Why AI Made Your Buyers Harder to Sell To

After leaving a long sales career, David Rubinstein spent a year meeting more than 300 founders across 41 countries and turned what he heard into a framework for how companies sell now. In this episode of Founded & Funded, David sits down with Madrona's Anna Baird and Eric Wong to dig into why AI left buyers with more information and less clarity, why deals stall out of fear rather than disinterest, and how founders can cut through. The conversation covers selling against build-it-yourself AI objections, the return of in-person selling, and why the founder's own brand is more important to drive pipeline. This was originally an AMA with Madrona portfolio companies, but we wanted to share David's full sales playbook with founders, GTM leaders, and operators for a grounded look at how buying behavior shifted and where to focus when the old tactics stop paying off. Full Transcript: Chapters 00:00 – Why AI Made Your Buyers Harder to Sell To 01:30 – How David Met 300 Founders Across 41 Countries in a Year 03:06 – Why the Old Go-to-Market Math Stopped Working 04:40 – AI Gave Buyers More Information and Left Them More Confused 05:27 – The SPRINT Framework for Diagnosing a Stalled Deal 07:03 – Give the "How" Before the Number So Results Read as Proof 08:54 – The Question Every Executive Buyer Asks Late in a Deal 10:16 – 3 Hidden Fears That Kill Deals During Implementation 12:00 – The Trigger Most Founders Leave Out of Their Customer Profile 15:24 – Why the First Seven Minutes of a Sales Call Are Wasted 16:19 – How to Sell Against "I'll Just Build It With Claude Code" 22:24 – Why AI Sales Prep Gives You the Average, Not the Edge 25:48 – Why Founder Brand Now Drives Pipeline 28:50 – Free vs. Paid Pilots and Why Skin in the Game Wins David's website: https://daverubinstein.com/ and ‪@100-Founders‬