I Crashed A Party To Build A $100M Empire

So I like sneak my way into this party. I find like the main dude, the publisher of this site called Cult of Mac. And I'm like, hey man, I got this bundle. Like, will you post about it? And he's like, I don't know, like fine, you know, like whatever. And so he gets one of his people to like post about our thing. And like, you know, the next day it goes live. We sell like 200 of these bundles in like a day. The next day, another publication reprints it and we sell another 100.

All right. So we got something really special today. I got my fellow JP, good friend Josh Payne here, who is a Bootstrap Giants founder. And we wanted to play around with a new format today, kind of exploring maybe deeper, younger motivational aspects of being an entrepreneur, at least in our case. But before we do that, I want to welcome Josh. And Josh is one of my favorite Bootstrap Giants founders. We probably met 4 or 5 years ago.

Yeah.

We've explored partnerships together. We've taken long walks together. Josh, welcome to Bootstrap Giants.

Thank you. Thank you for having me.

Let's just jump in and let's hear your sort of entrepreneurial story. Tell us how you got started, what you built, what you sold, and now what you're working on.

Yeah. Yeah, I think classic sort of founder story. You know, when I was younger, I always knew I wanted to start something. I think I had that like that that fire or drive in me from an early age, which is you know maybe something we'll talk a little bit more about where that came from. And but I grew up in a small town in Indiana. You know, my dad was in in sales, which is frankly like classic entrepreneurship. But like you know they had you know I had no idea how to become an entrepreneur or or You know, to get going. And I wasn't a programmer, so I couldn't really build my own thing. Although, you know, I went to— for undergrad, I did— I tried to do computer science, but I wasn't smart enough. So I did CIS, which is computer information systems.

Where'd you go to school?

I went to IU, Indiana. Yeah, which is a great school. Had a blast. And yeah, like over Christmas break of like my senior year, I interned at Intel in Silicon Valley my junior year, and then kind of caught the bug. Like, you know, was like, what year was that? It was like '99 or maybe— no, it was like 2001. And so Google was just like, just kind of getting breaking out at the time. And like, but anyway, yeah, I stayed home over Christmas break that following year to try to like, you know, build my own e-com store, sort of my first little Foray, and but you know I didn't have any money, so I went and took the full-time job from Intel. And funny enough, like funny story, I've said this before, but like Noah Kagan was also interning at that same time.

Oh really?

And I like saw him like sleeping under his desk a couple times, which is classic.

Noah was my one of my first clients at Ampush, believe it or not.

Oh really?

We used to buy all the ads for AppSumo. Yeah, he was the worst client ever, like the most annoying client in the history of clients.

No doubt. That's why he's the best. That's, you know, that's why they got to where they got. Um, and as Noah would— I'm sure you've read in his post or whatever, like, Intel was soul-crushing. But, you know, again, I was from this town, didn't know how to start, like, didn't know what to do, right? It was just— I tried, I built my own thing, but I didn't understand, like, how to run ads. And, you know, this was early days, like '03, '04. Um, so long story short, for the next decade, I really spent a decade preparing to launch the startup that would ultimately work called Stack Commerce. And we'll skip over it today. But like, there was a lot of things that happened in that decade, like other startups, you know, going back to business school because I didn't know what the fuck to do. Or like, you know, I kept thinking like, how do I meet, you know, how do I meet a co-founder? How do I write in? I was like, oh, maybe business school. And so, and actually the thing that did it was I went and worked for an incredible Silicon Valley, Sequoia-backed startup in the Valley. Worked for them for like a year. It was called Meebo with an M.

Sure.

Ended up getting fired after like a year, year and a half for a variety of reasons. And that was like this huge, one, experience of just learning from them. And then two, like getting fired was like, oh shit, okay. You know, kind of put a fire in my belly and ultimately kind of led to me starting this company, Stack Commerce in 2011. And, um, that company, you know, we can get into the details of it, but I ran, you know, essentially, uh, ran it for a decade. I was really conservative about how I approached it. Um, I raised a seed round of $750K, which at the time was like decent, used that money and got profitable, scaled the company to 9 figures and never raised again. And so I, I say, you know, I didn't really bootstrap it and we didn't really raise a lot of money. So I say that I seed-strapped it. Right. And that's a term that I coined, and now it's kind of pretty commonplace, I think.

Yeah, yeah, yeah. I call it bootstrapping. I mean, I think it's all— I always think I tell people bootstraps about a mentality, not a balance sheet. It's like, do you want to grow off your own profits? And are you trying to grow profitably?

I felt a little disingenuous telling people that I bootstrapped, even though— because it was a little amount of money, but you're 100% right. My mentality was like completely bootstrapped, and yeah, ran that company for a decade. Was a sole founder, and then sold a majority stake to a big private equity fund called TPG in late 2020. Who we know those guys stayed on for a year and then left there. There's a bunch of stories in there.

What did Stack do? Just so anyone listening can understand what it is.

Yeah. So Stack Commerce is was a It's still around, they're still growing, commerce and content platform. So at the time when we founded Stack, the biggest companies, believe it or not, the biggest companies in the world in 2010 and 2011, the fastest, not the biggest, the fastest growing startup at the time in 2010 was Groupon, which is crazy to say based on where we are today with OpenAI and everything. Yeah.

So at Ampush, we— I mean, LivingSocial was our biggest client for 2 years, and we, I mean, we probably had like 8 daily deals clients, and then they started verticalizing the daily deals. There was like daily deals for, for cooking only or whatever, like daily deals for sports.

