What if the same mindset that built a billion-dollar trading firm could change the way women relate to money, risk, and power? Jenny Just, co-founder of Peak Six and founder of Poker Power, joins host Annie Duke to explore how a career built on options trading taught her that you don't have to win every time to have a winning strategy. Jenny reflects on the experiences that shaped her approach to risk. From building one of the world's most successful trading firms to learning how luck and skill interact in every important decision, she and Annie discuss why the best decision makers embrace a range of possible outcomes, how fear can be reframed into curiosity, why waiting for certainty is often the riskiest choice, and what poker teaches us about thinking strategically under uncertainty.
Life is way more fun making decisions, right, than not, because you don't know what the outcome is going to be, no matter what. No matter how bad.
Key takeaways from this episode include why good decisions can still produce bad outcomes, how practicing decisions builds better judgment, why understanding risk is more important than avoiding it, and how teaching decision-making through games like poker can help people, especially women, become more comfortable making high-quality decisions in work, money, and life.
This is the Decision Education Podcast where we explore the science of decision-making with a diverse range of experts and offer practical strategies to transform our understanding of the role decisions play in our lives.
If you enjoy this podcast, then stay tuned for a limited series we're announcing this fall. Navigating Uncertainty features Alliance Executive Director David Samuelson in conversation with education leaders and policy makers to explore how they make decisions, what they've learned from getting it wrong, and what they believe it will take to give the next generation the tools and the agency to think for themselves.
Because in a world increasingly shaped by algorithms and artificial intelligence, the most important skill we can give young people isn't the ability to find an answer. It's the ability to own one.
I'm so excited to welcome my guest today, Jenny Just. Jenny is a visionary and one of the few self-made female billionaires in the United States. She co-founded Peak Six in 1997 with $1.5 million in seed capital as a proprietary options trading firm and has since grown it into a multi-billion dollar financial services and technology giant. Jenny is passionate about finding opportunities for women to succeed at every table from the classroom to the conference room to the poker room and the boardroom. This led her to launch Poker Power in 2020, a company that unlocks the power of poker to transform professional and personal lives through life skills such as strategic thinking, risk intelligence, and decision-making.
Jenny has created programs to help women advance their careers, including the Women's Trading Experience and Women's Technology Experience. She currently serves on the Women and Public Policy Board at the Harvard Kennedy School. Jenny's remarkable success has earned her a number of accolades, including being selected as a 2025 CNBC Changemaker and being named to Forbes' list of America's Richest Self-Made Women, Forbes' 50 Over 50, and Worth's Groundbreaking Women.
Jenny, I'm so excited to have you on the podcast. Thank you for coming and taking the time to chat with me. I really appreciate it.
My pleasure. So, how long ago did we meet? It was a long time ago. It was before the pandemic, I know.
It was before the pandemic. Yeah, for sure.
Yeah. And I came and spoke to Peak Six.
Which obviously you were a co-founder of. I would love to hear your journey in terms of your decision to co-found that. And then separately, at a time when this was, I mean it's still incredibly rare but then it was like really, really rare for a woman to be in that position.
Sure. Sure. Happy to do so and thanks so much for having me. So if we back up a bit, when I left school I had no idea what I wanted to do and I got into options trading by accident. So I wanted to be in Chicago. I interviewed anywhere I could. I happened to be a female who could answer the math questions quickly. It was a time when there was still the exchange floors and screaming and yelling. So I think I was a shiny new object and they took a bet on me, a company called O'Connor and Associates. So I was super lucky to basically go through O'Connor University in my early 20s and learn a skill. That skill turned out to be extraordinarily useful not just to actually trade and make money but to make decisions ultimately.
But as we were there, I also had an opportunity to start sort of be an entrepreneur inside the trading firm. They did a joint venture with Swiss Bank and I was part of the over-the-counter equity derivatives founding group. So there was two of us. My future co-founder was in there and another gentleman who had come in from Goldman Sachs. So, we started this department. I saw what it took to start something from scratch, right? All the different departments from HR and legal to ops and tech. And so, we got our feet wet there a bit and then when the bank eventually became UBS, moved to the east coast, we're like, well, we don't want to move. I really wanted to be in Chicago. It was the whole reason I was there to begin with. So, I'll just let's just do that again, which is now we're in our mid to late 20s at this point, quite naive of so, but we'll just do that again.
