a16z Podcast: 10+1 Lessons from Serial Entrepreneur Justin Kan

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0:00:21 – Hey, I’m Andrew Chen from Injuries and Horowitz
0:00:24 and today we have Justin Kahn, who is one
0:00:26 of our repeat entrepreneurs that we are very excited
0:00:28 to be working with on Atrium.
0:00:31 And so we’re gonna talk a bunch about
0:00:33 what is it like to be a repeat entrepreneur?
0:00:34 I think we were just going through the list.
0:00:37 There’s like five different companies on there
0:00:39 and you’ve learned a ton from every single one.
0:00:42 And so we’re gonna do a series of sort of compare
0:00:45 and contrast across quite a number of topics.
0:00:47 But as a very first step,
0:00:50 I think it’d be awesome to have Justin talk about
0:00:53 some of the companies that you’ve been involved in.
0:00:56 And I know the company you were running when we first met
0:00:57 where you were running around with a camera on your head
0:01:00 is not actually even your first one.
0:01:01 There’s one before that called Kiko.
0:01:03 So why don’t you talk about Kiko first?
0:01:04 – Sure, yeah.
0:01:06 So I’ve been an internet entrepreneur here
0:01:09 for the last 14 years since 2005.
0:01:11 Our very first company was called Kiko.
0:01:13 It was kind of like Google Calendar,
0:01:16 but it came out one month before Google Calendar came out
0:01:20 and wasn’t really that good when I’m honest about it.
0:01:23 And so that company didn’t work out super good.
0:01:26 We ended up fire selling it on eBay
0:01:28 after several failed acquisition attempts
0:01:30 with the Sullivan Valley players.
0:01:34 And then after we did that, we started another company.
0:01:39 This one was even less well thought out than Kiko was actually,
0:01:42 which was the idea was we would create our own
0:01:45 live video reality TV show on the internet.
0:01:48 I do think that tapped into several things
0:01:49 that were in the zeitgeist
0:01:50 that actually have become popular now.
0:01:54 But unfortunately, we as talent in our own show
0:01:56 were not very entertaining and not very popular.
0:01:58 And so we launched this live streaming show.
0:02:00 We called it Justin TV.
0:02:03 ‘Cause I was the only one in our four founders
0:02:05 who was stupid enough to put the camera on his head
0:02:09 and be like, I’ll make myself the subject of this show.
0:02:12 And you literally wore, I remember you wore a backpack.
0:02:15 – Yeah, so this was 2007.
0:02:19 So it was pre-iPhone, pre-good cellular internet.
0:02:21 So we had this computer in a backpack
0:02:25 with like multiple cell phone modem connections.
0:02:27 And we hooked it up to a camera.
0:02:30 So there was a camera, this computer virtualized the video
0:02:33 as a webcam, basically sent it over to the server.
0:02:36 And then we had this very hacky way of streaming it out
0:02:39 to the millions of people watching,
0:02:40 actually not millions, hundreds,
0:02:43 but the people who were watching at home,
0:02:46 they were following along, it was actually pretty fun.
0:02:48 They could text, we put our number up there,
0:02:51 they would text me, usually fairly offensive things actually.
0:02:55 But then eventually we launched this show,
0:02:57 people started coming because they were like,
0:02:59 what is this guy doing, this is crazy.
0:03:02 They were like, you’re very boring, I hate your show,
0:03:04 but I want to create my own live video stream.
0:03:05 So how are you doing it?
0:03:07 And then the light bulb kind of went off
0:03:10 and we said, aha, let’s create a live video platform.
0:03:12 And that became Justin TV, the platform.
0:03:15 And then after that, we ran that for a couple of years,
0:03:17 I’ve condensed it because it’s a very long story,
0:03:19 but we raised a bunch of money,
0:03:21 ran it for a couple of years,
0:03:24 hit the nuclear winter of video startups
0:03:26 where all the other video startups in Silicon Valley died.
0:03:30 We were pretty scrappy and survived on like a ramen budget.
0:03:33 Eventually decided we needed to pivot to some new ideas.
0:03:36 And from there we incubate a few ideas internally.
0:03:38 One of them was a video app called social cam,
0:03:40 which we spun off and eventually sold to Autodesk.
0:03:45 And another one was a site that we,
0:03:48 my co-founder really thought of,
0:03:50 which was the idea was focus on,
0:03:53 let’s focus on the video game related video on our site.
0:03:57 And that became Twitch, which kind of grew and grew and grew.
0:03:59 We eventually pivoted the entire company to Twitch.
0:04:02 My co-founder Emmett was the CEO of the company
0:04:06 and eventually sold it to Amazon for $970 million in 2014.
0:04:08 About five years ago.
0:04:10 Along the way started some other companies
0:04:11 to start this company called exec,
0:04:14 which is in the errand running/home cleaning space.
0:04:16 It’s kind of like a handy year home joy.
0:04:19 We actually ended up selling it to handy,
0:04:22 which through an act of God sold to Angie’s List this year.
0:04:26 And then more recently,
0:04:28 I’d been a partner Y Combinator for a couple of years
0:04:30 and then incubated a few companies.
0:04:34 One of those was this video Q&A app called Whale.
0:04:37 And then just fast forwarding all the way
0:04:38 up till the present day,
0:04:42 decided I want to really put all my eggs back in one basket,
0:04:45 precariously thrown around basket.
0:04:47 And so I decided I’d start a new company.
0:04:48 That idea was Atrium,
0:04:51 which is a technology enabled law firm for startups,
0:04:53 really trying to solve all the problems that I had
0:04:56 as an entrepreneur when dealing with legal.
0:04:58 To make legal faster, more price predictable,
0:05:00 more transparent for me, the business owner,
0:05:02 you know, the business manager.
0:05:05 And that’s what we set out to do about two years ago.
0:05:06 It’s going pretty well.
0:05:08 We’re serving a bunch of startups here in Silicon Valley
0:05:09 with all of their needs.
0:05:12 And it’s been great, but I’m sure we’ll get to that.
0:05:13 – Awesome, yeah.
0:05:18 Well, I think one place where I’m going to start on this
0:05:23 is a lot of the advantages of being a repeat entrepreneur
0:05:25 are that, you know, you can raise more money
0:05:29 and there’s more, you know, maybe easier to recruit talent.
0:05:30 And there’s, you know, there’s all these advantages
0:05:32 that kind of, you know, come along with that.
0:05:35 One of the disadvantages I find ends up being that,
0:05:38 you know, there’s so many like distractions, right?
0:05:39 Like you could, there’s a million different things
0:05:40 you could do.
0:05:42 There’s a lot of things pulling at your attention.
0:05:45 I’m really fascinated by, you know, your movement
0:05:48 from going from YC and an incubator
0:05:51 where you can maybe kind of dip into a lot of little things
0:05:53 versus kind of putting all your eggs in one basket
0:05:54 and trying to like start a company.
0:05:56 Like, you know, to talk to us about that,
0:05:57 that kind of decision.
0:05:59 – Yeah, that’s a great question.
0:06:01 So once you become, you know, successful in some way
0:06:03 in Silicon Valley, whether that’s, you know,
0:06:04 you’ve been the executive at a company
0:06:06 that’s, you know, rocket ship unicorn
0:06:08 or you’ve started a company, you know,
0:06:09 the world opens up, right?
0:06:11 People want you to be a VC.
0:06:15 They want you to, you know, work on projects with them.
0:06:18 You can start any company that you want,
0:06:19 which is great, right?
0:06:20 But there’s just paradox of choice
0:06:22 and focus can be a huge problem.
0:06:25 I know for a lot of friends of mine, it has been as well.
0:06:27 As an investor, as a partner at YCom,
0:06:28 there were some parts I really liked.
0:06:31 You know, I loved helping early stage founders out
0:06:34 and like really working with them on these problems that,
0:06:36 like I felt like for five to 10% of them,
0:06:37 it was like life changing, right?
