299 -->
00:13:33.100We'll have what your offer in your inbox by the time you land.
00:13:34.060 -->
00:13:35.100Offer was there.
00:13:35.500 -->
00:13:37.580I don't even know if I negotiated it.
00:13:38.060 -->
00:13:40.379And they're like, Can you be here next week to start?
00:13:40.460 -->
00:13:41.899And I was like, I gotta give notice.
00:13:42.060 -->
00:13:43.419Like, I want to drive across country.
00:13:43.500 -->
00:13:47.019Like, that was one of my bucket list items, which I, by the way, have still never done, which is embarrassing.
00:13:47.179 -->
00:13:49.500But like, they're like, We need you out here right now.
00:13:49.580 -->
00:13:51.179I'm like, Well, welcome to Silicon Valley.
00:13:51.259 -->
00:13:51.740Heck yeah.
00:13:51.899 -->
00:13:56.460I'm flew out, found an apartment in like a day, went down to start my job.
00:13:56.700 -->
00:13:57.259That's awesome.
00:13:57.340 -->
00:13:58.620What company was this?
00:13:58.860 -->
00:14:00.860It was called Clearwell Systems.
00:14:01.100 -->
00:14:04.620So Clearwell, uh, they did like uh e-discovery.
00:14:04.700 -->
00:14:14.139So helping, so it's kind of good with my legal background, helping companies um uh basically read through massive amounts of documents for lawsuits and things like that.
00:14:14.299 -->
00:14:16.700And like I was in the business development teams, like partnership team.
00:14:16.779 -->
00:14:24.620So I would go across the country and like go meet with these, there were these small companies that basically did this e-discovery work for law firms.
00:14:24.860 -->
00:14:29.740And we would go meet with these companies, train them on how to use our software and get them encouraged and excited.
00:14:29.820 -->
00:14:34.539So I like go in and like train them, get to know their teams, push them, all that other stuff.
00:14:34.620 -->
00:14:37.179Um, it was fun and it was a great intro to things.
00:14:37.259 -->
00:14:40.139And and then the company, by the way, got acquired after 18 months of me being there.
00:14:40.299 -->
00:14:46.139Not not directly because of me, maybe indirectly in a small teeny part, but like they got acquired for 400 million.
00:14:46.220 -->
00:14:49.419And I was like, heck yeah, like welcome to Silicon Valley.
00:14:49.580 -->
00:14:51.820Like, I got paid a bunch of money for my equity.
00:14:51.980 -->
00:14:52.940It was awesome.
00:14:53.179 -->
00:14:54.539Yeah, that's awesome.
00:14:54.700 -->
00:14:56.860And you so you stayed on post-acquisition, right?
00:14:57.179 -->
00:14:57.659I did, yeah.
00:14:57.820 -->
00:14:59.179I did stay on for about a year.
00:14:59.259 -->
00:15:02.779So um kind of quasi golden handcuffs, needed to stay on for a year.
00:15:03.019 -->
00:15:03.419Cool.
00:15:03.580 -->
00:15:07.659Um, and left basically right at my year mark and started my first startup.
00:15:07.899 -->
00:15:09.019What was your first startup?
00:15:09.259 -->
00:15:16.539So we were doing uh it was called Virtue, and we were doing uh Virtue.us, so we were Virtuous.
00:15:16.700 -->
00:15:19.580Um was the our our naming convention.
00:15:19.740 -->
00:15:23.740Um, but the idea like this is also goes out so crazy when you're out in certain location.
00:15:23.899 -->
00:15:42.460It was we were trying to be the trust layer for all the companies building what was called the collaborative sharing community, basically, where it was like, hey, like I want to I need a drill, I can share it with my neighbor, or and then it became it morphed into Uber and Lyft and all those companies.
00:15:42.539 -->
00:15:55.419Because you remember, think back when people first started getting in someone's random car for Lyft, or really Lyft started the idea, um, or going to rent out someone's extra bedroom for Airbnb.
00:15:55.980 -->
00:15:57.340That scared a lot of people.
00:15:57.419 -->
00:15:58.220Like it was scary.
00:15:58.299 -->
00:16:03.899I still remember a conversation I had with my friend who lives in Iowa, and she was like, There's no chance I'm getting in some random stranger's car.
00:16:03.980 -->
00:16:05.980And I was like, You did it all the time with a cab.
00:16:06.060 -->
00:16:07.500It's some random stranger's car.
00:16:07.659 -->
00:16:11.179Like, yeah, they're theoretically like governed by the cab company, but what do you really know?
00:16:11.259 -->
00:16:16.220And of course, now we're getting in, now in San Francisco, we're getting in, you know, Waymo's that aren't driven by anybody.
00:16:16.460 -->
00:16:23.820Um, but like the but so I saw this ride thing, this whole community rising up, and I was like, I'm gonna do a whole trust verification layer for this.
00:16:23.899 -->
00:16:34.620Like, I literally got a ride across the city, not as an Uber ride, but like because I was at a party with him from the CEO, not Travis Klanick, but the CEO of Uber, who was before Travis kind of came back to become CEO.
00:16:34.779 -->
00:16:36.700We were just at a party and he's like, Oh, I live on the other side of the city.
00:16:36.779 -->
00:16:37.419I was like, I do too.
00:16:37.500 -->
00:16:38.940So we got a ride, we rode together on that.
00:16:39.019 -->
00:16:42.139And like, those are those weird connections that just happened in San Francisco.
00:16:42.379 -->
00:16:43.259Yeah, that's awesome.
00:16:43.580 -->
00:16:46.139So, what uh what ended up happening to your first company?
00:16:46.620 -->
00:16:47.419Failed.
00:16:47.659 -->
00:16:50.460Um shut down, yeah, shut down, failed.
00:16:50.700 -->
00:16:51.179What happened?
00:16:51.259 -->
00:16:54.539Um the the what happened is kind of interesting.
00:16:54.700 -->
00:17:01.899Um, so we turns out people weren't really willing to pay to verify other people, at least not the way we were we were doing it.
00:17:02.060 -->
00:17:10.700Um, I do think if we built it overseas, so because in the US you have social security numbers and you have other ways of like doing background checks, um, it wasn't as valuable in the US.
00:17:10.859 -->
00:17:16.539Um, overseas, we might have been able to build a really cool company, but um, we're American, so we didn't really know that.
00:17:16.619 -->
00:17:20.059Uh, and so what we did is we tried to pivot into actually background checks.
00:17:20.220 -->
00:17:25.099And so moving away from like using social, we were using social data to gather, like where did you go to college?
00:17:25.259 -->
00:17:26.460Are you verified with your college?
00:17:26.539 -->
00:17:29.579Are you verified with your job trying to use that data?
00:17:29.819 -->
00:17:35.179Um, and we pivoted into background checks, but it was a little bit too little, too late.
00:17:35.500 -->
00:17:38.059So we had conversations with some folks to acquire us.
00:17:38.220 -->
00:17:44.940Uh, one of them actually, the big lesson, the big mistake we made actually was we we had conversations with Okta to acquire us.
00:17:45.099 -->
00:17:48.379And it was, it would have been like a aqua hire, right?
