Broke to a $1 Billion Dollar Exit with Bobby Castro – EP 176

Interview with Bobby Castro

Broke to a $1 Billion Dollar Exit with Bobby Castro

Featured on This Episode: Bobby Castro

✅ Bobby Castro Full Bio: Bobby Castro started his entrepreneurial journey with a modest ninth-grade education and a small but significant $1,700 gift from his mother-in-law, Dixie. This initial capital became the seed for founding Bankers Healthcare Group (BHG) in 2001, a venture that would grow his net worth to over $500 million.

Under his guidance, BHG flourished from its humble beginnings to achieve a billion-dollar exit and sale. Beyond BHG, Castro, alongside his wife Sofia, founded Ortsac Capital Group, LLC. This family office oversees a multifamily real estate portfolio valued at over $700 million, encompassing more than 2,500 units across states like Florida, Texas, and Tennessee. This venture alone generates over $500,000 in positive cash flow monthly, alongside various other successful investments.

Castro was honored with the Ernst & Young Entrepreneur of the Year Award in 2012, and BHG has been featured on the Inc. 500/5000 list an impressive 13 times. His achievements have been recognized by Fortune, Forbes, Entrepreneur, Hispanic 500, and Crain’s, among others. His journey and insights have also been highlighted in the Wall Street Journal, Bloomberg, Smart Business Magazine, and CNBC.

💬 Words of wisdom: “Everyone thinks money brings happiness and joy. Money brings resources and access. It allows you to have flexibility, but it does not bring you happiness. I can assure you that.” – Bobby Castro

🔎 Where to find Bobby Castro: Instagram | LinkedIn | YouTube | X

Key Takeaways with Bobby Castro

• Starting off dirt-poor
• How the super-rich think about money
• Why most people never become wealthy
• From broke to exiting for $1 BILLION
• The danger of letting your ego lead
• Working in the business vs. working on the business
• Rockefellers VS Vanderbilts
• Wealth creation should never be fully outsourced
• The role faith plays in life
• UPSIDERS by Bobby Castro

How Billionaires Think About Money | Bobby Castro

Bobby Castro Tweetables

Resources

• BobbyCastro.com
• Bobby Castro on Instagram | LinkedIn | YouTube | X
• UPSIDERS: End the confusion, kill your distractions & create permanent change by Bobby Castro
• Denny’s
• Rusty Pelican
• Better Business Bureau
• Tim Tebow
• Pete Vargas
• The Wellspring

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Read the Full Transcript with Bobby Castro

Justin Donald: Hey, Bobby. So good to have you on the show.

Bobby Castro: Thank you. Thank you for having me, Justin.

Justin Donald: Yeah. This is going to be fun. We’ve talked about, for a little while, getting you on the show and learning more about you and your story. And I just have to say, I’ve heard your name for a while. We’ve got a lot of mutual friends and many of them have told me about you over the years. So, it’s funny that it took us this long to connect and get you on the show but, that said, your story is one of the coolest and most inspiring stories of any entrepreneur that I’ve met. So, I can’t wait to just have you unfold all the cool things that are going on in your life.

Bobby Castro: Well, thank you for those kind comments. And for the ones that will listen and the ones that are listening right now, this is all true, true factual stories, but more so I want everyone to really focus, Justin, of how that progression leads to outcomes.

Justin Donald: Yeah. I think that’s great and I do think that it’s important that we have a focus on outcomes. In fact, at the end of every episode that we do, I talk about taking one step and what is that one step that you’re going to take some form of action on. So, we can definitely get into that. But I’d love to hear how you figured out, first and foremost, that you were an entrepreneur. How early was that in life?

Bobby Castro: Yeah. Super early. So, my mother, she was a waitress all her life. She’s still around. She’s 84 years old. She’s amazing. She’s definitely the anchor and the core of my life. And she was a waitress all her life. Before Denny’s, it used to be called Sambo’s, and my mother worked in the graveyard shift practically from midnight to 7 a.m. And that awesome waitress that used to wait on you, I’m sure when you get done with a wedding, whatever, that was my mom. And from there, she walked home. She didn’t drive home because there was no car to drive home, and we lived close to the restaurants. And then practically 4:00, she got into another uniform to Boswalli’s, an Italian restaurant, and she walked there as well. And she was a waitress at this Italian restaurant. And I saw my mom all my life give value to others and just working for that 18%, meaning no matter how difficult your personality is, no matter how bad of a day she had, and we grew up financially struggling like a lot of people that are going to be listening to this podcast or listening right now. We lived on food stamps, government assistance, just like a lot of people. And I witnessed my mom doing this all her life.

And at ninth grade, ninth grade back then, that was not high school, it was junior high, Justin, I told my mom, I said, “Mom, school is not for me,” because I was struggling in school because I just even today, it takes some time to put things together and I have to ask a lot of questions to really understand it. So, at ninth grade, I just finished in ninth grade and I left school and I started in the footsteps of my mother. Instantly, I knew I wanted something a lot more and how it was during growing up. There was fleas. There was roaches. There was a lot of things. No electricity, no water. I don’t say that lightly or exaggerate on it. It made who I was because I said, “This is just not normal. There’s something better.” And the reason I knew there was something better, my mother, including me when I was a waiter, when I started a company that I eventually sold for $1 billion with no raise and no money, etcetera, I found out to be true was I used to wait on people that actually entrepreneurs and business owners, but also I caught a disease that a lot of the people I was waiting on was a lot of flash dancers, and they had the gold Rolex.