0:06:39 Like me helping them out in a way,
0:06:40 I came up with some great idea
0:06:42 or helped them at a critical moment.
0:06:43 That was life changing.
0:06:44 But then there was a large majority of them
0:06:46 that probably could have been listening
0:06:48 to a YouTube video of me or this podcast
0:06:50 and like you get the same information, right?
0:06:54 And so I didn’t feel like the feedback cycle
0:06:56 was fast enough also as an investor.
0:06:57 And I didn’t really feel ultimately,
0:06:58 like after the first couple of years
0:07:00 that I was continuing to learn and grow.
0:07:02 And you know, I’m still in my 30s.
0:07:03 I was like, I need to do something
0:07:05 where I’m going to be forced to grow.
0:07:09 And really the number one vehicle for personal growth
0:07:11 that I’ve ever experienced in my life has been startups.
0:07:13 You know, so I went back to when I knew
0:07:17 and I really decided that in order to grow as a founder,
0:07:19 you know, we had a pretty big outcome with Twitch
0:07:21 and I’d seen a lot of different things
0:07:24 in order to really grow to the next level.
0:07:26 I would have to do something that potentially
0:07:27 could be even bigger.
0:07:29 And so I really felt like it deserved,
0:07:30 that deserved my full attention.
0:07:33 And so that’s kind of how I decided.
0:07:35 I don’t necessarily think it’s the right answer
0:07:37 for everyone because what I didn’t mention
0:07:39 was that I had selective memory at the time
0:07:42 and I forgot just how painful starting a startup could be.
0:07:45 And so for the first couple months of atrium,
0:07:46 I was like, oh man, this is a dream.
0:07:47 I’ve like finally leveled up.
0:07:48 I learned all these skills.
0:07:51 I’ve like, I made it as a founder.
0:07:53 And then reality boom set in.
0:07:56 And of course there were nothing ever goes according to plan.
0:07:58 There were pains, there were struggles.
0:08:01 And that was, you know, that’s part of the journey.
0:08:03 But then the good part is, of course,
0:08:06 when you experience pain, that is a catalyst for learning.
0:08:08 And so I really got what I wanted in the end,
0:08:10 which was forced to learn.
0:08:11 – Right, that’s great.
0:08:13 And I know one of the big differences
0:08:16 among some of the companies that you started
0:08:17 in the past versus atrium,
0:08:20 and something that you’ve talked a lot about is,
0:08:21 you had this sort of succession
0:08:24 of very like consumer oriented startup,
0:08:26 sort of like watching other people play video games.
0:08:28 Like that’s as consumers, basically.
0:08:33 And so very interestingly, atrium is a B2B thing.
0:08:36 And why did you choose B2B?
0:08:37 Was it just for novelty?
0:08:39 Was it just to push yourself?
0:08:43 Or do you think that there’s something different in mind
0:08:47 that maybe takes advantage of some of your new found skills?
0:08:48 – Yeah, well, Twitch, I guess, is really the,
0:08:50 it’s like the ultimate consumption thing,
0:08:51 ’cause it’s you’re consuming someone,
0:08:53 consuming video games.
0:08:54 – Right, right.
0:09:00 – For me, I felt like maybe this was an analysis
0:09:01 I’ve done like retroactively,
0:09:03 but I think I’ve had this discussion
0:09:05 with a couple people with multiple time founders.
0:09:07 And when you’re an early stage founder,
0:09:09 when we started Kiko and then Twitch,
0:09:10 when we started Twitch, we were like,
0:09:12 or just in TV, it was like we were 23 years old.
0:09:14 And we had no skills.
0:09:17 I never had a real full time job in my life.
0:09:18 And even though we were programmers,
0:09:20 we were like new college grad programmers.
0:09:22 We were not good.
0:09:24 We were horrible managers.
0:09:26 We basically had nothing going for us.
0:09:28 When you have nothing going for you,
0:09:31 except for your like willing to put in hard amount,
0:09:35 like long hours on a lot of blood, sweat, and tears,
0:09:38 then you should focus on things that are like,
0:09:40 where there’s a lot of market risk,
0:09:43 because ideas where there’s market risk,
0:09:45 you can potentially win those, right?
0:09:50 Now, as someone who has abilities and skills,
0:09:53 where I’ve learned skills over the last 14 years,
0:09:57 you wanna focus much more on like execution risk things.
0:09:59 And so I felt like B2B startups
0:10:01 are more about execution risk.
0:10:03 I felt like this legal market,
0:10:05 particularly was already a big market,
0:10:06 and you just have to figure out
0:10:08 how to do it 10 times better, right?
0:10:09 And I felt like I had a roadmap
0:10:11 for how to do that in my head.
0:10:14 And so that’s why I felt that this was a better use of time.
0:10:17 ‘Cause some of the consumer startups that I had incubated
0:10:18 and played around with post Twitch,
0:10:20 actually it was really hard to find product market fit, right?
0:10:22 Like, I don’t have any advantage
0:10:25 in finding product market fit with a consumer app
0:10:27 more than the 22 year old Justin.
0:10:28 – You might have a disadvantage.
0:10:29 – Yeah, I probably have a disadvantage
0:10:31 ’cause I’m like already more set in my ways.
0:10:34 I’m like less in tune with the culture.
0:10:36 I’m like, I don’t know what the kids are doing.
0:10:40 So, with the Justin of today, invent the Twitch of today.
0:10:41 Like, I don’t think so, right?
0:10:43 Like I’m an old guy now, man.
0:10:44 (laughing)
0:10:45 It’s game over for me.
0:10:48 – I wanna unpack this market risk, execution risk.
0:10:49 ‘Cause that’s obviously,
0:10:51 it’s such an important distinction,
0:10:55 but very colloquial, kind of in our understanding of it.
0:10:57 What do you mean by market risk
0:10:59 and sort of maybe new entrepreneurs
0:11:00 can have an advantage in market
0:11:02 and tackling something with new market?
0:11:04 How do you know if an idea has a lot of market risk?
0:11:05 – Sure, that’s great.
0:11:08 So, Twitch and H&M are the perfect examples, right, almost.
0:11:10 So, Twitch, it’s like when we started,
0:11:12 when we pivoted Justin DV to Twitch,
0:11:13 or even Justin DV is a good example,
0:11:15 but Twitch is the best one probably.
0:11:17 When we pivoted Justin DV to Twitch,
0:11:20 nobody believed that there would, this was a market, right?
0:11:22 No one believed, no investors,
0:11:25 very few of our even internal employees believed,
0:11:27 and even the founders were skeptical.
0:11:29 Emmett deserves the credit here, ’cause he had belief,
0:11:31 but a lot of the other co-founders were skeptical.
0:11:34 I’m like, does this exist as a business?
0:11:37 And so, the good part is that the competition there
0:11:39 was very low, right?
0:11:41 There weren’t experienced entrepreneurs being like,
0:11:43 this is gonna be a huge business, we should compete.
0:11:47 So, really it was, the entire thing was market risk
0:11:49 and figuring out, do we have product market fit,
0:11:50 how do we build product market fit?
0:11:51 – ‘Cause in that case,
0:11:53 you’re trying to be the first in the category.
0:11:54 There’s no substitutes really.
0:11:57 You’re watching someone else play street fighter
0:11:59 at the arcade, that’s a substitute.
0:12:00 – Exactly, you have a lottery ticket, right?
0:12:01 – You have a lottery, yeah.
0:12:04 – It’s a lottery ticket, and if you pivot a bunch of times
0:12:05 and listen to your customers,
0:12:06 you might be buying more and more lottery tickets.
0:12:08 But your lottery tickets are just as valuable
0:12:11 as the experienced entrepreneur’s lottery tickets
0:12:12 that he’s buying.
