“Life, like poker, is a game of strategy and risk. Embracing discomfort and taking calculated risks are essential for growth and success in both.”
In this episode of the Financial Feminist, Tori welcomes Jenny Just — one of 23 self-made female billionaires in the USA and co-founder of PEAK6 Investments to explore the intricate parallels between playing poker and navigating life’s challenges, particularly for women. With Jenny’s expertise in finance and entrepreneurship, coupled with her passion for empowering women, this episode promises to inspire and equip listeners with practical strategies for overcoming fear and seizing opportunities in both life and business.
Getting started in trading and the birth of Poker Power
Jenny shares her journey into the world of trading, recounting her early days navigating the fast-paced environment of Chicago’s trading floors. She details the pivotal moments that shaped her career trajectory, culminating in the inception of Poker Power. Reflecting on her passion for poker, Jenny speaks about the inspiration behind Poker Power, emphasizing its role as a vehicle for financial education and empowerment. “I was in a bar, watching a couple of guys play poker, and I just thought to myself, ‘This is the most interesting game I’ve ever seen in my life. It wasn’t just about the cards; it was about the strategy, the psychology, and the dynamics between players. I was fascinated by how every decision had consequences, and I knew I wanted to learn more about it.'”
Poker Power: Closing the gender pay gap and building risk tolerance
When discussing the mission of Poker Power, Jenny illuminates its transformative potential in empowering women to navigate the male-dominated realms of finance and entrepreneurship. With a keen focus on closing the gender pay gap, she emphasizes the importance of cultivating risk tolerance among women, citing poker as a safe and empowering avenue for skill development. “By teaching women how to be more comfortable with risk in the game of poker, we’re ultimately teaching them how to be more comfortable with risk in life.” Jenny’s insights offer a nuanced perspective on risk aversion, highlighting Poker Power’s role in fostering confidence and strategic decision-making.
Encouraging women in finance and entrepreneurship
As the conversation unfolds, Jenny sheds light on her endeavors at Peak6, a leading financial services company, and its initiatives to empower women in the fintech sector. Through partnerships with universities and innovative outreach programs, she champions diversity and inclusion, paving the way for women to thrive in traditionally male-dominated industries. Jenny’s passion for equipping women with financial literacy and leadership skills shines through as she shares, “We’re creating a space where women can come together, learn, and ultimately, transform their relationship with money and success.”
The intersection of wealth and empowerment
Exploring the profound significance of money in personal and professional spheres, Jenny offers poignant insights into the link between financial literacy and empowerment. With a nod to her favorite saying, “Money isn’t everything but everything is money,” she explains how money permeates every facet of existence, from daily decision-making to long-term aspirations. “What I’ve learned is that money isn’t just about wealth accumulation or material possessions; it’s about agency, autonomy, and the ability to shape one’s destiny. “When I say ‘everything is money,’ I’m not just referring to dollars and cents; I’m talking about the power dynamics, opportunities, and constraints that money represents in our society.”
The Poker Power experience
Concluding the episode, Tori and Jenny provide a glimpse into the enriching experience of attending a Poker Power event. From interactive workshops to immersive gameplay sessions, participants are immersed in a supportive environment that encourages risk-taking and strategic thinking. With a blend of camaraderie and competition, Poker Power events offer a unique opportunity for individuals to hone their skills, conquer their fears, and embrace the journey towards success, “At Poker Power, we’re not just teaching women how to play poker; we’re empowering them to play the game of life with confidence and conviction.”
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Meet Jenny
Jenny Just is the little-known billionaire powering Fintech firms. One of 23 self-made female billionaires in the USA, she cut her teeth on the male dominated trading floor at O’Connor in Chicago. In 1997, Jenny started PEAK6, with $1.5 million in seed capital and created a phenomenally successful alternative to traditional option firms. Her fintech empire has grown into a multi billion-dollar financial services giant housing the next generation of products & service brands. Jenny’s true passion lies in finding opportunities for women to succeed at every table – from the classroom, to the boardroom, to the poker room and that is how in 2019, this passion led her to start Poker Power. A woman-led company, with a mission to teach one million women how to play poker, not for financial gain, but because she believes the skills required to play poker are also fundamental to career and life success; strategic thinking, risk taking and decision making, to name a few.
She founded the Women’s Trading Experience and Women’s Technology Experience programs in order to create a path for more women in fintech as currently only 14% of the 25,000 money managers worldwide are female. She also created Fintech In Action (FIA), a coalition of action-oriented corporations to accelerate progress, innovation, and opportunity in fintech and finance for Black students and professionals. FIA seeks to tangibly increase the pipeline of Black professionals for careers in fintech and finance and affect long-term change through equitable hiring, promotion, and talent retention.
Transcript:
Jenny Just:
This whole thing really was about confidence for me in young women. How do we get them confident at, now I will represent a poker table like a money table, any table you’re sitting at where you are doing business, they sat up straighter. They wanted to win. They were competing all in good faith, but they weren’t just giving away their chips because someone else lost their chips, right? It was a whole new body language. I start to learn and I’m like, wait a second, this looks like that meeting I was just in.
Tori Dunlap:
Hi, Financial Feminist. So excited you are back. Welcome to the show. If you are new here, welcome. My name is Tori. I am a money expert. I’m a multimillionaire. I fight the patriarchy by making you rich. I also have a New York Times bestselling book called Financial Feminist, and if you’re listening on Spotify, the audiobook’s right there for you. If you’re a premium user, it’s right there. It’s free, it’s great. And if you’re an oldie but a goodie, you knew that. Welcome back. Welcome back to the show. Couple housekeeping things. You can review the show if you like it. You can share it with a friend if you like it. And you can also follow us on social media. We are a@FinancialFeministPodcast on Instagram. We would love to see you there. You can also submit voicemails to us by looking at the show description and we can take your voicemails, we can take your questions and we can answer them live on the show.
