#167 - Answering Your Questions On Investments, Businesses and Life
You would know more than I am, but this guy's Tim and his brother. I'm not that close with them. I'm friendly with them. I'm friends with them, but I'm not that close. Like, if you told me that they were worth over $150 million, I wouldn't be surprised. And they still act like they're poor and in kind of a funny way, which I enjoy. And they're—
they're super humble and they're like super hardworking still.
And they invest in everything.
Yeah. I feel like I can rule the world. I know I could be what I want to.
I put my all in it like no days.
So let's travel, never looking back.
Today we're going to answer a bunch of questions. But did you see Trung's tweet about the guy selling the card?
No.
What is it? Trung tweeted out this video that he found from probably the '90s or probably from the 2000s, early 2000s. And it's a guy who's got like— who's like trying to sell you on his like business card. That's a big square and you open it up and it's a pop-out and he's just really intense. But the video got— it's funny. You haven't seen this? No. Oh, well, this won't be any good then. But the video got like half a million views and people are making websites about the tweet or about the video based off his tweet. It was just funny.
It— you said half a million views now or like he tweeted something that already had half a million views?
No, it did now.
Oh, wow. Trung is a master of finding great content. That guy is really good. I have this apprentice who's working with me, Chris, for content.
He's basically the redhead guy.
Yeah, he's kind of shadowing me and he helps me produce my content and he's learning as he goes. And I told him, I was like, success is being Trung. So that's the level, that's the top bar. That's what you need to measure against. Here's 5 examples of awesome things he's done. And so he called Trung and he was like, what's your secret? What's your process? Basically, Trung was like, kind of browse the internet a lot. And, you know, there's no way you can, you know, it's like asking Michael Jordan, how do you jump so high type of thing? Like, it's not, it's not easy to describe how you do the thing that doesn't feel like a real process for you. You know, you're just doing it intuitively.
He's a machine. One time I called him at 11 o'clock his time. He's in Vancouver and he was at the park playing with his son. And I was like, Trung, like, I'm not trying to like get on you because I'm not your boss, but like, don't you have work to do? He was like, and he was like, bro, I wrote, I got up at 5 AM and I already wrote tomorrow's email already. I was like, all right, sounds good.
Um, okay, he's a machine. So I didn't see this video. Is it worth talking about given that I didn't see it or what?
It's too long to go through.
Basically, okay, people and myself, let's go to Twitter after this and let's go to Trong T. Phan, I think is his handle, and go look at his thing.
Dude, that slayed me. It was so funny. So he has OnlyFans, but he spells Phan, P-H-A-N, like his last name. And it's just a network for only people with the last name Fan. And I just found it so funny. Oh, that was yours?
Yeah, now we don't like it so much. Stupid ass idea.
All right, today we're going to answer questions. I, uh, we got, uh, it looks like we've got like 6 pages of text questions. So like dozens and dozens of text questions. And then we got a few dozen, uh, audio questions, like people calling in. But, uh, some of the text questions were good. I'm gonna start off, um, I'm gonna start, I'm gonna read a few that I think are cool. Let's do the first one. This guy's name is, uh, Johnny Volk. He asked, what are you both personally investing in right now?
By the way, do you know Johnny Volk? Do you know who this is?
He lives out here in the Bay Area. He lives like, I don't know, 15 minutes away from me. He's a super successful e-commerce guy, been in e-com for 10 years, sold his company recently, like, I don't know, a month ago or something for tens of millions of dollars. And he's a big investor in my rolling fund and several other rolling funds and really like ultra nice guy. So this guy's super legit. So he's asking, What are you both personally investing in? So you want to go first? I think you, uh, I think your answer is probably more interesting.
I'll go first. So right now the bulk of my liquid net worth is in publicly traded companies. Um, I own a bunch of HubSpot right now. I own a bunch of Airbnb. Besides that, I don't own anything else above $50,000. Uh, it's all in, um, so you're super concentrated in those two companies basically. Yeah, but then I have more money in the S&P 500. So like the total stock market index. I have, I'm going to invest around $250,000 to $500,000 in the next probably 18 months in startups. I own 6 figures worth of, into a variety of real estate funds, including Sweaty Startup, Nick Huber. And then I own my house and I'm in the process of buying multifamily properties.
So I would say I have, uh, if you just broke it out, you're like, you know, roughly you're like, okay, 70% is in the stock market, really in the two companies, you know, where, where my wife works and when I work, something like that.
No, I own way more just S&P 500 than I do HubSpot and Airbnb. Um, but I would say that, uh, 90% of my net worth is in the S&P 500. Yeah.
Simple stuff. And then my goal is to invest somewhere around 1 to 3% of my net worth over a period of time into angel investments.
Gotcha. Cool. And then some real estate mixed in, real estate being, you know, the house you live in and some other, you know, projects other people are doing. You're not currently buying and like owning real estate at the moment.
I'm going— I own my house, but I'm going to— I want to buy 16 units. I also have I mean, I'll say like half a million dollars in cash just sitting in a checking account, which I think is too much money. But when I bought my car, I just paid cash out of there. And then I own six figures of Bitcoin and Ethereum, of which I owned most of that Bitcoin from 2013. And I just bought like $75,000 worth of Ethereum like a few days ago because you and a few others told me it was interesting.
Nice. By the way, we got some criticism, constructive criticism, I would say, which was like, oh, the last few episodes feel like rich guys talking about ways to make a bunch of money, which honestly, good description for the podcast. But I get what the person's saying because they're like a fan and they're like, that's me raising my hand because I think I basically was like, oh, this BitClap thing is cool. And it sounds like a total Ponzi scheme. And so people are like, What do you got? Are we talking about like Jack selling like an NFT for like $70 million? So it just sounds like a little bit crazy. So I think, you know, although I think your answer is great because I like knowing how people invest their money, I think it's most people are very closely guarded with that info. People don't tell you what the hell they're doing. So you're kind of on your own to figure stuff out and you don't really have any data points triangulate because all the wealthy people don't want to talk about what they're doing with their wealth unless it's with other really wealthy people. And so I think it's great you said that, but I'm also, as you were saying it, that was just ringing in my head of like some guy being like, why you guys just talking about money? But it's like, well, that's also the theme of the podcast in a way.
