Jenny Just of PEAK6
How she is teaching women to take risks.
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 312: Jenny Just
Hi. I’m Charles Day. I work with creative and innovative companies. I coach and advise their leaders to help them maximize their impact and grow their business. To help them succeed where leadership lives - at the intersection of strategy and humanity.
This is Season 3 - “Leading The Future.” These next few months are going to be chaotic. Industries are being reformed, culture is being redefined. New rules are being written and rewritten. It’s happening already. Decisions are being made today, literally today, about how to compete for talent and relevance in this new world. So, how should leaders lead as we meet a world of new possibilities and expectations?
A recent study by the World Health Organization reveals that working more than 55 hours a week causes a significant increase in premature death.
If that’s true, it’s just one more reason why leaders should make decisions faster. And why they need to create an environment in which it’s easier for others to make decisions faster too.
What’s the reason that decisions often take too long to get made? Risk.
Risk of failure for sure.
But also, and no less importantly, the risk of being wrong. The human fear that is often hidden behind a carefully designed wall of over-analyzed data and needlessly complex strategies.
What’s worse than being wrong?
Allowing risk to prevent you from discovering that you might be right.
This week’s guest is Jenny Just - the co-founder of PEAK6 Investments. She’s been described as the most successful business woman you’ve never heard of.
She and her co-founder started PEAK6 Investments in 1997 with $1.5M in seed capital as a proprietary options trading firm.
Today, it's a multibillion-dollar financial services and technology firm that has never had a losing year — and an average annual return of 57%. They describe themselves as traders and investors, and dreamers and the businesses they own and have turned around, literally change the world.
Jenny believes that risk-taking is a muscle - and like any skill it needs to be practiced. Which is why she started Poker Powher - a company that teaches anyone who identifies as female how to play poker. And in the process gives them a place to practice strategy, confidence, capital allocation and risk taking - essential skills that you need to succeed at every table in life - from the classroom to the boardroom.
In any business that depends on unlocking creative thinking and innovation, risk is leadership oxygen.
Without risk, you’ll suffocate - and so will everyone who works for you.
But put risk in its proper place and you can, actually, change the world.
“Maybe I'm unusual in this way, I don't know. When I think about taking a risk, I usually don't think about it until after the fact. I usually think about getting through the risk to the other side so then the risk gets downplayed in the journey. It's just something that has to be done in order to get there.”
Our life exists through three prisms in time. The past, the present, the future.
The past informs us or holds us back. Your choice.
The present has already been determined. We are merely passing through it.
It is only the future that we can change. To use Jenny’s phrase, the other side. The place and state we want to reach.
If risk controls you, you won’t try.
If you don’t try, you’ll never learn.
And if you’re afraid to learn, you can’t lead.
How much risk is your future worth?
Here’s Jenny Just.
Charles: (03:52)
Jenny, welcome to Fearless. Thanks so much for coming on the show.
Jenny Just: (03:55)
Thank you so much, Charles. It's a pleasure to be here and to be part of your podcast.
Charles: (04:01)
Thank you. When did creativity first show up in your life?
Jenny Just: (04:07)
I think creativity for me as a young female, my mom was an artist, my dad was a surgeon, and while both of those are creative in their own way, I sort of followed my mom's path. But when I learned that I was good at math, my mom's dad told me, "You're going to be an architect someday." And so that's where I went. That's what I thought I was going to do until I got to the University of Michigan and took my first physics class and thought, “That is not what I am going to do.” But it really lead … and I say this today, I'm in a very left-brain world being in financial services for over 30 years. But I think the right brain side has really helped us to solve problems uniquely and especially being a female in a male dominated industry.
Charles: (05:08)
Do you have brothers and sisters?
Jenny Just: (05:10)
I do. I have four brothers.
Charles: (05:13)
Wow. Where are you in terms of age?
Jenny Just: (05:15)
I'm in the middle.
Charles: (05:18)
What was that like growing up with four brothers?
Jenny Just: (05:20)
I think that it had a much larger impact than I ever knew. Being in it, it was chaos. There's five kids, my dad worked all the time and my mom did her best, to keep her head above water. But I was stereotypically very male-oriented in my hobbies and activities besides my art. That was the one place where I was different than my brothers, but otherwise, I thought about sports, I thought about competing, I was a real tomboy, I think. It gave me comfort with my brother's friends. It gave me comfort being around men. And so when I ended up on the Chicago Board Options Exchange out of undergrad, it was crazy because the trading floors are crazy, but it wasn't crazy because I was female. Though people thought I was crazy for being female. They wanted to protect me. Literally the first week I was there, the men I worked with said they would protect me.
Charles: (06:28)
How did that feel?
Jenny Just: (06:32)
Of course, I didn't understand why they would need to at the time. As you start to learn, it's like a sporting event down on the exchange floor every single day. And it's all men and it tends to be large athletic type characters, with big voices. And the bigger you are, the more you're seen, the more trades you get done. So being female in there was highly unusual. And the great thing aboutwhat turned out to be protected was it was really protected... Well, they thought they were protecting a female. What I thought was, I'm getting protected by being part of the smartest equity options and other products, FX interest rate, companies out there. So I'm protected by being smarter, not by some physical situation, and I learned that pretty quickly.
