The Media Operator's Mindset: Nathan Baschez on Substack, Virality, and Building Ideas in Public

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Welcome back to First Builders, where we explore the journeys of those shaping the future of technology and business.
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I'm Amber Illig, founder and general partner of the Council, a venture capital firm dedicated to backing early stage companies in essential industries.
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And I'm Rachel Choi, partner at the Council, with a background in life sciences and health tech, working at the intersection of technology and patient care.
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This podcast highlights those who don't just join companies.
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They build them from the ground up.
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Whether founders or early team members, first builders have created functions, teams, and processes from scratch, tackling the toughest phases of growth.
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They don't just work at great companies, they join in the formative years and help define them.
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And it often leads them to even more exciting work down the road.
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Today we have the perfect guest to dive into this with, Nathan Baschez.
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Nathan is the founder of Lex, an AI-powered writing co-pilot that assists users with drafting, editing, and brainstorming text-based content.
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Last year, Lex raised a 2.75 million seed round led by True Ventures, fueling its growth as a leading AI-powered writing tool.
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Prior to Lex, Nathan co-founded Every, a non-traditional media company redefining business and tech writing through a network of smart writers and subscription-based publications.
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Before launching Every, he was also employee number one at Substack.
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Nathan, welcome to the show.
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We're super excited to dive into your journey, how you've built and shaped modern day writing with AI in today's landscape.
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Yeah, thank you so much for having me.
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Awesome.
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Well, you know, I'm always curious to know, did you always know that you wanted to build in media and content, or did you just stumble into it?
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Ooh.
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You know, I always knew.
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I remember when I was in college, there was this like extremely quirky blog that I read occasionally by this guy named Steve Pavlina, who anybody who's heard of him will be like, this guy's referencing Steve Pavlino right now.
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But he's like very kind of out there.
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But he wrote this one post that was like, if you want to know what you're supposed to do with your life, just sit down and write about it until you start to cry.
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And maybe it'll take 30 minutes, maybe it'll take a day, you know, maybe you have to keep chipping away at it for months.
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But at some point you'll cry and you'll realize like that's the thing you're supposed to do.
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And I remember I was, you know, kind of early on in college and uh not sure what I wanted to do with my life.
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I was like, for some context of what was going on in my life at the time, I was like on the debate team and like kind of interested in public policy and things like that.
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But I just had this sense like that's just gonna be a slog.
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Like you have these cool ideas about what, you know, could or should be done, and then it's of course not gonna happen, you know, probably.
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Uh, or at least you have very, very limited influence on it.
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And I always kind of felt this pull towards work that was more kind of like creative, that I could directly just do something, right?
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And um, so I started writing, and the thing that ultimately really stuck and landed with me, and it's like a vivid moment that I remember is when I realized like I want to help people be smarter because the thing that has mattered most to me in my life is the the feeling of kind of like, oh wow, like this taught me something.
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This sort of like gave me a different or better perspective.
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And I just felt like, you know, with the the internet, right?
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And and everything like now with AI and all this kind of stuff, there's just so many, there's so much possibility for that.
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And of course, there's possibility for lots of other things too, but that is an important piece of it, you know, the whole bicycle for our mind kind of idea.
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And uh, and I just realized like that that's what I want to do.
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I want to like work on technology that helps people kind of become smarter, more fulfilled, more kind of curious versions um of themselves.
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Cause I think that's really what a lot of people are really trying to do.
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Um and so, you know, media became kind of like the it just sort of like the the best way to do that, I think.
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And so uh yeah, it was I I don't know if I I wouldn't this and I definitely wouldn't say I always knew that, but I f I have always felt pretty like comfortable doing things that maybe aren't, you know, whatever in vogue in terms of like what's like the hot industry or whatever in tech right now or whatever.
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I just always have felt a pretty good the other I I would say the other force is like I always have felt pretty comfortable just doing things that are personally exciting to me.
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I know I'm like pretty ADHD, and so I just know I have I'm really good at things that I'm excited about, and I'm just awful at things that I'm not excited about.
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So just a a hard constraint for my life is I have to do things that I am personally pumped about.
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Um that has also helped probably me kind of like have have somewhat of a lane, you know?
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Yeah, that's awesome.
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Um, so and I know you spent some time at a media company post-college, and then you ended up being the first employee at Substack.
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Yeah.
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How did that happen and and what convinced you to take that leap?
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Because you were basically joining at a time where it wasn't obvious that they were gonna grow into a household name.
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Like now everybody probably listening to this knows what Substack is.
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So what was that what was that thought process for you?
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Well, there are two parts of it.
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One one, so I was at Gimlet Media when I first heard about Substack, and Gimlet was this podcasting network that created some really incredible artful, you know, shows.
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And this was kind of in the the I'll call it the first golden era of podcasting, of like, you know, when serial was a big thing, all this kind of stuff.
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Podcasting is yeah, it feels a bit, it feels a bit different now, like there's not as much of that kind of thing.
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But anyway, this was when that was all really hot.
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And uh I remember just the sort of team structure of like it was weird, it felt kind of like the company I'd worked at before that was General Assembly, which is you know, kind of education startup, but had had a similar kind of like startup y feel or whatever.
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But the difference between General Assembly and Gimlet was like, okay, they were each kind of roughly around 100, 150 people-ish, at least kind of in like the headquarters type of a thing.
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But Gimlet was like all these teams working on like shows that were like their baby, but they had to also be like a normal company, but it was just it was obviously really different.
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And I thought, like, well, you know, in book publishing, you don't have a company with like the authors having like teams or whatever, or like in Hollywood, like, you know, the creative forces behind the stuff that we love is like they're a little bit more like free agency.
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They have a little bit more ownership, they're a little bit more.
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I just thought the model felt weird to apply like a normal company model to like this creative endeavor that's like super high risk, high reward, and you just have to pour your soul into it, you know.
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And so when I saw Substack, to me, it felt like I I was in a position to see that it solved some, I thought, really big problems in media, and it created a model where creators could have their own baby, you know, and and and really become owners and entrepreneurs and publishers rather than, you know, whatever just talent or something like that.
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And I just thought it would work because I saw that's pro that's what like pretty much everybody wanted at all the creative people.
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They just they kind of they liked the fact that they were a part of the bigger thing, but they kind of if they had their drillers, they'd do their own thing, you know.
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And so um, you know, I reached out to I slid into Hamish's DMs uh and I just said like, hey, this, you know, I work at Gimlet, this is pretty cool.
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Maybe we could do something for audio with this if I think it would work, you know?
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Like for Gimlet to use it.
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Because we were also one of my things there was I was looking a lot into like the membership kind of programs.
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So like subscriptions were like on our mind.
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And from there I just got to know, you know, Hamish and Chris and eventually Jirage, you know, the three founders.
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And um, I just you know kind of gelled with them.
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I thought what they were doing was really smart.
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My bar wasn't like, oh, I'm not gonna join them unless I'm 100% confident that it's gonna be the next big thing.
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That wasn't the basis for the decision.
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And I think if you're joining an early stage company, you know, even if you're joining like post-Series A or whatever, which this was like when I first met them, I maybe they were in YC or it might have even been before they got into YC.
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But the the bar I think is just like, does this seem fun?
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Like, does this seem like do you believe in it?
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Do you want to take a shot at building it?
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And and if you view all the sort of like company building, financial success type stuff as like a cherry on top of like the real thing you're after, is like I I want to make a bet on this idea.
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I think it'll work.
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And if it doesn't work, I'll certainly learn something and have a lot of fun in the process.
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That's to me how I've always kind of evaluated things, and you know, it's uh maybe not the most like financially responsible strategy, but it's kind of like you know, the Paul Graham essay where he talks about like the people who kind of end up doing crazy things are the ones who are willing to do crazy things because they're not so rational about like opportunity evaluation.
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I definitely think there's a lot of truth to that.
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And friends I know who are probably objectively like definitely smarter than me, they're you know, I've seen some of them get kind of stuck at like things that are relatively more certain, but maybe they're not like taking the bet on the thing that just seems cool to them, you know.
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And so I think that I think that's a big part of it is just like willingness to just go with what seems fun.
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Yeah, I mean I think that's I hear that a lot actually, like from like founders and people who are like taking those risks, right?
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Like wanting to really just go for something that like they believe in.
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Yeah, and that allows them, you know, to take that risk.
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Um, one of the things I want to kind of um touch on a little bit because you were you were mentioning this around like one of the reasons of why you were joining Gimlet and Substack.
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And I was curious if this is also, you know, an impetus for co-founding Every, which was like your next spot, but the fact that creators wanted to kind of own their own, you know, what they were creating, essentially, right?
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So yeah, was there any kind of big learning that you had from building Every, you know, with regards to that?
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And does that also impact like how you build today at Lex?
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Yeah, definitely.
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I think it was it was like super directly and kind of linearly connected to every.
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And then Lex is a little bit more of like a slight detour, I would say.
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But so the you know, if the sort of like let's say like thesis, antithesis, synthesis kind of structure or whatever, like my in my mind it was like you know, traditional media structure is like thesis, maybe.
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If like you just you have a company and the people who are creating stuff are employees, and you know, maybe they've got like if you're a star, you get a bigger salary or you get some sort of like performance bonus or whatever, but like pretty much it's like a normal company.