00:17:48.460 -->
00:17:50.139It wasn't gonna be anything super special.
00:17:50.460 -->
00:17:56.619The mistake we made, and this is where I was just not too junior and didn't have good advisors in a sense, is like we should have said yes to that deal.
00:17:56.699 -->
00:18:01.019It would have screwed over over our investors, but we should we should have said yes.
00:18:01.179 -->
00:18:05.819Um, the reason we should have said yes is because one, we didn't know where Okta was gonna go.
00:18:05.899 -->
00:18:10.139And Okta's turned out to be a fantastic company, and we would have had really early equity.
00:18:10.219 -->
00:18:13.979Like literally, I'm sitting down with the CEO of Okta for lunch to talk through the acquisition.
00:18:14.059 -->
00:18:16.139Like that's how small they were at the time, right?
00:18:16.299 -->
00:18:19.259And like they were gonna give us like good jobs with good equity, all that stuff.
00:18:19.419 -->
00:18:20.379We should have said yes.
00:18:20.539 -->
00:18:24.139One, because it would have been great from an equity financial standpoint, but who wouldn't who knew?
00:18:24.219 -->
00:18:25.419Of course, you didn't really know that.
00:18:25.659 -->
00:18:28.459Two, what people don't get is you want to say you had an acquisition.
00:18:28.619 -->
00:18:30.779It would have been great for me to say, yeah, we got acquired by Okta.
00:18:30.939 -->
00:18:32.139Like that would have been fucking huge.
00:18:32.299 -->
00:18:35.899No one needs to know that I if I'd really hated it, I could have left the next day.
00:18:36.059 -->
00:18:39.339Got acquired, start one day at work there, and then quit the next day.
00:18:39.899 -->
00:18:40.779Could have done that.
00:18:40.939 -->
00:18:43.659Um, and you still can say, Hey, yeah, we got acquired by Okta.
00:18:43.739 -->
00:18:44.619That would have been awesome.
00:18:44.859 -->
00:18:47.259We didn't, though, because we were like, uh, is that a cool company?
00:18:47.339 -->
00:18:48.059Do we want to work there?
00:18:48.139 -->
00:18:50.539Like, if we were applying for normal jobs, would that be our top choice?
00:18:50.619 -->
00:18:51.500And we didn't know anything about it.
00:18:51.579 -->
00:18:53.019And we didn't, so we said no.
00:18:53.259 -->
00:18:56.139Um, and uh it was a failure on our part.
00:18:56.219 -->
00:18:58.939So we shut the company down, gave money back to investors.
00:18:59.019 -->
00:19:02.299So the right thing to do for investors, gave money back to them, and that was it.
00:19:02.539 -->
00:19:07.500What'd you uh what would you say is like the top takeaway, other than the acquisition piece, which in you did that?
00:19:07.739 -->
00:19:08.459Huge takeaway.
00:19:08.539 -->
00:19:13.419The other top takeaway was um actually that you never know where things lead.
00:19:13.500 -->
00:19:25.419So what I mean by that is because we had sort of pivoted into this background check and we were doing background checks, um, we had actually considered building a um automated background check system because the current systems currently sucked at the time.
00:19:25.500 -->
00:19:26.939And we were literally doing it manually for custom.
00:19:27.019 -->
00:19:31.019We were running with we had customers paying us revenue to do this work for them because it was so annoying.
00:19:31.179 -->
00:19:35.979We thought about building an API for that and we just kind of ran out of steam to make that happen.
00:19:36.219 -->
00:19:38.859Um, we should have fought through a little bit more.
00:19:39.179 -->
00:19:45.739The reason we should have fought through is because about six months later, a company that people might have heard of called Checker came out.
00:19:46.059 -->
00:19:53.019Checker does background checks, and Checker background checks has become, I don't know, they're probably worth many billions of dollars today.
00:19:53.579 -->
00:19:56.459We were there before them, had the right idea, we're doing it.
00:19:56.539 -->
00:19:59.659We some might not have been successful, but we were there before them.
00:19:59.899 -->
00:20:04.699So, one push through if you have an idea that's working and people are actually paying you money for, like, don't give that up.
00:20:04.779 -->
00:20:09.259Like, that is gold when people are willing, like the first idea that we had, people weren't giving us money for.
00:20:09.419 -->
00:20:10.779We pivoted into a new idea.
00:20:10.859 -->
00:20:14.459People are paying us money, not like hand over or fist, but they were paying us money for it.
00:20:14.699 -->
00:20:15.659One, stick with it.
00:20:15.739 -->
00:20:16.619That was a big lesson.
00:20:16.859 -->
00:20:18.619Two, if don't build something from it.
00:20:18.699 -->
00:20:26.459And what I mean by that is I was able to invest really early in Checker because I was like, that's gonna be a huge company because I literally tried to build that and I know there's a massive market.
00:20:26.539 -->
00:20:28.379So I was a really early investor in Checker.
00:20:28.619 -->
00:20:31.739So I got lucky, but I'm still an investor.
00:20:31.819 -->
00:20:35.099I would have rather been the CEO of it.
00:20:35.339 -->
00:20:36.459But those are lessons.
00:20:36.539 -->
00:20:39.099So those are probably two lessons is one, take the exit.
00:20:39.259 -->
00:20:42.059If you have an exit on the table, take it as a founder.
00:20:42.219 -->
00:20:43.179You should do that.
00:20:43.339 -->
00:20:49.500Um, and then two, use your knowledge about the industry to figure out how you can either invest or build something new thereafter.
00:20:49.819 -->
00:20:50.459That's interesting.
00:20:50.539 -->
00:20:55.099So I'm curious, like if that's like advice that you'd give across the board, like in terms of taking an exit.
00:20:55.179 -->
00:21:08.779Because, like, for instance, um, like I'm I'm building June right now, which is an AI interviewer, like we're very early stage, but we have pilots coming up with like really big names, and we'll be making like some pretty cool announcements soons.
00:21:08.939 -->
00:21:23.979But these are like very well-known tech companies that we have in our pipeline, and we've added probably 10 deals to our pipeline in the last month or so, five weeks, and so it's like it's one of those things it was moving really slow for about a year, and now like adoption of this tech is like out of nowhere exploding.
00:21:24.299 -->
00:21:31.019And so there's like there's going to be, I think, a lot of opportunities for very early stage strategic like acquisitions.
00:21:31.099 -->
00:21:33.659But it's like I kind of have mixed feelings uh about it.
00:21:33.819 -->
00:21:38.379Like we could part of it feels like the market's gonna be so saturated.
00:21:38.539 -->
00:21:43.739A lot of these all-in-one products are gonna be offering this, we're gonna be coming up and competing against them, you know.
00:21:44.379 -->
00:21:51.659Going to like a very early stage exit might make sense, but then it's also like, you know, I don't know if I'd really want to do something.
00:21:51.739 -->
00:22:03.019I I would almost like to build the company, get it further along, have a bigger exit, you know what I mean, versus just getting us to, I don't know, maybe mid-six figures in ARR, hopefully, in the next few months.
