Darryl Hicks, CEO of Flexpay | Episode 396

Darryl Hicks, founder and CEO of FlexPay, takes us behind the scenes of a problem costing subscription businesses millions each month – failed payments and the resulting involuntary customer churn.

From his early days cleaning toilets in his parents' commercial cleaning business to consulting for major telecom companies in the Twin Towers, Darryl shares his unique journey to founding a company that's now processing billions of transactions using sophisticated AI. What began as a solution he built for his own subscription businesses has evolved into a mission to fundamentally transform how payments work.

FlexPay stands apart through deep partnerships with financial institutions, sharing crucial data that has traditionally been siloed between merchants and issuers. This approach allows their machine learning models to continuously improve. For subscription businesses experiencing millions in monthly failed payments, even small improvements in recovery rates translate to substantial revenue.

The conversation reveals how payment system opacity creates unnecessary friction for legitimate commerce. When issuing banks make decisions without transparency – whether declining transactions due to suspected fraud or based on undisclosed policies against certain merchant categories – both businesses and consumers suffer. 

While excited about innovations like stable coins, Darryl remains pragmatic about the future of payments: "I would not bet against Visa and Mastercard." Rather than trying to replace traditional rails, he's focused on reducing friction within existing systems through better data sharing and transparency. For entrepreneurs, he emphasizes the importance of building strong advisory boards and following your natural passions.