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And then maybe if antithesis is Substack where there is no company, you're an entrepreneur, and you have the sort of like means of production to go direct and to own your own relationship with your audience and your own, you know, business and all that.
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I saw that there were problems with the antithesis too.
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So there's a lot of just hyper talented people who have a lot of potential and are just already super good, but don't have the distribution that struggle to go independent on Substack because let's say you're sort of, you know, you don't already have enough sort of fan goodwill or just size of your fan base to kind of make an ARR that's like roughly equal to your salary, you know, then it's just really tough.
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It's tough to get there.
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And so I thought maybe there's room for something that borrows a lot from traditional media where it's kind of like a a magazine, but it's still it still takes a lot of what's really good about the Substack model, and it does something where, you know, it's a bundle, but you get a sort of like very direct share of it, and it's uncapped upside.
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And you know, there's like so there's distribution and editorial support and de-risked sort of like there's like a floor on how much you can earn and all that stuff, but there's like no ceiling and you know, all and you have more of your own brand and more of your own control of your ed of your of your voice, and your it's it's built around you, you know, as like it's a it's a group of stars rather than like the old school magazine thing is kind of like one unified editorial vision and the editor kind of rules it all.
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And so that was the idea with it, which honestly I think is a good idea.
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The um the interesting issue with every, which they're they're doing an amazing job with it, but it's evolved a lot since that original vision.
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And you know, I have I've been working on Lex for like the last two years, so I'm certainly not the best person to speak about the state of every today.
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But at least in the sort of like early days, the thing we learned is our editorial vision was like for builders, and it's just so hard to find people who want to write like essays about tech because you have to be able to, like, in turn, you have to know about tech and you have to be willing and interested in like spending a lot of time writing and getting good at writing, and the sort of intersection of those two sets is really small.
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Um, so it's tough, you know, compared to like the athletic or something like that.
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The goal was not to have this like really unique new editorial vision, in a way it was, but mostly it was like, hey, there's a lot of local papers who are not doing an amazing job, and we could we could go get the talent and help them do a better job giving them more of a national platform, and but just keep doing what you're doing, you know what I mean?
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Whereas the sort of there's a lot of coverage in business of sort of like whatever scoops and breaking news from like the New York Times and Wall Street Journal and Bloomberg and the information and stuff, but there wasn't as much of this sort of like analysis and commentary.
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I mean, kind of like what we're doing here, right?
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It's like and this has become, you know, podcasts are such a great medium for it because you don't have to learn how to write a really compelling essay.
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But we we were interested in the sort of like written, written form of it, uh, which is always tricky.
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So anyway, that was that was the deal with every, and then and then now they've I think just started really growing quite fast because of AI stuff, which kind of leads into Lex as well.
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Yeah, can you tell us a little bit more about Lex?
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Yeah, so the you know, most of my career, like when I was at Gimlet, when I was at Substack, I did other stuff, but a lot of what I did was design, you know, in Figma or like write code in in like VS Code or something like that at the time.
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Now it's cursor.
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And and at Every, for the first time, most of what I did was write in Google Docs or edit other people's writing in Google Docs.
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That became my primary kind of like creation tool.
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And I just felt this super steep drop-off in quality from from Figma or VS Code, because these are tools that are like built for, you know, a sort of specific creative thing that a specific group of people are doing.
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You know, Google Docs is a million different things to a million different people.
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And so it's not, it's not, it's not great at like uh just a lot of kind of simple things.
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And then also there's some bigger things like you know, questions of like how is AI gonna play in the process, all that stuff that it was really new and nascent, and I just didn't feel like they were gonna lead the way on it.
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And so, and so I got interested in just as like a side project within every in building some sort of writing tool that we could use, and then also maybe that we could sell as like a SaaS service.
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And and I was thinking about it at the time as just like this could be a nice, like sort of part of our bundle, because we're already a bundle of of media, and maybe we could also be include software in the bundle.
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And so spent kind of like nights and weekends working on it for about a month and built some stuff that I thought was pretty cool.
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I you know, I just thought, okay, this will be a fun thing to like test out.
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And then when we launched it, it just did so much better than I ever honestly could have dreamed of.
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And and you know, I have to be really honest about it.
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99% of the reason is just that GPT-3 was so much better than anyone realized at the time because this was like a month before, or like maybe a month and a half before Chat GPT launched.
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So there was just this really unique window in time that I caught in a totally like lucky way where you know AI was sort of had gotten super good, but people just didn't didn't know it yet.
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And and I just kind of like, you know, you could play with it in like their API playground thing or whatever, but like a lot of people hadn't.
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And and they certainly weren't using it as a part of their regular like workflow, you know, it was just kind of like interesting to experiment with.
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And so um, you know, just building it into like something that felt kind of like a nicer Google Docs, simpler, but like a bit nicer in this way where the original feature was if you're just stuck and you don't know what to say next, you can which happens to me a lot when I'm writing, you can type plus plus plus, and then the AI will fill in like the next paragraph or two.
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And it just felt like you know, a lot of the time it's not something that you'd actually use, but it helps you.
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It helps you think through what do I want to say next, what would be what would kind of logically come next, and then it gives you something to react to.
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Um so anyway, that just did super well.
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And partly I saw that and I just saw like the kind of enthusiasm around it, but mostly I just it was again, it was like my own enthusiasm of just like all I want to do is work on this thing.
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I don't want to think about really anything else.
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I wasn't super interested in writing anymore.
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I had kind of honestly fallen out of love with writing a while before I started working on Lex just because it's tough to have like an opinion and trying to attract people's attention like every week.
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Like it's just I don't know, I'm tired of having opinions kind of that have to be interesting opinions and not just like, yeah, that's the standard take or whatever.
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The standard take is off and right.
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And so um, yeah, I we basically had a lot of conversations with my co-founder.
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We decided to spin it out as its own company, partially because it was just a way of allowing me to focus on it full time and uh and also because it felt like it made sense as kind of like more of a venture bet than the media company did.
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Um so so yeah, so we so we sort of parted ways, and uh yeah, I've just been focused on Lex full-time ever since.
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And it's definitely been I will say, of all the things I've worked on in my career, this is sort of like by far the happiest I've been.
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And I've thought a lot about kind of like well, what is it that makes a sort of work situation, a role, a company, a team, all that kind of stuff?
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Like, what is it that that works for me and like what did it take to discover that?
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And I feel like if there's one, there's like specific lessons that maybe are about like what suits me.
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And then there's this general lesson of like, I didn't start working on Lex until I was like, I don't know, 33 or something like that.
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And I didn't really know what the bar was for like what good felt like until then of like, aha, this is like this is a great fit, you know.
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And so um, if you feel like you should have had that figured out by the time you're like 27 or something like that, for anyone who's listening who's kind of like in that age bracket, like it could take another like you know, 10 years or something like that, and just keep trying different stuff and like different um I think um the thing that was so surprising to me is there are wildly different baseline levels of happiness that are possible.
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It's like a wider range, you know, than like and it's just part of it is always like, okay, like let's meditate or let's like you know, whatever.
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But part of it's just like put yourself in a different situation sometimes.
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Really works.
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Yeah.
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I love that you just said that because we've had founders come to us.
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A good friend of mine that used to work at Cruise in Vercell, like absolutely incredible operator.
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I was thinking about launching a company and she's like, Well, I don't know if I'm too old to launch a company.
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When I look at, you know, accelerator cohorts, they're all like 25-year-olds that just graduated college.
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I don't know if I have that, you know, level of energy anymore.
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Um, and but literally I see so many incredible operators that didn't discover what they really want to be building, and they just come out of the gates so much faster and stronger because they've had those formative experiences.
00:17:07.359 --> 00:17:09.359
Many times they're into their mid-30s at that point.
00:17:09.440 --> 00:17:19.200
So I don't think there's a right way or a wrong way, but I definitely think people can get overly caught up in the like, I'm too old or you know, I haven't, if I haven't done it by now, I'm never gonna do it, sort of thing.
00:17:19.279 --> 00:17:20.400
So thanks for saying that.
00:17:20.640 --> 00:17:21.519
Yeah, absolutely.
00:17:21.680 --> 00:17:26.720
And you also you make it seem just like so easy and relaxed, I would say.
00:17:26.880 --> 00:17:32.160
Like I'm curious if there's like anything just like in your background that like makes me more comfortable like with that risk.
00:17:32.319 --> 00:17:40.079
I wonder if like, you know, many founders are like this, or if there's something unique kind of like in your background that kind of allows you to to have that mindset.
00:17:40.319 --> 00:17:42.400
I think there's kind of like two two answers.
00:17:42.640 --> 00:17:47.440
One is I definitely think there's something in my background that makes me more likely to take risk.
00:17:47.599 --> 00:17:51.279
I wasn't always as relaxed about it as I am now though, for sure not.
00:17:51.359 --> 00:17:59.359
And so there's another thing, but a set of things that I think I learned over the course of especially going through every and then kind of like the spin out and then intellects.
00:17:59.519 --> 00:18:00.799
That was like really, really hard.
00:18:00.880 --> 00:18:10.000
And I was like a very stressed kind of person throughout a lot of that, and and I think I came out of it in sort of like a way better spot, but uh, or at least with a much better perspective.
00:18:10.079 --> 00:18:17.359
Um and so the first the first thing about like it's almost interesting, like it's there's a sort of a separation between like taking the risk was like something I kind of always did.
