The Dark Side of Ambition: What a Racing Mind Feels Like | JT White | Augie Studio

Shamil Malachiyev: Good morning, everyone. On this episode of The Founder's Code podcast, we have the co-founder of Augie, an all-in-one video studio designed to make video-first marketing attainable for any business. He's also the host of the Build for the Better podcast. And by this time, he's the author of a book that has just been released on November 18th, called Build for Better: How to Build Successful Digital Products and Companies. Please welcome JT White.

JT White: Hello, thank you so much for having me.

Shamil Malachiyev: So nice to have you. Can you tell us: how much discipline does it actually take to finish a book?

JT White: God, a lot. A lot more than I thought. If I had known how much discipline, I probably never would have gone down the path of doing it. It's hard. It's a weird exercise in a little bit of grandiosity about yourself, thinking that you have enough to say to do it, but then it's also really grounding. So it takes a lot of discipline, but I would also highly recommend everybody just try to put your thoughts down and see if something cool happens.

Shamil Malachiyev: How long did it take you?

JT White: Oh God. Well, it's been a five-year journey to getting published, for a bunch of reasons. The writing itself took about a year. It was about a full year before I had a thing that I thought was finished. I mean, I'm a product person, nothing's ever finished. But something that I would live with being out in the open forever — that took about a full year.

Shamil Malachiyev: And did you devote a couple of hours every morning? That's what I mostly hear from people: they would wake up two hours earlier and just make sure to write something in those two hours. Was it something similar?

JT White: Yeah — I'm a night owl, so mine was at night. When my kids and my wife would go to bed, I would lock myself in here and put on trance music and just try to put lots of thoughts on paper. What I would actually do is put a question up and say: okay, answer this question today. How would you answer this question? And I would write a bunch of stuff and then see if there was anything I thought was of interest. I have more things that didn't make the book than things that did.

Shamil Malachiyev: Was it really hard to keep the book short and focused?

JT White: Yeah. Verbosity is a problem of mine in general. I love talking. A lot of the concepts of the book, and just my life in general — there's a great German designer named Dieter Rams. He has a saying that I try to live a lot of my life by, which is "less but better." And so the entire purpose of the book is to be direct, to the point, and not superfluous. Trying to keep it really tight was a challenge, because I could go on and wax poetic about this stuff forever.

Shamil Malachiyev: And maybe we can do a bit of advertising for the book itself. Can you tell us who this book is going to be perfect for?

JT White: Sure. So it's kind of twofold. I think anybody who's in the product world. If you're a product manager — product management is not a degree you get, necessarily. Most people find their way into product from somewhere else. So product managers are definitely the most intended audience. But also founders. If you're a founder of anything and you're thinking about how you talk to other people, specifically in the digital space — what it takes to build a good team. For all intents and purposes, the book is a love letter to my failures. It's not a book of "I did all these amazing things." It's actually a book of "I did all this stuff and learned that it was bad — this was the wrong way to do that." So I would say anybody who's in the founding space, which right now, because of AI, should ideally be everybody. You can learn from my mistakes so you don't have to go through the pain that I went through.

Shamil Malachiyev: Do you think the product management of three, four, five years ago is going to be drastically different from the product management we see today, especially with the use of AI and how much control we give AI over thinking through the general concept, giving ideas and features? Because some people don't even do any user surveys. They just ask ChatGPT what that kind of person would think of this feature, and act on the result.

JT White: Yeah. I think about it a lot, actually. I don't have an answer, to be honest. I think there's no version of product management that doesn't change dramatically. It's changed a lot in the last six months. It changed a lot in the last year. I think it's going to continue to change. I think of it more as an evolution than a revolution for now. I still think someone needs to be orchestrating the whole concept and the whole vision. That's still really important. But to your point — I've never been a huge fan of 35-page PRDs anyway. If you're writing some novel about a requirement — if you can't tell me in a page or two what it's doing, I don't think you know what you want it to do yet. So consolidating a lot of that noise is probably good. But getting away from the users is terrible. Product is the voice of the user, ideally. And the best product people are the ones that can marry a business goal to a user end game and put those two things together. So I still think there's a lot of personal, human-in-the-loop nature to building products. What I do think has changed, though, is the scope of who can be a product person. My line has always been: I know enough to be dangerous with engineers to not get lied to, but you don't want me to code your platform — that's terrible, I can't do that. Now, because of things like Cursor, and because of ChatGPT and all these other LLMs that are out there — Lovable, Replit — the opportunity to become a product person has never been cooler. And I actually think that's great. I think it means more people are going to be makers, and I like makers. So I'm interested. I think it's going to change and evolve. I don't think it goes away. I think it changes dramatically.

Shamil Malachiyev: And can you tell us a bit about your personal journey of building a company? Did you always know that you were going to build a company one day?

JT White: So I have a weird backstory. I actually sold my first company when I was 16. And it was by mistake, and it wasn't cool. The company was cool — what we built was really cool — but the end game wasn't cool. I always tell people all I got out of it was enough to buy a car and a real distaste for the music industry. I think I've always wanted to be my own boss. I've always wanted to be at the table. That was always really important to me. It's just the way my brain works — if you're into Enneagram stuff, I'm a challenger and achiever. Big corporate structure doesn't really work for me. So I've always known that my path was probably going to be making stuff. And what I've learned in my journey is that the culture is as important as what you're building. I want to make sure that I can be as close to the culture as possible and influence it where it makes sense. So I've kind of always felt like this was my path.

Shamil Malachiyev: Can you tell us about the early experience when you were 16? I don't think that many people get to build a company, or sell one — or even sell it at enough of a valuation to be able to buy anything more expensive than a t-shirt.

