How To Build Your $100M Life w/ David Osborn
11 Dec 2025 · 100 min
David Osborn built nine-figure wealth through real-estate franchising, private equity, and distressed-debt investing. He talks about scaling from agent to franchise owner, leveraging people to build an empire, and how reaching multi-nine-figure net worth shifted his priorities toward purpose and parenting.
Questions this episode answers
April 30, 2025
$200 million
Right around 50
130 single-family homes
About 800 homes
Chapters
David Osborne is worth $200 million. How did you make your first hundred million?
Ryan, that's a good question. I worked as hard as I could and it's almost impossible to get out of the rat race even if you make 1 or 2 million a year, if all you know how to do is work hard and make money.
He is the owner of the largest Keller Williams franchise ever in history.
Why not me? I remember saying that to myself because I would have these doubts. Who am I? I viewed myself as a guy already worth 100 million. I just hadn't arrived at that destination yet. You trust your know myself, if I say I'm gonna do something, highly likely I'm gonna do what I say I'm gonna do because that's what I learned works. What works? You keep your word to yourself.
He is the owner of a multi nine figure private equity group and he's helped play a role in countless millionaire success stories.
You can't get there unless you get there through other people. I don't know anyone that builds massive wealth without other people doing it.
He's the author of several books. He is an active father, owns a private jet, lives the life that many people aspire to live, and today he sits down to share how to build that type of a life.
David, I usually ask people how they made their first million, but in your case, I want you to answer the question, how did you make your first hundred million?
Ryan? That's a good question. I've known you a long time, it's always good to hang out. I admire your work and I've enjoyed speaking for you@capitalism.com before.
Thank you for the compliments. Tell me how you made $100 million.
Okay, okay, straight to the point. You know, I was always a guy that loved money. Like I like to make money. I grew up with a rich uncle, a great uncle. We were poor and we were middle class, probably lower middle class. My dad lived on a soldier's salary, but my great uncle Ted had all the toys. He had the ranch, or in England it was called a farm. And he let us stay in his gamekeeper's cottage and he would have the Christmas dinners and he would sit at the head of the table and then there'd be 40 or 50 family members at his house and the kids were always at the junior table down the bottom. But I remember watching him make the speeches wearing his black tie because he was English and formal and I always kind of related to like. I was intrigued by what that looked like. So from an early Age. I think I made a decision to be financially free. Now, when you're little, that's not really a super conscious decision, but as I look back on it, I can see how that was formed.
So I would answer you. The number one way I made my money is by learning continuously. Anything I could learn that would lead me towards that goal of making my first hundred million. And it's interesting you bring that up because do you ever see the movie the Saint?
No.
With Val Kilmer?
No.
Okay. It's an old movie and it's based on an English TV series. So I grew up watching the Saint and they made a movie called the Saint. And in that movie, Val Kilmer. Kilmer, who's like one of the typical mercenary good guys that try, you know, hired. Hired gun for help. He has a number and his number was 50 million. And it. And he got a job and they paid him 15 million. It took him from 35 to 50. And now he was going to retire. That was his number. Of course things went bad, otherwise you wouldn't had a movie. But, you know, for me, I was.
Just up and to the right for the whole way.
That's what usually happens. So then I said to myself at a young age, I think I was in my 20s when this movie came out, I said, okay, I think I could do a hundred. That's going to be my number. $100 million. So that's my, that's my goal. So then I put my head down and I just worked at business from a lawn mowing company to the largest Kellerins franchisee in the country, to a private equity firm to go Bund. It's the entrepreneurial mastermind. Everything I did was to get to the outcome goal of being financially free. And for me, I had this belief, Ryan, that I viewed myself as a guy already worth 100 million. I just hadn't arrived at that destination yet. So everything for me was, what would it be like to be worth a hundred million? And why not me? In fact, I used to have this analogy in my head of a fakaisha tree, a foucosha tree, fakasha tree. And what that is is a giant tree that when it grows at first it has too many branches to support it. So you, you have to support that tree in order for it to grow into itself. And then when it has the trunk that's strong enough, it looks massive. And I viewed that as myself. I was like, I'm already worth a hundred million. I just don't have the structures in place to support Myself in that.
And so that's exactly where I am in my journey right now. Yeah, exactly.
Yeah.
Because I made a bunch of money and then I lost a bunch of money and then I had to relearn how to make and grow my wealth.
Right.
And that muscle is just strong enough now to where I say, oh, this is just time and reps. It's just like. It's just like going to the gym, you know, if I put in the work, I get the results. And now I have the plan. It's been demystified. I'm not wondering where to go and wondering if, is it this business or this route? It's whatever I water, that seed is going to sprout.
That's correct.
And if I am the best at that seed or that plant, I. Okay, this is going to happen.
Right.
So I'm. I'm exactly at that point in my life right now. And you made a comment to me before we started filming that I, I have a different energy than the last.
Time you do a gravitas.
And thank you. And, and, and it's this. It is this quiet confidence of knowing, oh, this, this just plays out. I don't need to figure out or chase. The tree's already there right now. I'm still supporting it, but I view myself right in that place of, oh, I'm going to be worth this. It's just. It's just time. And it doesn't matter to me if it's five years or if it's 50 years.
It's inevitable.
Yeah, it is inevitable.
And that's where I was. And by the way, I say this, you have to know you're going to get there. And I always knew. But that doesn't mean I had masses of doubts. At times things go bad, I would doubt myself. I would have a weekend or a month where something had gone bad, where I would tear myself up inside about, you didn't do it. Right. All these doubts. But the bigger energy of. David was always aware that I was going to be wealthy, I was going to arrive, and it was inevitable for me to end up where I ended up.
And you, you. Did you actually make the money in the Keller Williams franchise or in the private equity?
Yeah, I made it in Keller Williams had the.
Had the largest franchise, largest group of.
Franchises, got to multiple millions a year in income from businesses that I owned. But I want to go back to your analogy. So you said it's the reps in the gym, and that is correct. But if you want to be a boxer and you're going to the gym and exercising on endurance running, you might not be doing the right exercise. So, yes, it's reps for sure. It's knowing you're going to get there, and then it's figuring out exactly what's the workout that people do to become financially free.
Yeah.
And I think a lot of people that I see, they do the workout for making more money. They get really good at making money, but they don't do well at keeping that money and investing that money and having that money grow. And so, yes, it's going to the gym and then being aware that you're going to keep changing up those reps to get the right formula of reps for the body that you want to have. And so for me, that would be a mixture of strength, endurance, and flexibility. So I've got to work in my yoga and I've got to work in my lifting of weights, and I got to work in the. The endurance exercises. So for wealth, it's learning how to make money, which is all about bringing value to the marketplace, and then it's learning how to keep that money and invest it wisely. Because I think a lot of it, you said I lost a bunch of money, and I, too, have lost a lot of money. But a lot of us.
Cheers to us.
Yeah. Yay. Here's to losing money. Cheers. Such fun.
Yeah.
Yeah.
Tastes like poverty.
Yes. But the key is you go back and say, okay, I lost that money. Why did I lose that money? What was I thinking? Because I think entrepreneurs are the biggest suckers on the planet. Because we always think the next thing is going to be the home run. Because we're so optimistic.
We believe our own and we believe everybody else's.
You wouldn't work as hard as you did if you weren't optimistic. We work so hard and we're thinking, I, you know, a fool works as hard as most of us work. Like, for me, for 15 years, I worked as hard as I humanly could to the point of having health problems because of it.
I'm really glad you're saying this, because one of the questions that I couldn't wait to ask you is how the hell do you have so much time?
Right?
Because you have accomplished a lot and you never seem busy.
Right.
Active, yes. Busy, rushed. Never. Never seen you in that mode. So we can come back to this, but please, please point about 15 years of hustle, because I don't know that version of David.
Yeah, yeah. So. So here's what happens, right? I'm a c Student in high school. I have a lawn mowing company, so I make some money. So I got a little bit of a money vibe, but I didn't have that work ethic vibe, obviously, because I'm a C student. And then I get into the real world and I get into door to door computer sales. And that required hustle and that required courage. Courage is another one that I think people need to develop, which is making yourself do stuff that you're afraid to do. And I had the courage of walking right by the no solicitation sign and trying to sell computers to the person that said, we don't want to sell. We don't want any prospectors walking into our office. Right. So that sales skill was useful. And then I got into real estate and opening franchises kind of indirectly because my mom was a realtor in Austin. She joined Keller Williams. She'd opened up some franchises in Dallas. Those franchises were struggling. She had shingles from stress. She was at risk of losing it all. And I went up to Dallas to work with her in those businesses.
And that's where sort of the work ethic kicked in. And what I realized is even when I was in real estate sales, the amount of money I make is directly related to how hard I work at that stage, not today, but at that stage, when I was a real estate salesperson, every hour I put into finding prospects and selling them houses or finding listings and selling those houses was an hour that I got paid for.
When you say real estate sales, you mean I was an agent being a.
Realtor three years I was a realtor.
And that's where I started. That's working for money.
That was working for money.
Then you got into owning the business franchises where you have other realtors who are working for the business. And so what? What?
But let me be clear. So I didn't have the work ethic at first. Now, I worked hard, but I was inconsistent. Every time I applied myself. At school, I got an A. I loved working for a paycheck, so I was the best grocery sacker you could find. When I worked construction, I was a great construction worker. When I had my lawn mowing company, I worked a lot, but I was inconsistent. If there was nothing that felt worth my time, I would just lays out. So then I got into real estate sales and I was like, oh my gosh, like I'm making no money, I have no money. I came back from hitchhiking around the world and I had minus fifteen hundred dollars to my name. And then suddenly, if I put Ryan Moran in my car and I drive him through all these neighborhoods and I like him anyway, so we have a good time talking until he finds a house and then I get back. Then the commissions were small. It was like a $6,000 commission, right, on a $200,000 house. But to me, that was like, oh, how many Ryan Moran's can I get in my car in a one year period or listings can I take to make the most amount of money? And that's when my work ethic really started to develop.
How old were you at that point?
25, 6? 27. When I really started to grind.
When you started building the habit.
When I started building the habit, you.
Started going to the gym, if you will, you started putting in the reps. You started developing this. The, not even the strategy, but the. The habit of showing up and working hard. Didn't even start until you were 27.
