114: Founding 50+ Companies and a $10B/Year Real Estate Brokerage with David Osborn

Today, I’m speaking with David Osborn. At 26, David returned home from traveling the world, broke and unemployed. Within a decade, he built one of the world’s top real estate brokerages, with 4,500 agents and over $10 billion in annual sales.

David is not just a real estate investor; he’s also founded 50+ companies, is a speaker, wealth-building mentor, and author of books like “Tribe of Millionaires” and “Wealth Can’t Wait.”

In this episode, David joins the podcast to share his secrets to success. You’ll learn how his vision for making an 8-figure income came true, hiring strategies the ultra-rich use to maximize output and scale without burning out, and his blueprint for achieving a life by design.

Inspiring Quotes

• “Freedom requires tactical strategies.” – David Osborn

• “I can have as big an empire as I have talented people working for me.” – David Osborn

• “Some organizations, they get bigger and bigger and they stop looking after their people. And it’s the beginning of the death knell of the organization.” – David Osborn

• “The way I kind of pour into people is by letting them fall on their faces.” – David Osborn

• “The quality of your business life is going to be directly proportional to the quality of the five direct reports you have.” – David Osborn

• “The number one most important thing in building an entrepreneurial operation is great people.” – David Osborn

• “The more I’ve been abundant and let go of little things, the bigger my life’s been permitted to become.” – David Osborn

• “Wealth has a gravity to it. The more you have, the more you make.” – David Osborn

• “There’s no one that’s wealthy that doesn’t have wealth. And the way you have wealth is by earning, saving, and investing in something — yourself, a business or real estate, or the stock market. But you’ve got to play that game to get to financial freedom.” – David Osborn

• David’s entrepreneurial beginnings
• Pushing back against authority
• The jump from sales to entrepreneurship
• Going from 80-hour weeks to lifestyle design
• How your mindset shifts as you scale
• One-minute managing
• Making money by spending money
• Turning abstract visions into reality
• Replacing your income with real estate
• How David created a 9-figure net worth
• Aligning your investing with your wealth
• The exponential value of peers and masterminds
• Wealth advice for 7-figure earners

Brad Weimert: David Osborn, I appreciate you coming out.

David Osborn: It’s great to be with you, Brad Weimert. It’s been a while.

Brad Weimert: It has been a while. There are lots of things that I want to cover with you. You are known by many as kind of a real estate mogul. You’re top ten real estate brokerages in the world. You also have a couple of other facets that I want to talk about. Like, the mastermind group, GoBundance, that you have, a fund that you run. But before we dive into those things, how did entrepreneurship start for you? What was the beginning?

David Osborn: Yeah. So, I’m the son of a Green Beret colonel. And so, there’s a cliche that that’s a hard-ass dad to kind of live with. And it’s true. He was a hard-ass. And I grew up on farms in England. We moved all the time but my stability, I had a great uncle who had a farm in England, and he was a gentleman, Wall Street guy that had a 70-acre farm. It’s not like America. It was very good property, and he was the wealthy one in our family. And he’d have these dinners and he’d have 50 people around the big L-shaped dinner table at Christmas or Guy Fawkes Night. They don’t do Thanksgiving there. They go Guy Fawkes in England. And he held court and I thought, “Wow. What do I got to do to be that guy? Like, what’s going on with that guy? We’re living in the gamekeeper’s cottage on his property. So, even though we were moving all the time, this was the point of stability. We’d come back in the summers and we’d be in this English cottage that was on my uncle’s, my mom’s uncle, my great uncle’s property, and he was wealthy. And that seemed to be a common thread.

And then I would work on the farm and I’d get little jobs. My great Uncle Ted, he was good at giving me odd jobs, collect the eggs, or mow the yard, or just different things. And then he’d pay me. And I remember kind of liking the money like I was… My brother was an athlete. He was older than me. I was always on the second or third team. I’m like the JV team. And it kind of pissed me off but I was littler and I just didn’t have the aggression my brother had. But whenever I get those monies like I get a couple of pounds or a couple of quid, we call it back. And I was like, “Wow, there’s a certain like freedom I can get from that.” And I think early on I just started equating money with freedom. I was like, “If I have money, I’m more free.” So, I’m raised in a strict household with a very fun but also very aggressive father.

And then now I’m in high school, I’ve moved to America, my dad retires, I’m 14, he comes to America. And I’ve been in boarding school in England from age eight so I’ve been in a very strict environment but I come to America and I’m kind of a troublemaker. I’m a little kid so I’m kind of pushing. I don’t have a place to push my energy. I’m not good on the sports field. Not bad, but not good either. And so, I push back a lot. And I got kicked out of a school, and then I got kicked out of another school. Private school, so they’re easy to get kicked out of. But in the meantime, my best bud had a job bagging groceries. So, I went and got a job bagging groceries, and the same thing happened. I got that check, and I’m like, “Wow. Check this out.” I bought my first car. My parents split it with me. It was $1,500, so it was $750 I saved up and then they matched me. Now, I’m 16 years old. I got a car and I’m like, “How did I get this car? I got it with money.” And so, I think there was this thing all along of like, and I could work hard.

Like, I liked working. I was the second fastest bagger in the store, although no one knew that. I just knew that in my head because I was competing with all the other baggers. There’s one guy with really long arms that always. I was like, “Oh, he just beat me on that big like basket that came in.” And then I started a lawn mowing company. So, I’m like, now I’m 17 years old. I’ve worked construction. I went from bagging to construction, got fired from my first job. So, I got fired, kicked out of schools. So, I was just insulin. I kind of pushed back a little bit, and I pushed back against authority, probably to make up for the fact that I couldn’t push back at the house very much. Does that make sense?

Brad Weimert: Sure.

David Osborn: Then I was like, “You know what? I’m going to start my own company lawn mowing.” So, I did that.

Brad Weimert: Let me ask you a question on the authority thing. So, you pushed back on authority. That’s always an interesting question for me. And you just connected it to the father, right, the strict household. Do you push back on authority today the same way? And do you think it’s because is it irrational authority or is it all authority?

David Osborn: I think God has a good sense of humor in that I was so anti-establishment. God made me part of the establishment. You know, when you run a company with 4,000 people in it, you are the establishment. You can’t really rebel against yourself. Does that make sense? So, I’ve certainly learned to toe the line more. Also, being in leadership, you actually realize how hard it is. It’s very easy to sit in the back of the classroom and throw pieces of paper at the teacher and just bomb the class and make it difficult for everyone, and people laugh at you for doing that. It’s easy to be destructive, but it’s quite hard to build and run and manage something. So, I have a lot more respect for leaders now. I have a respect for how difficult it is. We all point fingers and laugh at the president or whoever runs our city, but actually, if you’re in that seat, it’s pretty freaking hard. Does that make sense? So, I have respect. I’m still innately a rebel. I’m innately like, I don’t like to be told I can’t travel or I can’t go places, or I have to stay in my house.

So, there are things that happened recently that I really struggled with, and I don’t trust authority, but I definitely have come back to the middle. When I was younger, I knee-jerk through against authority. I would speak back very quickly. I was just like a rebel without a clue, honestly.

Brad Weimert: Well, that was the point that I wanted to differentiate was if it was just a reference to authority in general or if it was what you’re saying doesn’t make any sense to me. So, I’m not going to do it because like today, I stopped sitting at red lights because it doesn’t make any sense. If there are no cars coming, I’m driving through the red light.

David Osborn: Nice. I do that sometimes. It’s not a rule for me, but if I’m running late and there’s no one around, I’ll pop that light.

Brad Weimert: It’s a rule for me.

David Osborn: And now that I have kids, I try to set a better example but for sure, I get it. I like it.

Brad Weimert: Yeah. And so, now you have to make sense of the rule, right? So, I don’t blow through red lights because that would be stupid.

David Osborn: That would be stupid.

Brad Weimert: I stop at all of them. And if there’s no traffic, I go because the…

David Osborn: The libertarian, man. I love it. It really doesn’t if you’re sitting on a country road and no one’s coming.

Brad Weimert: Right. What am I doing here?

David Osborn: It’s for the idiots.

Brad Weimert: Yes. And if I get a ticket periodically, I pay the ticket. That’s fine. And that’s the cost of having that rule set for me. I’m okay with that. But I kind of I think have adjusted to I grew up with the same mentality of f*ck authority. And over time, it sort of transformed into f*ck authority that doesn’t make any sense. It’s making choices that don’t make sense.

David Osborn: Yeah. I think being older, I toe the line a lot better. I have more compassion. I’ve had people tear my sh*t down in meetings and stuff where I’m like I’m just trying to lead you guys here and make this better for all of us and it’s not easy. And you got that little troublemaker bombing you in who I used to be. So, yeah, I’ve got a lot more respect. I understand how difficult it is. And I also don’t like rules that don’t make sense. I got a friend that never pays for parking. He just pays the tickets.

Brad Weimert: It’s my other rule.

