Joshua Silver has spent two decades in embedded payments. Before co-founding Rainforest, he built Patient Co, a healthcare payments business scaled to billions in processing volume and tens of millions of patients, then spent several years consulting with software founders on building their payments programs. Rainforest is payments as a service, purpose-built for vertical SaaS — and in this conversation Joshua makes a compelling case that embedded payments is not just a revenue opportunity but a competitive moat.

What We Covered

• Why vertical SaaS companies are still leaving money on the table with embedded payments
• The gap in the market Rainforest was built to fill
• How payfac as a service works and who it is designed for
• Why the number of registered payfacs is shrinking, not growing
• The $5 billion volume threshold for when becoming a full payfac makes economic sense
• How Rainforest differentiates from Stripe and Adyen for vertical SaaS platforms
• Vertical-specific risk models versus general-purpose tools
• Rainforest's real-time ledger and what it unlocks for complex payment structures
• Adding PayPal and Venmo for untapped vertical SaaS markets
• Expanding into Canada and building the playbook for international growth
• How AI is being used across the business and the rising threat of AI-driven fraud
• What success looks like for Rainforest in the next five years

Key Takeaways

Embedded payments builds a moat. Joshua's closing point is the sharpest: once merchants are running their money through your software platform, competitors face a much harder job dislodging you. Payments isn't just a revenue line — it's a retention strategy.

Vertical-specific risk models matter enormously. Stripe and Adyen have to serve everyone, so their risk tooling is built for the lowest common denominator. Rainforest has built models tuned to individual verticals — lawn care looks different from HVAC, which looks different from nonprofit donations — and it takes the fraud liability rather than passing it to the platform.

The $5 billion payfac threshold is the new reality. A decade ago the rule of thumb was around $1 billion in card volume. Regulatory and compliance burdens have risen so sharply that Joshua now puts the threshold at $5 billion with line of sight to $10 billion before it makes economic sense to go full payfac.

A real-time ledger is a competitive differentiator. Most legacy processors are batch-based, settled overnight on mainframes. Rainforest's ledger is real-time, enabling split payments, franchise fee hierarchies, and complex billing structures that batch systems simply cannot support.

About Joshua Silver

Joshua Silver is co-founder and CEO of Rainforest, a payments-as-a-service company purpose-built for vertical SaaS platforms. Before Rainforest, he co-founded Patient Co, scaling it to billions in healthcare payments volume before a sale, and subsequently consulted with software founders on building their payments businesses. He has been working in embedded payments for twenty years.

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Michael Tannenbaum became CEO of Figure in early 2024, taking over from founder Mike Cagney and leading the company through its September 2025 IPO. In this conversation, we get into the mechanics of how Figure's blockchain-based platform competes with Fannie Mae and Freddie Mac, what it actually takes to cut mortgage origination costs from $12,000 to $1,000, and where the real opportunities in tokenization lie.

What We Covered

• Taking over as CEO from Mike Cagney and the Big Rocks framework
• How Figure describes itself: building the future of capital markets on blockchain
• The B2B partner network and how it compares to Fannie Mae's function
• Cutting mortgage origination costs from $12,000 to $1,000 and 45 days to five
• Why Figure competes directly with Fannie Mae and Freddie Mac
• How blockchain eliminates third-party diligence and prevents loan double-pledging
• The Figure Connect marketplace and its rapid growth since June 2024
• Where tokenization adds real value — and where it doesn't
• YLDS: Figure's SEC-registered yield-bearing stablecoin and its role in capital markets
• The timing and mechanics of Figure's September 2025 IPO
• Building a rate-agnostic business across different macro environments
• Three growth areas: consumer mortgages, Democratized Prime, and on-chain equities

Key Takeaways

Figure's origination platform and its capital market are the same system — you can't separate them, and that's the competitive moat. Tokenization only creates liquidity when the underlying assets are standardized and fungible; putting unique assets on a blockchain doesn't conjure buyers. The recent fraud cases involving double-pledged loans (Tricolor, First Brands, MFS) have turned blockchain's immutability from a skeptic's objection into a selling point. And Figure is running at what Michael calls the rule of 150 — 100% year-over-year growth at 50% margins — in one of the most rate-sensitive and entrenched markets on earth.

