An interview with Jesse Pujji, founder & CEO of Gateway X

James, after this week, I feel like this is turning into your own personal reunion show.

I don't know about that, but it was really fun getting to talk this week with Jesse Pujji. Jesse was the co-founder of Ampush, which was kind of the biggest competitor to my first business. And since then, he has gone on to become, and I mean this really lovingly, Jesse, but basically Twitter famous. He's also just like a super inspiring guy and is doing a ton of stuff, and he's really committed to helping founders not get screwed over by VCs. He's just got like a super interesting perspective, and I also have known him forever, so very thankful that he's on the pod this week.

If you're a founder or an aspiring founder, this is the episode, so let's get into it. This week's episode of Taking Inventory is brought to you by one of our sponsors, Meet Market, your AI assistant for e-commerce marketing. Market isn't just another growth tool; it's a member of your team, helping you keep a pulse on your business and trained to save you time and make you money. It's also co-founded by James Barrow and myself. Visit us at withmarket.com. Now let's get to the podcast.

So today we have Jesse Pujji on the podcast. I've known Jesse for. Probably about 15 years now. He is a self-made entrepreneur who has bootstrapped a ton of businesses, the first of which— actually, probably not even the first of which. He'll tell us more about this. But the one where I met him was a business called Ampush that he turned into an 8-figure powerhouse. He's partnered with some amazing brands like Uber and Hulu. And today, he's building GatewayX. It's a venture studio, an investment company. that he's running out of St. Louis that is doing a ton of awesome things. You may also know him from Twitter or LinkedIn, where he's basically kind of taken the hood off of all types of things about how he's doing all the businesses that he's running today. And he's also got this awesome podcast called Crazy Ones. So Jesse, man, thank you for coming on the podcast today.

Yeah, for sure. Thanks for having me. As soon as you said that, I was like, what was my first bootstrap business? I think it was like My brother and I snow shoveling for people. You know, we— it was funny, right? It would snow and then we would shovel driveways and charge $20 or $30 a driveway. And, you know, in our neighborhood, my, you know, we were middle class, but like there were big driveways in our neighborhood. And my brother and I were like, it was like backbreaking work, right? Like shoveling snow is not a pleasant thing even when you're 13. And so we were like, fuck. And so then it snowed and And we told my mom, we're like, hey, Mom, take us over to like the neighborhood with kind of like the townhouses. Because what we found is they would basically pay you the same amount of money, but like their driveways were these tiny little squares. And so my brother and I were just like, optimize the hell out of our snow shoveling. And I'm not even kidding. I think we made 2 or 3 times the amount of money in the same period of time just by shoveling smaller driveways effectively. It was like $25 versus $30. But we figured that out in our neighborhood. Then people were like, will you shovel the driveway? We're like, nah, we're good. That was probably my first bootstrap business.

That's funny because there's, there's been this movement recently of, of especially kind of young entrepreneurs going into the hard labor as the cash-flowing business, whether it's like homework or pool cleaning, things like that. But we can get into that.

Yeah, I think that makes sense, by the way, as a young person. Like, I might have my kids do versions. Like, we just— my son's in Cub Scouts and he just got the popcorn sales thing and I'm like, He went around selling and I'm like, good, good. Like, you got to feel the excitement of selling something. And I agree. I think for teenagers, like power washing or all this stuff, I think that, you know, the Twitter, the dialogue on Twitter is like a little overdone in my opinion. Like, those are shitty businesses. Like, they're not boring businesses. They're shitty businesses. They're hard to scale. Labor's a challenge. They're low margin. Like, There's a lot in the dialogue and I'd say if that's what you can start, you should start it. But I feel like, I feel like, and I'm also, also not in the camp of go do big tech startups either because that has its own challenges. But I think the answer is somewhere in between those two. My, my hot take, I guess, on, on some of the Twitter chatter.

As, as a, a pretty big Twitter or X influencer, do you find, you know, like people who are putting out kind of like the bullshit advice, is that Are they putting it out there because they believe that or because it's just formulaic and they know it works? Like, can you— do you have a sense of that yet?

I think it's a little bit of both. You know, I think, I think when someone's truly being inauthentic, it just comes— it doesn't make it, you know, like, like Nick Huber is a good example. Like, I think he believes the things he's saying and I think he spices them up to make them purposely slightly controversial. And like, again, the algorithm these days is all about comments and conversations. And like apparently the comment to a comment is like the most valuable thing because that whatever, there's a lot of engagement there. So I think he's a super savvy guy. Like he, he purposely has adjusted his approach. Like I don't think he does big threads or anything. I think he does like things that are somewhat— they're his opinions that he believes. I don't think he's bullshitting, but he frames them in such a way that they're going to create an argument and they're going to go back and forth.

And I guess running— we're going to, we're going to go back in time then. I mean, you've now seen this. You've talked a lot about kind of how Meta has done its targeting, why it's not listening to you. I think that went viral a while ago, but I imagine a lot of this was formed as you built Ampush and started working with big brands and were really, really early. I mean, you and James were both very early in that industry of how do we help brands reach their customers, talk to them in an authentic way, and then start to put paid media behind it?

Yeah. Yeah. I mean, it's kind of cool that James and I, you know, It's funny to kind of reflect. We're old now, I guess, in the context of all this stuff. But at the time, James, how old were you, James, when you started Shift?

I was 25, maybe. I'm 39.

