Jesse Pujji on Bootstrapping a +$1B Business + Selling To The Ultra Rich

Here is a summary of the key points from the transcript: - Jesse and his co-founder started a high school version of Facebook called The High List in 2005. When Mark Zuckerberg wanted to buy the domain name, Jesse called Zuck pretending to be someone else to verify it was really him. Zuck outlined Facebook's whole expansion strategy on the call. - Jesse reflects on how joining Facebook early, even in a junior role, could have made him a fortune in stock options, similar to Noah Kagan's experience as an early Facebook employee. - Jesse started the digital marketing agency Ampush and later sold it. He now runs an "incubator" called Gateway X where he starts and grows new businesses. - One new business is Aux, which provides marketing diligence and advice for private equity firms looking to acquire companies. It charges $50k per week compared to consultants like McKinsey that charge $200k per week. - Jesse explains how he leveraged his expertise to get rapper Nelly to perform at his 40th birthday party by advising Nelly's team on ecommerce businesses for free. He ended up paying $60k to fly Nelly privately roundtrip so he could make the party date. - The key takeaways are to "sell to the rich" who are less price sensitive and identify what they need based on your unique expertise or network. Jesse also discusses finding purpose by identifying what you naturally do to help others be their best.

Speaker A: You said a couple interesting things, so let's break this down.

Speaker B: We have no money. We're bootstrapping. Let's get ourselves on GLG as experts. And I'm like, okay, my charge is $500 an hour. She goes, no problem. But we talked to someone after a few weeks, and he goes, do you guys have research? And we look at each other, we're like, yeah, yeah, we have a report. It's $5,000. So I always joke, that was ambush's angels round. We raised $150,000 selling research reports to hedge fund people.

Speaker C: That's pretty sick.

Speaker A: That's an amazing story.

Speaker B: And by the way, there's eight of them that all have, like, high eight or low nine figures in EBITDA. The whole category has, is just crushed.

Speaker A: The two takeaways from this, by the way, are sell to the rich. And then your way of figuring out what they need was.

Speaker B: Jesse.

Speaker A: What up, dude? How are you doing, man?

Speaker B: What's up, guys? I'm pumped to be on here.

Speaker A: Good to see you.

Speaker B: Where should we start?

Speaker A: You sent us a doc, had a bunch of cool ideas on it. Which one do you want to start with?

Speaker B: Yeah, I mean, maybe some of the stuff we've learned at Gateway X as we've been building new ideas. I think the idea I'm most excited about, which I think, Sean, you and I have talked about, is aux Insights.

Speaker A: Sam, do you know about this business?

Speaker C: No, what is aux insights?

Speaker A: Oh, dude, this is sick. Okay, tell us about this business.

Speaker B: You're going to love it, Sam. So, you know, one of the things, as we've learned starting new businesses, and some of them you guys probably know, like, Kahani, Sean, you are a customer of it. It failed. It didn't. We stopped doing it. And one thing I've learned sitting in this seat is it's really important to, like, understand demand and that there's a customer who has a problem that you need and then go stand up. The thing with growth assistant, that's what I did. I already knew people needed it. I just stood it up and immediately started to work. And so I started my career in finance, in consulting. I went to Penn. I got a million friends who were in private equity. And after we sold ampush, I would get a call from one friend once a month without fail, who worked at Blackstone or worked at TPG or worked at one of these fancy private equity firms, and they'd go, hey, I have this deal in front of my investment committee. It's a billion dollar company, and I'm getting asked all these questions about their Google and Facebook ads. Jesse, what if they don't perform well? Or how do we know they're good at them? And they're asking me to look at the web traffic and make some analysis. Jesse, I have no idea. And my investment committee is not happy because I can't convince them to buy this business. What should I ask them? So the first few calls I'm like, well, the same thing any of us would do well, go look at the Google Analytics. Well, how many creatives are they testing? And my fourth guy was like, dude, can you just do this for me? And I'm like, you know me, I'm like, well, yeah, a couple hundred thousand dollars, I'll do it for you. And he's like, oh, that's it? Yeah, done, let's go do this. And so Aux Insights is essentially a private equity consulting business. It works for private equity firms, specifically in the office of the CMO, marketing related diligence and what's called value creation. So value creations, after they buy the business, they want you to spend time helping them put together a strategy for how they grow the business. And there's businesses like accordion, the cool example, 300 million revenue, 100 million EBITDA. It's only a twelve year old company. They do the same exact business for office of the CFO.

Speaker C: What?

Speaker B: So anything finance related? Yeah, accordion. I mean you could look at Lek is 800,000,250 in EBITda. McKinsey has an over billion dollar business just for private equity firms that's got 55% EBITDA margins.

Speaker A: And when you say they're office for the CFO. So let's break this down. So you said a couple of interesting things. The first washing. It's a lot easier to succeed in business if you first find the starving crowd. So find the really hungry market versus how you and I, Sam, like started. At least I should just speak for myself. I don't know if you did the same thing, but I would always be like, what's a cool idea? Or what's something I could make or what's something that seems easy to do? And it was easy at the start because it's so familiar or it's just nearby, but I have no idea the demand or the demand is all in other broke people like me. Its going to be really hard to sell and make money or I need so many customers to make money. Whereas youre like, well let me work backwards. Who are the richest people and richest companies? Its like private equity hedge funds that type of customer.

Speaker B: Theyre not price sensitive at all. Theyre urgent, Preston, and theyre super rational.

Speaker A: Theyre like, cool if I can buy something for $100,000, but its going to help me make a $10 million decision. Great. The math, maths im in. They're wealthy, they're not as price sensitive. They're rational. And in your case, you figured out what the need was because you had one fortunate circumstance, which was like, they were calling you to ask you about this thing, and you basically. So what you built was like a marketing due diligence. So they're looking at a company. They need to know, is there, are there digital ads performing very well? Not so good. Is there any red flags in here? Any concerns in the same way that if I want to go buy a company and I get a bunch of financial statements, I might ask a super.

Speaker B: Financial, an accountant to go look at it? Yeah, yeah.

Speaker A: Like, hey, my accountant, like, can you look at this? Can we do a quality of earnings? Can we get, can we get some understanding of, like, are these numbers solid or not? They are really financially literate, but they're not as Facebook ads and Google Ads and Pinterest ads literate as you are. So you're providing that diligence. And then after they buy, then you're like, cool. And then we'll help you, like leverage. We'll show you some levers that might be able to grow this, this thing after you buy to create the value. Right.

Speaker C: You should get background. So you started and sold ambush for some tens of millions, I think, dollars.

Speaker A: Digital marketing agency.

Speaker C: And then with that money, you went and started Gateway X, which is almost an incubator.

Speaker B: Yeah, we call it a studio mutual.

Speaker C: Go where you have started three or four or five businesses.

Speaker B: We started six. We've shut down two. One is kind of going sideways, two have crushed it, aux being one of them, and one is new.

Speaker C: Got it. Okay.

Speaker B: And, and let me jump in and say two things that we, what we call it at Gateway X in the studio, Sean, is we have to have a unique insight and an unfair advantage. I want to build, like, in ten years. I want this holdco studio thing where we've got five to 15. I don't care what the number is. Operating companies, they're all profitable. They're compounding on top of each other. And we've got this super cool culture of builders basically inside of it.

Speaker A: You don't raise money at the start for them. Right?

Speaker B: We don't raise money. We tried it with Khani, as you know, and it didn't work. It just wasn't for me. I shouldn't say it was fine. Just wasn't for me.

Speaker C: What. What's Kahani?

Speaker B: Well, there's a great example of Sean's point of, like, a cool idea, so that you're going to think the idea is cool the second I tell you in, like, a shitty idea business, I was like, look, ecommerce sites look like they're ten years old. And meanwhile, Instagram and TikTok have got these, like, full vertical videos. So let's make a plug in to let ecommerce companies change themselves to look more like TikTok and Instagram. So the first product was the little stories navbar at the top of. Of every e commerce site. And we had it on Sean's site, and I was like, oh, it's going to. People are going to engage with it. The content's going to look bigger. It's going to. And we launched it, and everybody. People thought it was a really cool idea, right? But nobody actually like Sean, by the way.

Speaker A: I thought it was an awesome idea. In fact, I kind of still think it's an awesome idea.

Speaker B: It is a good idea, but it doesn't solve anybody's problems, and nobody's lining up for it. And then we're like, oh, it's improving your conversion. But then it's like, well, it's not sure it's improving our conversion. It kind of seems like people engage with it, and then people are like, it's kind of slowing my site down or takes me too much content, and they just ripped it off the site.

Speaker C: Was it basically just a plugin? It's a plugin, just a plugin.

