People ask all the time. They always ask Jenny, 'How can you work with your husband?' No one ever asked me how I work with my wife.
We know nobody does it alone. We are in it together. I think one of the reasons why our trading firm has made money for so long is because of that, the collective. So everybody's eyes are on the same basket.
New York City, the finance capital of the world. It has more ambition than one tiny island can handle. And it's not a bad place to get a bite to eat either. For three decades, we made it here on the markets, calling our shots and always speaking our minds.
But the best conversations happen across the table.
So pull up a chair while we break bread with founders, CEOs, and creators, all in the iconic spots that define the greatest city on earth. This is Standing Table presented by Apex FinTech Solutions. For today's episode, we look back at our conversation with Jenny Just and Matt Hollesizer at Apex Ascend Innovation Summit. Jenny and Matt are co-founders of Peak Six Investments and have been building successful businesses together since the '90s. In 2012, they bought the company that became Apex Fintech Solutions and helped shape it into the company we know today. Oh, and get this. Jenny and Matt aren't just partners in business, they're also partners in life. Married since 2003, they've made their mark as traders and business operators. And over the years, they've instilled a shared vision that technology can make financial markets more accessible, more efficient, and more inclusive. Today, we're sitting down with Jenny and Matt to talk about their journey from building businesses together to building a life together and ultimately building Apex.
Well, Guy and I were honored to be here at the Ascend Innovation Conference, first annual. Hopefully, we'll get asked back. We just got to at this point.
Yeah, we'll see. But we got to spend some time with these two. They couldn't have been more hospitable, so we thought we'd kind of lay it out here and we'll do it in front of all these guys. Guy, what are we doing here? Well, we're going to have a conversation and we're going to have a conversation about their background, how they wound up together, the amazing companies that they've built because I think getting to know the backstory is always the most interesting thing. So, Jenny, I'll start with you. Being a woman in back then a male-dominated field. Now, not so much as anymore, but back then it was. How did you vibe? How did you get going?
Well, first we will introduce ourselves because we are the owners of Apex. So, if that is helpful, we'll give you a little background.
I was going to say he starts out with back then. I just wonder how old he thinks you are.
No, no, I said I just had a whole conversation. She said, 'When I got to college, I said it was like 2015.'
It feels like the trading floor again.
I know what it's like. It's okay. As I said earlier, I can take them. Yeah. I started on the Chicago Board Options Exchange. Matt started on the MX. We both started with an amazing firm who was very infamous in options trading, O'Connor and Associates. And for me, it was no different than how I grew up. So, I grew up with four brothers and down on the trading floor. It was just like roll my eyes, here they go again type of thing. And I was there to do a job. I didn't know anything about options trading. I actually didn't even know I was going to the trading floor. I didn't interview on the trading floor. I interviewed in an office. You know, I was good at math. I answered the questions quickly and I was token female for sure.
So, Matt, how did you find the one woman on the trading floor? I mean, it seems like...
I mean what was your deal? Were you like a hot shot back then, huh?
You know, I came to Chicago actually to meet Jenny.
Yeah.
I mean, I was clearly a good investor back then, too. We had met because way back then banks trading used to be separated. They couldn't really do it. There was this thing called Glass-Steagall. Okay. We got bought, our trading business got bought by a bank and we're going to go out and create solutions for customers. And so who to decide that they're going to entrust this new business to but Jenny and myself and another gentleman who was from Goldman Sachs, a more senior, wisened person, which was a terrible mistake. And so we really cut our teeth together trying to build a business from scratch at Swiss Bank.
So what was pillow talk like back then?
I mean that's a little personal. What were we talking about? Like what were we talking? And were you guys competitive?
Well, there was no pillow talk back then. Pillow talk came later. And we weren't really competitive. He was too, you know, he's a cocky guy in trading like he doesn't think...
The good thing is that I turned out to be, you know, able to handle myself, right? We basically built this business inside the bank together, over-the-counter equity derivative business, which is basically off exchange equity derivatives. And it was huge and it quickly trounced the other business. So we're like in our mid-20s doing that. So we both got, you know, naively cocky doing that and now it's 28 years later and we've had many businesses. Real quickly, Peak Six is a company of companies. People think of us as investors and traders. We're really operators. So we've either started or bought and turned around roughly 15 companies over the last 28 years. Our trading business, most of you don't know us, it funded everything we did. So we didn't need outside investors. Our trading businesses have never had a losing year.
No. Which is amazing. And how many years is that?
28 years never a losing year. I mean that's pretty good for you. Yeah.
And you guys were at the forefront of technology. Guy and I just spent like 30 minutes talking about AI, not really talking it down, but you know at some point the game changed, right? You guys, it was open outcry, then you guys just said you were doing over the counter which was not on the exchange. At some point you had to lean into technology and you had to believe that this is where the business was going.
It's a funny one early on. The one thing you should know about Jenny is like we start the business and Jenny's like...
Yeah. Well, she's like we are not good managers. We cannot manage more than 10 people. Like we just don't have the skill to do it. So we may not ever be a big company but we're not going to manage more than 10 people. So I'm like, 'What the hell are we going to do? We better maybe we should use technology because that's the only way to scale.' So it wasn't necessarily technological foresight. It was really management and attitude that drove us into technology. We were the first firm to trade from off the floor.
