Diving Deep with Max Levchin

9 snips

Dec 31, 2025

Max Levchin, a serial fintech entrepreneur and co-founder of PayPal and Affirm, shares his journey from early mobile wallet innovations to modern lending practices. He emphasizes the importance of market timing and consumer-centric product design, revealing how Affirm avoids late fees and prioritizes transparency. Levchin discusses the evolution of underwriting powered by machine learning and his regulatory philosophy focused on consumer protection. He envisions a future where AI agents guide consumers to beneficial financial choices, enhancing overall outcomes.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

ANECDOTE

Too Early Tech: Palm Pilot Lessons

Max Levchin built encryption libraries for Palm Pilots expecting secure handheld payments long before the market existed.
The team realized their web demo solved a real problem: moving money online, which became PayPal's killer feature.

INSIGHT

Solve Valuable Problems, Not Just Puzzles

Valuable problems, not just hard puzzles, deserve multi-year focus from founders.
Ask whether the arrow of causality points from difficulty to value before committing time.

ADVICE

Design For Real Users, Not Yourself

Design products by embodying an average user's context and constraints, not your own preferences.
Observe real behavior (e.g., grocery checkout) to shape simple, habitual-friendly interfaces.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

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