#109 — Nothing To Prove — Justin Kan

What's up, all you delinquents? We've got a chaw episode for you today with Justin Kan, J. Kan, J. Mann, founder of Twitch, Justin.tv, prominent angel investor, podcaster, vlogger, and last but not least, friend. Today's conversation, it is going to be wild. I'm recording this intro beforehand, so I actually don't know if it's going to be wild. But I think it will. So Justin, why don't you come on in, have a seat, because we're doing this one in person, post-COVID PC. And if you want more conversations like this, lightly touch that subscribe button on YouTube. We just started uploading things to YouTube. Lightly hit that subscribe button also on your podcast players, the little ring thing on YouTube, the like button. Like button. Just lightly brush them all if you like conversations at the intersection of entrepreneurship, philosophy, and technology. So without further delay, let's get into it with our old friend Justin Khan. This is Below the Line. J-Man, thank you for coming on the podcast. This is numero tres, part three,

the third time I got to kick it off, and then I did your. First live one, and then now here I am again. You can't get rid of me.

It's actually even better because now, man, a lot's changed in the last 2 years from the first appearance to second.

Yeah.

To now we're here in LA. How long are you in LA for?

Just a couple weeks. Yeah.

What's—

experimenting, exploring. It's great down here. This is the place to be. Plus, I want to do all these content collabs, you know, and everybody's down here.

Oh yeah?

Yeah.

Yeah, we were chatting the other day. You were saying that I was asking you between content and investing, what are you most excited about each day?

Yeah, it's interesting. I'm most excited about— well, it goes in waves. I like investing a lot and I like creating content a lot and in different ways. The content, it's very activating. I have this YouTube channel that if people don't follow, they should go subscribe to my YouTube channel. Justin Kan Vlog. I guess you just search for Justin Kan on the—

We'll link to it. We're about to go film some stuff for that.

Yeah, we're gonna go make a video after this. So my YouTube channel, it's like me just start off as just telling startup stories and kind of giving startup advice, and then now I'm like making vlogs and making different kinds of videos and experimenting a lot. And it's a very creative process for me, just how do you tell a story or tell a narrative in Video format, you know, and how do I— I've never done that before. I never thought of—

And YouTube format. Yeah, not just video, but also YouTube format. We were talking a little bit about it, but what— when you create it, are you thinking YouTube first? Are you thinking Instagram first? I want the nitty-gritty of how you think through an idea to hitting publish on one of the video platforms.

Yeah, so I think, I think of it as YouTube first. Sometimes I'll test the ideas on TikTok. And, you know, if I talk about a certain topic like how to invest or something like that, I might like make a video on TikTok that's a short 1-minute video, see if it does well. And that's just really me holding the camera in my face and talking about startup stuff and then, or wellness, whatever, the things I'm into. And then if I like the idea, I'll make it into a YouTube video. And usually there's a couple different formats of YouTube videos that I've been doing. One is Uh, telling a story about something in the past. So I'll say, here's how Twitch got acquired by Google. Um, or sorry, by Amazon. Or here's how we almost got acquired by Google, which is a separate video. And I'll— those ones I start off very scripted, and I would just kinda tell the— I'd write it out and then I'd tell the story from that. And they did pretty well. Some of those early ones did pretty well. How long ago was that? That was like in January, so 5 months ago.

Yeah, dude, you have like—

I have 130,000 subs. Dude. So, it's all right, yeah.

Yeah, for 5 months, that's—

That's not bad. Yeah, it's awesome. It could be better, but it's all good.

And, if you're discovering us through the search algorithm with Justin, hit that sub button on Below the Line

as well. Smash subscribe and hit that post notification, the new video notifications.

Yeah, that's right.

So, start off with very scripted and I was Film this footage. It's like 25 minutes or something telling a story, and then like the editor would cut it down and put in like memes and, you know, graphics and transitions and stuff. And, uh, that was cool, but they were a little bit obviously scripted, right? I was reading on like an autocue or teleprompter, and it was like, okay. And so people started saying like— so I— they thought it was like a little less authentic than it could be. And so I started just making videos where I just turn the camera on, I tell the story or riff on something. just, you know, off the top of my head. And with the magic of YouTube editing, you can edit that into something that's like actually reasonable. And so I started doing those, and then now I've been making more vlogs where I just take the camera around and it's like whatever I'm doing, you know. Like if I'll make something in LA, like I'm coming to LA meeting with all these different, you know, influencers and creators, and, and maybe I'll show some behind the scenes of that. Or I went to Miami and, um, I did a video where I'm like giving my car away to my business partner Robin. Like, my— I shipped my car there and I'm like surprising him with it. And so just making a vlog of that, you know, just be random stuff. And then I try to work in some startup or wellness-related themes, like the stuff that I know about. I just like riff on it in the vlog or whatever.

Does— when did this in your head start of wanting to create content? I guess I mean that both in terms of the more immediate version and But then also, obviously, your tech start was Justin— or actually, no, after the calendar app, you had Justin.tv.

Yeah, so I've been thinking about content for a long time, right? I started Justin.tv where it was us doing a 24/7 livestream back in 2006, 15 years ago. And then about 8 years after that, I did this other— you know, I started making content on Snapchat. Making like startup advice on Snapchat, and that was very novel at the time. And then after that, you know, then I stopped that, and then I made you know this is the third wave where I'm making like YouTube videos and maybe some TikTok videos. And I would say each time it comes kind of randomly, you know, it's like I never really loved. I wasn't like someone who was like, oh, I always want to be creating content. I want to make movies or something like that. It was more the first time. It was kind of like this is a way for people. I had the semblance of an idea that social media would exist. Like people are interested in following people back in 2006. And so if you just showed someone a window into someone else's life, they would be interested in that, and you could make somebody into a celebrity, and that would be valuable, like in terms of advertising or you know creating businesses or whatever. So that was the idea behind Justin TV, and I think I was right. The problem is like a 24/7 livestream is not interesting. You have to like make it more edited and chopped up, you know, into more digestible parts. And so I think the spiritual successor to that was like the stories feature in you know Instagram and Snapchat. It's like showing people this window into like. someone's life. And, you know, celebrities are all— they're all doing stories now, and, you know, people kind of see that and they get to feel like they get to know them, right?

Yeah.

So then the Snapchat side, it was more of like an experiment. You know, I heard about Snapchat Stories and I was like, oh, this is kind of like the idea we had for Justin.tv but way better implemented. And so creating content for it was more of an experiment to understand the platform. And then I got into it and I was, you know, using it and having fun with it. I stopped because it kind of stopped growing, and I felt like I just started a new startup, so I was kind of switched focus. But I always really enjoyed it. And then this most recent time I got into YouTube— well, first I got— I was making a podcast and I started making the podcast because I recorded someone else's podcast. It wasn't yours, but it was someone else's. And then the company that was making the podcast was like, oh, you should have a podcast too. Mm-hmm. And so I was kind of like, oh, you'll do all the work and edit it for me. Like, I'll just— all I have to do is have this conversation. Like, I'll try it. And so I did that. I was having fun with that. And then I was trying to hire someone to help me produce the podcast after like 6 months. It was, you know, kind of working decently. And I recruited the person— I was like looking to hire someone, and then the person who— one of the people who I ended up hiring, she was like, you should do YouTube. And I was very resistant at first, but she kind of convinced me it would be easy to try it out. And so her name's Jen. She just convinced me to try YouTube, and I started.

Was she your producer for the podcast, or just—

Well, she actually hired someone else to produce the podcast, but I was like, okay, I'll work with you on producing a YouTube channel. And so she was the one who kind of introduced me to YouTube, this idea I could create YouTube content. And then I've had a lot of fun with it. So I'm— for me, it's like always about being open to new ideas and experiences and just trying.

