Risk and Reason

In this episode of Risk and Reason, Eli Wachs sits down with Ethan Singleton, Partner at FS Vector, to talk about what it really takes to launch and scale fintech products in today's regulatory environment. Drawing on years advising both banks and fintechs — from HSBC to FS Vector's build-focused advisory practice — Ethan shares how AI is reshaping compliance operations, where stablecoins actually have legs, and why the best fintechs plan far beyond their first product. Chapters (0:00) Fintec...

In this episode of Risk and Reason, Eli Wachs sits down with Shayanth Sinnarajah, Founding Engineer at Highnote, to talk about what it takes to build payments infrastructure from the ground up — and where it's all headed. Drawing on over a decade building at PayPal and Highnote, Shayanth shares why security has to be your first product decision, how stablecoins reshape cross-border payments, and why the future of commerce is agent-to-agent. Chapters (0:00) Introduction — Who Is Shayanth Sinna...

In this episode of Risk and Reason, Eli Wachs sits down with Brett Chereskin, COO of Dub, to unpack how real fintechs think about risk, fraud, and operational discipline at scale. Drawing on his background in military intelligence and aviation, Brett shares why incentivized growth attracts fraud, how attackers probe systems before striking at scale, and why early stage companies must calibrate risk based on what they can actually monitor. The conversation explores mission driven leadership, p...

In this episode of Risk and Reason, Eli Wachs sits down with Jason Brown, Director of Risk Operations at Imprint and former U.S. Secret Service agent, to explore the evolution of cybercrime and financial fraud. Drawing on nearly 25 years in federal law enforcement, Jason discusses the professionalization of fraud networks, why fraud is fundamentally human, and how AI can act as a force multiplier without replacing human judgment. The conversation also covers synthetic fraud, payment rails, st...