Tom Sosnoff has sold two companies for nearly $2 billion. He still executes more than 10,000 trades per year. At 69, he has launched a third fintech company — Lossdog — and is giving away $1 million in cryptocurrency to the first 50,000 people who sign up. The offer is a calculated opening move from someone who has made a career out of proving that individuals are being shortchanged by markets they do not fully understand.
A Career Built on Closing Information Gaps
Sosnoff began on the CBOE trading floor in 1981, spending two decades as a market maker, money manager, and running a prop trading firm. Options trading in that period was an institutional game — retail investors could participate in theory, but the analytical tools that made it profitable were firmly out of reach. Pricing models, risk calculators, probability frameworks: all of it lived on institutional desks. What retail traders had was guesswork dressed up as strategy.
Thinkorswim, co-founded with Scott Sheridan in 1999, was built to close that gap. The platform gave retail options traders professional-grade analytics for the first time, and TD Ameritrade paid approximately $700 million for it in 2009. Tastytrade followed — a financial media network that grew into a full brokerage platform and was sold to IG Group for $1.1 billion in 2021. Both companies operated on the same founding conviction: that access to better data produces better outcomes, and that most individuals have been systematically denied that access.
Lossdog applies the identical argument to the labor market. Employers have long used proprietary compensation data from firms like Mercer and Korn Ferry to price their workforce. Workers have navigated salary negotiations with Glassdoor ranges and LinkedIn estimates.
“The genesis behind Lossdog was that most people are underpaid and most executives are overpaid,” Sosnoff said. “People don’t optimize their portfolios, and they don’t optimize their wealth creation. My goal was to create software to help change that.”
The Platform and What It Does
Lossdog’s product is simple to describe. Someone uploads a resume, and the platform’s AI reads it against real government wage records. Then, it returns a single precise dollar figure representing what that professional is worth in their specific market at that moment. The platform identifies what is suppressing that number and provides a concrete roadmap to close the gap.
The claim behind that product is substantial. Lossdog’s foundational research found that a professional starting at $75,000 will leave roughly $3.9 million in nominal career earnings uncaptured over 30 years — not because of underperformance, but because of structural information asymmetry in the labor market. Most workers enter salary negotiations without knowing their precise value. Most employers do not share that disadvantage.
Alongside the salary tool, Lossdog runs a portfolio optimization layer that returns four specific outputs: an industry baseline return, a current expected return, a real-time strategic progress grade, and the lifetime dollar value of what underperformance is actually costing the user. Sosnoff has framed the two tools as a single problem: “Lossdog will be the closest one can get to a trading platform without trading.” Salary and investment returns, in his view, are the same wealth question approached from different directions — and most people have been operating without a clear answer to either.
The $1 Million Giveaway and the Bet It Represents
The promotional structure of Lossdog’s launch is tiered. The first 5,000 registrants receive $50 in cryptocurrency each. The reward decreases with each subsequent tier, reaching $10 for positions 30,001 through 50,000. Users receive an equal allocation of Bitcoin, Ethereum, Stellar, and Solana. Combined with 50,000 free first-year subscriptions worth $100 each, the total pre-launch commitment reaches $6 million.
More than 10,000 of the available 50,000 slots have been claimed as of early May 2026. The pace reflects something straightforward: a $1 million giveaway attached to a platform built by two people who previously generated more than $2 billion in exits tends to get attention. Sosnoff has described the logic without embellishment: “I rationalize it as just the cost of marketing. But like with thinkorswim and tastytrade, our marketing is either goodwill or content-based.”
The giveaway gets people through the door. The platform has to prove the claim once they are inside. If a professional uploads their resume and sees a precise, data-backed figure that differs materially from what they currently earn, the $100-per-year subscription sells itself. That is the same product logic Sosnoff used at thinkorswim: give retail traders tools precise enough to change how they see the market, and they will pay to keep using them. In his reading, the labor market is just another market where most participants have been working with the wrong data for too long.