Charles: (07:34)
You started PEAK6 in '97, right?
Jenny Just: (07:37)
Yes.
Charles: (07:38)
What gave you the confidence to start your own business?
Jenny Just: (07:43)
It was interesting. It was situational. Our company, O'Connor, had done a joint venture with Swiss Bank and eventually became UBS. They were moving out East so we didn't necessarily want to leave. But we had helped to build the over-the-counter equity during the business inside of Swiss Bank. So it was my co-founder, Matt Hulsizer, and myself and a gentleman they brought in from Goldman Sachs.
People wanted to talk to us. So we're in our mid twenties, and I always said, I was female and I'm talking equity options. I was so unusual, they would take the call. But O'Connor was so interesting to them. O'Connor had really never been out in the public domain, but was very well known for being the best. And so again, I was fortunate to be taught by the best and I think that helped bring that confidence. So when it was time, when the company actually ended up moving, we said, "Well, we're happy to do this here in Chicago, still, if you want to do this with us." And they said, "No, thank you." So we went out on our own.
Charles: (08:58)
Did that feel risky? Were you conscious of it being risky?
Jenny Just: (09:03)
I had a one-year-old and I was the breadwinner, but I didn't think of it that way. Maybe I'm unusual in this way, I don't know. When I think about taking a risk, I usually don't think about it until after the fact. I usually think about getting through the risk to the other side so then the risk gets downplayed in the journey. It's just something that has to be done in order to get there. And usually people get hung up right there at the risk itself. So I'm able to sort of trick myself into thinking that everything I hope and dream and want can happen. I just have to go down that path.
Charles: (09:52)
So you've always been outcome oriented, you've always been goal oriented?
Jenny Just: (09:58)
I don't know if it's goal necessarily as it is desire. I think I'm a curious person. My co-founder, Matt, would say I always like to pick a fight with the biggest person in the room. So it's a challenge, but I think that goes back to your original question about growing up with four brothers. It was a common occurrence for me to be around men who were challenging in some way or young men who are challenging in some way. And so it became a game of sorts, It's, I'm the only one in the room, what if?
Charles: (10:40)
And is he right about that? Do you like picking fights with the biggest person in the room?
Jenny Just: (10:46)
I think I have creative solutions to problems that people aren't otherwise looking at because I come from a different perspective. So when I'm constantly surrounded by men, my ideas look crazy. Poker Powher, one thing I know we'll talk about today, is seemingly crazy. It was even crazy when we first came up with it. It came up because of my daughter who was 14 at the time and Matt, my co-founder who is now my husband came back from a tennis match and said, "She's a very good tennis player, but she may as well be hitting against the wall. She may as well be hitting with her teacher. She doesn't realize she's hitting against someone who's strategizing on what they're going to do back. She needs to learn to play poker." And walks away.
And two weeks later, I mean, I did nothing with that information. By the way, I didn't grow up playing poker, interestingly in a family with four brothers and he doesn't play poker either. But of course, in owning a trading business, many people play poker. And I said, should I teach my eighth grader to learn poker? What a strange sort of concept all of a sudden. I was like, I should. And now, my biggest risk, of course, is that we have that entrepreneurial spirit. Of the 15 companies, PEAK6 has either started or gotten turned around 15 companies in 24 years. So we had the bug, clearly, lots of failures, lots of successes, thankfully. So I didn't want to put the cart before the horse in this one. I was like, and we did an experiment and we did a second experiment, and next thing you know, we're doing this with high school girls, with college women. I am teaching risk, taking risk, I'm teaching strategy, I'm teaching capital allocation, I'm helping them to make decisions. They feel so confident.
The confidence level of these girls from week one to four when we started this thing was with the high school girls and we've now moved to corporate, but I was floored. Whispering, sharing, "You can have my chips." You run out of chips. By the fourth lesson, they’re as straight as straight can be, looking at their cards appropriately. If they don't know what they're doing, goddammit, you would think they know what they're doing. I mean, it was so magical. And we're like, well, this is lightning in a bottle and our PEAK6 women started hearing about it and said, "Wait, if it's so good for them, why aren't you teaching us?" I was like, why not.
And what better than a product that gets pulled versus pushed. So now a year and change later and through COVID and everything else, we're signing every woman or who identifies as a female comes into PEAK6, starts with poker lessons.
Charles: (13:44)
It's an amazing story, and I do want to talk about Poker Powher. It was one of the things that struck me in getting to know about you. You guys talk about the issue of female leadership through a couple of lenses that I think are really important to bring up. So one of the things you say and point out is that only 7% of the world's CEOs are women. You also point out that only 20% of the C-suite are women. My belief, talked a lot on this podcast about the need for women leadership. We need way more women. I would rather live in a world that was predominantly run by women for all kinds of reasons. The system has been rigged for centuries. Misogyny has been institutionalized. I think most of us, people listen to this podcast certainly would agree with all of that. Before we get into Poker Powher and some of the attributes that it unlocks for women, what role do you think women have played in creating this reality that we are fighting against?