And there were a handful of ex-O'Connor partners who said we'll give you a little bit of money and we started with a million six and we were just going to do exactly what we had already done there. It is now almost 29 years later and we still haven't done that plan. So, we're a little bit behind, but we did start down the path of building this business and we actually had a bid to buy us very early on to do it for a bank again to do this over-the-counter equity derivative business for a bank. But in the meantime, while we were searching for a partner, we're like shoot we got to make some money. So, we started trading and we put a couple people on the trading floor and very quickly started using technology. I think in that was, you know, we definitely weren't visionary, we're definitely not Steve Jobs but we didn't know how to manage people. We were looking around and saying, you know, there's four exchanges I think at the time and we can't populate them because we don't even know how to manage people sitting right next to us so we better figure out how to do this thing differently and we happen to be, you know, one of the first off-exchange floor equity options trading firms back in '98.
And that tech took us really quickly into competing with the biggest guys super early. That business today, like I said, is almost 29 years old. It's never had a losing year. So what we were able to do with that is self-fund all these other crazy ideas that, you know, 20-somethings start to have and probably lose money in more ways than most people, you know, now, you know, a lot of people so I'm not quite sure that's entirely true but we definitely tried a whole bunch of different things so it's been a wild ride.
So you talked about, you know, I got lucky, right, when you were mentioning what was happening in Chicago, and I think a lot in sort of the path that our lives take, the types of decisions that we're making, the intersection between the decisions we're making and luck, and I'm hearing this across your story. You started trading options at a time when edges were wide, but you still had to be great at it. Right. You have to not only see this is a good solution for us, but this is a good solution for other people. We could actually think about this as a solution for other things we could do besides support our own trading, so on and so forth. So, I'd love to just kind of hear your thoughts about as you're thinking about these inflection points in your career. How do you think about that intersection between the skill of it all and the timing, which is really a luck question?
Mhm. Well, so we think about luck a lot and we think there's obviously a major component of it, particularly in the markets, but being prepared when your ship comes in to hold on with both hands and really ride it is the most important part. But it's also lucky that if you're preparing for the right thing, we know a lot, but we don't know everything. And so when we start to make business decisions, we also know we don't know everything. And I would say, you know, especially for me personally, I was a single mom and making decisions. I think it was my fear that drove a lot in the early days. What if I don't have income? I thought I was going to have enough, but what if I don't? I thought I don't know how to do this. And I know I came from a group of traders who tend not to be good managers. So if we have to manage a lot of people, that's a problem. And we actually happened to meet someone talking about these issues. And he and they said, well, you know, you could use technology, right? Which sounds very silly today.
And I said, no, I didn't. And so I immediately went down that rabbit hole because if that is one of my options, you know, truly one of my options in this case that I can cut off some of my fear and anxiety around how long this one thing will take to build and this other thing is, you know, sort of purely risky from just an income perspective. If I can cut that all off and go directly so I can test my hypothesis that much sooner, I'm going to try and do that.
You're kind of the opposite of this, you know, the classic story about Blockbuster, right? Like here's Blockbuster. They completely own the market. People go into their store, they rent movies, they bring them home, they watch them, they return them. They have an opportunity to actually acquire Netflix. So that they're not creating the technology themselves. But there is a company that is actually thinking about this from emerging tech. They can acquire them. They don't. They're just kind of like stuck. It's that enterprise problem of no, that will disrupt our business, right? Because obviously if you have a technology solution to delivering content, people aren't going to go into a store anymore. So it's that self-disruption thing, right? They're not willing to pivot. And you, this story happens over and over again. Meanwhile, it sounds like your story from the start of founding Peak Six is a story of self-disruption.
