Welcome to Collections Conversations, a new four-part podcast miniseries from Fintech Takes, sponsored by our friends at C&R Software.

The series digs into how generative AI is reshaping debt collections; what it enables, what it complicates, and why it might finally force the industry to retire the word “collections” altogether.

In Episode 2, I sit down with Ed Wallen, CEO of C&R Software.

We kick things off with a hard truth about fintech companies that pride themselves on being customer-centric: that promise most often breaks at the exact moment customers need the most empathy and the most options. 

As Ed puts it, you get the Apple experience of onboarding, where everything is sunshine and rainbows, and then suddenly you get the Mad Max experience in debt collections. 

Our conversation unpacks why that shift happens. One day early and one day late feel the same to the customer, but on the inside, they trigger an entirely different playbook.

If replacing a customer can cost hundreds of dollars, why treat hardship as a liability instead of protecting lifetime value?

What if the real choice was between a churn machine and a loyalty engine?

This episode is a blueprint for anyone reimagining collections, servicing, and customer trust.

Subscribe to catch more about how generative AI might finally make collections more human.

This episode is brought to you by C&R Software. 

More than just debt collection, C&R sets the global standard for AI-native, humanized credit management. They simplify the complex with end-to-end credit-risk lifecycle support, powered by automated workflows, AI-native intelligence, and real-time, data-driven decisioning. Learn more at https://hubs.ly/Q03Wl1DY0.

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 Ed:

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

Learn more about C&R Software here: https://hubs.ly/Q03Wl1DY0

Welcome to Collections Conversations, a new four-part podcast miniseries from Fintech Takes, sponsored by our friends at C&R Software.

The series digs into how generative AI is reshaping debt collections; what it enables, what it complicates, and why it might finally force the industry to retire the word “collections” altogether.

In Episode 3, I sit down with John McNamara, Chief Growth Officer at Avtal.

John's career spans the private sector and the CFPB, where he worked on Regulation F, dragging debt collection out of an era when the law literally referenced telegrams.

That makes him perfect for unpacking the biggest misconception industry has about regulators, dubious credit repair organizations, and AI fluffery. 

We start inside the CFPB itself. John explains what industry constantly got wrong: they didn't understand the voices shaping policy. His benchmark for whether a rule landed? A symmetry of outrage and vitriol. If both sides are pissed, that's probably right.

From there, we dig into what John calls the credit reporting mess — why the credit reporting system creates inaccurate data, and how credit repair organizations exploit that through endless dispute loops

Plus, John’s first principles when it comes to AI: data governance and permissible purpose matter more than models, and better digital engagement usually beats new forms of automation (if someone's on your payment portal, they don't want to talk to you).

Subscribe now to catch what’s next.

This episode is brought to you by C&R Software. 

More than just debt collection, C&R sets the global standard for AI-native, humanized credit management. They simplify the complex with end-to-end credit-risk lifecycle support, powered by automated workflows, AI-native intelligence, and real-time, data-driven decisioning. Learn more at https://hubs.ly/Q03Wl1DY0.

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 John:

https://www.linkedin.com/in/john-mcnamara-75a2982/

Learn more about C&R Software here: https://hubs.ly/Q03Wl1DY0

Welcome back to Fintech Recap. I’m Alex Johnson, joined (as always) by my partner in recapping, Jason Mikula. Even if we aren’t sailing to BaaS Island, the news keeps flooding in.

We kick off with crypto market structure, which nearly cleared Congress before imploding. The Clarity Act would’ve locked in broad crypto rules, including limits on stablecoin yield. Banks had momentum to close a key Genius Act loophole (until Coinbase pulled support at the last second). The backlash was swift: other crypto firms were blindsided, lawmakers were furious, and Brian Armstrong ended up in Davos, facing off with Jamie Dimon (who, reportedly, told him to stop lying on TV). 

Then it's onto banking charters. NewBank got conditional OCC approval. Ford, GM, and PayPal all made ILC moves. Affirm filed in Nevada, citing "flexibility and diversification," but this is about control. With rising scrutiny on partner banks and consent orders in the air, a charter gives Affirm cleaner economics and regulatory insulation. Like Square and LendingClub before it, the goal is clear: own the balance sheet, shift volume gradually, and keep options open.

From there, Capital One’s surprise acquisition of Brex for $5B. Most commentary focused on the exit. More interesting is what CapOne wants: startup spend volume and a wedge into high-growth business banking. Integration will take time, and as Ramp scales faster on a leaner model, pressure around ROI will be mounting.

