Why I Became a Fund Manager & Pursued Entrepreneurship

Bridger Pennington explains why he became a fund manager and entrepreneur, drawing on a conversation about why your early twenties are the best time to start a business. He uses Jeff Bezos's regret-minimization framework and America's safety net to argue the downside is lower than you think. He built seven businesses and a fund by going all-in instead of treating ventures as side hustles.
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Hey guys, welcome back to the show. So today I want to share a quick story about what initially got me into entrepreneurship and helped me get over that hurdle, that fear, that scariness factor of starting my own business and actually really going for it, right? Not just having a side hustle but actually going all in and starting my business and essentially my fund. So I was meeting— I had a family friend at the time, great guy, and he had been fairly successful in his 20s. At the time, he was 29 years old, multi-millionaire, had done very well, had this online presence, all this kind of stuff, and we were talking. He said, Bridger, and I said, yeah? He goes, well, what are you doing? I'm like, well, I got some of these side businesses. I'm still going to school. I'm really busy at school, but I have these side businesses because I had this entrepreneurship spirit, but I wasn't all the way in, and I had these kind of— everyone calls them side hustles, right, and he goes, Bridger, I want to ask you a question. He goes, when do you think is the best time to go all out and start a business? And I thought, well, probably, I don't know. I said maybe like most people think like 30s, you know, in your 30s, right? You've gained some experience in your 20s, you learn, and then in your 30s, maybe like 35 is probably the best time to go and start a business. He goes, wrong, and I was like, okay, it's very bold. He says the best time to start a business is your early 20s, in college, at school. He goes, that is the best time to start a business. I go, why? And I kind of disagreed. I said, no, you want experience and you want to gain that know, confidence in yourself, you want to learn from other people and he goes no and he goes yeah, for some people they might need that track but for a lot of people like me and you, you're early 20s, you don't have a mortgage, you don't have kids, you don't have like a serious relationship or commitment, you don't need one right now too, you don't have a house, you don't have family commitments. He goes right now you have this little window of time, couple years where you have stress-free life. I mean you're on student loans, no one expects a ton from you anyways. No one has these huge— like you don't have to meet some bar. I mean, you're just like early 20s. He goes, right now is the best time possible to go all out on something because you can. You can stay up late, you can work weekends, you can work, you can fly. I mean, you have so much time and secondly, your body is in the best physical condition it's probably ever going to be in its entire life so you can go harder, you can work longer and then third is as a college student, you have access to so many mentors. He goes, everybody wants to mentor a college kid and no one— I mean, not no one, but people tend to, as you get older, they don't want to mentor you as much. Once you graduate, you're in school, it's like, whatever. I mean, this is just a random dude. But a college kid comes, you can get mentors and have people help you start your business, and people want to help and invest in college businesses. They love that story. At the same time, I was listening to a podcast by another guy. I ended up being the same time, and it was on the same principle. He goes, in your early 20s, let's call it— I'm just gonna call it early 20s, but it could be just time of your life where you don't have all those risk skills. That is the least riskiest time ever to start a business. He goes, for me now, I manage a $50 million a year company. I've got hundreds of people that work for me. They depend on a paycheck from me and if I risk it all and I lose it all, it's pretty devastating for a lot of people. He goes, if you're 23 years old and you risk it all and you lose it all, well, okay, you lost like 3 grand, right? Your savings, right? You lost 3 grand, okay, back to zero. You can restart. You didn't lose that much and by the way, on that same note, it is They kind of said too is it is hard to fail in America, to truly fail, to truly hit like rock bottom homeless in America is pretty hard to do because you have bankruptcy, you have all these different safety nets as you fall. You know, to actually be homeless is actually pretty hard in America. I'm gonna say that boldly and I believe it. So he goes it's really low risk, high return, an asymmetrical return starting a fund or starting a business especially When you're low leverage, when you're not in a career, when you're not having a wife and family and kids or husband, whoever it is, right? It's way easier to start a business and that tweaked a lot of things in my mind and then I said, well, hold on, what about school or I gotta, you know, my job. He goes, do you think school's gonna be there in 2 years? And I was like, yeah. He goes, exactly. He goes, if all else fails, right, if your whole business tanks, it doesn't work out, guess what's always waiting for you? School. And I was like, wow, that's always true, right? School and it And a lot of us have this timestamp on us like we've got to get— we've got to be a millionaire by age 30 and, you know, have $10 million by 38 and we got to be a billionaire by 45, you know, like people have these timestamps. It's got to happen at this time and I'm gonna have kids at 30 and I'm gonna be married by 26, whatever it is for you, right, and your culture. It's nice to pull those off. It's always there, it's always waiting, it always can happen, right? School's always there but back to his point was there's— for For his point was there's