Podcast Summary: The Art of Manliness

Episode: How to Use Probability Hacking to Achieve Your Goals
Date: December 30, 2025
Host: Brett McKay
Guest: Kyle Austin Young, strategy consultant and author of Success Is a Numbers Game

Overview

This episode explores how understanding and strategically applying probability can help you achieve your goals more effectively. Host Brett McKay speaks with Kyle Austin Young about his new book, Success Is a Numbers Game, discussing the often-hidden odds behind goals and how to “hack” those probabilities to tilt the odds in your favor. Young shares personal stories, practical frameworks, and actionable advice for using probability to plan, pursue, and, when necessary, quit goals more intelligently.

Key Discussion Points & Insights

1. The Hidden Probabilities Behind Every Goal

• Every goal, from business to personal milestones, has an intrinsic probability of success/failure.
• Recognizing your odds is the first step to making smarter, more strategic decisions rather than just hoping for the best.
• Personal story: Kyle’s realization came after being laid off twice in 13 months, prompting him to intentionally diversify his career and seek ways to improve his odds of long-term success ([03:48]).

"I was really fortunate. The day after the second layoff, I had four different people offer me positions...there were a lot of people who liked me, respected the work I was doing. And yet I was unemployed. So ultimately...it wasn't enough to show up and do my job really well. If the projects weren't successful...I was still going to be at risk of losing my income."
— Kyle Austin Young ([03:48])

2. Three Common Approaches to Pursuing Goals

a. Playing Where Odds Are Favorable

• Example: “Nepo babies” or inheriting an established business.
• Advantage: Builds confidence and resources for bigger goals.
• Downside: May not align with passions and can lead to “playing it small.”
• NBA example: Height’s effect on odds for pro basketball (odds for under 6ft: 1 in 1.2 million, over 7ft: 1 in 7; [06:04]-[09:20]).

b. Chasing Unlikely Goals, Hoping for Luck

• Most common (not always intentional): People dive in without weighing the actual odds.
  • 9/10 businesses fail; 90–94% of New Year’s resolutions fail.
• Problem: "Winging it" leaves people vulnerable to avoidable failure.
• Takeaway: High failure rates are partially due to not optimizing odds or understanding risks ([09:49]-[11:49]).

c. Strategically Playing Bad Odds Through Multiple Attempts

• Entrepreneurs and artists succeed by making many attempts:
  • Instacart founder launched ~20 businesses before the big win.
  • Beethoven, Mozart, Van Gogh: prolific output improved odds of an enduring legacy ([13:17]-[15:51]).
• Miracle on Ice example: U.S. beat Russia after many previous attempts, mirroring the power of repeated tries to exploit probability ([16:06]).

3. Downsides of the “Multiple Attempts” Approach

• Not all goals allow for repeated attempts (e.g., college graduation).
• May waste time and resources if odds are extremely low ([18:57]).

4. What is Probability Hacking?

• Probability Hacking: Proactively identifying and adjusting the variables that influence the odds of achieving your goal.
• Foundation: Understanding how probability works, especially where people commonly miscalculate it ([20:02]).

a. Common Probability Mistakes

• People tend to average the odds of steps, not multiply them.
• Example: Running a marathon in 90 days
  • 70% chance of sticking to diet × 70% sleep × 70% training = NOT 70%, but ~34% total success chance ([21:16]-[23:42]).
  • "Your odds will never be better than the least likely step." ([25:19])

"What many people do...is called averaging...but in truth, you can't average. If you have something that has to go right...you have to multiply those odds together."
— Kyle Austin Young ([21:16])

5. Basic Principles of Probability for Goal Setting

• Odds of all possible outcomes always total 100%.
• To increase your odds of success, you must decrease the odds of bad outcomes—they "hide" the potential for good ([26:19]).

"Commitment doesn’t de-risk your goal at all...the odds that you want are hiding in your potential bad outcomes."
— Kyle Austin Young ([27:50])

Practical Probability Hacking Framework

1. The Success Diagram

• Definition: A map of every “critical point” (step that must happen) for your goal, with potential bad outcomes listed beneath each ([31:33]).
• Process:
  1. Establish the main goal.
  2. Break goal into sub-goals (“critical points”).
  3. List all possible bad outcomes for each.
  4. For each bad outcome, ask: “What can I do to eliminate or reduce this?”
• Strategy: As you decrease the likelihood of bad outcomes, your success odds rise—sometimes turning a likely failure into a probable success ([33:52]).

