Tom Sosnoff was one of those names I kept hearing as I came up in the Chicago tech scene.

A self made entrepreneur behind two massive outcomes, over $600M and $1B respectively. Someone who fundamentally changed how the finance industry brands itself and reaches consumers. A builder deeply tied to Chicago.

I knew early on that I wanted to feature Tom in my Chicago Futurist series. So I open sourced the ask on Twitter: who could connect us?

Less than a day later, we were talking.

One thing I quickly learned about Tom: he hates getting questions in advance. He'd rather follow the conversation wherever it goes.

So what follows is exactly that. My off-the-riff conversation with Tom Sossnoff:

TS: It was the last frontier of raw capitalism. Absolutely the rawest form.

You had ten to twelve thousand traders across all the Chicago exchanges, and every single one of them was exactly the same. An insane alpha male. Didn't matter if you had a law degree or were a high school dropout. The floor flattened all of that. What it rewarded was a specific kind of tolerance for brutality and an ability to make decisions instantly, under pressure, with real money on the line.

Most people failed. Ninety-five, ninety-seven percent. The ones that survived, you just could handle what the job actually was. Standing in one place, screaming, taking ridiculous amounts of risk every single day. Within two years I was making more money than my parents had made in their entire careers. I never even told them what I did. We were just stupid kids making a million, blowing a million, making it back. That was the whole game.

TS: The word entrepreneurship didn't even exist when I started. I'm serious. When we won Ernst & Young Entrepreneur of the Year, I got up on stage and said, I started doing this before that word existed. We just thought it was raw free market capitalism. There was no framework for it, no playbook, no community of founders to learn from. We were just traders who thought we could build something better than what was out there. It turned out I was good at that game.

Whatever game that actually was, I was good at it. I don't think entrepreneurs should be problem solvers, by the way. The best ones have a vision and figure out how to execute it tightly. Problem solving is reactive. Vision is something else.

TS: I felt the industry was going to change and I was right. High frequency firms were coming. The locals who'd thrived as market makers for two decades were going to get systematically pushed out by technology, and I didn't want to be there when the floor became a ghost town.

So in the late nineties I started thinking about what we actually knew. We knew options. We knew that industry inside out. We didn't know technology well enough, we didn't know consumer distribution, but we were very confident in two things: our options expertise was deep enough to build around, and we were really good at raising capital and telling stories. So we put all our own money in, bootstrapped it, and never had a down day from the start. The business was printing money almost immediately.

TS: TA Associates cold called us out of nowhere and offered $20 million on an $80 million valuation. The very next day, TCV shows up. They don't even ask about our business right away. They just go: what did those guys offer you? I told them. They said, we'll give you $22.5 million on a $100 million valuation. Before the guy finished his sentence, we said done. He looked at us like we were crazy. He goes, that was kind of a fast decision. I said: you made the offer, we took it. We're traders. That's how we operate.

We never even spent the $22.5 million. It just sat there. We didn't need it. We took it because you always take money when you can, not when you have to. When you need money it's too expensive. When you don't need it, it's easy.

Three months later they sat down at our first board meeting and told us we were the worst company they'd ever invested in. Then one partner turns to the other, just loud enough for us to hear, and says: do you think they're worse than Netflix? They had just put money into Netflix at some enormous valuation. The other guy goes, I don't know, they're just about as bad as Netflix. And I'm sitting there thinking, you have no idea what you have.

So we offered them their money back. Told them we actually thought we'd sold too low, that we had a higher offer from somebody else, and that we'd return the $22.5 million. They went into another room, talked for a few seconds, came back and said they'd stay in. We said fine — but on one condition. That was the last time we ever had this conversation about how bad we are. Because we're not wasting our time. We know how good our stuff is. That was the last time.

They made eight to ten times their money and then invested in tastytrade twice.

Always make your strongest deal, and remember it's just money. You don't need their help. Whatever got you to the point where someone wants to invest in you — that was you. They didn't do that.

Over time, the best-case scenario is you learn to coexist, and they learn to leave you alone. That's the ideal board relationship.