Yeah, exactly. And so we kind of did originally flash sales for, for Mac products and, and, uh, uh, tech products, if you will, and, and digital goods like Udemy courses and, and things like that. And eventually what I found was that acquiring customers as a marketplace or a flash sale site, direct-to-consumer, was really fucking hard. And I kind of stumbled upon this model that would help us scale that was incredible. So basically launched Stacked in that first month, we were failing to acquire a lot of customers. And I had put together this like one-time, 2-week deal. It was like, get 10 software apps for $50 or whatever.

Right, right.

And I had promised these guys I would sell 1,000 of these bundles, the app developers. So like we're one week in, like first night I get zero orders. Then I run some Google Ads, we get like 10 orders. You know, into the first week, 50% through the sale, I think I'd gotten maybe 75 or 100 sales. And I'm like, I remember like, you know, I called my dad, I was crying. I'm like, Dad, you know, I'm like—

You're sitting at home.

I worked on this for like, you know, a year, you know, this is, you know, I've tried so many things. I was just like cracking because it felt like, you know, I was 30 years old. I was like, this is the end of the journey. Like if this thing doesn't work, like I'm gonna have to stay in corporate America or, you know, go work for someone else. And like, it just, it was so, but it was killing me and I knew I didn't wanna do this, you know? And he's just like, you know, I can remember his advice is like, you know, when I'm— I got there when I was in sales, and the best thing you could do is pick up the phone, you know, and make more sales calls. You know, like, that's what you need to like, just keep going.

One answer.

Yeah, there's only one, you know, and, and, but, but a little bit differently than the prior week. And so I was actually working full time for Yahoo at the time. And I called in sick. And Steve Jobs was alive and there was a Worldwide Developer Conference in San Francisco and I was in LA. And so I book a— that Sunday night, I book a flight, fly up there Monday morning. I'm like handing out flyers in front of the Moscone Center in downtown San Francisco. No one fucking wants to talk to me. No one wants my flyers.

Yeah.

Total bust. And I meet someone, they're like, hey, come to this happy hour, like drink your sorrows away at this happy hour. I'm like, well, I'm not even invited. They're like, oh, just figure it out. So like, they're like, the owner of these Mac sites are gonna be there. So I like sneak my way into this party. I find like the main dude, the publisher of the site called Cult of Mac. And I'm like, hey man, I got this bundle. Like, will you post about it? And he's like, I don't know, like fine, you know, like whatever. And so he gets one of his people to like post about our thing. And like, you know, the next day it goes live. We sell like 200 of these bundles in like a day.

Oh.

You know, and then the next day another publication reprints it and we sell another 100. So the point of the story is we end up changing the model from that to be a white-labeled marketplace where we would create stores or marketplaces for media companies. And so 10, 15 years ago, media companies were the dominant—

Before you go on though, dude, like that feeling, I mean, that is like a high that, that is impossible. Like when it first starts working, when something is happening, I feel like Part of my entrepreneurial journey has just been like chasing the next version of that and being like, because it's not even about the big business and the money. I mean, that stuff's great. Don't get me wrong. But like, man, that moment. I mean, did you do you remember feeling in that moment or were you nervous?

It was insane. I mean, so it clicked. We went from like nothing worked, nothing, nothing worked, nothing worked, nothing worked to boom. And so I just globbed onto it. So I like call this guy back and I'm like, "Hey, will you do another post?" He's like, "No." I'm like. Like, okay, like, right? And then, and then you're just kind of going, and I'm like, all right, what if, you know, I'm like, why? And he's like, well, I'm not gonna shill for you. I'm not just gonna like send you, you know, just post about your shit to make a little bit of money. I'm like, okay, like, what matters to you? And he was like, you know, I want the traffic to stay on my site. I want to own the customer. I want to— and I'm like, oh, what if we create store.cultofmac.com? You know, and he's like, okay, well, like, how much could it make? And I'm like, He's like, he's like, look, if you can make me $1,000, you know, in a month, fine. I'm like, all right, I'll guarantee it, you know. And then I had the first check I wrote him out. We did it. The first check I wrote him at the end of the month was for $5,000. 5x his expectations. Yeah. So and then I was like, okay, we have something. And then so we just went down the line and signed up, you know, everyone in the space.

Yeah. I remember whenever I tell people about your business, I always give them like the store.cnn.com example because that was when you told me the first time we talked. Yeah. And everyone's like, oh yeah, I know exactly what you're talking about. I get it. Especially with digital goods.

Well, it's interesting now is like the whole thing is just, I mean, media companies have kind of like just gone away, you know? So, so Stack as a company has had to evolve and, uh, into more of an influencer, right? So enabling influencers to be able to sell goods and being the software behind that. So, um, as traffic has shifted away from traditional media.

So you sold the biz in 2020?

Late, yeah, December 2020.

And that was— what was the most surprising part of like the exit?

Yeah, so, so I, you know, I was on Sam's podcast MoneyWise and kind of told this story. But the most surprising thing, I thought my underlying motivations for being a founder and working so hard were, I thought it was money, to be honest with you. Like, I was pretty excited to get some money. I grew up, you know, with not much money and not a, you know, I guess like, you know, let's call it lower middle class or whatever, you know, but feeling like not as much. And so I can remember the wire hitting and, you know, being stoked for like all of like, a week, you know. And, and I think what I've, what I found out was that there was some validation there that I was seeking, you know, not external validation, more, more what I've, what I've determined on a longer, deeper journey is it's like an internal thing, right?

