ABC to CEO Interviews Jenny Just
Transcript of our conversation with Jenny Just
Sharon Fiehler
Welcome to the ABC to CEO Preparing for the Possibility Podcast. I'm Sharon Fiehler and today I am honored to be joined by Jenny Just, co-founder of PEAK6 and co-founder of Poker Power. I know you’re going to enjoy this conversation. Jenny is a visionary powerhouse and one of the few self-made female billionaires in the United States.
From the days of cutting her teeth on the trading floor in Chicago to now running a fintech empire, she has started and/or turned around more than 15 companies. We are so excited to have her on our show today to discuss her career as well as her mission to help prepare the next generation of female leaders, a goal we both have in common. Jenny, welcome to the show. Could you start by telling us some initial decision she made early in your career that helped you in the long run?
Jenny Just
First of all, thank you for having me here today. I'm thrilled to be part of the podcast – very fortunate because we have similar missions and goals which is to help future women achieve the goals they want to achieve.
I think when I look back, honestly, we talk about shooting the arrow and drawing the circle around. I didn't know, necessarily, at the time what was helping me. But when I look back, the one thing I was really good at was saying yes, meaning, if somebody asked me to try something new, try a different role or position, work in a different department, I didn't know to say no, so I would just say yes. Each one of those moments was a great opportunity to expand something we call compound experience. It's a little bit like compound interest. If I have a principle and have an interest and I get interest on my principal, if I then get my interest, I get interest on my interest. So, I have exponential growth. I was able to do that very early in my career. By saying yes early, I took risk early. Those experiences compounded on each other to allow me to do things probably earlier in my career than the average person. I had not only started a company inside the company I worked for but then started PEAK6 when I was in my late 20s. I had already done two companies at that point in my career. That early risk-taking was critical.
Sharon Fiehler
When I worked full time and had a staff, I would always tell my team that when you go into a meeting and a senior person asks you to do something, and you think, “Oh my gosh, I don't know if I can do that.” – don't say that. You say, “Let me look into that and see how I can make that happen.” I think it's kind of the same thing. People can do more than they realize, and never put your cards out, so to speak, until you really know what you have.
Jenny Just
It’s funny you say that. That exact example someone used yesterday. I know we're going to get to poker, but you are essentially bluffing, right? You don't have the perfect hand to show. But you don't have to show your hand, right? You can keep that to yourself. You can decide if you want to play it or not play it. It's up to you how you play that hand. Don't give away the hand before you’ve even thought about what the best outcome would be for you. I love that example.
Sharon Fiehler
Bringing up bluffing: In your own career, how was the bluffing part important? We always talk about it. That doesn't mean untruth. It just means you are keeping all the information to yourself. How would you explain it?
Jenny Just
I like to say it's not lying or cheating, that is not the point. It’s something I learned early. When I worked on the Chicago Board Options Exchange floor, we were buying and selling options on stocks all day long. Well, what's the real price? It's just what two people agree on. So when we're in a negotiation, whether it's about a salary, a deal, or a product. There's two of us who are going to decide. Maybe it's a larger group, but ultimately, there's no right price. It’s what we agree. I may think it should be higher. I may not have all the resources I need to make the price higher than I want it to be. Let's call it my salary for the moment. That doesn't mean I don't have a lot of solid assets or characteristics or whatever it might be that I'm bringing to the table. It's up to the other person to decide how they're going to judge that situation. Don't prejudge what you don't already know. They don't know your cards, so don't tell them the cards before they know. They might just by seeing you in that light. You don't know what their cards are either. They might see the outcome completely differently than you do, so give yourself the best opportunity. It's about the pause. It's about thinking. It's about strategizing. It's about thinking what the other person's thinking, not just thinking about your own cards.
Sharon Fiehler
Sometimes I hear people say, “Well, they just get lucky.” My definition of luck is being prepared for opportunities. Those more prepared for opportunities do seem to be luckier, but it's not a coincidence.
Jenny Just
I would totally agree with that, though, I think you might get some very good cards, you might get a pair of aces but that doesn't mean you necessarily win. You still must play with skill, because you don't know what other information is going to come out on the table. You don't know what other people are going to do. You have to have a) built up your skills, and then b) be prepared to take the risk when your ship comes in. How do you grab on with both hands and push at the right time?
