In this episode, we sit down with Lex Sokolin, a fintech veteran and founder of Generative Ventures, to unpack the latest in tokenized assets, crypto infrastructure, and the future of payments. Lex shares his insights on Robinhood's controversial OpenAI token launch, the evolution of security tokens, and why fintech giants like Stripe and Coinbase are racing to build AI-native payment systems. We dive into the regulatory hurdles, the shift from old financial factories to blockchain-powered rails, and how stablecoins could enable seamless commerce for AI agents. Lex also discusses the messy realities of public vs. private markets, the power of self-custody, and his new fund focused on the machine economy.Lex Sokolin: linkedin.com/in/alexeysokolin00:00:00 - OpenAI Tokens on Robinhood: What Happened?00:00:50 - Inside Robinhood's Arbitrum-Based Platform00:01:35 - Why Security Tokens Failed in 201800:02:38 - From ICOs to Enterprise Blockchain Attempts00:03:53 - How Robinhood's Product Is Really a Derivative00:05:13 - Eurodollars & Stablecoins: Regulatory Parallels00:06:21 - Launching Meme Coins vs. Tokenized Equity00:07:21 - Why Exchanges Build Their Own Chains00:08:30 - Who Controls Trading Rights for Private Equity?00:09:48 - Public Markets: Now Just for Cashing Out?00:11:06 - Why Exclude Private Equity from Financialization?00:12:19 - Rent Control for Assets? Markets Want to Flow00:13:37 - Fintech's Shift to Crypto-Native Products00:15:15 - How Commerce Drives Payment Processor Changes00:16:36 - Stripe vs. Coinbase: Battle for AI Agent Payments00:18:11 - Web2's Original Sin: No Native Payments00:19:27 - Stablecoins as Internet-Native Dollars00:20:57 - APIs for AI Agents: Machine-Speed Transactions00:22:17 - Where Are We in the Internet Payments Journey?00:24:07 - From Bitcoin to Stablecoins: What Changed?00:26:01 - Better Dispute Resolution with 402 Protocol00:27:42 - Why Blockchain Software Is Profoundly Better00:29:02 - Custody Risks: Lessons from Lehman & Hyperinflation00:30:24 - Self-Custody as an Option, Not a Requirement00:31:40 - Inside Generative Ventures & Machine Economy___Connect with Rex on social media:LinkedIn: https://www.linkedin.com/in/rexsalisbury/Twitter: https://twitter.com/rexsalisburyTikTok: https://www.tiktok.com/@rex.salisburyInstagram: https://www.instagram.com/rexsalisbury/