How to Do Your First Deal in 2026

Bridger Pennington shares how to raise your first fund, starting from his own experience at 22. He covers practical tactics like offering trial investments, aligning fees with returns, and leaning into constraints, plus a memorable example about sourcing deals through a Lamborghini.
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What's up, people? Welcome back. On this video, we're actually going to share something that we usually don't do. This is actually a video from our backend course. So it's a multi-thousand dollar course that we sell. We have a bunch of videos in there. I built a brand new section in that course on how to go about doing your first deal. Now, typically this is reserved for our paying clients that are looking to go out and launch funds or launch their business. But I wanted to share this with you guys today because I thought it was pretty valuable. And I thought people need to know that my approach, at least to going out, finding and structuring a good deal, even if you feel like you don't have the track record, you haven't worked on Wall Street before, you don't have an Ivy League degree or Whatever XYZ thing you think you need to have in your brain to go do a freaking deal. This is kind of my framework that I used at least to go out and do my first deal at 22 years old, go launch my fund, raise money. So I wanted to lay this out for you guys. So with that, we're gonna cut over to the backend training that we have. All right, people, welcome back. In this video, we're gonna talk about how to actually go and raise money specifically on your first deal. I know this can be super intimidating finding money. Bridger, I'm doing my first deal here. I've never done this before. Who is gonna invest in me? Who's ever gonna give me money? How is this gonna work? So I want to walk you through some of the stuff I did to raise my first fund. By the way, inside the course, you can see a bunch of other videos on raising capital. And I'm going to say this too, there is no one perfect silver bullet to raise capital that works every single time. You're gonna have to work with this, you're gonna have to play with this, you're gonna have to see what works for your personality, the investor types that you're working with. Okay, that's why we've made actually an ample amount of videos on raising capital, because there are a lot of ways to approach raising capital. I know some people actually in our Black Card group, they almost exclusively raise capital from just dentists, not orthodontists, not surgeons, literally dentists. They're in this dentist club on a Facebook group and they go out and they like, they raise millions of dollars just from dentists. And you put them in the same room with a lawyer and they have no idea how to talk to a lawyer. They don't know how to pitch a lawyer, how to get like a, you know, a lawyer to invest money. But you put them in a room with a bunch of dentists and they just close. So again, you're gonna have to play with this a little bit. You see what works for you. But in this video specifically for this section, I want to talk about raising money on your very first deal, how that looks, how it works. All that kind of stuff. That sound fair? All right, let's go down to the whiteboard here. Boom bada bing! We're gonna talk about raising money on your first deal. Now I'm gonna give you a quick example on my first deal and to put aside a lot of excuses that people have in the back of their brain. Bridger, I'm too young. I don't have experience. I didn't go to XYZ college or university. I didn't, uh, I don't have a, I don't have an ABC whatever MBA behind my name. I'm not a doctorate. I'm not all these things. How in the world is someone going to trust me with hundreds of thousands of dollars in a deal, an investment across the board? It's a good question. It's a question I've had before. It's a question I still have and a lot of people still have. If you wait, by the way, for the perfect moment that you got all the age and the experience and the university and all the names and all the titles, you'll probably be dead by that point. There's a moment, it doesn't matter how qualified you are, I've talked to people that actually have gone to Harvard, received the MBA. They still feel this inferiority, like, I don't know if I'm quite ready yet to take on capital. Everybody feels this imposter syndrome, whether you're at the beginning or the end or in the middle, wherever you're at. Everyone feels this. I just want to validate your feelings. Now, I'll tell you a quick story. I started my first fund at age 22 years old. I was very young, very inexperienced. Didn't even— I hadn't graduated, didn't have some cool thing behind my name. Why in the world would someone invest with me? And I remember asking my dad this question and I was like, Dad, there's no way. And if you guys know my story, I pitched my dad for money. He said no. I was like, well, Dad, no one's going to invest in me. Like, how am I going to do this? Some of you guys know he taught me the, what I call the Lamborghini example. And I'll share this with you quickly. You've probably heard of it before. But then he shared at the end something and I'll share something unique that you guys