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.
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 distribution
03:30 – Product vs distribution: what actually matters early
06:45 – Why most startups fail from internal misalignment
10:30 – Culture, communication, and focus as scaling constraints
14:40 – Hybrid work broke alignment
17:45 – Why offsites are becoming the new HQ
21:30 – Events as a go-to-market strategy
25:00 – AI, outbound fatigue, and inbox trust collapse
28:40 – “In-person experiences are becoming a premium”
32:30 – How to use events for customer and partner acquisition
36:15 – What makes a high-impact event vs a wasted one
39:50 – Dinners, summits, and unforgettable experiences
43:30 – Leadership, kindness, and “don’t be a jerk”
47:40 – Mental state as a competitive advantage
52:30 – Final reflections and advice for founders
Sponsors:
HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com
Guest 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: https://gtmnow.com
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The GTMnow Podcast 
