In this informal panel, host Sam Parr talks with Sean and Steph about the trade‑offs between developing expertise at a top‑tier company and launching an independent venture. Steph explains her current strategy: a well‑paid full‑time role that gives financial and mental stability while she pursues side projects for fun, positioning this as a safe runway before a potential billion‑dollar startup. Sam relays Steph’s confidence that any future venture will become a billion‑dollar company. Sean pushes back, arguing that the fastest way to acquire relevant skills is to dive directly into the activity you want to master, rather than spending years accumulating experience elsewhere. He stresses that markets, timing, and individual business dynamics change constantly, so a long‑term “skill‑building” path may not translate into entrepreneurial success. Sean also notes that entrepreneurship isn’t for everyone; many prefer the lower‑stress, defined role of a small‑team employee. Throughout, the conversation oscillates between supportive encouragement, skeptical realism, and personal reflections on lifestyle, risk tolerance, and the importance of honest self‑assessment before committing to a startup.
Chapters
become a billionaire.
It's like, oh, I know, but they grow up so fast, so I just want to cherish these. It's like my pre-billionaire days. I just want to really own these because I know how easy it's going to be to lose sight of these when I, when I do become a billionaire.
I— so for the record, I don't think that whatever I start is a guaranteed success. But to Sam's point, my, my point was just that what I want to do is focus on gaining as many skills as possible so that when I take my shot, it's a good shot. Versus I see a lot of people who are like It's time to drop out of college because I think I'm going to be successful.
Seth, why, why are you not working for yourself? Why don't you have a job? Why are you working for these other companies? Why are you making guys like Sam rich?
She's, she's got a good answer.
So my answer— let's see if Sean thinks it's a good answer. My answer is that currently I get paid well to do things that I like. And I have the freedom to work on my side projects, which I do, and is like a prerequisite to work anywhere. And so I personally like the financial stability and the mental stability knowing I get a good paycheck to do things I love, and then that means all of my side projects are purely for fun. Like, you know, the like con— or the common saying where it's like, you know, a full-time job, no full-time job is fun, right? So if I made my passions my full-time job, full focus, then I actually don't think I'd have as much fun. So eventually I do want to work on my things alone, but I'm pretty happy with my setup.
Yeah, but the second part you barely touched upon. So Sean, what she told me one time, and she said it very clearly, she goes, yeah, I was like, are you going to start a business soon? She goes, yeah, I am. I'm just plotting because when I start it, I'm going to become a billionaire, and I just want to make sure that like I'm ready for all that to happen. Uh, like, like she like very clearly told me like whatever she starts, it's going to become a billion-dollar company. And she was like, so I'm, I'm happy Yeah. She was like, I'm, she was like, I'm happy just to be doing this, what I love and building up like my bank account and savings. But when I do start something, um, I think I'm gonna become a billionaire. You have kids, it's like, oh, I know, but they grow up so fast.
So I just wanna cherish these moments. It's like my pre-billionaire days. I just wanna really own these because I know how easy it's gonna be to lose sight of these when I, oh, when I do become a billionaire.
I, so for the record, I don't think that whatever I start is a guaranteed success, but to Sam's point, my, My point was just that what I wanna do is focus on gaining as many skills as possible so that when I take my shot, it's a good shot. Versus I see a lot of people who are like, it's time to drop out of college because I think I'm gonna be successful. And I actually learned this from one of my very first jobs. I was like a contractor doing social media for a company. And it was this woman who was just like so poised, so put together and successful. And she was probably around 35. And I asked her that same question. I'm like, Why did you start your company now? Like, why didn't you start it 10 years ago? And she told me the same thing. She's like, Steph, a lot of people miss the value of learning for, you know, years in their career from people who have a lot more experience than you and who can basically like teach you all of the obstacles that you can miss. So that when she went into building this company, which was a success off the ground, she just knew what she was doing, right? She wasn't stumbling around. So I kind of I, I'm trying to embody that, that, that advice from that woman. I thought it was actually pretty wise.