About Michael Tannenbaum

Michael Tannenbaum is the CEO of Figure, a blockchain-based capital markets company he took public on Nasdaq in September 2025. Before Figure, he was an early executive at both SoFi (Chief Revenue Officer) and Brex (COO), and sat on the Brex board when it was acquired by Capital One. He began his career in investment banking at J.P. Morgan.

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Thomas Galbraith is the CEO and co-founder of Barkr, an AI-driven valuation platform for asset-backed lending. He spent his early career in high net worth insurance at AIG and AXA, where he grew comfortable with the challenge of pricing hard-to-value assets. That thread ran through every role he held until it crystallized into a company built around a simple but structural problem: in asset-backed lending, appraisers give you a price and then spend the rest of their report telling you they're not responsible for it. Barkr is built to change that.

What We Covered

• Thomas's background in high net worth insurance at AIG and AXA
• How a common thread across luxury assets led to founding Barkr
• Starting with fine art and private jets before expanding to other asset classes
• The two-part failure in traditional appraisals: accuracy and absence of liability
• How Barkr pairs an AI valuation with a contractual performance warranty
• The progression from Lloyd's of London to AXA to Munich Re
• $2 billion in covered valuations and what patience actually means in this business
• GPUs as a surprisingly durable and long-lived collateral asset class
• How Barkr finds clients, from pavement pounding to Nvidia referrals
• Monthly mark-to-market on hard assets throughout a loan's life
• Building a domain-specific LLM with human review in the loop
• Plans to build an in-house insurance vehicle to unlock capacity

Key Takeaways

Traditional appraisal firms hedge their liability by design. Page one is the price; the rest of the report is the disclaimer. Barkr's contractual warranty flips that model by standing behind the number.

Barkr's data on GPU durability challenges the conventional narrative. Chips five and seven years old are still generating revenue and still have meaningful resale value, which changes the risk calculus for lenders considering AI infrastructure as collateral.

Augmenting, not replacing, is the right positioning for valuation technology. Barkr actively encourages clients to keep using their existing appraisers and treats third-party appraisals as additional data inputs that improve their own accuracy.

Building a reinsurance relationship takes years. Barkr worked through Lloyd's, then AXA, before landing Munich Re, and each step required demonstrating proof of concept at the prior level first.

About Thomas Galbraith

Thomas Galbraith is the CEO and co-founder of Barkr. He began his career in high net worth insurance at AIG and AXA before founding Barkr to bring accountability and AI-driven accuracy to asset valuation in the lending market. Barkr has covered approximately $2 billion in valuations across art, private jets, vehicles, and GPUs.

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Patricia Montesi didn't start her career in payments, she started it in car rental. After nine years at Alamo and National Rent-A-Car, she was recruited into fintech with zero industry experience. That outsider perspective became her edge, and she never let go of it. Today, she's the CEO and co-founder of Qolo, a payments infrastructure platform that combines card issuing, money movement, and a bank-grade ledger on a single API-first stack.

What We Covered

• How nine years in car rental shaped Patricia's outsider approach to payments
• Getting recruited into Wild Card Systems with no payments background, and why that fresh lens became an advantage
• The fragmentation problem at the heart of payments infrastructure and why point products create hidden complexity
• Qolo's three-product suite: Quantum Ledger, Qascade money movement, and Qinetic card issuing
• Why Qolo isn't quite a side core, it overlays and integrates with existing bank cores rather than running in parallel
• Rail agnosticism and why Qolo still supports checks in 2026
• The dual go-to-market: commercial banks and B2B fintechs, same platform, different vernacular
• How the Synapse collapse changed the ledger conversation for banks and fintechs alike
• Winning KeyBank in a competitive RFP against much larger players, and launching virtual account management in nine months
• How banks are using Qolo to protect commercial deposits from modern non-bank competitors
• AI inside Qolo: from Glean to Claude, and their internal "Turning Hours into Minutes" program
• 130% year-over-year growth and 142% net revenue retention

Key Takeaways

The moat problem: Patricia set out to build a company where customers stay because of the value delivered, not because switching is too painful. That philosophy shaped every product decision at Qolo.

Ledger first: Most point-product fintechs have basic ledgers that only support one rail. Qolo's bank-grade dual-entry forward-posting ledger underpins every rail, making reconciliation and real-time money visibility a solved problem rather than a vendor management challenge.

