Business Insights from Drake Losing $30 Million on Roulette
2 Feb 2026 · 31 min
Podcast episode of Business Lunch (hosts Roland Frasier and Ryan Deiss) centered on a viral clip of Drake gambling on Stake (online roulette), allegedly winning then losing roughly $30M. Hosts play clips and use the episode to extract business lessons—risk management, sunk-cost bias, fundamental attribution error, timing, probability/house edge, sponsorship and brand alignment, audience influence—while referencing Buffett, Jim Paul, and Daniel Kahneman. The episode includes sponsor reads (Belay Solutions, Epic Deal Fast Track) and conversational analysis aimed at entrepreneurs on how to apply these behavioral and risk lessons to business decisions.
Chapters
Eddie, what did I tell you? It's my night tonight. Eddie, what did I tell you? It's my night tonight.
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Hey, everybody. Roland Frazier and Ryan Deiss here with an episode of Business Lunch for you. And we're gonna do something kind of fun and different today. First, Ryan, how you doing?
I'm getting over a bit of a sinus infection, so if I sound extra nasally, that's why I'm at that awkward part where I feel great, but I sound like crap. So I'm getting all of the sympathy. But it's too late. It's way too late. I needed sympathy like two or three days ago. No, I'm glad it's happening now. About to leave for a family vacation. Confirmed with multiple tests that it's not Covid. So other than that, nice.
So you're not reinfect Europe and make it closed again for all of us.
That's the goal. That's the goal. What about you? What you got going on?
Just coming off of the Memorial weekend holiday and enjoying basically having time to kind of catch up with a whole bunch of stuff and found a lot of interesting things, including what I want to talk about today, which actually my son Ryan, who is one of our producers here, shared with us, and we're doing some fun new tech here because theoretically we're going to be able to bring up a couple of clips so that you guys can see what we're talking about, and then we're going to.
Talk about the people listening on the podcast will be able to see it. Are we going to, like, have it Kind of Star wars style, like beam up from their phone or from their listening device?
Yeah, it's a holograph. And so if, if you're listening through something that does not have a visual surface and you don't see the holograph, please let us know because it means something's wrong with probably your equipment. That's my guess. Kidding, kidding, kidding. Okay, so this is one Ryan I kind of want to get your opinion on. Here's the deal. Drake is a spokesperson for an online casino that is based outside of the United States called Stake. He's basically coming on and gambling and they're videoing him gambling. And he wins and loses about $30 million throughout the course of this over about an 80 minute period. And I want to talk about, like, I want to play some of the clips and then I want to talk about a few things, you know, because I think there's some good analogies to, we're all somewhat gambling as entrepreneurs. When do you cut losses and when do you double down? That's to me a really interesting question. How about sponsorships? And how, you know, how do you want to show up in the world is another thing that I'd like to talk, particularly when you're influencing people on something that has proven to be an addictive challenge, but really anything that maybe isn't necessarily great for the world or for your audience and who do you want to kind of align your brand with with? So the interesting thing to me was that Drake exhibited a lot of classic gambler like gaming addiction type challenges by the things that he was saying. And I don't know that he's a gambler or, you know, or in trouble or anything, but it sure is a great way to get there. And I know with Phil Mickelson recently having a whole bunch of challenges and going all the way back to like Pete Rose betting on games, it's like there's so many people that have run into these challenges that I think it's dangerous to be, to put this kind of stuff out there. But I want to get, I kind of want to get your opinion on it and see what our, our listeners think. He starts with 10 million. They don't say whether this was something that was gifted to him or it's as actual money. I'm assuming it's probably gifted to him, but I think they should probably say. And then he goes up to about 30 million and then ends up losing it all.
Oh, my goodness. Get over.
Back to, back to back.
Yo, listen, when you have a good heart A pure heart. This is what happens.
So he's playing roulette religiously.
Oh. He was saying he was winning because he had heart. He was coming to it with heart.
Yeah.
Just the main reason that you win, you know, any gambling game. Yeah.
It's kind of like I'm, I'm. Because I'm passionate about my business. My business is going to succeed, but just like this. So the setup here, for those of you who are listening and can't watch, we are watching Drake, rapper Drake playing online roulette.
