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All right, you guys hear me talk a lot about my wins and making X amount of dollars and Y amount of days, yada, yada yada, but entrepreneurship is anything but rainbows and butterflies. There's a lot of hard, hard, sucky things that you gotta go through. And so today I wanna talk about some of those things. Six of those things to be exact. I wanna talk about six of my biggest failures of all time. Not six of, but my six biggest business failures of all time ranked from number six to number one. Number one being the worst. The biggest. And I'm measuring these failures just by how much they impacted me. Not by dollar amount necessarily or time spent on them, just how much emotional or mind space impact that they had on me. And here's the thing about social media. It does not reward people talking about their failures. The algorithms do not like it. Therefore, the people that are genuinely willing to share about their failures are disincentivized to do so because they don't have a positive feedback response reward loop after sharing those failures. With some rare exceptions. There are exceptions, but let's just get into it. Number six, no BS Crypto. So you guys might know the story back in 2018 when I launched a crypto business with John McAfee. If you want to hear that whole story, it is episode nine, way back in March of 2024. I tell that story in detail. It's one of my best stories. I love it. It's a great story to tell at dinner parties. But at the end of the day, that business failed and it took two years of my life. Now, I netted out ahead, financially speaking. But this business was a great lesson in not starting businesses where you have not enough control. Sometimes that control looks like not enough equity in the business to really have enough decision making power. Sometimes it looks like you being in a market that the business is highly dependent upon, as if you were in the oil business. It's boom and bust. And no matter how hard you work, you're going to have a really, really hard time making the business work during a bust cycle. Well, that's how crypto is. I've made the same mistake twice. Crypto peaked on December 17, 2017. That's when Bitcoin hit $20,000 and I launched this business a month later. Now, at the time, it felt like the perfect time to launch a business because bitcoin was just dipping a little bit. It had been 20, now it was 18. So we're quote, buying the dip. Little did we know it would end up at $3,000 down 84.5percent at the end of that cycle. And making a crypto business work in that market is like a goldfish trying to swim up Niagara Falls. It's just not going to work. And so yeah, I totally could have done things better. I could have been smarter about it, but I genuinely don't know how I could have made that work. We spent hundreds, if not thousands of hours building out a community, building software tools, writing an 18 page white paper, having a free airdrop, tons of content. We had a community with 70,000 people in it. We had people that invested into this token that we had airdropped out for free and they lost their money and I lost money. But I am grateful that I never held an ico, an initial coin offering where you basically sell your token. I never did that. It was just a free airdrop. But nevertheless, once it hit the exchanges, people purchased the token expecting it to go up in value. And it did sometimes, but most of the times it didn't and it ended up crashing. So this is a failure that I regret, but it was a great learning experience, especially when it comes to getting John McAfee's attention, getting in front of him, partnering with him, and learning that I'm capable of doing cool things like that. Alright, biggest failure number five. This was my business phone restore. Now keep in mind, these are failures of mine. It doesn't necessarily mean that the business failed. You'll see what I mean by the end of each section when I call it a failure. Because this business was objectively a success. I made a lot of money from it and I came out on top. But I had three iPhone repair stores. Well, four. One in Tuscaloosa, one in Birmingham and two in Huntsville, Alabama. I got approached by a competitor to merge forces. I didn't know the guys, they were throwing off yellow flags all over the place. They pressured me to sign a deal before the end of the year to keep taxes cleaner. My lawyer was dragging his feet on reviewing the contract and I just thought, eh, we'll make it work. This was before the days of ChatGPT. We're talking 2011, 2012. So I couldn't even have ChatGPT review my contract. And there were some big, dumb, stupid things in there that I never should have agreed to. We signed a contract. The deal was that I would get a third of the profits in perpetuity mailbox money without having to do any of the work. They both of them would get two thirds of the profits collectively. They would invest money into the business they would grow the brand. I got a little bit of cash at closing, nothing crazy. And everything changed after we signed the deal. I started another business in the same industry selling iPhone parts. I didn't have a non compete. I was fully elected, allowed to do that. I told them about it after I did it and my business started crushing it. And I think they saw that and they got a little jealous because they wanted to do the same thing, which I didn't know. They wanted to sell iPhone parts. So unknowingly I created competitor for them on a product line that they had yet to launch. And I started doing really well and they became a customer of mine, one of my biggest customers. But nevertheless, this played a role in decisions they made later down the line. I got that first mailbox money check the first month and I don't believe I ever got one again. When I maybe there was one more, two more, but never again, basically. And long story short, they ended up diluting my shares in half from 33% to 16% without my consent. They claimed to have my consent, but they didn't. They were basing it off some random conversation about