#216 - Why Today Is the Day to Ask For a Raise

Would you rather own a small piece of something huge or a big piece or everything of something much smaller?

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 off. On the road, let's travel, never looking back. Sam, where are you, dude? This looks awesome. You're at like a pool or backyard. You're in the Hamptons. What's going on?

I spent the weekend at my in-laws' house in the Hamptons and I felt pretty sick yesterday, so I just stayed the night here. I didn't feel well, but I'm feeling fine now. But I'm in, I'm in the Hamptons. It looks good, right?

I mean, it looks amazing. Yeah, it looks like what I imagine. I've never been to the Hamptons, not even close. Never got an invite. I don't even know anyone that lives in the Hamptons.

So let me, let me tell you my opinion. Okay. My opinion of the Hamptons, incredibly overrated. You want to know another thing that's incredibly overrated? Central Park. Central Park, so overrated. Central Park and the Hamptons, both overrated. The Hamptons, not— it's not that pretty. It's not that pretty at all. So very overrated.

So what's the appeal? What is good about it?

If you're in New York, it's only an hour, hour and a half away without traffic. So you can go to the beach there.

So it's a little bit like Sonoma or Napa. Like, I think those places are nice. They're not the best. They're kind of boring as far as—

Napa is— Napa and Sonoma are prettier than the Hamptons without a doubt, in my opinion.

Oh, okay. Interesting. And do you like— do you feel different? You walk around, every car is like a Bentley or better.

You have to have a Range Rover to fit in. It's crazy, man. It's not my style at all. It's very— it's not— it's not even remotely my style. Did you see the Jake Paul and Tyron Woodley fight last night?

Did I tell my wife I can't help with the kids' bedtime routine because I'm watching the Jake Paul fight? Yeah, I did that. And then watch that fight and I thoroughly enjoyed myself. It was an amazing fight.

I thought it was a good fight. I thought Jake Paul— I had higher expectations.

Drama was there. I'm not saying where the technical boxing was great. I'm saying the drama was there. I didn't know what was going to happen. Beforehand and then every round it still felt like anything could happen, which is what you want.

The drama was so high. My, my, my anxiety level was equal to the best UFC fight. Like, like the best grudge UFC fight. My, like, anxiety level was equal to it. I thought it was amazing. We had Jake Paul on the podcast. He was way different on the podcast than he was in, like, for the, for this whole boxing thing. But anyway, It was—

I was gonna tweet it out. I was like, hey, uh, congrats to guest of episode 170 on your victory tonight.

Yeah, it was, it was a fun fight. I'm happy I got to watch it. It was more, it was more intense than any— you have— as intense as any UFC fight I've ever seen. It was pretty badass. They've done an amazing job.

Also getting in a ring in front of a million people, getting in a ring in front of 50 people, it's incredibly frightening. Now to do it with someone who's like, even though Woodley is— yeah, he's at the end of his career, he's 40. He fucking kills people. Like, he crushes people. Like, he could— you definitely could die. I mean, it's not likely, but you could.

And that's incredibly bold and very likely you could get humiliated, knocked out brutally by this guy, you know, in front of everybody.

Yeah, 100%. And so I do think it's incredibly courageous, even though whether I agree or don't agree with like a lot of the shit they do, it's wild. I can't believe they've pulled this off. It's wild. It's incredibly wild. The crowd on TV, I've been to like 3 or 4 or 5. I forget how many. UFC fights, and I've been to some of the big ones at Madison Square Garden. The crowd on the TV, like on the— in Cleveland last night felt the same as when I saw UFC fight, like the same energy. It was pretty wild. They built this.

They— yeah, they did it. They pulled it off. Um, I also went to, uh, a live MMA fight, a local one here in San Francisco.

Where? In the, uh, the Dragon Den?

Dragon House. Yeah.

Amazing. You went to one?

We can go together this weekend. I went to one.

I've been to a bunch there. It's badass, right? It's way scarier than UFC.

Way, way more intense. So we get cage-side seats because they're only $50, right? So like, yeah, you know, it's not a huge stadium. It's Qizhar Stadium. It's a very small place. But we went there, we get cage-side seats for $50. Since COVID you know, started and they said like, oh, everybody's got to be vaccinated. They didn't check anything at the door. So that was not so great. But I walk in and the crowd is just lit. I don't know what—

they're all— well, they're all like super drunk.

Yeah. So, so I think there's like 4 or 5 factors going in. So first of all, it's their friends fighting usually. So like there's a whole— in every fight there's at least like 20 people that are there because they're friends with this person. Because these are amateur fights. These are people who by day, you know, they deliver for DoorDash or they like work at a, you know, consulting company or whatever. And then this is like a nighttime fight club thing for them where they just like decided, screw it, I'm going to try this. Because I get there early, I get there for the amateur fights. I find those way more interesting than the pro fights. And so first of all, there's 20 people that for that, that's their friend, that's their brother, that's their kid. I'm seeing moms just yelling like, kill him, because it's like their son in the ring or whatever. Second thing is it's like people are drunk.