Not live, but you know what I’m saying. Virtually live, but later, you got it. Would love to see you. You could also subscribe to make sure you don’t miss an episode. This show is expensive for us to produce, but free for you and you subscribing allows us to make sure we can continue doing the work that we’re doing and get incredible guests, so we appreciate the support. Okay, today’s episode, Jenny Just is the little known billionaire powering FinTech firms. She’s one of 23 self-made female billionaires in the United States, and she cut her teeth on the male dominated trading floor at O’Connor in Chicago. In 1996, Jenny started PEAK6 with $1.5 million in seed capital and created a phenomenally successful alternative to traditional investing firms. Jenny’s true passion lies in finding opportunities for women to succeed at any table from the classroom to the boardroom to the poker room, and that’s how in 2019, this passion led her to start Poker Power, which is a woman led company with a mission to teach 1 million women how to play poker.
Because she believes the skills required to play poker are also fundamental to career and life success, strategic thinking, risk-taking and decision-making. She founded the Women’s Trading Experience and Women’s Technology Experience programs in order to create a path for more women in FinTech because only 14% of the 25,000 money managers worldwide or female. She also created FinTech in Action, which is a coalition of action oriented corporations to accelerate progress in FinTech and finance for black students and professionals. In today’s episode, we talk about her background working in the very male dominated Chicago stock market, what brought her to Poker Power, why there is so much gender difference when it comes to risk taking and perfectionism, whether that’s in the poker table, in the workplace, how we manage our money and the power of building your resilience, and especially when that comes to taking risks. So we’re really excited for this episode. Without further ado, let’s go ahead and get into it. But first a word from our sponsors.
I hosted a Poker Power event three days ago in Manhattan, so yeah, it was so fun. It’s my second one. It was so great.
Jenny Just:
So fun. I know. Well, that’s the thing, it’s like worst case, you have a lot of fun, right?
Tori Dunlap:
Worst case. Yeah, no, it was great. And yeah, she owns a bourbon brand that’s her side hustle. She’s a lit Asian by day, bourbon connoisseur by night. And so yeah, it was a very, very fun event.
Jenny Just:
That’s awesome.
Tori Dunlap:
Yeah, first time I did it was at the Female Founders retreat in November, so yeah, got to see Erin both times, which was so fun.
Jenny Just:
I know. Yeah, she loves you by the way.
Tori Dunlap:
She’s fantastic. Yeah, we were just talking before, I don’t know if you heard, but she was on my flight that got delayed seven hours.
Jenny Just:
Exactly.
Tori Dunlap:
And she was right in front of me and I walked on and I was like, is that her? And then she got upgraded to first class and I was like, oh, it’s her. Because they’d come up and say your name and everything and I was like, ah, she got that upgrade. So I’m messaging her on Instagram and I go turn around and she just looks around and I’m waving like this.
Jenny Just:
That’s awesome. Oh my gosh.
Tori Dunlap:
Yeah, it was very fun. We’re just thrilled to have you on the show. Thank you for being here. We love bringing people on who have financial backgrounds and asking them what their first money memory was. What is the first time that you remember becoming aware of money?
Jenny Just:
Well, first of all, thanks so much for having me. I’m delighted to be here. And my first money memory, which is a little bit odd, and you’re too young, you might not remember, but when you used to get paper out of a printer, it was all connected. Yes, like an accordion. It didn’t come out piece by piece. And my dad came home from work, he was a doctor and there was always some lesson that came in the evening and I grew up with four brothers and this one I remember he handed me the stack of printout and he said, “Come over here.” And we were at the dinner table and I stood by him and I stood there and I must’ve been in middle school, and so I don’t know how tall I was then maybe I was, if I’m five eight now, maybe I was five, whatever and change.
And he said, “Hold it up and I’ll drop it.” So it all connected and it was the whole length of me and it was all single spaced names of patients who hadn’t paid. And I was like, “What?” The concept didn’t… I’d never heard of the concept. You go into a store, you pay for something, right? But there’s obviously for a young middle school student, especially without internet and all those things, how much do you understand about healthcare and why and how things happen? But it was a long list. And then there’s a column and a column. So then I was like, “Can you pay for the house? Can you pay our bills? How does this work if this pays this?”
And his famous phrase was, “Every day is a workday”, which I think is part of the reason why he’s 88 today and if he ever calls, he’s like, “You’re at work, right? Or you’re going to work?” Or there’s something about, I’m doing some… And if I’m having fun, he is like, “Yeah, but when are you working today?” So I think the visual of that for me was really impactful to risk, nothing is given and what can take away and how do you have to be conscious at any moment about what you think is next may not be. And then obviously around money as a young kid when your dad who you look up to, he has issues just like… As a child you think your parents don’t have those issues, you don’t quite understand that. So that was really eyeopening for me as a child.
Tori Dunlap:
Well, my work, we’re really focused on talking about what can you control about money versus what is the systemic factors? And that example is so deep, first of all, if you’re a child, but one is like yes, you pay your bill or that’s crazy that people can’t or unable or are not paying their bill. But on the flip side of that, it’s also wow, a healthcare system that costs this amount of money…
Jenny Just:
Right.
Tori Dunlap:
But also your father is a doctor. So yeah, are we getting paid? Are we not going to have money? And so that’s an onion, you just keep peeling back the layers on that one.
Jenny Just:
There’s so many ways you can go with it.
Tori Dunlap:
Right.
Jenny Just:
Obviously at the time I had the moment, but when I think back and I go, gosh, how much of that, and of course he didn’t know, affected my sequence of how I manage my money over the rest of my life.
Tori Dunlap:
Yeah. And for me, my dad was very similar in my financial journey where it was like, “What can I teach you? What can I give you to learn?” And so yeah, he was very instrumental and I think very similar as like, “What are you doing?” I’m like, “I’m working.” He’s like, “Yeah, of course. Of course you are.” And I’m like, “Yeah, we’re out here working. Capitalism’s popping off. We’re out here working. That’s what’s happening.”