Like you made out of yourself what you believed about yourself or something like that.

Yeah, yeah, exactly. So, so yeah, I think Entrepreneurship just, it means different things to different people. And I think for most of the most successful people, like money is a byproduct, but it's not really the reason.

Yeah. Yeah. It's interesting. I mean, I think, I think, yeah, money is an interesting topic. Well, because I think it's, I think there's like the classic adage of, oh, I get score. And I think there's truth to that, like keeping score. And I think there's like this thing of it's the byproduct. But I think a lot of people, at least young, young entrepreneurs, and you're going to, you're going to talk about me in a second. Like, I think In the beginning, money is a lot. People believe it's going to be the thing, and then you may almost almost everyone learns it's not the thing. Although I have lots of friends in finance and other places where they just keep making their number bigger because they're like, "Well, I made ten now." Like it must mean that it's not enough, so I must I'm going to make fifty. And okay, I made fifty now. I need to make two hundred. And and like you can just see their brain is like especially like I went to Penn and I have a million finance friends. Like that's just the way they're like. Well. Okay, just must I might not be I must not be at the number yet. Yeah, and my experience is a little bit different than that.

But the thing, yeah, and and and I would love to kind of dig into your stuff. Like what what I think about is there's something more than money that I think pushes you past those those inflection points, right? So like you know I'm I'm sitting in some cubicle in in San Francisco working for Intel, and I'm twenty three, and you know they're offering me raises, and I'm getting more and more comfortable. Financially, but like there, like literally would wake up sick to my stomach being like, "What the fuck? This is not me." Like I, I you know something's not right. I would I could remember being 24, 25 just like something's not right. Like I don't I didn't even know what it was. You know I didn't even you know that resonates a lot, man.

Yeah the the well I think at those times it's I mean you know I've kind of been on the spiritual journey, but it's like that's God or that's the universe talking to you like in in a way you may not even realize it's. coming. My version of that story, by the way, is, you know, I worked at Goldman and when I was 25, I made $400,000.

Holy shit.

And, and I and my boss, who was 29, was making $3 million a year.

That's crazy.

And it was like my dream job. Like, I thought, I thought it's what I wanted. And I had had an offer at another firm called Citadel, which is like very well known. It's like Ken Griffin's firm. And, you know, that, that job is interesting, but like, you know, it was a public markets investing role. And that job generally is like 40% spreadsheets, 40% reading. Like you read all the 10-Ks and 10-Qs, you read all the like sell-side research, you read, you just read, you're reading. And then 20% is meeting with management teams and just trying to— or doing site visits, you know, visiting certain companies. And I remember just being like, I'm just more dynamic than this.

Mm-hmm.

And I remember saying to myself, you know, I'm okay with half of my expected earnings, my earnings getting halved so that I can be like an entrepreneur. I can be a dynamic person. So cool. Just, you know, so I leave Goldman. I was also kind of like shown the door a little bit because I wasn't like loving it. And then I get a call from Citadel and the guy like knew my boss at Goldman. He's like, I know your boss. She wasn't great. You should just come back and work for me. You turned me down 2 years ago. Come back and work for me. I'm going to have an offer for you tomorrow. And, and I'm not kidding. It's not exaggerating. I probably could pull it up. He sent me like a $750,000 a year offer.

Wow.

Because Citadel has this crazy fee structure where normally they charge 2 and 20. Citadel charges fees and 20. And then so the fees, like the fees, they pay everyone out of the fees. So they're like, their comp and stuff is absurd. It ends up being like 7 and 20. But no one cares because their returns are so good. But in any case, so I call my co-founder and he was supposed to go work in finance and his company had blown up during the financial crisis. And I call him and we're literally in the process of moving to San Francisco to start Ampush. And I'm like, bro, like, I'm sorry, I can't do— like, what do you want me to do? You're like my best— he's my best friend. And he's like, he's upset, but he's like, man, I get it, whatever. And I basically like quit before I even started Ampush.

Right. Right.

And what you said earlier resonated with me. I woke up the next morning and I kid you not, I was like in bed and I like had this like weird semi-dream thing where I pictured myself in business casual with a badge walking into this orientation for this new company. And I felt nauseous. Yeah, like I felt sick to my stomach. And I was like— and I called the hedge fund guy and I was like, dude, I'm sorry. Like, I just— I'll call you in a year or two if this doesn't work out. But I cannot. I cannot do this. Like, I need to go. And my co-founder was super pumped about it. Like, you know, exactly. But I remember the same kind of feeling of like, I just can't do it again.

Yeah. And, and, you know, it's funny. I think this is the first reaction though, that a lot of people would probably have to that, which is like, wow, that, that like takes balls. Yeah. But I don't think it's that. I think it's something else. I think it's like, you couldn't go do that thing.

Like, I couldn't. My body was like, ugh, you can't do it.