an expansion plan. And I learned about this while I was in China at 2 in the morning. Incredibly depressing. It felt like two years of hard work had gone to waste and they had stole the business out from under me. That mailbox money I was promised never came. And to make matters worse, they still half the company. Massive failure. I had to retain a lawyer, I had to sue them. Thankfully their lawyer was an idiot. I'm happy to go on record and say that he was a complete moron. And a lot of the clauses in our contract did not hold up legally. It was an unenforceable contract in many ways, not in every way. And so that really helped our case. So my lawyer helped me claw back to about 29% equity, so up from 16 to 29%. And then they exited, they sold the business and I got a check for $275,000, something like that, cash. I was in my 20s and it was awesome. And I put it behind me. But that was a great lesson to not get married to someone you've never met. I mean, weeks had elapsed between the first time I had met these guys and when I first partnered up with them and basically handed over the keys to my business. Not basically, that's exact. I literally handed over the keys to my business without any visibility into the bank accounts, into what they were doing, and they took advantage of that. And again, business was Successful. It sold for seven figures. Those locations, most of them are all still there today. Fifteen years later. Every time I go back to Tuscaloosa to an Alabama game with my family, I drive by it. It's now called UBreak, I fix or Asurion or something, but it's in the exact same location right on 15th Street. And I just drive by it with pride and it feels good. And the other location in Homewood, Birmingham is still there. And the one in Huntsville has since moved, but it's still in Huntsville. Then the one I had in the mall that closed down, that was more of an experiment. That was our 4 location, but it was a failure in that I partnered up with guys that I shouldn't have and I, had I done more due diligence, I never would have partnered up. But also had I done more due diligence and not partnered up with them, that business may have just fizzled out. Like they genuinely did a better job at growing it than I did because they were all in, they were more invested, whereas I was somewhat distracted. So if I could replay that over and over and not partner with them, I wonder if I would have netted out ahead or behind. Certainly would have had fewer gray hairs, but. But I may have had fewer dollars in the bank account as a result. So that's number five. Number four, send eats. So this also was not a literal failure in the sense, but it was a failure in the sense that we had to let a bunch of employees go and we made some bad decisions that led to that. This was a third party logistics business which meant that E Commerce Brands would ship all of their products to us. We would store em in a warehouse and then as they got sales through their Shopify site, we would pick, pack and ship out their orders from our warehouse. This is a very bad business. You're competing with Amazon, but you can't compete with Amazon unless you have billions, which we didn't. And so we were making $400,000 a month in this business, but we were losing money. And 90% of our revenue came from one customer. And what a toxic relationship that was. They were a very, very difficult customer to work with. And it was very straining on my mental health. And I don't think I've ever said that about any other customer or vendor or business period. Like of all the 75, 80 businesses I've ever started, no relationship has ever been that toxic or that mentally taxing on me and my business partner and my employees. And I'll never forget I was sitting in the hospital in Houston, Texas, bedside of my daughter, who was literally in her deathbed at the time. It didn't become her deathbed, but she. It was not looking good. She needed a lung transplant. And I was at my wit's end. And this vendor of mine, customer who represented 90% of our revenue and 90% of our employees, was just berating me, just absolutely berating me over email. I just went nuclear on him after talking to my business partner first, because you have to make this decision, like, do we fire our customer and therefore fire 90% of our employees that support that customer, but stop getting abused by them, or do we just grin and bear it for the sake of our employees even though we're losing money? And it just made logical sense to fire him. And so I just went nuclear. He had been holding his power as a large customer over me and wielding that unrighteously, for lack of a better word, thinking like, you could never fire me. Because he knew how much revenue he represented in my company. And we called his bluff. We said, no, we will no longer ever ship your orders, ever. And they had thousands of orders ready to ship, thousands of customers waiting on those orders. And we said, we're done. Come get your crap, pay your bill, we'll palletize it up. You can come get all your boxes and your product and we'll ship it to the next third party logistics company that you choose. They freaked out. I mean, they freaked out, but we didn't budge. We absolutely did not budge. And they threatened to sue us and yada, yada, yada. And I said, I'll never forget. All right, I'm going to read this email because this is one of my prouder moments. October 21, 2021 at 6:55pm oh, man, this, like, is triggering to read, but it's also an amazing feeling to read this first name. You are volatile, hostile, and unpredictable to work with. You literally fired us this morning, but still want us to take the risk of scheduling our employees to come in and fulfill your orders. We are behaving like a company you fired and this upsets you, but your words have consequences. As I read this email, I'm remembering, like, he had fired us and basically like, expecting us to say, no, no, no, no. And we just said, okay, fine, we're done. I don't remember exactly how it went down, but yeah, we called his bluff, basically. And then he's like, wait, you have.