Speaker B: I mean, we had a big vision for it, right? You'd have landing pages, and you could put your influencers. And I still think someone's going to figure it out. But I sat there and I was like, I got this other business growth assistant. And here's a funny story. You guys will like this. We go to shop talk, and, you know, shop talk matches you. And I have one sales guy from kahani and one sales guy from growth assistant, and they both do the matching thing. The Kahani guy gets three meetings. The growth assistant guy gets 25 meetings, one selling marketing talent in the Philippines. And I go, man, if there's ever a signal for solving a problem versus just a cool thing, this is it. And that was one of the key decisions where I was like, I don't want to do this anymore.

Speaker A: And with ox. So with Kahani, he's like, yo, you want to invest? Would love to have you on board. Here's the deck. And I'm looking at it. I'm like, I kind of like the idea, but I'm not fully sold. So I ended up not investing with Aux Heddehe. He half tells me the idea to text message, and I'm like, I gotta invest in this somehow, right? Like, even I was like, instantly I was like, this shit's gonna work. This is a great idea. Much easier to solve. And one really cool thing I had heard, Jesse, can you talk about this? Which is earlier when you were doing ampush, you signed up for GLG, which is a, like, expert network where, where basically rich dudes on Wall street will call you and be like, hey, nerd, you know a lot about this biotech thing or you know a lot about newsletters.

Speaker C: It's like, uh, if a banker is about to take a company public, like a email software company public, they want to talk to all types of users of email software and ask them questions so they could have more conviction in their decision.

Speaker B: Yes. And by the way, there's eight of them that all have, like, high eight or low nine figures in EBITDA. To be clear, there's guidepoint Global, there's alpha sites. The whole category has just crushed.

Speaker A: And it's basically like, if Brad Pitt called you and was like, hey, you ever been to this italian restaurant in New York? He's going to take a supermodel there. But you've been there, and he's like, how's the? And you're like, that's pretty good, actually. And then they're like, cool. They hang up. You don't know why they asked you.

Speaker B: And they pay you $1,000 for the, for the, for the feedback. Well, here's a. The story of GLG is hilarious. So I don't usually tell this part of the story, but it starts earlier. Young Jesse's an associate at Goldman Sachs. He decides my best friend, who's my co founder's hedge fund, blew up during the financial crisis. So he doesn't have a job. So he kind of sits around. He's like, I don't want to get a job, Jesse. I want to start something. He gets me excited enough that I'm like, all right, I want to start something, too. Let's go start something. In a few months, I give my notice at Goldman. They're like, take 90 days, wind down. And I was like, me? I'm like, hey, do you mind if I use the firm's resources to research my future business idea. And Goldman, by the way, probably has a multimillion dollar subscription with GLG. So we have an unlimited calls. They don't charge us per call because at Goldman, they're paying them so much money. So me and my co founder line up three phone calls a week with digital ad experts and lead gen people, and we research e commerce. You name the category. We were talking to an expert in it for, like, the 90 days before we left. Before I left Goldman, we also had all the sell side analysts come and tell us, like, what are the Internet trends that we should be paying attention to? So this was the research before Ampush started. I'm 24, 25 years old. Then I start Ampush Quinn street, which you guys may or may not know is a publicly traded lead gen business goes public, and the same thing happens. A couple of my hedge fund friends call me and go, dude, isn't this what you're doing? Like, and I go, well, here's what you need to look at, and here's how their margins work. And then I get the idea. I'm like, we have no money. We're bootstrapping. Let's get ourselves on GLG as experts. So I call my old rep and I go, hey, can I be an expert on your GLG? Are they asking? They go, yeah, we need someone. I'm like, okay, my charge is dollar 500 an hour. She goes, no problem. So now me and my co founder are doing on the other side of the marketplace, we're doing five calls a week. We're making 25. It's good money. But we talked to someone after a few weeks, and he goes, do you guys have research that you can put together? Because you can. The way you're explaining is so helpful. And we look at each other, we're like, yeah, yeah, we have a report. It's $5,000. I'll send you guys a report. You can link to it. It's super outdated at this point. It's a 50 page report. It's going to explain the lead gen industry to you, tell you who the competitors are, blah, blah, blah, blah, blah. He's like, yeah, I'll take it. So we basically spend four days all weekend putting this report together, and then GLG is like, hey, we're getting a lot of other questions about this report. Can you sell more of it? By the time it was all said and done, we sold 30 of the reports. So I always joke that was ambush's angels around. We ran, we raised $150,000 selling research reports to hedge fund people.

Speaker C: That's insane. All right, guys, really quick. So back when I was running the hustle, we had this premium newsletter called Trends. The way it worked was we hired a ton of analysts and we created this sort of playbook for researching different companies and ideas and emerging trends to help you make money and build businesses. Well, HubSpot did something kind of cool, so they took this playbook that we developed and we gave to our analysts, and they turned it into an actionable guide and a resource that anyone can download. And it breaks down all the different methods that we use for spotting upcoming trends, for spotting different companies that are going to explode and grow really quickly. It's pretty awesome that they took this internal document that we had for teaching our analysts how to do this into a tool and are giving it away for free that anyone can download. So if you want to stay ahead of the game and you want to find cool business ideas or different niches that most people have no idea they exist, this is the ultimate guide. So if you want to check it out, you can see the link down below in the description. Now back to the show.

Speaker A: I don't know if you heard on the pod, but Anand from CB Insights did the same thing. Did you hear, did you hear his story? He basically no sold.

Speaker B: He's a smarter. He turned it into a huge business.

Speaker A: Well, he started with the, with the PDF, and he's like, you know, he's trying to charge like dollar 500, and then he's like, the best thing that ever happened to us was my buddy was like, no, no, you need to charge like $12,000 minimum 25,000 as your medium, and then have $100,000 option. He's like, dude, it's a PDF. Are you sure? They made like 300 grand that year.

Speaker B: It's a giffen. Good, right? It gets more value when people think it's more expensive. I mean, that's for pricing. For Aux, we charge $50,000 a week for a team of consultants and McKinsey, Bain and BCG charge $200,000 a week. So our argument is we're 75% cheaper than them, but way better. In our world of online marketing, the world that we know extremely well, how.

Speaker A: Come you don't charge 75% more and say we're better?

Speaker B: That was one of the things I didn't tell you when my friends were calling me and I was like, isn't there someone who does this? Why you keep calling me about this? And what they told us this is part of the market research was they said, look, McKinsey, Bain and BCG are $200,000 a week and they're not practitioners of marketing, Jesse. So they don't actually know the answers. And then every time we ask an agency, agencies come back with recommendations like change your match types or do more lookalike audience or whatever. And they're like, we don't know what the fuck they're talking about. We don't understand what they're saying. What they want is you do this and this much revenue and EBITDA will come. So a big part of our work is literally just translating marketing levers into revenue and EBITDA terms so that they can actually understand what they're, what they're going to spend money on or what the risk levers are in the business.

Speaker C: Do you run like fake ads? Like, um, like, you know, a lot of people when they have a company, they'll be like, you know, we want to make this product, but we're not actually sure if anyone's going to buy it. And so they make an ad for the product that doesn't exist. And sometimes the landing page will be like, oh, you caught us a little bit too soon. But let us know, uh, if you want this, whatever.

Speaker B: We've done it in value creation, we haven't done it in diligence. Diligence is like, you've got four weeks. They're trying to discern whether they want to buy the business. And you're just like, you have so much data, you have to figure out what's going on and be able to give them a smart answer. Value creation, you have twelve or 20 weeks sometimes, depending on the engagement there. We will definitely run experiments, we'll make ad changes, we'll do all these things and come back to them and say, hey, this is a good idea. This is not a good idea.

Speaker C: So to make this actionable, like even for me or Sean or listener, what do you look for? What can I look for in my business? And I assume obviously this is only if you are running digital ads, Facebook and Google, basically ads. What can you look for to be like, there's opportunity here, or, this is stupid, shut it down.

Speaker B: Yeah, I mean, we approach it a few different ways, right? One is top down. Like, we use Veros and a couple other third party data sources and our own data to figure out benchmarks of the company. So if you're an e commerce business with a, you're selling water bottles, what should your click through rate? What's your conversion rate by channel. That's our top down way of kind of assessing where they stand. And so that's just whatever. You can get that data anywhere online. And then the bottom up part of it is, for example, for Facebook, right? We'll say, like, is the account structured correctly? Oftentimes there's too many ads breaking the signal in too many different places, and it needs to be consolidated. The other question we'll ask is, is their event match quality good? Oftentimes, these old, old school companies owned by private equity, they don't even, they have like a three out of ten match quality, which means Facebook signal is super crappy for them. And I bet Sean's company and most startups have nine out of ten because they've, like, made sure Facebook's getting all the right data. Then there's all the creative stuff. Are they, you know, the easiest thing. Someone says my performance is bad. I go, how many creative do you test a week? A week? What are you talking about? Oh, we do two a month. Well, yeah, of course your performance is going to be horrible. Right? So creative testing is one of the easiest levers to pull in terms of improving Facebook.

