GTM: Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop

Episode notes

Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events. As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition. In this episode, we discuss: - Why in-person events are becoming a premium GTM channel in an AI-first world - How founders can de-risk distribution before building the product - The most common internal missteps that derail startups early - Why offsites are the new HQ for remote and hybrid teams - How to design offsites that drive alignment, not just fun - What makes a dinner actually work — including overlooked details like acoustics - How teams use events for customer acquisition and partnerships - Why kindness and positivity can be a real leadership advantage Healey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.