00:22:03.179 -->
00:22:04.379Like we're very early, right?
00:22:04.539 -->
00:22:09.099But if you know that that's sort of like the uh something we're kind of thinking through, me and a co-founder are thinking through.
00:22:09.179 -->
00:22:23.339It's like, do we want to just get into the six-figure ARR range and then basically sell to an all-in-one product that wants to add this, or do we just continue to push best in class, run solo and and maybe fundraise?
00:22:23.739 -->
00:22:26.939You know, I mean, look, uh there's no easy answer to that, to be clear.
00:22:27.099 -->
00:22:30.059And I think the market will dictate that for you to some extent.
00:22:30.299 -->
00:22:39.419However, um, I think most companies look, it's a really hard and long road to build a successful company, right?
00:22:39.500 -->
00:22:44.459You see these I I'm an investor in a company that you that you all should try called Whisperflow, if you haven't tried it.
00:22:44.539 -->
00:22:46.379So it's basically a dictation app, it's awesome.
00:22:46.779 -->
00:22:47.099Check it out.
00:22:47.259 -->
00:22:48.219Um look it up right now.
00:22:48.459 -->
00:22:55.500But the crazy thing about them is you know, like you hear these stories and they're they're now raising at I just there was something not publicly announced.
00:22:55.579 -->
00:22:56.459I don't know if it's even true.
00:22:56.619 -->
00:23:01.979So it's not any no private data that I have, that they're raising a new round at almost a 2 billion valuation.
00:23:03.099 -->
00:23:03.899That's crazy, right?
00:23:03.979 -->
00:23:04.619So this is the founder.
00:23:04.699 -->
00:23:06.059I've sat down with him for lunch, everything else.
00:23:06.139 -->
00:23:09.179Like, I don't know, he probably owns 25% of the company, right?
00:23:09.259 -->
00:23:10.619Let's even pretend it's 50%, right?
00:23:10.699 -->
00:23:12.379If it's 50%, he's a billionaire.
00:23:12.619 -->
00:23:15.339I mean, like, even if it's 25%, he's worth$500 million now.
00:23:15.419 -->
00:23:16.379That's insane, right?
00:23:16.459 -->
00:23:21.099And so people hear these stories and you're like, oh my God, like this is utterly crazy.
00:23:21.419 -->
00:23:24.779On the other hand, very, very, very few companies pull it off.
00:23:25.019 -->
00:23:27.739Um and their story is even indicative of that.
00:23:27.819 -->
00:23:28.459Like they pivoted.
00:23:28.539 -->
00:23:30.139So their original idea did not work.
00:23:30.299 -->
00:23:33.019They pivoted into this and it utterly took off.
00:23:33.179 -->
00:23:35.659So the market for them is dictated they should keep growing.
00:23:35.899 -->
00:23:45.419But I think for most founders, unless you either pivot into something you find that it's growing really quickly, and it is just like obvious how good it is, and you I would I would try to sell if you have an opportunity.
00:23:45.739 -->
00:23:46.379Yeah.
00:23:46.619 -->
00:23:47.659Yeah, it's interesting.
00:23:47.739 -->
00:23:48.619It's really interesting.
00:23:48.699 -->
00:23:49.500I'll keep you posted.
00:23:49.739 -->
00:23:56.619You should be using if you're not if you're not using a dictation app, you should be using your dictat a dictation app for literally, it's it's almost perfect.
00:23:56.779 -->
00:23:58.379It will format the whole thing for you.
00:23:58.539 -->
00:24:02.939I don't even read over most of the time what I say because it will automatically clean it all up and write it well.
00:24:03.259 -->
00:24:07.579They're still uh a relatively small company from an employee perspective, too.
00:24:07.899 -->
00:24:13.179They are, um, which also goes to show how crazy these businesses are now is you don't need a lot of people to build great companies.
00:24:13.259 -->
00:24:16.379And that's another thing that we I talk about a ton with what we do at Chore.
00:24:16.619 -->
00:24:21.259Like they still need someone to run back office operations and like they should be using us and all these other things.
00:24:21.339 -->
00:24:34.139Actually, Whispers not, they should be, but um, but uh you don't want to hire lots of people, and that's also once again the the crazy world we're in is you can build these companies that are worth two billion dollars, and I don't know, I have 20 people on the team.
00:24:34.299 -->
00:24:35.419Like, yeah, it's crazy.
00:24:35.659 -->
00:24:38.059It is bonkers nowadays.
00:24:38.699 -->
00:24:40.379And that's that's what people need to understand.
00:24:40.539 -->
00:24:45.899Is like you can the ability to build something that grows massively is not hard.
00:24:46.219 -->
00:24:52.859Well, it it's hard to, but it's hard to get that idea that people will uptake and be like, yeah, this is my dream come true.
00:24:53.099 -->
00:24:53.339Right.
00:24:53.659 -->
00:24:54.139That's hard.
00:24:54.379 -->
00:24:55.500Yeah, so tell us about chore.
00:24:55.659 -->
00:24:57.500Like, so what are you what are you building now?
00:24:57.819 -->
00:24:59.579Yeah, I mean, the whole thesis of chore is pretty simple.
00:24:59.659 -->
00:25:00.619We do the back office chores.
00:25:00.859 -->
00:25:03.259We we do we we do love the name, by the way.
00:25:03.500 -->
00:25:03.819Thank you.
00:25:03.979 -->
00:25:04.219Thank you.
00:25:04.299 -->
00:25:05.419It's totally memorable.
00:25:05.500 -->
00:25:07.899I'll you know, hold up my water bottle for the video viewers.
00:25:08.139 -->
00:25:11.500Um those who are listening, it just says chore on it.
00:25:11.579 -->
00:25:14.779It's a big big water bottle to get my my uh hydration in every day.
00:25:15.019 -->
00:25:16.859But yeah, the idea, the idea is pretty simple.
00:25:17.019 -->
00:25:27.339Like it is every company in the world has a standard problem called run your like back office operations, which is HR, human resources, finance compliance, and then for startups, equity.
00:25:27.419 -->
00:25:28.379Every company has this problem.
00:25:28.459 -->
00:25:30.859And yet usually what happens is the founders do that work themselves.
00:25:30.939 -->
00:25:34.619And what I just don't understand is most founders I know hate doing chores.
00:25:34.779 -->
00:25:39.019Like if someone said to them, you need to go do this chore, you'd be like, What are you talking about?
00:25:39.099 -->
00:25:40.379Like, no, I'm gonna hand it off to someone else.
00:25:40.459 -->
00:25:41.339I'm gonna delegate it.
00:25:41.419 -->
00:25:47.259I'm gonna give, I don't want to go do this because I make so much more money by doing the things that I'm great at that I love doing.
00:25:47.419 -->
00:25:48.459So that's what I'm gonna spend my time on.
00:25:48.539 -->
00:25:52.539And then when they say, Oh, but you need to do, but back office, most founders are like, Well, I guess I have to do that myself.
00:25:52.619 -->
00:25:53.819I have to go run HR myself.
00:25:53.979 -->
00:25:55.579It's like, no, what are you talking about?