Yeah. So I was 25 when I started Ampush. I'm 39. So you and I are mirror images. And it's funny just because, like, I think one thing I would just say that it's slightly different answer, Daniel, to what you're asking, but like When we sold Ampush, which was actually pretty recently, you know, we ended up going a while with it. You realize that the only thing that lasts after all of it— sure, you have money in your bank if it goes well, which is great. But the real thing, like I got 500 emails or 600 emails, like former employees, former clients, you know, former competitors. And it's funny because I think at one point James and I were probably pitching— 50% of our pitches were competitive with each other.

Yeah.

And same with like Nana against these other guys. And it's like, but even then, like, we're friends. Like, all of us are friends now. Like, you know, everyone knows each other. And it's almost like people who— it was almost a little bit like your sibling. You're like the only other person who really knows like Facebook. You got to do whatever they want. Like these clients, they're, you know, they think you're a miracle worker. And like, it's just a fun reflection on like ultimately the relationships of Jesse and James has way outlived all the business stuff. And so I think I especially encourage people who are— who play more zero-sum or like think even like we were literally direct competitors. I remember pitching Visa and they're like, Shift. And James walked out the door and I walked in to pitch Visa and I had to be like, well, I like James. He's a nice guy, but he sucks actually. And here's why our business is way better than his, right? We're good. And, and yet who cares? Like, you know, now today we're friends, we trade notes, we've, you know, we've helped each other. And so it's just a good thing to remind people is like, man, it's, it's, you know, It's more normal than you think to have these long, long-term relationships in business.

Totally. I had a mentor of mine told me that, like, you know, in most cases, actually, life is long. And like, so you got to remember that. And it is funny, like, I literally, like, 5 minutes ago, I was talking to Per from back in the day, Nannigans. And I talked to Jackie Pimentel. We had her on the podcast. And it's amazing, all these relationships. And I think it's like, You know, part of the reason why I think a lot of stuff that you're doing now where it's bootstrapped and it's not venture-backed, I feel like also creates an environment where like you can be more collaborative. Like you don't have, like, I guess the zero-sum games feel different. Like, is that a fair take? Like, do you feel like things are different now that you're like not beholden to some big VC?

Yeah. Yeah. I mean, look, I think the, when we started Ampush, We— the insight we initially had around bootstrapping, there was a couple of reasons for it. I think one was we wanted to control our own destiny. And what I mean by that is we wanted to learn on our own curve. We wanted to figure things out as we went.

We—

and we knew that the second you take money from someone, you know, we'd— I'd worked on Wall Street prior to the company, so I understood preferred equity. You know, it's debt like it's debt and a downside like you owe someone money. It's not that you just, you know, and, you know, you bring them in and So we were a little bit just resistant to that aspect of it. I think, I think the other thing was like we were, we were, and I still am obsessed with the concept of like ongoing cash flow and the idea that once you have cash coming in the door, you sort of, you can choose and pick and choose your own path. Right. And this idea on the venture funded, for me, it was just never appealing of like, I got to get money from someone, I got a clock on my head, I got to make it work in this period of time. And if it doesn't, I can't raise another. Like, I just didn't like that treadmill. And even we even tried it with one of the companies at GatewayX, as you guys know.

Yeah.

And I gave the money back and I was like, I don't like this. I don't like burning money. Like, it does just— it's not— and by the way, I'm not— one time Rick Elias, the founder of Red Ventures, you know, he said we were talking about Uber, who was a huge customer of ours, and they had just lost $1 billion in the year. And he's like, man, I could not sleep at night if I was losing $1 billion. And I actually thought in that moment he was criticizing Uber like he was shitting on them. And then I realized later, like, you know, that's not at all what he was doing. He was literally being just honest. He's like, I could not sleep. If I— and that's sort of how I feel about bootstrapping versus, versus VC, which is like, there's— I have friends who have crushed it. They've grown their businesses, they've exited them, or they've taken secondary or whatever, and they love it and they crush it. And it's just like, for me, my, my, like, I don't like it. I don't like the clock on your head. I don't like burning cash. And then to answer your question specifically, James, like, I You know, I always used to joke. I was like, if Ampush was venture funded, I think I would have been fired three times in the first three years or five years. It's like thank God it wasn't because I would have like and you know as I started growing, you know beyond the Ampush experience, I started working with a coach. It's been nothing short of life changing for me in so many ways: my personal life, my my business life. But what I realize is I really enjoy coaching and teaching other people, and that's the why for me beyond money, beyond business success status. Not that I don't care about those things. I'm a human. I saw— of course I care about them. But the thing that really gets me up in the morning is coaching and teaching others. And I wanted to create a business that allowed me to do that continuously. And that's a lot of the reason I chose GatewayX. And then to answer your question, yes, bootstrapping lets people— it's just more forgiving. Like we can have a down month, like we're having a down month in our e-commerce. Like it's okay. That's not a big deal. Like Carolyn, she's learning things. You know, she thought that— she thought she was good and then she realized like, nope, she's not good. And that was an important lesson for her and she's going to solve it. And like, she doesn't need the pressure of, oh my God, I have to go to a board meeting, tell these VCs they're worried about their markup. They're, you know, is it going to get to the next level or not? When can they raise the round? You guys, you got to get your time. All these external things that have nothing to do with the customer or the employee.

Right.

And so to me, when you're bootstrapping, it's just more pure. Um, in that you can focus on the customer and the employee and the development. Now, I'm not naive. I think like, I think some people, I think at times I've said this and I've been naive. Like the venture game is real. My brother is a big growth equity VC. Like it's a cool game. Like it, you know, like you, you, you've got these big ideas, other people pay for it. You go, you shoot for the, shoot for the moon. You know, even if you, even if you end up in an acqui situation, you probably make a few million bucks in that situation personally. Right.

Yeah.

