What if someone told you you’ve been underpaid by more than two million dollars across your career?

In this episode, Jason Henrichs speaks with fintech entrepreneur Tom Sosnoff. You may know Tom from founding thinkorswim and tastytrade, two billion-dollar exits that transformed retail investing. His newest venture, Lossdog, launching this month, focuses onsalary transparency.

Traditional compensation platforms rely on legacy salary benchmarks and anonymous, unverified self-reports that create wide ranges. Lossdog’s approach to compensation data is one that uses AI and verified data sources to deliver personalized valuations rather than vague, crowdsourced ranges. Think of it as whole-person valuation meets Machine Learning — a worth engine combined with AI onboarding surfacing overlooked value in resumes, including skills, certifications, pivots, and even career gaps.

It’s all about fair value and knowing your worth! Lossdog aims to give individuals institutional-grade tools to negotiate salary on equal footing with employers by generating accurate compensation valuations.

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