After leaving a long sales career, David Rubenstein 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