Pro Q & A 196: Tom Sosnoff Is In The Hot Seat

The Options Insider
The Options InsiderMay 27, 2026

Why It Matters

Lost Dog could reshape salary negotiations and personal investing, challenging traditional brokerages while tackling systemic wealth inequality.

Key Takeaways

  • Lost Dog launches as “trading platform without trading” for career earnings
  • Platform uses AI to estimate personal market value and missed wealth
  • Users receive crypto incentive and join a waitlist of 25k
  • Lost Dog plans 22 AI agents for portfolio optimization and tokenization
  • Tom Sosnoff remains bearish, shorting market despite recent rally

Summary

The video marks Tom Sosnoff's return after eight years, introducing his new venture Lost Dog, a fintech app that blends career‑earnings modeling with portfolio analytics.

Lost Dog leverages agentic AI to ingest resumes, LinkedIn data, and investment holdings via Plaid, then outputs a personalized “worth” figure and quantifies money left on the table. The company aims to narrow the U.S. wealth gap by empowering workers to negotiate higher salaries and optimize portfolios.

Sosnoff highlighted that his target demographic typically leaves $5‑10 million unrealized over a career, and that early adopters receive a crypto “welcome” bonus from a $1 million distribution. He noted a 25,000‑person waitlist, incremental roll‑outs of 5,000 users per week, and plans for 22 AI agents, a stable‑coin, and a daily “One Lucky Dog” show.

If successful, Lost Dog could shift bargaining power toward employees and democratize sophisticated portfolio tools previously reserved for traders. Its hybrid model may spur competition among fintech firms to embed AI‑driven compensation analytics into broader financial services.

Original Description

On this episode we are joined in the Hot Seat by Tom Sosnoff: Co-Founder of Thinkorswim & Tastytrade and now Co-Founder of LossDog.
Tom talks about his new venture Lossdog and also tackles your questions about:
🔹His thoughts on the current market rally
🔹His favorite options strat
🔹Crypto, MSTR and DAT risk
🔹The problems with options brokerage firms
🔹Is he trading 100 short strangles a day? and much more.

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