Leap Academy with Ilana Golan - From Homeless Shelter to Building a Billion-Dollar Mortgage Company | Damian Maldonado | E146

Episode Date: February 19, 2026

Before Damian Maldonado was negotiating billion-dollar valuations or building businesses across Puerto Rico, he was a kid living in poverty and sharing bunk beds in a homeless shelter with his brothers. But those early years didn’t break him. They led him to become the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S. In this episode, Damian joins Ilana to share how growing up in poverty shaped his relationship with risk, money, and resilience, and what it really takes to bootstrap a company through market crashes, massive layoffs, and billion-dollar decisions. Damian Maldonado is a serial entrepreneur, investor, and co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. In this episode, Ilana and Damian will discuss: (00:00) Introduction  (02:57) Growing Up in Poverty and a Homeless Shelter (08:42) Key Lessons from Early Jobs (11:42) Pitching to a CEO at 21 Without Fear of Rejection (14:38) Damian’s Journey into the Mortgage Industry (19:14) Starting America Financing With No Safety Net (22:30) Leading Through Layoffs and Downturns (27:07) Why He Turned Down a Billion-Dollar Offer (30:57) Leadership Lessons from Richard Branson (34:25) Building a Portfolio Career with Adventure (42:53) Q&A: Crafting a Response to ‘Tell Me About Yourself’ Damian Maldonado is the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. He also co-founded American Home Agents and has expanded his business interests into hospitality and lifestyle ventures in Puerto Rico, including a boutique beachfront hotel, restaurant, and kiteboarding school, creating jobs and adding value to the local community. Connect with Damian: Damian’s Website: https://damianmaldonado.com  Damian’s Instagram: instagram.com/damiankitepr  Resources Mentioned: Awaken the Giant Within by Tony Robbins: https://www.amazon.com/Awaken-Giant-Within-Immediate-Emotional/dp/0671791540 Think And Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331  Rich Dad Poor Dad by Robert Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612681131/  The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

My mom, hard worker, she's worked for the FBI, actually, at one point losing her job. And eventually, you know, she ran out of money, so we ended up being homeless. I thought it was like normal. I didn't really, because that was 10. We also sold door-to-door candy. But that was kind of scary sometimes. You know, they pick you up in these vans and you're 10 or 11 years old, and they drop you off in the neighborhood. And they say, you start here, and then you walk around the neighborhood and they don't meet you at this other point.

That was a great experience because you taught you rejection, taught you how to sell. Damien Maldonado grew up in poverty, spent time. I'm in a homeless shelter and with $5,000 line of credit, co-founded the American financing, a billion dollar business. If you're not getting rejected, you're really not even trying. I think a lot of people don't even try. They fail before they try. And I think that's the norm.

When you're an entrepreneur, you have a roller coaster that you need to deal with. How do you deal with this threat? Yeah, that's where we were talking earlier. It's not for everyone because... Welcome to the Leap Academy with Ilana Golan Show. I'm so glad you're here. here in the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons.

So lean in, this episode is going to be amazing. I'm in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast-track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know because this show has the power to change countess of lives. Deal?

Okay, so let's dive in. I love episodes where we get to go on a journey with someone who built themselves from basically nothing. Damien Maldonado grew up in poverty, spent time in a homeless shelter, and with $5,000 line of credit, co-founded the American financing, a billion-dollar business. Now he runs multiple businesses in Puerto Rico.

He kitesurfs. He plays chess with Richard Branson. I mean, the guy is so much goodness. So get ready for an incredibly inspiring story for anyone who wants to reinvent themselves and create something big and meaningful and fun life. Plus, at the end of the conversation with Damien, we will pick a career-related question

that one of you've asked in a comment on our YouTube channel. Hint, your answer to tell me about yourself will transform forever. So stay until the end. Now, Damien, I can't wait to hear your incredible journey. So good to have you. Thank you, Lana. I appreciate that. Very nice intro.

Appreciate it. So you are going to take us back in time because your story, it is one of the more inspiring stories we've had on the show. So you're born in New York. Tell us a little bit about some of those early memories. Your mom got divorced when you're really young. So tell me a little bit about that.

Born in New York, they divorced, I think. I was like maybe three. I have three brothers. Sadly one passed not too long ago. But yeah, two older brothers, one younger brother. New York City, I've been to rarely. Still have a lot of family there. But one of these terms, they call New Yorkans.

If you're born Puerto Rican, born in New York, it was a New Orican. I never heard that. term. And then you moved to Colorado. Your mom is basically a single mother of four at this point. And she works basically in a very basic paying job. So what do you remember from those days in early Colorado days? We got back to Puerto Rico maybe until I was like seven years old. But my mom, hard worker, she's worked for the FBI actually. But as a secretary, most she's made is the low 30,000 is back in the day. And I don't know how you support poor boys. at the time by yourself. We lived in Puerto Rico, ended up going to Texas,

did Florida for a short stint, finally ended up in Colorado, which I still have my main business there. She ended up at one point losing her job at the FBI. We lived with the family at some point for a very little short time. And eventually, you know, she ran out of money, so we ended up being homeless, ended up having to live in a shelter for a few months. Take me there for a second, because you're sharing it as a story, but I'm sure as a kid. At that point, you're what, seven? At this point, I'm 10. So take me there for a second.

Do you feel stressed? Do you see her sad? Do you feel anxiety? What does it take as a kid? What do you see in the house? Well, we were in a homeless shelter. This was interesting to me because we came from Puerto Rico, ended up going to Colorado, didn't have a lot of money,

but we ended up going to this area called Aurora, which is not by any means like a rich area, but in my eyes, like, wow, we're in a rich neighborhoods now. This is crazy, all these homes with two-car garages. It was really eye-opening, but I didn't know. It's really middle-class, but for my eyes, it was like, this is a rich area. So eventually, after she lost her job,

the shelter is called Samaritan's shelter in downtown Denver. Still there. I've gone to visit it several times since then, and I've done some volunteer things there. But I thought it was normal because that was 10. I had two older brothers. They were a little bit bigger, so I felt safe because they were there.

