BigDeal - #100 Master MONEY MAKING In 60 Minutes: Everything They Never Taught You | Jenny Just

Episode Date: October 22, 2025

Meet Jenny Just — billionaire investor, poker player, and pure force of nature. She went from the trading floor to 28 years of straight wins by mastering one thing: calculated risk. In this episode, she breaks down how poker shapes decision-making, why methodical reinvention beats blind ambition, and how her radical hiring experiments at Peak6 flipped finance on its head. If you want to win bigger, play smarter, and think differently about risk — this one’s your playbook. Thanks to GoDaddy for sponsoring this video! Head to ⁠godaddy.com/codiesanchez⁠ to get started with GoDaddy Airo® today. ___________ 00:00:00 ___________ MORE FROM BIGDEAL 🎥 YouTube: https://www.youtube.com/@podcastbigdeal 📸 Instagram: https://www.instagram.com/bigdeal.podcast 📽️ TikTok: https://www.tiktok.com/@big.deal.pod MORE FROM CODIE SANCHEZ 🎥 YouTube: https://www.youtube.com/@codiesanchezct 📸 Instagram: https://www.instagram.com/codiesanchez 📽️ TikTok: https://www.tiktok.com/@realcodiesanchez OTHER THINGS WE DO 🌐 Our community: https://contrarianthinking.typeform.com/to/WBztXXID 📰 Free newsletter: https://contrarianthinking.biz/3XWLlZp 📚 Biz buying course: https://contrarianthinking.biz/3NhjGgN 🏠 Resibrands: https://resibrands.com/ 💰 CT Capital: https://contrarianthinking.biz/4eRyGOk 🏦 Main St Hold Co: https://contrarianthinking.biz/3YfGa8u Learn more about your ad choices. Visit megaphone.fm/adchoices

In communities across Canada, hourly Amazon employees can grow their skills and their paycheck by enrolling in free skills training programs for in-demand fields. Learn more at aboutamazon.ca. Starting in trading is really humbling. We lose 40. Let's talk groceries, specifically your groceries. With Instacart, you want your groceries just the way you like them, right? Well, the Instacart app lets you do just that. they have a new preference picker that lets you pick how ripe or unripe you want your bananas.

Shoppers can see your preferences up front, helping guide their choices. Instacard, get groceries just how you like. 5% of the time. What does that feel like to lose tens of millions of dollars in seconds? The very first time it happened that way, that was rough. Do you think you can get rich if you don't take risk? Jenny Just is a self-made billionaire, co-founder of the legendary investment company, that has made money every single year for 28 years.

If you want to figure out how to bet big on yourself and whether the next right decision for you is to go left or to go right, you're gonna wanna listen to this episode. Time is massively important. It's definitely a marathon. It's not a sprint. When you have that great year,

think about it over a three-year timeframe. Don't think about it as today's money. What can poker tell us about reading the room in life? you have to be thinking about the other cards at the table. Then you have to think about what they're thinking about your cards. If I'm sitting across from someone and I want something to happen, I want more money, I want a different position. They have to think about what they're thinking.

What's the most amount of money you've ever lost in a single day? It's a lot. So you're a self-made billionaire, right? That's correct. That's probably what you lead with when you come in a conversation. You're like, Cody, really? First question. But I think it's really cool because one, billionaires are super rare, but to be self-made, then throw on you're a woman, not that many.

And then you did it in finance and investing. But what's kind of cool, you didn't start out that way. And you've said a line I loved, which is you've said failure shaped you more than anything else. What does that mean? Starting in trading is really humbling. We lose 45% of the time. So it's over and over and over. And that repetition, you know, that compounds, I always talk about compound experience.

Each one of those gets you a little smarter, a little braver, a little bit more nimble. I think I was really lucky to start in trading, on a trading floor in person and sort of feel what it was like, right, to lose those dollars. But I did it when I was young. multiple times a minute. So doing that allowed me then as I grew, I became put on my big boy pants and did a little bigger and a little bigger. You know, people think of me as a risk taker because of where I came from, but I became one. Yeah. Right. A lot of people maybe don't know what trading is. So really what this means is that you were either trading for your own, your own book, your own wallet you could think of or somebody else.

but you're on the line. Like every decision you were deciding, I'm going to put a dollar and bet, quote unquote, on X to happen. And if X doesn't happen, I lose money. That's right. So like to put this in perspective for people, what's the most amount of money you've ever lost in a single day, do you know? It's a lot. Tens of millions of dollars. Yeah. In, in seconds, right? It's not even, you know, a whole day. It doesn't have to go by for that to happen. You're like, can we break it down, Cody, the dead seconds was bad enough. Wow. What does that feel like to lose tens of millions of dollars in seconds? When it first happened, the very first time it happened that way, that was rough, right? Was all that stuff leading up to this, you know, fantasy? So a lot of second guessing. But

you get better and from it and you obviously don't want to do that again. But literally just yesterday, right? So we've been doing peak six for 28 years now. And there's always a situation in the market, right? It's why the smartest actually don't win. Long-term capital management is a great story for people to read about. And they were the smartest and they didn't win. So being humble about when things are going well and acknowledging what was lost. what was skill, and then recognizing a situation where that same thing, it's going to happen again. What am I going to do then when it does? I just have to assume it's going to happen. I think that is the – so now how do I get comfortable? Because, you know, the first losses weren't that big, obviously. Yeah.

