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: 

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Welcome back to the Fintech Takes podcast. I’m Alex Johnson, joined by Kiah Haslett, Jason Mikula, and Jason Henrichs. Four people. Two Jasons. It’s been a while!

Our group text has been arguing about the same thing for years, so we finally took it to the mic: is Die Hard a Christmas movie? 

The plan is simple. We spend an hour talking about Die Hard and pull it apart using ten questions I randomly came up with.

We start with how each of us came to the movie. VHS scarcity. Delayed first viewings. Pausing the movie mid-stream to Google financial instruments. From there, we get into Bruce Willis, the accidental invention of the everyman action hero, and why this movie doesn’t work with Stallone, Schwarzenegger, or a 70-year-old Frank Sinatra crawling through air vents.

Then we talk about villains, specifically, Hans Gruber. Along the way, we touch upon the FBI’s truly heroic ability to make everything worse, and just how many people in this movie are objectively bad at their jobs.

At the center of it all is the plot device that sends us down the deepest rabbit hole: bearer bonds. Kiah walks us through what they were, why they existed, when they disappeared, and why it’s not totally impossible that some are still out there. Yes, it’s more educational than anyone intended.

We wrap with favorite quotes, questions about workplace behavior in the 1980s, and the annual argument about what qualifies as a Christmas movie and who is allowed to die in one.

It’s unserious. It’s overthought. It’s our most festive episode yet.

Thanks for listening! 

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Kiah Haslett:

Newsletter: https://fintechtakes.com/banking/newsletter-subscription/

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

Bank Nerd Corner podcast: https://podcasts.apple.com/us/podcast/bank-nerd-corner/id1845925869

Follow Jason Henrichs:

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

Twitter: https://x.com/jasonhenrichs

Breaking Banks podcast: https://podcasts.apple.com/us/podcast/breaking-banks/id641357669

Follow Jason Mikula:

Newsletter: https://fintechbusinessweekly.substack.com/

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

Follow Alex: 

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

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

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

Welcome back to Not Fintech Investment Advice, where Simon Taylor and I do what we do best: talk about fintech startups we’re absolutely not giving investment advice on.

First up is Trudenty, a fraud intelligence network tackling first-party fraud. It uses federated learning to let issuers, PSPs, and merchants identify repeat abusers without sharing raw data. They’re starting with Worldline, JPMorgan Chase, and Mastercard, and keeping the pitch simple: they only sell one thing, and that one thing works. The stat that stuck with us? 80% of chargebacks are fraudulent.

Next is TidalWave, agentic AI for mortgage point-of-sale. Instead of replacing loan officers, it works like a 24/7 assistant (one that handles follow-ups, corrects docs, and chases data). They’ve raised $22M, with the largest homebuilder in the U.S. on the cap table. It’s mortgage tech that avoids the loan origination system entirely, steering clear of regulated decisions while cleaning up the messy front-end workflow that still kills conversion. 

Then there’s Kaaj, which is aimed at the part of small business lending that no software platform has ever fully cracked. Think about a business applying for a government-guaranteed loan or financing a new piece of equipment; lenders have to parse tax returns, bank statements, and identity documents that never look the same twice. The loans are too small for a credit team, but too complex for automation. Kaaj trains AI agents to read those documents and create the first draft of a credit memo that a human can review. The product solves a real problem, but the question is: can they win the category?

Finally, FinReach Solutions in India tackles the gap between micro and small business credit. Lenders have money. Credit guarantors are willing to share risk. What’s missing is the infrastructure between them. Every guarantee program runs on bespoke rules and manual forms. FinReach standardizes that process, automates the guarantees, and makes collateral-free lending possible at scale. Think of the US SBA, but rebuilt as actual software instead of paperwork.

Plus, some closing manifestations: AI for mortgage POS should fix the front-end friction that causes borrowers to drop out; SMB lending needs an actual platform between public money and private lenders; and rising chargebacks might say less about fraud and more about good customers who are tired of being treated like suspects.

Thanks for listening! 

