#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 I'm not that close with them. I'm friendly with him. I'm friends with them, but I'm not that close. Like I if you told me that they were worth over 150 million dollars, I wouldn't be surprised and they still act like they're poor in a in kind of a funny way, which I enjoy. And they're They're not going to be able to do it. Super hard things. And they invest in everything. I feel like I can rule the world, I know I can be what I want to

I put my law in it like my day song. On the road less travel, never looking back. Today we're gonna answer a bunch of questions. Uh but Did you see Trunk's tweet about the guy Selling the car. No. What is it?

Trunk tweeted out this video that he found from probably the nineties or Probably from the two thousands, early two thousands. And it's a guy uh 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. 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 uh about the tweet or about the video based off of his tweet. It was just funny. It

Do you see half a million views now, or like he tweeted something that already had half a million views? No, it did now. Oh wow. Trunk is a master of uh finding great content. That guy is really good. I have this like apprentice who's working with me, Chris, for uh content. He's been the redhead guy?

Yeah. Yeah, he's like kinda like shadowing me and he helps me produce my content and and he's learning as he goes. And um I told him I was like, you know, success is being trunk. So like that's the level, that's the top bar.

Um That's that's what you need to measure against. Here's five examples of like awesome things he's done. And so he called Trunk and he was like, What's your secret? What's your what's your process, basically? And Trunk was like, Oh, you know, like I kinda browse the internet a lot and you know, there's no way you can you know, it's like a 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 native uh intuitively. He's a machine. One time I called him at eleven o'clock his time. He's in Vancouver and he was at the park playing with his son.

And I was like, Trunk, like, I'm not trying to like get on you'cause 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 five AM and I already wrote Tomorrow's email already. I was like, all right, sounds good. Okay. So I didn't see this video. Is is it worth talking about, given that I didn't see it or what? It's too long to go through. Okay, people and myself, let's go to Twitter after this and let's go to Trong T fan, I think is his his uh handle and go look at his thing. And he the funniest thing that he's done lately is he owns onlyfans.com. Dude, that slayed me. It was so funny. So he has only fans, but he spells fans 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. Yeah. For some reason it's funnier than the when I think that he came up with that of brands. Yeah, no, we don't like it so much. Stupid ass idea. All right. Today we're gonna answer questions. I uh we got

Uh, it looks like we got like six pages of text questions, so like dozens and dozens of qu text questions. And then we got uh 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 Volke asks, What are you both personally investing in right now? By the way, do you know Johnny Volk? Do you know who this is?

He I talked to him on Twitter and he's Joe Spiser's buddy. He lives out here in the Bay Area. He lives like I don't know, fifteen minutes away from me. He Super successful e commerce guy, been in ecom for ten years, sold his company recently I don't know, a month ago or something for tens of tens of millions of dollars and Is he's a a big investor in my rolling fund and several other rolling funds and

Uh 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 interest 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 fifty thousand dollars.

Uh the 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 five hundred. So like the total stock market index. Um I have I'm I'm gonna invest around two hundred and fifty to five hundred thousand dollars uh in the next probably eighteen months in startups. Uh I ha I own six figures worth of uh

it into a variety of real estate funds, including Sweaty Startup, Nick Hoover. Um, and then I own um my house. Uh, and I'm in the process of buying multifamily properties. So I would say I have Like if you just broke it out, you're like Percent you know, roughly you're like, okay, seventy percent 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, no, I I I own way more just SP five hundred than I do HubSpot and Airbnb. Um, but I would say that uh ninety percent of my net worth is in the S P five hundred. Yeah. Oh wow, SP five. Okay. So just like low low low cost index fund, basically, Vanguard fund.

