BusinessMarketingTechnology

Mighty Finsights

CSTMR

Welcome to "Mighty Finsights," the podcast where finance meets formidable insights and spirited storytelling. Hosted by fintech and financial services agency CSTMR, this show delves into the stories that shape the world of finance and fintech, brought to you straight from the minds of those who know it best—the innovators, the disruptors, and the trailblazers.

Each episode of "Mighty Finsights" is a journey into the heart of financial innovation and personal achievement. We sit down with finance professionals, fintech founders, and visionary leaders to uncover the narratives that are often overshadowed by numbers and charts. From humble beginnings to groundbreaking achievements, our guests share not just their successes, but the challenges and setbacks that have shaped their path in the finance industry.

Whether you're a finance professional seeking to glean insights from leaders in the field, a fintech founder curious about the latest trends and technologies, or simply someone fascinated by the stories of grit and perseverance behind successful enterprises, "Mighty Finsights" is your gateway to understanding the complexities and capturing the spirit of the financial world.

Join us as we unveil the powerful insights and the incredible people behind them, offering not just lessons in finance, but also in innovation, resilience, and the continuous pursuit of excellence. "Mighty Finsights" is more than a podcast - it's an experience where finance and insight come to life: www.cstmr.com/mighty-finsights-podcast.

To be a guest on the podcast: https://cstmr.com/mighty-finsights-podcast-guest/.

Play

Open in

20 episodes
fortnightly
Avg 52 min
English

Episodes 20

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

#47
September 23 · 1 hr 10 min· Video
Interview with Sarah Biller: The Appalachian Approach to Fintech Innovation
In This Episode Sarah Biller, Co-founder of FinTech Sandbox, joins host Rory Holland to explore the deep intersection of data, human values, and market stability. Drawing from her roots as an 11th-generation West Virginian, Sarah reflects on how early lessons in independence and community shaped her approach to modern finance. The conversation touches on her early work using machine learning to detect credit risk, drawing an analogy to oceanic buoy sensors that alert coastal communities before a crisis hits. Sarah breaks down why high-quality data remains the ultimate bottleneck for startup innovation and how FinTech Sandbox helps entrepreneurs bridge that gap. Together, they unpack the risks of relying on AI speed over deep understanding, the urgent need to treat financial literacy as a public health imperative, and the power of authentic storytelling to cut through digital noise.
#46
September 4 · 1 hr 4 min· Video
Interview with Luther Maday: Practicing Risk in the Cockpit and on the Ledger
In This Episode Luther Maday, CEO of Stablecoin Partners and Head of Partnerships at Notabene, joins host Rory Holland on Mighty Finsights for an exploration of aviation, digital assets, and leadership. Drawing parallels from his experience as a private pilot, including the heart-stopping moment when he induced a tailspin in flight training, Luther breaks down how meticulous preparation, checklist discipline, and managing risk translate directly to navigating financial technology. From growing up as an expat across the Middle East to drafting landmark stablecoin legislation in Georgia, Luther offers a candid look at the evolution of money movement. The conversation opens up real-world use cases like cross-border refugee aid, corporate treasury optimization, and travel rule compliance, while reflecting on the human side of leadership, empathy, and grace in business. Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Luther Maday - Stablecoin Partners - Notabene
#45
August 17 · 40 min· Video
The CSTMR Team Unpacks Google’s Guidance on AI Search and Building Brand Authority
Host - Zac Garver- CSTMR- CSTMR LinkedIn Interviewed - Romina Gomez- CSTMR- CSTMR LinkedIn Brendan Bresnahan- CSTMR- CSTMR LinkedIn In This Episode CSTMR team members Zac Garver, Romina Gómez, and Brendan Bresnahan break down Google’s recent documentation on optimizing websites for generative AI features. As search behavior shifts and AI overviews reduce traditional website click-through rates, the group discusses why chasing short-term tactics or writing for algorithms instead of humans fails. They explore how foundational SEO practices remain essential for generative engine optimization and answer engine optimization, highlighting the importance of original, non-commodity content rooted in first-hand experience. By moving away from hyper-focusing on immediate clicks and exact-match keywords, businesses can build a durable, holistic Discovery Optimization strategy across search, social, and earned media.
