TOM SOSNOFF

Sosnoff grew up in New York and started his career on the Chicago Board Options Exchange floor in the 1980s. He was a market maker in equity options — someone who stood in the pit and continuously bought and sold options, providing liquidity to the market.

This gave him a granular, mechanical understanding of how options are priced and how volatility works that most retail traders never develop.

In 1999 he co-founded thinkorswim, a retail brokerage built around sophisticated options trading tools. The timing was good — the internet was making self-directed investing accessible — but the platform he built was genuinely better than anything retail traders had access to before.

It offered real-time options analytics, probability calculations, risk graphs, and volatility data that previously required institutional infrastructure. TD Ameritrade acquired thinkorswim in 2009 for $606 million.

Sosnoff stayed on briefly, then departed to start again.

thinkorswim, co-founded in 1999 and sold to TD Ameritrade in 2009 for $606 million, remains one of the most sophisticated retail trading platforms ever built. Even after the acquisition it continued to define the standard for retail options tools.

Many professional traders still use it today.

tastytrade (originally tastytrade financial network, launched 2011) is his second act. He built it as a financial media company — a live streaming show focused entirely on options trading education, with real trades made in real-time on camera.

It grew into a brokerage, tastyworks (now tastytrade brokerage), offering commission-free options trading with capped per-leg pricing. In 2021 IG Group acquired tastytrade for approximately $1 billion.

Sosnoff remains involved in the business.

Sosnoff is an options-centric, volatility-focused trader. His core approach, which he has systematized and taught through tastytrade, is to sell options premium — specifically to take advantage of the fact that implied volatility (what the market charges for options) tends to be higher on average than realized volatility (what actually happens).

In plain English: options are usually slightly overpriced because people pay a premium for insurance. Sosnoff''s strategy is to be the insurance company, not the insurance buyer.

He trades mechanically and at high frequency — many small positions across many underlyings, sized small enough that no single position can cause serious damage. He defines his edge as being short premium systematically across a diversified portfolio.

The thinkorswim sale to TD Ameritrade for $606 million in 2009 is the first major win. Building a retail options platform from scratch and selling it to one of the largest brokerages in America at the height of a financial crisis is a remarkable outcome.

The tastytrade sale to IG Group for $1 billion in 2021 is the second. Two separate billion-dollar-range exits in two decades, both built in the same niche — retail options education and infrastructure — makes Sosnoff unique.

Very few people disrupt an industry once. He did it twice.

Sosnoff has been transparent that short premium selling has losing periods that are severe and fast — when markets spike violently (2020 COVID crash, 2018 volatility spike), short options positions can lose money quickly. He has traded through these periods live on camera, which is either commendable transparency or an uncomfortable watch depending on the size of the move.

His broader criticism of the approach is that it requires true mechanical discipline: the strategy only works if you keep selling through losing periods, which is psychologically very difficult.

Sosnoff believes that most retail investors are sold products that serve the institution, not the investor — mutual funds with high fees, complex products with hidden costs, buy-and-hold strategies that underserve people who want to actively manage their portfolios. His philosophy is that options, used correctly, give retail traders tools that are genuinely superior to passive investing for active participants.

He believes in high frequency, small size, and mathematical discipline over intuition or conviction.

Sosnoff is married and lives in the Chicago area. He is known for being a devoted family man who keeps personal life out of his public persona.

His professional identity is entirely built around the trading and education businesses. He has said that what drives him is not money at this point — two major exits provide that — but the mission of democratizing sophisticated financial tools for retail traders.

State University of New York at Binghamton, BA. He is largely self-educated in options, having learned the mechanics from years on the CBOE floor before the internet existed.

He credits the floor as the only education that truly mattered.