Simple stuff. And then my goal is to invest somewhere around one to three percent of my net worth over a period of time into angel investments. Gotcha. Uh, 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 you're not currently buying and like owning real estate at the moment. Uh I'm going I I owe my house, but I'm I I'm gonna I wanna buy sixteen units. I also have

I mean, I'll say like half a million dollars in cash just sitting in a checking account. Um, which I think is too much money. But uh I uh when I bought my car, I I just paid cash out of there. And then I um

I own six figures of uh Bitcoin and Ethereum, of which I owned most of that bitcoin from two thousand and thirteen, and I just bought like seventy five thousand dollars with the Ethereum like a few days ago because you and a few others told me it was interesting. Nice. Uh by the way, we got uh some criticism, constructive criticism, I would say. Which was like oh the last few episodes. uh feel like, you know, rich guys talking about, you know, ways to make a bunch of money, which Um honestly good description for the podcast, but but I I get what the person's saying because they're like a fan and they're like

I that's me raising my hand because I think I basically was like, Oh, this Bitcoin 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 a N F T for like seventy million dollars. So it just sounds like a little bit crazy. Um

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 uh 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 talk about money, but it's like, Well, that's also the theme of the podcast in a way, right? 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 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, because Yeah, and also uh I put this out there in the manifesto when I started this thing, which is I 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 more 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. Um and People try to signal and say, Oh, it doesn't matter and all this stuff. I I know a lot of people that want more money. I 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 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 uh traps the information from others. So that's kind of my my my overall view of it. I 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 Um, 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 or 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 three or four 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 wanna learn about the fitness game. I like learning about the happiness game. How do you be a like 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, you know, a blu belt or a purple belt where I've done something, but I'm no by no means at the end. Anyways, that's a Tangent, but uh to answer John's question Did you wanna say something else about that?

No, I answered. To to answer John's question, uh I'm kinda similar. I I put I tweeted out my like holdings a while back. Maybe I'll do that again. I I need to go back and recalculate. But I tend to hold about Ten percent 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 something in the bank is nice for a rainy day, but it doesn't Earn you more money.

Um, right, the point oh oh one percent I get from Wells Fargo or whoever is not gonna like help me. Um I have A good size stock, you know, basically I would say Beyond that, it's almost like fifty fifty of

Public equities, so stocks. Um and Yeah, crypto right now. And uh I and uh and then angel investing. So I'm angel investing currently through the rolling fund, four 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 twenty percent 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 wanna 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 uh uh uh at opposites with each other. I don't invest in other people's real estate funds right now.

Has your um net worth Or like your total portfolio increase a significant amount since your deal because it seems like you've like weren't very active before and now you are very active and has that helped you? It has increased because uh, you know. The stock 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 eighteen fifty. Amazon stock price today is thirty one hundred. So just while working there, you know, you're gonna get pretty significant gain. And 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 has Bitcoin has done extremely well. Ethereum has done extremely well. So those have like really worked. And then um Kinda like the side hustle money. From

podcast, email, newsletter, stuff like that. um sponsorships, that that sort of thing has been really nice. So that that's that's actually picked up as well where I wasn't doing that before. Um So I'd say yeah, but I would also say Um

What really changed was my attitude. Like I just started acting like a guy who's got a hundred million bucks. For better and for worse. Like I take like bets that are kind of too big for my bankroll sometimes, and that's a risk. And I you know 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, you know Going from A to B, you know, like What if I just knew that I'll get to be

Uh 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. Uh, whereas before I was a little more conservative with how I was investing uh Which is uh a huge difference in our philosophies. I'm way more conservative than you. Way more conservative. Yeah. Um And uh I don't think I was telling a bree you he was like

'Cause I told him I started Angel Investment and he was like, Who do you think's gonna 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. Uh yeah, I think that's true. That's that's definitely true. I I guess like the style of w who you admire sort of dictates what you do you what blueprint you create. So like for example I was really inspired by like Krisaka'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 like was tr day trading in the stock market during the dot com boom. wrote it up to like a ten million dollar like took twenty five thousand and turned it to like tw ten million dollars.

