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A
You can actually take more risks with an S. You don't necessarily have to take bigger risk. Whether you're an entrepreneur, whether you're working in an organization. You have to be able to make decisions around money. You have to look at what you're doing every single day and say, why am I doing it?
B
Support for Net Worth and chill comes from AmazonOne Medical. When someone says Amazon, do you think healthcare, maybe you should? Amazon One Medical offers 24. 7 virtual care so you can speak to a provider within minutes. Not only that, there's also Amazon Pharmacy. So after your virtual visit, Amazon will deliver your prescriptions directly to your door. No more waiting in line with people who are sick with who knows what. Thanks to Amazon Pharmacy and Amazon One Medical, healthcare just got less painful. Learn more at health.Amazon.com what's up Rich friends? Welcome back to another episode of Net Worth and Chill with me, your host, Vivian Tew, AKA AKA you're rich, BFF and your favorite Wall street girly. And a couple months back, I was in Vegas celebrating a girlfriend's bachelorette. We did the whole day club, nightclub, dinner party thing, and as we were walking through the casino in our hotel to dinner, I noticed a poker tournament going on. And the one thing that jumped out at me about this tournament is that there were literally hundreds of tables with, you know, multiple people sitting at each table. They had these sunglasses on. They were mean mugging. But as far as the eye could see, I could not see a single woman. And that really bummed me out because I recently learned at a very cool dinner, a lot of women could learn a lot of really important life skills playing poker. In fact, this game might actually make you better at business, better at finances, better at investing. I'm serious, you have to know when to hold them, when to fold them, and when to cash out. But let's set the record straight. I'm not advocating for you to head to your nearest casino and play the slot machine or hit the craps table or put it all on red. I'm advocating for teaching everyone, women in particular, a set of skills via a card game that might just make them better at life overall. Today we have a very special guest who's gonna explain how poker, business and life are all interconnected. Our guest is a self made billionaire, mother, investor, and badass poker player. Everyone, please welcome Jenny. Just.
A
Hello. So glad to be here.
B
So good to see you again. I'm so excited to chat with you. But before we get into the really juicy stuff, for those of us who don't know. Cause I didn't know a couple months ago. Can you give me like a 30 second rundown of how the game of poker works?
A
Sure. It's really actually quite simple. So you're with a group of friends, colleagues at a table, let's call it six, eight, nine of you. And you're all going to get two cards hidden. Those are whole cards. And then there is going to be some cards, community cards, that come out in the center of the table. And when you look at your first two cards, you decide if you like them or not based on your approach and strategy that we like to teach. And you either bet or you fold your cards. When everyone has gone around the table, there'll be three cards that come out. It's called the flop. And then there's another round of betting. There's the turn, one more card, and the river, one more card. A round of betting at each. At the end, you will see who has the best five card hand, taking into consideration the community cards and your two hole cards, and that winner takes the pot.
B
So you mentioned playing with a group of friends. When did you start playing poker? How'd you learn?
A
So here I am espousing the game of poker. The interesting thing is I learned it only five years ago.
B
Oh, wow.
A
Okay. So, yeah, I learned it in 2019, right before COVID And I learned it because of my daughter, actually. So, like, you grew up on Wall street and surrounded by poker players, and I thought it was gross and definitely not something I was interested in and. And a waste of time.
B
Yeah.
A
And it turns out it's not, but I had no clue. So my daughter's 14 at the time. She's playing a tennis match, of all things.
B
Okay.
A
And her dad is frustrated cause she's losing. He's very competitive, as most of us girl dads are. And he comes home because he doesn't want to tell her and says, she may as well have been hitting against a wall. She may as well have been hitting with her teacher. She didn't realize that the person on the other side of the net was strategizing, was thinking about what to do to beat her in the game. She needs to learn to play poker. Throws up his hands. And I was like, you're ridiculous.
B
Like, what does that have to do with that?
A
Exactly. And I walked away. Now, the funny thing is he's not really a poker player either. He's more like a blackjack guy. But he knew he understood something that I didn't understand. Anyway, I ignored it like two weeks later I was like, should I teach my 14 year old daughter to play poker? And then I realized, wow, I would never make that same statement about my sons. I have three sons who are older and by the way, who already knew how to play. We'd have never taught them, of course, because they all seemed to figure it out.
B
Yeah. Probably had friends who taught them.
A
That's exactly right. So fast forward, I'm like a good entrepreneur would do. I do a little bit of an experiment. I go to her friend's moms and I'm like, I just want to try this. Let's just see what happens if we teach them this game. So we had 10 girls. They were eighth and ninth grade girls. And then the moms wanted to join. And I always like to say from lesson one to lesson four, literally the skies opened. What happened at that table with those girls is why I am sitting here with you today. It is why we have taught at over 300 companies in over 60 countries this game on our way to teach a million girls and women this game. The confidence of those young girls at the table was palpable. And what I eventually learned as I started to play that it actually looked like my work. It looked like a meeting I was in, it looked like a negotiation I was doing, it looked like a deal I was doing. And it occurred to me I had been playing poker my whole career. I just didn't know it.
B
I love that. I feel like I got chills from you.
A
Saying that gives me the chills too. It's crazy.