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To ship our orders.
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And we're like, no, you just fired us, bro. And we're happy to be fired anyway. Next paragraph. As previously stated, we are happy to continue working with you if you are not involved in the communication between us. So we basically said we'll keep working with your company, but we can never talk to you again in any form or fashion. We cannot risk our business on someone making emotional threats at every turn that have real life consequences on our business. There is a direct correlation between the strength of our working relationship with your company and your involvement therein. As previously stated, we'd love to continue working with and fulfilling orders for your company, provided your company agrees that we are still your fulfillment partner until a mutually agreed upon date and you are not communicating with us and you are not communicating with us any longer. Any damage caused by these interactions today will be a result of your pride and unwillingness to cease or take ownership of toxic behavior. Your continued involvement in this working relationship is a greater liability to our business than the current threats you are making. And I meant that basically it's a greater risk for us to keep working with someone as psychopathic as you than it is for us to stop being your vendor. And after that email, his team stepped in and took over to see things through and they ended up going through a couple more fulfillment partners that didn't work out either and they ended up just fulfilling themselves. A couple years later I spoke to his team who had since moved on to other positions and they agreed that that was an absolute terrible situation. So anyway, that was a failure. We should have managed that better. We should have been on top of our numbers so we didn't lose tens of thousands of dollars every month. We just weren't on top of our numbers. We could have prevented that. We should have fired them a lot sooner because we had 20 something employees that were reliant on them being our customers that we had to let go and or reposition within the company. All right, we are to number three. There's a good chance you've heard this story before as well, especially if you follow me on Twitter. I had a whole episode dedicated to it last year. I don't even remember what episode number it was. But long story short, I had a business a few years ago with a couple partners. Actually, I didn't know them at all when I partnered with them and we built a big business together. We had a $50 million offer on the table to invest in our company, which was life changing money. It was going to help us scale. It was incredible. And then the two partners went behind my back and said, dad, we really don't need Chris Here he's kind of redundant. There's not enough room in the equity stack for all of us, plus the investors. So let's just kick him out. And like legally we can't kick him out, but let's just close this business and start a new one. Because the investors like us. They'll start a new business with us that does basically the same thing and he won't be a part of it. Well, he'll have 3% ownership instead of 33% and he'll have to sign a non compete to where he can't compete against us ever.
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All right, I want to pause here just for a second to tell you.
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Why I've used beehive for two years.
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And I just actually sent my 100th newsletter edition.
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I love Beehive.
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And you see email's different from other platforms because social media platforms are own your audience. In fact, YouTube just banned me for a week because they didn't like one of my videos even though it was perfectly compliant. If Instagram changes their algorithm, your reach tanks. Same with TikTok, Facebook and anything else you're building on rented land. But with Beehive, I own my list, I own my audience. I'm not at the mercy of some nameless, faceless algorithm. Every time I hit send, they just get my emails. And Beehive makes this simple. Growth tools, monetization and a free website. And I can't get enough of their analytics.
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And the data I get from Beehive, this is data that I can actually.
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Use and share with potential sponsors. It's everything you need in one platform. The smartest creators out there are the.
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Ones that own their own audience.
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So go to beehive.com Chris to get 30% off your first three months. That's B E-E-H-I-I V.com Chris, and start.