Yeah.

So people are drinking.

There's only like one concession stand there.

There's one concession stand and it's only beer.

So they only sell— they only sell beer and Costco pizza, right?

Yeah, exactly. Uh, it's like beer and things that make you want beer. And then third thing is, um, I think so— well, I think the third one would be I'm so used— like, you're in the Hamptons right now, dude. I, I just hang out online on tech Twitter and crypto Twitter, and like, the group of people I normally hang out with are so nerdy, and like, they're just concerned about different things. The priorities are different. I went to this thing and everybody's like super dressed up, like not like fancy, but they were dressed up like, I might meet someone here. Like this is like a club to them, right? I just feel like everybody here, it was like more real people than the like kind of bubble that I usually live in. And so it was just different. It was like shocking. There was 3 fights that broke out in the crowd just after a fight would be done, a fight would break out in the crowd. And I'm sitting there with my sister and my brother-in-law and we're just hoping it doesn't happen near us. And the last thing was COVID. Like, COVID, I think, has riled people up. Like, when I came in, I was telling my brother-in-law, I was like, dude, this crowd is way better than the last time we came to Dragon House pre-COVID. He goes, dude, people are ready to live. He's like, people were just ready to get out. And you could see it, dude. People were just like— I don't know, I don't know how the kids use the word lit, but people were lit at this event. This was— the whole event was lit. It was insane.

I love going to those. I've probably been to of them. Were the Mongols there? I guess they weren't there because they can't travel. No, I've been there and there's— they have— there's like a large like contingency of Mongolians and, and they have their family.

There was one Mongolian fighter and he— yeah, his crowd was like— his crew was pretty crazy. And then he fought this Irish dude and I swear to God it was like Conor McGregor came out. As soon as the guy comes out, it's like, olé, olé, olé! The whole crowd is chanting olé. I'm like, what Where did this huge Irish contingent come from? He's got a tattoo silhouette of Ireland on the side of his body. He gets in the ring and they had a crazy fight. And so it was a lot of fun, first of all. So if you have like a, I don't know if people, I don't know if it's only for people who like UFC, but if you like the UFC, which is like maybe 1% of our audience, go to a local show.

I bet it's more.

Go to a local show. I didn't think it would be this good. It's like amazing. It was like truly amazing. But it also made me feel like, What is it about people who— why would anybody sign up to do this? And then I know you are the type who you signed up to get punched in the face quite a bit. What's the appeal and would you ever do this?

Well, I signed up for a smoker. So what a smoker is, is it's amateur. So there's no judges. And typically you can kind of have like in a— like you can like say ahead of time like, hey, I'm new, you're new. Like you don't actually— at the fight that you went into, they're going in with bad intentions. You know, they want to hurt you. With the thing that I signed up for, sometimes like you'd be like, hey, let's, let's get after it. And you'll try to knock people out and you might get knocked out, but it's like not nearly as angry. And you could like say, hey, we're going too hard, let's take it easy.

So I've said it's like above a sparring session.

It's above a sparring session, but it's not quite a real fight, or at least it doesn't have to be. And I signed up for it because it makes me feel alive. It makes me feel like I feel soft when I just sit in front of the computer all day. It makes me feel good to survive getting beat up because I know that I'm not gonna be stressed out about anything else that I'm gonna do throughout the day. 'Cause like when I stress out about like this podcast or if I get mad that our freaking internet wasn't working really well, I'm like, dog, I just got my ass kicked. Like, everything else is fine.

Exactly. I went skydiving once and we did it in the morning. It was like 8 in the morning. And so the rest of the day, like, you know, from 8:30 onward, skydiving only lasts like 5 minutes. Like you just, you fall for 60 seconds and then you kind of float down gently for 5 minutes. And then it's over. But the rest of that day I was like, I couldn't be bothered by anything. I was like, dude, I jumped out of a plane this morning. You think I'm gonna worry about this presentation I have or this person who didn't call me back or this person who cut me in line? Like, bro, I flew. I was flying in the air this morning. And so it was like, if I could bottle that feeling up and have it more often, which it sounds like you get by sparring or whatnot, that's pretty good. I also have been rewatching Breaking Bad. So did you watch Breaking Bad like once? Yeah. So I just started rewatching it and it's like enough years have gone by where I kind of forgot it. And that's basically the premise of the show. The show is basically this guy lived kind of his whole life, you know, by the book and was like always like kind of just like worried about, you know, he didn't wanna offend anybody, didn't take much risk, blah, blah, blah. And then when he finds out that he's got, you know, a few months to live, he starts doing this stuff initially to help his family. Like, how do I provide for my family if I pass away? I don't want them to have nothing. 'cause I'm just a teacher, I didn't save up too much money. And then once he starts to do it, it starts to feel good. He starts to feel alive. And so this has become kind of like a theme I'm thinking about. And like, if we wanna tie this to business, I'll force it here, which is there's probably a whole set of products or experiences that just make somebody feel alive and they're kind of counterintuitive. Like why would you choose to get punched in the face? Why would you choose to take this risk and almost get caught by the cops And then how do you bottle that up and package that in a product or service so that— because I think a lot of people do want this feeling, and once they get it, I think it's very addictive.

