Cascade #30 – Aaron Bai: Dropping Out at 17 to Build the Next OS for Small Business Finance
Aaron Bai is the co-founder and CEO of Affiniti—a fintech company building a financial operating system for overlooked small businesses, starting with a no-fee credit card.
Aaron started college at 16, dropped out at 17, and raised his first round shortly after. His first company, a neobank, failed—strong product, weak market fit. So he reset. He and his co-founder spent months reading 10-Ks, talking to small business owners, and figuring out why existing fintechs weren’t working.
They landed on a simple insight: trust is the bottleneck. Most SMBs don’t need more features—they need something they believe in. Affiniti’s wedge is the card, but the goal is deeper: become the financial back-end for businesses that don’t have a CFO.
We talked about underwriting human risk, why most fintechs chase the wrong SMBs, and how Affiniti is turning everyday transactions into a data-rich, trust-first engine for financial clarity.
Learn more about Aaron and his company below: