Tearsheet Podcast: Exploring Financial Services Together

Anthony Scaramucci bought his first bitcoin at about $6,000. In October 2020, he bought nine figures' worth for himself and his clients, and some of those clients fired him for it. He had been a skeptic, and he had already missed the run from $500 to $2,000. What changed his mind was working out what money is, and he now runs SkyBridge Capital as a crypto and late-stage private equity firm managin...

A $2 million general contractor pays subcontractors, invoices clients, issues employee cards, and keeps its own books. Most banks still serve this business the way they serve a consumer, just with a larger balance. Owners fill the gaps by stitching together a dozen or more apps. Digital banks competing for this market are pulling more of these jobs into the banking experience, building some tools...

For Episode 3, we asked a simple question: Which fintechs would we genuinely miss if they disappeared tomorrow? Millions of users don't necessarily mean a company has built a bomb product or something people can't live without. Customers might stay for convenience, better pricing, or simply because switching hasn't crossed their minds. Zack chose PayPal, drawing on his own experience with the comp...

Customers hold their banks to a standard they learned somewhere else. Brian DuVal, President of North America at Temenos, points to the speed and ease of use they have become accustomed to booking a hotel, renting a car or buying with one-click on Amazon. Yet their banking experiences don’t always measure up. This distance is the subject of “The Banking Expectation Gap: U.S. Consumer Edition,” res...

Why small businesses hesitate on AI in finance, and how BILL is addressing it by Tearsheet

Allen Bonde, Chief Marketing Officer at TreviPay, argues that a new generation of digital-native buyers is the biggest force reshaping how businesses buy and pay. Accustomed to frictionless consumer experiences, they expect the same convenience and omnichannel consistency from their suppliers. They are also more open to alternatives like stablecoins, net terms modeled on consumer BNPL, and AI as a...

Most AI startups chase breadth. They build a capable, general-purpose product and sell it across as many industries as are willing to buy it. Ari Malik, CEO of Salient, took the opposite approach. He picked one vertical, auto lending, and went deep enough that he eventually moved his company's headquarters to Los Angeles to be closer to a single customer, Westlake Financial. Two years later, Salie...

Nubank spent thirteen years building one of the most loved financial brands in Latin America, growing past 140 million customers across Brazil, Mexico, and Colombia. This month, that brand entered the US for the first time, launching Nu Global alongside a dedicated US product built around a Nu Account and a no-annual-fee credit card. Ethan Eismann is the executive tasked with making that experienc...

For the second episode of The Editors’ Room, we flipped the format around. One trend we think the industry is overhyping, and one that isn’t getting nearly enough attention. Managing Editor Sara took the overhyped side: the race to become a customer’s primary financial relationship. Founding Editor Zack’s underhyped pick was something that gets little attention in the larger scheme of things: the...

When Silicon Valley Bank collapsed in March 2023, it took with it a bank that had quietly become infrastructure for the startup ecosystem, holding the majority of the venture debt market and serving as the one relationship founders and fund managers trusted for everything from a wire transfer to an introduction. Bigger banks and a wave of neobanks moved fast to fill the void. Three years later, th...

Most banks seem to chase small business customers as one segment among many. Live Oak Bank was built around a bet that specializing beats generalizing — and it started about as narrow as a bank can start, lending only to veterinarians. Today, Live Oak has grown that thesis into 40 verticals, holds the top spot among all SBA 7(a) lenders by dollar volume, and has done it all without a single branch...

Amy Avery, Managing Director, Analytics, Modeling and Insights, took her job at Bank of America because of a number. When she interviewed at Bank of America, she was told that the bank interfaced with, at the time, 67 million clients. "Gosh, that's so much information," she remembers thinking. "Think about what you could do with that.” She started in January 2020. Two months later, the pandemic ma...

Welcome to The Editors’ Room, a new Tearsheet Podcast series where Editor-in-Chief Zack Miller and Managing Editor Sara Khairi take the conversations that usually happen behind the scenes about our biggest stories and put them on the record. There isn’t a rehearsed interview or carefully choreographed panel answers. It’s just two editors comparing notes, challenging each other’s takes and trying t...

