FLTA S2 E3 | Making Millions


What is the secret to making millions in real estate? It’s not always through a jackpot. In fact, most of those who achieved this goal had to make a lot of mistakes along the way. Most new investors would have this optimistic naivety, which is great, but only to a point. Seasoned investors like Cuthberto Ramos are more cautious with their approach, and with good reason. A 23-year veteran in the industry, Cuthberto has experienced the debilitating market crash of 2008-2009. Since then, he has always embodied the approach of, “Prepare for the worst and hope for the best.” This mindset is especially timely now that the whole industry is crossing their fingers and intently watching for what will happen next. Want to survive the next bubble? You might want to drop that jacked up optimism and listen to the voice of experience.

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Markets, Mistakes And Making Millions With Cuthberto Ramos

I’m here with an amazing guest. We are going to drop a lot and have some deep conversations on this show. This is a must-read. Before I jump into the conversation with my buddy here, I want to talk about the business. That is everything going on in the Flip Talk universe. I want to make sure that you are aware of it. Go to FlipTalk.com and check out what we have. For those of you who are new, we have some amazing free things there for you, some resources, contracts, videos, preferred providers, and all kinds of cool stuff.

If you are looking for a coach or a mentor, we have opportunities to apply to work with us. As always, if you are an active real estate investor and are looking for a mastermind community, which I think humbly is the best mastermind community, you can go to the FlipTalk.com page and find a way to apply. You can go to BeInThisRoom.com and apply for the ICE Community. With that out of the way, I got my guest, Cuthberto. How are you doing?

I’m doing great, Don. Thank you for having me.

I’m excited about this. We have known each other for a few years, and this is the first official buyer sales episode we are doing together. We have done a few with other people.

I think we did one.


FLTA S2 E3 | Making Millions


Typically, I want the whole backstory, and I might skip that a little bit, primarily because we are going through a crazy market now. There are a lot of big questions. You went through something very similar to what I went through as far as losing everything. Give a brief backstory on your journey into real estate, what you went through, and how you came out of that, and we will go from there.

That is a good way to start to at least cement how we got to where we are in regards to how both you and I think simply because we went through a similar loss in the market. My story starts with a market crash prior to. I have always brought up the story which I grew up in a family of entrepreneurs. In the late ’80s and early ’90s, my family was thriving, but then there was a serious real estate market crash known as the savings and loan crisis.

Even though I was young, I was an adolescent, in my teens, and so forth, it had an impact on my decision on what I wanted to do. It is the decision that made me go into real estate. It also is a decision that made me go into the type of real estate that I did. The savings and loan crash of the early ’90s affected me, but I didn’t learn what I thought I needed to learn. Both you and I always talked about the crash. It is known as the ’07-’08 crash. I always tell people it started at the end of 2005 and bottom at the end of 2009.

I went to that whole thing where I didn’t have the work ethic, and I also didn’t have the financial setting. I didn’t have the assets that I needed to be able to plow through that. I can go on and on, and you know the story, but the best way that people understand how I got to where I’m at is that I went through two cycles that affected my life and impacted incredibly to where it made me have posttraumatic stress from that moment.

I’m seeing and hearing a lot of people right now who didn’t go through that, and they are reminiscent. I hate to be the Chicken Little. You and I know that there is a cycle to this. Anything that has a cycle is bound to repeat regardless of what anybody says. A cycle doesn’t have a particular linear way of going. It doesn’t also have a timeframe, or it has to be ten years.

No, we both know that there are telltales, either years, months, or days before the actual crash. As long as you and I have known each other, we have always shared these insights that we have shared with a million people, but it seems to go right over their heads. Both of us are at peace when we say it. They don’t take it in because it is like speaking a different language to them. It is a different paradigm. They are going to get blindsided the way we all get.

The way I got here was by being a savvy learner of major screwups. That is the best way to describe me. I’m a years-long vet in 2022 in this whole real estate investing world full-time. I have been at the cutting edge of everything. I’m at the forefront, which is different than saying I was lollygagging. No, I have been a pro. I consider myself an all-pro in this industry. People would be like, “Let me hear it out.” Amongst my circle, I know the value and experiences I bring in and the model I have. That is a short, skinny explanation of who I am.