0:12:14 So, he’s a fool to play that game,
0:12:16 and I don’t think you see as many experienced entrepreneurs
0:12:18 playing that same game.
0:12:20 Whereas, with execution risk businesses,
0:12:23 my lottery ticket now is way bigger than the guy
0:12:26 who’s like the 22-year-old Justin, right?
0:12:30 So, for a B2B startup, I know, oh, I can attract talent.
0:12:32 I can hire a sales team.
0:12:34 I can raise capital.
0:12:36 And so, it’s a lot more, for something
0:12:39 where it’s very established that that’s gonna be a business,
0:12:41 or some business is gonna be in there,
0:12:45 it’s like he’s stupid to play against me, you know?
0:12:47 – Right, that makes sense.
0:12:48 Well, you know, and I always find it funny
0:12:51 that in the consumer startup world,
0:12:54 that if you look at the last kind of decade of hits,
0:12:56 if you were to tell people, oh, yeah,
0:12:58 the biggest hits are gonna be this app
0:13:00 that lets you get in strangers’ cars,
0:13:02 this app that lets you stay at someone
0:13:04 you don’t know’s like house,
0:13:07 an app where you swipe left and right
0:13:09 in order to meet people on the internet,
0:13:12 and an app that lets you watch other people play video games.
0:13:16 You would be like, that’s the craziest list of
0:13:18 billion-dollar companies I’ve ever heard.
0:13:21 And yet, that that is actually how consumer
0:13:23 the internet actually, you know,
0:13:25 the ecosystem unfolds, it’s insane.
0:13:27 – It takes a lot of people who have nothing to lose
0:13:30 to discover those ideas, right?
0:13:33 – Right, yeah, and so one of the things,
0:13:35 one of the clear advantages in all of this
0:13:38 is that, you know, let’s talk about fundraising,
0:13:42 and the decision on whether or not to raise
0:13:44 a bunch of money out of the gate,
0:13:48 versus doing the kind of, you know,
0:13:51 ramen profitable, you know, cockroach thing, right?
0:13:54 That’s sort of like, you know, one common contrast,
0:13:55 and then obviously you had a very unique
0:13:57 fundraising strategy as well.
0:13:59 So maybe talk about that decision,
0:14:01 and then kind of how you ended up pursuing it.
0:14:03 – Look, I’m not convinced that raising a ton of money
0:14:05 out of the gate is the right strategy.
0:14:08 You know, the Silicon Valley is littered
0:14:10 with dead bodies of these companies,
0:14:13 you know, the Juceros, and the Kools,
0:14:15 and like all these companies that have raised
0:14:17 a ton of money, and then like they,
0:14:20 when you have a ton of money, you spend a ton of money, right?
0:14:23 Now there’s other companies like the Jet.coms
0:14:24 that, you know, they made it work.
0:14:28 So, you know, I’m not convinced it’s the worst strategy ever,
0:14:29 but I’m not convinced it’s the best.
0:14:32 But for me personally, you know,
0:14:34 where it’s an execution risk business,
0:14:37 I’m too rich to like, fuck around with the like,
0:14:39 you know, okay, I’m just gonna do a seed round,
0:14:42 and like, and just like, take a long time, right?
0:14:45 Like for me, speed to market and execution
0:14:47 was really important, and I felt also like
0:14:48 this market really supported and required it,
0:14:51 because, you know, it is the legal space,
0:14:54 there is, you know, so a lot of value
0:14:57 in making sure that the clients and the talent,
0:15:00 the attorneys talent, and other legal providers,
0:15:03 like, think this company’s gonna be around, right?
0:15:05 So that’s very important.
0:15:06 And so, you know, this is a strategy,
0:15:08 I don’t necessarily recommend to anyone
0:15:11 who can raise a ton of money that this is the right strategy,
0:15:13 it’s just the strategy that we picked.
0:15:16 In terms of the tactics of like how we did our round,
0:15:18 especially our Series A, you know, my idea was,
0:15:22 because VCs are kind of naturally adjacent to legal,
0:15:25 right, like, for example, when you fund a company,
0:15:27 they need someone to help them on the legal side
0:15:30 with all of the, you know, paperwork
0:15:32 and the execution of that funding round.
0:15:35 We felt like getting a lot of VCs on our side
0:15:37 would be a good tactic, and so we ended up going out
0:15:40 and raising money for our seed round of, you know,
0:15:44 over 90 different investors from all over Silicon Valley
0:15:46 because I felt like it would be really good
0:15:48 to have those investors on our side
0:15:50 and recommending Atrium as a channel partner,
0:15:54 and so that was our tactic there.
0:15:56 – Right, and I think it’s something where,
0:16:00 you know, to your point, if something
0:16:03 that you’re working on is primarily execution,
0:16:05 then that means that, you know, you can,
0:16:08 there are times and places where you can use money
0:16:10 to solve it versus, it seems like, you know,
0:16:12 part of the market risk thing is it just, you know,
0:16:14 to your point, it sort of lets you buy more lottery tickets,
0:16:17 but it may not accelerate the process
0:16:19 of actually doing it, right, and so I think that,
0:16:21 that sort of feels like one main difference,
0:16:23 and then the other one is, you know,
0:16:25 that just to build on what you’re saying is that
0:16:28 if you are in an industry where trustworthiness
0:16:31 is really important, then being well-capitalized is key,
0:16:33 you know, the same way you wouldn’t, you know,
0:16:36 if you’re gonna, you know, for example,
0:16:39 you know, build a FinTech startup where, you know,
0:16:41 you’re gonna ask consumers to trust their money
0:16:44 with you, you know, like you wanna be legit,
0:16:46 you wanna be well-capitalized, you wanna have, like,
0:16:48 you know, super strong executives
0:16:50 and board members and investors, and like,
0:16:52 and that’s a strategy, kind of, that’s a little bit,
0:16:54 kind of, like, self-perpetuating as well.
0:16:55 – Yeah, that’s a great example.
0:16:57 If you’re gonna build, like, a new bank, right,
0:16:59 like an online, or like a mobile-first bank,
0:17:01 which is, I think, some people are doing,
0:17:05 would you wanna raise, you know, $1 million,
0:17:07 or $1 million seed round, or a $5 million seed round,
0:17:11 or a $50 million series A out the gate?
0:17:12 Obviously, if it’s available to you,
0:17:15 you want more money, ’cause you know people need banks, right?
0:17:17 It’s just a matter of can you do it better, right?
0:17:19 That’s a perfect example, and there’s, you know,
0:17:20 there’s many others here in Silicon Valley.
0:17:22 I think we’ve actually shifted more
0:17:25 as the cycle has changed over the last 10 years,
0:17:26 the tech cycle.
0:17:29 We’ve shifted more to these execution-risk startups,
0:17:31 and so, you know, you’ve consequently seen,
0:17:33 I mean, it’s a chicken and egg thing, really,
0:17:35 what came first, but like, you’ve seen these more and more,
0:17:37 like, bigger rounds, I’d say,
0:17:39 that are supporting these companies.
0:17:41 – Well, you know, one of my,
0:17:44 one of the partners here, Chris Dixon,
0:17:46 has talked about the idea that, you know,
0:17:50 if you have a set of problems that has not been able
0:17:52 to get solved and improved in, you know,
0:17:55 the 20 years of the modern internet,
0:17:59 then maybe all the techniques that we pioneered
0:18:01 in the last, you know, decade plus,
0:18:04 like being asset-light and just throwing software,
0:18:06 and just shipping really quickly, and being really lean,
0:18:09 like, maybe those techniques don’t work for a reason
0:18:12 in healthcare and fintech and legal services
0:18:14 in real estate, and like, you know,
0:18:15 some set of those things, right?
0:18:17 And so then, very quickly, you have to think,
0:18:19 okay, well, you know, if those techniques don’t work,
0:18:20 otherwise, it would have,
0:18:21 someone would have tried it already,
0:18:23 it would have, it would have sort of, you know,
0:18:25 a little bit like efficient market hypothesis.