Example: Landing a Senior Job at 21

Kyle aimed for a director role where most candidates were decades older ([34:45]):

• Potential bad outcomes:
  • He’d be seen as “too young” → grew a beard.
  • Lack of experience → wrote and distributed a book outlining his strategy.
  • Poor cultural fit with team → read all the books team had recently read, used their language in group interviews.
• Result: Got the job and rapidly advanced his career.

2. Tools and Tactics

• Front-Load the Riskiest Steps: If a step has a low chance of success, attempt it first, so you don’t waste resources on things likely to fail later ([25:19],[41:32]).
• "Strapping a Rocket to a Racehorse": Rearrange the plan to avoid unlikely steps entirely when possible (e.g., find alternative paths that don’t need approvals with a low chance of success, [39:46]).

"Is there another way to get around that? ...you made the conversation about something mutually beneficial."
— Kyle Austin Young ([40:07])

3. Reverse Probability Hacking

• Definition: In competition, proactively make others’ bad outcomes more likely (e.g., Obama campaign emphasizing Romney’s wealth to make him look out of touch, lawyers overloading discovery requests, [44:52]-[47:36]).

4. When to Quit (or Pause) a Goal

• After mapping success and trying probability hacks, if your odds are still too low, consider pausing.
• Don’t discard your plan: use it as a blueprint for what must change if you revisit the goal ([47:43]).

“If the odds look bad, don't think of it as quitting it. Think of it as pausing it...look for ways to rack up advantages...before they come back to fight the really big boss.”
— Kyle Austin Young ([48:40])

• Borrowed wisdom:
  "Would you bet on this?" – Annie Duke ([51:15]):
  Thinking in bets “forces you to stop and really do business with the things that might go wrong.”

Memorable Quotes & Moments

• On habits of success:
  "Success begets success. The connections or the resources or the experience that you get out of small wins...will often change your odds on more unlikely pursuits."
  — Kyle Austin Young ([06:04])

• On repeated attempts:
  "Van Gogh painted and sketched so prolifically...he averaged roughly one new work of art every 36 hours for 10 years."
  — Kyle Austin Young ([14:44])

• On probability calculation mistakes:
  "You can never outperform your most unlikely step."
  — Kyle Austin Young ([25:19])

• Practical advice:
  "Think negative. Everybody's telling you to think positive...just really practically list out the things that could go wrong and do everything you can to make those less likely."
  — Kyle Austin Young ([51:50])

Key Timestamps

• [03:20] Introduction of Kyle Austin Young
• [03:48] Kyle’s career setbacks and origin of his framework
• [06:04] First approach: pursuing high-probability goals (NBA height example)
• [09:49] Second approach: ignoring the odds; most people do this
• [13:17] Third approach: repeated attempts (entrepreneurs and artists)
• [16:06] Miracle on Ice example
• [18:57] Limits of the multiple attempts strategy
• [20:02] Why we misunderstand probability (little education)
• [21:16] Marathon example: mistake of averaging vs. multiplying probabilities
• [23:42] The most improbable step sets the ceiling on your odds
• [26:19] Odds for all outcomes = 100%; must reduce bad outcomes to increase success
• [31:33] Introduction to the “Success Diagram”
• [34:45] Probability hacking without exact numbers (Kyle’s director job story)
• [39:46] “Strapping a rocket to a racehorse”: redesigning your path
• [44:52] Reverse probability hacking in business, law, politics
• [47:43] Using success diagrams to know when to quit/“pause” a goal
• [51:15] “Would you bet on this?” – making predictions less vague
• [51:50] One thing to start doing today: Think negative (systematically)

Actionable Takeaways

• List all critical steps for your goal, then all possible bad outcomes.
• Attack those bad outcomes: for each, plan a specific mitigation.
• Predict your odds by multiplying the probabilities of each step. The lowest-probability step is your biggest barrier.
• Restructure your approach to eliminate or move difficult steps upfront.
• Be willing to pause or pivot if the odds remain too low, but keep your “success diagram” as a blueprint for future attempts.

Final Thoughts

Success isn’t just about talent or effort—it's also about understanding and manipulating the odds. Kyle Austin Young's approach shows how being systematic and “thinking negative” can give you a genuine edge, whether your goals are personal, professional, or ambitious world-changing dreams.

Learn More:

• Book: Success Is a Numbers Game
• Website: KyleAustinYoung.com
• LinkedIn: Kyle Austin Young

Notable Quote to Remember

“Think negative… really practically list out the things that could go wrong and do everything you can to make those less likely.”
— Kyle Austin Young ([51:50])