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BigDeal by Codie Sanchez

Master MONEY MAKING In 60 Minutes: Everything They Never Taught You | Jenny Just

My new book Own Or Be Owned is out now! I wrote Own or Be Owned to answer one question: How do you make more money, less miserably?

Jenny JustguestCodie Sanchezhost

Oct 22, 202559mWatch on YouTube

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

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CHAPTERS

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Chapter summaries

Failure, Repetition, and Losing Tens of Millions in Seconds
Codie opens by noting Jenny is a self-made billionaire and asks what it means that failure shaped her. Jenny explains that trading's constant losses build compound experience, and describes losing tens of millions of dollars in seconds.
- •Traders lose 45% of the time, and that repetition compounds into experience
- •Jenny learned to take risk on a trading floor by losing small amounts many times a minute when young
- •She lost tens of millions of dollars in seconds; the first time was rough
- •Long-Term Capital Management is cited as proof that the smartest don't always win
- •Staying humble about luck versus skill matters
28 Years Without a Losing Year: Thinking About Risk
Jenny explains that Peak6 has never had a losing year in 28 years by not chasing the highest high and by reinventing itself in roughly three-year cycles. Asked how to conceptualize risk, she says people think too binarily and should consider a wide range of outcomes.
- •Avoiding the lowest low means not needing the highest high
- •Peak6 thinks in roughly three-year cycles of reinvention, possibly shorter with AI
- •Assume the worst-case and slightly-less-than-worst scenarios, not just the best
- •GameStop is an example of a move that can repeat; Peak6 often gets out of the way
- •Peak6 trades options in 3 to 4,000 public companies daily
Learning to Take More Risk
Codie asks why so many people take too little risk. Jenny says risk is personal and can be learned, starting with small steps, and that she herself was not a risk taker when young.
- •Risk tolerance is personal; self-assess on a one-to-ten scale and ask what purpose more risk serves
- •Risk can be learned by starting small, like raising your hand in class
- •Jenny grew up with four brothers and wasn't fazed by the male trading floor
- •She is considering building a risk framework or tool
- •Even hiring the 10th employee felt like a big risk to her
Saying No to Jamie Dimon: Setting a Deadline
Jenny tells the story of circling a date on her calendar in 1999 and walking away from a bank deal when no answer came. Codie shares how she used a deadline in her first marriage and how Jenny's story inspires her approach to a banking partnership.
- •Peak6's plan A was a bank partnership for over-the-counter equity derivatives; plan B became the 28-year business
- •Jenny set a date and told First Chicago, where Jamie Dimon was, that they were out
- •Codie put an end date on her first marriage and kept her word to herself
- •Sticking to a deadline the first time is motivating and changed Jenny's trajectory
- •Codie considers a deadline for her banking relationship, otherwise buying a bank
Why Poker Is the Skill for Women and Risk
Codie asks if one skill or game could help women break out of risk aversion. Jenny describes how poker resembles her options-trading training, how she started teaching it to her daughter and 10 girls in 2019, and how it grew into a program taught at hundreds of companies.
- •Poker is the closest thing to options trading training and is accessible to anyone
- •An experiment with 10 girls and 10 moms started after her husband's comment about her daughter's tennis match
- •The program moved to Zoom during COVID and has reached about 370 companies in 60 countries
- •Poker involves decisions with imperfect information and reading people
- •Hands translate to negotiations, meetings, and where power sits
Risk, Mindset, and Money Myths
Jenny says people need to take action and accept some risk to get rich, and asks Codie's view on a quote about unlearning money beliefs. She then rapid-fires common money sayings, including saving and skipping coffee, deserving success, and patience.
- •Jenny believes it's harder to get rich without taking some risks
- •She has no good solution for teaching mindset beyond touchy-feely advice
- •Skipping coffee: have defense and offense, and enjoy yourself along the way
- •Deserving it: hard workers have succeeded at Peak6
- •Be patient: think of a great year over a three-year timeframe and stay conservative about spending
Being a Self-Made Billionaire and Who to Listen To
