Mindtrip Raises $12 Million in Tough Funding Environment for AI Trip Planners

Mindtrip, a trip planning and booking website powered by generative AI, said Tuesday that it has raised $12 million, its second round of startup funding.

AI trip planners of various qualities have been popping up since OpenAI released the first generative AI model in late 2022. Many of those planners have already failed, and few have raised money.

And yet Mindtrip has raised two rounds. The company raised $7 million in late 2023 and launched a beta version of its product in May 2024. It has been making updates since then, including a new group chat and planning capability released Tuesday. It’s also developing a mobile app.

The San Francisco-based startup was founded in 2023 by 12 people, including Andy Moss and Trey Matteson, who co-founded vehicle ecommerce platform Roadster and sold it to CDK Global for $360 million in 2021. The founding team also includes Garrick Toubassi, who previously led the Gmail engineering team at Google.

Against the Odds

The funding gives Mindtrip two to three years of runway to continue building the product, according to Moss, CEO of Mindtrip. 

The company will need to use that time wisely at it navigates the many variables against it. Generative AI is still a work in progress, though that tech is improving quickly. Mindtrip also has a lot of competition from small and large players. 

Expedia, Google, Tripadvisor, and many others have released beta versions of AI trip planners over the last several months. None of them, however, likely are strong enough yet to change the way travelers search and book. 

Moss believes that being a startup could be beneficial. 

“It’s just very difficult for a very large company to change the interface that their users are very used to. Most of the products and engineering talent at a large company is maintaining what’s already there, as opposed to building brand new stuff. That’s why startups typically do well in these sorts of markets,” he said.

And the venture capital — something most of Mindtrip’s small competitors don’t have — allows the startup to build a thorough product from the ground up with an experienced team, he said.

“There’s no part of the customer journey that we’re not trying to address,” Moss said.

The company’s two lead investors are Costanoa Ventures and Forerunner Ventures. Greg Sands, founder and managing partner of Costanoa Ventures, believes the winning AI trip planner will be one that makes a similar impression on users as the first time they used Uber or Airbnb. Sands, who had invested in Roadster, said feedback from travel industry experts leads him to believe that Mindtrip is on the right track. 

“The fundamental job right now is to delight consumers,” Sands told Skift earlier this year.

Making Money

One of the top hurdles now is to attract users, Moss said. He declined to share specifics about early traction but said the number of active monthly users is in the six figures. 

The company plans to establish more than one line of revenue. For example, Mindtrip would earn a commission when consumers book travel through the website. 

The company later plans to provide a consumer-facing AI tool for destination marketing organizations and other travel companies. It would essentially allow those companies to embed Mindtrip onto their own websites, integrating information related to those specific businesses. The company is working with six organizations to pilot a product.

“We’re just starting to put all the pieces in place to scale both parts of the business,” Moss said.

The good thing for Mindtrip is that all of the company’s competitors are working from a relatively level playing field — for now.

“It’s not often the world completely changes. AI is one of those moments,” he said.