10+1 Lessons from Serial Entrepreneur Justin Kan

a16z General Partner Andrew Chen (@andrewchen) talks with serial entrepreneur and co-founder & CEO Justin Kan (@justinkan) about lessons he's learned as a founder. Justin is a repeat entrepreneur who co-founded Kiko Software (a Web 2.0 calendar that pre-dated Google Calendar by 4 years), Justin.tv (a lifecasting platform), Twitch.tv (a live streaming platform for esports, music, and other creatives, now part of Amazon), Socialcam, and now Atrium, a software-powered law firm for startups. Justin reflects on his journey and shares 10 + 1 lesson he’s learned along the way: - The paradox of choice: choosing a focus - Tradeoffs between B2B versus B2C companies - Market risk vs execution risk - Fundraising strategy: go big or stay lean? - Managing the stress of being a startup CEO (again!) - Seeking out mentors, coaches, and peers for help - Intentionally designing a culture to avoid the pitfalls of “culture eating strategy” - Things he’s still doing in his latest startup—and things he’s doing very differently - Managing higher expectations now that he's not a first-time founder - What he’s reading and listening to - Bonus (+1): advice he’d give his 20-year old self just starting out in tech

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  The content here is for informational purposes only, should not be taken as legal, business, tax, or investment advice, or be used to evaluate any investment or security, and is not directed at any investors or potential investors in any A16Z fund. For more details, please see A16Z.com/disclosures.

• 0:19Andrew Chen?

  Hey, I'm Andrew Chen from Andreessen Horowitz, and today we have Justin Khan, who is one of our repeat entrepreneurs that we are very excited to be working with on Atrium. And so, we're going to talk a bunch about, what is it like to be a repeat entrepreneur? I think we were just going through the list. There's like five different companies on there. And you've learned a ton from every single one. And so, we're going to do a series of sort of compare and contrast across quite a number of topics. But as a very first step, I think it'd be awesome to have Justin talk about some of the companies that you've been involved in. And I know the company you were running when we first met, where you were running around with a camera on your head, was not actually even your first one. There's one before that called Kiko. So, why don't you talk about Kiko first?

• 1:03Speaker 02

  Sure, yeah. So, I've been an internet entrepreneur here for the last 14 years, since 2005. Our very first company was called Kiko. It was kind of like Google Calendar, but it came out one month before Google Calendar came out, and wasn't really that good, when I'm honest about it. And so, that company didn't work out super good. We ended up fire-selling it on eBay after several failed acquisition attempts with Silicon Valley players. And then, after we did that, we started another company. This one was even less well-thought-out than Kiko was, actually, which was, the idea was, we would create our own live-video reality TV show on the internet. I do think that tapped into several things

• 1:48Speaker 02

  that were in the zeitgeist that actually have become popular now. But unfortunately, we, as talent in our own show, were not very entertaining and not very popular. And so, we launched this live-streaming show. We called it Justin TV.

• 2:00Andrew Chen?

  Right.

• 2:00Speaker 02

  Because I was the only one in our four founders who was stupid enough to put the camera on his head and be like, "I'll make myself the subject of this show."

• 2:08Andrew Chen?

  Right. And you literally wore, I remember you wore a backpack.

• 2:12Speaker 02

  Yeah, so this was 2007. So, it was pre-iPhone, pre-good cellular internet. So, we had this computer in a backpack with like multiple cellphone modem connections. And we hooked it up to a camera. So, there was a camera. This computer virtualized the video as a webcam, basically, sent it over to this server and then we had this very hacky way of streaming it out to the millions of people watching, actually not millions, hundreds, but you know, the people who were watching at home, they were following along. It was actually pretty fun, they could text, we put our number up there, they would text me, usually fairly offensive things, actually, but then eventually, we launched this show,

• 2:55Speaker 02

  people started coming because they were like, "What is this guy doing, this is crazy." They were like, "You're very boring, I hate your show, but I want to create my own live video stream, so how are you doing it?" And then the light bulb kind of went off and we said, "Ah, let's create a live video platform," and that became Justin TV The Platform. And then after that, you know, we ran that for a couple of years, you know, condensed it because it's a very long story, but we raised a bunch of money, ran it for a couple of years, hit the nuclear winter of video startups where all the other video startups in Silicon Valley died, we were pretty scrappy and survived on like a ramen budget, eventually decided we needed to pivot to some new ideas and from there we incubated a few ideas internally. One of them was a video app called SocialCam, which we spun off and eventually sold to

• 3:39Speaker 02

  Autodesk, and another one was a site that we, my co-founder really thought of, which was, the idea was focus on, let's focus on the video game, related video on our site, and that became Twitch, which, you know, kind of grew and grew and grew, we eventually pivoted the entire company to Twitch, my co-founder Emmett was the CEO of the company, and eventually sold it to Amazon for $970 million in 2014, about five years ago. Along the way, started some other companies, I started this company called Exec, which was in the errand running slash home cleaning space, it's kind of like a Handy or Home Joy, we actually ended up selling it to Handy, which through an act of God, sold to Angie's

• 4:21Speaker 02

  List this year, and then more recently, I'd been a partner at Y Combinator for a couple of years, and then incubated a few companies, one of those was this video Q&A app called Whale, and then...

• 4:36Speaker 02

  Just fast forwarding all the way up till the present day, decided I want to really put all my eggs back in one basket, precariously thrown around basket. And so I decided I'd start a new company. That idea was Atrium, which is a technology-enabled law firm for startups, really trying to solve all the problems that I had as an entrepreneur when dealing with legal, to make legal faster, more price predictable, more transparent for me, the business owner, the business manager. And that's what we set out to do about two years ago. It's going pretty well with serving a bunch of startups here in Silicon Valley with all of their needs. And it's been great, but I'm sure we'll get to that.

• 5:13Andrew Chen?