You say that you went through two cycles. In the last cycle, you experienced quite a bit of loss. You always tell the story about the shoes in the car. I want you to share that with the readers.

I have some good news for you on that. The second crash was me more of a full-time professional adult. It had a direct impact. It wasn’t my parents and my family losing their stuff and being almost displaced. It is a different field. It is a husband and wife. I was already married, poor kid. You know it. You are going through that. I remember at the height of the inflated market, I had my thousand-dollar suits, shoes, and luscious convertibles. You go from a moment where it all dries up. I want to emphasize that. Because I experience an absolute dry-up, that is what people don’t understand about a crash. It could be maybe 6 months or 3 months only, but an absolute dry-up can destroy you.

Because I went through that dry-up, I was walking around with a dollar to my name and in suits with $1,000 shoes that had been worn out with holes underneath them. I’m completely living that whole Imposter syndrome. It drove you and me nuts. I know that we have shared that, and that has a lot to do with my conservative approach to investing.

When I say, “I want to emphasize conservative,” investing approach is not the same thing as what you think it is. Show me a real conservative investor, and I will show you who is awesome when I’m out there negotiating a deal. There is the conservative investor, and that is the guy who doesn’t get the deal. What I mean by that is cautious. It is not just overly cautious. It is cautious within the framework of knowing that something bad could happen.

I went through the holes in the shoes, shaking the house sofas to look for change because that was it. I was driving around with expired tags because I didn’t have enough to do it, knowing that if I got pulled over and they took those from me, that was it. You broke me. I’m driving that fear to the office, knowing that I have an expired tag and suspended license because I had gotten tickets for expired tags that I haven’t been able to pay.

You name the embarrassing feeling of an absolute crushing of what you thought your self-image was. If that happened, and that is going to happen to some folks, this market doesn’t necessarily mean it is going to be a bad real estate market. There are a lot of people exposed to other investments outside of real estate that is getting hammered now.

FLTA S2 E3 | Making Millions

Making Millions: This market doesn’t necessarily mean it’s going to be a bad real estate market, but there are a lot of people exposed from other investments outside of real estate that are just getting hammered right now.


I always talk about that optimistic naivety you have when you first start. You don’t think it is impossible for it to end or go wrong. You take chances that you normally wouldn’t take as a seasoned investor or business person that will pay off a lot. When they don’t, they don’t. We are watching a lot of that optimism, AKA arrogance, online now. I saw a post that said, “There is no bubble.” I don’t necessarily believe that there is a bubble per se, but I believe that there are opportunities for the market to slow or cool. There could fundamentally be something that makes it crash.

The argument that there is low inventory, so it can’t happen, is flawed because consumer confidence, access to capital, job security, and all those things come into play. Whether or not the interest rates make it affordable or not comes into play, and houses are going to move even if there’s low inventory. There are factors that we don’t know about. There have been things online about how rents don’t go down, and we knew, in 2008, they do.

If you don’t have something to cover that, good luck.

It is cool to always have these conversations. We sound like we are doomsdayers, but it is to prepare for the worst and hope for the best. You have been a prime example of preparing for the worst and hoping for the best, and I want to talk about that. First and foremost, when did you get back in the game?

After being depressed for a few years, when I was able to release everything, it was at the end of 2009. I have already reached rock bottom. My arms didn’t fall off. My skin didn’t turn green. I didn’t file for bankruptcy because even in all of that, I was still able to pay my debts off. I owed the IRS a huge tax bill. The craziest thing about that is that since I believe I’m some of the people who lost everything early, we are talking about the middle of ’06, I was able to recover a lot quicker. I want to emphasize that. Because I lost it early, there were no loan modifications when I lost everything. There were no foreclosures with bankruptcies. It was early because I was cutting edge, and I was in an industry that got halted.

I was a lender. It was my industry that caused the bubble. It was my industry that got the hose squeezed on them. I was going to be the first to have an economical loss. That is why I’m saying after the dust settled, it was the end of 2009. That is when I went full blitz on everything while I watched everybody for the next several years, almost zombie walk in the industry.

That is why I was able to surpass them because I was early. They were still going through their crisis. They were delaying the crisis. They had lawsuits over their head for their licenses, for doing modifications, and for having a shit ton of negotiations of short sales that they weren’t getting done. All of this was happening to them while I was restarting. I like to bring that up because that played a huge role in the success of the strong years.