And then went in the whole four million dollars. Like that was like a crazy degenerate gambling run. If you haven't heard me talking about my bets in crypto. And you know, I used to play poker, like I'm obviously have a gambling problem also, right? And so, you know, I have that risk and reward profile. But then the other thing he did that I thought I was pretty inspired by was he, you know, he bet on somebody who 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 like went all in in a way that most people do not. Most people would have let their twenty five K check sit and been really excited and fingers crossed, I hope Twitter becomes a thing. He likes Started quit he quit his job basically started showing up at the office every day being like

How are we gonna 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. uh 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, uh, in the way you approach it and like, hey, if you strike out Like I I kinda just think about it like this. I have a lot of faith in my skills. Even if I went to zero today, I think at three years, I'd be right back where I want to be. We're 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 uh a question that I actually have for you as well. Update us on your rolling front fun. 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 impressive. I was just like, Oh yeah, that sounds like a cool idea. Let me try and see what happens. But um I thought okay, I already angel invested. This is just gonna 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 a million dollars a quarter. I actually have to carve out more time. I have to like consciously go and invest in more companies. So it's uh it's more work than I thought initially, but uh I brought on Romine, I brought on Zach.

Ben helps me with it and so They do a lot of the heavy lifting. Like for this week's this this year's Y C batch. You know, Zack himself Referred in twenty two of the companies. He was the number one I think

refer into Y C So he knew a bunch of the Y C companies before they even got in. We looked at those deals. And then Romine basically and him went through every single deal on an air table. Vetted them, made a list of the interesting ones, did meetings with them, and then brought the like most interesting seven to me, and we're like, Hey.

We think these are the ones to do. And so that that like 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 Y C founder himself. That company didn't work out. He currently uh so so I met him because he listens to the pot, or I don't know what I don't know how he reached out, but he's like, Hey, I heard your thing about rolling fun. 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 uh 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 Y C and into on deck. And uh 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 and uh gave him a chance to, hey, now you can have some upside in this in this thing. That's badass. Um, and then are you more bullish or less? Um More, yeah, like the same. I don't know. I was

Yeah. Uh I have a friend. We have a mutual friend, Sully, who Uh he wanted to get involved in a business of mine. And he goes, he said he texted me something because I was like I was like kinda uh I don't know. Is this I don't want to give up equity, but like, you know.

Um I think you're good. 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 so I just loved it. I was like

I've I've just got to learn a lot from this guy's philosophy and 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 Sully, 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 dollars, I wouldn't be surprised, and they still act like they're poor in a in kind of a funny way, which I enjoy. And they're They're not going to be able to do it. Super hard thing still he is.

Yeah. And they invest in everything. So these guys are interesting. They're two brothers. Yeah. And Sulli'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 a dinner at your office. I didn't know who the 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 have you can mingle uh you know, meet all of them.

I was like, all right, fair deal. Well you can use my office. At that dinner, I meet Sully. Sully'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 them.

I find the story that back in the day He sold his he had this company that was like building Facebook apps and he sold it for not a ton of money, but like, you know, good for any normal person. Like two million or three million dollars or something like that. Between one and three million dollars is kind of what it sounded like. And uh and so And then what did he do with the money? He was like He had been building on the Facebook app platform. So he had been seeing that like 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 plot he was like Chris Saka, he aggressively started buying up Facebook stock back then before it was public. And and then he did and then he went to you know in in Florida and he bought a bunch of real estate. And I just thought Wow, this guy's really like

conducting himself. I I 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 gonna build my next business now, you know, right away. And um and so I just really admired him and I thought that that was a great example. To follow. He's a hustler. Um and I and I like him a lot too. Let's go to the next question, which is

This w we'll answer this one quickly. What Uh do 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. Um 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 uh fitness stuff, but I don't think it's on topic and I'm not an expert on expert on it.