  Awesome, yeah. Well, I think one place where I'm going to start on this is a lot of the advantages of being a repeat entrepreneur are that you can raise more money and there's more, maybe easier to recruit talent. And there's all these advantages that come along with that. One of the disadvantages I find ends up being that there's so many distractions, right? Like there's a million different things you could do. There's a lot of things pulling at your attention. I'm really fascinated by your movement from going from YC in an incubator, where you can maybe dip into a lot of little things versus putting all your eggs in one basket and trying to start a company. To talk to us about that, that kind of decision.

• 5:57Speaker 02

  Yeah, that's a great question. So, once you become successful in some way in Silicon Valley, whether that's you've been an executive at a company that's rocketship unicorn, or you've started a company, the world opens up, right? People want you to be a VC. They want you to work on projects with them. You can start any company that you want, which is great, right? But there's this paradox of choice and focus can be a huge problem. I know for a lot of friends of mine, it has been as well. As an investor, as a partner at Y Combinator, there were some parts I really liked. I loved helping early-stage founders out and really working with them on these problems that, I felt like for 5% to 10% of them, it was life-changing, right? Like me helping them out. I came up with some great idea or helped them at a critical moment.

• 6:41Speaker 02

  That was life-changing. But then there was a large majority of them that probably could have been listening to a YouTube video of me or this podcast and get the same information, right?

• 6:50Andrew Chen?

  Yeah.

• 6:52Speaker 02

  I didn't feel like the feedback cycle was fast enough also as an investor. And I didn't really feel ultimately like after the first couple of years that I was continuing to learn and grow. And you know, I'm still in my 30s, I was like, I need to do something where I'm going to be forced to grow. And really, the number one vehicle for personal growth that I've ever experienced in my life has been startups. So I went back to what I knew. And I really decided that in order to grow as a founder, you know, we had a pretty big outcome with Twitch and I'd seen a lot of different things. In order to really grow to the next level, I would have to do something that potentially could be even bigger. And so I really felt like it deserved, that deserved my full attention. And so that's kind of how I decided. I don't necessarily think it's the right answer for everyone because what I didn't

• 7:37Speaker 02

  mention was that I had selective memory at the time and I forgot just how painful starting a startup could be. And so for the first couple of months of Atrium, I was like, oh man, this is a dream. I've like finally leveled up, I learned all these skills, I've like, I made it as a founder. And then reality, boom, set in and of course, there were, nothing ever goes according to plan, there were pains, there were struggles and that was, you know, that's part of the journey. But then the good part is, of course, when you experience pain, that is a catalyst for learning. And so I really got what I wanted in the end, which was, you know, forced to learn.

• 8:10Andrew Chen?

  Right, that's great. And I know one of the big differences among some of the companies that you started in the past versus Atrium, and something that you've talked a lot about is, you had this sort of succession of very like consumer oriented startups, sort of like watching other people play video games, like that's as consumer as you can get, basically, right? And so, you know, very interestingly, you know, Atrium is a B2B thing. And why did you choose B2B? Was it just for novelty? Was it just to push yourself? Or did you, you know, do you think that there's something different in mind that maybe takes advantage of some of your newfound skills?

• 8:46Speaker 02

  Yeah, well Twitch, I guess, is really the, it's like the ultimate consumption thing because it's, you're consuming someone consuming video games.

• 8:53Andrew Chen?

  Right.

• 8:56Speaker 02

  For me, I felt like, maybe this was an analysis I've done retroactively, but I think I've had this discussion with a couple of people, multiple-time founders. And when you're an early-stage founder, when we started Kiko and then Twitch, when we started Twitch, Justin TV, we were 23-years-old and we had no skills. I never had a real, full-time job in my life. And even though we were programmers, we were like new college-grad programmers. We were not good.

• 9:23Speaker 02

  We were horrible managers. We basically had nothing going for us. When you have nothing going for you, except for you're willing to put in hard, like, long-hours and a lot of blood, sweat, and tears, then you should focus on things where there's a lot of market risk. Because ideas where there's market risk, you can potentially win those, right? Now, as someone who has abilities and skills, I've learned skills over the last 14-years, you want to focus much more on execution-risk things. And so, I felt like B2B startups are more about execution risk. I felt like the legal market particularly was already a big market, and you just have to figure out how to do it 10-times better.

• 10:08Speaker 02

  And I felt like I had a roadmap for how to do that in my head. And so, that's why I felt that this was a better use of time. Because some of the consumer startups that I'd incubated and played around with post-Twitch, actually, it was really hard to find product-market fit. I don't have any advantage in finding product-market fit with a consumer app more than the 22-year-old Justin.

• 10:27Andrew Chen?

  You might have a disadvantage.

• 10:28Speaker 02

  Yeah, I probably have a disadvantage because I'm already more set in my ways. I'm less in tune with the culture. I don't know what the kids are doing. So, would the Justin of today invent the Twitch of today? I don't think so. I'm an old guy now.

• 10:45Speaker 02

  It's game over for me.

• 10:46Andrew Chen?

  I want to unpack this market risk, execution risk. Because it's such an important distinction, but very colloquial in our understanding of it. What do you mean by market risk? And maybe new entrepreneurs can have an advantage in tackling something with new market? How do you know if an idea has a lot of market risk?

• 11:04Speaker 02

  Sure, that's great. So Twitch and Atrium are the perfect examples, right, almost. So Twitch, it's like when we started, when we pivoted Justin TV to Twitch, or even Justin TV is a good example, but Twitch is the best one probably. When we pivoted Justin TV to Twitch, nobody believed that there would, this was a market, right? No one believed, no investors, very few of our even internal employees like believe. And even the founders were skeptical. Emmett deserves the credit here because he had belief, but like a lot of the other co-founders were skeptical on like, does this exist as a business? And so the good part is that the competition there was very low, right? There weren't experienced entrepreneurs being like, this is gonna be a huge business, we should compete. So really, it was, you know, the entire thing was market risk and figuring out, do we have product market fit?

• 11:49Speaker 02

  How do we build product market fit?

• 11:50Andrew Chen?

