Jenny started her career on the trading floor in Chicago. She co-founded Peak Six in 1997 with one and a half million dollars in seed capital as a proprietary options trading firm. Now it's a multi-billion dollar financial services trading and technology firm. Really excited to hear from Jenny today. Please join me in welcoming Jenny to the stage.

Stupid women drivers! Stupid women helicopter pilots! It's not prejudice, it's just that men are naturally superior drivers. You're goddamn women drivers! Women drivers. Maybe women are competent drivers. Women drivers, that's the problem. When a woman's at the wheel, polyglass means more than mileage. Welcome everybody and thank you for having me here today.

As they said, I'm Jenny and I started Peak Six in 1997 as a proprietary equity options trading firm. We've evolved over time into a technology firm, including in the insure tech space. And the one thing I know about these videos, men are bad at math. As you can see, there's clearly no difference between driving abilities and insurance rates.

Now, 100 years ago, women were less than 10% of the drivers. It was deemed risky and a man's job. But 50 years later, we see that it's changed. We see these kind of trends again and again, where participation rate eventually equals skill or ability. We know that women are half of the voters.

They're more than half of the college graduates. A really, really important place it has not changed is in the financial world. So Peak Six also owns, as they were saying, the Apex FinTech Solutions. It's a SaaS-based clearing and custody firm. We have 220 B2B clients, 120 billion in assets.

We have tens of millions of end customers. The truth is, more than half of you are likely on our technology today and you didn't know it. We are the back end for more than 60% of the FinTechs out there. So think Webull, SoFi, Ally, Stash, eToro, Public. You're probably on our technology.

And what we know about that data is it's like driving and voting and education. There's no difference between investing, doing it between men and women. However, there is one big difference, and that is participation rate. I wonder why. I've offered our lovely sales assistant, Danielle Harrison, here $10,000 to shave a fucking head!

Yeah, you want this? Let's give a fuck! So while we have many different businesses at Peak Six, the heart and soul remains our trading firm. Now, when I started Peak Six in 1997, the world was very different. All the trading happened on the exchange floors. I was in those trading pits.

So it's clear to me that things could probably be done a little bit better. And in 1998, we actually started using technology and we became one of the first off-floor equity options trading firms in the world. And despite all the booms and bust cycles, the dot-com, the financial crisis, COVID, Peak Six has never had a losing year.

Now, we're not a fund. We don't have outside money. We had a little bit, you heard in the beginning. Those investors were paid back many times over very early on. You know, I could have invested in bonds or stocks or Berkshire Hathaway or Steve Jobs and Apple, but I invested in the best idea I could see.

I invested in the proposition that a female trader could hang with the guys. So how did that turn out for me? Bonds, $100 invested in 1997, now worth about $300. The market, about $700. Mr. Buffett, $1,200. Apple, $180,000. Peak Six? Well, a hell of a lot more. So how?

Well, it starts with understanding options. In the options world, there are almost 6,000 stocks that have listed options, and that's all the different times and expirations, so-called a million and a half-ish securities. At any given point in time, Peak Six will have positions in 3,000 to 4,000 of those stock names with their associated positions.

So while it requires a lot of technology, obviously, to manage this, we're not a high frequency firm. We actually carry the inventory. We have it on our books as we speak. So I think high frequency, it's more like a delivery service. They don't really take risk, and it's just about speed and efficiency.

A really good way to think about Peak Six is like a grocery store. So we're servicing our customers, and we need to manage the inventory well. We're much closer to like a Walmart or a Safeway. And like them, if we don't manage the inventory well, it goes bad. We lose.

So in the same way that prices at the store are going to move around based on consumer demand or on outside forces on supply like logistics or weather, option prices are moving around as well. Remember, we're trading in these 6,000 different names with different time frames, all unique characteristics, different earnings, different dividends.

We're trading hundreds of thousands of options every single day. So our biggest expense, as you might imagine, is technology. We're receiving billions of messages per second. So we get the entire marketplace. What do we see? What's moving into extremes? We might be looking at individual names that are doing that, industries, or the marketplace as a whole.

So what am I seeing today? Well, most people know that over time, stocks outperform bonds. You take risk. You should be rewarded. Now, if we look at how much better off you'd be by buying stocks, you can see it moves in a relatively stable line upward sloping with some periods where stocks are more or less expensive or cheap.

