Skift Take

It's refreshing to hear startup founders and business leaders talk about their mistakes, what they learned, and what is next. It does not happen often enough.

Series: Travel Tech Briefing

Travel Tech Briefing

Editor’s Note: Exclusive reporting on technology’s impact on the travel industry, delivered every Thursday. The briefing will guide executives as they decide if their companies should “build, buy, or partner” to stay ahead.

Learn More

Adam Goldstein, former co-founder of travel price comparison service Hipmunk, said this week that he is shutting down his latest travel tech startup and leaving the industry. 

He founded that startup, Flight Penguin, in 2021 as a browser extension that searches airline and travel agency sites and presents results in a single list. Goldstein and his Flight Penguin co-founder, Max Morlocke, decided to end the startup in light of financial struggles. Investors, who included former Hipmunk employees, agreed it was the best decision. 

While the company is retiring, the browser extension is remaining active and the code is becoming open source, allowing other developers to use and build upon it. 

“Instead of just taking our acorns and burying them, which is what the vast majority of startups do, we want to leave a gift for everyone who supported us,” Goldstein said. 

Goldstein’s previous company, Hipmunk, was sold to SAP Concur in 2018 and then was terminated in 2020. Goldstein was a Skift podcast guest in 2020, during which he said he likely would not stay in the travel industry, but he later decided to move forward with Flight Penguin to help fill what he saw as gaps when Hipmunk was terminated. 

Flight Penguin experimented with a couple of ways to generate cash flow early on as the founders were working to determine the business plan. One was a subscription model and one was selling small pieces of equity to users. The startup launched a crowdfunding campaign in an attempt to cover a year’s worth of operating costs, but it fell about three months short. 

“The biggest thing that I think that I contributed and that we contributed … is a new way to look at stuff,  a new visual experience, new way of thinking about how you talk about travel, acknowledging that it’s not always easy to travel or not always easy to book travel,” Goldstein said.

“I hope that my legacy in travel, let’s say 50 years from now, is that Flight Penguin has inspired a bunch of people to build their own products or companies or both. Hopefully, one of the successors to Flight Penguin will end up mounting a real competition for one of those established companies.” 

I have been covering tech startups in a variety of industries for several years now. From my experience, startup founders are eager to share what their companies do and how they aspire to take over the world. But when there’s a misstep that leads to a downturn or a shutdown and I ask what happened, the communication lines often go silent. 

There is value in being open and honest about failures — or, learning opportunities, as some prefer to call them. Venture capitalists would say they prefer openness from founders because it means they have thought about how not to fail in that particular way again. If nothing else, in the case of Flight Penguin, other startup founders can learn from those mistakes. 

Goldstein seems to be open about discussing failure compared to many other business leaders. But maybe the reason, he said, is because he does not plan to enter the travel industry again — and, he had a win previously by selling Hipmunk. 

Goldstein is now working on a stealth biotech startup that is combining biology with artificial intelligence. Meanwhile, Morlocke became co-founder of Truebiz, a Y Combinator company that simplifies background checks for businesses.

“I’m really excited by what’s happening in biology these days. I went back to school for biology, which is kind of wild. Not very many people in travel do that,” Goldstein said. 

“And I wouldn’t have done that if I didn’t think that it had a lot of cool stuff going on. I still enjoy traveling, and I still enjoy talking to people in the industry, but I’m not expecting that I’m going to start another travel company, ever.”

Sidenotes 

  • The company 777 Travel, which provides software primarily to airlines, has rebranded to GO7 as part of what it says is a broader strategy to unify the company following a few acquisitions
  • BODDY, the Switzerland-based tech startup that connects travelers with fitness and wellness operators, is merging with Denmark-based TrainAway, which connects travelers with more than 1,500 fitness clubs worldwide.
  • A new vacation rental platform startup, Portoro, is beginning to expand in the market with its first acquisition of a property management company, Texas-based StayLocalAustin. Portoro has joined a variety of short-term rental platforms that are looking to strengthen their standing in the busy market. Portoro is backed by investment partner Downing Capital Group.
Uncover the next wave of innovation in travel.
June 4 in New York City
See Who's Coming

Have a confidential tip for Skift? Get in touch

Tags: mergers and acquisitions, metasearch, rebranding, shutdown, Skift Pro Columns, startups, travel tech, Travel Tech Briefing, travel technology

Up Next

Loading next stories