But I would say that that's what you do with a lot of your investments, right? Like when I think about what you're doing with an NFT or what you're doing with crypto, to me it's a high adrenaline, high risk type of thing, right?

Uh, kind of. I think you'd think I take more risks than I actually do, but, but yeah, I could see that. That's definitely a piece of it. There's a bit of the roller coaster that you get to go on, and the roller coaster is for a thrill seeker. But I just think in general, like, you know, we were in LA, I went to Disneyland. Why are there even roller coasters, right? Well, because people— in 30 seconds you can get that feeling like you might die and then you live. And that little package, that thrill, it taps into this thrill seeker part of people. And I just feel like there's probably more experiences that could be built that are like that. I think if you're building in VR, for example, Instead of trying to build a VR kind of like fantasy land, I would build things in VR that make people feel a little bit afraid, a little bit scared, a little bit alive. And I think a lot of video games try this, right? That's why a lot of video games are about shooting people and stuff like that, 'cause it's cool and it's an escape and it's something you can't do in real life. So you get to live vicariously through this. But I just think there's a lot more that could be done.

So instead of talking about fear, can I tell you something that I read recently? It's about happiness. Can I tell you something that totally, like, kind of like— I read something recently and the data seems pretty clear and it totally, like, goes against what we've been told previously.

Can, can I tell you about that? So lay out, lay out what we've been told and then what you saw.

So the, you know, there's these, like, things that you see headlines. So one of these headlines is like, the average American doesn't have $500 in savings or something like that. That's, that's, that's mostly bullshit, by the way. That's, that's a bullshit headline. But the other one was that after you make $75,000, your perceived happiness level doesn't really go up significantly. And I read about that a while ago. We read about— I mean, when did that come out, you think? Like in 2012 or something?

2013? Yeah. I feel like I've heard this kind of my whole professional life. So maybe at least 12, 15 years, something like that.

I've always thought that that was bullshit. I've always thought that was bullshit.

Um, it didn't pass the sniff test for you.

Not even a little bit, not even a little bit. And so I came across this study, and so what these guys did was they got 40,000 people to install this app. And this app, at random times, would ask you, like, they would ask you a bunch of questions, but it would be on a scale of like 1 to 5 or 1 to 10. I see you're highlighting the app, you could click it and you could see it.

It's called Track Your Happiness.

Yeah, and it's pretty cool. It's just a simple app. And what they did was they got 35,000-40,000 people, and they ranged They had all types of ranges and they asked people how they felt during different periods of the week, of the day, and they would track your income. And what they found is, is that while it is true that after you get past a certain point, your happiness levels doesn't necessarily go up in proportion. But what this study found is like up until like $500,000, $600,000, $700,000 a year, it was definitely still going, going up.

And it may— like, the difference between $2 million and $3 million probably won't be significant. But like, according to this study, like, the difference between $10 million and $1 million is significant and does impact your happiness. And that totally, like, kind of broke my frame, even though I always thought it would be true. I thought this study was actually really interesting. And there's a few reasons why— a few reasons why basically the other one was nonsense was the first one was remembered feelings. So the $75,000 study, basically what they did was they asked people how they felt in the past. And that's kind of bullshit because you always think that you remember, uh, things better than you actually did. Or like during the— during one period you'll think it's great, and then you'll say how you remembered it and you'll think it— or sorry, you'll— during the time you think it's horrible, then you'll look back and be like, oh, that was actually awesome, right? This actually asked you right then and there how you felt. The second thing was before it said, were you happier then or were you happier now? And that's kind of nonsense because there's no variance. Like the variance is too low and like You know, sometimes like it could be a while, I'm a little bit better and that matters.

And so that's what this— It's too binary. It's, it's just yes or no. There's no, like, there's no granularity.

Yeah. So I don't know. I thought this was interesting. I wanted to bring this up because that's one of the, it's one of those studies that I always thought that people base, like you read this headline and you believe this to be true. And a lot of people probably make decisions based off of this. And I think it's important to say, no, that's, I think it's bullshit. And, and you shouldn't base your life on that data or that study.