They had this donation room where you go and get clothes and shoes, and I was like, wow, all this free stuff. But at nighttime, you were in a room with, say, maybe 20 or so bunks. And sometimes at nighttime, they were allowed men. to come in to sleep. So you'd hear at the middle of the night, these people going to these different bunks, that was a little bit intimidating

because they would let the single women that had children come in earlier until later looking back on it, I was like, wow, that was an experience. At the time, it looked like, well, this is normal, I guess. Wow. It doesn't sound like you feel major anxiety or sadness in the household.

Do you feel any of this, or it just becomes a new norm and it's okay? It became a new norm. and what I felt in hindsight as I got older is just like, well, I can't believe my mom had to go through that. I imagine as a single woman having to go to the shelter,

not having anywhere to go. And luckily, I think those programs are great when they're done well and people use them to get a job because then sometimes they help you get a job. Eventually she got a job. It was able to get us to an two-bedroom apartment. And at this point, me and my brother's sharing the room,

that's like, now we're in the big time if me and my three brothers and my mom, all in two bedrooms like this is a man. amazing in our own little place. I totally want my kids to listen to this. They're so spoiled. Like, oh, I don't have my, you know, room in a bathroom attached to it. You know, like, I need them to listen to this. I know the feeling I have to have my kids listen to it to you. So tell me, I think maybe that was, and I would love to hear some of your learning and what that stamp was for you because you started basically working really early. And I assume you realize

that you have to. So take us back in time. and kind of those really early jobs. And what did you learn in the homeless shelter? And what did you learn from working in those very, very early stage? I've always been good with money, kind of a saver and not trying to overspend. I remember early on my older brother, Oliver, which we've done several different ventures since then together. It's not easy work with family. I'm sure it was a lot of you guys have experienced.

He ended up doing like Avon sells door-to-door. So that was one of the jobs. And we also sold door-to-door candy. But that was scary sometimes. They pick you up in these vans and you're 10 or 11 years old and they drop you off in the neighborhood. And they say you start here and then you walk around the neighborhood and they don't meet you at this other point. So he was older, like three years older than me. So he's probably 13.

I'm 10. And we're knocking on these doors and I'm just sitting there supposed to look cute. And we had a pitch and they teach you a sales pitch of like, here, we're selling this candy for this cause. And just basically try to sell a candy bar or whatever we were selling. That was a great experience because you taught you rejection, taught you how to sell. That was really intimidating, though, because nowadays, it feels like you can't let your kids outside without some predators. I think back in the day, I think it was a little bit more you could do that. Imagine maybe it's still dangerous, but not like what it feels like now.

So that taught me just when you make your first little bit of money, you're like, oh, I made some money. We did door to door, also vacuums. We did newspaper route. That's actually great because, you know, you throw the newspaper. Then once a week, you got to go collect money. And that teaches you, I think, about business and also responsibility. You have to wake up at 4 or 5 a.m. that was a family event. So we'd all share in the money and just figure out how to make any kind of money at those days. Wow. So you're at 10, 11 ages that usually kids don't really work and you're not only working. You have these multiple jobs and you wake up early and you know, you learn about money and sales. And I'm sure you took a lot of the learnings into the business.

But talk to me a little bit of how did that all? evolved. So you're working in these jobs and then what's next? Like you eventually get into health and fitness. And your brother sounds like he's been like a really big model for you in those earlier ages. Am I right? Yeah. My brother Oliver, he got me to read Awakening the Giant Within Tony Robbins book, which I highly recommend to anyone. It's a big book. And I always tell people if you're going to read it, read it like you're going to college, take notes, do the exercises. Don't just read it like you're reading a normal book because I think it could change your life as it did mine. But that was when I was like 16. So my first real official W-2 job was at Toys R Us, 425 an hour minimum wage.

That taught, you know, you know, I guess, kind of how corporate America retail works a little bit. But I just learned how to make money and save. And I like to work. I like to make money. I feel lucky that I had to work for everything I've had. I've met some people that have been raised with money. And I think it's sometimes a little bit more challenging for them than like if somebody has this hunger that you don't have. And I'm, I'm raising kids right now to 10 and 12 and they haven't had to work. But yesterday they're doing things at the restaurant and carrying things. I'm like, yes, that's what you need to be doing.

And you need to work. It's working is great. I think it's fulfilling. And it gives you a purpose regardless what it is. And especially at a young age to figure out what you want to do. So after those jobs, my brother got a job at a company called National Fitness Corporation. They started Clearwater, Florida. And they would go to it.

So if you owned a Jim Lana where you live and it was like a regular fitness club, we'd go and start advertising. So we do telemarketing, direct mail, radio. We just blist it. And in that time frame, we'd sell the 4 to 800 memberships, two-year contracts back in the day before 24-hour fitness and all that.

And then people would pay $19 a month. But they send you a startup cost, they send you a $3,000 check, and then that would be your startup cost. You'd hire staff. It was a lot of telemark. I'll bond telemarking, which I'm not a fan of that business.

I know how to do it, but I don't like to get the calls, so I like to be in businesses that I don't like to be the customer. So we'd sell these members of them. I did it in 30 different states. I did it in New Zealand, Australia, the UK. By the time I was 21, that was my college. I learned all the sales of marketing.

I got saved up for like $15,000. And I'm like, I'm rich. I'm going to New York or L.A. And I didn't go figure out what I want to do with my life. So I was in England just finishing up one of these promotions. We used to call promotions. And I landed and my brother picks me up and he goes, hey, I got you a job.

