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

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 advantageHealey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world.Timestamps:00:00 – Why founders underestimate distribution03:30 – Product vs distribution: what actually matters early06:45 – Why most startups fail from internal misalignment10:30 – Culture, communication, and focus as scaling constraints14:40 – Hybrid work broke alignment17:45 – Why offsites are becoming the new HQ21:30 – Events as a go-to-market strategy25:00 – AI, outbound fatigue, and inbox trust collapse28:40 – “In-person experiences are becoming a premium”32:30 – How to use events for customer and partner acquisition36:15 – What makes a high-impact event vs a wasted one39:50 – Dinners, summits, and unforgettable experiences43:30 – Leadership, kindness, and “don’t be a jerk”47:40 – Mental state as a competitive advantage52:30 – Final reflections and advice for foundersSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.comGuest links:Instagram: https://www.instagram.com/healeycypher/?hl=enHealey’s podcast: https://www.dontbeajerkpodcast.com/Mentioned Resources:Host (Sophie Buonassisi) links:X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comHost (GTMnow) links: The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.