It's like, like what?

It'd be like, you know, it'd be something like, oh, you know, uh, at lunch today, uh, you know, I whatever, I, you know, this table was full, so I kind of had to go sit over there. Or it'd be like, you know, at, uh, you know, we're working on this project, I really wanted to get more done, but I got a phone call, I got distracted. Some people got off on high output. And so their happiness was like, it's like, "Oh yeah, we had to do that team meeting. And so I didn't get to go work on my project. I didn't get to write enough code today." Or it'd be something really, really small. It's like, "Yeah, I'm really dealing with this kind of back pain. So this chair's really uncomfortable." It was always things that I wouldn't have otherwise seen. And so it brought those to the surface and then I could decide, is this something I can affect and improve? Or Do I just like— at least I get a better understanding of them. So that was like one of the better products that we built. We probably should have productized it and made it an actual like work tool for other people to use.

Yeah, I used to use this thing called 15Five. You remember that company?

They're doing pretty well, dude. I think they're pretty successful.

I bet they— I would bet they are. So they kind of like went quiet for a little while and typically that means it's failing horribly or it's actually quite large. Like it's usually like one or the other. And so it was called 15/5, and basically they would send you 5— the whole product, it was very simple, and it's probably thrived during COVID But basically they send you an email every day and it takes— is it 15 questions that are 5 minutes to answer, or it's 15 minutes to answer 5 questions? One of those. And that's all it is, is they just send you an email at the end of the day and they say, what did you get done today? How do you feel?

Yep.

And that's all the product is. And I would imagine that it's quite large. Yeah.

Yeah, I think it raised at like $130 million valuation recently or something. So, you know, maybe that's a little out of date. That's 2019. So I bet it's doing, doing pretty well. Uh, all right, let's do a different topic.

What do you want to talk about? Let me tell you about a different, uh, a different company that I recently discovered. So it's called ESRI. Have you ever heard of that?

No, sounds like a government agency.

subscription revenue, nice.

Yes, it's software. It's a soft— I guess it— I guess you could call it information, but probably at this point software because it started in the '60s. So at the time it was basically information. But what it does is very simple. So 20,000-plus cities use it. So most cities, most like reasonably sized cities in America use it. Most states use it. Most Fortune 500 companies use it. And what it does is they have loads of information on maps. And so if you're a government, and you want to build new gas, new, new pipes or something like that in your city, you're going to take their data and you can also give them more data. And that's going to give you an interactive map that you can use to figure out where the other pipes are. And you're going to be able to build this, this, this pretty complex system that you can continually use year over year that's going to show where your pipes are. It's called geographic information system. You never heard of— you never heard of that term?

GIS. Yeah, I've heard that.

Yeah, I thought for sure you would have heard of that. It's almost like Google Maps on steroids. In the same way that Apple— or sorry, the same way that—

It's like B2B Google Maps.

This guy's name, by the way, Jack Dangermond.

Is that his name, right?

This Dangermond? I mean, come on. That's, uh, how old is he? I can see why people don't want to compete with this guy. Uh, he's pretty old. I don't know, he doesn't look— he's like, he's 80. It looks like he's, you know, well, he's rich. 60, 70, something like that. Uh, yeah, personal fortune. $4 billion himself.

Yeah. And he started with his brother when he was like 27. Crazy, fascinating business. Crazy, fascinating business.

And I can't believe he's never taken a cent outside of a $5,000 initial loan from Dangermond's mother.

Crazy, right? Crazy, fascinating company. And he seems for— I mean, you know what I read about him? He seems like a good guy, him and his wife. He's— so he's an environmentalist. So he started this because he cared about like wildfires and things like that. And he was building software to help create maps that somehow reduce wildfire, which I'm going to explain in a second. But basically there's a new company, there's a bunch of new companies coming out. The first one is called Felt. So go to felt.com. It totally is not—

I went to this, it looked, it looked, it looked— well, this is like an early access site, but my, I saw it and I said, oh, this is kind of interesting. So I started looking into it. I've read your notes on it. This Felt thing seems pretty cool. Are you investing in this? This seems like kind of awesome.

Nope. I, I, we just, I've, I've never talked to this person. So it started by a guy named Sam Hashimi. He used— his first company was called Remix. It was a city transportation planning startup that he sold for $100 million. And when he was doing that, he learned all about the inadequacies of like basically using maps and creating maps for your service. And he said, well, I'm going to try to create a better map business, something that people can add stuff to. And it's almost like where, where ESRI is like Google Maps, this is like Waze, so people can contribute to it if you use it. Kind of fascinating. And it seems very, very interesting. And I always like these old school companies. I mean, I like this company, this guy Jack started, I think it's badass. I love seeing the new guys that are going to try and take this and kick their ass. I think it's very fascinating.