Speaker C: And if a business that you're looking to buy has all of these things that they're doing wrong and they're still succeeding, and you, for you, you're like, there's opportunity here. If they get this right, you're going to be even better after buying this.

Speaker B: Exactly. And size. Right. So the key deliverable. The first five slides of every deck are, here's the grade for every channel, and then here's the waterfall that says, what's your current EBitda? And then if you improve the things that we think in a pretty moderate way, here's what your EBItda of the business could be. And that's the money chart. For a private equity guy, that's pretty sick. Yeah, it's a super cool business. And honestly, like, the validation that we've gotten, like, that's the other cool thing is that my, one of my other tests for a business is if in my discovery phase, people start asking me to buy it, I know I'm onto like, that's what happened with growth assistant. That's what happened with aux in early days of am push that happened. I was like, hey, this is an idea we have. We want to get you offshore marketing people. And they're like, can I get one of those people? And I'm like, oh, okay, we're good. Same thing with a private equity. I call some of my buddies and go, here's this idea we have we want to do is he's like, oh, I actually have a deal right now. Can you guys start looking at it?

Speaker C: That's awesome. How big is this business now? Is it a year old? Could you say, like, in year one?

Speaker B: It's like 5 million? It'll do 5 million this year.

Speaker C: Dude, that's insane.

Speaker B: Yeah, it'll be 5 million. And we, by the way, we invested one 10th of what we put into Kahani into it.

Speaker A: And by the way, Sam, I think the key, because you were like, what are the marketing levers? And he gave you as good as an answer you give, not having the thing you need. It's like, doctor, what can I do to be better? But here's none of my data and none of my scans and none of my knowledge. It's like, well, you should, I guess, check on your health. So the key here with this business, though, is he won't say this is not part of a sales pitch, but I. It's not that he has to be, like, this marketing savant that's going to find the genius levers. These companies are really buying certainty, and it's Cya. It's why a lot of consultants get hired in the world. There's a CYA component. You're doing a deal. You need to understand that the thing you're buying doesn't have any horrible warts. That's the first piece. And then. Cool. What is a best case, base case, worst case scenario of what we can do to grow this thing? And it's not even, like, a specific tactic. Like, oh, change the audience segmentation. But it's like, we need a plan made by people who know a lot about this. And that's enough to, like, kind of move the ball forward. And then, of course, like, when you could go in and you actually, like, do the shit, you'll figure it out case by case. Like, there's not like. Like, you go to 100 e commerce companies, and you could take the ten smartest people in Facebook ads and Google Ads. They're gonna give you ten different answers for every single company. Because one guy likes cost caps, another guy likes ASC, another guy says, simplify the structure. Another guy says, use all the new shit. Another guy says, do this attribution method. Another guy says, this. There's no real uniform answer for, like, how do you do? How does this work? Better versus worse?

Speaker B: Yeah. Well, I'll disagree. I'll show you. Can I share my screen?

Speaker A: Yeah.

Speaker B: I mean, this is an example of the internal tool or the internal analysis to give you the detailed answer, Sam, of everything we look at when we're trying to assess and grade inside of a private equity. Right. So there, it's top down, it's bottom up. How much spend is getting spend plays, what's campaign structure, what's how you made this? I mean, my team made this.

Speaker C: Yeah, that's so cool.

Speaker B: So this is what we go through and do, and we're going to turn this into software at some point.

Speaker A: By the way, any color coded excel sheet. We're like, oh, this is great. I remember Steph Smith came on and showed me like a, just like a beautifully formatted excel sheet. I don't think I even read anything that was in it, but I was like, you're great. This is fantastic. Like, I'm such a sucker for formatting on an excel sheet.

Speaker B: Well, and Sean's right, which is like the other thing I would think about too, that I think a lot of entrepreneurs miss because we're so caught up on ourselves, is the humanness on the other side of the table. So you say private equity firm and you're like, oh yeah, private equity firm. But what's really happening is there's a mid level partner. If they buy a business and Facebook blows up in a year on them, it's career limiting for them, right? So the human being on the other side wants to go in and sell this deal to their committee, be able to put a good case together. And the reason McKinsey and Bain both built billion dollar businesses doing this is because those people wanted to go, look. McKinsey says the market is big now. The dream is they go, look, Awk says there's x amount of EBITDA available in marketing. And look at the analysis they put together that's convincing of that.

Speaker C: What percentage of the deals do you say? It's shit. You're like, no, dude, like, there's no opportunity here.

Speaker B: We've had, I mean, it's a young business, we've only done 20 projects, but let's say on 25% we've said you should stay the hell away from, I mean, one, there was just straight up fraud and the SEO backlinking that they would have never spotted without us. That was a huge win. And they paid us. Obviously, they didn't do the deal. And then we've had a couple where we were not convinced that there was as much leverage. The management team puts together projections, so they share projections in these things, and we look at those projections and we basically go dude, this person would have to be the best Facebook ad marketer on the planet to hit these projections. We think they can grow, but we don't think the projections they put together are reasonable. And we need to double click. And as they double clicked on that, they lost excitement about the deal.

Speaker C: Wow, what a cool business. Good job.

Speaker B: Thank you. Much better than Khani.

Speaker A: So your thing was kind of office for the CMO. You talked about how accordion, and there's the equivalent for the CFO side. Can you talk about other businesses that are like this that sell to the ultra rich customers? So let's call it hedge funds, investment banks, whatever. I heard you talk about a business that I had never heard of called. I think it was first ring or first rain. What is that? That sounded very interesting.

Speaker B: Well, the first thing I always tell people to go, like, who's the richest man in New York? Sam, who's the richest man in New York?

Speaker C: I don't want to ruin your story.

Speaker B: Okay, fine. I'll say, ari, who's the richest man in New York? Do you think it's.

Speaker A: Here's the homie guess.

Speaker C: I hear the homie guess. A hedge fund guy.

Speaker A: Some real estate guy.

Speaker B: Yeah, Daniel Ock or Steve Schwartzman or whatever. Nope, nope, nope. It's Michael Bloomberg. It's the guy who's selling information. And so sitting at Goldman, I, like, had this terminal we were paying $1,200 a month for. And they never negotiate price. Every single terminal. They never do volume discounts. And you're like, damn. This guy's just. I mean, they're printing money in that business.

Speaker C: It also helps that he owns the entire thing.

Speaker B: Owns the entire thing. But duty, whether he did or didn't, the thing makes, like, 510 billion a year in EBITDA.

Speaker C: It's huge.

Speaker B: It's a ridiculous business, right? And so I'm sitting there, I'm an entrepreneurial person, and my boss comes up to me, and she goes, you got to set up first range, Jessie. And I'm like, oh, cool, what's first rain? I'm, like, looking through it, and it's like, pull the stock ticker and get an alert to your inbox when there's news about this company. And I'm like, this is just Google alerts. And she's like, what's Google alerts? And I'm like, what do we pay a month for this? She's like, oh, we pay, like, $2,000 per license. And I'm like, well, our group is, like, 40 people. Like, we're paying $80,000 no, no, we got a discount. It's $50,000 a month we're paying for this Google Analytics thing. I'm like, what the fuck? And so, you know, one of the. One of the categories for us now and again, remember, unfair advantage is very important. I happen to have lots of friends in this world because of where I went to college. Just whatever. Unfair advantage.

Speaker C: Where'd you go to college?

