Episode 239
War, Wealth, and Winning: The Mindset of an Elite Investor with Roy Dekel
Roy Dekel’s story is one for the books—Israeli Navy SEAL training, a leap into entrepreneurship with zero connections, and a relentless climb to building and selling multi-million-dollar businesses. In this episode, Matt talks with Roy about the trials and tribulations of scaling, making high-stakes decisions, and why most founders get caught up in the wrong metrics. Roy shares wild stories—from selling $2,000 vacuums door-to-door to navigating venture investing and why trust, not talent, is the real key to success. If you’ve ever wondered how to think like an elite operator in business and life, this one’s a masterclass in resilience, strategy, and making bold moves.
Chapters:
- 00:00:00 - Kicking off with a powerhouse: Meet Roy Dekel
- 00:00:56 - From Navy SEAL training to boardrooms: Roy’s wild journey
- 00:02:25 - Hard lessons: The real struggles of entrepreneurship
- 00:03:04 - Surviving Hell Week: Lessons from SEAL training that apply to business
- 00:06:46 - Starting from zero: The immigrant hustle in the U.S.
- 00:10:24 - Scaling to $12M+ in revenue—what it really takes
- 00:19:28 - When everything is on the line: How to make high-stakes decisions
- 00:27:08 - The art of strategic diving—and why it’s just like running a business
- 00:28:14 - Money, power, and politics: How venture capitalism is shaped by government
- 00:30:45 - Business in different states: Where you thrive and where you struggle
- 00:35:34 - What I look for when buying a company (and what makes me walk away)
- 00:40:31 - Spotting red flags before they sink your business deal
- 00:43:51 - The best advice I can give any entrepreneur right now
- 00:50:19 - Quickfire insights and final thoughts—wrapping up strong!
Book Recommendation:
- Never Split the Difference by Chris Voss and Tahl Raz
Links and Resources:
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