Yeah. Uh if I could do a podcast shooting the shit about basketball, the UFC, that'd be awesome. Uh, but nobody cares what I think about. the NBA or or the UC really. Um So that's one. And the other one I think would just be like I do kinda bring this in sometimes, but like 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 like doing that all day. Um what I spend a lot more time thinking about all day is like But 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 kinda 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 I do agree. I think about that stuff too, yeah. But it's 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.

Uh on a podcast you you you might record that thing for an hour and you're like I have no idea if even one person is gonna like wanna hear that and maybe they'll just all turn it off. What's uh 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 uh 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 gonna do it again. Maybe, maybe not. Right. Or at least like who knows what I'm gonna do. You know, I've thought it'd be cool just to like r retire and not work. Uh and we'll see if that's cool. Uh or not. I don't know.

But Um Whoa. I think that the answer Far Or the answer should be, but it is not enough.

Uh I just think this is cool. So like why are you doing this? 'Cause it's fucking cool. And I think that when I find something where it's gonna 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 Uh, 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 I I found a few things that fit that. But I'm still on a mission with HubSpot and I wanna 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 three to four 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 Like glad that they did this acquisition. You know what I mean? Like I want them to be like, Yeah, that was worth it, you know? And and for myself also I was like Well, cool. This is like a transition. Let me like try this new thing. Let me work at a big company, never done that before.

Let me have this like big cushy salary type of thing. Like never had that before. I was kind of just eating shit, you know, like doing my own my own startup, like sleeping on kind of an air mattress before. And so um So basically I was like all right, if my twenties were about starting my own company and just trying to figure out how to be an entrepreneur. Uh, what are my thirties gonna be about? And I've decided it was two things. I said, I wanna, you know

Uh, live a great life, like with my family. So you know, popped out two kids in the last like eighteen months. And so that That's actually like my project is being a dad and and having kids and Spending time and

Just being there, you know, for that and not trying to I must 'Cause you're like you said, now I know what it takes to start a company. I know how all consuming it is. So Gotta choose wisely. The second thing with choosing wisely is

My thirties 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 wanna do. I'm not doing it because it's the best business idea or it's the hot opportunity or whatever.

But uh what you know, some 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, let it compound for thirty, forty years. And I love doing it and it's the thing I'm uniquely good at doing. And I thought, okay, might maybe I'll dabble in some different things to figure out what that is. And I feel like I've found it, which is like Ironic, I found it where I wasn't looking.

I started this podcast for a different reason. But I 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 uh through the podcast, the email newsletter, through experiments like all access pass. Or I'm gonna launch some courses in the future, like My launch school like Basically I wanna 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 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 of I wanna do something that I never want to sell. Um So I'm in the same boat. Uh 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

Um, I don't ballot. I don't do anything on the side. Um 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 uh I'm not ashamed about that. Yeah.

Yeah, d there's different ways to like kinda organize your time. Like you see this from Elon Musk or Jack Dorsey running two multi-billion dollar public companies that once as CEO, right? Like kind of a crazy thing that Kinda seemed impossible before. And I would say I do it two ways. One is

I throw more hours at it. So like I don't take weekends off. Like I work seven days a week. I don't work All day, all seven days a week. But I

My weekend is just like my weekday. There's they're the same construction. So all of a sudden I got an extra sixteen hours on the weekend. Where I can do things. Same thing at night. Like I don't watch a bunch of like T V. I stopped watching s like, you know NBA games and stuff like that. Like I I basically was like, look, I could cut that out.

And that's two hours a night that instead I can create content, right? Or like when I do the podcast. Everybody else at the 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 r your office was literally like fifty steps away from From Twitch.

I would walk fifty steps away, go to the hustle office, and we would record from twelve to one. Everybody else has eaten lunch, I'm recording a podcast. Cool. I'll eat lunch on my desk 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 Romine 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 like rep 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 the like,'cause whenever I hear you say you got all these people, I'm like, damn, yeah, that must be a lot uh monthly Yes. My burn is expensive 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 uh only carry, so it's splitting the upside.

