Fintech Layer Cake

What to Look for in Your First Hire, and Why the Perfect Candidate Is a Trap with Lithic's Shirley Zhang

Fintech Layer Cake uncovers the secret recipes and practical insights from fintech leaders and experts. Host Reggie Young, chief of staff at Lithic, talks to the people building financial infrastructure from the inside. Shirley Zhang joined the startup Order as employee number seven, at 19, and built its people ops and recruiting functions from scratch. She later trained as an executive search recruiter, placing VP-level and above hires across a portfolio of venture firms, before joining Lithic, where she now leads recruiting and describes herself as a matchmaker as much as a screener. In this episode, Reggie and Shirley get into what to look for in your first handful of hires, why "ghosting" candidates is recruiting's most common unforced error, and why chasing the "purple squirrel," a candidate who checks every box, usually costs more than it's worth. They also cover how she balances hard data against gut feel, and how she went from actively avoiding a career in recruiting to building her whole identity around it. Chapters 00:00 Building people ops from scratch at 19 04:21 The three traits to anchor a first hire on 08:32 The "purple squirrel" problem 14:19 The biggest mistake in recruiting: bad candidate experience 18:07 "Recruiting is a team sport" 21:04 Assessing culture fit without just vibing 26:24 Her "sixth sense," and when to trust it 29:10 What makes someone a fit for a leadership hire 32:26 "People buy people first" 34:11 How she fell into recruiting after actively avoiding it 39:43 Why she loves it now Fintech Layer Cake is powered by the Cartesian platform, Lithic. We provide financial infrastructure that enables teams to build better payments products for consumers and businesses. Nothing in this podcast should be construed as legal or financial advice. Subscribe for new episodes. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.

How a $7B Bank Out-Loaned Chase, and What Fintech Policy Needs Now, with AFC’s Phil Goldfeder

Phil Goldfeder runs the American Fintech Council, the trade group representing nearly 170 fintech and banking companies. Before that he advised Chuck Schumer and Michael Bloomberg, served in elected office, and helped steer Cross River through the Paycheck Protection Program, where a bank with six or seven billion dollars in assets made as many loans as Chase and Bank of America. In this episode, Reggie Young talks with Phil about how policy actually gets made and changed. They cover the lessons he took from Bloomberg and Schumer, what it was like inside Cross River during PPP, how a trade group turns 170 members with different interests into workable positions, why relationships with regulators get built in rooms rather than in filings, and the window he sees for durable policy work over the months ahead. Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses. Chapters: 00:00 – Cold open: know what you know 00:12 – Meet Phil Goldfeder: Schumer, Bloomberg, Cross River, AFC 01:16 – What Bloomberg taught him about getting things done 03:16 – What Schumer taught him about time and showing up 04:33 – Inside Cross River when PPP hit 05:46 – "We have a responsibility to serve": the CEO's call 08:30 – Out-loaning the giants: a $7B bank matching Chase 09:39 – How a fintech actually advocates for policy change 11:52 – AFC as the nucleus: connecting companies, states, and regulators 14:13 – Who counts as a policymaker 15:21 – The high schoolers who changed his vote 19:01 – Managing 170 members who don't agree 19:48 – Flipping the compromise: everyone walks away a winner 21:04 – The compliance officer and the FDIC in the same room 23:13 – Banks want integrity, fintechs want speed, both can win 25:03 – Why friendly administrations don't guarantee progress 26:41 – The six-to-eight-month window to build things that last 29:36 – Consent orders as a step toward stronger companies 30:40 – Where to find AFC Nothing in this podcast should be construed as legal or financial advice. Subscribe for new episodes every other Wednesday. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.