Some of you remember the dot-com bubble. Some of you are pretty young out there. Most of us will remember the financial crisis. You can see that second star. Obviously COVID. And clearly no surprise to see these kind of disruptions show up. Then you can see today. Then you can see today.

Now, there are a lot of people who are talking about this. And for me, I've seen a lot. And it's really hard to call it top or bottom. And we don't pretend to call it tops or bottoms, frankly. But what's unusual this time is that when things get stretched, risk or the cost of options tends to be expensive.

Today, you can see the previous three from the last slide. And look at today. How low volatility is. This is why at this point, and in the month of August, we've owned more options in our portfolio than -- it's probably top five in our history. So, our key to success is to manage the inventory top down and bottoms up all day every day.

And when the great ideas, we've got to push all in. When they come, we push all in. And as good as this opportunity might seem, I'm going to tell you about an opportunity that makes that small in comparison. There is going to be a market correction. The correction is that half of the participants are going to identify as female.

How? I'll take it. Hopefully it's not a surprise to this room, but it's been right underneath our nose for a really long time. We are going to teach them poker. Now, most of you know that poker teaches indispensable life skills. Certainly our lovely host espoused this all the time.

It teaches strategy. It teaches taking risk. It teaches capital allocation. I could go on and on. But guess what? Men are getting those lessons, and women are not. Of the more than 110 million plus -- nobody really knows the number -- poker players in the world, less than 10% are women.

Just like driving 100 years ago. So we started a company. It's called Poker Power, even though they said Power Poker. I'll take either, as long as you're saying it. It's called Poker Power. We're on a mission to teach a million women this game. We have a team of companies who recognize how important this skill can be to their employees, and they are teaching this game alongside of us.

Some of the biggest tech companies in the world, the biggest banks, investment banks, law firms, you name it. So, when I look out at this crowd, frankly, it looks fairly similar-ish to the trading floor many years ago. And in five years, it's going to look very different. That is my prediction.

Hopefully sooner. How? Well, it starts by going -- actually going -- actually going all in. We're not all in if 50% of the population trades, invests, or plays poker. This podcast is not called "Men In." It actually has the word "all" in its name. So, we are going to challenge you guys.

Challenge the hosts. Challenge the future listeners of this podcast. To see how many girls -- and I say girls -- we can teach this game as early as seven or eight. How many girls and women can you bring to the poker table? We're going to kick off a competition today.

Over the next month, we want to see who can refer the most women to the Poker Power Play app. In my opinion, it's brand-new. First, gender-neutral, truly gender-neutral poker app on the market. Super easy. Love all the cameras I'm seeing. To get the QR code and to refer the girls and women in your life.

What's in it for you? Well, I was thinking the hosts could decide. Knowing them, maybe it's like a Laurel Piano something or Montclair. Maybe it's a buy-in to the WSOP. But whatever it is, it's my gift to you. So, let's not just trade or invest in the market. Let's make the market.

Let's go all in. Thank you. Thank you. Amazing. As a father of three daughters, I very much appreciate you making this your passion. It's absolutely fantastic. We've averaged about 32, 33, over the first two conferences, about 33% female. But we had to take a lot of steps to make that happen.

Scholarships and just, you know, finding women's organizations encourage more people to come. I'm curious, just looking at the world largely, we've seen a massive change. There are more women getting graduate degrees than men today. Earnings, positions of power. It's really changed a lot. Why do you think it's a little sticky in finance specifically?

And is there something in, we see it in venture capital as well. We've seen many more check writing females, not just window dressing, like here's the PR person, we're calling them a partner in the venture firm, and that kind of nonsense. But I'm curious why it hasn't happened in finance as quickly as maybe some other pursuits.

And then second question, when you do get women at the poker table, and it does click, what do you see change in them in terms of, you know, how they look at the world? You can take that in either order. >> Yeah, I mean, it's fascinating, I have to say.

So why hasn't it happened sooner? I'll do that one. So what I've learned, of course, being a female in a male dominated world for my whole career, I also grew up with four brothers. So it's no surprise maybe that I'm there. But also, like, begging to figure out how to solve the problem, I will tell you it squarely comes down to risk taking.

So it's -- and what we don't realize, so in our natural play and hobbies, typical, you know, the stereotype, how a young girl plays, I'm not taking risk. And one of the things that we have found, and what I see actually helps women at the poker table, it's -- because every hand is a risk of some sort.