But the more you put out, the more the chances for a big loss are. Yeah. I mean, the first time did you like when some – when you lost a bunch of money, you're like, I need to go to the bathroom, and then you just go get sick in the bathroom. Or you just like, do because I imagine like as you get older and better at it, those peaks and valleys, if you're going to stay at the game, if you can handle it and figure out mentally how to get through it, which I think by the end of this podcast, given everything I've read from you, we're going to help people get there, people to manage the peaks and troughs. But I imagine in the beginning, the highs are high. You're like, you know, bottle service at Tao on Jenny, you know. I know what you traders did in finance.

Yeah, that's right. That's right. But I imagine the lows are really low. They are. Yeah. And it's really about recognizing you don't have to have the highest high because you don't want the lowest low. And that's really hard for traders. And, you know, we've had 28 years, never had a losing year.

You know, let me knock on something. Wow. And that's really unheard of in our business. But that's also did we have the biggest year of anybody? Probably not. But methodically reinventing ourselves and thinking about how that next market opportunity, new advances in tech, new advance in people who are, how we're approaching the problem differently, right? Each one of those, we don't just assume that we're going to, we kind of think in three-year cycles roughly of the next Jenny and Matt, Matt is my co-founder, could be, you know, you know, in the garage, especially today with AI.

So they could be there. How do we, we probably have to, it's been three-year cycles, probably have to shrink that cycle down. But a lot is possible with very few people these days. What does it take to not lose money for 28 years in investing? That's, I mean, it's like you and what, Renaissance? And I think they even had one year that was down. What does that mean?

Like, for somebody who's never really thought about like a risk budget or like risk allocation, How could they conceptualize managing risk? You have to assume that you, the worst possible scenario. And you can also assume the best because people are already thinking about that, right? So I assume you're already thinking about what the best outcome is. But what is the worst possible? And then what is the slightly less than the worst possible? Like there is a wide range of outcomes.

I think people are quite binary in their thought process. And what if? and then using examples from the marketplace that have happened before, you know, people don't want to think game stop's going to happen again. And you turn around and then there's another one. So, right, even the smartest in the world at the time when that was happening, we're betting against that stock could actually go higher. It can.

Did you bet against it? Do we bet against it? No. We get what we often do in those cases, we get out of the way. Yeah. And then we'll figure out a good way to play it because we're active in three to four thousand public company names in their options every single day. So we have a really broad portfolio. So there's a lot of things and we like to be where the volume is for sure.

It's a really good way to think about it because by binary, you know, basically meeting everybody thinks either I'm going to lose everything or I'm going to win. and everything, and they're really at the broad end of both spectrums, as opposed to thinking, well, what would it look like if we just continuously won a little bit over time? Or simultaneously, continuously, continuously lost a little bit over time. Same thing. Interesting. You know, what I think is really interesting about you is a lot of what you talk about is, I even hate to use the word mindset, because it's like almost touchy-feely, and you're the opposite of that. You're like, very caught. But, you know, your mission right now, I think, is just sort of what I would call break low-risk mindsets. Can you talk about why, for instance, so many people take little risk,

don't take enough risk, and what you would tell them if they were listening to this? First of all, it's very unique to the person. Like, what taking risk to you means? It's different than what's taking to me. It's a very personal thing. And I think people have to be okay because they compare themselves. So if you self-assess, where am I? on this, like, you know, give yourself a risk scale one to ten. And then, um, what is the purpose, right? Do I have a purpose for taking more or less risk? And I think for most people then I'm, either that are listening to you or are coming and listening to me, they are yearning. Right. There is a desire. As much as I look like I take a lot of risk,

But nobody would have called me a risk taker when I was younger. You can actually learn it. We have to start. So what is a small risk for, you know, if you're a young kid in school, it might be raising your hand in class, right? Okay, I got over that first hurdle. Now, how do I get over the second hurdle? How do I get over the third hurdle?

But I have to make it a conscious exercise for myself, which is why when we talk about poker, I like poker so much because every hand is taking a risk, right? I mean, for a lot of people, just getting to the poker table is a risk, so especially for women. So you think young Jenny, she wasn't a risk taker? I don't think so. Was she tough? She was tough. She was tough.

I grew up with four brothers. Oh, yeah. Not a lot phased me. You know, I went down to the trading floor and, you know, it's a sea of men. And the first day, a gentleman came up to me said, don't worry. I'll protect you a guy on our team. And I was like, from what? You know? I was like a sea of dude. Yeah. But yeah, so that I, that was the good fortune, I think, that I had, that I didn't let the outside get in the way. I was always a high achiever in school, but I did what I was told. I didn't

sort of go on my own and take risk per se. Do you think that most people understand? the risk level that they are. Like, is that just, it seems sort of nebulous in some ways. It's like a hard concept to wrap your hands around. Yeah, we've been talking about building sort of a risk tool. Like a framework? Yeah, a framework because, you know, just putting a stake in the ground somewhere, do most people understand?

I think if they really were vulnerable with themselves, they do. And I think for people actually who call themselves risk taker, they also know there's a another level. And by the way, risk doesn't have to mean jumping out of a plane. It doesn't have to be betting all your money, right? It just has to mean taking more risk than you are today. You know, I was always looking, you know, in my re-review mirror when we were building our company and when we were winning. I was like, when's the loss going to come, right? And so I didn't want to take that next risk. Hiring our, gosh, hiring our 10th person, I was like, no way are we ever having more than 10 people. So, like, that was a really big risk to me. And so, like, I contextualize

all the time what I do. Can I take more risk than I do today? Yes. I mean, when we've been, just recently, right, in the last couple of years, investing in AI, like, how big and where? And, right? And it's, you know, it's another level for us. I have a funny story really quick. It's the one, I love this because I said no to Jamie Diamond. So we were, we had a plan A. And, and, you know, And 28 years later, we've never done our plan A. We were trying to get a bank to be our partner to do over-the-counter equity derivatives. That was what we were, that's what we left to go do. That's what we did when we left, O'Connor.