Every account payable and account receivable department runs on the same friction: invoices chased four or five times, payments late more than 30% of the time, and credit control teams that can run 20, 30, even 50 people deep at a mid-sized corporate. Virtual cards were built to solve exactly that problem, and the growth numbers show it — spend is projected to hit $17.4 trillion by 2029, according...

For most small and midsize businesses, financial operations still look a lot like they did a decade ago. Bills get keyed in manually. Receipts pile up. W-9s get chased down at tax time. While the tools have multiplied, the work hasn't gone away. “Most finance teams work in an incredibly manual way,” says Michael Cieri, Chief Product Officer at BILL. “There's a ton of work done by finance professio...

Welcome to the Tearsheet Podcast, where we explore financial services together with an eye on technology, innovation, emerging models, and changing expectations. I'm Tearsheet's editor in chief, Zack Miller. Fintech just lived through four distinct ages — pioneers, growth-at-all-costs, the 2021-22 hype cycle, and the brutal reset that followed. Now we're in a fifth: bigger, more profitable, and mo...

Debt consolidation has always rested on a promise lenders couldn't verify. A borrower takes out a HELOC, says they'll pay off their credit cards, and the lender hands over the cash and hopes for the best. Credit bureau data lags by 30 days. There's no mechanism to confirm the debt actually got retired. And a significant share of consolidation borrowers end up re-accumulating balances — leaving len...

Small business banking has always had a structural problem: the companies that hold your money and the companies that build your financial software have been two different things. One moves the money, the other tracks it, and small business owners are stuck in the gap between them. A new generation of fintechs has been trying to fix that, but most are still building horizontal tools for every busi...

Most people leave money on the table every time they swipe — not because they're careless, but because the credit card rewards ecosystem is genuinely complicated. Thousands of cards, millions of merchants, shifting bonus categories, buried benefits. The promise of AI is that it can do that optimization work invisibly, in the background. Today I'm joined by Tikue Anazodo, co-founder and CEO of Kudo...

Unlock how stablecoin infrastructure is transforming cross-border payments, global treasury, and enterprise fintech strategy. In this episode, Avinash Chidambaram, Founder & CEO of Cybrid, breaks down how stablecoin rails are becoming production-ready payment infrastructure for fintechs, neobanks, and enterprises seeking faster settlement, lower fees, and programmable global money movement. Discov...

The credit system in the US was built on a fundamental assumption: that past borrowing behavior predicts future risk. That assumption has left roughly 100 million Americans essentially invisible to lenders — no score, thin file, or a history that doesn't reflect who they actually are financially today. The result is a system that compounds exclusion, requiring debt to unlock debt, and pricing risk...

The pressure building on commercial banks today comes from several directions at once. Corporate treasurers are younger, more digitally native, and less tolerant of manual reconciliation. Business structures are more complex: A franchisee group running fifty locations needs fifty entities managed cleanly, not fifty separate bank accounts generating a month's worth of reconciliation work. And the b...

For two decades, Squarespace has been the platform entrepreneurs turn to when they want to build something that looks like they hired a designer. But over the past few years, something has changed. Squarespace has been building a financial stack. Payments launched in 2023. Capital followed in 2025, offering merchants flexible financing based on their sales history. And just two weeks ago, Squaresp...

Early Warning built Zelle into the dominant peer-to-peer payments network in the U.S. — processing over a trillion dollars in yearly transactions. Paze is their next bet: a bank-backed digital wallet for e-commerce checkout, backed by the same seven major banks, designed to bring that same institutional trust to online shopping. Serge Elkiner came on as GM in late 2024, brought over from Visa wher...

A mid-market company with dozens of bank accounts shouldn't have to deploy a small army to figure out where its money is. But for most commercial banking clients, that's still the reality because the systems tracking it haven't kept up. Banks know this. Most of their commercial clients know this. The gap between what legacy infrastructure can deliver and what today's treasury teams actually need h...