And that was also the question and I'm trying to answer it truthfully. But also when we started this podcast, when you started this podcast a year and a half ago or two years ago, it really wasn't a bunch of rich guys talking about, it was a bunch of hopefully soon to be rich guys talking about stuff. And we've been talking about the same stuff the whole time.
Yeah. Oh, you mean us?
Yeah. Yeah.
At that point.
Yeah.
Cause yeah. And also, uh, I put this out there in the manifesto when I started this thing, which is I think it's unfortunate that talking about money and how to make money and what you do with money to make, how you make your money work, uh, earn you more money. I feel like it's unfortunate that that's taboo, um, to talk about. Like, it's like kind of like a, it's like kind of like low class or something to talk about because. Look, the reality is most people want more money and people try to signal and say, oh, it doesn't matter and all this stuff. I know a lot of people that want more money. Most of the people in my life, if I had the option, would you like more salary or less? Would you like more in your bank account or less? Like the answer is more. And if all the people who have money are really guarded and don't talk about it and don't want to seem like they're bragging, well, what that really does is it kind of like just traps the information from others. So that's kind of like my overall view of it. I know you're similar because I remember being kind of stunned when we first became friends and you just Facebook messaged me. You're like, like, how much do you make? I was like, whoa, whoa, bro. Like, what's going on here? But I was like, okay, you know, ballsy question.
The reason why that I actually dislike that view that if someone criticizes you for talking about money, it's because they are making the assumption that because you have money or because you don't, you are somehow better or worse. And in my opinion, like, I don't— just because you have money, I, I, I, that's— you have no intrinsic value to me. Like, you either are interesting or you are not interesting. And what makes you interesting to me is that people are just— they try ambitious stuff and they do neat stuff. Oftentimes that's correlated with money, but it's not always. Like, I knew this lady who would do these amazing art exhibits where she would like paint gold phones and like just do interesting stuff. And I was like, Wow, that's super badass. That's so bold of you to try that. She wasn't wealthy at all, but I thought it was so cool. Right. Uh, so to me it's about, uh, just being an interesting person. I don't really care if it's money related or not, but oftentimes it is.
Right. For me, I have like 3 or 4 different, uh, life games that I'm very interested in. Like, let's say right now I'm interested in the fitness game and I'm a total beginner. I'm a white belt at the fitness game. And so I have a trainer. He's like more like a black belt, you know, look at his body, look at his lifestyle. He's extremely healthy. And so I want to learn about the fitness game. I like learning about the happiness game. How do you be a happy person? How do you control your mood? How do I master my mood? I'm really interested in that, and I think about that a lot, talk to people about that. Then there's like the money game, and then there's like the making things that people want game. And I like all these games, and I admire the people who have done well in them. And I'm better at some than others where I'm like a total beginner, and in some I'm like a blue belt or a purple belt where I've done something, but I'm by no means at the end. So anyways, that's a tangent. But, uh, to answer John's question— did you want to say something else about that?
No, I answered.
To, to answer John's question, uh, I'm kind of similar. I, I, I tweeted out my, like, holdings a while back. Maybe I'll do that again. I need to go back and recalculate, but I tend to hold about 10% of my wealth in cash. Um, I think cash is being devalued, and I don't want to hold cash. Cash doesn't Earn, you know, cash sitting in the bank is nice for a rainy day, but it doesn't earn you more money. Right. The 0.001% I get from Wells Fargo or whoever is not going to like help me. I have a good size stock, you know, basically I would say beyond that it's almost like 50/50 of public equities. So stocks and, you know, crypto right now and, and then angel investing. So I'm angel investing currently through the rolling fund, $4 million a year, but that's not my money. Uh, that's mostly other people's money, and I get a carry on that. Uh, I get a 20% carry of the profits. So that's kind of like investing, but I'm not investing my own money there. And I'm looking at real estate right now, but the problem with real estate for me has always been, A, I'm a beginner at that game, and B, um, I don't want to sign up for more work. So I'm looking for ways to get real estate that's I directly own, but I don't have to do a ton of work. And those two are kind of at opposites with each other. I don't invest in other people's real estate funds right now.
Has your net worth or like your total portfolio increased a significant amount since your deal? Because it seems like you weren't very active before and now you are very active. And has that helped you?
It has increased because, you know, the stock market's been doing amazing last few years. And then with the deal, you know, like where we, when we got bought, the Amazon stock price was $1,850. Amazon stock price today is $3,100. So just while working there, you know, you're going to get pretty significant gain in your holdings there. And because we got bought, like a large chunk of the RSUs were just in that one company. So that did well. Uh, crypto is Bitcoin has done extremely well. Ethereum has done extremely well. So those have like, really worked. And then kind of like the side hustle money from podcast, email newsletter, stuff like that, sponsorships, that sort of thing has been really nice. So that's actually picked up as well where I wasn't doing that before. So I'd say yeah, but I would also say what really changed was my attitude. Like, I just started acting like a guy who's got $100 million for better and for worse. Like, I take bets that are kind of too big for my bankroll sometimes, and that's a risk, and I might pay the price, but I sort of just started carrying myself and acting like, and basically making decisions like, what if I wasn't worried about money? What if I wasn't worried about going from A to B? What if I just knew that I'll get to B pretty much regardless? How would I bet if that was the case? And so I started making slightly larger bets and just being more active. Whereas before I was a little more conservative with how I was investing, which is a huge difference in our philosophies.
