Engaging regulators and product structure

Welcome back to the Fintech Takes podcast. Today’s episode kicks off a new long-form interview format I’m calling Diving Deep.

And in this episode, that’s exactly what we do with Max Levchin, co-founder and former CTO of PayPal and co-founder and the current CEO of Affirm.

This is what makes Max one of the most influential people in the history of fintech.

We start with Max’s early PayPal years, when building encrypted mobile wallets and secure handheld payments for Palm Pilots taught Max a lesson about timing, distribution, and the danger of solving puzzles before the market needs them (being right about the future means very little if you’re early in the wrong way).

From there, the conversation follows the spine of Affirm’s business, underwriting. Max explores how his experience at PayPal pushed him toward lending at the point of sale, which unlocked a different kind of math (and how Affirm built an internal engine that could evolve as machine learning grew smarter, without losing reliability, repeatability, or regulatory discipline).

That logic runs straight into product design. No late fees, treated as a constraint, not a revenue stream. Full Truth in Lending disclosures shown at checkout every time, even when advisers warned the extra screen would kill conversion. Credit bureau reporting when most other BNPL players avoided it. The throughline is incentives: design the system so the lender only wins when the customer does, and culture has a fighting chance to scale.

We end in the future, with agentic commerce. As machines get better at optimizing decisions, the financial products that survive will be the ones that were honest to begin with (but also what happens when software starts flagging bad financial deals before people do?). 

Sign up for Alex’s Fintech Takes newsletter for the latest insightful analysis on fintech trends, along with a heaping pile of pop culture references and copious footnotes. Every Monday and Thursday: https://workweek.com/brand/fintech-takes/

And for more exclusive insider content, don’t forget to check out my YouTube page.

Follow Max Levchin:

LinkedIn: https://www.linkedin.com/in/maxlevchin/

Follow Alex Johnson: 

YouTube: https://www.youtube.com/channel/UCJgfH47QEwbQmkQlz1V9rQA/videos

LinkedIn: https://www.linkedin.com/in/alexhjohnson

X: https://www.twitter.com/AlexH_Johnson