Not started. Moments, always sporadic moments where I'd put a lot of effort into and that'd be done. I actually smoked a lot of weed in high school, so I was just kind of hanging out with my buddies, getting stoned all the time, playing Dungeons and Dragons.
So 27's not too late to.
Not too late. No, no, no, no. And then, then what I found, Ryan, is like, that's why I love Tony Robbins, because Tony will teach you work ethic. Tony will show you that you can walk across fire. Tony will show you enthusiasm, energy, not letting your negative thoughts take over, but just switching to your positive thoughts. So I learned so much at that stage of my career from not just Tony, but Jim Rohn and all the motivational speakers. And this is where I started becoming an a student of life. Because I was like, oh, I want to get somewhere. I don't know how to get to it. I need a personal trainer for this gym. Not just one personal trainer. One to teach me yoga, one to teach me strength training, one to teach me endurance. And I became kind of addicted to learning. And I also, someone told me a long time ago, people have lived before you. You don't have to reinvent the wheel. So I became kind of addicted to finding that person that was just ahead of me and copying exactly what they did. So I also joined a mastermind with all these top, top, top agents when I wasn't even a top agent. But I got my way in there. I was the youngest guy in there because I was like, how do I model these guys? Like, what do they do? And what I learned, most of them are workaholics. So most of them worked 14, 15 hours a day, 350 days of the year and that's how they made all their money. So I modeled that for a while and for three years I did that. And then one day I was driving down the same street on the same for the third time on the same day saying the same shit, same thing, excuse my language. And I was like, you know what, I need to go do something different. This is not where I want to spend my life. So Now I'm almost 30 and I'm, I've had success. We're the number one team in Keller Williams, me and my mom and we've, we're, we're selling. I think we, we netted like 500,000 in our business that we co owned is the best she'd ever done. And it was great for me as well. And she'd open these franchises in Dallas that were doing badly and I decided to move to Dallas and just turn those around. So I moved up to Dallas. Keller Williams is growing very slowly at this point.
So this is what, this is what I'm hearing you say, David, is that you had developed a set of habits and a skill set as an agent. Right. As, as somebody who's building their career.
Correct.
Which then translated over to the business. And you could instill those habits in those strategies.
Yeah.
Into the business.
Because what I. Yes, because what you're missed me is I decided that that transactional way of living was not the way that was going to get me to the destiny. The 100 million.
Yeah.
I wasn't going to get there no matter how hard I hustled. I could make a million bucks a year as an agent and I see great agents way better than I ever was making one or two million a year. And it's almost impossible to get out of the rat race even if you make one or two million a year. If all you know how to do is work hard and make money.
Yeah. So you go from hustler to business.
Owner to business owner to builder to business builder. And I brought the same habits. So I went to Dallas and I would work as hard as I could, having as many appointments as I could to recruit agents to my offices and to Keller Williams as a whole and it would be non stop. And I was so bad at time management, Ryan, that sometimes I'd be like an hour late for my appointments and I would have to call someone in the office that I knew and say, hey, Ryan's walking in at 1 o' clock and I'm running late. Can you Meet him and show him around the office really, really slowly. So that's what I used to do. I was so bad at time management, but Dallas is also a big city and I was opening franchises and the goal of the franchise was to have a certain number of agents, and when you hit a certain number, you break even. And then every agent after that increases your profit.
That sounds exhausting. Well, it was.
I mean, I worked 12 hours, you know, every single day, six days a week, sometimes 14. I worked as hard as I could. I've met people that can work harder than could. So I would never be like, who's the guy I saw? Who's the guy that does 100x or 10x.
Gardone?
And then the other guy, what's the other guy that also did the wine? And now he's a big time social media.
Gary V. Is a great human being.
So Gary V. They were arguing about who worked harder on a, on a podcast I watched and guess what? I, they both outworked me. But I, but I worked freaking hard. Does that make sense? I worked as hard as I could and it was 12, 14 hours a day and it was non stop and for 10 years.
I'm sorry, I just, I shouldn't say. Gary Vee is a great person and Grant Cardone is not. I shouldn't say that. So let me modify. Gary Vee is a great human being and Grant Cardone is not.
I'm not going to comment on either of them, but I can see your point of view.
I've, I've met them both.
I've met them both too. And I like Gary Vee a lot and Grant is cool, but I don't know him very well.
Okay.
Okay, fair enough.
Continue.
Yes.
So. So you are not going to make $100 million being an agent. This is not going to have no.
Chance, almost no chance, unless you bought houses in like, you know, Simi Valley or something.
And could you see that there was a path to make $100 million in the same industry? But as a business owner, I could.
See that there was a pathway to free up my time. And so if you think about it, if you're selling your time, there's only a limit to what you can sell. You can, you got a limit of the number of hours you can work and you could, or you can make more money, but there's also a limit to the amount of money you can make. Now if you're a, a great ball player in the Major League baseball or the NBA, you can make 50 million a year, apparently, which is enough to probably get you to 100. But in the real world, where most of us exist, you're not going to make much more than one or two thousand dollars an hour, right? So that's going to bring you for to 2 to 4 million bucks a year. And then you have to learn to invest. But most people that know how to make money don't have any time to learn how to invest, which is why they blow all their money on stupid.
Deals and confirm which we've both done.
So, so what the offices gave me was leverage. So I could have a real estate franchise, I could hire a good manager and that business would grow without me and make me money. Does that make sense?
Yes.
So then I developed the skill of hiring people. That was my next. So my first lesson was how do I work really, really hard? How do I get good at sales? How do I get the right mindset? So this is all work ethic type stuff. And then it became how do I hire the right people to follow through on the mission that I need them to follow through on, which was to build a profitable office. And then all of a sudden I went from 3 to 5 to 6 to 15 profitable real estate offices that were making me on average a quarter million a year. So Suddenly I'm making 3,4 million a year and I'm working less. So all of a sudden I'm working less hours because I'm more focused. I'm actually, if you think about it, if I hire one great guy and they can take an office from break even to making me 200,000 a year, I'm better off slowing my entire life down to find that one person. So I would have hundreds of interviews, but not for agents to join my company. Now for leaders, by the way, they were similar kind of personalities. So I'd actually be doing both. I try to recruit an agent to my company while deciding in my head whether I thought they could lead the office. Because real estate managers are kind of like social club leaders. They're like preachers. You're looking for that strong social, leadership based personality. They don't have to be organized, they just have to be charismatic.
I have heard you say that when your focus shifted to creating millionaires, right? That is when your net worth started to skyrocket 100. When you started investing into other people's success. That was when your life really changed.
So here's what happened. So I'm hiring people to run my offices, but at first I'm not very good at hiring. I hired an Alcoholic. A person was dealing drugs out of the office, a guy that was threatening to beat up our agents. So I. I hired a lot of.
Is this the same person or three different.
Okay. I had a lot of experiences. You know, sometimes aggressive people are healthy, and sometimes they're not healthy. And you learn. There's a lot of distinctions out there. But so I am doing almost all the work. I would get a lot of mediocre managers, and I'd come in and interview agents, and I'd bring them in, and I just hope that agent, the manager, wouldn't run them off. But then one day, I hired a really good manager and I got her. People referred her to me, and people said, I know a great girl for you, but she will never come work for you. And I was like, well, let me be the judge of that. I had to keep training people. I'm like, even if you think the person that you think is talented would never work for me or would never change jobs, give me their name. Anyway, let me, you know, figure that out with them, because I found I was quite compelling. And I could bring people over for a pay cut to run a business by selling them on the idea because a lot of people get burned out. They get kind of cubbyhole. They're stuck in a little spot. And I could say, yeah, you're making 150. But if you come work for me for 75, with some upside and some potential equity, I'm basically going to be paying you to develop leadership skills. You're going to have a salary where you learn to lead. And if you do that for three to five years, you can go anywhere. So I was able to kind of sell people on the value proposition we had to offer. And I got this lady, she came and worked for me. Now in that office, I had a man, an agent that I had recruited that was one of my top agents. And after I had the new manager in place, and this is finally my first manager that was doing without me. So before that, I had bad managers. They were only doing with me like I was doing the work, and they were not blowing it. Then I got one that was doing without me. In other words, she was adding good people. And I never even met them. And I was like, oh, this is good. And then I went and had lunch with one of that. One of those first agents that I met. Sarah was her name. And she said, you know, David, when I first met you, I wasn't so sure about you, but now I think you are a great leader. And the only Difference, Ryan. I hadn't been in that office for a year. That was when the light went out. I was like, wow. Like, she doesn't respect me when she sees me all the time, but when I'm not here, she thinks I'm a genius. And that began to kind of alleviate some of the pressure. I was like, oh, I just got to keep hiring good people and let them build. And then all I have to do.
You have no idea how much that is resonating with me right now. There. There is some drama happening in a couple of my businesses right now that has shined a spotlight on a leadership gap.
Yes.
And when I am too busy, it means that someone on the team, usually me, is not leading properly. Or it means that there's the wrong people on the seat in the bus, which is also a leadership problem.
I mean. Yes.
Because I hired those people.
You're gonna have leadership problems in a business if you own it. You're going to have problems.
But I've just discovered the more I'm pulled into the weeds of every little decision or the more drama there is. There's a gap in leadership. Somewhere someone is minimizing other people on the team.
Right.
Might be me. It's often me.
Right.
But sometimes it's somebody lower down the chain who is micromanaging other people around them or has low expectations of the people that they manage and.
Or you've just put the wrong person in the seat in the bus.
Right.
Like you said, like, it's. So I had now this experimental playground of, say, seven offices, seven residential real estate companies, each with a different manager in different geographic areas. And I got to see how, when I was uninvolved, because when I was involved, I didn't see this as clearly. But when I was stepping back, I could see manager A is getting a results of. Of this. Manager Z over here is killing it. And there's no different. They have great territories, they have similar demographic areas. So the difference always came down. And the structure and the systems were the same. So the difference always came out to, who was Z? Who's that person? And how can I find more of them? Now, what was nice about this? You have. I know a diversified portfolio. Mine was a common thread. It was, can you show up as a leader, be enthusiastic, be charismatic, and recruit agents to our brand and our mission? So then I'm seeing this, like, I.