And so then the question to that is like, well, why? Like, where did that programming come from? You know, like what, you know, so, you know, I'm kind of curious about what it was like growing up for you. What did your parents do? Did you have this example? Was it a lack of like, A lack of money or a lack of belonging? I mean, a lot of times I think a lack of belonging is what leads founders to wanting—

Yeah, there's parts of my story and I've never talked about it in detail publicly, like, like really in detail. So it'll be fun for you to dig in. There's parts of mine that are very much the entrepreneur story and there's parts that are nothing like the entrepreneur story. And so we can, we can dive into some of it. For example, I mean, just some I was like class president. I was homecoming king. Like, I belonged. Like, I was very, very much a leader and very popular in my high school. I peaked in high school, probably. And, and that's a funny example. You know, I had a very high GPA at an Ivy League university. Like, like there's these funny things on Twitter sometimes where I'm like, yeah, this is not advice I want to give. Like, you could do it without a good GPA, but like, I don't know that I would give some of the advice. But anyway, so But, you know, I, I grew up, I'd say, middle class and— but like immigrant middle class. Right. And immigrants like my dad came over, the classic from India, 17 years old, $5 in his pocket, washed dishes at night to put himself through school here. And, you know, interestingly, he worked— he had balls. Like, he worked for 2 years as a government accountant. And after that, like, He like hacked the immigration system, but he like, he somehow bought into a travel agency with like loaned money. I don't know how he did it. He like gave himself a visa somehow to work. And then over time he bought this travel agency from the original owner.

Seller financing. Yeah.

Yeah. And so he had like, it was a corporate B2B travel agency and that was actually a pretty good business before 9/11. And I grew up going to that, you know, probably every single weekend and answering phones for him or just helping, you know, helping him with whatever. And he did a bunch of other stuff. He had a bunch of rental properties. And I think the— I think there was a lot imputed around that. Like there was some direct stuff. I mean, you know my family a little bit. My older brother is a partner at a law firm. My younger brother is a growth equity VC, and I'm the only entrepreneur, interestingly. But the 3 of us are known to be quite entrepreneurial people. And I think, you know, we just saw it. I think It's funny, my dad—

Your brother's a partner at Left Lane, right?

Yeah, yeah.

Yeah, they're huge.

Yeah, yeah. And he's a co-founder, like, he started it. And so it's just interesting, we all kind of are known to be sort of hustly, I think, you know, but I think there was a lot of focus on making it, like, on being— I've explored this stuff with Dave a ton, and it's like, and money for me was like safety. It's like, if you have enough, you don't have to be stressed about this and you'll, you'll be fine. And you don't have to like think about it or worry about it. 'Cause I think there was a lot of thinking and worrying about it in, in our house.

Did your parents give you like ultimatums? Like, uh, like I have a bunch of friends who are Persian and they're like, they're like, their parents are like, you can, you have 3, you can be anything you want as long as the doctor, lawyer, engineer.

Yeah. You know what's funny? My parents were pretty not like that. They, they were younger than most. They, we had my older brother and I when they were 20, 22 and 24.

Yeah.

They had grown up— they would tell you they grew up in the cities in India, so they were a little more like— they spoke English in the house, so they were a little more modern according to them, like versus maybe the traditional Indian or Persian example. They were— there was a lot of incentive systems in our household. Like grades were like, you know, if you get straight A's, you get $100 every quarter or semester or whatever. If you don't get straight A's, you have like massive privileges revoked, like no TV, no phone in your room, just because it was like— and the expectations were very high. It's like, we know you're smart. So like, if you're underachieving, that just means you're not working hard and that's not acceptable in the house. You know, my dad did interesting stuff, like he gave us an allowance, but he made us get in Quicken and actually like create like a full-on ledger for every dollar we spend. And if you didn't have the ledger, you didn't get your allowance.

That's pretty cool.

And so that was a good, that was a good lesson.

There's a, there's an app now called Greenlight that kind of like where you can put an allowance on. And I mean, it's not quite like that, but yeah.

Yeah, I was doing it on like a 486, like the blue screen and it, yeah.

Um, but these things matter, you know? I mean, yeah, that, that less— I mean, those lessons taught to you and, and the rigor, like I mean, I'm sure there's deeper things, but having that discipline and that care from your dad and your parents about pushing you and accountability and teaching you money, I mean, all of these are like little bricks in the entrepreneurial wall.

And then I had a brother. My brother is very similar in age to us, and we had a lot of energy, right? And did you have siblings?

Yeah, I have 4.

Are you what number?

I'm the youngest.

Yeah, we were, you know, he was the oldest. I was number 2. And for most of our— Vinny was born much later, but like, we were really— we were like, we had a lot of energy to do random shit. So we were like, do you remember? I don't know if you remember those. Do you remember those catalogs they used to send to sell you where you could go around door to door in your neighborhood and like sell shit and you either got points or $2 for every item you sold and then you could cash them in?

Yeah. Yeah.

My brother and I would, would just go crazy selling those things door to door.

Dude, that's crazy.

And then we sold— then we had like a snow shoveling business and like, we, you know, we would do stuff like we would like the— we did it in our neighborhood and people pay $25 a driveway at that time. And like, it's fucking backbreaking work. Like, it is not fun work. But dude, someone gives you some cash. And, and then the next time it happened, we had our mom take us to like the neighborhood of townhouses next door, like next, like neighborhood over. Because we realized like people would still— they still pay $25 for you to do their thing, but their driveways were like a quarter of the size.

Yeah.

