EXCLUSIVE: Tom Sosnoff Missed Investing In Uber — Now He Thinks He Found The Next One

Years ago, a young founder named Travis Kalanick was going around Chicago, raising money for his ride-hailing startup. It was Uber Technologies’ (NYSE:UBER) pre-seed round, and serial entrepreneur Tom Sosnoff was among those who passed.

He asked what seemed like the obvious question.

“Who’s going to get in somebody’s car that they don’t know? For some reason, it didn’t click with me,” Sosnoff said in an exclusive interview with Benzinga.

Yet the miss came with a lesson. When an outdated, broken service industry is ready for disruption by a peer-to-peer platform, you don’t say no twice. Sosnoff has spent most of his career making such bets in the financial industry, first as a co-founder of thinkorswim and tastytrade, and more recently through Lossdog.

The Lossdog Pivot

After the launch earlier this year, Lossdog has grown to about 35,000 users. "Videos and content have really picked up” Sosnoff says.

Not every feature caught on, though. The career and net-worth tools turned out to be “more of a one-and-done.” People checked what they were worth and didn’t come back.

So Sosnoff changed course. Lossdog is now a platform for optimizing portfolios and trades, and the team is adding “one new, crazy, new extensive tool every single week.”

Next expansion is One Lucky Dog, a free ideas platform Sosnoff calls “one of the coolest things I’ve built.” It’s meant for people who want to manage their own money but don’t know where to start.

“We’re not saying we know anything,” he says. “We’re just giving ideas. If you find something you like, try it out.”

Brains Over Bots

Sosnoff is also working with Zero Hash on an on-chain product. Before it can launch, they need to pick a debit card partner so people can use it for everyday spending.

His team of about 30 people runs on AI. “We token max every single day,” he says. But he doesn’t believe AI will fully replace the human element.

Drawing on his expertise in trading derivatives, Sosnoff sees it as an agentic tool that “optimizes the mechanic on the order entry page” and catches mistakes in trade size, capital efficiency, and outlier risk.

“I don’t see AI trading for anybody,” he says. “Ultimately, it’s brains over bots.” That belief in people over algorithms is also what led him to his first investment outside finance.

The Second Uber

Sosnoff met Dr. Yevhen Pavelko through a social circle. Pavelko’s co-founder and COO Natallia Panysh used to work at tastytrade, so he took the meeting to be polite.

“I was very skeptical,” he admits. “It’s definitely outside of my domain expertise.”

Then he visited Pavelko’s robotic surgery lab at the University of Illinois Chicago and spent time with the med school’s dean and chancellor.

“I was blown away by everything,” he says. “There’s certain people you just meet in your lifetime, and you just want to bet on them. I think he’s gonna kill himself to make it work.”

The business is Inviah, which Sosnoff describes simply as “Uber for doctors.” With three clicks in the app, you can send a board-certified physician to your home, hotel, or office and watch them arrive on a live map.

Sosnoff understands the problem firsthand. “It’s a pain in the ass to go see a doctor", he says. He pays top dollar for a concierge doctor, but believes Inviah opens up that level of care to far more people.

According to Pavelko, the math works for everyone involved. A hand injury that costs around $3,000 to treat in the ER costs $575 through Inviah, done at home. Doctors who worked 80 to 90 hours a week in hospital jobs can make $1,500 seeing five patients in an afternoon. Pavelko wants to pitch to major insurers too, arguing that lower bills could save billions on claims.

So far, Inviah has 71 active doctors and close to 500 completed visits, and it closed a seed round at a $45 million valuation. It operates in Chicago, but plans a nationwide launch soon.

When asked whether expanding into healthcare is a growth bet, or the purest way to hedge the extreme tail risk of his age, Sosnoff, who turns 70 next March, responds with laughter.

"There’s a little. There’s no question there. But I hope they can scale it – It makes all the sense."

Photo courtesy of Lossdog