INTERVIEW | Make Money by Thinking Like an Advantage Gambler with Kit Chellel

Summary

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Travis Makes Money — INTERVIEW | Make Money by Thinking Like an Advantage Gambler with Kit Chellel

Date: July 18, 2026
Host: Travis Chappell
Guest: Kit Chellel (Investigative Journalist, Bloomberg; Author of Lucky Devils)

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Episode Overview

In this episode, Travis Chappell dives deep with investigative journalist and author Kit Chellel, exploring the fascinating world of “advantage gamblers”—a rare group that consistently profits by applying data, technology, and sophisticated methods to gambling. Kit discusses insights from his new book, Lucky Devils, reveals the hidden truths and mindset behind consistent winners, and highlights valuable, transferable lessons for making money and managing risk in business and life.

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Key Discussion Points & Insights

Kit Chellel’s Journey Into Writing (02:30 - 03:01)

• Early Journalism Roots: Started career at a small local newspaper, gradually writing longer pieces until he moved to substantial investigative work (02:34).
• Transition to Major Work: “Basically no one stopped me. And then 20 years later, a book.” (03:01, Chellel)

Discovery of the Advantage Gambling Subculture (03:05 - 04:11)

• Introduction to Elite Gambling: Inspired by a friend’s story of a billion-dollar Hong Kong horse betting group using algorithms and computing rather than luck (03:52).
• Kit’s Investigation: Spent 9–10 months tracking down one of the key figures—ultimately finding him in Pittsburgh (“Horse Racing Hedge Fund”).

“They're not like normal gamblers. They're much more like sophisticated investors or hedge funds.”
— Kit Chellel (04:05)

The Big Reveal: Lucky Devils Explored (03:44 - 05:24)

• What the Book’s About: Chronicles the methods and mindset of elite gamblers (“advantage players”) and how they outperform the house.
• Unexpected Scope: Techniques work for seemingly "unbeatable" games like the lottery and roulette.

The Breadth of Advantage Gambling (05:24 - 06:17)

• Beyond Sports Betting: Methods are applied to sports, casino games, even online slots.
• Tiny Elite: “It might even be the 0.0001% of all the total volume of people who gamble.” — Travis (06:17)

The Scale of Global Gambling (06:17 - 07:20)

• Staggering Illegal Gambling Market: $5.9 trillion annual market—third largest in the world, just behind the U.S. and China (06:39).

Surprising Revelations & How Roulette Can Be Beaten (07:20 - 08:56)

• Roulette Edge: Tech-based advantage—using microcomputers to time the ball and wheel, predicting winning sectors and winning millions.
• Human Pattern Recognition: Some have played so much that they can intuitively “see” where the ball lands.

“There are people still today making millions of dollars using that technique.”
— Kit Chellel (08:56)

Origin of Card Counting and the Role of Technology (11:23 - 13:28)

• Ed Thorp’s Influence: Mathematician, early adopter of computers in blackjack and beyond. “He treats this…as a job, as a profession, not as a game.” (11:26)
• Computing Power: “We literally just physically did not have the computing capacity…to figure out what the odds were going to be.” — Travis (12:31)

Birth of Computerized Sports Betting (13:28 - 14:48)

• Mike Kent, the Pioneer: First used computers in the 1970s for sports betting. His syndicate grew to control national odds.
• Historic Anecdote: Kent used a giant Westinghouse computer for stats before betting with local bookies and then moving his operation to Vegas.

“They became the biggest in the country. They made tens of millions of dollars and they changed the odds nationwide.”
— Kit Chellel (14:39)

Why Regular Gamblers Rarely Win (15:14 - 16:45)

• Sophistication Gap: Amateurs vs. professional teams with proprietary data, supercomputing, and AI.
• AI’s Arrival: Top betting teams already utilize AI for increased edge.

“That tiny number of them have a huge advantage over everyone else.”
— Kit Chellel (15:32)

Gambling as a Training Ground for Risk & Decision-Making (17:18 - 19:32)

• Gambling as Education: More valuable as a tool for learning risk management than for making money.
• Reality Check: “If you have a bad idea, it loses money. You bump up against reality real quick…your bankroll just goes.” — Kit (17:18)
• Entrepreneurial Mindset Parallels: Gambling and entrepreneurship require discipline, risk management, and resilience.

