11 Dec 2025 · 18 min
Ryan Daniel Moran (podcast episode "I Lost $2 Million", Capitalism.com, March 29, 2021) recounts major business losses including a purchased business ($2.7M) that has cost him roughly $1.5M so far and could total $2M, other losing investments, and an expected $5M payout lost when the buyer declared bankruptcy — cumulatively described as roughly $15M in lost value. He reflects on the shame and paralysis those failures caused, the longer-term perspective of entrepreneurship, lessons about customer-first focus, and how failures improved his ability to advise others. He also promotes his mentoring group "the 1%" (linked to capitalism.com1) and notes a statistic that 99% of business owners never clear $1M.
Questions this episode answers
$2.7 million
About $1.5 million (projected to total $2 million if nothing changes)
About $5 million
About $1 million
20%
Chapters
We're going to take the stigma out of failure because I have failed really big. I have failed spectacularly well. I have failed on a grand stage. And so if I can fail and lose millions of dollars in my failures and be okay with it, I hope that it sets you free to swing for the fences and miss and own it and be cool with it and do it faster than I did, because it took me a few years to. To be cool with it. So I have one project in particular that has lost a lot of money. And I bought this business back three or four years ago, and at the time, it seemed like the right thing to do. I bought this business for $2.7 million with the intent of growing it and also launching other brands and businesses with in the umbrella of this business. And my business partner and I had a really great thesis for where we were going. It just didn't go the way that we thought it would. And as of this video, I've lost about $1.5 million from that project specifically. And if nothing were to change, and I think it will, but if nothing were to change, I'll end up losing $2 million from that project in total. However, that's not the end of it also. Well, back in 2017, I had the best business year of my life. I sold a business, and after, you know, my. I had a 50, 50 partner, and after I paid taxes and after everything shook out, I walked away with about $5 million. And that $5 million, if I had just put into index funds, if I had just put it into any, like, boring investment, It'd be like 10 or $15 million. But I didn't other things, one of them being this business and also some other businesses that I shouldn't have invested in. In fact, I lost another million dollars from one of the investments that I made from the money that I had taken home from that exit. Now, not only that, but I also maintained a 20% stake in that business that I sold with the expectation that that business would grow and then I would get another $5 million check later on. That didn't happen because the business that I sold my company to declared bankruptcy and I lost my 20%, which means that that $5 million expectation went away. So when you add up the money that I lost in the business that I bought, in the investments that I made, in the investments that I didn't make, and in the expected money that I did not get, I actually lost more like $15 million, in case you were wondering.
Yes, that hurts.
Yes, it does. Not feel good to have lost that amount of money. Now, of course, there's a little bit of this like coulda, woulda, shoulda going on and we've all got coulda, woulda, shouldas, right? Like we coulda, woulda, shoulda bought Bitcoin at $100, coulda, woulda, shoulda bought Apple stock at $10. Could, coulda, woulda, shoulda bought Tesla and held it for much longer than I did. Right? I mean, you could do this all day long about the things that you wish you would have done or hadn't done and how your life would be different if you had or hadn't done those things. And I carried that with me for years, especially the one where I bought this business. And I put a lot of heart and a lot of hard work into it and it just didn't work out the way that I wanted it to. But the strangest thing is that the more that I was upset about it, the more that I tried to force the business to work, the more that I beat myself up over the decisions that I made, the more I continued to make really bad decisions, the more I was stressed about the money that I didn't make or that I should have made, the more that I continued to make stressful decisions, the more that I continued to find reasons to be worried and to be stressed. Do you know how many times I played the numbers in my brain as I was falling asleep to make sure that I had enough money to make the debt payment on the business that I bought because we borrowed money to buy that business. And like a large majority of everything that I've made ever since then has gone to service that debt. That hurts like that made me feel paralyzed for several years. That made me feel like a failure. And it didn't matter that I have other successes. I've built several million dollar businesses. I've had an eight figure exit. I run an investment fund that is working with deals right now that I'm very confident are going to have sizable exits and be worth a lot of money and change the lives of the people that we're working with. I've helped create hundreds of millionaires. I have people who recognize me on the street everywhere I go around the world. From people who say, not only, hey, I like your videos, but hey, I built a seven figure business because I watched your content. And yet I was for a long time carrying around what felt like this scarlet letter of a loss on my record because I had a few projects that didn't work out. Listen, I'm telling you all this. First of all, it actually just feels good to say all of this out loud. But second of all, I want you to know that I have experienced that feeling of other people seeing the successes and me knowing about the failures. And when you keep that inside, all you ever think about is the failures. And you can't even accept the accolades that other people give you. It's like this terrible poison that is in you that just eats at you from the inside. And you know what I discovered throughout that whole process.
