How David Osborn Became A 9-Figure Real Estate Investor | The Capitalism Conference

David Osborn built a nine-figure net worth by starting businesses rather than just investing, taking big risks early, and pivoting until something stuck. He credits mentors like Richard Branson and Gary Keller, follows Warren Buffett's capital protection rules, and delegates everything from email to operations so he can focus on what only he can do.
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There's no way you can get to be a nine figure investor unless you build businesses. Real estate's a great investment. I love real estate. You can invest in real estate all day long and you can be a 10, 15, 20 million a year guy when you're done. But if you want to actually manifest giant wealth, you have to build a business. You have to roll out a business that has a multiple at exit. Most of you guys probably already know this, so that's the game we're playing to get to nine figures. When you're young, you can take massive amount of risks. And when you don't have kids, you should just be all in all the time. Nothing I like better than seeing a 20 something year old that quit their job to go all in for their business. Because what you're really getting, whether you win or lose, is the knowledge.
And then as you get bigger, then you've got to nurture the dollars. It's all about the dollars. The dollars have to earn a fair rate of return, right? So you have to take those dollars and invest them wisely. Warren Buffett's rule number one is don't lose any capital. Rule number two is, see rule number one. Okay? That's with your investment dollars, but on the other side, on your aggression dollars, you go all in when you see something that wins. I was sitting with Richard Branson on Necker island. Not because he's my friend, I'm not name dropping because he's my buddy. I paid 50 grand to go to his island for a week. It was nice. And I was sitting with him and he said, people said to me, I got lucky. He said, I got out of the record business right when it was dying and I got into the airline business. He said, and they're right, I did get lucky. He said, but you got to put yourself in a position to get lucky. And that's what I would say to you. If you're all entrepreneurs, you got to get out there and pivot, pivot, pivot until something works and then just go all in for it. And I got lucky early. I got at Keller Williams early. I had no idea who it was. There was less than 1,000 people in the company. Now there's 190,000. I had a mentor that was a billionaire at that time. He was worth negative net worth because he hadn't built Keller Williams yet, Gary Keller. But today he's arguably a billionaire. And I just went all in. I was 20 something years old. I had nothing to lose. My mom was a realtor. At his company, she was a legend, an amazing woman. And I just went all in because I didn't have any other option. And then it. It struggled, struggled, struggled. Back then, you know, a lot of them were failing. But we started having a breakthrough, and I just kept going all in and all in. And so I ended up the largest franchisee more by default than anything else, just because I went all in. But I could see it was working. So I just read Blitzscale. Anyone read Blitzscale? It's a pretty interesting book. And he says what the new companies do is they come in and they pivot, pivot, pivot until they find something that works, and then they go all in, right? So pivot, pivot, pivot. When something works, go all in.
All right. What else do I want to tell you guys?
So then the other thing I was telling you is, right, your peers, right? So dump the losers, man. And I'm not saying that like, I know it sounds harsh. I'm not trying to be harsh, but charity belongs in charity, right? You don't have to have friends that are a charity case. Sometimes you got family, you don't have any choice in that matter. Maybe some people would say, dump family. I can't go that far. But I will say that if you have a friend that's just sucking your energy from you, you gotta move on, man. No one obligated you to your high school buddy that never gets their stuff together, right? I judge a person by the energy I get when I'm around them. If I'm sitting with a person, their energy is sucking me a little bit. I'm okay with that a little bit, but I'll keep observing it. If I meet with them three times and every time I feel depleted, I'm out. Go find somebody else. By the way, when my managers that are sevens are not rising to the level they work under, the other managers that are eights and nines, we kind of move people around so that the eight, now, they have the opportunity to get there, but they gotta choose the path. So your peers, and then the other side is your coaches. Like, I've been through so many coaches. Like, Tony Robbins was a coach for me, right? He didn't know it, but I went to all this stuff when I was young when I needed motivation, I don't need motivation anymore. But when I needed motivation, I found Tony amazing. To this day, Jim Rohn has been my favorite of all time. Any Jim Rohn fans in here? What an incredibly beautiful and amazing human being. I got to meet him Once, and it was an honor. So coaches, they don't have to be living. They can be dead. You know, there's coaching all over the place.
And then massive action, which you already know, and then really just ruthlessly honest feedback with yourself.
But all I've done, really, in my business world, is just keep crafting on what works and what doesn't work, shed what doesn't work and add what works. Be around leaders, be around teachers, be around amazing human beings. My goal last year was to meet Peter Thiel. I failed at it, but it was my goal. Why? Because he's so contrarian. Like, what's this guy thinking? Like, he's a gay man from San Francisco that votes Republican and is a Trump fan. Like, how different is that, right? So I was very curious to meet them. I try to meet a billionaire every year or so because not because they're a billionaire, but because sometimes I'm like, ee, that guy's horrible. I wouldn't want to be like that guy. And other times it's like, wow, I can pick something up. When I was with Richard Branson, he was sitting on his couch with his assistant, and they were working. And I came over and I said, do you mind if I sit beside you? And the assistant shot daggers at me, like, go away. And he was like, just don't talk. So I sat down. I was so glad I brought my journal, because for 40 minutes, I just sat there eavesdropping on Richard Branson working with his assistant. And I figured I'd spend 50 grand, right? So I have the right to be rude. I was like, yeah, I'm. Can I sit here?
And what he was doing was because he's dyslexic, I guess he was dictating everything. He was like, she was reading all his emails, and he would say, okay. And one of them was to Sheryl Sandberg, which was cool. He's like, well, tell Sheryl I'd like her to be a part of this group and we'll do all the work and she could just be a part of it. And I listened from that, and I was like, man, I'm holding onto too much. I didn't get home, and when I got back, I let go of all my emails. I let go of all of them. So my team now read all my emails, and then they send me the ones they think that I need to look. It's the most liberating thing anyone else done that. Let go of all your emails. Cool. Nice. So that was picked up from Richard Branson So you just like picking up nuances from people, little bits and pieces you can add. But the basic one, the most basic one, is to get your implicit system on your side. You can say, I want to be a billionaire all day long. And if your internal system, if your subconscious mind doesn't agree with you, you won't get there. It will not happen. Athletes can get given $100 million and end up bankrupt. Why? Because their implicit system was not in alignment with it. So how do you coach and nurture that implicit system is through all these things I talked about, just like the framing of it. So your goals, managing your energy, having the vision at the top, your peers and then your coaches on either side. And then the foundation is your relentless and ruthless honesty with yourself about what's working and what's not working.











