Fintech Hustle

Hosted by Sam Kilmer & Cornerstone Advisors

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Latest episode

Mar 2026

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About the show

Join host Sam Kilmer, fintech advisor, in unscripted conversations with top fintech industry leaders. No planned corporate talking points, no scripts, no pitches. Just useful advice and insights. To keep it lively, Sam often brings co-hosts like author/researcher Ron Shevlin, former American Banker editor Mary Wisniewski, and former Bank Director President Al Dominick. Subscribe to the Fintech Hustle podcast here: https://qrco.de/bgfV6g

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42 recent

March 24, 2026Episode 427 min

AI in Banking, Core Systems & Fintech Trust: Insights from AFT Spring Summit

Live from the AFT Spring Summit, Sam Kilmer (Managing Director, Cornerstone Advisors) is joined by fintech leaders to discuss what’s really happening in banking and financial services right now. Guests include:Laura Kornhauser (CEO & Co-Founder, Stratyfy)David Eads (CEO & Co-Founder, Vine Financial)Kirsten Longnecker (Executive Vice President, York Public Relations)Tim Hamilton (Founder & CEO, Praxent) This unscripted “in the hall” conversation covers:The real impact of AI in banking (beyond the hype)Why trust between fintechs and banks is criticalCore system challenges still holding banks backThe future of software development with generative AIRisks of AI hallucinations and regulatory implicationsWhy entry-level talent may drive the next wave of innovationWhat’s working — and what’s still broken — in fintech From customer-centricity to infrastructure challenges, this discussion captures the current state of fintech innovation and where the industry is heading next. Click to watch more Fintech Hustle!🔗 https://www.crnrstone.com/gritty-insights/podcasts/fintech-hustle/ Connect with Sam on LinkedIn:🔗 https://www.linkedin.com/in/samkilmer/ Connect with Laura on LinkedIn:🔗 https://www.linkedin.com/in/laura-kornhauser/ Connect with David on LinkedIn:🔗 https://www.linkedin.com/in/kirstenlongnecker/ Connect with Kirsten on LinkedIn:🔗 https://www.linkedin.com/in/kirstenlongnecker/ Connect with Tim on LinkedIn:🔗 https://www.linkedin.com/in/timham/

March 6, 2026Episode 328 min

The Future of Credit Unions: AI, Innovation & Member Strategy

Recorded live from GAC, Sam Kilmer (Managing Director, Cornerstone Advisors and host of Fintech Hustle) sits down with a powerhouse panel of credit union and fintech leaders for an unscripted hallway conversation.Joining the discussion:Brandi Gregory (Managing Director, Cornerstone Advisors)Ned Tobey (CEO, Circuit)JB Orecchia (CEO, SavvyMoney)Nicole Haverly (VP Credit Unions, nCino)Rob Landis (CEO, Correlation)Topics include AI, member primacy, financial wellness, fraud risks, speed of innovation, and what credit unions must rethink in 2026.Click to watch more Fintech Hustle!🔗 https://www.crnrstone.com/gritty-insights/podcasts/fintech-hustle/ Connect with Sam on LinkedIn:🔗 https://www.linkedin.com/in/samkilmer/Watch the Video Episodes on Youtube!🔗https://youtu.be/LQOMuzfwl84

February 7, 2026Episode 233 min

AOBA 2026 Takeaways: AI, Deposits, Data, and What’s Breaking

Recorded at a location near AOBA 2026, this Fintech Hustle episode brings guests Aleda DeMaria (EVP & Chief Operating Officer, PeoplesBank), Mac Thompson (Founder & CEO, White Clay) & Christina Miller (VP, Alkami) for an unscripted hallway conversation on what’s changing right now. Key topics include:Deposit retention after massive outflows and why “acquisition” is not the finish lineAI everywhere, including fraud, and why banks must fight AI with AIVendor consolidation and the reality of fragmented tech stacksData strategy as a growth engine, not just a compliance toolWhy the branch still matters and how to modernize the in-branch experienceThe talent challenge for community banks trying to innovateA clear warning: community banks should stop trying to build what mega-banks build, and focus on partnerships and executionLet us know what theme you’re hearing most in your institution right now.Click to watch more Fintech Hustle!🔗 https://www.crnrstone.com/gritty-insights/podcasts/fintech-hustle/ Connect with Sam on LinkedIn:🔗 https://www.linkedin.com/in/samkilmer/

January 22, 2026Episode 133 min

Fintech Hustle 2026 Kickoff: AI, Stablecoins, and the New “Community”