So, waiting on individuals that appeared to have success and some of them actually did have success. But I was skewed and I got fascinated really quick on the profiles that had these dynamic personalities, these profiles that had an ego that I eventually learn the ego is not your amigo that had this big shiny Rolex, had a Mercedes, BMW, whatever. And I was fixated on it, and I called them in my book, UPSIDERS, flash dancers. I wanted to be a flash dancer, and I knew I wanted to be an entrepreneur. So, it was an exciting time but, yeah, it was a very confusing time that really did more damage in my life, which I’m very grateful. I, 56 years old, looking back of those mistakes, more so grateful for the lessons. It took me a while to stop repeating them and that’s when I knew I wanted to be an entrepreneur.

Justin Donald: Yeah. That’s awesome. Well, it’s cool that you have learned a lot of these lessons. Now, with the flash dancers, I think for a lot of new entrepreneurs that come into money or, I mean, even on the business professional side, so let’s say you’re not even an entrepreneur. You’re coming into money. This is more money than you’ve ever had, especially as you graduate college and get promotions and all this. You said that there’s a disease aspect to it, and I totally think that is like consumerism itself as a disease. And we got to be careful that we use it for the good, and we don’t overconsume, right?

Bobby Castro: Absolutely.

Justin Donald: We don’t spend money for the show, for the flash to become a flash dancer for the sake of doing it because I also think at a certain point, when you become successful enough, let’s call it on paper, financially. I think we have an obligation to be able to help others and use those dollars in a way that’s not just for our own consumption.

Bobby Castro: Yeah. Your relationship with money, a lot of people have a different type of relationship with money for good, bad, and ugly. And I had a relationship with money that just that being a flash dancer. Until I started realizing the power of money and how to leverage money, and once that I would love to just shoot out, if I may, with your permission.

Justin Donald: Sure.

Bobby Castro: It’s crazy. There was a lot of flash dancers. A flash dancer is basically what you just outlined, spending money they don’t have, having things they can’t afford to have just to have it for the sake of, “I’m doing good.” And we have a lot of that, unfortunately, on social media. So, check this out. One penny, one lousy penny that most will walk over and not pick up. Matter of fact, even if you offer it to a homeless person, they’ll throw it back at you being insulted. But let me just explain the relationship with money. There’s one data point of many. One penny a day compounded every day for a lousy 30 days equals over $5 million. Now, when you really think about the power of compounding and leveraging your money instead of spending your money, this is how the wealthy get wealthy, and this is how you can impact the world. This is what I found out to be fully true when we became financially free. See, a lot of people seeing Sofi and I exit a company selling it for a billion, but they have no clue for the last 20 years before exiting for a billion how we were compounding wealth, having a relationship with money, and more so not losing ourselves to money.

There was a time that Bobby worked for money instead of the money working for me. See, money amplifies who you really are at the moment and you see a lot of people loss, having not a relationship with money, and they’re just either blowing it or being extremely in debt, and they’re not ever going to create anything other than misery, depression, and self-destruct their lives like I did, including almost getting divorced many times. I’ve been married 33 years together, 34 years. I almost screwed it up not once, twice, many times. And I go heavily in the book. So, with a relationship with the money, everyone thinks money brings happiness, money brings joy, money brings resources and access. It allows you to have flexibility, but it does not bring you happiness. I can assure you that. I thought it would and it didn’t.

Justin Donald: Yeah. You know, that’s a profound statement because for most people, until they realize that themselves, like you have this big expectation that you build a company, you sell it, and then all of a sudden, you’re going to feel just amazing. It’s like everything you ever dreamed of. And unfortunately, it is exactly, I mean, it’s so far away from that that I find that most people, even inside the Lifestyle Investor community, it’s such a flip flop from reality because it’s not that because money didn’t solve it. And now not only did it not solve it, you had these grandiose plans that it would. So, it’s so far from the truth of what happens and it leaves a lot of people who come into money really depressed.

Bobby Castro: It does. Justin, let me tell you a stat that my wife and I are up against. In Las Vegas is betting on that we get it wrong and the odds are in their favor. Sofi and I created an event in our life. Over 73% chance my family is going to blow it, meaning that my daughter, my son, and their spouses are going to blow it off, blow it off, and they don’t have a relationship with money, and nothing is in there for our generations. The chances are very high that’s going to happen. And my wife and I have a 100-year legacy plan that we want to make sure our children don’t live this money life. If you meet my children, you will have no clue that maybe they have some economics within the family. They’re very humble. They’re being coached on every single day from Dr. Orlando and his team. I’m being coached one-on-one to make sure we continue to grow, grow, grow, and not have this money machine become a machine in our life to determine our happiness, our direction. And it’s a battle we have on our hands because I have grandchildren now. And I’m telling you, man, when I got that first wire transfer and it was a big wire transfer. I was not even phased. My wife, well, full transparency, she was very emotional, extremely over-emotional the most I’ve ever seen her because she felt bad for her family. She had a different reaction than I.