In other cases, you make hundreds of millions and it goes really well. So it's— there's nothing wrong with that game. It's just, again, like back to Rick's quote, like it's just not for me. It's not the thing that gets me excited. And I think the people I'm protective of are the really young founders who think it's the only way to go because they don't know there's another way. And I think what I don't like seeing is a founder who gets into that situation realizes I would be totally fine with a $25 million exit, but I can't have that anymore. because I took this VC money and I have to go get this big outcome, and if I don't, I'll be fired or I'm considered a failure or whatever. That's the person who I'm like, whoa, whoa, whoa, let's make sure this person knows the multiple options and that they don't just jump onto the venture treadmill just out of the default, like, state. So that's just sort of the— that's a long answer to your question, but that's kind of what, what's gotten me here.

Do you think, though, that mindset has shifted at least a little bit over the last few years as venture got really, really hot and now it's kind of tapered off. I mean, we've heard from a lot of e-commerce in particular, those types of founders saying, we don't want venture money anymore. We're willing to take kind of angel investment check with true operators that have an expertise, or we want to figure out how to grow this thing without external capital. Like, do you think that mindset's changing?

Yeah, I think it has shifted a bit. I still think that, you know, and we're starting this media thing called Bootstrap Giants, which I'll plug, but like, I still think the narrative is very heavy VC-backed or lifestyle business or like 4-hour— I call it 4-hour workweek business, you know? But I think me, you all like bootstrap the kind of like we call them Bootstrap Giants. We're like, no, there's a bunch of people who want to build ambitious companies from their own profits and their own cash flow. And that's part of the reason I'm starting it is because I feel like the amount of questions I get online and all these things like, There is— there are unique playbook elements to it, right? That like— and James, James and James and I played a lot with working capital in our first business.

Yeah.

We had media dollars coming in. We borrowed against them, but we did— I mean, I'm sure he did them. We did shenanigans left, right and center around managing working capital and having, having debt lines. And it's like, you know what? Like, I was a very, very precocious 26-year-old. Most 26-year-olds are not that precocious. And they could use, you know, Uncle Jesse now, I guess, at this point being like, hey, young man, like, you should understand debt and, and like, here's how you use it and here's how not to fuck yourself with it. And here's, here's the ways it can be. And like, for example, with the brand we have, we launched, you know, early last year, we invested $250,000 to get it off the ground. And it has been cash flow positive since June. It has never made a profit since June of last year. So, so it has yet to put up a profit, but it has been cash flow positive since last June.

Okay.

Well, how is that possible? Well, we work with Settle, like they fund our receivable, you know, they fund our inventory, they fund our media. We have credit lines from both our inventory and from Facebook, which I, you know, I made some phone calls to get some, some probably more credit than I deserved than a first-time entrepreneur could get. And so as long as our revenue keeps growing, we take the cash in today and we don't pay the bills for that cash for another 4 months, right? And so as long as we just make sure the revenue grows and we do it. And so anyway, that's like an example of something where, you know, I feel like I could teach people that, like, that's kind of the plan is to go teach people those things ahead of time.

I remember back in the Shift and Push days, I mean, we had, you know, we're doing hundreds of millions of dollars of, you know, spend, but it was on the wrong side of the float. And it was like a very, it was a very useful kind of lesson in like, okay, like Payment terms matter a lot. And, but yeah, to your point, like I was, you know, 26 and you were just like, you know, WPP was like, you know, take it or leave it. Here's net 90. And you're like, fine. And then, you know, $50 million later, you're like, fuck.

Yeah. Yeah.

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Yeah, well, dude, we did the opposite because we didn't work with agencies as much as you guys did. Remember, we were working with a lot of these brands, so we actually had the opposite benefit. We would borrow from Facebook effectively, like we'd charge on a Facebook line, We would bill through, we could borrow from our asset line from Silicon Valley Bank. And so we had periods where we were losing money as a company, but we were using— we were funding it using literally like the spread of media. Anyway, yeah, I mean, there's a lot of shit that— there's a lot more out there that people just don't know that I feel like we can educate and build around. And so, yeah, Daniel, I think there are people thinking about it more. But it doesn't— it, you know, it's where venture funding, the venture, like the venture approach 15, 20 years ago. Yeah, even, even 12 years. Like Uber raised their seed round at $4 million or something. Like back then it was like, oh, how do you get meetings with the VCs? How do you, how do you put a pitch deck together? That's where we were 15 or 20 years ago in VC. That's where I think we are in bootstrap giant, in the bootstrap playbooks. In other words, people want to do it. But they don't know how to. It's not a it's it's not an obvious thing. You need to know how to do it. Like it's a real thing to learn the the elements of doing it.

One thing that that you I've seen you tweet about it and you mentioned it here, but just like again, I've known you for a long time and I feel like I do feel like you have like a sense of clarity to what you're doing now that is a sincere and just like almost different than it was maybe five ten years ago. Like yeah, you talk about executive coaching. Can you just like, I've never had a coach. I think a lot of people are kind of almost scared of it. And I know you're a huge proponent of it, but like, just kind of curious, like, how did that actually change things? Like, can you like just kind of explain it to the people who are scared of it?

Well, I'll start by saying I was one of those people and not necessarily scared of it, but I met my coach originally in 2012 and I loved him. I thought he was a great guy, but then he showed me how much he cost and I was like, fuck that. Like, I'm a bootstrap founder. Like, I'm not paying you. $3,000 or $4,000, whatever it was, $3,000 a month to talk to me 2 or 3 times. Like, are you kidding me? And, you know, the— we had, you know, you remember all this, James. Like, we had all— we were on inside of a gold mine, all of us. We had gotten on top of this Facebook mountain. We were riding the wave. And we went from this vision of bootstrapping and taking a long time to grow out Ampush. And I actually have this deck I put together in 2009.