00:25:55.739 -->
00:25:55.979Right.
00:25:56.379 -->
00:26:01.179Like, James, you're world class of building hiring like workflows in in apps.
00:26:01.419 -->
00:26:04.059Why spend any time on like HR specifically, right?
00:26:04.219 -->
00:26:06.779Like that's not the kind of HR that you're good at, the hiring stuff.
00:26:06.939 -->
00:26:08.459Like, why spend time on that?
00:26:08.619 -->
00:26:12.779Or another example would be a simple one um to use real chores as an example.
00:26:12.939 -->
00:26:14.699I don't know about you, but I don't like doing laundry.
00:26:14.859 -->
00:26:17.099I don't like doing my laundry, I don't like folding my laundry.
00:26:17.179 -->
00:26:19.019I find it to be a bad use of my time.
00:26:19.179 -->
00:26:20.859Um, that's a chore to me.
00:26:21.099 -->
00:26:22.939To be clear, my wife actually likes doing laundry.
00:26:23.019 -->
00:26:27.339So for her, it's not, but she doesn't like doing anyone else's laundry but her own.
00:26:27.419 -->
00:26:28.459I have two kids.
00:26:28.619 -->
00:26:32.699So I guess what I do, and for most people, it just parents have to suck it up.
00:26:32.779 -->
00:26:36.299They do their kids' laundry, or at some point your kids get old enough and they do their own laundry.
00:26:36.459 -->
00:26:37.659I think that's silly.
00:26:37.899 -->
00:26:43.819So my time is worth more either with my my my work or with my family than doing laundry.
00:26:43.979 -->
00:26:44.939And so, guess what I do?
00:26:45.019 -->
00:26:49.099I take it to a wash and fold place near my house and they do my laundry for me, and I pay them for the privilege.
00:26:49.339 -->
00:26:50.299That is a good trade-off.
00:26:50.379 -->
00:26:54.779Or another example that I would say some people don't love cooking, or you just don't have time for it sometimes.
00:26:54.859 -->
00:26:57.739Like there's better things to do with your time than cooking a full nice meal every night.
00:26:57.899 -->
00:26:58.619So, what do you do?
00:26:58.699 -->
00:27:01.979You order a burrito, you order food out, you get it delivered to your house.
00:27:02.219 -->
00:27:11.979It is way more money to order burrito delivery than to just order that just to open a can of beans, get a tortilla, and like some chicken.
00:27:12.059 -->
00:27:14.939You can make your own burrito for cheap, but why do people order out?
00:27:15.099 -->
00:27:15.819It tastes better.
00:27:15.979 -->
00:27:20.779Someone else is doing the work, someone else is making the mess of all the pots and pans and everything else to do the work.
00:27:20.939 -->
00:27:23.500All you have to do is unwrap something from silverfoil.
00:27:23.579 -->
00:27:25.819I think the same thing applies to back office operations.
00:27:25.979 -->
00:27:28.779It's insane that founders think they need to own the stuff themselves.
00:27:28.859 -->
00:27:29.979So that's what we're building.
00:27:30.219 -->
00:27:33.099So you work with a lot of early stage companies or what like what?
00:27:33.579 -->
00:27:33.899Yeah.
00:27:34.219 -->
00:27:34.459Yep.
00:27:34.619 -->
00:27:35.899Early stage founders.
00:27:36.139 -->
00:27:39.500Uh to be clear, this problem exists with every SB in the world.
00:27:39.659 -->
00:27:41.019And frankly, every mid-sized company.
00:27:41.099 -->
00:27:42.779Like some of our customers are up to 200 people.
00:27:42.859 -->
00:27:44.859Like they're not early stage startups, really.
00:27:45.019 -->
00:27:50.779But yeah, I mean, this is a huge problem across the board where commercial, like, oh yeah, I'm doing this work myself.
00:27:50.939 -->
00:27:52.219I didn't even know there was a solution.
00:27:52.539 -->
00:27:52.859Got it.
00:27:52.939 -->
00:27:53.819Yeah, that that's great.
00:27:53.979 -->
00:27:58.139I'm assuming like you started what, three a few years ago, right?
00:27:58.539 -->
00:27:59.419Torge weird.
00:27:59.500 -->
00:27:59.659Yeah.
00:27:59.899 -->
00:28:00.059Okay.
00:28:00.219 -->
00:28:00.779Oh, go ahead.
00:28:00.859 -->
00:28:01.019Yeah.
00:28:01.179 -->
00:28:04.379Um, no, no, it's a weird company, and it's some good lessons too, I suppose.
00:28:04.619 -->
00:28:08.459We spun out of, so my last company was a company called Abstract Ops.
00:28:08.939 -->
00:28:13.899Uh, we started, we raised$10 million, top-tier investors with a very simple thesis.
00:28:14.059 -->
00:28:18.139We are going to automate back office work, the stuff that I just talked to you about.
00:28:18.299 -->
00:28:19.339We're going to automate the whole thing.
00:28:19.419 -->
00:28:22.619And once we automate it, it's going to we'll revolutionize the world, right?
00:28:22.699 -->
00:28:24.619And then no one has to do this work anymore.
00:28:24.779 -->
00:28:27.179Uh, we had a small services team internally, right?
00:28:27.259 -->
00:28:28.539This is a very standard for tech companies.
00:28:28.699 -->
00:28:31.099Like, okay, like here's all this beautiful, amazing tech we're building.
00:28:31.259 -->
00:28:35.339But until we get everything fully built out, we're gonna have a services team help us do the work.
00:28:35.579 -->
00:28:38.219So we had our services team doing the work.
00:28:38.459 -->
00:28:40.619Turned out two years in, we actually had a really good business.
00:28:40.699 -->
00:28:42.139Like we had real revenue, things like that.
00:28:42.219 -->
00:28:45.579It was like doing well, but the tech product wasn't really working.
00:28:45.739 -->
00:28:55.339Um, and we were losing money on our services business because we weren't charging the right amount because chakra, we were underpricing, so we could get customers for it and we were subsidized by venture dollars.
00:28:55.579 -->
00:28:56.859So, what did we do?
00:28:57.179 -->
00:29:00.219We ended up uh deciding we had to split the company in two.
00:29:00.459 -->
00:29:04.379So my co-founder took toward the tech company and pivoted that business.
00:29:04.619 -->
00:29:07.739I took the services arm and created chore with it.
00:29:07.819 -->
00:29:12.779So we already had some customers in business when we started and then have grown it pretty significantly since then.
00:29:13.019 -->
00:29:13.739Yeah, that's great.
00:29:13.819 -->
00:29:14.379That's awesome.
00:29:14.619 -->
00:29:24.059Are you exclusively focused on the founder profile or do you see yourself expanding outside of that tech founder early stage?
00:29:24.779 -->
00:29:26.299I've made some mistakes on that front.
00:29:26.379 -->
00:29:26.539Yeah.
00:29:26.619 -->
00:29:33.179I mean, like, look, I think we we've tried other verticals, but probably not in the way that really led to any success.
00:29:33.419 -->
00:29:37.019So in the short term, we're trying to stay super focused on the founder vertical.