I really didn’t because I passed that mark some years ago and a lot of people say, “Well, Bobby, now you seem like you’re so cool. You wear an Apple Watch. You just wear a pair of jeans.” It’s just I’ve learned my lesson of not having money control me. I was a money junkie. All I wanted was a transaction, money to go buy a Rolex. First, it was a fake Rolex. Justin, see what I got? I won’t tell you but I’m going to flex like this. And I live that life, which is called a lie. I lived it. I almost destroyed my marriage, my life, and so many relationships along the way. I am grateful for those mistakes. I am grateful for that younger Bobby. I am also grateful for the other Bobby that learned the lesson. So, guys, watch this money situation. When you’re combing through social media and you’re waking up and you’re scrolling, seeing all the parties, you’re seeing all this flexing, there’s not happiness there, guys. The most important thing is that what do you want out of your life? How do you feel? Forget about how other people feel about you, how you’re trying to impress them. I see so many people, Justin, I know I’m getting off-topic. I go to the mall and I see them in line at the Gucci store, then have the line on the Louis Vuitton and I know the behavior. That was me.

And I’m saying there’s a good chunk of people here that may not be able to afford this. Why are they doing that? Because you’re only buying that symbol that’s on that bottle, not because it feels good. Because I see these beautiful ladies in this beautiful shoe that they pay $1,000, and ten minutes later, they take it off because it’s so uncomfortable. But everyone’s buying this stuff for the purpose of someone else seeing them having good things or flexing. And I don’t think that’s personal growth. I think you will never create wealth if you’re on that path.

Justin Donald: Yeah. And I think a lot of that, there’s a mindset shift that needs to happen but it’s an internal thing. So, there’s a compensation for maybe not having as strong of a self-image as others. So, someone with a very high self-esteem/self-image, they don’t need the external to validate who they are. They don’t need possessions in people, anything externally to validate who they are. But a lot of people, I think, don’t have that. They seek their validation in other things, in spending money and what people will think. And so, that’s the danger right there because if you don’t, so first of all, it’s dangerous whether you have the money or not. But if you don’t have the money, then you’re spending money that you don’t have to earn it, right?

Bobby Castro: Yeah. You know, and one thing I want to just squeeze in there, and I know I can go on and on with this. And this is for the ones who are listening, check this out. I’m going to give you a path. I’m going to give you a bonafide path just my personal experience. I can give you a testimonial of anyone else’s life. How I used to give up on life meaning that I will start a business, give up. I would say I’m going to do something. I’m going to lose weight. Whatever it is, I give up because what I used to do, Justin, I used to look at these individuals saying, “Wow. They got this, they earned this. Even the ones that really earned it and incredible outcomes. And I’m saying, “Wow, that’s amazing.” But then when we dig a little deeper, at least when I dug deep, I said, “Wow. That’s a lot of sacrifice. Oh my gosh, putting it on the line.” Like, my God, not going out no more separating myself for some people. And then you start seeing what truly is involved and I used to quit on it. That’s why I never started.

And then when I started, I gave up on it because I started realizing, “Oh my gosh, this is a lot of work.” And then we just sit on the sideline and we become a fan of someone else’s life and I truly believe that’s why people don’t start. They settle. They quit. They’re looking at a Bobby or a Justin today. They’re not looking at the journey and the process to get here. And when they start digging further into that, they realize, “That’s too much work. No way. I want it now. I need it now. I need the results now,” because they have gotten themselves to the point where they’re comparing their stage with someone else’s stage. They like me here, and they’re missing the most important thing, my brother. The middle part, the incredible yellow brick road to get there, it’s a process. The process and the journey, it was the biggest turn-on and it is the biggest turn-on for me today. It’s so exciting and that’s why life has no ceilings. You can never reach perfect.

Justin Donald: I love it. I love all these epiphanies and life lessons that you’ve realized along the way. You know, it’s also interesting, as you built your business so generally, there are two ways that you’re going to build a business. You’re going to bootstrap it where you’re not raising money, you’re using your own dollars, heavy reinvestment or maybe it’s like a little bit from friends and family. Or you can go the venture capital route and you raise money and maybe in time, it’s many different series. Maybe private equity comes in, but at some point there’s an exit. You have partners, financial partners along the way. I did a really cool podcast episode with the Taylor brothers because they both started companies. They both sold their companies. One of them was VC-backed. One of them was bootstrapped. The numbers were all over the board except the end of the story number, take home dollars were almost identical, which is so funny. But usually, when you hear a company had $1 billion exit, I mean, almost every single time, this is a venture-backed company, this is a company that has raised money. And I’m just so fascinated on how you could do like how on earth were you able to bootstrap something to over $1 billion exit? I’d love to talk through some of the growth, the mechanics.

