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

Interviewed - Alex Preece - Tillo - Tillo LinkedIn

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.

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

Interviewed - Mary Ann Miller - Prove - LinkedIn: Prove

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.

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

Interviewed - Dori Yona- simpleclosure.com - LinkedIn: SimpleClosure

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 .

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

Interviewed - Charles Rosenblatt - butterpayments.com - LinkedIn: Butter Payments

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.

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

Interviewed - Colton Pond - socure.com / fintechnerdcon.com - LinkedIn: Socure

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.

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

Want to be a part of the podcast? Contact Rory today!

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

Want to be a part of the podcast? Contact Rory today!

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

Want to be a part of the podcast? Contact Rory today!

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

Want to be a part of the podcast? Contact Rory today!

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.