Jenny Just: (14:48)
I unfortunately think, and because I live in this male dominated financial and technology space… women, whether they're taught or inherently grow up feeling they need to be perfect, feeling the need to play it safe. And then accepting that. I blame the environments that we create and sort of nature, right? Hunters and gatherers, right? There's a reason there's two of those things out there, and Matt and I speak often about sort of the... We always laugh about the history of the world and it started with the dinosaurs. The opportunity for the female to step in and take ownership falls a lot on her plate. But as she's in that process, because it's a different process than it is for men. Because she doesn't do it growing up necessarily because she doesn't naturally, inherently or in the environment process, play, learn in this competitive way, she has to figure out how to build those skills.
And what I think today, given the fact that, I think it's McKinsey, came out with that first rung on the ladder, It's when the woman first comes to their job, they're completely equal. We know that today. They are completely equal competent with their male counterpart, but they don't take that first risk, that first promotion. They don't think they're quite ready. And the male will take that risk 60%. If he thinks he can do the job 60% of the way, he's in. So here we always thought it was maternity leave. You get to maternity leave, you're never catching them. So we have to actually change it, which is why when we started talking about teaching these skills that poker lends itself to, getting to the high school and the college women. The interesting thing though is, If you say poker to a female, they usually turn their head. They turn away. So it's never too late, but if the corporate women that we are talking to today realize, wow, I actually do have to practice some skills. I actually do have to practice risk-taking, I have to practice decision-making, I have to build my confidence, I have to do that in a tangible way, we call it stacking skills at PEAK6, how do we do that? And then by the way, I know I have a personal responsibility as a female to do that, but can we also teach the corporate institutions to give them time to learn those skills? So because the men get the opportunity to practice, fail, practice, fail, practice, fail their whole lives, by the time the women get there, it's too scary to play against someone who's already practiced and failed a ton of times. They're really used to taking that risk and failing and getting back up on their feet.
The consequences are too large. So we have to open up a safe space and I think the movement towards companies giving women time. I mean, let's talk about the chaos that's ensued over COVID and 2 million plus women who are out of work, I mean, we're decades behind. Companies actually have to change. So as a leader, we're changing inside of all of our PEAK6 companies. We're going to give women the time to practice. And if we give women the time to practice doing these skills, capital allocation, strategy, risk-taking, then they're going to be able to step into those roles when the opportunity comes around and compete head-to-head. It's two-headed monster. The woman has to acknowledge and respond, and I think the companies have to acknowledge and respond.
Charles: (19:11)
There are a couple of different points that I would draw out from this. One is that self-confidence is the attribute that I see most getting in the way of the women that I work with and it's one of the things that we spend most of the time on, is trying to help them understand who they are and how they see themselves as the rest of the world sees them. How do the skills taught through Poker Powher enhance a woman's self-confidence? What do they get from that process or experience, I guess better put?
Jenny Just: (19:45)
I always call it, it's like a force field around the poker table. It's really strange. This was pre-COVID. I had a woman come, literally met me in the bathroom and she's probably 23, a new employee, "I won a hand at poker. Thank you so much. I never thought I would be at a poker table, and let alone win a hand." I mean, it literally gave me chills. Why is that possible? What is it? And there's this stereotype around poker and men playing and a language that you can't understand and these unspoken norms. It's really sort of secretive. And just the challenge of sitting at that table. I always say, if you take a thousand freshmen young men in college and ask them to sit at a poker table, 990 of them will sit at the table without knowing anything.
You take a thousand freshmen girls, 990 of them will not sit at the table without knowing something. I mean, it is night and day. So there is something inherent in the game. At the time, pre-COVID, it was more than a hundred million people in the world play poker. Now with COVID, of course, so many more play. Less than 10%, to be safe, single digits of women play poker. They're not invited to the table and they're scared as hell to sit at the table. So if you think about what I've accomplished over my time and I didn't play poker, I'm scared to sit at the fucking table. And I know I have to practice before I sit there. There is a mental shift. There's something that happens and that is critical.
Poker's like a microcosm of events that happen in a classroom, in a meeting, at the boardroom table. So I can basically create a microcosm of events that are corollary to what happens in business or an industry. And I can relate the two and say, now go here and practice. So when you go here, you feel comfortable. And that women are just, their buckets are filling up with confidence from that. And the idea that you have to go around the table and make a decision every time. I'm calling, I'm folding, I'm raising, but I have to. I have to make an independent decision. And that piece of practice in all kinds of situations. Poker is… people talk about it like storytelling, right? It's a narrative that unfolds at the table, depending how many chips you have, how many chips they have, turning the cards, what's shown, what's not shown, where you're sitting at the table.