Right. No, I'm willing to disrupt it. I don't need to be pursuing one thing. I have different things I can pursue. I can try them. The things that work, I'll go do them. The things that don't, I'm going to discard them. I'm going to think about the cost to pursue them, of course, but particularly if I think the benefit is there, I'm willing to try a bunch of different stuff and see what happens. And then you discover something that's really successful, the tech business, and you still continue that mindset throughout. How did that inform the way that you approach this business? Why was it such a big advantage?
Yeah, I, wow, was I lucky? That's all I have to say about being taught that skill. I was a pretty good decision maker to begin with. I think I was relatively speaking. But now someone's training me to look at a range of outcomes. When the things are very fluid around you, there are, you know, shiny objects coming into your sight every minute or every hour or every week that you have to make some larger decisions on. And that repetition, that muscle that I just kept doing over and over and over again. But when the light went on, right, that's when the confidence came. That's when I realized, right, I don't have to win all the time for this to be a winning strategy. And I learn more and I decrease my downside the more I learn. And so each one of those execution points elevated my ability to, you know, jump into whatever that next thing because the next thing was just another trade. It was just another decision.
One of the things that I try to tell people is true competitive advantage comes from this ability to lean into the uncertainty. You lived in this place of like I'm looking at what the future might look like and I understand that I'm making some forecasts about what those futures might be. I have two venture clients, First Round Capital Partners and Renegade. Love them. They have adopted a more options trading mindset, right? But this is the mantra that I say all the time. Oh, if you have an amazing decision process in venture, here's the only thing I can guarantee you. You will invest in companies that fail and you will pass on companies that succeed. That will happen.
We're not going to create a process that will avoid either of those things occurring because they are, there's just luck.
That's just luck. So I said, this is the one guarantee I can give you. You're going to pass on a company that's going to do amazing. You're going to invest in a company that's going to do terrible.
Those two things have to be true. All we're trying to do is increase the probability that you don't pass on a good company and increase the probability that you do pass on a bad one. That is all we can do. And if you do better than the version of yourself that isn't actually thinking in this way and this process, you're good to go.
I love it. I love it. That's perfect. And I'm going to catch myself and make sure my team catches it because I think again what my learnings are in each one of those made my next decisions that went better.
So the other interesting thing I think when people get themselves into this cycle of it's hard to make a decision, right? Life is way more fun making decisions, right, than not because you don't know what the outcome is going to be no matter what. No matter how good or how bad. So getting those reps under your belt just make this, I mean this is why poker, I don't know if you know this but I didn't play poker my whole career until 2019 and right.
But you did though because it's the same thing. Right. But I didn't know. And I was like, well, first of all, that's what people are doing this because it's fun. But second of all, like that is the closest thing I've ever seen to what I learned, right? No wonder all these options traders are good at playing poker. But also, there's so much you can learn from just being in the game. And where's a place to get practice doing it for people who are uncomfortable doing it?
Well, exactly. And I think when you say life is, I love this. Life is more fun making decisions than not. Let's take this back to that word mistake. You said when you were, you know, trading, you had to learn that you're going to lose sometimes, but if you win more than you lose, then it's good because there's volatility and okay, right? You're just trying to grind those edges and whatever. When you're playing poker, you're gonna win some hands, you're gonna lose them. Okay? You can play a hand the best you've ever played a hand in your life and you can lose it because someone hits one card that's available.
Venture, same thing, right? I say this all the time about like ordering off a menu. Assuming you've never eaten at the restaurant before, sometimes you're going to order something, it's going to be a good choice for you given what you know, and then it's going to suck. Does that make it a mistake? Hope not, right? But we process it that way. So, let's now bring that back to life is more fun making decisions, right? This causes us to get into this inability to make a decision, which translates, of course, to just like having a very low risk tolerance. Why? Because when you make a decision, you could have a bad outcome. If when you get that bad outcome, you're really sad and you feel terrible and you think it's a mistake. How are you going to make a decision? Because you're going to be so afraid. You're going to want to have so much certainty around the choice to make it so it's got the lowest probability ever of getting a bad outcome, right? Which means that you can't possibly be making decisions that have high upside associated with them because I haven't come across too many things. There are occasionally some, but I haven't come across too many things where you're very certain that there's very little downside that have any significant upside associated with them. It happens occasionally, but it's rare.