Just want to make sure I understand. So you. You could start to see a trend in the adequate leaders or the excellent leaders. And it was more about personality and leadership style, being able to communicate a vision, create an atmosphere of success than any other thing, that it was work.
Ethic, it was courage to make the calls. Some people won't make the calls. It was a charisma and a force of personality.
And that was the key factor between a business that was struggling in this business.
Yes.
And a business that was. That was succeeding.
Correct.
Because I'm looking at the portfolio of businesses I have.
Yeah. And.
And I'm looking at, okay, this one, this one's growing really quickly.
Right.
This one's struggling. And I, and I regularly think need a different strategy. Something's broken in the tactics.
Right.
But when I look at. Through the filter of who's in charge, that's when I go, there's a correlation. Yeah, yeah. You can, you can find the connection. If I assume you're right, that it's a leadership problem first and foremost, meaning the person who is in charge is the biggest determining factor of if a business is going to succeed or fail. And yes, there are market conditions and strategic advantages. But first look at the leader. You know, my, my problem gets a lot clearer.
Yours is also a product business. So I assume there's something in. Some products do better than others. Of course, but mine was all the same product. So eventually I get up to 15 offices and I'm able to see this one guy, John, is killing it for me, absolutely murdering it. So then Ryan. So now I've gone from a work ethic person to a people person. I went from a I do it to we do it, which is where I had a team, which usually means big eye, little we, so that people get people following them. That might be where you are, might not, I don't know. But I see it a lot of times where people are like, I have a team, but the reality is they're the big alpha. And then there's a lot of little people following them around, trying to get it right.
I'm just on the other side. Like, I'm. I'm breaking through that right now. That has been me for a long time.
And a lot of people stay there.
And, And I have. Am just aware that I'm there.
Yeah, yeah.
And starting to invest in people.
Right.
That is, that is why I invited you. This is the transformation I'm going through right now of, you're so young, so.
You'Ve got so much time.
Thank you. Well, how old were you when you were going through this?
So this is all in my 30s. I got really good at it. By the time I hit my 40s. But it was, it was basically my 30s, was the time I learned all about leadership, all about how to hire great people. And so suddenly this guy John is killing it. And what I would do is now, let's say over here, I had, Let me think of, I can't think of the name. I don't even remember the bad ones. Isn't that funny? I only remember my good ones names. But let's make up a name. Peter's not doing very well. So then I, I was, I was like, okay, John, you're now in charge of Peter. And, and I am no longer dealing with Peter. Peter now reports to John. So I took my 15 offices, I took my three best leaders and I gave them each, I might've had 4, 5 of the offices that were reported up to them. So that's how I segregated away. And then of those three or four great leaders, one of them became uber great and began to make a lot of opportunity for me. And then Keller Williams had these untaken master franchise territories. So I went and bought one in California, I got a part of one in Canada, I invested in one in North Florida. And then I used these guys that were the best here to go help me build there. So that's where you go back to who could I make a millionaire? Right When I realized there were some people that just were going to crush it better than I could. Because remember that agent said to me, I used to respect you, but I didn't respect you at first. But now I think you're amazing. And the only difference was I hadn't been in that office for a year. So now I was okay, how do I keep a covenant relationship with this person so that we're in relationship for a long, long time and I can keep helping them build their world. And as they build their world, my world elevates.
You come from the Keller Williams world. And that is a theme that I have seen in that entire organization. This idea of empowering empire builders, of empowering the next generation. Could you give a two minute summary of that mindset or that idea? Because I haven't heard it, I haven't heard it outside of that structure. But you've moved beyond that structure. So this empire building model, could you summarize that?
Yeah. So the idea is that if you want leverage, the best kind of leverage, there's three types of leverage systems. Leverage, money leverage, and then people leverage. And the best kind is people. If you have the right people, money.
Is being able to afford those people well, raising capital to Acquire customers or advertise or scale run at a loss. That's money.
Money saves you time. Money gives you Runway. Money gives you opportunities to experiment. People really do all of it. So it goes back to, I do it, we do it, they do it. So when I got to they do it, and I was kind of forced to because I was selling all these franchises and I was buying all these franchises, okay? So the concept of empire building is you can build an economic model for a business and a strategy, and then you can hire someone to run that strategy for you and then reward them within that strategy. And that frees up all your time to go build a second strategy, a third strategy, a fourth strategy. Now, what was beautiful about Keller Williams is first, they had great training to all of this, how to hire, how to train. The part I haven't told you is within this great talent search I was on. I also met with them and held them accountable on a regular basis. And it started with a high level of accountability. But as they got better and better, and by better, I mean they're growing. My company agents are joining without me knowing those agents names. That's probably the simplest way to say it because before that I was doing all the recruiting. So suddenly I've hired this guy Ryan. He's kicking butt. He's grown my agent base from 100 to 150. Our profits are up for the year 20%. They were up 20% the year before. And I'm doing very little to help him do that or her do that, other than having meetings on a regular basis where I know my numbers, I look at my numbers, I know the growth. I know they're not lying because I've had a lot of lying and forgering, too, forging results which you don't usually pick up on for about a year. But I'm checking the numbers. I'm seeing the P. Ls and I'm seeing the progress. And I'm like, oh, I've got a winner. So once I have a winner, I'm like, okay, what's the next opportunity I can create for John so that he's going to drive something else in my world that's going to be bigger. In this case, it would be a second franchise so that he can have a manager that reports to him and he's building that franchise. So that's what empire building is. It's. It's finding talent, giving them opportunity within your framework. And then as they. As you have a hundred people in your company who are the best, three or Four. Taking those best three or four and creating new opportunities that they continue to drive. And you're always the major beneficiary of that.
Is this how you are able to maintain a lifestyle that never seems rushed?
Correct. That is how, as I began to realize that, I could make myself irrelevant almost. So here's the thing. I. This guy John is such a hard worker, and he's so good that when I give him three managers, he actually makes those three managers work better than when I was managing them. Does that make sense? So now I'm like, oh, I really am obsolete.
So.
And then I find another one, Leslie. And Leslie was amazing, too. Just a killer. Like a. A stone cold killer with a big smile and a warm heart. So then she's making me a lot of money, and I'm. And I buy this other territory and I put two of my people in it. Now the only thing I had to do is. What I learned also is pay attention enough, because people burn out, life changes happen. And you might think you have this killer quarterback, and suddenly something happens. They get divorced, their mom dies, they. I don't know, they just get tired. And all of a sudden that pedigree quarterback that I had is now fading out. And I'm like, oh, crap, I was making so much money. Now I got to go figure out another opportunity or another person or is there a way I can save them by kind of giving them my role, which isn't as demanding, and letting them run the next person. And because of their knowledge of building that business, it's still a win, win opportunity. So, yeah, so I'm learning to identify talent and put them in the right seats in the bus again with a common platform. And this is where I think you have a more difficult journey is. Mine was all real estate franchises. It was all about recruiting agents, and it was all really the same model over and over again. So that was my world until.
2010 or so.
How old were you when you reached $100 million net worth?
Right around 50.
And how would you have calculated that?
We just do this assessment, like this portfolio overview. So I would have given my offices a multiple, usually a fairly conservative multiple. I owned a bunch of real estate by then, and that's a whole other story which we can get into in a minute. And then I just have various investments in stock and bonds and my primary residence. You just do. Like if you went to the bank to get a loan and they asked you to do a financial statement, we basically do that.
Was it a big deal for you when you calculated that and realized it was what you'd hope to.
It wasn't. It wasn't. And here's why. I, by then, had gotten a little bit addicted to the game, and so I had now raised my target to a billion. I raised my target.
Move the goal. Move the goal.
Why not in the mid-40s?
And I was like, you know, I'm going to be a billionaire. And I also think, Ryan, and this is where I'm working on so much things now is once you find a groove that works now. I was kind of like a steroided up workout guy. I'm going to the gym, I know what works, and I'm doing so many reps, it's almost all I can think about, all I can talk about. So it doesn't necessarily make me the best father, doesn't make me the best husband, doesn't make me the best friend, because I'm just driven to work. So you never met that version of me, I don't think. But I, you know, you were still.
You were still a work. A workaholic is.
I was workaholic. And everything was about outcome. Everything was like, what? How can I use this to get me there? You know, you asked me. I haven't done as many podcasts. The only reason I did podcasts in the past was to sell books, but I don't have any purpose now. I'm not trying to drive anywhere. But back then, I'd moved the goalpost. I wanted to be a billionaire. So I didn't really think much of it. I hired a killer young guy to come work for me. Matt King, who's just amazing, started off as my assistant, now is the CEO of one of my portfolio companies. And he's just incredible. And I, when I hired him, I'm like, my world is like a mushroom cloud. And I just. He's like, what would I do? I just need your help. I just need people in. Because I kept starting new businesses because I learned what I did inside Keller, and then I started creating other businesses outside of Keller Williams, kind of following a similar pattern of like designing an economic model, putting someone, a person in place to run it and driving that and then driving another and driving another. So I was kind of in it. And my oldest daughter, who's a therapist, said, you were kind of a toxic masculinity. Now, we're not going to get into politics here. She's a beautiful, beautiful person, and she's married to her wife, and they're both lovely people and they're therapists and they're amazing. But I get what she was saying. I was so aggressive, and I was so focused on outcome, and really, I almost overplayed the. The testosterone. I'm like, yeah, we're gonna do. And I met a guy recently. He said, I asked to meet with you, like, 10 years ago. And you said, I'll give you 20 minutes. Don't waste my time. That's kind of the guy I was. I was like, I'm generous. I'm willing to meet with you, but don't waste my time. Like, I was kind of like that, which is okay. And the guy changed his life, he said, because of our conversation. So it was nice that he validated that. But he says, you seem so different now. And I'm like, I am a lot different. So, yes, I was super aggressive and super committed, and I was like a guy that had gone to the gym so much and gotten such wins out of it that I was obsessed with.
Continuing to win, so why not keep going in that direction?
Great question. So. So my dad dies. There's like a whole sequence of events, of things that made me show, made me realize life doesn't go on forever. I'm not immortal. Does that make sense? And then I thought I also had to look in the mirror. So now I've hit pretty close to 200 million. Because Covid was really juicy for my business. Like, everything I own.