Is I'm still here. I'm still playing the game. I'm still really successful. I'm still really good at what I do.
I'm actually better at what I do now because of all those failures and because I can advise all the entrepreneurs I work with to avoid those pitfalls. I know how much I beat my head against the wall trying to make certain things work that just didn't work and wouldn't work and will never work. That I can help someone else not beat their head against the wall. I know how to turn that company around now and how to turn other companies around now because I've made other mistakes that didn't work. And the good news of this is I'm still playing the game. Entrepreneurship is not a one year plan. That's ironic because I literally wrote a book called 12 Months to $1,000,000. But entrepreneurship is a life sentence. I'm going to be playing this game for another 60 years. I'm going to be playing this game for decades. I'm going to make tens of millions of dollars because I know how long I'm going to play this game and I know what I've done up to this point and what I'm going to do moving forward. And yet I couldn't shake the one failure because I felt such shame around it. And the minute that you just like, accept it for what it is and deal with it and grieve it and process it, there's no more shame around it anymore. And the irony of that is that that's when you're in a powerful position to change the situation. The more that you can accept the situation for what it is, the more power you have to change the situation. I couldn't fix the business that I was trying to fix because I was carrying around such shame around it that I wasn't in a position to be able to adequately address the problems that the business had. I had to accept it, deal with it, process it, and now move through it to even have the clarity of the Decisions to make, be able to turn that thing around. When you're afraid that the thing is not going to turn around, it's not going to turn around. When you can just take the gloves off and play the game and most importantly, take yourself and your ego and the own results that you're trying to get out of it, that's when you can actually be free to build a real business. The strange irony of entrepreneurship is that when you can forget about the results that you're going to get and you go all in on the customer that you're wanting to serve and you're creating products for them that they're going to love, that's when you profit. That's when you get all the accolades. Elon Musk wasn't nobody until he almost went bankrupt building a company that other people loved. He didn't become the richest person in the world until he built the company. That solved a problem that pretty much everybody in the world wanted to solve. That's why Elon Musk is Elon Musk. People see him now and say, must be nice, but he was serving other people through for decades before he got any accolades. Entrepreneurship is about being really fucking humble for a really long time and being in service to other people for long enough that you start to get the reward and then everybody looks at your success and your results and then you get a little bit of ego and then you forget about the humble roots you came from and then you slam get humbled and you remember that this is not about you, that it is all about your customer. I have been guilty of saying to clients that I'm working with who they're talking about, well, I want to make more money and I want to grow this thing. And I have been guilty of interrupting them and saying, fuck you, you don't matter. Only your customer matters. And I only know that, and I can only say that from a place of love. And they know that I'm saying it from that because I've made the same mistake. I've made the same mistake of looking at a business and asking the question, how much money can I make out of this? The minute, the second you ask that question, you start to do things that are for short term profit and short term results. And you stop acting in service to the customer, which means that your business is going to get taken over by somebody else who is more customer centric, which means that they're going to get all the customers, which means that long term they're going to win, which means that you are then Going to make more short term decisions to try to catch up in the marketplace, which is going to lead to more short term decisions. And you are going to go out of business. I only know because I've done it. I only know because I have made the mistake of trying to turn a business that I bought and I didn't want to lose and I didn't want to be a big failure into a short term cash machine to try and pay the debt off it and just became like a downward spiral. But I'm still here. I'm still playing the game. I've still got lots of wins. I've still got as much motivation and inspiration and knowledge and experience to be able to carry me into the next chapter of my career. But it took