00:18:17.599 --> 00:18:22.880
I just did it in like a stressed out way, and then being okay is like this other thing that I learned like much later.
00:18:23.039 --> 00:18:28.960
So taking the risk, I think it's just because for a long time I've known about myself that I just suck at things when I don't really want to do them.
00:18:29.119 --> 00:18:31.519
And if I really want to do them, then I'm like awesome at things.
00:18:31.599 --> 00:18:39.839
And so I've just always, you know, for better or worse, I don't really beat myself up about like, I wish I was like more diligent and like able to just do the things that I don't really want to do.
00:18:40.000 --> 00:18:43.680
I'm just like, no, I just gotta go with it because I'm just not gonna fight, fight my nature.
00:18:43.759 --> 00:18:46.480
I've like try every time I try, I kind of like fail on that front.
00:18:46.559 --> 00:18:48.480
So I've stopped trying a long time ago.
00:18:48.559 --> 00:18:54.640
I I mean I I go through spurts here and there where I like try and you know suck it up or whatever, but mostly I just don't try and fight myself.
00:18:54.880 --> 00:19:00.160
And uh so that's like just taking the risk is like I just do things that seem like I think that that would work.
00:19:00.319 --> 00:19:01.359
That seems interesting to me.
00:19:01.440 --> 00:19:02.079
That seems fun.
00:19:02.160 --> 00:19:06.880
I want to try that, and it doesn't it it's it doesn't loom so large to me, like what if it fails?
00:19:07.039 --> 00:19:10.960
So then the part about being chill with it, I was very perfectionist for a long time.
00:19:11.039 --> 00:19:27.599
I always thought we're on a tightrope, you know, if you make a mistake, like the whole thing could like lose momentum and you'll never get it back, or it'll be super hard to get it back, and everything's everything's gotta be like just right, and I've gotta be, you know, perfect, basically, in order for it to work.
00:19:27.759 --> 00:19:35.200
And it's I kind of think my mental model was like startups are super hard, and if you are basically perfect, they can work, but otherwise they won't.
00:19:35.359 --> 00:19:37.680
So, like that was that's a tough.
00:19:37.920 --> 00:19:45.839
I mean, imagine like tough pill to swallow every day, just like background that your being your thing of like this probably won't work, but it maybe could if I'm perfect.
00:19:45.920 --> 00:19:52.160
Like, it's just horrible, and so um, you know, I was kind of like a pain in the ass to work with.
00:19:52.319 --> 00:20:04.160
Like, if you ask Dan, my co-founder from Every, or like Chris, my boss at Substack, or like Matt, my boss at Gimlet, they'd all tell you, like, Nathan's great, but like, boy, is he sort of a pain sometimes.
00:20:04.400 --> 00:20:08.240
Because I I just thought, like, this is you know, we might be able to do that.
00:20:09.359 --> 00:20:10.000
Yeah, exactly.
00:20:10.079 --> 00:20:11.759
Um, and I was just super anxious in general.
00:20:11.839 --> 00:20:13.839
I think I think I'm just anxious, like for sure.
00:20:14.000 --> 00:20:15.599
That's that's just generalized thing.
00:20:15.759 --> 00:20:23.039
And it's kind of funny because yeah, I did still, I guess not anxious enough to like not take risks or whatever, but um, definitely anxious.
00:20:23.200 --> 00:20:31.119
And uh, I think at some point I just it became too much at every like you know, the the sort of relationship with Dan.
00:20:31.440 --> 00:20:35.920
I mean, that's tough for a co-founder relationship for for to kind of have that thing in your head, you know.
00:20:36.079 --> 00:20:52.880
And then, you know, just think like with with like my essays that I'm writing, it's like very personal of like why aren't people thinking this stuff is cooler, you know, like looking at other people who write essays that maybe become more popular or whatever, like what is it about the stuff that I'm writing that's not as interesting or whatever, or about the way that we're putting it out in the world or whatever.
00:20:53.039 --> 00:20:53.759
What can I do?
00:20:53.920 --> 00:20:59.200
You just rack your brain about that for too long, and it just becomes sort of like unbearable, and you just kind of have to shed it.
00:20:59.359 --> 00:21:11.279
You either you either like allow yourself to be consumed by it, or you just realize like I could actually just set this to the side and see how that feels and see if it seems like actually I'm performing so much worse now that I set that to the side.
00:21:11.519 --> 00:21:16.880
And then, you know, you do that for a little bit and you're like, oh, okay, actually I feel like I'm performing a bit better now.
00:21:17.039 --> 00:21:17.440
Interesting.
00:21:17.599 --> 00:21:20.079
Like if I'm just a little bit more loose about it.
00:21:20.319 --> 00:21:29.039
And so um, I think for me personally, the only thing that taught it through me was just going getting to a point where it was kind of like unbearable, you know, and I just like this obviously isn't working.
00:21:29.279 --> 00:21:45.839
And then the new the new thing, and like I've been sort of wanting to write about this, but I felt reluctant to because uh I I don't know, maybe I just feel like I need more time to kind of like bake, but I do feel like the past sort of two ish years have been like I've realized like there's this mythology of starting a company that it's gotta be super painful.
00:21:45.920 --> 00:21:48.319
And you know, you hear the quotes from people like Elon Musk or whatever.
00:21:48.400 --> 00:21:51.440
It's like chewing glass and you learn to like the taste of your own blood or whatever.
00:21:51.519 --> 00:21:53.839
And it's like there's this idea that it should be hard, right?
00:21:53.920 --> 00:21:55.519
Like startups are supposed to suck.
00:21:55.680 --> 00:21:57.599
And uh I kind of I just think it's bullshit.
00:21:57.680 --> 00:21:58.799
I don't think it's actually true.
00:21:59.039 --> 00:21:59.759
I don't think that.
00:22:00.079 --> 00:22:02.480
Like there it there are things that will there's like pain.
00:22:02.640 --> 00:22:04.400
Pain is inevitable, but like suffering is not.
00:22:04.480 --> 00:22:13.519
And it's just like this sort of Buddhist thing of like, you know, you can you can look at things and you can sort of like freak out about them, or you can be like, oh, interesting.
00:22:13.680 --> 00:22:15.839
Like, yeah, that that is happening.
00:22:16.000 --> 00:22:16.880
That's not good news.
00:22:17.039 --> 00:22:19.519
I'll allow whatever emotions arise to like come.
00:22:19.599 --> 00:22:20.799
I'll welcome them like a friend.
00:22:20.960 --> 00:22:26.559
I'll even learn to a little bit enjoy kind of like some of the anxiety in a weird way because I'm not like clinching away from it.
00:22:26.640 --> 00:22:28.000
I'm just kind of like, oh, interesting.
00:22:28.079 --> 00:22:30.079
Like I'm feeling that fear heavy right now.
00:22:30.319 --> 00:22:31.279
Wow, that's been a while.
00:22:31.359 --> 00:22:31.920
That's kind of fun.
00:22:32.000 --> 00:22:36.880
It's almost like becomes sort of like a movie where you're like, people watch scary movies because they like to feel that kind of stuff.
00:22:36.960 --> 00:22:41.359
And you or like you listen to sad songs because you like a little bit to feel the grief, right?
00:22:41.519 --> 00:22:51.359
And so if you learn to kind of like accept it a bit more as it comes, then it's like way more mellow and it's way just sort of like it becomes sort of like just this meaningful thing.
00:22:51.440 --> 00:22:57.599
Like, you know, like if you've ever been through really bad grief and you're like, part of it's actually kind of nice in a weird way that's hard to explain.
00:22:57.680 --> 00:23:07.359
Like you can kind of make that real about anxiety or about or or about grief for a potential possibility for like if you thought this investment was gonna come through and it was gonna be amazing, we were gonna get into YC.
00:23:07.440 --> 00:23:11.200
I was gonna be, you know, a made man or whatever, and then didn't even get the interview or whatever.
00:23:11.279 --> 00:23:13.759
It's like you can learn to kind of savor that, you know.
00:23:13.920 --> 00:23:19.119
And anyway, and then when you do, it's just like a very, very different experience of company building.
00:23:19.279 --> 00:23:28.480
And also, I think it's really important to kind of straighten out and kind of rationalize the sort of self-talk, you know, like the bad thing happening does not mean redoomed, it just doesn't.
00:23:28.799 --> 00:23:29.839
It's one bad thing.
00:23:30.160 --> 00:23:32.319
And you know, it's like, oh, like this.
00:23:32.480 --> 00:23:33.279
I was really pumped.
00:23:33.359 --> 00:23:40.960
I th I thought this, you know, potential, like, you know, whatever design partner customer was gonna be so excited about it, and then they're not interested.
00:23:41.039 --> 00:23:41.759
Oh my god.
00:23:41.920 --> 00:23:44.240
Like, actually, hold on, that's really useful information.
00:23:44.400 --> 00:23:50.480
Like, everything that we're selling to them is the thing that we made up like in a matter of weeks, like we can change a lot of it, you know?
00:23:50.960 --> 00:23:58.000
And so it's useful to to sort of run into the wall because then it tells you we need to point ourselves potentially in another direction, and it just becomes like lighter.
00:23:58.079 --> 00:24:01.839
I don't know, it just becomes becomes more like it's gonna be okay, you know.