Great for real estate.
Yeah. So, like, I've kind of blown through some numbers pretty quickly, and I'm just like, you're kind of a fraud. You know, I. I also had a miracle baby at 49. I had my son, who's now 8. We had had a still birth before that. My dad had died of cancer.
And I just began to see life a little bit differently. Ryan. I was like, how many toys do you need? You already have more money than you need. You already have more real estate than you need. You have the. I have the. I have everything I could ever want. So only. The only thing I can do is incrementally improve my airplane, my jet. I can. I can improve the quality of my houses. I can have even more expensive vacations, but there's not anything that's meaningful. Like, I've. I've hit that goal. And I remembered that kid that said, I want to hit 100 million. And I had to look in the mirror and go, you're a fraud. Because you said, you want to hit 100 million. That was your number to walk away from the game. And yet you're still in it and you're still pushing to make more. And the other thing I would say to you, Ryan, and it isn't true for everyone, but for me, I didn't 100% love the version of myself that was this jocked up steroid junkie that was saying to people, sure, I'll help you. I'll give you 20 minutes of my time. Don't waste my time. If I met with you, by the way, most people I wouldn't meet with most people I would say, look, you got to go read these three books. And if you read these three books, send me an email summarizing them and if I like the summary, I'll meet with you. That's literally what I said. But that you know what it's like when you're super busy. You're trying to protect your time and you're trying to push away people because there's so many people that come and try to draw from your energy. But I didn't love that part of myself and I kind of wanted to go back a little bit to my roots, which was kind of a kind, loving guy when I was younger. So I wanted to come back to that. So that required change. And that's the change I've been working on for the last seven years.
Do you think that it was the birth of your youngest or losing your father?
I think it was a whole. I think everything put a little crack in my armor. So losing my dad caused me to ask my current wife to have a baby with me. And that led to Bella, who's my beautiful daughter, who's 15. So that was the beginning and the being a father of Bella. And then we had a stillbirth three years later where we had Victoria, who was born still. That kind of put a little crack in my armor. And so I'm just seeing all these things about life doesn't go on forever. Do I want to just be a suit of armor that's very, very rich, or would I like to have a richer experience of life? And so that's where the choices I made. And then having Luke, who's my miracle baby, who also was a high risk pregnancy, and having him born and in the NICU for just a minute or two and I was just like, wow, what do I really want to do with my life now? I want to hang out with my kids. I want to be with my son and my daughter and be the best dad I can be.
Tell me about the relationship between your net worth and asking that question. Do you think that it was satisfying to cross a certain threshold of net worth that gave you the space to ask those questions? Or do you think that you would have been asking those questions based on those experiences, regardless of how much money was in the bank?
Look, if I had to be on the rat, you know, what do they call it? The rat race. If I was stuck in a job making a million a year, I don't think I could ask those questions. I think if I was at 50 million or 75 million or 20 or 100 million, I'd have been asking those questions. So I think I had to have a certain amount of space in my life where I had enough to make me feel safe. And a lot of my drive was for David to feel like he was sovereign over his world, you know? But I think the actual number doesn't matter. And if I look back at all the. All the.
It's a feeling.
It's a feeling.
Yeah.
And if I look at all the milestones, making a million dollars one year, I never really paid attention to him. You know, Dan Sullivan wrote with Ben Hardy, the gap in the game.
Yeah. Great book.
It is a great book. And I was always on the. I was never. I was always falling into the gap. I was always about the next thing, the next thing. I almost never paused and celebrated the accomplishment of where I'd come from, because in a way, there was a part of me that was like, who cares? Million bucks is nothing. You made a million in a year. Great. Wow. What's next? And that's kind of the way I pushed myself.
It's been my experience that when I have a goal, like having $100 million net worth, when I focus on the gap between where I am and where I need to get to, none of the progress feels fun.
That's kind of where I was at.
But when. When I can flip it around and I know I'm gonna get there, there's no doubt about how I'm gonna. About the fact that I'm going to get there. Right. Every inch of progress feels at least interesting, if not fun, curious, spectacular, enjoyable. There's a different experience about even those little incremental pieces of progress. The mind fucking is when you don't believe you're gonna get there, because then every piece of progress just contributes to doubt. Is this enough? Am I. Is. Is this big enough? Is this a biggest step forward? Or am I actually behind?
Right.
That's. That's where my mental noise will get really negative.
Yeah. Or. Or I see people doing the wrong things, like some people Just double and triple down on the wrong thing.
Tell me more.
So you might have figured out how to make a lot of money, but not how to invest that money to have the money make the money, because that's the other thing. So one game is we do it, they do it right. And the other one is you have cap, you work for capital, and then your capital works for you. That's like the. That's the ultimate game of money. When you're passive inc. When you're passive cash earns passive cash, you're at a whole new level in life. And so. So people I see that are very talented, but they never pause or slow down to say, okay, what am I doing with this money? And I'll meet people and they're like, hey, I just found this oil and gas company, and if I invest in it, I'm going to get a tax credit and not have to pay any taxes. Or another guy will say, hey, I just. I found this charitable trust thing, and if I spend 100 grand and all this energy setting up this trust, I'll never have to pay taxes. And it's. I'm always like, oh, man, the odds are you're wrong, first off, because no, you know, the odds are that there's not the clever system for you to not pay taxes. There are some systems that you can try and then one day the IRS finds out about it and they're like, oh, no, no, sorry, we're not allowing that you owe us $2 million in back taxes. Or there's the oil and gas guy that says he's going to give you all these credits and then takes all your money and disappears. So people spend so much time trying to be clever instead of just following, like, the fairway. That's right down the middle of, like, learn how to be a great earner, invest the capital wisely, rinse and repeat for 10 years, and you're at a whole new level. Instead of like, blowing the capital by trying to be so clever that they get set back and they do it over and over again. So that's what I mean. People double down on stupid stuff. And I meet people all the time that are trying to be so damn clever with everything they do. And I don't think that works out.
That's how I lost more money in my life than any other way. Right? It's trying to be clever.
Right?
Trying to beat the system.
We all do that.
Trying to find the way around what everybody else is doing and ignoring conventional wisdom, right? Makes you a great entrepreneur. It does makes you a terrible investor. So where's, where do you invest?
Well, real estate's still the greatest investment for the everyday man to be wealthy. So I was lucky enough to be in real estate franchising. And then outside of the stupid investments I've made, like we talked about where I did lose a bunch of money, I started buying a bunch of real estate. And a lot of this started in 2011. So until 2011, all my money had gone into my franchises. So every penny I went went into opening more franchises.
And in that case, your net worth is really being calculated on the value of the value of those businesses. So. So that would depend on someone coming in and buying all these franchises. So where you really start to move the needle more in your control is when you're taking that cash and you're investing that. I'm guessing that's what you're, what you're calling private equity.
Well, at first it was my family office, just my private investments. My private equity firm is actually a firm that I have that has 3 or 400 million in assets under management. That's a whole business run by a really smart young man who runs it for me called Waterloo Associates. So that's actually private equity. It's a full on business. So private equity gobundance, which is the entrepreneurial mastermind. And then Keller Williams, you know, his.
Daughter and my son go to school together.
Oh, I did not know. You know Mike Stewart. Yeah, yeah, he's a smart kid. Oh my gosh. So smart. So much mental horsepower. In fact, I have a friend who runs a $7 billion healthcare fund and he, he's got like 189 IQ and I'm like, holy Toledo. That is like some serious mental horsepower. But Mike, way more than me, by the way. And Mike also has way more than me when it comes to mental horsepower. So those are the kind of guys I like working for me because they can do what I can't do. But what I can do is provide that confidence, that courage, the capital, and then the accountability for him to hit his goals with and through me.
What did I get lost on there?
So where you invest your money?
Yeah, so I started off simply in rentals. So I had like five or six rentals.
Wait, you're making millions of dollars from your franchises?
Right, right, right.
And then you decide to put your money into just rentals.
So I already had been building a few rentals along the way. So if you. Let's go to the crash. So 0708, the economy crashes. So at that time you'd find that I had 15 franchises, a couple master franchises, all Keller Williams, a few million in the stock market, believe it or not, almost 4 million in cash. And then I bought a rental property in Austin and I'd bought three more in Lubbock. So I had like four rental properties, just randomly bought them. The one was I never sold a house I lived in. So every house I lived in became a rental property. Still haven't to this day sold a house I've lived in. And Today I have 130 single family homes that I own. But so I loved single family homes. I understood them. My parents had had rentals, so I was just kind of adding to a small portfolio. So then the crash occurs. In the crash, my overhead was 700, 000amonth. I had 3.5 million in the bank. And the economy just goes. And all my revenue goes. And I'm like, holy crap, I can only survive five months. I have if. If the revenue goes to zero. If it goes to zero, which it never did. But at the time you have to. When your reverend revenue creator is like, you know, 70, and your overhead, your fixed overhead comes down like 10% or 20%, you're like, this is bad. You can, you can run those two lines and it doesn't look good at all. But what happened is it stabilized for me around.08 and I was still profitable. Now my profits were down 75%. So I felt sorry for me, but nobody else in the world would feel sorry for me because I was still making over a million bucks a year and I hadn't had to dip into that cash pool. So I had three and a half million, which by the way, I'd saved that cash mainly to invest in other franchises. But then I look at real estate in like 9 or 10 and I'm in a group with, you know, go bundence with Pat and Tim, who are also real estate investors. And I'm looking at real estate prices and I'm like, this is overcorrected. Like I'm, you know, I'm still scared. It was still scary in 10 11. People don't remember, but I start putting my toe in the water and buying some stuff. And then by 2011, I am so convinced that it's the greatest time ever in your entire life to buy real estate that I start a class teaching my agents why now is probably the greatest time in your life to buy real estate. Because values had dropped so much because there was no liquidity in the marketplace and, and that nothing Made sense. I was buying 24 cap rental properties, 24 caps.
So I'd buy 20 gross, 20, 24%.
