Redefining Risk

Producer’s Note: This transcript was created using AI. Please excuse any errors.

Annie: Jenny, I’m so excited to have you on the podcast. Thank you for coming and taking the time to, to chat with me. I really appreciate it.

Jenny: My pleasure.

Annie: So how long ago did we meet? It was a long time ago. It was before the pandemic, I know.

Jenny: It was before the pandemic, yeah, for sure.

Annie: Yeah. And I came and spoke to, uh, Peak6.

Jenny: You did.

Annie: Which obviously you were a co-founder of. I would love to hear your journey in terms of your decision to co-found that.

Jenny: Mm-hmm.

Annie: And then separately, at a time when this was inc- I mean, it’s still incredibly rare, but then it was, like, really, really rare for a woman to be in that position.

Jenny: 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-

Annie: Mm-hmm

Jenny: … ultimately. Um, 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 s- 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, it eventually became UBS, moved to the East Coast, we’re like, “Well, we don’t wanna 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, you know, we’re in our mid to late 20s at this point, quite naive, um, so, um, but we’ll just do that again.

And there were, uh, 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 gonna do exactly what we had already done there. It is now 20- almost 29 years later, and we still haven’t done that plan. So we’re a little bit behind, but, um, we did, we did start down the path of building this business. And, 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, “Mm, sh- shoot, we gotta make some money.” So-

Annie: Right. Right

Jenny: … we started trading, and we put a couple people on the trading floor, and very quickly started using technology, I think. And that was, you know, we definitely weren’t visionary. We’re, we’re definitely not Steve Jobs, but we didn’t know how to manage people, and we’re looking around and saying, you know, “There’s, there’s four exchanges,” I think at the time, “and we can’t populate them ’cause we don’t even know how to manage people who are sitting right next to us, so we better figure out how to do this thing differently.”

And we happened to be, you know, one of the first off exchange floor equity options trading firms back in ’98, ’99. Um, and that tech took us really quickly into competing with the biggest guys, super early. That business today, like I said, it’s 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.

Annie: Right.

Jenny: 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, um, we definitely tried a whole bunch of different things. So it’s been a, it’s been a wild ride.

Annie: 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 paths that our lives take, the type 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.

Jenny: Mm-hmm.

Annie: But you still had to be great at it.

Jenny: Yep.

Annie: Right? You have to not only see, this is a good solution for us, but- This is a good solution for other people.

Jenny: Mm-hmm.

Annie: 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?

Jenny: Mm-hmm. It was. 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, 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 this, th- these issues, and he’s… And they said, “Well, you know you could use technology, right?” Which sounds very silly today.

Annie: Yeah.

Jenny: And I said, “No, I didn’t.” And so I immediately went down that rabbit hole. ‘Cause if that is one of my options, you know, m- 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’ll take to build, and this other thing is, you know, sort of purely risky from just a, an income perspective. If I can cut that all off and go directly so I can test my hypothesis that much sooner- I’m gonna try and do that.

Annie: 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.

Jenny: Yep.

Annie: 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 n- they’re not creating the technology themselves, but there is a company that is actually thinking about this from emerging tech.

Jenny: Yep.

Annie: 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 ac- you know, our business, right? ‘Cause obviously, if you have a technology solution to delivering content, people aren’t gonna go into a store anymore. So it’s that self-disruption thing.

Jenny: Right.

Annie: 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 Peak6 is a story of self-disruption.

Jenny: Yes.

Annie: Right? No, I’m, 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 gonna discard them. I’m gonna 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. W- how did that inform the way that you approach this business? Why was it such a big advantage?

Jenny: Yeah. I, I w- 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, 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, the, I don’t have to win all the time for this to be a winning strategy, and I learn more and I, I decrease my downside the more I learn. And so our, e- each one of those execution points elevated my ability to, you know, jump into whatever that next thing, ’cause the next thing was just another trade. It was just another decision.

Annie: One of the things that I try to tell people is true competitive advantage comes from this ability to lean into the uncertainty.

Jenny: Mm.

Annie: You lived i- 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, uh, First Round Capital Partners and Renegade, love them.

Jenny: Yeah.

Annie: Uh, they, they have adopted a more options trading mindset.

Jenny: Nice.

Annie: But this is the mantra that I say all the time, “Oh, if you have an amazing decision process in venture, uh, here is 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.”

Jenny: That will happen.

