The Compound and Friends

Tom Sosnoff Will Teach You Trading

52 snips
Sep 19, 2025
Tom Sosnoff, a veteran options trader and fintech entrepreneur known for founding Thinkorswim and TastyTrade, dives into the world of trading. He shares insights on his journey from pit trader to building a prop firm and emphasizes the importance of a contrarian mindset. The discussion also covers TastyTrade's unique math-driven approach to teaching trading, the impact of retail trading outcomes, and reflections on industry shifts, including Robinhood's disruption. Tom hints at future innovations in trading tools and community-building.
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ANECDOTE

From $50K To $18.75: Origin Story

  • Tom Sosnoff moved from New York to Chicago in 1981 with $50k backing and began trading on the floor. He remembers his first three days: the partners lost the $50k and he made $18.75.
INSIGHT

How The Pit Makes You A Contrarian

  • Floor trading forces you to take the other side of incoming orders, so you learn to be contrarian and opportunistic. Tom says that created his trader mindset: don't predict markets, respond to orders profitably.
ADVICE

Trade With Probabilities, Not Predictions

  • Use quantitative probabilities and volatility to set trades rather than bullish/bearish predictions. Improve your odds by choosing strike and time based on option-implied expected moves.
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