Intersection With Investing, Entrepreneurship & Life (19:32 - 21:23)

• Comparison to Hedge Funds/Investing: Most will not beat “the house”/market; intense competition, immense resources dominate.
• Warren Buffett’s Early Tip Service: Buffett sought “undervalued horses,” just as he seeks undervalued stocks (20:41).

“Looking for value at the racetrack is looking for value in the stock market.”
— Kit Chellel (20:41)

• Takeaway: Gambling mindset benefits career and personal decision-making—understanding risk, odds, and value.

Broader Application of Advantage Thinking (21:23 - 23:07)

• Entrepreneurship Lessons from Blackjack: Discipline to follow rules, capitalize on favorable situations, hedge when needed.
• Transferrable Lessons: “There’s so many little tiny lessons to take away when you’re playing those games correctly that apply directly to the entrepreneur, for sure.” — Travis (21:23)

Kit’s Career Philosophy (23:07 - 24:47)

• Writer vs. Gambler: Kit doesn't gamble, but applies “advantage player” philosophy to writing—spread bets, diversify, expect failure.
• Making Your Own Luck: “Advantage gamblers expect to fail. Failure is built into their mindset.” — Kit (23:24)

Choosing Book-Worthy Stories (24:53 - 25:35)

• Decision Criteria: Looks for complexity and density in a story—“If I come across something that’s so weird, that’s so inexplicable…I know there’s probably a book.” — Kit (24:53)

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Notable Quotes & Memorable Moments

• “I have learned from the way these guys think. And I think one of the best things that they taught me is…be bold enough to take lots of good bets. Don’t put all your eggs in One basket.”
  — Kit Chellel (23:24)

• “Gambling, betting is an incredibly useful way to improve your skill set…It teaches you a kind of a rigorous way to analyze and exploit risk, and it also teaches you hard realities.”
  — Kit Chellel (17:18)

• “I often actually talk about blackjack as like a siloed experience in what entrepreneurship is like…there’s so many, like, little tiny lessons to take away when you’re playing those games correctly that apply directly to the entrepreneur, for sure.”
  — Travis Chappell (21:23)

• “Looking for value at the racetrack is looking for value in the stock market.”
  — Kit Chellel (20:41)

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Important Timestamps

• 02:30 — Kit's journey into writing & journalism
• 03:44 — Introduction to Lucky Devils and the world of advantage gamblers
• 07:20 — How roulette can actually be beaten using technology
• 11:26 — Ed Thorp, mathematics, and the first card counting computers
• 13:28 — Mike Kent invents computer-based sports betting
• 15:32 — The gap between amateurs and professional advantage gamblers
• 17:18 — Transferable skills: risk management, critical thinking
• 20:41 — Warren Buffett’s horse racing betting and its parallels to investing
• 21:23 — Comparing blackjack strategy to entrepreneurship
• 23:24 — Kit’s career decisions and mindset

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Where to Find Kit Chellel

• Bloomberg Businessweek: Search for "Kit Chellel" for his articles and features.
• Books: Lucky Devils (latest), previous works on Amazon.
• Social Media: Active on X/Twitter and other platforms.

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Final Take:
Advantage gambling isn’t just about beating the house—it’s about understanding and managing risk, building systems, and developing a disciplined, evidence-based approach to life, business, and money. Kit’s research reveals that while few become wealthy by pure gambling, many of the best lessons learned apply to broader ventures and personal growth.

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Transcript

[Travis]

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What's going on, everybody? Welcome back to the Travis Makes Money podcast, where it's our mission to help you all make a little bit more money on this episode of the show. I have a new friend, Kit Shalel. He is a writer, investigative journalist, works with Bloomberg and has Too much Words, which is something he put out recently. Writes a bunch of Amazon reviews. An actual writer through and through. So, Kit, what's up, man? Welcome to the show.

[Kit Shalel]

Hey, Too Much Words is actually a review that was left on one of my books.

[Travis]

Oh, really? Is that what it is?

[Kit Shalel]

Yeah, which. Which I felt was, you know, kind of A harsh and redundant criticism for a book. Yeah, but I maybe last, so I stole it.

[Travis]

Also, grammatically incorrect, I think.

[Kit Shalel]

I mean, most of my words make sense. I think I can claim that. Yeah.