You didn’t make it to the St. Louis meeting, but we are talking about it in St. Louis. I have a buddy Shaun McCloskey who is big on work-life balance and stuff like that. At one of his events, he was talking about, “When you fall off a building, what kills you, the fall or the splat?” Ultimately, it is the splat. When you hit the ground, you die. In business, when you fall off the building, what kills you? Is it the fall or the splat? It is the fall that kills you. You are just sitting there trying to maintain and hold onto everything you can. You are bleeding. The faster you hit the splat, the faster you start over. You fell first.

When you fall off a building, it’s the splat when you hit the ground that kills you. In business, it’s the fall that kills you. The faster you hit the splat, the faster you can start over. Click To Tweet

I splattered first and got up. I’m like, “I’m still here.”

That is a prime example in business. If you have fallen off a cliff, instead of delaying the inevitable, rip the Band-Aid off, get it done and start over. That is a great lesson and analogy to hear when it is said. You rebooted in 2009. What were some of the strategies that you employed to get yourself going?

My background was in financing. I was able to partner up with Manny. We owned a direct lending branch. We realized that was only the sustained income, but we went straight at acquisition. That is what we did. On day one, we went to acquisition in a toxic environment. You got to understand what real estate looks like. It didn’t look anything like it did now. In December 2009, it looked nothing like that. It was doomsday.

People now, with hindsight, talk about, “I wish I could go to those days to buy real estate.” Believe me, if it was cheap and it declined, that means the environment was shit. You have to understand it. That is where you were operating from. It wasn’t what everybody thought now. We don’t wish a down market on people because it is bad for it to get like that. Bad things happen to everyone.

I got into private money immediately because that was the only thing that would lend at that moment. The conventional and the FHA were not going to lend in a distressed situation. I created relationships through private money. In the end, I started utilizing the accumulation of all the private money as a strategy to acquire. That allowed me to scale. Before all of this training came out, the scaling was more based on, “I can do how much my partner can do.” It is very gung-ho at that.

Thank God, through networks like the masterminds, and so forth, one is able to evolve there. The early masterminds with you, I was able to bring a lot of value because I was like, “I was at the forefront of that.” Manny and I were doing it all without saying, “This is what gets delegated. This is who the visionary is. This is who they implement.” There was none of that. It was a straight gung-ho. See who outworks who. That was it.

It was the strategy of private money that created the strategy of the BRRRR, but I was doing it in a portfolio level, in a pooling of real estate level. It wasn’t one house at a time. It was ten at a time in one loan doing the entire model of BRRRR. I used to call it flipping it to myself. I didn’t call it a BRRRR because this precedes the BRRRR. I was doing it with that. What took it to the other side of the wealth equation was when I learned to raise equity, not private debt, the way I had. It was when I learned what equity financing was, how I utilized it with the new refinanced portfolios, and how I added it.

For those who know me, they know I can nerd out on stuff like that. It was four years, from between the end of 2009 to 2013, I was refining that model. From that point on, even my family, who saw me as a regular Joe coming back, saw something different in me. They saw a different wealth that I had created. It was because I learned something that I looked around and was like, “This is in front of all of us. Why isn’t everybody doing this?” You and I know because you and I met at the place where I learned this finance model.

First and foremost, I want to give a shout-out to George Antone, who is the one who has helped you do this. He is an incredibly humbled-giving individual. He has a few books and does some training on his own. If I had to recommend anybody outside of my own coaching and education platform, George would be one of those people. He has become a good friend of yours and mine. If you ever want to know about wealth creation, leveraging debt, and everything else, he is one of the smartest people in the world.

You mentioned a few things. For somebody who doesn’t know what BRRRR is, it is Buy, Renovate, Rent, Refinance and Repeat. You talked about portfolios. For people who are brand new, a portfolio is multiple properties in one package. They could be commercial properties, single-family, multifamily, or mixed. Portfolio lending is when a lender lends on a package of properties and not one property. I want to make sure we get those. They cross-collateralized.

Forgive me, everybody. Me and my finance terms will annoy you.