0:18:26 – Yeah, that’s the thing.
0:18:27 – It would have kind of like happened already,
0:18:31 like, maybe you need a foundationally different approach.
0:18:34 And so, I think that is actually one of the reasons why
0:18:35 there’s more of these like, quote unquote,
0:18:37 full-stack startups that are going after
0:18:39 these really, really difficult areas.
0:18:40 ‘Cause like, you know, otherwise,
0:18:41 you wouldn’t be able to do it.
0:18:44 – Yeah, well, running experiment right now.
0:18:46 – Yes, yeah, right, no, I think that’s right,
0:18:48 I think that’s right.
0:18:50 So, you know, one of the fun topics,
0:18:52 one thing that I have a tremendous amount of respect
0:18:55 for you on is you’re very, you know,
0:18:58 you’re always on the leading edge,
0:19:00 thinking about, you know, self-improvement,
0:19:03 how to sort of, you know, your own, you know,
0:19:07 personal performance at work, you know, at home, et cetera.
0:19:10 And obviously, one of the big things about, you know,
0:19:12 running a company is that it is enormously stressful.
0:19:13 Right? – Yeah.
0:19:16 – And so, talk to us about like, you know,
0:19:18 when you were a first-time entrepreneur,
0:19:21 kind of Kiko, Justin TV, you know,
0:19:22 how did you think about, you know,
0:19:26 managing the stress of, you know, running a company?
0:19:27 And what was your approach there?
0:19:29 And then let’s talk about kind of like,
0:19:30 the new and improved Justin now, you know,
0:19:32 kind of 10 years later.
0:19:33 – Yeah, so in the early days, you know,
0:19:37 10 years ago, I was not doing anything
0:19:39 in terms of like improving myself.
0:19:44 In fact, I think I used to think about people’s attributes,
0:19:47 maybe not your skills so much in terms of like, you know,
0:19:48 it’s your skills at programming or stuff like that,
0:19:50 but more of like your attributes.
0:19:52 Like, I don’t know if you ever played Dungeons and Dragons,
0:19:55 but when you create a character in Dungeons and Dragons,
0:19:57 you roll this like 20-sided die and, you know,
0:20:00 your strength, it’s like 14, your intelligence,
0:20:02 you roll it and it’s six or whatever,
0:20:04 and that’s what you have, you can’t change it.
0:20:06 And so I felt like people’s attributes
0:20:07 were kind of like that.
0:20:09 And so I never worked on that very much,
0:20:11 self-improvement stuff outside of, you know,
0:20:12 like yeah, I became a better programmer
0:20:14 ’cause we were programmed, you know,
0:20:17 but I didn’t work on things to like make myself,
0:20:20 I don’t know, smarter, right, or harder working,
0:20:22 or like awake more hours of the day, right,
0:20:25 like alert more hours a day or anything like that.
0:20:26 So it was very happened, you know,
0:20:28 everything was kind of accidental.
0:20:30 Like we would, you know, I was not dealing with stress
0:20:31 well at all.
0:20:35 If there was a problem in the company,
0:20:37 I would be very emotionally avoided to it,
0:20:41 or I would like drown my sorrows in like alcohol, right,
0:20:43 which is not a very good coping mechanism at all.
0:20:46 And so, and then like, you know,
0:20:47 in terms of even just down to like
0:20:49 what we were like eating at lunch,
0:20:51 I was, you know, we were talking about this this earlier,
0:20:53 but I would, we would have like pizza every day
0:20:56 at lunch at Justin TV, and then I’d like fall asleep.
0:20:57 Like I’d go into like a carb comb,
0:21:00 like a carb comb in the afternoon, like every day.
0:21:04 And so now more recently, like with atrium,
0:21:06 it’s been a tremendous vehicle
0:21:08 for my own personal discovery,
0:21:10 because I experienced the stress again.
0:21:12 You know, I was like, oh my God, it’s stressful.
0:21:16 Again, this is crazy, why is it so stressful?
0:21:18 And so I started looking for ways to deal with that,
0:21:21 and I really, I mean,
0:21:24 if I had a number of things that started working for me
0:21:26 after I started really exploring it,
0:21:27 a number of things that started working for me
0:21:31 starting last year, you know, everything from,
0:21:33 friend of mine recommended a daily gratitude journal.
0:21:35 So I’ve just been doing that every day,
0:21:37 writing this gratitude journal, five minute journal.
0:21:39 You write down the three things every morning
0:21:40 that you’re grateful for.
0:21:42 And that seems like a very simple thing
0:21:44 and kind of hokey, actually, when I first heard about it.
0:21:48 But what I realized was it helps recontextualize
0:21:49 all the ups and downs that you experience
0:21:51 as an entrepreneur, especially, I mean,
0:21:53 the downs really, like throughout the day,
0:21:54 they’re not as big of a deal,
0:21:55 because in the morning, you’re writing down,
0:21:58 like, wow, I have this opportunity.
0:22:00 You know, I remember the day we came in and pitched,
0:22:02 you guys here, I wrote my gratitude journal,
0:22:05 I get to pitch, you know, Andrewson Horowitz.
0:22:06 That’s amazing, right?
0:22:09 Even whatever happens, that’s an incredible opportunity.
0:22:13 It puts me in the top 0.01% of people in the world
0:22:15 without opportunity, you know?
0:22:18 So that was like pretty amazing.
0:22:20 And then, you know, every day there’s something,
0:22:21 like if you really think about it,
0:22:24 there’s so many amazing things that happen to you
0:22:27 as a human being here in Silicon Valley.
0:22:29 Even just like actually one thing I think in the morning,
0:22:31 oftentimes it’s like the supply chain,
0:22:33 the global supply chain to deliver coffee
0:22:35 from like around the world,
0:22:38 so that I can grind up fresh coffee
0:22:41 and like a pour over in my Chem-X in the morning.
0:22:41 – Right.
0:22:42 – That’s amazing.
0:22:43 – It is amazing. – Like if you think about it.
0:22:44 – It’s totally amazing. – Yeah.
0:22:45 – Right.
0:22:47 – So the gratitude journal really working for me.
0:22:47 And then another thing–
0:22:49 – You’re still eating pizza for lunch every day?
0:22:52 – Yeah, so diet, another thing, I stopped eating pizza.
0:22:54 – So, entirely?
0:22:56 – No, well I started eating a ketogenic diet,
0:22:58 which is a high-fat diet,
0:23:01 but really the reason for me is like,
0:23:05 I just don’t get as tired in the day anymore.
0:23:06 And so that’s been really helpful.
0:23:07 And last year I was experimenting,
0:23:11 I did like some one meal a day, days,
0:23:13 you know, like four days a week.
0:23:15 Some of these weird like Jack Dorsey diets,
0:23:17 kind of Jack Dorsey light or whatever,
0:23:19 but it’s been good for me.
0:23:21 You know, you had to do what your body feels like,
0:23:21 it feels good.
0:23:24 So, you know, that’s some diet and exercise,
0:23:25 pretty religious about exercising,
0:23:28 you know, try to do something every day during the work days.
0:23:29 – Yeah.
0:23:31 – And then the last thing that was really big
0:23:33 is meditation for me.
0:23:35 Start off just with headspace, you know,
0:23:38 I’m not the type of person that people, you know,
0:23:40 assume would be a heavy meditator
0:23:42 or very introspective or anything like that.
0:23:46 But for me, just like starting off with headspace last year,
0:23:48 and then now I’ve been doing transcendental meditation,
0:23:51 which is kind of what Ray Dahlio talks about
0:23:53 and the principles, that’s worked really well for me
0:23:58 to just be more present during the day in my life.
0:24:02 It’s pretty amazing, amazingly profound effect.
0:24:03 – I feel like your Twitter stream
0:24:05 is part of your gratitude journal.