And a mortgage company, you start on Monday. And this was Saturday. I'm like, I don't want a job. I'm rich. I got $15,000. I'm going to go on my adventure and figure out what I want to do with the rest of my life. I just like, I went out on the limb for you. You have to start. I started at the company and then that's how I got into the mortgage business. That's incredible. And share with me because I think, first of all, you are right. College doesn't teach you this level of marketing, sales, rejection, trying again, getting back up. You don't learn these prices lessened. That's my biggest problem with college and

kind of why I started Leap Academy. So you get into the mortgage space, but if I remember correctly, you know marketing at a very different level than what they've been doing, and that's what hopes you rise above the noise. Share that story a little bit. So I started this company called Terra Funding. They're not around anymore. The old CEO founder was the Builden Cloud. Great guy taught me a lot about mortgages and business.

But I started, they were growing very fast. And they were doing those 125 mortgages. I don't know if you remember those. but it was 25% over equity. They said that's part of the situation that happened with the collapse in 2008, but one of the reasons, they're advertising with these postcards,

and they send out hundreds of thousands, and I don't know if, you know, but direct mail gets very, I'm sure you know what I mean, gets very low response rate. So they send all these, and you'd wait for a phone call, and they'd give you a script,

and you'd start answering. And I'm like, I did that for a few months, like maybe a month or two, and now they go, man, they're not doing all this other stuff that I know how to do. So I go and pitch the CEO, and I'm like, hey,

here's what I want to do. I want to do all this other stuff. I just learned on fitness clubs, but I want to apply it to the mortgage world. So I want a $60,000 base, this commission, blah, blah, and I pitched them. And so he said, fine, let's do it. What age are you at that point?

I'm 21. You're 21 at that point, and you have the courage to go to a CEO and pitch them that you know what to do. Where did that come from, do you feel? Well, when I saw what they were doing, I couldn't believe that's all the marketing they were doing. And so from my perspective, I'm like, man, we need to get telemarketers.

We need to do this. We need to do this. We script it out. It's going to work great. So the way I look at all businesses, it's a service for a product. Those are the two things we have, right? So in this case, it's a service and kind of a product, I guess you're lending money. All we have to just script it, let's get the telemarketers and it's going to generate leads.

And I thought it would be better than these postcards. So yeah, you know, when you see those opportunities, like this is a no-brainer. That was one of those. That's incredible. But again, it takes guts. I think a lot of people are sitting and, you know, and they have these ideas, but the fear is numbing. They won't take the action to go to the CEO and pitch themselves or somehow maybe because you were not a favorite rejection. Do you know what went through your head at that point?

Or you're just optimistic in general? For me, I really believe books I read like that Anthony Robbins book, Anthrox and Dr. Within and think and grow rich and rich that port out. Like these books, I think, are like essential to what I've learned. And when you know something to be a fact, it becomes easy. And I'm definitely not afraid of rejection. If you're not getting rejected, you're really not even trying. I think a lot of people don't even try. They fail before they try.

And I think that's the norm. And I think at that point, you understand various types of marketing. So what are some of the mega marketing things that you know that you felt like you brought to this mortgage company? And then that also helped you when you started your own, which we'll talk about because that's a very different thing. So being an employee and trying to start your own thing is like light years away. And, you know, I always tell people, if you're comfortable with getting a paycheck, please get a paycheck.

I think the myth of everybody needs to be an entrepreneur is BS. But talk to me a little bit about what did you learn and then what made you decide to start your own thing. Yeah, I agree with what you said. I don't think everybody should be an entrepreneur. I mean, the pressure is stressful. It's insanity. Yeah. people think it's very easy and it's not because you have a lot of weight on your shoulders,

especially if you have employees and you're building something. You know, it's nice to be able to clock out and go home and you're doing your own thing. You don't have to have that thing going on in your head all the whole time. So for me, it was, I just think a lot of the books I read and the people I admired, they started businesses. And I still believe that you don't really need the business to be successful. All great companies have a lot of great teams and a lot of millionaires and billioners that were helped build that company without being the founder or CEO. So there's so many different ways to make it in this world. But for me, I didn't know radio at the time. I knew telemarketing a lot. So the way I looked at it, you know, back then we paid $10 an hour. So you get one telemarketer,

four to six hours shifts. You don't typically do a long ones because it is a lot of rejection. For us, we try to get one lead or one appointment per hour. So if they work four hours, they should get one an hour, which takes however many calls. So everything to me is recognizing that pattern, everything's the numbers game, how many calls it to take to get one, and out of that, how many appointments do you actually see? And out of that, how many do you actually close? So that same principle we just put to the mortgages, started with the telemarketers. We hired 10 of them, and it worked really well. We were generating leads. We had a script. But here I am 21-year-old, new to the mortgage industry, telling these veterans how to handle the leads. It was a little bit

challenged because they were like, who's this, I think he is telling me how to do my job? And I'm like, no, you do your job well. I just think if you say these things and these rebuttals, when they tell you this, I don't think a lot of people know how to communicate well or they don't know how to sell. One of the things I think in sales is say the customer wants to buy the product and then they say, okay, yeah, I want to do that. And they go, okay, great, do you have any more questions?

It's like, they just told you they just want to go do it, just like get to the cell and just finish it. You don't have to, but they make their own objections. And so trying to teach people, hey, less is more. Because if you say if you have any more questions, your brain on my likely goes, huh, I'm going to sound dumb if I don't come up with the question. Yeah, exactly.

And now the question is. starts. Now you have to overcome that objection. And then after they do it, then they'll go again. Any more questions? I'm like, oh my God. A lot of people don't know they even do it. Now I need my sales team to listen to this. This is so good. But I think there's also a psychology. Marketing is psychology of understanding people's minds and what will move people's mind. And somehow maybe because you've done it at such an early age, maybe you somehow grew up with it, That's not necessarily natural to everybody. What do you think made you so good at that psychology or sales?

