Mastering the Odds: Probability Hacking, AI, and Building a Future-Proof Life
Thu Nov 27 2025
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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LinkedIn: /in/jackkrupey/
Instagram: /jkrupey/
Facebook: /jkrupey/
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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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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. CONNECT WITH JACK! LinkedIn: /in/jackkrupey/ Instagram: /jkrupey/ Facebook: /jkrupey/ Podcast: https://www.buzzsprout.com/2139703/share Signup to our newsletter: https://bit.ly/JKAMSub Passive Loss Calculator: https://calc.jkaminvestments.com/ 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 Instagram | Website | Facebook | Watch on YouTube LOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!