Plus, in our Can't Let It Go corner, we look at fintech's dumbest lawsuit: Prism v. TomoCredit. A fake cash flow underwriting product. A stolen trademark. Fabricated and backdated blog posts. An agreed settlement … that Tomo then refused to sign or memorialize. Meanwhile, the site still takes credit card details from consumers who can't unsubscribe. And somehow, it's still going!

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.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 the Fintech Takes podcast. I’m Alex Johnson, joined by Marc Rubinstein, author of the fantastic Net Interest newsletter. 

In this episode, we bounce through some of Marc’s most insightful writing from the past year (linked below) to spotlight the structural forces shaping 2026.

We explore why the U.S. has thousands of community banks, the idiosyncrasies of our 30-year mortgage product, the growing industry focus on agentic commerce, and why stablecoin infrastructure is coalescing around large, permissioned systems — and what all of that reveals about regulatory incentives, institutional power, and the future of financial infrastructure.

Highlights include:

Why the U.S. has thousands more banks than any other developed market

How agentic commerce is being driven more by investor decks than consumer behavior

Why OpenAI might accidentally save small merchants

Why stablecoins are moving onto permissioned, institution-backed rails (and will be increasingly shaped by players like Stripe).

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.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.

Net Interest pieces discussed:

Community First: https://www.netinterest.co/p/community-first-ca0

Inside the Affordability Crisis: https://www.netinterest.co/p/inside-the-affordability-crisis

Agentic Friday: https://www.netinterest.co/p/agentic-friday

Ready Layer One: https://www.netinterest.co/p/ready-layer-one

Follow Marc:

LinkedIn: https://www.linkedin.com/in/marc-rubinstein/

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 to Collections Conversations, a new four-part podcast miniseries from Fintech Takes, sponsored by our friends at C&R Software.

The series digs into how generative AI is reshaping debt collections; what it enables, what it complicates, and why it might finally force the industry to retire the word “collections” altogether.

In Episode 1, I sit down with Naeem Abraham, Senior Director of Product Strategy at C&R Software.

We kick things off with what I call the Collections Abundance Moment, tracing debt collection’s operational powerhouse roots (where empathy was sacrificed at the altar of efficiency) to a world where the old resource constraints no longer apply.

The episode dives into the mechanics of building safe, value-adding AI systems. Naeem outlines the “triangular dance floor” of competing pressures (risk, cost, and customer experience) and explains why the winners will be those who treat AI not as a system, but as intelligence. 

What if every customer had a personal banker in their pocket? 

What if cost no longer forced us to be adversarial? 

What if the prize wasn’t collections at all, but financial well-being?

This episode is a blueprint for anyone reimagining collections, credit, or customer care in the age of AI. Subscribe now to catch what’s next.

This episode is brought to you by C&R Software. 

More than just debt collections, C&R sets the global standard for AI-native, humanized credit management. They simplify the complex with end-to-end credit-risk lifecycle support, powered by automated workflows, AI-native intelligence, and real-time, data-driven decisioning. Learn more at https://hubs.ly/Q03Wl1DY0.

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 Naeem:

https://www.linkedin.com/in/naeem-abraham-b8a0ab10

Learn more about C&R Software here: https://hubs.ly/Q03Wl1DY0

Welcome back to Fintech Takes for a special bonus episode of Fintech Recap with Jason Mikula; Latin American sanctions evasion expert and author of a splendid ~5,500 word investigation on Kontigo that demands its own episode.

If you haven’t yet read Jason’s piece, “Kontigo: Y Combinator's Venezuelan Sanctions Evasion Startup” in Fintech Business News Weekly – the spine of this episode – you should (full link below).

This episode is a deep dive into Kontigo, a crypto‑fintech startup operating in Venezuela that marketed USDC off‑ramps and debit cards, raised money from Coinbase (among others!), and leveraged U.S. financial infrastructure (like JPMorgan Chase, Checkbook, Rain, Bridge, Lead Bank, and Stripe) … while operating in a heavily sanctioned environment.

The rise and fall of Kontigo raises urgent questions about accountability, compliance, and the risks embedded in stablecoin rails. 

We get into:

The foreign exchange arbitrage that made the model profitable

Why stablecoins are “speed-running BaaS” (but worse)

How product market fit in stablecoins can be code for money laundering, sanctions evasion, or financial crime

And the surreal online behavior of the CEO (shirtless hype videos included)

Plus, in our Can’t Let It Go corner: agave spirit startups, Kontigo’s logo that obviously nods at the Petro (Venezuela's failed oil backed cryptocurrency), and our favorite quote of 2026 so far!