Annie: We’re not gonna create a process that will avoid either of those things occurring, ’cause they are just-

Jenny: I love that.

Annie: … there’s just luck.

Jenny: There’s just luck.

Annie: No, th- that’s just luck. So I said, “This is the one guarantee I can give you.”

Jenny: I love that.

Annie: You’re gonna pass on a company that’s gonna do amazing, you’re gonna invest in a company that’s gonna do terrible.

Jenny: Terrible.

Annie: 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.

Jenny: Yes.

Annie: 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.

Jenny: I love it. I love it. That’s perfect. And I’m gonna 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-

Annie: Exactly

Jenny: … that much better. So, um, the other interesting thing, I think, when people get themselves into this cycle of i- hard to make a decision, right? Life is way more fun making decisions-

Annie: Right

Jenny: … than not. ‘Cause you don’t know what the outcome is gonna be, no matter what. No matter-

Annie: No matter what

Jenny: … how good or how bad. So getting those reps under your belt just make… This, I mean, this is why poker… And I don’t know if you know this, but I didn’t play poker my whole career until 2019. And-

Annie: Right. But you did, though. ‘Cause it’s the same.

Jenny: Because it’s the same thing. I… 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.

Annie: Right.

Jenny: No wonder all these options traders are-

Annie: Right

Jenny: are very 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 aren’t comfortable doing it?

Annie: 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.

Jenny: Yeah.

Annie: Um, you said when you were, you know, trading, you had to learn that you’re gonna lose sometimes. But if you win more than you’re, you lose, then it’s good, uh, 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 some.

Jenny: Mm-hmm.

Annie: You can make, 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 avail- whatever, it happens.

Jenny: Yep.

Annie: Venture, same thing, right? I say this all the time about, like, ordering off a menu.

Jenny: Mm-hmm.

Annie: Assuming you’ve never eaten at the restaurant before, sometimes you’re gonna order something, it’s gonna be a good choice for you given what you know, and then it’s gonna suck. Does that make it a mistake? I hope not, right? But we process it that way.

Jenny: Yeah.

Annie: 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 ve- 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 gonna make a decision? Because you’re gonna be so afraid, you’re gonna 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 cr- 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.

Jenny: Yeah.

Annie: 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 gonna be focused around not, quote-unquote, making a mistake.

Jenny: That’s right.

Annie: And that becomes really tough.

Jenny: And is tough, paralyzing, right? And by the way, not fun.

Annie: No.

Jenny: So therefore, I’m not gonna do it again. And then your possibility of you making a risky decision just goes way down.

Annie: Right.

Jenny: And you just… You, you don’t learn anything, and so you’re, you’re, you’re stuck in a, a vicious cycle that you can’t get back out ’cause you can’t see the, 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, a 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.

Annie: Yeah.

Jenny: 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? ‘Cause every day, hopefully, there’s a new, new opportunity to get better at it. If I just ignore doing that ’cause 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 gonna do that. So now what? What is your option?

Annie: Right.

Jenny: 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, um, for women through Poker Power. But each one of those layers opens up, it… Like, the flower starts to open a little bit more on the possibilities around you. ‘Cause range of outcomes is good because you don’t, you don’t have the upside without the down, as you said.

Annie: Again, occasionally there’s a f- what we would call a free roll, right? Zero downside, lots of upside. It comes up occasionally, but it’s very rare ’cause the market corrects for it, right? So, uh, it happens sometimes, but not that often. Um, um-

Jenny: I’ll take one.

Annie: Yeah. It looks… I, I’d love a free roll, right? Like, I’ll take it. Um, all right. So you mentioned Poker Power. I do wanna 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 risks 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.

Jenny: Mm-hmm.

Annie: Uh, that… And riskier doesn’t mean stupid, right? It doesn’t mean, you know, driving drunk at 120 miles an hour, uh, on the highway. Uh, 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, of that decision-making environment. So you’ve now founded Poker Power-

Jenny: Mm-hmm

Annie: 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?

Jenny: 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, um, a female in that seat, there’s so few women prior to us doing Peak6 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 would, 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 d- on in Peak6, I don’t know, this might be 2001 or something, we had an all women’s training 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 st- 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 gonna 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. They’re 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 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 planned.” And of course, o- our– one of our primary teachers is 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 gonna 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, and w- because of my daughter. And, uh, 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’ve been, should’ve beaten. She doesn’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, um, “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 th- 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 ’cause they all just figure it out.