#44
July 31 · 1 hr· Video
Interview with Alex Preece: Surviving the Horror of Startup Bankruptcy and Welfare
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Alex Preece - Tillo - Tillo LinkedIn In This Episode What connects jumping out of airplanes, surviving a $200k tax mistake over a single weekend, and turning gift cards into financial infrastructure? In this episode of Mighty Finsights, Alex Preece, Founder and CEO of Tillo, joins Rory Holland to share his path from British paratrooper to leading a global fintech engine. Alex breaks down how Tillo pioneered API connectivity in a legacy industry, turning simple branded currency into a tool that helps consumers pay down mortgages, fund pensions, and combat the cost of living. Along the way, he reflects on losing control, the therapeutic nature of horror movies for founders, and why true business endurance comes from treating your company like an evolving entity rather than an exit strategy. It is a candid conversation on resilience, trust, and expanding your vision beyond arbitrary ceilings.
#43
July 13 · 53 min· Video
Interview with Mary Ann Miller: What We Promised the Queen of England
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Mary Ann Miller - Prove - LinkedIn: Prove In This Episode Cyber fraud and identity veteran Mary Ann Miller, VP of Client Experience at Prove, joins host Rory Holland to unpack her thirty-year journey at the intersection of technology and security. From launching early neural networks in the nineties to navigating modern deepfake threats, Mary Ann highlights why authentic identity verification has become the essential welcome mat for digital interaction. The discussion blends high-level risk management strategy with a deeply human perspective, exploring the heartbreaking toll of scams on vulnerable populations like the elderly. Mary Ann also shares captivating stories from her personal adventures, including night diving with majestic manta rays and dining at the royal Clarence House while offering timeless leadership wisdom on leveraging community frameworks and knowing when to pause for the second beat.
#42
June 18 · 49 min· Video
Interview with Dori Yona: Recycling Failed Businesses into New Opportunities
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Dori Yona- simpleclosure.com - LinkedIn: SimpleClosure In This Episode Dori Yona, co-founder of SimpleClosure, joins host Rory Holland to explore how navigating one of the lowest points in his entrepreneurial life led to building a groundbreaking infrastructure business. Dori opens up about his time commanding a platoon of ships in the IDF Navy, sharing how high-pressure environments shaped his collaborative leadership style. After being forced by his board to shut down a previous startup, he experienced firsthand the isolating, complex, and expensive reality of winding down a business. That dark moment sparked the vision for SimpleClosure, an automated platform that helps companies close gracefully while monetizing their leftover code, data, and assets . This conversation dives into the emotional weight of founder layoffs, the power of persistent curiosity, and why clean endings pave the way for successful new beginnings .
#41
June 3 · 55 min· Video
Interview with Charles Rosenblatt: The Javelin Thrower's Guide to Building a Fintech Career
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Charles Rosenblatt - butterpayments.com - LinkedIn: Butter Payments In This Episode Charles Rosenblatt, CEO of Butter Payments, joins Rory Holland to pull back the curtain on the operational realities of global payments and subscription models. With over two decades of experience spanning traditional powerhouse banks like JPMorgan Chase to hyper-growth fintech exits like Hyperwallet and Payoneer, Charles brings an authentic operator perspective to the mic. The conversation explores the massive, often hidden threat of involuntary churn—where mechanical payment failures quietly alienate good subscribers—and how Butter utilizes machine learning as a seamless predictive layer to capture lost revenue. Beyond the technology, Charles opens up about his journey from a competitive college athlete to building a fintech career, the deep personal influence of his father, and the invaluable leadership lesson of prioritizing long-term victory over short-term battles.
#40
May 13 · 48 min· Video
Interview with Colton Pond: The War Fintech Didn’t Win
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Colton Pond - socure.com / fintechnerdcon.com - LinkedIn: Socure In This Episode Colton Pond, Global CMO of Socure and co-founder of Fintech Nerdcon, joins Rory Holland to discuss the technological landscape of identity and trust. Colton shares why the predicted "war" between banks and fintechs shifted toward collaboration and how traditional institutions are now embracing tech-first strategies. The conversation dives deep into the threat of AI-driven fraud, where deepfakes and automated attacks have reduced criminal expenses to near zero, requiring more sophisticated, proactive defenses like Socure’s global identity graph. Beyond technology, Colton opens up about his relentless work ethic—a mentality he calls "all gas, no brakes"—and his passion for fixing a broken financial education system for the next generation. From scuba diving adventures to the community-driven innovation of Fintech Nerdcon, this episode explores what it takes to lead with 110% intensity.