[Travis]

Well, I appreciate you taking the time here, man. What got you. What got you into writing? Why. Why writing?

[Kit Shalel]

Well, I started my life as a journalist, really on a. On a. A local newspaper. Remember those? Back when those existed? Kind of memories, but they exist a dead institution now. So I did local news stories, you know, missing cats and traffic accidents and all that sort of thing. And I gradually started writing longer and longer and basically no one stopped me. And then 20 years later, a book.

[Travis]

Yeah.

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[Travis]

So tell. Tell us about the. Tell us about the book.

[Kit Shalel]

Well, I've. I've. I've taken an interest in. In gambling. The very elite kind of gambling that maybe only few hundred people in the world can do really well, which is the kind of gambling that consistently makes money year after year. And there's a sort of secretive clique of these people. All them know each other, but they use similar methods and they have a similar mindset, and they're known as advantage players. And I kind of stumbled into this world by accident, got fascinated by it, found that I was learning from them in unexpected ways. And, yeah, I thought it would be interesting to write a book about what they do and how they do it.

[Travis]

What. What's the name of the new book?

[Kit Shalel]

The book is called Lucky Devils.

[Travis]

Lucky Devils. How did you even get. How did you even become aware that this existed?

[Kit Shalel]

I mean, like a lot of great stories. It started just chatting with my friends over a couple of beers. One of my friends works in venture capital, or he did at the time, and he'd heard of this company out in Hong Kong that had made a billion dollars betting on horses at the Happy Valley racetrack.

[Travis]

Wow.

[Kit Shalel]

You know anyone? If you know anyone who bets the racetrack or you've ever bet yourself. That number does sound ridiculous. But I thought it was a neat idea. And apparently the secret was using computing power and algorithms rather than, you know, the usual approach that you would take to gambling. It took me maybe nine, ten months to find these guys, but I did. It turns out one of them was still in the business after doing it for 40 years. And I found him and got on a flight and showed up in his home city of Pittsburgh and wrote a story about what he did. It was called the Horse Racing Hedge Fund, which is kind of an analogous to what these guys do. They. They're not like normal gamblers. They're much More like sophisticated investors or hedge funds. Yeah, that's kind of much closer to how they operate. And that story did. Did fantastically. People were just fascinated by it. I don't think many people really knew that this existed. I certainly didn't. So yeah, it got such a great reaction then. And then from. Through this guy that I wrote about, I learned that the same method works for stuff that should be impossible, like playing the lottery. You know, roulette in a casino. Stuff that you think is unbeatable. Using these techniques, they can do it. And that's what I. That's what Lucky Devils is all about.

[Travis]

Are. Are the majority of them doing this in like the sports betting world or are they using it in like table games and casinos and things like that?

[Kit Shalel]

Honestly, it's everything. Any activity you can bet on. There are people doing this. Yes. Sports betting is dominated by a very small percentage of very highly sophisticated gamblers whose data and analysis is better than mine and yours. That's undeniably true. But it's true of prediction markets. It's true of, you know, online casino games. Slot machines. You know, these slot machines on online casinos that people play. You think, God, that's a game for suckers. Yeah, mostly. But again, there's this elite 1% who have found a little advantage. They found an edge and they're exploiting it right now.

[Travis]

Yeah, it might even be the 0.0001% of all the total volume of people who gamble. I had this guy on the show actually yesterday. We did a. In person. He was here in Vegas and he's the. The president of Global or Gaming Commission International or something like that. GCI is the name of the company.

[Kit Shalel]

Yeah.

[Travis]

And they do. They basically help try to eliminate some of the illegal gambling. But he was telling me that illegal gambling as a market is like the world's third largest market behind the United States and China as countries. It has like a $5.9 trillion annual industry. Just an illegal gambling, not even counting legal. So yeah, I think a lot of people are doing this and doing it blindly. Where you have some of these elites who are doing, like you said, they're. They're operating it more like. More like their investors. What were some of. Like some of the more surprising things that you found out doing this piece?