Speaker B: I went to Penn. Fancy the Wall street, you know, training school. So a bunch of my friends work at hedge funds and private equity, and, you know, these guys want information like they're willing to pay tons and tons of money for. They're not price sensitive at all. If they can, they can roi of everything they. Every decision they make, because that was what we got told about first reign. They go, oh, it's $50,000 a month, but if it gets us one trade ahead of somebody else, it's paid for itself for the full year. So because of the numbers they're dealing in, they can just pay anything, right? Just like the $200,000 to diligence the project for a half a billion dollar deal. It's nothing for them, right? So this category is a great one to sell into. And actually, I have another funny story. You guys were like, so on GLG. GLG has been like my life, my savior in business. What happened for me? I became a regular. Take that term any way you want for hedge fund dudes, for Facebook. Every quarter, ten same people would call me and they would go, how's the quarter going, Jesse? Do you think spend is going to be up or down? Because they own huge positions in Facebook. So one of the guys eventually is like, Jesse, I want access to your data. I just want the aggregate I'm allowed to share. That's my data. At ampush, I'm spending hundreds of millions of dollars a year. And he goes, I want just full real time access to your data. I go, I can give it to you in aggregate. I can't give you any client data. And he's like, well, what can I get to you? And I was like, well, Bootstrap company. I'm like, we've been dealing with this working capital situation with our bank. Will you just give me a $5 million interest free loan? He's like, done. He's like, done. So this guy Peter, he's a good friend of mine. Now, he gave us a $5 million loan so we didn't have to pay any interest to our bank to do working capital and all I had to do was basically give him a real time feed from our tableau or whatever of our aggregate CPM, CTR, whatever, all of our data for Facebook. So anyway, first Reign is a basic software tool. You sell to hedge funds because they're willing to pay anything for it. And so one of my ideas, by the way, and if anyone's listening, wants to build this with me, I need someone very good at analytics and decent at sales, is just in my network. I could probably get 5 billion in meta Facebook. Spend a, and give people a survey every quarter. Did you spend more or less? How excited are you? Like a detailed survey, ITD have to be a really robust survey. Then id go to all these hedge fund people and id say you can have access to this data every quarter, its $50,000 a quarter and you have to guarantee me two years of a subscription. And I think ID have people align out the door of people willing to pay for that data. And then I would do it for Google, then I would do it for Amazon, then I would do it for all of these different platform, dude, dude.

Speaker A: Even easier, we like, why not just go to triple whale who already has all the data.

Speaker B: Yeah.

Speaker A: And be like, hey, triple. Well, let's do this line of business.

Speaker B: Basically 100%. Yeah, let me license your data for the exclusive use in the financial service because that's not going to be important for them. And then you can basically create a thing that hedge funds would pay for. And the best thing, what I would do to hedge funds, I'd say I'm only going to sell it to 20 of you, but let's do a reverse auction. So now make them bid against each other for this data. And as long as you limit it, they'll do that because they don't want everyone having the data. Right. That's a really important thing to them. Them. But anyway, the lesson here is that category alternative assets are a great thing to bootstrap into because one deal basically can make you as a business and then you can go from there. Robert.

Speaker A: Yeah, my old business partner used to call it just adding a zero. He's like basically, what market or product can we go into where we do the same exact work, but we just add a zero to the end of the dollar amount that we're able to charge. Sam, you told me this with your events too. You used to charge, I think like dollar 300 a ticket, but then other people charge 3000 and then I forgot who it was like recode or whoever it was charged $30,000 a ticket and.

Speaker C: It was like the same work, same product. It was ridiculous. And I did the exact same thing, Sean, that you said you did, where you're like, I have an idea, but I'm broke, so I'm just gonna assume that everyone else is broke.

Speaker A: That's what I go hang out with other broke people.

Speaker C: Yeah, easy thing.

Speaker A: Which, like, the two takeaways from this, by the way, are sell to the rich. You know, you're gonna be able to add a zero to what you're, what you're doing. And then your way of figuring out what they need was, you had friends in that circle. You could go make friends, or you were using GLG. You were like, I have one area of expertise that could be my calling card to get in the door, and then that will be how I, you know, understand what these people need, and then maybe I can pair what I know with what they need and to a, you know, either a data product or a consulting.

Speaker C: Yeah.

Speaker B: And to tie it, to get. Tie them together, actually, anyone listening, I would say, what is it that you know extremely well or a couple things that are cross sections of each other? And so first figure that out, and then figure out who's willing to pay you the most money for what you know. That's essentially what I did with, with Aux business. I was like, I know this thing. Who's going to go pay me the most for it? And that group is going to pay me the most by far.

Speaker C: Can I. You didn't put on this sheet, but I want to talk, I want to ask you a couple of questions about this, particularly because I don't know if Sean knows much about this company, and I know a little bit about it, but I know that what I know, they're like, crazy impressive. So I think you sold your company to Red ventures. Is that right?

Speaker B: So we saw, it's a longer story. We sold a minority. They wanted to buy the whole thing. We couldn't get to terms. We sold a minority. We gave them an option to buy the rest of the business. They started buying content assets and decided not to buy the rest of our business. So we ended up eventually selling it to someone else. But we did for basically, you got to know them for two years, we operated as one company because the plan was originally for them to buy us. So I know them and Rick incredibly well.

Speaker C: Do you know about this company, Sean? Red Ventures?

Speaker A: I know about the surface level. And actually, we've hit up Jesse being like, dude, this is fascinating. Should we get Rick on the. I want to know more.

Speaker C: Well, but there's one part of the story that I just want to mention, which was amazing, is like, he started this thing and then he was actually on the plane that solely landed in the, in the Hudson. And he like, gave this like, amazing talk when he was like, I was like one or two years into my business, and for some reason, that life and death, that life or death situation kind of changed his outlook on life. And now Red Ventures is known as like, one of the best places to work. And it sounds like they're, it's a great company. So, yeah, what's the background?

Speaker B: Yeah, so the story, the way that they tell it, they started the business in 2000. So Rick and Dan are the founders, and they're both friends and both multi billionaires. And they, they actually met as sendant in the late nineties. You guys know what send in is? They had like the coupon book. They launched orbits. They were like the original Internet hold company. They met there very direct marketing heavy. So in 2000, the two of them broke off on their own, literally months before the Internet imploded. They started Red F is what it was first called five years later. And their story they're telling of it, not mine. Rick says, dan, give me a dollar. Dan gives him a dollar, he goes, you can have my half of the business. I hate this business. I don't want to do it. So they do a hard reset. Five years in, I think they barely were doing a million EBITDA. And these guys are the best learners you've ever met. So then at the time, go back 2005, there was this new thing called Google Adwords, and there was agency starting, and there were lead gen businesses, and they, for whatever reason, they had a relationship with DirecTV. They said, hey, DirecTV, if you remember back then, was looking for satellite people to sell in the mall. Like theyre these resellers. So Rick or one of them had this idea of, lets go to DirecTV and become a dealer. So they go, hey, DirecTV, want to be a dealer? I go, sure. We love dealers. Whats your territory? They go, oh, this new thing called the Internet will be our territory. They go, okay, sure. We dont know anything. So they became Directstart TV authorized dealer of DirectV. But as a part of their thing, they owned all the web rights, they owned all the Adwords rights, they owned all the SEO, and in four years, they built a $75 million EBITDA business just selling DirecTV subscriptions because they would run the media, take the phone calls, and all these things that are commonplace today where, like, what you do on your website gets cookied and then, you know, on the phone call, they were, they were pioneers in all of that stuff.

Speaker C: And basically, if. If someone became a reseller of the tv tech dish network or whatever, it was, DirecTV, they gave red Ventures, like, a $1,000.

Speaker B: They gave $500 bounty for every single customer they get. And red ventures just had to do it for less than that, right? And so between their media and, of course, after a few years, DirecTV is like, well, we can't get rid of you because you're driving all of our customers, but we don't like the deal we made. So then they renegotiated a million different times. And I, they still probably work with them, but then they went and took that out. And then General Atlantic, the big private equity firm, invested and has crushed it on that deal. And they went and did that for any high Ltv purchase you can imagine. So every credit card company worked with them. American Express, Verizon Wireless, people who sell pest control. Anything that was a long term purchase, basically, red ventures was either running their marketing, and when they invested in us, we want to do the same deal for direct to consumer companies, which did not work nearly as well as it worked for them, which is a different story for a different day. But that's what they got to. Then they got to 2015. They're doing 2300 in EBITDA, and there's no more growth left, which is why they invested in us. And they did a bunch of other things. Rick's really smart, and he goes, okay, I'm going to invest in Jesse. He did five other deals at the same time, same year, and a year later, ambush is going, okay, the other one went down to zero one. You know, but they bought an SEO business that they use their same playbook, and within nine months, they took it from three in EBITDA to nine in EBITDA. And they go, oh, shit. So that worked. Okay, let's go do a bigger deal. So then they bought, like, a $10 million EBITDA SEO content business, and then they took it to, like, 25.

Speaker C: When you say SEO content business, you're talking about, like, the points guy.

Speaker B: Yeah, the first one was reviews.com. the second one, I'm forgetting the name of it, but, yeah, like, the points. Then they finally. Rick, like, a couple of those, and Rick's like, all right, I'm ready for the big time. He went and bought bank rate, which is a billion dollar publicly traded company, for 100, and EBITDA. It owns the points guy, it owns creditcards.com, it owns and in less than two years they tripled the EBITDA of the business and then they bought Healthline, they bought CNET. I mean so they basically took their, and now the services part of their business is a tiny part of their business and the SEO content part is a massive part of their business. But the same culture, the same playbook and it's an incredible business. Incredible.

