Sosnoff co-built thinkorswim and tastytrade. He still calls himself a junkie. Fifty trades before lunch. Offices next to Wrigley. No retirement. He also sold a CBOE seat, rolled a decade of winnings into software without telling his family, and ran a firm that was profitable from month one. That is not a daredevil postcard. That is a man who learned what a bad morning at a clearing firm feels like.
Mining is one of the most volatile listed games on earth. It is also full of illiquid paper, slow rock, and people who confuse a press release with an edge. Sosnoff’s life is a filter for that tape.
The Pit Was Not a Strategy. It Was Speed Plus Flow
He lasted six months at Drexel Burnham in 1980, when policy rates were near 21% and a political-science major could talk his way onto a training desk. Friends staked $50,000 for a Chicago seat so they could work orders through him. They blew the stake in two weeks. He made $18. He did not yet speak the language. A stranger later put up $100,000. In two years Sosnoff made the man about half a million, bought him out, and market-made for 19 years in the S&P 100, hedging at the Merc.
There was no grand model. Bid. Offer. Stay busy. Four hundred men in his pit. Lawyers, doctors, dropouts — same animal. Across Chicago, maybe 10,000 to 15,000 of that type. He figures 95% did not last. That ratio should be taped above every junior watchlist. Most names do not survive the financing cycle. Survival was the edge. Quickness and a math mind, not software. He tried code. It was too hard. The floor was still the product.
Then he felt open outcry dying. He did not know if the end was six months or six years. He sold the seat so he would have no conflict and went all-in with Scott Sheridan on thinkorswim. All the money from ten years. Wives not told. He still calls that stupid risk attraction. He also calls it the same habit that keeps him working.
A mining parallel is ugly and useful. The promoter wants you all-in on the story. Sosnoff’s all-in was on a cash machine he could see daily, in a market he already spoke. A pre-resource junior is not that. It is closer to the two-week stake that vanished while he was still learning the hand signals.
1987 Was Not the Chart. It Was Whether the Money Was Still There
The host asked about 80% index drops. Sosnoff would not rule one out. He would not pretend 2000 or 2008 rewired him the way 1987 did. In ’87 there was no vol skew. Calls and puts were priced as if the world were polite. Velocity of risk had no premium. Prices went everywhere. The scare was not only the print. It was Monday morning and whether Schwab, First Options, Spear Leeds, or the rumor around Continental Bank still meant your account was money.
After that, everything changed. Retail options now sit at the OCC. That is not the same as a bilateral hedge with a bank that can disappear. 2008 still scared him for the industry. thinkorswim’s book, he said, was manageable. He even asked Ken Griffin about a piece of E-Trade. Griffin told him he did not want it.
Today he does not name the next 1987. He names the recipe: complacency plus leverage at record highs. Governments learned after 2008 that they can flood the system. That does not erase the recipe. It hides it.
Resource investors already own a version of counterparty risk. The “hedge” is a financing window. The window shuts. The company issues at a discount. Your basis dies while the thesis is unchanged. That is not a put. That is dilution. Size the name so a closed window is tuition, not an estate event.
Calculated Does Not Mean Timid
The host, an ex-Goldman options trader, pressed the contradiction. Sosnoff says he is a risk taker. He also never touched a $22.5 million TCV raise on a $100 million valuation around 2002–2003. Profitable from the first month. Organic for ten years. No Robinhood spike. One capital raise, parked.
Sosnoff agreed he likes odds in his favor. He also said they chased free cash flow because they launched into the dot-com wreck. Nasdaq composite from 5,000 toward 1,000. They did not know if capital would exist. Promotion helped them raise anyway. Cash flow meant they did not have to.
That is the mining split people blur. A producer with a mill and a treasury is a cash-flow problem you can model. A story stock is a capital-markets problem. Rolling ten years of pit winnings into a profitable platform is not the same as averaging down on a name that needs a raise before the next hole. Probabilistic risk means you can write the ways you lose. If you cannot write them, you are not taking risk. You are taking a narrative.
He Does Not Care What You Think. He Cares About the Expected Move
After the first sale he decided financial TV was a dead end. Fundamentals: what does so-and-so think? Technicals: a chart religion he never bought. He wanted the reverse of Black-Scholes as a customer tool. Expected move. Once you have that number, he said, you can do the rest. No news. No guess. Math plus banter.
They tried to hire Second City comics to deliver PhD research. The comics were funny alone and terrible together. A week before launch, Sosnoff and Tony took the desk. Fifteen years later that was the network. One year to the largest digital financial shop of its kind, in 2011, by his count. TD later offered $200 million for the content engine. They walked, built another broker with the same CTO and CFO, and sold tastytrade for $1.1 billion four years after launch. He stayed so the buyer’s trade would look good. He calls that honoring the trade. thinkorswim, in his telling, became worth many times the sale. tastytrade maybe double.
A mining letter that only asks “what do you think about this camp?” is CNBC in a fleece. The Sosnoff question is narrower. What is the expected move if the hole is barren, the metal drops 20%, and the company raises 25% of the market cap? If the letter cannot say it, the letter is entertainment.
Illiquidity Is the Feature He Will Not Buy
He manages his own book. Bankers handle cash. His daughter yells. Fifty trades in a morning. Futures overnight. Options by day. When he invests off-screen, he invests in people — small checks to founders he likes, sometimes because his name helps the next check. He is a terrible real-estate investor. Never made a penny in Chicago property besides the places he lives and the office compound.
Real estate, he said, is horseshit if you do not live in it. Illiquid. Ugly fees. Opaque marks. Often levered with a balloon. His first mortgage was 16.5%. He had to fight for that rate. The 40-year gift of falling yields is not a law of nature.
A junior with no bid on a 40-cent stock is that asset with a ticker. You cannot scalp the expected move if there is no market. You cannot sell a call to improve basis if open interest is a rumor. You can still own a thin name. You cannot pretend it is a listed option. Size it like a private note that might never have an exit.
What to Steal Without Becoming a Pit Trader
Decide faster than the chat board. Write the loss cases before the gain cases. Prefer cash-flow rock to story rock when you need ballast. Treat a financing window as counterparty risk. Do not use house-flip logic on a claim. Do not retire from learning because a metal went up. Honor the trade: if you sell a name into strength, do not poison the well for the next buyer you might need.
Sosnoff’s advice to the 20-year-old is do the scary thing while the compounding clock is long. A 25-year-old resource speculator hears that as license to empty the account into one drill hole. That is not his career. His career is many small, priced bets and a few large, cash-flowing builds. Failure is tuition. A blown treasury is not.
He will not retire. When someone says they have, it turns him off. The useful version for a mining investor is simpler. Do not retire from the bid-ask. The metal will not.
Conclusion
Sosnoff’s life is a warning wrapped as a dare. Take risk. Make it fast. Make it small enough that a closed window is not the end. Hate illiquidity unless you can stand still for years. Count expected move, not interviews. Honor the people on the other side of the trade.
The pit killed 95% of the alphas. The TSXV is not kinder. Price the swing. Then take it.
Important information
This article is educational commentary based on an interview with Tom Sosnoff. Company histories, sale prices, and product plans are the speaker’s. This is not advice to trade options, buy or sell mining securities, or use any brokerage or app. Most junior miners fail or dilute. Speak with a licensed adviser. The author and publisher accept no liability for actions taken on this article.