And it was taking forever. And in the meantime, we started Plan B, which is a business, has been around for 28 years now. And, but it's not that we didn't want this other business to happen, but it was going on and on. We'd hired some people to work on it while we were focused over here. and Jamie Diamond was at for Chicago at the time. And so we got to the 11th hour with him. And it was dragging, he was dragging, he was dragging. So this is 1999.

And right, we don't have our phones or I had a little calendar on my desk. And I circled the date. And I was like, if we don't have an answer for this date, we're out. And they just didn't have an answer yet, right? And we called. We said we're out. So. I bet, Jack.

Jamie doesn't get told no very many times. No. Yeah. Well, for sure, less so today than then. But that is a hack right there. This is totally unrelated kind of, but like I'm divorced and remarried happily. But my first marriage, like we just couldn't figure it out. And it was not good. And I put a date on the calendar. Same thing. And I was like, we will either work through this and we will get, or if it doesn't come to the table and the way that we need to, this is the out date. And I remember when the day came up, I was like, what am I going to do? Not keep my word to myself. Right. Like, that's a pretty important word. Yeah. And I think when you do it the first time, you do something like that, it's definitely motivating and it's inspiring. You're like, all right, I did what I said. And because it's time, right? That's a ways out. You don't know how you're going to feel or think or anything about that. Obviously, you have the luxury of changing your mind if you want. But sticking to it, definitely changed my tradition.

You inspired me. Right now, actually, we do like, our members do like $300 million in small business transactions a year. Nice. And we have some banking relationships, but I want one deep banking relationship. And when I tell you, working with these SBA banks, what the piecemeal nonsense they want to do, where you can't actually see through to who bought, you know, the business. And they're like, well, why don't you email us when they, you know, close? I'm like, we have a hundred million eyeballs a month. Right. We're doing so many, we're doing more transactions in cumulative than some quarters you are. Yeah. That doesn't work. Yeah. And I think I need to put a calendar on the date to say, if we don't do it by this date, I'm going to buy a bank. Right. And then I'm

going to have no partners. Yeah. And it's another example of an industry that is so outdated for small business. It's so hard. That I'm like, you know, fine. I could buy one. And so, all right. Right. Now next time you talk to me, if I don't either have the partnership I want or have bought a bag, you have to yell at me. There you go. Which is annoying. I don't know if you were like this. But my mom, like, when I was growing up, she would always say like she was worried about risk, actually. Risk was bad. And I think if you were to ask her, she would still kind of think risks for a letter word just like the rest of us. For sure. And why would you do something that takes more risk? And, you know, I think she's a woman. You know, my family, she was a school teacher. She really wanted things that were quote-unquote guaranteed. Yeah. And I'm wondering, you think that there is maybe this one skill or even a game that can help women break out of that.

You want to talk about what it is? I've been a quiet person for 24 years. I was a quiet person until I learned the game of poker. And I didn't necessarily have to be out there for our companies. and but I have been trying to help women accomplish more what they want to do, which for me, it was clearly taking risk around money was like the biggest inhibitor. And when I saw poker, it was the closest thing I've seen to the training I got as an options trader, right?

Because people aren't just going to become options traders. First of all, there's not that many in the world, men or women. and I'm going to go study options trading is unrealistic, I think. Playing a card game, however, is not. And the irony of the whole thing is, you know, our firm is filled with poker players in the financial world. You see them all the time. And I just ignored the game because only the guys were playing, first of all. I thought it was a waste of time.

and little did I know. There's a little secret. They've been doing it for literally hundreds of years. And so I'll just tell the backstory real quick. So my daughter was 14 at the time, so it was in 2019, playing a tennis match, losing. Her dad was a college athlete, frustrated. She's losing to someone she looks like she should be able to beat and comes home and sort of chirps. to me, because he doesn't want to her, and says, you know, she may as well be hitting against

a wall. She doesn't realize she's playing against someone who's thinking and strategizing. She needs to learn to play poker. And he wasn't really, he's more than a blackjack guy. And I just thought he was being ridiculous and I walked away. And like two weeks later, I was like, shy, I teach my 14 old daughter to play poker. And then, of course, that annoyed me because I would never have three sons as well. I've never said that about them. And by the way, they already knew how to play because they all just seemingly figured out, you know. And so we, I did an experiment, right, when it does a good entrepreneur do. And 10 girls, 10 moms. And it's the only reason I'm sitting here, honestly. So the transformation in those girls from

lesson one, literally four one-hour lessons to lesson four was like literally, skies opened. It was so extraordinary. Now that at the time was really all about confidence. That's what I saw. But as we proceed and move forward, actually was going right into COVID. I was like, well, we'll do more of this. We had like three states, 17 clubs, something like that.