B
But you mentioned poker looked a lot like your work, a lot like your career. Can we rewind just a little bit? You are one of the few self made billionaires in the US and even a part of a smaller community. Self made billionaire women. But like in your childhood, were you good with money? Did you know you were gonna become a billionaire? Like, how does that happen, right?
A
No, no, of course not. No. I grew up in Wisconsin. I, you know, had really hardworking parents. My dad's phrase was every day's a work day. So I always had jobs. Yeah, I always was. I was not confident around money. But growing up with four brothers, I was just one of the boys.
B
And your parents were like working parents.
A
My mom stayed home, take care of the five kids and my dad every day. Every day's a work day. So he was a really hard worker. But I would say there was a moment that when I think about in time, because when I became really conscientious around money, we were definitely above sort Of a middle class level. But I was probably 13, 14 years old. My dad usually didn't bring work home. Like he wouldn't do paperwork at the table. But anyway, so this night he has this stack of paperwork. And now this is a while ago. And so it's when you would have a printout of papers and they were all connected to each other. So not quite that way.
B
With the frillies on the end.
A
Yeah. So the frillies. That was me. So he said, here, stand, hold this stack of papers. I did. He said, now drop it. So it was as tall as me, formed a pile at the end and it was a list of all the patients. He was a surgeon that couldn't afford to pay. And so I was. That was wildly eye opening for a 13, 14 year old. And then I suddenly was very nervous about, wait, you go to work so that you get paid. So that we live. Right. So I think it just set a tone for me. Like, nothing's given, nothing's free. Yeah.
B
Yeah.
A
So, wow.
B
And do you feel like that moment ultimately informed your career choice? That you were like, I need to get a job that pays money, a lot of money.
A
So that I wasn't smart enough about. And the only thing I really cared about was being in Chicago. So I grew up in Wisconsin. Like I said. Woo.
B
I went to school in Chicago, obviously, so we have that connection.
A
Exactly. And so I wanted to be in that, in the city. That was the big city to me. So I interviewed everywhere. And I was an advertising company, it was a bank. And I ended up at O'Connor and Associates, which was a very famous options trading firm. I knew nothing. I literally didn't even know I was going to the trading floor my first day. That was all a surprise. It was just a really.
B
What did you think you were signing up to do?
A
I don't know. It was just a cool place to interview because they were very early wearing casual clothes. They had a cafeteria, which was kind of unheard of in those days. They had Haagen Dazs and beer in the fridge. I was like, ooh, this is sexy. This is where I wanna be. I don't wanna be in a suit with panty. Cause that's what you would have to do. Pantyhose. Yeah.
B
With the nylons.
A
They're so itchy at the bank. Right. So it didn't really matter. I was just happy to have a job, something I paid, and then be what appeared to be like a really cool environment.
B
Yeah. And I started my trading career at J.P. morgan in 2016. And even then, that was only a couple years ago, like, I was still the only woman junior on my entire desk. I'm assuming back in your day, you were one of, if not the only woman sitting around your area. What was it like being a woman in a male dominated space?
A
Do you ever see that movie Wolf of Wall Street? Yeah, yeah. Not exactly. But I have to tell you, it's one of the few movies I walked out of because it was too real.
B
Yeah.
A
So of course there are some exaggerated points, but a lot is not right. I remember when billions came out and people were like, you have to watch. And I had to stop watching, but I didn't ever. Growing up with four brothers, right, Go down to a trading floor and see big, huge men screaming and yelling every day. That part didn't intimidate me. The part that intimidated me was learning options trading, learning how to take risk, trying to be comfortable in a setting that seemed to be really quite comfortable for those guys. So I think that was harder for me than the other, though. You know, my first day on the trading floor, one of the. One of our teammates came up to me, said, don't worry, I'll protect you. I was like, what are you protecting me from what? From what? Right. That's like the surprise. So it was. I also think it had its advantages. Right. In some ways because I was shiny ball, let's try some new things. And so I had quite a few jobs and opportunities in that seven years when I worked there. Probably five jobs in the seven years. So.
B
Yeah. Do you credit any of your success to like a mentor or was there someone who like, took you under their wing to like, teach you how to options trade?
A
So if I. When I talk about a mentor for me, ultimately, and what we've been able to do at peak six, I for sure, it's my dad. Yeah. In those early days of options trading, he thinks I'm crazy, of course, has no idea what I'm doing, and he wants me to go back to school and get my mba.
B
Classic dad move.
A
That classic dad move. So how do I secure? How do I help my daughter set the right tone and the foundation? Fortunately, CFAs came out at that time. I was like, I'm doing this new thing, dad. I'll do this cfa and that. The three letters, Three years of your life. Yeah. So the three letters saved me because nobody, of course, in trading was definitely getting mba.
B
Okay. And you mentioned how much you love Chicago. You wanted to be in Chicago. Unfortunately, O'Connor and Associates decides to move from Chicago to New York City. So you ultimately decide to leave the firm and you and a co founder, a close personal friend, obviously you guys pivot your career of the stability of working for a company to suddenly working for yourself. What was that like?
