Six things we learned from Bobby Healy at the Founder Fireside Chats at Stripe in Dublin

Thanks to our Dublin Travel Massive community who joined our Founders Fireside Chat at Stripe’s stunning new Wilton Park offices for an evening of insights and lively discussion. Stripe generously supported the event with craft beers and gourmet sandwiches, setting the tone for a relaxed but inspiring evening.

Here’s a recap from what we learned at the event, and some photos from the evening.

The evening began with Chapter Co-Leader Kevin O’Shaughnessy warming up the crowd by inviting John Maguire (CEO, TripAdmit) and Gavin Rooney (CEO, AnotherTrip HQ) to the stage to shoot the breeze. Both startups are recent participants in NDRC, Ireland’s national accelerator for high-growth tech companies.

• TripAdmit (2019 cohort) helps tour and activity providers sell online, with solutions for managing digital tips, and collecting reviews. A key customer is Gray Line - a global leader in sightseeing tours and activities.
• AnotherTrip HQ (2025 cohort) enables creators and operators to turn travel content into bookable experience maps.

Their conversation with Kevin offered a fascinating look at how Irish startups are redefining travel technology.

Interview with Bobby Healy

Once arrived (straight from the airport, no less!), Bobby Healy took the stage. Bobby’s remarkable entrepreneurial story spans many chapters including building Nintendo video games, founding Eland Technologies (later sold to SITA), and starting CarTrawler, the world’s largest mobility marketplace for airlines.

Bobby is now leading Manna, a “Drone Delivery as a Service” and Meili, an unapologetic competitor to Cartrawler, that focuses on smarter, leaner tech and less overhead.

Healy believes Manna’s drone technology can take on Amazon in the race for last-mile delivery, whether that’s a coffee from an independent cafe or a book from a local bookstore. When asked about use cases, he admitted coffee is adoption fuel for drone delivery.

Bobby was interviewed by James Lemon, who leads Stripe’s global growth across hospitality, travel, leisure, and transport. Lemon’s own experience (founder of Otolo, and leadership roles at IHG, Hostmaker, and Travelport) made him an ideal host for the conversation.

So, what did we learn? Bobby shared candid reflections on building companies, technology choices, and the future of travel:

• On Meili vs. CarTrawler: Owning the consumer came at huge cost (e.g., fraud, call centres, and customer management). Meili is designed to change that, with 48 people doing what once required 600.
• On Build vs. Buy: “Buy for market expertise or speed. But if it’s just a tech problem—build.” Manna outsources components and some software, as the key metric is time to market.
• On B2B vs. B2C: Focus on B2B for faster revenue; you don’t need huge capital to build travel tech.
• On Building in Ireland: “We can create billion-dollar companies here,” he said, praising Enterprise Ireland for its support.
• On Talent Acquisition: “Look around—how many women are in this room?” (the answer was “four” which is very unusual for a Travel Massive Dublin Chapter event). He noted Meili’s team is over 50% women and stressed the need for more programs to attract young talent, even before college.
• On the Future: Optimistic—citing the drop in compute costs, tech’s impact on healthcare, and global economic growth.

Taking questions from the floor, Chapter Co-Leader Amanda Campbell (T2RL) asked about an AI bubble. Bobby acknowledged “some punchy valuations” and warned that “there isn’t a future until we solve the energy problem.”

Ultan O’Brien (Airportr) turned to car hire, asking why it is still so frustrating for customers. Bobby cited “a race to the bottom on price” and “too much fragmentation”, but noted brands like Enterprise and Sixt are improving loyalty and experience.

— Thanks to everyone who attended and supported the event!

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