Synapse's legacy: The debacle forced banks and fintechs alike to ask harder questions about who actually owns the ledger and where money sits at any given moment. Qolo had been making that argument for years before the market was ready to hear it.

Bank as distribution: KeyBank and Huntington aren't just clients — they're strategic investors using Qolo to defend their commercial deposit base against modern non-bank alternatives.

About Patricia Montesi

Patricia Montesi is CEO and co-founder of Qolo, a payments infrastructure company she built from the ground up after more than 20 years in the industry. She started her career at Alamo and National Rent-A-Car before being recruited into fintech with zero payments background — an outsider perspective she has held onto ever since. At Qolo, she and her team built the ledger, money movement, and card issuing stack as first-party infrastructure, without relying on third-party processors underneath.

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Chris Walters is the CEO of Finastra, one of the largest financial software companies in the world, serving over 7,000 banks globally including 45 of the world's top 50. He joined the company a little over a year ago, bringing an unusually broad background spanning consulting, Bloomberg, The Weather Company, and several other technology businesses. This is a wide-ranging conversation about where Finastra is headed and why the conventional narrative around AI and software disruption misses something important.

What We Covered

• Chris's path from consulting to Bloomberg, The Weather Company, and beyond
• What attracted him to Finastra and the perception versus reality gap he set out to close
• How he spent his first 90 days listening to customers and internal teams before deciding direction
• The portfolio narrowing strategy, including divestitures of Treasury, Capital Markets, and student lending
• Finastra's core focus areas: lending, payments, and universal banking
• Growth vectors within an existing base of 7,000+ banks, including geography expansion, cross-sell, and data
• The AI center of excellence and why dedicated ownership changes the pace of deployment
• Internal AI use cases: an HR chatbot and automated sales approvals
• Operator Assist, a new product that uses AI to surface and resolve failed payments
• Agentic AI in mortgage origination, targeting documentation discrepancies
• Why Finastra views AI as a growth accelerant, not a cost-cutting tool, and why not all software faces the same disruption risk
• Community bank caution around modernization and why the economics will eventually force full core replacements

Key Takeaways

Companies that are systems of record with long-duration enterprise agreements are far less exposed to AI disruption than the public markets currently assume. The distinction matters, and Chris makes a clear case for why Finastra sits in the less-exposed category.

Dedicated AI ownership changes everything. Spreading AI enthusiasm across everyone's partial attention generates ideas but not scalable execution. The center of excellence model exists precisely to fix that.

Community bank core modernization is inevitable but slow. The banks most likely to win that market are those that can make transitions nearly frictionless, not those with the most advanced technology.

At $7 trillion in daily payments routed through Finastra's systems, the probabilistic nature of LLMs is not a minor technical detail. Chris's post-recording observation about where AI fits and where it doesn't is one of the more clear-eyed takes you'll hear from a CEO in this space.

About Chris Walters

Chris Walters is the CEO of Finastra, which he joined a little over a year ago. Before Finastra, he held CEO and COO roles at a range of public and private technology companies, including The Weather Company and a public wealth management and software business. He also spent seven years in consulting and held senior roles at Bloomberg.

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Ali Niknam is one of fintech's most unconventional founders. He built multiple unicorns before turning his attention to banking, then self-funded Bunq with nearly €100 million of his own money before taking a single outside investor. That conviction paid off: Bunq posted €85 million in profit in 2024, putting it in rare company among European neobanks. Now, having applied for a US national bank charter, Ali is setting his sights on the most competitive banking market in the world.

What We Covered

• Ali's background as a three-time unicorn founder
• Self-funding Bunq with nearly €100M before taking outside investment
• Pursuing a greenfield banking license, the first granted in the Netherlands in 35 years
• Why Bunq launched with a paid subscription model when everyone else was going free
• Bunq's core user base: digital nomads and cross-border travelers
• International expansion across the European Union
• Applying for a US national bank charter and dealing with three regulators
• The philosophy behind building a bank people actually trust for day-to-day use
• How AI powers transaction monitoring, real-time translation, and marketing at Bunq
• Why Bunq describes itself as the first Gen AI-powered bank
• The personal CFO vision for the future of banking
• What an AI-native bank looks like five years from now

Key Takeaways

Starting with a paid subscription meant Bunq only attracted users who genuinely valued the product, building real engagement rather than vanity metrics — and better unit economics from the outset.