They don't get enough repetition of risk. So we don't talk about taking larger risks. We actually talk about taking -- not taking more risk, sorry, let me step back, more risk. We talk about taking more risks with an S. So we need to get reps in. And those reps aren't part of our upbringing.

So for someone coming into trading, you get a lot of fucking reps, right? At the poker table. That's why if we can get these girls playing, I'm telling you, right, the guys are ahead. We know this. The study's been done. First rung on the ladder is where the woman falls behind.

The guy will take the job with 60% confidence, and the next managerial job become equal out of school, and she needs 90% confidence. Of course she does. She hasn't taken risks. So we have to get those under their belt. Whatever they look like. And by the way, they look different for everybody.

And watching what is a risk for your daughter, in fact, if you guys are up for it, I think there's nine daughters here. >> Two, two, three. >> Three. >> Three. Three, six, four. Yeah. >> It's like seven and a half. Seven and a half, I think. Just back of the envelope math.

>> Yes. But -- >> You see how fast I did that? >> You can't count in simple numbers, bro. >> But here's the thing. We're having this discussion, I think, in 2023 here, just even saying there are gender differences in this, and there are different ways in which girls are raised versus boys.

It's kind of the third rail, but listen, it is what it is. And maybe you can talk -- when you give them that push and they get 10 sessions in, 50 sessions in, now they play 1,000 hands of cards, 2,000 hands of cards, what do you see happen to them when they go out into the world?

What changes in them when they learn to take risks, when they learn to bluff, when they learn to re-raise, and when they learn to fold when they thought they had a really strong hand, but hey, that board's textured. >> Yeah. So we have -- we literally get testimonials, and there are many senior women who are part in this corporate work we do.

The senior women are sort of floored and flabbergasted, I can't believe, right? So I didn't realize I wasn't playing to win would be a very common thing. I didn't realize somebody would actually do that. >> Yeah. >> Right? Like, I didn't actually know everything when I went into that meeting.

I assumed I did, because I'm giving everything that I know. I'm not holding back at all. The thought of holding back is not part of the repertoire either. It's the giving and giving totally of self. So strategy is -- unless it's actively discussed, right, isn't seemingly as natural. Obviously when we have athletes or, you know, other types of experiences coming in, that tends to change it.

I think -- you know, I'll give you a basic question for a young woman who comes in, and she goes into a meeting, and she doesn't say anything. It's kind of like you folded a hand. Maybe you folded a few hands. We all know we need to fold a lot of hands to win.

But she keeps folding, she keeps folding. What is she waiting for? Because if she keeps folding, we know she's ultimately going to lose. If she never speaks up in a meeting based on Toby, we should never have been in the goddamn meeting. >> She's going to get blinded out.

>> Exactly. She'll be gone. So at some point she has to take a risk, even if her cards aren't great in that meeting, if she wants to participate. >> How do you define risk? Because for a lot of people in a naive context that haven't looked at probability and statistics and understood that something is unlikely to happen, but the payoff you're getting is worth it to take that.

It's a 30% chance of happening. But if it happens, you get paid 5 to 1. So that's a good bet to make. And is that the sort of kind of rubric that, you know, folks start to kind of go through to understand what it means to take risk, that it's not just about doing something scary or something unlikely, jump into anything scary or anything unlikely, because sometimes that risk isn't worth the payoff and sometimes it is.

>> It is. It is both of those things, actually. So when I talk about teaching poker and the first thing a man will do is say, well, if you're not playing for real money, you're not really playing, which is not a true statement. Play with your kids for, you know, pretzels and M&Ms or marshmallows and see what happens.

You're playing a real game and you're causing the brain to think differently. But we, so we start way down on the curve for our women, because the whole goal is to create safety and security and learning this game that is male dominated, where they feel like they're going to be judged.

And so probably it's around lesson four, so we have a curriculum that they're starting to learn the numbers as well. And how do I do it in, you know, a basic way, a quick, easy way, and then how do I get better and better as I go up the curve?

>> There's a great book written by Annie Duke called Thinking in Bets. >> Yeah, great book. >> And I would encourage all of you to read it, because I think, Friedberg, what you're stating is actually something that a lot of people have, which is a little bit of mathematical illiteracy around probability and probabilistic thinking.

And it is a very different mindset to think about expected value. Why do you make a certain bet some number of times? Why losing 15 times in a row literally can be okay, because over a distribution of 100 times, you may actually come out ahead. It's a very difficult way to train your mind.