A
So again, maybe similar to when I started quite naive. You know today back then we're not talking about entrepreneurship at school. No. We're not seeing all these people do startups. And the venture capital world looked very different. So it wasn't uncommon for people who traded to go start their own trading thing. Now we weren't gonna do exactly that we were thinking about. So fortunately we had an experience inside. So O'Connor did a joint venture with Swiss bank at the time, which eventually became ubs and we were part of that. It was a three team. My co founder and myself were two of the members and we started something called the over the counter equity derivatives group for the bank. And so we were sort of intrapreneurs inside of the bank, which I always tell people like even if you want to be an entrepreneur, there's so much you learn from being at these other firms. Right? What you want to do, but also what you don't want to do.
B
Use their resources to build your thing.
A
That's exactly right. So we were relatively confident now, interestingly so we had a plan A, we're going to go out now. It's just two of us in a room, right. Staring at each other. So we want to do this over the counter equity derivative business which you basically need a balance sheet for. So we started talking to banks and.
B
For everybody listening, needing a balance sheet just meant Jenny needed a lot of money very quickly.
A
Very quickly. Exactly. Which we were not going to have anytime soon. But so we actually hired somebody to help us do that. But it was taking time and time and we're looking at each other. I'm like, I'm basically a single mom at this point. How am I going to have income now? We had saved money, we had worked for seven years. So it wasn't dire but I was nervous. So I'm like, we have to do something in the meantime. The irony of the whole thing is that business is sort of the heart and Soul of Peak 6. It's been around for 27 years, it's never had a losing year. And we used technology really early on, so called 1998 to start trading what was exchange traded options from up in office. And so using tech early at that point was quite visionary. We weren't visionary. It was really out of necessity, like how are we going to do this? And we got lucky. And so today most people don't know about Peak 6 because we self funded everything else we've done with the profits from the business.
B
Yeah, I was going to say, I know you launched Peak 6 in 1997 with only $1.5 million, which sounds like a lot of money, but when you're starting a literal fund.
A
Right, Exactly. Nothing Exactly.
B
But you've been able to grow it into a billion dollar business. It sounds like you've been using money making parts of the firm to fund other parts until those are money making pieces and then continuing to grow. What was your first major success that you really like? Remember in your mind, it was actually.
A
Early and it definitely changed our trajectory. So when we started trading, I thought we were going out of business like a month later. Because you can go negative. Right? Quickly. Yeah, quickly. So I thought we were going out of business in August and then in October we actually had a really good trading month. We made our first million dollars, which is crazy cause we were basically around for six months at that point. So now it's like, hold on, do not lose this million dollars. So actually like in some ways was great, but in other ways was petrifying. Like, okay, don't screw this up. How often are we going to be able to make this happen? Theoretically, I mean, that's what we did for so many years at O'Connor. But why would the two of us be able to replicate something that this amazing firm had done for so many years? So I didn't count my chickens, but that first month that we made our million dollars definitely set the trajectory for two things. One is, oh, we can, but oh, how do you protect. Right. And so we always say, you know, in 27 years, any trading firm never having a losing year is an extraordinary fee. It has to be more than that. It has to be about how we operate. It has to be about the technology. But more importantly, we watch. We may not make the most money, but we definitely know how to cut our losses.
B
Yeah, that's that risk acknowledgement.
A
That's exactly right.
B
Understanding your risk. So we just talked about a big win. Your million dollar October. Was there ever a moment that you were just down so bad you were frustrated, you felt like everything was going.
A
Wrong at least once a week.
B
Yeah.
A
For 27 years. So I think the, you know, I heard someone say yesterday, probably online somewhere. Right. It's great to be number two. It's really hard to be the founder. Yeah, it's really Hard to be the founder. So I think for us, some of the biggest frustrations early on were and interestingly helped us. We didn't know how to manage people. We never had to do that at our firm. And all of a sudden, you needed bodies back in those days to populate the exchange floor so you could get the volume. And so if we didn't know how to do that, we're screwed. So using technology and then connecting to the exchanges by sitting at our desk allowed us to not hire as many people. Right.
B
Oh, okay. So you saved on labor.
A
We saved on labor by doing it that way. Now, of course, there's so many more exchanges, and thankfully, the world has changed for the better in the ability to access it. But at the time, it was a mountain that seemed too much to climb. Right. We're 27, 28 years old, and we already have a couple employees. And, you know that I remember I was like, we cannot hire employee number 10. Cannot. And because I also know my co founder, that was definitely not his skill. So. And if I know it's not mine. We're looking around at each other, and people are the best and the most difficult part of building a company because it is uncertain. Right. There are emotions involved, and especially in a trading firm when you're swinging.
B
Yeah, definitely. And speaking of people, how did you select your co founder? And are you two still friends?
A
Yeah, exactly. So, interestingly, we were intrapreneurs inside of the bank, and so our bosses, who eventually put in part of that million six, had selected us to be part of that team. So we had worked across from each other, this far apart from each other for six years at that point, or no, four years there. And then when we start peak six, there was another gentleman. It was actually supposed to be three of us. And at the last minute, he had a new baby, and it was decided he was gonna go with the bank. So he didn't. So now it's just the two of us.
B
If I'm him, though, by the way, I'm looking at your success right now. And I'm sick.
A
Yeah. Yeah.
B
Well, down bad.
