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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if your success isn’t about luck — but math?
In this episode, Jack sits down with Kyle Austin Young, author of Success Is a Numbers Game, to break down how probability, intentional planning, and strategic pessimism can radically transform your business, career, and investments.
Kyle shares how two back-to-back layoffs pushed him into fractional consulting, how he built a framework to “de-risk” any goal, and why thinking negative may be the most powerful advantage you have. They also dive deep into AI’s impact on jobs, the future of work, real estate investing, social media strategy, and how to tilt the odds in your favor no matter what industry you're in.
Whether you're an entrepreneur, investor, or anyone looking to increase your odds of winning, this conversation is packed with practical, actionable insights.
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00:00 – Disclaimer & Intro
00:42 – Meet Kyle Austin Young & His New Book
02:05 – Early Career Setbacks: Two Layoffs in 13 Months
04:12 – From W2 to Fractional Consulting
06:18 – Reinventing Success: The Birth of the Success Diagram
10:10 – Probability Hacking Explained
14:30 – Using AI as the Ultimate Pessimist
18:05 – Marathon Example: Why Your Odds Aren’t What You Think
22:40 – Real-World Application: Solving a Nonprofit’s Mystery Decline
26:50 – AI, Small Business, and the Future of Consulting
30:40 – Easy Hacks vs. Predictive Hacks
36:55 – How Kyle Landed a Director Job at Age 21
41:10 – Investing Insights: Rentals, Land, and Leverage
46:15 – Risk Management for Investors
50:22 – Social Media, Sales, and Why LinkedIn Wins
55:08 – Podcasting as the New Trust Builder
57:45 – Will AI Create Mass Unemployment?
1:01:40 – Why Trust Becomes Your Greatest Asset
1:05:30 – Parting Advice: Think Negative to Win More
1:07:10 – Where to Find Kyle & Final Wrap-Up
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