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.

In this episode of Risk and Reason, Eli Wachs is joined by Phil Goldfeder, CEO of the American FinTech Council and former New York State Assembly member, to explore how trust, regulation, and innovation intersect in modern banking. Phil shares how leading through Hurricane Sandy shaped his views on financial access and why fintech plays a critical role for underserved communities. They unpack lessons from Silicon Valley Bank and Synapse, the evolving bank fintech relationship, and why fear driven compliance can create more risk, not less. The conversation also looks ahead at AI in compliance and what it will take to build resilient financial systems without sacrificing consumer protection.

Chapters

(0:00) Intros
(2:00) Phil’s Path From Public Service
(5:10) Hurricane Sandy And Financial Access
(9:30) Banking Access Gaps And Consumer Demand
(12:20) Balancing Innovation And Protection
(14:54) Bank Closures And Fintech’s Role
(19:20) Trust, Crises, And Bank Fintech Partnerships
(25:00) Lessons From SVB, Synapse, And Consent Orders
(30:20) Building Compliance Muscle In Fintech
(34:00) Convening Banks, Fintechs, And Regulators

Follow Phil Goldfeder

LinkedIn:
https://www.linkedin.com/in/philgoldfeder

X (Twitter):
https://x.com/YPGoldfeder

American FinTech Council Website:
https://www.fintechcouncil.org

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 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, stablecoins, and what the future of risk management looks like in an increasingly digital economy.

Chapters

(00:52) Meet Jason Brown And His Background
(03:44) Building The ECTF And Early Cybercrime
(07:35) Operation Firewall And Carding Markets
(10:06) Teaming Up: Agencies And Corporates
(11:52) AI’s Role And Human Oversight
(14:58) Fraud As A Human-Driven Problem
(17:40) Specialization In Criminal Marketplaces
(19:15) Mule Accounts And Money Movement
(21:06) Secret Service Mandate And Focus
(23:13) New Rails: Stablecoins And Protocols
(24:26) Startups, Speed, And Risk Innovation
(25:19) Why Blockchain Traceability Matters
(27:42) Career Moments And Closing

Follow Jason Brown

Jason's LinkedIn:
https://www.linkedin.com/in/jason-brown-1a6054ba/

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.

Ryan Hunter (Director of Identity & Fraud Strategy at Built Rewards) joins Eli to unpack how fraud is evolving fast — from synthetic identities to first-party scams and global fraud rings that operate like real businesses. They dig into why legacy ID systems keep failing, where the biggest vulnerabilities live today, and what it will take to actually shift the playing field.

Chapters

(00:00) Ryan’s path into fraud strategy

(05:53) How fraud evolved: fake IDs → synthetic → first-party

(10:21) Why SSNs are a broken identifier

(16:38) First-party fraud, credit washing, and detection gaps

(23:29) Fraud’s hidden cost to every consumer

(25:11) Review decisions: phishing, recovery, mule accounts

(29:47) Why fraud stays interesting + geopolitics of fraud rings

Key takeaways

• Fraud hits everyone through higher rates and product costs
• Synthetic + first-party fraud now outpace classic third-party fraud
• Weak national ID infrastructure still fuels modern attacks
• Mule accounts and phone takeovers are major failure points
• Fraud rings are organized, coordinated, and often state-level
• Stopping fraud would unlock huge UX gains across industries

Follow Ryan Hunter

Ryan's LinkedIn: https://www.linkedin.com/in/ryanrussellhunter/

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.