David Osborn: Oh, that’s your other rule. Okay. I got a buddy like that too and I’ve started doing that a little bit myself, you know? But it’s so easy on the app nowadays but, yes, I will sometimes do that as well. But I dig that. Yeah. I’ve got more respect for authority. I just know how difficult it is. I mean, think about this. The day you’re elected president of the United States, 50% of 350 million people hate your guts like right away. Maybe not all of them, but a good chunk of them and that’s what life’s like. So, I see more of the nuances. When I was younger, teacher, anyone talk to me from a position of authority, my first reaction would be, “F*ck you. Who are you to tell me what to do?” But I’m not like that anymore. So, yeah, I’ve changed.

Brad Weimert: That’s helpful. Okay. So, entrepreneurial journey, you started doing your own thing, lawn mowing, etcetera. You’re 17, 18. You’ve got a taste for money. Also, out of curiosity, I just want sort of a benchmark. You referenced your uncle. Great uncle?

David Osborn: Yeah. Great Uncle Ted.

Brad Weimert: As wealthy. Do you have any idea what that meant?

David Osborn: I would guess for him, it would be a guess. The farm was worth a lot of money. It was in a high-end area. So, imagine a farm in Connecticut or if you don’t know Connecticut, like just in a really close to town. And then he was working as a stockbroker, probably making a few million in today’s money per year. My guess he was worth somewhere between 15 and 50. I know that’s a big range but I was 14 years old, so I don’t really know.

Brad Weimert: Got it. Okay. That’s helpful.

David Osborn: Yeah. So, that’s wealthy. He had two Jaguars. He went to the city and then he got cancer and died. And I remember he was pretty bitter about that, you know, angry at God that he got cancer at 70-something years old. So, I never really got the mentorship as I grew older. And my dad was a soldier and my dad was just tough as nails and hard as nails but I always remember looking at my dad and Uncle Ted and going like, “I think I’d rather be Uncle Ted.” Does that make sense?

Brad Weimert: Yeah, totally.

David Osborn: My dad really wanted me to be a soldier. He’s like, “You could be a general,” and I’m like, “I don’t want to be a general.” I just want to go make money so I don’t have to answer to anybody ever again. Now, yeah, I would say he was a good mentor for me. And then I came to America. Long story short, I got into sales, which was cool like because sales also, you don’t really have a ceiling. My first job was computer sales. Walking into a skyscraper and knocking on every door and just trying to get them to buy computer systems from my company. And then I got into real estate sales, and that was even better because there’s no limit to how much. Well, there is a limit, but you can make a lot of money in real estate sales.

Brad Weimert: Yeah.

David Osborn: And then after three years of that, the company I was in was very small, Keller Williams. It was expanding. And they were trying to sell franchises and I got bored of selling. So, I said, how about if I bought some franchises? And they said, sure. And so, we got into buying franchises. It was really fun. My mom was also a realtor at the company, and she was my partner. And growing up, she was just a housewife. So, she worked at MI6 as a secretary like Moneypenny. And then she got into real estate, like in her late 40s or early 50s, and just started killing it because she’s a very hard worker, made way more money than my dad ever did. And then, yeah, so we partnered up. She was great. I mean, she’s still great. She’s 89 years old and would be a fun interview for you still today.

Brad Weimert: Oh, I love it. I love it. Maybe that’s chapter two here. So, the jump from sales into actual entrepreneurship is a big one.

David Osborn: It is.

Brad Weimert: And it’s one that I think most salespeople think they can do and most fail at doing. Or they do in a very mediocre fashion. You might be a killer salesperson and a horrible entrepreneur because you need a lot of other skills.

David Osborn: Well, the story of life, Brad, is that everything that gets you to a certain point starts hampering you to get to the next point, in my experience. Maybe not everything. Let’s say work ethic’s useful. Having an ability to set goals is useful but salespeople, it’s all about you, and it’s all about you talking and persuading and influencing. And the better you are at that, the more money you make. But in a business, a really great business, it becomes about other people. So, it’s no longer about you. So, there’s a saying I’ve always loved, “I do it, we do it, they do it”, is how I’ve created my success. So, the reason I have three businesses, all three currently making me over millions of dollars a year to me that I’m not having to work that much on and I am paying attention, but I’m not deep in it is because I have learned how to work through very talented guys. Each person that runs one of those businesses earns seven figures themselves, and they run that business and that’s “they do it.” But a lot of people we do it is where you evolve to that but a lot of people see we do it is really I do it with a lot of little we’s following around, picking up the pieces.

And so, that’s been my entrepreneurial journey. Now, I do it. The reason salespeople I think struggle is just they get so stuck on the I do it. They know how to work hard. They have big personalities, and they’re just used to fixing everything and dealing with everything themselves. And that becomes an incredible weakness in building a larger entrepreneurial operation. You can build to pretty good, pretty big, and then also doing that kind of living. You’re a big personality. You tend to spend a lot of money on a lot of stuff. And a lot of those guys don’t have much left over. They have a business that from the outside looks big and shiny. They’re driving the pretty car. They got the pretty house. But ten years down the road, if it all stops, they got to find something else to go do because they haven’t built anything. They haven’t built any wealth or value creation or things like that.

So, I see that a lot in my business because we have so many amazing realtors that are just badass like they have more personality than me, more energy than me. They’re just super impressive humans but they just don’t drive their car very well and there’s a lot of damage. There could be like tax liens. They don’t pay the IRS. They don’t really understand the net value of money. They only understand the gross, gross volume, gross sales. And so, that’s a very interesting thing. That’s very interesting when you see a person you consider more talented than you, but they keep not performing at a higher level than you because they’re missing a little piece, which is maybe the tactical piece. I don’t know. It’s interesting.

Brad Weimert: Tactical mindset, ego. What gets in the way of actually making those jumps to the next desire, jumps to the next like true desire to the next level? I don’t know. I think it’s different for different people.

David Osborn: Yeah. People say it’s what, power, money, or fame. Right? Those are a version of the three things. So, I think a lot of people want fame, so they want to be known. They want to be significant.

Brad Weimert: Especially today.

David Osborn: And that’s the opposite of, to me, it’s not the opposite. It can help wealth but it’s nothing to do with wealth.

Brad Weimert: It can be at odds with it.

David Osborn: It can be add on. It can accelerate your strategy towards building wealth. So, if you’re famous on Twitter or now X and you’ve got all these followers and you drink the right drink, they pay you for that. So, it’s really useful. If you’re famous and you have an interview with someone and they think you’re famous, they’re more likely to want to be in business with you. That’s additive. But generally speaking, you still have to have that tactical, which I think freedom and possibly power, although I’ve never been super driven by power. But freedom requires tactical strategies. Like, my goal was to have more money coming in without me working than I needed to live. That was my number one goal, and originally, I wanted to do that through residential real estate investments. So, originally I was going to buy ten properties, pay them all off, and that would pay me $100,000 a year and I would never have to work again. Because I was young, I thought that was a lot of money.

Brad Weimert: Yes.

David Osborn: But then it eventually became businesses. But it was always like, okay, how do I get to where I don’t have to work anymore? And I think a lot of salespeople, they love the work, they love the grind, they love the adrenaline rush, and they just stay in that space.

Brad Weimert: So, through this transition of and I want to get a little granular, but salesperson to franchised Keller Williams office is like of the first that we’re doing it for Keller Williams to the current ecosystem where you’ve got all sorts of things going on. The I do it, we do it, they do it, moving from one level to the next is a challenge. Like you said, what gets you to one place frequently is something you need to let go of to get to the next place. At what point, and you can give me whatever metrics you want, headcount, revenue, whatever, income do you feel like you move from we do it to they do it?

David Osborn: So, the first move was from I do it to we do it. And then I said it before, I’ll say it again. Most people view we do it as actually I’m doing it and they’re supporting me and doing it. But that’s not we do it. That’s still, in my opinion, I do it. So, there was a moment where I’d open four franchises and I was trying to do it all through weak managers, and I had like a mini nervous breakdown. In hindsight, I would call it an identity crisis. So, my identity, I was really ambitious but who I was showing up as wasn’t going to hit the goals that I had. And I tried to work harder and harder. Everything from building the cubicles to fixing the computers to recruiting the managers, recruiting the agents. I was trying to do it all, and I just couldn’t. And I was failing and I had a manager that was dealing drugs and another that was an alcoholic and I was just like kind of broken inside. And it led to shingles and stress. And at the same time, I was being trained in the company about how to hire. They were teaching us how to hire talent.

They were teaching us that talent leaves clues. People that have been successful tend to continue to be successful. So, if you’re asking someone, “Tell me your life story.” Like, I’m going to light this match and I want you to tell me this story before this match burns out of your life story. And if it’s like ups and downs but like a leadership-based story, I was the captain of the football team. And then I start a business, and I failed and I crashed and burned but then I got up and I got into sales and I became the top salesperson, that’s a person that is probably going to continue to succeed. And if you meet a person in their 40s and I’m still living with my mom and smoke weed every day and I’m eating apple pie, that’s probably what they’re going to keep doing. It is possible to change later in life, but mainly your story leaves clues into who you are. So, that’s what we were being taught. And then I noticed that I had four managers and one of them, each office performed at the level of the skill set of that manager.

So, if I had a mediocre manager, I had a mediocre business. So, I’m learning all this while experiencing massive stress. And the stress, I think, was that I was doing more than I could. Like, I have a good engine, I can work hard, but I can’t work 100 hours a week for ten years. Some guys I know can. I know that… Who’s that real estate guy out of Florida that has…

Brad Weimert: Cardone. He’s a client of ours.