I want to make sure because we have a newbie out here that they know the term. Cross-collateralize is something that you become good at or your superpower. You and Manny have been partners for a long time. Partnerships have been tough for me along the way. What are some of the things you did in the beginning or along the way to allow yourselves to maintain that partnership? I’m sure it hasn’t always been roses, plums, and great sunny days, but obviously challenges. What are some of the things you guys have been able to do along the way to maintain that partnership and the integrity of that partnership?

This is obviously an exaggerated statement. This is, at least, we know where I’m hinting. It is easier to find a spouse than to find a business partner.

It's easier to find a spouse than to find a business partner. Click To Tweet

That is not exaggerated. That is the truth.

We have been thanked for a long time by people who see us and get inspired by our relationship. It starts with many things. It starts with open communication and battling for each other. We were both individuals that if you leave it for me to do it for me, I may not do it. If I have to do it for you, I’m going to give you the extra. We happen to both be those types of individuals. We don’t know how to give ourselves, and we suck at doing it for ourselves. In a weird way, we were doing it for each other. That is one.

The other part was that we learned how to respect each other’s fears, which doesn’t necessarily mean the same. I have always said that, for me, I’m okay if I don’t have a lot of money in the bank account, but as long as my money is deployed, it is in my balance sheet, and there is something cooking where I know income is coming, that is a wait, but that would freak Manny out. Manny wants to see money in the account. I don’t want to see money in the account because I think I’m not doing anything with it. Instead of fighting about it, we learn that we have to respect and honor those things.

There is a whole slew of things. With open communication, whenever there was an issue, Manny and I could air it out and talk about it. There was always a peaceful ending. I was probably more dramatic. Manny has always been more of a calm person. He is also a lot more of a fearful person and always has a need to improve something to control it. I have to know that because I have to understand that Manny is doing something that seems to be improving it, but his fears are controlling it. You have to honor those things. You don’t try to make that person change. You got to understand them and work with it because one is not perfect either.

You have managed to make that work and become partners over the last number of years. How important would you say in a partnership staying in your own lanes has been? Define the lanes and staying in those lanes.

First off, it defaulted because we almost got there by accident. That was the way to maintain peace. We ended up finding that every time we had something, the way to maintain peace was to honor and respect the lane. Through the evolution of the training that has been about the way people scale, it has helped us iron it out and make it more identifiable. Those are skills that you learned in the mastermind with you.

Once you recognize that, “This is where I’m at,” that is why we created our own where everything falls under. We believe everything falls under four places in us as holders, not as wholesalers because we are not wholesalers. Everything falls into four quadrants. We can share and do things all over the place, but we know that our strengths lie in one place and his lies in another. The more he is able to feel free to make the decision, the more I feel that I can do the same. When he is recognizing it, and there is some fear about it, he will let me know, and we will talk about it. Everything is always with the intention of completion would be the easiest way to say it.

I want to touch on how important it is to look out for each other. He is going through some stuff personally now with a family, and there are two ways partners can look at it. I’m sure there is always an internal challenge as a human being. One is, “He is going through stuff, and I’m holding down the ship. It is not fair.” The other one is, “We built this thing so that we could stand for each other when we can’t stand on our own.” That’s the other way to do it.

What I have seen with you two is you stood for him when he couldn’t stand on his own. That is a cool place to be. Let’s talk about that. What does it mean to you guys to have built something so he can be present when he needs to be present in his life and not worry about the business and know that you have his back?

To give some shadow, and I’m sure he is okay with it, Manny is dealing with the mortality of cancer inside his immediate family with his wife. As a husband, it is devastating for him. It has changed the entire course of his view of life. He is a major player in the role of the company. If we were to talk about visionary and implementer, he is the implementer. Imagine the implementer being gone. It was a big pivot in our business and outlook.

Thank God that we built a cashflowing operation that allows him to be able to be not at work forever. He hasn’t worked since August 2021. His full-time job is to save his wife’s life by any means necessary. That brings me from visionary to implementer roles, but I had to make a decision of three things at all times. I had to be the best brother to him. We are not related. We are brothers. The brotherhood is what helped the partnership for several years.

There is the partner who has important obligations to each other, like marriage, and there is being the best human being I can be for him. The first two have hidden motives. They have motives of selfishness around being a brother and being a partner. Every time I needed to make a decision that could support him, it came from being the best human being for him, being ready for if he ever came back.

