Welcome back to FinTech OGs! This week, I’m joined by two leaders whose careers have shaped the evolution of modern financial technology: David Haber, General Partner at Andreessen Horowitz and co-lead of their AI Apps Fund, and Owen Jennings, an executive officer and Block’s Business Lead.

From early ventures like Bond Street and the first days of Cash App to today’s frontier of AI in finance, David and Owen share how FinTech continues to evolve—what’s working, what hasn’t changed fast enough, and the massive opportunities they see ahead. We cover everything from consumer financial health to small business challenges, AI-driven automation, and the next wave of credit innovation.

This is a masterclass in FinTech past, present, and future.