Know when to Hold 'Em - Poker and the Power of Risk-Taking
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What's up, rich friends? Welcome back to another episode of Net Worth and Chill with me, your host, Vivian Tu, aka Your Rich BFF and your favorite Wall Street girly. And a couple of months back, I was in Vegas celebrating a girlfriend's bachelorette. We did the whole day club, night club, 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 the 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 going to 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. Hello. So glad to be here. 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, because I didn't know a couple months ago, can you give me like a 30-second rundown of how the game of poker works? Sure.

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. So you mentioned playing with a group of friends. When did you start playing poker? How'd you learn?

So here I am espousing the game of poker. The interesting thing is I learned it only five years ago. Oh, wow. 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. Yeah. And-

surrounded by poker players, and I thought it was gross and definitely not something I was interested in and a waste of time. 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. Okay. And her dad is frustrated because she's losing. He's very competitive. Yeah. As most of those 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.

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. Like, what does that have to do with that? 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? Yeah.

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. Yeah. We'd have never taught them. Yeah. Of course, because they all seem to figure it out. Yeah. Probably had friends who taught them. 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. Yeah. And I always like to say from lesson one to lesson four, literally the skies opened. Right.

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.

I love that. I feel like I got chills from you saying that. Yeah. Gives me the chills too. It's crazy. But you mentioned poker looks 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 U.S. 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 going to become a billionaire? Like, how does that happen? Right. No, no, of course not. No, I grew up in Wisconsin. I had really hardworking parents. My dad's phrase was every day is 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. And your parents were like working parents. My mom stayed home to take care of the five kids and my dad every day. Every day is 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 what

when I became really conscientious around money. Like 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 it's a while ago. And so it's when you would have a printout of papers and they were all connected to each other. Yeah. So they're not quite that way today. With the frillies on the edge. Yeah. So the frillies, that was me. So he said, here, stand, hold this stack of papers. I did. And 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,

Nothing's given. Nothing's free. Yeah. Yeah. So. Wow. 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? So that I wasn't smart enough about. And yeah.

The only thing I really cared about was being in Chicago. So I grew up in Wisconsin, like I said. I went to school in Chicago, obviously, so we have that connection. And so I wanted to be in the city. That was the big city to me. So I interviewed everywhere. And I was in 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... What did you think you were signing up to do? 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 like kind of unheard of in those days. Yeah.

They had Haagen-Dazs and like beer in the fridge. I was like, this is where I want to be. Like, I don't want to be in a suit with like pantyhose because that's what you would have to do. Pantyhose. Yeah, with the nylons. They're so itchy. At the bank, right? So this is – 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. Yeah. And I started my trading career at J.P. Morgan in 2016. And even then, that was only a couple of 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, you know, your area. What was it like being a woman in a male dominated space? Did you ever see that movie Wolf of Wall Street? Yeah. Yeah.

Not exactly. Yeah. But I have to tell you, it's one of the few movies I walked out of.

Because it was too real. Yeah. So, of course, there are some exaggerated points. But a lot is not. Yeah. Right. I remember when Billions came out and people were like, you have to watch. And I had to stop watching. Yeah. But I didn't ever, growing up with four brothers, right? I go down to a trading floor and see big, huge men screaming and yelling every day. Like that part didn't intimidate me. The part that intimidated me was learning options trading. Right. Right.

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 my first day on the trading floor, one of our teammates came up to me and said, don't worry, I'll protect you. And I was like, what are you protecting me from? 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, you know, the 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. Yeah. Did you – 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? Yeah.

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, he has no idea what I'm doing. And he wants me to go back to school and get my MBA. Classic dad move. Classic dad move. So how do I secure? How do I help my daughter, you know, set –

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. Say goodbye to three years of your life. Yeah, so the three letters saved me. So I, because nobody, of course, in trading was definitely getting MBA. Okay. And you mentioned how much you love Chicago. You wanted to be in Chicago. Yeah.

Unfortunately, O'Connor & 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?

So, again, maybe similar to when I started, quite naive. You know, 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 entrepreneurs.

people who traded to go start their own trading thing. Now, we weren't going to 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-person 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 entrepreneurs 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. Use their resources to build your thing. 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 staring at each other. And 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 for everybody listening, needing a balance sheet just meant Jenny needed a lot of money very quickly. 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 Six. It's been around for 27 years. It's never had a losing year. And we used technology really early on, so call 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 Six because we self-funded everything else we've done with the profits from that business. Yeah. I was going to say, I know you launched Peak Six in 1997 with only $1.5 million, which sounds like a lot of money. But when you're starting a literal fund, it's nothing. Right. Exactly. Nothing. Exactly. Exactly.

But you've been able to grow 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 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? Yeah, 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 because 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, like

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 feat. 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. Yeah. That's that risk acknowledgement and understanding your risk. That's exactly right.