And so I was like, let’s… W- 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?

Annie: Yep.

Jenny: Um, 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?

Annie: Right.

Jenny: 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 gonna be later? The irony, of course, is trying to get young girls to play. First of all, they don’t wanna play, and second of all, like, their moms are like, “Why am I… That’s weird.” So during COVID, we started t- saying to the family of companies in, 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. Morning Star heard what we were doing. Today we’re in, I think, almost 70 countries now, teaching around the world.

Annie: Yeah.

Jenny: 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, in media and communication firms. It’s cr- 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?

Annie: Mm.

Jenny: But they don’t talk about it, right?

Annie: Ah.

Jenny: 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. Hillary Clinton grew up playing poker. Malala grew up playing poker. And so it’s embedded in the culture of half of our-

Annie: Yeah

Jenny: … population distribution. It’s not in the other. 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, it becomes a, a really interesting question and, but also a hard problem to solve.

Annie: Yeah.

Jenny: Because it’s not obvious, and most people turn their head when you talk about a w- you know, “Do you wanna play?” And they’re like … So if they have not heard of something like Poker Power where, you know, you end up this, this really safe, comfortable, fun environment to learn, um, they’re not gonna do it naturally.

Annie: You know, one, one of the things that I think about when I, I was playing poker is how firmly people have it in the gambling category, which of course it’s not.

Jenny: Right.

Annie: Right? My definition of gambling is when you make bets that are negative expected value hoping to get lucky. For the majority of the population, when you’re playing blackjack, that would be gambling.

Jenny: Yes.

Annie: Uh, certainly if you’re playing baccarat, that’s gambling. If you’re playing craps, that’s gambling. There is no bet that you can make in craps where the house is not winning. So you’re gambling your money hoping to overcome the odds and get lucky. That’s gambling. That is not poker. If you’re good at poker, and not all people are, but if you’re good at poker, you actually are what we call positive expected value, meaning that for every dollar you put in you’re gonna get something more than a dollar back on average. It’s not gambling. That’s investing. Or trading.

Jenny: Or trading. Yep.

Annie: Right. But people would be like, “Oh, you’re a gambler. Have you gone to Gamblers Anonymous?” Now what I think is interesting about that is that nobody asks that of any of the men.

Jenny: Never.

Annie: So I think that there’s this societal interaction too which is a barrier to entry. So there’s all these men who are playing poker for a living. Nobody’s getting asked, “Oh, are you going to Gamblers Anonymous?” Like, “What’s wrong with you?” Right? They’re just like, “Ooh, cool. You’re a maverick.” Like the TV show.

Jenny: Exactly.

Annie: They would talk to me and be just like, “Oh, are you going to Gamblers Anonymous?” They’d ask me things like, “Oh, your husband must be rich.”

Jenny: Mm-hmm.

Annie: And like you, I was sole support. No. Um-

Jenny: That’s right

Annie: … this sort of side eye, like, “What kind of example are you setting for your children? You couldn’t possibly be a good mom.”

Jenny: Right, right.

Annie: And I think it’s not just this sort of, you know, why does this distribution look like this, right? Like, I’m sure there’s some evolutionary reasons for that, but a lot of it is just men can go out and play craps and it’s cool.

Jenny: Mm-hmm.

Annie: If women are doing that, they’re irresponsible. They’re not taking care of their children. They’re betting the grocery money. Why is it the women’s grocery money and not the men’s, right? So you know, I think that barrier to entry, like from a societal standpoint, like how do we normalize this idea that like it’s good for boys and girls. Like girls aren’t irresponsible if they’re doing this thing. Like how have you thought about addressing that problem?

Jenny: We are climbing the hill with, you know, hundreds of years of, you know, culture and society telling us that this is not what to do. With women not clamoring to do it, though the interesting thing, that is changing. Where, you know, our momentum, I would say, is good. I mean, in the beginning, it was too edgy to even have a conversation about. That was coming out of COVID. So here we are more than five years later, and it’s really normal now for me to talk about it w- in certain audiences, all-female audiences for sure.