00:24:02.000 --> 00:24:06.400
And I I've seen people tweet about sorry, I'm like rambling for a super long time on this, but one last point.
00:24:06.480 --> 00:24:23.279
I've been I've seen people talk about how like whatever, uh personal like content like Josh Wolf from Lux Capital, he's like personal contentment or whatever is like the enemy of societal progress, and uh, you know, you have to have like this huge chip on your shoulder and like this sort of like Elon Musk-esque, like something's broken with you and it causes you to like do crazy things in the world.
00:24:23.440 --> 00:24:24.240
I just don't buy it.
00:24:24.400 --> 00:24:29.680
For personally, I just feel like I'm doing the best work of my life as I've gotten more loose about it all.
00:24:29.920 --> 00:24:30.960
And so I don't know.
00:24:31.039 --> 00:24:32.640
That for for it, yeah.
00:24:32.799 --> 00:24:49.200
I I don't I by no, and the reason why I'm hesitant to like actually write about this or anything is like by no means do I feel like I've uh got I've like whatever at the end of some journey on this, and there's other people to listen to, like, you know, whatever Joe Hudson or Jerry Colonna who are like uh the real experts on it.
00:24:49.359 --> 00:24:54.880
But I will say uh that there is a sort of like there there is a definite like shift.
00:24:54.960 --> 00:25:03.519
I can mark a before and after in my life of uh kind of anxiety-driven uh relationship to work and a more chilled-out relationship to work.
00:25:03.599 --> 00:25:09.599
And it's I don't have a I don't know how I got there exactly other than just go getting to a point where it was unbearable, but yeah, it's it's a real thing.
00:25:09.680 --> 00:25:11.359
Yeah, I can totally resonate.
00:25:11.519 --> 00:25:12.319
Yeah, same.
00:25:12.480 --> 00:25:16.799
I was like just thinking that as well of just like, you know, what can I control?
00:25:16.960 --> 00:25:22.000
Because I usually like to control a lot of things, and then I realize that maybe it just comes with age potentially.
00:25:22.079 --> 00:25:31.039
The older I get, the real the more I realize that there are things so much out of my control that I have to just kind of focus on what I can control and kind of let everything else out to the side as well.
00:25:31.200 --> 00:25:32.000
So yeah, yeah.
00:25:32.240 --> 00:25:47.920
I resonated too, like I feel like I've been full-time on the council fund for now three years, and I think year one and even bleeding into year two, the mindset stuff and the anxiety was like very real because a like people are believing in you and giving you capital to go invest in companies and support those companies.
00:25:48.000 --> 00:25:54.559
And so I'd be like, if every single minute of every single waking day I'm not doing the absolute most, I'm failing.
00:25:54.799 --> 00:25:56.799
And um, that was very real for me.
00:25:56.880 --> 00:26:05.440
And then I think also similarly, like when you're having to pitch your fund, it's similar to pitching a startup or closing a customer or something in that everything feels personal.
00:26:05.519 --> 00:26:09.279
It's like, well, if you gotta know, it's like what's wrong with me, not what's wrong with the company.
00:26:09.359 --> 00:26:17.599
Uh so I think over time I learned to kind of separate myself from the entity itself and then also stop focusing so much on extrinsic value versus intrinsic.
00:26:17.680 --> 00:26:21.680
And I do feel like my performance really took off the second I kind of let go of all that.
00:26:21.759 --> 00:26:23.599
So I appreciate you going there.
00:26:23.839 --> 00:26:26.799
But yeah, I'd love to even shift back to something you said earlier.
00:26:26.960 --> 00:26:36.240
You talked about the luck that you had launching Lex three months before, or not even launching, starting to work on it three months before GPT-3 came out.
00:26:36.319 --> 00:26:40.960
And I'd love to challenge that because I think a lot of the things that you've done have not been pure luck.
00:26:41.119 --> 00:26:56.720
Um, and just from getting to know you even outside of this podcast for a while as a friend, I think one thing you do specifically well is you read the tea leaves and you kind of synthesize complex and seemingly unrelated trends into cohesive e insights uh for the broader tech and business industries.
00:26:56.799 --> 00:26:58.079
And you can see this in your writing.
00:26:58.160 --> 00:26:59.759
You can also see it when you're talking to you.
00:26:59.839 --> 00:27:06.799
I know when I was writing Software's Third Act about our thesis at the council, you were the number one person I wanted to grab coffee with to pressure test my ideas.
00:27:06.880 --> 00:27:13.839
And we talked a lot about these sort of shifts that happen, you know, every decade or so that usher in completely new eras of innovation.
00:27:13.920 --> 00:27:17.119
Um, and some of them are obvious, like obviously AI is here right now.
00:27:17.279 --> 00:27:18.160
We all know that now.
00:27:18.319 --> 00:27:23.680
Um, some of them, you know, six months before, 12 months before, 24 months before aren't so obvious.
00:27:23.839 --> 00:27:26.960
And they can be more subtle and kind of only stand out in context.
00:27:27.200 --> 00:27:34.559
Given you've written a lot about this and and you've been able to talk about a lot of this, I'm curious, like, how do you kind of identify those inflection points early?
00:27:34.720 --> 00:27:39.440
Sorry, this is a loaded question, but what signals really tell you that like an industry is about to change?
00:27:39.680 --> 00:27:40.640
Man, I don't know.
00:27:40.880 --> 00:27:51.039
Um I mean, one so like one thing that maybe is is interesting is when it feels like something's sort of weird at first, and then it just feels like it's not going away, you know?
00:27:51.279 --> 00:27:57.599
Because like there's a lot of weird things that might cross your radar, and then like if it kind of doesn't go away, like sort of like okay, maybe there's something there.
00:27:57.680 --> 00:27:59.519
Like some group of people really got attached to this.
00:27:59.599 --> 00:28:00.799
And then the question is like, why?
00:28:00.960 --> 00:28:05.440
And just because some group of people is like attached to it doesn't mean it's gonna be a big thing or whatever.
00:28:05.599 --> 00:28:12.400
But usually things that do become big things early on do have some group that's like that sees it and that get like they just they're stuck on it, you know.
00:28:12.559 --> 00:28:19.680
And so, like, for instance, I have no idea what'll pan out with this, but like right now, there's this thing in AI called model context protocol.
00:28:19.839 --> 00:28:24.400
And I'm just kind of like, I don't know, it's weird, it's hard to wrap your head around, it currently kind of sucks.
00:28:24.640 --> 00:28:27.839
But like there was some group of people, it just it wasn't kind of like going away.
00:28:27.920 --> 00:28:41.839
Like I first heard about it a couple months ago, and then it kind of kept and and and even before it's gotten like super hyped in the past whatever couple weeks or whatever, but like kind of even before then I just noticed like it was you know, people are kind of like some people just seem really stuck on it.
00:28:42.079 --> 00:28:50.880
And so then if that's like sort of the external outside view signal, and then the inside view is just like is it worth like spending an hour trying to wrap your head around it?
00:28:51.279 --> 00:28:52.880
And like then do you get it?
00:28:52.960 --> 00:28:58.640
Like inside view, and if not, then like you don't have to be excited about something other people are excited about.
00:28:58.720 --> 00:29:02.559
It's okay if they're I mean, actually, this is maybe different for entrepreneurs versus investors.
00:29:02.720 --> 00:29:07.920
Like, you know, for an investor to like have a big miss on like some huge trend or whatever is like maybe more real.
00:29:08.079 --> 00:29:18.240
For an entrepreneur, like I don't know, there's always I actually think this is another big thing is like it's really helpful to be in the mindset of I'm out there building stuff that I want to build and just doing the best I can.
00:29:18.319 --> 00:29:30.640
And it's really unhelpful, I think, to be in the mindset of like I want to make sure I don't miss like the biggest thing, like who's creating the biggest company competition is like one that you're always gonna lose, except for like one person a given time, and then you know, they whatever.
00:29:30.720 --> 00:29:49.519
It's just it's like a tough way to measure yourself, and a much better way is just to like keep plowing through and doing the best you can with like the thing that you're excited about or whatever, and evolve it over time, and it'll unfold in a way that can be very big, uh, maybe even cause one of these big trends that other people try and like you know work their way into or whatever.
00:29:49.599 --> 00:29:53.200
But like I think for an entrepreneur it's better to not to not worry too much about it.
00:29:53.359 --> 00:29:58.880
But yeah, I think um just yeah, noticing and maybe the other thing is noticing what kind of people seem to be stuck on the thing.
00:29:58.960 --> 00:30:03.200
Is it the kind of people who are very substance driven, or is it the kind of people that are a bit trend driven?
00:30:03.279 --> 00:30:14.960
And usually it's both, and it's really hard to if you get some trend trend kind of chasing type people interested in the thing, it's easy to actually get a false negative where you're like, Oh, all these people are hyping up this thing, therefore it sucks, or whatever.
00:30:15.119 --> 00:30:21.519
It's like, well, anything that's real, there will be the hype people and they'll be stupid as always, and like just but don't let them.
00:30:21.680 --> 00:30:28.079
It's like I I definitely think there's probably some anxiety right now amongst some people of like, oh, am I gonna start like yet another AI startup?