It's such an early age. Is that the experience? I think a lot of it is the experience and being accustomed to getting rejected. But then a lot of it is the books I've read. I think I go back to the books. I didn't go to college, a formal education, but these books. And one book will tell you which book, if you admire this person, they tell you to read that book, then you read that one.

And that one is going to have the same thing. And it's this trickle effect. And before you know it, I'm big into you. Is it the outliers? is the 10,000 hour rule that you become an expert. I really believe that in any industry, sales or what have you. A lot of people say, oh, I hate sales or I'm not in sales. Like, well, that just means you're going to be less successful than somebody that doesn't

say that because every job, if you're a doctor, you have to have cells. You have to explain things in a certain way. Every career, every job has to explain things to customers in a certain way for them to want to either buy it or to at least feel good about what they're doing. Right. And I think more than ever, you are becoming the product. And if you don't look at yourself as a product and you have your brand, you have your marketing, you have your sales, you're going to need to do all of it in order to be successful these days,

especially in this lack of trust era that everybody can fake it. But if you don't look at yourself as a product with the whole shebang, you're like, you're going to miss out. Especially nowadays. You're right. Everybody is the brand, the product, the service, everything. We need to pause for a super brief break. and while we do, take a moment and share this episode with every single person who may be inspired

by this because this information can truly change your life and theirs. Now, I want to check in with you. Yes, you. Are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be? Do you secretly feel you should have been further along in your income, influence, or impact? Do you ever wonder how to create not just a paycheck, but the life you want was a paycheck? The thought leadership, the legacy, the freedom. Because that was me, and that's exactly why I created the Leap Academy program, which already changed thousands of careers in lives. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. AQ, adaptability, reinventing, and leaping are today the most important skills for the future of work.

Building portfolio careers, multiple streams of income and ventures are no longer and nice to have. It's a must have, but no one is teaching this except for us in Leap Academy. So if you want more from your career in life, go to leapacademy.com slash training. Check out this completely free training about ways to fast-track your career and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com slash training. So you decide, though, to start your own thing. are you not scared, you know what it's like to not have money. And suddenly you have this pretty awesome paycheck. Tell me a little bit about that journey. I didn't get an awesome paycheck for a long

time. So me and my ex and my kids' mom started the business together. It was back in 99 and 98. So back when I worked for the fitness company, I used to make $500 a week. And we had to generate the sales in order to pay ourselves. Because if we didn't, the company didn't like to send you more money. So we have to get checks and put it into the talent to pay ourselves. So from a, Learning that, I was like, man, the cash flow is really important, but I don't get a paycheck. I don't think a lot of people have experienced that in their life, especially people that have had jobs, having to make enough cash. And that is for yourself. Like, you know, I've had employees back in the early days where I didn't make money, but they did.

I had to pay them. Yeah. So sometimes I couldn't make a check. And my co-founder and ex, sometimes she didn't get paid for a few months or maybe even a year. She was getting zero and that was getting $500 a week. And that was, we were able to afford, you know, her modest lifestyle then. But I'd had friends in that time frame coming to when we first started the business. My friend Carrie Hackeray came with this $20,000 check.

Here's my commission. And I'm going, oh, my God, I should go get a job. He's made $20,000. And I'm like making $500 or $2,000. He's making 10X. And here I am with this risk and have employees. And he's just living the life. And it took a while, years to really make a nice paycheck.

I mean, it's crazy. Yeah. But tell me before you started, because at that point, you were still in the mortgage business and then you decide to start your own, what made you start American financing? The market kind of got sour on those 125% loan-a-value deals. So they kind of had some rough years

and then it started thinking, well, man, I need to start doing something. So then we started looking into becoming a broker and figured out how to do that. Back to the day, it was a little bit easier. To start your own mortgage company back then was easier. But now it's very, very regulated. It's not an easy thing to do now.

So I'm glad that I learned it back early on. So it was partially necessity, But I've always wanted to start my own business back then from reading the books. My brother's very entrepreneur. We already had started a couple little businesses that didn't go well. They were great learning experiences. And a lot of times what entrepreneurs do is they steal the ideas from whoever they work for. So like at the National Fitness Corporation, they went a different direction.

We ended up doing the same thing and learning how it works. And it worked okay. It was nothing crazy. So then when we got to the mortgages, you know, you average a lot like a two-year membership for fitness. clubs is $19 a month times whatever it is. It was a $480 for two-year contract versus a mortgage you could make back in those days three to $5,000 to $5,000 a deal. We're like, whoa. So you don't have to have as many leads. You could do a lot less. And it's much more complicated and much more complex. But just doing the math, you're like, oh, man, this is great. And back then you

could just find a deal, broker it out to a bank and then they'd buy it. I think you could still do that now, but that's a different business. It's not the same now. But yes, to me it's just simple. The mathematics made a lot of sense. So you go for it. Yeah, just went for it. You know, I think a lot of times when you do the math, I love Excel or just even pen and paper and just going, this plus this plus this equals that. And then just working that problem out. And a lot of people don't even do that. And like, I'll ask people.

A lot of people don't even do it with their own personal finances, which is wild to me. But tell me, you start your own business. And like you said, the early days and even later when you have teams, like it's scary. And how do you, first of all, deal with distress? and how do you adapt to like hard eras, like housing crash, high interest rates, so many things that happen in a business that when your employee, it almost like, yes, you might be laid off, but it's in general, it just feels a little more stable. When you're an entrepreneur, you have a roller coaster that you need to deal with.

How do you deal with the stress? Yeah, that's where we were talking earlier. It's not for everyone because if you're an employee, you lose your paycheck. I used to go get another job. And right now, I mean, I think in the U.S. even now, I don't know how it's going to be here in the near future with AI, but there's a lot of jobs out. You could get a job if you want.