Webinar: How Fundbox Launched a Loan-to-Card Program in 7 Weeks

For most of the history of lending, approval and access were two separate events. A borrower gets approved, then waits days or weeks for an ACH to clear before the money is usable. For small businesses managing tight cash flow, that gap can be the difference between catching an opportunity and missing it. Cards are changing that. When a lender issues a virtual card at the moment of approval, credit becomes spendable right away, with no ACH delay and no separate account. In this webinar, Lithic product marketer Claire Jacobs sits down with Sarvesh Baveja, Chief Risk Officer at Fundbox, and Declan Callisto, Product Manager at Lithic, to break down how Fundbox built a loan-to-card program on Lithic and took it live in seven weeks. They cover the borrower experience from application to spend, the spend controls that let a lender manage risk at both the business and card level, the four partners required to stand up a program like this, and where SMB underwriting goes as static credit limits give way to dynamic ones. Fintech Layer Cake and Lithic webinars are powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses. Chapters 00:00 Why approval and access became two separate events 01:32 Sarvesh and Declan introduce themselves 02:00 Why loan-to-card is a new innovation 02:19 The SMB cash flow timing problem 03:21 Why the choice of issuer processor matters 04:13 The Fundbox borrower experience, from application to spend 06:00 What Lithic built behind the scenes: the credit ledger 06:56 Why spend controls work at both the business and card level 08:30 Where else card rails apply beyond SMB lending 09:36 The rent payment use case 10:29 The four partners required to launch a program like this 12:42 Why embedded payments matter for reaching borrowers 14:08 What Lithic offers that legacy processors don't 16:05 The biggest misconception about program timelines 18:15 Where SMB underwriting is headed: from static limits to dynamic ones 20:03 Closing thoughts Subscribe for more on card infrastructure and modern lending.

Nobody Loves SWIFT: Payments Inertia and Invisible Crypto Rails with Davi Strazza from Lightspark

Davi Strazza spent a decade at Adyen as the company scaled from around $30 billion to over $1.3 trillion in annual payment volume, running Latin America and then North America as president. Today he is Chief Business Officer at Lightspark, the company powering over 15% of Coinbase's Bitcoin transfers. In this episode, Reggie Young talks with Davi about what actually moves enterprise payments decisions. They cover why inertia keeps trillions on legacy rails, how challengers find their wedge against incumbents, what Pix's adoption in Brazil reveals about changing payment behavior, and how Lightspark uses Bitcoin and stablecoins as invisible infrastructure for global money movement. Davi closes with the risk he thinks fintech still underweights: the compliance work underneath every product that scales. Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses. Chapters: 00:00 – Cold open: most money still moves in fiat 00:21 – Meet Davi Strazza: Adyen, Lightspark, and $1.3T in volume 01:56 – Latam vs. North America: relationships vs. pragmatism 04:33 – Why enterprises don't rip out legacy processors 06:19 – Redundancy, and finding your wedge as a challenger 07:56 – Changing the org before the org wants to change 11:31 – What Pix taught him about shifting payment behavior 13:12 – Why it takes an Uber to teach consumers new payment habits 15:43 – What Lightspark powers, from Coinbase to cross-border payouts 18:42 – Global Accounts: offering the endpoint, not just the transfer 20:18 – Making Bitcoin invisible: the rail-agnostic thesis 24:10 – Selling infrastructure while the rules are still being written 27:53 – Why you no longer need to be Stripe to build in fintech 30:02 – The next decade: fiat and crypto converging 33:09 – Stablecoins are earlier than the headlines suggest 34:34 – The underrated work: compliance that scales 37:23 – Where to find Lightspark Nothing in this podcast should be construed as legal or financial advice. Subscribe for new episodes every other Wednesday. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.

