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

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.

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

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 - David Benskin - wealthaccess.com [http://wealthaccess.com] - LinkedIn: Wealth Access [https://www.linkedin.com/company/wealth-access/] Want to be a part of the podcast? Contact Rory today! [https://cstmr.com/mighty-finsights-podcast-guest/] IN THIS EPISODE 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.

Interview with Chris Levy: Rising from Intern to CEO in Just Over a Decade

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 - Chris Levy [https://www.linkedin.com/in/chris-levy-874831228/] - pursuitlending.com [http://pursuitlending.com] - LinkedIn: Pursuit [https://www.linkedin.com/company/pursuitlending/] Want to be a part of the podcast? Contact Rory today! [https://cstmr.com/mighty-finsights-podcast-guest/] IN THIS EPISODE 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.