online-travel
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James Hare knows how to start. The trick is starting again.
He helped build eDreams from a shared desk into a listed business. At Us2.ai in Singapore, James Hare is putting his appetite for partnerships, speed and stubborn persistence to work again.
Priceline sells the power of not knowing.
A hidden hotel name can be worth real money. Priceline built a travel business around that bargain, then spent decades learning which parts to keep.
Roberto Souviron and the value of leaving the queue
A frustrating wait for a plane ticket helped set Despegar in motion. After 18 years running the business, Roberto Souviron brought a familiar question to Argentine education: how do you make a good opportunity available to more people?
Luciano Barreto and the journey after the booking
He helped put Brazilian travel online. Now, as AirHelp’s managing director for Brazil, Luciano Barreto works on what happens when the itinerary comes apart.
Headout sells the afternoon your flight forgot
Flights get you there. Hotels give you a bed. Headout tackles the awkward bit in between: turning an unfamiliar city into something you can actually book and do.
Brigit Zimmerman Has Spent Her Career Making the Complicated Look Bookable
The Priceline CEO came up through airline distribution and commercial operations. Now she is betting that better data, candid leadership and a little humor can turn travel's hardest machinery into something that feels easy.
Trip.com Group Wants the Whole Trip
Flights, beds, train tickets, even the itinerary: Trip.com Group wants a role in every part of your holiday. Its sprawling business reveals both the value of a travel middleman and the trouble that comes with having too much power.
One Fare at a Time, Snapp! Built Iran’s Everyday Operating System
Snapp! started by putting a price on a Tehran taxi ride before the passenger got in. A decade later, that small piece of certainty anchors a 20-service super app built for the peculiar scale, sanctions and street logic of Iran.
Expedia Is Building the Travel Internet Behind the Travel Internet
The familiar booking brands are only the shop window. Expedia Group's more consequential bet is to become the shared infrastructure for travelers, suppliers, advertisers and thousands of businesses that want to sell a trip.
Tripadvisor
Tripadvisor built the internet's memory of travel. Now it is trying to turn a billion-plus opinions into an experiences-first marketplace before AI rewrites how people choose where to go.
TravelJoy
TravelJoy is an all-in-one software platform for travel advisors and agencies, bundling a CRM, itinerary builder, branded proposals, automations, and secure payments into one workspace. Founded in 2018 by Dayo Esho and Chris Kline, the San Francisco company helps independent travel entrepreneurs run their businesses and compete with DIY booking sites - and now facilitates more than $1 billion in annual customer spend.
Dmitrii Pistolyako
Dmitrii Pistolyako is the co-founder and CEO of LinguaTrip, a San Francisco-based booking platform for language courses and study-abroad programs that has served more than 100,000 students from over 100 countries. A math-and-economics graduate from Saint Petersburg, he turned a free study-abroad consulting side hustle into a venture-backed company, surviving more than 50 investor rejections before becoming the only Russian startup in his 500 Startups batch. He also leads Fluent.Express and shares his playbook for building a company in the US through his Russian-language YouTube channel and online courses.
Airbnb
Airbnb is a global travel marketplace that lets hosts rent out homes, rooms, and experiences to guests in more than 220 countries and regions. Born in 2008 from three air mattresses on a San Francisco apartment floor, it turned spare space into a category-defining business, went public in 2020 at roughly a $100 billion valuation, and in 2025 expanded beyond stays into Services and a redesigned Experiences product - positioning itself as an everything app for travel.