Speaker A: Can you explain what they're doing? So they buy these SEO businesses which is, let's just take bank rate as an example, people. Google best, yep, mortgage rate, more current mortgage rates, whatever. And they bankrate has done the content work and the SEO work to be the top thing that shows up on Google. So then you click it, you go in and they have like these affiliate offers and that's all great. And what Red did was they basically, am I right that they bought a business that was like primarily SEO driven and then they layered on paid to that. Is that the main thing that they did or what did they do to the assets?

Speaker B: There's four major levers they pull and the first thing I have to tell whenever I tell this story is Rick and it's the most unique culture. Like at some point you guys, I just take you there and you got to tour the campus and check it out because you've never seen anything like it. And there's a great New York Times article where they describe it as like part Wall street trading desk, part like southern politeness and part like hard nosed direct response marketing and that's exactly, it's a very apt description. But anyway, well, and that's why I.

Speaker C: Wanted to ask you about it because Rick seems like an anomaly. Like he seems like a, like a, like this is normally like kind of a not, this could be a shady industry. It often is a shady industry. He doesn't seem like a shady guy and it seems like a, like people love working there, which is rare.

Speaker B: He's one of the most special people I've ever met. He's one of the most special people in the world I think.

Speaker A: What would we notice if we toured the campus? What would we see?

Speaker B: It's funny you asked that. So one of my requests to him when they invest, I want to shadow your leadership team for a week. Me and my ten leaders are going to shadow your leaders and I want to see what you guys do. And what you'd find is these things that are like startup adages. They've done at a scale of 5000 people, every meeting is short. Every meeting starts with a bottom line. Numbers are the only thing that has ever talked about in levers. And every person is basically trying to optimize more EBITDA in any discussion they're having. And they don't talk about the work that gets done as independent of that. It's like another example is they shape teams for digital marketers. They don't say like we have a client team and we have a marketing team. They go, we have like team click through rate and we have team conversion rate and we have team traffic volume. Like they literally organize people by the KPI that they're trying to drive so that there's a deep, deep focus into it. They have these really cool things called business reviews where basically Rick and the leadership team sits and you have 20 minutes to come in, give an update on your business. Real decisions are made about the business. And he does like 40 of those, or like 40 over two days basically. So its a high energy, very smart, its a very unique culture. But anyway, the culture is a starting point by far because without it, I dont think any of this works. They have four main levers. The first is improvement of traffic acquisition, both paid and organic. So to your point, Sean, theyll layer on paid in a really smart way. They think a lot about cost per visitor and revenue per visitor and get that equation working extremely well. But theyll do a lot of SEO as well and theyll get volume up. I remember high level when they bought the points guy, Im making these numbers up, but it was doing $0.70 in revenue per visit and maybe $0.40 in cost per visit. And two years later was doing like $1.70 in revenue per visit and like $0.90 in cost per visit. But the visits were up by like a factor of two or something like that. Right. So first lever is traffic acquisition, second lever is theyre extremely good at onsite optimization. If you guys pull up the points guy or any of those things now, youll say, wow, platinum American Express is plugged here, but it's plugged in a smart way. But I want to click on it, but it doesn't feel too salesy. They're very good at getting basically the on site optimization to be significantly higher. The third lever is they're incredible geniuses when it comes to pricing to the efficient frontier of a customer's curve. You guys know what I mean when I say that.

Speaker C: You're using a lot of words, my friend, dependently.

Speaker A: But when you put them together that way, it's just a combination I wasn't familiar with.

Speaker B: So when you're a credit card, so you're American Express. Express, right. And American Express is probably worth willing to pay $700 per credit card application, but their person on their side will pay 200 if they can, right. So the only way, if you can figure out the exact willingness to pay for an incremental customer by your customer in their business, your profits skyrocket. So they basically, the simple way to say it is they're good at pricing. They can really charge more for what they get. And ill tell you a funny story. The guy whos retired now, but hes a good friend of mine. Hes a southern dude. Hes very disarming. But then hes smart as shit. And hes like, Jesse, we were 60 days from close. We were going to close this bank rate deal. And their team told me there was a bidded auction for how you bought credit card applications and no technology could beat it. He said, I looked at it and I said, discover is only paying 500 for an application. And they said theyre willing to pay 900. Why are we not charging them 900? Hes like, well, thats how the algorithm works. Hes like, buying this deal. He goes, the day we closed the deal, Jesse, I threw away that algorithm. I pulled up a spreadsheet. I called all the customers. I said, what are you willing to pay? What are you willing to pay? I got them. I charged them exactly what they were willing to pay, and I got 20% more in EBITDA overnight. Within the first month, I owned the business. And so thats the third lever theyre good at. And then the fourth lever is theyre not crash and burn people, but theyre very thoughtful about. And when they invested in ambushe, I cut the headcount under their sort of tutelage by more than half. And our revenue grew during that time. So they're very good at, like, truly challenging the bloat in an organization and being like, how many people do we actually need? Like, one story you guys will love is one of their executives that they bought some, like, government owned thing. It's a really weird business that mails you, all the mailers when you move. I'm forgetting the name of it right now, but I hate that. So it's actually was owned by the USP's. And then it got.

Speaker C: I hate that.

Speaker B: Now red Ventures owns it. I go, so how'd you decide how to reduce the headcount? He goes, we took the top three managers in the company, and we held a draft. So we basically put everyone's name on the board and we said, there's only 40 people of 80 staying. Now go draft your best people. And again, they're compassionate with, obviously, the people they let go. It's not meant to be a negative towards them. But these organizations, they're very good at leanly staffing. These organizations. Those are the four big levers, and that's how they get the results they get.

Speaker A: That's dope. Appreciate the red Ventures masterclass. That's great. They're like a juggernaut that I didn't know much about in terms of how they actually operate.

Speaker C: Your boyfriend, the guy from Silver Lake, the guy you love, who's the guy? What's his name that you have a crush on?

Speaker A: I should probably know his name if he's my boyfriend. Egan. What is it? Egan.

Speaker C: I think he's on their board.

Speaker B: Yeah, he's on their board. Ga is on their board. And I mean, look, they're all minority holders. They've never raised a dollar of primary capital. So they're, in my opinion, they're a bootstrap giant, right. They've taken secondary, but they've never raised primary.

Speaker A: Their headquarters is like North Carolina or something, right?

Speaker B: Yeah, they're in Charlotte. But again, dude, Rick is a hustler of all hustlers. It's right across the border in South Carolina. Because the state of South Carolina has paid for the whole thing. With tax incentives.

Speaker C: You have on here. Every profitable founder should understand PE and roll ups. What's that mean?

Speaker B: Yeah, I think one of the biggest value creation levers, if you're running a two to $5 million EBITDA business, is a roll up. And ill tell the story of the company that ended up buying ampush because its kind of like, still hurts me a little bit when I tell it. So there was a business called Elite SEM as an SEM agency, 4 million EBITDA same year that I think ambush had like six or something. In 2015. We went and did this deal with red Ventures, whatever, learned a ton. But these guys sold to a business called Mountaingate Capital. And lets assume. I dont know what they paid, but lets assume it was on eight times EBITDA, which is fair multiple. So they paid 32 million for the business. Right. The founders rolled 30%. I don't know for a fact, but I'm just making that up in this scenario. Founders roll 30% of the value, they take 20 million off the table and they roll the rest in. Mountaingate goes and buys another six different businesses in the one to 2 million EBITDA range. Now, for those businesses, they pay, like, four to five times EBITDA. Then they grow the whole thing organically, right? So then they go for, was it math? Four. Let's say they buy another five or six companies. They buy ten and EBITDA, right? Total invested. Capitals call it 60. Ballpark.

Speaker C: But now the business is worth 15 times.

Speaker B: Correct. And it was bought by New Mountain, who bought ampush. It was bought by new mountain for 15 times 15, which is 225 million EBITDA. So the founders got 20 million plus, then got another byte of call it 40, or something like that. Plus the PE firm obviously crushed it on it. My push to founders would be like, if you understand that multiples are a function of growth, stability, and like, and margin or defensibility, however you want to think about that, and all those things improve with scale. And so there's just what they call the finance nerds call it multiple arbitrage, which means I can buy at a low multiple, and then I can sell in a few years for a higher multiple. And I think a lot from, if I'm a profitable bootstrap founder, including myself, like, even for growth assisted and other things, I'm like, this seems like such an obvious path to create a tremendous amount of value that's. That's, like, better than the venture path for so many different reasons. More apt on more just, you know. But, yeah, I think everyone should look at it in their space. And by the way, I think I've been approached multiple times and pitched on this, and it's on my list of, like, creative AI meets roll up. So, Jesse, go. Let's go buy a creative agency, redo their processes with AI. Right? Then once you figure that out, let's go buy ten more of them. And not only will you be able to roll up and get all this multiple arbitrage, but you will create a much more profitable business. So I think there's a lot of strategies out there. And I would say, like, I think a lot you can do with private equity without private equity, but the founders of running these businesses should be the ones leading them. And the more the founder has the strategy, the better they're going to do with the PE firm if they ever need the capital to go do it right.