Bobby Castro: Absolutely. So, here we go. And for the ones listening, pay attention, man, because your minutes are nonrefundable. You’ll never get them back. So, invest your minutes by digesting this. Look at the podcast again. Put your device away. Put everything away and dial in because you’re seeing somebody that has no motives. I’m not here to sell you anything. I have nothing to sell you. I am here to help another Bobby and Sofi. First, I would like to say I’ve come to learn. Bobby, what you give energy, full energy, and what you give focus, full focus, only one thing is guaranteed to happen. It grows crazy big. Question is, what do you give energy and what do you give focus to? Bobby used to give a lot of focus and energy everywhere. That’s why nothing grew. So, what happened was I was a waiter at the Rusty Pelican in Miami on Key Biscayne, starting over again, living at my in-laws’ house. And before that, I was a train wreck and then I just started. So, I’m passing some stuff up, and then I got my act together. I got two jobs when I was unemployed. My wife was working. We had a little baby and I was just that Bobby that was in… I was a lazy Bobby. That Bobby is not the Bobby today. That’s why constant growth is constant.

Anyways, I get a job at the Rusty Pelican. I said, Justin, enough of my mind to myself. Enough of starting to try to get from A to Z skipping the process. I am going to win right here. Forget about where Justin is. Forget about where this flash dancer is. I am right here and I am going to win like a champion. I’m going to hit that ceiling. And when I hit the ceiling, I’m going to make sure I won completely before I go. I used to be a skipper. So, anyways, I’m working on the Rusty Pelican Key Biscayne, and during the day I’m selling memberships for the Better Business Bureau, a sales job, pure commission, waiting on tables just like my mom, just like I used to do. Starting over. I used to be a classified junkie before that. My wife almost, when she was my girlfriend time, she almost left me because I actually had an addiction. No different over narcotics or alcohol. My addiction was the classified ads. There was no internet back then. Any tagline in any classified national paper or local paper that said, “Become a millionaire. Make $10,000 this month,” whatever, I was a junkie, just like a needle in a vein and I was sent away for the package.

And I would get all stimulated and just whatever. And nothing was going on to the point where my fingers were black and all that, to the point where it’s almost a turnoff for my girlfriend, Sofi, who’s my wife, because it was like nonstop this blah, blah, blah, I’m going to do this. I’m going to do that, the big talker, the big shot, the big flash dancer, that’s freaking broke. She was getting turned off, not turned on. Long story short, I walk out of her mom and dad’s house and we’re young, as you can imagine, a black Mustang on a weekday on an afternoon, late afternoon pulls up out of Pedro and in Dixie’s house, my in-laws who are no longer around, and most amazing individual, especially Dixie. Boy, God connected me to Dixie and I’ll tell you why. I don’t speak Spanish. My last name is Castro. My dad is Puerto Rican. My mother’s Jewish and Irish. Never picked up Spanish and Dixie, my mother-in-law never spoke English, but we had this good connection. I burned a lot of bridges with a lot of relationships. No one believed in me. It went to the point where I didn’t believe in myself. So, I’m starting over. But before I started over, the day happened, my ha-ha moment, there’s only three that’s in my life.

Black Mustang pulls up and we live here in South Florida. It was in the summer. Humidity’s outrageous. Windows are rolled down on this black Mustang, and I talk about it in my book. And Sofi, my wife, is in the front seat driving and she has the biggest smile to me. She’s so red because it’s so hot. And then there’s somebody behind her, a little baby, a little baby, maybe less than one years old. And that’s my daughter Priscilla, who’s 33 years old now, and she is smiling and that red because it’s so hot and it had reverse fumes in the Mustang because it was a beat up car and we used to drive with this reverse fumes coming in the air condition. That black Mustang was given to us, that my in-laws had to bust their butt to buy us a Mustang because I was so frigging lazy, full of excuses, full of the blah blah blah, I couldn’t even get a car. I walk out that day, Justin, and it hit me, man. I don’t know what happened. You can call it God. You can call it whatever you want. It hit me where I didn’t feel shameful. I said enough’s enough. Enough’s enough. And I was really a mess. Not on drugs. I was just a mess. I was a mess like a lot of people out there wants this success, but I can’t figure it out. And I’m driving myself crazy, destroying everything around me, and a lady I love. And I have a daughter now, dude.

That day I said enough. I’m living at their house, paying no rent. I’m living in the room. These people are busting their butt, blue-collar workers. That day forever changed Bobby. The new Bobby came out. And this is where I started getting into personal growth. That Bobby got a job. His frigging butt got a job at the Rusty Pelican, Key Biscayne, and got a second job selling membership to the Better Business Bureau during the day. I said, “Enough. I’m going to stay frigging here and I’m going to win here. How can I win here if I can’t win here?” So, that goes on. Sofi’s driving me there, this, that. I stopped the classified ads, Justin. True story, dude. Maybe I’m going to guess. Don’t quote me on it. It’s been a long time. A couple of months goes by or three months, I don’t know. I hit the drug again called the classifieds. I hit a classified ad, dude, without Sofi knowing. It was that bad. Because if I hit another classified ad, she was going to leave me. I know it sounds ridiculous. That’s why I say there’s an addiction of different ones, procrastination, excuses, drugs, alcohol. There’s a form of an addiction you can decide what you’re going to be addicted on.