So they have they they get it they I took some of my my twenty percent 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 five years. That's great. And I get to like learn a bunch about investing. I get to put together a portfolio so if I wanna go get a job doing this or I want to start my own fun. I'll have a track record to point at and say no I

I did these investments before. I've I've been doing this for years. So that's kind of like what's in it for them. Um So I I do have a you know significant burn I would say it's like Two hundred to three hundred thousand dollars a year.

Of like people cost 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. We're we're But

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 nine to five like s strict schedule. Like Cool, I'm just gonna punch the clock for forty hours a week. No no no. Um I'm here to do this mission. You want this job done.

Great. I'm gonna get that job done. Here's the trade. I 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. Uh like not in such a like confrontational way, but like it's an understood agreement. Like they know what I do. I'm not I'm very open about like, hey, I have a podcast, I have a Newsletter like The CEO of Twitch subscribes to the newsletter and like will DM me about it, like sometimes, right? Like 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 Uh. My trainer told me this one day'cause I told him, I said, I'm feeling a little bit guilty like You know I wonder 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? It's like, Well, yeah, like I'm

I perform, like they they get the results they want. So okay, well you're that dude. And I was like, what do you mean? He's like, 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 uh 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. That was Uh, 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 and that's you know, like Big companies understand like look, you

If you have a kid, my my first kid, I only took 10 days off, which I really regret. I should have uh I should have taken the whole leave. And so this time I decided I'm make I'm gonna make sure I take the 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 gonna do here. Uh My wife's kinda got it under control. Let me go back to work.

And so this time I kinda realized That The idea of like oh this project is so important and like If I take this time off then you know, blah blah, let me do it l I'll take time off later. And later never came. And that was a big lesson for me, like

Don't don't put important things off till later. Do them now. Um, w who's the worst person? This is such an interesting question, Claybert. Uh, I bet you I know who that is. Uh Who's the worst person you admire?

Yeah. Do you have one for this? Well, like I it's a great question and it's you can get in trouble e answering this one. Um, I'm gonna tiptoe a little bit around it because it's just weird, but I actually love learning about dictators. Um, I like I read a ton about dictators. There's actually a podcast called Dictators. So like I like learning about Benito Mussolini.

Uh I read a lot about Hitler. I've read a lot about Fidel Castro. Um, who else? Um So I think I got in trouble with this before because I remember I was in sch 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. Because the other thing was that like Honestly, the 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 his marketing prowess. Yeah. Uh Joseph uh Gibb uh yes, he's like the head of propaganda. He he made movies. Exactly. Or I forget his name.

He's the famous guy. He's like his number two 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. Oh yeah, go Goebbels, Dr. Goebbels. Yeah, yeah, yeah. Joseph Goebbels. Yeah, yeah, yeah, yeah, yeah. So so they had movies made and they used entertainment. to kind of like get their message across, get their story across.

They had like Um a whole bunch of like Dis 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 S 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 your options. Yeah, exactly. And that's that's the point I'm getting at, which is like it's so fascinating that someone

Can Convinced in in my opinion, like a lot of dictators, I'm like, Man, if they like Just like move 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, 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 they It never existed. I always have been bat fascinated by like a guy like Che Guerrera or someone who like Was this like Or uh uh what's his name? Uh Benito Mussolini, who I just read about. Like this was a

Like a supposed to be a poor kid and somehow he convinced all these people these to do all this horrible, horrible stuff. Um, and that like to me is fascinating how he just bent the world around Right. And like

That's just crazy that a people buy into that stuff and it's crazy that someone that he had the courage to do that. Uh which sounds like I'm glamorizing these people. I'm not at all. But hopefully You guys understand the nuance here and and 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 Vishall, the guy who's kinda like a young guy who I'm like, This guy's definitely gonna be a billionaire and he's also kind of like Totally hell bent 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 I spend more time on. He's the opposite. Whatever he talks about here, he's ten times more obsessed with it outside of this. And I love him for that. And I remember when I met him, he was he he was like

Send me this documentary about like Just like warlord in Africa who just like Just like the g like the absolute like gang gangster shit this guy did. He's like, Oh I love this movie. I love this guy. I was like, Oh, it's kinda like heemas crimes, you know? And he's like, Oh no, it's crazy. They told me the story about this guy who became the emperor of China. He started off like as a like uh an orphan.