It's exactly like the boardroom table. The funny thing I said after all this time, so of course now I've learned poker. I said, "I've been playing poker my whole life. I didn't even know it." I didn't even know it. And think about how much that's helped me, which is why I know now everything becomes a poker analogy to me. My co-founder Matt, he was not a poker player either, which is also interesting, but we use the analogies all the time.
Charles: (23:15)
One of the things that our mutual friend, Joanna Coles, was telling me about what she's learned from Poker Powher and learning how to play poker was that it's taught her discipline and it's taught her patience, both of which I think are more readily available in my experience in women than men. But I'm interested because both of those things can also be seen to be inhibitors. They can actually be things that prevent you from leaning in and taking risk. How do you marry the confidence that comes from learning how to play poker with the fact that it teaches you discipline and patience, and how those things do not actually become inherently in conflict with each other?
Jenny Just: (23:54)
Yeah. That's a really interesting question, and depending on your juxtaposition, I think you come up with a different answer. But I will tell you immediately, for someone like myself, the patience was incredible. But of course, and similarly I think for Joanna, because she's been in a leadership position for a very long time. So, you're catching yourself. Wow. Okay, wait. I have to wait for my spot. However, for people who don't have that experience, who are young leaders, who are trying to grow, the strategy around the discipline and patience, that's what the female historically doesn't get. So now I not only have to think about what I have and what's going on, I have to think about what they have, but I also have to think about what they think I have. That is not a normal process for a female. She did not think about how that player is going to be thinking about me, given what just happened with the other three players. That is not how our brains work.
So all of a sudden, it's a really complex game. It isn't blackjack. Poker, it became a mind sport in 2009. It's like chess. Chess is a mind sport. It's a game of skill. We don't gamble in our clubs. We don't use money in our clubs. The best hands win less than 20% of the time. That's crazy. That's how skilled you have to be at this game.
So back to that original part of your question, being at that table, just going to the table, leaning in isn't enough. You have to go to the table, sit down and fucking play. And you've got to play and you've got to play and you've got to play. And you've got to lose and you've got to play and you've got to win and you can play, so that you get the feeling. It is about you. This is that responsibility the woman has to make change in her career, and hopefully the counterpart, the company helping to make change.
We have something really, I don't want to jump in before your question, but I think a really creative solution we haven't deployed widely yet. I think it's super interesting. You’ve got mentor-mentee programs out there. Everybody's trying to fix it. Everybody tries to make it. If you find a magical mentor-mentee situation, great. And oftentimes some of your best leaders will say, "I had this, great," but there's a large part in the middle there that never goes anywhere. Someone's a mentor or a mentee because they had to be in this situation. Oftentimes it's male-female, especially in male dominated industries when the female is yearning for that mentor. And it's another cup of coffee and it's another lunch and it's ‘what am I doing’ right? Am I really getting somewhere? And by the way, is that person the best teacher for me? I don't really know.
We are starting to put mentor-mentees at the poker table. So the man typically knows poker. If he doesn't, he's totally game. This is fun. Mentor-mentee and I play poker. I'm in. But for the female, now I have a responsibility to play the game. And now let's talk about a hand. Let's talk about what happened in that hand and how it was like that negotiation I was just in and how it could have played out differently and how I should have thought about it and how I should have strategized differently. Let's talk about when we were playing together, and I was thinking what you had was this and why. What do you think you could have done differently? All of a sudden, I have really tangible things to hold onto, to go back and play the chess pieces in my head again. I don't know, I think it makes for a really fun environment, worst case. There's a reason why a lot of people play poker, because it's really fun, but we're really excited about that idea of bringing the men and women together in something that's skill-building, particularly for the women.
Charles: (28:10)
Yeah. And I think that's an important element of this actually, because there is, certainly, I think pre-COVID and pre George Floyd's murder, there was a real moment of talking about how to empower women in the workplace. I was having a lot of conversations on the podcast about that. I think obviously those two subjects have somewhat consumed people's attention, not somewhat, have completely consumed people's attention over the last 15 months. So I think women's empowerment has taken a third place position in that conversation and we need to ramp that up again. But one of the pieces of this that I think is so important, it's exactly the point you just made, which is if we don't do something, if we don't do enough to make sure that the relationship between men and women is actually constructed in a different way, then, no matter how much energy we put into female empowerment, we're not going to create an environment in which businesses are actually successful, or those relationships are actually constructive, or we're teaching the next generation of women leaders how to be even more effective and even more powerful.
So I think your acknowledgement or recognition and building that into the process, into the business, I think is going to be really important. One of the other things I want to just bring =up and get your thoughts on is, obviously one of the things that Poker Powher talks about, and we talked a little bit about it through your lens, is that how you help women to assess risk and evaluate risk is critical. Creativity and innovation, unlocking those things in the business world is dependent upon your willingness to take risk. You've talked about taking risk in your own business life. You're an expert in risk. What's good risk versus bad risk?