00:30:28.160 --> 00:30:44.799
And it's like, you probably should, you know, like it's I don't know, like I mean, don't do just like some some you know whatever thing that you feel obligated to do or whatever because it's but like if you see a thing like and you're and you're genuinely excited about it, don't let some thought that it's cliche to start an AI startup like get in your way.
00:30:44.960 --> 00:30:46.079
It's whatever, it doesn't matter.
00:30:46.240 --> 00:30:58.079
So anyway, I I think I think um not being turned off even when there's sort of hype people that seem sort of vacuous getting interested in a thing is another another good good uh lesson to learn on it.
00:30:59.359 --> 00:31:04.480
Yeah, there's an incredible amount of herd mentality that goes on, I think, between like the VC and founder community.
00:31:04.559 --> 00:31:07.359
It's it's pretty amazing to watch it happen over and over again.
00:31:07.680 --> 00:31:08.400
Yeah, totally.
00:31:08.559 --> 00:31:15.680
Yeah, and I think it's good to not be reflexively like you know, another one, and also not to be reflexively anti-it just because people are into it.
00:31:15.759 --> 00:31:17.519
And it's so hard to get that balance right.
00:31:17.839 --> 00:31:18.400
Totally.
00:31:18.559 --> 00:31:18.960
Yeah.
00:31:19.200 --> 00:31:24.400
Do you think there's anything like happening right now, like an inflection point that might be eclipsed by AI?
00:31:24.559 --> 00:31:32.000
Like I'm curious from your perspective, you know, if there's something that, yeah, you know, may may be more exciting or should be more exciting.
00:31:32.240 --> 00:31:33.200
That's a great question.
00:31:33.359 --> 00:31:33.839
I don't know.
00:31:34.000 --> 00:31:45.039
I mean, I think it's probably ultimately just a part of the AI story, but it could end up being like the very biggest part of it is what it might do for like biotech, molecular engineering.
00:31:45.200 --> 00:31:46.480
Are we gonna CRISPR humans?
00:31:46.640 --> 00:31:48.400
Have y'all seen the guy who did CRISPR on a human?
00:31:48.559 --> 00:31:49.759
His Twitter is just insane.
00:31:49.839 --> 00:31:51.519
Of like No, I need to check that out.
00:31:52.319 --> 00:31:56.079
But you know, and obviously there's all sorts of that's like a longer, longer term thing or whatever.
00:31:56.240 --> 00:32:09.359
But I mean, yeah, if like we if we have like super powerful AI that is capable of of really good genetic engineering, that is that reshapes the world in really, really, really huge ways, if harnessed really huge good ways if harnessed correctly.
00:32:09.519 --> 00:32:12.640
Uh but yeah, I think I think it's all kind of just like AI, to be honest.
00:32:12.720 --> 00:32:19.599
Um, I think that's I think that's a part of the it's probably could be the obvious most important part of the AI story in the end, but I think it's all AI for sure.
00:32:19.759 --> 00:32:24.559
Um because if you think about it, like intelligence is like this fundamental input to any value creation.
00:32:24.799 --> 00:32:26.559
It's so generic, just intelligence.
00:32:26.640 --> 00:32:27.039
What is it?
00:32:27.119 --> 00:32:29.279
It's like making the right decision, doing the right thing.
00:32:29.440 --> 00:32:30.079
You know what I mean?
00:32:30.240 --> 00:32:30.799
Like what?
00:32:30.960 --> 00:32:35.039
Like that is we're learning how to like synthesize that to some extent.
00:32:35.200 --> 00:32:36.480
So it's it's wild.
00:32:36.559 --> 00:32:40.079
And and I don't think that there's much uh that could be more fundamental than that.
00:32:40.240 --> 00:32:53.119
I think looking back, uh, you know, assuming all of it goes well, which I'm more on the optimistic side of things with it, but like looking back, it's sort of like when the internet came, it felt like it made computers, like the personal computer, feel like a footnote.
00:32:53.200 --> 00:33:02.160
I think AI makes the internet feel like a footnote, like is the thing that a lot it was just the precondition for this more important thing rather than well it's another thing, you know, like mobile and whatever.
00:33:02.319 --> 00:33:03.839
Like, no, AI is the thing for sure.
00:33:03.920 --> 00:33:04.640
I think that's my view.
00:33:04.880 --> 00:33:06.160
Awesome shifting gears.
00:33:06.240 --> 00:33:11.680
So basically, throughout your whole career, you've been pretty much a strong advocate for high quality independent writing.
00:33:11.839 --> 00:33:17.039
What advice do you have for builders today trying to create content that actually stands out in a crowded space?
00:33:17.279 --> 00:33:18.799
Ooh, that's a great question.
00:33:18.960 --> 00:33:24.799
I would say the number one thing is just knowing why you're doing it and who you're doing it for.
00:33:24.960 --> 00:33:37.039
And I think probably the most sustainable best motivation, stack kind of, because there's always multiple motivations, but the stack of it has to be like the base of the pyramid is you've identified that the process of writing feels good.
00:33:37.279 --> 00:33:41.359
You are you find it fun to some extent, and it's obviously not going to be all fun.
00:33:41.440 --> 00:33:43.119
It's like you know, working out or something like that.
00:33:43.200 --> 00:33:46.799
So you've identified some joy in the activity itself, even if it is strenuous.
00:33:47.119 --> 00:33:50.799
Maybe a less like working out, actually, more like maybe playing a sport or something like that, ideally.
00:33:50.960 --> 00:33:56.480
And and and you find that you come out of it feeling refreshed and better equipped to handle anything that's in front of you.
00:33:56.559 --> 00:33:58.000
I think that's the base layer of the stack.
00:33:58.160 --> 00:34:03.279
And if you can't connect with that, then like I would say just try and focus on cultivating that.
00:34:03.440 --> 00:34:06.720
And so you don't even really have to publish, although that this gets to the other things.
00:34:06.960 --> 00:34:12.639
The next layer up from there is um the potential relationships that it can build.
00:34:12.880 --> 00:34:19.440
So it's not about like, don't, I would say when you're starting, like, literally don't measure who's reading it, like how many people read it.
00:34:19.519 --> 00:34:21.840
What's my open rate, you know, all that kind of stuff.
00:34:22.000 --> 00:34:30.880
There's like a whole separate game around like, do you want to be some sort of content creator influencer type and like you want to optimize, you know, the clickbait and all that kind of stuff.
00:34:31.039 --> 00:34:34.400
I think for builders specifically, that's probably not the game you want to play.
00:34:34.559 --> 00:34:42.239
You don't, you don't want because what it does for for startup people is you just end up the gradient descent leads you to get rich quick, you know?
00:34:42.320 --> 00:34:43.440
So like that's where it goes.
00:34:43.519 --> 00:34:49.119
It's like, here's this new interesting AI technology, here's how these AI people are like getting way more efficient at their thing.
00:34:49.199 --> 00:34:52.239
Here's how to make this startup really fast, here's how to get rich quick.
00:34:52.320 --> 00:34:53.280
Like it just ends there.
00:34:53.360 --> 00:34:55.360
All the incentives pull you there.
00:34:55.519 --> 00:35:00.639
And so you don't want to you don't want to be in that, you don't want to create your value from like clickbaiting a bunch of people.
00:35:00.800 --> 00:35:04.400
What you want to do is create your value from building something valuable, a valuable company.
00:35:04.559 --> 00:35:08.239
And so then, okay, what's the purpose of creating really thoughtful content?
00:35:08.400 --> 00:35:20.960
It's for like a hundred people in the world, like in the world, the right hundred first people to like kind of really be able to download the best version of your thinking and then what that does for your relationship or your ability to collaborate with those people.
00:35:21.119 --> 00:35:23.920
Maybe they join you, maybe they fund you, whatever.
00:35:24.079 --> 00:35:25.360
That's what the writing is for.
00:35:25.519 --> 00:35:36.800
It's for your own discovery process and learning and straightening out your own thinking, and it's for relationship building with like specific people where you meet them at some thing and you start talking about a thing, and you're like, I wrote a thing about that.
00:35:36.880 --> 00:35:37.920
I would love to hear what you think.
00:35:38.079 --> 00:35:41.119
Like, here's my thing, and then you, you know, that that helps.
00:35:41.280 --> 00:35:51.199
And then, like, above that, it's kind of like publishing it online publicly and building some sort of some sort of like whatever like audience kind of a thing can be nice.
00:35:51.280 --> 00:35:57.119
It certainly makes it a lot easier for things like recruiting or getting beta testers or whatever, if you're kind of building the right kind of audience.
00:35:57.199 --> 00:36:03.920
But it's so I think people flip the pyramid usually in in startups and they see like you know, people doing the content creation thing.
00:36:04.000 --> 00:36:11.840
Like right now, the whole big thing is um whatever, like the technology brothers or whatever, and it's totally in this, it's like, you know, it's cool, like I like it, it's fun.
00:36:12.000 --> 00:36:14.639
But the game they're playing is like get a lot of eyeballs, right?
00:36:14.719 --> 00:36:16.960
They want to be sort of like a bar stool sports for tech.
00:36:17.119 --> 00:36:28.800
So, like, if what you're actually trying to do is build some totally different kind of company, you're not building a media company, you're building, you know, whatever, like AI that helps companies stay aligned with their like OKRs or whatever, like that you're building something totally different.
00:36:28.880 --> 00:36:31.920
Like, don't, you know, don't start to do the media thing.