I mean, Nick would be like, dude, we can get this done in a second. And we like, we tripled our output for the same, you know. And so we were, you know, and I don't know, I think it, it obviously came from, from our parents. It came from my dad especially. And I— but I like, I don't remember him saying all that much. I remember him talking about customer service. And being important. I remember one time I said at his office, like, he was busy to a client and he's like, never, ever say that again. Like, I never want to— like, I'm not supposed to be busy for my clients. Like, I'm going to be— I'm going to say I'm on another line or whatever. Like, be specific or just don't say busy, though. That's like a real— so I remember that. That's like a random lesson I remember. He didn't like teach us business necessarily. I mean, he started investing in the dot-com bubble. And that really piqued my interest. Like, I had stock of Dell back in the day. Like, I remember that very distinctly. And that got me a little interested in the stock market also. But, and I remember watching him go up and go down in the stock market. And that was like a really like— and he— there was, you know, we— I don't know if I've told you this, like, we moved from my age 6 to age 14. My family moved 13 times in a— in a— and this kind of relates back to probably in a 2-mile radius.

That's insane.

Because my dad started like a home development business.

Like, he would build, you know, buy out— Yeah.

Buy a piece of land, he'd do construction, and then we would move into one of the houses and it was like, oh, we have a baller house all of a sudden, right? And then the other one wouldn't be selling and he'd be like, well, we need to sell the one we're living in. And then we'd get a trade-in. And then like, we— like, I grew up not having— my walls were white and pristine. my entire childhood because we couldn't put stuff on the walls because like there'd be an open house on Sunday. And so that was— I think that relates to some of my like money is safety. Like I just— I probably to a fault with my kids, they don't ever feel the ups and downs of, of my situation. They really have never felt it.

How do you, how do you think that will impact them?

Right.

You kind of grew up in this environment that was, you know, a little bit lacking and that probably gives you or gave you a lot of motivation, and now they don't have that.

Yeah, I'm a little torn, honestly. Like, there's a part of me that's like, oh man, they're gonna be spoiled rich kids, right? And you and I talked about that. And, and, but then part of me is like, well, hold on, is it, is it the worst thing in the world for them to not have the scarcity of money for them to go choose what they spend their time on? And I think, you know, I, I've— I'm on the board of a big grocery store here in St. Louis, like a $3 billion grocery store, and The family that's been running it for 80 years is very wealthy. And, you know, one of the things they shared with me that I thought they're like, you know, none of them are spoiled, by the way. They're all really wealthy and they all seem— I'm sure I don't know all of them, but like the ones I've met all seem very good head on their shoulders, hard work, whatever. And they're like, you know, you got to overindex in values if you have money because then the value— like the values, it's not the money that screws anybody up. It's like the lack of values. It's like the The parent who's working hard, not paying attention to the kids and making money and using money as the, as love or whatever, that, that really can, can versus if you give your kids values, hard work and ingenuity or care or empathy or any of these things. And so, we try our best, I think, to orient them that way. And in some ways, I'm excited for them that not to be a— like, for me, it felt like I didn't— your joke about the Persian thing, it wasn't so specific.

Right.

Like, you have to be this job. But I think, I think there was like a, you need to make a lot of money.

Like, what did they say when they're like, wait a second, you're walking away from being a banker? We know that you make hundreds of thousands of dollars. What, you know, maybe they did or didn't know the exact numbers, but like—

No, they knew.

Were they pissed?

They were not supportive. Yeah, yeah, yeah. I mean, my, my mom was, you know, she's nicer, but, but she kind of said, well, like, where am I going to tell my friends you work now? Because like, I used to say you worked at Goldman Sachs, like, that was baller, right? And now I have to say you're like, I moved, moved We, by the way, we moved back into my parents' house, my co-founders and I.

Oh, wow.

So we were like, because we were bootstrapping, we were bootstrapping from the get-go. Like, no, we literally each took our, like, basically half of whatever Wall Street bonuses we had earned and put them in a bank account. And we each put in a—

What year was this?

This was 2010.

Yeah.

And, and did you have any—

Did you have any regrets? Well, I want to— I'll let you answer that. And then the next question, did you have any regrets, like, 3 or 4 years into it, you know, like, are you doing the cat— like, oh shit, if I was making—

I'll tell you. Yeah, yeah, that's a great question. I, um, the— so my, my dad, who had struggled as an entrepreneur to make, you know, he made, I don't know, several hundred thousand a year sort of thing, and maybe good years and bad years, the real estate or whatever, he didn't understand. He's like, your boss is 29 and she's making $3 million a year, like, why would you walk away from that to be an entrepreneur? Like That seems absurdly stupid. And he wasn't wrong. He's like, you don't know anything about digital marketing. Like, what are you doing? Right. And we had sort of— I think we knew we were being pulled to being entrepreneurs. We also felt, me and my co-founders, like those guys, we'd all done like we had fancy resumes and we were sort of like, look, we can do this for 2 years. Worst case, we write a really nice business school essay and we go to one of the top business schools and we're right back on, you know, back on track. Right. So, yeah, we— I tell a lot of entrepreneurs, I don't— mine was not a ballsy choice. It was like a pretty, uh, like I had padded my resume and I took a very calculated risk before I made the jump. But to answer your question, you know, I think over time I've gotten kind of away, pretty far away from money being a thing. It's still every now and again will pop up, but like the first 2, 3 years, we were like, we are kings.

Mm-hmm.

Because I mean, I don't know if I've ever told you this, but we, I mean, in our second year in business, dude, we did like $4 million in EBITDA and we just distributed the whole thing out.

Holy shit.

So each of us were like 27 years old and we were like, like everyone, like everyone bought a house in the Bay Area.

Like, dude, I had no idea that you did that well out of the gate. That's incredible.

Well, we just, I mean, was it more of an agency? No. So it was the first version of Ampush was a lead gen business.

Oh, that's right.