Jenny Just:
That’s right.
Tori Dunlap:
You are still based in Chicago and I want to talk to you about your days on the Chicago trading floor. Tell me how you got your start there. What was that like, especially as a woman?
Jenny Just:
Yes. So first of all, I still talk about it as one of my most favorite years of working. I’ve worked a lot of years, still one of my most favorite. For those who are under a certain age, they wouldn’t necessarily know what those trading floors were like, but if you watch Trading Places, it seems like it’s a movie version, but that’s real. It’s really how it was. It was crazy down there. It’s like a sporting event, huge room, thousands of large men and very few women. But I ended up there really by accident. I wanted to work in Chicago out of school, and so I just interviewed at any job and they were literally all across the board.
I went to business school undergrad at Michigan and go blue, when I interviewed at this company called O’Connor and Associates, who was quite infamous for options trading, which I did not know that at the time, I came to the interview and it was the first time there was casual attire in the workplace and they were one of the groups ahead. I was interviewing at a bank and at an advertising firm and whatever, everybody was still dressed and I was like, I love this. I don’t have to get dressed up. And they had Haagen-Dazs and beer in their fridge and I was like, I’m a college student. This is the place to go. And by the way, I had no idea I was going to the trading floor.
Tori Dunlap:
Wow.
Jenny Just:
So I interviewed in the office. I’m sure they either thought I knew or understood or told me, but I didn’t get it. So I did not actually know I was going down there. And the funniest thing is that first day, you put your jacket on and your badge, and I was taken down there and Drexel Burnham had declared bankruptcy that day, which is an extraordinary part of financial history, just that whole story. And of course the market is going crazy and there’s steps on the side so the pit’s in the middle, steps on the side where the booths are that belong to each company, and they stuck me on the steps down at the end of the booths and they left me there all day, never came back for me. And I didn’t know, I was like, aren’t they going to need me? Of course, they didn’t need me at all. I didn’t go for lunch, I wouldn’t even know where to go.
And women’s bathrooms, God only knows where they are, they’re nowhere close. So I was like, I can’t leave because what if they come to get me and I’m at the bathroom? Anyway, so I was left there all day. But yeah, that’s how I ended up there. But to tell you the truth, the interesting thing about money is that it’s interesting. All of these companies, all of these stories, they’re all people stories and we burden ourselves with the math of money or the budgeting of money, and there’s so many positives around money that are interwoven in our lives every single day. And so I think the beauty of you actually got the physical energy of money down there. So I think for someone who didn’t know she was interested in the markets, it was a great way to be exposed and unfortunate that a lot of people can’t get exposed in that way today.
Tori Dunlap:
Yeah.
Jenny Just:
Because I think obviously there’d be a lot more women down there if there was something to do down there, but most of them are closed, and so we have to find other ways. But yeah, I think I was super lucky to be down there.
Tori Dunlap:
I will say, and you can speak more to this, the first day and you describing that first day feels like the metaphor for women in finance in general or women in FinTech, which is just like, we’re maybe going to let you in the door and then once you get here, we are not going to tell you how anything works and we’re basically just going to abandon you and you’re going to have to figure it out for yourself.
Jenny Just:
And nobody’s ever said that before, but I think that’s dead on. The good thing is we’re strong enough and capable enough to do it. The problem is the expectations should be a little bit higher. Unfortunately, they fall short.
Tori Dunlap:
I realize it’s one day, but wow, what a day to go from what you’ve built now so you were saying “Money is interesting and I grew to understand not only its importance, but the power of it.” So how did you get from ‘Day one, total deer in the headlights, I don’t know where the bathroom is’ to ‘Fucking self-made billionaire.’ How do we get from that day to now?
Jenny Just:
Well, it’s definitely a marathon, it’s not a sprint. That’s what I would say.
Tori Dunlap:
Sure.
Jenny Just:
I laugh a little bit because back to the household that I was raised in with my dad, every day is a workday, and my mom who’s raising basically five kids by herself, so every day is even a bigger workday, frankly, for her than probably him. And I kept my head down, what I didn’t know at the time, I was learning a skill, a valuable skill, options trading was the actual skill. But really the interesting thing about financial products, once you start to understand them a little bit more, they’re like puzzle pieces and you use different pieces of them at different times depending on what’s going on. So I think I was really lucky to learn what I learned, not really understanding. I think the other thing in retrospect that worked well, I didn’t know I was a risk-taker, but I would probably call this taking risks at the time, somebody would give me a job and I got offered a lot of jobs young, I think probably because I was one of few women so I was noticed.
Yes, I probably was above average, but I don’t think I was great at my early jobs. But I kept saying yes, mostly because I didn’t know I could say no. And so, okay, yes. So each one of these experiences I started to have, I talk about it as compound experience, like compound interest. It’s working for me because I take these risks early in my career and each one of those help me with the next risk and the next risk. And I’m taking, I’m failing. I’m succeeding early on as many as I can. So the compounding starts to happen earlier. So when I get an offer in my mid-20s to start this department at O’Connor, O’Connor was doing a joint venture with Swiss Bank, this over the counter equity derivative world, a whole nother product that I didn’t really even know existed basically off exchange floor.
I said yes, because was I going to say no? And then all of a sudden I’m building a business inside a business. And that gave me the confidence later in my later 20s when the bank was moving to the East Coast and my plan was Chicago. We heard that in the beginning, it was all about Chicago for me, that I just did this, so I’ll just do it again, naively. There’s so many naive thoughts around that but that was okay. It was my version of what I thought I could do. And my co-founder was interested in staying in Chicago too, and he had helped do the same thing inside the bank with us. So I think it was one foot in front of the other process. It wasn’t any massive vision that got me there, but I was okay not succeeding. I think success for me was trying.
