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I sat down with Tom Sosnoff, one of the most successful entrepreneurs in financial services. Tom spent 19 years on Chicago’s CBOE trading floor and then left to build Thinkorswim, the first online broker specialized in options, which he sold to TD Ameritrade for $700 Million. He then built Tastytrade and sold it nine years later for $1.1 Billion dollars to IG Group. He is now building Lossdog, a career optimization platform to help fight wealth inequality.
What I enjoyed the most of this conversation is how genuine Tom is. He’s kind and cares about fairness and inequality. Prioritizes legacy over money. And he is a builder at heart that loves to take risks.
We discussed how a political science major accidentally fell into trading and never left, why the trading floor was the ultimate school for risk-taking and fast decision-making, the story behind building a platform that changed a $500 billion options industry, and why Tom believes tokenized derivatives, not tokenized assets, are the real future of finance.
From the Trading Floor to Thinkorswim: How a Political Science Major Changed a $500 Billion Industry
Tom Sosnoff never planned to end up in finance. He was a political science major who figured he would become a lobbyist or a lawyer. But he graduated into a recession, and the only interview he could land was on Wall Street, at the legendary investment bank Drexel Burnham Lambert. A few colleagues there convinced him that if he moved to Chicago, they would put up the capital and trade through him, so he flew to Chicago, walked onto the trading floor at the Chicago Board Options Exchange (CBOE), and fell in love instantly. That was over 44 years ago.
Sosnoff spent the first 19 years of his career as a floor trader, an era he describes as the most visceral form of capitalism imaginable. A kid could walk onto the floor with $20,000 or $50,000 and turn it into millions. Only a small percentage survived, but those who did lived like athletes. What the floor taught Tom more than anything was a complete absence of fear around risk. He makes decisions fast, lives with the consequences, and moves on. In his view, that combination of processing speed, decision-making ability, and tolerance for risk is the single most important ingredient in independent wealth creation. By the late 1990s, he could see the trading floor was dying, so he and his business partner Scott Sheridan left and decided to build a technology platform. They knew almost nothing about building technology. They hired smart people, got lucky, and built what became Thinkorswim.
What made Thinkorswim revolutionary was how it repositioned options. The industry had long marketed options as a leverage vehicle. Sosnoff saw them differently: as a strategic tool, an intellectual challenge, and a capital-efficient instrument. Nobody at the time understood the art of spreading or the strategic side of options. Thinkorswim changed that. When Sosnoff started, the options market handled roughly 100 million contracts per year. Today it processes about 10 billion. Retail traders accounted for essentially 0% of volume back then. Now they represent roughly 25%. He sold Thinkorswim to TD Ameritrade for approximately $700 million. By some estimations, had they kept it independent, it could be worth $20 billion today. But he does not dwell on what he left on the table. He is a builder, not an optimizer of past decisions.
The tastytrade Playbook: Building the World’s Largest Digital Financial Network for $1.1 Billion
After the Thinkorswim sale, Tom stayed at TD Ameritrade for two years under a multi-year deal. When his contract ended, he went to the CEO and was as upfront as ever: am I ever going to run this company? The answer was no. So he decided to build something new.
He pitched the CEO of TD Ameritrade on TD becoming his partner for a new venture called tastytrade. The pitch was unconventional: Sosnoff wanted to build a digital financial network, not a traditional media company like CNBC or Bloomberg. It would be a math network, turning finance into a logical equation, challenging people through quantitative content rather than talking-head opinions. The CEO committed on the spot and invested $20 million through TD Ameritrade.
Within five years, Tastytrade became the largest digital financial network in the world, with viewers logging in from 190 countries. The format was unlike anything in financial media: hosts cracking jokes, having fun, and spending their airtime on complex math equations and derivatives pricing. People loved being challenged intellectually rather than being told what some pundit thinks about bonds going higher.
Tastytrade started sending TD Ameritrade significant customer flow – the viewers not only wanted to learn, but they also wanted to trade! The volume became significant and after five years, TD offered to buy the whole company for around $200 million. Tom did the math and figured if someone wanted to buy you for $200 million, you are worth much more. They politely declined and built their own brokerage firm instead. Four years years later, Tastytrade sold for $1.1 billion to IG Group.
These outcomes were the result of hard work, but also smart business building. Throughout both Thinkorswim and Tastytrade, Sosnoff maintained a rule: $1 million in revenue per employee. When they sold Thinkorswim, they had 500 employees. When they sold tastytrade, they had 350. Both companies were hugely profitable. And in both exits, Sosnoff and his partner Scott gave away a combined $50 million to employees above and beyond their equity, with zero legal obligation to do so. They never publicized it until many years later.