a lot of pain and shame to get to the place where I could finally just accept that. I've got losses too, and really big ones. So here's what you need to know. You're gonna make mistakes. You're gonna make errors. I've made them and I made really big ones and they hurt. The bigger you get as an entrepreneur, the bigger your mistakes are gonna be. This idea that as you grow, you're gonna make fewer and fewer mistakes is wrong. Because you're going to grow faster and faster and do things on a bigger and bigger scale. That means that your mistakes are going to be million dollar mistakes. You will never stop making mistakes. You will never stop losing at things. You're just going to win bigger and lose bigger. And the second thing is that it doesn't affect who you are. Having losses and having setbacks. First of all, they're temporary. You're still playing the game. You're still alive. You still got time. Do you have any idea how quickly things happen when they're lined up right? Do you have any idea how much better you are in position to win really big when you have learned from a treasure trove of mistakes from your past? I am in such a better position to crush the every project that is put in front of me because not only have I learned things from my failures, but I've learned to deal with them. I've learned that they don't affect who you are, that they don't change your value. And you know what else doesn't change your value? Winning really big, having a lot of money doesn't change who you are. Having a lot of success doesn't change your value as a human. And when you know that your value, your character, that who you are is the same whether you win or you Lose. That's freedom. That is being at choice. That is when you can decide which projects you're going to go all in on and swing and miss and hit a few base hits and smack a couple home runs. And you didn't need anything from it because you're good with who you are, man. That's the game. So I lost $2 million. It's actually a lot more than that. And I'm better for it. And I'm almost to the point where I'm thankful for it. Not quite there. It still hurts. It's still not fun to talk about all the time. But I know I'm better for it. And I know that because I'm better for it, I will have the opportunities that far surpass what I have lost. And somewhere along that journey, I'll be grateful for the losses. The losses are short term. You're in this game for the long term. So accept them, deal with them, move on. You're the same person whether you're living in a shoebox, whether you're living in a closet, or whether you've got a mansion worth $10 million. I know because I've experienced.
Not quite both of those, but, you know, experiences closer to those two extremes of the, of the spectrum. And if you're not in this game because you love this game, then you're in the wrong game. And one more thing. After losing and winning and experiencing all of it, you realize you get to the point where you just start picking the projects that you're going to enjoy. Please, just go after the projects that you find value in, you find excitement in, you find joy in. Because that's why you want to play this game anyway. You want to make the money so that then you can do the projects that bring you meaning, or you can just do the projects that bring you meaning. If you recognize that you're going to feel pretty much the same with debt or with a million dollars in the bank, you're going to be about the same person. Then just go after the projects that give you meaning that you want to do, because those are the ones that are going to end up putting a million dollars in your bank account anyway. Failure is not the opposite of success. It is part of success. It is part of learning what not to do so that you can focus more on. On what to do.
It's a true stat that 99% of business owners never clear a million dollars. And that is why I started a mentoring group called the 1%. I have helped hundreds of entrepreneurs cross seven figures. There's a reason why that's the case, and it's because we have a formula that works really well. And this year in 2021, we've introduced mastermind groups at each level in the process. That's the grind, the growth and the gold.
So when you come join us inside.
The 1%, you'll be partnered with other entrepreneurs who are at your level to help you get through that level and accelerate onto the next step in your journey. You'll be following the same roadmap that I teach in my book, 12 months to 1 million. That's why we have such a high success rate getting people to where they want to be. So go to capitalism.com1, scroll to the bottom, hit the join button and for less than you spent on eating out.
This past month, you'll be in a.
Room of entrepreneurs who are pushing you to go from where you are right now to the next step in the process. It'll be the best investment that you make all year. Come join us. We're ready for you. Go to capitalism.com1.