When dads hear the version, you know, they don’t always hear me, but they’re like, “I can’t believe it. Why didn’t I… Why did I teach my sons and not my daughters?” So it’s becoming the norm. It’s Like anything, nobody’s ever figured this out on the planet, um, which is crazy. But like we’re in East Kenya teaching marginalized girls through the Global Give Back Circle. Nobody’s even heard of poker there. The Maasai chief had to watch our lessons via Zoom. This amazing woman who started Gl- the Global G- Give Back Circle, she had an arrangement with some, uh, some of the tech firms. That’s how the tech was already set up, and the girls then built their own poker tables. It’s been so powerful. And so now here we have all the noise of the US, is it really poker, is it not? How are these girls who really have next to nothing, how are they using poker? And what you see, it’s been so powerful to them, it’s now become their leadership course.

Annie: Oh my gosh.

Jenny: The girls stand in front of the board, right? ‘Cause now we have got, gotta go to the board ’cause Linda’s gotta talk about why, you know, why are we teaching these girls poker? And they say, “I’m better at math. I can negotiate with my dad to go to school five days a week instead of carrying water two days a week. I am changing my life because this game. W- I … It’s … Which is really interesting to me how this game makes them feel, because we know in the US for women right away it makes them feel sort of cool and, and badass and all those things because of what society has created. But even there where they don’t know the game, it’s changing.

And so they’ve now created something called the Risk Lab. And so they’re learning how to take risk in different ways in different places besides just sitting and playing poker. It’s fascinating. So I think where it’s going is, you know, we can’t say which path will take us to where this, you know, half the poker players on the planet, I mean, ’cause that’s a lot of people that we have to-

Annie: Yeah, yeah, yeah. Of course

Jenny: … bring poker. But just being part of society when people realize it’s not … It’s a little bit like finan- when you think about financial education, right? Being wh- why haven’t we figured that out? It’s a little bit crazy or a lot crazy, and why it’s not required in the US and all these different things. Those things are gonna converge, ’cause every single day I’m taking … First of all, every day I’m taking risks even if you don’t think you’re a risk-taker.

Annie: Well, w- when you go down the stairs, you’re taking risks.

Jenny: Right. And so, and then I’m spending money every single day, and that’s a risk at where I’m choosing to allocate my capital every single day. So these things will converge into, I think part of it, it’s a language, the language of risk-taking, the language of decision-making, the language around money where there’s a lot of discomfort, right? That language of poker. If I can … Right away, like women are turned off ’cause I don’t know what they’re saying. When they say they, they checked. What? Right?

Annie: Right.

Jenny: All of a sudden, I don’t wanna make myself look stupid ’cause I want what’s coming out of my mouth to have somebody else interpret it the wrong way. Same thing around money decisions. All those different things. So I think our ultimate goal is obviously to get these women to play poker, but really about to be comfortable taking risk around money. Because building equality has everything to do with power, and power is everything to do with money. So these, the, they, they have to come together in order for us to have, uh, you know, a different planet that we’re living in.

Annie: You know, I think it’s interesting. I was, I was talking to Corinne Low, who wrote a fabulous book called Having It All. A book m- mainly for women, although, uh, men would certainly get quite a bit out of it. I think they should read it also. But it’s really approaching how you make decisions in life through this idea, you know, of utility, right? Like, what’s gonna bring you the most utility? And in there, how are you understanding risk versus not risk?

And, uh, I’m just listening to what you said, and I keep just wanting to go back to, I feel like risk particularly is applied to risk-taking. Um- Has a negative implication in the way that we kind of use it colloquially, right? Like, ah, you, you w- you know, it has this idea of, like, too risky, right? A- as opposed to risk as a neutral term. That there’s just risk and everything has a cost benefit associated with it, and you’re trying to calculate do the benefits outweigh the costs within my risk tolerances, right? And your risk tolerance would just be how much are you willing to lose in order to gain, and how are you thinking about that, and are you thinking about that in a way that’s rational versus not biased.

But she points out, and I think that this is something so important for women to hear, that women very often, and I think this has to do with what you’re talking about with, like, empowering girls to, like, go to school, know, understand money, understand how to allocate your capital, which isn’t just money, but also your time, attention-

Jenny: Right

Annie: your resources, that women in, in, like, the more trad wife type of tradition view themselves as not taking on risk. But it’s because they haven’t been taught about risk because she said, of course, there’s a tremendous amount of risk-

Jenny: Mm-hmm

Annie: … associated with making that trade, that you’re gonna put time into the house and the kids while someone else makes the money.

Jenny: Yeah.

Annie: Because what if they decide they don’t wanna be with you anymore?