David Osborn: Yeah. And who’s that other guy up north that’s in Philadelphia or whatever? It was Wine.com guy.

Brad Weimert: Gary Vee.

David Osborn: Gary Vee. So, those guys work incredibly hard. And I saw them in a little podcast arguing who it worked harder. I wouldn’t be in that competition but I did work very hard, as hard as I could work. So, we’re talking 60, 70, 80 hours a week for ten years. But I reached my breaking point. I broke and then I kind of rebirthed myself as a new person, and I just stopped doing all the little things. I stopped doing all the insignificant things. And I just did the most important activities every single day. The richest guy I knew at that time, I asked him, “What’s your secret at success?” He said, “Write down the seven most important things you got to every day and do the top three. Let everything else fall by the wayside,” which, by the way, is something Ford said. Way later, I read it in another book. So, I started doing that. I prioritize everything ABC and I just try to do the top stuff, and all of a sudden my results got better, I got happier, and life was better.

Brad Weimert: All right.

David Osborn: You sound like you’re groaning.

Brad Weimert: I am groaning. So, as one that is currently navigating that and I’m way down the path but when you are in sales and when it is I, you get the rush from doing.

David Osborn: Of course.

Brad Weimert: And when you want to jump to management and leadership, there has to be a change in mentality around in a forced constructed, it doesn’t just happen. You need to figure out how to get a rush or happiness or satisfaction not from doing but from something else. How did you bridge that gap?

David Osborn: Well, again, I have this internal drive for freedom. Maybe that serves me more than power or significance. So, if those are the three things, fame, power, and money, freedom and money meant to me. So, I started just looking at my bank account and my game became this internal game of how much wealth can I build? I was in a mastermind with Dr. Fred Grosse. I met this guy, Pat Hiban, who became one of my best friends and my peer partner. We held each other accountable. He was the number one RE/MAX agent in the world and then the number one Keller Williams agent in the world shortly after that. I recruited him over. And so, we’re ‘97, ’98, I have kind of this breakdown, as I recall. And then ’99, 2000. It’s only in 2001 I make $1 million in a year from all these businesses I’ve created, maybe $1.1 million I think it was.

Brad Weimert: In the businesses at that time, or the…

David Osborn: Franchises and real estate. I bought some real estate, but 90% of franchises because I built… So, if you remember, there was the crash of… No, no, I started in the business in ‘92, and we had this big rise all the way up until like 2005. So, I really got in a good time, too. And the timing is very important in life, too.

Brad Weimert: In real estate.

David Osborn: In real estate especially. So, I’m opening all these franchises and I’m struggling and I have bad managers from sort of ‘96, ‘97, ‘98 and I have my kind of mini nervous breakdown or identity crisis. And then I start hiring good managers, and I’m being taught how to hire them. And I’m noticing the matchstick story. And then I’ve started all these businesses that were mediocre but then they start getting better. So, in 2001, now I’ve got like six and they’re all starting to make money, and I am the majority owner of all of them. And I was very good at bringing in partners and equity sharing but I would always be 50-ish percent, 60% of them. And so, now they’re all let’s say they’re making 200,000 on average, or 300,000 on average and I’m 50%. And suddenly, I make $1.1 million and I’m like, “Wow.” This is from like eight different sources of income. And then I’m really learning the game of people. So, that’s what my game became. It wasn’t like the rush of that other world. It was the rush of performing and building businesses that made me money.

And it was very lonely because I couldn’t really talk to a lot of people. I could talk to the other Keller people that were doing well but they also a lot of them because they’d been burned before, they kind of stopped at one or stopped at two. And I hadn’t been burned really badly in business then. So, I just kept going. Like, at one point I wanted to own 100, and once I got the talent piece, I was like, “I can have as big an empire as I have talented people working for me.” I think also, Brad, being a younger brother and the youngest of three kids and a fairly aggressive family, maybe I just didn’t need that front-of-the-room pop as much. I could do it, but I didn’t seek it. I mostly thought like, “I wonder how many of these I can create.” And it was a very internal game.

Brad Weimert: And so, this is the jump from I to we.

David Osborn: This is the jump from I to we.

Brad Weimert: And was there friction moving from we to they?

David Osborn: Yeah. The biggest friction is feeling worthy enough to have a business that you’re not really paying attention to, that you make a lot of money from. I mean, I pay attention to the numbers and what was going on with the business, but I wasn’t in it every day. I didn’t know which agent was mad at which agent, and what deal was going bad and what deal was going good, and whether the copy machine worked. I just hired somebody to do all that. And then I paid attention to the numbers and the relationship I had with that person. They’re holding them accountable to perform and making sure I had a bench of people to replace them if they burned out, and then learning how to put the contracts in place to protect me from competition and from people stealing my people and things like that. So, the harder part I think was learning all the nuances of how it can go wrong and right.

I had one business with a partner. We had zero paperwork. We just started an LLC together. It’s 50/50. And then it went bad. And we don’t even know how to get out of business. So, we have this mediocre business making $60,000 a year. We don’t like each other, and they sue me. So, I’m like, “Well, screw you, I’m going to sue you back.” So, we get in this big fight and a year and a half or two years and $150,000 later, I buy them out for what I’d have probably paid on day one. And so, these are the kind of things I started learning. And then when I read their deposition, this was the most eye-opening part, I thought they were in the wrong. And then I read their deposition. I’m like, “Well, this is pretty much what happened.” The only difference is I thought they weren’t doing well at $60,000 a year. I thought we should be making 200. And they were quite happy making $60,000 a year. So, I did apply pressure and I did replace the manager, and I did try to drive that business up. And in their opinion, I was disrupting their business.

And so, I’m not saying they were right. I’m just saying I was like, “Oh, it’s just two sides to the story.” So, I learned to put the contracts right so that I would have control of the business and I could buy the people out if I needed to. I have compassion for other people. I understand most people are doing their best. I try to always treat people well but I learned how to put the contracts in place that enabled us to get out of business more quickly if things weren’t working with a payment.

Brad Weimert: Yeah. Reminds me of the sentiment that is Gary Keller, I think, which is referencing contracts not as agreements but as disagreements because the time that they’re relevant is only when you have a disagreement.

David Osborn: That’s right. That’s right. And it’s all about like thinking about the divorce, right? So, if you do, people have these horrible bloody divorces all the time because they didn’t have a prenup. But if at the beginning when they loved each other, they’d said, “Hey, honey, let’s sit down and discuss what would happen if we divorced. Who would raise the kids?” Then that’s the time to do it and that’s what we do now in the beginning of all our operations. So, you said, how do they do it? So, that was one learning is how do I structure it so that if I have they, if they’re performing really well, how do I reward them? If they’re failing, how do I get out of business with them? And if they just want to move on and they’ve kicked ass for us, how do I take care of them and pay them well and look after? Because I really believe in looking after people. And some organizations you see they get bigger and bigger and they stop looking after their people. And I think it’s the beginning of the death knell of the organization. So, take care of the people, but have the cards in your hand to do so.

And then on the other side of that, it’s learning how to really trust other people to do a job for you, let things burn so that they fix it and you don’t fix it. The one-minute manager, you remember that book? I mean, it’s an amazing book. So, the guy brings him a problem.

Brad Weimert: Is that Ken Blanchard?

David Osborn: Yeah. He’s like, “Boss, I have a problem. The sales machine isn’t working or the manufacturing machine,” and the boss doesn’t solve it for him. He sits there and he says, “Well, Brad, what do you think you should do?” He goes, “I don’t know. That’s why I came to you.” He goes, “Well, why don’t you think about it and come back with your three best ideas on how to solve that problem?” The guy goes back. He comes back. He’s like, “Okay. What of those three ideas, which one is your favorite one?” “Okay. This one.” “Okay, go try that.” That’s one-minute managing. Most people swoop in and fix it all for them. And guess what? Every time you solve someone’s problem, you took their job back. And if you do it too often, they’ll quit thinking for themselves and they’ll start asking you. And my experience is and again, this is learned and I didn’t start there. I loved being the significant guy that could come in and solve the problems. “Oh, that agent’s about to leave. Let me swoop in and buy them back or fix it.” But now it’s more like let it burn and you are going to learn. If you’re the right person and I let you burn something in my business, you’ll be that much better next time. And it’s the way I kind of pour into people is by letting them fall on their faces.

Brad Weimert: I love this. So, first off, we internally use that structure and we refer to it as 1-3-1, which is one problem, you better give me three solutions and then tell me which one you want to go.

David Osborn: Beautiful.

Brad Weimert: That’s how we start. But if you come to me with a problem…

David Osborn: You better have a solution.

Brad Weimert: We have a problem. Yeah. And the problem is not what you think it is. It’s I’m not thinking for you.

David Osborn: That’s great.

Brad Weimert: But it is something that consistently needs to be managed, right? Because you have to also teach your team that that is how we behave. And like you said, as soon as you slip from that structure, it goes away entirely, and then they go back to leaning on you for the solution.