#39
April 23 · 59 min· Video
Interview with Bill Bloom: Lighting Money on Fire and the Quest to Pay off $1B in Consumer Debt
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Bill Bloom - dianemoney.com - LinkedIn: Diane Money In This Episode In this episode, Rory Holland sits down with Bill Bloom, wealth architect and founder and CEO of Diane Money, to explore what it really takes to break free from the debt cycle — and why so few people ever do. Bill reflects on his path from Prudential financial advisor to building an app named after his mother, a woman who carried 45 credit cards and inspired a mission to eliminate a billion dollars of bad debt. They discuss why the financial system is engineered to keep people in debt, how most of us inherit our money beliefs before we ever earn our first paycheck, and what it actually looks like to build a roadmap out of the cycle. Bill also gets candid about pouring over $200,000 into failed development attempts — and why he never quit. Beyond the app, Bill and Rory get honest about their own financial struggles, the shame that keeps people silent, and why the most powerful financial tool available to anyone might just be a real conversation.
#38
March 31 · 46 min· Video
Interview With David Benskin: A New Brand, a New Category, the 13-Year Evolution to Connected Intelligence
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - David Benskin - wealthaccess.com - LinkedIn: Wealth Access Want to be a part of the podcast? Contact Rory today! In This Episode In this episode, Rory Holland sits down with David Benskin, the founder and CEO of Wealth Access, to explore the grit required to change the way financial institutions use their data. David reflects on his 13-year journey as CEO, from his early days at Merrill Lynch to navigating the global financial crisis and launching a platform to solve the fragmented data problem plaguing financial institutions, wealth advisors, and clients alike. They discuss the decision to rebrand from a data aggregator to a connected intelligence platform, the vital role of clean data as a foundation for AI, and why technology should empower—not replace—the human element of financial advice. Beyond the boardroom, David shares how coaching his kids in wakeboarding mirrors the responsibilities of a CEO.
#37
March 17 · 45 min· Video
Interview with Chris Levy: Rising from Intern to CEO in Just Over a Decade
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Chris Levy - pursuitlending.com - LinkedIn: Pursuit Want to be a part of the podcast? Contact Rory today! In This Episode In this episode, Rory Holland sits down with Chris Levy, President and CEO of Pursuit, a mission-driven community development financial institution (CDFI). Chris shares his remarkable homegrown journey, rising from a summer intern to the head of the organization in just over a decade. They dive into the discipline required to complete a law degree while working full-time, the strategic decision to rebrand a 70-year-old institution to unify its identity, and Pursuit’s pivotal role in deploying $780 million in PPP loans to small businesses. Chris also reflects on the human side of leadership—balancing a high-stakes career with the transition to first-time fatherhood and the value of embracing tough feedback to grow as an executive.
#36
March 3 · 36 min· Video
Rory Holland and Jack Macy: A Conversation about Choosing the Right Agency and Partnering for the Long Haul
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Jack Macy Download the Definitive Buyer’s Guide for Hiring a Financial Marketing Agency Want to be a part of the podcast? Contact Rory today! In This Episode In this special episode of Mighty Finsights, host Rory Holland is joined by CSTMR co-founder and COO Jack Macy to pull back the curtain on the agency selection process. Drawing from decades of experience on both the client and agency sides, Rory and Jack discuss the Agency Buyer’s Guide, which is a strategic framework designed to help fintech and financial services leaders find the right marketing partner. They explore the three essential themes of connection, credentials, and collaboration while identifying the red flags that often lead to failed partnerships. Whether you are scaling a mature business, modernizing a legacy brand, or launching a new product, this conversation provides the practical wisdom needed to move beyond passive execution firms and find a strategic operator invested in your long-term success.
#35
February 17 · 57 min· Video
Interview with Levi King: From Sign Shop to $100M Founder
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Levi King, Nav.com, LinkedIn: Nav Want to be a part of the podcast? Contact Rory today! In This Episode In this episode, host Rory Holland sits down with Levi King, the serial entrepreneur and visionary behind Nav. Levi’s story is a masterclass in building a mission-driven brand, starting with the deeply personal "pact" he made to secure the Nav.com domain to honor a small business legacy. The conversation moves far beyond typical fintech metrics, diving into the "brutal" 360-degree feedback exercise that transformed Levi from a boss into a leader at age 26. He also speaks transparently about his personal journey with mental health and panic attacks, advocating for a leadership style rooted in psychological safety and empathy. From his Main Street roots fixing electric signs to raising $100 million in venture capital, Levi provides hard-won insights on navigating the complex world of business credit and the human side of leadership.
