INTERVIEW | Make Money by Thinking Like an Advantage Gambler with Kit Chellel
Kit Chellel is an investigative journalist, Bloomberg Businessweek writer, and author of Lucky Devils. After uncovering a hidden world of elite professional gamblers who consistently beat casinos, sportsbooks, and betting markets, Kit spent years researching how these "advantage players" think—and discovered their mindset has applications far beyond gambling. In this episode, he shares the surprising parallels between betting, investing, entrepreneurship, and decision-making under uncertainty.
On this episode we talk about:
How elite advantage gamblers consistently profit from betting markets
Why gambling, investing, and entrepreneurship all rely on finding an edge
The surprising history of computer-driven sports betting and advantage play
How AI is transforming sports betting and predictive markets
Lessons entrepreneurs can learn about risk management, probability, and making better decisions
Top 3 Takeaways
The world's best gamblers don't rely on luck—they rely on data, probability, discipline, and finding small edges that compound over time.
Thinking in probabilities instead of certainties leads to better business, investing, and career decisions.
Rather than betting everything on one opportunity, consistently making many well-calculated bets increases your chances of long-term success.
Notable Quotes
"They're not like normal gamblers. They're much more like sophisticated investors or hedge funds."
"Failure is built into their mindset."
"The best thing you can do is be bold enough to take lots of good bets."
Connect with Kit Chellel:
Other:
Bloomberg Businessweek: https://www.bloomberg.com/authors/AQgXoqAi4I0/kit-chellel
Book: Lucky Devils
A Word from Our Sponsors:
- Visit DrinkAG1.com/TMM to get a free AG1 Travel Case with 7 free AG1Travel Packs in your Welcome Kit with your first AG1 subscription order while supplies last.
- Go to Leesa.com for 25% OFF select mattresses (through July 26, 2026) PLUS get an extra $50 off with promo code TMM, exclusive for my listeners
- To learn more about Mode Mobile and its investor community, go to https://invest.modemobile.com/travismakesmoney
-Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.
Capture leads, nurture them, and close more deals—all from one powerful platform.
Get an extended free trial at gohighlevel.com/travis
Learn more about your ad choices. Visit megaphone.fm/adchoices