A
Yeah. Yeah. Well, I think, you know, he's had a lot of success. And, you know, it is interesting. You know, things happen for a reason, for sure. And. But when we decided to do it, it wasn't. It was more him choosing me than me choosing him, really, I would say, which was highly, highly unusual at the time. So he has a very strong mother and a very strong sister. One of the few female hand surgeons in the country. Right. When she started to do that. And so. And because we had worked together already, I feel very lucky. But I think he also feels very lucky. Right. That I said yes. And that now we're gonna be equal partners though. Right. Which you ask any male at that point in time, you're gonna be an equal partner in an options trading firm with a woman like that is. So I give him a lot of credit for that. Six years later, into Pig 6, we got married.
B
Wait, I don't think I even knew that.
A
Yep.
B
Wait, okay.
A
So we knew each other for 10 years.
B
Oh, my God.
A
We knew each other for 10 years.
B
Maybe I should have done better homework, but I don't think I realized that. Well, I think it's just because, well.
A
We don't have the same last name. No. Yeah. I go by my maiden name.
B
Yeah. Wow.
A
Isn't that crazy? And nobody would have ever guessed it. We laugh about this often. In fact, I was at a dinner last night and people were laughing because there's a fine line between love and hate. Like, it was an all out one. Early days of the firm because there were so many highs and so many lows. And learning to figure that out. Our first employee, who was actually an ex O'Connor gentleman who came and worked with us, he had to take a leave of absence at one point. It was so tough on him to deal with what was going on. And there was no tiebreaker. Right. When you have two people who are that headstrong. That headstrong. Exactly. So it's really hard. And we would say, you know, he or she who has the most passion wins. So there's a ton of passion.
B
That is incredible.
A
That's crazy.
B
And now we have a quick break to share the tip of the day presented by Amazon One Medical. Since it's 2025 now, I know a lot of you guys are probably thinking about leveling up your money and getting your bag. If you didn't get that raise last year, or maybe you wanted more than you got, now is the time to start preparing. We are going to make something called a brag book. I want you to make a folder in your email and label it brag book, raise, receipts, promo pitch, whatever, and the year. So in this case, 2025, and throughout the rest of the year, you're going to send every good piece of feedback from your colleagues or clients into that folder. This way, when it comes time for your mid year or end of your review and you're asking for that raise, you have the receipts to back up everything. You're saying so. So you'll be able to make a compelling argument since you'll have a laundry list of all of your wins. Oh, my God, I can't believe that Sheri was able to do that. Daniel did such a good job leading the team. Anything like that, put it into that folder. The most successful people are not the smartest or the hardest working. They're the ones who can best advocate for themselves. And that is what you need to be doing every single year to ask for that race. Now back to our show.
A
Wow.
B
Okay. So this, I feel like, clears up so many things in my head now.
A
Okay.
B
Because obviously Peak 6 starts out as a proprietary options trading firm.
A
Yes.
B
But these days you're dabbling in tech, you're dabbling in other industries. Like.
A
Right.
B
How does that happen? Because there are likely so many other options trading firms that are like, ah, we're going to have a successful year and have a successful 27 years. They'll just keep doing that and don't do anything else. What made you want to do other stuff?
A
Well, I think a couple of things, and it's interesting that you say that because there are a lot of those firms who say to us, we wish what we did, what you guys did, because it's a healthy diversification for sure. But we weren't that smart at the time. A couple things happened. One is we made more money trading than we knew how to put back into trading at that point in time. Right. So we've obviously over 27 years got bigger, but we had some of those early wins. I don't know how to redeploy the capital at the time. Seems like I would have known, but we didn't. The other thing is what you started to see were some other options trading firms that didn't do well start doing other things. For example, they started retail broker dealers at the time. So think generation pre Robinhood. And we're like, wait, if they did that and they didn't have a successful trading firm, well, we can do that. And so little do we know. That was a whole different animal. Right. When you're providing a service, a trading screen for somebody else, it's not about that screen. It's about marketing, frankly, to them. Right. That's the win. So we were certainly naive in many of the things we did. Easy, low fees. That's right, exactly. All the, all the bells and whistles. But the other thing we started to learn about ourselves over time was that we were really good operators. So when you have really consistent returns like we did, we actually, our business model was different than the typical trading firm. And so we looked at Walgreens as a role model, Walmart. And so we have this inventory of options. How would they manage it? How do we manage it? And so it was a large inventory system.
B
Yeah.
A
And we said, and it's really consistent. What if we apply that technology to other industries? So we started doing that in Insurtech and we started doing that in the Edutech space. So we certainly have dabbled in places we shouldn't have dabbled. We like to say we've lost more money in more ways than most people, you know, combined. But the good thing about it is we knew how to manage our downside. So we tried things and we're really good at exiting either, you know, fails, obviously, or things that probably aren't going to go anywhere.
B
Yeah. And speaking of cutting your downside, you know, you are clearly incredible at managing risk. This might be a philosophical answer, but how do you know in your life when to cut bait?
A
So when I talk about risk with people, it's such a personal, such a personal thing. For somebody, raising their hand in a meeting is risky. For other people it's to the extreme. Right. It's skydiving at risk. Exactly right. So you really have to look at yourself. And this is something actually we're working on productizing how to self assess where you are. And now it's about where you want to go and why. Because you can actually take more risks with an S. You don't necessarily have to take bigger risk, two different things. So it is that repetition of doing it more often that will get you very far. Right. And then you can decide if you wanna level up at the size of the risk you're gonna take. Obviously over time. What I didn't know when I started on the trading floor, like I was just learning to take risk of my own money every single day. But it's the same thing I was just saying where we didn't know how to redeploy more money at the time. Today it's like 2:00 in the afternoon. I deploy that much risk right at the time. So you have to learn.