Yeah.

that actually looks extremely similar to GatewayX's business plan. But, but like, we knew nothing before starting. So we started Ampush. All of a sudden we were in this gold mine. We're like, okay, you know what? Grow this thing as fast as we can and sell it. Like, that's the best business plan here. So we put our heads down, we grinded, we hired, we got to 2015. And, you know, you might— I think James will remember this. Like, at one point, Rocket Fuel and Marin were like billion-dollar public market caps.

Yeah.

And so the idea was, dude, if we— I'm sure we were saying the same thing in our boardrooms, James, like, If we are at $30 million in net revenue, we should be worth $150 million, right? And so that was what was in my brain. So we go out to run this process. By this time, Rocket Fuel and Marin are down 95%. They're socks. And all these guys are like, wow, really impressive business, guys. It's worth $70 million. We were fully bootstrapped. 3 people owned it. And, you know, I had lost all perspective. I was like crestfallen. You know, in retrospect, I didn't even know what I was feeling in that moment. But what I was feeling was disappointment and sadness. Right. And at the time, I didn't know. I was just like, oh, they're wrong. Like, you know, this is— and so we ended up kind of taking this deal that was— there was a lot of like, in retrospect, I don't regret anything. Like, we learned a ton from Red Ventures and all this great stuff, but we basically took a deal that was like, we're going to— they're going to let them invest, then they may buy us in the future, they may not. We're going to shift our whole business around. So we kind of signed up for this very strange For people who are ready to sell their company, we signed up for like the opposite of selling your company. We signed up for change your whole strategy and like grind again to figure this out. And so I'm sharing all of that because about a year and a half after that deal, I was as burnt out as I've ever been in my life, as I've ever much ever seen a person. And what it looked like for me was I'd wake up at 8:30, you know, or I'd wake up as my wife would leave for work. She worked at Twitter. And I was like, oh, it's 8:30. Okay, let me cancel 3 meetings. Hey guys, I'll be in by 11, you know? And then I'd get in at 11 o'clock and then I'd be like, it's like 3 o'clock. I'm like, yeah, yeah, somebody else take my 2 afternoon. I'm like, I, for 6 months, I basically was barely at work. And then, you know, I talked to a lot of mentors and other people and especially even Rick from Red Ventures. I was very honest with him. I was like, man, I don't feel like doing this anymore. Like, maybe advertising is not my thing. Like, I was, I was kind of circling and And him and a bunch of other people said, you know what, dude? Like, you're, you're a really lucky guy. You have like 2 beautiful children. You have this business you started. You're 31 or 32. You're rich. Like, you know, so the fact that you're feeling the way you're feeling, there's some inner work to be done, right? Like, you've lost perspective. And so, you know, I actually ended up calling back Dave, who's my coach after 5 years. I'm like, are you available? And we actually ran a process. We met a handful of coaches and he ended up being the right one for us. And so I guess I'm sharing all of that just again, the prelude to it is like, man, I'd gone through this like somewhat crazy journey and I felt really burnt out. And that like, I would tell people not to wait until that time. Like, get like both of you, you definitely, James, should work with a coach. Like it's a game changer. And so anyway, so I started working with him and, you know, I think there's a lot of things that coaches do. I think at a super high level, and I'll give you a couple specific examples, like They hold up a mirror to you and they really reflect back things that you otherwise aren't seeing in yourself or aren't able to know that you're doing. Like a silly example, but a powerful one was in the first, like, 6 months of working with Dave, he was like, you know that you and Nick use the word should a lot. We should reorg. We should make sure we change the plan to this. We should do this. And I was like, whoa, so what? He's like, is that an inspiring word? Do you feel happy and excited when you say the word should, or do you feel like weight is coming on your shoulders? And I was like, well, what's a different word you would use? And he's like, what about like or want? I'd like to do this. I'd like to do that. And it's so funny, in my marriage, my wife and I have completely shifted the word, that word. We don't use the word should in our marriage. Like we used to say, oh, we should go to these people's party this weekend. We should really get back to so-and-so, you know? And we both, we say, I'd like to, I'd like to, I'd like to do this. I'd like to do that. And think about how different the conversation is with—

Yeah.

What happens— like, there's this concept of arguable and unarguable language that the coaching stuff teaches you. If your wife comes to you and says, you know, we should go to Susan's party this weekend, that's arguable language. You'd go, why? Susan didn't come to our party, or, no, we're busy. We got other priorities. We shouldn't go there. And I know, yes, we should. No, we shouldn't. Yes, we should.

No, we shouldn't.

That's argument. If she came to you and said, hey, honey, I'd really like to go to Susan's party, how would you argue that with her? No, you wouldn't like to. Yeah.

Yeah.

You would never say that. You might say, well, I don't, I don't think I really want to go. Okay, that's interesting. But now you're both just kind of talking about what you want and you go, well, well, can we go for an hour? Is that okay? Oh yeah, that's great. Cool. No fight, no argument. No, you just kind of discussed where you need to be. Right. And so that's a tiny example, but that was one. So they hold up a mirror to you. They are an accountability partner. So there's things all of us have on our list, man. I want to work out more. I want to get better at running meetings. I want to So, they'll not only, like in Dave's case, he'll teach you things. Like, he helped me level up my meeting skills and he helped me level up how I give feedback, but then he also held me accountable. He'd be like, okay, so you're gonna change your meeting format to this and by when are you gonna do it, Jesse? And like, he'd be like, within a month. Okay. And then a month later, he's like, hey, you said— I'm not holding you accountable. I'm helping you hold yourself accountable. You said this to me. I'm your coach. Did you actually do this?