And back then, before I started the business, I had three jobs. I was a janitor, did Loms, and it was a Kmart cashier. So I saved up money in order to start a business. So for me, like starting a business was way better than having three different jobs to pay the bills. And the whole point of having those three jobs was to save enough money for the business. And the way I thought about it, well, if I lose this nest egg, this little money that I saved,

then I could just go get jobs again, make it back up, and then start again, and then learn along the way. But I don't think right now, the work ethic is not what it used to be, from my opinion, having three jobs. I don't know many people that have that anymore. Back in the day, I just know quite a few people. Like, yeah, I had two jobs. That was normal.

And maybe it's still happening. Maybe I'm not seeing it. But as the crashes go down, we've been in business now 26 years since 99, yeah, dealing with those things. I've always been one of those that lives well below my means. I always have money in the bank. I've never borrowed a dime. I've bootstrapped and it could be a blessing or not.

There's companies that are much bigger than mine that have gone public or in the same industry. And I've just not taken those risks, but yet, and I may in the future. But I've never felt that nervous because I always had enough in the bank. And I knew what my nest egg was. I knew I could survive. They always say at least three months, but I knew I could survive much longer than that because I just didn't overspent. So for me, it wasn't that bad.

Our worst year, we lost $26 million. Those are rough, but I knew I could take that hit. And a lot of companies in my industry didn't take the hit. They ended up going out of business. They just didn't plan for it. And by the way, in the U.S., failure is a part of success. If you fail, you learn from your mistakes, try not to duplicate them, and you start back over. We have bankruptcy in the U.S.

Luckily, I've never had to do anything like that. But some countries, you can't do that. But here, you learn and you start again. So take me to a hard day like this. I think every entrepreneur will have their own hard days and that they needed to lay off or they needed to whatever. Like, take me to the evening before or whatever.

Like, how do you, you know, rationalize it? What do you do? How do you not give up? I've had two big layoffs in our organization since we started like 2008, 2009 mortgage collapse. We had to layoff people, but we were much smaller than maybe around 80 to like, say, 60. or 50 and those are rough because sometimes

in employees it could have been with you for 10 years. So that's really sad when that happens. But more recently after interest rates went up the fastest in history, we were from 1,200 employees down to 50. That was really, really rough. Again, I think as a room for me, being raised in that with a lot of money,

is you have fear of losing it all, right? And I still have that fear. I think companies and people are much more successful when we have lost it all. So that could always happen to you if you just make a few bad decisions. So I think looking at the math and saying, okay, we could survive here at this and then having that faith to just go for it. And even I don't make any money. At least my team is there

and I can rebuild when the time is right, which is we're kind of now because we went from, you know, billion dollar evaluation back in a $201, $22 billion dollar offer to sell. I didn't take it. And then to the next year losing $28 million. And then those things are like, wow, should have taken that. Maybe who knows what's right or wrong. Yeah, oh my God. I mean, this is a crazy ride. And I think there's also, you talked about a little bit of what's going on now. And I think there's like books like the four-hour work week and other books that almost make you feel and seeing people on social media that it's always easy for everybody and they just work a little bit. And only I'm grinding. Right. But that's not true because in order to build what you created like bootstrap to a billion dollar valuation. Like that is. is not normal. Talk to me a little bit also about that offer because, yes, not everybody gets this kind of an offer. And what made you say no? And how do you even rationalize something like this? I want to go touch on here four-hour work week. Like, by the way, I used to recommend that

book. I do not recommend it anymore. What it did for me, it made me lazy. And I'm like, wow, I could do all this. And by the way, it works. I could do that. But would I rather be chilling at the beach or playing golf rather than Elon Musk, which I don't think. ever sleeps or stops. I'd rather somewhere in between. I don't want to be like the guy only just four hour working and I don't want to be only working, but the other one really gives you this ability that you could still get results with very little effort. Like I'd rather give a lot more effort and even my results on there. Just keep on learning and right. Because that's how you stay fulfilled. And you know, I've had that where you don't work enough and that's not great. But the

billion dollar offer came and we went to market and I don't know if you've ever gone to market. It is a process. You got to get all your financials imperfectly. You get a data room and you get a firm to then go and pitch you. So they pitch you to all these organizations and they'll get a list. Okay, okay, out of everybody we sent this thing, there's this many companies that are interested. And then there's strategic investors that are in your same industry that may want to buy you to add into your fold or all sorts of different or your employees or what have you or your list. And then there's this P firms that, you know, kind of outside want to compete with the market. So we looked at strategics, by the way, you got to be very careful what information you give them because some of them are,

just trying to steal your data. They already know you're successful, like, well, how much can it take? And they lead you on even. They'll say things like, oh, we're really interested. We're going to put an offer in. And then right before like, oh, you know what? Something was wrong. So I'm very careful with giving any information out.

And then a P-Firm came, gave us a $960 million offer. And I'm like, wow. And we kind of knew where their valuation was because we before did an evaluation somewhere 900 to even went as high as $1.5 billion. Evaluations are just what somebody is willing to pay and what you agree on. I mean, so I saw it, and it was 450 million up front, but our best year, you know, we did whatever was hundreds of millions of dollars gross and then say 150, 160 net. And then when I did the math, it was like two years of EBTA in my eyes. And that was before I knew rates were going

to skyrocket. I'm like, well, I'm going to make that up in two years. Plus there's an earn out. So I like, you know, I'll hold off. I'm not going to do it right now. And then rates skyrocketed shortly thereafter, not right there. And then I don't even look at it as a negative as a learning experience. I believe now we're positioned to even grow better and bigger than we were before as rates go down in this market right now. So we'll see. But it was definitely a learning experience. How do you morph as a leader?

And then we'll talk about Puerto Rico because now you have this whole portfolio career. But how do you feel like you're morphing as a leader that can steer these kind of ships? I mean, this is a big ship. I've always thought, and even now, like, you know, I have a boutique hotel on the beach and restaurant and I have a great manager and she runs it and we have meetings if we need them. I try not to get involved in my main business, American financing. You know, we have two weekly meetings. I'm very involved in the numbers.