[Kit Shalel]

Roulette was a big one. I mean that the bouncing ball and a roulette wheel. It's so counterintuitive that anyone could make a career, a profitable career reliably making money from roulette. But you absolutely can the trick is, essentially, you just need to be better. Better than blind luck, right? So you pick number randomly, and you. Or you pick black or red. Let's say that's. That's roughly half the world. You've got slightly less than 50% chance of winning. You only need to be a little bit better than that. So, you know, if you can rule out a quarter of the wheel and say the ball probably isn't going to land there, and then bet all the other numbers because the odds, because the payout's so high, you do that a thousand times, you're probably going to make money if you're right. So there were people who use little computers to measure the speed of the ball and time the rotation of the wheel, and it would beep into their ear which section of the wheel the ball was most likely to land in. It wasn't always right, wasn't perfect, but it was good enough. They won enough that they could end the night 10, 20, $30,000 up on a good night. Applying the same principle. There are people who have played so much roulette that their brains are trained to identify patterns. They see the wheel moving, they see the ball, and they kind of play it forward in their mind, and they have a rough idea where it's going to be, and they're good enough and quick enough to bet that section, and they just do it with their brains alone, that works. I mean, it took me a long time to establish that it does, but that really works. And there are people still today making millions of dollars using that technique.

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did you ever read anything from Ed Thorpe?

[Kit Shalel]

Yeah, of course. He's the godfather of this method. He's, he's basically the inventor of card counting and he shares characteristics with my characters and lucky devils in that he's a scientist. He's mathematician. Yeah, mathematician. He treats this, he treated this as a job, as a profession, not as a game. And he used the power of computers to get his advantage. The reason card counting exists is that he ran all these scenarios through an early IBM and they told him with any given number of cards out of the deck what the advantage of the dealer versus the player is. So what the. A key characteristic of this method is to crunch these numbers to run all these scenarios to be able to make accurate predictions about the future. You need to do a very advanced data analysis that most of our brains are capable of and generally you need a computer for that.

[Travis]

Yeah, right. That, that was always most wild. I read his, his autobiography Blanking on the Name a Man for all markets. Markets.

[Kit Shalel]

Yeah, yeah, yeah.

[Travis]

Was that was the autobiography. And that was probably what stood out to me the most was that it was just a matter of that we, we literally just physically did not have the computing capacity to be able to run the numbers to the degree that you could figure out what the odds were going to be. And then because he was a math professor or something like that, he had access to an early computer that took up, you know, two full rooms back in the day and just himself coded those computers to come up with the algorithms to figure out what exactly, you know, it meant for this person has the advantage. And then he started applying it beyond just blackjack to all these other table games. And roulette was the one that I was like, surely there's no way to, you know, be able to hedge or quote unquote, invest your money at the roulette table. But, you know, leave it, leave it to the hands of the people who are way smarter than me to figure this stuff out. But apparently it works and people are doing it.

[Kit Shalel]

Well, you, you talk about sports betting. I write in Lucky Devils about the very first guy probably to use a computer to bet on sports. Now, of course, these days, in the age of sort of fangual and fantasy sports and betting by the minute, everyone uses a computer to make their bet. And anyone who does it seriously will have a spreadsheet, they'll have some system. You know, a lot of people consider themselves to be statistically based gamblers. But when this began, it was 1976, 1977. This was back when to use a computer you had to go into a room and the machine was as big as the room you put a piece of cardboard in and it punched holes in it. Okay. And it was. This was a Westinghouse computer that was being used for top secret government research. But he was bored, so he started running the numbers from his company softball team and then he started betting on college games with his local mobbed up bookies in Pittsburgh. And then he moved to Las Vegas and he built the first computer analysis based sports betting syndicate. And they became the biggest in the country. They made tens of millions of dollars and they changed the odds nationwide. They were that good because they were first.

[Travis]

Wow.

And is this, there's an article in Bloomberg that you wrote. The sports betting revolution started with the board nuclear engineer. Was that, was that this person you're talking about?

[Kit Shalel]

That's the guy. Mike Kent. Yeah, he was. I can't imagine anyone else. Access to a computer back then was so rare and you know you have to remember back in the 70s, it was basically illegal to bet on sports anywhere outside of Nevada. So there probably weren't and there probably weren't people in, in Las Vegas who had the capital and the resources to, to use computers. They were quite rare objects back then. So, yeah, I believe he was the first.

[Travis]

Yeah. What does this look like now with the volume of compute power that we have even just in the palm of our hand? And, and if, if there, if access to them for is, if access to the information is ubiquitous, then why are people not using that to make smarter moves when they're gambling?