JT White: Yeah — look, to be clear, it was a 1997 Dodge Avenger. It wasn't a nice car. What happened is — invention is always born out of necessity. I've always been very into music, and I've always loved hip hop in particular. At the time there were a couple of different sites where you could go and try to up-level your game as a lyricist, and the predominant one at the time wasn't really a friendly place. It was a lot more competitive and battle-y than it was a cipher, which is more about collaboration — helping people up-level. And so me and my friend were like: we could just build this. It was a vBulletin board — it wasn't a complicated tool — but we decided to take all of our favorite people, put them on a different platform, and try to change it. And in the process of doing that, we unintentionally built focus groups. We didn't know that — we had no idea what we had — but we wound up with a really, really good community for artists to come and try some of the stuff they wanted, to see if it was going to work or not. And again, it wasn't some huge thing for us. For the buyers it was: okay, this is a cool little thing, we can harness this community to do something else, and these kids will go away. And that's what happened. They took it, and I have no idea what happened to it — I wasn't a part of it anymore. But it was a really neat experience. I learned a ton about what not to do, how business actually works, and what acquisitions really feel like. I'm super grateful for it, but it didn't materially impact most of my life, to be honest. Plus, the only car accident I ever got in was with that car. So I didn't even get the car.

Shamil Malachiyev: Oh my. What about Augie?

JT White: Augie's great. Augie was a really cool experience. My co-founder and CEO Jeremy has been a friend and a mentor of mine for 15 years. We were always on the same speaking circuit at South by Southwest and Digital Hollywood — we were on panels together and we ended up hanging out a bunch. And he had this really interesting idea. This is before LLMs were out in the world, before Stable Diffusion and Midjourney and all that stuff existed. And I had pretty deep experience in the ad tech background. So he floated this idea past me and, without him asking, I just wrote a five-page user story document: this is every use case I can think of, there's a lot of them, and I think it's really cool. And from there it was just a matter of moving from a really ugly prototype to "we can actually make this work," to fleshing out the business case, to "there's a business here — who are we going to serve and what's that going to look like?" And then the fundraising process, and growing a business, and trying to make a thing that matters and also does what you want it to. It's been an incredible almost four years now, and I'm super grateful for it.

Shamil Malachiyev: And how was the start of your co-founding relationship? Did you have to think that through? Because a lot of people, when they come into a co-founding relationship, ask: okay, if shit hits the fan, how do we split up? Did you have to do something of that sort?

JT White: Yeah. So I think Jeremy and I did it in a really fun way, and it's one that I would really recommend. We had built stuff together before, and we're both product people. I'm in a weird position as the chief product officer — working as a product person for a product person is definitely a weird up-chain. But he's really gracious, and he's really smart, and we respect each other, and we had built stuff together. I don't want to say it wasn't meaningful — it was meaningful to us — but we didn't build companies, we built projects. We had a podcast together that we loved that was just about movies. During the pandemic we built this thing called Wingman Daily, which was just an email that went to your inbox with three fun things that we thought were cool every day. But in the process of doing that, we figured out a workflow. We knew where my strengths were, we knew where his strengths were, we knew where we could pick the other person up. So we had already built a really healthy mechanism for building. And because of that, I would say we've had very, very few altercations. And also, because we're both senior and have been doing this for a long time, if he's really passionate about something and I disagree with it, he can take it. And he does the same thing for me — if I get really nerdy about something, he's like: okay man, go do that. We just have a lot of respect for each other, and I think that's why it works. It works because we ultimately respect the other person. We figured out where we're not good. He knows what I'm not good at, so he knows there are certain things he's going to have to hound me about, because I'm just going to forget — it's just not high on my list. And likewise, I'll do the same for him. That profound respect for each other is what everything is rooted in. And also, he's my friend. I want to build stuff with him. We like each other. I want him to win, he wants me to win, we want us to win. So it's been an incredible relationship, and one that I value, and I can't put words to it.

Shamil Malachiyev: It's just that I always hear there are two camps. One says you have to build with somebody you've been through some battles with, someone you've learned to engage with. And other people say: don't mix friendship and business together.

JT White: Yeah, I think there's value in both. It depends on the person. It depends on what kind of friendship you have. Jeremy and I — our friendship is rooted in making stuff. We like to make things, and we like to bounce ideas off each other, whether it's working out, or cars, or fashion stuff. We just like to talk to one another and challenge each other to do stuff. So in that instance, I think it works great. I also have a really weird thing: I hate when companies say "we're a family." No, you're not. Family is an obligation. That sucks. Don't be a family. You could be a community, though. Be a neighborhood, where you all look out for each other, and you want to make sure the property values rise, and you take care of your lawn so everybody else's lawn looks good — so the neighborhood looks good. That's what it is: it's a community. And by building community as opposed to family, everybody understands their roles and has their own house and does their thing, but ultimately it's for the greater good. Rising tides raise all ships, or whatever.

Shamil Malachiyev: Were you ever in a situation where you thought that when you're building something, it has to be a family first? Because almost everybody makes that mistake. I used to make it. I remember myself back in the day — I would have five, six people working for me in the early days, and we were like: yeah, we're a family. And only five years afterwards I realized how detrimental that is to the success of a business.

JT White: Yeah, I've been through every version of it. I went through one where — and she's still one of my favorite people on the planet, my kids think she's their aunt — we were a family. There were three of us and it was really, really tight. And there were huge benefits to it in the early days, but there's bad sides too. Everybody's too close, and that becomes an issue. But then I've also been in companies where it got really cold, and it didn't even feel like a community. So I do think there's a balance. In my youth, I think I really benefited from that feeling. I think it was good. It gave me confidence. It gave me an opportunity to explore in ways that I wouldn't have been ready to otherwise, which I'm eternally grateful for. But ultimately now, as someone who's in the driver's seat of building companies, it's just not for me. I think community-based is the right approach for the kind of company that I want to be a part of right now. Because again, that obligation of family is really intense. It's a really intense feeling. And that doesn't mean you shouldn't love your coworkers, and it doesn't mean you can't be in each other's weddings — I'm a huge fan of that. But it should feel like you opting into being a part of something, as opposed to having to be a part of it. And it's challenging, especially in early-day startups. You just go through so much war together, you have so many battle scars, that I think it's natural that it starts to feel that way from the jump. And you just have to be mindful of it as a leader, to make sure that people still have enough space to be themselves and not feel like they're obliged to do things.