David Osborn: That’s right. It’s very easy for people to lead or follow. And I think we create the culture which causes them to lead or follow them. And I see all these guys in the company that like they bought a franchise and then they’re the big dog in it. They hire a manager, but the manager really is that little… This is the we do it where they’re the little we. And it’s so funny to me. I’m like, you bought a business so you could earn money and not work but your need for significance is forcing you to stay in that business and be the man or the woman, and you’re not really giving yourself the chance to multiply and spread out.

Brad Weimert: So, let me give you another reason that that might happen. It is scary to watch things burn when you know you can put the fire out.

David Osborn: It is.

Brad Weimert: And I know for me, personally, a big part of not wanting to let things burn is and was my relationship with money and growing up with this mentality of money doesn’t grow on trees, as opposed to money as a lever that can be used for different things, and you can always make more of it. At what point in your journey did you establish a relationship with money where you decided it’s okay to watch it burn in the name of somebody else growing?

David Osborn: That’s a great question. I think I had a certain abundance mentality already coming in. My parents definitely were the same like, “Money doesn’t grow on trees. Turn the lights off. Are you trying to air-conditioner America?” like all the things. My dad and mom used to see how far into the summer they could go before they turned on the AC. I know it’s murder. We’re like, “It’s March. Let’s set it at 63.” It’s probably right now at 67 in our house. But somehow along the way of my mindset, maybe again the rebel in me was like, “Well, screw you guys.” But there was a little bit of me that was like abundant. And then the other thing is in Keller Williams you had to have multiple franchises. We owned the region as well, the master franchise. So, we had to sell franchises to stay in our development schedule to keep the region. We were building it for Keller Williams as they were pouring systems into us. I mean, the company was nonexistent. It was nothing. People thought it was a paint company. And then we went out, took territory from our competitors, got great training from Keller Williams. And I wasn’t good at selling franchises, so I ended up buying them to stay under my development schedule.

Brad Weimert: Oh, wow.

David Osborn: I was young and I was goofy and people didn’t believe in me enough to buy them. So, I bought the first five or six. And then I got better selling them and I was more credible so then it all kind of fell in place. But now, if you imagine I have six businesses that are going to make 250,000 a year, and I’m 50% of them.

Brad Weimert: Each?

David Osborn: Yeah, each one. It’s easier for me because one of them burning isn’t the end of the world because I got the other five and they’re all spread out. So, it’s not like a fire from one is going to spread to the other. So, that’s part of it. I think the second part of it is, honestly, I just had a little bit of a lower level of talent than maybe you’ve got. Like, I see guys that jump in, I sometimes would cause more problems than I would help fixing it. You know, I remember one time asking my…

Brad Weimert: I’m sure I do too.

David Osborn: Well, I remember saying to my manager, “Why haven’t you signed the lease?” And he goes, “You told me to send you the lease and you were going to review it.” And I go back to my bench, and sure enough, in my inbox is this 80-page legal lease that I said I wanted to read for some strange reason, even though I was a C student that got thrown out of three high schools. So, I learned there that I was often the bottleneck in my organization. So, I let it flow. So, I let things go, let them happen, let the people fail, let it burn. But having six was easier than one. All my eggs weren’t in one basket. I was in one basket called Keller Williams. But it wasn’t like I had one giant shop that the problem could put me out of business, which would probably stress me more. And then I watched my manager show up and I had this like proving ground of like, who’s good, who’s not? You could do the same if you had a sales force. And then I’d be like, “Oh, this manager’s really good, and this manager is really bad.” And I’m tired of talking to this manager because the energy would drain me.

Like, I could always tell if I sat with somebody and I felt depleted, they weren’t good leaders, right? That’s a bad sign. But I would take my good manager and I’d say, “You now have an opportunity. You’re leading this office. Here’s your guy. Train him up.” Some people have an amazing capacity just to pour into. Let’s say people are ranked on a 1 to 5. Some people have an incredible capacity to pour into a 3 and make him a 4 or pour into a 2 and make him a 3. I don’t have that capacity. I need a 4 or a 5 that I’m dealing with. But if I take a five and I put them over a 3, they might make that 3 a 4 or a 3.5, but then I don’t have to deal with it and then I could create an opportunity for that next guy. So, came this game of creating opportunities, and I got so committed to it. I learned this concept too. And by the way, there’s also risk. Sometimes you take your best salesman, I think you know this, and you make them a manager and they suck as managers. Because all they know how to set production and then you f*ck up the relationship because it’s really hard to send them back into sales.

Brad Weimert: Yeah.

David Osborn: So, it’s kind of like reading the people and having an intuition and like paying attention. But today, like, I also learned from another consultant, if I hire a guy at 500,000 a year, what am I really risking? So, you’d think that’s a big freaking salary. Why would I pay him 500,000 a year? But the truth is, in about 90 days, I’m going to know if they’re any good or not. So, divide 500 by 12 is about $60,000 a year. I’m risking $180,000. I would risk that all day. You spend that on the build-out of this office space. I spend that, yeah, on my jet fuel in a third of a year.

Brad Weimert: Yeah, I think that that’s an important… Look, running the numbers, period, is an important exercise for entrepreneurs to do at every stage.

David Osborn: That was a hard lesson for me to learn. You’re 100% correct.

Brad Weimert: Yeah. Until you actually, you have to get out of the way of saying, “I can’t do this,” right? Just get that phrase out of there. And then you also have to commit to at least let me do the exercise to see what it looks like. Because you’re right. You get scared by can I afford a five…? And it depends where you are on the journey but can I afford a $500,000 a year person? And then what’s the risk mitigation there? And as you said, it’s three months.

David Osborn: Yeah. I remember I was hiring my first assistant after going through this training about your life is directly in quality of the five people that report to you every day, like the quality of your business life is going to be directly proportional to the quality of the five direct reports you have. So, there was this girl I wanted to hire to work for me. And I remember I wanted to spend, it was going to be my first personal assistant, and I think I was making $100,000 in my businesses at that time. And I wanted to pay 25 and she wanted 45. So, I said, “Okay. Screw it. I’ll do it.” And I took a $20,000 pay cut. I went down to 80. She’s almost making as much as me. But she had administered 300 doctors in a hospital. She was a badass. I mean, she was amazing. And she took my world and put me in the right place. And I began to learn like all I need to do is be in front of people, opportunities, and create vision. So, talent, opportunities, and vision, that’s my gift zone. That’s all I need to do. And if people can take everything else off of me, our whole world is going to get bigger and bigger.

And then so I find an opportunity to build something. I find talent that can run that thing. And then I keep creating vision and paying attention to the numbers to make sure the architecture is in place for that to grow. And this woman, Kelly, she was just incredible. She just I’d say everything you do, I want you to put it in an operations manual. And she wrote this whole operations manual. Because the other thing I’d seen is top performers get held hostage by their assistants. So, I had to write down a one-pager, everything she did. And then I’m like, “Oh, if she ever leaves me, here’s the job description for the next person.” But she did that for my meetings, my training events, how to run the market centers, a regional operations book, which Keller Williams then copied about half of them and made it part of their operations, which was one of Gary’s genius, is taking the things from the field and putting them back into the organization. So, yeah, it was great, man. And then it’s become all about the people. So, to this day, like I would say, the number one most important thing I think in building an entrepreneurial operation is great people.

Brad Weimert: Okay. So, recap here is I asked you about we to they and that movement and some of it is in your head. And then we talked about kind of when is it okay to let it burn. And you did have a different structure, but you had six entities. And basically, you said if one of them burns, it’s not the whole house.

David Osborn: It’s not the whole house. I’m giving that manager an opportunity to figure stuff out.

Brad Weimert: And it’s 15% of the whole portfolio.

David Osborn: Correct. Because today I have 14. So, it’s less than 10%.

Brad Weimert: Yeah. And so, I think for anybody listening to it and thinking about it, it’s if you’re putting the whole house at risk, maybe you’re still in the space of I or we.

David Osborn: Right, right, right, right.

Brad Weimert: Right? It’s not effective delegation. It’s abdication at that point. And you need to know when to have that risk.

David Osborn: And there is the time to fire the guy. For me, there was like one bad situation with an agent that the agent was going to leave, which is kind of like a burning fire is one thing. If five agents come to me and say the manager is playing favorites and they’re referring stuff to their husband, and there’s like some weird stuff going on. So, I’m not suggesting I let every fire burn unchecked. But I think there’s a lot of fires like there’s a leaky roof or the copier is broken and they got to learn how to deal with a copier company. Like, those are the kind of things you just got to let them fix it.

Brad Weimert: Yeah. Okay. So, I, we, they. I love that framework.

David Osborn: There’s another one we didn’t really touch on which you hit on just now that I forgot. Like, the other part is me mentally, not having to apologize to my people for doing what I want to do. Like, there was a part of me who always wanted to be seen as working harder than them or like I would tell them even my assistant sometimes. I have appointments this morning when I’m actually golfing like I had that imposter syndrome. And there was a part of me that, like, was embarrassed when I first bought a private plane. I was like, “Don’t tell anyone.” I still can be a little nervous around that. But the truth is you just got to live your life and not make apologies to other people and not worry what anyone else thinks about you. Maybe that’s easier for you. I think it’s easier for some than others, but I remember in my world there was a part like, who am I to deserve the success? Why do I get to go play golf today? I should tell everyone I’m working and almost like living like an assistant instead of like the king. Does that make sense?