Kicking off 2026 with a strategy-focused episode of Fintech Hustle. Sam Kilmer (Managing Director, Cornerstone Advisors) and co-host Kelli Schultz (Principal, Cornerstone Advisors) are joined by Erica Pilon (Head of Strategy, Jack Henry) and Scott Hildenbrand (Chief Balance Sheet Strategist, Piper Sandler) to discuss what’s changing in banking and fintech, and what winners will do differently.Topics include: vendor strategy and fintech partnerships, stablecoin and payments, customer-first balance sheet thinking, redefining “community,” why bank valuations aren’t reflecting performance, and the missed marketing opportunities banks keep repeating.What’s your top strategic priority for 2026?00:00 Intro + 2026 kickoff01:00 Erica Pilon intro + strategy shifts05:00 Jack Henry priorities, fintech alliances, ecosystem09:30 Scott Hildenbrand: ALCO, balance sheet, M&A12:00 Deposit chaos and customer-first ALCO14:00 Redefining “community” and loyalty vs trust17:30 What’s “broken”: integration + standards24:00 What’s “broken”: marketing and telling the story29:45 What’s “jazzing” them: stablecoin + opportunity32:30 WrapClick to watch more!https://www.crnrstone.com/gritty-insights/podcasts/fintech-hustle/Connect with Sam on LinkedIn:https://www.linkedin.com/in/samkilmer/

November 17, 2025Episode 914 min

2025 in Fintech: The Best Insights from Fintech Hustle Podcast

Host Sam Kilmer looks back at the year’s most quoted hallway moments—packed with real-world takes on AI (purposeful, not buzzwordy), stablecoins (watch the fiat on/off-ramps), data activation (from “we have it” to “we use it”), and go-to-market alignment. Highlights include an AI reality check from a startup CEO, pragmatic stablecoin guidance from an investing leader, compliance and fraud implications for the AI era, organizing sales + marketing around bookings, and why community FIs must aim for personalization beyond product silos. Plus a few road-warrior stories (Grace Potter sighting, sun-safe merch) to cap a big year.LinksSam Kilmer (LinkedIn): https://www.linkedin.com/in/samkilmer/Fintech Hustle (Cornerstone site): https://www.crnrstone.com/gritty-insights/podcasts/fintech-hustle/Key Moments00:04 Flashback setup: a “greatest-hits-ish” reel—AI, stablecoin, data, GTM 01:23 AI culture shift: a CEO’s take on leaders who hoped to “retire before it hits” 03:06 Stablecoin sanity check (rooftop chat): focus on fiat ↔ stablecoin conversions now 05:07 AI’s compounding edge: “It’s the dumbest it will ever be today”—early adopters win on efficiency, profitability, M&A leverage 07:18 Purposeful AI: define the outcome first (ops efficiency, intimacy, personalization), then pick the tech 08:25 GTM org design: marketing + sales co-own accounts and bookings; content ≠ handoff forms 10:48 Data to action: banks have data—now align strategy, frontline, and offers to actually use it 12:03 Sign-off: community, road notes, and gearing up for 2026’s guest slate

October 29, 2025Episode 847 min

Purposeful AI, Tokenized Mortgages, and What Community Banks Must Do Next

Host Sam Kilmer gathers Reva Rao (Head of Digital Transformation, Blend), David Ladic (SVP, Zafin), Adam Aspes (Partner, FINTOP), and co-host Kelli Schultz for a candid hallway conversation. They trade “day-in-the-life” views (and nonstop event planning), argue for purposeful AI over buzzwords, and unpack regulator-ready AI governance (from “know your agent” to vendor disclosures). The group debates blockchain/tokenization in mortgages, smart-contract enforcement, fraud realities, and whether consumers even care about the rails—so long as pricing and trust improve. It closes with a challenge to community FIs: get entrepreneurial, use your data, personalize beyond product silos, and solve for outcomes—not tech for tech’s sake.Key Moments00:11 Guest lineup and setup from the halls of fintech to real operator stories08:45 Events as strategy why orchestration and education matter as much as product13:22 Purposeful AI prioritize problems, outcomes, and ROI rather than buzzwords20:36 Governance and exams “know your agent,” vendor AI disclosures, anonymization, and risk28:32 Tokenization debate on chain home equity, cost dynamics, smart contract enforcement, and whether consumers care42:10 What’s broken and what wins data driven personalization and a call for FI entrepreneurship47:03 Wrap and takeaways solve outcomes first and let tech follow

September 22, 2025Episode 718 min

Data, Trust & The Death of Product-Centric Banking | FinovateFall 2025

Recording “in the hall” at FinovateFall, host Sam Kilmer is joined by Wayne Miller ( SVP Innovation at ICBA & GP at BankTech Ventures), Tiffani Montez (Principal Analyst, EMARKETER), and Har Rai Khalsa (CEO & Co-Founder, Swaystack). They discuss what a fintech leader’s day really looks like, the urgency of AI adoption, the shaky logic of bank-issued stablecoins, and why personalization and life-stage experiences must replace product silos.Key Moments00:04 Live from FinovateFall, NYC — Sam introduces Wayne, Tiffani, and Har Rhai.01:10 Day-in-the-life: matchmaking fintech + banks, research for clients, go-to-market hustle.04:24 Hallway buzz: AI and stablecoin — time to focus on how, not why.07:25 Industry pain points: inactive accounts, lack of engagement, and missing 360° customer views.12:16 Positive outlook: AI as augmentation, personalization at scale, and shifting from products to customer life-stage journeys.