Sharon Fiehler
You’ve obviously had a long list of successes in your life and in your career. I'm sure there have been some failures, but maybe some failures with some silver linings. Could you talk about some successes that you're particularly proud of and maybe some failures that had a silver lining in them?
Jenny Just
Yes, I'm happy to do that. We always say we have more collective failures than most people we know combined. The interesting thing about coming from the trading world is that you're used to trading all day and having lots of failures. It didn't feel as emotional or traumatic as maybe it often does. I'll say this last thing about failures, which is that your failures are part of your journey. Let's talk about relationships. There's no perfect relationship. It doesn't always go up. What you take home from your work at the end of the day, how you feel about it, that's not going to be perfect either. And then when you go to invest, that's not going to be perfect either. There must be ups and downs. You don't get on a plane without some bumps on your journey. If you expect your money to go one direction, you're likely not taking enough risk. And if you're expecting any of these journeys to be perfect, you're probably not completely understanding the journey you're about to approach, or you’re not fully present in it.
Successes: One I'm particularly proud of would be the one that most of your listeners would know about today. Actually, they wouldn't know about it, but they are likely using our technology. And that is the backend technology for the likes of SoFi, Ally, Webull, eToro, Public, Stash – almost 60% of the online retail broker-dealers today use our backend technology. That company is called Apex Fintech Solutions. In fact, Robin Hood, when they started Wealthfront and Betterment, two of the very early first robo advisors, used our technology. The reason I talk about that as a success for us is not because of where we are today, but because of where that started. That company was the very first company we bought and turned around.
It's a long story, but it's a clearing and custody firm, and we were using it ourselves for a company called OptionsHouse which we built and ran for almost nine years, then merged and sold and eventually ended up under Morgan Stanley E*TRADE. That firm was clearing its trades, and all its money sat at this firm Penson. Penson got into trouble. There was announced fraud, and the SEC came and asked us to buy it on a Monday by Friday. We were quite a young company, and it was quite a bit of risk. And of course, we initially said, “No, find somebody else,” but we ended up doing it 13 days later. We had to put quite a bit of capital into the business to make it run, and then, fortuitously, like you were talking earlier about the luck, we were working on the technology for ourselves at OptionsHouse and making new account opening technology. That's when the new generation of online broker-dealers came around: Robin Hood, Wealthfront, Betterment. There was no new account opening technology out there. We were the ones, and we started having customers. Though Penson had a bunch of customers, we had gotten rid of a bunch of customers and were just focusing on the technology for ourselves. The luck presented itself at a time when we had been preparing ourselves.
So today, also because we represent more than 25 million clients out there today, we're proud of the stability and wherewithal of that business. Robin Hood today does their own custody and clearing, but when you talk about scenarios like meme stocks back a little while ago, and what happened to Robin Hood but didn't happen to Apex and its clients, we're proud of the knowledge base and the collective understanding. It’s a very difficult industry because there are a lot of old pipes that exist and old regulations that exist. It's very complicated, and having been in the industry for such a long time, the trust and stability that our clients expect from us we can hold up even in those most extreme moments. That's a very proud moment for us.
Sharon Fiehler
I see where that's a proud moment. That's an amazing success story. Maybe we could talk a little bit more about poker and risk-taking. I love all the analogies between poker and life and careers. So why don’t you tell us a little bit more. Beth, chime in if you've got some other questions here too.
Jenny Just
I think you know, maybe one of the most interesting things about Poker Power is that I didn't play poker until almost four years ago. I didn't know the benefits, but once I started to play – my work, what I do every day, what I see in meetings, when I do a deal, when I have a conversation or negotiation – suddenly, I said, “This looks like my work.” I had no idea. The beginning of it was really for my daughter. That was about strategy, that was about decision making, that was about building confidence. These two worlds collided when I started to teach my daughter and her friends, and I saw this one little door open such a wide array of opportunities for practicing building confidence in these different areas: dealmaking, negotiation, setting a strategy, and approaching a problem.