And this is all about being in person. we you know months in we're like I guess it's not about being in person anymore so we better figure this thing out so we actually go to peak six employees a few thousand employees said we want to teach your daughters and your sisters and your nieces and in the one when we're like oh so good for them why aren't we learning and I was like great idea so we start doing it on zoom of course and morning star large international firm heard what we're doing us to do it and today now we've taught it over 300 I think it's like 370 companies 60 countries

and through that process I started to learn and that's when I saw that same repetition playing that hand making that decision with imperfect information

playing people right because we're trading right there's a customer on the other side even if I don't see them there's somebody there what are they doing why are they doing it right

a thought process that I seen outside of trading was right there in this card game. And when you think about, right, how men espoused a game for so many years, but, you know, our presidents play. I just met a man the other day who would play with Obama in the White House when Michelle was on vacation, you know. So it was... Naturally. Yes. And I think a Trojan horse, honestly, for women, to learn this game, play this game, build those skills. By the way, this isn't something that you are naturally, someone might be naturally good at it.

There's zero reason why you cannot be good at poker. And then once you start to understand the core of it, how it translates, not just to business, but to life too, whether it's relationships, decisions that you have to make in life, right? You can see how that hand you just played looks like that. negotiation you did, how that hand you play looks like that meeting you were having. Like, where is the power, right? Is the person with all the chips, certainly. But what if a couple people have the chips at the table? Now where's the power? Well, where's the position that they're

sitting at the table? Each layer is quite an extraordinary way of, you know, unfolding stories in your life. And when you start talking to people about why they played a hand a certain way, there's so much to gain about how other people think and how they approach. My last bit is the most fascinating thing we've been doing this because obviously we're teaching mostly women. We will teach men. We're teaching some of your men today. But most men already know how to play and we're teaching people from scratch. But the surprise, the surprise when they start playing the game, what's actually happening. and how quickly they can translate it to what they do at the office every single day.

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No, it does not hurt that. And I always thought about it as gambling, you know. And I don't like gambling. I don't like risk. Right. So I'm like, I'll bet on myself all day, which if you think about it is another type of gamble. But, you know, it wasn't until I first started talking to you that I thought, huh, this is interesting. Because you and I talked last time about, you know, the thing that I, the thing that keeps me up at night.

Because I know there are people listening right now. And we could give them every tool and every tactic and every how-to. But if they don't have the right mindset, if they're not willing to actually take action, which is a risk and increase their risk tolerance, because my belief is by and large, it's harder to get rich. If you don't take some risk, it just seems harder. And that part, I've never had a really good solution for how we could teach them that. Because it's all the touchy-feely stuff, right?

Like manifest and fluffy and blah, blah, blah. And I'm not so good at that. And so, but then I read this thing the other day that I want your take on. The quote was, making money isn't hard on learning everything you know about it is. Money goes to people who treat life like strategy, not survival. This isn't about luck. It's about leverage, understanding the rules, then bending them in your favor. Do you think that's true?

I think there's a lot of truth to that. I think there are a lot of things we're told about money that may or may not be true. I'd be curious your take if I could rapid fire some like money sayings to you. And you could tell me, what do you think about? that true, false, and what are your thoughts? Okay. Here's the first one. You should just save and skip the coffee. I think you've got to have your coffee. But, you know, if you're not saving somewhere, we're really good at defense as well as offense. So, and I think you have to have members of your team on both sides.

But if you're not enjoying yourself along the way, none of it's worth it. Yeah. What about if you deserve it, you'll get it? That's a little tougher for me, I would say. On above average, I'm talent, right? But, and, you know, we've done a lot of experiments at P6 on types of people we've hired. And maybe deserve is the same as the hard worker. I'm not sure.

I don't hear it that way, but the hardest working people are the people that have succeeded on our team. And people stay because they know they're rewarded for working their butt off. And the version of them that comes, right, it's not the most obvious person. I think peak six has done a really good job of bringing, you know, a wide range, including a lot of females, more than anybody else in the market in terms of capital allocators. actually making decisions around money, we kill them. And, you know, honestly, I think one of the reasons why we succeeded is because I brought a different viewpoint. You have to remember, the 1997, like for my co-founder to choose a female, but wildly unheard of. Well, there was very

few to pick from to begin with. Did I deserve it, right? I work my ass off. Yeah, I like it. Yeah, I was watching the video the other day. And it was like, I just want you to keep repeating, like, I will be rich. I deserve to be rich. So I was like, we're going to need to add a few steps to this process. Because that's not going to get you there. Yeah, I was like a lot of conviction, you know, the young woman had. But then I saw it, had a million and a half views. And I sat there thinking, oh, man, you know, sometimes we've got to ask ourselves,

are the people that we're listening to the ones who have actually done the thing that we're trying to get? Right. That's why I think it's interesting when people who have made a lot of money, had a lot of success, are willing to talk about it. It's not that common. Right. Like, does it still feel weird for you to talk about, like, when people call you a billionaire, are you like, ah, it feels awkward? Yeah, it feels awkward.

Yeah, it's weird. But I also think, I also know, like, to represent, like, it's important. Totally. So, yeah. You know what's crazy? We've had three female billionaires in here in the last week. Wow. Is that great? Because there's not very many. So then I was like, what's our percentage? We got a high swing ratio here. That's pretty good. This is pretty good. What do you think about be patient? Wealth comes with time. For sure. Time is massively important. It's definitely a marathon. It's not a sprint. I do think there are, you know, moments that are not exactly that, right? You know, unexpected days. we make a lot more money than we should have.

I, you know, we tell our traders too. When you have that great year, think about it over a three-year time frame. Don't think about it as today's money, right? We don't want, because traders can be like athletes in many ways, way too much money and too young of an age. And we're really proud that people tend to stay a really long time with us. and being a role model who's conservative around spending, right? We're really also super conscientious there, maybe too much so.

