Podcast Summary: BigDeal — Master MONEY MAKING In 60 Minutes: Everything They Never Taught You | Jenny Just

Date: October 22, 2025
Host: Codie Sanchez
Guest: Jenny Just (Co-founder, Peak6, investor, billionaire)

Overview

This episode dives deep into the unfiltered financial and personal lessons from Jenny Just—one of the rare self-made female billionaires in finance and co-founder of PEAK6. The conversation centers on mastering risk (and developing risk tolerance), leveraging poker for life and business strategy, navigating failure, and the kind of mindset, systems, and habits that actually build long-term wealth.

Jenny brings a quantitative, no-nonsense approach to risk—demystifying what it takes to win (and survive) in the world of trading, finance, entrepreneurship, and, surprisingly, poker. The episode is packed with actionable insights on reframing failure, building risk-taking muscle, making disciplined decisions, and learning how to own your financial future.

Key Discussion Points & Insights

1. Early Lessons from Trading & The Reality of Losing

• Trading as a Foundation: Jenny started on the trading floor, where losing was common and frequent—nearly 45% of the time.
• "Compound Experience": Each loss, Jenny explains, helps build intelligence, courage, and resilience as much as any win.
  • “Starting in trading is really humbling. We lose 45% of the time. So it's over and over and over… Each one of those gets you a little smarter, a little braver, a little bit more nimble.” — Jenny [02:42]
• Facing Massive Losses: She’s lost “tens of millions in seconds,” but learned that risk doesn’t mean recklessness—it's about continuous adaptation and humility.
  • “Long Term Capital Management is a great story… they were the smartest and they didn’t win. So being humble about when things are going well and acknowledging what was luck, what was skill, and then recognizing a situation where that same thing, it’s going to happen again.” — Jenny [04:26]

2. Long-Term Success in Investing

• Methodical Reinvention: PEAK6 has made money every year for 28 years—not by chasing the absolute biggest wins, but by constantly reinventing and adapting.
• Three-Year Cycles: Rather than focusing on annual results, Jenny thinks in multi-year timeframes—“It’s definitely a marathon, not a sprint.” [01:36][28:43]
• Risk Isn't Binary: Most people think in all-or-nothing terms, but long-term success is about small, cumulative gains (and controlled losses).

3. Redefining and Quantifying Risk

• Personal Risk Scale: Jenny advocates for everyone to honestly self-assess their risk appetite on a 1-10 scale and revisit it frequently.
  • “It's very unique to the person… Give yourself a risk scale, 1 to 10. And then what is the purpose? Do I have a purpose for taking more or less risk?” — Jenny [09:56]
• Risk Management Framework: Always consider the worst possible outcome, not just the best-case scenario.

4. Poker as a Training Ground for Risk and Life Skills

• Poker Develops Critical Skills: Jenny discovered poker when teaching her daughter, realizing it perfectly mirrors the imperfect-information world of trading and business.
  • “Poker was the closest thing I've seen to the training I got as an options trader… Playing that hand, making that decision with imperfect information, playing people…” — Jenny [17:16]
• Breaks Gender Barriers: She launched Poker Power to teach thousands of women, believing poker builds confidence, negotiation, and strategic thinking.
• Scaling the Lesson: Now, Poker Power has taught women at 370 companies in over 60 countries.

5. Mindset, Money Beliefs, and Unlearning

• Myth Busting: Jenny debunks common money myths in rapid-fire Q&A:
  • "You should just save and skip the coffee": “If you're not enjoying yourself along the way, none of it's worth it.” [25:46]
  • "If you deserve it, you'll get it”: “I worked my ass off. The hardest-working people are the ones that succeed.” [26:17]
• It’s Not About Being the Smartest: Hard work, curiosity, and the willingness to learn (and fail) beat raw talent in her experience—as shown by PEAK6’s diverse hires.
  • "We train people with no knowledge coming in. ... Matt has an English major. I was a business major... We're looking for people at the end of the day who work really hard, who are curious." — Jenny [32:29]

6. The Power of Failure (And Keeping Score)

• Failure as Fuel: Jenny keeps a literal list of her biggest business failures on her desk—an ongoing reminder to learn and stay humble.
  • "You know, just the list." — Jenny [41:33]
  • "Time heals things, you know, and that pain and suffering of some of those, I don't want to make that same mistake… Why should I lose $5 million or $50 million on something if I truly know better?" — Jenny [42:21]

7. Building Systems, Running Experiments, and Scaling Up

• Hiring from Unlikely Backgrounds: PEAK6 ran experiments hiring poker players and hockey statisticians as traders, discovering success isn’t always linked to traditional backgrounds.
• Inventing Solutions: Drawing inspiration from unlikely sources (like a Wendy’s order system), she applies cross-industry innovation to keep PEAK6 ahead.