So I'd buy a house for 40 grand that I could rent for 800amonth. So that's. Wow, that's 24 caps. It was crazy. So I would start buying, I started buying as much as I could. And in 2011, 2012 and 2012 or so, I started buying distressed debt on real estate because the market for real estate was getting pretty frothy. In fact in 2013, so by now I bought 800 homes. So this is what I'm talking about, private equity. So I started raising money. I was like, oh, I don't have enough money to buy all these deals. I'm seeing. I remember I was sitting with my CFO one time analyzing 3 million dollar deals, and he's like, which one should we buy? And I'm like, well, really, we should buy all three of them, but we don't have enough money, so we're gonna have to buy one. So I went to some buddies I knew. I didn't know any rich people back then, Ryan. I was the richest guy I knew. But I went to some people and I was like, hey, do you want to invest in a deal? And I raised 300 grand. I put some guys in a deal. I made them 27 in nine months, which is 41 annualized. And only two of them re upped with me on the next deal. And I'm like, oh my gosh, I need to know more wealthy people. And I was buying all these single family homes. We bought 800 of them. I was gearing up to buy a thousand of them in 2013. And then the funds got in and they started buying everything, you know, Blackstone and the big guys. And they killed my margins because they would buy stuff and I would like, I would think to myself, these guys are going to get killed. But they wouldn't because the real estate market just went through the roof. So I kept around 100 back then. And then I started buying distressed debt on real estate. So I, I found another in through a guy. He's like, hey, you should buy distressed debt, but you have to be a bank to do this. So I'm still running all my franchises, but by now I've got John running this for me. I got all these great guys running it. So I'm only needed in my real estate company 20 hours a week or something like that. It wasn't taking a huge amount of my time. So I have a lot of Time I bought all these single family, but now that's dying down, so I have to let go those employees. And then I find this distressed debt angle. And I hire a guy that used to work for Andy Beal, who's a multi billionaire who bought distressed debt. Really interesting guy. They wrote a great book about him. The. The professor, the Suicide King or something. He was a big gambler in Vegas. It's really worthy of a read. But I get distressed debt, and we ended up buying $120 million worth of distressed debt for something like 60 million bucks and making 30 million on that. So we were just buying debt. And then that market went away from me. And I. I, at this point was when I realized I need to make. I need to know more people that have money because I can't raise any money. This is 2014. That's when I joined Tiger 21, which is an investment group for people with over 10 million in. In investable assets.
It seems like the core strategy that you have followed throughout your career is learning how to make relationships and develop people.
I would say that's true. And be opportunistic in a space that I understand, which is real estate. So the other thing I believe is you find a niche, and then you take advantage of that niche. So that one community I told you about, where we were buying $40,000 homes and renting them for 800amonth is in a little community south of Memphis. And we probably ended up buying 100 plus homes in that community. And I wish I'd bought two or 300, honestly, like I was. You know, you go back and what could you have done different if you're making the perfect shot on goal? And I'd have just bought every single home that came up in that community.
You would have gone really deep in a niche that you understand.
In a niche that I understood.
And you sort of. You definitely did that in Keller Williams franchises. I did that in Keller's franchise. And then your next opportunity was pouncing into real estate.
Correct. And then distressed debt, but it was all related. The debt was on real estate. So I was really just underwriting the real estate. Some guy had bought a shopping mall. He'd built it for 3 million bucks. He owed the bank 2 million. The mall was worth 1.2 million. We'd bid 800,000 on the note. The banks were just selling this stuff. They're trying to get rid of it. Then we call the guy and say, hey, we are your new lender. And you know what they often say? They'd say, thank God. I've been trying to get hold of my lender, and they've been ignoring my calls. Sometimes they'd say, I've got a refi. And then we go to them and say, look, your Property is worth 1.2 million. We will take 1 million, 100,000, and you'll be 100 grand in the equity. If you can buy us out in 90 days and someone would just buy us out, and then we'd have made 300 grand on 800. In other cases, the guy wouldn't be able to do anything, and he'd just give us the property. He'd be like, I am screwed. I got nothing. And then we'd say, okay, we'll take the property. Just give us keys. Sometimes we give them 50 grand, they give us the keys. And then the other. The few cases of people would fight, they'd be like, ask for you. I'm going to sue you. I'm like, okay, well, let's go. And then we just spent a lot of money on legal fees, and we ended up foreclosing on the property and getting it that way. But we always tried to be cooperative and kind and let them walk out with some money because that made everything go smoother, faster. And that was just our philosophy of helping everyone win.
What you're helping me put together in my mind, is that there's opportunities everywhere. And once you understand the opportunity in the market deeply and then you focus on building the relationships in that industry, that is where you can build a strategic advantage.
Correct.
It's almost as if you mentioned strategy, capital, and people being the three points of leverage.
Yeah, systems, actually, but yes.
Okay. And it seems to me that this, the systems and the strategy is where people cut their teeth. It's what people develop first most of the time, because it can be learned.
Right.
But I think very few people move beyond that and get to the point where they're leveraging people in combination with systems and strategy.
Very few people leverage people at the level that I leverage people. Warren Buffett does it 10 times, thousand times better. Even Richard Branson, when I met him and I kept asking him, how do you run 300 companies? How do you run 300 companies? And he never actually directly answered me, by the way. I think he's one of the patron saints of business. But he. Eventually, one of his people came up to me and says, richard has a highly, highly talented group of three people that run all the businesses. So you got Richard Branson at the top. These three incredibly talented people that are like the board of directors for their 300 companies or whatever. They have the Virgin brands, and those guys are the ones that actually run the business. So it's the same thing. It's leverage. Warren Buffett buys a company, leaves the leadership in place. Leverage. So those are the models I follow. I think there's other models of people that are individualistic, that just drive and build, and I'm not that guy. Maybe. Maybe Jeff Bezos was more of the deep, deep driver and never quit till he finally quit.
I want to know how to find those people.
Yeah.
And it sounds like your experience was that you had a collection of people and you looked at their performance and you invest in the winners.
Right.
And in the case read somebody who wasn't performing, you had them report to the winner.
Correct.
It sounds like that was a learned response.
Yeah, well, again, I was forced to. I had 12 franchises. Every one of it loses money I had to write the checks for.
But would you have done it differently in retrospect?
No, probably not. I mean, what I learned was. Okay, let's also look at this. I have thousands of people in my world, and amongst those thousands of people, I might have found 10 people that are at the level of talent I'm talking about. I'm sure I missed some along the way. Now, keep in mind, let's say I have a rating system of 1 to 10. And if you're a 5 and below, you can't work for me. So it only really gives me a rating system of 6 to 10, which is 4. And I never give tens. So that really gives me 6, 7, 8, and 9. So I really got a system of. Of. Of 1 to 4. But if you're a 6, you might be salvageable. And I'll put you under one of the nines. If you're a 7 or an 8, really a 7, you might actually be fine. You just gotta. Let's say I've got a business in Tyler, Texas, or Waco, Texas. I can never. I'm not going to put a 10 in Waco, Texas, because they won't stay. So I put it, if I got a seven there, they just run that business. Maybe it makes 150 to 250,000 a year. And then there's low drama. That's what I do with the sevens. But the most interesting ones to me are the eights and the nines.
Is this subjective?
It is subjective. I don't have a. This is.
Dave, this is your call.
This is my call. But here's how I make my judgment. How much drama is there and how much money am I making? And what are the numbers? So these. There are metrics that I look at, like, every day. I meet with my team all the time, and we run through the business, and I say all the time. It used to be monthly, but now it's probably twice a year. It should be quarterly, but I'm. I'm not as on it as I used to be. But let's say it was monthly. Every month I'd sit down, I'd have a giant book full of all the numbers put together by our bookkeepers, because one of the systems is accurate bookkeeping. So we said systems, capital and people. The systems are your economics, how you run the business. Make sure you've got accurate financials, make sure you have accurate reports on who they're recruiting. And so that would be meeting with the people. So. And then there's the numbers, which is like, how much money am I making? And then the drama is more of an intuitive thing. It is a form of art. But there are specific metrics you can look at to see if you're doing well. So. So with my private equity firm, I meet with Mike probably three or four times a year, and we go pretty deep. How much capital have we raised? How's our capital doing every JV and every fund we've created? What's the rate of return net to the investor? What's our team look like? Who do we need on that team? And these are just conversations I have with my people. And. And there's two. If they look like a deer in the headlights, that's revealing. Or if they're like, Mike, they're, like, so far ahead of me that I'm following their lead all the way down the road of where we're going on this business. Then I'm like, oh, I got a nine or, you know, eight or a nine here, because I don't give tens. So my definition of a nine would be somebody that shows up every day, takes the business better, makes us more money, has low drama, and I need to do almost nothing. And every day the business is growing. So that would be a nine for me. An eight, it grows a little, maybe a little less drama. Seven, they're just maintaining and managing. Six. If they don't become a seven, they're out. But, yes, it's just my subjective assessment of the person.
How do you evaluate a new opportunity? Now you're in a different mode of life.
Yeah. So for a while, Ryan, I was just starting business after business after business in Fact, I look at myself 10 years ago and I exhaust myself, you know, I look at myself 15 years ago and I'm like, wow, you're crazy. So I would create a, I created a Spanish language school. It failed. I created, you know, some tech companies that failed. I, I tried create a little hub where people could come open businesses and I take a piece of equity. It failed. You know, there's so many failures on this journey, but it was always following the same model of like, do I see an opportunity, do I see a leader that could run it? Can my capital help it grow and can my accountability or systems help them get better? And if all that was a yes, then I'd move forward with that. But I always started with the person, you know. In fact, there's this guy I just met and got to know recently called Liora and He has like 30 businesses and his number one question he asked himself is, could I hang out with this person a lot? Do I want to spend my life with this person over the next six to ten years hanging out with them? Do I enjoy them? And I think that's a pretty good metric. But back then I was kind of like anything I thought that could make money, I would go after today. I have now offloaded everything. Matt King, who's my right hand man, who kind of runs and is the CEO of GoBundance, also runs my family office. And I've actually found that he's a better decision maker than I am because I'm an optimist. So I always see the best in people. I always see the best in an opportunity. And he's much more pessimistic than me. So now I just drive everything through him. And if anyone somehow slips to me and Matt doesn't get there to block him, I usually say yes. I'm like, yeah, hey, we're going to do this. And then I send it back to Matt and he slows it way down until I've forgotten about it and then it just goes away. Or we do it if we both agree on it.