But it's rare. So, if we're afraid that when things don't go our way, it's a mistake, then all of our decision-making is going to be focused around not quote unquote making a mistake.
And that becomes really tough and is tough, paralyzing, right? And by the way, not fun.
So therefore, I'm not going to do it again. And then your possibility of you making a risky decision just goes way down and you just you don't learn anything. And so you're stuck in a vicious cycle that you can't get back out because you can't see the forest from the trees. I think it's ultimately if we want to learn to be better risk-takers, it is a skill you can build and be better decision makers. It's a skill you can learn. And not only is it to your point, which I love, you can hear somebody how they make decisions in the way they communicate. When we talk about, you know, the great one is women raising money and how they raise less money, right? The people can see through that you don't think you have a lot of upside.
And you're really protecting your downside or whatever story you might be telling the other side, especially if they're good risk-takers and decision makers, they're interpreting those words. And so just ignoring this idea of, you know, I have this great idea, but how do I take a risk and do it and then do it again and do it again and do it again because every day hopefully there's a new opportunity to get better at it. If I just ignore doing that because it's hard, it comes through in who you become. Back to this, you know, did I know what nobody would have sort of declared where I got to from where I was. I literally learned the skills. I learned how to make good decisions taking risk around money through learning options trading. Most people aren't going to do that. So now what is your option, right? It is to learn from experts in it like yourself. It is to play poker hopefully for people who are not sort of already doing it. It is for those who play poker and think about it differently. I think that's an interesting thing I think we found in our process of starting to talk about poker for women through Poker Power. But each one of those layers opens up, like the flower starts to open a little bit more on the possibilities around you because range of outcomes is good because you don't have the upside without the down as you said again occasionally there's a what we would call a free roll, right? Zero downside, lots of upside. It comes up occasionally but it's very rare because the market corrects for it, right? So it happens sometimes but not often.
Yeah, Alexa, I'd love a free roll, right? Like, I'll take it. All right. So, you mentioned Poker Power. I do want to definitely talk about that. So, when we think about population distributions, and I want to be very careful to say population distributions, on average, women are willing to take less risk than men. So, are more risk averse than men are. Again, when we just look at the population now, obviously you're an outlier in that distribution. You've taken on a tremendous amount of risk, I would imagine even going into options trading just to succeed at that, you were probably riskier than the average woman.
That and riskier doesn't mean stupid, right? It doesn't mean, you know, driving drunk at 120 miles an hour on the highway. I mean riskier in the sense of being willing to decide under uncertainty where there is this distribution of outcomes and some of them are bad and being tolerant of that decision-making environment. So you've now founded Poker Power really focused on women and risk. So, can you talk a little bit about what it's been like for you thinking about I'm such an outlier in my world. I know the power of being good at taking risk. I see this population distribution issue. How have you thought about addressing that throughout your career and then landing on Poker Power and the founding of it and what is it doing?
I'll start with, you know, we were being totally selfish when trying to come up with a solution for our own firm. So, what do I see with me being there? I see an options trading firm that is doing things differently than any other options trading firm that we know of has done in the past. If you look at our portfolio, if you look at what we've become, if you look at that range, squarely has to do with me, also has to do with my partner. But having a female in that seat, there's so few women prior to us doing Peak Six that were trying to solve the problem. Like if you think our first technology was built because I went into Wendy's at the time, which was right around the corner from our office, and I saw what they were doing. And so our first technology was built after what the restaurant was doing, taking orders. One person would do the fries and one person would do the hamburger. And I'm just looking at the problem differently. So we knew different people, different sets of brain power. And if half the population isn't represented, that's probably a good bet to make if I can get smart women from the other part of the population. Problem was we couldn't get them very early on in Peak Six. I don't know this might be 2001 or something we had all women's trading day and way more men came than women came. So just getting them there was the problem. So as we continued through the process we had multiple fails. It wasn't until we created something, now it's almost nine years now, Women's Trading Experience where there was a woman, a very senior woman who worked for us who, and experiences kind of weren't a thing yet and said if you're smart, you're curious and you're a hard worker just come see what this is about we're going to pay you to learn because at the end of the day markets are also fun, right? Particularly the equity markets are fun they are just stories there are stories about people doing things with companies, right? And so come and learn. Now the interesting thing about that is when we started doing that, we started to get the women. Keeping the women was hard and it's still not difficult today. But we get way more women than we did. But I think the most interesting thing is back then I was like this has to be the best internship they've ever seen for whatever reason so that they love it no matter what. Every hour of every day has to be fun. And of course, one of our primary teachers was a poker player. And so he said, well, I'll teach poker.