So, anyways, I hit the classified ad without her knowing. And it was equipment leasing and finance. And it was a tagline. And I said, “Well, that sounds like an interesting industry.” She has no clue. But check it out, my brother. Some light came into my life. At the same time, more or less, and I’m reviewing this package without her. And it was a business opportunity. I have no money to buy the darn thing. But guess what? At the Better Business Bureau, every day they would hand the salespeople leads to call companies that they think that may have an interest in their membership. They gave me a lead and it was the same company that sent me the package.

Justin Donald: Oh, wow.

Bobby Castro: Now, talk about pulling the RPMs on my addiction. Forget I went through the roof. I don’t even know what. I had to go ahead and tell Sofi. I said, “Sofi, listen. I have to tell you this but this happened, and this is kind of weird how it happened.” And Sofi thought it was kind of weird too. And I’m so excited, my brother, that I’m saying this in her family, in her mom and dad’s house, and it’s a tiny house, man, maybe 1,000 ft². Dixie, my mother-in-law, who’s no longer here, she passed of lung cancer some years back, she’s over here in the excitement of this Bobby, and apparently, she’s believing in me. And it was $1,700, give or take. And back in the day, these incredible ladies had their beeper, had 100 keys to 100 doors, they had all their belongings in their bra and their life savings. She pulls out and she says in Spanish, “Here.” And it was give or take around $1,700. I’m fast-forwarding a lot of the story. So, I’m just trying to fast-track it. And that was such a moment for me where I knew it was everything. I knew these people have sacrificed. They believe in me. They’re just like it became so real.

That $1,700 took me to sell for $1 billion 20 years later on my friggin terms, not on anybody’s terms. I wanted to fly free. But more so, there was a lot of lessons. Before the billion, I’m fast-tracking it. I exited at 250 million. It was all cash, no stock, no nothing, 600 million, and then the billion. It was in transition. I learned so much along the way. There was a lot of mistakes before that. I’m missing a whole bunch of stuff where I then fell victim, got distracted, got into some real estate. We guarantee the company. We almost filed bankruptcy with the same company we sold for a billion. This was years prior. We have a journey. I talk a lot about it in my book. The point I’m trying to make. I gave focus, undivided attention focus of the issue and the stage where I’m at, the reality. If I want this, I have to win here. And I see a lot of people today, they don’t do this. Win here because guess what, brothers and sisters, the stages are endless. There’s no ceiling in life. It continues to get better and better if you feed that focus and energy to really what you want. And what happened with Bobby, Justin, a lot of people disconnected from my life. I just faded, family members and friends. Beautiful people. Beautiful.

But I had to take this journey with myself and be true because nobody I was around believed this was possible. We were all stuck. It’s almost like having a crab bucket, throw a bunch of crabs in. When one go on YouTube, one tries to get out, all of them pull them down. They don’t know any better. And I’m talking about family members and friends. These are beautiful people but we were all here. I had to remove myself from a different zip code. Talk about influence. Surround us. Not because they’re bad. I just needed new information and I needed to define this. I was so eager.

Justin Donald: Yeah. Peer group is everything. Mentorship, peer group, getting around people that have done the thing that you want to do, not people that tell you on social media that they can do things but don’t have the background. Because everyone’s an expert. You know, everyone today wants to be a social media influencer, and it’s actually quite disturbing, the percentage of high school students that want to become what is their dream job. The percentage now of those that want to become social media influencers is through the roof. So, yeah.

Bobby Castro: And there’s no enterprise value there, right? Once I want to do that, I can tell you, you can never sell it. I could have never sold my company for $1 billion if I wanted to be an influencer. There’s no enterprise value. There’s no scale there, guys. You’re not impacting nothing.

Justin Donald: Yeah, 100%. And it’s cool that you had three bites at the apple. It sounds like.

Bobby Castro: Yes.

Justin Donald: Which means there’s a lot of learning. I think you did great, being able to get all cash on the first exit. Most people aren’t able to do that. Most people, there’s an earn-out. They’re getting some stock or there are some sort of metrics that they have to hit in order to get different payouts. So, it’s kind of cool here and that you were able to do that all cash the first time. The second time, was it more of a mix or was it all cash?

Bobby Castro: I know. It was cash the first time. A real quick story. It’s incredible, guys. You can never stop learning. That’s why I say, man, don’t have an ego. It’s not your amigo. It will destroy growth. So, check this out. We get a knock on the door. After we rebuilt our business, when we got distracted, we almost filed bankruptcy for stupid mistakes. “Hey, we want to buy 30% of the company based on a $250 million valuation, and we’ll pay all cash. We’ll wire $75 million.” So, of course, quick to the trigger, “Yeah, yeah, yeah, yeah, yeah, yeah, yeah.” Well, this is going to take a long time to sell. I mean, what’s the reality of that? Well, give or take less than four months, maybe even sooner, it closed. Very quick. Wow. That was strange. It’s like exciting. And again, this is why my wife was very emotional. I was more curious. It’s like, “Why would someone just close so quick? I mean, they must have gotten one heck of a deal.” We had no clue what we’re holding. We knew we had a decent company but not to the magnitude of what the market likes, what the market wants. This other world I wasn’t familiar with called multiples had a really enticing give value your company, so it’s worth X.