  Because in that case, you're trying to be the first in the category. There's no substitutes, really. You're like, it's like, you know, you're watching someone else play Street Fighter at the arcade. That's like, that's the substitute.

• 11:59Speaker 02

  Exactly. You have a lottery ticket, right? It's a lottery ticket, and if you pivot a bunch of times and like listen to your customers, you might be buying more and more lottery tickets. But your lottery tickets are just as valuable as the experienced entrepreneurs lottery tickets that he's buying. So he's a fool to play that game. And I don't think you see as many experienced entrepreneurs playing that same game. Whereas with execution risk businesses, my lottery ticket now is way bigger than the guy who's like the 22-year-old Justin, right? So for a B2B startup, I know, oh, I can attract talent. I can hire a sales team. I can like raise capital. And so it's a lot more, for something where it's like very established, that that's gonna be a business, or some business is gonna be in there.

• 12:42Speaker 02

  It's like, he's stupid to play against me, you know?

• 12:45Andrew Chen?

  Right, right. That makes sense. Well, you know, and I always find it funny that in the consumer startup world, that if you look at the last, you know, kind of decade of hits, if you were to tell people, oh yeah, you know, the biggest hits are gonna be this app that lets you get in strangers' cars. This app that lets you stay at someone you don't know's like house. You know, an app where you swipe left and right in order to meet people on the internet. And, you know, an app that lets you watch other people play video games. You would be like, that's the craziest like list of, you know, like billion-dollar companies I've ever heard. And yet that that is like actually, you know, how consumer, you know, internet actually, you know, the ecosystem unfolds, which is insane.

• 13:25Speaker 02

  It takes a lot of people who have nothing to lose to discover those ideas, right?

• 13:30Andrew Chen?

  And so, you know, one of the things, one of the clear advantages in all of this is that, you know, let's talk about fundraising and the decision on whether or not to raise a bunch of money out of the gate versus doing the kind of, you know, ramen profitable, you know, cockroach thing, right? That's sort of like, you know, one common contrast. And then obviously, you had a very unique fundraising strategy as well. So maybe talk about that decision and then kind of how you ended up pursuing it.

• 14:01Speaker 02

  Look, I'm not convinced that raising a ton of money out of the gate is the right strategy. You know, the Silicon Valley is littered with dead bodies of these companies, you know, the Ducearos and the Kools and like all these companies that have raised a ton of money. And then like they, when you have a ton of money, you spend a ton of money, right? Now, there's other companies like the Jet.com's that, you know, they made it work. So, you know, I'm not convinced it's the worst strategy ever, but I'm not convinced it's the best. But for me personally, you know, where it's an execution risk business, I'm too rich to like fuck around with the like, you know, okay, I'm gonna just gonna do a seed round and like, and just like take a long time, right? Like for me, speed to market and execution was really important.

• 14:46Speaker 02

  And I felt also like this market really supported it and required it because, you know, it is the legal space. There is, you know, so a lot of value in making sure that the clients and the talent, the attorney's talent and other legal providers like think this company's gonna be around, right? So that's, that's very important. And so, you know, this is a strategy. I don't necessarily recommend to anyone who can raise a ton of money that this is the right strategy. It's just the strategy that we, that we picked. In terms of the tactics of like how we did our round, especially our Series A, you know, my idea was because VCs are kind of naturally adjacent to legal, right? Like, for example, when you fund a company, they need someone to help them on the legal

• 15:27Speaker 02

  side with all of the, you know, paperwork and the execution of that funding round. We felt like getting a lot of VCs on our side would be a good tactic. And so we ended up going out and raising money for our seed round of, you know, over 90 different investors from all over Silicon Valley because I felt like it would be really good to have those investors on our side and recommending Atrium as a, as a channel partner. And so that was our tactic there.

• 15:54Andrew Chen?

  Right, and I think it's something where, to your point, if something that you're working on is primarily execution, then that means that you can, there are times and places where you can use money to solve it versus, it seems like, you know, part of the market risk thing is it just, you know, to your point, it sort of lets you buy more lottery tickets, but it may not accelerate the process of actually doing it, right? And so I think that that sort of feels like one main difference. And then the other one is, you know, that, just to build on what you're saying, is that if you are in an industry where trustworthiness is really important, then being well-capitalized is key. The same way you wouldn't, you know, if you're gonna, for example, you know, build a fintech

• 16:37Andrew Chen?

  startup where, you know, you're gonna, you're gonna ask consumers to trust their money with you.

• 16:43Speaker 02

  Yeah, exactly.

• 16:44Andrew Chen?

  You know, like, you want to be legit, you want to be well-capitalized, you want to have, like, you know, super-strong executives and board members and investors, and that's a strategy, kind of, that's a little bit, kind of, like, self-perpetuating as well.

• 16:54Speaker 02

  Yeah, that's a great example. If you're gonna build, like, a new bank, right, like, an online or like a mobile-first bank, which is, I think, some people are doing, would you want to raise, you know, $1 million or $1 million seed round or $5 million seed round or is it a $50 million Series A out the gate? Obviously, if it's available to you, you want more money, because you know people need banks, right? It's just a matter of, can you do it better, right? That's a perfect example, and there's, you know, there's many others here in Silicon Valley. I think we've actually shifted more as the cycle has changed over the last 10 years of the tech cycle, we've shifted more to these execution risk startups. And so, you know, you've consequently seen, I mean, it's a chicken and egg thing, really, what came first, but like, you've seen these more and more, like, bigger rounds, I'd say, that are supporting these companies.

• 17:39Andrew Chen?

  Well, you know, one of my, one of the partners here, Chris Dixon, has talked about the idea that You know, if you have a set of problems that has not been able to get solved and improved in, you know, the 20 years of the modern internet, then maybe all the techniques that we pioneered in the last decade plus, like being asset light and just throwing software and just shipping really quickly and being really lean, like maybe those techniques don't work for a reason in healthcare and fintech and legal services and real estate and like, you know, some set of those things, right? And so then very quickly you have to think, okay, well, you know, if those techniques don't work, otherwise it would have, someone would have tried it already, it would have

• 18:22Andrew Chen?

  sort of, you know, a little bit like efficient market hypothesis.