Jenny Just: (29:43)
Once I take a risk, this is the interesting thing about risk, because what is a risk? Walking outside was a fucking risk in COVID. Going to the grocery store was a fucking risk. So people by the way, got really good at taking risks in the last year, as far as I'm concerned. But people make it out to be like jumping out of a plane or putting your house at risk or something. There are risks that are taken every single day, and if you can contextualize them in a framework around... I'm applying for a job and I don't have all the skills, but that's a lot different than putting my house at risk. But people get really stuck there. They get really stuck. I think as leaders, we do a not very good job of appreciating the risks people do take because they're taking baby ones every day. The person who's asking a question who hasn't asked a question in a meeting, the person who's stopped that leader when we're pre-COVID getting coffee or they went into their Zoom room and they spoke up. Oh my gosh. If we could get to a place where people are appreciating the getting out of the comfort zone that people take every day, I think as leaders, we open up the creativity. That's where creativity blossoms. The easiest thing to do on creativity and innovation is squash it as a leader, because you're running so fast. You're not really listening or paying attention. People are nervous about upsetting the apple cart along the way.
You have to step back. Talk about the patience from poker. And ask questions of everybody in the room. I don't care how junior they are. They might have the goddamn best idea out there, and it's huge risk for them to speak up. The interesting thing is people… all of these words, innovation sounds like such a big word. It's not that big of a word. The slightest of innovations when you talk about texting to tweeting or to snapping, it's very subtle, but really important. We truly believe everybody has that creativity and that ability, that innovation isn't discreet, it is continuous.
So if you constantly allow some freedom in the workplace and safety, and I hate that word because what you think is safe isn't safe to somebody else, which is also a mistake I think by leaders. What makes that person feel safe versus that person over there feel safe is completely different, and now you're in one meeting with both, you screwed it up for one of the two of them. And acknowledging that, and then having your managers acknowledge that. If we can get the smallest of risks, in particular, I think about the women taking those very small risks, those small risks, that practice, that fail, that practice, that fail. It's just a trade.
Charles: (32:58)
Let's talk about the human side of leadership. You're a wife, a mother, you and your husband are in business together. How do you balance all of that? How do you prioritize?
Jenny Just: (33:10)
Well, I'm really lucky I think to work with someone who loves to do the same thing I love to do. PEAK6 has always been like one of our kids.
You opened up by talking about how the world would be different if there were more women leaders. And I think it's fascinating. So all of a sudden, now I have to say, okay, my kid's doctor appointments, I never wanted to miss them. For whatever reason, I just didn't. So I never did. That was something I prioritized. So I had to decide. I had a nanny very early on. She loved to give the kids a bath. I love to give the kids a bath, but I had to make that decision. So again, the cost benefit analysis not of money, but emotions tied to things, I had to weigh them against each other. And I think obviously having supportive family and friends and husband, spouse, and then kids, honestly, who really, they were in it with us. My one-year-old is now working for us. Of course, he got a job somewhere else first because he had to prove he could do that, but we're all in it together.
And I think that's the other interesting thing, being a husband and wife team. And I think a lot of people, as you know, a lot of people look at us like, gosh, I wish I could... First of all, the first thing they say is, "I could never work with my wife." They don't say, "I could never work with my husband." They say, "I could never work with my wife." But I think secretly, how fun to share in all those challenges together. It makes it a lot easier. I would say, the last thing I would say, as a leader, we had great role models at the firm I started out at school, O'Connor, as it was a partnership. So no one person had all the answers. So I never felt… if I wasn't the smartest person in the room on that subject, I was going to be okay because I'm going to find the smartest person and hopefully, God help us, they're going to work with us.
And thank God, Matt and I had very complimentary skills and then our third partner complimentary, and on and on. I mean, most of our partners worked over 20 years together and I encourage every day that our new young leaders, who is your partner? You're looking up to us, but why aren't you looking across to each other? You should know him or her better than you know me. So I, as a leader, I'm doing something wrong if you haven't done that because hopefully I'm setting as a role model. But when we share the load, so when someone goes through something human, when someone goes through COVID differently than somebody else, when someone, all of a sudden our partners pick it up. And by the way, when we have people who don't act like partners, it's pretty obvious and they probably don't end up in the organization for very long.
Charles: (36:12)
Did you have role models who were women?
Jenny Just: (36:17)
There were, one in particular, when I came out of school, traders on the trading floor who worked at the same place. Thank God they existed. That's what I would say. In fact, Matt started on the American Stock Exchange and I was on the Chicago. And between the two of us, so when we started PEAK6 and we tried to hire women, we knew less than 10 women between the two of us, which is pretty scary. But I would say my biggest role model was my dad from a work perspective. So he had extraordinary work ethic, and we always say this to date. And hopefully people hear this who are listening. We weren't the smartest, but we had an extraordinary work ethic.