haven't heard before. But if you haven't heard, I'm going to dive in. He said, Bridger, imagine we found a Lamborghini Aventador. Lambo, here it is. And there's a lady in Billings, Montana that wants to sell this car. And she's, she's going into bankruptcy. She's in a tight spot. She needs cash this weekend. By Friday, she needs $50,000. It's a legit Lamborghini. We've had a mechanic look at it. It's 100% legit. We believe we can turn around by Monday or Tuesday. We could, we could fire sale this car for $250,000. It's probably worth $350,000, but we could probably sell it quickly for $250,000. And she doesn't, for whatever reason, she can't sell it. She's in a lawsuit. There's all these reasons why she needs cash to just sell on Saturday. Just go with me for a second. Bridger, and I'm asking you the same question. Could you come up with $50,000 by Saturday morning? Can't use any of your own money. But if you come up with 50 grand, we're 95% confident we can turn around and sell this car for a quarter million dollars. We're going to make a $200,000 spread over the weekend. Are you in or out on this deal? Okay. And he's like, could you find 50 grand? And I said, huh, you know what? I could talk to a former boss, a college professor, a family friend, a neighbor. I could just knock business doors. I was like, you know what? I'm in college. We're going to make a $200,000 this weekend? Like, yeah, let's do this. And he was like, okay. And I was like, you know what? I was like, actually, I probably wouldn't sleep for 3 days, but you know what? I bet I could come up with $50,000. He said, huh, that's interesting. I said, well, yeah, like, you know what? We're going to make that much money. I could do it. He goes, Bridger, what about $100,000? Could you find $100,000 by this Saturday? And I kind of thought about it. I said, yeah, you know what? I think I could. And he said, why? And I said, well, dude, the deal is so good. Like, you told me I'm going to make $200 grand this weekend. Like, it's a night. Like, You know, it's obviously a fake example. I'm like, dude, the example is so good. Like, this is a pretty— it's a pretty easy deal. We have a hard asset we can just buy. Like, it's not that hard. And he goes, aha, there it is. He goes, 3 minutes ago, you were telling me that you were inexperienced, you were too young, you didn't graduate from college, and all of a sudden you're telling me you could raise $50,000 to $100,000 by Saturday morning. And he goes, because— this is the aha moment for me— the deal was so good and you understood this niche So well. Now, I've had a lot of people ask me about this example and they say, Bridger, I don't know where to find my Lamborghini. This happens in real estate all the time. This happens with— in my example was debt. We were doing loans. Now, I want to give you some color, a real actually true story example. So I was 22 years old. I didn't have any of this stuff. I went out to raise my first fund and I went and pitched investors and they would ask me, well, Bridger, come on. How do we expect you to know about macroeconomics and the Fed and trends and all this cool stuff that's going on? Like really, you You expect us to know all that? And I said, no, I actually don't expect you to know that at all. I said, guys, I understand that I'm young. I actually told them this. I go, I understand I'm extremely young to be in front of you today talking about this investment deal. I get that you're typically listening to someone with gray hairs that's 50 years old, that's already made it in life, all these things. But let me tell you why I have an interesting advantage over them. First off, if I was 50 years old and I'm this bigwig, I've probably got a nice house, cars. I've got a lifestyle I've got to live up to. And I actually, you know, I don't work that hard maybe if I was 50 years old. I like to go home on the weekends. I like to go boating. I got family. I got kids. I got other stuff to manage. I watch Netflix at night. I'm not, you know, I'm only working on this a couple hours a week because I got other stuff to do. Oh, and by the way, if things go south, if I was 50 years old and had a big house and cars and mansions, whatever, I have a higher propensity to commit fraud because I actually have to maintain this lifestyle. I said, on the contrary, it's just me. I work 80 hours a week. This is all I do. I live in an apartment that I pay $300 a month to live in. I have no reason to commit fraud because there's nothing to even buy. I have— my living expenses are like zero. This is all I do. And my whole goal of this fund, yeah, I want to make some money, but I want to knock your socks off as an investor. Because I know when I'm older, when I'm 25 and then 28 and then 35 and then 48, I want to build a track record of amazing investors like you that are going to, for years, going to say, Bridger has been a great steward of my capital. He's done well. He's given me returns. So because of that, guess what? I'm not going to charge you any management fee. 0% management fee. I'm going to work for free for you. I only make money if you make money. And if we make money together, let's just do an 80/20. You make 80%, I'll make 20% when we make money. Does that sound fair? We can even change