I might’ve failed, our plan A by the way has never happened. It’s 26 years later, and really plan B is what allowed us to make our early money, which allowed us to do a whole bunch of other things, but that early taking risks, I always talk about taking risks, not more risk. It doesn’t have to be huge risk, but every single day I wake up and I do something I didn’t do the previous day or I do a little bit different or I try a new strategy with a different person. It gets my foot going forward each time and then I’m going to get pushed backwards several times. But I think all of those small risks I took in my 20s for sure, allowed me then to take some bigger risks along the way. And then of course I got comfortable doing it, all that practice just builds on itself.
Tori Dunlap:
Right.
Jenny Just:
So I think that’s how we have a nice long journey, that was not easy. Lots of ups and downs. I always talk about a money journey. It’s not supposed to be smooth and up and to the right. So if we don’t take those risks earlier, it’s more painful to do it later. It’s like any relationship in your life, is it going to be perfect? No. And your relationship with your money, it shouldn’t be perfect either. Otherwise, it’s going to be limited.
Tori Dunlap:
Yeah. Let’s talk about risk more because I’ve thought about this so much with talking with women and in my own life, I remember seeing the Girls Who Code, her incredible TED Talk where she talks about we teach boys to take calculated risks. We teach girls to be perfect, right? And it’s like I think that this is ingrained in us at a very young age as women, but specifically then too, when we talk about women investing, we hear the word ‘risk averse’, and I love Sallie Krawcheck, she says ‘risk aware’, not ‘risk averse’, which I think is such a good reframe, but I think that that is such a thing that we’re so hesitant to do as women. And let’s talk about Poker Power specifically, so you’ve built this incredible company that teaches women life and career skills through the game of poker. And let’s talk first about what poker can teach us about risk or how we can be more comfortable with calculated risks in our life.
Jenny Just:
I appreciate you asking about Poker Power. I’ll back up for one second, I am a quiet person my whole career and for many reasons, one of them, because I have four kids as well and a lot to do, but I also didn’t think I go, I actually have something, options are hard to understand, backend technology, hard to understand, how am I relatable? But I always said if I had something, I would go out there and do this. The thing that by the way is a risk for me, being public is a risk for me.
Tori Dunlap:
Jenny, can I pause you for a second? I would love to define options trading for our audience because if you’ve never heard of it, what is it?
Jenny Just:
Yes, of course. So options trading, options are a financial instrument. They are derivative of an asset, so you can think about options on stocks, options on fixed income products. You can think about options on currency. So there’s lots of these products. The ones in particular that I do are options on stocks. And so instead of buying a stock or selling a stock, you can use options instead. But the difference is I spend less money upfront. Let’s say I want to buy a call option on a stock. I will spend less money upfront to do that. Because I have the right to do it in the future, not the obligation.
Or let’s say I want to sell a stock in the future. I have the right to sell a stock in the future. So the one is a call option, the other is a quit option, both for sure are more advanced financial instruments, but they give you a chance to have a little bit more leverage. You get to hold on to the total dollar amount of your stock and just spend a small amount of money today. You can also sell options. That’s a different risk profile that I wouldn’t recommend necessarily for beginners unless you are doing overwrites, which something we won’t go into detail today. But like a lot that happens in the FinTech world, there’s a lot of language that gets used that seems complicated.
Tori Dunlap:
The jargon.
Jenny Just:
Exactly. And so I would say that this is not too complicated of a product, especially at its most basic level to use for those who are comfortable buying and selling stocks already to learn about.
Tori Dunlap:
Yeah, totally. I didn’t mean to interrupt you. I just want to get a definition because I know people are going to hear options trading and be like, “What exactly does that mean?” So yeah, we were talking about risk. So talk to me about calculated risk. How do we learn to be more comfortable with risk? And maybe if you want to take it through the lens of what you’re doing at Poker Power.
Jenny Just:
Absolutely. So when I started Poker Power, it wasn’t because I was interested in poker per se. In fact, I was the opposite, I’m like the 93% of the women on the planet who don’t play poker and don’t give a shit about poker. And in fact, there’s so many poker players that I’m around, there’s a lot of traders play poker that I was like, you are wasting time. You should be doing work instead. So I was against it. I learned about it accidentally and it was because of my daughter. She was 14 at the time playing a tennis match. This is not what you’re expecting to hear here. And her dad was super frustrated because she was losing. And he comes home, and he tells me because he doesn’t want to tell her how frustrating he is and she may as well be hitting against a wall.
She may as well be hitting with her teacher. She doesn’t realize that she’s playing against someone who’s strategizing, not just based on what they brought to the game, but what’s going on in the game and she’s just missing it. She’s not thinking, she needs to learn to play poker. And then I was like, forget it, whatever. And I literally walked away because I didn’t care about poker. And two weeks later I was like, should we teach our 14-year-old daughter to play poker? And it bothered me because I would never ask… I have three sons, I would never ask that about them and now I’m asking it about my daughter, like it’s strange or something. I was like, what planet are we on? It’s 2020, it was 2019 at the time. Anyway, fast-forward I was like, I want to do an experiment.
I go to her friends’ moms and I’m like, “Can I borrow your daughter? Let’s just see what this thing is all about.” And next thing you know, the moms are like, “Can we play too?” So it’s 10 girls, 10 moms, and literally the skies opened. I always say that we wouldn’t be sitting here today. I wouldn’t know, you, you wouldn’t have gone to these cool events with us. And if that specific thing happened, which was the girls and how they changed from lesson one to lesson four. So we did four one hour lessons and it was shocking the amount of confidence that was built. And so this whole thing really was about confidence for me in young women, how do we get them confident at what now I will represent poker table like a money table. Any table you’re sitting at where you are doing business, and they sat up straighter, they wanted to win, they were competing all in good faith, but they weren’t just giving away their chips because someone else lost their chips.
