I don’t know anyone who enjoys filing their taxes. It is something we begrudgingly do every April, or earlier for the well-organized, and it is usually a somewhat painful exercise. What if filing your taxes was easy, taking less than 30 minutes? What if tax planning wasn't a once-a-year chore but an embedded feature in your banking app, payroll platform, or investment account?

In this episode, I sit down with Ben Borodach, founder and CEO of april, the first company to build a nationally licensed tax engine in over 15 years. Ben shares how april is transforming tax from an annual burden into real-time financial intelligence, partnering with banks, fintechs, and payroll platforms to embed tax services directly into the financial tools Americans already use. We discuss the massive technical challenge of building tax infrastructure from scratch, why embedded tax makes sense for financial institutions, and how bringing tax decisions to the point of transaction, whether selling stock, adjusting payroll withholding, or buying a home, can fundamentally change how people manage their financial lives.

In this podcast you will learn:

• How he came to the idea of building a fintech company focused on tax.
• How april was incubated inside Team8.
• Why they decided to create an embedded tax solution rather than go direct to consumer.
• What their product offering does.
• How they are helping consumers to think about taxes beyond once a year.
• The three categories of companies they are focused on.
• Why banks should be offering tax services to their customers.
• Why being integrated into the banking cores is not a high priority right now.
• How april is different to the big tax providers, TurboTax and H&R Block.
• How their customers present the tax offerings.
• What it means to be a nationally licensed e-file provider.
• How they integrate with the IRS and the state tax agencies.
• How they are leveraging the growth of embedded finance.
• What is involved from a technology perspective to integrate with april.
• How he thinks about tax policy, as a tax infrastructure company.
• Ben’s vision for april.

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Today, I sit down with Daren Guo, co-founder of Reap, the stablecoin infrastructure company and the world's largest stablecoin card issuer, processing over $6 billion annually. Daren shares his journey from being employee #90 at Stripe to building the next generation of financial rails based on stablecoin infrastructure, serving everyone from neobanks in Brazil and Africa to traditional financial institutions expanding globally.

The conversation explores why stablecoins represent more than just faster cross-border payments, they are the foundation for a fully tokenized economy where FX, bonds, equities, and real estate all move on-chain. Daren discusses Reap's recent MPI license in Singapore, their expansion into the US market, and how programmable money enables entirely new financial products like payroll streaming and on-chain escrow that simply weren't possible with legacy infrastructure.

In this podcast you will learn:

• Daren’s background setting up Stripe’s Asia business.
• Why he decided to leave Stripe to start his own company.
• Their initial product vision.
• His thesis around stablecoins and why they represent the future of payments.
• Why they decided to start with stablecoin-powered credit card infrastructure.
• Where they are a Visa Principal member and the markets they serve.
• The types of companies that Reap is working with today.
• How the flow of funds work for users of Reap’s credit card.
• Who is providing the stablecoin collateral.
• Reap’s expansion plans for the US market.
• Why they applied for a Major Payment Institution (MPI) license in Singapore.
• The product suite that they are working on right now.
• The scale that Reap is at today.
• How they are serving traditional firms as well as crypto-native companies.
• Daren’s vision for the next generation of money movement.

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Today I'm talking with Darragh Buckley, the CEO and co-founder of Increase. If you've been following fintech for a while, you probably know Darragh as employee number one at Stripe, where he built the team responsible for moving money at a massive scale. At Stripe, he learned a crucial lesson about infrastructure: when you're stuck solving business, technical, and risk problems all at once, you need to drop down a layer. That insight led to Increase, which does something quite novel, instead of connecting to banks one by one, they connect directly to the Federal Reserve itself, operating their own banking core that exposes all this functionality through APIs. With a team of less than 20 people, they're now processing over $100 billion annually.

In this conversation, we dig into the lessons Darragh learned scaling Stripe, why he believes compliance and accounting should be built into engineering from day one rather than bolted on later, his vision for a future where community banks serve specific communities like dentists or families managing elderly parents' finances, and why he's personally investing in community banks across the Pacific Northwest. We also get into real-time payments infrastructure, including a great story about buying a car on a Saturday. Now let's get on with the show.

In the podcast, you will learn:

• How Increase was born out of early challenges at Stripe.
• What he learned about scaling fintech companies at Stripe.
• The advantage of dropping down a layer when building fintech infrastructure.
• How Increase is able to connect directly to the Federal Reserve.
• The concept of a side core and how it integrates with banking cores.
• The different types of companies they work with.
• A fun story about paying a car dealer with a real time payment on a Saturday.
• The scale that Increase is at today.
• Why they decided that now is the time to spread with word about Increase.
• Why it matters to build compliance into your product very early.
• What lessons compliance can learn from software engineering.
• How they are managing real time risk.
• Why Darragh has personally invested in several community banks.
• What will have changed in financial services if Increase is successful.

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Today's guest is Jason Lee, a fintech veteran who has been at the forefront of employee financial wellness innovation for nearly a decade. After co-founding and scaling DailyPay into one of the pioneering companies in earned wage access, Jason went on to launch Salt Labs, an innovative employee rewards platform that Chime acquired just 18 months after its founding. Now, as the leader of Chime Enterprise, Jason is on a mission to make financial health benefits as ubiquitous in the workplace as health insurance.

In this conversation, we explore why he believes every employer will eventually offer these programs, not out of altruism, but because it makes compelling business sense. Jason shares fascinating insights about how financial stress undermines productivity, why employees value Salt's non-dollar rewards even more than cash, and his ambitious vision for building an employer-focused financial health platform that could parallel what Fidelity achieved in retirement. It's a conversation about the intersection of fintech, HR technology, and the future of work – and why the employer may be the most powerful catalyst for improving Americans' financial lives.

In this podcast you will learn:

• Jason’s high profile background in fintech.
• The origins of Salt Labs and how they became part of Chime.
• The premise for Chime Workplace.
• Why they are fundamentally in the productivity business.
• How they are able to measure financial wellness outcomes.
• Why employers are caring more about the financial health of their employees today.
• Jason’s prediction for employers and financial wellness.
• The target market for Chime Workplace.
• What they hear when they first go into a new employer.
• Why they don’t charge employers for Chime Workplace.
• How their SALT rewards work.
• Jason's vision for the future of employer-driven financial wellness.

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Today I'm delighted to be joined by Clive Kinross, CEO and co-founder of Propel Holdings. Propel is one of the most successful fintech lenders serving underbanked consumers, and what makes their story particularly compelling is how they've achieved it: profitably, almost from day one.

Since founding the company 14 years ago with just $4 million in capital, Clive and his three co-founders, who are all still with the company, have built a business that now serves a market of 100 million consumers across the US, Canada, and the UK. The company went public on the Toronto Stock Exchange in 2021 and has been the best-performing stock in its vintage.

In our conversation, Clive shares how his background as a chartered accountant shaped his disciplined, unit economics-focused approach to building a lending business, how Propel uses AI to analyze over 80,000 applications daily and make credit decisions in six seconds, and why he believes the opportunity to serve underbanked consumers in developed economies has never been stronger.

In this podcast you will learn:

• Why Clive decided to tackle credit for his second major business.
• How the company has evolved since its founding 14 years ago.
• The different brands they have in the US, Canada and UK markets.
• How their credit graduation programs work.
• The typical consumer coming to Propel for credit.
• How they differentiate themselves from others in the market.
• How their AI models work and the data they are feeding into these models.
• How Clive views the potential of AI throughout Propel’s business.
• Why he decided to take Propel public in 2021.
• How they were able to become a profitable fintech lender quickly and sustainably.
• What Clive is most excited about for the future of Propel.

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Nubank co-founder Cristina Junquiera joins the podcast to discuss one of fintech's most remarkable success stories, from a Brazilian startup that had customers begging to get off the waitlist to a publicly traded company serving 127 million customers and reaching 60% of Brazilian adults.

In this wide-ranging conversation, Cristina shares the origin story of how three founders from different countries came together to fight complexity in financial services, the challenges of conducting simultaneous IPOs in New York and Sao Paulo to give their customers access, and lessons from expanding into Mexico and Colombia. Most notably, she reveals why Nubank chose the massive US market as their fourth country, detailing their de novo bank charter application with the OCC and her relocation to Miami to lead the charge. Cristina also discusses Nubank's approach to digital assets, their partnership with OpenAI, and why she believes there's far more ahead for the company than behind it.