I'm way more conservative than you. Way more conservative. Yeah. And I don't think I was telling a brain. He was like, because I told him I started angel investing. He was like, who do you think is going to have a better portfolio? And I was like, that's kind of interesting. And I, and the answer was like, my answer to him was, I think my portfolio has a higher chance of being pretty good. Whereas Sean's portfolio has a higher chance of being Amazing or zero, right?
Yeah, I think that's true. That's definitely true. I guess like the style of who you admire sort of dictates what blueprint you create. So like, for example, I was really inspired by like Chris Sacca's approach to how he went from like, you know, he's like me, he's like a bit of a degenerate gambler. Like he went, you know, he took like his law school money and then was day trading in the stock market during the dot-com boom, rode it up to like a $10 million, like took $25,000 and turned it into like $10 million and then went in the hole $4 million. That was like a crazy degenerate gambling run. If you haven't heard me talking about my bets in crypto and I used to play poker, obviously I have a gambling problem also, right? And so I have that risk and reward profile. But then the other thing he did that I thought I was pretty inspired by was he bet on somebody who he believed in, which was Ev Williams when he started what became Twitter. And then when he saw that it was a winner, he went all in in a way that most people do not. Most people would've let their $25K check sit and been really excited and fingers crossed, I hope Twitter becomes a thing. He quit his job, basically started showing up at the office every day being like, how are we going to make this thing grow? I want this thing to grow. He went and personally was fundraising for the company, even though he wasn't even a part of the company. But he was out there pitching investors to invest in Twitter, and then he ended up buying billions of dollars of Twitter stock before it went IPO and was their, I think, first or second largest shareholder at IPO and made billions of dollars off of his Twitter holdings because he knew when you have a winner, you got to go all in. So what I've seen is in technology, the winners get really, really big. And so you kind of want to like play small bets initially and then follow on really hard. And like when you see something that actually works, be really bold in the way you approach it. And like, hey, if you strike out, I kind of just think about it like this. I have a lot of faith in my skills. Even if I went to zero today, I think in 3 years I'd be right back where I want to be, right back where I am today. So like, I don't feel like there's a huge risk in terms of that. But anyways, that's a little bit off topic for one question.
All right, let's do the next one, which was a question that I actually have for you as well. Update us on your rolling fund. Is it what you expected? Are you more or less bullish on it?
It is not what I expected in that I didn't really think too much about it before I started it, to be honest, which is, you know, I'm kind of impulsive. I was just like, oh yeah, that sounds like a cool idea, let me try it and see what happens. But I thought, okay, I already angel invested, this is just going to be that with some bigger checks, or, you know, do a few more deals. Um, but I would say now that I have to deploy $1 million a quarter, I actually have to carve out more time. I have to like consciously go and invest in more companies. So it's more work than I thought initially. But I brought on Romain, I brought on Zach, Ben helps me with it. And so they do a lot of the heavy lifting. Like, for this year's YC batch, Zach himself referred in 22 of the companies. He was the number one, I think, referrer into YC. So he knew a bunch of the YC companies before they even got in. We looked at those deals. And then Ramin basically and him went through every single deal in an Airtable, vetted them, made a list of the interesting ones, did meetings with them, and then brought the most interesting 7 to me and were like, hey, we think these are the ones to do. And so I've been able to handle the additional— so it's more work than I thought, but I found really good people, so that's helped.
Who's this guy, Zach?
Zach is a young engineer. He was a YC founder himself. That company didn't work out. He currently, so I met him because he listens to the pod or I don't know how he reached out, but he was like, hey, I heard you were thinking about Rolling Fund. I'd love to help. I just want to see a bunch of startups and help a bunch of founders while I think of my next thing. And it just turns out he's just like super well connected with the like young founder community. And so because of that, he's like referred a huge number of people into YC and into On Deck. And so he's got this really great network and he's like able to like see things earlier than most. And so I brought him into the fund and gave him a chance to, hey, now you can have some upside in this thing.
That's badass. And then are you more bullish or less?
More? Yeah, like the same. I don't know. I have a friend, we have a mutual friend, Sully, who he wanted to get involved in a business of mine. And he goes, he texted me something because I was like, I was like, kind of, I don't know, is this I don't want to give up equity, but like, you know, um, I think you're worth it. Uh, yeah, so, so basically he goes, um, he goes, look, uh, if I try, I win. And with this, I'll try. And, uh, and so I just loved it. I was like, I've just got to learn a lot from this guy's philosophy in business. He just has zero of the doubt and fear gene. I think that's through experience.
You would know more than I am, but this guy's Suli. It's him and his brother. I, I'm not that close with them. I'm friendly with them. I'm friends with them, but I'm not that close. Like, I— if you told me that they were worth over $150 million, I wouldn't be surprised. And they still act like they're poor in kind of a funny way, which I enjoy. And they're—
they invest in— humble, and they're like super hardworking still. Yeah.
And they invest in everything. So these guys are interesting. They're two brothers.
Yeah. And Suli's the same way, actually. When I first met him, I met him at— you, you hosted the HustleCon dinner at my office. This is how crazy the world works. This is like one of those You can't connect the dots looking forward. You can only connect them when you look back. You reached, you cold emailed me saying, hey, I wanna host a dinner at your office. I didn't know who the hell you were, but you made a strong pitch. You said, I'm gonna have all my speakers for my conference there. You can, you can ming, you know, meet all of them. I was like, all right, fair deal. You can use my office. At that dinner, I meet Suli. Suli's now my best friend. We've done tons of deals together. You know, like that wouldn't have happened if I hadn't said yes to something that was kind of a random thing.
That's funny.
At that dinner, I was like, dude, this guy's amazing. I've never heard this guy's name before. Why don't people in Silicon Valley know this guy? So I started Googling him. I find this story that back in the day he had this company that was building Facebook apps and he sold it for not a ton of money, but good for any normal person.
Like $2 million or $3 million or something like that.