And it's a matter of hiring the right people and making sure they're the right cultural fit and just managing at that level. And as, you know, both of us know Richard Branson pretty well. And I've seen him how he operates. And I mean, he's running a lot of businesses and he's one man and he's doing it with keeping amazing culture. If you go to the Virgin Airlines, Virgin Cruise Lines, Necker Island, the service is just like you feel like your family in these businesses. And he has to have amazing managers and amazing PAs.

And it's really interesting when you have so much knowledge that you've built up that you're able to make decisions extremely fast because you've already been there, done that. And you don't have to like analyze and like this is the right thing. and you have somebody you could execute that. So you touched it. So I have to go there. I think Richard Branson has become one of the biggest mentors in my life. It looks like you've been around him for a long time.

You play chess with him. Every time he sees you, he's like, damn, man, chess. That's really cute. What do you feel are some of the things that you learn? Because he's big on delegation, you're right. But what other things that you feel like you learned from somebody like him and from that level of proximity that you put yourself in? he's an amazing businessman, but an amazing father, amazing husband. He's just an amazing person.

I've never seen him in a bad mood. We were climbing Mount Blanc once, and he thought a rock hit his son and Sam and Noah, and that was the first time I seen him spooked because he thought that they died. But other than something that dramatic, we're climbing these amazing 14,000 foot elevation gains, which is very painful. And it takes a long time. He's still smiling. If you go next to him on a bike, he's saying, hello, how are you with a smile? And those kind of scenarios where really physically demanding, he's like that. But then on a regular life, how he treats everyone exactly the same. It's really humbling because somebody as magnetic and as big personality of the world, a world leader, I consider him

not just a business leader, because he's very involved in so many different things. To be that humble and nice and kind to everyone is really eye-opening because you meet people that aren't even close to his level, treating people badly. And I'm like, why do you do that? Oh, and I love that. And it sounds like you embed that too, because from everything I hear, even people that you guys had to lay off now they're coming back because it's like that's the kind of culture that you created. And I think a lot of it is like when you are in the proximity of leaders that you appreciate and aspire to, you learn a lot even just by seeing it. They don't need to like actually mentor you, you just see it and you start becoming a different leader. Do you see that too?

Yeah, I definitely agree with you. Like you see these little things and we've traveled around the world with, say, with Richard Nuthersvich, just seeing how they are even saying, you know, we just took a trip to India. And arguably India is not the easiest country to travel and what you see is really eye-opening and you're like, wow. And, you know, one of the speeches we saw on the strive that we were together on is when, what was the guy's name? that was traveling with us? Maybe Vishal. Yeah, Vishal, Michelle, that's who it was, yeah.

But one of his speeches, he said, he was brought up, like, a lot of the people that we've rode on our bikes were, like, extreme poverty, like the kind of poverty that I experienced, having a shelter and a system for that. I imagine they have that in some areas in India, but I don't think the majority of India has even a system.

Like, you're literally homeless. There's nowhere to go to get a bed and a food, and that's very wild. But he goes, when I was growing up like that, I didn't even know I was poor. And that was really eye-opening to me because as we were riding through that, I'm like, huh, I wonder if a lot of them know they're poor.

And he goes, until I went to university, then I'm like, oh, wow, I'm very different than a lot of the people here. And that was really eye-opening to me. And so to see how we're us going through there as a group of entrepreneurs and just seeing how everybody treats, I think that group itself treats people,

even to do strive, you've got to be a certain type of person. And I think we've all learned from similar people, and I bet you we've read a lot of the same, books and that being in that state of mind of it's being kind to everyone, I think it's really important. We need to pause for a super brief break and while we do take a moment and share this episode with every single person who may be inspired by this because this information can truly change your life and theirs. Now, every cool opportunity you will ever find is most likely from a

hidden market. It's the people who think about you when you're not in the room and bring the right opportunities to you. This means that the people you hang out with truly matter. That's why we created our flagship live event in San Jose, California, in the heart of Silicon Valley. It's February 26 to 28th, and it's the number one conference for reinvention, leadership, and careers in the United States. It has speakers like the former president of Starbucks and many other leaders, including yours, truly, myself. And I'd love to personally welcome you, give you a hug, and here we're, what you think about the podcast. We'll have many networking opportunities, photo opportunities, and we already know every single person after this event will go supersonic on their reputation

and career. So grab your tickets quickly because this event always sells out. So go to leapacademy.com or you can search on Google leapcon, LeapCon, 26. It's L-E-A-P-C-O-N. Don't miss out where the most impactful leaders hang out in February. go to leapacademy.com slash leapcon. I will see you there. How did you get to Puerto Rico? Why Puerto Rico out of all the places in the world? And I'm sure kite surfing has something to do with it. But take us there. David. Yeah. So I love the kite surf. I've started kite surf in 2008, 2009. The company wasn't doing well, but we had enough savings. So got an apartment in South Beach. And I saw these guys kite surfing in the back. And I'm like, oh, my God, I have to do that.

I don't know the first time you see the sport, you're like, went to kite and your cruiser on top of the water. It's amazing. So I got hooked. It took me a long time to learn because I bought gear from a guy on the beach, and then I tried to teach myself with YouTube. Bad idea. I think you should go and get lessons.

Now we have a kite school school, but it takes five to six days, total immersion, get lessons and do it. But I met my partner, Dylan, in Puylo Carmen and Mexico, and him and his wife, Shadi, the hotel that were behind was kind of like renewing their deal, and they didn't want to renew their kite deal. So I'm like, we should open up at high school together. So we're looking around,

we're like somewhere in the Caribbean. We're looking everywhere. And we went to Dominican Republic and this place Cal Cabarette, which is beautiful kitesurfing village and other water sports too. And we're looking on the map and my buddy goes, what about Puerto Rico?