Speaker A: You mentioned AI. I want to ask you about that because you were early to the social networking wave. I think you were doing a social networking type of thing in the first year of Facebook. I think there's some story where Zuck called you.

Speaker B: I called him on a cell phone and pretended to be somebody else. That was a good one.

Speaker A: You called Zuck. Tell that story.

Speaker C: By the way, who did you pretend to be?

Speaker B: So summer of zero five, we're like, Facebook's. Oh, my God. Mark Zuckerberg's a year old. He's our age, right? We're like, he's our age. He's going to crush it, but he's never going to go into high school. Somebody should start a high school Facebook. And we're like, why not us? So we started the high list. I have the docs, we have these little iconography and all this stuff. We basically rebuilt the clone of Facebook. And at the beginning of the summer, we went to go buy HS facebook.com dot and some kid at Columbia. I don't even remember his name. Maybe he's listening and he can phone himself. He owns it. And he goes, well, I'll sell it to you for, like, $20,000. And we're college kids. We're like, no, thanks. We'll call it the high list. And we say, peace. We build the whole product. We launch it. Literally, on the eve of the launch, he calls us and he goes, Mark Zuckerberg wants to buy HS Facebook. So I'm giving you a last chance, buddy. You can get it. And I was like, oh, my God, we need. And I was like, my first question was, is he gonna launch in high school? He's like, yeah, he says he is. And I'm like, no. Are you sure? Like, I think the guy's bullshitting me. So I'm like, prove it. So he forwards me the email from Zuck, and this is just a guy named Mark Zuckerberg. He's not Zuck. Zuck today, right? And the guy includes a 917 area code number. Sorry, Zuck. Your area code's 917 on your cell phone. And I don't know what the rest of it was. I don't remember. But basically it has a cell phone number. So I'm like, okay, how do we call? And how do we verify this is true? So I call Zuck, by the way, I call him from my summer internship office at Bain Capital. So I'm, like, sitting inside some finance company calling him, and I go, my name is Tom Goldberg. I'm partners with this guy Bob, and we own Hs Facebook together. So I want to make sure that you're not, like, I'm not getting cut out of this deal that you apparently have with him. And he goes, yeah, I'm going to buy it from him. And you need to sort that out with him. And then I go, well, what are you going to do with it? And I kid you not, he spends 30 minutes and to his credit, he outlines the entire strategy of Facebook has executed. He goes, first we're going to go to high schools, then we're going to go to workplaces, then we're going to go into pods, then we're going to like, he had the whole strategy. This is in zero five, dude. This is a year into Facebook.

Speaker C: And he's like, he's wearing chains and.

Speaker B: Cool shirts right around the world. He's like 22 or when I'm 21. And then he's like, wait, by the way, what was your name again? And I'm like, click. Needless to say, our high school Facebook plan did not work out. They launched and they crushed us and we went and got jobs in finance.

Speaker A: That's an amazing story. And by the way, isn't the funny thing that like, the actual answer was go join Facebook. Like, just do whatever you want.

Speaker B: Every point in my life that has been the right answer to maximize my outcome. When I started ambush dude for ten years, like, I was before all their ads and I did the math because a buddy of mine got a job with same resume, got like a corp dev and he didn't take it. I was like, he's an idiot, but he didn't take it. But he, we have his offer. We have his physical offer still. It's like, oh, that would have been worth $75 million, dude, I talked to.

Speaker C: A guy the other day who was like the two or 300th employee of Facebook and he was like, I had $100 million in Facebook stock. Yes. He worked there for seven years or something like that.

Speaker B: What I should have done is said, hey, look, I started this high school competitor, do you want to hire me, dude? Because I'd probably be a billionaire right now because it was a year into the business existing.

Speaker A: And by the way, to start Facebook, unbelievable amount of work and genius to be the founding. Kind of like 1st, 510, 1520 people there. Tremendous amount of work. You're scaling something that's, that's massive and you got to be like really sharp or you're going to get washed out. To be the hundredth or 200th person at Facebook. Don't need anything special, to be honest.

Speaker B: Like, hey, get over here.

Speaker A: Can you lift boxes for a bit? All right. He lifted boxes for a bit. Hey, can you, um, we got a bunch of spammers. Can you look at all these and figure out like, what we're going to do. Tell the team, like, we need people to filter this by employee 200. You no longer need to be at the top of the genius curve or work, you know, an incredible amount, and you still get rich.

Speaker B: I, four years into am push, I was looking for a head of sales, and our best place to hire salespeople was from Facebook itself because they knew how to navigate the beast and get us more kind of leads from that. Get this guy. We love each other. On the first dinner, you know, he meets two other people on teams, and he's four. Four interviews in, and I do the classic talk. All right, let's talk comp for a second, right? We're a startup. We'll give you a couple points of equity. And he, like, gets this very scared look on his face. He goes, Jesse, I'm investing $800,000 a month in Facebook stock. How are you going to match that? And I'm like, I'm like, dude, what? What? Good to meet you, buddy. I'll see you later.

Speaker C: That is absolutely insane. Uh, Sean, have you heard the story about Noah Kagan and how Noah was hired to work at Facebook? Noah was the 32nd or 30th employee. And basically what happened is he was out at a party and he was drunk or something like that, and he tells a reporter, a TechCrunch reporter, we're going to launch this thing and that thing, and it's going to be the best thing ever. And it becomes a news article the next day. And Zuck goes to his desk and he goes, you're fucking with my company. You're out. And he fires him on month nine. So Noah was three months away from his first vest, and Noah's told me, he goes, had I just made it that three months, those shares today would be worth about $100 million, those three months. All because he kind of had a big mouth when he was 21 and drunk at a party.

Speaker B: He was ambush's first Facebook ads client, believe it or not. Appsumo Washington.

Speaker C: That's awesome.

Speaker B: I bought his first. I got his first customers for him.

Speaker C: Yeah. And now it's like, you know, a business that does 100 million a year in revenue, so it kind of worked out, but it would have worked out a lot easier if he kind of kept his mouth shut.

Speaker B: Yeah. You know, but my thought, I don't know how you guys feel about that. I've done that math, and I'm like, but I don't think I could have worked. Like, I don't want to work for someone.

Speaker C: Of course you can't look back and.

Speaker B: Be like, but even if I could even now make that decision, I'm like, I don't think I would have wanted to work for Facebook or anywhere for that, that long. Or like, dude, I would.

Speaker C: That would have been awesome. Are we going to say, sean, I.

Speaker A: Think they're both right. So the math on this, just to put it in perspective, let's say you join when Facebook is valued at a billion dollars, which I think it was like a fee, like a few years in. I don't think it was like right away at the time, it was unclear social networking would be that big. And so let's say you join at a billion dollar valuation and your employee, you know, 400, and you're so junior. You're a junior and they give you $10,000 of stock a year. You're going to make, you get a hundred thousand dollars salary and you're going to get 10,000 of stock. Over four years, you've accumulated $40,000 of stock. Even at a billion today, Facebook is a $1.35 trillion company.

Speaker B: So that's, you get thousand bagger, multiply.

Speaker A: By 1300 times your 40,000. It's a $54 million stock option you got for being the janitor at Facebook at the right time. Which tells me a couple of things. Number one, picking the right company and project will be like, by far picking the right market to be in the. And then the winner of that market, if you're in the tech industry, is by far the most impactful thing you could do in your bit, in your, like, career. It'll, it'll beat your hard work, it'll beat your own, like, you know, intelligence, it'll beat being right many times in a row. Like, you just had to be right once in the right time. And I should point this out, which is that, but at the time, or like every kind of, like four years, it's pretty obvious what, like, winning companies look like. So my version of this was I only did two job interviews in my life. The first one was at Monkey Inferno, which is the studio I ended up joining because I wanted to be in a studio. And the other one I did was stripe. And I could have told you right then, like, stripe is the winner. Like, it's the winner of the startups. The reason that was the only other interview I did was because I was like, stripe is the winner. It was super obvious. And I've done the similar, like, heartbreaking math of like, wow, even if I had joined, I would have just been like a sales guy, biz dev guy. Like, I had no, like, I would. No seniority, would have made an absolute fortune. Now, the other hand, you have the Jesse thing, which is like, do you want to do it? Would you, would you actually have stuck it out? And even beyond that is, would you have held? Because there is no chance that I would have held. I bought bitcoin in 2014. I did not hold all the bitcoin. I gambled for bitcoin away on a poker night one night because I was just, like, playing online poker. I did all kinds of things. That's now a four times $60,000 thing. At the time, bitcoin was like $300. So it was like, I thought $1,000 investment. It was actually a quarter million dollar investment. And so the idea that I would have held is ridiculous. And I don't think the math is actually real because nobody holds for that long.

