EPISODE · May 27, 2026 · 40 MIN
#138 Healey Cypher on Loneliness, Human Connection, and Building BoomPop
from PreVetted Podcast · host Federico Ramallo
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-podcast00:00 Introduction to Hailey Cypher and Boom Pop02:46 The Loneliness Epidemic and Human Connection05:50 Networking and Authentic Conversations06:49 The Creative Process of Building Companies09:43 The Impact of Leadership on Lives12:46 The Journey of Co-Authoring a Book18:57 The Burden of Leadership20:29 Purpose Beyond Profit21:39 Introspection and Personal Growth23:27 The Pain of Migration25:50 Creating a Trusting Company Culture29:26 Values in Decision Making32:33 Balancing Life and Work35:06 The Importance of Family37:55 Privilege and Choices40:15 Final Thoughts on Success
What this episode covers
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-podcast00:00 Introduction to Hailey Cypher and Boom Pop02:46 The Loneliness Epidemic and Human Connection05:50 Networking and Authentic Conversations06:49 The Creative Process of Building Companies09:43 The Impact of Leadership on Lives12:46 The Journey of Co-Authoring a Book18:57 The Burden of Leadership20:29 Purpose Beyond Profit21:39 Introspection and Personal Growth23:27 The Pain of Migration25:50 Creating a Trusting Company Culture29:26 Values in Decision Making32:33 Balancing Life and Work35:06 The Importance of Family37:55 Privilege and Choices40:15 Final Thoughts on Success
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#138 Healey Cypher on Loneliness, Human Connection, and Building BoomPop
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