It was a whole new body language. I start to learn and I’m like, wait a second, this looks like that meeting I was just in. So now it doesn’t happen because you just learn the game, right? There’s, again, a lot of jargon. There’s a lot of rules, a lot happening at a poker table. But after I got into those multiple lessons and started playing more, I was like, I started actually personally using it as a framework for what cards I would say to my partners, I would say to my co-founder, “We’re doing a deal. What cards do you think they have? Where are they sitting at the table? How big is their chip stack?” And I started using it and I was like, this isn’t just about confidence for these young girls. This could actually work, creating a framework for grown women, for anybody, male, female, it doesn’t matter who I’m talking about around strategy.
So what are you doing, why are you doing it and who are you doing it with? All of those things come into play in business. So all of a sudden I had these young girls building confidence, and now especially women, because women don’t play this game, I realized that men are getting practice doing this when they’re 12 and 14. And then again when they get to college and they play hand after hand after hand. So they’re testing out how to negotiate, they’re testing how to take more or less risk. They’re testing out like, wait, what do I actually know? What can I infer? Oh wait, more cards came out, information’s changed. Now what’s happening at the table as a result of new information? And now I can start to see when I have to make real life big decisions. Of course, men will always tell us that you have to play poker for money. It’s like you do not have to play poker for money to get the benefits of poker. You can eventually pay for money if you want, but you will start to see that strategy didn’t work.
It worked before, with a new person it didn’t work so well. Why is that? How come? What did they do differently? Poker is like chess. It’s a mind sport, it’s a game. It’s a proven game of skill, but you’re still given two cards at the beginning, which are luck. That is the little nuance there. So what do you do? I always love this example. If you’re in a meeting and you get bad cards, what you expected to happen is not happening. If you never play your cards, you’re automatically losing because in the game there are antes and the money will be taken away. It doesn’t matter what my cards are, I have to figure out how to play anyway. And if I want to be asked back to that next meeting, I have to take risk with not such good cards. And by the way, if I practice doing that before I’m actually in that scenario. Amen. I’ve seen it before. Of course I’m going to be more comfortable, practice helps everybody in anything they do.
This is one place women never practice, in their hobbies, in their play as they’re growing up. So now all of a sudden I get to practice taking risk and get smarter and recognize all those physical feelings that happen from doing it. And then the beauty of tech, now I can practice on an app and I was never a big app game player. I’m like, I’m shocked how much I know about somebody, Evelyn G, because the way she plays me, God dammit, I’m going to beat her. But Poker Power has created a community, a safe place to go and play and to practice. And so we can get those reps under our belt on taking risk. I am not a big believer, and maybe I grew up with four brothers, I’ve worked with men most of my life that there’s really any difference. I think there’s some, for sure, there’s some human things that make us different in taking risk.
I think that majority though of the biggest differences come from there’s a whole decade of risk taking they’re taking before we even really start to, and then at that point, we have so much at risk. We have our first apartment, we have our first house, we have kids, we have… And now it’s like, shit, that’s not a good time. The good time is to do it young, which is why the beauty of Poker Power, we’ve taught it over 250, either companies or organizations, which is really crazy. Because this really was about starting girls young, but if we can teach these 20, 30, 40 year olds, 50 year olds, they can teach their daughters so they’re not in the same situation, that we can change a generation of women practicing taking risk much sooner in their lives.
Tori Dunlap:
I will say one of the most badass things I’ve ever experienced was sitting down at that table, it’s almost going to make me cry, truly. It’s like, I am such a brand ambassador for what you all are doing because it taught so many things in just this very… I am extremely confident and I’ve had a lot of pretty fucking badass moments in my life and I will say one of them is just stacking chips and just feeling like a baller. And I’m like, I do not smoke cigars, but I need a cigar in my hand. And I am literally man spreading at the table and I’m like, this feels so powerful because just like you were saying, I think that there’s so many things you can learn from it. And one of the first things when I sat down at the table at this event where one of your incredible poker players was teaching us is it’s like you’re not playing the cards, you’re playing somebody else.
You’re playing the people at the table. And so even that is okay, me as an entrepreneur, every single time I walk into a meeting, you’re exactly right. Yes, I’m playing what the situation is, what the cards are, but I’m really trying to figure out what do you want? What do you value? What are you trying to get out of this? And in a negotiation, even if you’re not a business owner, if you negotiate your salary, of course you want more money, that’s why you’re negotiating. But the question is like, okay, what does my boss value? Because if I can give them what they value, then I can show up as the best version of myself to get a raise, to get more money. I have to figure out the other person across from me. And then to your point about calculated risk, there’s times where, okay, even if I feel a little bit unsure, I need to put more of my money, my energy, my time into something to see if this pays off.
And it might not, but you learn something from it. And then to your point before of like, okay, you have to participate because if you don’t participate, you lose money. You’re left behind. This is also directly related to how women manage finances. If you do not opt in, you’ve opted out, no doubt. But surely if you have not come in and said, “I am an active participant in my own life and my own money”, it doesn’t matter. So yeah, there were so many things. And then when do you bet high? When do you not bet at all? When do you just say, “You know what? Actually these cards are shit and the smart decision is to just say ‘Fold’ and to just give the cards back.” I just loved it and I hope everybody has the opportunity to go to a Poker Power event, but just it was such a good encapsulation of I think every single aspect of being a woman generally, but specifically trying to get your financial together as a woman and also navigating the world as an entrepreneur. It was just so helpful.
Jenny Just:
It’s so helpful. And we were talking earlier, worst case, you have fun, right? And the other surprise that we found since we started was the networking, right? This is what men use for networking and all of a sudden…
Tori Dunlap:
Golf, it’s like golf, but golf’s not as fun.