And it sounds like you're also keenly aware of just different type of content for different tools and really interested in the actual tool versus—

I think it's interesting to understand like what are the formats that work and like understanding, you know, because I've been the content platform creator and creating like a platform is interesting because you're creating this space for people to try different ideas. And now I'm like on the other side where I'm like trying different ideas and seeing what's working and understanding how the platforms work is interesting. And like, how platforms work is ultimately, it's a combination of the technology, but it's also human psychology. Like, what do people like to consume? And like, how do they interact with the content and engage with it?

Right.

And so, you know, with YouTube, for example, just understanding, oh, there's this content shift that's going on, and it's probably obvious to people who are in content, but for me it was, even as somebody who helped create Twitch, you know, it wasn't obvious. It's like the— you can now edit. The acceptability on, like, how authentic the content is is much higher than, like, let's say TV. But then also how you edit. It can be edited super tight. Mmhmm. Right? And so, you know, I might take— if I spitball something about investing in startups into the camera, you can take, you know, if I, if I don't, uh, say it exactly right, you know, say the lines right, or there's like stumbles in my sentence, you can just cut that out and like edit like one sentence together from multiple clips. And that's like considered okay, right? Like in TV, that would never happen, right? But it's, it's like fine on YouTube.

And even on a podcast, that would be hard.

Yeah,

it'd be hard to listen to if there's the shift in, and, you know, intonation in the voice.

Yeah, well, usually like you would do it in a way that it's not You know, super obvious. But yeah, I've seen, I've seen a lot of that where if you look at someone like Emma Chamberlain's videos where she's just riffing in front of the camera 90% of the time, it's like she'll edit, you know, she's probably recording like 20 minutes of content and then just editing out this like great 4 minutes or whatever, you know.

And are you— how involved are you in the editing process?

Like, I don't do it. I just punt it, right? Because I don't actually care that much about the editing. I like I have an intuitive understanding of like, if I just say enough interesting things, then like someone can edit it into like something that's pretty good. And that's what's worked so far. So actually, I do get the draft back and then I usually make some slight like feedback, but it's very light usually.

How much time are you spending per week on the content creation side?

I do like one podcast a week on average. I mean, usually they're clumped up and that's about 90 minutes. And the podcast, my Quest podcast is like kind of telling other— it's a guest-style podcast, so kind of like Below the Line, and bring people in. And then just— it's a— for me, it's a chance to have a conversation with someone.

Oh, it's the best.

Yeah, even if I don't— at first I was like, if nobody listens to this, I'm actually not even gonna look at the stats so that I can see that I'm doing it for intrinsic reasons. And after I did it for a couple months, I was like, oh, I just— even though nobody looks at this, I— it's It's awesome to be able to have this conversation with someone where I wouldn't normally sit down with someone and have a 90-minute conversation about them.

Yeah, there's like no social convention to allow for a 90-minute conversation, no phones.

Yeah.

And it's just us, and it's going deep into— I feel like there's— you turn on the mic for someone and— or you put a mic in front of someone and it's like the— I don't know what it is, but the honesty light comes out.

Yeah, I think it—

Which is strange because you— with an audience, you'd think it'd be the opposite, be a little bit more cagey,

but Maybe it feels like some form of catharsis, right?

Right.

Um, so I do that podcast every week, and then the second thing is making YouTube videos. And they don't take that long, actually, 'cause I probably record— it depends. If I'm, like, vlogging, then I'll take it with me, and that's kind of while I'm doing stuff. If I am making, like, a sit-down talking-head video, then I'll probably spend 30 minutes on it. You know, I'll just put it— set it up, record it, like, me riffing on something, and then I'll just ship that footage off.

So like 8 hours a week, 6 hours a week on creating content that—

It might be like, it might be like 5 or 6 hours. Yeah.

Yeah, it is. And it's awesome. It's great content. Both the podcast I love as well as the YouTube content, as well as you have the 4-person podcast.

Yeah, I

have this

podcast on my YouTube channel called Only Friends, which is me and some of my other like kind of long, like old friends that we have this one chat group, right, that we've had since like 2000 2010 probably, or 2009, whenever there was like multi—

You, Seibel.

Seibel is on it. So CEO of Y Combinator, who's my co-founder of Justin.tv, and then Emmett, who's the CEO of Twitch now, is co-founder of Justin.tv and Twitch. And then we'll— it rotates through like whoever from the chat group wants to join. So we got like T-Con, you know, who, you know, who's the co-founder of Scribd, and we've been friends with forever. And then Jamie Quinn was an early YC guy who was head of growth at Reddit, and, and And Notion, and then some of our other friends will like rotate through, you know.

Is there— are there any content projects you've picked up in the last year that you, that you think, okay, we might have to sunset that? Or any projects that you picked up around any of these things where you try it and it doesn't work?

Well, I would say like on TikTok, for example, I've started to make less content on TikTok. I was like really into it in January, February, and started making less, 'cause I feel like it's just right— like, the fit for me is not 100%. Like, I think the audience likes it, but it's like I prefer to be able to have a longer format to tell a story.

OK.

It's just easier to— I think with TikTok, it's gotta be— you know, the attention span is so short. It's gotta be really tight. And it's more for— like, there's a lot of comedic stuff, kinda like really punchy comedic stuff works, or, like, visual juxtapositions. Like, Whereas that's not really my style, right? As much. I'm more, I'm just gonna tell you some authentic stuff and, you know, people, some set of people like that, you know? But it's not as viral, I guess, in the same way. I think YouTube rewards my YouTube content more than TikTok rewards my TikTok content.

Yeah. Dude, I think in terms of platforms, well, I'll ask you, if you were to put all of your investment in one platform, investment of energy, even, you know, if you were to make a bet with $1 million on one platform that would pay off the best in 10 years, which one would it be?

YouTube. Hands down, YouTube. I think YouTube has a long way to grow. I think the channels part of YouTube, like people following channels, I mean, they've had that for a long time, obviously since the beginning actually, but like now YouTube's really gone all in on channels, right? Like on people creating their own channels, and I think the influencer or creator world is just getting started. You know, you have like MrBeast making MrBeast Burger and becoming pretty huge overnight because he's able to drive all this attention. I think the same is gonna be— there's gonna be creators in every different category, you know, including business entrepreneurship and wellness or whatever. And so, it's a great platform. And I do feel like I'm reaching a lot of people in a positive way. I get these notes from people who are like, Thank you so much for content, like, really helped me through this, like, tough time, or, you know, whatever. I talk a lot about failing, and, you know, people see me as like, oh, you've been really successful, but just knowing that, like, I've wrestled with anxiety and depression, or I failed at things, you know, even post being successful, is, I think, a message that helps a lot of people. So YouTube is great, and I think it's only gonna grow. And so I'm all in on YouTube, you know. Yeah.

Yeah, I think YouTube, yeah, if I could make a bet in any mature technology, not even just content platforms, I agree, I think YouTube is the one where it's just getting started. It is outrageous that I will choose to watch a podcast on YouTube that probably cost $2,000 to produce of 2 hilarious comedians or an episode of yours. I will choose that over— A movie. A Will Smith Netflix movie that they probably put $100 million in. Yeah, that I'm like taking a flyer on. I don't know if I'm actually gonna get into it versus, all right, this is like ongoing character development of knowing this individual or the style of— Well,

that's what I'm talking about. People, you know, you— that's what I said with the Justin.tv thing. It's like people follow people, you know, and that kind of like authentic connection that you have with like with a creator is very powerful. Yeah,

yeah, it's— there's— and there's something very human about the algorithm in that it's— it's— Balaji was on the, the podcast recently. He's famous for, uh, a phrase recently that he said. I bet you came across it. It was, um, along the lines of, if code scripts machines, media scripts humans.

Yeah.

And I think humans script algorithms. And it's not the other— Right, it's a reflection.

I mean, they're showing you people what they want to see. What you're showing— It's a reflection of like what you're— what you want.