#34
February 4 · 1 hr· Video
Interview with Joey Bouchard: The Insurance Industry Needed a ‘Human+’ Model
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Joey Bouchard, QuoteWell Want to be a part of the podcast? Contact Rory today! In This Episode In this episode of Mighty Finsights, host Rory Holland sits down with Joey Bouchard, Founder and CEO of QuoteWell, to discuss the modernization of the wholesale insurance industry. Joey shares his journey from the high-stakes environment of Palantir to solving the Gordian Knot of insurance quoting. They explore the Human+ model—a philosophy that uses technology to empower brokers rather than replace them. Joey explains the importance of the underdog mindset, the value of choosing applied learning over traditional academia, and why the clearinghouse for risk is ripe for digital transformation. Whether you're interested in insurtech innovation, tactical leadership advice, or the connection between dating and sales Joey’s perspective is well worth a listen. Key Takeaways The "Human+" Philosophy: Success in insurtech isn't about total automation; it’s about using technology to remove friction so human brokers can focus on high-value relationships. The Underdog Mindset: Joey highlights how his hatred of losing and intense work ethic—honed as a non-Ivy League recruit at Palantir—drive his success at QuoteWell. Solving the Data Gap: QuoteWell was born from the realization that wholesale insurance lacks standardized data, creating a massive opportunity. Wholesale Insurance as a Clearinghouse: Despite being a legacy sector, wholesale brokers facilitate 25% of commercial transactions, making them a critical infrastructure for the economy. The Power of the Caesura: Joey discusses the importance of "taking a beat" or a pause before making major decisions to ensure clarity and strategic alignment. Applied Learning vs. MBA: Joey explains why he chose a hands-on strategy role at Aon to learn the messy reality of insurance instead of pursuing a traditional graduate degree. Mission-Driven Work: Innovation in insurance isn't just about software; it’s about the real-world impact of ensuring businesses can survive catastrophic losses. Chapters 00:00: Young, and Determined 02:14: Introduction with Rory Holland 03:30: Austin Eateries and Sales Wisdom 08:05: The Hunter Mountain ACL Incident 11:15: The Palantir "Bootcamp" Experience 14:15: Learning Perseverance and Grit 17:45: The Decision to Tackle Insurance 20:45: Five Countries in Five Days 23:30: Niche Expertise as a Career Catalyst 25:30: Growing Up in a Pawn Shop 28:30: The Pawn Shop Bait Counter and Samurai Swords 31:15: A Legacy of Hard Work 34:00: Defining QuoteWell and Wholesale Brokerage 39:15: Building the "First 30" 43:00: Empowering Brokers 44:45: Corporate Consolidation vs. The Collaboration Economy 49:15: Why Mission Matters 53:30: The Ruthless Elimination of Hurry 57:30: Connecting with QuoteWell 58:33 Closing Remarks with Rory Holland
#33
January 20 · 35 min· Video
Interview with Jack Macy, Brendan Bresnahan and Romina Gomez: Gaining Maximal Visibility in the AI Age
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Jack Macy, Brendan Bresnahan, Romina Gomez Want to be a part of the podcast? Contact Rory today! In This Episode Join Rory Holland and a panel of CSTMR specialists—Jack Macy, Brendan Bresnahan, and Romina Gomez—for a deep dive into the world of digital discovery. As AI tools like ChatGPT and Google’s AI Overviews challenge conventional search tactics, financial brands must shift to a mindset that expands brand visibility across digital channels. In this episode, the team introduces Discovery Optimization, a strategic framework encompassing SEO, Answer Engine Optimization (AEO), and Generative Engine Optimization (GEO). You’ll learn how to leverage your brand’s authority to win in the new AI-enabled ecosystem, why the fundamentals of quality content matter more than ever, and how to protect your brand from channel volatility. Whether you are a fintech founder or a marketing leader, this discussion provides the roadmap for staying discoverable and trusted in the age of artificial intelligence. Key Takeaways SEO is evolving, not going away: Traditional search remains massive, but it is now part of a larger, more fragmented digital ecosystem that includes AI chatbots and voice search. Total visibility mindset: Brands must stop thinking about "SEO vs. AI" and instead focus on total brand visibility across all possible discovery channels. Understanding SEO, AEO, and GEO: Discovery Optimization integrates Search Engine Optimization (SEO), Answer Engine Optimization (AEO) for AI features, and Generative Engine Optimization (GEO) for citations in tools like ChatGPT Fundamentals still fuel consumer discovery: What works for SEO—high-quality, authoritative content—is also what powers success in AEO and GEO. Authority is the gatekeeper: For "Your Money or Your Life" (YMYL) financial topics, showing Experience, Expertise, Authoritativeness, and Trustworthiness (E-E-A-T) is essential to be cited by AI. Consistency across channels: To build trust, financial brands must maintain messaging consistency across their blog, YouTube, press coverage, and community forums. Gen Z is leading the shift: Adoption of AI search is highest among younger demographics, with 76% of Gen Z and younger millennials trusting AI answers over traditional search results. YouTube is a discovery engine: YouTube is increasingly critical, accounting for a significant percentage of impressions and mentions in AI-generated overviews. Chapters 00:00 Discovery Optimization and the Evolution of Online Visibility 05:55 Navigating the "Acronym Soup" of Modern Search 14:20 Owning Your Channels: Why Consistency Is Key for Financial Brands 18:40 Gen Z and the Future of Search Preferences 23:07 Content for People, Not Machines 28:50 Looking Ahead: The Future of Digital Discovery 35:44 Outro
#32
Dec 9, 2025 · 1 hr 2 min· Video
Interview with Frank Young: Why Adaptive Leadership Can Save Fintech Firms Millions
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Frank T. Young, Frank’s Substack Want to be a part of the podcast? Contact Rory today! In this Episode Episode 32 of Mighty Finsights features Frank T. Young, strategic advisor, angel investor, and former executive at Google and Global Payments. He joins Rory Holland to discuss what it’s liking building products at some of the biggest names in financial technology. This conversation tackles pivotal moments in payments modernization, including an insider look at why Google Wallet failed to secure a business model where Apple Pay succeeded. Young offers candid analysis on the fundamental culture clash between fast-moving tech and slow, regulated financial institutions, and explains how adaptive leadership is key to navigating that divide. He also shares personal stories—like a piano recital that helped him get hired at Google—and how Kobe Bryant’s Black Mamba ethos influences his approach to consulting. Key Takeaways The role of Embedded Fintech: The highest standard of user experience in payments is one that is largely "invisible" (embedded fintech), allowing users to focus on commerce, not transactional complexity. Data vs. Privacy-First Business Models: The fundamental psychological problem for Google Wallet was that bankers did not trust Google with their data, an issue Apple circumvented by positioning itself as the "antithesis of Google" on data. Take the Time to Correctly Define Problems: A critical leadership lesson in consulting is to never misdiagnose an adaptive problem (like cultural readiness for change) as a technical problem. Market Dominance Does Not Equal Brand Recognition: Global Payments, despite massive growth, struggled to establish brand recognition as a "value-added service provider" due to insufficient investment in marketing. The Willingness to Become a Student Again: Young's personal story of a piano recital at age 39—on the day his daughter was born—illustrated the humility and relentless improvement necessary for leadership. Banks Require Technological Consistency: Google's internal "engineering cycle" often led to new teams re-architecting and re-engineering products soon after launch, sometimes hindering operational continuity. Chapters 00:00 Introduction and Dunkin' Donuts Discussion 01:17 Interview - Start 02:23 How Frank Young Ended Up at Google 05:42 Unfolding the Google Wallet Experience 08:45 Why Google Wallet Struggled to Gain Traction with Partners 12:38 The Philosophy Behind Apple Pay's Rise to Dominance 13:50 Rory Holland - Commentary 14:20 The Philosophy Behind Apple Pay's Rise to Dominance - Continued 15:18 Transitioning from Google to Global Payments 19:13 Frank's Decision to Learn Piano at Age 39 21:58 Creating the Googley Factor by Living Life Out Loud 24:40 Wisdom Earned While Working at Global Payments 27:42 Why Brand Recognition Matters So Much in Fintech 29:13 Rory Holland - Commentary 29:39 Why Brand Recognition Matters So Much in Fintech - Continued 30:49 Falling Down the Rabbit Hole of Financial Technology 33:14 A Family Passion for Music 36:40 The Half-Fast Walking Club 39:25 Mamba Mentality and Personal Growth 41:48 Bringing Adaptive Leadership into His Consulting Practice 44:58 Rory Holland - Commentary 45:20 Bringing Adaptive Leadership into His Consulting Practice - Continued 51:39 Frank's Angel Investments and Work with Fintech Startups 56:40 Insights Into Frank's Current Season of Life 58:53 Closing Remarks 01:00:30 Interview End