Brad Weimert: Yeah, 100%. And I think the irony in that, and by the way, I very much am like that too. And I think the irony in that is that what humans relate to most is authenticity to yourself. And you can in sales, the expression is you can say anything with a smile. But in life, you can say anything and do anything as long as you just f*cking own it. The moment that you’re bashful, ashamed, and dip your chin down and look down, that’s the moment that it gets weird.

David Osborn: It is weird. And it’s weakness. And it’s not really living into your full potential.

Brad Weimert: Agreed.

David Osborn: And it took me a while to learn that. And I think as I’ve learned it, my life’s got bigger and bigger and better and better. So, yeah, it’s an interesting thing life. You look at a guy like Donald Trump and he just does whatever the hell he wants and he’s still hanging in there. Or Elon Musk, he’s a perfect example. He’s got every reason to shut up. He owns publicly companies like X that’s going to lose subs. He just does whatever he wants and he’s done just fine. Yeah, that’s been a lesson I had to learn as well.

So, I had to become the person. And then there’s another piece like, you just have to be willing for the universe to show up through you in a big way. Does that make sense? Like, I don’t think it’s me. It’s me getting out of my way as much as anything. Like, I believe there’s got to be an Elon Musk. There’s got to be a Richard Branson. I believe that when a tree is planted, it just fricking grows and it becomes a giant tree. And it’s never like thinking as an acorn. Like, I wonder if I’m too big of a tree, or I wonder if I– I think, for me, a lot of what I’ve had to do is just getting out of my own way. And then I said earlier, vision, people, and opportunity. The vision is just having a massive vision of what’s possible and not really worrying about how it’s going to show up. Just let it show up. Does that make sense?

Brad Weimert: It does, it does. And some of it’s abstract, and I think that that’s the challenge for a lot of entrepreneurs, specifically A-type people, like me. They’re like, yeah, yeah, yeah.

David Osborn: Right.

Brad Weimert: But how the f*ck does it happen, right? And so, on your journey and some of these, I think, the stories that you’re telling about your path are really helpful because it shows people how it happened and some of the mindset behind it that helps facilitate it.

David Osborn: Right. Well, I think the thing is the drive is to be crazy ambitious. Like, I was very ambitious for financial freedom. Very. So, then if I’m creating this vision of, like, I’m going to be at 100 million net worth by this date and I’m going to have 10 million a year in income and I’m going to have five guys that report to me to make a million a year, that seems abstract because it’s not specific as to how, but it’s a pretty clear, driven vision that I had for years and years and years. And by the way, when I’m telling people that I want five guys that make a million a year and there’s some guy that thinks they should make a million a year, I’m kind of putting something out there in the universe that might attract talent to me, and I realize it’s not, okay, we’re going to start a payment processing company or a real estate company and we’re going to add 500 agents and then a thousand agents. Like, it’s not that kind of scaffolding, but it’s still a mental scaffolding and a mindset that you’re willing to live into.

Who was it that said, be bold, there’s genius in boldness or something like that, and if you try bold things, mysterious forces will come to your aid? I mean, my experience is that it might be airy fairy. It might be true, true, and unrelated. But the more I’ve lived into this bigger vision, the more talent has been attracted to me, the more I’ve been abundant and let go of little things, the bigger my life’s been permitted to become. So, I don’t know. It is weird. It is a bit abstract.

Brad Weimert: Yeah. But I also think to that point, you gave a couple examples of how it might work, right? So, I think that a lot of the time, an exercise that I like to go through is for those abstractions and for those things that are airy fairy. What is a rational reason that it might happen? And that exercise, for me, helps me get along with a wider group of people, first of all, because I stop shooting down somebody’s belief system just because it’s not directly in line with mine, and it helps me understand it. So, one, to the point of being bold, one reason could be you just do more f*cking reps. You are doing more when you’re putting yourself out there. And so, it’s possible when you do more, you’re more likely to come across the right opportunity.

David Osborn: And I think, for me, the vision meant goals every year like 60, 70 goals, a 5-year vision, a 10-year vision, and a 40-year vision, that’s compelling in and of itself. And the goals would be around health, nutrition, intellectual, personal growth. One of my goals is always to speak 20 times a year, do 20 podcasts. And then one of my goals that was the most driving in business, have five guys report to me that make a million bucks a year.

Now, one day, I’m teaching in Canada to a group of people and I said to the group, “I’ve got two guys so far and I’m looking for the third.” And this has been a mantra of mine, five guys who make a million a year, because you know what happens when a guy makes a million a year, Brad? How much accountability do you think you need for a person that makes a million a year? Zero. Nobody makes a million a year that isn’t freaking driven. You don’t have to call him. You know the guy that makes 75,000 a year? Hey, where were you Monday? Oh, I have a doctor’s office. You were partying all weekend, you dumb lying, son of a gun. You just didn’t come to work because you’re f*cking lazy. But the guy that makes a million a year wants to make 5 million a year, and they’re driving, right?

So, anyway, I do this speech up in Canada, and this guy comes up to me afterwards. He goes, “I’m number three,” and I don’t know what he’s talking about because I already forgot what I said. I’m like, “What are you talking about?” He’s like, “I’m the third guy that’s going to work for you and make a million.” And I used to say, I pay them a million, they make me 2 million, because it’s a covenant contract. That’s how it works. We’re going to build a business big enough for there to be 3 million in profit. They’ll get a million and I’ll get two. So, I make $2 for every dollar they make, but I create the opportunity.

So, he comes up to me and says, “I’m number three.” Well, long story short, the entrepreneurial mastermind business that I own today, he was influential in building it. And I think I made $2 million from it last year. Now, we were partners for a while and he wanted to be bought out, so we paid him a very fair price. He made hundreds of thousands of dollars. And he’s doing his own thing, and we’re still friends to this day.

But I just thought of that as you were saying, it’s abstract, but it could create opportunities. There’s a lot of other pieces in that story, but without getting lost, that’s the bottom line of what happened. He came up to me and said, “I want to be in your world.” We built a friendship. This opportunity showed up. He’d been with Tony Robbins a long time, so he knew how to kind of step into that opportunity. His name is Rock Thomas. And then that business got created with some other partners. And today, it’s 13 million last year in revenue, on its way to 19 this year.

Brad Weimert: I love it. So, that’s where I want to go is the I, we, they, at some point and this is both kind of a wealth creation moment and a lifestyle moment and also, a vision and goal setting thing. So, you talk about 10 years in putting in 60, 70, 80 hours a week for 10 years. And this is all around building out the Keller Williams ecosystem largely to produce income. But you had this idea in your head also, you need a mechanism to pay for all your expenses without income. And so, you start investing in single-family homes?

David Osborn: I started investing in single-family homes and graduated to multifamily homes. And that would be the fourth leg of my world, which is kind of like a family office, which everyone’s heard of now. When you make a bunch of money, you got to put it somewhere and that becomes a business in and of itself. But really, it was really just Keller Williams franchises and then master franchises. So, I ended up buying five master franchises. I was deep into that ecosystem. I loved it. Still do.

But we were being trained every day to how to build these franchises. The best ideas in the field would go up to corporate. They would embody them and put them back out to the field. We were helping one another. We were running around the country taking territory. So, that was where the majority of that wealth was coming from.

Brad Weimert: And what’s your income like at this point?

David Osborn: I mean, it’s eight figures, like a good year. I think the best year I ever had was 16 million in a year. And it can drop as low as 7 million. It’s not very good right now because of the interest rate.

Brad Weimert: At 2024, February 20th right now, yeah.

David Osborn: But I still think I make pretty close to 10 million. We’ll see this year. And everything has a cycle. And it’s just been such a fun journey. But yeah, anyway, keep going.

Brad Weimert: So, I ask because I think that it’s really important for some people to anchor to a specific thing and say, “Hey, now is the time.” And for other people, it’s not. And by the way, your number for when it happens isn’t everybody else’s. But the question is, at what point did you say, “Hey, I need to start diversifying or splitting my focus to something else”?

David Osborn: So, really, it was 12 years. I can tell you because I started in real estate in ‘94. I got into sales. For three years, I worked my ass off. Then at the end of ‘96, really beginning ‘97, I went up to Dallas, started opening franchises. I came back in ’06 to Austin and went to work for corporate. And really, it was almost like 15 years of just working as hard as I could, but then…

Brad Weimert: Why did you do that? Why did you come back and work for corporate? You had this whole empire of running franchises, regions, and you go back and work for f*cking corporate.

David Osborn: I know, I know, I know.

Brad Weimert: And you’re making 10 million a year or something.

David Osborn: Back then, it was probably more like 4.

Brad Weimert: I mean…

David Osborn: Yeah, it was a lot of money, but I had great people. And so, I was continuing to follow my path of creating opportunity for people. And I hired a guy to kind of run it. So, now, I was stepping back from running the 14. So, if you think of it that I always said there’s individual managers, but I’m kind of running the fleet. I would say like, “I’m the admiral of the fleet.” People say, “Thank you for giving me the opportunity.” And I’d say, “Well, you shouldn’t thank me because you’re the captain of a battleship and I’m the admiral of the fleet, and we’re going to go into battle. And if you get sunk, if you get killed or lose, I’m going to replace you as the captain of that battleship. But if you win, you’re going to get medals, honor, glory, and opportunity. So, that’s it. Don’t thank me. Just go perform.”