Yeah, this is cool. I like this a lot. There was a company called— what's the name? They're based in— they spun out of like this lab. Hold on. I think you actually might have their name here.

And while you're looking for that, so felt— they describe it as the world's first collaborative mapping tool, and it serves a wide range of use cases. So I imagine— they haven't said this, but I imagine actually anyone can use it. A user can use it. So if you're going hiking with your friends, if you're planning a trip, you're allowed to use this. I imagine what they're doing is— their grand scheme though, their, their niche, their wedge is to help wildfires, uh, uh, go down. And so the way that you could do that is you can actually use data and and you can figure out where wildfires are, where they're gonna happen, and then cities will pay money to use your mapping data in order to reduce wildfires. And I imagine what they're gonna do is they're gonna create this really cool, because if you go to feld.com, it looks very user-focused, whereas they're gonna make all their money from B2B, so it doesn't look the same. It doesn't look like a B2B product. I imagine what they're gonna do is like, just like Waze, they're gonna let the consumers use it and map out really interesting shit, and then they're gonna go and sell the data and mapping tools to businesses, and that's how they're gonna win. Crazy fascinating.

Like they're putting their own—

They were their own balance sheet. They were just betting basically, and they were They're showing that, look, we can actually generate returns using this strategy. That's how valuable our data is. And I think since then, I think that was early on when they were just making the technology and playing with it. But either it was them or them and a partner doing that. And now I think they have a lot more customers who are looking for this, whether it's an agriculture company that has some need because they need to predict the way that the world is changing, the way that anything, any data that you can get from satellite imagery is basically what they do. So I really like that business model as well. Some people are doing that in terms of getting satellites into space and other people are doing it, taking the satellite imagery and making more sense of it, making more, getting more actionable data and insights from that.

Did you say the name of the company in front of the founder?

The name of what company? Oh no, he told me. Am I saying it wrong? Is it like French?

Have you heard of the philosopher?

Descartes?

Yeah. What's the French philosopher's name? René Descartes.

Maybe, maybe that's what it is.

What did you call it?

Descartes.

It's Descartes. Yeah, it's Descartes. It's like the— I forget. René Descartes. Is he the guy who said, "I think, therefore I am"? Anyway, that's what I—

Well, "I think, therefore I know." I know that I got that pretty badly wrong. I met this guy years ago, so I don't even fully remember the idea. I just remember thinking, "Oh, that's interesting." All my friends are making apps to order pizza and to-do lists and stuff like that. And this guy's basically taking satellite imagery and looking at it. And my two takeaways were, I should probably invest in this guy. And the second thing was, why am I not doing something more interesting with my life? Because that sounds way more cool and interesting and probably valuable than competing around ideas that everybody has and that everybody could kind of do. And so that was a takeaway I had during that process.

You want me to keep going or you want one?

No, do one.

All right. Let me tell you a quick story about a guy named Wayne Huizinga. I love Wayne Huizinga. I read his book. I believe it's called Building Blockbusters. So there's this guy named Wayne Huizinga. All right. Now I'm going to sound uncultured. Is he from— I always get it confused— Holland in the Netherlands in Dutch? They all the same thing.

Dutch is a way to describe people, I think, from the Netherlands. I think Holland might be a part of the Netherlands. I'm not sure.

I don't know. I'm sounding uncultured. I'm sorry, but what does it say? What does Wayne Huizenga say?

So he's of Dutch descent.

We'll go with that.

Came to the United States from the Netherlands. All right, good.

He also started something else, right?

He also started Automation. Yeah. So the guy, All right. So he's in waste management. He's in Blockbuster at this point. He's in his 60s. You think, all right, you're now— you're just going to chill. Absolutely not. He starts AutoNation, which is at this point it's the largest seller of used cars in America. So he went from waste management to Blockbuster to cars. And then throughout this whole period, he's also doing the same with resorts. So have you ever heard of Extended Stay America? I believe now it's owned by Marriott. You ever heard of Extended Stay of America? So basically they've got, they've got something like 5, 6, 700, uh, motels that are nice enough that you could stay for like, uh, a handful of, or for like a month or like 2, 4 weeks at a time. He started that. He also started a bunch of different golf clubs. And then in the '90s, he eventually buys the Miami Dolphins. And I think he bought another Florida, uh, what's the Florida football team?

Wait, the, so that's the Dolphins. And then he bought the, the Florida Marlins, also the baseball team.

I mean, these roll-ups happen kind of in every industry. I feel like people have done it with dentists, dentists' offices.

Right now, dentist is like the hottest thing going.