00:29:37.259 -->
00:29:42.699The simple fact is most founders, not all of them, but most generally understand their time is valuable.
00:29:42.859 -->
00:29:43.500Number one.
00:29:43.659 -->
00:29:50.299Number two, they realize that they're probably world class at doing something, which is not back office work, right?
00:29:50.379 -->
00:29:53.500If they were world class at doing back office work, I hope they start a competitor to chore.
00:29:53.659 -->
00:29:55.819Like that's what you should do if that's your world-class skill set.
00:29:56.059 -->
00:30:01.099And in most cases, they realize that time, once you get funding from VCs, you are on the clock, right?
00:30:01.179 -->
00:30:04.539So we've, you know, I've done 200 plus investments as an angel investor.
00:30:04.779 -->
00:30:12.859You're on the clock when you get money from a VC, like when you talk about fundraising for you, for you all, once you raise, you have 18 months to make it work or not work.
00:30:13.019 -->
00:30:13.579That's it.
00:30:13.739 -->
00:30:20.299So if you waste any of that, and investors give you the money not to save it in some bank account with low interest rates.
00:30:20.779 -->
00:30:23.259They give you the money to invest it.
00:30:23.659 -->
00:30:24.859And what does investing it mean?
00:30:25.019 -->
00:30:28.219It means putting it in ways that help you grow the business.
00:30:28.619 -->
00:30:36.379One of the key ways to grow the business is give yourself, because you have a superpower as a founder, give yourself those superpowers to grow the business as fast as you can.
00:30:36.619 -->
00:30:40.779Um, which means delegating everything that's not your core product, including back office work.
00:30:41.019 -->
00:30:41.179Right.
00:30:41.339 -->
00:30:42.699Most founders understand that.
00:30:42.859 -->
00:30:44.539So that's our target market right now.
00:30:44.619 -->
00:30:46.859And once we conquer that, we're gonna conquer the world.
00:30:47.579 -->
00:30:48.619Usual statement.
00:30:48.939 -->
00:30:49.659Nice, nice.
00:30:49.819 -->
00:30:51.979So, what's your obsession for 2026?
00:30:52.459 -->
00:30:55.579My main obsession for 2026 is AI, um, understandably.
00:30:55.659 -->
00:30:57.579Um, look, I live in San Francisco, I'm red pilled.
00:30:57.659 -->
00:31:01.099I can talk all about the dangers and things that I see there right now.
00:31:01.339 -->
00:31:06.379Um, but before before we get talking about the meta dangers, it's the answer, it's AI.
00:31:06.619 -->
00:31:08.699So you said something interesting to me earlier.
00:31:08.779 -->
00:31:21.019You said that uh basically companies that aren't focusing on transfer transforming their business to an AI native business in 2026 are gonna be out of business by the end of 2027.
00:31:21.259 -->
00:31:21.579Yeah.
00:31:21.819 -->
00:31:22.299Right.
00:31:22.619 -->
00:31:28.299So with your business, like what are like specifically, what are you doing?
00:31:28.699 -->
00:31:30.459I mean, so we're a services business, right?
00:31:30.539 -->
00:31:32.459And so people would say it's hard to AI that.
00:31:32.619 -->
00:31:39.979Um, we're building a ton of things to automate the work that our team does, how they do it, the data that they get, the steps they need to take to get that work done.
00:31:40.139 -->
00:31:50.939We're tracking every single element to see if we can reduce time and cost and every aspect of that, um, leading to hopefully a doubling of output for the same amount of time a person's working.
00:31:51.019 -->
00:31:56.699I'm not asking my team to work more hours, but I want them to work smarter hours overall.
00:31:56.859 -->
00:31:57.979And so, because guess what?
00:31:58.059 -->
00:31:59.979You can have AI do a lot of the different work.
00:32:00.219 -->
00:32:07.979So the thing that a lot of people don't really realize for for most jobs, for better or worse, your job is like moving data from one place to the next.
00:32:08.059 -->
00:32:13.259Like you're essentially copying data around, which is kind of crazy if you break it down into its component parts.
00:32:13.500 -->
00:32:16.859Um, AI is really good at that and it's really fast.
00:32:17.339 -->
00:32:22.939So, like if your job is moving data from place to place to place to place, why can't AI do a lot of that?
00:32:23.179 -->
00:32:32.939And that's what we're focused on is getting rid of the mundane, boring copy-paste work and letting AI do that and then have the humans do the part that is actually difficult.
00:32:33.179 -->
00:32:43.579So, like when you think about like implementing AI as a services company, are you gonna be leveraging agents and tools behind the scenes, or is this gonna be stuff you're actually implementing in your customers' environments?
00:32:43.979 -->
00:32:45.500Um, agents and tools behind the scenes.
00:32:45.579 -->
00:32:56.619And so, like, we'll have a full platform that people will be able to log into, use at some point, even hopefully like almost a SaaS product that customers can turn on to run their operations themselves and kind of call for human help when you need it.
00:32:56.699 -->
00:33:05.579Because like the work we're doing is still you can't, to the best of my knowledge, I've never seen anyone actually really get something that can be fully automated end to end with AI in the back office.
00:33:05.819 -->
00:33:09.659Like, once again, I spent$10 million of EC money trying to do this with like old tech.
00:33:09.819 -->
00:33:14.939Yeah, and we're now being smart, we're using our own cash from our own money that we make because we're bootstrapped at chore.
00:33:15.259 -->
00:33:18.219We're using our own cash to try to build the stuff ourselves today.
00:33:18.379 -->
00:33:21.500Um, but it's hard and you still need people doing some of the work today.
00:33:21.659 -->
00:33:24.699It's not, you're not, we're not at a point where you can be automate, automated all of it.
00:33:24.939 -->
00:33:25.899Yeah, for sure.
00:33:26.139 -->
00:33:26.619Got it.
00:33:26.779 -->
00:33:27.019Yeah.
00:33:27.179 -->
00:33:29.179And just to dial in on hiring, right?
00:33:29.259 -->
00:33:32.619Because it's primarily our show is about talent acquisition, right?
00:33:32.699 -->
00:33:34.939And a lot of talent acquisition leaders tuning in.
00:33:35.019 -->
00:33:37.500So, you I mean, as a services company, you do a lot of hiring, right?
00:33:37.579 -->
00:33:40.859And you do a lot of hiring with folks that are probably interacting directly with customers.
00:33:40.939 -->
00:33:47.500And it's like you're like these are to some extent like what's driving revenue, truly, like directly.
00:33:47.819 -->
00:33:56.139Um and so I'm just curious, like from a talent acquisition standpoint, like what is most important for your business?
00:33:56.219 -->
00:34:03.099Like, what are you focused on when it comes to hiring and how you do it to ensure that your company can continue to be successful?
00:34:03.339 -->
00:34:05.339So I'm gonna give you a macro answer to start.
00:34:05.419 -->
00:34:07.019Um, and maybe not quite answer your question.
00:34:07.099 -->
00:34:08.780So make sure you come back to that and push me on that.
00:34:09.019 -->
00:34:14.460Um the macro answer is basically I think it's insane that companies want to hire more people.