Exactly. So if you're complaining about the, the insanity or the state of the world based on what Facebook or Instagram is showing us, it's, it's just a mirror back towards what that person wants to see,

right?

And, and YouTube, I think, has the most human algorithm and are pro human algorithm in that it rewards watch time, it rewards engagement with the channel, and it rewards long-form content. And anything over 10 minutes, I'd say, is long-form in the world today. So, like a 25-minute video around this time, XYZ topic, YouTube wants to serve you up more and more of those, and it ends up being It's not 10 seconds on like a TikTok that is visually engaging and usually I think like sexually provocative and so much of TikTok is and there's very little— it's almost like YouTube is made for ideas and long-form discussion of ideas. I don't know if there's any other platform, maybe podcasts, but that's not really quote-unquote a platform For long-form idea discussion.

Well, I think that, um, to be fair, I do think there's like lots of different content on TikTok, and it's more of like a format versus which support, you know, it's more the format versus like YouTube. Like TikTok allows— there's like, you know, there's everything. There's like people who are doing— That's true. Content on TikTok, or like—

The Reels on Instagram is very— Yeah, Reels is actually, uh, like, at least when they're kicking off the product Yeah. A few months ago it was just all dancing.

Yeah.

But yeah, TikTok does have some very cool education stuff.

Yeah. And then with YouTube, I think, you know, they have Shorts and they're adding, you know, I'm not sure if they really reward like the really long-form content, but it's, yeah, YouTube is, it's interesting because I think their algorithm surfaces their content to new people, right? Just like TikTok does. And that helps you build an audience.

What is, how do you compare and contrast to Twitch?

Well, Twitch is kind of a grind, to be honest, right? Like, that's the, that's the, the hard part is like with Twitch, it's like you've got to be on Twitch all the time to grow on Twitch. And with YouTube, like, you know, from— take me, right? Like, I'm not going to be on Twitch because I got a job, right? I'm investing full-time, incubating companies. I got other things to do in my day than be on Twitch. And so Twitch is, I think, really good because For people, like, you don't have to be— you have to be a certain type of entertaining, but you don't have to think of like viral ideas or anything like that, right? You just like go on and play games, or there's like, you know, the acceptable— it's more like talk radio where you can like kind of fill in the white space with, with something, um, very easy. Whereas with, you know, maybe if you're, you know, MrBeast or something, you're trying to come up with like viral ideas and like kind of crazy, uh, ideas. It's like, that's pretty hard to implement. Right, so Twitch can be harder than YouTube, I think. Or sorry, it can be easier than YouTube in some ways, but then it's hard. It takes a lot of time.

It's like a newsletter, a good newsletter to hook people. God, that seems so onerous to write a great newsletter every week or to keep up with the demand for your streams on Twitch. Does— okay, tell me about LA. What is the— you were here before during the pandemic. You're back for a few weeks. Um, and I think you sold your place in SF. So, maybe give me just an update, a life update on you during the pandemic. And

yeah, well, I, uh, you know, sold my place. I moved out of San Francisco, moved to like rural California.

How come?

Well, you know, whenever— the point of living in a city is to be around other people, and during the pandemic it was not, you know, did not— you couldn't do that really, right? So Moved out to the middle of nowhere, which is really nice. And so still live there, but it's good to come and see other people, you know, once in a while. And so taking this trip to LA with the family, and it's been pretty good. I mean, I've only been here a day so far, you know.

Is there plans to move back to SF?

No, no, no.

Actually, I'm asking you as a friend now.

Yeah, no, I'm not moving. I'm never moving back to SF.

How come? Why do you say it like that?

Why, why, why should I? The SF itself is like going through, I think, has really serious problems, you know, like there's like the crime, or at least the, you know, the site crime stats going down in some areas, but I think that's wrong because I think reporting crime has like gone down as well. I think the crime is like rampant in SF. People don't feel safe, right? And so You know, safety is like really low on Maslow's hierarchy of needs. So I think that's, you know, now maybe I'm just like an old complaining guy, you know, saying that.

No, dude, even when we were— when you and I both were living there, our car got broken into 3 times in the first year. Yeah, I was there, and it was like laughable to try to report it.

Exactly.

People set the tone for—

yeah, people are always breaking in. to, you know, steal my car or steal my bikes, my car, etc. Like, I've dealt with that constantly, you know, and there's nowhere you can live in SF that's like immune from that. You could be in the nicest neighborhood, which is not the one that I want to be in anyways, but like, and it's still the case. So I think SF has some structural problems with how it's managed, uh, which make it tough to live there when you, you know, with your family and Stuff like that. So, and then in the remote world where you can live anywhere and do your job, like, is SF the place that you would choose? You know, I think it's beautiful in many ways, and I love the city in a lot of ways, but I don't know if it's the place I would choose to live. Maybe it's time for something new for me.

What is, uh, what is the natural question? What is the place that—

Well, I mean, I live right now in the countryside, and I like that, you know. So I think that might be it, and then I'll just come visit once in a while.

Yeah. Do you think being an investor, do you think it's gonna take a hit at all?

I don't think so. I think for founders, it's better to meet all these investors by Zoom and be able to do back-to-back meetings, and then you can just raise your round in like days. It's so much easier for both sides, right? And the investors, I don't think they're gonna want to go back to only meeting in person because it's really efficient for investors and you can live anywhere, right?

Dude, I went to a meeting yesterday in person here in LA over on Montana. It's 0.8 miles, maybe a mile away.

Yeah.

Barely a mile. And to get an Uber, it was 17 minutes, so that made me late. Uh, so by the time my wife got back with the car, I was like, all right, I'm gonna take the car. So I was 15 minutes late, looked for parking for another 10 minutes, sat down. The whole thing was like an hour. A Zoom meeting, the default is nicely at 30 minutes, so it's default. The long story short, it was An hour and 45 minutes for a meeting that— I mean, this whole podcast is built around candor. Within 7 minutes, I was like, this is, this is a poor use of time.

Yeah.

It was, it was actually— it, that's the first coffee meeting that I was like, okay, let's do it in person for the novelty.

Yeah. Now you're never going back. Never going back. You're only gonna do Zoom meetings from now, from this studio.

Exactly. Either Zoom for 30 minutes or Or a podcast deep convo for 90. But there really shouldn't be anything in between.

Yeah, no, I, I agree with you. I think this is a great format, and seeing people in person for this kind of interview is— that's great. But like, for most things, especially you're just getting to know someone, you don't need to do that.

Right, right. Or with friends doing it in a group, um, then it really makes it worth it. Yeah, to go in person. But, um, okay, so within Investing, within 5 years, just out of personal curiosity, what would the ideal scenario be for you between content and investing 5 years from now, the absolute vision board version?

I don't know. I think I'm living it. I spend most of my time investing and incubating companies. So, GOAT Capital, our fund, we also incubate companies out of it. And so, we're working on a few of those. That's most of the day. We do content. That's great.

What are some of the spaces you've been investing in? Or let's say this past week, that is—

Last week I haven't invested in anything.

Okay, but in the last week, what has pulled your attention space-wise, company-wise, where it's been rolling around in your head?

There's like some healthcare ones that I've been thinking about. So healthcare's an interest area of mine. And, you know, we have— I incubated this company called Alto a couple years ago, and that's doing really well. And after that, that kind of got me It's a digital pharmacy company. And after that, I got into healthcare investing. And so I made a couple investments out of a fund in the healthcare space, and that's one big area.

What areas of healthcare?

So oftentimes, like, software to make things more efficient, you know, or make— connect people in better ways. It's probably pretty boring from the outside. Like, I think the industry is just so massive and things are done so poorly in many ways. With, you know, just like having more startups innovating is a good thing. Mostly it's mostly on the process side though. It's not like new treatments or anything like that.

