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 helps fintechs and banks verify identity, prevent fraud, and manage compliance with end-to-end onboarding and risk infrastructure.