Jenny Just:
Right. And we take all different women, all different age levels, all starting at the same place, learning together. And whether you’re doing it… Some of our law firms have been unbelievable, but the law firms, they’ll take their clients and they’ll learn with their clients together. You are building relationships at the table even though you’re competing. The coolest thing for the women too at a poker table is even though everybody wants to, and we are playing to win, we are teaching them to win, everybody’s so happy for everybody at the table.
Tori Dunlap:
Truly.
Jenny Just:
You’re making new friends and that network can spread more. And we’re always looking for something, right? Yes, I love a good wine night or a book club, but here in 2024, we can do a two-for-one. We can learn skill and network and have fun, like bonus.
Tori Dunlap:
Yep. Yep. And I remember, so the event I went to, it was my second one a couple nights ago in the city, and it was literally, there was a woman across from me. And granted, I’ve done this before. It was my second event, so I knew a little bit more, but the woman across from me, we were the only two still in the round, and I could tell she was hesitant with her cards and she’s learning so she was like, “I don’t think I have good cards.” And so then for me, I was like, “Well, I don’t have good cards either, but I am just going to bet her until she’s not confident anymore.”
And so then that’s what happened is she folded and I got the pot and I looked at her and I said, “What’s your name?” And she told me her name because we hadn’t introduced ourselves yet. And I go, “My cards were shit.” And I showed her my cards and I was like, “And obviously you wouldn’t have said in a real game, ‘I don’t think my cards are very good’, but I could tell you were not confident. And so I bet up to the point where I knew you weren’t going to be comfortable matching my bet so that I got the pot.” And she was like, “Oh.” And so it was like this moment of so much learning, it was so cool.
Jenny Just:
And how each individual takes those moments back for their work. So I love the differentiation, we have a nutritionist in her version of it and then an HR executive and her version of it. And then obviously someone who’s in FinTech, their version of it, everybody thinks about it differently and relates to that situation slightly differently, but we’re all benefiting. And then when we all speak about it, even better. Negotiation is of course the big one that comes up, negotiating salaries. Negotiating divorces frankly comes up a lot too. But it’s an opportunity for us all to go, “Yep. I’m in that situation and that reminds me of…” And then I can share it and what did I do and what happened as a result and how I could do it differently the next time. How I’m going to think about it differently, again, so back to that idea of compound experience.
If I can’t get those experiences every year I’m doing a different job or whatever it might be inside a company, whatever allows you to have those experiences. I can play hands and I can get experience through hands. I can get experience playing hands of poker, and that’s what I want women to know. There are other ways that you can help yourself today that are different, unusual, and really beneficial to your… There’s a lot of analogies people have from poker to life, but for us specifically, we want to talk about poker to money and your job and how do I do that? Get my reps in, get my reps in playing. And whether it’s online or in person, the in-person part is just so fun. Yeah, we do that all the time if we could, but in the meantime, I can do it in my PJs on the couch.
Tori Dunlap:
Right. You were saying before about poker also teaches women to win. And I just want to talk about that because I fucking love it every time I get to win at anything, but especially anytime I get to do this and just grab chips and bring it towards me, it’s very fun and powerful. But I think that a lot of women, through no fault of our own, again, because we’re taught to be perfectionists and we’re taught to be so altruistic, and I mentioned this in my book that almost to a fault, this altruism of just put everybody else first before you put yourself first. Do we have a fear of success? Do we have a fear of winning? And how can poker help us not feel so fearful of winning?
Jenny Just:
Yeah, there’s a lot in that. I’ll start with the tactical and then maybe bottoms up and I’ll go top down. Every time we don’t negotiate, whether it’s a job, it’s your mortgage, it’s the price of the house, not just the mortgage. I remember being in a room, a very senior woman one time, and a woman who runs a bank, she said, “How many of you have ever negotiated your mortgage?” Three people raised their hand and there were 30 some in there. If we’re not negotiating these things, all of those dollars back to compounding, the male is compounding more dollars than you are compounding. We are never catching up. This is why they talk about such long periods of time for equal pay to happen, equal pay or equality around money to happen for men and women. It’s not an option to not negotiate those things for us to catch up because every dollar that isn’t in there today doesn’t compound tomorrow. So that’s bottoms up. So really the question, is is fear of success really fear of failure? What do you think?
Tori Dunlap:
Again, if we’re teaching girls to be perfect, and that is what we’re striving for, while also very realistically understanding that perfection is completely unobtainable. That should be a release of, you know what? I’m going to do the best that I can, but understand that this is never going to be perfect, and that’s just going to be the way it is. But I think rather it’s this crippling debilitating thing, which is if I can’t do it perfect, I’m not going to do it at all. And I am sure you’ve seen this, literally I’ve talked with thousands of women at this point, and it’s the same thing with investing. I need to be an investing expert before I open an account. I need to know exactly that this account is the most perfect account I can open, Roth IRA versus traditional IRA, and then once I actually open one, okay, well, I have to find the perfect investment and I’m going to spend hours and hours and hours researching.
But then of course that never happens because you encounter sexism or you encounter jargon and you just end up bailing because you’re like, if I can’t do this perfect and know that it’s 100% the right decision, I’m not going to do it. And so I think that when we’re told that this is the thing we should aspire towards is perfection, it impacts our money, it impacts our relationships, it impacts our careers. Rather than understanding my number one rule as an entrepreneur is done is better than perfect. Yes, we work to improve it along the way, but sometimes you’ve just got to get things started or things done. So it is interesting that you’ve even framed it as is a fear of success a fear of failure? Because even in trying, I think that is succeeding even if the outcome isn’t what we want.
It’s the same thing with negotiating. I tell people, “A successful negotiation is not you’ve got what you wanted because there’s other factors. You could go in being the most hard worker, best prepared bunch of data saying you’re underpaid. And still your boss could say, ‘Well, why aren’t you just grateful?’ Like that successful negotiation is, did I try, did I prep? Did I do everything I possibly could within my control to make the outcome something positive for me?” I know I just said six things there, but I think that yeah, maybe the fear of success is what if I don’t succeed? What if I don’t succeed and what if I fail?