• 18:25Speaker 02

  Yeah.

• 18:26Andrew Chen?

  Would have kind of like happened already.

• 18:27Speaker 02

  Yep.

• 18:28Andrew Chen?

  Like, maybe you need a foundationally different approach. And so I think, I think that is actually one of the reasons why there's more of these like, quote unquote, full stack startups.

• 18:36Speaker 02

  Yep.

• 18:37Andrew Chen?

  That are going after these really, really difficult areas. Cause like, you know, otherwise you wouldn't be able to do it.

• 18:41Speaker 02

  Yeah. Well, running experiment right now.

• 18:43Andrew Chen?

  Yeah. Yeah, right. No, I think, I think that's right. I think that's right. So, you know, one of the, one of the fun topics, one thing that I have a tremendous amount of respect for you on is you're very, you know, you're always on the leading edge thinking about, you know, self-improvement, how to sort of, you know, your own, you know, personal performance at work, you know, at home, et cetera. And obviously, one of the big things about, you know, running a company is that it is enormously stressful, right?

• 19:12Speaker 02

  Yeah.

• 19:13Andrew Chen?

  And so, talk to us about like, you know, when you were a first time entrepreneur, kind of Kiko, Justin TV, you know, how did you think about, you know, managing the stress of, you know, running a company? And what was your approach there? And then, and then let's talk about kind of like the new and improved Justin now, you know, kind of 10 years later.

• 19:31Speaker 02

  Yeah. So in the early days, you know, 10 years ago, I was not doing anything in terms of like improving myself. In fact, I think I used to think about people's attributes, maybe not your skills so much in terms of like, you know, it's your skills at programming or stuff like that, but more of like your, your attributes. Like, I don't know if you ever played Dungeons and Dragons, but right when you create a character in Dungeons and Dragons, you roll this like 20 sided die and, you know, your strength, it's like 14, your intelligence, you roll it and it's six or whatever. And that's what you have, you don't, you can't change it. And so I felt like people's attributes were kind of like that and. So I never worked on that very much self-improvement stuff outside of, you know, like, yeah, I became a better programmer because we were programmed, you know.

• 20:14Speaker 02

  But I didn't work on things to like make myself, I don't know, smarter, right? Or harder working, or like awake more hours of the, you know, of the day, or like alert more hours a day, or anything like that. So I was, it was very happen, you know, everything was kind of accidental, like we would, you know, I was not dealing with stress well at all. If there was a problem in the company, I would be very emotionally avoidant to it. Or I would like drown my sorrows in like alcohol, right? Which is not a very good coping mechanism at all. And so, and then like, you know, in terms of even just down to like what we were like eating at lunch, I was, you know, we were talking about this, this earlier, but I would, we would have like pizza every day at lunch at Justin TV, and then I'd like fall asleep,

• 20:56Speaker 02

  like I'd go into like a carb coma in the afternoon, like every day. And so now, more recently, like with Atrium, it's been a tremendous vehicle for my own personal discovery because I experienced the stress again, you know, I was like, oh my God, it's stressful again, this is crazy, why is it so stressful? And so I started looking for ways to deal with that. And I really, I mean, I've had a number of things that started working for me after I started really exploring it, a number of things that started working for me, starting last year, you know, everything from, a friend of mine recommended a daily gratitude journal. So I've just been doing that every day, writing this gratitude journal, five-minute journal. You write down the three things every morning that you're grateful for, and that seems like

• 21:41Speaker 02

  a very simple thing and kind of hokey actually when I first heard about it. But what I realized was, it helps recontextualize all the ups and downs that you experience as an entrepreneur, especially, I mean, the downs really, like throughout the day, they're not as big of a deal, because in the morning, you're writing down like, wow, I have this opportunity, you know, I remember the day we came in and pitched, you guys here, I wrote in my gratitude journal, I get to pitch, you know, the Andreessen Horwitz. That's amazing, right? Even whatever happens, that's an incredible opportunity. It puts me in the top 0.01% of people in the world with opportunity, you know? Right. So that was like, pretty amazing. And then, you know, every day, there's something, like, if you really think about it, there's so many amazing things that happen to you as a human being, you know, here in

• 22:25Speaker 02

  Soakin Valley. Even just like, actually, one thing, I think in the morning oftentimes is like, the supply chain, the global supply chain to deliver coffee from like, around the world, so that I can grind up fresh coffee and like, a pour-over in my Chemex in the morning. Right. That's amazing. If you think about it. Totally amazing. Yeah. Right. So the gratitude journal, really working for me. And then, another thing- You're still eating pizza for lunch every day? Yeah, so diet, another thing, I stopped eating pizza. Tiredly? No, well, I started eating a ketogenic diet, which is a high-fat diet, but really, the reason for me is like, I just don't get as, you know, tired in the day anymore. And so that's been really helpful, and last year, I was experimenting, I did like, some

• 23:08Speaker 02

  one-meal-a-day days, you know, like, four days a week. So I'm on these weird, like, Jack Dorsey diets, kind of, Jack Dorsey light, or whatever, but it's been, it's been good for me, you know? You had to do what your body feels like is, feels good. And so, you know, that's some, I had an exercise, pretty religious about exercising, you know, try to do something every day during the workdays. Yeah. And then, the last thing that's, that was really big is meditation for me. Started off, just with Headspace, you know, I'm not the type of person that people, you know, assume would be a heavy meditator, or very introspective, or anything like that, but for me, just like, starting off with Headspace last year, and then, now I've been doing Transcendental Meditation, which is kind of what Ray Dalio talks about in Principles.

• 23:52Speaker 02

  That's worked really well for me, to just be more present during the day, in my life. It's pretty, pretty amazing, amazingly profound effect.

• 24:01Andrew Chen?

  I feel like your Twitter stream is part of your gratitude journal.

• 24:05Speaker 02

  Yeah.

• 24:05Andrew Chen?