Jenny: That’s right.

Annie: Right? As an example, right?

Jenny: Yep.

Annie: So, so we need to start to think very clearly about the risks associated with any decision, and understand that what feels like a safe choice if we’re not trained-

Jenny: Mm-hmm.

Annie: .. in thinking about this may not be actually as safe as doing other things that might be scarier-

Jenny: Yeah

Annie: but actually weirdly safer. That’s not to say that you might not choose that path anyway, and I certainly don’t criticize for any- anybody for choosing that path, but choosing that path because it feels safe, we need to train women to think more broadly.

Jenny: Yeah.

Annie: Right? Uh, about, like, what does risk mean? Not good or bad, just what is it?

Jenny: Just what is it.

Annie: How do you think about managing it? How do you think about cost, benefits, risk tolerances? What makes sense for you?

Jenny: Yeah. We, we often talk about taking risks, with an S, as opposed to-

Annie: Yeah

Jenny: … just taking risk because of the, the, the interpretation that people, you know, stereotypically have around it. The opportunity when we allow ourselves to go to the uncomfortable spot, which is usually where someone thinks that that’s therefore is risk, the more I, you know, stay in that pocket and allow myself to think about, again, back to range of outcomes- The easier it’s going to be each time. The irony of this, right, is that initial decision in a case of staying home or not staying at home, if we had d- done the training earlier, it’s going to be naturally part of the equation that it’ll be more obvious what the true risk you just took is. Because of course, as time goes by, it’s harder and harder to g- to go back and undo what you did. And I will read her book and, um-

Annie: I, I think you would, I think you would really love the book because it is approaching life decisions through an economist’s eye.

Jenny: Yeah.

Annie: Right? And I think it would be great for, uh, as a recommended reading for the people in Poker Power too, for-

Jenny: For sure

Annie: And again, I just want to be clear, if someone makes a decision to be a stay-at-home mom, I’m completely happy for them. The thing that I want is for them to be thinking about the risk, r- right? That are so … Like, what risk are you exposing to, yourself to? What are the benefits that you’re accruing-

Jenny: That’s right

Annie: from that decision? And just actually be thinking about it through that lens so they can make a decision that works for them in terms of what their expected utility is. What’s the happiness that they’re, they’re gonna derive from that-

Jenny: Right

Annie: … choice versus the downside associated with it.

Jenny: Yeah, taking, taking the emotion out of it, just put the facts on the table. Just you have all the data, right? Right. Why, why ignore part of the data? I mean, it’s the same thing with entrepreneurs. Why am I ignoring the fact that the chance that this doesn’t work is quite high? Like-

Annie:Right

Jenny: … the more I normalize Both sides of the, the possibilities. And when I normalize that in a regular life, it’ll, it’s gonna be a lot easier to make those decisions and make better, theoretically better decisions going forward. It’s not about hiding my head in the sand-

Annie: Yeah

Jenny: … on something I don’t want to see. But again, if I practice when I was, you know, like boys do, and I’m 10 and 12 and I start playing poker, and then I’m 16, I might play for, you know, a dime or whatever, a dollar or something that they pay for, and then I go to college and I start to play. Like, all of those reps of like knowing I’m not expected to win all the time, okay? That’s really helpful to know. Like, every time I make a decision, if I were expected to win, boy, I, you know, the sky’s the limit. But I’m not. And the boys already know it, which is why you can already move on from it. ‘Cause I wasn’t supposed to anyway. I don’t have to get hung up.

The emotional component of poker, as much as you don’t know what’s necessarily going on, like especially when you watch on TV and those type of things, but like the intangible things that it can bring. Like for me, the biggest one, ’cause you can imagine growing up as a trader, patience was an incredible virtue that it has given me so many times. And I mean, we all have, you know… You, you have an incredible poker journey. But like for people who it’s new to, there’s so many aspects as you move through it and you play with different people, and then you connect it back to your life. The cards are your data, and then, then the data you don’t know. Same thing.

What, what are my life decisions that I make in any given point in time? And by the way, I can bow out of this game. I can fold till the blinds bleed me out. I can do a whole bunch of things, but I can play another poker game. I als- also have another opportunity to play a game with a different set of people. What is that gonna be and how is it gonna be different than the first one? Each of these are opportunities for women. They, they aren’t, we’re not taking anything away. We’re actually giving them more-

Annie: Right

Jenny: … by showing them the data and informing them. And we’re not judging. You, you make your own choice on your risk-taking.