Your life's purpose is not to grow the Harvard endowment. It's to deliver for your customers, your users, and your employees. The investor is there to help you accelerate. That's the whole job.

TS: I talk to Edward almost every day. He's one of the best young CEOs in Chicago, in the Midwest, and maybe anywhere.

The story of how we met is funny. It was late, around 4:30pm, most of the tastytrade team had already left. I buzz these two young guys in. Edward and his partner. They're like 22 years old. He says: I read about you, can I pitch you on something? Oxford, then MBA from MIT. He had the pedigree.

He pitches me a cannabis exchange. I told him I knew how hard it was to get exchange licenses, that it was almost impossible. He said he knew, but he had a game plan. I said: go out and get close to a million dollars, come back, and I'll put in the last hundred or two hundred thousand to close it out. I wanted to see if he could actually execute.

Two weeks later, he's back. He got the million. I wrote him a check. They worked hard on that cannabis exchange but never got CFTC approval. Eventually they wound it down. But Edward returned everybody their money with no profit, no loss, everyone made whole.

That was the moment I thought: this is a good kid. He could have disappeared. He didn't.

He did that. I was just there to support him.

TS: Something has always bothered me. The wealth gap. I think executives make too much money and the average employee is underpaid over their lifetime by a significant amount — somewhere between $6 and $8 million in the demographic we're building for.

The reason isn't that companies are evil. It's that employees don't know what they're worth and they have no real context to negotiate. You can't legislate that away. You can't mandate it. But you can fix it through education and through technology. AI gives us the depth and accuracy to actually do this right.

You upload your resume, we tell you your exact market salary. Not a range, a specific number, weighted for your city, your school, your experience, the projects you've worked on. Then we also look at your investment portfolio and tell you how much you're leaving on the table by not optimizing your approach. There are thirteen agentic portfolio tools in development. The whole thing is: arm people with information they've never had before.

TS: When it comes to finance, I personally would not invest in anything that wasn't in Chicago. I'm all in on this city. It's just a different world here. The DNA goes back to the exchanges, the floor culture, the way people here understand risk at a fundamental level. That doesn't exist in the same way anywhere else. On the payment space specifically, that's where the future is.

Crypto as a store of value is fine, but it's dead money to me. It doesn't churn. Payments churn. The digital asset space will be around forever, but the payment infrastructure layer is far more interesting. That's what Edward's been building, that's what a lot of these Chicago companies are building.

I love that Chicago isn't tied to one thing. You've got finance, life sciences, manufacturing, logistics. That diversity is rare and valuable. We're not a one-sector city.

At the end of 2025, I shared an update about Waymo and the possibility of it coming to Chicago. Since then, we’ve seen Waymo vehicles on the street (not picking up passengers yet) but mapping the roads for future use.

Chicago has to keep thinking about the next big space if we want to compete and remain a destination for innovation. Autonomous vehicles are the next logical step.

Not only because I would love to see Waymo’s in Chicago, but I also feel that if Waymo can figure out how to operate here, it can do it anywhere.

While Waymo is mapping the area, legislators in Springfield will also need to adopt a policy solution that will allow these vehicles to operate on the roads.

Senate Bill 3392 is currently awaiting action in the Senate Executive Committee. When it is called for a vote, we want legislators to know that we want Waymo in Illinois.

To help us get the word out, please fill out this form to take action.

Skepticism around autonomous vehicles is natural, but it’s no different than any other new technology that you learned to use.

The truth is, because these vehicles remove humans from behind the wheel, they also remove the risks of distracted, drowsy, or impaired driving. Waymo vehicles use the most advanced fully autonomous driving technology in the world, using a mix of cameras, radar, and lidar to engage with their surroundings. As these vehicles spend more time on the road, they continue to learn and adapt.

Because of these capabilities, Waymo has reported a 92% reduction in serious injuries and 83% fewer airbag deployments in the markets where they currently operate.

Currently Waymo operates in 11 US cities, including their most recent expansion into Nashville. (I’ve tried Waymo in 4 cities)

With your help, we can make Chicago the 12th.

Sign up today to take action, contact your local legislators, and tell them, we’re ready and bullish on Waymo!

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