00:34:15.179 -->
00:34:17.900Like, so so my macro answer is don't hire people.
00:34:18.059 -->
00:34:19.260Don't hire more people.
00:34:19.500 -->
00:34:22.780Um, the reason I'll actually pause there.
00:34:23.019 -->
00:34:24.619What questions do you have about that?
00:34:25.500 -->
00:34:27.500So uh I know this is the hiring show.
00:34:27.820 -->
00:34:28.619No, I mean I get it.
00:34:28.699 -->
00:34:34.380Like, I mean because well, I mean, I have an embedded recruiting and RPO firm, so it's um and and also June, the AI interviewer.
00:34:34.539 -->
00:34:41.420It's like both essentially are helping companies limit the amount of W-2s that they hire, right?
00:34:41.579 -->
00:34:55.019Like, so they can leverage uh Secure Vision's embedded RPO, get great senior recruiters or tech or process, delivery lead, everything without actually adding W-2 headcount, or they can optimize with AA AI with June, right?
00:34:55.099 -->
00:34:57.900So that they get additional capacity back to their existing team.
00:34:58.059 -->
00:35:03.420So it's we help I help companies essentially not hire W2, right?
00:35:03.739 -->
00:35:07.019And let me so so I mean I'll tell you my thoughts on like why, right?
00:35:07.099 -->
00:35:12.059So here's what people need to the old school mentality, always was like, hey, we have a task that needs to get done.
00:35:12.219 -->
00:35:13.339I don't know how to do it.
00:35:13.500 -->
00:35:15.420Let's hire someone to go do this for us.
00:35:15.579 -->
00:35:17.420And you'd hire someone internally.
00:35:17.659 -->
00:35:18.859Here's the problem.
00:35:19.339 -->
00:35:23.019Like the stats, I wrote a post in this, but I'm still gonna butcher some of the stats.
00:35:23.179 -->
00:35:26.299The stats for full-time employees freaking suck.
00:35:26.619 -->
00:35:29.099Like, most employees are bad employees.
00:35:29.179 -->
00:35:33.259And don't get me wrong, like, I love my team, I think they're great, but most employees are bad employees.
00:35:33.420 -->
00:35:38.539So the fact is, like, something like 50% of your employees will fail within two years, just because like it didn't work out.
00:35:38.619 -->
00:35:41.259They're not good, they don't get it done, they don't like it, whatever.
00:35:41.420 -->
00:35:45.980Um, I think the other stat is like 50% of your employees at any given time are looking for other jobs.
00:35:46.219 -->
00:35:49.099Maybe not actively, maybe passively, but they're like looking for their jobs.
00:35:49.339 -->
00:35:54.380Um, something like 10 or 20% of them are like actively working against the company at any given moment.
00:35:54.619 -->
00:35:59.739It's like, by the way, this is this all comes from a post about why AI is going to replace most workers.
00:35:59.980 -->
00:36:03.980Because like most employees aren't good at like overall what they do.
00:36:04.139 -->
00:36:08.219And yet people still think, and I come across founders all the time, they're like, well, I need to hire someone for this role.
00:36:08.380 -->
00:36:13.819I actually talk to a company today and they're like, well, we're deciding like, do we keep using you guys or do we like hire internally?
00:36:13.980 -->
00:36:16.940And like, why would you ever want to hire internally for this role?
00:36:17.099 -->
00:36:19.819Yes, we are more expensive than a full-time person.
00:36:20.139 -->
00:36:24.219So I get it, and we don't you don't get as many hours from us as a full-time person.
00:36:24.380 -->
00:36:26.940So I understand that trade-off, but that's a this is a big company.
00:36:27.019 -->
00:36:29.179It's not for smaller companies, it definitely doesn't make sense.
00:36:29.339 -->
00:36:32.059But if you're like looking even one-to-one, sure.
00:36:32.219 -->
00:36:32.859But guess what?
00:36:33.019 -->
00:36:34.139You don't have to manage us.
00:36:34.219 -->
00:36:36.219You don't have to recruit us at all.
00:36:36.380 -->
00:36:40.139Like you don't have to spend all the time interviewing a dozen plus people to figure out what to hire for.
00:36:40.539 -->
00:36:42.619Two, you don't mess up the hire.
00:36:42.779 -->
00:36:50.380Because like if I'm a, you know, if I'm an AI expert and I'm now trying to hire a head of HR, I've never hired a head of HR in my entire life.
00:36:50.539 -->
00:36:52.940How am I gonna be good at hiring for that role?
00:36:53.259 -->
00:36:55.500Probably gonna fail because I've no as a blind leading the blind.
00:36:55.579 -->
00:36:56.299I'm gonna mess it up.
00:36:56.380 -->
00:36:59.259Then I have to onboard them, maybe train them a little bit.
00:36:59.420 -->
00:37:00.779I'm gonna fail all of that.
00:37:01.259 -->
00:37:02.699So these hires don't work out.
00:37:02.940 -->
00:37:08.059Like they just like it literally the cost of a hire, if you actually look at the numbers, let's pretend a hire is 100K a year hire.
00:37:08.460 -->
00:37:10.940The actual end-to-end cost for that person is double it.
00:37:11.019 -->
00:37:24.779So like the numbers still pretty clearly, like it's about double the cost for that employee when you look at the all-in cost of like, once again, the time it takes to recruit, to onboard, to train, get them going, then to have them get sick, then they leave a year and a half in, then you're back to square one.
00:37:24.940 -->
00:37:30.940All these costs add up versus hiring a vendor who say, get me this job, get this, do this job for me.
00:37:31.099 -->
00:37:32.619If you do it, I'll keep paying you.
00:37:32.779 -->
00:37:36.859And if you don't, I'll let you go and I'll find another vendor who says they can do it better.
00:37:37.579 -->
00:37:43.500Okay, yeah, I'm paying the vendor a little bit more money, but the vendor's delivering me exactly what I want when I want it.
00:37:43.659 -->
00:37:46.940And it's up to them to figure out how to hire, train, manage, get people.
00:37:47.179 -->
00:37:49.339They will build the best tools for the work that they're doing.
00:37:49.500 -->
00:37:58.699I don't have to worry about building, like, once again, you talk to some big AI company, and it's like, wait, you're trying to build your own AI HR workflows.
00:37:58.779 -->
00:37:59.900Like, what are you talking about?
00:37:59.980 -->
00:38:07.819You have a core product you're trying to build over here to get to market to your customers, and like you're gonna try to automate AI processes because you have clawed code.
00:38:07.980 -->
00:38:09.099Like, what are you talking about?
00:38:09.259 -->
00:38:11.659What a bad use of your time! Like, that's not your product.
00:38:11.739 -->
00:38:12.460You can't sell that.
00:38:12.699 -->
00:38:14.299You don't want to maintain it, anyways.
00:38:14.380 -->
00:38:15.259So I keep ranting.
00:38:15.339 -->
00:38:21.339The short and then the last piece, I guess, last piece I'll add is like speaking when you're going to fundraise, what do VCs care about?