A Former Prosecutor on How Fintechs Become Targets, with Laurel Loomis Rimon from Jenner & Block

Laurel Loomis Rimon has spent her career on the enforcement side of fintech. As a federal prosecutor she brought the first case against a digital currency company in the US, years before Bitcoin existed. She later served as an assistant deputy enforcement director at the CFPB, and today she co-chairs the fintech and crypto assets practice at Jenner & Block and founded the firm's payments practice. In this episode, Reggie Young talks with Laurel about how enforcement and prosecution of fintech actually work in practice. They cover what puts a company on an investigator's radar, what genuinely exposes fintechs and banks to enforcement, how regulators and prosecutors assess good faith, and how she is advising clients to navigate debanking, KYC, and a fast-moving regulatory environment. Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses. Chapters: 00:00 – Cold open: the risk everyone underrates 00:22 – Meet Laurel Loomis Rimon: DOJ, CFPB, and Jenner & Block 02:15 – Prosecuting E-gold, the first digital currency case 04:24 – The legal hooks before crypto law existed 05:48 – Money transmitting becomes a baseline concern 06:10 – What actually makes a company a target 07:13 – Why the company is rarely the target at the start 08:02 – Don't become the platform of choice for illicit actors 08:25 – Regulators are consumers too 09:39 – When the complainant is the regulator's own family 09:57 – What fintechs worry about too much 10:16 – The most boring risk: documentation 12:06 – Product thinking as a compliance skill 12:26 – How regulators assess good faith 12:58 – Why staffing is always key, even in the age of AI 14:18 – When growth outpaces compliance investment 15:40 – Where debanking comes from: Operation Choke Point 17:45 – Reputation risk and the regulatory whiplash 21:02 – How KYC changes amid the debanking pushback 22:25 – The executive order tension banks are caught in 23:34 – Advising fintechs to build for the next administration 25:41 – Where to reach Laurel Nothing in this podcast should be construed as legal or financial advice. Subscribe for new episodes every other Wednesday. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.

Payments at Square, Etsy, and the Agentic Era, with Drew Edmond, Partner at Glenbrook Partners

Drew Edmond has spent 15 years inside payment operations, first at Square from its scrappy hardware days through IPO, then at Etsy running payments across a marketplace with sellers in 230+ countries. Today he advises merchants at Glenbrook Partners and hosts the Payments on Fire podcast. In this episode, Reggie Young sits down with Drew to trace how payments actually work from the operator's seat. They cover what changes when a payment goes card not present, the data and testing work most merchants skip, why global expansion demands a plan for every country rather than every region, and whether agentic commerce is real yet. Drew's answer on that last one is more measured than the hype, and more useful. Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses. Chapters: 00:00 – Cold open: why card not present changes everything 00:35 – Meet Drew Edmond: Square, Etsy, and Glenbrook 02:53 – Inside early Square: free readers and a new class of merchant 04:40 – The chain of trust that holds payments together 07:13 – Living in constant negotiation with banks and networks 10:43 – Trusting "the Twitter guy" with your money 11:46 – Square vs. Etsy: the three jobs every platform shares 12:38 – What e-commerce and going global really change 14:51 – Why there's no such thing as a "Europe strategy" 18:53 – The optimization lever most merchants underinvest in 21:44 – How fraud quietly tanks your approval rates 25:32 – Why the optimal amount of fraud isn't zero 26:44 – The hidden complexity of subscription payments 33:13 – The "miasma of payments" and 900-page network rulebooks 35:38 – The CVV era of agentic payments 41:03 – Why discovery is harder than the payment itself 44:57 – Who controls the agent layer wins payment selection Nothing in this podcast should be construed as legal or financial advice. Subscribe for new episodes every other Wednesday. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.

From Fannie Mae's first PM to Pathward Innovation with Suhas Reddy

What if millions of Americans had already proven they could handle a mortgage payment — and the system simply refused to count it? Reggie sits down with Suhas Reddy, Head of Product at Pathward Bank, to unpack what it really means to build product inside the most regulated corners of financial services. Suhas was among the early product leaders at Fannie Mae, driving the Lighthouse Project that later transformed one of the world's largest secondary mortgage institutions into a customer-centric, digital-first product organisation. He now leads product at Pathward as SVP of Product Management across the Nasdaq-listed sponsor bank's B2B products — payments, issuing, lending, acquiring, and commercial finance — developing the products that enable fintechs and brands to reach customers at scale. The conversation covers the 10-year product build that became an overnight pandemic success story, why Suhas treats risk and compliance as design constraints rather than roadblocks, and the title insurance battle he fought — and lost — years before it became national policy. They get into the philosophy of “Legos, not unicorns” as a framework for building scalable fintech infrastructure, and the human-centric conviction that turned rental payment history into a mortgage underwriting signal — unlocking homeownership for borrowers the system had previously ignored. Suhas continues to build infrastructure that expands financial access for underserved communities through Pathward's product platform.