Yeah. But it's. It's interesting because it's online video roulette. Yeah, it's videoed. So it's an actual roulette wheel if you're listening, as opposed to like a computer generated thing. So you've got a live roulette wheel operator, a rouletarian, if you will, who is spinning the thing and then they're showing us where the ball lands. Is saying the amount of logical fallacies that come out of Drake's mouth are just kind of mind boggling. It's so many things. Yeah.
I mean, he said it's all luck, but you don't want to redirect your energy.
But it's timing too.
It is luck, but it's also. Okay.
Yeah. So it's timing. If you can time your luck to the times that you're making big bets, then that's really how you ought to gamble. Okay, that's. I think that's really the message that's coming across there.
But like, I mean, one thing. I mean, so like, you know. Cause I love poking fun to celebrities as much as the next guy. I do think there's something to the. I think like there's obviously something to passion in business. Right. And there's something to timing and focus. There's definitely something to luck.
Right.
In business. So if we're going to apply some of this advice to business, I can see how this makes sense. But we're literally applying this to a game of chance. So this just feels to me like maybe a misapplication of good ideas just at the outset. And I'm seeing this the same time as everybody else. I hadn't watched this before.
Yeah. And two things. One is what he was saying. There is. He's saying people are telling us to better on zero. But. But I don't want to interrupt the energy. And I thought that was actually interesting. We could take a business lesson from that, which is a lot of people will tell you to do something else or to run their strategy or their game plan, but you really got to stick with yours until you see how it plays out.
Well, especially if they don't have any money in it, they don't have a vote. Right. There's lots of opinions with no skin. So I guess I respect that.
I do respect.
We're just still playing roulette. We're just still playing roulette here.
Yeah. And then also at one point he says, well, this hasn't been working. He starts losing a lot of money. I think he loses about 10 million. And he's like, so I'm going to do something different. I'm going to stand up. But that also, while that doesn't to me seem like it might have an impact in how the roulette wheel that is not even near him is going to operate, it does also go to business is that, you know, if you have given something a chance to run and it's not working, then don't be insane by expecting the same thing that you've always done to get you a result that's going different from the one you've always got. So he is, you know, so there are some. Some of the brilliance of his entrepreneurial nature I think does show through, even though it's through the lens of I'm playing remote roulette.
All right, well, I guess steak won tonight.
Yeah, unfortunately, next time.
People won tonight, man. Yeah, well, that's all that matters. The people won tonight. As long as you guys got blessed. I'll make it back. I'll be on late night, you know, go get some dinner and then get fried and maybe come back on and try and win my money back.
Yeah. When things don't go well.
Right. Have dinner.
Just go get high.
No, we'll have dinner. First you go, you gotta eat, then you get fried.
Yeah.
And then you make your money back. Yeah. Right. It's a good plan. It's a three step plan, Ryan. All the best plans are three steps.
Yeah. First you get the money, then you get the power, then you get the women.
Yeah.
No, I've seen that movie too. Yeah, I guess. So a lot of things here. Like if I were just to throw out what's popping into my mind kind of in real time, there's a lot of false attribution error going on. Like, I'm going to assume that because I stood up and like that's going to change something when it's not. And you and I have talked about this before. Like I'm a religious guy, like I'm a practicing Christian and So I did.
Not know that you played roulette, but now I do not roulette.
But I mean, that being said, far be it for me to, you know, as a religious, spiritual person, like to kind of mock somebody else's religion, superstition, whatever you want to call it. But I think you've got to be really, really, really careful about over applying the way that you feel into something that is inherently out of your control. And I do think that it's important in life and business to be really open about the categories of. There's categories over here. There's all this stuff that I can control and then there's all this stuff over here that I can't. And the second you start to pretend like you can control the things you can't control, that's when one of two things is going to happen. You're either going to get delusionally confident if you just get lucky and happen to be right. And now we're going to begin to apply that to other areas where it doesn't apply or you're going to get like it's going to be hopeless.
Right.