00:38:21.500 -->
00:38:27.099The new metric now is ARR, annual annual recurring revenue, current FTE.
00:38:27.500 -->
00:38:28.940So full-time employee, right?
00:38:29.019 -->
00:38:29.900Or full-time equivalent.
00:38:30.059 -->
00:38:32.699If you have contractors, they're not considered an FTE.
00:38:32.859 -->
00:38:36.859So you can have lots of contractors, and your numbers can look great who are flexible, fire them anytime.
00:38:36.940 -->
00:38:39.420You don't owe me severance if you fire chore.
00:38:39.819 -->
00:38:41.420Why would you ever hire people?
00:38:41.900 -->
00:38:43.019Sorry, that's my rant.
00:38:43.099 -->
00:38:46.699But like, I seriously, like the the answer should be for most people today.
00:38:46.859 -->
00:38:51.579Either hire a contractor to do the work or try to build it with AI and automate it.
00:38:51.659 -->
00:38:53.339The last resort is hiring a person.
00:38:53.579 -->
00:38:56.699How do you ensure that you hire great people for your team?
00:38:57.339 -->
00:39:01.900We, this goes to actually the point of why you should never try to hire people, at least for the type of work we do.
00:39:01.980 -->
00:39:04.460But once again, I believe that's the case for many industries.
00:39:04.619 -->
00:39:05.900Um, it's really hard.
00:39:06.139 -->
00:39:10.380It's really hard to hire great people for the work that any company does.
00:39:10.539 -->
00:39:13.259Um, I was talking to my executive coach this morning on this exact topic.
00:39:13.420 -->
00:39:15.179He's like, he's working with a bunch of different companies.
00:39:15.259 -->
00:39:17.339He said, It is so hard to hire good people.
00:39:17.500 -->
00:39:19.259It's always been hard to hire good people.
00:39:19.420 -->
00:39:22.380He actually thinks it's harder now, which I find I actually disagree.
00:39:22.539 -->
00:39:29.019I think it's getting easier to hire good people because more and more people are unemployed and they're having trouble getting jobs.
00:39:29.099 -->
00:39:32.059So it's actually easier to hire good people nowadays.
00:39:32.380 -->
00:39:34.139Um, but how do you ensure it?
00:39:34.219 -->
00:39:38.299We have a very detailed process we've we've updated over three and a half, almost four years.
00:39:38.460 -->
00:39:41.659Where, like, so for us as an example, we have a whole hiring process.
00:39:41.819 -->
00:39:44.460And to be clear, you can't just apply on it.
00:39:44.619 -->
00:39:48.299There's actually a bunch of embedded tests in the process, which people don't even know about.
00:39:48.539 -->
00:39:49.980Like, I'll give you one example.
00:39:50.219 -->
00:39:55.179Um, we have very specific instructions in the application of what to do.
00:39:55.739 -->
00:40:01.980Like, literally, one of the, I think one of the things is like, please make sure you put in the subject line, you know, we love chore.
00:40:02.139 -->
00:40:04.699That's not what it does, but I but let's pretend that's what it says, right?
00:40:04.940 -->
00:40:08.699If you don't follow that instruction exactly, it means you're not detail-oriented.
00:40:08.940 -->
00:40:12.299And it means you're not a fit for the job we need you to do here automatically.
00:40:12.619 -->
00:40:14.940Because your your folks need to be incredibly detail-oriented.
00:40:15.259 -->
00:40:15.579Correct.
00:40:15.739 -->
00:40:25.259And so if you can't while you're applying for a job, if you can't get it right when you're applying for a job, which is like you're hopefully showing off the best if you're ever gonna be, you're definitely not gonna do it when you're here full time.
00:40:25.339 -->
00:40:31.019And until we so we've created tests that you can't AI, you can't answer the AI like some AI exercise.
00:40:31.179 -->
00:40:37.819It's literally various parts of the entire hiring process itself have been set up as a test.
00:40:38.059 -->
00:40:39.099Yeah, for sure.
00:40:39.339 -->
00:40:41.579How much do you focus on behavioral fit?
00:40:41.819 -->
00:40:46.940Um, a decent amount, but be what it means to have a behavioral fit continues to change.
00:40:47.099 -->
00:40:51.659So we're more and more focused on like, does someone have agency, like high agency individuals?
00:40:51.819 -->
00:40:53.179Do they take action on our their behalf?
00:40:53.420 -->
00:40:55.420Yeah, I guess it sounds like in a way that's that's behavioral, right?
00:40:55.500 -->
00:41:00.859Like you try to have this profile of like, you know, like the type of person that's successful.
00:41:01.099 -->
00:41:01.420Correct.
00:41:01.500 -->
00:41:02.059And we absolutely do.
00:41:02.139 -->
00:41:03.900So that's a big focus for us right now.
00:41:04.139 -->
00:41:09.500Um, but it's hard to find that in higher flat because everyone says, like, oh, look at all the things I've done in my past, and I take care of.
00:41:09.579 -->
00:41:12.539And it's like, but we we try to look for that a lot.
00:41:12.619 -->
00:41:17.179And if we don't find it pretty quickly, we also have gotten really good at letting people go.
00:41:17.819 -->
00:41:19.900Yeah, you gotta let people go quickly.
00:41:20.139 -->
00:41:22.859I mean, everyone says that, but it's harder, easier said than done.
00:41:22.940 -->
00:41:23.900But I'll give you an example.
00:41:24.059 -->
00:41:29.019I've we've kind of revamped our entire go-to-market team over the past two months.
00:41:29.339 -->
00:41:31.980Um, and as part of that, let a lot of people go.
00:41:32.139 -->
00:41:40.299And uh as a clear example, we've hired three salespeople, and I've let two of those three go within two weeks of them being here.
00:41:40.380 -->
00:41:41.179And they were shocked.
00:41:41.420 -->
00:41:45.179I'm like, I laid out pretty clear metrics for what we expected when we started.
00:41:45.259 -->
00:41:48.059We all agreed on the metrics that you're targeting.
00:41:48.699 -->
00:41:50.139You didn't ask me more questions.
00:41:50.219 -->
00:41:51.980You just said, yep, we're things are great.
00:41:52.059 -->
00:41:53.500Two weeks later, you didn't get it done.
00:41:53.819 -->
00:41:55.579I don't have time to look over your shoulder every day.
00:41:55.739 -->
00:41:56.779I need you to be self-driven.
00:41:56.859 -->
00:41:58.699If you're not, it's not gonna work.
00:41:59.259 -->
00:42:08.059Yeah, I mean, I I think um being able to quickly identify whether somebody's gonna work out or not is is incredibly important.
00:42:08.219 -->
00:42:14.299And you need to know the role well enough and have clear enough uh performance standards to where you can identify it quickly.
00:42:14.460 -->
00:42:18.219Like which is why you shouldn't hire people in your company.
00:42:18.460 -->
00:42:24.539Because most founders, if you're a world-class founder, you're world-class at something.
00:42:24.699 -->
00:42:27.259Like that's why you got funding, that's why you're doing what you're doing.
00:42:27.420 -->
00:42:28.539You do not have knowledge.
