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 Sinnarajah

(3:24) From PayPal Intern to Founding Highnote

(8:45) What Makes Payments So Compelling

(13:17) Security as the Bedrock of Fintech

(18:10) What Highnote Does and Who It Serves

(25:26) Conversational Commerce and Agent-to-Agent Payments

(33:10) The Economics of Agentic Payments

(37:58) Building an Engineering-Driven Company

Follow Shayanth Sinnarajah
LinkedIn: https://www.linkedin.com/in/ssinnarajah/

Follow Eli Wachs
LinkedIn: https://www.linkedin.com/in/eliwachs/

Check out Footprint
https://www.onefootprint.com

Footprint is an AI-native platform powering identity verification, fraud prevention, and AI fincrimes agents for banks and fintechs.

In this episode of Risk and Reason, Eli Wachs sits down with Zach Trunsky, Founding Business Operations at Comun, to explore how early-stage fintechs build fraud and risk programs from the ground up. Drawing on his experience at Capital One, Mercury, and now Comun, Zach shares why zero fraud losses is an unrealistic goal, how fraudsters operate as sophisticated full-time professionals, and why the era of massive BPO review teams may be coming to an end.

Chapters

(0:00) Can You Actually Eliminate All Fraud?

(1:25) From Capital One Intern to Founding Risk Hire

(5:42) The Cat-and-Mouse Game With Fraudsters

(11:15) Why Zero Fraud Means Zero Revenue

(18:25) AI as a Weapon on Both Sides

(24:06) Why BPOs Are Holding Fintechs Back

(27:38) Rating BPOs vs. AI Copilots

(33:11) Advice for New Risk Leaders and 2026 Predictions

Follow Zach Trunksy
LinkedIn: https://www.linkedin.com/in/zach-trunsky-436879125/

Follow Eli Wachs
LinkedIn: https://www.linkedin.com/in/eliwachs/

Check out Footprint
https://www.onefootprint.com

Footprint is an AI-native platform powering identity verification, fraud prevention, and AI fincrimes agents for banks and fintechs.

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, prudent risk taking, and why operations is often the most underrated competitive advantage in fintech.

Chapters

(0:00) Incentives, Growth, And Fraud Tradeoffs
(1:03) From Military Intelligence To Fintech Operations
(4:28) Aviation Lessons On Risk, Buffers, And Failure
(8:43) Why Operations Is A Startup Superpower
(14:55) Mission Command And Prudent Risk
(18:30) Scaling Fraud And Compliance The Right Way
(29:35) Rapid Fire: Metrics, Discipline, And Dub’s Advantage

Follow Brett Chereskin

LinkedIn: https://www.linkedin.com/in/brettchereskin/
X (Twitter): https://x.com/bchereskin

Follow Eli Wachs
LinkedIn: https://www.linkedin.com/in/eliwachs/

Check out Footprint
https://www.onefootprint.com

Footprint is an AI-native platform powering identity verification, fraud prevention, and AI fincrimes agents for banks and fintechs.