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 wrong? At least once a week for 27 years. So I think –

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. Yeah. And so if we didn't know how to do that, we're screwed. Yeah.

So using technology and then connecting to the exchanges by sitting at our desk allowed us to not hire as many people. Oh, okay. So you saved on labor. 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

I remember I was like, we cannot hire employee number 10. Cannot. Because I also know my co-founder, that was definitely not his skill. 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. Yeah, definitely. And speaking of people, how did you select your co-founder, and are you two still friends? Yeah, yeah, yeah, exactly. So interestingly, we were entrepreneurs inside of the bank. Yep.

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, you know, this far apart from each other for decades.

six years at that point. And, or no, four years there. And then when we start peak six, there was actually, there was another gentleman who was actually supposed to be three of us. And at the last minute, he had a new baby and it was decided he was going to go with the banks. We didn't. So now it's just the two of us.

If I'm him, though, by the way, I'm looking at your success right now and I'm sick. Yeah, yeah. Down bad. 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. Yeah, for sure. But when we decided to do it, it wasn't –

It was more him choosing me than me choosing him, 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 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 going to be equal partners though, right? Which...

You ask any male at that point in time, you're going to 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 peak six, we got married. Wait, I don't think I even knew that. Yep.

Wait, okay, so your co-founder... We knew each other for 10 years. Oh, my God. We knew each other for 10 years. Maybe I should have done better homework, but I don't think I realized that. Well, I think it's just because... Well, we don't have the same last name. No, I go by my maiden name. Yeah. Yeah.

Wow. 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 war early days of the firm because there were so many highs and so many lows. Yeah. 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 and both equal. 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. Yeah.

That is incredible. Yeah, that's crazy. 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

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 year review and you're asking for that raise, you have the receipts to back up everything you're saying 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 wait.

that Sherry 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.

Wow. Okay. So this, I feel like clears up so many things in my head now. Okay. Because obviously, Peak Six starts out as a proprietary options trading firm. Yes. But these days, you're dabbling in tech. You're dabbling in other industries. Like, 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 not do anything else. What made you want to do other stuff?

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 that we weren't that smart at the time. A couple of 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

It's about marketing, frankly, to them. 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 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, 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. 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, you know, we certainly have dabbled in places we shouldn't have dabbled. We always, we like to say we've lost more money in more ways than most people you know combined. So, but the good thing about it is we knew how to manage our downside. So we tried things and we're really good at managing

exiting either fails, obviously, or things that probably aren't going to go anywhere. Yeah. And speaking of cutting your downside, 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?

So when I talk about risk with people, it's such a personal thing, such a personal thing. For somebody, you know, raising their hand in a meeting is risky. Yeah. For other people, it's, you know, to the extreme, right? Skydiving is risky. 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. Mm.

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...

That will get you very far, right? And then you can decide if you want to level up at the size of the risk you're going to 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 our 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, you know.

2 o'clock in the afternoon I deploy that much risk, right? At the time. So you have to learn. You didn't have as much muscle memory. 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 going to get better either by, you know, 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 going to get better. And the truth is, is boys and young men do that far more often. Poker is a great place to be doing that than women. Why is that?

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.

It's a learned habit. 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. 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. Okay. 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? Yep. And that changed my life. I'm sure. Because –

It made it half as scary and half as bad. That's right. And suddenly I could think a little bit more clearly versus being like, oh, man, the number is getting really, really big. 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 a data point.

Hey there, I'm Peter Kafka, the host of Channels, a show about technology and media and the future. And this has been a tremendously busy couple of weeks for the tech industry. There's Donald Trump and his embrace by the men running the world's most powerful companies. There's TikTok and its future in the US. And there's DeepSeek, the Chinese AI engine that just shook Silicon Valley and Wall Street. I wanted to get an insider's perspective on all of that. So this week I turned to Jessica Lesson, the veteran tech journalist who runs the Information

Jessica told me why Deep Seek is so important, who she thinks might end up owning TikTok, and why some of the Valley isn't just playing nice with Donald Trump, but really thinks he'll be good for them. You can hear all of that on channels wherever you listen to awesome podcasts. And so I have a number and you might say, well, I want to get to...

whole number again, not just half of it. How do I get there? 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 going to play another hand. Yeah. And you have the opportunity to get back in and do something different. Yeah. You're forced. You're forced to do it. But I also love that you mentioned like you can take smaller risks versus one mega risk. It's like the micro risk. Exactly. Right? Yeah. You just increase them more and slowly you become-

I guess like, I don't want to say desensitized because that's typically a negative connotation word, but like you become less scared every time you take one more risk. That's exactly right. That's exactly right. Yeah. Okay. So onto the topic of poker. Poker power has become a really cool part of the Peak Six 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, in

What inspired you to do that? Was it just that dinner table night with your girlfriends and their daughters? So it all started there. Yeah. 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.