But then I replaced myself as the admiral, so I had a new admiral running the fleet. I wanted to open a mortgage and title company. Keller Williams hired me as the President of Core Services to do mortgage and title. So, I was figuring, they’ll pay me. I created a plan where I could make a million a year if I hit my numbers, and I figured they’d be paying me and I would be learning what I was trying to do in North Texas anyway. This was throughout the mortgage and title company.

Brad Weimert: Got it.

David Osborn: Then, I’m there.

Brad Weimert: Instead of just doing it all on your own, which you had to do anyway.

David Osborn: I had to do it anyway, and I still had a team in place to do it through. We had a mortgage company up there. But this is ’06, you know what happened in ‘06, right? ’07 was the big crash. So, I’m back in Austin.

Brad Weimert: I might have some battle scars from that.

David Osborn: Yeah, that was a tough one. All of that stuff crashes. But my dad got cancer, my fierce Green Beret father. So, it’s like almost a God thing. God brought me back to Austin. I wasn’t fit for corporate because in my world, I was used to telling people what to do and they did it. And in corporate, you tell someone to do and they go ask– I was the President of Core Services, but it didn’t seem to matter that much. There was a CEO or somebody else and like, it would all just get lost in this atmosphere of that world for me.

I’m sure when Gary says to do something it gets done and maybe, the CEO of the time, but– and for me, it was just confusing. It was a murky place and there was politics and things that I couldn’t really grasp. But then my dad gets cancer anyway and I want to nurse him. So, ‘08, he’s dying of cancer and I basically work 20 hours a week. First time, I just shut the brakes down on work in 15 years.

Brad Weimert: Wow.

David Osborn: And from ‘94 to ‘08, whatever number of years that is. And then I was like, I’m going to be with my mom, I’m going to be with my dad. I’m going to work 20 hours a week. And now, I had this guy that I’d hired to be the admiral in North Texas, and this was the biggest shocker. I thought, it’s going to slip a little because I’m not there. But when I replaced myself in ’06, ‘06 and ’07 just right through the roof, like it just kept going. Then ’08, it crashed, ’08, ’09, but that was more because of the market. So, then I was learning also. First off, I spent a year working 20 hours a week and really nursing my dad all the way to the grave, which I really am proud of. I don’t regret that one bit.

I have my daughter Bella with my wife Tracy, so there’s a lot of personal changes. And then we went through this massive crash, and when the crash happened and we come way down, like we’re down 60% in revenue and profits are down 75%, I began to realize, and this is my new learning as you get more mature, is the market is bigger than any of us. And then when the market’s booming, that’s why I say, I got it in ‘94, the market went all the way up from ‘92 until 2007 or so, the market went up. So, I was lucky there was a timing component. And I’ve seen that over and over again in my life now, where you can’t be bigger than the market.

So, you can have a manager, you think, oh my gosh, this manager’s made me an increase of 30% a year for the past eight years. Then the market drops 50%. And if they’re really, really good, you drop 40%. So, you can’t really measure it in the way I used to think, which is like, just get me 20% growth a year and I’ll consider you a B-plus player. Give me 30% a year and I’ll consider you an A-plus player.

So, yeah, the market crashes, my dad dies, I have a baby, and my life is in a whole different place. My income goes way down from 3.8 million down to 1.8. No one in the world would be sorry for me except me. I feel sorry for me, but no one else does. But then it stabilizes. And in 2009, I start investing, 2010, I go in a little more, and by 2011, again, intuition being in the business, I’m like, real estate is mispriced. It’s still scary. People don’t remember, it’s still scary. You think that the whole world’s going to end, all the banks are going to still die. There’s still a lot of blood flowing in the streets. But it’s becoming clear to me that that building that sold for $6 million last year that now won’t sell for 2 million is mispriced. You couldn’t build it for 4 million. So, I start buying stuff and then I go heavily in in ’11. In 2012, I go all in and I build a business buying distressed assets. And I built a business buying distressed homes, single-family homes.

Brad Weimert: I want to highlight something there because I think that when you say it’s mispriced, in real estate, in particular, the most common, let’s go residential for a moment, mechanism for value is comps, right? Comparable property. And you have to, at some point, trust yourself. And what you did was use a different comp, which was can I f*cking build it? And that is a much more rational approach than just the neighboring properties sell for this value or has it sold for this value. That’s not relevant. It’s not that relevant.

David Osborn: No. There was definitely a dawning on me that really was probably the biggest buy signal. By 2013, it was the biggest buy signal I’ve ever had in my body. My body’s like, buy everything. And I didn’t know any rich people and I didn’t have any access to money, but we just started buying the best we could. I raised money from buddies. And yeah, actually, I got that from Sam Zell. So, again, to give credit where credit’s due, Sam Zell said he always tried to buy property at 40 cents of replacement cost. So, I never wanted to be a slumlord, but that resonated with me. You could feel the market coming back. I had a coast-to-coast representation through Keller Williams. Interest rates were crazy low, and there was just this scar tissue from the collapse that was causing everyone to hesitate.

So, I even taught my agents, like, go buy real estate now. In 2012, I taught a class, why now might be the best time in your life to buy real estate? And about 15 of them, like I taught hundreds and hundreds, maybe even thousands, but I know about 15 bought real estate and those ones come up with me all the time like, thank you so much. That was such great advice. Thank you for telling me. Most people don’t take action in life. That’s one of the most frustrating things about life.

So, then I’m buying all these assets and I’m buying. And then a guy comes to me and says, “Hey, if you buy the debt on real estate, you get an even better price because there’s less buyers.” So, this guy came to me with this proposal. I hired him. And by the way, I had learned by now that lesson of, like, hire people, give them an opportunity, because now I have enough money. So, you keep trying to find the guy with the ambition and you give him an opportunity, and most of them fail. But every now and then, one of them succeeds.

Now, this guy didn’t succeed, funnily enough, but I’m paying him 80 grand a year. He got me all the paperwork to be approved as a– so I look like a lender that can buy other loans, right? It’s a process. I got FDIC approved so I could buy bulk homes or whatever, the FHA approved, maybe. And we go through all this paperwork, we get that done. But this guy could never pull the trigger. We bought one set of assets, but then I hire another guy away from Andy Beal. Andy Beal is a billionaire in Dallas. And he’d hired 100 MBAs, analyzed a bunch of stuff, fired them all, hired them back, analyzed a bunch of stuff, fired them all. And he’s worth, like, 12 billion, right?

But one of those guys comes to me and I hire him. And then we built a business called Security Lending, buying distressed loans. And we bought $120 million worth of loans. It probably made $35 million on those loans. Unfortunately, he went away, but that was a business we created as well. And then, meanwhile, I’m buying all these single-family homes. So, I buy about 800 single-family homes, maybe a thousand. We sell most of them. I kept 100. In hindsight, I should have kept 200 or 300. And we were building a business, getting ready to go buy a thousand homes a year.

Then, suddenly in 2013, the market just shifts. All the big guys get in Blackrock and they start buying everything at prices we thought were crazy because we’re on the ground, we know it. And they would buy these homes and leave them vacant for a year, which doesn’t work. You need your rent, you need to turn them, right? But the truth was, they knew something we didn’t, which again, the market was about to go up. They knew there was a tailwind.

And then, even those homes they left vacant for two years, they still made money on because the market went up. As you know, from 2013 till today, real estate’s probably up 200% and you’re using leverage and they’re able to get leverage at 2% and 3% and 4% when we’re paying 4% and 5% and 6%. So, that market, that business went away, still had my distressed debt business. But now, I’d bought a bunch of assets. The market recovers. All my Keller Williams stuff goes up, all this family office stuff that I bought in distressed debt and, suddenly, I’m pretty rich. And that’s when I was like, oh, I’m suddenly– like 2013, 2014, I’m like, yeah, I’m worth 40 million bucks. Then I joined Tiger 21, and that’s when I started investing in other opportunities. And until then, I was all focused on only what I did. So, in 1994 till 2014, 20 years, just all in on single family or real estate of various kinds.

Brad Weimert: I love it. That’s super helpful. And in 2014, and this is a very logical segue here, Tiger 21, for those that don’t know, is one of several longstanding traditional mastermind groups, where there are financial minimums that you need to get into it. So, it’s a significant vetting process.

David Osborn: I think it’s 20 million today.

Brad Weimert: Is it dependent on location? Like, YPO is dependent on location, Tiger 21. Is it structured differently?

David Osborn: It’s 20 million across the board, but they have groups that you have to be– you can set your own group guidelines. It’s only 15 people per chapter.

Brad Weimert: There you go.

David Osborn: So, there are people that got to have a G5 in it to be in the chapter. That might be YPO, but there’s like– and then I joined another group recently that’s R360. That’s 100 million minimum to be in it. So, yeah, like, I was a terrible student, got thrown out in three high school, C student most of my life, got out of college with a 2.3 GPA. But that’s the other thing, I’ve been a student of life once I got into business, like I’ll spend 100,000, 150,000 a year on education every single year, and I have for 25 years since I could afford it.