So when we're hiring smart people, which we do, we hire a hell of a lot of them, we're looking for the work ethic before the smarts, because that's where we're going to find the innovation and the creativity because they're embedded. They live it, they breathe it, they feel it. So all of that, eventually, they're learning to take risks, hopefully working for us and that comes out. But I think that without partners, it's really hard to have your freedoms, to be able to be your best self, because they take the weight from you when you need them to, and then they are smarter when you need them to be. And then frankly, it makes it a hell of a lot more fun.
Charles: (38:02)
Yeah, I think there are so many people who want to be and need to be the smartest person in the room. How have you been able to be comfortable with that not being a goal for you, whether you are or not?
Jenny Just: (38:13)
That's funny. I guess it was always fairly easy for me because I wasn't, because I knew it. But it's easier to not pretend than pretend, I think, getting back-
Charles: (38:35)
How did you know it? Who told you you weren't the smartest person in the room?
Jenny Just: (38:40)
Well, I think it was obvious. So I always say that when I started at O'Connor and I interviewed there, and I still remember this at college. That morning, they were asking questions, math questions, and it used to be because you had to be really fast on the trading floor, so you had to do math very quickly, and difficult math quickly. And I was able to do it. I always said, "Well, I answered the math questions, I was female, so I was in."
But once I got in there, and you are working with some of the most extraordinary minds in the financial world, they were at O'Connor, it was blatantly obvious that I was not one of those, even though I'd done well, I'd gotten good grades. I was a female who was strong in math. So they didn't have to tell me.
But what I found was in fact, one person who took a risk on me, and if we talk about this, a mentor for both Matt and myself, Manny [inaudible], who is one of the extraordinary risk managers in the world, in terms of options. He took a bet on me, but it was around my work ethic. And if he didn't take a chance when he did, PEAK6 would never exist today. And we're talking about a multibillion dollar organization that's thousands of people, and changing industries. He's a single person, if he hadn't seen me and took a chance. So I do think at the end of the day, knowing my place, knowing that my work ethic was as good as anybody, I was smart enough, but I wasn't the smartest.
And I think that ownership of who you are, that makes... Going back to all of those balance things, as a mom, as a business leader, et cetera. I suck at cooking. I suck at it. I shouldn't do it. And I feel bad, my kids all cook, I'm like, "Where did you get that from?" But I shouldn't. I feel bad every time you cook for me, and I don't cook for you, but goddamn, I make a good chocolate chip cookie, and it's okay, because there are other characteristics that I'm proud of or that people can look to me as a role model. Did I grow up thinking balanced in that way? No, but I do also think there's probably being part of a large family, everyone has part of the attention, and I wasn't the one. I was the female in the group, but I was just one of five kids, so we had to spread the wealth and the energy, and for my parents, and I think I just learned to be part of a team, probably. I really liked being part of a team. It's a hell of a lot more fun.
That's what I find really interesting. Whether it's the leaders who are on your podcasts or the people who are leading, when the burden, you can see when your up-and-coming people, and they start to take the burden, take the burden, they don't release the burden to partners around them, of course, you're going to fall over. Of course, that's going to feel bad, And God forbid in a Zoom world where the day never ends, I think it's a really hard place to be. So that balance, calling yourself out, getting help, being a partner, those are the things that, at the end of the day, you can survive this really intense work environment that exists.
Charles: (42:30)
Do you make time for yourself in all of that?
Jenny Just: (42:37)
I think I do. I have some really good friends, I have a group of friends from high school, there's 13 of us. So we just went on a girl's weekend for the first time since pre-COVID. But I don’t think I need a lot, going to our kids' games, thank God they're happening again, because they don't want to play another board game with me, but that's where… getting on the pickleball court for Mother's Day with my kids, that's the me time. That's what I love to do. And so, but making PEAK6 the best version of itself, and now that we have multiple companies who are trying to grow, and then we have so many new leaders. Seeing their successes is really my joy.
Charles: (43:30)
A lot of people are intimidated by money. How has your relationship with money changed over the years?
Jenny Just: (43:38)
I think it's actually changed a lot, but in maybe not an expected way. What I realized about money, which it's funny because there's a really brilliant woman, her name is Margo Cook. She was at Nuveen forever and a very senior position, and when I talked to her about poker, she said, "I started playing poker as a kid." And I love what she said, she goes, "It made me not afraid of money." And when I was in the process of bringing Poker Powher out to the world, we were also working on our female employee groups internally, and risk and money have really come to the forefront for me, for women.
When you look at large banks and they're going to claim some 20 to 30% women. I don't think it's fair assessment, because it's not women in what I'll call capital allocation positions. They're certainly the portfolio managers are far and few between, but they're not the women in the room making this decision around the money. And when I started going down that path, and I started even watching in our own firm, and when we started talking about poker… I don't care if you're a not-for-profit or a for-profit, all the decisions happen around the money. And so, if you don't have the confidence, if you don't start practicing, whether it's practicing through a game of poker, or practicing in some other way in your institution or outside your work by stacking skills in some other way, you're never going to be in a position of leadership. You have to understand the money, right?
