Your Best Customers Are Costing You Too Much. Now What? Anthony Pompliano

Anthony Pompliano built an AI financial assistant people loved. Then his most engaged users started costing him too much money. That’s a good problem to have. But it’s still a problem. His solution came from an unlikely place. Olive Garden’s breadsticks. Here’s how Silvia cut costs without cutting what users love, and got 25% of monthly active users to pay. Find Anthony's book here! This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness. Jason wants to help solve your impossible problem! Click the link below to sign up: https://entm.ag/levelup2026 Timestamps: 0:00 Intro 0:38 The idea of a “better problem” 2:05 Anthony’s book, How to Live an Extraordinary Life Volume Two 5:00 Silvia’s power-user problem 6:50 The Olive Garden breadstick lesson 9:15 Weighing every possible fix 11:07 Building a model router 12:55 Bracketing: a military trick for making decisions 16:50 Experiments vs. archaeology 18:15 Training their own model (97% cheaper) 19:10 Rolling out the paywall 20:40 Why people pay 21:45 How to spot this problem in your own business 24:16 Where to find Anthony and Silvia Learn more about your ad choices. Visit megaphone.fm/adchoices