00:36:32.000 --> 00:36:34.719
That's like you're cargo culting something that doesn't serve your goals.
00:36:35.039 --> 00:36:37.280
I think that's the main mistake I see people probably make.
00:36:37.519 --> 00:36:48.079
Yeah, no, I mean that's super helpful, and I think like you really see it like in the type of content that comes out and which ones feel true and authentic versus the ones that are just kind of like like what you're saying, like click baby, right?
00:36:48.159 --> 00:36:49.119
Like out there as well.
00:36:49.280 --> 00:36:52.559
So yeah, so you know, going back a little bit to Lux, right?
00:36:52.639 --> 00:37:03.039
And like how you're building there, um, obviously you've like seen the build of different products at Substack where it was really early and it scaled up, and then you know, obviously now like with Lux as well.
00:37:03.360 --> 00:37:11.119
Is there a difference or what might be the biggest difference in how you've approached product strategy, like depending on the different stages of the company that you've been at?
00:37:11.440 --> 00:37:13.519
Interesting, like at Lex versus Substack.
00:37:13.599 --> 00:37:13.840
Yeah.
00:37:14.000 --> 00:37:19.199
It feels so Lex and Substack to me, like the basic approach feels very, very similar.
00:37:19.440 --> 00:37:23.280
Every is a bit different because it's the media company difference kind of makes it different.
00:37:23.440 --> 00:37:32.960
But like, I mean, basically you just build this thing and it's just like hand-to-hand combat almost of like recruiting individual users to like try and get feedback and all this kind of stuff.
00:37:33.119 --> 00:37:40.320
And the thing that is also super similar about Substack and Lex is like it matters a lot to us like what type of user is using it.
00:37:40.400 --> 00:37:47.840
Like if you really write a lot and and and it's like you're you have high standards for like that's the kind of person who we really want feedback from.
00:37:48.000 --> 00:37:51.920
And you know, there's a lot of other types of people that are kind of like AI tourists that might sign up, right?
00:37:52.000 --> 00:37:52.880
Like any given day.
00:37:52.960 --> 00:38:01.280
So uh, you know, we want to take feedback from everyone, we want to make you know, people users happy, but like in the end, we have like a specific kind of person that we that we have our eye on.
00:38:01.440 --> 00:38:02.880
And it's like the same deal with Substack.
00:38:03.119 --> 00:38:08.159
In the early days, we wanted to get like writers who would succeed on the platform to get excited about the platform.
00:38:08.400 --> 00:38:13.679
So that's sort of the other thing I think that's very similar, it's like a it feels like an inevitable shift in some ways.
00:38:13.840 --> 00:38:15.760
It also feels like a hard sell in other ways.
00:38:15.840 --> 00:38:28.159
And I think this is one of the things that's a really big difference between Lex and some other, like you know, like the AI products that are like zero to ten million revenue and ten, you know, whatever with zero employees and ten days kind of a story that you hear on Twitter all the time now.
00:38:28.320 --> 00:38:31.599
So like Substack didn't do that, and and Lex isn't doing that either.
00:38:31.679 --> 00:38:38.320
Like, we're growing really well, but it's not like that because there's a lot of um there's a lot, there's a little bit of like it's a big different thing to do.
00:38:38.400 --> 00:38:40.960
It's a big, it's it's a little bit of a leap, you know.
00:38:41.199 --> 00:38:46.559
And so for writers, like you know, using AI is um a bit foreign, a bit scary.
00:38:46.719 --> 00:38:57.119
There's a lot of people who are very curious about it, but also like kind of reluctant, and finding the people who are willing to sort of like try the thing early and then kind of stake their reputation on it to be like, no, this is like a good workflow.
00:38:57.199 --> 00:38:58.880
Like, we're not producing slop here.
00:38:59.039 --> 00:39:10.480
We're using this to produce better writing than we would have otherwise and have a better like writing flow overall that's more enjoyable, is you know, it's it's it's there's definitely like the kind of crossing the chasm challenge is very real.
00:39:10.559 --> 00:39:18.400
And it's like in in with Substack's case, you know, getting the early big name writers to be like, yeah, I'm gonna do this new business model.
00:39:18.559 --> 00:39:21.360
It's like it's it's sort of it's a big ask of someone, right?
00:39:21.519 --> 00:39:30.719
And so anyway, it's I think there's some similarities there where like sometimes things that are a bit of a hard and uh honestly, early stories I hear from like how it was like with Figma in the early days is kind of similar.
00:39:30.880 --> 00:39:36.880
Like you're telling me I'm gonna design in my browser, like design apps are like desktop software, like you don't design in a browser.
00:39:36.960 --> 00:39:41.199
Oh, and like my manager can have the tab open and like peer up my cursor while I'm going.
00:39:41.280 --> 00:39:43.280
Like, I don't actually know if I want that, you know.
00:39:43.440 --> 00:39:52.159
And so some some of the products that end up growing the fastest are the ones that there's some kind of tough membrane that's a little bit hard to permeate, and you have to like have like stick it through.
00:39:52.239 --> 00:40:01.119
And so I think I think there's some similarities there too, of just like not taking just because something isn't sort of like an overnight success or whatever, doesn't mean it's not worth doing.
00:40:01.280 --> 00:40:06.079
Like, you have to have some understanding of how adoption will happen in your market and see some examples.
00:40:06.159 --> 00:40:14.559
And like, honestly, if I hadn't been there and seen firsthand what it was like in the early days of Substack when we were having the conversations like, do we have product market fit?
00:40:14.719 --> 00:40:17.199
Do we need to substantially change our offer?
00:40:17.360 --> 00:40:20.239
You know, like that was a real thing when I was at Substack.
00:40:20.320 --> 00:40:22.239
It wasn't obvious that we had product market fit.
00:40:22.400 --> 00:40:35.760
It was uh, and then seeing it kind of gradually, there wasn't necessarily just one thing, there were certain moments that were like big boosts or whatever, but it's kind of a lot of little things, and then the attitude starts to change, and there's this like cascade of acceptability that can kind of happen, and then inevitability that happens.
00:40:35.920 --> 00:40:40.960
If I hadn't been through that, I probably wouldn't have the conviction to stick with Lex and like look, I could be wrong with Lex.
00:40:41.039 --> 00:40:45.679
We're still kind of like we're growing, but it's not like this like whatever, 10 million error R kind of thing yet.
00:40:45.840 --> 00:40:50.719
And so, but I definitely wouldn't wouldn't be sticking with it had I not seen how it worked um at Substack, that's for sure.
00:40:50.960 --> 00:40:54.480
And you were really early to building a B2B SaaS and AI, as we discussed.
00:40:54.559 --> 00:41:01.840
Um, what's been your kind of biggest learning about building in an era of tech that is so it's just kind of like changing all the time?
00:41:02.079 --> 00:41:02.400
Yeah.
00:41:02.559 --> 00:41:10.000
I mean, one of the big things is um it's really important not to uh if you're building an application, not to romanticize building models.
00:41:10.159 --> 00:41:26.000
It might make sense at some point when you've got massive product market fit to build your own model, but uh application layers companies need to, and I think most of them are now, but this was not at all the case when we first started working on Lex, they need to be like, they need to own being at the application layer and like build just a great application, right?
00:41:26.239 --> 00:41:34.320
And there's so many merits to it that are much more, it seems, widely accepted now than they were a couple years ago when I first started working on Lex.
00:41:34.480 --> 00:41:40.079
It used to be the thought the idea that like, well, unless you have your own big model, like you're easy to copy.
00:41:40.159 --> 00:41:41.599
You're just a rapper, kind of a deal.
00:41:41.760 --> 00:41:46.719
And I always sort of thought, like, well, okay, on day one, a rapper's easy to copy, you can copy it in a day.
00:41:46.880 --> 00:41:49.280
On day 10, it was a little bit less integrated.
00:41:49.360 --> 00:41:49.519
Yeah.
00:41:49.840 --> 00:41:52.159
Day six, or sorry, month six, it's a little harder.
00:41:52.320 --> 00:41:53.599
Okay, you're starting to build a brand.
00:41:53.760 --> 00:41:55.280
Okay, there's like kind of some switching costs.
00:41:55.360 --> 00:41:57.280
There's a maybe there could be a little bit of a network effect.
00:41:57.360 --> 00:42:04.800
There's, you know, like application, application layer companies are like where value accrues in value chain generally.
00:42:04.880 --> 00:42:16.639
And what I mean by that is if you're at the interface that is like the necessary, like, so you take sort of like these raw AI capabilities and then you actually make it useful and you put it in people's hands, and it's a brand that people associate with.
00:42:16.800 --> 00:42:22.079
It's, you know, all that kind of stuff, like that's that's the kind of place where value usually accrues in software value chains.
00:42:22.159 --> 00:42:24.320
You know, AWS is a big business, right?
00:42:24.559 --> 00:42:29.760
But it's not like a it's not as profitable as like, you know, some of the like Google search or whatever.
00:42:29.840 --> 00:42:37.280
Like these application layer things have historically been where most of the value lived in the value chain and and and not just sort of pure infrastructure plays.
00:42:37.519 --> 00:42:46.400
And so, you know, as long as there's like two competing companies that offer good LLMs, pricing is a massively different story than if there's only one.