  Because I read your Twitter stream and I'm like, oh, this is like very philosophical. You know, it's not like just pulling out like, oh, here's a blurb from the latest S1.

• 24:14Speaker 02

  Yeah.

• 24:15Andrew Chen?

  Like you're like, you know, you're like sharing ways that the startup community can, you know, to think about themselves.

• 24:21Speaker 02

  Yeah, the way I think about it is like, if you want something to be part of your identity, talk about it. If you want to learn something, teach it, you know, and I really believe that. So for me, putting out, you know, what I've been doing on the mindfulness side and for myself to be more emotionally kind of stable throughout the days and weeks and months as a startup founder, that's been really valuable to me. So if I can spread that to other people, it's going to help reinforce it as an identity for me, but it's also going to hopefully help those people as well.

• 24:48Andrew Chen?

  Right.

• 24:49Speaker 02

  You know, one thing I've been working on a lot as well, last thing I'll say is just working on realizing that your attachment now, in the very early days of Justin TV and Kiko and all these companies, I had a huge ego attachment to the outcome of the company, right? My identity and the companies were like very intertwined. And more recently, I realized, that was the same at Atrium, actually. Like, again, I was like creating that same pattern, but it was like, it's a very unhealthy pattern. So what I realized was I needed to start telling, reminding myself that no matter what happens with this company, I'm not going to be any happier or any less happy in the long run. There might be a short burst of unhappiness if it fails or happiness if it succeeds, like, you know, amazingly, but you know, you're not going to get any happier, really. If you're relying

• 25:34Speaker 02

  on outside things, external factors to drive your inner happiness, you will always be disappointed in the long run. And the funny thing is, I've actually run the experiment, not an A/B test, but a linear experiment on that, because we've had more and more success over time. Like, we started off, you know, really like paying ourselves, I think with Kiko, $7,800 a month, but we only paid ourselves every other month. And so... Then we raised funding for Justin TV and we were able to make like a little salary. Then we became profitable. We made a lot more and then we sold like one company and then we sold a lot of companies. And so we like kind of ramped over time and I, after you know, the basics in, you know, the basics of Maslow's hierarchy of needs were taken care of, you know, I felt like I could go out to eat. I don't know if that's on one of those Maslow's hierarchy of needs,

• 26:19Speaker 02

  but after that basic thing, I could, I could afford to go out to eat.

• 26:22Andrew Chen?

  Yeah.

• 26:22Speaker 02

  None of, it never mattered, you know, it never made me sustainably more happy. And so just reminding yourself of that and try to remove those attachments in your mind. It's easier said than done, but having that as like an active practice has been really important to me.

• 26:35Andrew Chen?

  Let's talk about mentorship as part of that, right? So, you know, when you're building Kiko, Justin TV, and you're, you're a first time entrepreneur, there's a lot of experienced, kind of, you know, experienced people who are kind of like, quote unquote, ahead of you in the thing. And so that's fantastic because you can, you can learn a ton.

• 26:54Speaker 02

  Yep.

• 26:55Andrew Chen?

  Would love to hear kind of, you know, who, who you thought of as your kind of lifelong mentors, people that, you know, have helped you for a long time. And then the other problem that's, that's super interesting is, you know, then you start Atrium and you know, you've had, you've had some major successes behind you. And then in some ways, the, the number of people you can learn from is a, is a much smaller pool and sort of like, how do you kind of curate your mentorship? Maybe how, how has it changed over time?

• 27:17Speaker 02

  Yeah.

• 27:18Andrew Chen?

  That's a broad, broad topic, but would love to hear your.

• 27:20Speaker 02

  Sure, absolutely. So like the best part about Silicon Valley, in my opinion, is that there are people here who have done it before, who are willing to help you, you know, that we would never have made it here, even day one, without people who helped us when it was like economically bad, you know, waste of time. We weren't like, didn't look like a hot prospect company or anything, right? So those people, Paul Graham, great example, founder of Y Combinator, Paul Buchheit, who was like a partner of Y Combinator, but the inventor of Gmail inside of Google. These are people who invested in us very early on, mentored us very early on and helped us out. And that was, you know, pretty, pretty amazing. And really that. That ethos perpetuates itself. You know, because then as a partner on Y Combinator, even to today as an entrepreneur,

• 28:05Speaker 02

  where you know, there's like lots of conflicting, competing interests for my time. I always make sure to spend a little bit of time mentoring other startups. Because you know, it's kind of like a pay it forward thing. You know, you, you do the thing that, that people did for you when you were, when you were younger.

• 28:21Andrew Chen?

  One of the really obvious sources of mentorship is actually peer mentorship, right? And some of the folks that kind of came up with you at the same time.

• 28:29Speaker 02

  Yeah.

• 28:30Andrew Chen?

  And you know, ended up running, you know, really interesting companies on their own. And, and I know they all live in DeBose with you in San Francisco. You know, talk to us about some of your friends that you, that you consider your mentors.

• 28:42Speaker 02

  Yeah, so you know, it's great to have friends who are kind of doing the same path in a lot of ways, but are one or two steps ahead of you. So it's still, still the case, you know, obviously Emmet, my co-founder, who's still running Twitch. It's over a thousand people. You know, I think it's like 1,500 people or something like that. My brother, who's, you know, COO of Cruise, co-founder of Cruise, the self-driving car company. And they're like over a thousand people. And like Steve, the founder of Reddit. You know, they're like 400 something people or whatever. So, you know, seeing what their problems are, you know, obviously, the problems are always the same, actually. The problems are always like, I don't have the right alignment among my team and I don't have the right executive team. It's usually some variation of those things. But you know, hearing it from, from the horse's mouth

• 29:23Speaker 02

  is, is super helpful in terms of making decisions for, for me. And then, you know, even outside of DeBose, sometimes I venture into Soma and having some of those, you know, kind of early YC founders who have really made it. You know, like Drew from Dropbox, for example. And just knowing like, how do they think about every, all those things, executive hiring, et cetera. It's really helpful, helpful to me. So luckily here in Silicon Valley, I have a lot of great resources. And the last thing I will, I'll shout out is,

• 29:52Speaker 02

  I have this new executive coach, Matt Mochary, who's like amazing. This guy is the guru. He mentors a lot of different fast-growing startups around here.