#31
Nov 25, 2025 · 59 min· Video
Interview with Mike Nellis of Austin Community Foundation: How Community Foundations Can Restore Trust in Philanthropy
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Mike Nellis, Austin Community Foundation - LinkedIn: Austin Community Foundation Want to be a part of the podcast? Contact Rory today! In This Episode In episode 31 of Mighty Finsights, Rory Holland interviews Mike Nellis, CEO of the Austin Community Foundation (ACF), about the pivotal role of community foundations in today's economy and philanthropic landscape. Mike discusses how ACF serves as a "charitable bank" and community endowment, connecting people and resources to tackle issues like housing affordability. They explore the generational wealth transfer and the skepticism younger generations hold toward traditional philanthropy. Learn why ACF is focused on trust-based giving, and how they use flexible capital and deep community knowledge to deploy capital with sustained impact, moving beyond simple transactional giving. Generational Wealth Transfer: A massive transfer of wealth is underway, posing a huge opportunity for organizations like community foundations to help younger generations invest capital meaningfully. Skepticism in Philanthropy: Younger individuals from wealthy families are often skeptical of traditional philanthropy, requiring challenge and guidance on how to use their capital and influence for significant positive change. Beyond Charitable Banking: Community foundations function as both a charitable bank (managing Donor Advised Funds or DAFs) and a permanent community endowment, ensuring capital is available for both today's and future needs. DAFs Offer Flexibility: Donor Advised Funds (DAFs) allow donors to receive a tax deduction today while making gifts over time, offering efficiency and flexibility in charitable giving. Trust-Based Giving: A shift is occurring away from prescriptive giving to a trust-based philanthropic perspective, where funds are invested in high-impact organizations and their leadership, moving beyond focusing on overhead minutiae. Solving Housing Affordability: The Austin Community Foundation is tackling the local housing affordability crisis by providing cheap, fast, and flexible debt to developers to unlock other capital for housing production. Data and Future Relevance: ACF remains relevant by using data to understand regional challenges, which informs their grant-making and long-term strategy, enabling them to meet the community's needs in perpetuity. Living Minimal Is Freeing: Rory and Mike talk about their experiences living in RVs on the road and how those experiences shaped them as people and shaped their relationships with others. Chapters 00:00 EP31 - Teaser 00:40 EP31 Introduction 01:49 The Billionaire Philanthropy Workshop 06:00 Skepticism in Philanthropy: The Younger Generation's Perspective 07:35 Journey to Austin from the Midwest 12:01 Driving from CA to TX 13:50 Coffee, Colorado and the Flatirons 15:49 Rory Holland - Commentary 16:27 Coffee, Colorado and the Flatirons - Continued 17:11 What Is the Austin Community Foundation? 22:18 Differentiation Community Foundations from Private Foundations 24:46 What is a Donor-Advised Fund? 27:01 Tackling the Housing Crisis in Austin and Beyond 29:56 Rory Holland - Commentary 32:11 Tackling the Housing Crisis in Austin and Beyond - Continued 35:26 Supporting Artists and Cultural Preservation 37:31 The Guadalupe Floods in the Texas Hill Country 41:32 Selling Everything to Live Down by the River in an RV 43:08 Rory Holland - Commentary 43:40 Selling Everything to Live Down by the River in an RV - Continued 48:58 The Wealth Transfer and How to Make an Impact 54:29 ACF and the Future of Philanthropy 57:02 Closing Remarks
#30
Nov 6, 2025 · 1 hr 4 min· Video
Interview with Jason Henrichs of Alloy Labs: Why Brand Differentiation Is the Vital Strategy for Community Banks and Credit Unions