Mm-hmm.

And so I think that's super valuable for people at our level because who else is going to do it?

Yeah.

Your board is not really doing it. So, so those are 2 things. They kind of play the role of therapist. Like there are, there are certain things you cannot say to anybody. Like I can't say to my co-founders, I can't say to my wife, I can't say to my employees. And man, I just sit with a person and go like, man, you know what? Fuck that guy. I hate that person. Like just to say it sometimes. It's so therapeutic, right? Just to get it out of your body and to sort of say it. And then I think the extreme version, the last thing I'd say is there's parts of you, of everyone, that wants to grow, that wants to change or develop, and they create this really safe space for you to be able to face those things and be able to grow in those different ways. You know, one of the crazy things is like most of my conversations with him, I'll give you a couple of the frameworks actually, 'cause they're pretty interesting. So one of the frameworks is the types of motivators. So this, you know, he uses this thing called the Conscious Leadership Group and they've written this really great book. My favorite book to give people is 15 Commitments of Conscious Leaders. And they have this framework where they say like the, There's the 5 motivators. We all have these motivators. We all use them all the time, but we tend to be fixed on 1 or 2 of them. There's fear. You were scared of something. There's extrinsic, like status, titles, money. There's intrinsic, like wanting to beat your own score. There's genius or play. It's like, oh, it's just fun, so I want to do it because it's fun to do it. And then there's love, which isn't like how you love your family or kids. It's like the human experience, like you're adding some value to the human experience and you're being empathetic to people. And just to kind of talk through them a little bit, like fear. And by the way, none of them are good or wrong or bad. They're all what they are. Fear is one of the most powerful motivators out there. If I put a gun to your head, you're going to run faster than you've ever run in your life, right? And most of society, most of governments and companies and history has been built off of the fear thing. It's a very effective way to motivate people. It's also very biological to our bodies. We were designed— humans were not designed to be happy. That's a really important thing. We were designed to survive. Well, if you wanted to create this thing that was made to survive, you'd make its fear indicators very strong. You don't want it to get eaten by a lion, so it needs to be paying attention to all these problems. So, we naturally are problem-oriented. We naturally are fear-oriented, and it's very effective. And then society has reinforced it over many, many, millennia, essentially, right? But it's really effective. Now, the down— like, the down— the 2 downsides of it are it's a non-renewable resource, and it's a— it leaves a negative residue on you and other people. It doesn't feel good, right? It's not a pleasant experience to be in fear, even though— even though you would have gotten away from the person by running. Now, what happens when the guy is not chasing you anymore? You start walking again. You're not feeling motivated all of a sudden. And I'm sure for you, James, and for me, You know, we, we were young. We're like, oh, we're starting these companies. Fear, fear. Oh my God, it's going to be successful whenever we say. Then, then we've both had successes and you can't tap into the same reservoir. Reservoir is gone now. You have whatever, plenty of money in your bank account, as do I. And it's like, oh, so in that case, what a lot of entrepreneurs do, like a couple of funny examples they share. One is Bill Gates, most fear-driven guy on the planet, right? There's a story like he sent software in a coffin to Lotus. The guy was just a beast, an animal. But then, he became the richest man in the world and this company, which by the way, has gone on to be a multi-trillion-dollar company, he didn't find interest. He couldn't stay motivated running it. So, he jumped all the way to this and said, I want to cure polio. And this one all the way on the other side, it tends to be very powerful and very renewable. It's not like you ever get sick of curing diseases or helping people or helping some part of the human experience. So, Or like another example on the play genius front is like Warren Buffett. Like the guy's alive because he just like loves investing. Like, you know, he's, he's just totally in, in, in loves that shit. And another good fear example is Travis Kalanick. You know, just again, like, I don't know him, psychoanalyzing him from far away, but like they say, like he, he, this is what I've been told. Like, you know, he had this big chip on his shoulder. He grew to be the biggest tech company on the planet and then he sort of sabotaged himself. Like he did did self-sabotage and got himself kicked out because he wanted to feel the fear again. And maybe the deal— the reason I took the deal I did on some level was like I wasn't scared anymore and I was like, oh, let me blow my whole business up and partner with this new company and do all this new stuff. I want to feel that fear again. So entrepreneurs tend to get addicted to feeling that fear. And other versions of it we're more familiar with is, oh, I made $10 million. Well, I thought I'd be happy at $10 million, but now I need $100 million. Okay. I thought I'd be happy at $100 million. Now I need $1 billion. It's just this thing constantly. It's like another way people deal with it. So, a lot of the coaching is to shift you both broadly, but even in the moment, moment to moment, like someone's sharing bad news with me. Do I feel fear? Do I feel like I'm being threatened right now? Or do I feel like, oh, this is what I'm here to do as a leader. I'm here to teach and coach people. Well, like, that's what I enjoy doing. So, a lot of the journey of coaching has literally been reprogramming my insides, which were very programmed around fear.