I'm gonna disagree with that advice. Um, and the reason why I disagree, and I'm almost hesitant to even say this because, uh, you know, everybody should do what they wanna do and I, I fundamentally believe that. So, you know, uh, and if you're happy doing what you're doing, fantastic. It's not like a career advice to you. So I'm kind of talking to you, but I really am just talking to like anybody who's listening to this. Uh, which is the best way to build your skills so that you'll be successful when you go do that thing is to go do that thing now and just keep doing it until you figure it out.
Yeah.
Figuring out other games to try to then parlay them into the game you want to play, that works when you didn't realize what game you want to play, right? So like, I learned a lot of skills in poker that helped me in business, but if I wanted to be great at business, I would do business, not poker. Um, it's just at the time I didn't know I wanted to do business. I thought I wanted to do poker. And so those skills, yes, they do cross over. They will help me for sure. But like all the things you're saying sound good, sound reasonable. They're just a story that you're telling yourself. Like if you really wanted to go do that thing, you should go do the thing. And the fastest way to get good at that and to like, you know, be good right off the bat or like, you know, like, I don't know, Sam, you've done many businesses. I'm sure each time you do one now, you have a higher likelihood of success than you did before, but it's not like you just do them and they just magically work now because you've, you've, you've crossed the magical threshold of skills and knowledge and wisdom that now mean businesses that you start will succeed. No way. Right? It's like, and it's always changing. Every market's different. Every business is different. Timing is always different. And so like the reality is if you, if you're doing it to build up skills, you're building the wrong skills. The skills to build is to go do, if you're building up skills to go start a business, the best way to build that skill is to go start businesses. These skills that you have today will help you. Don't get me wrong, it's just not the op— like you're taking the long path rather than the, the direct path. That's kind of my, my pushback.
I think I have something in my contract where I can't say anything.
I can't comment.
I can't persuade. I can't persuade. Isn't there some— don't I have like a thing in my contract where I can't like poach our, our past, our past people? Yeah. Yeah. So I, I can't really say too much except I think Steph should do whatever makes her happy and she's, pretty much capable of doing anything she wants.
And by the way, all right guys, I quit.
No, I'm kidding.
I'm done.
You know, the, the other thing is that not everybody actually wants to be an entrepreneur. There's a whole bunch of ways to have, uh, like the fun of business building without the stress of business building. And so like for some people, I think that's the honest answer is like, actually I wanna work in a small team. I don't wanna go to sleep every night worried about how to make the whole fucking thing work. I like that you go to sleep worried about that and I worry about my part. and I enjoy my part. Like, and that's the trade I want to make. And I think that like more people should be honest when that's the case for them. And they say, you know, right now at this phase of my life, I don't want that stress. That's, that to me means more than like I'm building my skills up, right? It's like, because once you do commit to doing a business, it is, you know, there's no like kind of way, there's, you know, there's not really an easy way out. And, you know, it's pretty full-on commitment. And I don't think you should just make full-on commitments unless you like want to and are ready to and are down to deal with like the pros and cons of that. And so like I have a bunch of people who work for me that I tell them, I say, look, there's like 3 scenarios here. Either you suck and you're fired. Um, you're great and you're, you're great and you're gonna realize you're great and you're gonna grow here, right? So you're great and you're gonna grow, your impact's gonna grow, your comp's gonna grow, your, your rewards are gonna grow here. Or we're gonna realize that like, you're, you need to be doing your own thing, in which case, you know, I'll be your first kind of like backer investor or I'll partner with you on something in some way. And I just try to be honest with people. Like, I kind of only want you to land in one of those 3 spots. There's not really like another spot. There's not really like another landing destination. Like, this flight only goes those 3 places. And so, you know, choose which one, which one you want.
I think that's smart though, because a lot of businesses treat people like there's like 10 outcomes and they kind of slot people like, "Oh, you're pretty good, so we'll keep you around," or like, "You're not that bad, so we're not going to fire you." But really, like, if you're trying to operate a business effectively, it should be mostly those 3 outcomes. Like, you're either amazing, you're driving value, so we want you around, we're going to incentivize you to do that, or like, there's probably somewhere better for you.