Lossdog: A New Venture to Attack Wealth Inequality with Career Optimization and AI
Tom Sosnoff did not want to build a third trading platform. Instead, he had what he calls a crazy vision: attack wealth inequality head-on and just a few weeks ago in early 2026 he announced his latest venture.
The data behind Lossdog’s thesis is clear. The average employee at most companies is undercompensated over the course of their lifetime by a few million dollars. The average CEO is overcompensated by tens of millions. Nobody needs to make 500 or 1,000 times more than the average employee at their same company. Tom believes this gap can be addressed the same way he changed derivatives trading: through education and quantitative transparency.
Lossdog’s core product is a career optimization platform for individuals earning between $50,000 and $200,000 (roughly 100 million people or half the US workforce). Users can upload their resume and get data-driven insights about what they should be worth, what they are leaving on the table, and what they could earn if they switched careers or cities. The platform also includes portfolio optimization tools and statistical analysis of outlier risk. All of it is free.
Like any tech company launched in 2026, the company is layering in agentic AI tools for portfolio creation, risk monitoring, and other capabilities that do not exist on traditional platforms. That is why Sosnoff calls it “a trading platform without the trading.” Lossdog also runs a daily live call-in show called One Lucky Dog, which is gaining traction in the same grassroots way tastytrade did.
Lossdog is targeting young people, not just mid-career professionals, and they are already signing up thousands of university students. The idea is to reach people before they enter a system that structurally undercompensates loyalty and rewards job-hopping.
And there is also a crypto play. Lossdog is launching a stablecoin to build the rails for tokenized derivatives markets. They seeded their user base by giving away $1 million in crypto, aiming for 20,000 to 30,000 users with real money in their accounts at launch.
Tokenized Derivatives, Zero Turnover, and the Restless Builder Who Won’t Retire
Tom Sosnoff has spent years deep in the tokenization space. He even built and sold an exchange called the Small Exchange twice: first to Crypto.com for a quarter billion dollars (they sold it back to him for $10 million when they didn’t need it), and then to Kraken for $100 million. His view on tokenization is contrarian. Tokenized assets, in his assessment, are essentially dead money. You buy tokenized stock or a tokenized asset and it just sits there, much like crypto. The real future lies in tokenized derivatives: options, futures, anything that is leveraged and strategic. That is where liquidity pools become transformative. Sosnoff designed a mechanism for futures liquidity pools that would allow ordinary customers to participate in market-making, not just institutional players like Citadel. He sees Robinhood as probably the closest retail platform to making tokenized derivatives a reality, though he doesn’t think they’re quite there yet. The regulatory environment, with Gensler gone and new leadership at the CFTC, is finally conducive to this kind of innovation, but Sosnoff is not going through the full exchange-building process again. Instead, Lossdog is building the access rails.
The same restlessness that drives him into new markets also defines how he builds teams. He does not consider himself a corporate culture person. He calls himself a “next person up” type of leader where everybody is expendable and replaceable. And yet his companies have had virtually zero turnover for the past 25 years. The paradox resolves when you understand his hiring philosophy: he hires friends he knows will be loyal and work relentlessly, but also hires genuinely smart people and challenges them nonstop. No country club atmosphere. It is more like: step up or we will find somebody else. The people who came through his orbit now run much of the retail trading industry. The person who runs trading at Robinhood, the people who ran Thinkorswim, tastyworks, E-Trade: many of them started on the floor with Sosnoff. None of them wanted to come over at first. They all eventually did as the floor died. It changed their lives.
At 69, Sosnoff lives modestly. He has no real hobbies. He does not have an office. He works seven days a week, still tries to be the first person at work after 45 years. He made 50 to 60 trades from his phone and laptop during a press tour in New York the day before this interview and placed a few trades on his Uber ride before meeting me at 8am. His daughter manages the family’s generational wealth because he has no interest in doing it himself. What motivates him now is legacy. He wants people to say he was a really good entrepreneur. He does not need more money or more success. He just wants to keep building cool stuff that challenges people, his team, and himself. The worst thing he can imagine is sitting on a beach or going to a country club. Tom is a real leader and a great example for many generations.
Book Recommendations
When Genius Failed by Roger Lowenstein. Tom calls it his favorite finance book, one that proves even Nobel Prize winners do not have all the answers. His key takeaway: “Genius fails when you forget that size matters.” Trade size, in his view, is one of the single most important variables in investing, and the book is a masterclass in what happens when brilliant people ignore that principle.
The Unfiltered Q&A with Tom Sosnoff
Miguel Armaza: Tom, you have a very interesting background. Maybe tell us how you got started in finance.
