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

Interview with Mary Ann Miller: What We Promised the Queen of England

Host - https://www.linkedin.com/in/roryeholland/Rory Holland [https://www.linkedin.com/in/roryeholland/] - https://cstmr..comcstmr.com [https://cstmr..com] - https://www.linkedin.com/company/cstmr/Linkedin: CSTMR [https://www.linkedin.com/company/cstmr/] Interviewed - Mary Ann Miller [https://www.linkedin.com/in/cybergalmam/] - Prove [https://www.prove.com/] - LinkedIn: Prove [https://www.linkedin.com/company/proveidentity/] 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.

Interview with Dori Yona: Recycling Failed Businesses into New Opportunities

Host - https://www.linkedin.com/in/roryeholland/Rory Holland [https://www.linkedin.com/in/roryeholland/] - https://cstmr..comcstmr.com [https://cstmr..com] - https://www.linkedin.com/company/cstmr/Linkedin: CSTMR [https://www.linkedin.com/company/cstmr/] Interviewed - Dori Yona [https://www.linkedin.com/in/dori-yona-b8369877/]- simpleclosure.com [https://simpleclosure.com/] - LinkedIn: SimpleClosure [https://www.linkedin.com/company/simpleclosure/posts/?feedView=all] 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 .

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

Host - https://www.linkedin.com/in/roryeholland/Rory Holland [https://www.linkedin.com/in/roryeholland/] - https://cstmr..comcstmr.com [https://cstmr..com] - https://www.linkedin.com/company/cstmr/Linkedin: CSTMR [https://www.linkedin.com/company/cstmr/] Interviewed - Charles Rosenblatt [https://www.linkedin.com/in/charlesrosenblatt/] - butterpayments.com [https://www.butterpayments.com/] - LinkedIn: Butter Payments [https://www.linkedin.com/company/butterpayments/] 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.

Interview with Colton Pond: The War Fintech Didn’t Win

Host - https://www.linkedin.com/in/roryeholland/Rory Holland [https://www.linkedin.com/in/roryeholland/] - https://cstmr..comcstmr.com [https://cstmr..com] - https://www.linkedin.com/company/cstmr/Linkedin: CSTMR [https://www.linkedin.com/company/cstmr/] Interviewed - Colton Pond [https://www.linkedin.com/in/colton-pond-469b11ba/] - socure.com [https://www.socure.com/] / fintechnerdcon.com [https://www.fintechnerdcon.com/] - LinkedIn: Socure [https://www.linkedin.com/company/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.

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

Host - https://www.linkedin.com/in/roryeholland/Rory Holland [https://www.linkedin.com/in/roryeholland/] - https://cstmr..comcstmr.com [https://cstmr..com] - https://www.linkedin.com/company/cstmr/Linkedin: CSTMR [https://www.linkedin.com/company/cstmr/] Interviewed - Bill Bloom [https://www.linkedin.com/in/bloomfinancial/] - dianemoney.com [https://www.dianemoney.com/] - LinkedIn: Diane Money [https://www.linkedin.com/company/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.