Brad Weimert: Yeah. Well, and I think one of those questions is, what does that mean “since I could afford it”? And the same thing is true of the transition to investing in other things. It’s what are the points in life where you allow yourself as the driver to say, “Now is the time to shift focus, diversify,” however you want to look at it.

David Osborn: Yeah. So, for me, it was 40 million. But it was partially because I joined a group which Tiger stands for The Investment Group for Enhanced Returns in the 21st Century, Tiger 21.

Brad Weimert: I didn’t know that.

David Osborn: So, they pitch, they show us deals every week. And you’re getting more sophisticated in your analysis of deals. But I did a lot of stupid deals. So, as soon as I got in, I was like, “Oh, I put some money in that, put some money in that.” I would bet if you took, I probably put 20 million in a lot of different deals over the 10 years I was in Tiger, and I bet the return on that would be no better than what I would have done with that money by myself. Probably, almost slightly worse. But I had more fun. I made a bunch of stupid stuff, like dog food and tech. And I had one tech fund go really well. So, that one’s been kind of put in a million and got a 1.15 million out, but it’s kind of downtrended to about 7 million because I didn’t sell everything. But still 1 to 7 is really good. You can’t do that in real estate in a five-year period. But I have a bunch of others that went to zero, put 2 million in a deal that went to zero, started another business that went to zero with a million bucks. Now, okay, so here I’m in the journey. I bought all these assets. One thing I realized is like, if in 2013, I’d had 100 million, I could have turned it into 300 million. But I didn’t have any money.

Brad Weimert: Through real estate.

David Osborn: Through distressed debt was actually the bigger play. But yes, distressed debt on real estate. So, you think about the real estate. There’s a real estate home that was selling for 6 million. They’re selling it for 2 now. And you know you couldn’t build it for four. So, that’s one analysis. But now, all of a sudden, you have a multifamily apartment that has a $10 million note on it that’s worth 4 million today. It’s 50% vacant. But the bank is trying to get that off the books so they’ll sell it for 2.7 million. That’s what I started doing. So, you buy the note and then you’d call the owner, say, “Hey, you owe me 10 million. I know you can’t pay that. Can you pay 3.5 million? Or do you want to give me the property?” Or if I really like the property, I’ll give you 50 grand to sign all my papers and give me the property and go away. So, cash for keys. Only foreclose if they’re jerks. Like, I always try to treat people well. I think treating people well is so important. I mean, we’re only here once on Earth, so I just try to treat people well.

So, then I started meeting wealthy people. Tiger, one of the reasons I joined Tiger is full of wealthy people. Then I started a private equity firm because we were buying this distressed debt. So, of that 120 million in face value of debt that I bought, we made 30, 35 million, I probably raised half that money or maybe two thirds of that money. I was the other third or half. I can’t exactly remember. We did eight funds, never lost money on any of those funds. The best term is like 40%. The worst one was probably 10%. That was at the very end, maybe 8%.

Brad Weimert: Are you still doing that?

David Osborn: So, then that got me into private equity. And I had a partner, and we didn’t see eye to eye on how to run the business. A lot of respect, but we got out of business. Still respect, but not in business. So, I started my own private equity firm. That guy didn’t work out, my first CEO, but we tried really, really hard. We got two years in. I had to hire another guy from another company. And now, that private equity firm is starting the S-curve, it’s doing very well.

Brad Weimert: So, it’s been around since ’14?

David Osborn: No, I was in with somebody else in ’13 as a partner. At first, they were helping me raise money. Then we started a business probably in ‘16. We got out of business in ‘18. I started mine in ‘18. So, now, it’s six years old. But I’ve been in the business now for almost 10, and I think it takes 10 years to get good at anything really. Like, again, that’s a rule of thumb, but I think there’s some truth to that. And I think it takes 10 years for business to get great. There are exceptions, and I know in tech, it can be different, but it just takes time in the business as I do to learn all the nuances and what has to happen. And there’s really no way to learn them. There’s no way to learn private equity except by doing it.

But now, we’ve got the right guy. And by the way, the guy that I had before, good guy, but just not a good CEO, but said all the right things, like charismatic, big personality but didn’t get anything done he said he could do, but you too believed he could do it, like everyone believed him because he was just so confident. Hired another guy who’s more intellectual and much less kind of in your face, but works his butt off, and took a long time, like a year or nine months to get him to come over, got him over. Took another year for him to get familiar and get his confidence. But he’s so good. He’s so good at the structure piece, the piece you’re talking about, getting the numbers right, having the spreadsheets, really getting into the mechanics of each and every deal.

And now, that business, we’re about to raise our third fund, which we have a pre-commitment of 75 million. The first fund was 32 million. The second fund was 50 million. We did a bunch of sidecars. That’s how we got to our 200 million in equity and maybe 400 or 500 million in assets. And then this new fund will be 75 million if these guys come through. But they’ve already put about 10 million with us. And it’s just been such an interesting journey and a further validation that you hire the right guys. You pour resources into them, you pay attention, and then you let them run. And so, that business, I think, is on really solid footing.

Brad Weimert: So, we had a pivot point here, which is the transition between these two things. You mentioned Tiger 21. And the other business you have is Gobundance. And you mentioned that it did 13 million last year, on track to do 19 this year. Gobundance is sort of a less traditional format of a mastermind than Tiger 21. And I want to talk about the structure and format, but first, I want to talk about the role that sort of community masterminds, relationships have played in your life because that came at this transitional element from, hey, a 20-year chapter of building Oone business isn’t closing, but you’ve opened the door to other things, right? What role did Tiger play definitively? And what role do masterminds play on going with you?

David Osborn: So, in Tiger, until I got to Tiger, I only knew Keller Williams people who were successful. I’m a son of a soldier. It’s not like I grew up– I mean, my great uncle, but he’s dead. And his kids didn’t do well like he did. So, that was like he died when I was 19 or something. So, it’s not like I’m surrounded by wealthy people. I knew some wealthy people that were clients of my mom’s who was a real estate agent or whatever, but I didn’t know them. I joined Tiger 21 and suddenly, I’m in a room with a dozen successful guys that made their money in something other than residential real estate sales. That was a big eye opener for me. I’m like, oh, because I was deep in the Kool-Aid and deep in the– this is the way and this is the way everyone knows.

Brad Weimert: And how old are you then?

David Osborn: I was 43 or 44, kind of your age. It was a big eye opener for me, really, it was. because I’d only known people in real estate. So, I knew multifamily guys that had bought a Keller Williams’ master franchise. I knew people that bought offices that were builders. I knew a guy that had student housing that had bought Keller Williams. So, the wealthy guys I knew in Keller Williams had made money in real estate and had bought Keller Williams as an additive to their world. But I hadn’t met anyone outside of real estate. Suddenly, I meet a guy that has a tech company and somebody that did jet aircraft engine. This is disassembling and selling. And now, I know a guy that’s got a health fund. So, that was a big eye opener that there’s more than one way you can make money. And then, sorry…

Brad Weimert: That’s the Topo for you.

David Osborn: Yeah, that’s the Topo. So, then that was a big aha, and then the masterminds for me have been everything, like I would say, even going through Fred Grosse when I was at Keller Williams or going through the masterminds Keller Williams taught, like, your peers are so important. I think you learn more from your peers than your teachers. So, Pat Hiban being my right-hand guy, my peer partner for so many years since 1997 and him becoming financially free, and I’m like, “God, if that guy can do it, I can do it.” You begin to realize, in Gobundance, we have now a thousand members and they’re not– I have a friend who runs a $7 billion healthcare fund. He’s a freaking genius. He went to Stanford at age 15. He’s the exception.

The thousand guys I know in Gobundance just like me are just scrappy. You’re scrappy. You’ve got the heart of a lion. You want something. You got a bigger vision for your life than what everyone else has for their lives. You’re just not willing to compromise and work for the man and then enjoy your weekends. You actually want to build something and it’s a lot more about the want to than about the naturally gifted ways of being. And that’s super compelling. It’s super contagious.

You hang out with a guy like Rock Thomas and Tim Rhode and Mike McCarthy, and they want to get up to something in life and that’s contagious. So, I think peers are possibly more important than almost anything. And if your buddies all just want to play video games and watch the Super Bowl and get drunk, that’s probably what you’re going to do. And if all your peers and friends want to build big businesses and be financially free and have multiple homes and fly around in a jet, at least you got a chance to do that.

But if you’re on an island unto yourself, it’s really hard to think bigger than your own island. Does that make sense? So, I’m a big fan of peers and masterminds, and I’m in a bunch of them and I’ve joined a bazillion. I was in YPO for a while and I wasn’t tired, just dropped out after 10 years. I’m looking at this family office network, which is 200 million and above to be in. I’m in one called R360 that’s 100 million. And again, I learned from those people. I spent 60 grand to go hang out with Richard Branson on Necker Island. And you know what I learned is the energy of Richard Branson is so clearly the energy of an entrepreneurial predator. And he cares, he wants to make a difference in the world.