For so, once a week or twice a week, whatever it was, they're going to learn to play poker. I was like, great, fine. I don't care what it is as long as they're engaged. This time I did not play poker. It's 2019 when I learned to play poker. And because of my daughter and, just really quickly, she's playing a tennis match. Her dad's watching, upset she's losing. Comes home, she may as well be hitting against a wall. She doesn't realize this is someone she probably should have eaten. She didn't realize someone's thinking and strategizing on the other side of the net. She needs to learn to play poker. Now, he is not, he's more of a blackjack guy, but he knows right what she's missing. Top down, she's not thinking about what they're thinking. And she needs to play poker. And sort of said it flippantly. And then I was like, "You're ridiculous," and walked out. And like two weeks later, I was like, should I teach my 14-year-old daughter to play poker? And then I was annoyed because I have three sons. I would never have said that about my sons. Turns out they already knew how to play. I didn't even know they knew how to play because they all just figured out. And so I was like, let's, we end up doing an experiment. 10 girls, 10 moms. And you know, it's one of the reasons why, you know, of course we knew you through trading, but like that I'm public at all today is because what I saw there was the closest thing I'd seen to what made me personally comfortable taking risk. And there I am hand after hand. It's the same thing. Trade after trade, making those decisions, having to put my resources behind that decision. And I use your line about your chips are your voice. Some version of that, right?
Because now it's not just about that trade or that money transaction. It's about speaking up in that meeting. It's about that negotiation you're about to have. How do you use your, sort your ammunition there to get the most effect at the right time against certain people? And then when that changes, how do you then change with it? So all of a sudden I was like, this is what was going on in, you know, my trading program. Of course, you see poker being taught at some of the best firms already, but nobody was taking it on for women, right?
And for me, it's all about young girls ultimately, because if they get all the practice when they're young, just like the boys get the practice playing poker, how are they going to be later? The irony of course is trying to get young girls to play. First of all, they don't want to play, and second of all, like their moms are like, why am I, that's weird. So during COVID, we started saying to the family of companies at Peak6, you know, we want to teach your daughters. And then the women were like, wait, if it's so good for them, why aren't we learning? Taught them. Morningstar heard what we were doing. Today we're in, I think, almost 70 countries now, teaching around the world.
On a mission to teach a million girls and women the game, but teaching at the biggest banks, at the law firms, at the tech firms, at, you know, at our media and communication firms. It's, it's kind of crazy, but what those women are learning is so eye opening. And the other little tricky little note I have in there, as I've talked to more and more senior women through the process, how many senior women actually grew up playing poker,
But they don't talk about it, right? Adena Friedman who runs NASDAQ, or the only woman, Maggie Wilderotter and her sister, they were the only Fortune 500 CEO sisters, and she was a Fortune 500 CEO twice, grew up playing poker at age six and seven. Like we just have this long list of people. Clinton grew up playing poker. Malala grew up playing poker. And so it's embedded in the culture of half of our population distribution. It's not in the other.
Yeah, yeah.
And then at the end of the day, it was like, how would the world be different if half of the poker players were women? So, I mean, it becomes a really interesting question, and but also hard problem to solve.
Because it's not obvious. Most people turn their head when you talk about, you know, do you want to play? And they're like, so if they have not heard of something like Poker Power where, you know, you end up in this really safe, comfortable, fun environment to learn, um, they're not going to do it naturally.
You know, one of the things that I think about when I was playing poker is how firmly people have it in the gambling category, which of course it's not.
