Declined Payments: Why 39% Of Shoppers Walk Away | Jack Cregan, Co-Founder & CEO at Paymend

39% of shoppers whose card is declined at checkout don't come back. The merchant paid to get them to the checkout page, and the sale is lost, that’s a problem! This week I speak with Jack Cregan, Founder of Paymend, and we discuss recovering declined payments Paymend gives merchants a second network once its own processors have failed a payment, opening up another 12 or 15 acquirers and routing each transaction by how the customer's issuer has performed with each one. For subscriptions, Paymend holds a failed payment for generally 30 days and bills when the card schemes signal that funds are available again. This one is for the founder or CPO who is watching paying customers get declined at checkout and has no idea how many of those sales are recoverable. What you'll learn Why 39% of declined shoppers at checkouts don't come back, and why that wastes the money already spent to win them Why a failed payment can still be approved by a second network of acquirers after your own stack gives up How routing by each issuer's history with each acquirer changes which payments get approved Why subscription declines are recovered by holding the payment for 30 days and billing when funds are available Why insufficient funds is the decline merchants can't see into, and why blind retries on paydays are the best they can do alone How to test a payments idea with real merchants before you build it Who is liable when an AI agent's payment turns out to be fraud, and why nobody knows yet Timestamps 00:00 — Cold open: what a declined card does to a customer 02:13 — Why cards get declined in the first place 03:15 — The 39% who don't come back 08:57 — How a second network of acquirers recovers failed payments 12:34 — Subscription declines and the 30-day recovery window 16:15 — Why insufficient funds is the decline merchants can't fix alone 19:24 — Founder story: leaning on senior advisors 21:02 — Selling a company and starting again 24:59 — Test the idea with real merchants before you build 29:58 — The bet on insufficient funds, and the AI agent fraud question 31:23 — How the team uses AI, and what it costs 34:18 — The founder mindset: a network of intelligence 👉Connect with Jack: Paymend: https://www.linkedin.com/company/paymend-us/home/ LinkedIn: https://www.linkedin.com/in/jack-cregan-paymend/ 👉Connect with Monica: LinkedIn: https://www.linkedin.com/in/monicamillares/ Purpose Driven FinTech. English: https://www.youtube.com/@monica_millares/videos Purpose Driven FinTech. Spanish: https://www.youtube.com/@MonicaMillares_Español/videos Disclaimer: This episode does not constitute professional nor financial advice and does not represent the opinion nor views of my current, past, or future employers. The guest has agreed to record and release our conversation for the use of this podcast and promotion on social media.