Yeah.

to be— play more in the play genius and the, the lump, like the love sort of drives and motivates. And again, it's not just a big thing. It's also a very small thing. Like in— like my coach has taught me in a meeting to notice what I do when I'm feeling scared, when I'm feeling threatened by what I'm feeling, what I'm hearing. Oh my God, our business is down or this, you know, the e-commerce business isn't having a good month. Am I threatened or is that my opportunity to coach the CEO and say, hey, this is a really cool learning opportunity for you. Here's how it can get better and blah, blah, blah, blah, blah. And so that's like one of the core paradigms. The other one I'll share briefly and I'll shut up is like they relate is like context versus content. And so oftentimes we as entrepreneurs, as business people, spend all of our time in content. Like when I was feeling unmotivated at Ampush, my first thought was, why am I doing advertising? I was like a finance guy. Like, how did I find my way into this strange place of like digital ads? And my coach would say like, that's all nonsense, Jesse. That's content. You can do anything like context is the motivators you're, you're using in that moment. And so the example you can think about is, you know, a lot of people go, oh, I've been doing these things. I'm going to go join a cancer curing startup. This startup cures cancer. It's do-gooding. Or there's a lot of like, there's a lot of green tech shit. People are like, I'm going to go do this. You could be at a cancer curing startup. But if, if you're motivated because you want to raise your next round or the culture, you know, you want to be on in front of magazines or whatever, like look at Theranos, right? Like, If your context is still fear and extrinsic, it doesn't matter if your content is really altruistic. It's still going to be a shitty culture. It's still going to be unmotivated. Like it's still going to burn people out, right? That's, that's sort of what's going to happen. The flip of that is like there's like insurance brokers, some super boring business, like some local insurance broker who they sell a completely commoditized business. They suck at it, but they wake up every day going, I'm going to help my clients. Like, I really care about the humans I'm selling my insurance to. And I'm going to make them really good. And that could be a very inspiring and sustainable place to work, essentially, or sustainable thing to build. And so, again, a lot of this is like, as you shift up that curve of motivators, it's more sustainable and it's just more gratifying and more sort of positive energy. And so, what you're noticing, James, a guy who's known me a long time, is that exact thing is like 10 years ago, I was like, I was battling. I was like in fear. I was in threat. I got to beat shift. Got to be, you know, got to whatever, whatever. Got to become an SPMD. And now it's like, well, it's more positive. Some it's like, no, I want to do these things that I want to do. They get me excited in the morning. They energize me. And I'm going to trust that like the rest will take care of itself to some degree.

Yeah, it's interesting you say because even for us, like for our current business, you know, we originally, you know, we pivoted. We had a fintech business and now we're back into ad tech. And the— and I think to your point, the fintech thing was was us believing that the content was going to be the thing that motivated us because we were tired of ads. We were like, listen, like, we're tired of just being ads guys. And we totally fell for that, I think, trap. And now since we've pivoted back to like kind of where we belong and we started this podcast, like, I can— I know I'm happier. Like, I can tell people, and I think people actually want to be around me more, and it makes like a huge difference. And, you know, It definitely was like one of those things where we like we did spend a long period of time and we executed well. But the reality is, is like we were all pretty unhappy once we figured out that the, the content didn't make a difference. Yeah.

And you're probably doing it for the wrong reasons. You were like, well, no, ad tech is not sexy, so I have to go do fintech now. Or like, I, you know, you're choosing it because of the status or the extrinsic. And like one of the funny things that happens, like I, you know, James, a lot of my employees worked for me for a long time, especially my senior folks. And I had at least two that took me aside at some point and said, you know what's weird, Jesse? When there's a problem in our business, you don't say anything different than you did five years ago. I mean, triaging a broken ad account, as we both know, is like it's it's the same process. They clicked the rate up. Is it down? Like they go, but I just feel different. Like I feel different coming out of the meeting with you. And it's funny people said that because like I worked on my coach specifically instead of showing up with being threatened by something bad happening, showing up like a teacher. Like he said, okay, those are the moments where you can be a teacher. Now again, what the content is no different. There's no way you can do that any differently. You're like, what are the numbers? Let's look at them side by side. What's changed? You know, like, but if you're showing up like a teacher to someone versus showing up as like a boss to someone, they feel very different. And so that's just another good illustration of like context versus content.

It's also interesting that you, I mean, you very just clearly love teaching and kind of imparting this wisdom and like helping founders and just people that are interested in this journey. And with GatewayX, you have a one-to-one connection with a lot of your CEOs, with a lot of the teams, but you also do the newsletter and the podcast, which is more of a one-to-many kind of education.

Yeah.

I mean, do you, how do you approach the two and like, Do you prefer one or the other? Like, how do you think about the difference between reaching people, you know, passively listening to you versus somebody that you can speak with and get that feedback in real time?

Yeah, yeah, that's a great question. You know, I'm kind of the same person everywhere. I think I'm not— I try, like, I've tried to be fake in my life and I'm just no good at it. Like, and so I kind of just stopped. So I think the, you know, there's a different feedback mechanism for the public stuff. Like, I get a ton of DMs on Twitter. I get a ton of messages on certain podcast episodes. They're sometimes— at first they were overwhelming, honestly. First they were really heartwarming, then they were very overwhelming. And now I've kind of like somewhere in the middle of trying to figure out how to deal with them and maybe just not feeling the need to respond to everyone. But I think the interaction of the CEOs, it's like, it's less, you know, like what I just explained to you guys around this, like that's kind of a good for public consumption version of it. With like, with one of my CEOs, their last startup was a big failure and he's been really struggling with like shifting out of the fear mode of like, oh, what if he screws up here and there's another failure? And so the— The conversation is a little bit more intimate and deep around what are you actually afraid of? How can I support you in not feeling that way? Like, you know, there's a whole different level of kind of depth around it, but it does inform a lot of the things I do. I think the public stuff also, like a lot of people before they do it, I was a little skeptical that it's like real, you know, like I was like, does anyone care what I have to say? Even if they do, is it real? And I think like the amount, like when, when there are certain things I've shared that have gotten people like all kinds of people like out there responding to me, like I've had the craziest one probably is now he's become a dear friend. But the, the CFO of Facebook is from St. Louis and reached out to me on Twitter.

Wow.

And now we've become friends because he's actually spending more time here. His family's still here and he's like, Yeah, I like your content and it's helpful. And I'm like, holy shit. So, there's been a lot of instances like that where you feel the realness of it and it doesn't just feel like a hollow thing. And then, by the way, there's times where I've tried to get ghostwriters and other things to do and it hasn't really worked that well. And so, there's times where I myself have almost betrayed my audience or hollowed it out trying to scale or trying to get it off my plate. It doesn't really work. You can almost see it in my numbers. If you just looked at the charts, you could probably guess when I was doing a lot, when I tried to not do like— and it's kind of crazy that there's still a pretty meaningful feedback loop there.

And are you now— because it's funny, legitimately one of the reasons why we started this podcast was based on a conversation I had with you. I think it was like 9 months ago or something like that when you were like, dude, you should just like start tweeting, like telling people some stuff. It's just like you've had interesting stories. And I kind of had the same thing where I was like, does anyone really care. And then I found that for me at least, I struggled writing. It's easier just as a medium, just talking. But if there's other people like that, probably a lot of our friends, that like, how would you recommend people do get started? And like, how did you actually get started? Like, was it like you're like one day you're like, you know what, I'm just gonna start like telling people what I think? Or is it like a concerted effort, like with your coach?

Yeah, I think it had been on my mind for at least a year or two prior to starting it, and I'd obviously been reading what people were doing. There was like some people were early to it, and then I moved back home to St. Louis from the Bay, and like there was definitely a part of me that was like, shit, like I'm not going to be in the room where it happens anymore, right? Like I'm just going to be sitting in the Midwest, whatever. So like it would be valuable to create some other room for myself that I'm in. And then I think like a lot of things, like, so I ended up getting to know Patrick O'Shaughnessy pretty well and like him and I recorded a podcast on his thing and like, and I was like, all right, well, this is as good an effort. Like, this is as big of a thing as I've ever been on. I might as well start putting like, let me go put some meat behind this. And prior to that, by the way, I had like The one thing I'd started doing was like I was probably a reader for a year or two of Twitter, and then for probably six to twelve months I was like a commenter. And I always tell people when they ask me, I'm like, start by just like engaging in the conversation. And like if you don't see people liking your things or following your things, like it probably means you're not saying anything that interesting or valuable. You know, and like again, like James, you and I have seen a lot of shit, and like we just had a very interesting perch for ten years. We saw I got to see Facebook and Twitter and Pinterest and all these guys grow up, and we saw all the Smart things they did and the dumb things they did. And the same thing with all these brands, like. And so I just started kind of responding with learn like things I knew, and I was like, oh shit! People are following me or they're liking it, or I'm like you know I'm getting a DM, and that kind of gave between that and then being on the podcast, it gave me the courage to like okay let me go do this. And then I think the first six months were just super fun. Like I was like, and the way I started by the way was I picked up like you know everyone has their stories that they tell. They're like I call them the dinner stories, like the stories I tell people at dinner where people are like loving the story I'm. telling. And I'm like, okay, I'm gonna just take these stories and I'm gonna turn them into threads, basically. And so, and then they started working. And then like, it wasn't just the growth of my followers and all that stuff. I was also getting a lot of DMs being like, thank you for writing this. This was, you know, really unstuck me in the following way. Or, and so when I think that really opened my heart up a little bit and I was like, oh shit, this is like really, people are actually benefiting from this. And that I think, yeah. So I think that first year or so was super fun. I think it started to feel a little bit too forced at some point and I tried to like pivot around in it. And now I'm still experimenting with things like this podcast. Like I was telling you guys before we got on the recording, like I've been working with a couple of people on the team here of like, okay, can you listen to me talk and can we turn this into written content that's compelling? And it's been, it's been much harder than I expected it to be. even with transcripts and everything else. But like, we're getting better at— like, we had this viral tweet on Sunday about Marc, how Marc Benioff runs Salesforce, allegedly. And like, it was one where it came from an old Crazy Ones episode that I did not write. I looked at it and reviewed it, but so it's like, oh shit, if we can do that. To your point, like, writing can be hard and I don't mind if it comes through me. Like, my best threads have been ones where like I woke up and I was like, oh shit, and I just wrote it and it took me 30 minutes to write and it was like pure, just coming from my heart. The shittiest threads I've written have been like, okay, Jesse, it's Wednesday. You said you'd post a thread on Thursday. And I'm like, all right, what am I going to write about? Like, so I think there is a creativity element to it that, that's important. You can't force it.

And one thing I've sort of struggled with, with even just this podcast is like, I'm trying to be— we're starting to get DMs, we're starting to get people commenting and like, it seems like we're providing value. But then, you know, and I want to respond fast because That's like, even like in business, I've always like been like the person who's like, okay, like one of my superpowers is like, I can outwork you. I can respond fast. I have more energy. And I found myself actually be really distracted at home, just like with my kids and my wife. And it's like the balance there. And especially given like how big of a megaphone you have now, like how do you draw boundaries there?