So we had picked performance marketing and it was like online education and we had our moment similar to yours where I put this cool financial model together. I was a financial analyst. I was like, look, if I can get like a 5% conversion rate and a $1 cost per click, my cost per lead's $20. University of Phoenix will pay me $40 a lead, so I'll be a money machine, right? And we run these campaigns on Google, and our conversion rate is like 0.1%.

Oh.

So our cost per lead's $1,000. I go out, I'm living with my parents. I left my job at Goldman. My dad at the time is a triathlete, and so he runs an eight-minute mile, and I don't run.

Right.

And so he's like, "Let's go for a run." I'm like, "Okay." And like we're running a nine-minute pace, which and I'm like dying. Yeah. And he's fully has all his lung capacity, and he's like, "I don't know if he was yelling, but he was like, 'What were you thinking?' Like, you know, you're so upside down in this business. What are you gonna do? Blah blah blah blah." And we did a com similar to you, by the way. We did a combination of some affiliate deals, like and my wife literally my wife today was my girlfriend then was cold calling. Publishers being like, and like 2 publishers worked with us because they're like, I just really like you. Like, you seem like a really sweet girl. Like, that was there. And they moved over from, from a different provider. And then we were kind of puttering along. But then, but that was right around the time Facebook launched the first version of their self-serve ad platform. And you and I are old guys. We remember it was like desktop, right rail. You could micro-target. And I made the first ads. It was like Substitute teachers in California. And it was like, sick of being a sub? California teachers can make $20,000 more a year if they get their master's. Like, come check out our programs here. And dude, it was like a 75% gross margin. And then we started printing cash basically from that.

That's a lesson that I have seen happen again, time and time again over the past couple decades is anytime a new platform launches, there's arbitrage available, right? The Apple App Store, the Facebook Marketplace, OpenAI, like whatever it is, like for a, for a period of time, if you're first to market, you can really crush it.

Yeah. Yeah, dude. And so we, I mean, I think the stats, I don't know if I've told you this, but we, in June of 2010, we did $100K in gross revenue, maybe $40K in gross profit and like $20K to $30K in EBITDA. Or no, sorry, $20K to $30K in costs, like $10K in EBITDA. The following August, 14 months later, we did $2 million in gross, $1.2 million in gross profit, and like $600K in EBITDA.

That's crazy.

It was nuts, dude. And so anyway, we— I mean, at that— to answer your question originally, I was like, well, there was points where we were early on, we were like, oh, you guys are still associates at like investment banking, like private equity, like we're crushing you. And then there was points where that curve inverted, right? where like the business started getting a little flat and we're like, oh my God, we haven't— like, my friend is now managing director. And like, you know, eventually you stop comparing, I think. But like, but there were definitely— it wasn't just initially it was good. Then I was like, oh, wow. And, you know, some friend of ours, like one of my, one of my early colleagues at Goldman started a hedge fund. And, you know, hedge funds, really easy to figure out how much money someone makes. It was— she started like it was like a half a billion dollar hedge fund. She was up 25% in her first year. she takes 20% of that carry, right? And I'm like, oh shit, like, you made as much as an exit in one year.

Yeah.

I mean, it's just obviously you have to, to your point around money, like at some point you have to make your decisions around how you want to spend your time and what's happy, like what's purpose, joy, enjoyment, happiness for you. And but otherwise you will spend the rest of your life because it was, it was so funny how it like inverted in multiple directions over a 10-year period.

Right. I love that.

And every now and again, you know, you go, damn, if I had stayed in finance, I'd be doing this. But like, but then I always like the other part of me is like, but you would have never stayed in finance, buddy. Like you couldn't listen to anyone. Like nobody could tell you what to do. You wouldn't have played the politics well. Like, so I'm like, yeah, it's kind of a silly scenario because it would never have been real for me.

That's a good point. Yeah. If you had stayed, like maybe you, maybe you would have been a bad MD.

You know, like, maybe I don't think I would have ever made it there because I, I mean, dude, I didn't like the hours when I worked at Goldman as an associate, right? Yeah.

You didn't want to sign up for that forever.

And I didn't. Yeah. And I didn't.

I just—

yeah. You know, to answer your question, it was like one of the example things I remember, the— my dad, I never heard him complain about an employee or ever complain about a boss his entire life. And as I didn't realize this until later, I heard him complain about employees because he was always an employer. And I saw how much freedom he enjoyed. And I remember sitting there with some of my colleagues at Goldman, and one of my colleagues was like, my dad is a dentist. The other one's like, my dad's a civil engineer. And they were kind of like, man, our dads have worked their asses off and we're making more money than our dads now. And they've worked their ass off for 20 with no flexibility. And I was thinking to myself, I hate being chained to a desk. I hate living—

It's the same thing.

Yeah, like it just didn't. And so that example definitely loomed large for me.

I think a consistent theme that I hear from entrepreneurs too is that they're bad employees. Like I was not, as I look back in like my 20s, like I was a pretty bad employee at just about every place. And because I was always thinking about something outside, right? Like I wasn't really committed to growing myself inside of my organization. I was just, and actually, You know, that trend— when I graduated college, you know, 20-something years ago, most people wanted to work for a company and they wanted to grow up in it and make as much as they could. And now it's just not the case. Like, everyone wants to start their own company. So like, getting people to be happy and content working for you is like, it's insane, you know, because everyone wants to start their own.