00:42:28.699 -->
00:42:33.900I'll just use operations because we know well, you know, you're a world-class recruiter, right, James?
00:42:34.059 -->
00:42:36.219Like, you know how to run those businesses, what that looks like.
00:42:36.380 -->
00:42:40.299But you have no context of what a world-class operator looks like.
00:42:40.539 -->
00:42:43.500You don't know what a great person to run your operations is.
00:42:43.659 -->
00:42:46.699You've never hired for those people, and maybe you have a little bit, but like you don't really know.
00:42:46.859 -->
00:42:48.059You don't really know what the job looks like.
00:42:48.139 -->
00:42:50.219So, how do you measure and metric outcomes for them?
00:42:50.380 -->
00:42:51.179You don't know how to do it.
00:42:51.339 -->
00:42:53.819And so you're gonna mess up that hire and it's gonna go bad.
00:42:53.900 -->
00:42:55.179So just hire a contractor.
00:42:55.339 -->
00:43:00.299Like, once again, like just don't hire people except in your core areas of expertise where you know you can hire well.
00:43:00.539 -->
00:43:02.460Yeah, everybody else is a distraction.
00:43:02.779 -->
00:43:05.420So when you look at the the future, right?
00:43:05.500 -->
00:43:11.420I'm curious to to like just to kind of zoom out and kind of bend on a more like holistic note.
00:43:11.659 -->
00:43:14.779Um, what do you really focus on over the next few years?
00:43:14.859 -->
00:43:15.900Like, who do you want to become?
00:43:15.980 -->
00:43:18.219Like, how do you want to continue to improve and grow?
00:43:18.460 -->
00:43:18.940Yeah.
00:43:19.099 -->
00:43:21.099Um, as an individual or a company?
00:43:21.259 -->
00:43:23.980Yeah, I mean, just like wherever your head goes, like is totally fine.
00:43:24.059 -->
00:43:25.579It could be more professional, personal.
00:43:25.739 -->
00:43:30.059Just like what's the first thing that comes to mind when you think about what the next best version of yourself looks like?
00:43:30.380 -->
00:43:33.099Well, look, so I mean maybe I should start by answering really quickly.
00:43:33.179 -->
00:43:36.779Like, I'm I'm live in San Francisco, I'm kind of red pilled on like AI and where that's going.
00:43:36.859 -->
00:43:41.339And like, look, I've I'm a short-term pessimist and long-term optimist when it comes to AI.
00:43:41.579 -->
00:43:49.420I think we will end up in a world of massive abundance in the next like 10 or 15 years, but we're gonna go through a really rocky and scary period in the meantime.
00:43:49.659 -->
00:43:55.179Um, and so what that means for me individually is I want to stay as close to the cutting edge as I can.
00:43:55.420 -->
00:43:56.699But even that is not good enough.
00:43:56.779 -->
00:44:00.940Like, I don't think anybody can stay up to date really on this because things are changing so fast.
00:44:01.179 -->
00:44:11.179Um, so the best I can do is try to lead my life well, try to meet people like you in person, um, be a good father, parent, husband, all that stuff, friend.
00:44:11.420 -->
00:44:20.059Um, and try to lead my company in a way that that I believe comports with my ethical beliefs and what the right things are to do.
00:44:20.139 -->
00:44:28.699Um, and essentially I'm gonna try to be the best human that I can because AI is gonna be better at me in a lot of things that I used to get joy from.
00:44:28.859 -->
00:44:30.219And that's a scary thing to say.
00:44:30.460 -->
00:44:37.099Like the simple fact is like I've spent, I don't know, 16 years or something building my career, right?
00:44:37.179 -->
00:44:40.139I'm essentially at like what people would view as like your peak of your career.
00:44:40.779 -->
00:44:44.699Where it's like, I'm hopefully still like I'm mentally not in decline, right?
00:44:44.779 -->
00:44:46.380You start going down, declining, probably over 50.
00:44:46.859 -->
00:44:48.059Start like there's a lot of data that shows this.
00:44:48.139 -->
00:44:49.980Like, no offense to 50 year olds, I'll be there soon.
00:44:50.139 -->
00:44:53.019But like you start going negative declining, all these other things aren't happening.
00:44:53.099 -->
00:44:58.380So, like, I'm at the peak of my career mental powers, my experiences, all these other things.
00:44:58.460 -->
00:44:59.339I should be right at my peak.
00:44:59.500 -->
00:45:07.420The simple fact, though, is like everything that was true for me being at my peak is essentially no longer true because of AI.
00:45:07.579 -->
00:45:09.259And that's that's scary.
00:45:09.420 -->
00:45:12.940Like that is that creates an unmooring feeling that I have.
00:45:13.099 -->
00:45:14.619Like, I don't know where I should go.
00:45:14.940 -->
00:45:15.579What I should do.
00:45:15.659 -->
00:45:16.219How do I do this?
00:45:16.299 -->
00:45:18.859So best I can do is try to try to be the best human I can be.
00:45:18.940 -->
00:45:25.579And and and hope that means that um it keeps enabling me to live a better life and a good life.
00:45:26.619 -->
00:45:27.900On the one life that I have.
00:45:28.059 -->
00:45:28.299Yeah.
00:45:28.619 -->
00:45:29.579It's awesome, man.
00:45:29.659 -->
00:45:30.139It's awesome.
00:45:30.299 -->
00:45:32.699Well, Adam, look, I I really appreciate you coming on today.
00:45:32.779 -->
00:45:33.900This has been a great episode.
00:45:33.980 -->
00:45:46.619I I do uh very much so appreciate the advice uh that you've shared with us and your life experiences and how you think about building companies and investing and and not hiring and uh these types of things.
00:45:46.699 -->
00:45:47.819So uh don't hire.
00:45:48.059 -->
00:45:48.539Don't hire.
00:45:48.699 -->
00:45:49.500I really like seriously.
00:45:49.579 -->
00:45:50.699I'm sorry, I don't keep going on this.
00:45:50.940 -->
00:45:51.339Don't hire.
00:45:51.420 -->
00:45:53.019I'm just trying to end here, but like don't hire.
00:45:53.099 -->
00:45:56.380The reason you should not hire, like, the the world's best companies are gonna be companies like one person.
00:45:56.619 -->
00:46:02.219Be one founder in dozens or hundreds of uh vendors and contractors or agents doing the work.
00:46:02.380 -->
00:46:04.380That is the future of business.
00:46:04.940 -->
00:46:07.739If you hire, you are just slowing yourself down right now.
00:46:07.900 -->
00:46:08.699So sorry.
00:46:09.420 -->
00:46:09.819Continue on.
00:46:09.980 -->
00:46:10.619Yeah, very cool.
00:46:10.699 -->
00:46:11.420Well, yeah, thank you.
00:46:11.579 -->
00:46:12.539It's been a lot of fun.
00:46:12.619 -->
00:46:13.900We'll have to do it again sometime.
00:46:14.139 -->
00:46:14.460Absolutely.
00:46:14.539 -->
00:46:15.500Thank you for having me on.
00:46:15.659 -->
00:46:16.219Of course.