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Building something you actually own. So one of these guys I had gotten to know really, really closely over the year and a half that we had worked side by side, our family's vacation together, I think twice, maybe three times. Our wives were very close. Our sons shared the same birthday. They were very close. They live right down the road from me. They just sat down and said, hey, you're out, dude. I know it sucks, I know it's wrong, but you're out. I'm doing this anyway. I know it's wrong. I'm doing this anyway. And those words just still echo in my ears. And that was a failure. Like that. I had a lot of money, that was a net failure. No matter how you look at it on the monetary side of things, not like the life lessons learned side of things. But I lost money on that. I lost every bit of equity or potential future value that that company would ever gain. The reason it was not a failure was because of basically I took all those learnings from within that business and helped them catapult my career ever since then. And I started writing content about that industry and that, you know, occasional tweet or two about that industry turned into the content I produce today, which is over 150 million views a month across all platforms combined. And I don't think I would have ever even thought about making content had that experience never happened to me. And I don't know where I'd be today. I'm sure I'd be doing something cool and having fun, but I don't think I'd be where I am financially speaking or in my career. I think that terrible event like, was a net win for my career, although a net loss for me on paper. So kind of the opposite type of failure is my first couple that I mentioned. A net win on paper, but really just a net loss experience all around. But I firmly believe that like any, any, any bad thing in life that happens to us, as long as we like keep trying, we stay at it and keep trying to be a good person. Given enough time, that bad thing will turn into a good thing. Like, I firmly believe that there's only one or two things in my life that I haven't seen the good of already. One or two bad things that have happened to me and, or my family members and I've yet to see the good. But I think that one day in the future I will. So any failure, right? If we really want to get ticky tacky about any failure could be a good thing if given enough time. That was a big failure. And it was dumb of me to partner with a couple guys that I didn't know. I mean, I just keep making that mistake over and over. But I like working with people, you know, it's just funner to do it together. It really is. And like, despite all the partnership headaches I've had, I still recommend that people get a business partner, do it the right way. I have a lot of thoughts about that. That could be a whole other episode in and of itself. I've written a newsletter about it. But I think it's taken me a lot of time to realize that I don't make a super good business partner unless I have a very small slice of the pie. And I contribute a disproportionate amount of value to the business and the partners, I'm clearly distracted. Like, that's the whole theme of this, right? 80 businesses in 15 years. I'm always moving on to the next thing. I don't regret that. And I think that that has been one of the major reasons why I've done well is because I've compounded all my learnings across various industries. But as a business partner of mine, that could be really tough. Hey, Chris. Hey. Hello. That shiny object might be cool for you, but I thought we were doing something together. That's tough. And I've tried to get a lot better about that. When people approach me and say, chris, let's do X, y or z business. And I'm oversimplifying this, it's not how these conversations go, but for the sake of an example, let's just say, all right, Chris, I want you to put in 10 hours a week, and I'll give you 10% of the business. Nowadays, I'm much more likely to say, how about you only give me 2% of the business and you only expect three hours a week from me? I really, really, really try to under promise and over deliver now. And I tell people upfront. I don't really need to tell people upfront because I publish everything on the Internet. But even so, clearly I'm doing a lot of things. I'm very distracted. This isn't going to be my only thing, FYI. And so I know you want me to have a bigger role in this. I'd much rather have a smaller role and an even smaller proportional amount of equity for the time and effort that you're expecting from me. And then I try to over deliver, but it's taken me a long time to learn that, you know, when you have 15 business partnerships and most of them don't work out, at a certain point, you got to look at the common denominator and say, you know what, Chris? Either you really need to take a much smaller slice of the pie so your partners have less expectations from you, or you need to just do things yourself. Which I've learned to really enjoy that. All right, failure number two of six, man. That was a company that my best friend, partner and I started four years ago this month. Now, a bitcoin mining company. We launched that at the worst possible time. But at the time, it felt like the best possible time. In the summer of 2021, China banned Bitcoin mining. And so if you don't know about bitcoin mining. To explain it very simply, there's a few variables at play. Number one, the price of bitcoin, all else equal, the higher the price of bitcoin, the more profitable bitcoin mining is. Number two, the hash rate, which is basically determined by how many other bitcoin miners are trying to mine bitcoin. The more bitcoin miners there are, the more competitive it becomes to mine a bitcoin or a block of bitcoin, right? So if the price of bitcoin is not going up, but the hash rate, AKA the competition is going up, then the profitability of bitcoin mining goes way down. Because the statistical chance of you