Shamil Malachiyev: And do you think it's important to instill a certain culture and make it official within the company? Or does that come at a certain scale, or number of people in the company?

JT White: It's a really, really good question. I think scale matters a lot. I'm a huge proponent of culture in the sense that it has to be set from the top. You have to set expectations. In the book, I actually talk about signals. If you as a founder are responding to emails at 2 a.m., that's a signal. You're signaling to people: hey, you've got to do that — now I'm doing it. Well, no — you're a founder. You can write the email and then schedule it to go out at 8 a.m. Because the signal you're going to send is not the right one for the kind of company I want. I'm not taking the piss at anybody who wants to have a 24/7 work culture — that's on you, some people like that, not for me. So I do think even simple stuff matters, like the tools you use. What's your Slack culture? Is it sync or is it not? Because if it's asynchronous, that's totally fine — when you get to it, you get to it — specifically if you're working with creatives or engineers, where they get in flow states and you don't want to mess up the flow state. And if you need it to not be asynchronous when it's usually asynchronous, what's the mechanism? Is it a certain word? Do you use a certain GIF that tells people they've got to break out for a minute? Just set precedent so people know what the expectation is. Because expectations is the enemy of joy. If you set all these expectations and constantly break them, or you tell people that we're an async company and then you're not — you're firing emails off at 3:30 in the morning when you wake up in a cold sweat because you're a founder, because that's what we do — the signal is wrong. The signal has to match the practice. And I really think that founders should sit in a room together, ideally for a week if you can, and ask: what do we want this to look and feel like, and how do we enact that? And then hold each other accountable when you break it — because you will break it. You're going to break whatever stupid rules you put in place. You're a human. That's what's going to happen. So how do you hold each other accountable for that? And then make it a practice, because I think the practice is really important.

Shamil Malachiyev: And what about the tough times? With building anything, you have to be a little over-optimistic to have enough charge to start something. When the reality hits — can you tell us about some failures within building a company, some challenges that you went through, and what kind of frame of mind helped you persevere for four years now?

JT White: Yeah. So there's a couple of different answers, and some of them are going to get a little bit weird, but that's who I am as a person. Look, the biggest challenge is always funding. That's the thing you constantly have to be paying attention to: your runway. And it sucks that that's the case, because in a perfect, utopian world, you're just building until it's good, and then you're like: yay, we did it. But that's not how this works. So being really mindful of capital — what it means to you and how you want to spend it early — is a big deal. You should spend real time talking about: what do we want to spend money on? What bets are we taking? What bets are we not taking? Why are we taking the ones we take? I think that's really important. For me — I meditate. That's a thing that I need to do, because I don't know if I'm diagnosable, but I've got a lot of markers for ADHD stuff. And it's real easy for me to get distracted. That's an unfair generalization, but I think a lot of people in the startup space tend to have a brain like that. I like problem solving. And so it's really easy for me to fixate on a problem and go: ooh, I could do that, ooh, let's fix that. And then all of a sudden you're totally scattered and nothing's getting done. So harnessing calmness, and really being mindful — and I hate that word —

Shamil Malachiyev: What do your meditation practices look like? Because they seem to differ for so many people.

JT White: Yeah, I could do a whole hour on this. I'll make it quick, though. I personally fully misunderstood what meditation was. I thought that meditating was sitting down and having your brain turn off and just chilling. What I learned is that that's not my meditation. My meditation is accepting all of the thoughts that never turn off in my brain, acknowledging them, and then moving on. So it's taking time throughout the day to be like: whoa, there's a lot happening in my brain right now, I've got to move past some of these things. Whether it's a walk, or sitting — I'll sit and just turn everything off and be quiet for a minute: okay, brain's overloaded, moving too fast, have to slow down. Watch my heart rate, get my heart rate lower, turn off a lot of the noise, and get to a place where I feel like I'm better suited to handle something. Because you can't be at 110 percent. If you're operating at a hundred percent and you have lots of problems coming in — one of my challenges as a human is to over-index or under-index based on what I think I can get done. And that's not what being a founder is. Being a founder is prioritizing based on what it's going to mean to you, not what you can fix. My goal is: I want to fix stuff. Sometimes you have to move past the things you know you can fix to handle a bigger problem you don't know how to solve yet. So for me, it's literally just slowing everything down, taking a couple of minutes to be like: okay, we're not in a position to do good work right now, let's reframe this and just chill for a minute, and then go back and re-establish what we're trying to solve for. I try to do it every night. I meditate every night before I go to bed too, because again, my brain doesn't turn off, so I need to get my brain in a place where I can actually sleep — because sleep's really important. And it's the same thing during the day. All of a sudden I'll just realize — my joke is that I have tabs open in my brain. If I have too many tabs open, I'll be like: we've got to close some tabs. And so I'll go through and settle myself down, and then go back: okay, these ones don't actually matter right now, I can close these and get back to it later.

Shamil Malachiyev: Did you have to go through a lot of self-awareness moments to get to that point? Because I remember myself, when I tried it — I would think: okay, if I go to the gym, I'm going to be in a better frame of mind, I'll be fresher. If I go for a walk. But then I would have so much on my plate, I'd think: well, instead of going to the gym, I could spend those two hours trying to fix the issues. Identifying them, mapping them out, mind-mapping, writing them down on a piece of paper. And then you never actually get to the walking — to disconnecting from thinking, to letting your anxiety, letting your brain rest for a bit.