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Jason Henrichs, Alloy Labs - LinkedIn: Alloy Labs Book Recommendation: Team of Rivals by Doris Kearns Goodwin Want to be a part of the podcast? Contact Rory today! In This Episode Join us for Episode 30 where host Rory Holland sits down with Jason Henrichs, CEO at Alloy Labs and co-host of the #1 global fintech podcast, Breaking Banks. They dive into Jason's journey, from co-founding Perk Street, an early concept of Banking as a Service (BaaS), to leading community bank innovation at Alloy Labs. They explore the critical role of trust in building financial brands, especially in today's environment. Jason offers frank insights on why many community banks are facing a crisis of identity and brand, as well as how collaboration—like Abraham Lincoln's "Team of Rivals" approach—is key to making the pie bigger. This is a must-listen for anyone curious about the human motivations shaping the future of financial services. Key Takeaways The BaaS Origin Story: The early Banking as a Service model (like Perk Street) was driven by a deposit arbitrage to help community banks gather deposits, not just a Dodd-Frank interchange arbitrage. Trust as a Deliverable: Building trust requires real value and delivering on promises. Customers will choose you if you put "meat on the bone" of their expectations. The Anti-Wall Street Brand: In the wake of the 2008 financial crisis, brands could be built on an "anti Wall Street" sentiment, resonating with consumers looking to "take back Main Street". The Community Bank Challenge: Many community banks and credit unions will likely "die" if they don't find a real problem to solve and a unique selling proposition that customers truly value. Deposit Erosion: The consumer deposit base for community banks is aging, and the money of younger consumers is already fragmented across various platforms (like Amazon or pre-funded deposit intermediators). Competing with Scale: Smaller banks struggle to compete with large banks that are now tech-driven (like Chase) and startups (like Chime) that have raised billions in capital. A Portfolio of Bets: Alloy Labs helps banks thrive by focusing on a portfolio of strategic bets—ranging from high-flying problems (like payments via Rebolt) to more mundane necessities (like AI adoption via the AI Action Center). Beyond the Center of Money: Innovation should focus on the "edge of money," recognizing that money is a means to an end (e.g., getting a loan to open a new business location, not for the sake of the loan itself). The Power of Cooperation: The cooperative model (like Land O'Lakes in the dairy industry) can serve as a blueprint for how community banks can collaborate to survive and thrive. Lincoln's Leadership Lesson: Leaders should follow the "Team of Rivals" philosophy to bring forward diverse thought and solve big problems together, rather than protecting their existing "share of the pie". From Desperation to Inspiration: Jason's decision to found Alloy Labs was motivated by the frustration of seeing bankers who were "so f***ed" if they didn't take ownership of their future, leading to the creation of what he jokes is a "giant therapy session" for bank CEOs Chapters 00:00 EP30 - Teaser 00:37 Introduction 01:56 Interview Starts - Upbringing, a Gift, and Running 08:43 Founding Perk Street and the Birth of Banking as a Service 13:05 Building Trust in Financial Services 15:39 Rory Holland Commentary 16:03 Resume Interview 16:42 How Financial Brands Are Dealing with Consumer Distrust 18:41 Alloy Labs: Innovating for Community Banks 22:59 How Alloy Labs Evaluates Fintech Partners 29:25 Telling the Ugly Truth to Community Bankers 32:57 Rory Holland Commentary 33:19 Resume Interview 35:14 What Problems Does Jason Think Are Worth Solving 38:59 The Challenge of Differentiating as a Community FI 44:03 The Market Is Shifting Under the Feet of Community Bankers 48:10 Lessons from History: Leadership and Trust 50:46 Rory Holland Commentary 51:10 Resume Interview 51:50 The Intersection of Entrepreneurship and Stewardship 56:20 Abraham Lincoln as Head of People 01:00:48 Wisdom from Jason's Current Season of Life 01:03:03 Outro
#29
Sep 9, 2025 · 39 min· Video
Interview with Alex Bates of Dark Rock Cybersecurity: Using SOC 2 to Enhance Your Business, Not Just Manage Risk