Yes. So then we're like, we'll see you later when we can get back in person. Obviously, it lasted a little longer than everybody was expecting. Two weeks to flatten the curve. That's right. Oh, yeah. Please, two years later. That's right. So roughly late spring of 2020, I was like, well, we're going to have to figure this out if – because I –

I believe it can profoundly impact young girls' lives, right? So that was a premise. So we went to the Peak Six families. Everyone's trying to do stuff on Zoom. We got an app, which is super disappointing when you go to the traditional poker apps, right? Because they're not gender neutral at all. And they're also like very much like being inside of a Vegas casino. It's like super hyper stimulation lights. It's horrible. Yeah, it does not feel good.

But that's all we had at the time. And we said, well, we're going to teach online. So we went to the Peak Six family, several thousand people at the time under there. And we said, we want to teach your daughters and your nieces, et cetera. And then the women at Peak Six 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, right, was sharing ideas during COVID, a woman at Morningstar knew a woman at Peak Six said, oh, can you teach us? 30, 60, 90 women later. Now we are at companies all around the world and 60 countries doing this for women.

corporates, doing it for their junior employees, doing it for their senior employees, doing it with their clients. We're, you know, 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. Yes.

Yay. Super exciting. 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? 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 didn't not want to teach the young girls, but what I realized was this could be a really interesting flywheel because I'm going to have to get a buy-in from those women anyway to teach the daughters. Yeah, of course. I'm probably going to get a 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 within 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. Right. So of the 100, nobody really knows any of our poker players in the world, but less than like 7%, 6% are women. So 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 are...

Whether they're in legal or they're compliance or they're marketing or they're 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 have what we call limping in, right? They all want to just match if they want to play. Yeah.

And we tell them about two times, but three times the big blind. And it just stops. Everything stops. And it's so unnatural. And these are women who are senior. Yeah, these are like C-suite women. 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-assess. Now, the other thing we talk about all the time is,

is capital allocation, right? I always say where you want to be and where you are today, the difference between those two places is taking risk around money. Yeah. And so money- Wait, 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. 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. 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, 'cause you have to risk the chips to get more chips.

So how are you going to do that? You can't just fold every hand. Exactly, because you eventually will be blinded out. The antis 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. You don't get pocket aces every single time. 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? Yeah.

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. 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. 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. No. Right? There are some 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're already doing around money. And then there's this one slice that we just ignore. 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. There's this whole language. It feels uncomfortable. It looks like something I shouldn't be doing. It's the exact same thing. Yeah. Yeah.

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? Marrying my co-founder. 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? That's right. No, really? Like literally. Yeah. It was a conversation, never had been a kiss, and it was a discussion. Yeah.

Wait, okay, so, sorry, 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? 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. Who opened up the conversation? Probably me. Look at that risk-taking. That was risk-taking. Well, because it had gotten, I mean, it was a really intense conversation.

experience. 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 in the markets, right? Tempers are short and emotions are high. 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. Yeah. Because I don't know what I don't know here. And, you know, we always talk about your chips. Annie Duke was a famous for saying, you know, your chips, you use your chips as your voice. Yeah. You are asking a question. So I put those chips out. I'm going to get some kind of answer. Yeah. And so I put my chips out.

And it worked out. Yeah, it worked out. That's incredible. Yeah, I got lucky. 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. That's great. And, you know, you were already quite successful, but you said you didn't start learning poker until 2019. Right. What is one thing that you feel like you've improved about yourself having since learned? So...

I saw a lot of what I already do. Yeah. 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 for...

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's my risk. Yeah. Being public. Being a public figure. Being a public figure.

Is that something that doesn't come naturally to you? Definitely not. Really? Yeah, definitely not my natural inclination at all. So for sure. In fact, we laughed because it's sort of simultaneously, Peak Six 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. It's your money that you are trying to grow. That's it. Yeah. That's right. So as...

We're starting to do other businesses. Well, somebody needs to do it. And who's got the short straw? The female in the room. So I was clearly going to be me. It just so happened. Your husband's not going to be in front of the camera? 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. Yeah. Behind the scenes. Behind the scenes. Yeah. Yeah.

Keep our secrets secret. 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? It's another skill. Yeah. It takes practice. Yeah. Yeah. And... I love that advice. Yeah. Yeah.

You can always be better at anything through practice. That's right. That's right. 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 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?

Well, that's easy. Play poker. Play poker. But it's really bigger than that, right? It's about – we talk about something called compound experience. 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 having different experiences tomorrow than today, that's going to compound quicker. Compounding is all about time. Yeah. And so today is the best day possible for you to start to change that trajectory and take different types of risk.

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. You can find us on social on Instagram and TikTok at joinpokerpower. You can find us online at pokerpower.com. And you can find us in the app store at Poker Power Play. Amazing. I can't wait. I play every night, guys. Download it.

Thank you. 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 podcast at yourrichbff.com. Follow Net Worth and Chill Pod 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.