JT White: Yeah. I mean, even with the people that I work with, I'm a big fan of: take a minute. I work out every day. I love the gym, I lift, I also ride bikes — I love riding bikes. So I make a point that it is on my schedule, in the morning usually, because that's when I need the endorphin hit, because I usually slept poorly. I need that. And if I don't have it, I feel it — I can feel it, and the people that work with me can feel it. I have really cool people that work with me who'll be like: did you work out this morning? And I'm like: no. They're like: yeah, we can tell. Calm down a little bit, you're coming in too hot. I think those things matter. Again — less but better. I want to focus on fewer things and be better at the things I focus on. And as a founder — and not just a founder, as an employee of anywhere — it's never like you have a lack of things you could be doing. You could be doing all the things. But it's about doing them well. And I hate rework. I hate having to go back and do something again. And by the way — I'm 40, I just turned 40, and this has been a whole self-discovery for me, to your point about self-awareness. This was not 20-year-old JT. It wasn't even 30-year-old JT. I've had to really look into myself and be like: oh, you're a nightmare sometimes. You need to calm down. And so now — whether it's age, or meditation practice, or working out, or, I don't know, maybe it's having kids — there are all these things that are obviously part of my story. But for me, a lot of it has been the settle. Okay: what are we going to do today that's going to be meaningful and impactful, that you could actually move forward on? So that you don't have 50 tabs open and all of them get partially done, and then you don't feel like you checked anything off the list. I know some people are really big on lists, and I'm not. I'm not good at lists. I don't want a list of "I did three things today" — it's just not the way my brain works. But I do take a very similar approach, which is: okay, what did I do today that was good? Did I focus my time well? Did I miss anything? And then be better — just get better tomorrow.

Shamil Malachiyev: I can never do lists as well. My brain keeps telling me that making lists is an amazing way to go about it — structure everything, draw everything out. But I just never actually get to do them, because I don't feel like they're that effective.

JT White: Well — I don't want to speak on your behalf, but I think you might have the same problem I have, which is that I'll hyper-fixate on the list. So then the list takes me an hour and a half, and now that's dumb. I'm so worried about the list being thorough that I'm like: I should put it in a spreadsheet, and then I should — no, this is stupid. I'm just going to take a step back and ask: okay, what are the three things I can positively impact today? And another thing — it's not directly your question, but I think it's meaningful, and I really try to preach this to the people that I work with: I've also come to terms with the fact that some days you're not on, and that's all right. Now, it doesn't mean don't do things — don't just take the day off — but if you're not in your best place, whether it's personal or sleep or whatever, tackle the things that you can tackle that day, so the ball moves forward. And if you need a day or two to tackle the bigger thing, tell people. Again, this is the community part, not family. Community is: hey, I can't do this today. It's too much, it's overwhelming me. I need help. Ask for help. And if they can step in and help, great — maybe they'll move it forward for you. If no one can do it but you, that's okay. And sometimes you're going to have to swallow it, specifically as a founder at the top — there are just going to be days that you don't want to do it and you have to do it. But even just saying out loud: I'm struggling with this right now, because it's overwhelming, or it's confusing me, or I don't know the answer and I can't find my way out of it — say it out loud. Don't suffer in silence. Go tell somebody on your team: hey, can you walk through this problem set with me for a couple of minutes? And maybe they free you up, or maybe you find out you really are stuck. That's also okay — now you know that you're stuck. Now what? What's next? I think in those moments we forget how human we are. You're not infallible. There are going to be days that are tough. You're going to sleep poorly. You're going to have a bad Monday. You're going to have a tough Friday. You're going to be worried on Tuesday about a meeting on Wednesday, so your Tuesday is going to go down. It's just part of the thing. So acknowledging it, figuring out how to work through it, and leaning on the people around you to help you get back to a place where you can do your best work, I think, is better than that "just work harder" thing — Nat Allison had a great Medium post, like ten years ago now, called "hustle porn." Well, no — don't. Because you can work really hard and be wrong. So don't do that. If you're stuck, be stuck for a minute, and take the time to figure out how to unstuck yourself. And if you can't, ask for help. And if nobody knows, then you've got a bigger problem, and that's okay too — but then approach it as that: we're at an impasse, this is a big decision, now what? As opposed to just trying to muscle your way through it — which at the gym is my favorite thing to do, but in life is bad.

Shamil Malachiyev: And I really like that you actually identified that there are bad days. I think I heard Alex Hormozi talk about this a few months ago, and he said: well, 10 percent of your days are just going to be bad. If you wake up and today's just a bad day, treat it as such. Don't set any higher goals for yourself for that day. Just make sure you do what you can and move on.

JT White: Yeah. It changes everything. And it's hard — listen, in certain disciplines it's easier than others. If you're in sales, it's easier to have a bad day, because you can just do follow-up emails and not worry. If you're an engineer and you're in the middle of a sprint and you've got a bad day coming, it's harder to say: I can't do this today. But again, that's where I think having a really open communication line with the entire team and your organization matters — making sure that people feel safe enough to have that space. Now, also, as a founder there are lines that you're going to have to draw. There are going to be days where you're going to have to say: no, we need to do this. This needs to happen. So then it gets into the "what would have to be true." You get to say to somebody: okay, listen — what would have to be true for us to get you to be able to do this today? Do you need other stuff off your plate? Do you need focus time? Do you need us to take something away from you? What has to happen? And that just has to do with being cognizant of the human condition throughout the process, and hopefully having a team that can trust you — that when you say we're here to help, you actually mean it. You're not going to set their chair on fire and make them sit there, and it turns into the meme: "This is fine." You don't want that.