Between $1 and $3 million is kind of what it sounded like. And then what did he do with the money? He had been building on the Facebook app platform, so he had been seeing that his app was growing really quickly and his app wasn't a great business. It was like You know, those like silly Facebook apps. But he's like, Facebook is not silly. So he basically took a bunch of that money and just— he was like Chris Sacca. He aggressively started buying up Facebook stock back then before it was public. And then he did. And then he went to, you know, in Florida and he bought a bunch of real estate. And I just thought, wow, this guy's really like conducting himself. At that time, I was just kind of like, I thought of myself as an entrepreneur, but I acted more like an employee. Like I wasn't playing the game to win. I was playing with these like invisible handcuffs on me. Like, I saw these companies that were awesome. I didn't even go try to invest in them. And like, when I saw that this guy, when he knew something was good, he was like, how do I take all the money I have and put it into this Facebook thing? I believe in this. And simultaneously, I'm going to build my next business now, you know, right away. And so I just really admired him. And I thought that that was a great example to follow.
He's a hustler and I like him a lot too. Let's go to the next question, which is this. We'll answer this one quickly. What do you not talk about, or do we not have the chance to talk about because it's low priority or off topic, that you wish you could talk about? For me, it would be, I love talking about UFC. I'm a big fitness guy, so I love sports. I love weightlifting and I like running, and I wish we could talk more about like fitness stuff, but I don't think it's on topic, and I'm not an expert on it.
Yeah. If I could do a podcast shooting the shit about basketball or UFC, that'd be awesome. But nobody cares what I think about the NBA or the UFC, really. So that's one. And the other one I think would just be like, I do kind of bring this in sometimes, but it takes up a lot more of my life than I let show here on the pod, which is like, on the pod, I'm just talking about a bunch of different business ideas, ways to make money. In reality, I'm not just doing that all day. What I spend a lot more time thinking about all day is my mindset. So What is my life operating philosophy as I go about my day to be like the happiest and best person I can be? And it's just kind of cheesy to talk about and like no one kind of gives a shit, but like I give a shit a lot about it and I care a lot about it and I think a lot about it, but I don't really talk a lot about it. I do.
I think about that stuff too. Yeah, but it is silly to talk about and it could be embarrassing, particularly if you're still working through stuff, right?
It's cool to talk about that. I found when you're in a small group of people or you're in front of, if you're in person with some people, because you can get a sense for Do they give a shit about this or not?
Right.
And it's also like kind of personal. On a podcast, you might record that thing for an hour and you're like, I have no idea if even one person is going to like want to hear that. And maybe they'll just all turn it off.
What's— you guys are awesome at coming up with incredible ideas, knowing how to execute them. What would it take for one of you to pull out of Twitch? Or I guess they meant, in my case, HubSpot now, and pursue it full force? That's actually a great question. And I have a— I think is a good answer.
Um, go for it.
Which it, which is, um, first of all, starting a company is really hard and I've like joked, but I'm kind of serious. I don't know if I'm ever going to do it again. Maybe, maybe not. Right. Or at least like, who knows what I'm going to do? You know, I've thought it would be cool just to like retire and not work. Uh, and we'll see if that's cool, uh, or not. I don't know. But, um, I think that the answer far, or the answer should be, but it is not enough. Of I just think this is cool. So like, why are you doing this? Because it's fucking cool. And I think that when I find something where it's going to be like, oh, this is badass. This is cool. Like, there's not like for me, there's often not like a mission where it's like, let's save the world or let's, it's like, ah, it's just kind of badass. It's just awesome. Like there's not, there is no logic other than this is, this is, this is cool to me. And when I found a few things that fit that, but I'm still on a mission with HubSpot and I want to make it great. And after that, then I'll pursue the next one I get. I don't like doing what I think, Sean, you do this a little bit and a lot of people do it. I don't like starting lots of little stuff. I prefer to dedicate my life to something. Um, and I'm very cautious about what I'm willing to do that with because you probably can only do that 3 to 4 times in your life. And so, um, there's a few things, but I'm not, I'm not finished with this chapter yet. And that's why I haven't done it.
Yeah, that's a great answer. Um, I, uh, similarly, I basically was like, all right, well, what's this chapter of my life about? And, uh, So when we got acquired, I was like, well, I want them to feel like glad that they did this acquisition. You know what I mean? I want them to be like, yeah, that was worth it. And for myself also, I was like, well, cool, this is like a transition. Let me try this new thing. Let me work at a big company. Never done that before. Let me have this big cushy salary type of thing. Never had that before. I was kind of just eating shit, doing my own startup, sleeping on kind of an air mattress before. And so So basically I was like, all right, if my 20s were about starting my own company and just trying to figure out how to be an entrepreneur, what are my 30s going to be about? And I've decided it was two things. I said I want to live a great life with my family. So popped out two kids in the last 18 months. And so that's actually like my project is being a dad and having kids and spending time and just being there for that and not trying to be like, oh, I must Because like you said, now I know what it takes to start a company. I know how all-consuming it is. So got to choose wisely. The second thing with choosing wisely is my 30s are about building a family, and then it's building a project I don't want to sell, which is basically like—
I totally agree.
How do I build my next thing? Same thing you said, that this is something I want to do. I'm not doing it because it's the best business idea or it's the hot opportunity or whatever. But the thing that I just want to keep doing that I don't want to get rid of, I don't want to sell it. I just want to build it and let it compound for 30, 40 years. And I love doing it, and it's the thing I'm uniquely good at doing. And I thought, okay, maybe I'll dabble in some different things to figure out what that is. And I feel like I found it, which is ironic. I found it where I wasn't looking. I started this podcast for a different reason, but what I realized was, oh, I really like this thing where I can be kind of like perpetually curious. Like, I could just be curious about the world. I can learn a bunch of shit, and then I just share what I'm learning, and I'm kind of like a teacher. And through the podcast, the email newsletter, through experiments like All Access Pass, or I'm going to launch some courses in the future, like I might launch a school. Basically, I want to do things like that. Something that lets me just be really, really curious and learn a bunch of things and try a bunch of things and then share as I go. Because that's what I would do if I— let's just say if work couldn't pay you money, how would you spend your time? That's how I would spend it. So might as well just do that as my work. And so that's what I think I'll do next, which won't look like a traditional startup or company.