B
You didn't have as much muscle memory.
A
I did not. So you have to create it. Which is why I say if you're not a risk taker and you want to change your trajectory, you have to start today. Because you're only gonna get better either by closing your eyes and plugging your ears and praying. Right. If you start practicing and Start exercising that muscle. That's the only way you're gonna get better. And the truth is, boys and young men do that far more often. Poker is a great place to be doing that. Why is that than women? I think it's cultural. I think it's part of our society. I think it's part of how we're made up. I think there's all kinds of reasons, but it's not about capability or ability. It's not.
B
It's a learned habit.
A
It's a learned habit, so we can do it. I'm a great example of it. I would not be where I was if I hadn't learned how to take risk. Every minute of every day, you are making a decision. That's why we love poker. It's a place to practice. That's what's so cool about it.
B
Yeah, that's so funny, because when I was learning how to trade equities, one of the things that I would struggle with is I would hold onto a losing trade for a little too long, and my mentor, she'd be like, why don't you just cut half your risk, AKA sell half of what you have or buy half of your short back, and then see? And that changed my life, I'm sure, because it made it half as scary and half as bad.
A
That's right.
B
And suddenly I could think a little bit more clearly versus being like, oh, man, the number is getting really, really big.
A
That's exactly right. But if you didn't do that, go through that, otherwise you sit in that place of uncertainty. So now, the next time you have.
B
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A
Number and you might say, well, I want to get to that whole number again, not just half of it. How do I get there? Yeah, it's not. Again, it's not going to happen overnight. You don't just change how we emotionally assess risk. Right. You have to learn those feelings, which is why when you fold a poker hand over, but then you play a hand and you lose, it's an experience. But right away at the poker table, you're gonna play another hand and you have the opportunity to get back in and do something different. You're forced. You're forced to do it.
B
But I also love that you mentioned you can take smaller risks versus one mega risk. It's like the micro risk.
A
Exactly right. Yeah.
B
You just increase them more and slowly become, I guess, like, I don't wanna say desensitized. Cause that's typically a negative connotation word. But like you become less scared every time you take risk.
A
That's exactly right. That's exactly right. Yeah.
B
Okay, so onto the topic of poker. Poker power has become a really cool part of the Peak 6 business. It teaches women how to play poker, you know, trying to get them to be able to take better and smarter risks in their businesses, in their lives. What inspired you to do that? Was it just that dinner table night with your girlfriends and their daughters?
A
So it all started there.
B
Yeah.
A
But the interesting thing is, so that was May of 19 as we started to play poker. And it was really about poker clubs for young girls. How do we build their confidence at a table that they would generally not feel comfortable at? Covid came.
B
No.
A
Yes. So then we were like, we'll see you later when we can get back in person. Obviously it lasted a little longer than everybody was expecting.
B
Two weeks to flatten the curve.
A
That's what I mean. Oh, yeah, please.
B
Two years later.
A
That's right. So roughly late spring of 2020, I was like, well, we're gonna have to figure this out. Because I believe it can profoundly impact young girls lives. Right. So that was the premise. So we went to peak six families. Everyone's trying to do stuff on Zoom. We got an app, which super disappointing when you go to the traditional poker apps. Right. Cause they're not gender neutral at all.
B
And they're also like, very much like being inside of a Vegas casino. It's like super hyper stimulation lights. It's horrible.
A
Yeah, it does not feel good. But that's all we had at the time. And we said, well, we're gonna teach online. So we went to the peak six families, several thousand people at the time under there, and we said, we wanna teach your daughters and your nieces, et cetera. And then the women at Peak 6 were like, wait, if it's so good for them, why aren't we learning? And I was like, that's a good idea. So we started teaching them. And because everybody was sharing ideas during COVID a woman at Morningstar knew a woman at Peak 6 said, oh, can you teach us 30, 60, 90 women later? Now we are at companies all around the world, in 60 countries doing this for corporates, doing it for their junior employees, doing it for their senior employees, doing it with their clients. We're on stages at these women's conference all the time. We have 26 teachers across the United States and just a mighty team that's in there. And then we built an app. Right. To go alongside of it and to go alongside of the lessons, which are in person and virtual and coming on demand soon.
B
Yay.
A
Super exciting.
B
Okay, that's exciting. A little teaser there. Can you just give us a couple examples of how poker translates into the workplace or in life and like how people can benefit?