Because you're going to attempt to control the uncontrollable. So so much in business is just saying, okay, what can I control about this situation? What do we have control over in this situation? Great, I'm going to control that to the best of my abilities. Now what don't we have control over? Well, there's a whole list of things you don't have. Great. How can we, you know, mitigate against some of these risks? How, how can we hedge against some of these possible uncontrollable things so that if they happen out of our control, it doesn't take us out? I know for me we do well, but I'm not going to put 10 million down on the roulette wheel. So just what you're buying is.
Yeah, yeah. And I think, I think that's a really good point. I think the danger is Drake's a brilliant music musician, a brilliant business person entrepreneur and he has experienced great success and, and probably created a reality distortion field like Steve Jobs that has helped him throughout his career to overcome any odds that he might have faced and rise to be crazy, crazy successful and super wealthy. But that can that success misapplied towards something that truly is chance. Particularly something that's chance. Where the odds are stacked against you can be challenging. And for him it might be what the odds were stacked against. Me being this successful, having this many hits, making this much money, you Know, doing all these entrepreneurial deals, I'm doing. So this is just another thing like that. And I mean, it would be, it would be hard to argue with that, except that absent illegal application of some force or something, he cannot, his actions cannot affect the outcome of the spin of the roulette wheel, whereas his actions could affect the outcome of all the other things. Right?
Yeah. So do you know, I just googled it, by the way. Do you know Drake's net worth according to Google, which, you know, is obviously.
I'm guessing it's a few hundred million.
260 million according to Google. So if this is true and if he did in fact lose $30 million.
10% of his net worth, right.
And like, and like you said, it's possible that they just staked him for 10 million and you know, had he won 30, then they would have gotten their 10 plus some whatever back. Like casinos will do that from time to time for, you know, for celebrity type folks, show that they're in there. But if he truly did lose $30 million of his own money, that would be more than 10%. That's a lot. I mean, I know when, when we are talking about portfolio allocations, we'll say that 2, maybe up to 5% is going to kind of be in that YOLO fund, right? That, that, that kind of asymmetric bet. So like, if you want to go and you know, dabble in crypto or in NFTs or you want to invest in your buddy's pizza restaurant because you like your buddy and you know, it's probably going to make no money, but you get to walk in and walk behind, you know, pull yourself your own draft beer. Like all of these are kind of the, you know, whatever. This would be fun. And at no point should your total risk outlay be anywhere near 10%. So I do think that it's important, right? When you're thinking about, and this is, this is individuals and it's also businesses, right. You got to create these different categories of how, how confident are we that this particular project is going to work? And one of the things that we look at is like a good, better best, when we're saying what do we believe the outcome is going to be and the better outcome, we want to feel like there's at least 80% baked in. Like there's about 80% chance that we're going to be able to get there. We got to figure out the other 20%, but we got 80% kind of baked in. When you're putting this level of risk on the table, in this case, literally, boy, that's nowhere near 80%. So I think so much of this is just risk management. It goes back to Warren Buffett's rules of, like, just don't lose money. Don't lose money. But, you know, like Drake said, my guess is if he wants to go and make 30 million next month, he can go out there and make 30 million if he wants to. It's just money.
So I think that that's really important. I want to take a break to give a little shout out to one of our sponsors and then when we come back, talk about a lesson that Buffett teaches and how that applies here. I want to kind of show you the progress of his activity during the gaming and then maybe talk a little bit about probability and how it can affect, how it can have a really surprising effect. And then last but not least, talk about associations and branding. So let's take a little break and then we'll come back and talk about those things.
Ryan here. And look, if you're an entrepreneur, you're busy, right? Whether it's replying to emails or scheduling.
Meetings, whatever, there is a lot of.
Work and a lot of hats that we need to wear as entrepreneurs. And that's why, as entrepreneurs, especially if you're a visionary founder, you need help, right? And I don't know about you, but at one point for me, I was getting so overwhelmed with all the little day to day tasks that, let's face.
It, they got to get done, but.