Like servant. And then ended up by the end of his lifetime as the emperor of China. I forgot his name, but like one of the ancient emperors of China was like started off as an orphaned boy with not a dollar to his name and then like ruled. Genghis Khan or something. Yeah, and he was like and it like not just like got there, like it's not just a hero story, like he also like You know, like slayed his enemies and like enslaved people, or I don't know what he did, but like it wasn't all, you know, just like underdog, you know, 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 kinda 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, you know, like And I don't think that's cool, but I love Louis C and I still love Louis CK and like

I think he's awesome. Um As a comedian, I didn't say he's an awesome character, you know, as an awesome human being, and I want to be like him. No, I think he's an amazing comedian and I love his comedy. Um Connor McGregor, I you know I had a poster behind me of him, you know, painting that I had made of him.

behind me for half these podcasts. He's been accused of sexual assault. He's been you know, he people say he's on drugs and he's kind of a uh asshole and like other things too. He's an amazing fighter and I love his drive of how he went from like 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 gonna 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 gonna be the greatest and here's what I'm gonna do. I'm gonna do X Y Z. And he did it all. I admire that. But I also think he's does a bunch of scumbag shit and like I'm okay with that trade, you know. So there's like uh a bunch of people that are like that. I was driving me and Sarah one time were driving by uh Chick fil A and we were like, I wanna get that.

Do you want that? And she was like, Yeah, I want that so bad. And we're and she was like, But do we want to support them? Uh this was right when they like did some stuff uh anti-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 it's okay. I think we could like the chicken, but also or

It 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 they're homophobic or not. So we could probably eat it. Um, all right, let's answer uh 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 being able to choose who I work with. I'm just concerned that all that friendship could uh go away when there's Something as important as like business. And money.

involved. Um I have a pretty strong opinion on that, which is no. Uh 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 a business owner or a 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 co workers and any time 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 co workers, so I don't exactly follow all this, but it uh I think that I'll might regret some of that. We're opposites on this, so uh You know what'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, 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 I Could it come? Yeah. Well, what's funny is like when you like start a business and you work a lot, like you don't really have that many friends. Like I've I'm friends with you and Jack and Ramon and like four I've got like four friends, but my co workers 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 I realized pretty quickly, oh, they don't want me around. Uh and I was like, but it's weird. I'm such a good guy. And so anyways, that that part didn't work, not because I 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 for me on the hiring side is Um

I would say hire your competent friends. So um My very first business I started, I started with two of my best buddies from college. And we were just like, Yeah, we're gonna do this. Ah, we you know, well, and 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 like put too much thought into it'cause we were just like twenty one year old kids. Didn't really know much about anything.

And like Fast forward a year later, we had to have like a very uncomfortable conversation with one of the guys which was like Hey dude, like I feel like You're not pulling your weight. And he was trying, but like we were just like You're kind of just doing this part and like we're we feel like we're doing these other eight 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 I what I would say is like The 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. Um the second thing is They are reasonable and they will underst they will understand if you're really clear up front about like Look, here's the dynamic. Like

We're buddies. But I sometimes I'm gonna have to tell you if I feel like Job's not getting done. And I actually I want you to tell me too if you think that's true. Like, are we okay if it's gonna be kind of uncomfortable? Like We're not just gonna be able to just shoot the shit. Like we gotta also have these two modes that we can operate in. And I wanna make sure like you're on board with that. So I'm

I think with it 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, like 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 there are people you already enjoyed who you invite into the car because they're your buddy and you wanna do this company with them. I think when it works

When you do it with your friends It's the best. And um when it doesn't work, it's w even worse than if they were they were not your friends. So you gotta take the good with the bad. But um

