Fintech Hustle

Cornerstone Advisors
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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.

  1. NOV 17

    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. Links Sam 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

    14 min

  2. OCT 29

    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 Moments 00:11 Guest lineup and setup from the halls of fintech to real operator stories 08:45 Events as strategy why orchestration and education matter as much as product 13:22 Purposeful AI prioritize problems, outcomes, and ROI rather than buzzwords 20:36 Governance and exams “know your agent,” vendor AI disclosures, anonymization, and risk 28:32 Tokenization debate on chain home equity, cost dynamics, smart contract enforcement, and whether consumers care 42:10 What’s broken and what wins data driven personalization and a call for FI entrepreneurship 47:03 Wrap and takeaways solve outcomes first and let tech follow

    47 min

  3. SEP 22

    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.

    18 min

  4. SEP 11

    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 Takeaways AI 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).

    31 min

  5. JUL 17

    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.

    45 min

  6. MAY 14

    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

    31 min

  7. APR 1

    Exploring Fintech Trends at AFT Conference // Alex McLeod, Ben Metz & Will Bryant

    In this episode of the Fintech Hustle podcast, host Sam Kilmer sits down live at the AFT Spring Conference with Alex McLeod (CEO, Parlay Finance), Ben Metz (CTO/CDO, Jack Henry), and Will Bryant (COO, Quantalytix) for a high-energy conversation about the future of financial services. The panel dives into key fintech trends, including the real-world impact of AI in banking, how institutions are rethinking efficiency ratios, and why consumer empowerment is reshaping the market. Beyond tech, they explore the cultural side of fintech – highlighting how music, creativity, and community fuel innovation. Whether you're a bank or credit union leader, fintech founder, or just love the hustle of financial innovation, this episode delivers strategic insights and fresh perspective straight from the field. 🎧 In this episode: Why AI is more than just a buzzword in fintech (and how leaders are applying it)How collaboration and culture can solve banking’s toughest challengesWhy efficiency doesn’t always require AI, and what to prioritize insteadThe increasing importance of human-centered digital experiencesHow events like AFT spark real industry transformation🔑 Keywords: Fintech podcast, financial services, banking technology, AI in banking, fintech innovation, efficiency ratios, consumer empowerment, AFT conference, credit union trends, financial collaboration, future of fintech

    26 min

  8. FEB 3

    Insights from the Acquire or Be Acquired Conference // Margaret Hartigan, Nikhil Lakhanpal & Todd Schell

    The Acquire or Be Acquired conference was buzzing with optimism, big ideas, and strategic conversations about the future of banking. In this episode of Fintech Hustle, host Sam Kilmer and co-host Al Dominick sit down for an unscripted discussion with Margaret Hartigan (Founder & CEO, Marstone), Nikhil Lakhanpal (Co-founder, Narmi), and Todd Schell (Managing Director, Warburg Pincus) to break down what’s ahead for the financial services industry in 2025. This candid conversation covers: The push for growth and scalability in an evolving marketWhy fraud concerns are rising across the industryThe challenge of integration pain and how banks can overcome itThe shift toward open APIs and stronger fintech partnershipsHow banks can move beyond pricing strategies to drive real innovationThe importance of understanding customer needs and forecasting effectively Like every episode of Fintech Hustle, this one is completely unscripted—just real insights from leaders who are shaping the future of financial services. Whether you're running a bank, credit union, or fintech firm, this is a conversation worth tuning into.

    27 min
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About

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.

Information

  • Channel
    Cornerstone Advisors
  • Creator
    Sam Kilmer & Cornerstone Advisors
  • Years Active
    2023 - 2025
  • Episodes
    38
  • Rating
    Clean
  • Copyright
    © 2025 Cornerstone Advisors
  • Show Website
    Fintech Hustle

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