They don't necessarily need to get done by you. And so when I came to this realization, I said, I got to get help. I need to get a virtual assistant. I got to get a social media manager. And that's when I called my friends at Belay Solutions. Belay Solutions are an incredible organization. Now, look, I don't know about you, but I tried to work with VAs in the past. It was always a disaster. And so I was really, really suspicious of being able to make it work. But their process was fantastic. They found out the type of work that I need done, the type of people I like to work with, and they really did match me with a person. Perfect. Virtual executive assistant. And this person's been with me now for three years and counting. So obviously it worked for me and I think it's going to work for you. So here's what you need to do. All right? The good folks at Belay, they're actually giving listeners to this podcast. $300 off the startup cost for their virtual Assistants, you'll pay less than I did.
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Okay, so we are back. And I wanted to. I mentioned before we broke that I want to talk about like a. A Warren Buffett thought on this. And one of the things that Buffett teaches is I think his first rule is don't lose money. And that's easy to say when you are the oracle of Omaha. But at the same time, it is also a good lesson for us is like, a lot of us will ride bad ideas down. We'll ride bad businesses down. And you got to remember that a business is there to support you and generate money. And if you see that it's not working out, you've got to cut your losses. There's one of my favorite books is I think it's How I Lost. I'm gonna let Ryan talk in a second and I'll look it up for you. But I think it's how I lost a million dollars in the stock market. And it's from a guy that. And he actually lost it in the commodities market because he didn't sell. He kept seeing the market go down, but he was like, man, I don't want to lose. I don't want to. If I sell now, I lose my money. It crystallizes when you sell your loss. And this is good to talk about in the context of what's going on in the stock market right now, because we're in successive multi week losses in the stock market, then we have a little bump up, and the question is, well, do we sell? Well, you don't lose your money until you sell. But also you can lose in a business in particular, or in commodities, where this guy was trading or gaming, where Drake was. There you go. It's what I learned losing a million dollars. Thank you, Ryan. Who's the author? The author is Jim Paul. Jim Paul. Fantastic book, by the way. I listened to the audio. It's a really great story because he started out and then he had success, success, success, success, success across the board in everything that he did. And he says, you know, I got to the point where I thought it was me, that I was like, I was always. I was just one of those people that always won. And he'd never had a setback and then he lost everything. And he lost everything because he didn't cut his losses when he saw he had the chance to. So I want to get your, your thoughts on this, Ryan. So you got Buffett who says, rule number one is don't lose money. You got Jim Paul here who says, hey, I lost everything because I didn't see that it was going down. I didn't. I wasn't focused on capital preservation, and I held on way too long. But then you also have the philosophy of, well, don't sell your stocks or your crypto now because they're going to come back around. How do you reconcile those different philosophies from a lot of really successful people?
Yeah, I mean, there's two things at play here. The first is what's called fundamental attribution error. And fundamental attribution error is just a fancy way of saying I fundamentally attributed the wrong thing to something else. Right. And in this case, like he talked about, I thought it was just me. Right. You have Drake saying, well, I'm going to stand up. We've had other people, like, we've been in the position where we have delusionally believed that the cause of something was something that it was utterly unrelated to, and then we begin to misapply that in other places. I don't want to say the cure to fundamental attribution error, because it's very common in all humans, is to make a list of what are the things that I can control, what are the things that I can't, and really do that just as dispassionately as you can. These things I can control, these things I can't. If you can honestly look at that you're attributing to your success is in the things you can't control list, then you gotta know right then and there, probably a fundamental attribution error. If you're like, I can't be sure, right. That's not something that you can really hold onto. So that's kind of the first thing that I can see is just being crystal clear on that list. The second one is sunk cost bias. Right. And sunk cost bias, man. We talked about this in other episodes, previous episodes of this podcast. This is the one I struggle with the most so hard. I mean, you know, this, you know how I lost this book's how I lost a million dollars. You know, we could have written the how we lost two and a half million dollars on sunk cost bias from pursuing certain business models over business ideas over a couple of years. When we finally did the math, it was like, oh, combine. Those are about two and a half million dollars that we basically just lit on fire. Why?
Because we were always this close to finding the success.
We were always this close. And that's the thing. So here's the solution to that. Decide ahead of time before any cost has been sunk, okay? Before any cost of capital. And here's the biggie. Before any cost of pride, before any cost of capital, before any cost of pride has been sunk into an idea, a business, an investment, a spin of the roulette wheel.
