#1 Agent In The World: I Was Worth $5 Million At 23. Then Came The Crash. | Leo Pareja

I owned 14 rental properties. My account had just told me I was worth $5 million. And within eight months, that number went to negative a million dollars.

So I went from what I thought was success and that was like a half a million dollars a year, 20 $30 million in production to jumping up to becoming number one in the world. There's a formula to everything. Everything's a math problem. The big pivot was I would advise people to actually

So the interesting part about that question is it was actually the most empty and meaningless feeling of my entire life. And if I were to take you back when I got into real estate at 19 and I learned that that was a thing I could achieve. I had two singular obsessions when I was about 20 21 which is one I wanted to be on N's 30 under 30 list and then I wanted to be number one at Kell Williams and it became an obsession like for eight years in the road it's all I cared about. I tracked, you know, and it was a fun process because I went from I wanted to be number one in my office, then I wanted to be number one in my region, then I wanted to be number one in the East Coast, and then like slowly climb, then, you know, I made it to like number four a couple times and number three. But the second I got it, I woke up the next day and it was actually very sad and depressing because I didn't feel different. It wasn't my most profitable year. Nothing changed. I didn't get this unlock of wisdom or transformational aha. And I didn't actually know what I wanted to do after that because it became such a core driving version of who I wanted to be. And once I got it, it almost left me confused. And it's been a really interesting anchor for me because it just reminds me that, no matter what role I talk up about seasons of life, I'm super happily married with two amazing little ones right now. And so the season I'm in, I just don't want to screw that up for them because in that journey, Daniel, I actually got to be in front of 100 millionaires and billionaires. And I got into the habit of asking each one of them like, 'What would you do different? What's the one thing you'll tell me?' And they all, mostly in the early 2000s, baby boomers, they all had the exact same reaction, which is don't screw up the time with your little kids. And so that's become a core thought process that no matter what chapter I'm in, I've had some really cool titles like number one in the world or founder or CEO of a $5 billion enterprise business. I get to be on the news and on big stages. But from that one experience, I also remember that this is just a role I'm playing. And when I'm taking my last breath, hopefully as an old man, I'm going to be surrounded by people who care about me because I showed up when it was important. And it wasn't like I was sacrificing for them. No, it's about actually showing up and not forgetting the important parts. While the people we've talked to, like you said, the most successful people almost always say their biggest regret is they missed out on their family stuff, their kids' recitals, whatever it was. They were just not there for their children or it even ended their marriage. It had a turn on their personal life.

Yeah. So the gift I've gotten that I just think I'm the luckiest kid in the world and I give it to the universe or God, whatever you believe, is I just had really good luck as a young person. And the luck I had was getting the kicked out of me in the financial crisis. So I was 23. I owned 14 rental properties. My accountant had just told me I was worth $5 million. And within eight months, that number went to negative a million dollars. And I was in the fetal position, crying, negotiating with banks to take some properties back. Called BMW and said, 'You need to come get your car.' And I realized in that moment, as I was driving towards my goals, I always had this thought process of when I get there, I will do X, whether it was giving back or spending more time with my family. And I lost it all in seven or eight months in dramatic, chaotic fashion, which again was not unique. If you haven't seen the movie, I recommend The Big Short. I remember when we watched it with my wife, she looked over and I had my shoes on the couch, in a fetal position. She said, 'You got real PTSD just watching this movie.' But that early experience taught me that it's all a moment in time. It can all vanish super quick. From friendships and relationships to the roof over your head. Actually, in that moment, my wife, who was my girlfriend back then, we both decided we were going to be mentors with Big Brothers Big Sisters because I always thought when I have more money, I'm going to start a foundation and give back. And then it all disappeared.

It's doing it in the moment. And so when it comes to giving, I've always told people just give to one person and that could be way more impactful than writing a $1,000 or $100,000 check. My wife and I did start a foundation once we had money. But whether it's spending time with loved ones or a cause you care about, I now reverse engineer everything. When I plan the 2027 calendar for eXp globally, my kids' calendar goes in first: spring break, all the things we can plan ahead of time. And again, every school drops some nonsense on you two weeks out. But I've created a culture where my people understand that's my priority. If I say I'm canceling today because it's my kids, they understand that's my priority. And I think it's shown a version of leadership that's different than what you normally expect at a public company. Very real story: I had an offsite with my executives and there was an executive who looked really upset. I asked what's wrong. She said, 'I'm missing my kids moving to college.' I said, 'Why are you here? This is insane.' She said, 'I know these only happen once a quarter and I didn't want to miss it.' I said, 'If I catch you doing something like this, I will fire you. This was a terrible judgment call. You should have just told me because you can't undo that.' And again, none of this is wisdom. I missed some of my best friends' weddings and bachelor parties. And Daniel, for the life of me, I can't remember what was so important that I didn't show up. So the gift I feel I got is that I got that really early and I screwed up friendships versus my kids. I remember the crash of 2008. Unfortunately, I lost my job and had to live in a tool shed. So although I didn't lose homes, I definitely lost my dignity and motivation. It gives me PTSD when I think about how horrible that experience was.

Well, no. This is where I sound maybe a little schizophrenic and I talk about seasons. I think the world is too soft on young people. I think you should work 12 hours a day, seven days a week because youth is wasted on the young. Energy is a superpower.

There's a really interesting concept: when you're 19, all you have is energy. And so I can create more output now in two hours than I could at 22 in 12 hours. That's the gift of life and experience and wisdom. But when you don't have experience and wisdom, all you have is time. So go put in reps. I tell young people to compress time as much as possible. In real estate, that means join a team. In entrepreneurship, go join a founder that you want to be like when you grow up because the best teacher is osmosis. To quote Hamilton, just get in the room where it happens. I was a sponge, always sought out mentors, and after meetings I'd call them to get the replay: 'Why did you ask that? Why did you pause? How did you know they were going to say that?' You realize there's a framework, a tactic, a structure to a conversation. That only comes from experience. You can't read it, you can't buy it, you have to be in the opportunity and have it blow up in your face. I encourage young people to create as many experiences as possible. I am the biggest proponent of osmosis. I could have never been successful in business if I didn't work for somebody else.