Tom Sosnoff: I actually grew up in New York, and when I got to college, I got a job on Wall Street working for Drexel. I met a couple of guys who were also starting out there, and after about six months, they said, if you move to Chicago, we’ll put up the money. They wanted to trade through me. So I took a trip out to Chicago, went to the trading floor at the CBOE, loved it. Fell in love just walking on the floor. I quit Drexel basically the next day, moved to Chicago, and I’ve been there going on 44, 45 years now. Being in the world of finance is an accident for me. I was a political science major. I had no interest in Wall Street. I got out of school in the middle of a recession, and the only interview I could get was on Wall Street. They offered me a job, so I took it. Everything’s a fluke.
Miguel Armaza: What did you learn on the trading floor that you can’t really learn behind the screen?
Tom Sosnoff: There’s no such thing as floor traders anymore. I was in a generation where that was the frontier of the most vicious form of capitalism. That was entrepreneurship before there was entrepreneurship. A kid could go to the floor with $20,000, $10,000, $50,000 and turn it into millions. None of that exists today. But I think what I learned more on the floor than anything else was that I’m not afraid of taking any amount of risk. It doesn’t even feel like pain. I make a lot of decisions fast. Over the years of all the trading, you learn how to make instantaneous decisions, whether they’re right or wrong. You just make them and you live with it. Brain processing speed and decision-making ability, not having a bias against risk, that’s really hard to overcome as far as wealth creation goes. If you’re starting out like everybody else, starting with nothing or very little, speed of decision-making, how fast your brain processes things, and how strong your ability to take risk is, that’s really the key to wealth.
Miguel Armaza: At what point did you start to notice that the trading floor era was dying?
Tom Sosnoff: When I got to the trading floor in 1981, I never wanted to leave. I never wanted to go on vacation. I used to tell my buddies, this is not going to be around forever. Money is not going to fall onto your lap. You’re not going to sit down as some 23-year-old and make $10,000 a day because you’re entitled to it. This is a gift that we’re getting right now. So just get whatever you can, because it’s not going to be here forever. And it stayed a long time. But in 1999, the craziness of the NASDAQ rally, the dot-com explosion, we were starting to sense that the business was going to go fully electronic. That’s when we decided to take a crazy amount of risk, leave the floor, and build Thinkorswim.
Miguel Armaza: Thinkorswim today, as an independent platform, could be worth maybe a tenth of Schwab, maybe $20 billion or more. Tell us the story.
Tom Sosnoff: I think it’s probably worth that. When we came up with the name, I was walking through my living room and I was like, think or swim. I called my partner Scott and he goes, I don’t really have much opinion on it, but if you like it, let’s go with it. We didn’t know much about building technology. We hired some really smart people, we got lucky, and we built an amazing platform. Schwab hasn’t touched this platform in 25 years. It’s an incredible piece of technology. When we sold it to TD, the first thing the CEO said to me was, I hate this name, I gotta change it. I’m like, don’t change it. He goes, I’m gonna call it the ultimate trading platform. I go, Fred, don’t do that. At least promise me you’ll go out and have somebody do a study. They did, and 90% came back preferring Thinkorswim. It survived. I don’t look at this as, oh man, we left $10 billion on the table. As any entrepreneur, you just move on. Building tasty was one of the coolest things we’ve ever done, and that was worth a billion dollars. I just build really cool stuff and whatever happens later, I don’t care.
Miguel Armaza: When you started, there were about 100 million options contracts per year. Today it’s about 10 billion. Retail was about 0%, today it’s about 25%. What happened?
Tom Sosnoff: We changed the entire industry with a crazy little platform. Options are the reason that I loved finance, that’s where I learned the business. But I figured out before anybody else that there was a side to options that was not about leverage. Even the exchanges used to promote options as this incredibly efficient leverage vehicle. That’s not how I saw options. I saw them for retail investors as a strategic tool, as an intellectual challenge, as strategic finance. I also saw options as capital efficient, because nobody really understood the art of spreading and strategic options. That’s what we built at Thinkorswim. That’s what changed the whole industry. Firms like Robinhood have blown it open since, but it all started with us.
Miguel Armaza: Let’s talk about tastytrade. You exited Thinkorswim for about $600 million, and then you quickly turned around and started building something else.