Speaker B: I agree.

Speaker C: That's insane. I've got the same story, by the way, with Airbnb. I think I was going to be employee 120 or something. And I don't know. Also, it was a $20 an hour job. I don't even know if the equity would have been a lot. But you do the math and it does sting a little bit.

Speaker B: But, dude, the one way I worked at Goldman, I was 25. My 29 year old boss made $2 million a year. My 35 year old boss was making $15 million a year. And I got off that path because I was like, I don't want to sit here and look at spreadsheets all day. It's a very not dynamic job. I didn't. I looked at my boss, I said, do I want to be them one day? And I said no. And I literally wrote this down to keep myself honest. I said I would. I'm okay with, like, half my personal expected value to be able to, like, do my own thing in the future.

Speaker A: I don't know.

Speaker B: I've never rerun the math, but, but I had to, like, make that, you know, decision for myself.

Speaker C: What's, what's a $15 million a year employee at Goldman do?

Speaker B: There's a bunch of jobs that make that kind of money, but in my world, I was in the, like, the buy side hedge fund. They were investing. We had a $7 billion fund. Two and 20. If the thing delivers 10% a year, they make. The fees on 7 billion are like, what, 140 plus 10% is 700 million. It's like 350 million in carry. And there's four senior people now. Golden White. It can even get half of it or whatever, but they're paying 50% out of whatever people make in this world. But then bankers make that much. I mean, all these financial services at a senior already level, they all make tons of money. There was a guy who endowed a scholarship I got when I was at Penn, who was a partner at Goldman, at the head of the infrastructure fund. I was making 55 a year is what he told me.

Speaker A: And then when he told you, did he just like, smirk, the biggest smirk you've ever seen in your goddamn life? And it just. It was permanent. He had a facial, but I saw that.

Speaker B: I was like, yeah, but you've been there 30 years, and like, if you've ever been to those atmospheres, none of the three of us would last more than two or three years in those atmospheres. They're not, they're political. They're smiling. It's nothing. I don't know. There's more than money, right?

Speaker A: I totally agree. I think our actions have showed that. But I also think it is entertaining to see just the sort of mind bending amounts that people make doing certain things. And in the case of joining companies early, wow, that's kind of it. That's all you really had to do in terms of financial success. There's a funny tweet that Chamath put out the other day where he was like Bill Gateshead, you know, if he had just basically held his Microsoft stock, would be, I think, the richest man in the world, or number one or number two, something like that. And instead he did the Gates foundation. He did a whole bunch of other things he sold and then has his family office. And the top reply, which was a huge ratio, was like, now do you with meta? Because he leaves Facebook. He's like, great, I got a billion bucks. And then I'm going to do social capital. I'm going to do this, I'm going to do that for, you know, to do SPacs. I'm gonna do all these things for like, you know, the next twelve years, 15 years. And if he had just simply like, held the meta stock and chilled, he would have financially out far outperformed his own, you know, his own brilliance doing all this different investing action.

Speaker B: Yeah, you know, but that's the thing. That's why you got to do things that you actually care about or that light you up or that you motivate you in a way that's different from cash. Because, I mean, dude, the other thing, how many? I mean, you guys probably have friends like this. I have friends who are worth more than I am, who have much more money, and I. But they got it through, like, a meta type situation. They're, like, the most insecure. Like, they're like, oh, I just got lucky. They're afraid to talk about it. Like, it seems like a horrible existence. And there's a lot of people I know like that. I met one of the founders of YouTube once, and the guy was like, my lotto ticket success, you know, I don't, like, he was very unhappy with the amount of money he had made. So you think that it's like, I'm on easy street. I get it. Like, but the psychological thing, those people feel like fraud. I mean, it's a whole nother. There's a whole nother vector of challenges that come with it, versus I think all the three of us are founders. You start a business. Whatever it is you made, you made it. You know you did it. Like, there's a different element to it, in my opinion.

Speaker A: I like talking about it the same way I like looking at mega mansions on the Internet. It's fascinating to one part of my brain, but then the main part of my brain is like, I wouldn't even want that out.

Speaker B: Like, yeah, exactly.

Speaker A: Like, not even in the. It's like, dude, that's way too big. That wouldn't be fun to live in. That'd be uncomfortable. And, man, the maintenance of that would be like a pain of the ass. That's not what I want. In the same way that when we got acquired by Twitch, I had thought in the last seven years, I had worked towards, like, I want to build a, you know, like, a successful tech company, right? I was in the venture capital world. Success in that world, as you build a billion dollar plus company, we were doing, like, a social type of product, a media product, and Twitch is, like, one of the ten winners that, like, actually existed. And then I saw Emmett's day to day, and I was like, oh, man, I would be miserable if I was doing this. And not even in a, like, like, it was just, that wasn't fun. Like, his job fundamentally was, like, putting out fires and all problems roll up, basically. And, like, it's the worst problems that roll up. Yeah, shit rolls uphill. Exactly. It's the worst problems that rolled up past your executive team, because they would solve a bunch of them, but the ones that they can't really solve cleanly roll up to you. So you get the worst of the worst that roll up to you. And he would sit in the conference room and basically on, you know, his calendar was managed by somebody else. There's a 30 minutes block and another 30 minutes block, another 30 minutes block, and he's reading memos and he's doing decisions all day. And I'm like, man, this is not like. Like, the fun factor is not there. And that's when I started asking a question. That's why I started this podcast is, I was like, who's having the most fun? Rather than who is the most successful, who is the most rich. It's just fundamentally who's having the most fun. And I remember looking at Joe Rogan, I was like, I think Joe Rogan's having a blast. It seems like he basically, the podcast, which is like an unedited, unscripted thing, he's hanging out with comedian friends or super interesting scientists and I paleontologists and just fascinating people like that. And then on the side, he does comedy, which is like a craft that he really cares about, that he does. He does the UFC, which is his hobby, and he gets to commentate for that, sit ringside. But he also doesn't overdo any of the things, meaning he doesn't do his podcast in a way that's optimized for views. He's not like, I want to do a three hour conversation because that's what I want, not because that's optimal for the algorithm for UFC. He doesn't travel. He's like, I'll do the ones that are nearby me, but I'm not going to fly around the world every weekend commentating this. Like, I hope that works for you guys. Same thing with this comedy stuff. He's like, you know, I'm going to do it the way that I want to do it. And when I saw that, I was like, okay, that is a different model of success that I, you know, I want more than, than kind of what I wanted in my twenties.

Speaker B: You use Joe Rogan, but I honestly think you can apply that to anyone. Like my hedge fund friends who love hedge funding. They're happy. They love it. It's finding your thing. It's finding the thing that you really enjoy and then just going all in on it. Those are the people, I think, who are winning.

Speaker C: You really got to enjoy doing it a lot because it all really sucks to get there. Do you guys remember Zuck in zero six to maybe it was zero eight to 15? I would not have trade places with him. I would never in a million years trade places with Elon Musk. But the idea of having all these things.

Speaker A: Me neither.

Speaker C: No trade.

Speaker A: I also reject that trade Sam far.

Speaker C: Yeah. Very, very, very fair of him to say that, but it does seem cool. I guess what I mean is I could acknowledge that that seems awesome. That would be cool to have, and also, I'm not willing to do it, but that's fantastic.

Speaker B: Yeah.

Speaker A: I think one of the most powerful things is figuring out there's a difference between cool for you and cool for me. Right.

Speaker B: That's right.

Speaker A: There's so many things where I see people's life setup, and I'm like, that is super cool for you. I don't mean that in a negative way. It's like, I do think it is super cool, and I think it's even cooler that it's what you wanted. But I have to figure out what is cool for me.

Speaker C: Look, like, you know what's funny is our last episode, you talked about the seven spiritual roles, and you talked about that book that you were reading or how you were thinking about reading or something like that. And I went and bought it because, personally, I'm in a little bit of a place now where it's like, I think some people call it the second mountainous. You know, you already, like, achieve a little something to where you're like, you're secure, but you're like, all right, but what's a problem that I want to work on or a way to spend life that may be a little bit higher up on Maslow's hierarchy of needs? And so I'm personally still, like, asking myself, it's not defined yet for me.

Speaker A: Jesse, do you have one? I'm curious.