Right. Yeah, right. Yeah, it is. It is like that's a world where the technological infrastructure is just completely missing, or at least modern technological infrastructure is completely missing.

Oh, well, I think it's, you know, slowly being upgraded over time, just like anything.

Not like— I would— I'd say not like most things, it's so heavily regulated that it is, it takes someone with a really big pickaxe to say, okay, we're gonna build the information infrastructure. Or a company, I'm an investor in a company called NexHealth, where it's just an API communications layer between doctors' offices. Cool. And that's just a massive, that's not Slack, that's not building out a communications layer like Jira, that's like, Everything that you're trying to do is 3 times as heavy.

Yeah.

Within just the compliance side of things.

Yeah, it's, it's a, um, I mean, like, yeah, there's a lot of like regulatory lift on that side, you know, building a healthcare company for sure. It's not great.

Is it? Are there, uh, what are some other spaces that GOAT— and does it actually, just backing up, does GOAT Capital, do you think about things in terms of spaces or Theses?

Well, it's just interesting because my partner and I, uh, are a little bit different. So Robin— it's just the two of us, uh, and it's a, you know, we're like a seed fund and we participate in some Series As. And, um, Robin is much more— he's like a hunter-gatherer. So he's like— or like a hunter, I guess. He's like going out, he has a thesis, and he's like, okay, I want to go find a company like this, right? So for example, maybe a year and a half ago, he was like, oh, Justin, we should, you know, someone should create a genetically modified organism, like a GMO tree company, like a company that has GMO trees to pull more carbon out of the atmosphere. Wow, yeah. And then we actually went and found it. So, we found this company called Living Carbon. They do exactly that, based in San Francisco. Founder Matty Hall's really incredible, dynamic young founder. And that's an example. If you think he has a thesis of like, this is a way you could attack a certain problem, or here's a big industry that's about to happen— climate change is one of the ones he's particularly interested in. Maybe we both are. And so, uh, then he'll go out and like find a company, right? And then I'm more like— I would consider myself like a farmer. I'm like agriculture, right? I'm out there making my YouTube videos, and I got a lot of like relationships He does too, actually, probably more than me, but like of people who send me stuff. And then I just aggregate all the deals and kind of parse. And then I'm more interested, kind of like the Y Combinator style. It's like YC funds the companies where that apply, right? It's like funds out of a pool of applicants. I'm mostly like looking at the people who I get in touch with or get in touch with me, and I'm like, okay, this is a good business, and this is a good business, this isn't. And I just try to fund the ones that I think are good.

Yeah. Is there anything that has changed over the years that you've been investing? Where your mindset has shifted, where you're doing it differently?

Yeah, I think I've gotten more picky, you know, and more willing to trust my gut. I think a lot— I used to invest more into things where I thought it was a good idea, but maybe I like had some feeling that it was like wasn't quite right for whatever reason. Maybe the founder wasn't right or whatever. Um, and I think that's always a mistake.

Is—

I've never been like—

What's a mistake? Say it again.

I've never thought like, this is a, you know, I've never had the gut feeling that it was like actually probably not a good investment, but like it seemed like really good on paper, so I invested anyways, and that's been good. Yeah, yeah, had a good outcome.

Has part of that been Robin and having a partner?

Yeah, Robin's— it's good to talk through things with someone. So like, it's also like I don't make on-the-fly decisions very much anymore where I'm like, oh, I for sure want— I used to be like, have one meeting, be like, okay, I want to invest. Now it's like It's— I think I'm a little more disciplined around like, okay, I'll wait a day and see how I feel and then like do some more research and, and then, you know, decide then.

How do you compare investing versus building for how it speaks to your soul?

Investing is like way easier, you know, in so many ways. But I think more importantly, um, you know, with— I realized that I just like the things you have to do when you're investing than I like the things you have to do when you're building something. Right. So in investing, it's like you are learning about new spaces, you're meeting new people, and you are raising capital. Like, I love those things, right? And helping people out and mentoring them, right? Once you've made the investment. On the building side, you're like managing people, you are recruiting, you're building product. It's just like, I don't wanna do those things most of the day, most times. Like, I'd rather spend my time doing the investing side.

Do you ever look at a founder that's going into that and you're like, man—

I think there's certain founders where they'd be better off as investors, for sure. But I mean, everyone should have their try.

Well, and Warren Buffett says, you know, it's— and I believe this strongly, that being a businessman, in his viewpoint, he says, being a businessman has made me a better investor, being an investor has Yeah, I believe

that 100%.

I wouldn't know what to imagine. Would you have been a decent investor had you not—

Well, I think right now everybody's a good investor because they're investing in this massive, like, you know, 12-year bull market,

right? So do you think—

like, I probably would have been.

Yeah, the same, same kind of on-paper success story as an investor, you think?

Yeah, I think so. I mean, just anyone who's like been investing in technology for the last 12 years looks like a genius. is right now. So, you know.

That is so, so true. Yeah, I had some that have done really well, and it's so easy to be like, oh man, I think I'm really good at this.

Yeah.

And especially in comparison to, I actually had this sad realization probably a year ago. I was like, man, I think I'm a better investor than founder.

Why was that sad?

It was sad, I guess sad because I, I love making things.

Yeah.

Really love making things. And I'm happy to be pleasantly surprised if I'm wrong in this, but I love making things, and I think building a company is just the most sustainable way to continue to make things.

Yeah.

So the investing side is more of a money management type of pursuit, and it is encouraging. I love encouraging creators. That is also speaks to my soul. But if I couldn't make things, then, uh, yeah, that would, that would totally destroy my soul. So figuring out that I was a better investor than someone that could maybe make things on a grand scale, yeah, was like, shit, okay, this kind of sucks. Because I love making, and I really, I guess I tie companies and entrepreneurship to the most sustainable, you know, artistic expression.

Well, I mean, it occurs to me that you could make stuff and not be the best in the world at it and be okay with that.

Right, right. And I think it's actually this concept that I am trying to put out in the world is surrenderipity. So, serendipity from just surrendering to whatever the universe kind of has in store.

I love that.

And so, I'm okay with making that observation of, okay, heretofore, 14 years into building things, maybe I'm a better investor. Maybe in a very good, in a good positive way, you're right in that, no, the bull market makes you think that, makes me think that I'm a decent investor, but it's actually—

Well, I think there's some part of it, some of both, right? You're like a pretty smart guy and able to meet people and do some analysis on their businesses, and you've picked some really great businesses, you know? And you've been investing in this massive bull market, so you're very lucky to be in the right place at the right time.

Right.

Yeah, probably some of both, just like entrepreneurship.

Yeah, definitely. There's a, uh, timing is, is so, so important in it. Do you think there's a— this is the, the dumbest and yet the most interesting question to ask really smart friends, but when you say it's been a 12-year bull market, there seems to be some implicit communication that you think it's— it could be coming to an end.

No, I actually don't think that necessarily.

Really? Yeah. Okay, so tell me more. What do you think Is going to happen with— or how would you respond to someone saying, all right, it's been a 12-year bull market, a crash could be coming, and tech is so wildly overvalued?

Well, I don't think tech in general is wildly overvalued. I feel like we're going through this massive digital transformation of our economy that's going to take 100 years, and we're like 30 years in, you know. And so to me, it's just huge. It continues to be a huge opportunity. You know, it's like Bitcoin. It's like super valuable now and appreciated 10x in the last year or whatever, 5x in the last year. But I think it's, you know, you know, my price target is in the hundreds of thousands of dollars. So I think it's probably, you know, it doesn't— just because of what has happened in the last whatever period of time doesn't necessarily mean anything about the future. I think, um, for tech, it's just— I think it's every company is becoming a tech company, so there's just huge opportunity. I think in to fueling that transformation. So I think now's still a great time to invest. But I— but also, like, we've been riding that train, and so the point is more like, you people who've been on the train for the last 10 years have done really well. So, you know, that's— they've been lucky also,

and arguably are in the best position to—

To continue being lucky.