0:24:06 – Yeah.
0:24:07 – ‘Cause I read your Twitter stream and I’m like,
0:24:09 oh, this is like very philosophical.
0:24:11 You know, it’s not like just pulling out like,
0:24:15 oh, here’s a blurb from the latest S1 or something.
0:24:17 Like you’re like, you know, you’re like sharing ways
0:24:20 that the startup community can, you know,
0:24:21 to think about themselves.
0:24:23 – Yeah, the way I think about it is like,
0:24:25 if you want something to be part of your identity,
0:24:26 talk about it.
0:24:28 If you want to learn something, teach it.
0:24:29 You know, and I really believe that.
0:24:31 So for me putting out, you know,
0:24:33 what I’ve been doing on the mindfulness side
0:24:37 and for myself to be more emotionally kind of stable
0:24:40 throughout the days and weeks and months,
0:24:42 as a startup founder, that’s been really valuable to me.
0:24:44 So if I can spread that to other people,
0:24:46 it’s gonna help reinforce it as an identity for me,
0:24:48 but it’s also gonna hopefully help those people as well.
0:24:49 – Right.
0:24:51 You know, one thing I’ve been working on a lot as well,
0:24:54 the last thing I’ll say is just working on realizing
0:24:56 that your attachment out in the very early days
0:24:59 of Justin TV and Twit, Kiko and all these companies,
0:25:03 I had a huge ego attachment to the outcome of the company.
0:25:04 – Yeah.
0:25:06 – Right, my identity and the companies
0:25:07 were like very intertwined.
0:25:10 And more recently, I realized that was the same
0:25:11 at Atrium actually.
0:25:13 Like again, I was like creating that same pattern,
0:25:15 but it was like, it’s a very unhealthy pattern.
0:25:18 So what I realized was I needed to start telling,
0:25:21 reminding myself that no matter what happens
0:25:24 with this company, I’m not gonna be any happier
0:25:25 or any less happy in the long run.
0:25:27 There might be a short burst of unhappiness
0:25:30 if it fails or happiness if it succeeds amazingly,
0:25:33 but you’re not gonna get any happier.
0:25:35 Really, if you’re relying on outside things,
0:25:38 external factors to drive your inner happiness,
0:25:40 you will always be disappointed in the long run.
0:25:43 And the funny thing is I’ve actually run the experiment,
0:25:45 not an A/B test, but a linear experiment on that,
0:25:48 because we’ve had more and more success over time.
0:25:51 Like we started off really paying ourselves,
0:25:54 I think with Kiko, $7,800 a month,
0:25:57 but we only paid ourselves every other month.
0:26:00 And so then we raised funding for Justin D.V.
0:26:02 and we were able to make a little salary,
0:26:05 then we became profitable, we made a lot more,
0:26:07 and then we sold one company, then we sold a lot of companies.
0:26:09 And so we kind of ramped over time.
0:26:14 And after the basics of Maslow’s hierarchy of needs,
0:26:17 we’re taking care of, I felt like I could go out to eat.
0:26:18 I don’t know if that’s on one of those Maslow’s
0:26:20 hierarchy of needs, but after that basic thing,
0:26:22 I could afford to go out to eat.
0:26:24 None of it never mattered.
0:26:26 It never made me sustainably more happy.
0:26:28 And so just reminding yourself of that
0:26:30 and trying to remove those attachments in your mind,
0:26:31 it’s easier said than done,
0:26:34 but having that as like an active practice
0:26:36 has been really important to me.
0:26:38 – Let’s talk about mentorship as part of that, right?
0:26:41 So when you’re building Kiko, Justin D.V.
0:26:45 and you’re a first time entrepreneur,
0:26:49 there’s a lot of experienced people
0:26:52 who are kind of like, go ahead of you in the thing.
0:26:55 And so that’s fantastic ’cause you can learn a ton.
0:26:57 Would love to hear kind of who you thought of
0:26:59 as your kind of lifelong mentors,
0:27:01 people that have helped you for a long time.
0:27:04 And then the other problem that’s super interesting is,
0:27:06 then you start atrium and you’ve had
0:27:08 some major successes behind you.
0:27:11 And then in some ways, the number of people
0:27:13 you can learn from is a much smaller pool
0:27:16 and sort of like, how do you kind of curate your mentorship?
0:27:17 Maybe how has it changed over time?
0:27:20 That’s a broad topic, but would love to hear your opinion.
0:27:21 – Sure, absolutely.
0:27:23 So like the best part about Silicon Valley, in my opinion,
0:27:26 is that there are people here who have done it before
0:27:27 who are willing to help you.
0:27:30 That we would never have made it here even day one
0:27:35 without people who helped us when it was like economically
0:27:37 bad, waste of time.
0:27:40 We weren’t like, didn’t look like a hot prospect
0:27:41 company or anything, right?
0:27:44 So those people will, Paul Graham, great example,
0:27:45 founder of Y Combinator, Paul Buhay,
0:27:47 who is like a partner in Y Combinator,
0:27:50 but they invented Gmail inside of Google.
0:27:52 These are people who invested in us very early on,
0:27:54 mentored us very early on and helped us out.
0:27:57 And that was pretty amazing.
0:28:01 And really that ethos perpetuates itself,
0:28:03 because then as a partner in Y Combinator,
0:28:05 even today as an entrepreneur,
0:28:08 where there’s like lots of conflicting,
0:28:09 competing interests for my time,
0:28:12 I always make sure to spend a little bit of time
0:28:14 mentoring other startups,
0:28:16 because it’s kind of like a pay it forward thing.
0:28:19 And you do the thing that people did for you
0:28:21 when you were younger.
0:28:25 – One of the really obvious sources of mentorship
0:28:26 is actually peer mentorship, right?
0:28:28 And some of the folks that kind of came up with you
0:28:32 at the same time and ended up running
0:28:34 really interesting companies on their own.
0:28:37 And I know they all live in DeBose with you
0:28:39 in San Francisco.
0:28:40 Talk to us about some of your friends
0:28:42 that you consider your mentors.
0:28:44 – Yeah, so it’s great to have friends
0:28:46 who are kind of doing the same path in a lot of ways,
0:28:48 but are one or two steps ahead of you.
0:28:49 So it’s still a case.
0:28:52 Obviously Emmett, my co-founder who’s still running Twitch,
0:28:53 it’s over a thousand people.
0:28:56 I think it’s like 1500 people or something like that.
0:28:59 My brother, who’s COO of Cruise,
0:29:01 co-founder of Cruise, the self-driving car company.
0:29:02 And they’re like over a thousand people.
0:29:05 And Steve, the founder of Reddit,
0:29:08 they’re like 400 something people or whatever.
0:29:11 So, you know, seeing what their problems are,
0:29:13 you know, obviously the problems are always the same,
0:29:14 actually the problems are always like,
0:29:16 I don’t have the right alignment among my team
0:29:19 and I don’t have the right executive team.
0:29:21 It’s usually some variation of those things.
0:29:24 But, you know, hearing it from the horse’s mouth
0:29:28 is super helpful in terms of making decisions for me.
0:29:31 And then, you know, even outside of DeBose,
0:29:32 sometimes I venture into Soma
0:29:33 and having some of those, you know,
0:29:35 kind of early YC founders who have really made it,
0:29:38 you know, like the Drew from Dropbox, for example,
0:29:41 and just knowing like how do they think about
0:29:44 every, all those things, executive hiring, et cetera,
0:29:45 it’s been really helpful, helpful to me.
0:29:48 So, luckily here at Silicon Valley,
0:29:49 I have a lot of great resources.
0:29:51 And the last thing I’ll shout out is,
0:29:55 I have this new executive coach, Matt Mocharri,
0:29:57 who’s like amazing.
0:29:58 This guy is the guru.
0:30:01 He’s, you know, mentors a lot of different fast-growing
0:30:02 startups around here.