Speaker B: Yeah. You know, I've done, I think, Sean, you know, this. I've spent probably the better part of six or seven years on this personal growth journey, which has turned into, like, a spiritual journey. And the defining moment came for me maybe three years in when my coach was like, what's the one thing you can't not do? It's like, a really weird question. And the exercise for you can do it, Sam, right now is, what's the one thing you can't not do? Write down a few sentences, and then every week, look at those sentences and see if they seem to grow with you.

Speaker C: That's a good idea.

Speaker B: And in one funny way, he says, what's the thing that comes in the room when you show up? What's the stench? Because his point was, we try to make purpose this far out thing we have to go get. And it's actually the thing already inside of us that we just need to, like, tap into and live more fully. And for me, it was. I love helping other people, like, be the best versions of themselves. Like, raise their game to the next level of what they're capable of. Even in this podcast. Like, I think I taught you guys two new things. Like, it just, it comes out, it's not purposeful. I've made it more purposeful now, but, like, at the time, it wasn't, but it was a thing anyone, my friends would tell you about me, any of my employees would tell you about, like, dude, jesse walks in and like, the bar goes up and it's an exciting go up. And so one of the interesting examples of this, he goes, how do you keep your to do list, Jesse? And I was like, oh, initiatives or clients? And what if you kept your to do list based on your people you worked with, like, executives and how you're helping them be the best versions of themselves? He's like, you'd probably still, like, get the work done that you need to get done, but you do it in this very inspired way. And Gateway X, I mean, Gateway X is a whole function of me going, the thing I want to do is help other people learn and grow. I'm not the CEO of any of these companies. Like, now I do actually keep my to do list that way. I don't write growth assistant or Aux, I write Adrian and Casey. And I'm like, how am I helping those people? And I find it's a weird thing when I frame my success or my life through the p and ls of those businesses, I get very, like, I'm not, I'm not as powerful. I'm like a more scarce minded person. And when I frame it as the, like, how do I help those individuals? Which is the same shit, because they're running the businesses, I'm, like, creative and I'm happy, and I'm more flowing. And so for me, it's like, that's the thing. And it feels really energizing for me. I think I could do it for a really long time. And obviously, the setup, the way I've got it set up, matters a lot, too. Like, I'm not running any of the individual businesses. I don't think I want to. I don't want to run staff meetings. I don't want to run comp plans, hiring, all these things. I did it. You guys have done it. It's not what I want to do, but I do want to help grow each of these businesses.

Speaker C: Dude, you're awesome. I appreciate you doing this.

Speaker B: Thanks, man. What do you think?

Speaker A: Great to see you, by the way. How'd you get Nelly at your birthday party? What was that about? Tell that story before we go do quick one.

Speaker B: So I turned 40 in May, as you guys know, and I have a cool video montage of the party. My wife find an awesome party, but I've been telling all my friends about St. Louis since I was 18, so I went to college. I'm like, St. Louis is the best city, whatever. And everyone's like, I was. I'll move back there one day. They're like, no, you're not. And then I moved back, and they're like, oh, shit, you moved back. And so I had 200 people in town who I've been raving to about St. Louis for, like, ten plus years. So I'm like, what's the most ridiculous thing you could do if you're me? Having your 40 like Nelly? I mean, you guys are somewhere similar in age. From my high school to early college, Nelly was, like, the biggest rapper on the planet, and he's from my hometown.

Speaker C: Nelly was our guy. He was the first famous St. Louis guy. And it doesn't matter what race you are, how old you are, Nelly was like our son. He made us so proud.

Speaker A: If you're in your thirties or forties, just close your eyes. I'm just gonna say a few words that'll just take you back. Country, grammar, air force ones. Ei shot, and her. Oh, my God. Like, just the memories that come with those words.

Speaker B: So I'm like, all right, what's a ridiculous thing? I could have my party. I'm like, have Nellie perform there. So my wife goes through the normal channels. They're like, you know, he basically doesn't do this, right? So he's like, look, it's 300,000 just as a starting price. By the time you do it all, it's half a million dollars. And I'm like, I want to die with zero. But that's a little rich for my blood.

Speaker A: I don't want to live with zero.

Speaker B: Yeah. So I'm like, all right, we're not going to do that. And then I kind of am sad for a few months, and then the entrepreneur goes, wait, come on. There's got to be another way to approach this, right? So St. Louis is not a big place. I ask a couple of people, I go, you know Nelly's people, right? And I'm like, can you introduce me? And so I get to know they're great by, there's this guy, Mike Chafe, and there's these wonderful guys. I get to know them, and you know, they introduced me as this guy who's, like, an expert digital marketer, e commerce guy. So I'm like, hey, what's going on? What's going on in your world? Nelly's actually working on two big e commerce businesses like his team is. And I go, ooh, tell me more. And they tell me all about it, and I'm like, okay, well, here's the thing you should think about and make sure you tag this problem. And they're like, oh, wow, you know a lot about this. And I'm like, okay, how can I be helpful? Right? And then I just basically have been working with them. And right here's the Shopify app. Do this. Here's a good contractor for this, really helping their team get it going. And at some point, it came out. The aux business came out. And I'm like, yeah, I charge private equity firms, like, two, $300,000 to do that. Nice, right? And they're like, oh, but you've just been doing it for free. Like, what? Can we be helpful? I'm like, it's funny you ask. A young man's dream would be to have Nellie at his birthday party, and, you know, they're his people, so they're like, well, let's go talk to him. And they go, well, he's got to meet you because he doesn't know who you are, and if he doesn't know you. So I take my wife, you know, I get my, I get my sort of urban, like, going, I'm there. And we become. He's super nice guy, really friendly dude.

Speaker A: Have you ever been more nervous walking up to that meeting?

Speaker B: I was nervous. My wife was super nervous. She's like, why the hell am I here right now? We meet him in, like, this soho wannabe in St. Louis, club wannabe.

Speaker A: You go for the handshake, dap up. What are you doing?

Speaker B: Yeah, you know, not the handshake, but the, you know, pull in. Yeah, yeah, of course. And so that goes really well.

Speaker C: Yeah, my guy. You start using that phrase, my guy.

Speaker B: Yeah. And he asked me, what do you want to do? And I think, like, I was like, oh, man, you got to come out to EI. We got to have the intro. It's going to be like. And he, like, looks at me, he's like, okay, you're a real fan. I'm like, yeah, man, this, like, you were. You were the guy. So then they're like, okay, Nellie loved you. We're in. Then they're like, wait, what was the date again? It's May 25. Like, well, he's in Napa on the 24th night at some festival, and then he needs to be in Vegas on the 26th day for a day party. And they're like, he would do it as a friend now or because you've helped him, but he just can't make the date work, Jesse. And so again, I'm depressed for 48 hours, and then I'm like, no, fuck this. I'm like, what if I fly in private both ways? And they go, we'll talk to him, come back the next day. Okay, he'll do it, but it's got to be a g four or better.

Speaker C: Oh, my God.

Speaker B: Nelly does not fly in anything below a g four. So I go and I do a bunch of, like, you know, I've been flying private a little bit since the amplifier sale. And I was like, talk to a bunch of these brokers and I basically get them to beat each other up. And it was round trip, so it got a little cheaper per hour than it normally would, but for 60 grand, I got him a round trip on a g four. Napa to Stl. Stl to Vegas. And he rolls into the. You know, he rolled and he. By the way, he was amazing at the party. Like, I'll text you guys videos and stuff. Like, he. It was scary because he wasn't under any contract with me, so he could have come out, said, hey, happy birthday, Jesse. Ei. Ei. And he could have left. He ends up doing a 45 minutes set. And he told, like, his manager. Manager told me. He's like, dude, he was, like, so hyped. There's, like, all these indian people who, like, knew his music. Like, he was so pumped that you guys are all just, like, rapping. My brother and I are on stage rapping EI with him. Like, it was. Dude, it was a top three life moment. Like, it was unbelievable.

Speaker C: That's so awesome.

Speaker B: Yeah, it was the best. Like, it was honestly one of the best hours of my life.

Speaker C: That is so cool.

Speaker A: Little dicky. If you're out there listening, I would. I'm turning 40 in a few years. I would love to start, you know.

Speaker B: Yeah, you gotta save that money, dude. You gotta save that money.

Speaker A: You.

Speaker C: Yeah, you have to hope that his career just goes down.

Speaker B: Why? Tell my wife I'm like, for your 50th, I'll get Beyonce. Because hopefully by then I'll have a little more money. And you will. Her stock will be down.

Speaker A: Yeah, we gotta just catch them right before they hit cameo, so they can't be peaking. They gotta be on some sort of a decline, but, like, not all the way rock bottomed yet. So that's. That's what we're going for.

Speaker C: Um, Jesse, we appreciate you. You're the man. Thanks for doing this, you guys.

Speaker B: Good to see you.

Speaker C: All right. That's it. That's the pause.