Tom Sosnoff: I signed a multi-year deal when I left Thinkorswim. After two years, I went to the CEO, same guy, and I said, listen, am I ever going to be the CEO of TD Ameritrade? He goes, not over my dead body. So I go, listen, I got to do something different. I can’t just work here. I told him I got this idea to build a company called tastytrade. He goes, oh my god, I can’t believe you came up with another name I hate. So he goes, all right, I really think you’re an interesting, great entrepreneur. I want to be your partner. I want TD Ameritrade to be your partner. How much money do you need? I said 20 million. He goes, done. On the spot. That’s why I loved this guy, because he’s a fast decision maker. And instead of a traditional financial network like CNBC or Bloomberg, we were going to build a math network. We were going to turn finance into a logical equation. We were going to challenge people through math. People wanted to be challenged intellectually. Nobody else was doing that. Within five years, we built the largest digital financial network in the world. We had people logging in from 190 countries. After five years, TD wanted to buy us for around $200 million. We sat around and figured, if TD wants to buy us for 200 million, we must be worth a lot more. So we politely declined and said we’re just going to build another brokerage firm on our own. Four years and five years later, it turned out to be worth 1.1 billion.
Miguel Armaza: What kind of culture do you build in your companies?
Tom Sosnoff: I’m not what you would call a culture person. I’m a next person up type. Everybody’s expendable. Everybody’s replaceable. But we have, virtually for the last 25 years, zero turnover. We hire differently. We have no issue hiring friends who we know are going to be loyal, but they’re going to work their asses off. We also hire really smart people, and we challenge them nonstop. We found that the single most important thing is to challenge everybody. Don’t make this like some country club. Either step up or we’ll find somebody else. And when it comes to compensating, when we sold Thinkorswim, Scott and I gave $20 million just to our employees after the deal. When we sold tasty, we handed out $30 million just to our employees after. On top of whatever stock they already had. Both times, we gave away $50 million total. Zero legal requirement. We never publicized it. We never said a word to anybody. That’s just the way we are.
Miguel Armaza: You told me you’ve built Lossdog. You’re building a trading platform without the trading. What’s going on?
Tom Sosnoff: I had this crazy vision that I could try to do something that nobody else has done. We built technology without knowing how to build technology. We built media without knowing how to do media. So I’m figuring, well, we can attack one other thing, which is wealth inequality in America. It’s gotten significantly worse over the past five years. Executives, specifically CEOs, are grossly overpaid. Nobody needs to make 500 times or 1,000 times more than an average employee at your same company. We started to research it and found that the average employee at most companies is undercompensated over the course of their lifetime by a few million dollars. The average CEO is overcompensated by tens of millions. So we started down the path of career optimization for individuals, anybody making between $50,000 and $200,000. You can upload your resume and optimize your career path. We’re not interested in fixing your resume. We’re just interested in telling you what you should be worth and what you’re leaving on the table. Same thing with your portfolio. Then we’re adding all these agentic AI tools to allow you to do everything from portfolio creation to risk monitoring. That’s why I said it’s a trading platform without the trading. It’s all free. Then we’re launching a stablecoin, because I want to build the rails to deliver access to tokenized derivatives markets.
Miguel Armaza: What do you think is going to be the biggest benefit of tokenization for the consumer?
Tom Sosnoff: Tokenized assets to me aren’t that interesting anymore, because they’re a little bit of dead money, kind of like crypto. You buy some tokenized stock or some tokenized asset, you’re going to sit with it. It does make it easier for international customers, not having to convert to US dollars, you don’t need clearing, all that kind of stuff. But I think the real future is going to be in tokenized derivatives. The strategic side to tokenization, that’s where I can see this exploding. Options, futures, anything that’s leveraged, anything that’s strategic, liquidity pools. We designed an incredible mechanism for liquidity pool functions for futures. Essentially, why should Citadel get all the action? Let everybody participate. If I’m a customer and I want to put up $100,000 to make markets, why not?
Miguel Armaza: After all this time and all this success, you’re clearly having fun. Is that what motivates you?
Tom Sosnoff: What motivates you at a certain point in your life is your legacy. What are people going to say about you? I want people to say, hey, he was a really good entrepreneur. I don’t need any more money. I don’t need any more success. I’m motivated because what we’re building today is another challenge, and I want to keep building really cool stuff that challenges people, that challenges our own teams, that challenges myself. I can’t imagine anything worse for me than sitting on a beach or going to a country club. I would seriously lose my mind. I love working 10, 12, 15 hours a day. I love building stuff. I don’t believe in retirement. Why would you ever retire?
Miguel Armaza: If you were starting over as a 20-something year old with $10,000 in savings, how would you invest it?
Tom Sosnoff: It doesn’t matter. I would take as much risk as you can. Don’t overthink this. Spread it around. Either you’re going to learn how to win or you’re going to learn how to lose. Doesn’t make any bit of difference, but just learn how to take risk. Every time you come to this crazy little fork in the road, go the way that you think gives you the best probabilistic chance of success with the greatest reward. Take as much risk as you can. The Gen Z generation is a little bit on the gutless side. I got out of college in the middle of a recession, interest rates were 20%. Just take as many chances as you can. Don’t be conservative about anything.
This interview has been edited and condensed for clarity.
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