Annie: Yeah.

Jenny: But it, uh, you have a wider set, like your aperture has widened by understanding all the outcomes.

Annie: Well, obviously, huge fan of what you’re doing in that space. It will be linked in the show notes, obviously, but people should check out what you’re doing at, at Poker Power. It’s, it’s an incredible nonprofit that is really changing, hopefully, the way that, that women are thinking about risk and making decisions.

Jenny: That’s right.

Annie: What decision-making tool or idea or strategy would you wanna pass down to the next generation of decision makers?

Jenny: You know, obviously, the literal tool for me, for those who are trying to get better, is poker. If you’re already playing poker, and I think your opportunity connects poker, uh, we do this now all the time. We, in fact, our leadership teams play poker with each other. It’s a fascinating way to learn about the people that you work with.

Annie: Mm-hmm.

Jenny: When you can’t quite understand, like, what is it? What’s driving them? What risk are they are not taking as a result? And the other way we’re using it is with mentor-mentees, right? It’s awkward, you know, because we have a lot of men. We’re trying getting women up to speed, whatever it is, but poker neutralizes it. Let’s set it a game. Let’s play, and why did you play that way? What were you thinking about? How do you relate it back to that meeting we had that… And the, the mentor could ask the question or the mentee can ask the question in regards to w- how a hand got played. It takes you out and gives you a broader perspective on approach to a problem.

And then the final way that we’ve been doing it, of course, is with using it as a tool with customers. It’s a fascinating way to, uh, obviously, networking has always been a part of poker, but when you are teaching a customer something, and maybe you’re learning alongside them, maybe you’re not, the connection is so much deeper. So I think all of those ways that poker can be used as a tool in a different way than historically has been used.

Annie: Ah, love that answer. Love it, and very unique answer. I love it. You obviously know about the Alliance for Decision Education. What do you think the impact on society will be when the alliance succeeds in its mission to ensure decision education is part of every K through 12, uh, student’s learning experience?

Jenny: I think the stress and the weight that people place on sort of their actions and, and life can go down. I actually think it could be a way for society to breathe better for this generation of, we know they’re more highly anxious coming out of COVID, et cetera, all this da- these negative data points. When they’re given a toolbox on what to do in certain scenarios or any scenario really, ’cause isn’t everything a decision of some sort?

And I definitely think as being a, uh, I guess, still a student of decision-making, you know, every single day, my kids seeing it, I watch how they go through that process. And so as we get these generations of more skilled decision makers, like it makes it easier and easier for those interactions between parents and kids, and more detailed conversation about the why, hence more understanding between the parent and the child. I think there’s an enormous opportunity. Like when I first heard that it existed, um, it’s hard to believe it, that we don’t do it already.

Annie: Yeah, I mean, I think… I actually think about the Alliance and Poker Power in the same place. Like why haven’t we been teaching kids these skills? Like I… Why are we, we teaching them trigonometry? What’s going on with that? Like it seems like these are much more important core skills-

Jenny: Yeah

Annie: … that are actually gonna change lives in a way that these other things won’t. So I think in the exact same space in that sort of head scratching about why wasn’t someone doing this before? Um, and I feel the same way about what you’re doing. Where can people go if they wanna learn more about your journey, about Peak6, about Poker Power and what Poker Power is doing, maybe, uh, to be able to support Poker Power? Where would you send them?

Jenny: Yeah, I appreciate that. Thanks. For sure, you can find me, Jenny Just, at the, at obvious places on, on LinkedIn and Instagram and the like. Poker Power for sure. Because of all of our corporate work, a heavy LinkedIn and, and Instagram following. Find us online at our p- new Poker Power community, which is new and is taking off.

Annie: Awesome. Well, thank you so much for coming and having this conversation with me. You gave us so much time, which I really appreciate.

Jenny: Yeah. Well, my pleasure.

Annie: I love your journey. I admire you so much. I love what you’re doing with Poker Power. Um, I learned something new about your work in, in Africa with Poker Power now, which is so exciting.

Jenny: That, yeah, isn’t that cool?

Annie: Um, and just so happy to be able to have this conversation with you, and so grateful. Yay.

Jenny: Uh, good. I appreciate it. Thank you so much.

Annie: Thank you.

Published August 19, 2026