Designing high ROI offsites

Healey covers planning, pacing, intentional programming, and avoiding overscheduling for better event outcomes.

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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.

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