I think a lot— I mean, I think that world is saturated by venture money. which is a whole nother topic for another day because I think there's too much money chasing too little actual talent.

Yeah, true.

But yeah, what I'm trying to think about, anything else from my childhood since you got me there? I mean, dude, the other thing I would, I would say actually, and you mentioned this, like it took you 10 years. I will tell you a couple other cool stories. I started a DJing company in high school with my now brother-in-law, my, my brother, and one of our other best friends. And we cornered the like Indian bhangra market in St. Louis. Because they weren't, you know, and again, people like, that's weird. I'm like, well, no, you actually have to go to like Toronto and London to get all the music back then. And we like the equipment because it wasn't— there's no Spotify, there's no streaming music. So yeah, we would make probably, dude, $20 grand a summer just DJing.

And then you were an entrepreneur from the get-go. Like it was just sort of in your blood. That's not—

I'm going to give you a list of a bunch of businesses.

Yeah.

In high school, in college, I started a t-shirt business called The Shirt Guys. And it literally made bulk apparel for sororities and fraternities because that was like a big business and we just saw it. And we had sales reps and we had— we were the whole kit and caboodle. And that was cool. It did like $200,000, $300,000 in sales. We started a high school version of Facebook, which failed miserably, or we kind of quit on it. It was a mixture of the two.

You've told me about your infamous conversation with Zuck, right?

Zuckerberg. Yeah, that was like Crazy to imagine that. We start— we didn't start that well. We dropped out and then we decided not to drop out to start a medical tourism business. Do you know what medical tourism is?

No.

So it's like this— it's actually like it has never become a big industry, but like it's— you can go to Singapore in particular, which is this like pristine place, right? And you can get like a knee surgery that maybe insurance doesn't cover. You don't have it for like 80, 90% less, right?

A lot of people are going to Turkey for like hair replacement.

That's the idea of like you could be the like go-to platform. And like we thought about doing that. I think we were juniors our senior year. I regret this actually. Instead of like traveling and partying like normal humans who had jobs lined up, we launched a sports social network called Sportster. We pitched Josh Kopelman and he was like, no, I'm not interested in this. Um, because he's a Penn guy. But it was, it was a— he actually said, I remember distinctly what he said, he said, I'm gonna cheer you guys on from the sidelines. But it was the idea of like, you know, Cardinals fans should be friends with Cardinals fans. And like, if you remember, like Ajax and RSS feeds were big back then. And so it was this idea of, could you have like a Cardinals home place with all these feeds from all the content coming in from all over and chat boards? And like, we had— it was a cool idea, just— It was— it wasn't right. So we were just— and then the last dumb idea we had before we actually started a real business was, uh, I still own all the fucking domains. Do you remember that there was like this period of time where there was all these random forum sites that popped up? And one of the biggest ones was F My Life.

Hmm, I don't remember that one, but—

It was like, oh, I was like eating a hamburger today with my white t-shirt and I got ketchup all over it. Like, fuck my life.

I do remember that, yes.

So we bought My Life Is, and then we bought My Life Is Everything You Can Imagine. Like, My Life Is Finance, and we started one for like finance professionals to joke around. And we had My Life Is Black, My Life Is Indian, and then we were hoping that it would be this, like these niche content, like UGC sites.

Essentially what like social media has turned into.

Kind of, yeah, yeah. Like a little subculture-y type site. And so we just, you know, we did so many different things that— and I think one of our big— at least for us, this is different for everybody. For us, we could never do something on the side, right? We just— and it wasn't until we committed and we sort of burned the boats that we—

I think this story is really— this underlying— these underlying stories and businesses are really important because you're like, oh hey, I, I did my— I did Ampush at 24. Yeah, I left Goldman. And people are like, oh man, like Totally. They think of that as the beginning, like, but really your beginning was 10 years before that, right? When you're 14, you're shoveling snow all the way to, I mean, all these businesses through high school DJing, and then in college doing the frat t-shirt thing, which there was always someone doing that. But like, you were the guy, like you were the guy doing that. Like, you know, and so that was, that was really 10 years of entrepreneurship.

I tell, because people do do that comparison. And you said, you know, it took you 10 years from the first time you thought of it to actually That's my actual heuristic. I tell people, I go, the first day you think you're going to be an entrepreneur, it's going to be 10 years before you actually become a real one. And like, to your point around this, you had the story about your e-com site and, and, you know, this thing, dude, we, we had this t-shirt business and it was like a pretty big business for, for college kids, $200,000, $300,000 in sales. And we had, uh, there's this huge thing at Penn called Spring Fling. And it's like, you know, it's the debauchery. Everyone's gonna get drunk and like there's concerts and all this stuff. And so we were like, oh man, this is like shooting fish in a barrel. Let's make stuff to sell to people during this. And so we made, you know, those yardneck bottles.

Oh yeah. Yeah, those were huge.

New Orleans or whatever. Yeah, like official Spring Fling. And, and we were like, look around at each other. We're like, hey guys, let's, let's put 2 G's into this. And that was like a lot of money for us. The business made $50K a year in profit. So it wasn't like, let's put 2 or 3 G's, let's order 2,000 of these bottles and we're going to sell them, buy them for 2 or 3 and sell them for 10. Yeah, right. And we went to every major event around our campus. We hired freshmen to help us do this, to sell these things. You know how much money we made?

No idea.

We sold 3 bottles out of 2,000. 3.

No way. And like, why? What happened?

Dude, people were drunk. They didn't want to carry around like a bottle.