• 30:02Andrew Chen?

  I just talked to him for like a 360 pick.

• 30:04Speaker 02

  Yes.

• 30:05Andrew Chen?

  Yes.

• 30:05Speaker 02

  This guy.

• 30:06Andrew Chen?

  That was great.

• 30:07Speaker 02

  Incredible, highly recommend. Can't speak, he's like changed my life. So I feel like he's an angel sent down from heaven to teach me finally after 14 years, how to like manage a system. And I've learned a lot from him, so.

• 30:21Andrew Chen?

  That's great.

• 30:21Speaker 02

  Those are kind of three sets. Executive coach, the peer mentors, and then kind of those early-stage mentors that I had back in the day.

• 30:29Andrew Chen?

  That's great. And I know one of the topics that you must end up talking about often is that when you're building something that has a little bit more just execution risk, you've raised some real money to kind of get started, a lot of it ends up being sort of like organizational complexity, company culture. I know this is the big, big, big area of focus for you. And that's something that is very different when you're trying to build something for the long run versus when you're kind of just trying to find product-market fit and it's kind of like 10 people and you're just like, is this even going to make it? Let's not even work on this. So talk to us about kind of how your approach has changed on building the company and your leadership style.

• 31:07Speaker 02

  That is a great question because it's something I think a lot about. So I had never thought before, a couple of months ago, and this may sound stupid in a way, but I never thought, what is the kind of company that I want to show up to work at? So 14 years later, finally thinking about it. But the real answer is like when you're a 22-year-old just starting your company, or you're in Silicon Valley and you're thinking funding rounds and exits, you're always thinking, what's the next milestone? Like, how do I just claw my way desperately, however, whatever it takes? How do I get to that next milestone? It's do or die. And for some, oftentimes it is do or die. You don't have the luxury oftentimes of thinking about like what kind of, or you feel like you don't have the luxury of thinking about what kind of company you want to build culturally.

• 31:51Speaker 02

  And so I started Atrium actually very much in the same way of like, what are the metrics milestones we want to hit? What's the next metrics milestone? What do we need to get to for a Series B or a next round of funding? And so. The problem with that was that a year in, I realized, oh, shoot, I need to like, there are like a lot of things that I've neglected that are actually affecting our ability to execute. And the number one thing there was, what's the culture gonna be? People didn't know, like, what are we, what's the alignment aspect of like, what are we building? What kind of company are we? Who are we? What are we building? And then, what's the culture? How are we being intentional about it? So, you know, we did a lot to work on that, ran through a collaborative values process over a year ago,

• 32:35Speaker 02

  where we brought the whole company together, figure out what we care about. And then more recently, I've been thinking about, after, you know, a lot of this self-work in terms of making myself feel, you know, kind of consistently good every day, and remove my attachments to outcome, I've realized, you know, there's a set of principles that I want to implement at the company, and that I think that execution will flow from those things, right? If we build a company that has a high empathy for each other, where we have care for each other, where people are very collaborative, where we are, you know, people feel like the locus of control for what's happening is inside of them, instead of outside of them, you know, things are happening through them, not to them, I think that, all the execution will actually flow from that.

• 33:19Speaker 02

  You know, one of the things I never understood before, which I feel like I really understand now, is that saying that culture eats strategy, right? I felt like I had very good strategy with Atrium, but I forgot about culture in that first part of the company, and now I realized, I've, you know, kind of realized how important it is. Right, right. You know, one of the things I'll say that we're doing is, recently I read this book called The Fifteen Commitments of Conscious Leadership, which is an amazing book, but it's really about building a certain type of company, what, you know, the authors call a conscious company. But I would, I would center it around, you know, that locus of control question, like, do you have radical responsibility for what's going on in your life, in your company, you know, regardless of who you are?

• 34:00Speaker 02

  And read that book, and I realized this is the type of company that I want to work at. You know, it's a company populated by team members who really believe in these sets of, you know, these principles. And so, we're kind of going through a process of trying to implement that at our company, and... Really, culture is one of the highest. It went from something that I didn't prioritize to my top priority.

• 34:22Andrew Chen?

  Yeah, well, and I think that's it's really interesting because it's you because you'd started Kiko like like out of school.

• 34:29Speaker 02

  Yeah.

• 34:29Andrew Chen?

  Right, and so unlike some folks who maybe, you know, they go and they work at Google or Facebook or something, and they maybe have a template for the company culture they they want to create. This is something that you kind of had to learn and adjust.

• 34:42Speaker 02

  Right.

• 34:42Andrew Chen?

  Over many, many kind of company iterations of various companies that you had built.

• 34:46Speaker 02

  That's right, we had never worked at a place with good culture or a culture, right? Because we had always worked at our own company, so we were just making it up as we went along. When you're not intentional about your culture or type of company you want to be, then you make your the culture ends up being the accidental collection of good and bad choices and like personality quirks and good and bad behaviors that your founding and executive teams propagate, right? And it's accidental, right? And oftentimes, there's things that are not good behaviors that get propagated culturally. And oftentimes, there are people justify it because they're like, well, they conflate their correlation with causation, right?

• 35:26Speaker 02

  They're like, because we, you know, are have behavior, maybe we're like, we're like a low empathy company, let's say, but they don't call it that. They're just like, we make decisions based on like meritocracy, right? And they're like, but we the best idea is going to win, but then maybe that's like because that's that's a behavior that they've propagated, but that might not be the real reason why they they've actually been winning, right? I think a lot of companies in Silicon Valley kind of succeed despite their management, actually, not because of it. And what I mean by that is like, the idea was so good that a bunch of 25 year olds could run the company, right? That core product market fit was so good, it was just a rocket ship, and then people were just trying to hang on. Now, eventually, I think they do figure it out, but oftentimes in those early days,

• 36:10Speaker 02

  I think it's actually quite, you know, not intentional and oftentimes not that good.

