Mighty Finsights

CSTMR
  • 4.9 (8)
  • MARKETING
  • UPDATED BIMONTHLY

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/.

  1. Rory Holland and Jack Macy: A Conversation about Choosing the Right Agency and Partnering for the Long Haul

    1D AGO

    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 EpisodeIn 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.

    36 min
  2. Interview with Levi King: From Sign Shop to $100M Founder

    FEB 17

    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 EpisodeIn 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.

    57 min
  3. Interview with Joey Bouchard: The Insurance Industry Needed a ‘Human+’ Model

    FEB 4

    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 EpisodeIn 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 TakeawaysThe "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. Chapters00:00: 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

    1 hr
  4. Interview with Jack Macy, Brendan Bresnahan and Romina Gomez: Gaining Maximal Visibility in the AI Age

    JAN 20

    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 EpisodeJoin 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 TakeawaysSEO 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 ChatGPTFundamentals 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. Chapters00:00 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

    36 min
  5. Interview with Frank Young: Why Adaptive Leadership Can Save Fintech Firms Millions

    12/09/2025

    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 EpisodeEpisode 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 TakeawaysThe 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. Chapters00:00 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

    1h 3m
  6. Interview with Mike Nellis of Austin Community Foundation: How Community Foundations Can Restore Trust in Philanthropy

    11/25/2025

    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 EpisodeIn 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. Chapters00:00 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

    1 hr
  7. Interview with Jason Henrichs of Alloy Labs: Why Brand Differentiation Is the Vital Strategy for Community Banks and Credit Unions

    11/06/2025

    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 EpisodeJoin 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 TakeawaysThe 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 Chapters00:00 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

    1h 5m
  8. Interview with Alex Bates of Dark Rock Cybersecurity: Using SOC 2 to Enhance Your Business, Not Just Manage Risk

    09/09/2025

    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 EpisodeJoin 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 TakeawaysSOC 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.” Chapters00:00 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

    39 min
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About

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/.

Information

  • Creator
    CSTMR
  • Years Active
    2024 - 2026
  • Episodes
    42
  • Rating
    Clean
  • Copyright
    © Copyright 2025 CSTMR LLC.
  • Show Website
    Mighty Finsights