It doesn't interest me personally, but if I wanted to become a billionaire, I think that this would be one of the lower-risk ways to get it done.

Murdoch did this with local newspapers also. So Rupert Murdoch, this is kind of what he did, local newspapers and then local radio stations, local television stations, whatever. He basically bought local media companies and then aggregated them and rolled them all up and created like giant, basically News Corp, which is his mothership brand. So yeah, by the way, this guy Wayne Huizenga, if you're watching on YouTube, put this guy's face on here from his Wikipedia. Looks like an evil Steve Ballmer. So that's what this guy looks like. Bradley Jacobs, the other guy you mentioned who's done this with XPO Logistics and a couple other companies, literally looks like couldn't be a sweeter, you know, someone's sweetheart dad who, uh, you know, coaches the local soccer team. Uh, I, I love looking at these type because I think to do this you got to be pretty— I don't want to say ruthless, but extremely aggressive, ambitious, a great deal maker. And, um, and, and you're moving like at a freight train's pace. And so I love to meet these people. Now you can't meet them sometimes. I love to just even look at their photos and just Just read their bios. Who is this person? Where did they come from? Because it takes a very specific attitude to be able to go do this with self-storage or local, you know, landscapers, pool construction companies, you're rolling them all up.

I've read a lot about both of those guys and I've seen them talk on YouTube. And my opinion of them is that they seem highly ethical. They seem incredibly high energy, super high energy. And they seem very entrepreneurial, even though they both look like Wall Street suits that don't like create. These guys definitely are creators, even though they buy stuff and you think, well, that's not like, and you're not inventing anything. And maybe they're not inventing anything from scratch, but they're definitely creators. And I, cause I remember I saw that guy Bradley Jacobs and I saw what he looked like and I'm like, dude, this fucking suit. Like he's just like, he's just some arbitrage square. And he's not, he totally, he's a creator. And it's really interesting. He's maybe not like Mark Zuckerberg where he is like coding shit, But he's a different type of creator and I really like these types of folks.

Doesn't this seem a little low? This guy's net worth was $2.8 billion when he died. I feel like, how is this guy's net worth so low compared to doing AutoNation, Waste Management System, doing Blockbuster? How does that add up?

I think that the number that we have there could be wrong, but—

I think it's wrong.

What I read about in his biography was that with Waste Management, because they raised so much money and because they bought so so many companies, they simply didn't own that much of it. I mean, they owned a smaller piece of a massive pie and they were okay doing that. And so when he started Waste Management and when he left, he was the largest individual shareholder, I believe, but he probably owned like single-digit percentage, right?

No, I'm going to Google it. Is that how it's spelled?

So timeshares, I mean, timeshare is a huge business. I like the idea of a timeshare is not bad. I would, I would be into owning one. It's just that I don't want to go like through the sleaziness of, of, of, you know what I mean?

Like you don't want to sit through the webinar.

Yeah, I don't want to, I don't want to go to the seminar. So it's weird. So I think it could be cool. Why is it worth so much so fast?

Yeah, I don't know. I mean, they've grown, so Picasso valuation. I saw it because there was a big protest going on. So Picasso raises $75 million, goes from launch to unicorn in 5 months. So I think part of it is—

What was the protest?

What's that?

You said there was a protest.

Oh, the protest was basically in Napa, the home that they bought, the neighborhood was like, "Yo, what is this? We don't want We don't want this. We don't want this timeshare rental. We don't want all these different people coming through. Why are they doing this? And so they basically, they were trying to say, hey, timeshares are not allowed. And what this company says is it's not a timeshare. In a timeshare, you own a block of time. In this, you actually are a part owner of the home. So it's different than a timeshare. And then people were like, dude, you can't just call it cooperative ownership, make up a new term. And It's a timeshare. And so they're kind of going back and forth about that.

So the guy who started, his name is Spencer, Spencer Raskoff. Is that how to say his name? So he started—

Well, and Austin Allison. So she's actually the CEO. They were both execs at Zillow.

So yeah. So one of the co-founders' name is Spencer. Have you seen what this guy's done before?

No, the name sounds familiar. Wasn't he one of the original like founders of Zillow?

Like, yeah. So check this out. In '99, at the age of 24, he founded Hotwire.com, a leading travel internet company. I mean, obviously that's hotels, right? They sold it for $700 million. Then he started Zillow and he took it public. He was the CEO through its IPO and bought loads of different companies. He resigned in 2020, so I guess he's out entirely. Then he started .LA, which is a media company for California startups. So I guess that's kind of like a passion project. And then now he started Picasso. This guy's prolific and he's on the board of Palantir.

This is why it's worth $1 billion, because it's like, oh, the ex-CEO of Zillow is doing this new real estate thing. Cool, we're in and we're sort of price insensitive on the valuation. So I think it has more to do with the team than it does probably the traction in terms of that valuation.