And I agree with that. I want to do something that I never want to sell. So I'm in the same boat. The question is directed towards you, but I'll give you my answer really quick, which is, Sean, how do you balance side hustles while performing at Twitch? My answer to that, and I've said it before, is I don't balance. I don't do anything on the side. And frankly, I have no idea how you do it. Our good friend Ramon is able to do it really well. I get some people can do it. I personally can't do it and I don't even try. And I'm not ashamed about that.
Yeah. Yeah. There's different ways to like kind of organize your time. Like you see this from Elon Musk or Jack Dorsey running two multi-billion dollar public companies at once as CEO, right? Like kind of a crazy thing that kind of seemed impossible before. And I would say I do it two ways. One is I throw more hours at it. So I don't take weekends off. I work 7 days a week. I don't work all day, all 7 days a week, but my weekend is just like my weekday. They're the same construction. So all of a sudden I got an extra 16 hours on the weekend where I can do things. Same thing at night. I don't watch a bunch of TV. I stopped watching NBA games, stuff like that. I basically was like, look, I could cut that out, and that's 2 hours a night that instead I can create content, right? Or when I do the podcast, everybody else, back when we started this, everybody would go down to the cafeteria at Twitch for lunch. I would walk across the street. The studio was— your office was literally like 50 steps away from Twitch. I would walk 50 steps away, go to the Hustle office. We would record from 12 to 1. Everybody else is eating lunch. I'm recording a podcast. Cool. I'll eat lunch on my desk. Like later, doesn't matter, right? So there's these little pockets of time you can unlock. That's the first bit. Second bit is hiring. I bring on people. So when I say I'm doing X, it's rarely just me doing X. It's like Ben or Zach or Romaine or Chris, or I have a whole bunch of people that I say, hey, I'm doing this interesting project, who wants to do it with me? And they're like, I find great people who want to do interesting things together. And I say, cool, what's in it for you? Do you want money? Do you want learning? Do you want You don't want to build your network? What do you want out of this? I'll make sure you get it. And they let me, like I said, be in two places at once because I could be doing this and they could be doing that.
What's your burn on all that? Like, because whenever I hear you say you got all these people, I'm like, damn, yeah, that must be a lot, uh, monthly.
Yeah, my burn is expensive, but the things now bring in money, so it's, it's okay. It offsets it.
But like, uh, but the angel investing doesn't bring in money, and that's angel investing.
I don't pay salaries. It's only carry, so it's splitting the upside. So they have, they, they get it. They, I took some of my, my 20% carry and I took it down and let them have more carry. So, um, which, you know, for them is fine because they make money doing other things. So they're like, cool, this will pay off in 5 years. That's great. And I get to like learn a bunch about investing. I get to put together a portfolio. So if I want to go get a job doing this, or I want to start my own fund, I'll have a track record to point at and say, no, I, I did these investments before. I've been doing this for years. So that's kind of like what's in it for them. Um, so I do have a, you know, significant burn. I would say it's like $200,000 to $300,000 a year of like people cost to do these things. My goal is for them to break even. Um, but if not, like, that's what money is for. Money is to be invested in things that will grow. And so I kind of like just look at it like an investment and, uh, it's worked out so far where the side hustles more than pay for the money I put in. Um, now the last thing is basically an acknowledgement. And I talked, I was pretty transparent with the people at Twitch, which was like, look, I operate not on a 9 to 5, like strict schedule. Like, cool, I'm just going to punch the clock for 40 hours a week. No, no, no. I'm here to do this mission. You want this job done? Great. I'm going to get that job done. Here's the trade. I can make sure this job gets done. You don't ask me how and when and where and why and how, you know, like all the technical questions. Not in such a confrontational way, but it's an understood agreement. They know what I do. I'm very open about, hey, I have a podcast, I have a newsletter. The CEO of Twitch subscribes to the newsletter and will DM me about it sometimes. I'm not hiding any of these things. They know I do these things. They know they take some time, but they're okay with that trade because I deliver the goods in my projects. And so my trainer told me this one day because I told him, I said, I'm feeling a little bit guilty. I really like these people. I don't want them to feel like I'm shortchanging them. He goes, well, do you deliver the goods? I was like, well, yeah, I perform. They get the results they want. He said, okay, well, you're that dude. And I was like, what do you mean? He's like, they don't pay you to sit in your chair for certain hours. They pay you to deliver the results. And so just make sure you deliver the results. And if you're delivering the results in less time, that's because you're that dude. Maybe not everybody could do that, but you could do that. And I was like, oh man, what a pep talk., you know, made me feel good about something that I was feeling, you know, uncertain about or uneasy about before.
And you're on paternity leave now, right? Yeah. So that helps too.
Yeah, exactly. And that's, you know, like big companies understand, like, look, you, if you have a kid, my first kid, I only took 10 days off, which I really regret. I should have, uh, I should have took the whole leave. And so this time I decided I'm gonna make sure I take time off. And this time my family actually really needs me there. Whereas the first time I was like, I don't know what the hell I'm going to do here. My wife's kind of got it under control. Let me go back to work. And so this time I kind of realized that the idea of like, oh, this project is so important, and like, if I take this time off, then blah, blah, blah. Let me do it. I'll take time off later. And later never came. And that was a big lesson for me. Like, don't put important things off till later. Do them now.
Who's the worst person? This is such an interesting question. Claybert. I bet you I know who that is. Who's the worst person you admire?
Do you have one for this?
That's a good question. Yeah. Well, like I, it's a great question and it's, you can get in trouble answering this one. I'm going to tiptoe a little bit around it because it's just weird, but I actually love learning about dictators. I like, I read a ton about dictators. There's actually a podcast called Dictators. So like, I like learning about Benito Mussolini. I've read a lot about Hitler. I've read a lot about Fidel Castro. Who else?
