A Big Bet on ‘Mystery Vacations’: Travel Startup Funding This Week

Megha Chaturvedi has been married nine years: She booked their vacations, and her husband usually didn’t even know where they were going. Now she’s turned that idea into a company.

Chaturvedi and two partners just raised 1.75 million British pounds ($2.1 million US) of seed capital to turn London tour operator Journee into a bet that other people are like her husband: Surprise them thoughtfully, and they’ll have a good time.

It works a bit like Netflix: Tell Journee’s algorithm what you’re looking for – scenery, history or local food – and it plans a trip that fits the customer’s budget. The company picks lodging, flights, activities, even restaurants for four days or more. (All trips leave from London). Then Journee makes a proposal telling the customer about where they’re going, without naming the city. The customer then decides whether to buy it or not.

“We’ve never sent someone to Paris,” Chaturvedi says. “We can match them to a trip they end up loving, but would never think of themselves.”

The most common destination so far: Romania. It’s off the beaten path, pretty, and has lots of medieval history, she said.

Chaturvedi and her cofounders, Ed Tribe and James Gillard, worked together at online fashion site Depop. Depop’s founder Simon Beckerman and CEO Maria Raga both invested in Journee, in a round led by Fuel Ventures. The company opened Journeetrips.com in 2019, but the Covid pandemic set them back, Chaturvedi says. More than 1,500 customers so far have taken the plunge, she said.

The customer gets a written Trip Pack a week before departure that contains the name of the destination, but most open it at the airport, the company says. No one has backed out of a trip when they learn where they’re going, Chaturvedi said. The company has a 4.9 rating on consumer-review site Trustpilot, which reports 179 Journee reviews.

“At the end of the day, it works because people have an amazing time,” Chaturvedi said.

In other travel-technology funding this week:

• New York-based Kasheesh came out of stealth mode, announcing $5.5 million in funding led by Tribe Capital, Anthemis and Courtside Ventures. Other investors included NFL receiver Odell Beckham Jr. and actor Robin Wright. Its product is a browser extension that lets customers split payment for travel and other purchases over different debit and credit cards. The idea is that Kasheesh lets consumers spread debt over cards they already hold, and maximize their garnering of reward points. Kasheesh generates revenue from fees paid by credit card companies. Loyalty innovation has helped drive travel’s recovery from the Covid pandemic, according to Skift.
• Britain’s easyGuide, a business-to-consumer site selling destination attractions tickets, raised perhaps the most unusual funding round of the week: 1 million pounds from UKTV Ventures, an affiliate of the British Broadcasting Corp. The wrinkle: The investment is in the form of advertising. The campaign starts next month and lasts for a year, CEO Blake Anthony Reddy said in an e-mail.
• Kiwi.com, a Czech online travel agency, said it raised 100 million euros in a deal led by an undisclosed investor. Skift covered the deal here.
• Omio, a Berlin-based seller of ground transportation services like bus and train tickets, raised $80 million to support its expansion, mostly in the U.S. Skift’s Matt Parsons explains here.
• Distribusion, another ground transportation platform, raised 30 million euros in a round led by Lightrock. The company, also based in Berlin, has focused on Latin America and says it will serve 100 million people yearly by late 2024.

Skift Cheat Sheet

Seed capital is money used to start a business, often led by angel investors and friends or family.

Series A financing is typically drawn from venture capitalists. The round aims to help a startup’s founders make sure that their product is something that customers truly want to buy.

Series B financing is mainly about venture capitalist firms helping a company grow faster. These fundraising rounds can assist in recruiting skilled workers and developing cost-effective marketing.

Series C financing is ordinarily about helping a company expand, such as through acquisitions. In addition to VCs, hedge funds, investment banks, and private equity firms often participate.

Series D, E, and, beyond These mainly mature businesses and the funding round may help a company prepare to go public or be acquired. A variety of types of private investors might participate.