finding a block goes way down. Right? So the perfect storm happened in 2021 when the biggest bitcoin mining country in the world, China, said, no more. We don't believe in this, we're out. It is now illegal. So then all of us enterprising Americans raised their hands and said, all mine bitcoin. That sounds awesome. So at the same time, bitcoin was in a huge bull run. It was hitting an all time high. It was insanely high in value. And the hash rate, the difficulty rate of mining plummeted literally overnight, like thousands of miners. Unplugged. Literally unplugged. And mining became very, very profitable. Basically, you could spend like $500 in electricity to mine a $5,000 bitcoin. I'm oversimplifying, but it was like stupid. Mining was insanely profitable. And so around that time, Nick and I bought a bitcoin mining facility for three quarters of a million dollars. That way we were able to sell bitcoin miners and sell the hosting to go along with it. Because you can't just plug these things into the wall at your house. You need three phase power, you need ventilation, you need sound control, everything. It's a whole deal. So you can't really sell miners unless your customers have a place to put them. And if you have a place to put them, then you might as well sell miners. So we started doing that and we made $10 million in our first 90 days without any paid ads. It was just right place, right time, perfect product, market fit, yada yada yada. We felt like geniuses, like we're on the top of the world and we were profitable on that $10 million, right? And we just thought that we could do no wrong. But just like the no BS crypto story, we were fighting an uphill battle. Because what happened at the end of 2021, Bitcoin crashed. It crashed, it started crashing, right? It's a years and months long process. And the difficulty rate only went up and the price only went down. And all these miners we sold, the people that were fully expecting them to be very profitable, myself included, were not profitable. They were at first a little bit, and then less so, and then less and less so. And then they became unprofitable. And we could never turn that around. We can't change the price of bitcoin, we can't change the difficulty rate. And so every single year in business, our sales dropped and dropped and dropped. Profitability dropped and dropped and dropped. Customer sentiment dropped, Stresses went up, the losses piled up. I put in hundreds of thousands of dollars, my partners put in even more. Hundreds of thousands of dollars. The investors put in hundreds of thousands of dollars and net of net on the whole, looking back, that whole experiment lost money. Lost money for me, my partner, my investors, the customers, bitcoin miner investors, everyone really. The only people that won were the hosting facilities that we partnered with that marked up the rates. They won. And the companies in China that sold the miners, they won. And it sucked. It sucked because I sold some of these miners to friends and family. And I'm always very, very careful about that, very wary about that. Overly so. Like any investment, Bitcoin is the most attractive when it's the most expensive. And then as soon as it gets cheap, no one wants to buy it. That's how any type of investing works, period. End of story. Real estate crash, stock market crash. As soon as it's cheap, everyone's afraid. Soon as it's way too expensive, everyone's greedy and hungry. And so I was getting calls and texts every single week from friends and family. Hey, don't you sell miners? Hey, isn't mining profitable? And I was buying miners myself, I was eating my own dog food, I had my own miners in my own warehouse. Because I'm like, heck yeah, this is a legal money, literally a legal money printing machine. And so most of our customers lost money. And me and my partners invest everyone. So massive failure, no matter how you look at it, financially, emotionally, it's just a failure. I don't know what I would have done. The whole business was built on the thesis that retail mining needs to happen. I was very still am very passionate about that. That mining should not be in the hands of these mega corps, these multi billion dollar corporations, that mining should be distributed, that people should have a miner in their garage, that they should have one hosted at a data center full of other Retail miners. And if you look at the hash rate today, it is outrageously high. Mining is still not great, despite the fact that Bitcoin is 112,000, because the difficulty rate has grown much faster than the price of bitcoin. And so even though bitcoin's near an all time high, bitcoin mining for retail investors is still dead. And I'm honestly pretty pessimistic that retail mining will ever be alive again just due to the nature of what mining is. You have to have cheap energy. And the only way to have cheap energy is to be at scale or to be in some random third world country or to be flare gas mining in the middle of west Texas where everything breaks down because of all the dust and heat. You just need scale to have cheap energy. And even when you have cheap energy, you're exposed to all these price fluctuations. And when do you sell? Do I hold the bitcoin after I mine it? Do I sell it immediately? You kind of have to become a trader in a sense. It's just an impossibly hard business and one that I had not nearly enough control over. But that's not my biggest failure. Almost lost a friendship over it, but did not. Happy to say that we are still doing great, but we went through some rocky points. But my number one biggest failure is my biggest failure because of the friendship that I lost over it. I had a company for seven, eight years that sold wholesale iPhone parts. This is the company after my iPhone repair company. And I launched it by myself. But I soon brought my best friend on a few months after founding, gave him a quarter of the business and he moved his family to Texas. And he had big hopes and