And I'm like, and I'm Puerto Rican, but I hadn't thought of it that way. And start looking at the data is like, it's very windy here. Eight to ten months out of a year, it's windy here. Most places are, there's three, six, seven months,

a lot, a lot less time. So we end up coming back, scouting the island and finding this little boutique hotel called Nomadono and ended up buying that to open up the kite school there. And that's what we did. And it came with a little restaurant, came with a little boutique hotel. We only wanted to do the kite part. We ended up with these two other businesses and ended up being a cool business and a cool location. But kite surfans, well, chasing the wind got me back to Puerto Rico. Wow. I love how you're just not afraid of change. Like, I think that's the big theme that I'm

getting out of this conversation. Like, you're almost leaning. into the change because it's exciting and it brings adventure and it brings, you know, fun. I mean, we talk a lot about portfolio career. We have, you know, a big event, LeapCon, which is probably the only conference and event that teaches how to create portfolio careers and it's happening in February. But you live it. You have a huge business. You have a surfing school. You have the beach house. You have podcasts. You have movies. You have like all these things. And you combine it with adventure. How do you do it? I'm very comfortable with uncomfortable. And, you know, if I'm going on a trip, I buy a one-way ticket and just try to figure out sometimes

I have a hotel, sometimes I don't. Yeah, I'm really comfortable and just not having any kind of plan. I think no plan is the best plan. Sometimes it backfires, you know, he end up having to figure out where to sleep in a corner somewhere. If I'm alone, if I'm with trauma with somebody, you can't do it quite the same. But yeah, I'm very much into just figuring out as you go, I don't. I don't know where I got that for because it's not the, I think I should plan a little bit better, though, just a little bit. I'm curious, except for what we talked about. Do you think there's some event in your childhood or early career that kind of built you

to Damien that we see today? I used think the books, having the right mentors, asking a lot of questions. I ask a lot of questions, and I see my kids doing that now, too. I took them to one of the strives in Necker, and they, I know. I remember. That's how I met them. Oh, so cool. That was so inspiring, by the way. Thank you. They loved it and I can't wait to take them again, but they were sitting with the adults asking questions and they didn't want to sit with me and I'm like, they're asking really good questions. And one of the questions they even asked Richard was like, do you like being famous? And I'm like, you know, most people would not ask that question to him or other famous people. It's kind of an interesting question. He's like, hmm, you know, because I could reach anybody when I need to reach them, for that reason, I like to be famous. And it's such a good answer. because I think... That's a beautiful answer.

Yeah, and I think learning from just those types of things, but I think it's been a kind of layering, and I'm still figuring it out. I don't have anything. I still have a lot more to do, and I definitely don't consider myself like I've arrived or anything like that. Where do you see your future?

Well, as we continue to build our main business make and financing, which we're really excited about the future here. I invest in a lot of different businesses. I'm invested in one fund that invests in our business, stage startups. For Puerto Rico, there's a lot of tax advantages here. I didn't move here for that, but as I get into this next phase and continue to build these business that I'm already involved in, I want to incubate businesses, like early, early stage businesses, get them to move to Puerto Rico, help them with what I've learned and help them build their brand and also have fun with them

and do it in a beautiful place and something that's scalable. So I think that sounds fun. I think it sounds fun also for my kids to see that. I think learning that from an early age, then you kind of look at the world differently. It's what sounds the most fun. I haven't thought of anything that sounds more interesting than that. And I think the fun factor, adventure, fun is always kind of a theme, the impact, like the businesses, all of it, but also you always blend it with like fun, which is really, really cool. So Damien, I'll ask two things. One, if our listeners are hearing, you know, when they're hearing this and they want to help, or they want to get involved or they want to find you and follow you.

So first of all, how do they follow you? But also, what kind of help if people want to be in your vicinity? How can they help you? Like, I think sometimes as we see these leaders and we're like, I don't know how I can help them, but if I can't help them, I can't get out of the people's pile, right? Like, I'm always in this people pile. I'm always, like, begging them.

But how can they help you? I think if anybody has good ideas that they want to kind of build out, I think just Puerto Rico in general is just a great place to do it. But if anybody's looking for that kind of thing, you know, coming to Puerto Rico and checking it out for yourself, it's just, it became one of those. I'm not like a digital nomad place for a little bit while during COVID and has good infrastructures.

So anyways, just, you know, reaching out. My main little boutique hotels called Numidto Uno. It's right in this area called Ocean Park. It's 15 minutes from the airport, which I need to get you here one of these days. Come for a few days. Totally need to do this. Yeah.

Like totally. You'll like it. You can do your podcast from here. I have like a studio set up and an operation here. Obviously I think your business has a lot. It's very cool. You know, as I learn more about it and you're teaching basically entrepreneurs how.

Professionals and entrepreneurs, how to be successful. Yeah. So everything I wish I had 20 years ago. That was great. I mean, I've had to do it through books, but like the courses that like teach you is like a shortcut to,

you know, learning from other people's mistakes and just getting the fast track, I think is really important. And I think it's one of those things you could do for the rest of your life. There's no cap of how far you could go. So I'm glad you're doing what you're doing. Oh, thank you. So what would you say to your younger self? Like if you met little Damien, what would you tell him right now?

I would say keep reading and keep implying what you learn, keep surrounding yourself with great people. this quote from Anthony Robbins is success without fulfillment is failure and I went to a seminar years ago in Denver another one I've got to a few of them and that hit me really hard

because at the time I didn't feel fulfilled and I had reached a lot of my goals and I think it's like when you get too comfortable at any stage in your life you start going well what's it all about and you're asking the wrong questions

rather than if you're still keeping yourself busy especially physically, you know, hitting the gym, cardio, all those types of things. I would say, you know, don't ever take a break from that. Always just keep on striving and keep on because no matter what level of success you reach, just keep on going. Oh, mic drop. This was so good.

