What if AI didn’t keep us on screens… but actually got us together in real life more often?

In this episode of the Everything AI in Travel podcast (now sitting in the top 3 travel-technology podcasts on Apple Podcasts), Tony sits down with Healy Cypher, co-founder & CEO of BoomPop, a company that just raised $25M to make planning in-person events, offsites and group travel radically easier with AI.

We dig into Healy’s wild founder journey — from growing up in Saudi Arabia, to selling his first startup to eBay just seven months after joining, to rolling out those touchscreen kiosks in McDonald’s, Wendy’s and more (including the legendary “temptation cookie” upsell)… and why all of that led him to build BoomPop.

Then we zoom out to the big shift: post-pandemic hybrid work, half-empty offices, and $1.7T in “freed” office spend that companies are quietly redirecting into in-person experiences, offsites, sales kickoffs and client events. Healy explains why group travel & meetings are the last undigitised corner of travel, and why AI is finally the unlock.

You’ll hear how BoomPop uses AI to:

• Turn a simple prompt (“Offsite within 2 hours of SF in Q1, X budget, Y vibe”) into venue options, dates, full itineraries and a live event website

• Match corporate events with hotel “need dates” so everyone wins on price and occupancy

• Learn a “taste graph” for organisers and companies to recommend better venues and experiences over time

• Handle all the messy coordination: negotiations, blocks, RSVPs, guest messaging, packing lists, dinner changes and more
  — plus how a 35-person human planning team plugs in when you need a real expert, not just an agent.

We also talk about the future of event agencies and travel advisors in an AI world, the incumbents like Cvent and the old-school RFP process, and what a new competitive landscape looks like when AI-native platforms start hitting escape velocity.

If you’ve ever:

• Burned months of an EA’s time on a single annual offsite

• Run a remote or distributed team that lives for its one big IRL gathering

• Worked in hotels, DMOs, or meetings & incentives and wondered “why is this still done by fax and spreadsheets?”

…this conversation will be painfully familiar and seriously hopeful.

🎧 Listen now to learn how AI, group travel and in-person experiences collide — and why this is one of the ripest opportunities in travel tech.

👤 Guest
Healy Cypher – Co-founder & CEO, BoomPop
BoomPop: AI-powered platform for offsites, retreats & corporate events
Podcast: Don’t Be a Jerk – conversations with high-performers who prove you can win in business without being an asshole.

📌 If your team has an offsite, retreat or client event coming up
Before you sacrifice six months of someone’s job to planning it… check out BoomPop and see what AI can take off your plate.

👍 If you enjoy this episode:

• Subscribe to the channel

• Drop a comment with your biggest takeaway

• Share it with someone who organises events and desperately needs their life back

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