So how does the money, I don't care if you're sitting at a receptionist desk, or you're sitting in a management role in a county, how does the money connect to you? And then how do you save, or add more in your position? And then how does your sub group or team, or then division, how does it work? It's shocking to me the lack of understanding around money. And again, I think this goes back to, I talked about my 17 year old after quarantine. We had played a bunch of ping pong, then we weren't, and when he come back, we were in Arizona and came back in the summertime, he was going to play ping pong. I'm like, "Why don't we play ping pong anymore? You were playing so much." And he's like, " Well, play for money." And I was like, "First of all, where'd you get the money? But second of all, my daughter would never do that, right?" It's really natural for him to go there. As much as they have an account through us under 18, all these kids are... But he naturally is inclined towards that money, whereas my daughter I'm like, "You need to look, what's in your account. What are you doing? Why? Try fail, try, fail, right?"
So, I don't know if it's because of the job I took right out of school, around money, if it's what my parents taught me around money, but what I do know that that made me comfortable making decisions around money. But I do know, if we were talking about the five pillars of what we think internally, the skills that women need to stack around: risk, strategy, networking, communication, the most important for us is money. And if you don't want to learn about the money because math wasn't your skillset, I'm telling you, if you can understand how your house works and how to pay your bills, you have enough math knowledge to understand the money, but if you're not going to go there, you shouldn't have expectations of being a senior leader. You can't just skip that step.
Charles: (48:05)
Yeah. It's absolutely right, it's fundamental. And I think it's interesting actually, how many people get into positions of senior leadership and do have some level of intimidation about money. Where do you get inspiration from?
Jenny Just: (48:19)
I think there are probably two things. One, and I think I get this actually, my grandfather was like this, and my mom was like this, and one of my brothers is really like this too. I'm for sure, an extraordinarily curious person, so I can get inspiration anywhere. So, I'll tell you real quick, so my grandfather, he had his newspaper open every day, and he had a ruler and he put the ruler, he'd find an article that everybody should read, and he took a ruler and made sure you perfectly pulled that article out of the paper, right? Pull it down, rip it off, but he had to have the ruler there to do it. My mom does the same thing to this day, and I used to do it too, but now of course, I know it's silly to have the newspaper, so I send it via email or Slack or something. But my mom is, I mean, it's fascinating what she sends me. And thank God, she opens my eyes up to whatever the subject might be.
"Did you know how 5G worked?" "No, I didn't, mom." "Do you know that C-130 plane, how much it..." It's just, it's crazy what comes, but what an interesting way to go about life, right? And so it's easy to get inspired. I think the other part as I've matured at work is just the idea that we actually can change the world. Apex FinTech Solutions is changing how people live and operate, and because I can see where this might be going and we could be part of it, it inspires me to work harder, do more, and it's fun. It's fun to try.
If I fail... And I always like to say we failed in more ways than most people you know collectively. A lot of those failures we took really early on at PEAK6. So you're a trading firm. You make a bunch of cash. What do you do with it? Because you don't need a lot of capital for the business. So then you just do dumb things, so we did a lot of dumb things. We had a chicken cleaning business, we had an oil field. You name it, we did it. Everybody does a restaurant. So what? Our restaurant went down in flames, like literally. But that opportunity to try, like I said in the very beginning, the risk is mitigated by the excitement for the possibilities. And obviously we've had a lot of experiences now where we've had a bunch of success, so that makes it easier, but it doesn't make it perfect.
Charles: (51:04)
You must have learned so much in those early days that must've carried you forward, extraordinary lessons and experience. How do you lead?
Jenny Just: (51:18)
I think we are hands-on, historically. I think we've learned to be better teachers, but we're not perfect. I think some of your best leaders are those who show you how to take risk, and I think that's definitely something we do, and hopefully not squash, like we talked about earlier, people's ability to take risk alongside of you. Because sometimes when you're so confident taking risks, it makes them less confident just by definition. So, how do I bring up a really junior person taking risk? I think we lead by taking risk, and I think we lead by setting the pace.
The pace is aggressive at PEAK6. It's not for everybody. I think part of that comes from this idea of trading. There's a lot that's happening in the world, and we want to be a part of it, and how can you, how can we do that together? And if we can't, we're okay with quickly failing and moving on, but it's a grind, particularly in Zoom world because it feels like it's never ending. But I'd like to be able to show people how to set a pace that's required for success and then allow them to feel safe taking risk.
Charles: (52:57)
You've been described to me as perhaps the most successful business woman that people have never heard of. Why is it the most people have never heard of you?
Jenny Just: (53:10)
I've been busy. That's funny. Wasn't necessary, first of all, for what we were doing for our businesses to start with. We've mostly been behind the scenes, and we're happy to be there. Happy for others to shine and happy for me to have more time, frankly, for my family, again, back to the balance and priorities. There was one mistake though in all of that, and that was the finance world and the technology world need role models. When my daughter was 14, she said, "Mom, if you're..." In pre-COVID, we had talked about me being out there. She said, "Mom, if you're ever going to do it, if you're ever going to go out there and have people listen to you, you better do it soon because you're going to be too old and they're not going to care."