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt 

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 Simon:

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

Substack: https://sytaylor.substack.com

Follow Alex: 

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

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

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

Companies featured:

https://trudenty.com/

https://www.tidalwave.ai/

https://kaaj.ai/

https://www.finreach.in/

Welcome back to the Fintech Takes podcast. I’m Alex Johnson, joined by Dave Wasik (Partner at 2nd Order Solutions) for our new series, Facing Credit, where we unpack what’s happening in lending right now.

First, we kick off with the big picture in December 2025, starting with delinquency rates. TL;DR: Things don’t appear to be improving, and if you squint, they may be eroding.

Next, credit cards and BNPL. Dave explains why cards hold up, thanks to their clear value prop, rewards stickiness, and issuer concentration (the top 10 issuers control 82% of cards). Minimum payments are flexible and low, helping riders through cash-flow crunches. On the other hand, BNPL has shifted from big ticket items to everyday spending like groceries and restaurants (we discuss why the shift raises concerns, especially with limited bureau reporting).

Finally, auto, student loans, and the thing at the top of Dave’s worry board: private credit. It’s enormous, growing rapidly, and hard to manage (there’s no data to either corroborate or refute the risks; leverage plus interconnected bets can turn a small shock into a cascade).

Plus, we’ll close each Facing Credit episode with our guest’s take on one trend shaping the industry. This time: what does the breakdown of FICO as the standard mean for credit scoring and underwriting?

Tune in for Dave’s take!

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Dave Wasik

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

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

Welcome back to Fintech Takes. I’m Alex Johnson, joined (as always) by my Jason Mikula, my partner in recapping — who I’ve been lucky to see a lot of lately, which makes recording this over the internet feel oddly impersonal?

First up, open banking updates. JPMC has updated data-access contracts with Plaid, Yodlee, Morningstar, and Akoya; covering, reportedly, 95% of data pulls on its systems (but is silent on players like Finicity, Stripe, Trustly, and MX). Meanwhile, the CFPB wants to finalize its 1033 rule by year’s end, possibly skipping key steps like the small business panel. The rule may allow data fees tied to “cost recovery,” but what counts as cost (and who has the leverage to charge it) is still very much in play.

Then it’s onto digital IDs. Apple now lets users create an identity credential in Wallet from a passport, using NFC and a liveness check. Jason tested it. It works, but usage is limited to select TSA checkpoints. And adoption faces the same slow climb as Apple Pay, but with higher risks if it fails. Identity credentials aren’t like payments: you don’t want them glitching at airport security!

From there, Green Dot (which some might describe as an OG fintech company) is going private and splitting up. Smith Ventures is buying the non-bank side, while CommerceOne (also backed by Smith) takes over the bank and folds it into a new holding company. It’s a move that looks like extraction (pulling the combo out of public markets that never knew how to value it), which raises questions for other banks trying to thread the same needle.

Plus, in our Can’t Let It Go corner: Jason dives into the latest lawsuit against Meta, where internal docs reveal the company blocked safety features that threatened growth, ran a 17-strike policy before removing sex traffickers (described as a very, very, very high threshold), and drew its own comparisons to Big Tobacco. And I flag a podcast moment so surreal it sounds fake: the CEO of Roblox endorsing prediction markets for kids (as long as they’re framed as “educational”).

Thanks for listening! 

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Jason:

Newsletter: https://fintechbusinessweekly.substack.com/

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

Follow Alex: 

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

LinkedIn: https://www.linkedin.com/in/alexhjohnson
Twitter: https://www.twitter.com/AlexH_Johnson

Welcome back to our Engineering the SMB Capital Stack, sponsored by our friends at Fundbox.

In this four-part series, we’re exploring small businesses, small business lending, and the forces shaping how small businesses access capital. I’m joined by Prashant Fuloria, CEO of Fundbox, as cohost.

In Episode 4 (our finale!), we turn to the role of banks (and how they fit into an increasingly unbundled lending ecosystem), and what collaboration between banks and fintechs really looks like in 2025.

