Skift Take

Tripnotes was among an increasingly crowded space for new trip planning tools powered by generative AI. It won't be the last of them to shut down.

Tripnotes got a lot of attention in early 2023 as one of the first experimental AI trip planners powered by ChatGPT. 

A demo of the product went viral on LinkedIn and Twitter in January and was shared by Foursquare founder Dennis Crowley. Tripnotes has been referenced consistently since then by media and industry professionals.

But in mid-December, the founders shut down the Tripnotes website several months after selling to Dorsia, a members-only restaurant reservation startup. Dorsia also bought Welcome, a city guide app similar to Tripadvisor and the owner of Tripnotes.

Why the sale? Tripnotes had buzz, but it needed money – which wasn’t easy to raise in 2023, especially after Silicon Valley Bank collapsed in March. 

“It was just a moment where everything froze,” Tripnotes and Welcome co-founder Matthew Rosenberg told Skift. “And it just became clear to us that even if you have a good idea, even if you have what I would consider really great early traction — we just found ourselves in a situation where we were going to have to find a different outcome than being able to raise another round and keep going.”

The Goal To Reinvent City Guides

Tripnotes was among the first travel companies that said it was fully dedicated to building a trip planner powered by generative AI. Rosenberg told Skift in February that Welcome was fully refocusing its resources toward the Tripnotes project, which he saw as a way to better compete with industry leaders.  

Rosenberg had big plans of reinventing the city guide category with personalized recommendations and in-app travel booking. The team had been gathering data from user searches and online resources like blogs and social media. Tripnotes reached a million users within 45 days. 

There have been many generative AI trip planners released this year by small and large companies. None are reliable replacements for traditional trip planning yet. 

“I just haven’t seen anyone doing what we had imagined. And I deeply feel like what we were working on would have found success with enough time,” Rosenberg said. “I’m still optimistic that someone’s going to solve this problem in a really unique way.”

This situation aligns with early predictions that the large online travel agencies may end as the big winners — they have the resources to continue refining their AI trip planners.

What’s Next For Dorsia?

Rosenberg, now vice president of product for Dorsia, was the CEO and co-founder of mobile video editing platform Cameo, which he sold to Vimeo in 2014. Many of the developers from that team co-founded Welcome and are among the team of six that has joined Dorsia.

“Personalization and AI — that was a core thing that was super important to us, and we didn’t have that muscle,” said Marc Lotenberg, founder and CEO of Dorsia. “To build that team and to know who the right people are is a bit tough … They have the history, they have the knowledge base, they have all that, so we wound up doing a deal.”

Dorsia released a beta version of its reservation app in summer 2022. 

Users can make reservations at certain popular restaurants exclusively through the app. Unlike apps like OpenTable, Dorsia requires the user to commit spending a certain amount of money at the restaurant, based on supply-and-demand pricing, to secure reservations. Or they can preorder specialty items like champagne or Wagyu beef.

Users can also pay within the app and split the bill with members and non-members, allowing them to leave the restaurant without having to wait for a bill. 

Lotenberg said Dorsia is focused on creating more personalized experiences, which the Welcome/Tripnotes team is helping to develop. 

“Personalization is going to be a key focus for us in the next year, especially as we continue to expand into new verticals around hospitality,” Lotenberg said. “What we’re going to really be using that for is all around driving loyalty. Personalization is where we start, but loyalty is a key part of that.” 

One of those upcoming features is location sharing, giving the restaurant a more accurate estimate of when the party is arriving. That would enable the restaurant to greet guests by name at the door and have pre-ordered drinks waiting on the table. All of that information about preferences is saved, paving the way for future features like personalized offers.

Dorsia is used by more than 200 restaurants in New York, London, Miami, Los Angeles, the Bay Area, and the Hamptons in the summer. 

Lotenberg is aiming for 800 restaurants in 2024, with expansion to Las Vegas, Dubai, Dallas, and vacation spots like Aspen, Colorado, and European summer destinations. The company is also onboarding several hotel groups for use of the Dorsia app as part of a concierge service.

Dorsia has raised about $30 million in total through a series of previously unannounced funding rounds.

That includes $13 million in various safe contracts in 2022 and $12 million in early 2023 in a pre-series A round led by Index Ventures. The company also raised another $5 million recently and is working on closing a series A round next year.

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Tags: artificial intelligence, chatgpt, mergers and acquisitions, restaurants, startups

Photo credit: Tripnotes was acquired by Dorsia. Pixabay / Pixabay

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