Fintech One-On-One

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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