Let’s be honest. We have talked about this. We don’t know if he could ever come back. What does that mean? Does that mean he becomes homeless? No. His life’s intentions may have switched so much that he doesn’t have the ambition and motivation to work 60 hours on some operation. The mortality of our partnership is very much in limbo. Instead of being a victim of it, I have to operate for him, for his sake and his whole family’s sake, in the best human way possible. I was like, “I’m going to be here for you. I’m going to make sure everything gets settled. I will halt our visions of acquisitions and eating up the world. I will stall it. We will wait. If a tragedy happens or a miracle happens, we will be here for you.”

It is an honor to do that, to have that experience. Within the drama, there is the gift of the understanding of honor and integrity. That is a human element that makes everything worth it. Did it change my outlook on how blindly ambitious I was? Yes, it did. Did it change my outlook on how to prepare for the future? This has blindsided us the way markets will blindside somebody in an inflationary market. I’m going through a blindside very different than somebody who lost 75% of his wealth on a deep of crypto or something. That is the best way to put it.

You bring up so many points. The first one is the integrity of the partnership, the relationship, and being able to look out for each other. Why do we do all this? We do all this so we can be in the place where we need to be and when we need to be there. People are out there saying, “This isn’t going to happen. That isn’t going to happen.” Life throws us curve balls, and they aren’t always market conditions. Imagine if he didn’t have his finances or his partnership in order, and his wife was going through this, and he was losing everything because he couldn’t work or pay the medical bills. There are a lot of reasons to run a good business and have good relationships.

I probably will annoy people by having a risk mitigation table of the what-ifs and what-to-dos if something happens. It is like, “That came in hand here.” We had an ABC of what to do if one of us passed away. None of us passed away, but the immediate absence of a partner is there, and we had entire steps on how to mitigate that because there is an obligation, assets, and capital in question.

If he had to be working while all this was happening, or if this happened to him when I partnered up with him in late 2010, it would have been devastating because he is there attending her, looking for all the clinical trials, and turning all of the stones. If there is a miracle that happens, it will be because he gave her 100% of his attention.

If, God forbid, the worst happens, at least he was able to be there as much as he possibly could. Manny is an incredible person. He is a great human being. I have always had the pleasure of being in his company. That leads to another thing you mentioned. You hit on this. In August 2021, you guys were in San Antonio with me. Manny wasn’t able to make it. You were in consume everything by everything mode. You got the news later that week or a week later. You were able to pivot your entire operation to, “Let’s tie up loose ends, and let’s go into a holding pattern.”

That was in Austin. After that, I bought $15 million in real estate in a three-month span. We were going to go more, and it all came to a halt. There was a plan in place, but it required two all-pros. Both of us couldn’t suck. Before that happened, we both realized, “We have come a long way, and we are effing good.” It required both of us to bring all of our skills.

Because that happened, it changed everything. You are right. There is a pivot to hold off. Since then, all I have been working on is settling. I’m making sure that we get rid of debts and deleverage. It is important that I want to tell this to the audience, and I learned this with George. Everybody always talks about a market crash, worrying about a market crash. The thing about a market crash is that it is an event that causes A, B, and C. That’s what a market crash is, and that is one foot.

There are at least two other things that are the equivalent of a market crash. That is the loss of a partner and job and income. Those two things are equivalent. When the 65-year-old man who has been working at the job for 40 years retires and no longer works, he experiences the equivalent of a market crash. Ladies and gentlemen, don’t just be out looking for a market crash to be the end all be all, “If this is that, then I’m going to start pivoting.” There are other events that caused it. That caused a market crash for us.

FLTA S2 E3 | Making Millions

Making Millions: There are at least two other things that are the equivalent of a market crash: the loss of a partner and the loss of a job.


Similar to 2005, I’m going through the market crash first, and I’m doing the auto-correction that most people are going to be doing down a few months from now. Why? It is because it wasn’t because I went through the market crash of the economy. I’m going through my market crash because of the absence of a key player. That is making me do everything, reorganize my asset protection and my trust. It is making me do extended liability coverages, deleverage, and all of these things that a human being does when they are in danger.