Like, you just missed the mark.

You just— and I think, but the point, to your point around the 10-year thing, is like, there's so much failure that goes on. And you, I mean, again, you know what that feels like now. And I know it's like, we're embarrassed. Like, your face is flush. By the way, we had all these boxes of cups. We had no idea what to do with them. We literally said, we lent them right before the end of summer. We dropped them off at the patios of our biggest And we're like, uh, congratulations for the shirt, guys. Like, use this sometimes. We had our dorms, we had to move out.

And we were like, dude, it's so good.

The amount of stories I have like that where we screwed something up, where it didn't work out, where we quit probably too early. Like, I think to your point, I think you need 10 years of that stuff, um, before you're gonna start the thing that that probably happens. And I think it's, I think it's an important call out.

100%. I think that founders today, especially with this idea of AI, oh, I can, I can vibe code, you know, an app and like, it's, you know, it's gonna take off. I think in the same way that when Instagram came out, whenever it did, and it set people up for like, you know, body dysmorphia or like image dysmorphia, like, you know, like, oh, like my body should look like that. There was like a period of time when Instagram first came out where like, you know, it was like a thing of like, oh, this is crazy. I think I see the same thing happening now where it's like founders having the expectations that they should be making $10 or $100 million in like a year, you know, and like, oh, like I'm failing, you know? And it's like, I'm not like so-and-so who, you know, and it's like, no, like that's not normal. Like you need to grind and it's going to take you a decade. And yeah, there will be exceptions to the rule and there's the, The kid who founded a company 6 months ago and sold it for $80 million. But that's like one out of—

But I think before, for you, for anyone listening, before you get so excited about that person's story, I know a lot of people like that and they live in constant insecurity that they were a one-hit wonder, that they couldn't do it again, that they just got lucky, including Alex Lieberman, who's obviously a good friend and he's a killer entrepreneur. But he's a younger guy, and the first time I talked, he's like, yeah, dude, I have a lot of worry that Morning Brew is just— I'm like, what are you talking about? You're so smart. He's like, yeah, but it's a feeling that you can't let go of until he starts more successful things. And so I think that to your point, I think there's a lot of— even when you have the big win young and early, I've seen those people be some of the most unhappy people I've met and some of the most stuck people I've met.

Yeah.

They also like, they can't start a new thing because it has to be bigger than the thing they did. Like, there's just all these weird— the stories we tell ourselves, right, are the things that really mess us up.

You tapped onto something really important, is initially it's about one thing, and that one thing might be money or success or validation, but eventually it becomes about a couple things, you know, and it's that underlying contentment and belief in yourself and And the money, right? Like, you, you know, you kind of realize, oh wow, like just having success turns out to not be really enough, you know? And, and people that don't have, um, you know, that want that, that want a ton of money and don't have it, are like, dude, are you like crazy? But the problem, like, those people have contentment, so they don't have the money, you know, because they're content, you know? And then the people without contentment—

That's like, you ask anyone why they want money enough times, they'll say contentment, they'll say Freedom, they'll say peace. And I mean, there's famous parables about this, obviously. But you know, it's interesting. I have this like it was much. It's all just the lies and the stories we tell ourselves. Like I was. It was much easier to lie to myself when I was running Ampush. And I'll give you a specific example that's come up for me very recently. You know, I as you know, I've started a bunch of these companies, but I'm not running the day to day of any of them. And and very recently, in the last couple weeks. I announced a pretty meaningful internal calendar shift, and I learned from a couple of friends who run holdcos that like they basically don't— they don't talk to clients or employees unless the CEO asks them to. Like one of my friends runs a holdco, and that's— that was not the case for me. And I was like more of a fractional president across the companies than I was like a chairman of the holdco, right? So I told everyone like, I'm going to stop doing that. Unless, you know, unless I'm— because it's going to force you to use me when you need me and whatever. Great. Everyone's like, good, Jesse, good for you, buddy. Like, no one cared. And which kind of sucked, but I was like, fine. And then my calendar has been really empty.

Interesting.

And dude, I've gotten a lot of anxiety from my calendar being empty. It hasn't changed the performance of the businesses. So at Ampush, I kept myself really busy because I was like, this is— I'm the CEO and this is my livelihood. And now what I'm realizing, I was talking to my coach about it. I'm like, dude, it has nothing to do with the money. Or the success of it. It has to do with like, I've got some weird, I need to be busy thing, or I start feeling— I start freaking out a little bit. And it's like a purpose attached to work, right? So anyway, it's interesting just to like, you start to disconnect these things and you go, oh yeah, you used to lie to yourself and said that, oh, it's because it was your first company or because you hadn't made it yet. And I'm like, well, it's weird. I have the same feeling when my calendar is empty where I'm like, whenever I have an hour on my calendar, I'm like, why do I have an hour available on my calendar? Like, what work should I be doing? How should I, you know? And it's such a, like, addiction, the work. Um, and it's like, it's not even per— like, I feel purposeful. I have this big platform and all these people, and I'm like, but it's like my own individual time has to be busy. Otherwise I'm not like, I'm not of worth. Like, there's a really— it's even deeper than money and all these things.

Like— Well, we could spend a whole nother, you know, hour on that topic. But yeah, I feel like we've, uh, we've, we've covered some really interesting things, and I feel like this the— hopefully the start of something, uh, bigger.

All right, good times, dude. Thanks for all the questions.

Awesome.

All right, see you, Josh.

Thanks for having me. Okay.