• 36:14Andrew Chen?

  Yep. You know, in our conversation today, we've talked about all the things that you've changed.

• 36:20Speaker 02

  Yeah.

• 36:21Andrew Chen?

  You've changed from consumer to B2B. You've changed how fast you fundraise. There's been a lot of different changes. Is there anything that you feel like there's a core that you're like, okay, there's this thread that I'm trying to do the same between all the companies? Or is it just really iterating very quickly and you're doing a lot that's different?

• 36:44Speaker 02

  Well, I think that core ethos of iterating quickly, that's like a YC ethos. That's something that we really did carry on at the very beginning. So, speed was something that's pretty important. I think that really being helpful in the community, not just your startup, I mean, including your startup, but also the community of startups, that's something that we learned, behavior we learned from the early days of YC. And even like our community of friends who were founders who all became successful, helped each other out. And then now today, it's an ethos that would take to Atrium to really build a company that's kind of for startups, by startups, that helps out these fast-growing startups.

• 37:28Speaker 02

  So, that ethos is probably something that's pretty similar. Kind of similar to like what you guys have at Andreessen, right? Which is like, if we can be the most helpful in terms of providing these networks of services, that is something that is going to kind of pay dividends for us as a brand. That's something I believed personally and then also at Atrium throughout my entire career.

• 37:50Andrew Chen?

  Right. Yeah, I mean, as you know, one of the things that's great about the Bay Area is that it ends up being this very long-running, relationship-driven place where you meet people like, I mean, we met like 10-plus years ago, right? And that's the kind of interesting thing where there's many, many cases where you can work together. And so, focusing on value creation as opposed to like, how am I going to try to position myself to like, capture the most value? Like, I think that certainly runs, like, I think it's one of the very special things about the Bay Area culture.

• 38:24Speaker 02

  Absolutely. Where we're at, you know, where all these people who I saw in the early days, like 13 years ago, all these different founders, you know, these two-person startups that weren't even anything, where they're at, their company might not have succeeded, but they have like created some value here in Silicon Valley by being in that ecosystem, being helpful and then, you know, maybe becoming an executive at someone else's company or becoming an investor, early-stage investor at another company that really worked. And so there really is like a feeling of if you kind of get out what you've put into this community. And that's one of the things I really love about it.

• 38:57Andrew Chen?

  How do you think about the idea that, you know, when you're first getting started, you're a first-time entrepreneur, there's kind of like low expectations, right? Because you're like, maybe this'll work, maybe this won't work. People's expectations of you are like kind of low too. Because they're kind of like, I don't know, who knows? You know, Justin's off in San Francisco doing this thing. He's running around with a camera on his head. And it's just kind of a fun thing. And then now, several companies later, because also you've raised money and because you've done a lot, et cetera, you know, the expectations must be higher. Like, how do you think about, you know, how do you think about those expectations, managing your own, you know, your own expectations around that?

• 39:42Speaker 02

  Yeah. Well, I always think that every entrepreneur's expectations for themselves are very exceedingly high, right? If you're the type of person who was a PM or engineer at, you know, one of these fan companies and then you're like, I'm going to start a startup because I see other people doing it,

• 39:56Andrew Chen?

  Yeah.

• 39:57Speaker 02

  then you don't think, you don't go into it thinking, well, I'm just going to create like a whatever, something that's like a nice, small business, right? You go in being like, I'm going to raise Series A from Andreessen and we're going to be, you know, this product that just goes poof, the next Snapchat or whatever. And so I think that like it's always a battle against your own, like the kind of devil on your shoulder who's telling you, you're not good enough. You know, you're not doing well enough, you could be doing better. And I think the way that you win that battle is by really internalizing and realizing that Whatever happens, you're gonna be fine.

• 40:35Andrew Chen?

  Right.

• 40:36Speaker 02

  And you're probably gonna be the same. You're not gonna be happier or less happy, actually. And now, most people do not actually successfully internalize that well enough, in my opinion. But it is true. I firmly believe it's true. And it's something that the sooner you start practicing that in your head, really, you know, feeling that and experiencing that in your, in your, um, in yourself internally, then the happier you'll be. And that's not to say that a lot of, you know, people I come into contact with, like friends even, or where people work for me are like, well, my drive, like that, that need to win at all costs is my edge. But I really don't believe, I mean, maybe that's true for other people, but for me, I never found that to be the case.

• 41:17Speaker 02

  It's like, no, it was just like the kind of unhappiness that was created around it that would make it actually less sustainable for me to continue on. Because I was always, you know, you can't, human beings don't wanna live in a high-stress, high-anxiety state for too long. That's how you burn out.

• 41:31Andrew Chen?

  Yep.

• 41:31Speaker 02

  Right? So startups are not, I mean, contrary to popular belief, it's not a sprint, it's a marathon, right? There's these overnight successes. Twitch, right, came out of nowhere. Eight years from incorporating that company to selling it. Almost exactly eight years. Right? So that is a long time. And in order to last a long time, you need to figure out a way that you're okay with what's going on. And what's going on is always gonna involve bad things. Like, things, you know, there's gonna be good and there's gonna be bad. So if you don't figure out a way that you psychologically are okay with that, you're gonna give up. And if you give up, you're never gonna see it to the ultimate potential that whatever your startup is can be.

• 42:12Andrew Chen?

  Great.

• 42:14Andrew Chen?

  I'm gonna throw in kind of two, two, two last questions in here. One is, you know, what are you reading these days? Do you have any sort of recommendations, podcasts that you like? Kind of media consumption is kind of a way to, to, to learn yourself.

• 42:30Speaker 02

  Yeah.

• 42:31Andrew Chen?

  And anything sort of especially super impactful over the last couple of years that, that you wanna, you wanna reference?