Shamil Malachiyev: Do you personally ever struggle with motivation?

JT White: No, I don't. And it's hard, to be honest — not a woe-is-me hard, but there's just something in me. I don't know if it was my childhood, or how I grew up, or my circumstances, but my instinct is work. My instinct is to do stuff. I do not sit well. I'm very lucky — I live in Charleston, South Carolina. I live really close to the beach. I love the beach, I love the water. I don't sit. We go to the beach and my wife can just read, just lay in the sun, and it looks awesome. Nope — I've got to be surfing, or I have to be building a sand castle, or I bring a putter and I'll make a whole course for the kids. I have to be doing stuff. I'm very bad at sitting. So it's not a thing I struggle with, and I'm very grateful, honestly — it's worked out pretty well for me. But I've also had to put a lot of stuff in place to fix that. Because it's not always healthy, to be honest. Sometimes you do have to take a day off. The gym is a great example: you can work as hard as you want, your body needs to rest. It needs to. So you have to be really mindful about what days you do what. Maybe you take a cardio day, or a meditation day, or a yoga day or something. You have to build mechanisms that fit your personality type. My personality type is 100 percent to just fly at stuff. And so my work is not that — my work is to slow down.

Shamil Malachiyev: There are a few similarities that I've noticed among really high-performing founders, and I want to ask you a probably very generic question: has your why changed over the years? How so?

JT White: Big time. So I'm going to be a little ethereal for a second. In the US in particular, we have these two competing factors: there's freedom and there's safety. Safety is what boomer culture was raised on. You get a job, you work there for 25 years, you get a 401(k) or a pension, and you get to buy a house in Destin, Florida, and you're good. And then I think Gen X, and millennials more so, really want freedom. And freedom is not the absence of responsibility — it's really about time. Who owns your time? So the collision of those two things — you want freedom and safety — that's money. You need to have enough money that you can tell people no about your schedule. And that's what we all work towards. And for me — being from New York and seeing the volume of wealth that existed, and the kind of wealth that was achievable — I had a really, really unhealthy relationship with what I thought success looked like. And so my why was — can we curse on this podcast? Okay. I wanted fuck-you money. That was my end game, always. I love cars — anything with an engine, I'm into. So I was like: I want stupid cars, and I want multiple houses. And now — being a parent is a big part of it for me, for sure, but also my wife's a better person than I am in every capacity. It was figuring out that what I actually want is balance. Because I like working. I enjoy work. It's fun for me, and it's good for me — it's good for my brain. So now — look, I still would love fuck-you money, don't get me wrong. I'm going to continue to try to build products that can change things, because it's just who I am and who I want to be. But my definition of success has changed dramatically. Success for me now is living comfortably, my kids being safe, my wife being safe, having good friends, and building stuff that I like with people I like. That's success. Now, if that turns into fuck-you money, that would be incredible. But if it doesn't, I don't feel like I failed. And for a long time, that felt like failure. So I've had a total mind-flip. The times are weird right now, for a lot of reasons. Being able to say: look, my family is safe, and I've afforded myself enough freedom that I can go to the gym in the morning, and on the weekends I can go surf or ride my bike, and my kids get to do the things that they are passionate about right now, and I don't have to worry about that financially — that's sort of my new end game. That's way more important to me than either of those other things. It's somewhere in between: having enough safety and enough freedom to live a life that's meaningful and impactful, and with people I love.

Shamil Malachiyev: What I notice is that for a lot of people, the journey to fuck-you money actually starts at around 38, 40. Once they have enough experience, connections, greed and the ability to be assertive when they need to, they're no longer playing the startup game — they're building for the outcome. And until 50, 55 — that's where I see a lot of men blossom in their founding journey. And has your motivation changed much with having children?

JT White: Yeah, big time. It changed everything for me. Because before, I was doing it for me. A very selfish act. Everything I'd done up to the point of my kids being born was selfish. It was status, and it was wealth, and it was sort of a fuck-you. And by the way, I'm not ashamed of any of that. Where I came from and all that stuff — I had something to prove. I hate the whole chip-on-your-shoulder thing, but I did. And I wanted to give the middle finger to everybody that said I wasn't going to do it, or that I couldn't do it, or that circumstances, whatever. I was like: no, fuck that. I'm going to do this, and I'm going to rub all your faces in it. And you're going to know, because I'm going to pull up in whatever — that stupid shower thought where you take a helicopter to your high school reunion, that sort of shit. Super boring, but all of us have been there. Everyone's had that moment. It's a very schoolyard mentality. Kids, for me, reshaped everything, because all of a sudden it wasn't about me anymore, finally. And then, to be honest, it should have been about my wife more beforehand, but she's a trooper and she hung out with me. And so now I frame everything in — not legacy, because I don't really buy into that as much — but more: what does it mean for the people I care about? And my friends are the better for me having children, because now I care about them differently. It's changed the way I think about everything. And again, it's still selfish — I'm not a saint — but it's more selfless than it used to be. Now it's about: what can I create that is meaningful, that gives us the opportunity to do cool shit? Because we're a collection of atoms floating on a rock in the middle of space, and space is never-ending, and no one understands that. So have fun, have a good time, build cool shit, and do it with people you love, and it's probably good. If you can achieve that, that's a 1 percent problem. That's a really, really blessed place to be. And unfortunately, money is a part of it, because capitalism. That's still the game. And if you can find a way to play the game — and I'm still trying to figure it out, by the way, I haven't figured this out by any stretch — but if you can find a way to play the game where you're doing good shit, and you like what you're doing, and the people around you are better because of you, then you won. So that completely reframed everything for me. Because before, I said it was for me — I don't know, I think it was for everybody else. I think I was worried about everybody else seeing me as a success, because intrinsically, somehow, that would bring me value. The value I brought would be my success, as opposed to being a good human.