We've definitely been criticized for that in the past. Like we're watching the pennies to close him. It's like, well, if you don't want me to watch your pennies, I won't, but I'm going to watch mine. So what? You said you do a lot of experiments at peak six. What are some experiments you do with your employees or to determine, and strategies. Because it does seem like you're a very systems-oriented thinker. Yeah, we are.

Well, we like to know what is working. It's really hard to discern, you know, what actually it is. I'll give you, this is a fun example. So my co-founder grew up playing hockey. Six years in, we got married as an FYI, so I know him very well. But always interested in the NHL. And so when the opportunity was there to potentially, you know, be part of a team, we were looking at it. At the time, so let's call it, you know, early 2000s, there were like six guys talking about hockey statistics on the internet, you know.

And so, and he was one of them. But they're all really bright. And we said, well, what if we took all of those people and we just brought them in as a class? And is there something about their approach, the way that they're. they think that might make a different type of options trader. We did that with poker players many years ago. Before I knew poker, we'd done that with taking the smartest people that would possibly come to us.

That was a complete fail, by the way. But anyway, so back to our hockey people. So they came on, and they were okay. They weren't great traders, but they were there working on, you know, hockey analytics. so if indeed we ever had a team or not. Anyway, they ended up leaving going to hockey teams. And we were talking about this the other day, which is why I was thinking about it. I think the last 12 Stanley Cups, five were either one, I think four, and then one was second place.

Whatever, runner up, whatever you call them, loser. But were X-Pix-6 data people. Wow. Well, they're data of people for the hockey teams, but yeah, XB6 employees. You're like, what's that movie with the baseball guy? Money ball. Yeah, you're like the money ball of NHL. Yeah.

Oh, yeah. I mean, Matt loves, loves, loves, loves. Should you have taken a little piece of those teams? Yeah, exactly. Wouldn't that be nice? Yeah, the Panthers is one of them. But we ended up being part of the Minnesota wild for a little while. Interesting.

And then not anymore, but. So then is it true? that the smartest people that you've hired for traders do not make the most money? We train. People have no knowledge coming in. So you don't have to know. You don't have to have a finance background, an econ background. You can have a history background.

Matt has an English major. So that was an English major. I was a business major. So we're looking for people at the end of the day who work really hard, who are curious. And obviously, they have to be above average intelligence. like just to get into the math side of options trading. As measured by IQ? Do you give people IQ tests?

We don't give them IQ tests. But there are lots of interesting, you know, mathematical ways to solve problems. Yeah. You know, Google, when they first started, all those creative ways of testing people, we like to do that. Do you have like a question? You ask them every time if I want to come work for Ginny. Do I got to? No, we don't, no.

You know, because I obviously don't want to interview these young kids anymore. but, you know, we keep it fresh because there's so much sharing and stuff that happens now. Otherwise, they'll cheat. Yeah. But there's a lot of culture that's involved in our hiring, too. We're different than a bunch of the other trading firms on who we bring in and who we don't bring in. But it is they love it when they come. That is one of the things we're most proud of.

Though the other interesting thing is, is if they leave, we haven't had any. X-P-6 people really, you know, create a firm like we created a firm. Interesting. Though that is also true of many. You see that actually some of the other financial firms, you'll find some. But not so much. It doesn't happen that often, right? There's not that many option trading firms, for example.

But the, you know, Saskwana, who is O'Connor, where we were at, competitor forever, is still there. Yeah. Yeah, well, I met a bunch of those guys at AEI. I think I was telling you last time. And I didn't, to be fair, I didn't really understand. You know, when I was in finance, I was in private equity and asset management, but, you know, like index funds, commingled funds, that sort of thing. And I always thought about trading. Maybe I did that in the beginning, but it was really like arbitrage trade.

It was like for, you know, State Street, just making a market. And then I met those guys. And I was like, and I think I could say this about them and they would be fine with it. I was like, you guys are weird. Like this is a different crew. Yeah, it's a whole different animal for sure. Yeah. They're like physicists and rocket scientists that now trade online. That's, yeah. So half of what you're looking for are these people who basically they just see the world slightly different. There's some like sort of asymmetric little spin they have that everybody else doesn't have. Because it's really a commodity at the end. of the day, but, you know, being in equities, this is what I always say, especially for females. Like, companies are about people's stories, right? Just like here, you know, it's about your story. And following people is really interesting. Following the AI story is really about the people who are doing it. And so I think it's a great place in the equity world for women to get their feet, dirty because they can they draw out that and they have real nuances about what they can understand or not understand again because I see myself like why why was I able to I was trained by someone

who was really good at what they did and that's what we do for our people so if you're interested in the markets at all going on the equity side is a really interesting place to start so is the framework for being able to take more risk and thus potentially have more reward it sounds like, and tell me if this is wrong, something like you have to do it more. This is your compounding experience. Then you have to do it, I don't want to say the correct way, but with some sort of mentorship or guidance, just any sort of risk taking, probably not great. It has to be some sort of structured risk taking. I think it helps. It helps move the ball systematically forward. Yeah. I don't think it has to be. But I do think that helps for sure.

And then what's the next step? If it's take a lot of risks, structure the risk. and then take bigger risks? I think the next step is, you know, again, there's this idea of risk management that I'm doing. How am I evaluating my doing? And you need time to go by. We don't know if a trader is going to be great at their job or not for a while. just like you can go and be a beginner poker player and be a pro. You can.