Yeah, this guy's a badass. I mean, he's a hardcore badass. Would you want— when I think of these types of things, these companies that raise all this money, we talked about Zillow, or we talked about this company Picasso, And this guy looks like Spencer, that's his history.

Also a podcaster. He's got the Office Hours podcast. There you go.

Oh, we should have him on here. Spencer, if you're listening, come on. Do you think that— do you like this strategy of raising— would you rather own a small piece of something huge or a big piece or everything of something much smaller?

Um, I don't think about it that— like, that wouldn't be the deciding criteria. If it was just between those two, I would rather own the own the whole thing of a smaller thing. I find it to be more fulfilling, and I think economically you end up doing better, or you have more options, because when you own a small piece of a bigger thing, if it happens to go a little sideways and doesn't have big unicorn exit, doesn't go public, doesn't get sold for $3 billion, it's very easy to kind of walk away with very little, because you raised all this money, so now you have the first $100 million go back to investors, and maybe you only sold it for 70 or something like that. Whereas you owned like a huge amount of the hustle. I think that path is better 'cause you could sell for $12 million and walk away with $10 million, you know, like out of it. And so I think it gives you more options on how to build your wealth. Now, that being said, there's something fun about building something massive and going for something that's like truly game-changing with 3 extra zeros on the back of it. So like, you know, I respect both paths. If I was picking between those two, I would own, I would want to own more of a smaller thing because it gives me more options.

What do you think is easier?

Oh, for sure owning a small thing. Now, easier in one sense, which is it is easier, I think, on a day-to-day basis because you don't have to worry about fundraising, shareholders, other shareholder management, and again, you can exit for smaller amounts. The harder part, when you go raise, like these guys just raised $75 million, they're not gonna feel like they're like roughing it every day. Whereas when it's your company and like, I don't know, you probably ran payroll for, you know, the first year of The Hustle. And you probably had to worry, like let's say, you know, advertisers pull out, you know, you probably were feeling that pinch because you were more or less bootstrapped. You raised a little bit of money, but like, I don't think you ever felt like, you know, you have this huge cash cushion that you can just fall back on.

Well, yeah, I did not, but I normally would have agreed with you, but we had Marc Lore on the podcast and I had a lot of his coworkers reach out to me after the podcast. And basically Marc Lore is at Jet.com. What he's done is he— what was his vision? He had this phrase and I forget the phrase, but it was like vision, capital, people. Is that what it was?

Yeah, that's his fund name now. So we can look it up. But yeah, it's vision, capital, people. Yeah, you got it right.

VCP. Vision. And so he like, that was his whole premise. He's like, everything, I come up with the vision, I get the capital, we get the people. That's what we do. And when he says that, I'm like, that, like, what does that mean? Like, that's a pretty like a vague fluffy thing. But I started talking to people who worked with him and they're like, he did that so well where he would raise all this money and he really like, he did a lot of work, But it wasn't like he wasn't like doing like, like, like, like, you know, the shit that you do when you're just starting out when you don't have any money, you know, like I ran my own payroll, I did all the banking, I did, you know, I would go out and get all the vendors. He was like, he just like hired amazing people and they did most of the work and he just took care of the hard part of like selling people to join the company and selling people to give them money. And I thought about that. I'm like, Dude, that does sound so easy. It sounds pretty awesome.

It's not that it's easy, it's awesome. That's how I'd put it. Nothing's easy. Anything valuable is typically— you don't go to it because it's easy necessarily. But I'm totally with you. What's more fun, a small vision or a big vision? A big vision, right? What feels better, having a lot of ammo in terms of capital or being strapped for cash and always not only having to worry about how to get customers and grow, but Can we pay the bills every single month? Yeah, definitely.

But on the other side, if Sean wants to fuck off for a little while, you can do that. Yes, exactly. You can bail for a little.

Well, I remember we were talking about that with HustleCon when you were doing HustleCon. The HustleCon ticket was what, like $200, $300, something like that?

Yeah.

On average. And you had told me, 'cause I was like, "Dude, why are you doing this like events business?" You're like, "Dude, events business is gonna be big. Look at this one, look at that one." And I went and looked at 'em 'cause you were right. They did actually like make tens of millions of dollars. But I was like, "Dude, the ticket price of this is 3 grand minimum. And it looks like they have a $15,000 ticket package for like," some people, yours is like 10 times cheaper than that. And you were like, yeah, we should, we could, but you didn't feel comfortable going that route or whatever. I don't know what your reason was because you knew it.

