EXCLUSIVE: Tom Sosnoff’s Next Big Bet Is On Your Career

Tom Sosnoff is a name that needs little introduction. A seasoned entrepreneur with notable exits, he still approaches new ventures with the same urgency and curiosity as in his early days.

Despite eventually becoming a big success, he admits that his first venture, thinkorswim, was far from user-friendly in its earliest form.

“We launched without a charting package,” Sosnoff says through laughter from his home office in Chicago.

 “I had years of experience as a floor trader and didn’t even know what technical analysis was. Back in the pits, we traded the order flow.”

The adjustment came quickly. His next venture, tastytrade, was built on the idea of the internet as a live media platform for traders—an approach that ultimately led to a ten-figure exit.

A New Chapter

Now Sosnoff is turning his attention to a different kind of problem. His new venture, Lossdog, will help individuals optimize their careers and financial decisions in measurable, data-driven ways.

“The platform is for anyone, but probably the best value will be for Gen Z and Millennials—mobile-first users earning between $60,000 and $250,000 a year. They leave so much money on the table,” he explains. 

“It’s not only about how much they’re underpaid relative to their value, but also how little they plan for their financial future.”

Although sometimes criticized for his stance on passive investing, Sosnoff draws a clear distinction.

“I’m not opposed to passive investing—I’m opposed to passive behavior. Without education, and without leveraging technology to optimize the careers of younger generations, it will be impossible to reduce wealth inequality.”

Lossdog is designed to do exactly that. Instead of focusing on trading activity, it aims to quantify the financial impact of everyday decisions, such as career moves, compensation structures, savings rates, and portfolio allocations, using real data and analytics.

As part of its debut this month, the company is waiving the first-year subscription fee for the first 50,000 users.

“Lossdog will be the closest one can get to a trading platform without trading,” Sosnoff says. “I don’t know any place where you can go that will optimize your career in a quantitative fashion, or optimize your portfolio in the same way. It will be new technology.”

The idea is to give users hard numbers—clear, measurable insights into how their choices affect long-term outcomes—rather than relying on generic advice or passive defaults.

New Ventures, Old Partners

For this venture, Sosnoff has once again teamed up with longtime collaborator Scott Sheridan.

“I’ve known Scott for nearly 40 years, and it’s wonderful how our skill sets come together. I’m much more of a software guy, while he’s operational.”

Working with a lean team of about 15 people, Sosnoff says the environment feels familiar, similar to earlier startups, but with one important difference.

“At this stage of our lives, there are certain privileges. We don’t have the financial pressure to deliver, and we can relax and do what we do best.”

When asked about the scale of the problem and the long history of failed attempts to reduce economic inequality, Sosnoff remains undeterred.

“The problem is immense, but with technology, we can change the way people look at their compensation. We can change how people view their portfolios by giving them hard numbers. I’m committed to seeing this through.”

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