Mighty Finsights

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Bill Bloom - dianemoney.com - LinkedIn: Diane Money

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.

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - David Benskin - wealthaccess.com - LinkedIn: Wealth Access

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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.

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Chris Levy - pursuitlending.com - LinkedIn: Pursuit

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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.

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Jack Macy

Download the Definitive Buyer’s Guide for Hiring a Financial Marketing Agency

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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.

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Levi King, Nav.com, LinkedIn: Nav

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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.

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Joey Bouchard, QuoteWell

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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.

• 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.

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

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Jack Macy, Brendan Bresnahan, Romina Gomez

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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.

• 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.

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

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Frank T. Young, Frank’s Substack

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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.

• 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.

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

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Mike Nellis, Austin Community Foundation - LinkedIn: Austin Community Foundation

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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.

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

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!

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.

• 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

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