To continue to be lucky in the next 10. This episode is brought to you by a little sipper Called Magic Mind. Ever wake up in the morning wondering, what am I doing with my life? Well, what you probably aren't doing is sipping on them Magic Minds. Magic Mind is a 2-ounce shot— matcha, nootropics, adaptogens, functional mushrooms— everything in a morning ritual drink that you've ever wanted. You take it alongside your morning coffee or tea, you get 7 hours of creative productive flow. It has 12 magical ingredients that all combine for everything you'd want in a shot: energy, cognition, de-stressing, immunity support, everything in this 2-ounce beautiful shot that tastes delicioso. So go check it out, magicmind.co. Enter promo code BTL— that's BTL for Below the Line— for 20% off. Magic Mind, Go check it out and get them sippers. Tell me about your personal transformation. So, maybe your mindset hasn't shifted too much on the investing side, but your personal transformation. We find ourselves in LA. You got long hair. It's come a far— a long way from— we met January of 2012.

Yeah, it's been 9 years. Yeah, I realized I was thinking about that this morning. It's like, wow, you know, now we're old friends. Dude, I know. You're— we're both old.

We are both old. We both have kids. Yeah, I remember the first time I met you. We met in the back of YC. We were in the same batch, and you had been third before, so you really knew ins and outs. Yeah, and we were in the back of the room. We sat in down next to each other eating dinner, and I think everybody in the batch knew who you were. And we were sitting down eating dinner, and there— and then you, you kind of ended the conversation. Everyone was continuing talking, you were typing, and I think you were coding for Exec at the time.

Yeah.

And I remember feeling like, this guy's kind of tough, he's a tough cookie.

Oh yeah, well, what, what made you say that?

I think there was, to be honest, I think there was a look at other companies. I think it was almost— I got the vibe, and this could have just been in my head, that it was like, this is competition. These other companies are competition. And maybe, maybe not direct way, but some indirect way.

Yeah, I think I have a, you know, one thing I've learned a lot about myself in the last couple years, and we kind of talked about this on the podcast in the last couple episodes, right, that we did together. And one of the things I've learned about myself more recently is that I have a look by default that's, like, disinterested, but then it goes to, like, I'm very warm and engaging. I can be very warm and engaging, but then I also, like, have this flat, disinterested look, like, by default. So it's, like, um, kinda like a random reward ratio for people. Mmhmm. Like a variable reward system where people, like, they're like, oh, I want the engaging Justin, but sometimes I'm getting the, like, Justin, who just like looks like he's like not interested. And, and I think that makes people want it more, actually. And so I've gotten this feedback from people in, um, various contexts where it's like, if I was just like not engaging all the time, people would be like, okay, fuck that guy, right? And they'd just be like, whatever. But because it's kind of like, so there's like a glimpse, or they like see that, like, you know, in that, that, that thing that pulls them in, and then it's like taken away. It's like a, it creates this like, people are like kind of like, what the fuck? Or they're like left wanting more. And I think that was a learned behavior from when I was a kid where, well, I think part of it's natural, like genetic or whatever. That's kind of like my natural state. But then I think part of it is like a learned behavior from when I was a kid. And one of my friends, I did this program called, Leaders in Tech. I think I might have talked about it before on this podcast, but basically it's like a, um, it was kind of a program, like a, like a year-long group, right? Like monthly meeting group. And it's kicked off with this like, and this, this like intense workshop basically called a T-group where everyone, you know, you have 12 people in a circle, it's facilitated, and you just talk for like 40 hours about how the other people are making you feel.

For 40 hours?

40 hours over the course of 4 days. Yeah.

All right. Damn.

It was like 36 hours or something like that. It was like a lot. And I learned about my— so much about myself and reflected by these other people who are strangers, right? You don't know anyone in the room. And, um, anyways, after that, in one of these like follow-on meetings, one of my friends told me, she was like, you have this natural way of creating a power dynamic between like putting yourself in a position of relative power to the people around you. And it's almost like Uh, like a reality distortion field or whatever. And there's many ways that you can— you do it. And I was aware of some of them, but I had never heard of it like that.

Is this someone that knew you well?

Yeah, she knew me through this program, right? Like, I mean, once you spend like 36 hours with someone, and then like, you know, we were in the group, ongoing group together, so we'd spent like, you know, 70 hours together, right? Or something like that. Um, in like really intense, like workshopping-style conversation, not just like casual. And so it was interesting to hear that, and it resonated with me. And I guess my point is, like, when we first met, I think there was probably some of that dynamic at play that I was just doing subconsciously without even knowing it.

So from my experience, I was— there was kind of this— I think there was a physical distancing of maybe an inch or 2 of like, who is this that's coming to sit down next to— maybe there's like 2 or 3 other people, kind of physical distancing. There was kind of a— I don't know why I remember this kind of coldly, I think, or vividly, and the coldness of it, I think because in our batch you were well known. And so it was, I don't know, maybe 3 weeks in, 2 weeks in, I was like, oh, okay, sweet, I'm gonna sit next to Justin and say hey. And it was, yeah, this 2-inch just tilted head kind of distancing and kind of a little bit of a cold look. Not not super cold. I'm being yeah, I'm being like no tell it later. Yeah, I'm not I'm not sugarcoating this at all. And then kind of like it's interesting that you articulate that way. There maybe there was this establishment of you're on probation right now of of this conversation. But I will say that's so different than I feel like the Justin last. 3, 4, 5 years.

Yeah.

And I obviously— part of that could be our friendship, but I actually think it's you also. Your default, it seems to have changed towards— I remember we were going into another friend's apartment, and I remember seeing you as we were going in, whatever, 8 in the morning, and you saw me from 50 feet away and the warmest smile, like, dude, James!

Yeah.

And I was, I was like, I think it took me by surprise. But since then, that's, that's probably been 2 years, uh, 3 years. Each time I see you, there's a default really high warmth.

Well, so, so I don't remember if you remember, but, um, that was always there, right? And that, like, uh, you'll remember, like, we had that party bus that we funded with Tilt, right? And so, like, I love to host people and engage with people, and, like, in that I think that was the first time we really hung out, and that was like we were as friends, right? Not just like we're in the same YC batch or whatever. And I don't know how your impression was, but like I think it was, you know, I remember myself being very engaged with people around, you know, during that. I think the difference is just most of the time before, like before this, like, you know, transformation the last couple years, I was like mostly engaged with ideas and not that interested in other people. I was mostly interested in myself, actually. I was like someone who put myself in the center of the universe. And, um, I think more recently I've like just become more interested in people and like been interested in engaging and curious and excited about the people around more than the ideas.

Walk me through part of that transformation. We've chatted about— we've broached the topic on previous episodes.

Yeah, well, I think it's a lot of it. I think a lot of it is really learning that, that people you can learn something, really internalizing that you can learn something from anybody. You know, you can learn something from anybody and everybody, and there's something interesting about every person. And having that mindset, you know, and really trying to, you know, hold that context has really been a big part of it, I think. And then the other part is, I think before I was really engaged with the world of ideas and, you know, specifically startups and business, but I was Engaged with the world of ideas because I was like, this is you know. I was always an extrovert. I wanted the attention and connection with other people, but I didn't know how to get it. I think when I was a kid, so I created this like defense mechanism around you know kind of these ways of putting myself in in positions of relative power is like how I'd put it. Then I was like, well, if I just get become successful, then and then all people will be attracted to me, right? And that was what I you know the whole thing of working on. Twitch and startups and eventually becoming successful. And then of course it doesn't like change anything really. And then after that, it was realizing this— there's a shift where I was like, oh, actually the real way to connect with people is just to be curious and interested and open to them. Like, you don't need to be super rich or famous or whatever, you know? And that like works a lot better actually. And so I think that realization plus the like becoming genuinely interested in the people around me is like What the transformation was.