Do you enjoy your life more now than when you were in the hospital?
I mean, it's all been awesome. Honestly. I've loved my life. I've loved the part of me that pushed really hard. I'm proud of that young kid that had a chip on his shoulder and had something to prove. But I'm really enjoying my last seven years learning to slow down, learning to kind of unfuck myself, you know, like to un. Like there's some drive that some of that Drive comes from some trauma. So I'm working through that trauma, trying to really be more at peace with what is and be in the moment. I would say for 15 or 20 years I was in the future almost all the time. I was driving my life towards the future. Right now I'm doing a much better job of being in the present. I have better friends, I have better community, I'm a better father. I'm finding ways to give back with the kids in Nepal. We're supporting a bunch of orphanages out there and we raised a half million at one of my events which supports like 50 kids for 10 years or 500 kids for one year. And so it's so fun finding ways to make a difference. So I'm really enjoying the process I'm going now of kind of getting to know myself better. But it's all been great. I mean, even the pain was great. The pain was some of the best parts in hindsight, not in the moments.
You have an 8 year old.
I do. Who's going to marry your daughter?
I believe I'm open to an arranged marriage.
Okay, good. Yeah, we've talked about that.
Depending on how big the dowry is.
Of course, David, as long as I don't blow it, it should be pretty good. But your daughter's so sweet and lovely, so she's definitely a candidate.
Thank you.
What lessons do you hope to impart upon your 8 year old? Yeah, I think and specifically when it comes to building wealth because there, there are, there's, there's different versions of David, if you look back at your life and your career, of course, and each one has different lessons but they're not always applicable at the same time. So.
Yeah.
What do you hope to impart upon your children as they go out and they have big shoes to fill so that they're or, or if they want to compare themselves to dad, that's a big comparison. So what lessons do you hope to impart upon them to encourage them on that journey?
Well, one of my favorite quotes is if not if you're not embarrassed by who you were 10 years ago, you're not living life. Right. So I think it's important that we learn to continually grow. For my kids, the number one thing I've worked on, Ryan, is kindness because they're going to be wealthy and no one likes a rich. I know people talk about not giving their kids money and all the rest of it and at one point I wanted to build an empire for my kids to take over and then I went in my head 100 the other way, where I was like, I'm going to give it away and I'm giving them nothing. But now I've come back to the middle of, like, it's not really fair to give.
I'll give them a hundred million, not the full two, though.
Well, I know that. That I think it was Warren Buffett, but it might have been Bill Gates said, I'm not giving my kids anything. And then the other day I read that they're all billionaires anyway, Right? Because you can't be around that kind of money and not have money. It just doesn't happen. Right. So my goal is, number one, that they be kind. That doesn't mean they're not driven. I mean kindness to. To the servers, people that are serving you food. So I make them look them in the eye, thank them for the food, ask for their order, say please. Because I know I can teach that.
The work ethic. I try to pour into anything they want to do. My old. My oldest daughter's a therapist. She's already set. She's a beautiful human. I'm very happy with her. We're very, very different. But she's amazing. Her wife's amazing. I have my first grandbaby. My daughter Bella is a musician and an artist. I just want them to have purpose. What I try to teach them over and over again is it doesn't matter what you do with your life. It matters that you do something that you love enough to get through the difficult parts. So you have to love whatever, and if it changes, change. But always have something you're purposeful on and that you're driven towards, that you're really enjoying.
That's different than follow your passion.
It's a lot different than follow your passion.
Passion assumes it's going to be amazing.
And it's not amazing.
You're going to know half of life fucking sucks, so you're going to get.
Kicked in the nut so damn hard, you have to have enough love for what you're doing to get up in spite of the fact that you just got kicked in the nuts. And while my daughter will never get kicked in the nuts. You get what I'm saying?
It's 2025.
Don't project that onto her.
That's true.
But the idea of purpose.
Yeah, purpose.
Something that you care about enough to.
Take a price for. Yes.
Those difficult times.
Correct.
Could you define what your purpose is or what it has been? I can't mine. And some people criticize that. I've had people like you don't know who you are if you can't define your purpose. None of us, I say none of us know who we are or what our purpose is. It's not a fingerprint.
Yeah, I think.
Could you, could you define it for yourself?
So I came up with a mission statement for me when, you know, one of those classes that we all do where they say, and mine was to achieve success in life through helping others achieve success. And that's kind of help. That's a thread that has followed me, that has stayed true to me all through life. I agree with you that the purpose thing is a little wishy washy because I. My goal was to be rich, and I am, so I live that value proposition. But I really, I don't think it comes down to a nice catchy phrase. Although for me, achieving success through helping others achieve success works. I think purpose changes. I think what matters is that you have a purpose. That guy, the guiding light that takes you through the dark woods.
Well, you said what your mission is. What would you define as the difference between mission and purpose?
I think your purpose is to be the best version of you, Ryan, that you can possibly be on this earth. And I think my mission is to be the best version of David I can be. And I think my son Luke's mission should be the best. Be the best version of Luke that he can be. But when people look for purpose of like, oh, it's to bring shoes to people that don't have shoes or glasses, I think all of that changes. Yeah. I know that Scott Harrison does charity water, and early on he stayed with that and God bless him. But for me, like, I like the room in my life to pick a purpose for a while, maybe give it 10 years, and then find a new purpose for a while. Mine with my purpose.
Do you mean mission when you say that? Are you using those terms interchangeably?
Yeah. Yeah.
So you have a mission statement. So are you hoping that your kids have a mission?
I hope my kids have something that turns them on enough that they are willing to pay a price for that thing.
I know I'm being pedantic here, but, but, but this, this, this matters because I think there is a distinction you're. You're highlighting, which is the difference between purpose and a purpose. Purpose is a feeling. It's a drive. It's a way you orient your life. You do things that are purposeful.
Right.
A purpose is how you define what something means. A purpose is my life means this. And I find that very limiting. I find that very.
I I find it elusive and kind of stupid, but doing purposeful things is a way that I can live every moment of my life. I can show up to this podcast with purpose, but I don't have a purpose for this podcast.
I get that.
And that distinction we sort of throw around, but I think it trips us up when it comes to defining what we really want and what turns us on. And that's why I hammer on this point so much. As you talk about what you hope to instill upon your children.
Well, we're getting pretty deep here and pretty esoteric, but for me, when an. When a acorn is planted and that acorn grows into an oak tree, it grows towards the sun. And for me, when things light me up, when anything in a movie or a show or a charity or something with my kid lights me up, that little bit of light is, to me, the sun or God, if you will. And I'm not super religious giving me a hint that I should put more effort into that. So I like my kids. It's. It's way more than words. It's. You were given this gift of life. Don't fucking waste it. Do something with it. And I don't care what it is. Just don't sit in your room playing on your phone. You can do some of that, but make sure something lights you up all the time. And that thing can change, but be leaning into whatever it is that lights you up on a continuous basis. And if you do that, you'll get more space for the light to show up in you, and every area of your life gets more fulfilled and easier. And when I was going through hell building my businesses, I held onto that. And today I have a lot. I have the most amazing life. I'm grateful when I get home to see my kids. I'm grateful when I fight with my wife because it gives us something to work out and to figure out. I'm grateful that I get to go to the beautiful places with my beautiful friends that I get to go to. And all of that is, I've attracted great people in my life because I've always tried to let the light come through and come out.
Light you up gives means, gives you energy, brings you curiosity, makes my skin.
Tingle, makes me excited to learn it about something, makes me lean into something, anything. That's like, oh, that's curious. Okay, first it was like, what's it like to have money? What's it like to be a leader?
That's what lit you up?
It lit me up, and it scared the crap out of me. And I think also what scares you is the, is the direction you should go in. Like a lot of times, you know, I think Carl Jung said, be careful what you fear for, that's your destiny. But for me, leadership scared me when I was 27 years old and I've got 50 year olds reporting to me. That scared me a little bit when I drove up to Dallas and I'm looking, I remember driving from Austin to this giant city and I'm like, I've got to go conquer the real estate market in this city for residential real estate agents. I remember thinking, who am I to do that? And then I remember thinking, who am I not to do that? Like, there's that, that's the tension of, like, I'm not worthy, fuck it, I'm going to do it anyway. Like, that's the part that I think is where all the fun is, maybe I can't do this. Well, let's give it a shot. And that for me is what lights me up. And the edge of that, like right now I'm trying to be a. I'm trying to figure out a lot of stuff with my wife and I. It's almost like we've been together 24 years and it's almost like we're newly married. Not in the best of ways, but in the way of we're trying to figure out why does this keep happening with us? Why does this happen, this happen and then this happen where I do something, you get pissed off and then we're cold, like what happens? Let's try to unwrap that. Let's figure out what so we can get more light in and more love. Does that make sense? So it's, for me, it's always that edge of like, what is available to me now to understand so that I feel more light, love and fulfillment in my life.
And you see those insights as an indication that you're on the right path?
I do.
When there's excitement or curiosity or tension.
Correct.
You're seeing those as the things to lean into. You're seeing those as indications.
The light from the sun, you lean into what you love to do. Because most people, I believe, repress themselves. They are taught early to repress themselves. So they get a job, that's okay. They have a lifestyle, that's okay. They have a relationship, that's okay. And they do everything in, in the world of okay with some, you know, I'm sure some amazing things too. I'm not trying to judge all people, but I'm saying for Me, we've been given this gift of life, and I think that fully experiencing as much of what that life has to offer is the miracle of life. And so for me, that was first being a businessman, actually very early on, traveling the world, then being a businessman. And now it's like, okay, why, why do all these things show up? Why am I doing that? Like, what, why is that structure inside of me? Why did I want to make so much money? Let's go back and look at that. And it's just like such a great exploration. So, and I think that's curiosity. I'm so curious. And then when I, when I live this way, I find that I attract people that also have that level of living, and they're really fun people to hang out with.
In my head, I'm sort of reverse engineering David osborne's path to $100 million net worth. And, and what I am synthesizing is it starts with listening to where there's curiosity and listening to that edge. That's the first sign. And, and, and that gives you an indication of where you can work really hard and learn the strategies and the systems and along the way, meet the people. And at some point the shift is empowering other people as a point of leverage for them to build their own edge, build their own lives. And by continuing to do that over many years or decades, in any field, in any opportunity, you have a shot at building generational type of wealth. Would that be a fair summary of how you see wealth?