So I think I got in trouble with this before because I remember I was in school and I took a history class and the question I asked the teacher was, look, this sounds so messed up what was going on back then. This sounds totally screwed up. Like, how did this guy come to power? And he explained like, well, here, first you have to understand the state of Germany at the time, blah, blah, blah. He goes, the other thing was that, like, honestly, he, I forgot who Hitler's second in command is, but he's like kind of like a famous guy for like his, almost like his persuasion prowess, like his marketing prowess.
Yeah. Uh, Joseph, uh, uh, yes. He's like the head of propaganda. He made movies.
What's his name?
I forget his name.
He's kind of a famous guy. He's like his number 2 guy. He's the head of propaganda. Exactly. And they did very simple things. Like everybody else was putting out, like, I forgot, like their flyers when they were running for whatever president, whatever their equivalent of president was, was like, all in color. So he did everything in black and white to stand out. Or if everyone's black and white, he did color. Like, he just did a whole bunch of things. I found it really interesting. Like, oh yeah, Goebbels, Dr. Goebbels. Joseph.
Yeah, yeah, Joseph Goebbels. Yeah, yeah, yeah, yeah.
So they had movies made and they used entertainment to kind of like get their message across, get the story across. They had like a whole bunch of like, they distilled down their philosophy into these like really catchy nuggets. And so there's all these things that I thought, wow, that's like, If you just abstract the good and evil away, the skill of accomplishing a very hard thing, which is like getting millions of people to follow you, there's a lot to be learned from that. And I kind of was like, oh, that's really cool. And people were like, dude, you said Hitler's cool. Like, you're, you're out. Yeah.
And that's, that's the point I'm getting at, which is like, it's so fascinating that someone can convince, in my opinion, like a lot of dictators, I'm like, man, if they like, just like moved that early on, like clicked it a few notches to the left, and then that trajectory would have like put them in a totally different atmosphere. I'm like, man, it like, it's, but it is fascinating how someone can come from nothing and just create something, whether it's an idea, a business, a piece of art, whatever. Like, I love that like idea of manifesting. And even though it's horrible and the worst thing on earth, and I wish it never existed, I always have been fascinated by like a guy like Che Guevara or someone who like Was this like, or what's his name? Benito Mussolini, who I just read about, like this was an, like a, supposed to be a poor kid. And somehow he convinced all these people, these to do all this horrible, horrible stuff. And that like, to me is fascinating how he just bent the world around him. And like, that's just crazy that, hey, people buy into that stuff. And it's crazy that someone that he had the courage to do that, which sounds like I'm glamorizing these people. I'm not at all, but hopefully you guys understand the nuance here and why it's kind of intriguing.
Yeah. Uh, two things. One, um, when I met, I've talked a little bit about my friend Vishal, the guy who's kind of like a young guy who I'm like, this guy's definitely going to be a billionaire. And he's also kind of like totally hellbent on becoming a billionaire. And he lets every part of his other life go. Like what we were talking about earlier where I was like, well, on the podcast, I talked a lot about business and money, but like in my real life, I'm doing, I'm really actually more passionate about these other things I spend more time on. He's the opposite. Whatever he talks about here, he's 10 times more obsessed with it outside of this. And I love him for that. And I remember when I met him, he was like, send me this documentary about this warlord in Africa who just like the absolute gangster shit this guy did. He's like, oh, I love this movie. I love this guy. I was like, oh, it's kind of like heinous crimes. And he is like, oh no, it's crazy. And he told me this story about this guy who became the emperor of China. And he started off as an orphan servant and then ended up by the end of his lifetime as the emperor of China. I forgot his name, but one of the ancient emperors of China started off as an orphan boy with not a dollar to his name and then ruled.
I mean, it sounds like Genghis Khan or something.
Yeah. And he was like, and not just got there. It's not just a hero story. He also slayed his enemies and enslaved people, or I don't know what he did, but it wasn't all just underdog. It wasn't just David and Goliath., and he told me that story and I was like, you're a maniac. But, um, you know, I actually would love to invest in you because that's the kind of like maniac you want being a founder of these companies is like somebody who is wired a little bit differently. And, uh, so I remember hearing that, but anyways, the phrase you say that's like every great man is also a bad man. Yeah, that's kind of true. Everybody, I like my favorite comedian is Louis C.K., who I believe is currently canceled for, you know, like doing something gross in front of a bunch of women or whatever. And I don't think that's cool, but I love Louis C.K. And I still love Louis C.K. And I think he's awesome as a comedian. I didn't say he's an awesome character, awesome human being, and I want to be like him. No, I think he's an amazing comedian and I love his comedy. Conor McGregor. I had a poster behind me of him, painting that I had made of him behind me for half these podcasts. He's been accused of sexual assault. People say he's on drugs and he's kind of an asshole and other things too. He's an amazing fighter and I love his drive of how he went from a plumber on welfare to the wealthiest fighter of all time. And he said the whole time from the very beginning, that's what it's going to be. He called it. And there's videos of him when he's alone in his bedroom, not even a professional yet. And he says, I'm going to be the greatest and here's what I'm going to do. I'm going to do X, Y, Z. And he did it all. I admire that, but I also think he does a bunch of scumbag shit and like, I'm okay with that trade, you know?
So there's like a bunch of people that are like that. I was driving, me and Sarah one time were driving by Chick-fil-A and we were like, I want to get that. Do you want that? And she was like, yeah, I want that so bad. And we were, and she was like, but do we want to support them? Uh, this was right when they like did some stuff, uh, anti-gay stuff.
Anti-gay marriage. Yeah.