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Escheatment Primer + Innovation with Eisen CEO Allen Osgood

What if every dormant account in your fintech is a ticking compliance clock — and you didn't know the timer started three years ago? Host Reggie Young sits down with Allen Osgood, CEO and co-founder of Eisen, the company modernising escheatment — the process by which dormant accounts and abandoned funds get transferred to state governments. It's an obscure corner of financial compliance that touches every bank, fintech, brokerage, and increasingly every crypto platform. More than one in seven Americans has money sitting in state hands because of it, with over $80 billion held by state governments at any given time. Allen and Reggie cover what escheatment actually is and why it matters, the wild story of a retiree who planned his retirement around an Amazon investment — only to find the state of Delaware had liquidated it. They dig into why crypto is about to smash headfirst into dormancy periods nobody planned for, why the 'deal with it later' mindset is a trap that hits three years faster than founders expect, and how proactive compliance can flip a cost centre into a retention engine.

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Why Credit Cards Are Hard with Scott Bass from Ensemblex

What if the decision that kills your lending business is one you made six months ago — and you just don’t know it yet? Host Reggie Young sits down with Scott Bass, Managing Director at Ensemblex, the fintech lending and credit consultancy. Scott brings a rare combination of perspectives: he helped build Capital One’s data-driven credit operation before it was a household name and was one of the first two Americans hired to launch Monzo’s US business. Scott and Reggie cover what Capital One actually got right that most people miss, the lessons Monzo taught about building products that feel nothing like a bank, and the most predictable mistakes fintech founders make when building credit products. They dig into the six-month lag problem in lending, why being “light on the fin in fintech” is a slow-burning liability, and why Scott believes credit cards remain the most complex — and therefore most defensible — financial product a fintech can build.

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The Future of Payments is Agentic and Tokenized, with Basis Theory CEO Colin Luce and CTO James Armstead

The payments industry spent years turning tokenization into a business tool for lock-in. So what does it mean that the same technology might now hold the key to making agentic payments actually work? Reggie Young sits down with Basis Theory’s Co-founder and CEO, Colin Luce, and CTO, James Armstead — the team behind the programmable token vault platform that has quietly become central to the agentic payments conversation. Colin and James break down what tokenization really is, how it was co-opted as a competitive moat, and why they believe it's the foundational layer that agentic commerce needs to get right. They get into the reality of agentic payments today — what's hype, what's actually transacting, and why human-in-the-loop is a feature, not a bug. The conversation covers the technical choke points legacy infrastructure wasn't designed to handle, the intent and fraud problem nobody has solved yet, why the industry is over-complicating protocol selection, and what a smarter approach to tokenization could unlock. Plus: Colin's bold prediction on the fate of PANs, James on why the early winners will just accept the volume, and the pair on why a misspelled email might be the highest compliment you can give someone in 2026.

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Building the Modern Tax Engine with Gavin Nachbar, Column Tax co-founder and Aiwyn CPO

If AI is about to transform tax filing, why do 55% of Americans still trust a human to do it for them? In this episode, host Reggie Young sits down with Gavin Nachbar, founder of Column Tax and Chief Product Officer at Aiwyn, to unpack what it really takes to build in one of fintech’s most complex and overlooked spaces: tax filing. Gavin shares how Column Tax built the first modern embedded tax engine in the US, what AI is about to change for the 55% who still rely on a human preparer, and why he’s genuinely bullish — not worried — about the road ahead. They also dig into his lessons on entering a regulated space as an outsider, the unique challenges of a seasonal product, and the hard-won takeaways from going through an acquisition.