So I had a mentor who was transformational in my life. He took me under his wing because I was 23 and doing pretty well. We developed respect and friendship through my hustle. After the crash, he was a well-heeled investor and we bought real estate. I did the work and he kept most of the upside, which is how it works when you're young. I called him Uncle U because he walked into banks and co-signed for me. But when I was turning 30, he sat me down and said, 'You're no longer this child prodigy phenom you've crafted your identity around. You're now just an average successful guy in real estate. So you better get pretty good at something else and create a different persona.' That was interesting around identity. When people make their career their identity, they can have traumatic falls. You're multifaceted: I'm a father, a son, a husband, an advocate, part of multiple communities. I see entrepreneurs become one-dimensional. Even if it goes perfect, I got another heads up: when I was about to sell my first company, a friend hugged me and said, 'This is going to be the most traumatic experience of your life.' I said, 'What do you mean? This is what I've been driving towards.' He said, 'M&A is brutal. Their job is to hurt you and take from you.' And no matter the outcome, when you sell a business, you give away a big part of your identity. On the first one, you learn to have an email address unrelated to the business. When you hand over your email, that's how you log into everything. You lose status because you're no longer the founder and CEO. It's just the guy who took over your company. So there have been interesting life experiences of 'Who am I?' outside of being a founder.

Yeah, that was one facet of it. One was being a student of history and realizing I thought I was really good at real estate, but I just had a real estate license during the greatest real estate bubble with slightly more hustle. Then I realized I wasn't actually good at lead generation, conversion funnel, follow-up process. I was flying by the seat of my pants. Then the next chapters became about total addressable market, CAC, LTV, leverage, retention, churn—actual systems and processes. Everything's a math problem. Building a business is like caloric deficit. You need to create more revenue than expenses. That's a factor of lead funnel to conversion to retention. The big pivot was realizing it's not about being gifted; it's a math problem. How big is the total addressable market? How do I capture an unfair share at a unit acquisition cost that makes sense? And how do I scale it defensibly so someone can't just come and take your cheese.

I spent 10 years in tech. A service business is easy because it's geographically tied. For real estate, you can only serve 30-45 minutes away. In tech, you build something cool, and Google or Amazon can just build it themselves. That's capitalism: arbitrage is an efficiency in the market, and as a segment matures, margins compress. That's part of the game. Sometimes a movie ends through consolidation or acquisition. We're living through the death of most SaaS as we know it. AI is grossly overhyped and underhyped at the same time. Most things are overhyped in the short term and underhyped in the long term.

We're on version 17. V1 was an iPod that allowed me to make phone calls. This thing today gets me into the country, has my credit cards, starts my Tesla. It's so far removed from V1. We're seeing that overhypeness in AI. Historically, every technology transformation—steam engine, internet in 2000—created massive overinvestment followed by a crash, but the infrastructure left behind changed everything. AI is similar. I was a non-technical founder who founded a tech company. Previously, I could go to a courthouse to check permits or drop a tennis ball on a construction site. In tech, I couldn't look at the code. But now with tools, I can get into GitHub and do things. I think we're going to witness the death of most enterprise SaaS because it's overengineered. Businesses at scale will build their own workflows.

That's a great question. When I talk about AI with agents, they have anxiety. The people overhyping it are financially incentivized. Always pay attention to the source of fear. Two, we're in the MySpace era of AI. Nothing says OpenAI will make it. I bet on Gemini because they have the most resources and can make it free to choke out competition. Apple isn't first but wins with ecosystem. Understand who can put you out of business overnight. That's how you get acquired. There's a balance. I won't sign NDAs because I don't want liability if someone shows me something I've already built. I tell entrepreneurs to form relationships early but be aware. I've been on both sides. The little guy has the advantage of speed. What keeps me up at night are the two kids in the basement who can move my cheese. I advise people to form relationships early.

Bouncing back from the financial crisis. I went from what I thought was success—half a million a year, $20-30 million in production—to becoming number one in the world. But what sunk in was that I didn't feel different. There was disappointment, and also the realization that you're never ready. Life is like that. I wasn't qualified at 19, but I did it anyway. I wasn't qualified to buy a house at 20, or sell that volume, or get Fanny Mae and Freddie Mac to let me sell foreclosures, or raise money from top VCs, or be a public company CEO. The moment you realize you're going to die, you might as well have fun and take calculated risks.

I still have it. You can't be human and not have it. Remember that everyone around you has it too. It's comforting. My nine-year-old is into jiu-jitsu. He competed and the kid in the finals had a thunderbolt shaved into his head and was pounding his chest. My son wanted to go home. I told him, 'He can't kill you. Figure out the worst-case scenario. It's not death. Just tap and the fight will be over. What's the worst? You'll lose, and you lose every day at the gym.' Courage is doing the thing in spite of fear. I say that to my kids and myself. Even after speaking in front of 5,000 people, I still get nervous when I get the microphone.

No, he lost. But he came in second at a huge tournament. The kid who beat him is homeschooled and trains eight hours a day. I don't care about the win. I want him to learn how to lose gracefully because the educational system is broken. Getting up is the game in entrepreneurship and life. It's about how many losses you can take and get back up. Leo Pareja, CEO of eXp. This was longer than my conversation with Mauricio. Don't tell him I said that.

Send him a text and tell him I said that. But don't tell him I said that. Thanks for having me.