That happens, you know? And so you need enough time to go by and then some assessment of that data to start to tell a story. It's like playing a hand versus playing, you know, an entire game of poker. That's where the hands add up to the game. and hopefully, you know, the game, you know, that your table, then you're moving, it's like more like a tournament, right? Then I'm moving on to the next table and I'm moving on to the next table. So along the way is, and maybe it's, you know, the context switching happens so much as you're taking risk. You open yourself, like your aperture opens up so much that your,

you're regrouping becomes more important, not less important. Like as we take more risk in AI, I make sure we step back and say, okay, is that really what we meant to do? Because all of a sudden we're in, we're in so deep. You know, it's the same thing, you know, like I'm on the turn. I'm on that fourth card that comes out on the table. And I've got a lot of money in this thing. You know, the one thing as a trader you do, you go home at night, you mark to market everything. If I had to start tomorrow, would I do exactly what I'm doing today?

and if I didn't and if I shouldn't and I should pivot I got to get out or you get out of that hand in some way and some things you can't get out of obviously it's one thing to fold the poker hands and other things you get out of a business or a business line or something along those lines but the reassessment the loop right you don't have to go all the way back to beginning once you know you're on 10 times of doing this you're going back to five and you're reassessing five to 10 because you got better you went to a different level, one to five, then you went to five to ten, right? You're going to come back and reassess,

you know, I mean, there's no, I think there's no stopping learning. I think people think once you get to a certain like dollar amount or something like, ooh, you know it, you know the answer. Oh, no, there's, there's a lot more to come, right? I remember, you know, Matt used to say, you know, so what's your number, right? Yeah, totally. And we all would say it to each other. What was it? Well, it was, it was 10 million bucks, right? Then it was a hundred million bucks. Like, wait, so then what, right?

It's the same idea. How do you, life moves, right? And if you have figured out a way, but that doesn't, it's not a given. I mean, you know, we've had some serious investments that have been really big valuations that have gone to zero. You're talking $13 billion a zero. So those are real.

You're watching some of these AI stocks move around. Like people are getting hurt. And a lot of people are making a lot of money, right? If you're in crypto. So like every step opens you up, I think, differently. But I also think what I love and I love about some of the people who, you know, are following you, is that I know where I want to go, and I don't need to go to that next. You know, I think I have a, you know, a little bit of an entrepreneur's, you know, disease.

You think so after like 15 turn around. So I was looking at all the companies. Yeah, it's not, I have to really consciously tell myself to know. Because it's interesting to me. And people who are entrepreneurs are interesting to me. And I want to see them, I want them to feel what I got to feel, you know, even the bad moments, right? They really have to be ready. I think that's the, you know, me in 1997 versus someone starting today.

It's, it's, you're not sharing your fails, you know, you're living your fails. Like I just keep my fails on my desk, you know, just the list. Do you really? Yeah. Like a piece of paper with all the things you lost money on? Yeah. Wild. Is it one page?

Two page? Oh, it's not all the trading because there's so many trades, right? But it's the company fails, right? Wow. That's amazing. That reminds me of like Astro Teller from Google X. He used to put on his wall in his office, his failure resume. Yeah.

You know, that's fascinating because my other friend who's a hedge fund manager, he does the same thing. In his bathroom, he has a picture, like really big one, and on it are. all the companies that failed that he invested in. And like some of the emails of people telling him, like, you shouldn't do this. And then he did it anyway. Yeah. What is that? Is that like an inoculation to remind yourself you're not superhuman? You know, time heals things, you know, and the pain and suffering of some of those. I don't want, I don't want to make that same mistake, just because I can. Why should I lose, you know, $5 million or $50 million on something if I, I truly know better?

When you have quantity, right? And I think I heard you say recently, you know, why I have three businesses there? Okay, we can have one really good one. I totally agree with that. It's distracting. It's a heavy burden. But some people are just built for that. So the fun and the drive and the curiosity, can I?

Right? So we've created two billion dollar, two multi-billion dollar businesses. Do I want to create a third? Absolutely. I wish I didn't. I wish I didn't. I really do, though. I want to prove it.

Why? So who? Well, it's really, it's really to me, you know? And nobody knows. Nobody really knows anything because we're a private company. But, you know, it was one whisper, one moment in time because we were supposed to take one of our companies public. And then we didn't. It was sort of in the spec craze.

So that's one company gets leaked and that's how that whole story goes. But it turns out that story is great so that I can get more women playing poker. Right. So that's what drives me to be in public at all and talk. But it's an itch that you want to scratch and you have to be super conscientious. I don't care if you have a big business or a small business. But that desire, that's what the failure list. By the way, I have a live event.

I only do one a year. It's huge, how big, really big, in Austin, Texas, just for people who want to make more money, buy businesses, build businesses. It's called Main Street over Wall Street. So if you liked this episode, you're probably going to want to be there. There's only a couple hundred spots left. So click below. I want to shake your hand in person in Austin, Texas, or go to ms ows.com. M-Sows. We'll see you there.