aspirations, as did I, for what that equity would turn into. And it was a ton of fun to work side by side with each other, grow this business. We grew it really fast. It was really profitable for a long time. But I was just a stupid leader. Like I was just young. I was in my mid to late 20s. I was all over the place. I was unorganized. I had 25 employees across four different states, four different warehouses. I wasn't keeping track of anything closely. I was, you know, testing other business ideas. I was not being a good steward of this business, of this revenue, of this equity. And the tide turned. The barriers to entry in this business were very, very low. Basically, if you had a free Alibaba account, you could import iPhone screens for 15 bucks and sell them for 28 bucks. That's all we were doing. That's it. If you could learn how to, you know, import stuff through FedEx and DHL 3 Day Air. You could be in business. If you could scrape off and repair stores and cold call them cold email them, you could be in business. If you could build a shopify store, you could be in business. And so over the years, we saw more and more competition, and some of them took this business very, very seriously. They raised money. They were sophisticated, they had good leadership. They had their own warehouse, they fulfilled their own stuff, and they just outsmarted us. And we did some really cool things in that industry. We pioneered the lifetime return policy. We were the first to start it, and then everyone copied us. We did tens of millions of dollars of revenue. But there was this weird dynamic between me and my best friend. He was like the CEO. I was just kind of the owner, but, like, he was kind of the CEO in name only, and I wasn't really treating him as such. And there were a lot of ambiguities between him and the other employees. And, you know, as the owner of the business, it was my responsibility to. To clear that up and to set the record straight. And then one day in 2017, I had this call with my accountant, and he said, hey, bro, you've lost money this year. You're losing money every month. And that floored me. I didn't know I'd been losing money for I don't know how long. And I had no idea. I'll never forget that phone call. And we had to make, like, immediate changes to the business. We had to let people go. We had to close warehouses, and I had to cut back. I had to eliminate profit distributions for all the shareholders, including my best friend. And I didn't show much grace or leniency in doing that. I made too big a cuts too quick to people that I loved. And I could have done it better. I could have rolled it out slower. I could have given them more breathing room, more Runway. I'm trying to tell both sides of the story here, because there's always two sides of every story. So I'm trying to tell both sides at the same time. Obviously, I'm biased, but given the benefit of time, I have been able to see more the error of my ways. And it took me years and years to. To see that. I think for the first several years, both me and him were pretty bitter about it. And that's a hard place to be where both people. Well, where neither person thinks they did anything wrong, or at least each person thinks the other person did more of what was wrong. But given enough time, I think I've come around and I'm more on the other side of the table than my own side of the table at this point. And thought, man, I really could have managed that better from day one. So I have a lot of regrets about that business. I think people say that they live with no regrets. They aren't introspective enough. I think it's good to have regrets because regrets drive us to be better. If we truly don't have regrets, then what are we really improving towards? So that is my number one failure, even though I netted out ahead on the balance sheet, right. I lost a great friendship over it, and it eased me up inside, even though it's been like eight years now. And that's a lot more valuable than money or equity. So when it comes to partnerships, I can honestly say that a business partnership is more difficult than a marriage. It's more critical, even not more important. Right? Of course, marriage is the most important relationship in your life. But, like, I think it's a lot harder to make a business partnership work than a marriage, frankly. I think that there's no stigma attached to partnering with someone too quickly, whether. Whereas there is a stigma attached to marrying someone too quickly and for good reason. That could be a mistake, right? You got to get to know the person. But in business, it's like, oh, yeah, these guys met in their dorm room and they built the business. Yaddy. And we hear all these success stories, but it's all survivorship bias. We hear about the ones that worked, but the ones that don't work, you know, no one's really talking about them on podcasts, even this podcast, except for, you know, one episode out of every 230 or so. But in my opinion, the 80, 20 of business partnerships are 50. 50 rarely works unless both partners are in person together. Not remote in person, side by side, all in both. Feet first, not working another job, not as a side hustle, but literally in the same room, building the one thing together all day, every day. 5050 can be great there. Outside of that, if you're remote, one of them works, the other one doesn't. One of them put in money, the other one didn't. One put in more than the other. It's not going to work. Sorry, it's just not going to work. I think it usually needs to be someone in the driver's seat. 60, 40, 80, 20 equity split, an investor and an operator. That can work. That's more likely to work. Going to business with your friend, it's a lot of fun. It really is a lot of fun. But, man, watch out. Be careful. Know what you're getting yourself into. High risk, high reward. Hope you enjoy this episode. I might regret publishing this one day, but what's done is done. Thanks for hanging out on the Kerner office.