A
Sure. So we love our women. It's a fascinating experience. And just to back up when we teach our grown women what ended up happening because they wanted to learn, I did not want to teach the young girls, but what I realized was this could be a really interesting flywheel. Cause I'm going to have to get a buy in from those women anyway to teach the daughters or buy, I'm probably going to buy in from the dads, but I got to get a buy in. So I teach them. And now they know that they can teach. But what we see with the women is consistent time and time again. So we create this safe environment, typically on women. Of course our men are willing to join, but it's for someone who's never played. So of the 100, nobody really knows any more poker players in the world, but less than like 7, 6% are women. So we're all, we're the newbies. And when they come in and learn, they are fascinated very quickly by what kind of risk takers they are. I just literally, I was at a big telecom company on Tuesday and they're all the senior women who are there for a holiday event and sort of training with Us and their eyes, whether they're in legal or their compliance or they're in marketing or their sales or they're in operations, whatever it might be, they all understand where everybody is. And when they are taught from our teachers how to approach strategically the hand that they are dealt, they all want to do the same thing. They all what we call limping in. They all wanna just match. What if they wanna play? And we tell them bet two times, but three times, the big blind. And it just stops. Everything stops. And they're like, it's so unnatural. And these are women who are senior in their.
B
These are like C suite women.
A
These are C suite women. And so when they start to learn, they quickly self assess. That's been the most interesting thing about the senior woman. She starts to self. Now the other thing we talk about all the time is capital allocation. Right. I always say where you wanna be and where you are today. The difference between those two places is taking risk around money.
B
Yeah. And so for everybody who's listening, capital allocation in just a very quick and easy way to understand is where you are putting your money and towards what purposes.
A
Right, exactly. And if you aren't making those decisions, you want to be in that seat because that is where the power is held.
B
Yeah.
A
That is why you will be a leader. You have to learn that skill. And so when you start with a set of chips, the goal is to win the chips at the table. Right. And how do you get more of those chips? How do you hold onto your chips? Right. How are you the last woman standing? And that process of taking risk because you have to risk the chips to get more chips.
B
So how are you supposed to fold every hand?
A
Exactly. Cause you eventually will be blinded out. That happen at the table will take you out. You can't just sit there and expect things to come. You cannot wait for perfect cards.
B
You don't get pocket aces every single time.
A
That's exactly right. You certainly don't. And you may not even get a pair of anything. So now how do you play as if you did? So I think risking those chips becomes really easy with repetition. But if you don't do it at all today and you want to do that in your future because you want to reach wherever you're working, whether you're an entrepreneur, whether you're working in an organization, you have to be able to make decisions around money. You have to look at what you're doing every single day and say, why am I doing it? To what end?
B
Yeah.
A
How am I helping the firm make Money. How am I helping the firm save money? Whether you're at A, for profit or not for profit, everything comes down to the money.
B
What do you want to say to women who are listening, who really prefer to be hands off with their money? They want to defer and say, my husband will do it. My dad will do it. Whoever will do it.
A
Ultimately, money isn't everything. Yeah, but everything is money. So if you want to survive and thrive, you have to own and be accountable to your money. And that money can be a collective we. Whoever your partner is, there's no reason not to. But the other big thing around your money is if you want to build real wealth, A, it takes time, and B, you have to invest. So every time you decline an opportunity to learn about money, you take steps back from that road, which does take time. People don't become investors overnight.
B
No.
A
Right. There are some natural, naturally inclined investors. But every time you say no, because your investment into your home is an investment you're already investing, if you're making that decision when you invest in this furniture versus that furniture, you're already investing, there's so much we are already doing around money. And then there's this one slice that we just ignore. We ignore.
B
Yeah.
A
And of course, again, it's not hard. We are totally capable of doing it. It's just about getting involved. And the earlier you start, and the earlier you do it also with your kids, the more comfortable. It's just a language. It's like the poker table. Right. There's this whole language. It feels uncomfortable. It looks like something I shouldn't be doing. It's the exact same thing.
B
Yeah.
A
Yeah.
B
You obviously have an incredible lucrative career, but I want to talk about your personal life. What is the biggest risk you've ever taken personally?
A
Marrying my co founder.
B
Wait, how does that happen, by the way? You were just, like, late at the office one night and you're like, are we secretly, like, enemies to lovers?
A
That's right. It literally. Like, literally. Yep. It was a conversation. Never had been a kiss. And it was a discussion.
B
Wait, okay, so, sorry.
A
Literally.
B
Can you just walk me through this? Like, you're working late one night and you look at each other and you're like, we're in love.
A
Basically. It was more like a question, Right. Is there more here? There's a fine line between love and hate. I tell you, it's real.
B
So who opened up the conversation?
A
Probably me.
B
Look at that. Risk taking.
A
That was risk taking? Well. Cause it had gotten. I mean, it was a really intense experience. I think. I think sometimes, depending on the type of business you're in, they are more or less emotional. I think being in a trading business, especially being in the markets. Right.
B
Tempers are short and emotions are high.
A
Emotions are high. So that's what's really real. When you see movies and those things, those things really happen. And by the way, I'm either in or I'm out. Right. So I need to know, because I don't know what I don't know here. And we always talk about your chips. Annie Duke was famous for saying your chips. You use your chips as your voice. You are asking a question. So I put those chips out. I'm gonna get some kind of answer.
B
Yeah.
A
And so I put my chips out.
B
And it worked out.
A
Yeah, it worked out.
B
That's incredible.
A
Yeah, I got lucky.
B
I love that story so much. Honestly, Tumblr could not have written a better love story. Like that is the best meet cute I've ever heard.
A
That's great.
B
And you know, you were already quite successful, but you said you didn't start learning poker until 2019.
A
Right.
B
What is one thing that you feel like you've improved about yourself, having since learned?