Amen. Thank you for being in the show, for inspiring, for the incredible journey, for everything that you're doing. And can't wait to meet in Puerto Rico, but also in Iceland. Yeah, that's going to be a lot of fun. Well, thank you for having me on the show. I love hearing your story as well. I look forward to connecting again, Iceland, Puerto Rico, anywhere. Okay, so once a week, we pick a question that you submitted and you put in a comment on our YouTube channel, Leap Academy with Zilana Golan. And we take that question and I answer it live. And our question today is from Maya Nasirio.

And she asked a beautiful question. And she basically said, if I'm asked, Tell me about yourself, which is, by the way, the most common question you've ever going to be asked, whether it's in an interview or networking or a pitch for investors or whatever. Tell me about yourself. How do I know who's in the room with me? How do I know how to craft an answer that they will relate to? So let me give you one of the most important lessons in your life about Tell Me About yourself. And it's completely going to transform the way you introduce yourself in every conversation. so buckle up leading in in the next few minutes. So I don't know if you've ever done

what is called the disc assessment. If you haven't, there's plenty of free disc assessment, short, long, et cetera, more elaborated. We do one in Leap Academy, but there's plenty of free ones on the web. And the disc assessment just basically shows you how people behave and how people adapt to different conversation,

different situations that happen around them. In general, humans are divided into four sections according to this, the first section is the Ds, the high D disc, right? So the high Ds are dominance. They are basically driven by achievement's results. We'll see how that relates. The high eyes are the influence. They are the one that are kind of the light of the party. They're enthusiastic. They really care about social stuff. The steady, the S disc is for steady. There needs stability. They want to help others, et cetera. And the conscientious, which is the C. They need accuracy. They need quality. etc. Now, how is that related to tell me about yourself? Here is a nugget, okay? So the high Ds

lose patience the fastest, okay? They need to hear achievements, achievements, results, numbers, numbers, otherwise you lose them. You lose them within 30 seconds through their thoughts or their phones, okay? So the very first thing is to, in every pitch, is you want to make sure you don't lose the high Ds. And in order to not lose the high Ds, you need to talk. about your achievements, your numbers, we grew X, we reached a million, we are one of the fastest growing, whatever it is, you need to talk about achievements and result. It needs to be tangible, it needs to be specific. It has to have numbers or something that they can actually relate to. It's not the fluff. The eyes, you're going to lose their patience in about a minute.

So if the high Ds, you're going to lose them in about 30 seconds, the high eyes, you have a little longer to lose them. What this means. Now, the high eyes, because there are social people, they will really, really relate to name dropping. They will very much relate to fear of missing out. So if you have something that will create, oh my God, everybody else wants them, you need to want them. They will want you. Okay. So they are very motivated by a fear of missing out and name dropping. The studies, you have more time. You're going to not lose them very easily. need to hear that it's a proven system, that it's engineered process, that it's worked for others. So they need more details. And the Cs, the conscientious, you will never satisfy everything that they need

in one pitch. Hence, if you're going to try to create a story that is too long, too much details, you're actually going to lose the high Ds and the high eyes. What does it mean about Tell Me About Yourself? So let's dive in. So in the Tell Me About Yourself, the very first, you're going to tell me about first few sentences have to be achievements, numbers, et cetera. Right after that, it's going to be all about name dropping, things that you've done, companies you work with, investors that invested in you, whatever it is. And after that, you're going to talk about the proven system because then your pitch will satisfy all of them. So let's take a look at what does it look like, for example, if I need to introduce myself, because what I'm going to touch is every single one of them.

Right. So in Leap Academy, we help driven professionals and entrepreneur reinvent leap their careers. And we are one of the fastest growing private companies in America for two years in a row. In 2003, we were startup of the year. So this has worked for thousands of people. Our programs, you're going to see people that moved from director to CEOs, ring the bell in NASDAG that landed board seats, landed advisory roles, building incredible portfolio careers, did speaking opportunities, And by the way, our podcast speaks to some of the biggest leaders of our time like Rachel Branson and Gary V, the founders of Airbnb and Zillow and Wikipedia, and I can go on and on. Our event, LeapCon, is the number one event for reinvention and leadership and portfolio careers

in the U.S. And it's already proven. So, again, we have proven systems that work for thousands of people. It's very simple to follow, not easy to do. but it's very simple to follow and it just works for any single person who is driven, to reinvent, and leave their full potential. That's our pitch. Like, I don't know how long it took.

It's probably a minute. But basically, think about it. It touches all the different components. It talks about the achievements. It talks about the results. It talks about maybe if I would add a little longer, I would say people landed in companies such as Facebook, Microsoft, and in venture capital and private equity and startups, et cetera. So maybe I would add.

that a little bit to the pitch, but that's about it. So tell me about yourself. I want you to write down your three big achievements in big numbers. Like, what have you actually achieved that is relevant to words where you want to go? You're going to add name dropping, and then you're going to add why it's a proven system and why they need to hire you or why your product works. Okay. So that's it. You know, in just a few minutes. If you like this, let us know in the comments on YouTube. If you have more questions, comments so that we can choose your question and talk about it next week. I'll see you soon. Remember this episode is not just for you and me. You never know whose life you're meant to change by sharing this episode with them. And if you love today's episode,

please click the subscribe or download button for the show and give it a five-star review. This really means the world. Join me in helping tens of millions of individuals reinvent their career and leap into their full potential. Look, get it. Getting intentional and strategic with your career is now more important than ever. The skills for success have changed. AQ, adaptability, reinventing, and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures, are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in life, go to leapacademy.com slash training.

Check out our completely free training about ways to fast track your career. You'll even be able to book a completely free career strategy call with my team. So go to leapacademy.com slash training.