All right?
Decide ahead of time what winning looks like. And this is big. Over what period of time that should take, right? If Drake would have decided ahead of time that winning is doubling my money, then as soon as that happened, he'd been out and he'd have walked away. 10 million left some money on the table. But yeah, 10 million do the good, right? If you decide this much, whatever. If you decide that, you know, doubling within this period of time, I'm in. And if I get down by more than 20% over this period of time, I'm out. So deciding ahead of time before anything is sunk is the way putting these rules. That's the way that you remove the bias that will inherently creep in, because none of us want to admit that we're wrong. And sunk cost bias is just a fancy way of saying humans, especially successful, prideful ones, like only every entrepreneur I've ever met, doesn't want to admit they're wrong, yours truly included. So. So, yeah, I think it comes down to being crystal clear. This is what we can control, this is what we can't. And deciding ahead of time before anything is sunk. What does winning look like? What does losing look like? Over what period of time? What is the downside risk that we're prepared to accept? And just as importantly, at what point are we going to take chips off the table? Because just like you can ride it too far down, you can ride it too far up and miss the peak or get anywhere near it and take it all the way back down.
So that's.
That would kind of be my advice to resolve all of the above.
I like it. And Nassim Taleb's book, if you want to pull it up real quick. Excuse me. Kahneman's book, Thinking Fast and Slow is a great resource for you guys to read if you. If you haven't already read it or listened to it. It's. It's basically goes into several of these biases and studying all these different biases that can affect how we process and think. I think this behavioral economics field is fascinating to help us be better entrepreneurs and business people. So, yeah, Daniel Kahneman thinking fast and slow. Fantastic book. Couldn't recommend that highly enough. Now, I want to play a little bit more of the clip where he talks about how the risk part works.
Roulette's a heartbreaking game, ladies and gentlemen, especially if you play the way I play. I play, like, very religiously. So I've had some rough nights, but I've had some incredible nights. Tonight is still an incredible night that we definitely doubled our balance so far. I see you guys saying put something on zero. But, you know, you know, the key is I hate to direct the energy anywhere else than what we believe in. I always feel that, like, by the way, this is all luck, chance, and timing. So if you direct the energy somewhere else, it means you're nervous. I don't like to direct the energy away from what we believe.
Yeah. So I thought that was really interesting because I don't think a lot of people think about that. Like, that slight edge can really help us in business, and it can really kill us if we're not aware of what it applies to here. It's not like, hey, I had 10 million, and I was playing with that 10 million the whole time. It's. I'm betting constantly. And if over that period of time, I bet 2 million, 1 million, 3 million, 5 million, 6 million, and I end up across the board at a total bet of 200 million, when I add all those little bets up and the edge was 5%, then that means I basically lose my entire stake. I thought that was something that was really cool.
Well, there's another factor there as well, because, like, the 5% edge. I mean, Roland, I know you hate gambling. I made you put, like, I don't know, a couple hundred bucks on the craps table just for. For fun. We lost it instantly because you're horrible luck. Which fundamental attribution error. No, literally every time, 100% of every time I've gambled with Roland, I've lost all of my performance.
My wife and your wife were there, too. So it might be that it's the collection of those people and, you know. Yeah.
The collective negativity of all those folks. No, but you don't like to gamble at all. I only like to do it just for fun with money that literally, it's like, this is what I would spend on a ball game or a movie or something like that with good friends. So what I know, though, back to the 5%. In blackjack, there's this thing called playing by the book. Right. And it's literally like the dealer's book. And I'm sure the same is true with roulette. I don't play roulette, but there's a right way to play it. And the 5% assumes that you're generally playing it the right way.
Right.
If you put your chips, if you put your bets on low probability winners, then my guess is that the house edge goes more than 5%. Just like if you show up at the blackjack table and you do all the dumbest things in the world, like you hit when you're not supposed to hit and, you know, you keep hitting on 20, for example.
Right.
Your edge just went way down. And so a lot of this is also being skilled and understanding how is the game supposed to be played, whether the game is blackjack, roulette, or the game of business. Because those edges, you can, even in Vegas, you can play in and around those edges a little bit.
