Tom Sosnoff spent roughly two decades as a market maker on the Chicago Board Options Exchange before deciding retail traders deserved professional-grade tools. In 1999 he co-founded thinkorswim, sold to TD Ameritrade for about $606 million in 2009, then co-founded tastytrade, later tastylive, acquired by IG Group for roughly $1 billion in 2021.

Along the way he became options trading's loudest evangelist, preaching high-probability, mechanical, small-and-often trading to a grassroots audience that grew into millions. His mantra, "trade small, trade often," reframed how a generation thinks about risk and edge.

In September 2025 he stepped away from tastylive to build again. He is now founder and CEO of Lossdog, an AI-driven platform, home of the daily One Lucky Dog show and a stablecoin play aimed at tokenized derivatives, seeded the same grassroots way tastytrade once was.