Problem Solvers
Problem Solvers
Entrepreneur Media
Your Best Customers Are Costing You Too Much. Now What? Anthony Pompliano
25 minutes Posted Oct 19, 2026 at 7:00 am.
Intro
The idea of a “better problem”
Anthony’s book, How to Live an Extraordinary Life Volume Two
Silvia’s power-user problem
The Olive Garden breadstick lesson
Weighing every possible fix
Building a model router
Bracketing: a military trick for making decisions
Experiments vs. archaeology
Training their own model (97% cheaper)
Rolling out the paywall
Why people pay
How to spot this problem in your own business
Where to find Anthony and Silvia
0:00
25:31
Download MP3
Show notes
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:
Learn more about your ad choices. Visit megaphone.fm/adchoices