A
So I saw a lot of what I already do.
B
Yeah.
A
And if we back up, I never had any intention. Nobody knows Peak six. I became public post Covid. Nobody knows my name. Right. Until more recently. And I was looking for something. I was looking to get more women into my industry. But also I also said I would never be public unless I could bring something that was tangible for women to change their trajectory. And so when I learned poker, I was like, this is what got me here. I just. It wasn't in the form of the game. It was in the form of options trading. Now, most people aren't going to become options traders, Right. But everybody can learn a card game. So if I can change that course of history and if we can start, especially if we can start young, that was my risk.
B
Being public, Being a public figure.
A
Being a public figure.
B
Is that something that doesn't come naturally to you?
A
No, definitely not. Really? Yeah, definitely not my. It's definitely not my natural inclination at all. So for sure. In fact, we laughed because it sort of simultaneously, Peak 6 was starting to do some other businesses and having outside customers. When we do our trading business, it's proprietary trading. There's no outside. There was original outside.
B
It's your money that you are trying to grow.
A
That's it. Yeah, that's right. So as we're starting to do the other businesses. Well, Somebody needs to do it. And who's got the short straw? The female in the room. So I was clearly gonna be me. It just so happened.
B
Your husband's not gonna be in front of the camera.
A
No, he would choose not to be. Too. Right. And that's what we learned in options trading. It's why you don't hear about many of these firms. They are typically quite quiet.
B
Yeah. Behind the scenes.
A
Behind the scenes. Yeah.
B
Yeah.
A
Keep our secrets secret.
B
Exactly. Yeah. What is one thing that you've learned from being in the public arena and having to speak more publicly and be front facing?
A
It's. It's another skill.
B
Yeah.
A
It takes practice.
B
Yeah.
A
Yeah. And I love that advice. Yeah.
B
You can always be better at anything.
A
That's right. That's right.
B
Yeah. Okay, so final question is, do you have anything that you would want to say to our listeners right now? We have. It runs the gamut, but it's, you know, people who are. Who are just starting out on their financial journeys as people who are, you know, high earners who are not rich yet, but everybody wants to be smarter with their money. Is there one piece of lasting advice that you'd like to give everybody?
A
Well, that's. That's easy. Play poker, but it's really bigger than that. Right. It's about. We talk about something called compound experience. And it's like compound interest. Exactly. If you get those experiences earlier. So it doesn't matter if you're more mature in your career or not. If you start doing. Having different experiences tomorrow than today, that's gonna compound quicker. Compounding is all about time.
B
Yeah.
A
And so today is the best day possible for you to start to change that trajectory and take different types of risk.
B
I love it. And that's a really nice way for us to end. Thank you so much for being here and talking to me and all of the besties listening. Let us know where we can find you.
A
You can find us on social, on Instagram and TikTok at Join Poker Power. You can find us online@pokerpower.com and you can find us in the App Store at Poker Power Play.
B
Amazing.
A
Yes.
B
I can't wait. I play every night, guys. Download it.
A
Thank you.
B
Thank you for being here. Thanks for tuning into this week's episode of Net Worth and Chill, part of the Vox Media podcast network. If you liked the episode, make sure to leave a rating and review and subscribe so you never miss an episode. Got a burning financial question that you want covered in a future episode? Write to us via podcastorrichbff.com follow Net Worth and Chillpod on Instagram to stay up to date on all podcast related news. And you can follow me at yourrichbff for even more financial know how. See you next week. Bye. Support for Net Worth and chill comes from AmazonOne Medical when you think of Amazon, what's the first thing that comes to mind? Probably convenience, fast delivery. Everything you need with the click of a button. Now when you think of healthcare, what do you picture? I'm guessing the exact opposite. Well not anymore because Amazon is now getting into healthcare. It's called Amazon One Medical and it offers 24. 7 virtual care so you can speak to a provider within minutes. And they've also got Amazon Pharmacy so after your virtual visit, Amazon can deliver your prescriptions directly to your door. After all, convenient fast delivery is what Amazon is known for. Thanks to Amazon Pharmacy and Amazon One Medical, healthcare just got less painful. Learn more at health Amazon.com.
Networth and Chill with Your Rich BFF: Episode Summary
Title: Know when to Hold 'Em - Poker and the Power of Risk-Taking
Host: Vivian Tu
Guest: Jenny Just, Self-Made Billionaire, Investor, and Poker Player
Release Date: January 15, 2025
In this compelling episode of Networth and Chill, host Vivian Tu delves into the relationship between poker and effective risk management in business and personal finance. Vivian shares her experience witnessing a predominantly male poker tournament in Las Vegas and highlights the scarcity of women in such settings. This observation sparks a conversation about how poker can equip women with crucial life and business skills.
Vivian introduces her special guest, Jenny Just, a self-made billionaire, investor, mother, and accomplished poker player. Jenny explains how her journey into poker began unexpectedly and how it became a cornerstone for her success in the financial world.
Jenny Just [02:30]:
"Poker is a game where you’re dealt two hidden cards and use community cards to create the best five-card hand. It involves betting, folding, and strategic decision-making based on the strength of your cards and your read on other players."
Jenny breaks down the basics of poker, making it accessible for listeners unfamiliar with the game. She emphasizes that poker is not just about luck but about strategy, risk assessment, and psychological insight—all valuable skills in business and investing.