Pursuing a full greenfield banking license from the start, while far harder than working around incumbents, lets Bunq compete directly with the largest banks on equal regulatory footing.

AI at Bunq isn't a marketing term. It powers transaction monitoring, real-time multilingual customer support, and marketing automation in ways that materially reduce costs and improve security.

The vision for the AI-native bank is a personal CFO that makes abstract financial goals tangible — connecting daily spending habits to the things users actually want in their lives.

About Ali Niknam

Ali Niknam is the founder and CEO of Bunq, the Dutch neobank. A serial entrepreneur with three unicorns to his name, Ali was born in Canada to Iranian parents and has been based in the Netherlands for most of his life. Before Bunq, he founded TransIP, now rebranded as Team Blue, the world's third-largest domain name and web hosting provider. He is also the author of a book on entrepreneurship.

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Timothy Li, CEO and Co-Founder of LendAPI, has spent nearly a decade trying to solve the same problem: launching a lending product takes too long and costs too much. With LendAPI, he's built a no-code platform that lets banks, credit unions, fintechs, and retailers go from idea to live lending product in weeks, not months or years. Think of it as a GoDaddy-style experience for financial services. Timothy joined me again on the show (he was last on in 2017) to talk about what's under the hood, what the Sunglass Hut deal reveals about embedded finance, and where he thinks AI is actually useful in lending today.

What We Covered

• Timothy's path from the Fluid college credit app to building LendAPI
• How the drag-and-drop product builder works for non-technical users
• Python model deployment for credit risk officers inside the same platform
• Winning Best in Show at Finovate
• The Sunglass Hut deal and how it came together in three months
• Why retailers are moving away from pure-play BNPL providers
• Integration options: bank cores, side cores, and direct e-commerce embed
• The 300-plus partner marketplace and the SEO strategy behind it
• Doc AI and single-task AI agents for document processing and underwriting
• Timothy's experience in the CURQL accelerator and how credit unions differ
• Teaching FinTech Fundamentals at USC
• The five consumer verticals with the most opportunity in fintech

Key Takeaways

The build vs. buy debate is essentially over. When Timothy talks to bank CTOs today, the conversation is "can you launch this next week?" not "should we build this ourselves?" Speed to market has become the dominant concern.

Pure-play BNPL approval rates are outside a retailer's control and can swing 10 points overnight. Private label embedded finance, built on infrastructure like LendAPI, lets retailers and banks own the underwriting criteria and the customer experience, which matters especially for high-ticket items where the financing decision happens in-store.

Single-task AI agents are the near-term opportunity in lending, not fully automated credit decisions. Automating document verification, data extraction, and intake workflows saves minutes per application, and at scale, that compounds quickly.

The five consumer fintech verticals worth building in: mortgages, auto, credit cards and personal loans, payments, and bank accounts. If it's in someone's wallet, there's still work to do.

About Timothy Li

Timothy Li is the CEO and co-founder of LendAPI, a no-code lending platform that launched in 2024 and won Best in Show at Finovate. He previously built Fluid, a credit-building app for college students, and has been building lending infrastructure across multiple ventures over the past decade. He also taught FinTech Fundamentals at the University of Southern California.

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Kareem Saleh is the CEO and co-founder of FairPlay, an AI enablement platform helping financial institutions test, tune, and monitor AI systems in production. Four years after his first appearance on the show, Kareem returns to discuss how FairPlay has evolved from credit model fairness into a full AI enablement infrastructure layer and why the rise of generative and agentic AI has made that work more consequential than ever.

What We Covered

• How generative AI changes the definition of fairness in financial services
• The shift from model validation to continuous, system-level testing
• FairPlay's three core capabilities: testing, optimizing, and validating AI systems
• How one customer added one day to their model development cycle but saved 60–90 days in compliance review
• The 25–33% of declined applicants who would have performed as well as the riskiest approvals
• Why the question for legacy institutions has flipped, from "is AI safe enough to try?" to "is it riskier not to adopt AI?"
• The political environment and how fairness demand reconfigures, not disappears, across administrations
• State-level regulatory frameworks filling the federal enforcement gap
• Kareem's Congressional testimony on AI and algorithmic bias
• The agentic AI opportunity in KYC, BSA, and AML workflows
• Regulatory look-back risk and why today's decisions can become 2029's consent orders
• Cash flow underwriting risks and climate risk as underappreciated threats to credit portfolios

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