Host: Chris Koerner
Date: October 24, 2025
In this raw solo episode, serial entrepreneur Chris Koerner peels back the curtain on his six biggest business failures, sharing the stories, mistakes, pain, and lessons that shaped his career. Rather than boast about multi-million dollar wins, Chris gets highly personal, ranking the failures based on their emotional, mental, and career impact—not just on financial losses. This candid deep dive is intended as a reality check for fellow entrepreneurs, with the goal of saving others years of hardship by learning from Chris’s costly mistakes.
"Entrepreneurship is anything but rainbows and butterflies. There’s a lot of hard, sucky things you gotta go through." — Chris Koerner
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Lessons:
Quote [02:58]:
"Making a crypto business work in that market is like a goldfish trying to swim up Niagara Falls."
Memorable Moment:
"...learning that I’m capable of doing cool things like that." [05:18]
Story:
Lessons:
Quote [09:26]:
"I literally handed over the keys to my business without any visibility into the bank accounts…and they took advantage of that."
Memorable Moment:
Story:
Lessons:
Quote [11:45]:
(Excerpt from the October 21, 2021 Email)
“You are volatile, hostile, and unpredictable to work with…there is a direct correlation between the strength of our working relationship with your company and your involvement therein.”
Memorable Moment [12:33]:
“We are happy to continue working with you if you are not involved in the communication between us.”
Story:
Lessons:
Quote [14:36]:
“I know it sucks, I know it’s wrong, but you’re out. I’m doing this anyway. I know it’s wrong. I’m doing this anyway."
— Partner during their falling-out
Big Idea:
“…any bad thing in life that happens to us…given enough time, that bad thing will turn into a good thing.”
[16:43]
Story:
Lessons:
Quote [19:22]:
“Mining became very, very profitable. Basically you could spend, like, $500 in electricity to mine a $5,000 bitcoin…I’m oversimplifying, but it was like—stupid.”
Memorable Moment:
“I was eating my own dog food...but most of our customers lost money.” [22:24]
Story:
Lessons:
Quote [26:27]:
“If we truly don’t have regrets, then what are we really improving towards? I think it’s good to have regrets because regrets drive us to be better.”
Memorable Closing Thought [28:21]:
“A business partnership is more difficult than a marriage…There’s no stigma attached to partnering with someone too quickly in business, but there should be.”
The Pattern: Chris’s biggest mistakes consistently stemmed from poor partnerships—whether due to lack of due diligence, unclear roles, or misplaced trust.
Business Partnerships:
Enduring Principle:
“Given enough time, any failure can become a win—but only if you keep moving, learning, and striving to be better.” [16:55]
This episode delivers a rare, unfiltered look at the messy side of entrepreneurship, emphasizing hard-won wisdom you won’t find in Instagram highlight reels. Chris’s humility, candor, and actionable advice offer significant value to founders, side hustlers, and anyone interested in building — and sustaining — successful ventures.
“High risk, high reward. But, man, watch out. Be careful. Know what you’re getting yourself into.”
— Chris Koerner [29:38]