In this conversation, Adhi Rajaprabhakaran and Gary DeWaal explore the evolution of prediction markets, the impact of technology on trading, and the role of regulation in shaping these markets. They discuss the historical context of the CFTC, the rise of crypto, and the development of event contracts.

This episode of 50¢ Dollars goes deep with Ron Bernstein, the co-founder of InTrade—the original real-money prediction market. Together they trace the rise, fall, and lasting influence of InTrade, from its regulatory battles with the CFTC to its impact on today’s platforms like Kalshi and Polymarket. It’s a rare firsthand look at the origins of the prediction-market industry and where it’s headed next.

• (00:00:00) - Free Money
• (00:00:15) - Predicting the Future With Ron Bernstein
• (00:02:01) - Intrade: The Startup That Changed Sports Trading
• (00:06:53) - InTrade CEO on Sports and Political Betting
• (00:13:25) - Crowdfunding and the Regulatory Arc
• (00:16:37) - Political Prediction Markets: The Rise and Fall
• (00:17:49) - InTrade Group chairman on the CFTC
• (00:25:00) - InTrade Ventures and Augur: The Crypto Story
• (00:30:06) - Predicting Markets: The Unprofessional
• (00:31:48) - War Markets: Do They Work?
• (00:34:28) - Marcelo on Augur and His Exit
• (00:40:40) - Trade of a Lifetime: Tradesports and Ethereum
• (00:43:36) - Ex-Coin CEO on Zero X Trading
• (00:45:26) - Barron's: Crypto Prediction Markets Will Go Mainstream
• (00:50:24) - Have We Reached a Dominant Crypto Market?
• (00:54:56) - Ronald Feist on the Crypto Ecosystem
• (00:57:11) - Ron Krupa