0:30:04 I just talked to him for like a 360 thing.
0:30:05 – Yes. – Yeah, yes.
0:30:07 – This guy. – Yeah, that was great.
0:30:09 – Incredible, highly recommend, can’t speak,
0:30:11 he’s like changing my life.
0:30:13 So, I feel like he’s an angel sent down from Heaven
0:30:16 to teach me, finally, after 14 years,
0:30:19 how to like manage a system.
0:30:21 And I’ve learned a lot from him, so.
0:30:21 – That’s great.
0:30:23 – Those are kind of three sets, you know,
0:30:26 executive coach, the peer mentors,
0:30:28 and then kind of those early stage mentors
0:30:29 that I had back in the day.
0:30:30 – That’s great.
0:30:33 And I know one of the topics that you must end up
0:30:36 talking about often is that when you’re building something
0:30:39 that has a little bit more just execution risk,
0:30:42 you know, you’ve raised some real money
0:30:44 to kind of get started.
0:30:46 A lot of it ends up being sort of like organizational,
0:30:47 complexity, company culture.
0:30:51 I know this is the big, big, big, big area focus for you.
0:30:53 And that’s something that is very different
0:30:54 when you’re trying to build something for the long run
0:30:56 versus when you’re kind of just trying to find
0:30:59 product market fit, and it’s kind of like 10 people,
0:31:00 and you’re just like, is this even going to make it?
0:31:02 Like, let’s not even work on this.
0:31:03 – Yeah.
0:31:05 – So talk to us about kind of how your approach has changed
0:31:07 on building the company and your leadership style.
0:31:09 – That is a great question because it’s something
0:31:10 I think a lot about.
0:31:15 So I had never thought before a couple of months ago,
0:31:18 and this may sound stupid in a way,
0:31:20 but I’d never thought, what is the kind of company
0:31:22 that I want to show up to work at?
0:31:25 So 14 years later, finally thinking about it.
0:31:28 But the real answer is like, when you’re a 22 year old,
0:31:30 just starting your company, or you’re in Silicon Valley
0:31:33 and you’re thinking funding rounds and exits,
0:31:35 you’re always thinking, what’s the next milestone?
0:31:37 Like, how do I just claw my way desperately?
0:31:39 However, whatever it takes, how do I get to that
0:31:40 next milestone?
0:31:41 It’s do or die.
0:31:43 And for some, you know, oftentimes it is do or die.
0:31:46 You don’t have the luxury, oftentimes, of thinking
0:31:48 about what kind of, or you feel like you don’t have
0:31:50 the luxury of thinking about what kind of company
0:31:51 you want to build culturally.
0:31:54 And so, I started at Atrium actually very much
0:31:56 in the same way, but like, what are the metrics milestones
0:31:57 we want to hit?
0:31:58 What’s the next metrics milestone?
0:32:00 What do we need to get to for a Series B
0:32:02 or a next round of funding?
0:32:05 And so, the problem with that was that a year in,
0:32:07 I realized, oh, shoot, I need to like,
0:32:10 there are like a lot of things that I’ve neglected
0:32:13 that are actually affecting our ability to execute.
0:32:15 And the number one thing there was,
0:32:18 what’s the culture going to be?
0:32:21 People didn’t know, like, what’s the alignment aspect
0:32:22 of like, what are we building?
0:32:24 What kind of company are we?
0:32:25 Who are we?
0:32:26 What are we building?
0:32:28 And then, what’s the culture?
0:32:29 How are we being intentional about it?
0:32:32 So, we did a lot to work on that,
0:32:35 ran through a collaborative values process over a year ago
0:32:36 where we brought the whole company together,
0:32:38 figure out what we care about.
0:32:40 And then more recently, I’ve been thinking about,
0:32:43 after a lot of this self-work in terms of making myself
0:32:46 feel kind of consistently good every day
0:32:49 and move my attachments to the outcome,
0:32:53 I’ve realized there’s a set of principles
0:32:55 that I want to implement at the company.
0:32:57 And that I think that execution will flow
0:32:59 from those things, right?
0:33:01 If we build a company that has a high empathy
0:33:04 for each other, where we have care for each other,
0:33:06 where people are very collaborative,
0:33:10 where people feel like the locus of control
0:33:12 for what’s happening is inside of them,
0:33:13 instead of outside of them.
0:33:16 Things are happening through them, not to them.
0:33:19 I think that all the execution will actually flow from that.
0:33:21 One of the things I never understood before,
0:33:23 which I feel like I really understand now,
0:33:26 is that saying that culture eats strategy, right?
0:33:28 I felt like I had very good strategy with Atrium,
0:33:31 but I forgot about culture in that first part of the company,
0:33:34 and now I realized how important it is.
0:33:37 So one of the things I’ll say that we’re doing
0:33:39 is recently I read this book called
0:33:41 “The 15 Commitments of Conscious Leadership,”
0:33:42 which is an amazing book,
0:33:46 but it’s really about building a certain type of company,
0:33:49 what the authors call a conscious company.
0:33:54 But I would centered around that locus of control question.
0:33:56 Do you have radical responsibility
0:33:59 for what’s going on in your life, in your company,
0:34:00 regardless of who you are?
0:34:03 And read that book, and I realized this is the type
0:34:05 of company that I want to work at.
0:34:08 It’s a company populated by team members
0:34:11 who really believe in these principles.
0:34:13 And so we’re kind of going through a process
0:34:15 of trying to implement that at our company.
0:34:18 And really culture is one of the highest.
0:34:20 It went from something that I didn’t prioritize
0:34:22 to my top priority.
0:34:24 – Yeah, well, and I think it’s really interesting
0:34:29 because you’d started Kiko out of school, right?
0:34:33 And so unlike some folks who maybe,
0:34:35 they go and they work at Google or Facebook or something,
0:34:36 and they maybe have a template
0:34:39 for the company culture they want to create,
0:34:41 this is something that you kind of had to learn
0:34:44 and adjust over many, many kind of company iterations
0:34:46 of various companies that you built.
0:34:48 – That’s right, we had never worked at a place
0:34:51 with good culture or a culture, right?
0:34:53 Because we had always worked at our own company,
0:34:55 so we were just making it up as we went along.
0:34:57 When you’re not intentional about your culture
0:34:59 or type of company you want to be,
0:35:02 then the culture ends up being the accidental collection
0:35:05 of good and bad choices and personality quirks
0:35:08 and good and bad behaviors that your founding
0:35:12 and executive teams propagate, right?
0:35:13 And it’s accidental, right?
0:35:17 And often times there’s things that are not good behaviors,
0:35:19 they get propagated culturally.
0:35:22 And often times people justify it because they’re like,
0:35:26 well, they conflate the correlation with causation, right?
0:35:29 They’re like, because we, you know,
0:35:34 or have behaviors where maybe we’re like a low empathy
0:35:35 company, let’s say, but they don’t call it that.
0:35:36 They’re just like, we make decisions
0:35:38 based on like meritocracy, right?
0:35:40 And they’re like, but the best idea is gonna win,
0:35:43 but then maybe that’s like because that’s a behavior
0:35:44 that they’ve propagated,
0:35:46 but that might not be the real reason
0:35:49 why they’ve actually been winning, right?
0:35:51 I think a lot of companies in Silicon Valley
0:35:55 kind of succeed despite their management actually,
0:35:56 not because of it.
0:35:59 And what I mean by that is like the idea was so good
0:36:02 that a bunch of 25-year-olds could run the company, right?
0:36:04 That core product market was so good,
0:36:05 it was just a rocket ship
0:36:07 and then people were just trying to hang on.
0:36:09 Now, eventually I think they do figure it out,
0:36:10 but often times in those early days,
0:36:12 and I think it’s actually quite, you know,
0:36:14 not intentional and often times not that good.
0:36:15 – Yeah.