8. Risk, Reassessment, and Adaptation

• Iterative Risk-Taking: Take risks, structure them with mentorship, analyze outcomes, and reassess regularly—even as your aperture for risk widens.
  • "Every step opens you up, I think differently… but the reassessment, the loop, right? You don't have to go all the way back to the beginning…" — Jenny [36:55][36:39]

9. Navigating Entrepreneurship & Getting Promoted: Read the Room

• Poker and Business Parallels: Good poker play (and good business) requires thinking not just about your own hand but everyone else's motivations.
  • "If I'm sitting across from someone and I want something to happen… I have to think about what they're thinking." — Jenny [01:49][55:41]
• Winning Over Investors (and Bosses): Jenny evaluates entrepreneurs by their realistic risk-awareness and ability to acknowledge failures, not just blind optimism.

Notable Quotes & Memorable Moments

• On Compound Experience:
  "Each one of those [trading losses] gets you a little smarter, a little braver, a little bit more nimble." — Jenny [02:42]

• On Surviving Big Losses:
  "When it first happened, the very first time… that was rough. But you get better from it… being humble about when things are going well… acknowledging what was luck, what was skill." — Jenny [04:26]

• On Risk Appetite:
  "Give yourself a risk scale, 1 to 10. And then what is the purpose? Do I have a purpose for taking more or less risk?" — Jenny [09:56]

• Poker as a Trojan Horse:
  "Poker was the closest thing I've seen to the training I got as an options trader… It's the Trojan horse, honestly, for women to learn this game, play this game, build those skills." — Jenny [17:16][21:34]

• On Hiring and Building Teams:
  "We're looking for people at the end of the day who work really hard, who are curious, and… above average intelligence. …But you don't have to have a finance background." — Jenny [32:29]

• On Learning from Failure:
  "I just keep my fails on my desk… It's the company fails." — Jenny [41:33]

• On Mindset and Money:
  "Making money isn't hard. Unlearning everything you know about it is. …Money goes to people who treat life like strategy, not survival." — Codie quoting [25:23]
  "I think there's a lot of truth to that." — Jenny

• On Risk and AI:
  "Wildly important that you get your hands dirty. …You can't mess it up, which is super cool." — Jenny [52:08][53:01]

• On the Purpose of Wealth:
  "At your level of the game, I imagine… it's also something bigger. It's like, what are you gonna do? Take all the jets to the grave, you know?" — Codie [60:35]
  "That would be a pure joy for us to be able to do that." [Refers to creating competitors out of students.] — Jenny [60:20]

Timestamps for Major Segments

| Time | Segment | |-----------|-----------------------------------------------------------------------------------------------------| | 01:09 | Facing major losses in trading | | 02:42 | How failure shaped Jenny’s mindset | | 04:07 | Biggest single-day losses and what it teaches | | 07:31 | Risk management over 28 years of investing | | 09:56 | Quantifying and contextualizing risk | | 17:16 | The poker experiment: teaching her daughter, and launching Poker Power | | 21:34 | Poker as a Trojan horse for women and anecdotal poker history | | 25:23 | "Making money isn't hard. Unlearning everything you know about it is." Rapid-fire money myths | | 28:43 | Patience, time, and the marathon of wealth | | 32:29 | Hiring and the true traits that succeed at PEAK6 | | 36:39 | Iterative, structured risk-taking and continuous reassessment | | 41:33 | The failure list and why it sits on her desk | | 52:08 | AI: fear, optimism, and advice on getting involved | | 55:41 | Using poker for context-setting and negotiation in business/life | | 58:57 | Final advice for risk-averse women; why poker is the best teacher | | 59:55 | Poker Power app availability and Jenny’s ongoing mission | | 60:20 | Creating competition and legacy for the next generation |

Advice and Takeaways for Listeners

• Embrace Loss as Growth: Every failure compounds into greater wisdom and resilience.
• Risk is Personal and Evolves: Start small, self-assess regularly, and consciously expand your appetite for risk.
• Systems and Mentorship Unlock Scale: Seek guidance, structure your risks, and keep learning through feedback and iteration.
• Poker Teaches Life and Business: Playing poker builds the strategic, risk-savvy mindset essential for financial and professional success.
• Own Your Failures: Make them visible reminders for smarter future decisions.
• Action Over Affirmation: Hard work, curiosity, and discipline consistently outperform mere positive thinking or entitlement.

Resources Mentioned

• Peak6: Jenny’s investment firm (notable for diverse, non-traditional hires and constant innovation)
• Poker Power: Organization teaching women poker as a tool for confidence and decision-making ([Poker Power Play app now available] [59:55])
• Books/Stories: Long Term Capital Management as a cautionary tale of risk ([04:26]), Moneyball for analytics-driven decision making ([32:01])

Closing Thought

"If I could have learned poker when I was younger, I think I would have saved 10 years out of mistakes in my career."
— Jenny Just [58:57]

This episode is a must-listen for anyone looking to cut through the noise on risk, money, and building a more empowered financial life—with tools, not just talk. Jenny Just leaves listeners permission and a playbook to think bigger, fail smarter, and bet confidently on themselves.