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Jack Macy, CSTMR and Alex Bates, Dark Rock Cybersecurity - LinkedIn: CSTMR and Dark Rock Cybersecurity Want to be a part of the podcast? Contact Rory today! In This Episode Join us for Episode 29 of Mighty Finsights, where Rory Holland interviews Jack Macy, founder and COO of CSTMR, and Alex Bates with Dark Rock Cybersecurity about the journey CSTMR took to achieve SOC 2 compliance. They explore the importance of SOC 2 for building trust with clients, the challenges faced during the process, and the benefits of being a certified vendor in the financial services industry. The conversation also covers the selection of the right SOC 2 partner and offers advice for organizations considering pursuing SOC 2 compliance, including why it’s helpful to have an expert coach to guide you through the process. Key Takeaways SOC 2 compliance is an excellent way to improve organizational health and build client trust. CSTMR's proactive approach to SOC 2 is unusual for service-based business, especially agencies. The SOC 2 process helps formalize risk management practices and “harden” security protocols. Data breaches incur significant costs and reputational harm for organizations. Selecting the right SOC 2 partner will make a big difference in your experience and the quality of your results. Investing in compliance should be viewed as a long-term strategy. Training and educating the organization as a whole is key to successful implementation. SOC 2 is a report of compliance, not a “certification.” Chapters 00:00 Episode Introduction 01:58 Why Did CSTMR Pursue SOC 2? 03:58 The Importance of SOC 2 for Professional Services 06:09 Challenges in Achieving SOC 2 Compliance 09:52 Real-World Security Failures 12:57 The Direct Impact on a Brand 14:27 The Prevalence of SOC 2 in the Marketing Space 16:56 Benefits to CSTMR's Clientele 19:48 Selecting the Right SOC 2 Partner 22:21 What to Look for in a SOC 2 Vendor 24:13 How Playing Competitive Sports Informs Alex's Work 29:20 How to Know If SOC 2 Is Right for Your Organization 30:28 How CSTMR Tackled the Challenges of Passing SOC 2 34:07 Unpacking the Gap Analysis 35:44 Trust Service Criteria
#28
Jul 8, 2025 · 43 min· Video
Interview with Jorge Garcia of Linker Finance: Solving Commercial Banking Tech the Hard Way and Winning
Host - Rory Holland - cstmr.com - Linkedin: CSTMR Interviewed - Jorge Garcia, Linker Finance - LinkedIn: Linker Finance Want to be a part of the podcast? Contact Rory today! In This Episode Join us for Episode 28 of Mighty Finsights, where Rory Holland interviews Jorge Garcia, Co-founder and CEO of Linker Finance, about the digital banking needs that community banks have for their commercial clients. Jorge shares his journey from Honduras to the U.S., lessons learned as an internationally competitive swimmer, and how these experiences shaped his entrepreneurial spirit. Jorge also talks about how his relationship with his wife and co-founder has also affected the growth and health of the company overall. The conversation also explores the unique economic role that community banks play in the U.S., how the future could play out for those institutions, and why doing things the hard way can actually be a key to success in a crowded marketplace. Key Takeaways Linker Finance provides digital banking solutions for commercial banking clients. Jorge's background as an international swimmer instilled a long-term goal mindset paired with skills to execute in the short term. Community banks are responsible for the amazing health of small businesses and the U.S. economy Fintech companies are increasingly looking at the commercial banking sector as an opportunity to innovate. Building relationships is key in marketing to community banks. Jorge emphasizes the importance of celebrating small wins in business. Linker Finance aims to connect business banking technology with the needs of community banks. Strategic partnerships are playing a big role in Linker’s next phase of growth. Jorge believes that community banks can thrive with the right technology. The future of fintech is uncertain - it could greatly reduce the role of community banks or it could make them stronger. Chapters 00:00 Introduction to Linker Finance 02:56 Jorge's Journey from Honduras to the U.S. 06:00 The Birth of Linker Finance 08:56 Understanding Community Banks and Their Needs 12:06 Working With Vault.Bank and Gaining a New Investor 14:39 The Impact of Competitive Swimming on Business 19:51 Brand Positioning in a Competitive Market 21:35 Building Relationships in Business 23:45 Spouses and Co-founders: A Match Made in Honduras 27:29 The Importance of Community Banks 31:12 How Constraint Satisfaction Helps Build Companies 34:24 Innovations on the Horizon for Linker 36:28 Holistic User Experience in Community Banking 40:31 Reframing the Data on Community Banking and Technology 45:47 The Essence of Linker: Connection and Innovation

Showing 1–20 of 20 episodes