You get on Google. That’s why I love Google. You get on Google, and if you really give focus and energy to what you want to find out, you will. If you’re following a lot of people on social media and you want to really give focus and energy of how to make sure you follow the right people, stop on the wrong people. Long story short, Google tells us it’s like, “Oh my God, we gave it away.” We had no clue because the market was looking here. We were more focused on here, like your typical small business owner. We weren’t building the business. We were maintaining the business. We used to work in the business versus on the business. There’s two different outcomes. So, okay, so they had the first right refusal meaning, “Guys, if you ever decide to sell anymore, we have the first right to match or beat it.” “Absolutely.” Well, when you find out, okay, good. And again, remember we talked about? What you give focus and energy to, what happens? It grows. But question is what are you going to get focus and energy to? We gave focus and energy to this area they were looking at. Eleven months, practically under a year, we go back.

Remember, we still own 70%. We sold 30%. “Hey, guys, we’re going to take 19% more off the table meaning we’re still going to own and control 51%.” “Perfect. We love what you guys do. You guys are rock star. Count us in. We want more of it.” “Great. But it’s not $250 million. It’s 600 million.” “You’re crazy.” You agree. When you’re negotiating, when you’re a salesman, you agree. You never push back. I see a lot of salespeople do that, so I’m just throwing gems in there. It’s the power of agreeing. It’s very much just that power, and I understand. Well, fast forward 4 or 5 months later, it closes. And again.

Justin Donald: All cash?

Bobby Castro: It pretty much worked. All cash. And then a few years later, we were looking to exit because we had grandchildren like our grandbabies. Ocean, who was eight years old today, or not? She just turned eight years old less than 30 days ago. And Oakley, our grandson, was five and a half. My daughter, Priscilla, is 33 years old. She’s married to an awesome husband of nine years. My son is married to an incredible lady, and we’re all healthy, happy. And remember, when you build a business, remember I talked about when people realize, “Oh my gosh, you mean I have to go all in? This is that sacrifice?” Well, that’s what Bobby and Sofi did. Now, we want to enjoy some of the fruits of our hard-earned efforts so we can then be grandpa and grandma because, yes, I had to sacrifice with football games, all that stuff to build this business. There is a sacrifice. There is a trade-off, guys. You can’t be a head coach and build a company from nothing. I’m sorry. At least for me. I’m sure there are people out there but I don’t know how to do that. Fast forward, we said, “You know, it’s our time now.” So, we were negotiating at one time 1.6 billion, 1.7, 1.5. It all worked out to $1 billion on the final exit, the valuation, and it was all cash based on our balance.

Justin Donald: Unbelievable.

Bobby Castro: And then we decided that we are going to now focus on our family office, give our family. Because what happens, Justin, a lot of families, and for the ones that are curious about this and again, invest your minutes in this. Don’t spend them. Don’t give them away. Follow what I’m saying. There’s two families out there called Rockefeller and the Vanderbilts. Rockefellers have multiple generations and they’re still extremely wealthy. They have family policy. Vanderbilts bled out all their money. They kept going to the piggy bank. Everyone kept spending the money without investing it and having policies around it. We wanted to make sure we were not going to be a Vanderbilt. So, what we want to do is have a family office and really, a lot of people are very selfish out there. Me and Sofi, we have enough money that we can do a whole bunch of things and leave nothing behind. We want a 100-year legacy plan. We want a policy. We want to make sure 100 years from now somebody mentions Poppa and Mimi, and that’s a lot of hard work. There’s a lot of focus and energy that goes towards here.

We’re being coached by some of the best. I have a personal fitness coach that I pay a lot of money. I have a family coach. I pay a lot of money. I have eight pretty much eight coaches that I deal with on a monthly basis to make sure to coach me in this new chapter in life. So, that’s why we sold it because, and we’re having a great time. I’m spending more time with my children than I have ever spent and now my grandkids.

Justin Donald: That’s amazing. And by the way, this is what life’s all about. It’s about the time spent with those that you love most, creating the experiences that are going to be memorable for you.

Bobby Castro: That’s freedom. Forget about the Ferraris. Forget about the freedom that I can go on a Monday, jump on the plane, take my grandkids to Disney World with their traveling teacher, home school. Hit Disney. Come back. Do a couple of school stuff. Hit Disney. You know what? And then come back at 5:00 on a Monday. That is what I am talking about. I am not talking about taking you out for a $30,000 dinner. I want it with my family.