Yeah, he mentioned too. So I'd like to. So know your odds, know the rule book, know the game, know the rules, and try to take that into consideration as you're playing in business, gaming, or anything else in life. I'd also want to talk a little bit about. He mentioned, I think he said it was 73% of the Twitch audience. I think he said 73% of these guys are under 35. Highly influenceable males looking to role models. What do you think about. And this isn't judgment on Drake, by the way. None of this is because obviously he's very, very clever business person and artist. But what do you think about this? What do you think about this in terms of alignment and, you know, kind of decisions in and who you might want to have as a endorsement deal or something like that?
I mean, if he's an avid gambler, loves it and thinks it's a great idea, and he's being consistent and authentic with his values, I mean, I'm not going to, you know, just. That's kind of the measuring stick that I hope somebody would put against, you know, me up against. Right. If somebody were to hold a mirror back.
Yeah.
And I'm actually not. Let me, let me rephrase because I'm not asking about him in particular. I'm saying when one is considering an endorsement deal, what do you think are the pros and cons of that should be considered? That's, that's really what I'm doing.
But that's. That is the first Right. And so using that as an example, like, so for us, it needs to be something that we actually use or like, would use, plan to use kind of thing. Like, it needs to be consistent with your basic values. If somebody. My thing is always just the mom test. Like, if my mom were to open an email or listen to this podcast and be like, what is that? And my own mother could like, call me out, then I know that that's a bad fit. So I think that's kind of just your base permission to play type. Type level. Now, beyond that, I think you have to look at what are the other groups and people that could be associated with this that you don't necessarily know about. And so in a strategic partnership, who are the other players that maybe you don't know? Like, I've had the experience role, and I'm sure you have as well, where I'd agree to participate, to speak at an event. This happens a lot of times with virtual events. Why don't agree to speak to at them anymore. And they'd ask me to speak. It's like, yeah, sure, fine. And invariably there'd be other people who were speaking too, who have very different values than what I have. And now you're associated with them through some kind of connection. Now, if I was lied to about that, if I said, hey, who all is involved and I got the list and it wasn't on there, then shame on them. Right. But if I never asked, if I never did my due diligence, then shame on me. And so I think anytime you're going to engage in any type of strategic relationship or partnership, whether you're being paid as. As a sponsor or it's just a business partnership, you need to do your research. It may not be marriage, but it's pretty dang close to it. So you should date. You should know who you're getting in bed with.
Yeah, it's diligence. It's just like when you buy a company, you do due diligence, but before you go into a partnership, a marriage, or on business or anything, it's. It's. Diligence is required, I think. Right.
Yeah. And we think you could make the argument. And I. Look, I have.
Right.
I didn't know about that. I was, I was a paid, you know, speaker, but I don't think that's good enough. Right. I. Even for me, it's like, you know, I didn't know I was a paid speaker. I showed up to do my job. I didn't know the other folks that were there. But I should have checked. And so I'm sorry, you know, that, that is, that's kind of all that you can do. But yeah, I think the, the diligence, when you're going to engage, when you know for a fact that somebody is leveraging your brand or your company's brand to elevate their own status, you better make sure that when their status is elevated and they're sitting right next to you, that you're happy they're there.
Yep, absolutely. Well, I think there's a. It's really fun to me to look at things like this. And last episode we talked about Elon Musk's Twitter offer breakup thing. That the, the information that's out in the world can just kind of wash over you, or you can really take a look at it, question everything, look at the source, see if they've got agendas, look at what biases you might have, and then take lessons from these things that we see successful people doing and say, how can I apply what I know and what they're doing to see if I can extract some kind of lesson that's going to help me going forward. So I really enjoy getting your opinion on these things and bandying these things about. And if you guys enjoy this stuff too, we would love for you to subscribe to the Business Lunch podcast and give us a five star review if you like the kinds of stuff that we talk about. Anything you want to say before we close out?
Yeah, I just want to tell everybody, please, for love of God, don't gamble a crypto roulette with 10% of what you make. All right, just objectively that's a bad idea. Lots of lessons to be learned. No judgment, but God dang it, don't do that. And you know, I think we can leave it there.
All right, we'll see you guys next time.
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