Were there any specific events or any specific—

Not really. It was just like a lot of learning over time, you know.

Really?

Yeah.

Is part of that a growing security with yourself and, and not needing to, uh, get to a certain place in your mind through business or through—

You know, that could be. I think that that's a valid question, and maybe that's part of it. I think a lot of it was That part was always, always there. And I think that there's a part where I like love people and I like love to engage, you know. I was a very warm person, and I think that came out when I was hosting people.

You're right, and you are totally right on that. They— I remember going to your apartment and in the party bus, and it was complete like hospitality and warmth,

right? That was just like 5% of the time, and 95% of the time was like, okay, I'm working on this business, and like, what are you talking about? You're boring, right? Like, and then so people would would get this like random reward ratio and they'd be like, want the— it's like a slot machine, they want the like warm Justin, right? Right. And then I think it's just the ratio has changed a lot, you know?

Yeah, I remember I wanted you to become an investor in Tilt so that we would— it was almost like, it's like— and I think maybe part of this—

yeah, you wanted it super badly, right? Like, I think— yeah, yeah, I remember that.

Really? Tell me what you remember of it.

Well, I remember you coming around and like being like, hey, I want you to invest. And I think there was I broke down. I do remember I broke down. I was like, look, if it was like a $50 million valuation or something like that, and I was like, this is like not a good investment for these, you know, economic reasons. I don't remember what the reasons were at the time, but I think the valuation just like— I was like, here's the range of outcomes that I think it would possibly be.

Yeah.

And then I was like, so I just think that's like the out— the range of the expected value is like not high enough, right?

No, you can be totally— I want you to be totally— No, I think that's what I said, right? As well.

Something like that. Yeah. And then I think you— did you make the deal better for me?

I think so. I've made you an advisor as well.

Yeah, so you made the deal better for me, and I was like, okay, that like brings it into the range, so I'll invest. But you didn't have to do that, right? You had all the money you needed. You didn't have to do that. I think you specifically wanted me to invest.

Yeah, and I think it's because maybe it's that—

that— So I'm in your head? Yes.

No, you were. I think you were living rent-free in my head. Like, I've got to get Justin, and I think maybe part of this, I wonder if you being the oldest sibling is also part of the, the comfort of this power dynamic. I, I always have discomfort as the youngest of 5. I always have discomfort. Yeah. I, I hate authority. Like, I distrust it with, uh, 4, specifically 3 older brothers being, you know, tyrant, tyrant authority figures in the household. But I remember also being so wired, or no, I am so wired. And I remember having this realization a few years ago that I'm so wired to— it's not just I want everyone to like me for the benefits of being liked. Being the youngest of 5, I think it's in my head of like, I don't get to belong unless I'm spot-checking, making sure that everybody wants me to be there.

Yeah.

And, and, uh, and then I'm liked.

Yeah.

And so I remember, uh, with almost every YC partner invested, and I was like, Justin didn't even show interest. So yeah, I came to pitch you. Yeah. To get you to join.

Yeah, I remember that. Um, yeah, I think that's right. I'm the oldest, right? And so it's— for me, I think a lot of it came from my mom. I would see that how she, you know, she was— I'm very similar to my mom in a lot of ways. And then also my dad in some ways. My dad is like He kind of has that passive look that's just like not into the— kind of like disinterested look by default. Like, I don't think that necessarily reflects what's going on on the inside all the time, but like, that's kind of like his default look. So I think I have that similarly. And my mom can be very warm and effusive and like connect and really interested in people. So it's kind of like flips back and forth between those, you know.

Where do you think it comes from with your, with your dad?

I think he's, he's a little bit like doesn't You know, that's kind of just the— his family environment. Like, they were not that communicative, you know? That was the impression I got. I wasn't there, but yeah.

Yeah, I— yeah, and I remember, um, this feeling of like, God, there's some distance between, um, this person that I admire and I want to get him on the same team. So I was like, I— even before getting into IBS, it was like literally like How do I just— we're gonna— we bump into each other a few months and I want him on the same team. And I was like, oh, let me get him to invest way after seed round. And it— so there was— it does, I think, work in your favor, and that it does—

I think it— I think it does. I think it does work in my favor. I think it's a learned habit that's like a defense— defense mechanism might be the wrong word, but like a way that I've learned to— it's an adaptive response to shape the world to revolve the world around me, you know? And, and that makes me feel— because I always felt like, like an outsider and like I didn't connect with people— that like makes me feel like I'm an insider. You felt like that? Yeah, when I was growing up.

Really? Why?

Yeah, I think in school settings. Yeah, in school. And just like, I, I don't think I got the approval from my peers that I always wanted, you know? And so that was a major driver in like, oh, become successful, etc. And so I think that this is like a learned behavior to create, you know, put myself in the position of power and like have the world orbit around me, right?

What was 13-year-old Justin like?

I mean, I was a, I was a nerd, and, but I was kind of like the, the popular nerd in the group of nerds, right? And so, you know, I kind of created my own like little domain, but, um, I was always like looking at the cool kids and like wanting to be, wanting to be accepted.

That's, that's interesting. I think I was probably the nerdy kid in the popular group. And so the, the inverse of that, still looking in, barely let in.

Yeah.

To the border and looking into that, you know, epicenter that, uh, you, you want to be in, or that will serve some validation that you're doing this whole life thing right.

Yeah.

I was kind of in there, but I was definitely the, the, the nerdiest of of my group of friends. It was almost like forced to be into the interests that they had when I had these separate interests, but it was like, my own separate interests be damned.

Yeah.

I need to feel this belonging.

Yep.

In this group. There's an interview question that I can't remember who, who says the question, but it's along the lines of, tell me something that happened between— before your 18th birthday that helped shape who you've become. You've been on the podcast before and I've asked, tell me 3 stories that have helped shape who you've become. But I wanted to ask you if there was something before the age of 18 that you'd look back and say, okay, that certainly shaped who I've become.

That's a good question. I have to think about that. Is there something that's shaped who I've become from— I mean, I'm sure like everything, right? But it's like hard to draw the parallels back to a specific Um, like, what are the memories that I remember even? I have like a very bad memory of my childhood, which I feel like is probably some sort of adaptive response too, you know? There's probably a lot of things that like were like memories that I have of being in the outgroup, you know? Um, like, I remember— Which ones? Like, I remember, you know, when I was like 13 or something, I had like— I was wearing like some t-shirt that was like super big, and like this one girl in my class was like, making fun of me of this like t-shirt. She was like, it looks like you're showing cleavage, you know. It was like big neck hole or something, like a total— like it was probably what I would be wearing today, to be honest, like in LA, you know, like a giant— yeah, it's come back in style. Yeah, giant neck and baggy t-shirt, you know, um, looking like a DJ or something. But at the time it was not cool. And I just remember— I remember that, like feeling like I was on the outside. It's a small thing, you know, it wasn't like the biggest thing. I'm surprised this took Dude,

I remember in 6th grade, so I was wearing a yellow, apparently a too bright yellow shirt, and someone said, I wouldn't be caught— a friend's older brother at school was like, I wouldn't be caught dead in that shirt. I was like, that's a weird phrase. Yeah. I remember the first time I came across that phrase, I was like, he wouldn't be caught dead in this shirt? I need to be thinking about the clothes I'm gonna potentially be caught dead in, and it shouldn't be this shirt. And yeah, that totally stuck with me. I never wore that shirt ever again.

Yeah, maybe it's those small things, you know. But I can't point to like one like big thing where it's like, this is— this was like shaped me in the specific direction, you know. It's probably like all these small incidences.