Justin Donald: That’s amazing. Now, here’s an interesting thing. What I have found and the Lifestyle Investor community is made up primarily, it’s probably about 80% entrepreneurs, 20% business executives, or business professionals. It could be doctors, lawyers, highly paid salespeople, C-suite executives. So, 80% entrepreneur, 20% highly paid business or highly paid professional. Of the 80% for, you know, probably half of them have had an exit and the other half, they have a lifestyle business or they are working on transitioning themselves out. But the big thing that we have found is the people that have had an exit, they always think they’re going to be a great investor but a great entrepreneur is often not a great investor because there are two different skill sets, right? And there’s probably a lot of lessons. If you’re not careful, there’s probably a lot of failures that are going to happen along the way unless you enlist help and you work on your education in this department. And I’d love to get your thoughts on that because you have been able to figure out it sounds like, just knowing you, you’ve done really well in real estate as well. But I’ve got to mention there were some bumps and bruises along the way.

Bobby Castro: Absolutely. Justin, you hit it on the nail. So, before we sold our business on the very first slice and then so on, we were investing our money in real estate. Today, we have a little bit over $700 million worth of apartments. No investors. It’s just us, our family. We have no fund, no nothing. It gives us every single month my wife and I is on full transparency. I live in transparency because I’ve always been on audited financials from building that company, half $1 million a month. That’s just that one vehicle and, of course, feeds my children, my family. But you said something very important. That’s why I have coaches to make sure I don’t screw it up. And I did screw it up. When I exited, my mind was a little wobbly. I was in a different ecosystem, a different environment, a different stage. It is completely night and day to this stage. So, I screwed it up, burnt a few million dollars doing it the wrong way. Got back to the fundamentals. Of course, you make the mistakes. You got to recognize that. And that’s why I literally have eight coaches and we do very well with our investments extremely well. But you’re 100% right. It’s a different environment. We’re in different mindset. We tend to relax really quick. If anything, Justin, I have to be more my game in this world than that world.

Justin Donald: Yeah, and it makes total sense, right? You’ve built up an expertise like truly 10,000 plus hours, you are an expert as an entrepreneur, as someone that scales a business, as someone that has had multiple exits. You’re newer at this point as an investor, right? And for anyone, any entrepreneur like your reps are over here on the business side and leadership and vision and strategy. So, the investment is a whole nother skill set. And I do think it’s important to enlist a team.

Bobby Castro: 1,000%.

Justin Donald: But most people, they either try and do it themselves or they try to totally outsource it. And I think your wealth creation should never be fully outsourced. You need to put the time, energy, and attention to educate yourself so that no one can take advantage of you so that if something happens to these key advisors that you’re not so reliant upon them.

Bobby Castro: 1,000%. And that’s exactly what we’re doing. And you hit it so well. And, man, I see so many entrepreneurs working so hard to get that event. And, man, it takes 20 years to build it. Almost like Warren Buffett says, “It takes 20 years to build a relationship. Seconds to destroy it.” Same thing with money. It takes 20 years to create this wealth and, literally, in minutes, it can be vanished. And the same people that got you from point A to point B, it’s necessarily not the same people at this stage. And I see a lot of entrepreneurs like myself continue to maybe use the same people with the old skill set at the old stage you’re at and trying to migrate them at this new area. Investment and operating a business, two different worlds.

Justin Donald: Yeah, 100%. And what’s really been neat is you and I met and got a chance to hang out at an event with Tim Tebow, which is so fun. We’re part of a group called the Wellspring. We have mutual friends, Pete Vargas being one of them. Pete’s coming on the podcast here soon, too. But, for me, in my life, my faith has been so important, and it’s gotten me through a ton of tough situations, both in my life or with people in my life. And it seems like this has been really something new for you, right, your faith journey. I’d love to just hear any thoughts about that.

Bobby Castro: So, I never believed in God. I was one up to recently and the last time recently was we were at Thanksgiving. Not this past Thanksgiving, Justin, the prior. And it was at this house and my awesome daughter, Priscilla, was saying a prayer and all our family was around. And I never forgot this dude. I looked up saying, “Wow. She’s doing a long one.” Like being almost sarcastic like, you know, without bad posture and all that? And I’m here like, “Man, that’s a long one.” When I did this, I’ve seen everyone in a moment of God or whatever they were feeling, and I was the only one not. And this is my family. This is everything to me. These are the ones that I love, man. This is why I do what I do. And I felt like I’m missing something. Fast forward, a few months later, I’m in Cabo, Mexico speaking at an event of entrepreneurs and then finishing up doing a podcast before I was going to hop on a plane and head back to Florida. I met a gentleman by mistake on a balcony and his name is Pastor Keith. He’s out of Texas. And he’s an entrepreneur. He’s also in real estate. He and I started just really jiving together. Had no clue of whatever his association, his relationship to God. By the time I left, I accepted God in my life.