But I do. I feel a sense of responsibility, and frankly, I think the people internally at PEAK6, they're really proud of what has been built, and most people don't know the name. And they'll now know Apex FinTech Solutions as a public company, but there are plenty of other companies that we've either started and sold or grown that people don't know, and employees like that. It's just we were busy being our own best version of ourselves, and we were happy to live that life. Obviously, I'm hoping that the people want to hear the stories now, that it's an opportunity.
I think we've narrowed our ability too, to really, what can people learn from my mistakes, or my successes? And we've also done that internally at PEAK6. I don't think it's about my words, like this whole cheerleading waving hands, rah rah, go women thing. I want to teach you how to get there. I'm going to be tough. I mean, tell you, like if you work at PEAK6, you're going to know. No, if you think you belong there, I'm going to tell you why not, but I'm also going to tell you how to. I'm going to let you take the risk too.
I want to get answers so people can try things. It may not be the perfect answer, but being out there is going to let at least the finance and technology worlds, as far as I'm concerned, see what PEAK6 is doing to solve the problem differently and hopefully make a big change. We're changing internally from where we were in the last 20 years, and I think we can share that with the world.
Charles: (56:22)
What are you afraid of?
Jenny Just: (56:28)
That's a great question. I'm definitely afraid of COVID. As a mom, I'm always afraid of my kids' happiness. As a business leader, I think the biggest fear... So we do something, I call it innovation for innovation's sake. You always know there are a bunch of let's call it small t-shirt size. Small, medium, and large innovations that are going on. You can see them. If you're close enough to your business, if you're talking to enough people, you see them, but small ones can't always be small, and you want to survive. Now we say who's your worst or your best competitor, however you want to describe it. I don't care if you don't know who they are, if you don't even think they exist. Someone's there, so we always have run knowing that they're there.
The lifecycle of companies is so much shorter today than it was years ago. And so I think that risk of that competitor getting that close... I always say... I'm laughing. Matt always says about me, but I'm definitely the half empty glass in the room if nobody else is going to be. We have too many families that we support now that you may not be a lifer at PEAK6, but PEAK6 needs to survive, so what are we going to do to do that? That, it doesn't necessarily keep me up at night, but over some extended period of time, it's always in the back of my mind.
Charles: (58:32)
So I used to wrap every episode by offering three themes that I've heard. I haven't done it for a while, but I think I'd like to today, if you'll allow me to. So three themes that I think contribute to your leadership success that I've taken away from today. One is, you've mentioned this a couple of times, but I think it's very obvious. Your curiosity. You're interested in what's next, why something works the way it does, how might it work better, and what is important to the people around you? I think that that curiosity is essential.
Two, I think you bring an instinctive and very natural humility. Not the humility that comes from an absence of a confidence, but a humility that comes from genuinely caring about what happens to people around you, and I think that is driven through empathy. And then I think three, and I see this in almost every successful leader that I know, you genuinely want to make a difference to the world. You want to make a difference to the people, not just around you but on a broader remit than that, and creating, whether you think about it through the lens of legacy or impact, that clearly in my perspective matters to you. How do those resonate?
Jenny Just: (59:42)
I appreciate that. For someone who talks to a lot of leaders, that if you were to summarize me in those three ways, my parents would be proud. Interestingly, and I see those characteristics in my parents, so they for sure would be proud. I think my kids would be proud, and I would hope that the people who work at PEAK6 recognize that as well. And I would say it wouldn't surprise me if they came up with curiosity, humility, and making a difference.
It gets hard in the 100,000-foot level to recognize those 500,000-foot level characteristics sometimes. Especially, like I said before, it's tough, We're a tough crowd, but I think that's because of these things. Because we believe, because we're so passionate about it, because who knew we were going to make a difference. Because we have, it makes you want to do more. I also think when you're coming post tragedy, and you can't help in a COVID world - I'm not a frontline worker, I'm not a healthcare worker, I'm not... How can I just help humanity. I think that PEAK6 changing families’ lives but also changing how they interact with the world from a technology perspective, democratizing the world. Whether we're democratizing it from improving female skills or putting hands in the technology of everybody, not just certain people, so everybody has the same equal opportunity to participate in the growth of the stock market in the country. And they have the knowledge to do that. How can we be a participant? We'll see what happens 20 years from now, but I'd love to say that those three characteristics really, really help to drive significant change in females in our workplace, because as we started in very beginning, what a difference the world would be. The data has already proven and shown if we have all different types of people at the table.
Charles: (01:02:32)
Jenny, thanks so much for joining me today, and good luck with not only everything you're doing, but obviously specifically with Poker Powher. I think it has a chance to really make a difference.
Jenny Just: (01:02:39)
I really appreciate it. So nice to meet you.
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