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.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.

Read Jason’s “Kontigo: Y Combinator's Venezuelan Sanctions Evasion Startup” here: 

https://fintechbusinessweekly.substack.com/p/kontigo-ycombinators-venezuela-sanctions

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

Hello, and welcome back to Cash Flow Conversations, a miniseries sponsored by our friends at Nova Credit.

If you’ve followed my work, you’ll know that I’m obsessed with cash flow data (and underwriting more specifically) because it has enormous potential to positively reshape consumer lending in the U.S. 

Cash Flow Conversations tracks that shift, from theory to practical use across the lending lifecycle.

In Episode 5, recorded live at Money20/20, I sit down with Doug Swift (Navy Federal Credit Union) and Chris Hansen (Nova Credit) to talk about how cash flow underwriting has evolved over the past 18–24 months.

Cash flow data has gone from lenders’ best-kept secret to an infrastructure-supported tool with real traction. The vintages have matured; the use cases have expanded (second look underwriting, line assignment, portfolio management, delinquency support, loan rewrites, extensions, settlements, and credit line changes, to name a few). 

And Doug brings it to life with examples from Navy Federal’s collections workflows, which you won’t want to miss. 

Hope you enjoy the conversation as much as I enjoyed facilitating it! 

This episode is brought to you by Nova Credit. 

Nova Credit is a credit infrastructure and analytics company that enables businesses to grow responsibly by harnessing consumer credit data. Learn more at novacredit.com.

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 Chris:

https://www.linkedin.com/in/chrishansen10/

Follow Doug:

https://www.linkedin.com/in/doug-s-5794036/

Learn more about Nova Credit here.

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 stablecoin banking startup Kontigo, whose founder declared: “Kontigo is not a bank. Banking services are provided by the freaking blockchain.” We unpack the very fast arc that followed: getting deplatformed through its partner stack, the Venezuela and sanctions questions that can come with being “global by default,” and then the hack (Kontigo promised to reimburse affected users).

Next up is Givefront, corporate card and spend management software built for nonprofits. We get specific about what “built for nonprofits” means in practice: IRS 990 reporting, grant restrictions, donor policies, and the go-to-market riddle of reaching over 1.5 million organizations that rarely rip and replace systems. 

Then there’s Beycome, which promises an AI-assisted home buying journey. They charge sellers a flat fee to list their home and close (including a $399 package, marketed as saving sellers an average of $13,185 in fees). We talk about why real estate fees are such a durable profit pool, and why distribution’s the hardest part of this business.

Finally, we close with Cash App. Okay, not quite a startup at the same level, but there’s been a real vibe shift – as evidenced by a slew of new feature releases and capabilities inside Cash App (which we run through!). 

Plus,closing manifestations (manifesting some good outcomes for Cash App, and more episodes of Not Fintech Investment Advice for 2026).

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.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://www.kontigo.com/en

https://www.givefront.com/

https://www.beycome.com/

https://cash.app/

Welcome back to Fintech Takes. I’m Alex Johnson, joined (as always) by my partner in Fintech Recapping, Jason Mikula. In our first episode of the new year, we recap all of 2025 — through the big themes that shaped the industry and set the stage for 2026 (you’ll want to catch our predictions at the end).

First up, Regulation in the Upside Down. We dig into Trump’s second-term reshuffle which replaced independence with centralization. Tailoring became code for deregulation, and regulators started talking less about consumer protection and more about “making community banks great again” (their shorthand for rolling back rules under the guise of helping small banks).

Next up, stablecoins. With the GENIUS Act signed into law, 2025 was their breakout year. PayPal, Klarna, SoFi, and even Wyoming launched coins. We dig into whether yield-bearing stablecoins will reshape deposit markets or just become the modern equivalent of the free toaster you used to get for opening an account.

Then, it’s the latest in the open banking saga. And then, it’s looking at gambling as our national culture. (Prediction markets like Kalshi and Polymarket became sports betting apps in all but name, monetizing financial nihilism with bets on divorces, political violence, even war.)

Finally, the IPO window reopened. Klarna, Chime, Circle, eToro, Figure, and Wealthfront all went public. (And we both agree that staying private isn’t always a sign of strength, but some structure is better than none.)

We wrap with 2026 predictions (tune in to find out!), and in Can’t Let It Go, we offer up a crypto neobank that launched with a WWE-style promo, plus eerily targeted sports betting ads on YouTube…

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.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 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