Split decision: New app aims to ease group travel planning, payments

As pandemic restrictions have lifted, travel, accordingly, has experienced a resurgence. Case in point: Revenue from hotel stays in Tampa and Hillsborough County topped $758 million last year, shattering a record set in 2019 by $50 million.

Groups are also traveling again, and as anyone who’s taken part in a destination wedding, bachelor/bachelorette party or other trip involving people outside their immediate family, splitting costs can get complicated.

“I'm at that point in my life where everyone’s getting married, having bachelor parties, going on trips with old friends from high school, from college, all that kind of stuff,” says Chase Harris, co-founder of Takeoff, a new app that aims to make booking and paying for group travel easier. “I was noticing my calendar filling up with these group trips. Flights and lodging [costs] are pretty easy to settle up, but dinners, events, renting a boat, renting a car, whatever you’re doing while you’re on the trip, it can be super hard to keep track of payments. Things just get out of whack.”

‘We found this big ‘white space’ in the concierge industry. There’s no market-share leader.’ Chase Harris, co-founder of Takeoff

Harris, 30, a 2015 University of Florida graduate, says he’d had enough of trying to split bar tabs, restaurant checks and excursion costs so that everyone paid their fair share. So he came up with Takeoff. After a soft launch about nine months ago, he and his St. Petersburg-based team of five formally debuted the service at the Synapse Summit in Tampa in mid-February.

But with less than 100 downloads of the app, to date, and just a handful of itineraries booked, how big is the market for such a service? And how will it effectively compete with the myriad travel booking websites and services that already exist?

First and foremost, Harris says, Takeoff has honed in on a specific gap in the planning process for group travel — namely, the highly fragmented landscape of concierge service providers.

“We focus solely on the itinerary,” he says. “Flights and such, they’re already captured by multiple websites, and then Airbnb, Hotels.com and such, they’ve captured lodging. But we found this big ‘white space’ in the concierge industry. There’s no market-share leader.”

Despite the service being used for just a handful of trips thus far, Harris has already laid the groundwork for a revenue-sharing arrangement with a trip-planning company in Miami and Las Vegas. The company's business model is to generate other revenue-share arrangements. 

“We’re still inking the deal, so I can’t say the name, but they could set up your entire trip — restaurants, nightclubs, maybe you want to book a yacht or a round of golf … they would handle it all for you.”

Where does Takeoff fit in the process? One of the group travel participants acts as the host and, via the app, invites the other members, who are then able to communicate with each other and select potential activities and experiences from four categories to add to the itinerary.

Takeoff, Harris explains, “starts curating your itinerary and breaking it down by cost per person.” He adds, “So, it’s a digestible number, as opposed to a grand total, which can sometimes be a little scary. From there, once you get everything booked and confirmed, you can start making payments, and they can be incremental leading up to the trip.”

Once the first payment is initiated — and anyone can make it, not necessarily the host — Takeoff’s concierge partner enters the picture, getting the itinerary set up and finalized and making contact with the host. The end result, Harris says, is greater control and transparency, with fewer complications, for people who want to travel together.

Takeoff is also about “democratizing the concierge business,” he adds. “A concierge service seems so luxurious, so some people don't want to use them. They think they can do it all themselves, but in reality, it's not that much of a difference, and [Takeoff] is such a headache solver. We’re bringing this idea of concierge-driven trip planning to the everyday person.”

Takeoff, however, still has a ways to go before it really takes off. Harris funded the business for six months with personal savings from a previous job in real estate (he worked for Robert Milligan at Preferred Shore Real Estate in St. Petersburg). It’s currently in a pre-seed funding stage, with a seed round “on the horizon,” he says. “We’re still in deliberations as to how much we want to shoot for, but it’ll be anywhere from $2 million to $3.5 million.”