Yeah, I knew it. I was being a— there's a few things. One, I was a pussy, so I was just— I was being fearful. And number two, when I started my company, I was like 24. What I don't— and I never had a job before. What I don't understand is how these young guys like people who are 21, 22, 23, like when the folks who started Box.com, which is an enterprise cloud company, they were like 20 or 19, like in college still. What I don't understand is when you're a 19, 20, or in my case I was 24, when I thought about the company, I was like, well, like I don't have any money. I would never buy something that was $2,000. Now that I'm older and I have more experience, I realized, well, $2,000 is not a lot of money. And so what I don't understand is how these young guys who are in their early 20s and don't have a lot of experience, how they even fathom that someone's willing to spend all this money on their product. They're either just courageous or they have more faith. I don't know what it is, but I— but kudos to them because when I was 24 and starting my thing, even though I could have charged way more money and I tell everyone to do it now, I did not have the courage or the knowledge to do it back then.

Right. And you see now because you're inside HubSpot, you see how much companies spend on just stuff. Like what amount of money— it's like going to a really wealthy person's house and then you see them tip, you know, they tip some guy $100 or they, you know, they buy this fancy espresso machine for $8,000. It's like, oh, these are normal expenses for them. So then when you're on the outside, you're like, I should be charging a lot more. But when you've never been inside one of these big companies, it feels like a $3,000 ask Dude, I better be giving them like my left arm. And it's like, actually they feel more comfortable with larger price tags. And that's like, in fact, a $300 product is a little bit off-putting to them and sort of strange to them.

But it's like insecurity, right? Because at the beginning you're like, oh, I just want some customers. It's not that big of a deal. Then you kind of— then that becomes the anchor point that you mentally anchor to and the market anchors you to. And then you're afraid if you raise prices, is everybody gonna run out the door? You know, what happens if I raise these prices? I'm gonna get complaints, people are gonna quit, you know, blah blah. And so it's really like a form of insecurity. It's like a corporate insecurity. And so if you're out there, I tweeted this the other day, I was like, if you're working at a company, go ask for a raise today.

Do you think anyone did that?

I was kind of like—

Except if you work for me, don't come ask me for more money. That doesn't count because I gave this advice. So don't ask me. But other people, this is for other people.

I was notorious at the hustle because when people would ask me for a raise, I'd always say yes. I was horrible at confrontation. I just said yes to everything. I'm like, "Oh my God, I don't feel like dealing with this." That is not true, dude.

You told me a hilarious story. We can bleep this out if you don't want to tell it. I don't know if you remember, me, you, and our friend Suli, we were at Della Rosa, or we were at some restaurant. Restaurant and you told the story of— okay, bleep this. Do you remember this? No, I don't remember that fully, but you were just like, no, and you can leave if you think that. And it was just like, it wasn't just no, it was like, you don't understand.

Like, oh yeah, yeah, yeah, yeah, yeah, yeah, yeah. So the story was like, well, yeah, so I remember this. So I should rephrase this. When people do good, I say yes to everything. When people do bad, they're like, well, I want a raise. I'm all right. So you're like, you are a machine to me. This sounds horrible, but it's like, look, like our business is a machine and like humans are like part of the input. Humans' effort are part of the input. And you're asking me for a raise right now. I think that the money that you are paid like breaks even. So like we put money into this, into this machine, we put input, same amount out, and we get the same amount out. If I were to give you more amount of money, I'm putting more input. How much bigger is the output going to be? Because right now I don't think it's— I don't think that it's worth it. And so I don't think it's worth it. It's— and so if you don't think that that's fair, then you should go to some other machine and figure out where that input can have a bigger output because right now it ain't working.

Right. Yeah, exactly. So I love that. I love that because A, it was honest. B, it was a little bit brutal. And, you know, it wasn't like I would say you have many, many super strengths, like A+ skills, like I would pick you over anybody. Uh, softly wording things is not, not one of them. So I found it to be super funny. But it— but really, again, even if you find that information out and it hurts in the moment that this person says, look, it's not like— it's not on the table with the way things are currently at. If you find that out You know, that's a good piece of information. It hurts in the moment, but it's a good piece of information to know, 'cause you might say, "Shit, I need to create more value here." What would it mean? And you can have a conversation. You can say, "Well, what would I be needing to do for you to feel great about paying me double what I'm making today?" That's a question you can ask. They might not know the answer on top of that, but they'll come up with it. They'll help work with you on it. And then you'll realize, "Oh, that's where the value is created in my business." And so maybe in this machine, that's where the machine needs the oil. I should go oil that part of it and create all this new output. And then of course they'll give me some more because I've created all— I've created disproportionately more value out of it. And so it's a good conversation to go have if you haven't had it, you know, with, with the people you work with.

All right, good. Well, let's see if we're going to do that. All right. Good pod.

Yeah, let's get out of here. I feel like I could 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.