From the trading pits of Wall Street to building some of the most influential fintech platforms in the world, Tom Sosnoff has spent 45 years redefining how people engage with financial markets. A self-described “markets junkie,” Tom began his career as a market maker before transitioning into financial technology, where he built groundbreaking companies like Thinkorswim and tasty. Now, as Co-Founder and CEO of Lossdog, he’s embarking on a new chapter—one that reaches beyond trading and into the future of worker fairness and optimization.

In this interview, Tom reflects on an unconventional career path that started with a single job offer on Wall Street and evolved into a lifelong passion for building. Rather than trying to “solve problems,” he focuses on creating products he personally believes in—platforms that challenge industries and reshape expectations. From transforming derivatives trading technology to pioneering digital financial media, his ventures have consistently stayed ahead of their time.

Today, with the launch of Lossdog, Tom brings his fintech expertise to a bold new mission: helping individuals optimize both their career value and portfolio performance through an AI-driven platform.

From Trader to Platform Builder: Tom’s 45-Year Obsession with Markets

Tom doesn’t describe himself as a visionary, a disruptor, or even a serial entrepreneur. He calls himself something much simpler: a “markets junkie.” For 45 years, that obsession has shaped his life. The first 20 were spent in the chaos of the trading pits as a market maker; the next 26 building financial technology for traders who wanted something smarter, faster, and frankly, cooler. Trading wasn’t in his DNA—his mom was an art teacher, his dad a civil rights attorney—but one Wall Street interview after college changed everything. He took the job. He never left the industry.

If you ask Tom what drives him to keep launching companies, the answer isn’t some polished leadership philosophy. It’s much more blunt—and much more human. He doesn’t have hobbies. Days off don’t excite him. Long weekends make him restless. So he builds. Platforms, networks, tools—if there’s something he wishes existed, he creates it. “I just build stuff,” he says, and you can hear the shrug in his voice. For Tom, entrepreneurship isn’t a strategy. It’s a default setting.

That mindset shaped Thinkorswim and later tasty. He wasn’t trying to “solve problems” in the traditional startup sense. In fact, he pushes back on that idea entirely. “I’ve never tried to solve a problem in my life,” he says. Instead, he focused on building technology he personally wanted to use—first transforming derivatives trading for retail investors, then reinventing financial media by talking about what others avoided: math, probability, and strategy. People called it crazy. It worked anyway.

“I Just Build What I Want”: Why Tom Thrives on Pressure, Freedom, and Starting Small

Spend enough years in the trading pits and you develop something most founders desperately need: thick skin. Tom laughs when he says it, but he means it. Decades in the markets made him “pretty immune to pain,” and that resilience became one of his biggest leadership assets. After multiple exits and years of building, he’s earned something even more valuable than capital—the freedom to create without constantly looking over his shoulder. As he puts it, “The freedom to build whatever the hell you want is kind of cool.”

But here’s the twist: experience doesn’t make it easier. Each new company is still a grind. Different industry, different team, different problems—same intensity. Tom is clear about one thing: there’s no shortcut. If you want to build something meaningful from scratch, you have to throw yourself into it completely. Every time. The only real advantage experience gives you is pattern recognition—spotting past mistakes before you repeat them. The effort? Just as brutal. The fun? Just as addictive.

And while many founders dream of scaling to thousands of employees, Tom lights up when he talks about something else entirely: small teams. Ten to fifteen people in a room, building fast, experimenting, arguing, trying things that might fail—that’s his sweet spot. He’s done the 500-person company. He’s managed hundreds. But what he loves most is the early-stage chaos, when no one fully knows what they’re building yet. With Lossdog, he’s back to that phase—testing, challenging users, “throwing things against the wall,” and seeing what sticks. For Tom, that uncertainty isn’t scary. It’s the whole point.

The Black Sheep Strategy: No Club, No Favors, Just Results

Tom doesn’t network. He doesn’t play the insider game. And he definitely isn’t part of any cozy Wall Street circle. In fact, he proudly calls himself the black sheep of finance. Despite building platforms that now account for a massive share of U.S. derivatives trading, he says the industry still doesn’t exactly invite him to the party. There’s respect, sure. Credit where it’s due. But inclusion? Not really — and he wouldn’t have it any other way.

“I don’t owe anybody,” Tom says, and that independence is clearly a badge of honor. Over more than two decades, he’s raised outside capital just once. No constant fundraising roadshows. No chasing approvals. Just building, scaling, exiting — on his own terms. For Tom, success isn’t about being liked in the right rooms. It’s about legacy. Generational wealth for his family matters, of course. But personally? He keeps it simple. “I just want people to say I was good at building stuff.”

Getting customers, though — that’s the real grind. There’s no magic “go viral” button, no shortcut switch you can flip. In the early days of Thinkorswim, they hustled for every single user. Partnerships, live events, shaking hands in cities around the world — Tom has spent 25 years on the road telling the story. At tasty, they doubled down on content and community, racking up millions of users and views. And now with Lossdog, he’s doing what he’s always done: showing up, giving value first, even giving away money to spark interest. Because if there’s one thing Tom believes in, it’s this — build something bold, tell the story relentlessly, and let the outsiders stay outsiders.

“Every Chance You Get, Take the Risk”: Tom on AI, Disruption, and Building Without Fear

If you think Tom is slowing down at 68, think again. He’s not talking about retirement — he’s talking about quantum firms, AI integration, and building a brand-new headquarters near his home in Chicago so he can keep creating without missing a beat. “I do not plan to slow down,” he says, half serious, half daring the universe to challenge him. For Tom, the future isn’t about winding down. It’s about doubling down — especially now that he’s free from regulatory constraints and able to experiment more boldly than ever.

What really has his attention right now? AI — but not in the hype-cycle, buzzword way. He’s focused on where he has an edge: finance. That’s his lane, his battlefield, his playground. He doesn’t waste energy worrying about things he can’t control. In fact, that mindset frustrates him. Why obsess over forces you can’t influence? Instead, he’s bullish on the collision of AI and financial software, convinced that smarter tools can create real leverage for everyday people. And with Lossdog, he’s zeroing in on worker fairness — helping individuals understand their true market value so they don’t leave millions on the table over a lifetime. It’s disruption, yes — but practical, targeted disruption.

When asked what advice he’d give aspiring founders, he doesn’t hesitate. “Every time you have a chance to take risk, just take it.” No overthinking. No endless analysis. Just action. Tom believes most people talk themselves out of opportunity long before failure ever gets the chance. His philosophy is simple: if you take enough smart risks, you get better at taking them — and things usually work out. It’s not polished. It’s not cautious. But after decades of building, exiting, and starting again, it’s the mindset that still fuels him.