Codie reflects on taking advice from people who haven't done the thing, and asks Jenny how it feels to be called a billionaire. Jenny says it's awkward but that representation is important.
- •Codie questions whether the people we listen to have achieved what we want
- •It's uncommon for successful people to talk openly about their wealth
- •Jenny finds being called a billionaire awkward
- •She knows representing women matters
Peak6 Experiments and Hiring Approach
Jenny describes experiments with hiring types of people, including hockey statisticians who later worked for NHL teams and poker players. She explains Peak6 looks for hardworking, curious people with no required finance background.
- •Hockey analytics enthusiasts were brought in as a class; they weren't great traders but later worked for hockey teams
- •Hiring the smartest people possible was a complete fail
- •No finance background is needed; hard work, curiosity and above-average intelligence are
- •Culture matters in hiring, and questions are kept fresh
- •Jenny suggests the equity side as a place for women to start in markets
Compounding Risk, Reassessing, and the Failure List
Codie proposes a framework of repetition, structure, and bigger risks, and Jenny adds the need to reassess like marking to market. She talks about chasing a number, billion-dollar investments going to zero, and the list of company failures she keeps on her desk.
- •Evaluating risk takes time and data, like hands adding up to a poker game
- •Mark to market: would you do the same thing if starting tomorrow?
- •The 'number' keeps moving, and investments valued at billions have gone to zero
- •Jenny keeps a list of company failures on her desk
- •Codie mentions others who display failures, such as a friend's picture of failed investments
Entrepreneurial Itch and Staying Curious
Jenny explains her drive to build a third multi-billion-dollar company and how poker advocacy motivates her public presence. Asked whether the love of the game can be taught, she says it needs inherent desire fueled by curiosity and amazing people, and tells the Wendy's story behind Peak6's first technology.
- •Jenny wants to create a third multi-billion-dollar business, mainly to prove it to herself
- •The public story is useful for getting more women playing poker
- •Curiosity and surrounding yourself with amazing people fuel desire
- •Peak6 looks for people who don't have all the answers
- •Its first tech, an inventory management system for options, was inspired by a Wendy's
Proud Turnarounds, Big Industries, and Small Business Opportunity
Jenny says she takes pride in turning around struggling companies and acknowledges more failures than successes. She discusses insurtech, why smaller businesses appeal to her, and the opportunity in the current cycle.
- •Pride in turning a hemorrhaging business around and sparing its people
- •There are more fails than successes
- •Insurtech is an old industry resistant to change
- •Smaller businesses offer opportunity to small teams
- •The current cycle offers unique opportunity with AI
Getting Your Hands Dirty with AI
Codie notes many people are scared of AI. Jenny says to get your hands dirty by building tools yourself, as she does with Claude Code, since most people are not experts.
- •Jenny builds tools herself for Poker Power's app and marketing
- •Doing so helps you think through problems and communicate with technologists
- •It doesn't matter if the tool goes nowhere
- •Everyone else is also learning; 98% of the world is like you
Entrepreneur Tells and Reading the Room
Jenny says an entrepreneur's biggest tell is overexcitement with no defensive thinking, and what Peak6 wants to see. She then explains levels of thinking at the poker table and how having managers play poker reveals team dynamics.
- •Overexcitement and naivete are the biggest tells in entrepreneurs
- •Red flags: no defensive answers and no acknowledgement of past failure
- •Think about what others think about your cards and what they owe their bosses
- •Set the table in full color by addressing context
- •Managers playing poker learn about their teams, like who tiptoes in
Final Advice: Learn Poker and Poker Power
Codie asks what Jenny would tell a woman who knows she isn't taking enough risk. Jenny says to learn poker, adding she'd have saved 10 years of career mistakes, and they close with Poker Power resources and the mission behind it.
- •Jenny's advice is simply to learn poker
- •She believes learning it younger would have saved 10 years of mistakes
- •The Poker Power Play app is out, plus in-person and virtual teaching
- •Jenny's co-founder would be pleased if the program created competitors

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