#138 Healey Cypher on Loneliness, Human Connection, and Building BoomPop

May 27
40 mins

Episode Description

Healey Cypher is CEO and co-founder of BoomPop, a company using AI to help teams plan and host meaningful in-person events. A 4x founder, former COO at Atomic, and former Head of Retail Innovation at eBay, Healey has built and sold companies across commerce, retail tech, and event experiences.


In this episode, Healey shares why he believes the loneliness epidemic is one of the most urgent problems of our time, and how BoomPop is tackling it by making it easier for people to gather in real life. He explains how AI can serve human connection rather than replace it, and why building a company around a mission that matters is what keeps pulling him back to founding.


Healey also opens up about his leadership philosophy: the practice of asking "what would make my son Theo proud" as a decision-making filter, the power of vulnerability in authentic networking, and what four companies have taught him about culture, trust, and staying grounded as a leader.


If you are building, leading, or simply trying to be a better person while doing it, this conversation is for you.


About Healey Cypher 🚀🤝

CEO and Co-Founder of BoomPop | 4x Founder | Board Partner at Atomic

- 💼 https://www.linkedin.com/in/healeycypher/

- 🌐 https://boompop.com/


About Federico Ramallo ✨👨‍💻🌎

🚀 Software Engineering Manager | 🛠 Founder of DensityLabs.io & PreVetted.ai | 🤝 Connecting 🇺🇸 U.S. teams with top nearshore 🌎 LATAM engineers

- 💼 https://www.linkedin.com/in/framallo/

- 🌐 https://densitylabs.io

- ✅ https://prevetted.ai


🎙 PreVetted Podcast 🎧📡

- 🎯 https://prevetted.ai/podcast

- 🐦 https://x.com/PrevettedPod

- 🔗 https://www.linkedin.com/company/prevetted-podcast



00:00 Introduction to Hailey Cypher and Boom Pop

02:46 The Loneliness Epidemic and Human Connection

05:50 Networking and Authentic Conversations

06:49 The Creative Process of Building Companies

09:43 The Impact of Leadership on Lives

12:46 The Journey of Co-Authoring a Book

18:57 The Burden of Leadership

20:29 Purpose Beyond Profit

21:39 Introspection and Personal Growth

23:27 The Pain of Migration

25:50 Creating a Trusting Company Culture

29:26 Values in Decision Making

32:33 Balancing Life and Work

35:06 The Importance of Family

37:55 Privilege and Choices

40:15 Final Thoughts on Success


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