00:42:46.480 --> 00:42:48.320
So, like with NVIDIA, it's kind of like there's one.
00:42:48.400 --> 00:42:49.840
With TSMC, it's like there's one.
00:42:49.920 --> 00:42:56.719
So that's that's where you get into the like there's danger or whatever with the people up the stack, but it just doesn't seem like that's the way the future is panning out with models.
00:42:56.800 --> 00:43:03.440
So anyway, yeah, number one advice don't get too enamored with building your own model or getting super advanced about like fine-tuning and evals and all that stuff.
00:43:03.519 --> 00:43:12.079
Like, just build something that's basically good as software, and then you can entrench yourself with all that stuff later on, but it's like the thing to deepen product market fit, not the thing to find product market fit.
00:43:12.239 --> 00:43:12.960
Yeah, totally.
00:43:13.199 --> 00:43:25.039
So, yeah, so I'm curious too, like, you know, in the process of building Lex, like, has there been any point where you hadn't made a pivot or you know, or double down on something that you're like, oh, this is really working well?
00:43:25.119 --> 00:43:28.239
I'm just curious, like, if you've experienced that already along the journey.
00:43:28.559 --> 00:43:28.880
Yeah.
00:43:29.039 --> 00:43:37.199
I mean, the biggest one was so originally it launched as kind of this like when you're stuck, it will give you the next paragraph as inspiration or whatever.
00:43:37.360 --> 00:43:41.519
And I kind of knew, like, quickly, it was sort of like, okay, that's not gonna be like the end thing, probably.
00:43:41.679 --> 00:43:46.719
What's the like, what's the what's the best way, what's the best interface for interacting with AI when you're writing?
00:43:46.880 --> 00:43:58.559
And we realized um partially because it's I think it's just a more flexible interface, and partially because it's also what the sort of companies upstream of us, like OpenAI and Anthropic, we're building against, is like this chat paradigm.
00:43:58.719 --> 00:44:04.639
And so that that That became kind of like the the by far more important feature of Lex over time.
00:44:04.800 --> 00:44:07.039
And we could still go through more of those, you know.
00:44:07.199 --> 00:44:12.880
Like I think it is kind of a little bit crazy of like, you know, the company maybe voice becomes more important actually.
00:44:13.280 --> 00:44:16.239
And people aren't quite used to it yet, but we're like shipping more voice stuff.
00:44:16.320 --> 00:44:24.320
And I mean you can imagine how frictionless is it to like just select some text, hold down some keys on your keyboard, and then say, like, can you fix this?
00:44:24.400 --> 00:44:27.599
It's a bit clunky, and then let up and then it's like and it does it or whatever.
00:44:27.760 --> 00:44:29.440
And you like hit enter and you hit accept or whatever.
00:44:29.519 --> 00:44:32.639
Like that's coming to Lex in like I don't know, less than a month, hopefully.
00:44:32.960 --> 00:44:38.000
But like maybe that becomes actually the main best way of using Lex is a more voice-first thing.
00:44:38.079 --> 00:44:47.280
And so I think we're not done with like it's not pivots, it's just the technology is advancing, and user behaviors and expectations are also advancing.
00:44:47.440 --> 00:44:56.239
And something that feels like the obvious way to work with it now could feel really antiquated in like you know, a year, like the autocomplete deal, it feels a bit antiquated, you know.
00:44:56.320 --> 00:45:00.239
And so, but then you gotta have like the north star of like who are we serving?
00:45:00.400 --> 00:45:03.199
Basically, what problems do they have, and basically what is our role.
00:45:03.360 --> 00:45:07.280
And in our case, who we're serving is people who are doing reasonably serious writing.
00:45:07.360 --> 00:45:14.639
They want it to be good, they're willing to put in some work to edit it because it's like they they want it to come out in a really compelling, clean, effective way.
00:45:14.800 --> 00:45:19.920
And I believe that people will be doing that long after AI is capable of producing super high right now.
00:45:20.079 --> 00:45:22.079
A AI is capable of producing like okay writing.
00:45:22.159 --> 00:45:27.519
Even when AI is capable of producing like amazing writing, I think people will still be writing because writing is a way to form our thoughts.
00:45:27.599 --> 00:45:30.079
And if people are in charge, we need a way to form our thoughts, right?
00:45:30.239 --> 00:45:31.760
So hopefully people are still in charge.
00:45:31.920 --> 00:45:33.840
I think if people are still in charge, they'll still need to write.
00:45:33.920 --> 00:45:38.719
So anyway, the role we play is to just reduce friction because that's how I feel when I'm using cursor.
00:45:38.800 --> 00:45:43.920
When I'm writing code, it just feels like I'm skating on ice now, like I'm moving so much faster than I used to.
00:45:44.079 --> 00:45:47.920
And so that's the goal for writers is to it's you're still creating your thing.
00:45:48.000 --> 00:45:55.679
We're just reducing tons and tons of friction to help you get it, get it done in a way that feels better, faster, easier, better than what you would have come up with otherwise.
00:45:55.760 --> 00:45:58.159
Um, and like you've thought it through really thoroughly, you know.
00:45:58.320 --> 00:46:01.760
It's not you're not producing uh, you know, slop, as they say.
00:46:02.000 --> 00:46:08.880
And so, anyway, that's it's important to be super anchored on something, but then at the same time being willing to change the way that you get the job done.
00:46:09.119 --> 00:46:09.440
Awesome.
00:46:09.519 --> 00:46:12.480
All right, so shifting gears, let's do a quick fire round of questions.
00:46:12.559 --> 00:46:15.760
So for each one, just share the first thing that comes to mind and it can be super short.
00:46:16.000 --> 00:46:16.880
Rachel, you want to start?
00:46:17.039 --> 00:46:17.360
Yeah.
00:46:17.599 --> 00:46:20.880
What's your best uh book or resource for early builders?
00:46:21.119 --> 00:46:23.599
The innovator's solution, not dilemma solution.
00:46:23.840 --> 00:46:26.079
Most underrated skill for a first builder or founder?
00:46:26.320 --> 00:46:30.000
This is weird because it feels not super underrated, but coding.
00:46:30.159 --> 00:46:30.960
Especially now.
00:46:31.119 --> 00:46:34.800
Non-technical founders should just build their own thing to start and become semi-technical.
00:46:35.119 --> 00:46:38.079
What's a piece of startup advice that's actually uh bad?
00:46:38.320 --> 00:46:38.719
Hmm.
00:46:39.039 --> 00:46:44.079
Potentially controversial, but that it's it's better to have a co-founder than not to have a co-founder.
00:46:44.320 --> 00:46:45.679
And what's on your information diet?
00:46:45.920 --> 00:46:47.039
Oh my information diet?
00:46:47.199 --> 00:46:48.719
Oh man, it's all right.
00:46:48.800 --> 00:46:56.000
The I would say the good, the so like, you know, there's like Twitter slop, and then there's like, you know, YouTube stuff of like cooking or whatever.
00:46:56.159 --> 00:47:01.840
And then like kind of the down the middle, like relevant to this is probably like I'm I'm loving Dwarkesh podcasts lately.
00:47:02.000 --> 00:47:07.840
Because he's getting into like, so I have this weird, like, I don't know, like intellectual hobby fascination with cultural evolution.
00:47:07.920 --> 00:47:19.599
I think it's like the most important idea in the world that nobody like we're taught evolution of like, you know, genetics and stuff, like in in organisms, and we're like, it's like this huge foundational important idea in science.
00:47:19.840 --> 00:47:40.480
And then like there's this whole other type of evolution that happens called cultural evolution, and it's like groups are selected based on the behaviors that they've and actually it's when you tell me about your thesis of who you invest in, I'm just like cultural selection at the company level, and you get enculturated in an effective culture, and then you go reproduce it in a new domain, and you're like more likely to succeed or whatever.
00:47:40.639 --> 00:47:43.519
Like everything you're saying about that, I just see it through this lens and I love it.
00:47:43.599 --> 00:47:52.320
And so, anyway, Dorkesh interviewed one of the main thinkers in that space, Joseph Henrik, uh, who wrote The Weirdest People in the World and The Secret of Our Success, two really phenomenal books.
00:47:52.480 --> 00:48:03.679
And so I just love that there's like some kind of zeitgeisty like tech influencer type person who's like talking about this to me somewhat obscure like intellectual uh hobby or niche of mine that I've gotten fascinated with.
00:48:03.760 --> 00:48:05.119
And um, so that's kind of cool.
00:48:05.440 --> 00:48:05.920
That's so cool.
00:48:06.000 --> 00:48:06.960
I'm excited to check it out.
00:48:07.199 --> 00:48:16.880
If you have a had a magic, this is like a three-part question, but if you had a magic wand, what's one wish you'd make for number one yourself, number two, Lex, and number three, the future of content?
00:48:17.119 --> 00:48:18.000
Man, magic wands.
00:48:18.159 --> 00:48:20.000
So it's like self, company, and industry.
00:48:20.880 --> 00:48:21.119
Yeah.
00:48:21.360 --> 00:48:23.519
Me, Lex, future, content, magic wand.
00:48:23.679 --> 00:48:29.199
Oh man, me personally, I think the main thing that I want is uh, I don't know.
00:48:29.360 --> 00:48:32.400
I feel like I kind of have it to be able to keep doing what I'm doing.