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Simon Taylor on Where Agentic Spend is Going

Will stablecoins replace cards — or is that narrative missing how payments actually work? In this episode, Reggie Young sits down with Simon Taylor, founder of Fintech Brainfood and Head of Market Development at Tempo, to unpack one of the most debated topics in fintech: agentic commerce. Simon challenges the idea that stablecoins will displace card networks, explaining why cards don’t move money, how stablecoins actually fit into the stack, and why virtual cards may be the first real payment primitive for AI agents. The conversation explores machine-native payments, the rise of agents as customers, and Tempo’s Machine Payments Protocol — a new attempt to rebuild payments infrastructure for the internet era. Simon also shares where adoption will come from, why most narratives get the timing wrong, and what the next battleground in fintech will be.

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A Primer on US Fintech Expansion with Klaros' Andy Kampf

What actually breaks when a fintech expands to the U.S. — product, licensing, hiring, or assumptions? In this episode, host Reggie Young sits down with Andy Kampf, Partner at Klaros Group and former Klarna US legal lead, to unpack the real framework behind cross-border fintech expansion. Andy breaks down the four pillars every foreign fintech must get right — product, bank partnerships, hiring, and budget — and the hidden pitfalls that derail U.S. launches. From misconceptions about European e-money licenses to choosing the wrong bank partner, Andy shares practical insights drawn from advising global fintechs entering the U.S. The conversation also dives into cultural underwriting differences, lessons from Klarna’s speed-first model, and what Europe’s proposed “28th regime” could mean for startup migration and capital flow. A must-listen for fintech leaders thinking seriously about international expansion.

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Middesk CEO Kyle Mack on AI, Good Data, and Business Onboarding in 2026

What happens when you try to build AI-driven fintech products on top of messy, incomplete, or unreliable data? In this episode of Fintech Layer Cake, host Reggie Young sits down with Kyle Mack, CEO of Middesk, to unpack why data—not AI—is the real bottleneck holding fintech innovation back. Kyle explains how KYB has evolved far beyond a compliance checkbox, why poor data foundations can amplify risk instead of reducing it, and what it actually takes to support real-time, automated decisioning for business onboarding. The conversation dives into agentic workflows, performance constraints, first-party data strategies, and why trust and explainability still matter in a regulated world. Kyle also reframes business verification as revenue infrastructure, not just risk management, and shares why identity should be thought of as a “rail” connecting businesses, banks, and governments.

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Reducing Oversight Costs for Fintechs and Banks with Narrative CEO Gokul Dhingra

In this episode of FinTech Layer Cake, Reggie Young sits down with Gokul Dhingra, Co-Founder and CEO of Narrative, to unpack how AI is reshaping compliance, oversight, and growth in the fintech ecosystem. Narrative is tackling one of the industry’s biggest pain points—the rising cost of compliance and risk management—by turning oversight into a source of efficiency and even competitive advantage. Gokul shares how banks and fintechs can align around shared objectives, why complaints data is an overlooked goldmine for growth, and how Narrative uses AI to reduce operational thrash while keeping humans in the loop. The conversation digs into the misconceptions about AI “hallucinations,” the subtle ways bias shows up in both humans and algorithms, and why empathy is the ultimate differentiator in building trust with customers and regulators alike. If you’ve wondered what it takes to scale innovation in a highly regulated environment without sacrificing trust—or how AI can be deployed responsibly in financial services—this episode offers a roadmap from someone building it in real time.

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2025 Cards Year in Review with Matthew Goldman

Why are crypto credit cards exploding — and what does the Coinbase x Amex partnership signal about where the card ecosystem is heading next? In this episode, host Reggie Young sits down with Matthew Goldman, founder of Totavi and one of the most respected card experts in fintech, for their annual “State of the Cards Union.” Matthew breaks down why 2025 became a breakout year for crypto-linked cards, how Amex is selectively stepping deeper into fintech partnerships, and why HELOC-backed credit products reached an unexpected inflection point. He also shares what surprised him most this year, the underwriting innovations reshaping access to credit, and why consumer obsession with rewards has gone fully mainstream. The conversation moves through the history of program management waves, the rise of cloud-native processors, and the real economics behind modern card programs. Finally, Matthew looks ahead to 2026 with predictions around stablecoin settlement, hyper-personalized rewards, and the next big opportunity in gig-worker credit.