We had a podcast with this guy uh on the speed called Mike Brown. You introduced me to him, I met him at your office. Yeah, he's full of shit. He w he had a successful business, then he brought both of his brothers on board. And I was like, Why did you do that? Let most people say, you know, 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

If 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, like 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. Um Bass question. Someone asked who could squat more weight. I think I think me, Sean. I have uh I have Osgood Slaughters in my knees. If you 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 uh of that issue. Um, okay, this is a deep one. It's cool. We'll answer it. What are your biggest insecurities uh both uh what are the biggest insecurities both of you struggle with? Uh I'll say I'll go first. Sometimes I'm I I get incredibly insecure that m 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 crafts 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 in Andreas and Horwoods, I'm like, dude. N like I kinda wanna 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. Um Mine I would say I I don't even know if there's an insecurity as much as like

'Cause 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 you know, your um your weakness or your your flaw. I I would say like And something I I I kinda worry about, which is I don't really filter myself.

Um And I 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, like I said, with a rolling phone. 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 Um

I would say that fear I have and the insecurity I have is around Actually like hurting people's feelings. Like sometimes I could say stuff that's inconsiderate or Um Or hurtful in some way, or like

You know Two opinionated and no they didn't nobody asked for your fucking opinion type of thing. Um so I I'm kind of conscious of that. Like I I would say I'm pretty self self conscious about that. That that's the word not insecure. I'm self conscious that While 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 that How other how how others will feel about it? And um 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 knuckle dragger. I'm just like 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 when I meet people who are doing really amazing things like Scott Harrison's you know, he's been on a fifteen 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 d 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 uh he kinda like looked like Jesus in the moment. I thought he was Jesus in the moment. And like he's totally humble. He hated that they were celebrating him. He was there like Not for that reason.

But um That's the reality of the impact of his work is he literally changes like The lives of Entire like towns, essentially, in Africa. And um

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? You know? 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. Um, last question.

Uh When are you guys gonna do since Covet is pretty much in the past, when Is the next meetup gonna happen. I'm actually doing a meet so I'm driving to Saint 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 thirty or forty or fifty people, I forget how many people R S V P'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 two week tour or something where we go from place to place to place. I don't know if we could Drive. I don't know what you'd want to do, but I'm I'm totally down for like a two week thing. Yes, uh totally agree. I think like if we just said, all right, this fall, we're gonna go on tour, we're gonna go to these seven cities, seven cities in seven days, or seven cities in ten days, or something like that. And we just say Set up the events.

I would love to do that. Uh I think that would be just 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 gonna show up in uh Oklahoma City. Can you get like Can you book me a hotel? And uh set up like an event, right? And I'll tweet it out and um

Well we can have her do that and help uh help us do that. You uh do something really great that I think you should tell people, which is When you you host an event, but you make the themes Great. So like you used to do this thing called pizza and forties.

Um, so can you give me I 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. Cause I've been to a lot of Silicon Valley networking events are 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 g 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. Uh 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. Um 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, because a 40 ounce beer takes like an hour to drink. And as and so we only would have pizza because we are 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's done, the talk's done, and the answers get a little bit wilder as they get deeper into the beer. Um, we did two X, which was focused on women telling their story. It stands for Two X chromosomes. Um we had like Did you go to the one that we had in the marina? No, what's that? Um, we used to do two X at this thing called Palace of Fine Arts, and we had like literally two thousand 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? Hustle con, con. Uh, which is Con Con is the startup that's uh the content conference. I thought Concon was a funny name. What else? Uh anything else? Have you d I feel like you've done some breakfast thing before. Have you done a breakfast thing? Rise and grind. Yeah, we did rise and grind. Um, which was we would talk about different stuff in the morning over 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 catch 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 uh 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. Uh huh.

I feel like I can rule the world, I know I can be what I want to I'm putting my all in it like my day's off On the roadless travel never looking back

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