I think so. I think you can't get there unless you get there through other people. I don't know anyone that builds massive wealth without other people doing it. But the curiosity you're talking about, here's one more I'll add to you is like, why not you? Why not me? I remember saying that to myself, because I would have these doubts. Who am I to go to Dallas and build the largest real estate company in Texas, which I did. But who am I to do that? And then the answer would come to me of like, eventually, after soul searching and some pain and failure was like, why not me? And everyone listening to your thing could be saying, whatever it is you want to do, why not you? Somebody has to do it. Somebody has to be number one in whatever field, or number 10, but whatever it is, something significant, why not you? Because that's the answer to all the self doubt. Because whenever my little doubters show up and like, who are you to do that? I'm like, well, why not me? Somebody's got to do it. So why not me? Does that make sense?
Do you still doubt yourself?
Not nearly as much as I used to know I've got. I'm very happy and comfortable with who I am. I know how hard I've worked. I know how hard I've accepted my mistakes, accepted my failures, been willing to look hard at myself and change things. You know, where it shows up now is like, am I doing the right thing as a father? Because that's scary, right? Because you're like, I take that on. So, yes, I still have doubts. My doubts are, am I spoiling my kid? Am I being too hard on my kid when I occasionally lose my temper, which is very rare for me, but sometimes I do. Am I letting him watch too many screens? So my doubt now is in more, you know, sensitive things. In the past, my doubt would be like, who am I to build a business? Am I worthy? But I've proven myself in multiple times that I can do that by never quitting and driving myself towards the outcome I want. But my doubts now come more in the emotional space, which is kind of fun too.
Do you think that the confidence that you developed was because of outcome that was created or because of habits and obstacles that you overcame?
I don't know how to separate the two. I think if I had failure, I probably wouldn't feel so confident. But I have confidence because I know what I do works. So I know exactly how to do it. I could do it over and over again. I could be a billionaire without any question if I was willing to give the next 10 years of my life to 40 or 50 hours worth of work a week. But I'm not willing to do that right now. I want to be a dad.
That's interesting because I experience confidence when I overcome an obstacle more than when I accomplish a goal.
I agree with that. What I'm saying is my habits and my behaviors are set in that way. I'll give you an example. A friend of mine said the other day, let's do a 30 day, no sugar challenge. I said, okay, I'm in. And then he said, here's the reward. Here's the. He sent me this whole list. He gamified it. And I'm like, jer, I don't need the game. When I tell you I'm in, I'm in. I won't eat sugar for 30 days. Because I said I wouldn't. The me of 20 years ago would want that game so I could gamify it. Does that make sense? That's the difference between me now and me 30 years ago.
You trust yourself.
I know myself. If I say I'm gonna do something, I'm not gonna say 100 because no one's 100. But it's highly likely I'm gonna do what I say I'm gonna do, because that's what I learned. Works. What works is you keep your word to yourself.
That's the muscle that you built, that gives you confidence, is you. You know you can rely on yourself because you have undeniable proof in a myriad of different ways. You have it in wealth, you have it in business, you have it with building up other people.
Even my health, I'm in better shape now than I probably was 30 years ago. All of it. I know A, what to do and B, I know that if I invite myself to do it, I'll do with about a 90% success rate, which is.
A, how do you think someone can develop that?
I think you surround yourself with people that do that. I think you have a clear vision of where you want to go. And if you don't have the discipline, be around disciplined people. That's what I got from the realtors. Those realtors aren't as wealthy as me to this day. Not a single one of them. Even though they were way ahead of me when I met them. But what they did have was discipline. The realtors that I met that were working 60, 80, 90 hours a week, you know, you join the Masterminds, you join GoBundance, you join Genius Network. You join capitalism.com. you join.
Yeah, you do.
You just be around people. You join them. I'm in. To this day, I'm in a group for 100 million net worth people. I'm in a group. I was in Tiger. I was in ypo. I'm obviously in gobundance. I've been in Joe Polish's deal. I've been to your deal. A bunch like you can't have enough of that. Because we learn as humans through. We're pack animals. We learn through osmosis. We learn to be badasses by hanging out with badasses. And you learn to sit around doing nothing with your life by hanging around with people that sit around and do nothing. It's that simple.
You're in a mastermind of only people who are sent to millionaires worth a hundred million dollars.
You have to have a hundred million to be in this group.
What's that like?
It's fun, man. It's like it was. Tiger was similar. Like, I'd been in real estate so.
Long, I only Knew what are the people like?
Okay, so Tiger was 20 million. It was 10 originally. Now it's 20 million to be in it. This group is our 360. It's 100 million plus. And they're, there's just, they're just the similar but further developed people. They are super confident, they are super self reliant. They are really good at doing what they say they're going to do. And in some cases they're really intelligent. Sometimes they have big personalities. They have all have great work ethic. I haven't met a single one that didn't have a great work ethic.
There's a few that inherited some wealth too, so. But the majority of them are just people like you heard me describe. They can count on themselves. They don't need anybody else. They're not needy, they're not asking you for anything. In Tiger there was still some aspirational people that try to sell you on something or raise money for their deals. Nobody does that in this group. They talk about their next hundred thousand dollar vacation to go see the gorillas and Rhonda. They struggle sometimes in relationship, but it's just, it's just what I told you man, is that level of confidence just goes through the roof. You look at Donald Trump and Elon Musk right now, they're changing a lot of stuff in the country. We don't know if it's going to work or not work. But one thing's for sure, they are confident in their action steps. You know, that's, that is the ultimate pinnacle of what you see in these people is just more and more confidence and capability and capacity, work ethic, self direction. They're cool people. They're usually kind of islands, you know, like unto themselves. Like they have everything they need. They're like a small country or something.
Would you draw a distinction between confidence and conviction? And, and I'm, I'm asking because what you're describing as confidence, the examples that you're using sometimes involve a new adventure or a new direction. Elon Musk has never made decisions that impact a country.
Correct.
Before, Right. You had never gone on a 30 day no sugar challenge. These are things that are not domains that you are used to, but you are confident in the decisions and the directions in which you are going.
So I love the way you distinguish these words. I have done some no sugar challenges before, but I could. You could, you know, you could say any challenge and I know if it's physical, I can do it. But is it conviction or is it confidence? I think you can fake confidence. And early in my career I learned to fake confidence and it probably was almost showed up as arrogance because I wasn't as certain of it. But I knew you had to be confident to win, so I overplayed that hand. Do I think Elon Musk is convicted that he can make.
Well, what I'm really getting at is in this group, yes, that is all people with 100 million dollar net worth. She said that they are all, all very confident. And I'm not imagining the arrogant confidence that you are referencing.
It's just a.
There's an internal confidence that comes from something other than I've created $100 million in net worth. I don't think that you get to $100 million in net worth. And I could be wrong, I've never done it. But I don't think you get to that level and magically you unlock a level of confidence. I think the confidence comes first. I agree with you and I want to understand that if that is a mentality that all sentimillionaires that you know, or the vast majority of them, if that's a character trait that they possess, I want to know how that was developed. Not because I think it will get me to the hundred million, but because I know that that is a part of who I need to become in order to accomplish that type of, of accomplishments.
I can only speak for me and I think it's probably true of all of them. I have had some really hard times. I've had some moments where I thought I couldn't go forward, where I thought I was going to quit. I had the 06 crash before that. I had some real. When I said I had an alcoholic, a drug dealer and a guy that was threatening to beat up my agents, I'm not kidding. Those were three of my first six managers.
And I wanted to quit and I wanted to stop. And I still got up every day and went to work. I still made my calls and I pushed through that dark time. And I've had that multiple times in my life where I just thought I don't think I can go to work today. But you know what I did is I went to work that day. And I think when you just keep going forward in the spite of being assailed by life, which will happen when it's kicking you in the nuts. Been there and then you know, you can count on yourself. And that's what I think these people have, they've been through the multiple times. Like my friend that has this 189 IQ. He had started his fund. He was up to 800 million, and he got a disease that nearly killed him. He had to get a bone marrow transplant. And he worked every single day while in the hospital getting a bone marrow transplant while having his blood cleaned by a. Whatever those things are. So, I mean, he's going to be a billionaire for sure. He's probably halfway there.
And it's not like even an arrogance. He's just like. He just knows that when the shit's really bad, he just keeps going. He doesn't quit. And that doesn't mean you can't quit on Friday as long as you go back to work on Monday. So I always want to emphasize that sometimes it's overwhelming, and you're like, I can't do this anymore. Then you get a good night's sleep and you wake up. I can do it. Does that make sense?
It does, because I used to think that confidence came from winning. Yeah. And I. And there are people who believe that, but it has not been my experience. Confidence, for me, has come from losing and getting better through it. Not quitting, getting punched in the mouth and leaning back into the fight. That has been more for my. That has done more for my confidence than success ever has. The thing. The irony is that the more confident I get in losing, the more I win. When I had my losses.
I made a whole bunch of money when I sold a company, and I'm confident, but not in the quiet, calm way. I think I've got the Midas touch. Overconfident. It's not real confidence.
This is early.
This is 10 years ago. Okay. And then I invest that money and I experience a whole lot of losses. Now I'm depressed, I'm anxious. I worried that I'm washed up. It was the process of getting better. Mentally, physically, emotionally, spiritually, financially. The recovery in which I felt like most of the time. Most of the days, yes. And learning to go through it and learning that I could rely on myself during those dark times, that is what built my confidence. And after I went through that process, now I feel bulletproof. And this quiet confidence that you said you perceive in me, in which I have a knowing that I'm gonna get there, but I also don't care that much. I care way less.
Than when you were younger.
Than when I was younger.
Striving, yes. Yeah.
I am more confident and I care less. And I rely on myself more because I know what I am capable of. Not in the good times, but in the dark times.
Amen. I think that that.
That to me is confidence. And I'm curious if. Is that the confidence that you mean?