But when he looked me in the eye, when I was in the Serengeti, a lion looked at me in the eyes. I was sitting on the edge of my car looking at a lion killing. The lion looked up at me and I remember it looked, I was like, “That thing wants to eat me.” I was like, “I taste good.” It was looking right at me that way. That’s how Richard Branson looked at me. It’s like the eye of the tiger. And so, that’s compelling and it’s attractive and it can infuse your soul with your energy. So, that’s why I love masterminds. I love the Gobundance guys because they’re all so scrappy and hard working.

And the other thing I learned about Richard Branson, it was amazing. As a small segue, he was sitting with his assistant one day, so I went and asked him, “Hey, can I sit here?” She gave me dagger eyes, like she didn’t want me around. And he said, “Yes, just don’t talk.” So, I said, “Okay.” So, I sat down and listened. Thank God I brought my journal. And all he was doing was going through email after email with her and telling her what to say. One of them was to Sheryl Sandberg, and I remember, he was like, “Yeah, tell Sheryl, blah, blah, blah, blah blah.” And I’m like, “Oh, you know what? I don’t have to do my emails anymore.”

So, I came back from Richard Branson experience, having paid the 60 grand, and I just said to my team, “You guys do my emails.” I might look at it on my phone, but I’m not answering them. And you’re going to guess what to answer. Most of them, 90% of the time, if you receive an email from me, it’s my team guessing what they would say. Now, my texts are still my last private castle or citadel, which I might even give those up because, yeah, I mean, so that’s what Richard Branson taught me. And I’m like, “How much has that been worth?” Well, that was– I don’t remember when that was, like 2015 or something, it’s been worth hundreds of hours that I’ve gotten back and not stressing about stupid emails.

And now, even if there’s a bad news email on Friday, my team doesn’t tell me till Monday, so I don’t stress all weekend. Say, we got sued by somebody, I don’t stress all weekend going, “That’s son of a gun. I can’t believe he sued me.” I’m just like, enjoying my weekend. I’m oblivious. And then, on Monday, when I can actually do something about it, then we have the talk. We get the lawyers on the phone. We try to work everything out. So, yeah, it’s created a lot of peace in my life. And that’s an example of what masterminds and proximity and peers do for you.

Brad Weimert: I love that. Well, I’ve got a thousand questions about that. I also want to respect your time here. I do want to, at least spend a minute on wealth because it can’t wait. So, you wrote a book by that title.

David Osborn: Wealth Can’t Wait, yeah.

Brad Weimert: And it’s a great book. I have, as you do, hundreds of friends that have written books. And most of them, I don’t say that about.

David Osborn: Yeah, it is a good book. Thank you for saying that. I mean, it doesn’t flow like the E-Myth or whatever, but there’s a lot of wisdom in that book.

Brad Weimert: It’s incredibly tactical. It’s strategic at the same time. It is an important map for a way to build wealth.

David Osborn: There’s good stuff in there. I probably should have written four books instead of one, but that’s going to be seven years to write that book. When my dad was dying, I was like, “I need to write a book.” And it took me seven years to finish that because I am such a bad writer, and I’m like a stream of consciousness blurter, but it’s good. I think it’s good, too. I don’t know that it’s great because of the flow, but I think if you are working out, because we did in so many small chapters, you can just listen to nugget after nugget after nugget.

Brad Weimert: I listen to it running. I vividly remember listening to it running in California. I was in Carlsbad. Yeah, running in California, listening to it.

David Osborn: Probably running a mountain like Everest or something, like you tend to do.

Brad Weimert: And it’s great. But I think, people read books. I read books for different reasons. And this one is a very prescriptive one. And I’m going to go for an absolute because they’re fun and they’re rarely true, but if there is a fundamental principle of investing, you waited until you were at 40 million net worth to invest, which is probably not necessary for people.

David Osborn: Well, to be fair, I was dabbling in the dot-com craze and I got burned. So, it kind of spooked me because I was making a bunch of money on dot-com companies, and then people started asking me for advice because I wear glasses, they think I’m intelligent. And I said, “No forever.” And then late 1999, I was like, “Okay, I’ll tell you guys what I know.” And then I had a little group together and I was telling them, and then the ship blew up. And I realized I didn’t know what the hell I was talking about.

So, I got really spooked by Wall Street. So, I was investing only in me in real estate and things I understood, and I quit because I got burned a little bit. And when I say burned a few hundred grand because I wasn’t worth that much in ‘99, 2000. Remember in 2001, I made 1.2 million, but it was like my first year of making money and all my money was going back into launching market centers. And then I told people and I felt like an idiot. I was like, “Yeah, I thought I knew what I was doing, but I didn’t know sh*t.” So, I just went away from investing in things I didn’t understand.

Brad Weimert: So, let’s not look at your wealth strategy now and let’s take it to the people that are making a million, a couple, a few million a year. At that point, what do you think a functional wealth strategy is?

David Osborn: Yeah. So, here’s what I would view my– you got employees, your money is also an employee. Dollars are employees. And they should go to work every day and earn you 10 cents on the dollar. So, every dollar you’re not putting into your business or in your personal growth, which the best investment you can make is in yourself, but then think of your money as employees and they got to be working. And if you put them in an investment that doesn’t pay you, you should fire that investment. And it could be through growth or through cash flow. I’ve always loved cash flow. But that’s the way.

And you can’t build– wealth has a gravity to it. The more you have, the more you make. And it’s funny, I could make a million on an investment, which is the money I told you probably that I made in 2001. I wouldn’t even notice it today. I mean, it would be great, but it’s not moving my needle. Does that make sense? And it’s almost easier than it used to be because I have a lot of capital so I can make a lot of mistakes.

But my point is that early on, you got to accumulate wealth because wealth has a gravity to it. The more you have, the more you make. And the way you do that is by saving some money and putting it to work for you, and you can put it to work in real estate, you can put it to work in dividends. You could do in the FAANG or the top 7, whatever they call it, the mighty 7 tech stocks. But it’s got to go to work and you’ve got to put it to work for you.

And there’s a risk factor. Like, I think real estate is a low risk. I think you should succeed in nine out of ten real estate investments. Starting a business is high risk. Probably one out of 20 businesses makes any money. The stock market, in general, like index funds, pretty low risk. If you’re in the Vanguard 500, you should probably make 8% or 9% a year. But if you want to take high risk, you go into like Facebook and those other ones, maybe you make 30% a year, but maybe you lose 50%.

But at the end of the day, your money has to be working for you. And the more you can save, earn, invest, save, earn, invest or earn, save, invest, earn, save, invest, the sooner you’re going to get to wealth. And there’s not a single person in this world that’s a billionaire that doesn’t have $1 billion worth of investments or assets. Otherwise, you couldn’t be on that billion-dollar list. And then, the best way to make money is by starting a business that succeeds, but it’s also a really, really good way to lose a lot of money. So, you’ve just got to decide your temperament, who you are, where you are in life.

Real estate, I think, is the best way for the everyday person to make money. Most people would say 50% of net worth is in their house. And I’m always like, “Why do you only own one house? If 50% of your wealth is in a house, why do you own one? Why don’t you own five?” But then you want to buy cash-flowing real estate. And the risk about what we’re talking about in investing here is like, it’s the 10-year thing again. You’ve got to spend 10 years doing this to learn at it and get good at it.

So, whatever I say on this podcast doesn’t matter because they have to listen to it over and over again and make the mistakes and do the right things for 10 years. So, I guess the number one thing to remember is there’s no one that’s wealthy that doesn’t have wealth. And the way you have wealth is by earning, saving, and investing in something, yourself, a business or real estate, or the stock market, but you’ve got to play that game to get to financial freedom.

Brad Weimert: What I think I heard is that you need to understand the investment vehicle that you’re investing in.

David Osborn: Correct. Very much so. And businesses are my favorite. But I see so many people fail. So, I’m not, just because I’ve gotten lucky in a few. By the way, I failed in dozens, but I failed when I had enough money to be able to afford to fail. Early on, when I took the franchises, if I’d have failed then, it would have been a whole different story for my entire life, I’m sure.

Brad Weimert: So, early on, it’s pick a vehicle.

David Osborn: And just go.

Brad Weimert: And double down on that vehicle.

David Osborn: Yes, for 10 years, maybe.

Brad Weimert: And understand it.

David Osborn: Yes. Become the expert in it. Then you have an insight advantage, because when you know it, you have an insight advantage. In 2012, I had an insight advantage on real estate as a whole, especially residential real estate. And I knew it was mispriced with 99% certainty, but I wouldn’t have done that and known that if I hadn’t spent 10 years in the industry already.

Brad Weimert: Yeah, that’s great. Awesome, David.

David Osborn: Brad, it has been fun.

Brad Weimert: Yeah, it has been great, man. It’s always great. I don’t see you enough.

David Osborn: I’m missing my workout right now.

Brad Weimert: Well, let’s get you to it. Where do you want to point people, if anywhere?

David Osborn: You know, you can buy Wealth Can’t Wait. You can go to iamdavidosborn on Instagram, but I’m really not trying to be up front anymore. I’m just enjoying my life and…

Brad Weimert: I love it.

David Osborn: Yeah.

Brad Weimert: Love it. Well, I appreciate you carving out time, man.

David Osborn: It’s been great. Good to see you.

Brad Weimert: You too.