In this podcast you will learn:

• How Cristina’s time at Brazil’s largest bank prepared her for Nubank.
• How she met David Velez, the CEO and co-founder.
• What she saw was missing in the Brazilian market.
• When they realized that they were on to something special with Nubank.
• What they had to change when they expanded into Brazil.
• How consumers use credit cards different from Brazil to Mexico and Colombia.
• Why they took on the added complexity and cost of allowing their retail customers to participate in their IPO.
• How becoming a public company has impacted their mission.
• With 60% of adults in Brazil, how Nubank can still grow in their home market.
• When they decided that the U.S. was going to be in their expansion plans.
• What they see as the opportunity for Nubank in the U.S.
• Why they decided to file a de novo bank charter application rather than acquire a bank.
• Nubank’s approach to digital assets.
• How they are partnering with OpenAI and their approach to AI in general.
• What Cris is most excited about for this new chapter for Nubank.

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In this special episode recorded live at Money2020 in Las Vegas, we dive deep into what I think is the most transformative development in lending over the past decade: cash flow underwriting. I welcome back to the show Jason Rosen, CEO and co-founder of Prism Data (I last had Jason on the show back in 2019 when he was with Petal), to explore how real-time bank account data is revolutionizing credit assessment in ways that traditional credit scores simply can't match.

Jason explains why the financial disruptions of 2020, from pandemic relief to widespread job changes, exposed critical gaps in conventional credit reporting, and how cash flow underwriting is filling that void. The conversation covers the breakthrough adoption of this technology by major traditional banks, the limitations of FICO scores in capturing a complete financial picture, and why cash flow underwriting represents a once-in-a-century shift in how creditworthiness is measured.

In this podcast you will learn:

• How Jason first got interested in cash flow underwriting.
• The origin story of Prism Data and how it was incubated inside Petal.
• How he describes Prism Data today.
• What goes into building their unique credit models.
• How their CashScore is created.
• What matters most in how they distill all the semi-structured data into a score.
• Why credit decisions are more intuitive when being made with cash flow underwriting.
• The lending categories where they are seeing the most rapid adoption.
• How smaller financial institutions can avoid being left behind.
• Jason’s view on why traditional credit models have become less predictive.
• How lenders are using cash flow underwriting in their application flow.
• How the friction in connecting a bank account is being reduced rapidly.
• The impact of the Chase-Plaid deal on cash flow underwriting.
• What sets Prism Data apart from the others in the cash flow underwriting space.

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In this episode, I sit down with Davi Strazza, who leads Adyen's business in North America. Davi brings a fascinating global perspective on payments, having spent over a decade at Adyen working across Brazil and now the US market. We dive into how Adyen's banking license, which they've held since 2021, fundamentally changes what they can offer to marketplaces, digital businesses, and SaaS companies that need to embed payments and finance into their platforms.

Our conversation explores the competitive dynamics of the payments landscape, the future of stablecoins as a payment rail, and the five critical boxes that payment companies need to check to scale successfully. We also examine what American fintech can learn from Brazil's Pix system, discuss whether pay by bank will gain meaningful traction in the US, and look at how AI is transforming everything from personalized customer experiences to fraud prevention. For anyone interested in the infrastructure powering modern commerce, this is a must-listen conversation about what may be the most exciting time to be in payments.

In this podcast you will learn:

• Davi’s journey in fintech from Brazil to here in North America.
• How he describes Adyen today.
• Why they decided to get their own banking licenses in the US, UK and EU.
• How the banking license helps make their payments business more attractive.
• What is driving their momentum in the US.
• What brands get by working with Adyen over the legacy payments platforms.
• Why they talk about “unified commerce” and what it means exactly.
• How Adyen is preparing for a world where agentic commerce is commonplace.
• Davi’s view on the future of stablecoins as a payment mechanism.
• Whether pay-by-bank has a future in this country.
• What the US can learn from the rapid adoption of Pix in Brazil.
• What he is most excited about for the future of payments.

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