[Kit Shalel]

I think people are most people who, who want to have a serious chance of making money from their bets, which is everyone really, you know, no one likes losing money, will try to do this. The reason they fail is the level of sophistication. And it's a bit like in financial markets, people who trade stocks as a hobby or in their spare time versus a hedge fund that has a room full of people with PhDs, access to a supercomputer and a high speed wire that's feeding them data, you know, 10 split seconds faster than you're getting. All these advantages give them an ingrained edge that's incredibly difficult to overcome. And it's the same in, in, in betting markets, however good you think your system is. You know, I have met the people who run the really big betting systems, I have met their staff. I have seen the decades it takes to build your algorithm using proprietary data that you collected yourself to make it that much faster than everyone else's. And you know, the reality is, is that that tiny number of them have a huge advantage over everyone else. And of course the latest thing to upend this whole market is AI And AI has arrived in sports betting in a big way and the top players are already using it.

[Travis]

What do you think the, the for, for somebody who's a novice who's like kind of, you know, getting that gambling itch, what, what do you think is the game or sector that they should start in if they want to try to make some money on their, on their bets? Like, is it, is it sports betting? Is it prediction markets, is it table games at a casino, is it online poker? Like what exactly is the thing that you found is like this is probably the most simple one to understand the basics with and to excel at quickly.

[Kit Shalel]

So I, first of all, I would say if you want to make a lot of money, it's gambling is one of the hardest ways to do it. It's just tough it's extremely competitive. The game is fundamentally weighed against you in a way that you don't find in other areas of life. What I would say is that gambling, betting is an incredibly useful way to improve your skill set. There's a reason so many successful hedge fund managers will say, you know, I came up through university playing poker, or I used to make money counting cards in casinos when I was 17. It teaches you a kind of a rigorous way to analyze and exploit risk to your benefit. And it also teaches you hard realities. It disabuses you of your illogical ideas. If you have a bad idea, it loses money. You bump up against reality real quick. When you're gambling, your bankroll just goes. So it teaches you to be evidence based in your thinking, and it teaches you really, really careful about risk. Like, you know, you make a lot of bets and you don't want any of those bets to wipe you out. So you have to manage your risk really carefully. There's a good, it's a great educational tool. It's a great way of thinking about the world as a, as a way of making money. You know, I tend to think it's best to leave it to the kind of guys that I write about, unlucky devils who are doing it so well.

[Travis]

Yeah, I mean, it's the same thing with investing, too. Like, even, like day trading and things like that. You know, it's like you said earlier, it's, you know, you're, you're the armchair, you're the armchair expert. You know, you got a bag of Doritos watching the football game and you're betting on companies on the side doing a little bit, little bit of day trading. It's like, what are the odds you're going to be able to figure it out when you have entire teams of people that are managing billions and billions of dollars and they have the brightest minds, the best technology. They actually know how to use it and deploy it. And even them, like, they're still not crazy, outperforming what you're going to get, just throwing your money in the S and P and forgetting about it. You know what I mean? So, and it's kind of the same thing with gambling. It's like there's entire teams of people running from using billions of dollars and all that have all this crazy data. They know how to use it, they know how to deploy it, and even they still don't have, like a crazy advantage. So what are the odds we're going

[Kit Shalel]

to be the top performers in, in financial markets and Actually this this mindset applies to venture capital as well. It applies to health. Any science like this way of thinking about the world is incredibly useful.

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[Kit Shalel]

See terms I found out that Warren Buffett, when he was a teenager ran a horse racing tip service that he sold to and he, he has said publicly that, you know, he sees the similarities between looking for value at the racetrack, looking for and looking for value in the stock market. He's looking for things. He's looking for horses that are underpriced, where the odds are too long, where the market is wrong about how good that horse is. That's what he was looking for in his tip service. That's what sustained his long career as maybe the greatest investor in history. Maybe a better way to think about gambling is I'm probably not going to make my fortune gambling, but it might make me better in making life decisions, in making career decisions, and better at managing my money.