>> By the way, I think it's really important in a broader social context, so that not everything is right or wrong. Not everything is I will win this bet or I will lose this bet. It requires a second dimension attached to every decision, which is the probability, which most people don't do, and it's what also makes conversations around things like social policy and politics difficult, because people say this is one way or the other, but it's like, hey, if we do this this way, there's a 30% chance it might work.

There's a 70% chance it might not. But if it does work, it's ten times the return. That's worth us doing. So we should expect failure. But if we succeed, it's going to be in an outsized way. If we get to make enough of those sorts of decisions, things can move.

We get caught up in a lot of our decision making, you know, and social policy as well. >> David's a huge feminist thinker, and I'm curious, David, you're taking all this in right now, and I can see the wheels turning. Your thoughts on, you know, in the postmodern feminist world, how do you think poker plays into -- >> The lunch break is not going to be fun.

>> I recognize that face. I see that. >> You see the compassion and the EQ. >> I haven't learned how to virtue signal quite as well as you do, Jack Alpert. >> Just try genuflecting one time. Give us one genuflect. >> I do have an observation, actually, on this, which is I think the point you made, actually, that safety is the opposite of risk is a really interesting point, because the thing that you hear over and over again, for example, in these debates we have over free speech, is safetyism.

We have to make the environment safe for people. We don't want them to hear arguments they don't like. They need the safe space. I've never bought that as an argument for censorship, for example, but you're making, I think, a different argument, which I hadn't really appreciated before, which is if we don't make people comfortable with risk, then they're not going to be successful in these areas.

That's another downside of this aggrandizement of safety. >> Psychological safety when you come to work is a fallacy. Right? I mean, this is the worst thing you could do to somebody is to make them psychologically safe. The world is not safe. >> Right. >> I have a market question.

I apologize for my jumping. >> Can I just say one thing on that? So I literally was at a dinner last week, and there was a man from a very old, successful firm, and he said, after too many drinks, all the women who come and ask to be partners at our firm, they always come with a perfect track record.

They never have lost money. And I was like, and you're surprised? >> Right. >> Right? I mean, it's so backwards that these extraordinarily successful women feel like that is the journey that has to be had. In fact, it's the opposite of the journey. What we all want them to see is how they have failed, how often they failed, how they kept the failure to a minimum.

>> So in some ways, these are like the highest performers. >> Exactly. >> Perhaps if they were men in this country. >> No, it's not even just men. >> They would take more risk. >> As an immigrant, my first job was on a trading floor, and I had an incredible boss who took me aside and taught me the difference between batting average and slugging percentage.

And that's another concept that's poorly understood, because when you're at the bottom looking up, you think you have to be perfect. That's batting average. But when you realize that in baseball, the best batter in the history of baseball, you know, is basically a 400-hitter, but that was like once, and that's an aberration in the '50s or '60s, that'll never happen again.

You realize, okay, we're hitting for slugging percentage. And that means implicitly huge error rates. >> Yes. >> Tons of losses. And unless you internalize it and figure out how to manage it, you can't make a ton of money. I just want to shift the conversation. >> Yeah, yeah, yeah.

>> You're an incredible business person. You have a vantage point that I find really fascinating, and you put on a chart up there where -- about inventory of options now, you're sort of at this really interesting moment. Financial vol is kind of like been decimated. What does that mean as you look forward based on your pattern recognition of the past?

Where are we headed into? And knowing where your firm is positioned in all of that. >> Yeah. So we're in an odd place right now, I think, right? It has a .com-esque because of AI feel to it, but we have the Fed maybe is going to raise a little bit more, but not.

Inflation may be slowing, but it may not. We have sector rotation. We have a lot of push and pull. You're right in the middle. And so what is going to snap that one way or another? Definitely not something our firm tries to make the call on, but we're saying it's ready.

It's ready and it can if a handful of things happen, whatever they may be, exogenous events, whatever it might be. And we want to be ready. And by the way, we might be wrong. We'll just waste a bunch of money holding the inventory that's going to rot. But -- >> But basically you're long vol, is what you're saying.

Massively long vol and you're waiting for something in one direction or the other to break the market. >> It's a good time of the year, right? We're going to go into next earnings cycle. >> We have to wrap. I really appreciate you coming out, sharing your story. I encourage everyone, the QR code, we'll share that and everyone can hopefully download the app and promote.

>> And just as girl dads, thank you. >> Yeah. And thank you so much. >> Thank you for doing this. I appreciate that.