I’m blessed to at least say that I am a year early and at least in the modification of the operation to be able to withstand what is coming and flow in neutrality as the stuff is happening. I would say a year because the shit hit the fan in August. You were there. You were one of the first people I told this to. I want to make that emphasis to all of the readers that a market crash isn’t the only event that causes ABC. There are things that are equivalent that have nothing to do with the economy. It is something that does it. You have to be able to respond adequately.

That’s amazing foresight and advice to the audience. I’m going to pivot a little bit because we have been talking for a little bit. If somebody was starting out in the market, what advice would you give them?

Don’t look at a market crash as the end. That’s when you start pivoting. Click To Tweet

There should be a two-faced plan regardless of what you do. Whether you are going to do wholesaling, flipping, be an agent, a lender, a developer, or anything, it doesn’t matter. The first is capitalize. Make sure you have a system in place to get extended liquidity. Within the extended liquidity, there should be ways to borrow, whether it is private money or institutional money.

Regardless of what it is, you have to create a plan to capitalize. It can be a five-year plan. It doesn’t matter. It has to be a high-yielding return of influx of capital at a time because you need to capitalize. In order to survive in this industry at any moment, capitalization is key. That doesn’t mean reserves and liquidity. It means that you can turn that liquidity into investments, and the assets become the same thing because they are helping you survive.

The first is to capitalize regardless of what you want to do. You can be a loan officer or a wholesaler. It doesn’t matter. The way to capitalize is not the blue butterfly that makes you lose your focus. Focus on doing what you do to increase your influx. I believe wholesaling is the best. Unfortunately, I’m such an old dog in this game that before wholesaling even took off, I already had a full-blown operation that was successful. I couldn’t pivot to that. I believe wholesaling is the best to do because you get a large influx of capital. There is an investment to do it, but that is the cost of doing business.

The second part of the phase would be to start buying assets. I know real estate in and out. I know the boring parts of even title insurance. That is how much I know. I know exactly how a transaction works in real estate. If I knew that about crypto or stocks, I would be there. Because I know the absolute ins and outs of a real estate transaction, that is where I invest my capital into.

I am a large volume holder, for those who don’t know. That kicks off a yield, and I always reinvest my returns. It is got to be those two. I like to say those two, the capitalization and buying assets, because those are universal. You can do that with anything. That is what I would do. I would say get into a mastermind to learn and to be in the environment. You can get the questions and answers there, but reach out to get a mentor. That is different. Just because you are in the mastermind, it doesn’t mean that the guidance you are going to get is different. That is going to be more for the mentorship. You got to learn those two things.

You know me. I have been a self-improvement junkie forever. I can’t recommend a mastermind enough and surrounding yourself with the right people, being in the room with those people, and being in the room where everybody talks and shares. There is not a pastor up in the front hugging up all of the knowledge. It is everybody coming in and sharing with each other.

During the capitalization phase, being involved in groups like the mastermind is crucial. I don’t believe you can do it without being around people who are already doing what you want to do. That is the first phase. The second phase is a whole different thing. You have to learn your asset. I’m sorry, you can’t wing it and join. You got to learn your asset once you start acquiring an asset and become an asset manager of your own assets. It is two black and white, very simple things, but they require a lot of effort.

FLTA S2 E3 | Making Millions

Making Millions: During the capitalization phase, being involved in groups like the mastermind is crucial.


One of my biggest regrets is not acquiring more assets along the way. In my flipping and wholesale through the years, I should have held onto more. That’s good advice. Tell everybody how to get ahold of you. If they want to find you or reach out to you, how would they reach out to you?

Email would probably be best because at least you can introduce yourself, and it is CuthbertoRamos@gmail.com. I can give you my cell phone and all that, but an email where we can have a conversational thread if there are any questions you want is probably the best.

If you are getting value from this show, make sure you like and subscribe. If you got value from this interview, reach out to Cuthberto and have a conversation with him. He is a giver. Make sure you are sharing this wherever you can share. Make sure that you are giving us any of your remarks, feedback, or compliments on iTunes, Google Play, Stitcher, or wherever. Make sure you check off FlipTalk.com if you are interested in being a part of Flip Talk and anything else we have going on. Berto, I appreciate you being with me, and I always enjoy our conversations.

Thanks, I appreciate it. Thanks, everyone.


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