World’s Greatest Trader: How To Win In Chaos | Tom Sosnoff - The Pomp Podcast Recap

Podcast: The Pomp Podcast

Published: 2026-03-16

Guests: Tom Sosnoff

What Happened

Tom Sosnoff, the founder of Lostog, has sold two companies for a total of one billion dollars, demonstrating his prowess in the trading world. He notably scalped two exchanges for 350 million dollars, showcasing his ability to navigate and capitalize on market opportunities. Additionally, he built the small exchange and sold it to crypto.com for a quarter billion dollars, then bought it back for just 10 million, reflecting his strategic acumen.

Sosnoff's new venture involves building an AI platform that empowers individuals to know their worth and optimize their investment portfolios. This platform includes an agentic AI that allows users to create crypto portfolios with a simple command, aiming to revolutionize how independent investors manage their investments. The AI tools are designed to monitor and manage portfolios 24/7, catering to investors who prefer self-management over relying on financial advisors.

Sosnoff emphasizes the importance of a diversified portfolio, combining both active and passive investments across various liquid asset classes. He illustrates the volatility within markets, particularly in crypto, which trades at three to four times the volatility of the S&P 500. Volatility is mean-reverting, contrasting with price trends, and Sosnoff prefers shorting volatility rather than buying it, as evidenced by his strategies in the oil market.

The episode delves into the income disparity between CEOs and average workers, with some ratios as high as 800 to 1. Sosnoff is also giving away a million dollars in Bitcoin, Ethereum, Solana, and Stellar to the first 50,000 sign-ups on Lostdog.com, structured to benefit earlier sign-ups and referrals. This giveaway reflects his commitment to engaging with the community and promoting financial literacy.

Retail trading firms like Robinhood, Tasty, IB, Thinkorswim, and Schwab are heavily involved in options trading, which makes up 85% of the trading industry. With stock trading declining due to high costs, options and futures are becoming more dominant. Zero-day options have gained popularity due to their speculative nature, with speculation now seen as a positive driver for wealth creation and the economy.

Sosnoff discusses the challenges faced by prediction markets due to high costs and lack of strategic value. Event-based trading can be expensive, with costs significantly higher than those for stocks, options, or futures. Despite these challenges, there is potential for more exchanges in prediction markets, with companies like DraftKings, CBOE, and Kraken showing interest.

AI's role in the trading industry is evolving, with high-frequency trading firms using it for monitoring rather than direct trading. The RIA space is expected to be impacted significantly by AI, leading to reduced fees and more informed advisors. Advisors may become more empathetic companions to their clients, as self-directed investment continues to grow as an additive force in the financial advisory industry.

Sosnoff and his teams face challenges, with a contentious relationship between his AI and software teams. Despite these challenges, quantum proof encryption is highlighted as a growing area of interest due to increasing security concerns. This reflects the ongoing evolution and integration of AI and technology in the financial landscape.

Key Insights