What we talked about
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.
Show notes
Healey Cypher describes BoomPop as an “anti-AI AI company”, one that uses artificial intelligence exclusively to get people together in real life. His motivation for founding it came from a striking statistic: 79% of 18-to-24-year-olds report feeling lonely, a number that crystallized for him what he calls the most important problem a company could try to solve.
What we covered
- Healey identifies loneliness as the core market opportunity behind BoomPop, arguing that despite digital connectivity, humans are more isolated than ever, and that coming together in person is “primordial”, the trait that made humans the dominant species. BoomPop’s AI agent handles the full event workflow: planning, negotiating, booking, building a website, and communicating with guests, so the friction of organizing an event never stops people from showing up.
- On breaking through transactional networking, Healey described opening a dinner conversation the previous night by sharing that he and his wife had struggled to have children. The other person immediately “sunk down” and they spent 30 minutes in genuine connection, his point being that vulnerability in the first three minutes sets the entire tone of a relationship, far more effectively than leading with accomplishments.
- His third company built the touchscreen ordering kiosks you see at McDonald’s, Burger King, and Wendy’s, he deployed them across the top 40 quick-serve restaurant chains before selling that business. He describes each company as “the ultimate form of creative expression,” funded by people who hand you money to build something you believe should exist in the world.
- On company culture, BoomPop runs a weekly “Unicorn Award” where one employee publicly tells a story about a colleague that connects to a company value, then passes the award on. Performance reviews formally rate employees on their values alongside their output, creating accountability that keeps principles off the wall and in daily practice.
- Healey’s personal decision-making compass is his son Theo. When he is unsure about a choice, he asks himself whether Theo, finding out about it later, would be proud of his father. He frames this as “full stack values”, company-level values and personal values should align, and if they don’t, he says, “don’t do that job.”
- He described doing a creative visualization exercise, imagining himself at age 80 or 90 at the end of his life, and realizing that what mattered most was his wife, his children, his parents, and his community, not his company’s milestones. He uses that realization to hold a hard line on not missing his kids’ recitals or his wife’s birthday, even while running an aggressive, VC-backed company.
About Healey
Healey Cypher is a four-time founder and CEO of BoomPop, an AI-powered platform designed to eliminate the friction of organizing in-person events. He previously served as COO at Atomic and Head of Retail Innovation at eBay, and his prior company built self-service kiosk systems deployed in the top 40 quick-serve restaurant chains across the US.
- LinkedIn: https://www.linkedin.com/in/healeycypher
- Website: https://boompop.com
Episode 138 of the PreVetted Podcast.