A couch is an economical place to establish a customer-service department. In 2003, John Prince’s San Diego apartment supplied one. Tim Hentschel answered customers there; Prince wrote the software. Between them sat a rather less domestic ambition: make booking hotel rooms for a group easier than a prolonged exchange of calls, bids and paperwork.
The arrangement had the advantage of clarity. “He was customer service sitting on my couch, and I was the programmer,” Prince recalled. There was no need for an organizational chart. Everyone could presumably hear everyone else.
Today Prince is HotelPlanner’s co-founder and co-CEO. The job has grown to encompass a product roadmap, technology teams and a business serving travelers across borders. The original attraction remains recognizable: find a troublesome piece of the booking process, then build something that helps people get through it.
A checkbox, then a career
Prince grew up in Maine. Computers caught his attention early, when the family PC was slow enough to invite investigation. He took an interest in its components as well as its software. The curiosity preceded any polished notion of becoming a technology executive.
Choosing a college subject was less preordained than the finished biography might suggest. He has recalled weighing accounting and mathematics before selecting computer science. He liked computers, although some fellow students arrived knowing more programming. A checkbox on an application had become a commitment to catch up.
At Northeastern University, he studied computer science with a mathematics minor and graduated magna cum laude. Engineering work at IBM and Capital One followed. Those employers supplied experience inside established organizations before he began building a company whose early development department consisted of himself.
For HotelPlanner’s first few years, Prince was its sole software developer. That is a specific sort of responsibility. Product decisions eventually have to become functioning software; in those days, there was one person to do the translation. His later executive title sits on top of that practical beginning.
The awkward arithmetic of a group trip
The opportunity was hiding in a familiar inconvenience. Booking one room had become a workable online transaction. Arranging a block of rooms still required dealing with hotel sales teams, collecting offers and comparing terms. A wedding party or sports team could generate rather more administration than its organizer had volunteered for.
Hentschel brought a hospitality background. Prince brought the ability to build the machinery. Their original model allowed hotels to compete for a group’s business, reversing the direction of the bidding. Instead of asking an organizer to conduct a separate negotiation everywhere, the platform gathered hotel offers around the request.
The original idea / simplified
Dates, destination and a block of accommodation.
Properties bid for the group’s business.
Compare the options and arrange the stay.
There is a useful modesty to the problem itself. Nobody organizing a reunion sets out hoping for an absorbing new hobby in hotel procurement. The reward is a booking that leaves time for the actual occasion. Prince’s contribution was to help turn that repeated, cumbersome task into a product.
The partnership also gave the product somewhere to go. Hentschel knew the industry’s working habits; Prince could build around them. In Hentschel’s later account of their relationship, mutual trust and respect over more than twenty years mattered to the company’s growth. Complementary skills are easier to list than to keep working together for that long.
A different coast, a wider map
In 2010, the founders chose West Palm Beach after looking at several Florida locations. International working hours, access to the local business community and quality of life all figured in the move. Prince, who had once worked as a commercial fisherman, had made another change of coast.
HotelPlanner acquired Meetings.com in 2012. International operations developed too, with offices including London and Hong Kong. The apartment business was acquiring a geography.
By 2023, Hentschel was describing a company that powered group bookings for major travel sites, while also offering individual travelers access to closed-user-group rates. The original group-booking specialty had become a foundation for a wider service. The technical work needed to travel along with it.
Sports make the usefulness particularly visible. Teams and leagues travel repeatedly; an event has a location and a date whether the accommodation has been sorted out or not. HotelPlanner’s relationship with USA Archery illustrates the sort of organization the booking system serves. A reservation platform may be digital, but the people eventually have to arrive somewhere.
The listing that did not happen
The corporate story contains a conspicuous change of plan. In August 2021, HotelPlanner announced a proposed three-way combination with Reservations.com and Astrea Acquisition Corp., a special purpose acquisition company. The transaction would have taken the combined business public. Prince was designated to serve as chief information officer.
The plan included spending on technology, artificial intelligence, machine learning, travel-agent onboarding and acquisitions. It was a statement about the business the executives wanted to build as well as a proposed route to financing it.
On February 14, 2022, the parties announced that they had mutually agreed to terminate the combination. The listing envisaged in those earlier interviews did not follow from that deal. It is an essential turn in the chronology, especially when watching Prince discuss the company’s future in material recorded during 2021.
Prince and Hentschel establish HotelPlanner in San Diego.
A proposed public-market combination is announced, then terminated.
The founders win EY’s Florida award and become national finalists.
HotelPlanner reports an Inc. 5000 ranking of 917.
The subsequent business has its own measurable record. Travel Weekly’s 2024 Power List recorded HotelPlanner’s 2023 sales at $685 million, up from $350 million in 2022. Those are company sales figures for particular years. They give the next chapter substance without turning an abandoned transaction into a completed one.
A voice on the other end
Prince’s interest in voice booking was already public in 2021. He described an Alexa feature that collected a traveler’s destination and stay dates, then passed that information to a human booking agent. The handoff mattered: the customer would not have to explain the same request all over again.
It was an incremental product, and Prince described it that way. The initial version gathered information and connected the caller to an agent; further capabilities were ambitions for later iterations. Even in a technology interview, there was room to say where the working product stopped.
The later AI work develops that interest in spoken reservations. Prince has described using the experience of human booking conversations to help train the system. The challenge includes timing and understanding what a caller needs, alongside the mechanics of making a booking. A fluent voice still has to get the travel details right.
There is a pleasing continuity here. In the apartment, one founder handled customers while the other built software. Years later, the engineering problem still involves getting a conversation and a reservation to cooperate. The furniture has become less central to the operation.
What the awards actually mark
In June 2025, EY named Prince and Hentschel among its Entrepreneur Of The Year Florida winners. An independent judging panel considered growth, long-term value creation, entrepreneurial spirit and impact. Later that year, the pair appeared among the national finalists in technology, media and telecommunications.
The recognition gave a public marker to a partnership dating back to 2003. It also placed them alongside founders and executives from other industries, outside the narrower circuit of hotel-booking technology.
Another marker arrived in April 2026, when HotelPlanner announced a USA TODAY Top Workplaces award. That program uses confidential employee feedback collected by Energage. Prince’s response focused on engineering: giving people the ability to explore, adopt and build with newer technology, including AI.
The change in responsibility is worth considering. A sole developer can make the next improvement directly. A co-CEO must also help other people do the work. Prince’s emphasis on giving engineers room to experiment suggests how he describes that part of the job.
Still making room
In August 2026, HotelPlanner announced a ranking of 917 on the Inc. 5000, with 370% three-year revenue growth. Prince connected the growth to investment in people, AI and an expanding range of travel experiences. He described packages including hotels, air travel, car rental, event tickets and activities.
Three-year revenue growth reported by HotelPlanner, which announced No. 917 on the 2026 Inc. 5000.
Company-level figures. Revenue growth period: 2022–2025.“We have so many opportunities ahead.”
John Prince / August 2026
The scope has widened considerably from a block of hotel rooms. His stated direction is to bring more pieces of a trip into the offering while continuing to invest in the people and technology behind it. That is an aspiration with a recognizable connection to the original work: reduce the number of arrangements a traveler must assemble separately.
Prince’s career has accumulated titles, awards and a much larger business. Its most memorable image remains the small one: a programmer at work, his business partner on the couch, customers already needing help. An enterprise requires many things as it grows. In the beginning, it is useful if someone answers the call.