And, uh, We were like, well, my taste buds don't really know if you're homophobic, so I think we'd be— it's okay. I think we could like the chicken. But also, or it was something, maybe we were at some place and they had the chicken there, and I was like, I don't think my taste buds could tell if you're homophobic or not, so we could probably eat it. Um, all right, let's answer a video question. Lately I've been thinking about trying to hire my friends as operators of sorts and I'm just worried about like damaging that relationship. Like, I think it's an awesome idea of being able to choose who I work with. I'm just concerned that all that friendship could go away when there's something as important as like business and money involved. I have a pretty strong opinion on that, which is no, I think you actually shouldn't. In most cases, don't do it. In some cases it makes sense,, but in most cases I actually think it's a bad idea. And I also have myself failed at doing this a little bit, but I actually don't think you should be friends with your coworker or your friends with your employees. If you're a manager, you shouldn't be friends with your employees. If you're a business owner or CEO, I actually don't think— I think you should be friendly, but I think you should be really careful about being friends with your employees. Um, and so my opinion is no. I also think that like, You probably disagree, Sean, or maybe you do, but like, even if they're, if you're worth your coworkers and anytime in the evening and alcohol shows up, I think you should leave. I don't even think you should be in the same room. Um, so I'm pretty strict about that, although I am friends with a lot of my coworkers, so I don't exactly follow all this, but I think that I might regret some of that.
We're opposites on this. So, uh, you know, it's funny. I always try to be friends with my employees and I feel like they don't want to be friends with me. So I'm like, yeah, I'm trying to be friends with them. And then I'm like, oh, that's weird. You guys all got together that Saturday? And like, oh yeah, I was just at home. Could have come over.
Well, what's funny is when you start a business and you work a lot, you don't really have that many friends. I'm friends with you and Jack and Ramon and like 4— I've got like 4 friends. But my coworkers are like— I'm like, will you guys be my friends? I'm with you all the time. And I don't get invited to anything either.
Yeah. So I realized pretty quickly, oh, they don't want me around. And I was like, but it's weird. I'm such a good guy. And so anyways, that part didn't work. Not because I didn't intentionally try not to be friends with them, they just didn't be friends with me back. That's okay. The main thing for me on the hiring side is I would say hire your competent friends. So my very first business I started, I started with two of my best buddies from college and we were just like, yeah, we're going to do this. There's no CEO, there's no hierarchy here. We'll all just make decisions together. We'll all split the equity perfectly equally. We didn't really put too much thought into it because we were just like 21-year-old kids, didn't really know much about anything. And fast forward a year later, we had to have a very uncomfortable conversation with one of the guys, which was like, hey dude, I feel like you're not pulling your weight. And he was trying, but we were just like, you're kind of just doing this part. And we feel like we're doing these other 8 parts. And in retrospect, I don't even know if that was really true, but it definitely was an uncomfortable conversation and I could see the downside of it. But what I would say is the saving grace for me has always been I only have hired my competent friends. And competent friends do two things. One is they perform. So you don't have this— you're not just hiring a buddy because you're your buddy. You're hiring this person because they're good, but you only know them because they're your buddy. The second thing is they are reasonable and they will understand if you're really clear up front about, look, here's the dynamic. We're buddies, but sometimes I'm going to have to tell you if I feel like the job's not getting done. And I actually, I want you to tell me too, if you think that's true. Are we okay if it's going to be kind of uncomfortable? We're not just going to be able to just shoot the shit. We got to also have these two modes that we can operate in. And I want to make sure you're on board with that. So I think with a little bit of good communication up front, you can get the big benefit, which is it's way more fun to do stuff with friends. Companies are hard. They take a long time. It's like a really long road trip and you want to be in the car with people you really like. And so whether those were new people who you just happen to enjoy, great, or they're people you already enjoyed who you invite into the car because they're your buddy and you want to do this company with them. I think when it works, when you do it with your friends, it's the best. And when it doesn't work, it's even worse than if they were not your friends. So you got to take the good with the bad. We had a podcast with this guy on the feed called Mike Brown. You introduced me to him. I met him at your office.
Yeah, he's cool as shit.
He had a successful business, then he brought both of his brothers on board. And I was like, why did you do that? Most people say, don't do business with family. It gets messy. He's like, these are my brothers. I love these guys. I want to see them every day. I want to hang out with them. I want to win together. I want us all to win. He's like, I feel blessed that I got to set this up where I get to do business with my best friends. And I was like, well, when you say it like that, what the hell am I thinking about? That's obvious. That sounds great. And so I think there are downsides, but I'm of the mindset of if you pick competent people, you won't regret it.
All right, we'll do a couple more fast questions. Someone asked who could squat more weight. I think me, Sean.
That's definitely you. I have Osgood-Schlatter's in my knees. If you have it, you know. If you don't have it, you don't know. But because of that, I don't squat. I can't squat. I never squatted. My whole life because of that issue.
Okay, this is a deep one. It's cool. We'll answer it. What are your biggest insecurities? Both. What are the biggest insecurities both of you struggle with? I'll say I'll go first. Sometimes I'm— I get incredibly insecure that anything I make won't be good enough because I move too fast and I just do surface-level shit and I don't treat it like a craft, like a craftsman enough. And I don't like think things through. Um, I get pretty self-conscious when I meet really smart people who I meet a ton of them through this job. I'm like, oh my God, this person's IQ is just like, they are so much smarter than me. I just cannot keep up. Like, 'cause, uh, so I, I, I'm insecure about that. I'm insecure, um, that I, um, like I didn't go to Stanford or like a fancy school. And when I meet people in the in-crowd, like when we meet guys like Andrew Chen who, who, who works at Andreessen Horowitz, I'm like, dude, No, like I kind of want to be in the in crowd, but like, I don't want to work that hard to do it. And I just don't care that much, but I wish I did. I feel a little insecure about that. Um, um, and I feel, uh, I get insecure because I'm pretty loud and that sometimes makes people not take me as seriously as I think they should. So those are mine.