Well, and I, and I'm sure for being an older brother to 2 super smart younger brothers, I'm sure that's been, uh, that's been part of that just Continuation of shaping you. Do you ever, do you ever think about sibling order in terms of—

Well, I think the sibling order definitely affected our family a lot. You know, I think I'm classic first kid, you know, like achiever. Like my mom put a lot of energy into like making sure that like I was good at math, for example. I was like remedial at math when I was in grade school. My mom is a physics major, was like, there's no fucking way I'm gonna have like a kid who's like bad at math. So she would like make me do extra homework Basically. And she would do it by writing the problems, like multiplication problems and addition, you know, basic arithmetic, in like colored pencils. So it'd be— she would call them colored problems. And it'd be like, you know, I'd have to basically do this extra problem sets, like, to practice so that I could be like decent at math. And

Dan didn't get that?

No, I don't— I— maybe they did a little bit, but they were just, you know, it's like you have, as a parent, naturally you have more demands on your time when you have second, third kid. So I think it was— they didn't get as much, you know, pushing slash tutoring slash, you know, you know, help in that way. And so I think I was a classic achiever for older kid with a big chip on my shoulder. I'm like, am I doing enough to like achieve enough? I think Daniel was like classic like middle brother, like a little bit in my shadow, in my shadow, and like resentful of that. And, um, That also drove him, obviously, to do really big things. Well, maybe that's not the only. I shouldn't say that's the thing that drove him, but like you know, I think that was that is something that he you know. Let's just say that I was super thrilled when you know when they sold Cruise. My brother's co-founder Cruise, and they sold Cruise to GM for a billion dollars. I was like that was I was so happy because I was like people. I remember one person. I was at a conference or something, and someone was like because he was in Silicon Valley for like years, right? Right.

Oh dude, he's in our batch.

Yeah. Yeah. We started a company together. He was still in Silicon Valley for years, and then people would always be like, oh, you're Justin's brother, right? Because I was like out there, I was like, I'm doing this startup, and I was like very vocal and visible. And I think he hated that shit. And then I remember there was one moment when we were at a conference and somebody was like, are you Dan's brother? And I was like, oh, there we go, tables are turned.

Does that play in an older brother— I've got 3 older brothers, and curious if that plays in your head of your success Does it go through your mind of, okay, this is gonna have its implications on, on my family members?

Oh, like, are they gonna have some jib about it? Yeah.

Either that interpersonally with you, or just, I don't want them to compare themselves to, to me when we're sitting around Thanksgiving dinner and, and it potentially comes up.

Yeah, no, it's just I've always been like somebody— I think by default I always put myself in the center of the universe, so it's like that has never crossed my mind, to be honest. Yeah, go ahead. Yeah, I was gonna say my youngest brother Damien is— he's like classic youngest brother. He's like, he's finding a new axis of competition, you know. He is like, no, not interested in competing in the like, oh, I'm gonna be the best startup founder or something like that. He's more interested in like climbing and like living his life, like, you know. And, and I think that's like much more healthy in many ways.

Yeah, that's, uh, that's interesting.

Although he did end up founding a company that's like pretty successful.

Which one did Damien found?

This company called Shogun. I think they just announced they raised like $67 million.

They're huge. Shopify.

Yeah, the Shopify app.

Yeah, yeah, dude, that's awesome. I didn't know he was a co-founder of Shogun.

Yeah, they started out of my house like 6 years ago, something like that.

Oh shit. Oh, that's awesome. Yeah, dude, the Kan Bros. I got to keep tabs on all 3 of you. There's just 3 of you, right?

There's just 3.

All right. Well,

I have a cousin. She's at HBS right now. I have a lot of cousins. I have a lot of cousins, but one of my favorite cousins is at HBS and she, you know, maybe one day she'll start a startup.

She's gonna get in the startup game?

Well, she's currently a McKinsey consultant. And I'm like, she was in startups and then now she's interning at McKinsey. Tell her it's a waste of life.

Yeah, dude, if you're listening to this episode, what's her name?

Ariel. She goes by Victoria.

Victoria, terrible idea. Terrible idea.

Terrible idea.

Especially if you think it's gonna broaden your horizons and open doors. That is literally what systems tell you to gobble you up and never let you go.

Were you ever a consultant?

No, dude. All I know is startup stuff. Look

at that look of disdain. I love that.

Oh dude, it's, it's like, it's like, you know, getting a PhD. It's basically just a corridor within a narrower corridor within a narrower corridor of of just basically like, it's like investment banking. You go do the 2-year analyst program because it's gonna open doors. To be fair, I do think it did. You're gonna have so many options on the other side of it.

Yeah, people do. I mean, if you want to go into finance, you get options.

Yeah, options. But then the options, then it's like, now you do this other thing. Now you become, uh, go be a principal at a hedge fund. It's gonna give you options. And then you, you find yourself, you're 45, and you're like, fuck, I have quote-unquote options, and I've been chasing options the whole time.

Yeah.

Instead of actually living life, designing life, being— I think being useful.

There we go, PSA.

Yeah, yeah. Consultants are the— I mean, you know the adage, it's they'll steal your watch and tell you what time it is.

Yeah.

And so I think it's— maybe it's interesting for a year or two, but as long as it's leading towards Or the realization that making something is better. I think that's a question I have for you on the investment side and content creation side. After Atrium, do you think you're gonna start something again? And you're incubating ideas. Well,

we're incubating ideas, but to be clear, I'm not the CEO of it. You know, I got to work with partners who have like a lot of guts and energy still. You know, I'm an old— I'm old and washed up. You know, I'm like, I'm like the drunk at the bar who's like a retired boxer who's got knocked out too many times that, you know, you're drafted into becoming the coach.

Yeah, you still got ideas.

I'm gonna train Creed, you know.

Yeah, that's right. That's awesome. Do you really think of yourself like that, or do you think—

Yeah, for sure, man. I'm too— I'm way— like, when, when, like, we started Justin.tv, I would have slit my own wrist to be successful. Mm-hmm. For sure. Like, it was my whole ego, my whole identity. It's very unhealthy in many ways, but now I wouldn't. Like, I'm like, I'm— my life is great. I got a family. I spend time with my family. Like, I, you know, I didn't have those constraints when I was, when I was a kid.

How do you, as a, as a friend that thinks so deeply and is trying to, I think, in a similar vein of, of my work with this podcast or investing in writing, elevate the consciousness around creation, how do you balance That mentality you have with, I don't know, next Tuesday making an investment in a company where you're like, I kind of like that founder.

Well, the honest truth is everybody has to go through their own experience. You know, I can tell somebody, oh, it's not gonna make you happy to be successful, but there's gonna be some percentage of people who need to figure that out on themselves. This is one of my favorite books, is a book called Siddhartha. Have you read it? By Hermann Hesse?

Yeah, oh yeah, yeah.

So in the book, Siddhartha has a kid that he doesn't know about, and then later in the later part of the book, kid, uh, he was reunited with his kid and his kid is like, um, you know, into all this bad behavior. And he's like talking to his friend and he's like, oh, why can't I teach my kid to avoid all these mistakes that I made? Basically he's like, you can't. Like, he has to go. You can't deprive him of that experience. He has to go live him— live his life for himself. Hmm. So I think that when I invest in companies where the, the founder has like a major chip on their shoulder and they have something to prove, it's like, well, They got to discover it for themselves. Who am I to deprive them of that journey?

There's a lot of truth in that. And it's— what's the quote of, a fool must persist in their folly to become wise. But is there an ideal mindset that you'd say that you will look at from the other side of the proverbial table as an investor where you're like, OK, I really dig this person's mindset?

Well, I think it's people who are learning, right? Like, a lot of people have something to prove. But if they have a mindset of learning and a growth mindset, It works in the beginning. It's like the bootloader. Like, having something to prove works in the beginning, but eventually you get some— you get burned out of that and you have to find a higher purpose for your work. Mm-hmm. And sometimes people have that in the beginning, right? And sometimes people think they have it and they don't yet. That's okay too. And eventually though, every great CEO that I know has found— has transformed from somebody who had a lot to prove to somebody who has a higher purpose for their work. And I think that is a natural transformation. So if I can help them, you know, if they have a growth mindset, I think they'll eventually get there. And so if I can help them, guide them in that direction, that's great.