Jenny Just:
Right. And I think if we don’t reframe. So the interesting thing about, and especially those who identify as male when it comes to money, is that not only is it they don’t expect perfection, they do expect to lose. And I had an interesting story recently, and it was a gentleman who didn’t know what I did, and he was talking at his firm, which is a large financial firm. And a woman who came and asked, which was great, to be partnered, and then she went through all of the things that she was perfect at. So she clearly has had a fairly long-ish career, and the only thing he wanted to hear was about her fails. She didn’t have any because she thought she had to be perfect along the way. Because not only is it a learning opportunity, and not only… People want to see how you get back up, people want to see and know that you can get back up. So it actually isn’t helpful to be perfect in many cases.
Tori Dunlap:
Well, and without opening a whole other can of worms too, I think we are living in a society that demands perfectionist women, and we need to talk about this another time, but one of the things that absolutely drives me bonkers about any sort of woman who has a chief success in entrepreneurship is that we’re just waiting for her to fail. And when she does, typically her company is devastated because of it. And we’re out here with Adam Newman getting a bunch of money every single he wants to start a new company. So that’s a whole other side of it but we are, I think, again, conditioned to achieve perfection, both because we feel the internal need, but also the external pressure of like, you must be perfect or else you could lose your career. You could lose your job, you could lose your business.
Jenny Just:
No question. And for sure, if someone were to look at who I was when I first started in the business, I would definitely fit that mold. I would’ve expected, again, I had to say yes. Well, how could I say no? In order to do what I believe they thought was being perfect was me saying yes. But the interesting thing about my career, and the only reason I know this, the beauty of being in trading as a young person is you never win 100% of the time.
Tori Dunlap:
Right, right.
Jenny Just:
We have a super high fail rate. So if you looked at our trades, it’s 46% of the time we fail. That’s a really high fail rate. So only way I got comfortable with it was doing a lot of it. Now, it doesn’t mean you have to lose a lot of money along the way. Again, the earlier you take risks, the better. The more you learn, the more they compound. But if you take no risk and then expect to take risk, it’s much harder. So you just set yourself up for a more difficult journey. So how awkward does it feel to, I don’t know, you’re in another country and someone says, “Oh, it’s all about negotiation” and you’ve never negotiated anything and want to negotiate the price of something like, oh God, it just…
Tori Dunlap:
It’s uncomfortable and you have to get comfortable being uncomfortable.
Jenny Just:
You have to be comfortable being uncomfortable. So if you start to do that sooner, it’s a new year. If this is not something we’re comfortable with playing poker, oh my God, the first time I was at a real poker table, oh my God, and this is…
Tori Dunlap:
Dry heaving.
Jenny Just:
This is COVID. This is in ’21, this isn’t that long ago. Think about all the things. Well, you don’t know my whole history, but I’m not young and I sat at the table, I thought my heart was going to come out of my chest. What have we done that we created this thing around poker in our society? It’s crazy, but it exists. It’s real. I understand it. But if I didn’t do it, first of all, what am I representing? But second of all, I still have to go. All those feelings that society has put in us, they’re there.
They’re not going away. The only way they’re getting better is if we go through them. People ask me about risk. I always think, well, I don’t have an option to not take risk, so I may as well go through it and suffer the ups and downs of it sooner. So more risks with an S rather than bigger risk. Each one of these small ones, it helps all that physical stuff that happens when you take risk too, the more you do it. It’s funny because on the Poker Power play app, when you play, even though the women don’t know the women, because you can have a different name or whatever it is. And yes, you can use video and you can play and have this cute community that’s up on the screen, but assume you’re playing and your name’s up there and it’s 10:00 PM at night. Even though the women might have learned with us getting on the app, that’s just a risk in and of itself.
It’s one of the reasons we call our first lesson ‘Courage’. Just playing this game, doing these things that are uncomfortable. There is something really peculiar about the game of poker, but also makes all of those other risks you’re going to take seem a little bit smaller. If I can do that thing, all these other ones I can start to do, and by the way, I fold a lot of hands and I don’t have perfect cards and oh, and I bluffed, oh wait, I have a bunch of different strategies for different situations. What is that like? What would I do? How would I think about it? And I’m sure maybe, I don’t know if you had any hands like this, but you’re in big on a hand and that last card comes on the table, you’re like, oh, and then you have to fold. You have to fold when you have all that money in.
Tori Dunlap:
I didn’t fold, Jenny. I should have, I did not. My eyes were bigger than my stomach. And yeah, I did not fold.
Jenny Just:
Right.
Tori Dunlap:
Right?
Jenny Just:
But you learned.
Tori Dunlap:
Right.
Jenny Just:
Yep. And you learned. You go, “Next time, do I fold or don’t I fold?” Right? Obviously in the one hand you didn’t fold and you got all the chips.
Tori Dunlap:
Yeah. Well, and not to harp on the point too much further, but this failure of success too, the flip side of it, I do think when we do taste success as women, I think it scares us because I think we’ve been taught to not trust ourselves, and we’ve been taught to not trust our own power and our own intuition. And so even again, at a table, I feel this, I can see this with other women. Even when they get good cards, they’re like, “Should I bet?” I remember the first time I went, the first time I experienced it, I remember our lovely person at the table was like, “No, you need to bet more chips than that. You have Aces, you have pocket Aces. You need to bet more chips than that.”
And so even that is that fear of success. I think on the flip side of it, let’s say we do succeed, I think that that’s also scary because it means that we have to intend to go all in on ourselves. It means that we have to trust ourselves enough to run a business or to lead a department or to run a household. And that’s scary on the flip side of it too.
