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. Interview with Charles Rosenblatt: The Javelin Thrower's Guide to Building a Fintech Career

    Jun 3

    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 EpisodeCharles 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.

    55 min
  2. Interview with Colton Pond: The War Fintech Didn’t Win

    May 13

    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 EpisodeColton 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.

    48 min
  3. Interview with Bill Bloom: Lighting Money on Fire and the Quest to Pay off $1B in Consumer Debt

    Apr 23

    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 EpisodeIn 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.

    59 min
  4. Interview With David Benskin: A New Brand, a New Category, the 13-Year Evolution to Connected Intelligence

    Mar 31

    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 EpisodeIn 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.

    47 min
  5. Interview with Chris Levy: Rising from Intern to CEO in Just Over a Decade

    Mar 17

    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 EpisodeIn 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.

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

    Mar 3

    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
  7. 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
  8. 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
See All (47)

Trailer

4.9
out of 5
8 Ratings

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
    47
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 CSTMR LLC.
  • Show Website
    Mighty Finsights