never a better time than right now to do it, especially in the economy we're in, especially in what's going on in the world, especially right now with coronavirus. We have so many opportunities out there that are being created by a market correction. Why why let them go to waste? At least I'm not and I'm not saying quit your job or quit school right now. I'm just saying keep your eyes open for those opportunities. Jobs are always. I mean, it is right now unemployment has spiked because of coronavirus, right? But I mean last year, I mean unemployment. It was pretty much just people switching jobs, right? There's no one really truly unemployed, can't find work, right? There's plenty of work. Back to Jeff Bezos, he has the regret minimization theory. He says he does everything in his life based on what will I regret the least, and if you're gonna regret working your job or staying in school for 8 years or 10 years and never taking a chance on yourself, you're gonna regret that more than hopping out and, you know, taken a different entrepreneurship route. His theory is you should go after whatever would create the least amount of regret when you're old on your deathbed and so those kind of things all— I don't know, that's kind of a few random points that I've picked up from different people and different mentors and kind of brought together and said you know what? I've got my whole life ahead of me and we got plenty of time whether you're 22 or whether you're 35 or whether you're 55. We've got lots of life ahead of ourselves. If you're 55, you still got like 30 years, 40 years to live. Think about that for a second. Yeah. If you're 55, You've got about 30 years left. 30 years, that's a lot of time. A lot of us spent— you've probably spent 30 years in the workforce, 30 years. Imagine what you could do with 30 years again. Anyways, there's so much time. So back to my point is, and there was never a better time, at least that he mentioned, was for me at that point. And so I made a decision that I was gonna go— I wasn't gonna dabble, I wasn't gonna tell because it's this facade, oh, I'm working on a side hustle, you know, I got these little things going on, and it's cool to tell people at a barbecue or something but you're not actually, it's just It's something cool to say. You're not actually going for it. The moment I said I'm going for it, I didn't tell people, I didn't like go on Instagram and be like hey, I'm going for it. I just went for it like internally, right? Stayed up late, I worked harder and I had 7 businesses. Kind of do okay, kind of fail, kind of do okay until I started my fund and that actually did really well. 7, okay? So we got time, just keep getting up to the plate and swinging, right? There are plenty of people in this world on the sidelines In the peanut gallery that like to make fun or poke or say you can never do that but they're not in the game. People like me and you, we get up to the plate, we swing the bat and yes, we're gonna strike out sometimes. Yeah, you're probably gonna spin around, you're gonna look dumb but at least we're at the plate and if I knew as long as I could get up and keep swinging the bat, if I could keep swinging away, I'm gonna get— eventually I'm gonna hit a single and I'm probably gonna hit maybe a double and eventually maybe I'm gonna hit a home run over the fence but millionaires are still made on singles and doubles. Right, but at least we're at the plate and before he talked to me, I wasn't at the plate. I was in the sidelines, I was in the crowd eating popcorn and I knew how the game worked, I thought about it a lot but I wasn't in the game. I talked to people like I was in the game but I was on the bench. I wasn't actually out there swinging the bat and finally it kind of freed up my mind of okay, worst case scenario, I lose 3 grand of my savings, I go to zero and I go get a job at McDonald's. To pay for rent and I slowly work up from there. Worst case scenario, right? That was in college. For now, it's like worst case scenario, my business tanks, I go bankrupt or whatever, and I go get a job at a firm, right? And they would probably love to take someone like me, right? When we have an amazing place to work in America. I know jobs are all over the place right now, but there's— I mean, there's plenty of jobs out there. And worst case scenario, I go start a landscaping business, mow lawn. I mean, there's just so many ways to make money. So I just keep looking at worst case scenario, right? It is hard to be It's hard to be homeless in America and I said that before, I'll explain that for a second but just like there are bankruptcy, there's welfare, there are so many of these safety nets. I have a family friend, he's got 2 of his siblings are actually homeless. They grew up in a great home, they have a handful of kids, some of the kids are doing great and 2 of the kids are actually homeless and sell drugs and they always say you're welcome to move home, you're welcome, you have a warm bed, you have a fridge full of food whenever you want and they say we don't want it. We want to live in the streets. We're gonna do our thing, we're gonna stick it to everybody, we're gonna go sell drugs and they say okay, if you want to come home, that's fine and they don't, right? They choose to be homeless. There are 2 people that choose to be homeless right now. Their story to other people though is oh man, my parents never— no, I talked to their parents, their parents like yeah, we tell them, you know, they can come whenever they want, they have a warm bed if they want to come home whenever and they don't. Anyways, I'm rambling on a little bit. There you go, that's what got me into entrepreneurship. Hope that helps a little bit or helps free up a few things in your mind like, I don't know if I can do this, never a better time than now. And look at your situation where you're at and try to live a lower-leveraged life so you can do that. So anyways, love you guys. See you on the next episode. Peace. Bye.
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