It was the perfect moment on the balcony unexpectedly and whales were breaching in the background. It was the most beautiful sunset I’ve ever seen. I was just present. So, I accepted God in my life. What does that mean? I don’t know. I’m still on this journey. The Bible is very intimidating. It’s a lot of information there. I’m being guided by some incredible people. I went to Tim Tebow’s event. I love Tim Tebow, his family, what he’s doing so much, me and my wife, at that weekend when I have seen you, I donated a quarter of $1 million to his cause because it’s incredible what he and his staff are doing every single day when no one’s watching. And I noticed, man, everyone that has a relationship with God, they have this vibration as I do all of our life, how they see positivity everywhere. It’s like this shirt, “PMA all day, everyday,” positive mental attitude. And it just started slowly. At 56 years old, the dots are connecting that God was all along directing all this and putting me in these spots. And I used to say, “Man, you got to put yourself in these opportunities.” God put me in those opportunities. I was prepared, and when the opportunities there and magic happens, I am in this journey. I’m still here. This is just all new for me.

But you know what? This only that matters. It feels good. Feels good saying it and more so feeling good. Now, I’m saying I saved myself. Thank you God. Thank you God. Thank you. Thank you that younger Bobby. Man, I’m surfing in life now, man. I’m like I always said I feel like I’m on a milky way, man, but I feel like I’m really. And then I used to be paranoid up to just recently that, God forbid, when my time comes, what’s going to happen to my family? Just nerve wreck. I was just, again, so much better knowing that it’s in God’s hands. And I’m not here to preach God to anybody. I’m just giving you my testimonial. It feels good. God was all along part of this. And there you go, dude. And I met you at that incredible all these business owners with Tim Tebow in Jacksonville and pretty cool.

Justin Donald: Well, I think it’s powerful. And I also think that what a great antidote to caring less about what other people think and living a life that is honoring and is service-oriented to others. So, to me, it’s like what a great way to really fight, putting people on a pedestal and what they think of you and possessions, and all these things because that’s not what is most important, at least for me, right?

Bobby Castro: You know, I have to. You just led this in there. You remember I told you the story of Rusty Pelican when I was a waiter?

Justin Donald: Yeah.

Bobby Castro: I had this flash dance ego. You would never see me waiting on tables at that stage. I’m waiting tables in the Rusty Pelican. I’ll never forget this night. There was like an A top. It was a big top. It was eight people. I knew majority of all the people on the A top. I used to flash dance with them. So, I know the crowd. I know them all pretty well, and they have no clue. They haven’t seen me for a couple of months. You know, I just disappeared off the map. And here I am. They’re sitting at my table in my section.

Justin Donald: Oh, man.

Bobby Castro: Hey, no. Dude, God was on my side. I didn’t care. I went there. I gave them so much love. I gave them the best freaking service where I was working for that gratuity, the value. I didn’t care. I was on a mission to improve my life. That’s when I knew I was ready.

Justin Donald: That is powerful. And I love like those of you that are listening, you can’t see this, but those of you that are watching this on YouTube, you can see Bobby’s background. It’s a picture. It’s a painting of all the sayings, the phrases, the things that have meaning. I mean, it is unbelievable.

Bobby Castro: Yeah. And it reminds me, man, remind me what’s more important, how you feel, because I am very proud of myself. And for a long time, I couldn’t say that.

Justin Donald: That’s awesome. Hey, Bobby, you’ve built an incredible life. I’m excited about the new journey in your faith and where that’s going to lead you. I think it’s amazing what you’ve been able to do in the past. I think what’s even more exciting is what you’re going to do to help and coach and mentor people to do it wisely, do it well, do it better than you, do it differently, quicker. You know, we’ve got a mutual friend in Tyler, who is coaching with you and just has the greatest things to say about you and the impact you’re having on him. He’s actually joining the Lifestyle Investor Mastermind.

Bobby Castro: Awesome. Wow. Him and his wife are just awesome individuals.

Justin Donald: Well, we’re thrilled about that. Hey, I would love to have our community support you. Where’s the best place that we can, A, learn more about you and, B, support you in the book, UPSIDERS, that you wrote?

Yeah. So, UPSIDERS, I always say it’s on Amazon. It’s Upsiders, Bobby Castro. If you can’t afford the book, DM me. I’ll send you the book free. It’s $14. I’m here to help another Bobby. If you read the book, check this data out. I’m a data freak. Over 80% of books that are purchased, regardless of the dollar amount, Justin, never get open. The 20%, give or take that do get open, the majority of them never get finished. If you buy this book, finish the book, but more so after you finish it, read it again because you may get some nuggets there but then give it. Pay it forward to somebody else that you know and your family, co-employee, and employee that can use it. Give it to them. You can get it on Amazon. My handle on Instagram that my son put up when I sold the company, it’s officialbobbycastro. I try to respond to every DM. I am here for a moment in time. What does that mean? I don’t know, but I think God will give me that message when I do know.

Justin Donald: That’s awesome. Well, you’ve shared some amazing things with us here today, and I always love to end every episode with a question. I kind of hinted at it earlier. But for those of you that are listening, for those of you watching, my question for you this week is the same as every week. What is one step that you can take today to move towards financial freedom, to move towards living life on your terms, a life that you truly desire so not one by default like most people do, but truly living a life by design? And how can you take one thing that Bobby shared today as that action step to moving towards financial freedom? Hey, Bobby, thanks so much for joining us. This is a ton of fun and I look forward to connecting again here in the near future.

Bobby Castro: Thank you, Justin. Thank you, man. Much love.