Shamil Malachiyev: But at the same time, were you ever scared of success? Seeing that you would become too successful for your existing friends — that everyone would feel jealous of you?

JT White: No. I think I'm a little different in this sense. That never crossed my mind. The thing that's interesting for me — and I want to be clear, most of my life I've taken way more losses than I have wins — is that there's two different people. There's people that love to win, and people who hate to lose. I think most people fall into the first category, where winning is adulation and it feels good. I don't feel anything when I win. It's relief. I feel a profound sense of relief, where I'm like: thank God it's over. And if I won, I'm like: great. If I lost, I'm mad. And I'm not necessarily mad because I lost — I'm mad because now I have to do the retro, and go back and ask: what could I have done? What didn't I do to get to the place where I felt relief? But because of that, I feel very grounded in the people in my life. I have my best friends from high school — we're still friends. We go on vacation every year. Their kids are my nephews and nieces, even though we're not related. There's nothing that I would do to lose that crew. They're my favorite people on the planet, and there's no amount of money that would get me far away from them. There just isn't. And it's because they've been on the journey with me. I have a lot of respect for people that have been on the journey. Because the journey of any founder — I don't care how good it went, even if it's your first time out of the gate and you crush it — it's exhausting. It's mentally taxing. It takes a lot out of you. And I don't think people see the second- and third-order consequences of this lifestyle. My favorite podcast that I ever did on my podcast was with my wife, because I sat down with her and said: hey, let's have a really honest conversation about what it's like for you to be in this shit. Because you're in this shit too. She's been a founder of this company, and she's been through three exits and five startups. She's seen all of it. It's hard, because the stress level is not more or less — but it's different. So I'm very lucky, I think — my mom who raised me gave me a real appreciation for people that dig in the foxhole with you. So that was never a concern. But the adulation thing is weird for me. It literally does nothing for me. It's a very weird thing.

Shamil Malachiyev: And can we talk a bit about the fuel for founders? It's another interesting thing that I've noticed a lot of co-founders have. Two weeks ago I was in Seattle, talking to a founder friend of mine. And she told me that right now she's trying to get rid of this internal need to prove herself to everyone — to her parents, that she can do something. And she said: once I get rid of it, I'll be more free to creatively engage in a different way. And having done so many podcasts, having talked to so many founders — the main thing that unites them is that so many have been worse off during their childhood, trying to prove to their parents that they could do something, to earn their love. And then that keeps growing within them. They constantly try to prove something. They create companies, sell one, start another — and it's never enough. And it seems like that kind of fuel is almost essential for somebody to persevere. Did you have anything like that?

JT White: That's really interesting. Yeah — whatever, I'll share it. So I have a weirder background, in the sense that I was raised by a single mother, and she was the fucking best. My mom was the best. I didn't have to prove anything — she just loved me for who I was. She let me be weird, she let me try all the things. She was great. But she passed away when I was 16. And she and my aunt were the only two blood relatives I had, and my aunt died two years later. Listen, it's part of my story. Everybody's trauma is their trauma. The thing with me is that it was never "prove." I sort of burdened myself with her legacy, where I realized that she's never going to get to do all the things that she could have done, because she passed away at 52, and she was fighting to keep a roof over our heads. So for a long time, I think I put her on me, where I was like: my existence in this world is a direct reflection of her, and she's not here to stand up for herself, so I'd better be really fucking good. And that was my chip. My chip was: I need to do this, because her legacy is on my shoulders now. And that was really fucking unhealthy. Entirely unhealthy. And then I think you sprinkle it in with imposter syndrome, which all of us have at some point — and if you don't, you're probably a sociopath. Eventually you wind up in a room with people that are billionaires or millionaires that have all this money. It's very rare — I've met a couple of people like this — it's very rare that you walk into that room and immediately feel at home. It takes reps. It's the 10,000 hours thing. You've got to put in reps to feel comfy in that room, and not let their opinion of you and your company change how you feel about yourself. So I think you're right. I think there's always some sort of something that you're chasing. It's either adulation, or it's just proving everybody wrong, or it's proving somebody right, or whatever the case may be. I definitely think there's a line there. And I think for me in particular — having kids changed that for me a lot. I stopped chasing it, because I stopped doing it for her and started doing it for them, which is what she would want me to do anyway. So I at least can talk myself into why that's the right choice.

Shamil Malachiyev: Now it's on their shoulders to continue the legacy. A good legacy.