Those are really good ones. And I think very relatable, probably for most people. Mine, I would say, I don't even know if it's insecurity as much as like, because when people say insecurity, it's usually like, what's something you worry about, but it's not really true, but you kind of worry too much about it. I think mine like is true. So it's more like, here's your weakness. Here's your weakness or your flaw, I would say. And something I kind of worry about, which is I don't really filter myself. And so I just talk a lot and I don't really think about it before I do it. I don't really think, I don't even filter myself with actions. Like I said, with the rolling file, I was like, oh, that's cool, let's do it. Can we do it today? Let's just do it now. I don't want to think things through. And so I would say the fear I have and the insecurity I have is around actually hurting people's feelings. Sometimes I could say stuff that's inconsiderate or hurtful in some way, or you know, too opinionated and nobody asked for your fucking opinion type of thing. So I'm kind of conscious of that. Like, I would say I'm pretty self-conscious about that. That's the word, not insecure. I'm self-conscious that, wow, I do that and I don't really like that part of me that, like, I will say things and do things that I don't really think about how others will feel about it. And also, like, when I meet people like our friend Ramon, who's so considerate, I just feel so inconsiderate in comparison. And I'm like, oh, I want to be that way. But man, I'm like the opposite.
And like, you know, I'm like a, I'm like a knuckle dragger. I'm just like, yeah, a Neanderthal.
So I feel really bad about that. And then I would say like the other minor insecurity is like, am I just wasting my talents? Like, so when I meet people who are doing really amazing things, like Scott Harrison. He's been on a 15-year mission to bring clean drinking water to the world. I went with him to Africa, and we went to a town where they had installed one of the water wells. And literally, the town was like, it was like a parade that Scott was here. They literally thought this guy was Jesus. And he kind of looked like Jesus in the moment. I thought he was Jesus in the moment. And he's totally humble. He hated that they were celebrating him. He was there not for that reason, but That's the reality of the impact of his work, is he literally changes the lives of entire towns, essentially, in Africa. And so then when I see that, I'm like, what am I wasting my— do I need to do this silly e-commerce thing? Do I need to do this newsletter? Who gives a shit? And so sometimes I feel really small about the way I decided to use my time and my talents. Completely agree with that compared to other people.
Last question. Uh, when are you guys going to do— since COVID is pretty much in the past, when is the next meetup going to happen? I'm actually doing a meet— so I'm driving to St. Louis to spend a week with my family there, and I'm stopping in Oklahoma City because that was just like the middle ground. And I tweeted out, so I've got like 30 or 40 or 50 people, I forget how many people RSVP'd, for a breakfast in Oklahoma City. And if you're down, Sean, although you just had a baby, so, uh, imagine we're gonna have to wait a little while. I would totally be down of doing like a 2-week tour or something where we go from place to place a place. I don't know if we could drive. I don't know what you'd want to do, but I'm totally down for like a 2-week thing.
Yes, totally agree. I think like if we just said, all right, this fall we're going to go on tour, we're going to go to these 7 cities, 7 cities in 7 days or 7 cities in 10 days or something like that, and we just like set up the events. I would love to do that. I think that would be amazing.
Well, we just, we just hired a community manager. Her name's April. Um, and she set this event up for me. I just said, hey, I'm going to show up in Oklahoma City. Can you get like Can you book me a hotel and set up like an Eventbrite and I'll tweet it out? And well, we can have her do that and help us do that.
By the way, you do something really great that I think you should tell people, which is when you hosted events, but you make the themes great. So like you used to do this thing called Pizza and Forties. So can you give me— I don't even know what other ones you've done, but like tell the people of some of the different events you've done because I think it's really smart. When you set those events up, people want to come and they behave differently because of the theme of how you set up. Because I've been to a lot of Silicon Valley networking events, they're boring as shit. You don't want to go. And when people go, they're all like surface level, level, like they, you know, it's not a fun place to be. They don't let their guard down. Your events are very different. So can you— what are some of the different themes you've come up with? And like, do you have a theory on why that works?
No, I don't have a theory. I just think it's fun. I do it for the, what I said earlier in the episode. I, it just, 'cause it's cool. That's the only reason why. So I do the Anti-MBA. That's a book club where we get an expert to come in and discuss the book's topic. I've done, this sounds douchey to say, but like I don't even drink, so this is why it's funny, but we have this thing called Pizza and 40s. So the speaker gets a 40-ounce beer 'cause a 40-ounce beer takes like an hour to drink. And as, and so We only would have pizza because we were poor and that's all we could afford. And we would give the speaker a 40-ounce beer. They've got to drink the beer. And when the beer is done, the talk's done and the answers get a little bit wilder as they get deeper into the beer. We did 2X, which was focused on women telling their story. It stands for 2X chromosomes. We had like— did you go to the one that we had in the marina?
No.
What's that? We used to do 2X at this thing called Palace of Fine Arts, and we had like literally 2,000 women there. In San Francisco. It probably was like the largest contingency of like, uh, uh, tech women probably in the world or in the country. It was kind of interesting. Um, so we did that. What else did we do? HustleCon, ConCon, uh, which is ConCon is the startup that's the content conference. I thought ConCon was a funny name. What else? Uh, anything else?
Have you— I feel like you've done some breakfast thing before. Have you done a breakfast thing?
Is that something else? Rise and Grind? Yeah, we did Rise and Grind. Um, which was, we would talk about different stuff in the morning over, and it was like a grind, like coffee, like coffee, but also like work hard grind.
You're good at this. You're good at coming up with kind of a catchy name and a catchy theme for people to get behind. Uh, and the vibe is very different. So I think that's, if somebody's doing it, like that doesn't take any extra money. It just takes like a little creativity and like you've made your thing better and cooler, more fun for you to do, more fun for people to come to, more fun for speakers to attend because it's different. Than the average thing.
So long story short, uh, maybe late summer if you're down.
Yeah, I'm definitely down.
All right, great. That's it. We'll do it.
I feel like I can rule the world. I know I could be what I want to.
I put my all in it like no days off.
On the road, let's travel, never looking back.