In This EpisodeMarco Castaneda, EVP National Production Manager at Velocity Mortgage Capital, joins host Rory Holland for an exploration of resilience, accountability, and leadership. Marco reflects on his journey from fax boy to executive, sharing how hitting rock bottom after the 2008 financial collapse redefined his perspective on success, money, and humility. He breaks down the dynamics of private lending for real estate investors and small business owners, emphasizing why long-term stability requires adapting to market shocks.Together, Rory and Marco discuss the crucial distinction between being a nice leader and a good one. As well as the necessity of direct communication, and how to coach the rising generation of mortgage professionals through authentic relationships.
Oct 15
1 hr 5 min
In This EpisodeSarah Biller, Co-founder of FinTech Sandbox, joins host Rory Holland to explore the deep intersection of data, human values, and market stability. Drawing from her roots as an 11th-generation West Virginian, Sarah reflects on how early lessons in independence and community shaped her approach to modern finance. The conversation touches on her early work using machine learning to detect credit risk, drawing an analogy to oceanic buoy sensors that alert coastal communities before a crisis hits. Sarah breaks down why high-quality data remains the ultimate bottleneck for startup innovation and how FinTech Sandbox helps entrepreneurs bridge that gap. Together, they unpack the risks of relying on AI speed over deep understanding, the urgent need to treat financial literacy as a public health imperative, and the power of authentic storytelling to cut through digital noise.
Sep 23
1 hr 10 min
In This EpisodeLuther Maday, CEO of Stablecoin Partners and Head of Partnerships at Notabene, joins host Rory Holland on Mighty Finsights for an exploration of aviation, digital assets, and leadership. Drawing parallels from his experience as a private pilot, including the heart-stopping moment when he induced a tailspin in flight training, Luther breaks down how meticulous preparation, checklist discipline, and managing risk translate directly to navigating financial technology. From growing up as an expat across the Middle East to drafting landmark stablecoin legislation in Georgia, Luther offers a candid look at the evolution of money movement. The conversation opens up real-world use cases like cross-border refugee aid, corporate treasury optimization, and travel rule compliance, while reflecting on the human side of leadership, empathy, and grace in business.Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Luther Maday - Stablecoin Partners - Notabene
Sep 4
1 hr 4 min
Host - Zac Garver- CSTMR- CSTMR LinkedInInterviewed - Romina Gomez- CSTMR- CSTMR LinkedIn Brendan Bresnahan- CSTMR- CSTMR LinkedInIn This EpisodeCSTMR team members Zac Garver, Romina Gómez, and Brendan Bresnahan break down Google’s recent documentation on optimizing websites for generative AI features. As search behavior shifts and AI overviews reduce traditional website click-through rates, the group discusses why chasing short-term tactics or writing for algorithms instead of humans fails. They explore how foundational SEO practices remain essential for generative engine optimization and answer engine optimization, highlighting the importance of original, non-commodity content rooted in first-hand experience. By moving away from hyper-focusing on immediate clicks and exact-match keywords, businesses can build a durable, holistic Discovery Optimization strategy across search, social, and earned media.
Aug 17
40 min
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Alex Preece - Tillo - Tillo LinkedInIn This EpisodeWhat 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.
Jul 31
1 hr
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Mary Ann Miller - Prove - LinkedIn: ProveIn This EpisodeCyber 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.
Jul 13
53 min
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Dori Yona- simpleclosure.com - LinkedIn: SimpleClosureIn This EpisodeDori 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 .
Jun 18
49 min
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Charles Rosenblatt - butterpayments.com - LinkedIn: Butter PaymentsIn 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.
Jun 3
55 min
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Colton Pond - socure.com / fintechnerdcon.com - LinkedIn: SocureIn 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.
May 13
48 min
Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Bill Bloom - dianemoney.com - LinkedIn: Diane MoneyIn 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.
Apr 23
59 min
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