JT White: Yeah, right. Well — I've got to be good first, right? Modeling behavior. I have to do a really good job so that they have a high target. But I do think there's something to that. I mean, look — being a founder is crazy. You have to be crazy. Everyone knows the stats. 99 percent of businesses fail. Period. Hard stop. The end. That's not noise — that's a signal. And yet here we all are, right? Not saying it out loud, but thinking about the billion-dollar valuation, and who could buy us, and: what if we did this? I wonder if it would unlock this. It's the Mad Hatter. You've got to be a little bit nuts to think that you could pull this off. And the thing that I have learned in my time — and I think what you said earlier is really important — my dad... so, then I got adopted. A longer story for another podcast, but I was very, very lucky that I kind of walked into another family that kept me whole, and has made me whole, and taught me a ton of cool stuff. And my dad always said: look, you don't make money till your forties. And I was like: well, I've made really good money. And he's like: it's not about the number. It's about what the money is — what you can do with it. You can make big salaries, but when you're a kid — I pissed away more money than I can begin to tell. Now look, I've got a lot of fun stories because of it, and I don't regret any of it — well, I regret a little bit of it. But for the most part, it's what you know to do with the money. How do you invest in your future, and how do you invest in your time? Those things you're just not capable of when you're 26. Most people aren't. There's some special people out there, but the vast majority of us are just trying to figure it out. And it took me until probably my mid-thirties to really start to hone in on who I actually was, and who I wanted to turn that person into. And those were two very different things. There's who I wanted to be, but some of it was incongruent with who I am. And I had to figure out: well, this is who I actually am — how do I mechanize and mobilize this person to be the person that I want? And it's work. You've just got to put in the work, and figure it out, and try stuff, and fail, and whatever. And I think now I'm in a position, finally, for the first time, where I can see the next ten years, and I'm like: okay. I feel pretty comfortable in the steps that I think I have to make to get to where I'm going to make the most impact for the people I love. And then, ideally, do the same thing for the people that I serve, by building cool products and companies, so that everybody who works with me is having a good time and is successful, and their parents are proud, and they're proud of themselves. And the thing that we make is making people's lives easier and better, and they feel better because they have it, because it makes them feel fulfilled. It's that whole circle thing of trying to figure it out. But if you'd asked me at 30 — I had no idea. It was: more money, more stuff, bigger titles, cool titles. Okay — but why, though? To what end? I didn't have an end game. The end game was success, and it was a really vague definition of success.

Shamil Malachiyev: And then once you have it, it feels easy, because you have that goal, and life is easy. You just have a goal. You're running towards that goal: make lots of money, be successful. That's it. Don't worry about anything else. And it's a very simple life. You don't have to think about anything else. You wake up, there's the goal — let's go. But then, the closer you get to it, or the older you get, a lot of weird transformations happen within you. And in your story about how you've transformed through the ages — I've been feeling the very same way. And the main question in me is: is it possible to induce those transformations earlier on? And another one: should it be done, even if it can be done? Or maybe just enjoy the ride — we're all going to die someday, these are the patterns that happen, enjoy all of them.

JT White: Yeah, that's a really good question. My immediate instinct is: don't induce anything. The journey is the destination sort of deal, right? All the stuff that I know now mostly has come through failure and mistake. And so if I'd been able to skip that part, I don't think I would actually be a more interesting person. I think I'd be a boring person. I mean, I know some people that have done incredibly well very early, and they just seem to have their head on their shoulders, and whatever worked, worked. But one of my favorite examples is lawyers. I have a couple of friends that were lawyers — great lawyers, great schools, brilliant people, absolutely some of my favorite people in the world. And they're not lawyers anymore, because they didn't like it. Because they thought: it's a lot of money, and it's status, and lawyers are good, it's a good career, or whatever. And now they're doing not-for-profit work, because they're like: fuck that, that was terrible. It just wasn't what they thought it was. Expectations, the enemy of joy: you think it's going to be one thing and it's something else. And so I think there's a lot of value in fucking around. I think you just need to fuck around more. If anything, with younger people, I would encourage them to do more things. Go work in a kitchen for a while. It doesn't matter — just learn it. Work in the service industry. It'll change the way that you approach everything. Just have all these different experiences, and then cobble together the person that you think you are, and then just keep evolving on it. And inducing it — I love the idea of it conceptually, but I don't think it works. I'm going to think about that a lot. I'm going to think about that for the next couple of days. It's a really good question.

Shamil Malachiyev: It's something that keeps me up a lot. I keep reading books about transformations and people — especially as a founder — going through different stages. And I think: well, why can I not start thinking now in the same way I will be at 50, if 50 is a high-impact kind of place? But then — should I be doing that now, or should I be living my — you know, I'm 34 — my 34-year-old kind of path, which I have at the moment?

JT White: I think an interesting exercise for you is to do both. Be really present. I'm a big fan of being present in general. You just have to be really present — and it's hard. It's almost impossible.

Shamil Malachiyev: How do you do that? It's so hard.

JT White: I'm such a futurist. I'm always looking forward. I'm always three, five years out: okay, if I do this and this... I can't stop myself. But that's part of the reason I meditate now: chill, shut up. I need to shut up a lot. I have to stop talking to myself all the time. But two things can be true, right? You can be looking into the future and making sure that you're doing things, and still be firmly planted in being 34. I'm doing the same thing at 40. I don't like long-term goals, but my only long-term goal is — my mom passed away when she was 52. And so my goal since I was a kid has been that at 52, I want to retire. I won't — but I want the right to walk away. Because she didn't get to. And so maybe, if I could be in a position at that point in my life where I could go fuck off and travel and do all the shit she didn't get to do, maybe that would be some beautiful Eat, Pray, Love story for me, or whatever the fuck I've told myself. And I think that's still a healthy goal to have for me. It doesn't hurt me in being sure that I'm mindful about capital and spending and so on. But really, what I'm now realizing is — to your point, we're all going to die. The more time I spend there, the less time I'm here. So if I could just be here, and have a life of purpose, and make purposeful decisions today that are going to positively impact the people in my life right now, who are on this part of my journey — it's probably better, I think. I don't know. But that's kind of where I'm at right now. The people who are tied to my ship today — well, let's do cool shit for us, and maybe it'll work out. I don't know.

Shamil Malachiyev: And the more I think about it, the more I feel worried about the next generation. Because we're also just thinking about starting to have kids. And from what I see right now, everybody is still doing what we millennials did back then: trying to find freedom, trying to create startups, trying to make courses, make money. Every piece of advice online is: you want a lot of money, you want a chance at freedom — build a business. Everybody says build a business. And you know what? Ten years ago it was still fucking easy to build a business compared to what it is right now, because the scope of what could be done by humans was just so large that you could pick any part of it and build a business around that. Right now, a lot of that is automated with AI. And the chances of building something great — even at that time they were not that high, and now they're getting even smaller. So I keep thinking about what the kids are going to be doing — still trying to get over that wall, when the chances are getting slimmer and slimmer every day.