What would be an example in your mind where you've seen that transformation? They started with a certain set of reasons for starting their company.

Well, I don't want to say— like, it's hard for me to be like, put people on blast and be like, I don't think their reasons were like good in the beginning, right? Like, but let me just say there's like a lot of decacorn companies friends that like I feel like that was the case where they started off with like, you know, they just want to create a company and like have be successful, which is not bad. Like that's most people in our society, right? Thinking like if I'm successful, then a lot of my problems will be solved. But eventually they turned into like, wow, I really care about this community, this being a leader, being like being building this product. Like that's, you know, that's the thing that that drives me. more than any of the other, like, outside accolades or anything like that. And to me, the most successful founders who still run their companies make that transition.

Uh, for our last question, since we last chatted, um, and it was during my book launch, it was a lot, man, that was a live event, so very pre-COVID. What is the— can you walk me through the, the emotional arc with Atrium and, and having to wind it down. Um, how long ago was that?

That was a year and a half ago.

A year and a half ago.

Or like right before COVID

Yeah. So what was— walk me through the emotional arc of Atrium even 6 months before.

Well, I think that's when we last talked, right? And so, I mean—

Well, even before starting Atrium, like walk me through that emotional arc of, okay, I'm going to start something again. And all the way through to winding it down.

Yeah, I mean, so it's like excitement, right? You know, I was excited about this new idea. I love ideas, and I started it, and then there was just like huge stress and difficulty in terms of really making the business work. It's a very operationally intensive business. I don't think I was particularly well suited for that or prepared for it. And then eventually, like when, you know, fast-forwarding the shutdown, it's like, Usually people shut things down when they run out of ideas, and we did not— I did not have any ideas for how to transform the business to what I thought was a venture-backable business. And it got to the point where it's like, this is not a business I would invest my own capital in, so we should like shut it down to return the money, because otherwise we're just wasting money, in my opinion.

And were you at an emotional low, or was this—

No, I was just actually— I don't think I was in an emotional low. I think I was in an emotional low years before that, you know. And so this was actually like just more Oh, this is a— if I'm being honest, right? Like, um, if I'm being high integrity with like what I actually think, and then this is my truth, you know? I don't believe that this is a good business as it stands. And so then the right thing to do was shut it down. And it was difficult. It was very sad. There was a lot of grief because I built a team that I really loved. But, um, at the end of the day, it was like, that's the right thing to do, is what it felt like.

What were some of them, some of the learnings that you reflected on afterwards for if you, if you were to go back to you?

I think the most— yeah, the most important thing is just like start something where you have that higher purpose. Tying back to what I just said, right? That you want to start something where you have a higher purpose. Now you're not a mercenary, you're a missionary. Because then when things like don't look like a great business or they're like things are going badly, like you're gonna want to stick with it, you know.

What would you say to someone that's listening to this that might say, well, you'd already sold a company for $1 billion, and so was it out of just— would you have been able to make that decision of, okay, let's just wind it down and walk away if the $1 billion—

Maybe not. It could have been different.

Has that informed— has that experience informed your investing of second-time founders that have been wildly successful?

Yeah, I think I'm much more skeptical. I'm skeptical of investing in second-time founders. Just, I think a lot of people just wanna invest in them because they've done it before, and I think you really have to like think, is this person highly motivated? Are they, you know, are they working on a good business? Are they gonna, yeah, I think there's a lot of, I would just still do the, you know, check the boxes instead of getting caught up in the reality distortion field.

Right. What is the ideal— this is so high level, so it's very hard to take this away, for a listener to take anything away from this verbatim, but what would be the ideal if a second-time founder that's been wildly successful before, you're skeptical of, what would the archetype of the founder where you're 7 minutes into the conversation and you're like, Okay, I really dig this type of individual.

I like— I really like the people who are humble, but they're grinders, and they're like, they don't have a lot of ego. They're just dedicated to like, this is my mission, and I'm gonna keep my head down and figure it out. And those are the people who I think are, you know, build the best companies.

Is there someone that comes to mind that you invest in?

Yeah, there's a couple companies more recently that are like kind of newly, you know, doing really well. Not newly, we're doing really well, but maybe more in the public eye. But my Matt Gamash Aselin from Alto, co-founder of Alto, is the CEO, and he's like that way, just like heads down figuring things out, you know, just like always learning from people around him. But really, at the end of the day, they do whatever it takes to like get it to work, and he's like a very humble person. The same is true of like one of my friends Moses Lowe, who started this company called Zendit, which is kind of like Stripe for for Indonesia and Southeast Asia. And the company's doing really well. Similar things, just a very humble person who's like always learning from people and just building like an amazing company one step at a time.

It's really after the fact that I learned to love founders so much more, but send updates, they're just knocking things out, and there's really little to no celebration around it, but it's just, Like whether it's a growth graph going up and to the right, and they're like, you talk to them about it and it's so nonchalant.

Yeah.

And there's no— there is no growing hubris because you also have— I'm sure you have founders in your portfolio where you, you can see a growing hubris as they start to accomplish more.

Yeah, for sure.

And yeah, it's, uh, which is a ticking time bomb.

Yeah, you want the people— like, humility is important because There's always things you're gonna have to learn and like figure out from that are hard. And if you are not humble about it, you're not like— that's gonna prevent you from having an open mind.

What is your— what would you say in all of your reflection for someone that's done so much? I know I said last question, but this will be the last one. That said, so much internal reflection, transformation, uh, in so many ways, I would say. What is— what are your strengths and weaknesses? Like, what are the things that you just now know you are not good at?

Yeah.

If you were looking at yourself to invest in your next thing— well, you already said you, you won't start it. Yeah. The boxer that would rather train, train other boxers than go out again.

Yeah. So my strengths, you know, my strength is I'm a great evangelist, you know, for things. That's the number one thing. I'm great, a great evangelist, and I can catalyze people into action. Um, that's like the really the superpower. Like everything else is kind of like, I think I'm a okay at a bunch of things. And, you know, that's it though. And then my weakness is that I— is also strength. It's like my strength is also I'm interested in new ideas. Weakness, I'm also interested in new ideas. Every— I actually think everything that's a strength is also a weakness, right? Right. So like with new ideas, it's like I'm interested in new ideas, I'm open to new ideas, but the downside is like it's hard for me to stick to one thing, right? With the— which, you know, if you want to be great at something, you got to stick to something. With the evangelism, it's like I'm great at recruiting people and catalyzing around an idea. The downside is like oftentimes I'm like drinking my own Kool-Aid too much, you know? And then it's like I'm not— that's its own form of not being open to feedback in a way, right? If I know all the answers on like why this is gonna be an amazing business, then I might not learn enough about like what I, you know, downsides or things that aren't working or whatever, you know? Yeah.

So— Makes for a great, great investor.

Yeah, I think so.

Why'd you pause?

I'm just trying to think, is that true?

An evangelist and someone that loves new ideas.

Yeah, that's why I think investing is very activating for me. Mm-hmm. You know, I

think you're gonna be— you already are great at it, but I think you're gonna be, despite losing your money with Tilt, which apologies.

No, it's alright.

Listeners, you can become friends with— you can stay friends with your investors even if you lose their money.

Exactly. If they are sufficiently wealthy. If that was the only money I had, I might feel a little— some type of way about it.

I didn't know at the time, but thank God Twitch did well. Well, Justin, thank you so much for your generosity of time and insight, man. I love chatting with you, and I hope to get you down here in LA more and more as time goes on and maybe permanently.

It'll happen. Maybe.

I love it.

All right.

All right, buddy. Thanks, bro. Thank you.