it if you want. My whole goal is to help you have an incredible experience investing. And then I said, on the other question, I know you talked about macroeconomics, understanding other stuff. I said, hey, I don't profess to know everything in the universe. But what I do know is this. We're doing these short-term loans. They are incredibly lucrative. I've worked in this space for, I was like at the time, like 2 years. I've seen We're doing loans that are $2,000 to $3,000 a loan. They're fast turning. We can do them about 2 to 3 months. We've seen about a 1 to 3% default rate across the board on these loans, and they produce about a 15 to 25% return over about 2, 2 and a half months. So annualized, that's 30 to 60% per year if you take out defaults. And if you add in defaults, kind of the lower end, if you take away defaults on the higher end. So with Pennington, all that, you know, with the business, I'm very focused. I know this one niche. I know what we're doing right here. I'm only making money if you make money. We are equally yoked. yoke in the line to make money together? Can I put you down for an investment of X amount of dollars? And I'll tell you what, at 22 years old, I actually closed a high number of— I didn't close everybody, but I closed a high number of people. And I said, hey, give me a trial investment. Don't give me a big investment. Give me a trial investment. Whatever a trial investment means to you, give me a trial investment. I'm going to knock your socks off over the next 6 to 8 months, 12 months, and you're going to be begging me to put more money in the fund. Do you want to get involved? It actually worked. It's crazy enough, it worked. My first little fund, we raised about $50,000, just right on that Lambo mark. It was plenty of money. We actually had more money than we needed because we're doing these small little loans. We then— our next fund, we launched it, we raised about $800,000 on our next little fund. We then grew that and we were doing multi— we were doing millions and millions of dollars of loans every single year. I ran that fund for 3 years, did very well. Then we had a competitor actually come in and buy us out of the fund. Now I say that because I did that from ages 22 to about 25 years old. I didn't have experience. I wasn't a college grad. I was a sharp kid, but you know, I didn't have the XYZ, all that stuff. And yet people trusted me with millions of dollars to manage. You guys can do the same thing. So when you're approaching raising capital, if you can lean into your constraints, your constraint of I haven't been to Harvard, lean into that. If you've noticed with Fund Launch, we lean into that hard. I say, hey, you can start a fund if you haven't gone to Harvard. I tell people I've never been to Harvard. I haven't gone to Harvard. And guess what? We have multiple fund managers running and scaling funds because we see the world from a different view. I lean into the experience. If you notice earlier, I said because I'm young, that actually gives me an advantage. I can work harder. I can work longer hours. I don't have a propensity to commit fraud. If you can find constraints and lean into them, it actually produces some really cool things. And by the way, everyone has constraints. Everybody. An awesome example, there's a lot of people online that have leaned into constraints. People that are really overweight, they lean into it. You know what? I am fat and I'm going to lose weight or gain weight, whatever they're going to do. Fit to Fat to Fit. Have you guys seen that? Fit to Fat to Fit where this trainer, his clients kept saying, well, you're fit. You're already a trainer. You can't train me because I'm like 300 pounds overweight. You're fit and in shape. You don't know what it means, what it feels like. So he says, okay, I'm going to lean into that constraint. I'm actually going to become fat. So he actually put on, I can't remember, it was like 50 pounds of fat, kept it for 2 months, and then got it. He went from fit to fat to fit. People have done this across the board, and leaning into your constraints is a massive way that you guys can have success. Now I'll say this as well. There is something to be said about some of these constraints as well. If you feel like you really need to have that university degree or that XYZ thing or that experience, guess what? Change your question from how to who. Who can I partner with who has that experience? Tell you what, Harvard and Yale, they're graduating thousands of people every year that have no clue what they want to do with their lives. And if you can come partner With these types of people, you can actually bring and leverage their experience onto your team. My partner in my fund right now, he's a multiple Inc. 500 winner. He's been on the board of Intel, Intel's board of advisors for 15 years. His name's Dan Young, incredible business partner. We leverage that experience. He's never ran a fund. So he leverages my experience that I've ran 3 funds now and I know what that is. We actually co and do very well together because we bring different aspects of this game to one table. So if you feel like you don't have it, go find someone who does. Well, Bridger, why would a Harvard guy partner with me? And I'll just