Lossdog is the third venture from Tom Sosnoff and Scott Sheridan. The pair have already built two platforms that changed how retail investors operate — thinkorswim, sold to TD Ameritrade for $750 million, and tastytrade, sold to IG Group for $1.1 billion. Their latest company focuses on the two numbers that determine a professional’s financial life: What they earn and what their money earns.
Two gaps. One platform.
Lossdog addresses two common challenges professionals face salary optimization and investment performance, arguing that they are the same problem wearing different clothes. Both gaps exist because individuals have been operating without the quality of data that the other side of the table has always held.
On the salary side, employers have long used proprietary benchmarking data to price their workforce with precision. Workers have countered with publicly aggregated salary data, which tell a professional where the market generally sits, not what their specific background is actually worth. Research conducted byLossdog estimates the financial impact of this data A professional starting at $75,000 could leave roughly $3.9 million in nominal career earnings uncaptured over 30 years. The research brief’s bottom line is: “You do not need to feel underpaid to be underpaid.”
On the investment side, many individual investors have historically underperformed market benchmarks by material margins. This is often because of a lack of acces tothe probability-based frameworks that institutional desks have always used. Sosnoff spent two decades watching that gap play out on the trading floor. His response at thinkorswim was to put institutional-grade analytics in retail hands. His response at Lossdog is structurally identical, applied to a portfolio rather than a derivatives position.
“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.”
What the platform actually delivers
Lossdog’s salary tool analyzes a user’s uploaded resume. The platform’s AI reads it against real government wage records and returns a single precise dollar figure representing what that professional is worth in their specific market at that moment. The platform then identifies what is suppressing that number and maps a concrete path to close it, whether through negotiation positioning, skill prioritization or career moves that maximize earning trajectory.
The portfolio tool runs tits mathematical logic on a user’s investment holdings. It 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 the gap between those two figures is costing the user. From there, the platform delivers specific actionable strategies to improve returns and reduce basis. There is no advisory fee. No human intermediary. Just the data, the gap, and the steps to close it.
While other services focus on professional networking or general salary estimation, Lossdog aims to provide specific, data-driven estimate for both compensation and portfolio performance.. The subscription is offered at $100 per year, currently free for the first 50,000 registrants as part of the platform’s launch offer.
Why the track record matters
Sosnoff began on the trading floor in 1981, spending two decades as a market maker, money manager and operator of a prop trading firm. When he co-founded thinkorswim with Scott Sheridan in 1999, the platform provided retail options traders with analytical tools, including probability calculators, risk modeling and professional-grade pricing frameworks, previously limited to institutional desks. TD Ameritrade acquired the company for $750 million. The platform remained a respected brand and in use for years after the acquisition.
Tastytrade launched in 2010 as a streaming financial network before becoming a full brokerage in 2017, offering advanced derivative trading technology for retail investors. IG Group acquired the company for $1.1 billion in 2021. Across both companies, the founding logic has been to provide individual traders with institutional-quality data access to drive better financial decisions.
Lossdog applies this conviction to both the labor market and the retail investment space. Sosnoff still executes more than 10,000 trades per year. Cofounder Sheridan has nearly three decades of experience as a market maker. The company is now applying their established approach to these two distinct markets.
Disclaimer: As with any investment, like trading, there are risks. That’s why it’s best to educate yourself and consult with a professional financial advisor about which investments are right for you.