To unpack it all, we’re joined by Jackie Reses, CEO of Lead Bank (and former Head of Square Capital, a pioneer in embedded capital for SMBs, particularly for B2C SMBs).

Highlights include:

How Square Capital redefined micro-lending, serving millions of U.S. businesses under traditional bank thresholds

Why embedding loans in software (not branches) rewrote the risk model for SMB credit

The rise of unbundled lending: fintechs, balance-sheet partners, and the capital markets “maturity curve”

How banks like Lead are re-bundling infrastructure to power fintech lending safely and at scale

The regulatory horizon (from agentic commerce to stablecoins and the next wave of small-business oversight)

From unserved salon owners to national infrastructure shifts, Jackie reminds us why access to capital is still deeply human, and why technology wins when it’s built with empathy for the entrepreneur.

If you want to understand where banks truly fit in the future of SMB lending, this finale is essential listening.

This episode was brought to you by Fundbox. 

As a leading capital infrastructure provider behind the digital SMB economy, Fundbox is focused on enabling platforms to embed financial tools directly into their user experiences. Learn more here: https://bit.ly/4o1cWVG

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 Alex: 

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

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

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

Follow Prashant:

https://www.linkedin.com/in/fuloria/

Follow Jackie:

https://www.linkedin.com/in/jacqueline-reses-938b7850/
Learn more about Fundbox here: https://bit.ly/4o1cWVG

Welcome back to the Fintech Takes podcast. I’m Alex Johnson, joined by Carlos Caro (author of the Free Toaster newsletter and host of the Free Toaster podcast) for the second episode of Facing Credit, where we unpack what’s really happening in lending right now.

This one’s about marketing; the overlooked starting point of every loan. 

Everything in lending sits downstream of how you acquire customers and what it costs to reach them. And right now, that system is in flux.

AI has upended the old rules of digital acquisition. Google’s “Helpful Content” update triggered what Carlos describes in his writing as the “SEO Apocalypse”, a collapse that’s wiping out 50–90% of organic traffic and forcing publishers, affiliates, and lenders to rewrite their playbooks. The rise of AI-generated search results and zero-click answers means the economics of attention have changed for good.

Carlos and I dig into:

How AI is breaking traditional digital marketing and reshaping lender acquisition costs

What Google’s updates mean for SEO, SEM, and the affiliate ecosystem

How creators like My Rich BFF and MrBeast are becoming the new distribution channels for lenders

And what “Generative Engine Optimization” (GEO) might mean for the next phase of search

Tune in for Carlos’s take on how lenders, publishers, and fintechs can survive the SEO extinction event (and what it’ll take to win attention in the AI age).

Plus, we reference these three Free Toaster pieces throughout the conversation; consider them required reading:

The SEO Apocalypse Has Arrived

How New Balance's CMO Turned Around A 15-Year Decline

Reddit Isn't an Affiliate Channel

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Carlos Caro:

LinkedIn: https://www.linkedin.com/in/the-carlos-caro/

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

Welcome back to our Engineering the SMB Capital Stack, sponsored by our friends at Fundbox.

In this four-part series, we’re exploring small businesses, small business lending, and the forces shaping how small businesses access capital. I’m joined by Prashant Fuloria, CEO of Fundbox, as cohost.

In Episodes 1 and 2, we explored the state of small business lending and how capital actually reaches small businesses. 

In Episode 3, we move to the heart of the SMB lending stack: underwriting (the core of how lenders evaluate and manage risk).

Joining us is longtime SMB lending leader, Bernardo Martinez, currently at SoFi. Bernardo is the executive leading SoFi’s SMB efforts (in addition to other initiatives like SoFi at Work, which is an employer-branded program to help companies support their talent through financial products).

Highlights include:

Why analog ops and missing data have always constrained SMB underwriting, and how overdue digitization and vSaaS are finally changing the picture.

What a true 360 degree view looks like when you blend bank transactions, payment processing, invoicing, and ledger data all together (and even flavor with non-financial signals like repeat visits, foot traffic, and even satellite imagery).