JT White: Well, it's a hard thing to think about, to be honest. As someone who has a nine-year-old and a six-year-old — two little girls, and I love them with every ounce of my being — my thing for them is: don't build a business, build a life. What's the life that you want? Because — and this is going to sound crazy coming from a guy who's spent the last decade in AI — I'm really bullish on the trades right now. I mean, you've seen robotics. They're not painting your house. They're not fixing your plumbing. They're not running electrical. We're a ways out from that. They can do spreadsheets, though. Hoo boy, can they do spreadsheets. So that kind of stuff is interesting. My oldest daughter is really into art, and I'm like: great, be an art teacher. It's fun. You're not going to be a millionaire — but also, curate your life. Do you love what you're doing? Are you fulfilled? Are you happy? Do you have freedom to do the things that you want? Are you joyful? That's so much more interesting. And the one thing that I am very bullish on Gen Alpha for is that they seem to be more driven by happiness than capital. And that's fascinating, because that's not how we grew up. We were chasing dollars, period. Because that's what was happy. Daniel Tosh has that great line: money can't buy happiness — did you ever see somebody sad on a jet ski in the French Riviera? No. But that's the kind of comedy we grew up with. Comedy and music are a really good understanding of where a moment in time is. That was a joke because it was funny — because all of us were trying to get a jet ski in the Riviera. That's what we thought we wanted. Now I look at these kids and I'm like: yeah, these guys just want to have a good time. They're just trying to have more fun. Even Gen Z in the workforce now — they care a lot more about the environmental impact of the companies they work for, and the work-life balance. There's a healthy thing happening that is almost in direct opposition to the tech that's available right now. And so there's going to be some middle ground that needs to get figured out. And I don't know what it is, and I'm not smart enough to figure it out. But what I do know is: the people in my life, I'm just going to encourage them to do things that give them joy and make them happy, and try to find a way to weave that into their everyday life. Because you spend more time working than you do anything else. So how do you find an intersection? I've been very lucky that I stumbled into building digital products. This wasn't intentional — it just sort of happened to me. But it happened for me long-term, because this is the shit I like to do. So the longer I can do this, great. And I just want my kids, and the kids in my life, to find the same shit, whatever that is. I don't know what it's going to look like in five years, because the acceleration of AI in the last two has been unbelievable. But there's still a lot of stuff that I think is very specifically human. And so I'm hopeful that those things will still matter.

Shamil Malachiyev: And do you believe that spirituality is going to be an important factor? I remember watching this film called The Secret — about how the universe can hear your thoughts. To be honest, I took it skeptically, but there is something to it, with the way the universe functions. And then you look at the quantum waves, and everything is like: okay, we don't know everything. Somehow, somewhere, it interlinks. And for me, what is interlinked with quantum physics can be called spirituality. Did you ever have hunches about your way of interacting with the universe?

JT White: Yeah — this is a deep one. No, it's good, I love it. I mean, look, I was raised Catholic. I'm a reformed Catholic now, as most Catholics my age are. I don't know. I'm very comfortable in not knowing what's happening. I will tell you — I love Ryan Holiday, and the work that he does with the Stoics I think is really interesting. I've read Eckhart Tolle. I'm into the idea that all of this is connected somehow, because none of it makes sense. None of this experience makes sense. There's nothing about gravity — what? What are you talking about, gravity? That's ridiculous. All of it's nuts. I do think there's some level of interconnectedness within us, and within the universe, and within humans and animals and the planet. We're all here. It's all atoms, right? And so there's definitely some cool shit happening here. And I don't know what happens with your consciousness after you die. I'm pretty sure I know what happens with your body — I went to school for evolutionary psychology, I believe in science, so your body's fucked and it goes away. But what happens to the rest? I don't know. Is there a shared consciousness? It kind of feels like quantum. There could be, in some capacity, right? My mom really had this idea of old and new souls, which I always thought was really fun. You meet somebody, even when they're little, and you're like: this is not your first trip here. You've been around — something in you kind of gets what's happening here. And then sometimes you meet full-ass grown adults and you're like: it's your first time. Like a golden retriever — isn't that nice? It's cool. I don't know why that is. It doesn't make any sense to me, but it feels like something's happening, for sure. And so my goal, at least with my kids, is — I believe in all paths to God. Actually, I believe in all paths to a good life; for religion it takes God, and that's great. Whatever makes you be a good person — I'm on board. That's great. The only thing I can do is try to guide my kids in such a way that: just be aware that everybody's a person, and they're trying to do their best, and it's really fucking confusing, and no one knows what's happening. So be aware of it. Be good to animals, and don't treat the world like shit, and you'll probably be fine.

Shamil Malachiyev: Well, and on this fantastic note — man, thanks so much for this episode. This has been fantastic. So many small things to take away and think about for the weeks to come, I think.

JT White: There's my big exit: try to be cool, you'll probably be fine.

Shamil Malachiyev: You're an amazing human being and a really cool professional. I really look forward to reading your book, which is going to be out by the time this episode airs. So I push everyone to go and grab a copy. It's already available on Amazon.

JT White: Thank you. Amazon, Target — anywhere you buy your books, it's there. Speaking of capitalism. Listen, you asked incredibly thoughtful questions, and this was a ton of fun, and I'm really grateful that you had me on. You're a brilliant interviewer, and this was a blast.

Shamil Malachiyev: We're still capitalistic, you know — the endangered species. Thanks, man. I have to say a lot of thanks to you, because my job is fairly simple when I have someone like you on the other line. So thanks for that. Have a fantastic week — it's only Monday. Let's stay in touch. All the best.

JT White: Great. Thank you so much.