• 42:36Speaker 02

  Yeah, that's, that's great. I'm so, uh, reading a lot, actually, because I deleted all the entertainment apps off my phone. Including the browser and I'd locked it so that I don't can't install new apps because I was a total phone addict. That includes.

• 42:49Andrew Chen?

  Wait, how do you lock, how do you lock your?

• 42:50Speaker 02

  So you can lock installing new apps, you can delete the app store and put a passcode lock on it. I gave my wife the passcode, she put in a passcode, I don't know what it is.

• 42:58Andrew Chen?

  Right.

• 42:59Speaker 02

  So I can't.

• 42:59Andrew Chen?

  This is like a parental lock.

• 43:00Speaker 02

  It's a parental lock, yeah, exactly. So I don't have control over my own phone anymore. But the consequence of that is I read a lot more books, which is good. A couple of ones that have been particularly impactful to me. Number one is this book called The Untethered Soul. So this book changed my life. It's really about, the idea is that you are not the thing that you think you are. You know, most people go through life thinking they are the experiences that they've experienced, the thoughts that they have, or the emotions that they have. But really, you're just the observer of these, these things that are happening. And by creating, it's almost like you're watching a movie, right? Like a, you know, movie that has all the five senses plus emotions plus thoughts. So like a seven dimensional movie of, of, you know, the just in life, right?

• 43:46Speaker 02

  And I think that was a very important message to me to realize, like and internalize that like actually these attachments, these things that I think will happen, that will like drive happiness, like experiences or events or whatever, will never actually drive true internal happiness. So amazing book, The Untethered Soul, highly recommended. Another book that I think made me a very, a much better leader was this book I read called Leadership and Self-Deception.

• 44:11Speaker 02

  Amazing book. The book, the purpose of the book is really there's two ways to treat other people. Inside the box and outside the box, but really I mean like without empathy or with empathy, like treating them like a, you know, like an object or a person, right? And if you, the idea, the fundamental idea behind the book is if you treat people like an object, that number one, they don't like it, right? But the second thing is, if you treat people like objects who are just there to fulfill something for you, right? Like at work, it would be like to, you know, hit some number or metric or whatever, do some job. The problem is that you will lie to yourself about, when there's negative situations, about what your role is. You'll self deceive, you'll say, oh, this person is a hundred percent at fault and I'm zero percent at fault.

• 44:54Andrew Chen?

  Right.

• 44:55Speaker 02

  And I found myself actually doing that a lot of times. I realized, you know, I felt like I, I was. You know, had a high degree of empathy and for other people. But I realized that was for people who I felt like were performing really good, where my observation was like high performance. But I wasn't where my observation, where my feeling was that there wasn't high performance. I felt like I would slip into this like low empathy mode. And the problem is that when you're in that mode, you don't admit what are the things that I have done. What, you know, Justin, what are the things I have done to contribute to that situation? So examples could be someone that put someone in the wrong job. Didn't give them clear enough criteria for success or failure. Didn't support them with the right resources, right?

• 45:39Speaker 02

  There's many reasons why I could have contributed to some situation failing. And I found that like I would lie to myself in those situations. So, you know, that was a really important book for me. Those are probably two ones I really recommend.

• 45:53Andrew Chen?

  That's great. Are you doing a lot of podcasts right now?

• 45:57Speaker 02

  Listening to them?

• 45:57Andrew Chen?

  Yeah. That kind of is entertainment.

• 46:01Speaker 02

  I'll listen to some podcasts. I've been listening to some of the Joe Rogan experience.

• 46:06Andrew Chen?

  Nice.

• 46:07Speaker 02

  And that's probably the, this is probably it. I like, I just listened to the one with Alex Honnold where he's talking about climbing. You know, so it's pretty interesting.

• 46:18Andrew Chen?

  I'm gonna ask you the time travel question. So if you were today, an enlightened repeat entrepreneur, to go back to yourself when, you know, you're 22, 23, just getting started doing this thing, you know, what advice would you give yourself?

• 46:34Speaker 02

  When I'm just getting started, you know, probably join Facebook. No, but the, maybe the real answer, I've actually, you know, I don't, I don't really regret any of the like economic choices or anything. I think I've had this tremendous opportunity.

• 46:51Andrew Chen?

  Yeah.

• 46:52Speaker 02

  To like build and discover these new things and build, build companies. And I wouldn't trade it for anything. I think the thing I could have done better or like learned, you know, back then is, you know, self-improvement is a thing. You should probably like work on that. Maybe that's number one. The second thing would be.

• 47:10Andrew Chen?

  Stop eating pizza at work.

• 47:11Speaker 02

  Yeah, stop eating pizza at work. Number three would be you should.

• 47:16Speaker 02

  You know, things take time. Like, don't be in such a, you know, it's not like a one-year, one-and-done, like, no, you're a billionaire. You know, like, if you look at the, let's say, any sort of, like, the Amazon share price or, like, market cap over time, right? It looks, like, even through, like, the last couple of years, it looks like an exponential curve, right? And so, you know, if Bezos had been, like, you're, you know, like, 15, which is a long time to be starting a company, like, oh, man, I made it, I'm done, like, I'm gonna retire, like, well, you know, the company would look a lot different, right? So, you know, things take time, and I have to constantly remind myself that. I think humans, you know, here in Silicon Valley especially, but then human beings

• 47:58Speaker 02

  in general are wired to, like, always want the new, you know, look for the new thing, what's new, what are, like, what's your new thing? It's something that everybody's asking about in Silicon Valley, they're always, you know, that's a question here.

• 48:09Andrew Chen?

  Right.

• 48:10Speaker 02

  But the best entrepreneurs here, the ones who've created lasting companies and lasting value, they stick with their thing for decades, you know? And that's what impresses me most now, and I wish that I had kind of realized that, you know, before.

• 48:27Andrew Chen?

  Awesome.

• 48:28Speaker 02

  Better late than never.

• 48:30Andrew Chen?

  Awesome. Justin, thank you for coming by.

• 48:32Speaker 02

  Yeah.

• 48:33Andrew Chen?

  Really good discussion.