September 11, 202531 min

From the Rooftop of JAM Fintop 2025 // Steve Soukup, Todd Clark, Erin Simpson, Karan Kashyap

Host Sam Kilmer records live from Hyatt Nashville with Steve Soukup (DefenseStorm), Todd Clark (Investifi), Erin Simpson (Encore Bank), and Karan Kashyap (Posh). They swap “day-in-the-life” notes, why AI went from “go slow” to “why aren’t we live,” practical stablecoin prep, real-time payments use cases, ERP integrations, deposit outflows to wealth apps, and why “seamless integration” usually isn’t. Rooftop vibes included.Timestamps:00:04 Scene-set + guest lineup (DefenseStorm, Invest Defi, Encore Bank, Posh).03:29 “Day in the life”: small-company stretch roles, startup rhythms, running bank ops, CEO still coding.09:00 AI mood shift: boards from cautious to urgent; “web-banking déjà vu.”10:36 Stablecoins: watch, don’t leap; near-term priority is fiat↔stable on/off-ramps.12:41 Bank priorities: real-time payments and ERP integrations for commercial clients.15:07 Integration reality: solving treasury onboarding with true end-to-end partners (docs + core push).17:23 Deposit defense: 5–10% outflows to investment platforms—be the investing on-ramp.18:02 Cyber angle: pace of change ⇒ more risk; move from whac-a-mole to proactive controls.22:38 Live AI wins: disclosure review pipeline; measuring AI ROI (tokens, accuracy) and loan-doc diffs.26:00–30:26 What’s working now: banks leaning in, co-building with fintechs, deposit/treasury innovation, optimistic tone; wrap.Top TakeawaysAI urgency: Boards and execs moved from “slow down” to “why aren’t we live?”—time to graduate from licenses to application-layer outcomes.Stablecoin stance: For banks today, focus on compliant on/off-ramps and multi-currency readiness rather than speculative use cases.Payments & ERP: RTP adoption and deep ERP integrations are must-win commercial banking battlegrounds.Integration reality: “Seamless” is oversold—pick partners who’ll do the unglamorous workflow plumbing end-to-end.Deposit defense: Mind the wealth leakage to investing apps; offer native pathways before funds walk.Security ≈ survival: Rapid change expands the attack surface—proactive cyber risk management is table stakes.Prove AI ROI: Track tokens, accuracy, and cycle-time reduction; start with auditable, high-impact workflows (e.g., disclosures, credit-memo vs. docs diffs).

July 17, 2025Episode 544 min

Deals, Data & the Digital Shift with Kelley Michalik & Stephen Baker

In this episode of Fintech Hustle, host Sam Kilmer engages with guests Kelley Michalik, Kelli Schultz, and Stephen Baker to discuss the evolving landscape of fintech, focusing on investment trends, the integration of marketing and sales, and the competitive dynamics between community banks and megabanks. The conversation highlights the importance of trust, the challenges of integration, and the potential of AI to transform the industry. The episode concludes with a tribute to Barb McLean, a notable figure in the fintech community.Takeaways:The fintech landscape is seeing increased investor interest and momentum.Community banks are gaining traction against megabanks by focusing on personalized service.Integration challenges remain a significant hurdle in the fintech industry.AI has the potential to level the playing field for smaller financial institutions.The shift from marketing to sales is crucial for creating a seamless customer experience.Trust is eroding in big banks, creating opportunities for community institutions.The importance of storytelling in marketing to attract younger customers.Collaboration between marketing and sales teams is essential for success.The need for integration standards in fintech is still pressing.Fresh perspectives from new entrants can drive innovation in the industry.

May 14, 2025Episode 431 min

Off the Stage at Finovate Spring 2025 // Maya Mikhailov, Jason Henrichs & Andy Ivankovich

Forget the keynote fluff and polished demo, this episode of Fintech Hustle drops you straight onto a sun-drenched San Diego balcony with the real players of Finovate Spring 2025. Host Sam Kilmer is joined by fintech rockstars Maya Mikhailov (SAVVI AI), Jason Henrichs (Alloy Labs), and Andy Ivankovich (Baker Hill) for a breakdown of what’s actually happening behind the scenes of the industry’s flashiest conference.If you’re tired of hearing "AI for X" without substance, wondering what bankers are really doing with data, and curious whether fintech is facing a vibe shift—this is your episode.What You'll Learn:AI Hype vs. Reality: Why everyone’s claiming to be “AI-powered”—and why that’s a problemFrom Vibes to Value: The dangers of “vibe-based banking” and the shift to data-backed decision-makingData Ponds vs. Oceans: A practical new take on building usable data systems without drowning in complexityFintech Frustrations: The biggest annoyances of the show—and what needs to be fixed, fastWhat’s Actually Working: Real use cases where small banks are doing big things with automation and AIInside Jokes & Honest Talk: Classic rock, Torrey Pines trivia, and bucket-list podcast moments