So exchange product sitting on a desk sending in electronic orders into the then yelling and screaming pit. We were the ones doing that. You know we talk a lot about risk as well. Risk-taking is a skill you might be able to learn, but I think at least in my career, it's sort of innate with some people. And I gave an example of a gentleman was at Goldman Sachs on the currency desk that in a year lost about $150 million, which is a lot of money. Today, it was a shitload of a lot of money back then. In the ensuing year, he made partner at the firm. And I think the thought process was if you're able to lose that kind of money, by definition, you're somebody that probably has the temerity to be able to make that in spades. And that is not a chip that I possess to that degree. But understanding risk, taking risk, that's something that I think you'll say you learn, but to me that was probably innate with you, Jenny. So talk about that.
Yeah, I definitely think it's a combination. But I think for people who never test it, how do you know, right? People go about their lives. Particularly the risk-taking that I'm most concerned about is women taking risk around money. And if we never try, we don't really know what we're capable of. I'm the perfect person. I got into trading because I answered math questions in an interview. I didn't even know what O'Connor was. Nobody knew what it was. And I probably inherently growing up how I grew up. I had a really intense father. Mom took care of the five kids. You know, four of them were boys. I was right in the middle. So I think I was more inclined but I definitely wouldn't have called myself a risk taker. People wouldn't have looked at me as a risk taker. I was probably a rule follower more than a risk taker.
And you mentioned the fear of taking risk. I have a husband. I have a wife. I have kids. I'm paying for college. I can't take that kind of risk because it's career risk and that can be paralyzing that fear. So how do you push through something like that in your opinion? If you have dreams and goals and you actually want to achieve them, there's no option besides getting over some hurdles. Many of them are around your fears. One of the things I think we can do, you know, just looking at the age, you know, a lot of you have young kids out here, having your kids get used to practicing taking those risks over time, whatever they are. For some kids, it's just if they came home and they raised their hand in class and they never do it, like that's a massive risk, you know, for a young girl who cuts her hair off from here to there. We've done some studies on this. It's amazing what they perceive as risk. So talking about it so you normalize the idea is incredibly empowering particularly for young children of all genders and particularly girls.
So Matt, at what point do Peak Six, right, you guys started, you take a big risk, right? You take a bet on each other. You stay, you have a handful of employees. At what point do you say to yourself this is it? This is what we're going to build and we're going to hire lots of people. We're going to invest in technology because there probably had to be a few instances where you're like, you know what, let's just go back to the floor and let's just trade.
You know, I'd love to say that there was like a specific moment. You always say like what's the epiphany moment?
It just happens over time. And by the way, it's not like it's completely happened. Like we're still figuring out what to do after 28 years. It's a healthy dose of paranoia. I think at one point I wouldn't say it was any sort of brilliance on our part like we were electronic and then the market went electronic that just we were just first it was just smart to be first. So Apex the story of Apex is really about us having we owned a brokerage business I don't know like Peak 6 we started many businesses so we had operated the brokerage business and we ended up stepping in and purchasing the assets of Penson and creating what became Apex in 2012. Well, but you know, you sort of gloss over that because I think it's really important. You didn't stumble in any I mean, I'm sure there were a few sleepless nights you both had thinking about what are we getting ourselves into, yet you move forward. Probably one of the outside of getting married to one another, probably some of the best decisions you made. But speak to that because it wasn't just fell into your lap. I mean, you had to really think about this.
Yeah, it was a perfect storm. Okay. So, clearing custody firm gets in trouble. Okay. Announced fraud.
Public company. Okay. They need money. Monday morning, we get a call from the SEC. They want us to fund $70 million. By Friday, it's announced fraud. Okay. Rough scenario. But Jenny and I innately understood the clearing business because we had worked at O'Connor. We were self clearing. We had actually worked in a long time ago the DK room. We had done night outs. Okay? Some of you may know that. Younger folks will not understand what I'm talking about. But you had to match up. You had to show up. And so we understood the masonry of clearing and custody. So you have this fraud, you have money that's needed. Jenny likes to say, 'Why the heck are you calling us?' But we actually bought the assets 13 days later. So it's chaotic. Okay, there's 600 correspondents at the time. Of the 600 correspondents, we had plenty. There was lots of bad behavior that had gone on at the correspondents. People, customers, retail customers showing up at the door looking for their cash. And the correspondent had stolen the money years earlier and had been sending fake documents to their retail customers. There's no cash. We have no record of this person and they're looking. One Eastern European gentleman showed up with his associates, right? Two huge guys at the door. We had a higher security like 'Where's my money?' And I think when you say trader, Jenny is definitely a good trader because she doesn't really get phased during times of chaos. She actually finds clarity and Jenny turns to everybody and says, 'Let's build, let's fix this, but the way we're going to do is let's build what we would want as a broker, as a correspondent. What is the big pain point for our customers?' And that's actually the genesis of Apex was like, look, it's onboarding. It's so painful. Compliance is a huge issue. And that was the one thing that we really focused on.