Jenny Just:
That’s right. What we teach at Poker Power, right, that it is a game of being aggressive. And if you don’t, you will lose all your chips.
Tori Dunlap:
Right. And ‘aggressive’ is not a bad word. That was one of the lessons too, is that like…
Jenny Just:
And ‘aggressive’ not a bad word. Yeah, ‘aggressive’ is not a bad word. It is a representation of your confidence in your hand, whether you actually have the cards or not nobody knows, just so you know. But if you represent something weak, now, by the way, that might be a strategy, but the initial inclination on majority of women when we sit at the table is like just going to match that bet. I’m just going to put the minimum amount I possibly can in. Well, guess what happens when you do that? The entire dynamic at the table changes. They now understand something about you. What did you just represent? So when you think about being in a meeting, when you think about going and raising money as an entrepreneur, if you’re, what they call in poker, limping in, what did you represent about yourself? Versus if I came out and I did three times a big blind or I made a larger bet, you have to think about what the other person is thinking.
And I think we miss that. It’s all about, because I don’t want to screw up because I have to be perfect. Back to your original point, there’s all kinds of logic why this is happening the way it’s happening, which is why we have to make a conscious decision, not a subconscious decision to do something differently. And so when you meet our Poker Power teachers, they’re there for you to say, “Nope, we’re doing this.” And you’re like… But you’re all there together in a safe place and safe environment, understanding. By the way, guess how men learn? When they’re 10 or 12 or young boys learn or whatever it is. They learn by betting a little bit and a little bit, but pretty soon they learn by betting a little bit, it doesn’t work, which is why they then become more aggressive at the poker table, just like life.
They learned it. So we just have to learn it. It’s not that we can’t do it, we just have never been given the opportunity. There’s no place that we are learning this, we’re not learning it in school. We’re not learning it with our play, with our friends. We have to learn. We can say these top down words about not being perfect, but now we can actually practice it. We have to practice not being perfect. I don’t have the perfect cards. What am I doing in that circumstance and what do I do, especially if I actually want to win the game?
Tori Dunlap:
My last question for you, you have said that money isn’t everything, but everything is money. Talk to me about that.
Jenny Just:
Sounds good when you say it and there’s a long pause. So one of the things that I learned, certainly being here and trying for a very long time to get more women in a position of what I always say, capital allocation, allocating money, making decisions around money. That was for my own as a firm’s benefit, having diversification of people who are making decisions around money. But what I learned as I expanded into other businesses is that it’s not just about what I was thinking about for a trading business. It’s about every business. So if you are not connected to the money in some way, you are not going to be in a position of leadership or power where you are, unless of course you’re doing it yourself. Which then of course, then if you’re doing it yourself, you’re connected to money directly. I don’t care what your job is, but if you’re not thinking about how you are either making money or saving money, and what directly you are doing every day is doing that, you are ultimately not going to be pulled up into those leadership ranks and where you want to be.
I always say that where you want to be and where you are, what’s in between that is money. Now, so does that mean you have to be an expert in money and an expert in math? No, absolutely not. You are a totally capable human being who is running your life and running your home, and you have all the skills you need. I’m 100% certain. You just now have to be brave enough to say, “I can represent the money side of this. I understand it.” So everything you are doing, frankly, this is to personal life and to business. You wake up, it is somehow about money. What am I doing that day? How am I making my choices, how am I going about things? There’s a money side to that equation every single time. Now, nobody wants their… Well, some people do, but we don’t necessarily want our life to be about money.
It’s just a byproduct of living. And if we want our money to work for us, we have to be cognizant that it is surrounding us at all times and that we have to consciously make a decision whether we want to control it or have it control us. And my choice would be control, which then means you need strategy. You need to understand taking risk around it, and then you need to be able to execute. And that all comes from practice doing it and being really aware around it and not avoiding it. I always say, you have to be in a minimum conversation about money, which is the basics to live. But every step you can take to be integrated, especially at your place of work, around how you connect to the money will benefit you in all aspects of your life.
Tori Dunlap:
Jenny, thank you for your time. I could talk to you for about 62,000 more hours, but where can people find out more about you? We didn’t get to touch about your business. We’ll have you back on to talk about all of that. But tell me more about Poker Power. Tell me more about where we can find you.
Jenny Just:
Yeah, absolutely. So PokerPower.com, we’d love to see you there. You can come learn with us as an individual, as a company, as an organization, as a group. Poker Power Play is our app where you can go on and start to learn on your own and practice every day. And PEAK6.com of course, is our family company that we have lots of different ways we’re touching your viewers who are using FinTech tools every single day, including yours. We got to come back and talk about yours at one point too.
Tori Dunlap:
I would love that. Thank you. Thanks for your work.
Jenny Just:
Of course.
Tori Dunlap:
Thank you to Jenny for joining us for this episode. You can go to JennyJust.com to learn more about her or look up Poker Power. You can literally download the Poker Power app and get started playing. We love and appreciate highlighting women doing really, really cool work in these spaces. So hopefully you love this episode. Feel free to share it with a friend. As always, Financial Feminist, thanks for being here and we’ll talk to you soon.
Thank you for listening to Financial Feminist, a Her First 100K podcast. Financial Feminist is hosted by me, Tori Dunlap, produced by Kristen Fields, Associate Producer, Tamisha Grant, researched by Ariel Johnson, audio and video engineering by Alyssa Midcalf. Marketing and operations by Karina Patel, Amanda Leffew, Elizabeth McCumber, Masha Bakhmetyeva, Taylor Chou, Kailyn Sprinkle, Sasha Bonar, Claire Kurronen, Daryl Ann Ingman and Jenell Riesner. Promotional graphics by Mary Stratton, photography by Sarah Wolf, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K team and community for supporting the show. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit FinancialFeministPodcast.com.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over one million women negotiate salary, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of almost 250,000 on Instagram and more than 1.6 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
