Tom Sosnoff on Risk, Trading, and Building Billion-Dollar Companies

Tom Sosnoff is the co-founder of thinkorswim and tastytrade, two of the most influential trading platforms in modern finance.Before building billion-dollar companies, Tom spent nearly 20 years as an options market maker in the pits of the Chicago Board Options Exchange. In this conversation, he sits down with David Heacock to discuss how trading rewired the way he thinks about risk, entrepreneurship, decision-making, and wealth creation.They cover:- Why most people completely misunderstand risk- The psychology of great traders and entrepreneurs- Lessons from the 1987 crash and the 2008 financial crisis- Building thinkorswim from scratch after leaving the trading floor- Why thinkorswim was profitable from month one- How tastytrade used content as a competitive advantage long before creator businesses became mainstream- Why Tom believes content and attention are now the real moat in finance- His views on retirement, legacy, and building companies late into life- Why he hates real estate investing- How options trading changes the speed and quality of decision-making- Why young entrepreneurs should take far more risk than they think- His new AI-driven company, Lost Dog, focused on career optimization and wealth inequalityTom also shares stories from the early days of Chicago trading pits, competing against Interactive Brokers, selling billion-dollar companies, making 50 trades before breakfast, and why he still wakes up every day obsessed with building.If you enjoy conversations about markets, entrepreneurship, risk-taking, investing, and building enduring businesses, this episode is for you.