00:48:32.559 --> 00:48:36.000
Like, love this is kind of gets to some of the stress stuff earlier.
00:48:36.159 --> 00:48:44.480
Like the scoreboard of like how well Lex does is like far less important to me than like the feeling of like it's working and we're doing the mission and whatever.
00:48:44.559 --> 00:48:46.400
And like right now, I have that feeling.
00:48:46.480 --> 00:48:48.880
Like the team that I'm working with is like incredible.
00:48:49.119 --> 00:48:51.360
It feels like it's like we're learning things and it's awesome.
00:48:51.519 --> 00:48:55.599
We're in kind of like the newbie gains phase of public company building, you know.
00:48:55.679 --> 00:48:59.840
Like when you first go to the gym or whatever, you're like, oh, I can lift like 20% more weight each week or whatever.
00:49:00.000 --> 00:49:04.239
We're kind of like we can ship A B tests that increase conversion of paid by like 50% or whatever.
00:49:04.320 --> 00:49:04.880
It's just like fun.
00:49:04.960 --> 00:49:06.159
We're not gonna always be able to do that.
00:49:06.320 --> 00:49:12.480
And so just kind of keeping this vibe is like maybe the wish for myself, even obviously as it changes and things, whatever other things happen.
00:49:12.639 --> 00:49:14.960
Just the current feeling of it is great for Lex.
00:49:15.039 --> 00:49:22.079
It's probably the most important thing is to maintain the kind of like again, same deal, like maintain the soul and the culture that we have right now.
00:49:22.239 --> 00:49:30.079
It feels like you know, it's been it's been kind of a process to get to this point of discovery, and we're we're at a thing that feels great team-wise.
00:49:30.320 --> 00:49:38.639
And so to keep as the team grows on other stuff and changes over time, keep at least this sort of soul of the spirit, it'll feel different, but to have the essence of it be the same.
00:49:38.800 --> 00:49:43.280
And that does feel like attachment, so I just have to say, I'm gonna have to work through that later.
00:49:43.519 --> 00:49:45.280
And then the last thing, what was it for the world?
00:49:45.679 --> 00:49:46.639
For the future of content.
00:49:46.800 --> 00:49:47.920
The future of content.
00:49:48.159 --> 00:49:53.840
I don't know that it that it that it uh stuff finds a way, and it always does, so I'm not too worried about it.
00:49:53.920 --> 00:49:58.079
But you know, there's always people out there just trying to make the number go up and they'll say what it takes to do that.
00:49:58.159 --> 00:50:02.480
They're just doing gradient descent on like an audience with audience captioning, all the bad stuff that happens from that.
00:50:02.639 --> 00:50:10.000
And um, then you know, there's people who say things that are heartfelt, and uh, you know, something that's heartfelt could be it doesn't seem heartfelt, it's just like whatever, some academic paper or whatever.
00:50:10.239 --> 00:50:11.199
But it's authentic.
00:50:11.360 --> 00:50:12.639
It's authentic, exactly.
00:50:12.800 --> 00:50:17.599
And I think it always finds a way, even though it's a little bit sometimes it's hard to it it ebbs and flows.
00:50:17.679 --> 00:50:19.920
But yeah, I think the wages for it to continue to find a way.
00:50:20.159 --> 00:50:20.800
Totally agreed.
00:50:20.880 --> 00:50:23.519
Well, Nathan, this has been such an insightful conversation.
00:50:23.760 --> 00:50:27.119
Before we wrap up, is there um where can people find your work?
00:50:27.280 --> 00:50:28.639
You learn more about Lex.
00:50:28.880 --> 00:50:30.480
Unfortunately, Twitter still, yeah.
00:50:30.639 --> 00:50:33.280
So N-B-A-S-H-A-W uh on Twitter.
00:50:33.440 --> 00:50:34.239
That's the that's the one.
00:50:34.639 --> 00:50:36.239
And we can link it in the show notes as well.
00:50:36.480 --> 00:50:37.840
Yeah, I'm probably stuck there.
00:50:38.000 --> 00:50:38.559
All right.
00:50:38.880 --> 00:50:40.159
Thank you so much for joining us.
00:50:40.239 --> 00:50:41.519
It's been an awesome conversation.
00:50:41.599 --> 00:50:46.000
Um, and we appreciate you sharing your journey and your thoughts and being so real with uh the listeners as well.
00:50:46.159 --> 00:50:48.960
So thanks again, and we're excited to see what's next for you and Lex.
00:50:49.119 --> 00:50:49.360
Thank you.
00:50:49.440 --> 00:50:50.159
Thanks so much for having me.
00:50:50.400 --> 00:50:51.199
So funny.
00:50:51.760 --> 00:50:52.079
Awesome.
00:50:52.239 --> 00:50:53.599
That was such a fun conversation.
00:50:53.760 --> 00:50:56.719
Rachel, after talking to Nathan, what was your biggest takeaway?
00:50:57.519 --> 00:51:05.599
Oh, there's so many, but I think for me, the biggest one was really writing as a way to get clarity on your strategy.
00:51:05.760 --> 00:51:08.400
I feel like I use that a lot for myself.
00:51:08.639 --> 00:51:25.599
And then the other one for me was how he really emphasized his mindset shift, moving from being very anxious and a perfectionist to letting yourself just feel the emotions and enjoy the journey or enjoy the ride, essentially.
00:51:25.920 --> 00:51:27.679
Yeah, that really stuck out for me too.
00:51:27.760 --> 00:51:29.840
I feel like it's so much easier said than done.
00:51:29.920 --> 00:51:34.239
And I meet so many founders that have just gone through that or are currently going through it.
00:51:34.320 --> 00:51:42.480
And many times I notice that they're embarrassed to even admit that they're going through it, but in retrospect, they'll share that it was really tough that first year, first couple of years.
00:51:42.719 --> 00:51:46.000
So I hope that a lot of founders could take that away from this conversation.
00:51:46.159 --> 00:51:55.199
But in some ways, it is part of the journey, even going through that to get to the point where you can recognize where when things are happening that are just part of the journey in terms of your mindset.
00:51:55.519 --> 00:51:56.239
Totally.
00:51:56.639 --> 00:52:01.440
The thing that I noticed come up a lot in the conversation was quality over quantity.
00:52:01.519 --> 00:52:11.440
So he talked about not writing just for clicks and views, but writing for the top 100 readers that you hope something reaches, that you hope you thoughtfully react to what you're saying.
00:52:11.599 --> 00:52:21.039
And then not just founding a company just to follow a trend, but also not not founding a company just because it seems like it's in too hyped up of a space.
00:52:21.199 --> 00:52:28.400
And then uh making gut-based decisions, being drawn to areas where you can build and have direct impact on what you're building.
00:52:28.559 --> 00:52:32.960
So that just came through for me throughout the conversation, just the authenticity.
00:52:33.039 --> 00:52:44.480
And I think it kind of maps back to something that we look for in founders, especially his desire to not build anything that he does not feel passionate about and you know, giving other founders that advice.
00:52:44.719 --> 00:52:59.440
One thing that I look for even in the first conversation with founders is their mission alignment with what they're building, because I believe that if there is no mission alignment and they're not that passionate about it and just doing it to make money, they will give up the first time it gets tough, and it will get tough because startups are always hard.
00:52:59.519 --> 00:53:03.280
So even if they're enjoyable, they do have hard times and rough patches.
00:53:03.440 --> 00:53:07.199
So that was what really stuck out to me is just that quality over quantity.
00:53:07.360 --> 00:53:27.280
And then the other thing was uh he really didn't start Lex until he was 33 years old, which totally goes against that archetype of founder that just dropped out from college or just graduated and is has all this energy to start their first company and can build really fast and never sleeps, just the stereotype that's out there.
00:53:27.519 --> 00:53:45.519
But I think it was so valuable to him because he had had those early career experiences, such as being at Substack and having to discover what is true product market fit and really debate that internally because I think that probably helped him get to product market fit a lot faster on Lex because he could really recognize it when he saw it.
00:53:45.679 --> 00:53:56.639
I see a lot of founders think they have product market fit, but they're they're really, you know, they're giving something away for free and they're not really gonna know until they charge and just different things like that traps that founders fall into.
00:53:56.719 --> 00:54:03.039
I think he probably fast-forwarded past a lot of that stuff because he had years of experience dealing with that.
00:54:03.360 --> 00:54:04.480
Yeah, absolutely.
00:54:04.639 --> 00:54:12.800
I think that's something that we see a lot with the high slope mindset of these types of founders, you know, being adaptable, relentless.
00:54:12.880 --> 00:54:15.119
They are able to problem solve so quickly.
00:54:15.199 --> 00:54:24.400
And it really makes, you know, these early stage um employees so valuable and also translate really well into early stage founders.
00:54:24.800 --> 00:54:45.039
Yeah, that's that's really what we try to even emphasize at the council capital on the venture side is that the first builder archetype isn't just about having started something and building a company, it's really having been in the right place at the right time in the past and learning those lessons on the fly during that high slope period and then knowing how to execute much faster in the future as a result.
00:54:45.840 --> 00:54:47.039
Absolutely.
00:54:47.280 --> 00:54:52.880
Well, if you love this episode, please subscribe to First Builders or share this with a fellow builder as well.
00:54:53.039 --> 00:55:01.119
And would love to hear um what topics you want us to cover next to.