answer this quickly, but it goes back to dating for me. I'm gonna say, how do you date a 10? Like someone that's a 9 or a 10, super smoking hot. How do you date a 10? Well, there's a lot of tricks and gimmicks and you can do pickup lines, whatever. And there's a lot of ways that if you're a 5 or like you're like me, you're probably like a, I'm like a 3, 3 out of 10, but I married like a 9 out of 10, right? How do you do that? There's a lot of tricks and gimmicks and pickup lines you can do. But also the easiest way to date a 9 or a 10 is to just become a 9 or a 10. If you can learn this game and kudos to you to being in the Fund Academy course, you can learn this game of funds. You can become a 7 or an 8 or a 9 or a 10 at actually structuring, putting funds together. Maybe it's raising capital. Maybe it's a different facet of the business that they don't know about. You can then come to them and maybe you find someone that's really— they've done real estate for 30 years. They have no idea how to run a fund. You can couple together and do very well together. I'm getting off track. I told you this video would go in a few different directions. There's a lot of ways to raise money. We have a whole section of the course on how to raise money, but I want to share that for you guys specifically on doing your first deal. And by the way, there is so much leverage. I'll end with this. There is so much power in doing a deal, even if it's small. Bridger, we're only going to make $10 on this deal or whatever the number is that's low for you. My first fund, I literally raised $49,500. I made, I don't know, I ran this thing for this first little syndicate fund. I ran this for like 6 months or a year or something. I didn't make that much money. But what I did is I built a track record. I built an investor base that got, we got a 64% return on our money from doing this. They loved it. And then I said, oh, I'm going to leverage that into our next fund. And it helped me to raise our next group of investors. We went out and raised, I think that initial raise we raised like, it's like $785,000. Don't quote me on this, but about $785,000 on our next raise at 23 years old, I raised that. I never would have been able to raise 3 quarters of a million dollars if I hadn't done this first. And then we launched our next fund, Ugly Unicorn. We raised $10 million on our initial launch. How did we do that? It wasn't just luck. It's because I had ran this fund and I treated those investors well and I had ran this I treated those investors well. Your reputation is the biggest thing you'll take with you. We are playing the infinite game. Stop trying to play the finite game. Finite games, we try to put scoreboards in time like, you know, a soccer game or a basketball game. There's a scoreboard, there's a winner and a loser. That's a finite game. Most things in life that have value are infinite games. You don't win at marriage. Marriage is not a game you win. The goal of marriage is to continue to stay married and be hopefully happily married and even happier But you never win at marriage. Same with business. The goal of business is not to win at business. The goal is to stay in business and continue to grow and expand. And typically infinite mindset, the infinite frame always dominates the finite frame. When you're playing the fund game, doing your first deal, it might seem small, it might seem minuscule, but play the infinite game. Play this game how it's going to play out over the next decade or 2 decades or 5 decades. I've been able to study some amazing fund managers— Ray Dalio, Leon Black, Stephen Schwarzman. You'd study people like Warren Buffett. Almost all of them started their first fund in their 20s. Now we look at Warren Buffett. Wow, he's amazing. He is what he is. He's like 90 years old. He started his first fund, I believe, at 27 years old. And he played the infinite game. He just did it. He did it. I think he raised $105,000 on his first little deal. He started doing a bigger deal and then a bigger deal. Ray Dalio, 27 years old, started his first little fund. And they started trading and doing this other stuff. And they got bigger and bigger. And today, Ray Dalio is this big king. He's been doing it for 5 decades, people. Don't think you're going to just win on the first little deal. Play the infinite game. Treat your investors right. If it means sacrificing a dollar, guess what? Things compound in this game. That's why you're in the greatest game on freaking earth as far as business goes is with funds. Because funds compound. They get bigger and bigger and bigger over time. And each fund typically compounds on the last one. All pending you have a good reputation, you treat your investors right, and you follow the process. So don't underestimate small wins today will be catastrophic, amazing wins down the road. So go get that first deal done. Use this as a reference. Send me a freaking message online wherever we're at and tell me about your first deal. I want to hear about it and I want to hear what you did, how you structured it. If there's stuff we should add to this, let me know. You guys are amazing. I'm excited to see your first deals and we'll go from there. Peace out.
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