Al Goldstein has started companies before every AI cycle got here — a publicly traded consumer lender, a 13-year-old fintech now eyeing an IPO, and now StoicLane, which has made 90-plus acquisitions since 2021, applying AI to small business services. In this conversation, he and Ram Ahluwalia of Lumida Wealth Management cover the AI-and-education debate playing out in their own households, why banking is quietly becoming one of the most contested categories in tech, his family's journey from the Soviet Union to the American Midwest, and the AI-powered roll-up playbook now being copied across the industry.
00:00 Introducing Al Goldstein: Enova, Avant, and StoicLane
01:18 What Al learned hosting 57 episodes of his own podcast
02:31 Trust, media, and the rise of creators as a news source
04:22 AI, critical thinking, and raising kids in this era
05:36 Alpha School, Y Combinator, and rethinking education
07:56 Inside Avant: mission, scale, and the credit builder product
09:23 How Al thinks about a potential Avant IPO
10:12 The new wave of fintech bank charters, including Erebor
17:24 Al's family story: Soviet Union to Chicago
19:32 Teaching STEM and math in the age of AI
22:13 AI inside Avant: 100x engineers and a mobile app rebuilt solo
23:57 AI voice agents now handle most of Avant's customer service calls
24:43 Building toward a "personal CFO" banking experience
28:11 The White House AI summit, Elon Musk's reversal on AI risk, and Jevons paradox
32:18 Does AI widen inequality between the curious and the complacent?
32:57 Midterms, populism, and the state of free markets
38:23 Inside StoicLane: rolling up accounting, payroll, and IT services with AI
47:46 Competition heats up as capital floods into AI services roll-ups
49:52 Comparing the model to industrial roll-ups like Brad Jacobs'
50:02 Avant's NASCAR partnership and closing thoughts