I think, I think I did the thing where I just got like Overwhelmed to the point where I basically gave up. So, yeah, I don't like I don't basically respond. Like if if I happen to be in my DMs or maybe if I see a name like yours that I recognize or someone that I think is you know big deal, I'll get back. Otherwise, I have like a growth assistant, you know, sitting in all my DMs basically. And then we have a triage system for like, okay, is this a person looking to interview? Route them here. Is it someone who like knows Jesse personally? Like at first I just gave up for 6 months. I just stopped responding to all of them. And I like, you know, I think I don't ever want to be the guy, like you said, I don't want to be— I pride myself on being responsive. I also don't want to be the arrogant guy who's like, oh, I'm going to like make you jump through 3 hoops to talk to me. And like, If someone really wants to talk to me, if I really am important to that, like they should find a way that's not my DMs to get to me.

Yeah.

Like email me at least, figure my email out or ask a person, you know, like, and by the way, I will, if someone sends me a DM that's pretty thoughtful and is like thought about whatever, like adds value, whatever, then I'm like, all right, that's a little more interesting. If someone's like, hey, great to hear you on that thing. Mind if we set up 15 or 20 minutes? Like, I just— and I hate to be a dick, but I'm just like, I can't. I like, I just can't do it. I can't respond.

You know, one thing you mentioned, Growth Assistant in there, just before we get into our Daniel's famous rapid fire. But do you use all of your— is it kind of interesting now, like the Gateway products, how many of them you actually use like in your life? Like Are you like taking Unbloat Me? You're using Growth Assistant?

Like, yeah, yeah. I'm like, they're all, yeah, we, I mean, Growth Assistant is GatewayX is probably one of the biggest customers of Growth Assistant. And like, it's become almost like everywhere inside where we can use someone who's not, you know, who's not US-based, we'll try to do that. So that's the most obvious. Unbloat, I took for a long time. I like it a lot. I take cholesterol medication, so I— if there's like a weird— you can't have magnesium or whatever. So I had to stop taking it. You know, today actually Kahani is pitching Unbloat on using the new Pivot and like I purposely told them, I was like, don't use it because like you guys are like sister, like make sure that you actually think it's a good product that you'd want to use. And Ox Insights will be an interesting one because it's kind of got the Ampush benefit of like a lot of good people, like a lot of talented people. It's a services consulting business, but it is actually— we've used Unbloat, like a lot of the infrastructure I built there for the e-commerce. We're like, we've ported over into Ox is like because a lot of the clients are these private equity firms. Well, they're the private equity firm portfolio company. So we have a couple of clients who are Huge businesses like $300 million in top line, $50 million in EBITDA, and they have 5% of their business or 3% of their business is digital. And looking from the outside, you'd be like, dude, this should be 20%, 30% digital, right? And they just like— like we were sitting the other day with a management team and the private equity partner and no one had ever explained to them how incremental conversion rate is basically straight to your bottom line in terms of EBITDA. And they're really smart. So once we explained it to them, they got it. I mean, they were like, oh my God, that is really important. I see conversion matters a lot. But we use all this infrastructure from when we launched Unblow to basically how we were gonna launch this for Aux. So that's been cool. Like there's definitely a lot of overlap, but none of it's forced. That's like a big, big rule for me.

We'll kind of jump into the last set of questions before we close out. But, um, let's start off with— you've talked a lot about bootstrapping and that being, uh, you know, very viable and should be a path that a lot of founders look at. Who's your favorite bootstrapped founder?

Oh, good question. Uh, it's probably Rick at Red Ventures. You know, um, I always tell people he's the first person I ever worked with in my life who I wanted Like when I worked at McKinsey, I'd look at the partners and I love a lot of them. They're like mentors and friends. I was like, I never wanted their job. They're on airplanes all the time. They work even at the hedge fund. Like I saw this guy made $10 million a year and he would sit in spreadsheets and like look at data. I was like, I don't wanna be that guy. And Rick is like the first person who, he's an entrepreneur, he's a business guy, but he's still a family man. Like he's bootstrapped, he's been profitable since day one. So probably him.

Is there a single piece of advice that you've received that you put into practice and kind of attribute a lot to? Hmm.

That's a good question. I think I don't have like a pithy quote, which is weird. Normally I do, but like, I think, I think just like the most important trait in a person or in a founder or whatever is self-awareness. And that's like the one thing that the more you develop it, it sort of like develops everything else. And like, I don't know if you guys know Johari's window, like they share it in different contexts, but it's like what you know about yourself, what you see about yourself versus what other people see about you. And you're basically trying to grow that box of the matrix, right?

Mm-hmm.

Which is like everything other people see of me. Like, I wanna be able to know myself and know the way other people are seeing me. I mean, that self-awareness is really, really powerful. And so, You know, another version of it I like to give inside companies is like, if you have a good system for feedback and response of feedback, like, what do we do? Did it work? Did it not work? Like, you'll just keep getting better, right? And you'll be evergreen. And like, I really related to it as like something Rick definitely says, but I agree with is like the only true long-term differentiator of any company is culture. Because over time, like, I mean, dude, you look at the iPhone, it's great. Like, but Samsung made the same. Like, everything can be competed away. But culture cannot. And like, to me, those all kind of relate to each other. Like if you have a culture of self-awareness, continuous improvement, getting better, you can just kind of take anything on.

Love that. And Jesse, so you're doing a lot of things, you're in a lot of places. So where can listeners find you?

Yeah, you know, Twitter is a good place to start. We're this Friday, we're going to launch the new kind of full-on new Bootstrap Giants newsletter. We're going to, we're going to give out templates every week with different things I've used to scale businesses, different lessons I've learned. So That's kind of becoming the owned audience, if you will. And we're going to— so that would be sign up for that email list if you want to hear directly from me.

Okay, great. We'll put that and some of the other things you put out in the show notes. But Jesse, this was great. Thank you so much for coming on.

All right.

See you guys.

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