Where machine learning and generative AI actually belong in SMB lending, from stitching together CRM, accounting, banking, and marketing data to delivering CFO-style guidance that saves owners time (and lowers probability of default).

The next decade in small business finance isn’t about originating loans more quickly. The real unlock will be how well you feed the data back into the business itself (the better that business runs, the safer the loan becomes). 

That means translating raw signals into value added services that help owners strategize growth, spot risks early, and above all, save time!  Our data and tools are finally catching up to the needs of SMBs, which makes this an exciting moment for anyone building products for them.

Don’t forget to subscribe to catch future episodes and insights!

This episode was brought to you by Fundbox. 

As a leading capital infrastructure provider behind the digital SMB economy, Fundbox is focused on enabling platforms to embed financial tools directly into their user experiences. Learn more here: https://bit.ly/4o1cWVG

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 Alex: 

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

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

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

Follow Prashant:

https://www.linkedin.com/in/fuloria/

Follow Bernardo:

https://www.linkedin.com/in/bernardo-martinez-639293/

Learn more about Fundbox here: https://bit.ly/4o1cWVG

Welcome back to the Fintech Takes podcast. I’m Alex Johnson, joined by Mike Milotich, CEO of Marqeta (who stepped into the role after serving as CFO,) and now leads a cloud based issuing platform approaching 400B in annual payment volume. 

First up, we focus on Marqeta’s platform. It’s built out of configurable building blocks, and Mike gets specific about what that means in practice; walking us through clear examples, including how delivery platforms used virtual credentials to remove driver fraud, and how early BNPL providers relied on Marqeta to pay merchants behind the scenes (without integrating with every retailer).

From there, we shift to agentic commerce and why the issuer’s vantage point changes the conversation. Issuers face different constraints. They create the credential, set the controls, and carry the risk when something goes wrong. Mike unpacks how an AI agent could fund and configure a virtual card with narrow parameters so it can only execute the purchase the user intended, and how AI is being applied to fraud, risk, and disputes (plus how dynamic rewards will push cards toward real personalization).

We also dig into the insights Marqeta is seeing across its network. BNPL is moving into more everyday categories as a cashflow tool. And SMBs are starting to treat modern payments as real operational leverage (because automated controls and real-time tools replace the manual work that used to eat their time). 

For more insights, their 2025 State of Payments Report is linked below.

Thanks for listening!  

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Mike Milotich:

LinkedIn: https://www.linkedin.com/in/mike-milotich-7b78402/

Access Marqeta’s 2025 State of Payments Report here: 

https://www.marqeta.com/asset/state-of-payments-2025

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

Welcome back to the Fintech Takes podcast. I’m Alex Johnson, joined by Jennifer Tescher, founder and CEO of the Financial Health Network (who’s spent the last two decades measuring, defining, and holding the industry accountable for consumers’ financial well-being).

We dig into the latest FinHealth Spend Report, which found that U.S. households paid $455B in interest and fees last year (a $100B jump in just two years!), and unpack what that says about the fragility of American households.

From student loans and BNPL to agentic AI to the design of financial products, this conversation covers the hidden costs of “frictionless” finance … and why real innovation might mean adding friction back in.

Highlights include:

Why the $455B consumers paid in fees and interest is a canary in the coal mine for the economy (and how credit card debt and student loans are driving the jump)

How the uncertainty around student loan forgiveness has frozen households in place, changing decisions about careers, housing, and family

Whether BNPL helps or harms consumers (and why frictionless payments may have gone too far)

Why agentic commerce risks turning AI into a 24/7 sales engine (and what it would take to build AI that actually improves financial health)

How Financial Health Network’s new product design standards are nudging banks and fintechs to compete on doing right by customers

This episode is a sweeping, candid look at the real state of consumers’ financial health (and how design, data, and AI could either fix it or make it worse).

Thanks for listening!  

This episode was brought to you by Marqeta. Don’t sacrifice agility for stability. With Marqeta, launch payments experiences that perform at scale and flex with your business. Learn more at https://marqeta.com/ftt

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 Jennifer Tescher:

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

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