I have four kids, three are boys and one is a girl. Not all boys are learning poker, but many of them are and even if they're not learning poker, they are learning other things in their hobbies and play. They might play ping pong, but they'll play ping pong for 50 cents or $1. They're playing games all the time where they're competing for something that's on the line. And in our hobbies, most of our young girls aren't doing that. Maybe the closest we might get to it is in sports. The boys are getting practice because every hand is an opportunity to see patterns, test strategies, see what happens when I fail. How does it feel? “Oh, wow, I can get back to the table. What do I have to do? And how would I do it differently?” Our young girls are not doing that. So when I started to learn, and I started to see how it’s applicable here, I thought to myself, “Gosh, if I had had these 10 years earlier, 20 years earlier, or whatever it might be, let's call it five years earlier, I would have saved myself five to 10 years of learning that I had to do.” Those compound experiences that I talked about in the beginning.
What I think is happening is that men are playing for fun. By the way, worst case, it's so much fun! But when you start to look around you and you see some of the Bill Gates of the world or our financial male leaders, poker is an important part of their lives and their growing up, and they would say that. There are more than 600 books written on poker, and not just about how to play. There are women, too, who have very distinctly talked about poker and life, but we haven't figured out how to cross that barrier. When women hear poker, and I was this person, they turn away. They have, first of all, no interest. Why would you? The stereotypes–why would you walk yourself into that?
There's a forcefield that exists around that whole concept of playing this game, which, it turns out, can be very beneficial to life. When I started to learn that, I thought, “Why don't we teach our younger girls first?” Then by the time they get to be 21, they're coming out of college, they have similar experiences, they have similar abilities to men. Then we know the male takes the risk for that next job with 60 percent confidence when she doesn't take it until she has 90-plus percent confidence. If we can get them there! That was my goal. But it's hard to get those young girls to believe they should play this game. It's one thing for me with my daughter when she was 14. Thankfully she was 14 because if she had been 16 or 17, I might not have been able to make her play. She got to play at a really young age. There are about 2,000 people at PEAK6. When we started wanting to teach, we said, “We want to teach your daughters and your nieces and your sisters. Bring them to us.” The women of PEAK6 said, “Well, if it's so good for them, why aren't we playing?” This was in the middle of COVID. Why not? One thing led to another, and Morningstar, a large international firm I'm sure you're familiar with, said, “Can we learn too?”
Today, we're in 40 countries. In over 150 companies, we've been teaching everybody from the Googles and AWSs to Northern Trusts and the large banks, the large law firms. It's amazing who we've touched and why. We teach these women, and hopefully, they can very quickly realize they need to teach their daughters and their nieces. If we can't get to them, at least they'll be able to get to them.
This very interesting thing has happened since I started talking about this out loud. Of course, I'm in the fintech industry, so I speak to many fintech players. The number of senior women, and I wasn't one of them, obviously, who played poker growing up, usually because of their grandmother, is around 65 percent. I'm talking the most senior. You know that we know there are not that many of them out there, but a crazy number of them learned to play poker growing up from their grandmothers. That has been the consistent story. I met a lawyer just last week who is at the top of her game she learned to play from her grandma. She says my training at Goldman Sachs and my poker are the two things that I point to as the reasons for my success.
Sharon Fiehler
I just love hearing that. It makes me sad to think of those generations before us of women who didn't get the chances that we're getting. Hopefully, the next generation will get more. What a loss to our whole society.
Jenny Just
Exactly. Nobody knows the real number, of course, because there's so much poker that goes on that we don't can't count, but about 120 million people in the world play poker. Less than seven or eight percent are women. What if half of the poker players in the world were women? How would the world be different?
Beth Chesterton
It reminds me of what we talk about at ABC to CEO. We talk a lot about the behaviors that we want to see in young women, such as raising their hand for stretch assignments or promotions before they're ready, which you sort of referred to as taking a seat at the table, contributing when you have something to say, not waiting to be asked to contribute, to jump in and make a contribution because so much talent is sitting on the sidelines. It sounds like what you're saying is if they knew how to play poker, it would build that muscle. You're going to lose, you're going to win when you have a losing hand, you're going to lose when you have a winning hand, but you're going to keep coming back to the table, and it gives you permission to practice skills and behaviors that help.