0:36:18 You know, in our conversation today,
0:36:20 we’ve talked about all the things that you’ve changed.
0:36:21 – Yeah. – Right?
0:36:24 You’ve changed, you know, from consumer to B to B,
0:36:27 you’ve changed, you know, how fast you fundraise,
0:36:30 you know, there’s been a lot of different changes.
0:36:33 You know, is there anything that you feel like you,
0:36:35 like there’s a core that you’re like,
0:36:37 okay, there’s this thread that I’m trying to do the same
0:36:39 between all the companies,
0:36:41 or is it just really like iterating very quickly
0:36:44 and, you know, you’re doing a lot that’s different?
0:36:46 – Well, I think that core ethos of, yeah,
0:36:50 iterating quickly, you know, that’s like a YC ethos,
0:36:52 that’s something that we really did,
0:36:54 carry on at the very beginning.
0:36:59 So speed was, you know, something that’s pretty important.
0:37:04 I think that really being helpful in the community,
0:37:06 not just your startup, I mean, including your startup,
0:37:08 but also the community of startups,
0:37:09 that’s something that we learn,
0:37:11 the behavior we learn from, you know, the early days of YC,
0:37:14 and even like our community of friends who were founders,
0:37:17 who all became successful, you know, helped each other out,
0:37:19 and then now today, you know, it’s an ethos
0:37:21 that would take the atrium to really build a company
0:37:24 that’s, you know, kind of for startups, you know,
0:37:26 by startups that helps out these, you know,
0:37:28 fast-growing startups.
0:37:30 So that ethos is probably something
0:37:33 that’s pretty similar, you know, kind of similar
0:37:35 to like what you guys have at Andreessen, right?
0:37:38 Which is like, if we can, you know, be the most helpful
0:37:40 in terms of providing these networks of services,
0:37:43 that is something that is going to, you know,
0:37:45 kind of pay dividends for us as a brand.
0:37:47 You know, that’s something I believed personally,
0:37:50 and then also at each room throughout my entire career.
0:37:51 – Right, right.
0:37:54 Yeah, I mean, as you know,
0:37:56 one of the things that’s great about the Bay Area
0:37:59 is that it ends up being this very long-running,
0:38:02 relationship-driven place where, you know,
0:38:05 you meet people like, I mean, we met like 10 plus years ago,
0:38:07 right, and that’s the kind of interesting thing
0:38:11 where there’s many, many cases where you can work together.
0:38:14 And so, you know, focusing on value creation,
0:38:16 as opposed to like, how am I going to try to position myself
0:38:18 to like capture the most value?
0:38:21 Like, I think that, you know, like that certainly runs,
0:38:22 like I think it’s one of the very special things
0:38:24 about the Bay Area. – Absolutely.
0:38:26 If I think about where we’re at, you know,
0:38:29 where all the people who I, you know, saw in the early days,
0:38:32 like 13 years ago, all these different founders,
0:38:33 you know, these two-person startups
0:38:35 that won’t even anything, where they’re at,
0:38:37 their company might not have succeeded,
0:38:40 but they have like created some value here in Silicon Valley
0:38:42 by being in that ecosystem, being helpful,
0:38:44 and then, you know, maybe becoming an executive
0:38:45 at someone else’s company,
0:38:47 or becoming an investor, early-stage investor
0:38:48 at another company that really worked.
0:38:51 And so, there really is like a feeling
0:38:55 of if you kind of get out what you put into this community,
0:38:57 and that’s one of the things I really love about it.
0:39:02 – How do you think about the idea that, you know,
0:39:05 when you’re first getting started,
0:39:07 you’re a first-time entrepreneur,
0:39:09 there’s kind of like low expectations, right?
0:39:11 ‘Cause you’re like, maybe this’ll work,
0:39:11 maybe this won’t work,
0:39:15 people’s expectations of you are like kind of low too,
0:39:16 ’cause they’re kind of like, I don’t know,
0:39:18 who knows, you know, Justin’s often in San Francisco
0:39:20 doing this thing, he’s running around with a camera
0:39:24 on his head, and it’s just kind of a fun thing.
0:39:27 And then, now, several companies later,
0:39:30 because, you know, also you’ve raised money,
0:39:32 and because you’ve done a lot, et cetera,
0:39:34 you know, the expectations must be higher.
0:39:36 Like, how do you think about, you know,
0:39:38 how do you think about those expectations
0:39:39 managing your own, you know,
0:39:41 your own expectations around that?
0:39:46 – Well, I always think that every entrepreneur’s expectations
0:39:49 for themselves are very exceedingly high, right?
0:39:52 If you’re the type of person who was a PM or engineer
0:39:53 at, you know, one of these fan companies,
0:39:55 and then you’re like, I’m gonna start a startup
0:39:57 ’cause I see other people doing it,
0:39:59 then you don’t think, you don’t go into it thinking,
0:40:01 well, I’m just gonna create like a whatever,
0:40:04 something that’s like a nice small business, right?
0:40:06 You go in being like, I’m gonna raise series A
0:40:08 from Andreessen, and we’re gonna be, you know,
0:40:10 this product that just goes,
0:40:12 the next Snapchat or whatever.
0:40:16 And so I think that, like, it’s always a battle
0:40:20 against your own, like, the kind of devil
0:40:22 on your shoulders telling you, you’re not good enough,
0:40:24 you know, you’re not doing well enough,
0:40:25 you could be doing better.
0:40:27 And I think the way that you win that battle
0:40:31 is by really internalizing and realizing
0:40:36 that whatever happens, you’re gonna be fine.
0:40:38 And you’re probably gonna be the same,
0:40:40 you’re not gonna be happier or less happy, actually.
0:40:43 And now most people do not actually successfully
0:40:46 internalize that well enough, in my opinion.
0:40:48 But it is true, I firmly believe it’s true,
0:40:51 and it’s something that the sooner you start practicing
0:40:54 that in your head, really, you know,
0:40:58 feeling that and experiencing that in yourself internally,
0:41:00 then the happier you’ll be.
0:41:02 And that’s not to say that a lot of, you know,
0:41:04 people I come into contact with, like, friends even,
0:41:06 or people who work for me are like,
0:41:11 well, my drive, like, that need to win at all costs
0:41:12 is my edge.
0:41:14 But I really don’t believe, I mean,
0:41:15 maybe that’s true for other people,
0:41:17 but for me, I never found that to be the case.
0:41:21 It’s like, no, it was just like the kind of unhappiness
0:41:23 that was created around it that would make it
0:41:25 actually less sustainable for me to continue on,
0:41:27 because I was always, you know, you can’t,
0:41:28 human beings don’t wanna live in a high stress,
0:41:30 high anxiety, stay for too long.
0:41:31 That’s how you can burn out, right?
0:41:35 So startups are not, I mean, contrary to popular belief,
0:41:37 it’s not a sprint, it’s a marathon, right?
0:41:39 There’s these overnight successes,
0:41:42 Twitch came out of nowhere, eight years from
0:41:44 incorporating that company to selling it,
0:41:45 almost exactly eight years, right?
0:41:47 So that is a long time.
0:41:49 And in order to last a long time,
0:41:52 you need to figure out a way that you are okay
0:41:54 with what’s going on, and what’s going on
0:41:57 is always gonna involve bad things.
0:41:59 Like things, you know, there’s gonna be good
0:42:00 and there’s gonna be bad.
0:42:01 So if you don’t figure out a way
0:42:04 that you psychologically are okay with that,
0:42:06 you’re gonna give up, and if you give up,
0:42:09 you’re never gonna see it to the ultimate potential
0:42:12 that whatever your startup is can be.
0:42:12 – Great.
0:42:18 I’m gonna throw in kind of two last questions in here.
0:42:23 One is, you know, what are you reading these days?
0:42:25 Do you have any sort of recommendations, podcasts
0:42:27 that you like, kind of media consumption
0:42:30 is kind of a way to learn yourself?