[Travis]

Yeah, yeah. I often actually talk about blackjack as like a siloed experience in what entrepreneurship is like. You know what I mean? Like it's the discipline to hit on 16 when you're facing a non busting card every single time, even if the low cards in the deck are seemingly already out. You know what I mean? It's the, it's the fortitude to be able to increase your bet when things are going well. To double that. Like when things are going really well, you got to Increase your bet. You got to double, you got to split, you got to make the money when, when energy is good and then things go bad. Now we, we decrease our bets and, and we're going to be a little, a little bit safer here. We're going to hedge, you know what I mean? Like, there's so many, there's so many, like, little tiny lessons to take away when you're playing those games correctly that apply directly to the entrepreneur, for sure.

[Kit Shalel]

And, and the, and the great thing about gambling and the great thing about betting as an educational tool, as a way to improve what you do. You know, science is often quite detached from the reality of human experience. You know, scientists in their laboratories are creating artificial scenarios or running numbers. It's maybe a little different to real life, but if you bet in a casino or if you play poker or if you play cards, you have to take into account your opponent's behavior. You have to deal with those unquantifiable unknowns that you just can't predict. How is the casino going to behave If I make $2 million in one night playing roulette, which happens in the book, what's going to happen in my sports betting market if my system is so good that I'm doubling my money each time? You know, poker, Poker is all about game theory. It's all about dealing with a world that's uncertain because of the way other people react. Those lessons are incredibly important.

[Travis]

Okay, what is, what, what does your career look like when you put this much thought and energy into a single topic? Like, is this something that you're going to dive into for quite some time? Or is it sort of like, hey, let me. I wrote this article, went really well. I wrote the book. Now I'm fascinated by something else.

[Kit Shalel]

Well, look, I, you know, I'm a writer. I'm not a gambler. I'll be honest. I, you know, I don't love gambling casinos, and I don't have the brain to be able to do it like these guys do. So, you know, I'm never going to. This was never going to be something that was viable for me. I write stories. That's what I'm. What I'm good at. But I have learned from the way these guys think. And I think one of the best things that they taught me is when you're looking at an uncertain future and you're looking to sort of chart a path through it, best thing you can do is be bold enough to take lots of good bets. Don't put all your eggs in One basket. Don't say my entire career hinges on this one thing. You have to have a dozen more good, viable outcomes, good bets that you can make. Now advantage gamblers expect to fail. Failure is built into their mindset. And you know, it's the same for me in the way I write. I not, not every subject that I choose is going to be a smash hit. Not every story I do is going to be, you know, the best thing I've ever done. But I've got enough knowledge and I can analyze those risks enough to know that if I pick 10 really good ones, maybe a couple pay off. So, yeah, I won't. It. I'm not an. I've learned not to put all my eggs in one basket. In my career as a writer, I've learned to spread myself. So, you know, I'm not doing so many gambling stories anymore. I'm doing healthcare and weird science and cloud seeding and lots of other things in the hope that a few of them pay off.

[Travis]

How do you decide to turn something into a book versus just leaving it in an article?

[Kit Shalel]

That's a really good question. I mean, I think it's the, it's the density of the story. A lot of subjects you kind of feel you learn all you ever need to know in 5,000 words. They're relatively easy to understand. There's not a complicated history behind them. Some things, some characters, some stories are a tangle of different competing narratives and complexity that, you know, just kind of draws me in and I want to understand it. And if I, if I come across something that's so weird, that's so inexplicable, so baffling that I just want to spend the next five years of my life thinking about nothing else or thinking, you know, a lot about this, then I know there's probably a book.

[Travis]

Yeah, yeah. Fascinating career, man. I appreciate you for taking the time to write the book, to come on the show. Where can people go to get more from you and what you're working on?

[Kit Shalel]

Well, I'm, I'm, I'm on staff at Bloomberg. I write mainly for Business Week, so if you put my name into Google, you'll see all my, all my crazy stories for BusinessWeek. And I've done lots of different things. I have another book out. People Like Lucky Devils on an entirely different subject. And I'm on X and all social media, too.

[Travis]

Kit Chalel C H E L L E L Kit Shalel Go check out some of the stuff that he's posting over on Bloomberg and then pick up a copy of Lucky Devils. It's a fascinating read. I'm definitely adding it to my list as we speak. I already ordered the book, so. Waiting for it to get here. Kid, I appreciate you taking the time. Everybody else tuning in. Remember, money only solves your money problems. But it's easier to solve the rest of your problems when you got some money in the bank. So let's start there. Here on the Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.

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