Jenny Just
Two things I want to say about that muscle. We talk about this as exercise a lot. When you exercise, you're not going to lose weight or build muscle or other things without doing it regularly. Poker is the same thing we want you to play regularly. My daughter talked about this. We did a TEDx Talk together. She played 30 to 50 hands in a 45-minute to one-hour game, once a week, over 52 weeks a year. You have 5,200 practice sessions. How is that not beneficial? There are a lot of tools and toolkits, but we're talking about a little bit of time, and you get a lot of focus practice. It's really like exercise.
When you play poker, the pros will fold their two cards they get–everybody gets two cards and beginning–80% of the time. Now when we're just teaching, the women ask, “When do I play?” So we teach them when to play. Our goal is, after 30 minutes in a lesson, you're playing in the next 30 minutes, and you know how to play poker. You're not the best poker player in the world, but you know how to play the game well enough that you could go practice. We teach you what you're looking to play. Here are the three types of cards you're looking to play. The woman said, “Well, I never get the cards,” and the teacher had said to her, “Well, next hand I want you to go in.” She said, “We're not going to go in because I'm going to lose. I'm not supposed to play those cards.” “I just want you to try.” She didn't try. With the next one, she tries, she goes in and ironically plays two awful cards and gets a full house.
That's so interesting about poker: If nobody ever played their cards, nothing would ever happen. There are antes. They call them the small blind, the big blind, and it goes around the table, and you must put them in. If you never play your cards, you will lose. Period. If you never say anything, you will lose. The opposite is also true: If you only play your best cards, you will also lose because the room will know your strategy. Now what are you going to do? If you never play your cards, it’s like going into a meeting and never speaking. People are going to wonder why you're there. By the way, if you never get the perfect cards, you'll walk out not having said anything, and the team doesn't know how much value you can add. So you're prepared. Your curveball is not having such good cards. What's happening in that meeting is not what you really thought was going to happen. You must think on your feet. What is your strategy, what are you going to do in this scenario, based on an unexpected action from a colleague? I think that player is that type of player. Not today, they seem very aggressive! I don't really understand why they have a ‘large chip stack.’ What am I going to do? How am I going to respond? If I just keep folding to them, they will never invite me back to the table.
Sharon Fiehler
And how can you bluff if you're predictable?
Jenny Just
Exactly, you cannot! You can work on your toes.
Beth Chesterton
And how much is business suffering by not having the best and brightest talent making the contribution?
Jenny Just
That's exactly right. We have to contribute. You have to play the game. You can't just stand in the room and watch. You have to walk over, sit down, and you have to play. Playing means you can’t fold every time you have to play your cards, because otherwise, you'll lose one-hundred percent of the time. You know the adage: You miss 100 percent of shots you never take. It is absolutely true for women going into a meeting and deciding not to speak. Annie Duke used to say it used to say this, which is quite brilliant: “Your chips are like your voice. You don't get any questions answered without putting your chips out there.” You don't learn anything without speaking. Now I get to practice. It's funny because I have this all the time, with at least 90% of our women when we initially teach them to bet fairly aggressively: Don't ‘limp in,’ which is a poker term. Everybody feels uncomfortable doing it. Everybody. I don't care how senior or how junior they are. “Really? Three times to make blind? That's how much I'm going to put in?” They would never do that. They would just test the waters. I'm going to go to that meeting. Maybe I'll raise my hand towards the end. Maybe I'll say something in the next meeting. Each one of those steps Iost opportunity.
Sharon Fiehler
I have a 13-year-old granddaughter. Guess what I'm going to be introducing her to?
Jenny Just
That's great. You'll be the grandmother that she talks about someday. If it weren't for you… I think that's really special.
Sharon Fiehler
Jenny anything else?
Jenny Just
We're, like you, hoping to impact a million women to play this game. People can find us at pokerpower.com. We'd love to see you. We’d love to teach you. We do everything from real life to virtual, and we just built what we believe is the first gender-neutral poker app that’s out in the marketplace. We're really excited to have recently rolled that out.
Sharon Fiehler
Jenny, thanks so much again for coming on the show today. In closing, I want to remind everyone that ABC to CEO is a not for profit organization on a mission to inspire and prepare one million young women for top leadership.