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Sarah Wilson, Circle's General Counsel, on the IPO Process, GENIUS Act, and More

In this episode of Fintech Layer Cake, host Reggie Young sits down with Sarah Wilson, General Counsel at Circle, to explore how Circle is shaping the global legal and regulatory frontier for stablecoins and digital assets. She shares her path from big law to fintech, why stablecoins represent the perfect intersection of finance, technology, and regulation, and how Circle manages compliance across 185 countries. Sarah breaks down the Genius Act—its real scope, biggest misconceptions, and what it means for payment stablecoins. Sarah also offers a behind-the-scenes look at Circle’s IPO journey, what shifts when a company goes public, and how Circle built Arc, an institutional-grade blockchain platform. Packed with insights on compliance, innovation, and digital finance governance, this episode is a must-listen for fintech operators, lawyers, and anyone shaping the future of financial infrastructure.

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AI Adoption Survey and Fintech Trends with Jas Randhawa

In this episode of FinTech Layer Cake, host Reggie Young welcomes back Jas Randhawa, Founder and Managing Partner at Strategy Brix, for a candid look at how fintechs are really using AI in compliance. Drawing insights from a new survey of nearly 100 fintech companies, Jas shares what’s hype versus reality, why most teams are still in the ‘talking’ phase, and where budgets and talent investments are falling short. He also explores how AI will reshape compliance roles, the importance of training over tooling, and why regulation might never catch up. Finally, Jas explains why he’s bullish on crypto and stablecoins—and how traditional banks are quietly following fintechs’ lead. For anyone building, leading, or scaling in fintech compliance, this episode delivers clear-eyed perspective and practical takeaways.

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MTLs and Money Transmission Primer with Evan Minsberg

In this episode of FinTech Layer Cake, host Reggie Young speaks with Evan Minsberg, Partner at Morrison Foerster, about the nuanced world of money transmission licenses (MTLs). Evan explains what MTLs are, why fintechs need them, and the trade-offs between pursuing a license, partnering with a bank, or using alternative models. He also unpacks the hidden costs, both in dollars and time, behind getting licensed, and how fintechs can think strategically about when it makes sense to pursue one. From agent-of-payee exemptions to the risks of operating without proper licenses, Evan offers a practical primer for founders navigating regulatory quicksand. He also shares trends in state-level adoption of the Money Transmission Modernization Act (MTMA), rising anti-money laundering scrutiny, and myths about “FBO” and “BOBA” accounts. Whether you’re building a payments product, exploring embedded finance, or just trying to future-proof your business, this conversation is packed with insights you won’t want to miss.

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Imprint CTO Will Larson on Fintech Engineering Strategy

What does it take to run engineering at the heart of modern fintech? In this episode of Fintech Layer Cake, Imprint CTO Will Larson unpacks lessons from leading engineering teams at Stripe, Carta, Calm, Uber, and more. Will shares how fintech engineering differs from SaaS, the tradeoffs executives face when joining new companies, and why the art of leadership lies in balancing seemingly incompatible frameworks, moving fast while preserving reliability, innovating while managing legacy systems. He also dives into the hype and reality of large language models (LLMs). Will explains why today’s “AI engineers” may simply be tomorrow’s product engineers, why prompt-crafting is more artisanal than strategic, and how agentic tools could redefine workflows. From the shifting expectations of tech executives over three decades to what really drives innovation inside scaling companies, this conversation is equal parts practical and forward-looking. For anyone navigating fintech engineering or curious about the future of AI in product development, Will offers a grounded perspective on what matters most.

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