Hey, it's your friend Cody. By the way, guys, I just realized that a bunch of you are not subscribed, which is crazy because I feel like we hang out every week and we talk about how to make your life better, how to make your bank account bigger. And I want to do more of that. So one, thank you for being here. Like sometimes I might pinch me moment, you know? And also share this with a friend, subscribe. The only way we grow is, when you share it. And we only show up on your feed when you subscribe. So I promise that if you do that, I will continue to make this podcast a way for you to steal all my rich and successful friends so that your life can be even better every single day. Do you think you can teach people to

love the game like that, like to become obsessed with just playing, whether the game's business or poker or life? And if so, how do you, how do you teach yourself to love hard to things in business. So I think there has to be some inherent, like, desire that starts it. Can you put fuel on the fire? Absolutely. I think part of the way to do that is be surrounded by people who are amazing, right? Amazing in whatever way. So, like, we really, we yearn for, you know, in the arts, right? When we, you know, fashion, whatever it is, like somebody, you know, Matt's some energy company in the middle of Utah in the middle of nowhere the other day, just because we're so curious. And so I think that curiosity builds, you know, sort of the awe of being a human, what other humans are

capable of doing. And we so enjoy watching that. People enjoy, you know, hearing financial stuff from us, especially in Austin, which has been really funny. They're like, we don't know you people down here. Very much so. Yeah. So that's been. funds since we moved to Austin. We don't have you people. Now they will. Yeah, now they will. But yeah, I think when we are looking, I know you talk about green and red flags, we are looking

for someone who doesn't have all the answers. We are looking for someone who's curious and wants to figure them out. Because I think it's inherently drawing ideas. We do this a lot. Like our very first piece of technology was because I went into a Wendy's. and which is funny and whenever I see them like why was I eating it

Wendy's but anyway you look like you frequent the place right right exactly but literally there was someone there taking the order and then there was you know it used to be that big boulder of a screen was in the corner

and maybe you don't remember that but I do and someone was doing the fries and you know we used to laugh you're the fry guy you know but we that was our that was our tech we built and because how were we gonna

as a couple people in a room we're going to manage because you have to the you have to be broad enough in your trading, right? It's not like we're Goldman Sachs and we have flow, right, which is two people in a room. So we have to get a broad enough portfolio for this thing to make sense. But eventually it became, it was Walgreens, it was Walmart, like we created an inventory management system for options trading. And nobody had talked about that before. We

literally had off the shelf models where everybody was like, the smartest people were creating the best models themselves. Whereas we just bought. So we just approach the problem differently. How do you do that? I think by being curious about the worlds, you know, being curious about learning new things and, you know, abstract or angular to what you normally do. What companies have you invested in or built or turned around that you're really proud of, but you don't talk about a lot? Because you have a lot of them. Like, are there a couple that you're like, you know what? We did this thing and nobody even knows.

I think there's a lot of pride in turning anything that's like hemorrhaging into not hemorrhaging. Like there's a lot of pride just in that. There's a lot of pride in helping the people who are, who put their heart and soul into it to not feel like they caused a calamity and were really part of something that worked. It just needed some small tweaks. I think there probably isn't, I think there's probably more that, I'm pretty tough. I'm not, I'm not the one to pat on the back very often. I think there's a lot more that I think we could have done a lot more for. Ultimately, there are people who are behind these things, right, that I wanted some other outcome, right? There's more fails than there are,

successes. And, but even ideas we had that we, you know, thought could be interesting. You know, we were, we were either cocky or stupid or, you know, we just didn't really understand it so much. You know, we've entered the insure tech space, which is fascinating. You know, I didn't think anything was older than sort of like the way the financial world, the meat and the, you know, the pipes of the financial system work, oh, no, yeah, just go into the insurance side of it. And it's a whole other. And that doesn't mean people want to change. And so those are the things where, I mean, I just the weight of the world on like, I know we can. Does anybody care? Right. And I'm trying to bring a team along to care with us and be different, an approach solving the

world differently. But, you know, they're big industries. That's what I think. All right. I think also why get the entrepreneurial itch because there are, you know, these smaller businesses that you can continue to do that give amazing opportunity for a small team of people that you don't have to take on that, that massive world. Unfortunately, you know, we're sort of in that space. So, but yeah, I think I'm big now. So, yeah, you know, you can't get the same thing out of like a million dollar laundromat. No, no, no. I don't know, maybe. You never know. You never know where in my show. It's funny, though, because one of my partners, he talks a lot about those types of businesses, and he and I would always talk about them.

And so I'm fascinated by it. I think there's an incredible amount of opportunity, you know, in sort of cycles. I think we're in a really good one right now with AI to help you sort of leverage it faster, like unique opportunities that come along. And what does that mean? It's either just helping you on the marketing side or it's helping you on the research side or just helping you execute the bones of getting a company off the ground, which is always more burdensome than people think it is. But you have all those tools in your toolkit just got fucking awesome. That's amazing because I think a lot of people are really scared about AI right now.

They're like not as optimistic. Maybe the like builders, people who really understand tech are. like, oh my God, every day I almost can't keep up with the new things. But what would you say to somebody who right now is like, I'm super scared of AI? I actually think it's going to take over and make me irrelevant. Yeah. Wildly important that you get your hands dirty. Right. So, you know, for poker power, we're building tools all the time for our app, for marketing reasons, et cetera. I'm like, I'm going to get in there and build a tool myself. Right. So. What are you using? What are we coding with? What? Well, Claude. Cod. Code.

Do you ever use Replit, too? I have not, but I've heard of it. But I think it's really important. Who cares that it doesn't go anywhere? It helps in so many different ways from how to think about solving the problem to how to get a thought into the world in some form or fashion. At a minimum, having communication with somebody else or technologists, who knows. So I think getting your hands dirty And you can't mess it up

You can't mess it up Which is super cool Yeah And by the way Everybody else is getting their hands dirty now too They're not experts Yes there's some technologists We're not trying to compete with those people

Right? There's 98% of the world Who's just like you So we talked a little bit about poker But if business is a poker game What are the deadliest tells and entrepreneurship. What do we have to watch out for that we are signaling to other people as entrepreneurs? I think entrepreneurs, their biggest tell is their over-excitement about the possibility.