Jenny recounts how she initially dismissed poker as uninteresting and a waste of time. However, a pivotal moment occurred when her daughter struggled in a tennis match, prompting Jenny to reconsider the importance of strategic thinking and risk-taking. This led her to teach poker to her daughters and, subsequently, to a larger group of young women.
Jenny Just [05:23]:
"The confidence of those young girls at the poker table was palpable. It was clear that poker was not just a game, but a training ground for strategic thinking and risk management." [05:23]
This experiment evolved into a global initiative, teaching over 300 companies in 60 countries how poker can empower women by enhancing their decision-making and financial acumen.
Jenny shares her background growing up in Wisconsin with four brothers, instilling in her a strong work ethic and a keen sense of financial responsibility. Her entry into the world of options trading at O'Connor and Associates marked the beginning of her financial career.
Jenny Just [10:00]:
"Being one of the few women on my trading desk was challenging, but it taught me how to navigate a male-dominated industry and hone my risk-taking abilities." [10:00]
In 1997, Jenny co-founded Peak 6 with her business partner. The firm quickly saw success, making their first million dollars within six months—a testament to their effective risk management and strategic operations.
Jenny Just [16:11]:
"Making our first million was exhilarating and petrifying. It set the tone for our future, emphasizing the importance of protecting our gains and managing risks meticulously." [16:11]
Recognizing the parallels between poker and business, Jenny expanded Peak 6’s mission to include teaching poker to women and young girls. The initiative aims to build confidence and strategic thinking, translating poker skills into business success.
Jenny Just [34:37]:
"Creating a safe environment for women to learn poker allowed them to discover their risk-taking abilities and apply these skills in their professional lives." [34:37]
The program has grown exponentially, now encompassing corporate training, senior employee development, and global workshops, all designed to empower women through the strategic elements of poker.
Jenny discusses the importance of understanding and managing risk, both in trading and in everyday decisions. She emphasizes that risk management is a personal endeavor, requiring individuals to assess their own comfort levels and gradually build their risk-taking "muscle."
Jenny Just [26:45]:
"If you’re not a risk-taker and want to change your trajectory, you have to start today. Practice taking smaller risks to build confidence and capability over time." [26:45]
This philosophy is central to Peak 6’s approach, ensuring that while they explore new ventures, they do so with calculated risks and robust safeguards.
A touching moment in the episode reveals Jenny’s personal risk—marrying her co-founder. This unique intersection of personal and professional life underscores the deep trust and strategic partnership that defines Peak 6.
Jenny Just [40:39]:
"Marrying my co-founder was the biggest personal risk I’ve taken, blending our professional strengths and personal lives seamlessly." [40:39]
Jenny reflects on her role as a public figure, advocating for women in the financial sector. Initially reluctant, she embraced the spotlight to drive change and inspire a new generation of women to engage with finance and risk-taking.
Jenny Just [43:46]:
"Being a public figure wasn’t my natural inclination, but it became essential to advocate for women and share our tangible strategies for financial empowerment." [43:46]
Concluding the episode, Jenny offers a powerful message to listeners about the significance of embracing risk and investing time in financial education early on.
Jenny Just [45:28]:
"Start taking different types of risks today. The compound experience of making varied decisions will accelerate your growth and financial trajectory." [45:28]
Through her journey, Jenny Just illustrates how poker serves as a microcosm for business and life decisions, emphasizing that strategic risk-taking and confidence-building are crucial for financial success. This episode underscores the importance of empowering women with the tools and mindset to navigate and thrive in the financial landscape.
Notable Quotes:
Jenny Just [05:23]:
"The confidence of those young girls at the poker table was palpable. It was clear that poker was not just a game, but a training ground for strategic thinking and risk management."
Jenny Just [10:00]:
"Being one of the few women on my trading desk was challenging, but it taught me how to navigate a male-dominated industry and hone my risk-taking abilities."
Jenny Just [16:11]:
"Making our first million was exhilarating and petrifying. It set the tone for our future, emphasizing the importance of protecting our gains and managing risks meticulously."
Jenny Just [26:45]:
"If you’re not a risk-taker and want to change your trajectory, you have to start today. Practice taking smaller risks to build confidence and capability over time."
Jenny Just [40:39]:
"Marrying my co-founder was the biggest personal risk I’ve taken, blending our professional strengths and personal lives seamlessly."
Jenny Just [43:46]:
"Being a public figure wasn’t my natural inclination, but it became essential to advocate for women and share our tangible strategies for financial empowerment."
Jenny Just [45:28]:
"Start taking different types of risks today. The compound experience of making varied decisions will accelerate your growth and financial trajectory."
Connect with Guest and Host:
Jenny Just:
Vivian Tu:
About the Podcast:
Networth and Chill with Your Rich BFF is a Vox Media Podcast Network show hosted by Vivian Tu. The podcast transforms traditional financial discussions into engaging, relatable conversations, making complex economic concepts accessible and actionable for everyday listeners. Each episode features experts and influencers who provide tips and strategies to help listeners maximize their financial potential.
Disclaimer: This summary focuses solely on the content of the episode and excludes advertisements, intros, outros, and non-content sections as per the provided instructions.