That is the confidence. I mean, when you're willing to do whatever it takes. And you've been tested on this, so you're like, I'm gonna do whatever it takes to make 100 million. Then you get punched in the face. You're like, oh, and I guess I'm not willing. And then you're on the ground and someone kicks you in the stomach, and you're like, oh. And you're like, am I really willing to get up and do this again? And then your answer is yes. And you get up and do it again, and someone kicks you in the nuts and you go down again. And then someone betrays you and steals your money and some bad happens, and you're like, okay, am I willing to do whatever it takes? And then you say, yes, and you get back up. And that's where that muscle, the. The resilience shows up. And that's what. That's what I try to teach my son. I don't know how to teach my son that in the abundant life we live. But it's those. And. Yeah. And it's getting. You have.
You've proven to yourself.
Yeah.
By getting kicked in the nuts and recovering.
Right.
That you indeed were willing to do whatever it took. And now that confidence can be translated over to other domains of life. That's the confidence that you're describing in this group of people are worth a hundred million dollars.
Correct.
So what I take out of that is that the value or the habit that each of those centimillionaires possess is that they've gotten kicked in the nuts many, many times and gotten back up and continued. And so the secret is not to avoid getting kicked in the nuts, to get better at getting back up and moving forward.
Having iron nuts.
Yeah, I think. I think. I think that is it. It's like that resilience. I used to ask people when I met him, because, again, I was trying to copy people that were successful to become successful. I'd ask, what's the three traits that got you to where you are? Like, what are the three things that you think are most important to your success? Two of them would always change. Vision, hard work, you know, knowing technology, whatever, hiring good people. But one of them always showed up, always. And that was resilience, tenacity. I never quit. I. You can't keep me down. Like, it was always some version of I keep coming back. And so that's What I say, if you're willing to do whatever it takes, you won't fail. And if you read every story of almost every entrepreneur, there's a point where they were right at death's door, and they came through. Elon Musk was. I don't think Warren Buffett ever was. But Zappos, Tony Hsieh, God bless him, rest in peace, he had that story. Richard Branson, Donald Trump, all of these people have been on. On the edge, and they've come through it, and then they're like, oh, I see what life is like. If you just keep going, life will eventually yield. If you're willing to do whatever it takes, you never, almost never have to. And by the way, I got into a lawsuit recently with a bigger. A very big company that tried to come at me, and I was the same. And it. We. We settled it. And I got paid in a few months ago, but we settled a few months ago. I'm supposed to get paid a month, but it was the same thing. I was like, yeah, you can come. You got more money than me. You're bigger than me. You can push. You can push on me, but I will fucking die before you win. And I know this about myself. I know that I am not gonna. I'm either gonna take the whole house down or we're gonna come to a fair settlement on this deal, but I will not be pushed around by.
And you're at peace either way.
I'm at peace either way. The Navy seals say if you go into a battle, you have to imagine yourself as already dead, and that's how you fight the best. And I think that shows up for a lot of these people is like, yeah, they don't have the fear. They know that if they decide something.
They'Re not going to quit. And therefore, eventually what they've decided on will show up.
I want to close by asking you about the three books that you would have forced someone to read in order to get 20 minutes of your time.
Right.
I don't want to know what they were when you were an.
I want to know what they would be today. When you've got a. A full calendar and someone asks you for 20 minutes of your time and you say, go read these three books and summarize them. Today's version of David.
I'm trying to think, what would those three books be? I'm trying to think if they've changed. Because you're talking about an entrepreneur, because most people that reach out to me want to be wealthy, so it's not like I get the guy trying to decide if he wants to be a chaplain to reach out.
And I think the greatest books for wealth haven't really changed ever written. I mean, there's probably five or six or 10. But one of them for sure is As a Man Thinketh, which is a tiny book from 1800s. And it's really all about like your thoughts generate your outcome as you think so shows up your life. That's called As a Man Thinketh. I. I think by Wilson, but I'm not 100 sure. The second one would be Think and Grow Rich. Really, I think it's just an amazing book from way back when.
That one surprises me. Okay, but continue.
So as a man, think and think and Grow Rich. And then I love the Cash Flow Quadrant by Robert Kiyosaki, but I also love my book Wealth Can't Wait.
And I used to tell them to read my book Wealth Can't Wait or Tribe of Millionaires because I would always throw one of mine in there because I know it so well that if they fed it back to me. Now you're shocked. But I will tell you that when.
I was young, I'm more shocked by Robert Kiyosaki, I think, than.
Well, what Robert's. The Cash Flow Quadrant is life.
Yeah.
It's the employee, the self employed. So the E is the. You've given up. You're letting someone else determine your life.
This is, this is what this is.
Self employed, business owner, investor. That's been the journey.
What's coming up for me is since we're talking about, we've talked about people and building up people.
Right.
What's coming up for me is I can.
Is hard for me, but I can look at something like rich dad, poor dad, or the Cash Flow Quadrant and recognize that they are wonderful pieces of work that have impacted my life and the lives of millions of people, irrespective of my opinion of Robert Kiyosaki.
Right, right, right. I got you.
And the same is true with Thinking Real Rich. That is a wonderful piece of work that has helped and transformed many, many people.
Napoleon Hill. Right.
But I have different opinions about Napoleon Hill as a, as a person. And that is a tough line to walk sometimes I think for all of us of separating the creation from the Creator and respecting one, even if you don't respect the other and recognize that they are, they are separate things. And this is, this is true about Cardone too. Is. Is. He has created some amazing things, irrespective of my personal experience with him, which is totally subjective. And so you saying those is sort of. It's holding up a mirror and challenging me and seeing where I still have some judgment around an individual that might color my experience of their work, which is, which is actually limiting my experience to benefit from what they've created. So that's, that's the processing.
Two questions come up. This is interesting. One, the first question I have is.
Well, I want to know what your three books would be. And then second off, I would say to you that again, I refer to the Bible a lot. I was raised very Christian. I'm not very religious today. But judge a fruit by the judge a tree by the fruit it bears is one. Meaning that Robert Kiyosaki impacted a lot of lives. He's a crazy old coot. I've met him. I've had him speak for us. He's. He's crazy. Yeah.
What fruit do we taste in here with Robert, his tweets or his books?
I'm. I don't follow him.
And which. And which ones did he actually write?
Right. Well, there's another debate. There is that. But that's one is cash flow quadrant is the most simple reflection of what you want to do. If you want to get financially free, you want to go from an employee to a self employed to a business owner to investor. That is the journey of multi generational wealth.
But he also wrote prophecy which predicted that the great crap.
Yeah, but.
But that's also his fruit.
But you're also judging humans that are hugely flawed. Every human is flawed. And if you look into anyone's life. I used to put people on pedestals and guess what? Every one of them's disappointed. Yeah. Even when I was starting private equity, I had guys, I reached out, looked up to put them on a pedestal, got advice from them. Some of it was good and some of it was bad, but they are no longer on a pedestal.
That's exactly what I mean. What, what I'm realizing even as we're is I'm seeing that I try to do a good job of analyzing each individual piece of fruit, not the tree. Meaning I try to look at a piece of work and say, how did this benefit me, my life in the world and not allow that to color my experience of something else. But it's hard, it is hard to not bring your judgments of one thing over into something else. I get flack for this, but I evaluate presidents the same way. There are things that Joe Biden did that I liked, even though I didn't vote for the guy.
Right.
And I had to separate my judgments of whether or not I thought he was fit to run the country versus the individual decisions that he makes. And the same is true with Donald Trump. Whereas I think most people say, do I like them or do I not like them? And I will judge all of their decisions through that lens.
I don't do that at all. I think I have. I think, I think for me, it's hard to be into politics because I always think every president does some good stuff.
Yeah.
And some stuff I don't like. And I can't. If you're stupid, if you're a blind faith follower of any person, because every person is going to screw up some stuff and do stuff. Well, if you were perfect, you would be God. There are no gods that I know of walking the earth. So therefore every human you're taking advice from is flawed in some ways and not flawed in other ways.
And I've set. I met some of the people that God has made and I wonder if even he is perfect. Now that you asked me the question of my three and I would say straight line leadership.
Okay.
By. I can't say his name. Deuce. And he's just a mysterious person who wrote a great book.
Okay.
Number two would be the Slight Edge by Jeff Olsen.
And the third.
I'd say the One Thing by Gary Keller.
Interesting.
I would say if you were to combine the one thing I bore your pen. I would say that if you were to combine the Slight edge and the one thing that would summarize how I see.
Success and wealth and generating results over the long term. And then straight line leadership is leadership and slight Edge.
I've read the One Thing was something that Dan Sullivan kind of taught when I was in the strategic coach, which was, you know, if to focus on the one thing you need every day.
Those two of those books, though, I've never heard of, so that's cool. I'll have to go read those.
Good.
But if you expect people to be flawed, there's so much wisdom and knowledge out there. I mean, it's, it's in abundance everywhere. And I respect your desire to see the whole package instead of the individual value. But if you, if you look deep enough, every single hero out there is going to disappoint you.
And, you know, when I saw a T shirt the other day, it said, God must love stupid people because he made so many of you.
So. But I think we're hard. I think you're hard on people. People are pretty limited for me. I always judge people based on who they are, not what I want them to be. So if I have a manager and I and they're doing 70% of the job good.
I have to accept that 70%. And if I'm super mad about the 30 I think they should be doing but they keep not doing, then I'm just going to be unhappy. If my wife does 70% of the things I love, but 30 that I hate and I'm going to obsess about the 30 that I hate, I'm going to have a terrible relationship. Even said I validate and appreciate her for the 70% she does, I love, it's going to be a lot easier. So that's all. That's how I look at life.
How do you hope that people judge you?
I hope people judge me by the impact that I've had on people when, when, when I'm done. If a hundred people say my life was changed because of the way David chose to live, that would make my life worthwhile.
Beautifully said David. Great to see you my friend.
Great to see you Ryan. It's been a blast.
It is very hard for most people to get an hour of David's time. I am able to bring him to you because he's in my network and I've known him for more than five years. I would like to be able to bring to you the people that I haven't met yet, the centimillionaires that can offer value to you on your journey to wealth and success. So if you enjoyed today's discussion, you can pay it forward by helping us go find the next guest for capitalism.com by liking this video and subscribing to the channel. My name is Ryan Daniel Moran. I help entrepreneurs build seven figure brands and have multi million dollar exits. And I hope you enjoyed today's episode. I'll see you next time. Take care.