And so they have a great hand. I'm just not playing, you know, because I don't believe. So, or it might play strongly against them, meaning I might exit. So, and we see that a lot. because we do see a lot of newbies that do come in. We're happy to think and listen and hopefully mentor a little bit, but nothing can go wrong. And it's like, I don't know, that flush might come out and all yeah, I have as two pairs. And they're just not cognizant.

Yeah, just a little naivete, I think. How do you flip that around? So if you are really excited, what do you need to do to temper that? Is it having plans A, B, and C? Is it being honest about the risks? How would we get Jenny on board? If I'm like, I'm an entrepreneur, I want to do something with Jenny, I want to show her how great I am, but also show her what a smart thinker I am. Yeah.

There's a bunch of things. We always say there's like sort of not a formula. It's more like a picture. I think they have to be aggressive on the offensive opportunity. They do. But if they can't address anything defensively and or they have not shown where they have failed in the past or acknowledgement of failure, you're in some former fashion, whether it's in this product or somewhere else, I think those become definitely red flags for us. I want to know like you're going to conquer the world, but I also want

to know how you're going to methodically get from A to B to C. I think a lot of times it's really important as an entrepreneur to understand what's happening in the room around you. Like context is super important, not only in, you know, running a business, but let's just say there's somebody and they want to get promoted or they want to do better in their job or they want somebody to take them more seriously. What can poker tell us about reading the room in life? What cues? Yes. This one I love only because it's so relevant, the context, right? We talk about levels of thinking. So if you're just thinking about your cards, they might get lucky. You have to be thinking about the other cards at the table.

Then you have to think about what they're thinking about your cards. Right? So if I'm sitting across from someone and I want something to happen, I want more money, I want a different position, I want a different challenge, I want something. I have to think about what they're thinking. And I have to think about what they're thinking about, you know, it's my boss, the rest of my team. I have to think about what they're thinking about what they owe to their boss, right?

I have to set, literally set the table. in, you know, full color as opposed to black and white. And that's where we get messed up. It's like, I would love to give you more money. But did you hear, were you in that meeting over there? It's probably not a good time. You know, it's just there are some things that are wildly simple, and people are just so adamant.

They're like, they've been so frustrated, and they come in, and they just want A, B, and C, and because they're not addressing the context. That's why when you sit at a poker table and you start to learn, right? And now you're like, oh, I'm going to play with my family. Oh, I'm going to play with my friends. I'm going to play with strangers. Like, all of a sudden you go, oh, that's why this is like the office. That's why it's like that meeting.

That's why it's like that conversation. Because I don't know everything about the people I work with. And one fascinating thing we've done with our management teams is have them play poker together. It's amazing what our managers learn about their teams by playing poker with them. them and vice versa but you know obviously I hear more from the senior managers but would an example be like um Mary always folds really early or doesn't put a lot of chips on tail absolutely she doesn't take a lot of risk yeah absolutely no question and then now it's a conversation yeah you know it's a conversation with Mary like I notice this um like you want to do it in a way so that Mary still keeps

come back to the table right because you want her there, but you want her to recognize, you know, so what do you see? How do you approach Mary? And, you know, what did you do on that hand? Why? What if? One thing you can probably work on, right? And all of a sudden, she starts doing it, because that is way uncomfortable for Mary to do three times a big blind when she goes in. She just wants to tip you toe in. So what message are you sending? And they start to learn. This is where the self-assessment starts to come in and go, Oh, wow, I didn't realize. So to wrap up, if there is, let's say there's a woman listening out there right now.

And she knows, like you said, her gut, she knows that she's not taking the right level of risk that she wants to in her life. She is a little scared. She's not sure what to do next. And, you know, she might not have even understood all the things that we talked about today. Like, what would you tell her, hey, if you want to level up your life next and if you want to change your mindset about risk, and your capability, what advice would you give her? For me right now, because now I've seen the impact with so many women, hundreds of thousands, the emails I get, the LinkedIn stuff we do, the DMs,

learn poker. And I also say, like, if I could have learned poker when I was younger, I think I would have saved 10 years out of mistakes in my career. You would have had your third billion dollar company. That's right. I'm behind. Real slacker. Jenny, this was such a pleasure.

I love your mission. We're going to put in the show notes the link to your website, which I think is, I loved the risk question at the bottom of the website, too. It made me think about what my risk was for today, too. And then also about peak six. And then also, most importantly, poker power, where they can go and learn more about how to play poker. Now, I think you were working on an app last time I talked to. Is that out now? Yeah, the app is out.

Poker Power Play. That exists. So we teach people in person. We teach them virtually. And, you know, we're doing it every day. We have 20 some odd teachers across the U.S. who are traveling or being online to help move the ball forward for anybody who's interested. That's wild.

Do you think you're just created a bunch of competitors now because you're going to get all these women now? That's so funny, you said it. So my co-founder, Matt, he said. He said exactly that. You literally, like, one hour ago. And he's like, that would be a pure joy for us to be able to do that. I love that. I think most people don't understand that, like, at your level of the game, I imagine,

yeah, you want to keep winning, you want to keep building, but it's also something bigger. Yeah. It's like, what are you going to do? Take all the jets to the grave, you know? No, at least some behind. Jenny, thank you so much for being here.