0:42:31 – Yeah.
0:42:33 – And anything sort of especially super impactful
0:42:37 over the last couple years that you wanna reference?
0:42:38 – Yeah, that’s great.
0:42:40 So reading a lot, actually,
0:42:43 ’cause I deleted all the entertainment apps off my phone,
0:42:45 including the browser, and I’d locked it
0:42:47 so that I don’t can install new apps
0:42:48 ’cause I was a total phone addict.
0:42:49 That includes Twitch.
0:42:50 – Wait, how do you lock?
0:42:51 How do you lock your–
0:42:51 – So you can lock installing new apps,
0:42:52 you can delete the app store
0:42:54 and put a passcode lock on it.
0:42:55 – Oh.
0:42:56 – And I gave my wife the passcode,
0:42:58 or she put in a passcode, I don’t know what it is.
0:42:59 – Right.
0:43:00 – So I can’t–
0:43:01 – This is like a parental lock.
0:43:02 – It’s a parental lock, exactly.
0:43:04 So I don’t have control over my own phone anymore.
0:43:07 But the consequence of that is I read a lot more books,
0:43:09 which is good.
0:43:12 A couple of ones that have been particularly impactful to me.
0:43:15 Number one is this book called The Untethered Soul.
0:43:17 So this book changed my life.
0:43:20 It’s really about the idea is that you are not
0:43:22 the thing that you think you are.
0:43:25 Most people go through life thinking they are the experiences
0:43:27 that they’ve experienced, the thoughts that they have,
0:43:29 or the emotions that they have.
0:43:33 But really, you’re just the observer of these things
0:43:34 that are happening.
0:43:36 And by creating, it’s almost like you’re watching a movie,
0:43:39 right, like a movie that has all the five senses,
0:43:40 plus emotions, plus thoughts.
0:43:45 So like a seven dimensional movie of the just end life, right?
0:43:49 And I think that was a very important message to me
0:43:52 to realize, like an internalize that like actually
0:43:55 these attachment, these things that I think will happen
0:43:57 that will like drive happiness, like experiences or events
0:43:59 or whatever will never actually drive
0:44:01 true internal happiness.
0:44:04 So amazing book, The Untethered Soul, highly recommend it.
0:44:07 Another book that I think made me a much better leader,
0:44:10 I was this book I read called Leadership and Self Deception.
0:44:12 Amazing book.
0:44:14 The book, the premise of the book is really there’s two ways
0:44:17 to treat other people inside the box and outside the box,
0:44:21 but really I mean like without empathy or with empathy,
0:44:25 like treating them like an object or a person, right?
0:44:28 And the idea, the fundamental idea behind the book
0:44:31 is if you treat people like an object,
0:44:33 number one, they don’t like it, right?
0:44:36 But the second thing is, if you treat people like objects
0:44:38 who are just there to fulfill something for you, right?
0:44:40 Like at work, it would be like to, you know,
0:44:43 hit some number or metric or whatever, do some job.
0:44:46 The problem is that you will lie to yourself about
0:44:50 when there’s negative situations about what your role is,
0:44:51 you’ll self deceive, you’ll say,
0:44:53 oh, this person is 100% at fault
0:44:55 and I’m 0% at fault.
0:44:58 And I found myself actually doing that a lot of times.
0:45:02 I realized, you know, I felt like I was,
0:45:07 you know, had a high degree of empathy for other people,
0:45:09 but I realized that was for people who,
0:45:10 I felt like we’re performing really good
0:45:13 where my observation was like high performance.
0:45:16 But I wasn’t, where my observation,
0:45:19 where my feeling was that there wasn’t high performance,
0:45:23 I felt like I would slip into this like low empathy mode.
0:45:25 And the problem is that when you’re in that mode,
0:45:27 you don’t admit, what are the things that I have done?
0:45:29 What, you know, Justin, what are the things I have done
0:45:30 to contribute to that situation?
0:45:34 So examples could be put someone in the wrong job,
0:45:37 didn’t give them clear enough criteria for success or failure,
0:45:39 didn’t support them with the right resources, right?
0:45:42 There’s many reasons why I could have contributed
0:45:44 to some situation failing.
0:45:47 And I found that like I would lie to myself in those situations.
0:45:51 So, you know, that was a really important book for me.
0:45:53 And those are probably two ones I really recommend.
0:45:55 – That’s great.
0:45:57 Are you doing a lot of podcasts right now?
0:45:59 – Listening to them? – Yeah.
0:46:01 – Been listening to– – That kind of entertainment.
0:46:03 – Yeah, I listened to some podcasts.
0:46:06 I’ve been listening to some of the Joe Rogan experience.
0:46:09 – Nice. – And that’s probably the,
0:46:10 this is probably it.
0:46:12 I like, I just listened to one with Alex Honol,
0:46:15 where he’s talking about climbing, you know,
0:46:16 so it’s pretty interesting.
0:46:20 – I’m gonna ask you the time travel question.
0:46:24 So if you were today, an enlightened, repeat entrepreneur,
0:46:27 to go back to yourself when, you know,
0:46:30 you’re 22, 23, just getting started doing this thing.
0:46:34 You know, what advice would you give yourself?
0:46:37 – When I’m just getting started, you know,
0:46:40 probably join Facebook.
0:46:45 No, but the, maybe the real answer,
0:46:47 I’ve actually, you know, I don’t really regret
0:46:49 any of the, like, economic choices or anything.
0:46:52 I think I’ve had this tremendous opportunity
0:46:55 to, like, build and discover these new things
0:46:59 and build companies and I wouldn’t trade it for anything.
0:47:01 I think the thing I could have done better
0:47:03 or, like, learned, you know, back then is,
0:47:07 you know, self-improvement is a thing.
0:47:08 You should probably, like, work on that.
0:47:09 Maybe that’s number one.
0:47:10 The second thing would be–
0:47:11 – Stop eating pizza at work.
0:47:12 – Yeah, stop eating pizza at work.
0:47:14 Number three would be,
0:47:18 you should, you know, things take time.
0:47:20 Like, don’t be in such a, you know,
0:47:22 it’s not, like, a one-year, one-and-done,
0:47:24 like, no, you’re a billionaire, you know?
0:47:26 Like, if you look at the, let’s say,
0:47:29 any sort of, like, the Amazon share price
0:47:30 or, like, market cap over time, right?
0:47:32 It looks, like, even through, like,
0:47:36 the last couple years looks like an exponential curve, right?
0:47:39 And so, you know, if Bezos had been, like, your,
0:47:41 you know, like, 15,
0:47:44 which is a long time to be starting a company,
0:47:46 like, oh, man, I made it, I’m done,
0:47:47 like, I’m gonna retire, like,
0:47:50 well, you know, the company would look a lot different,
0:47:52 right, so, you know, things take time
0:47:54 and I have to constantly remind myself that.
0:47:57 I think humans, you know, here in Silicon Valley,
0:47:59 especially, but then human beings in general,
0:48:01 are wired to, like, always want the new,
0:48:02 you know, look for the new thing.
0:48:03 What’s new?
0:48:05 What are you, like, what’s your new thing?
0:48:07 Something that everybody’s asking about in Silicon Valley?
0:48:10 They’re always, you know, that’s a question here.
0:48:12 But the best entrepreneurs here,
0:48:13 the ones who have created lasting companies
0:48:16 and lasting value, they stick with their thing
0:48:19 for decades, you know?
0:48:21 And that’s what impresses me most now
0:48:25 and I wish that I had kind of realized that, you know,
0:48:25 before.
0:48:28 – Awesome.
0:48:29 – Better late than never.
0:48:30 (laughing)
0:48:31 – Awesome.
0:48:33 Justin, thank you for coming by.
0:48:33 – Yeah.
0:48:35 – Thanks for having me. – Really good discussion.
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