Outside expands its outdoors media empire with acquisition of booking software developer

Outside Interactive Inc. has purchased Inntopia, a Vermont-based booking software developer the Boulder-based company hopes is another step in the plan to become the one-stop-shop for outdoor content, events and travel. 

Inntopia’s software is used by 200 resorts, helping hospitality businesses book visitors. The company’s research helps destination communities better manage those visitors with booking, marketing and analytic tools that measure tourism business trends.

The deal — the latest in a five-year acquisition binge — will help Outside and its partners offer travel packages with lodging, activities, gear rentals and ticketing to events. And it’s an example of a surging trend that blends retailers with media companies.

Linking retailers and media companies, a strategy called “retail media” or “commerce media,” is a way to diversify revenue, said Keith Bryan, the founder and CEO of Minneapolis-based Colosseum Strategy. Bryan created Best Buy Ads in 2010 through which the retailer works with the CNET technology news website, just like Instacart works with New York Times Cooking.

“I see retailers entering deeper and deeper relationships with specialty publishing — general merchandise, grocery, fashion, beauty, health, fitness and electronics,” Bryan said. “There is going to be a lot of activity at the intersection of retailers and specialty lifestyle publishing. What is happening at Outside may be the first time many people read about this blending of commerce of media, but it will not be the last.”

Inntopia’s resort partners get access to Outside ad deals and the company’s network of nearly 1 million Outside Plus subscribers, which corrals 25 brands into a single membership accessing magazines, apps and events. Outside also gets Inntopia’s business intelligence research and analytics platform, which “will empower Outside to gather and analyze key insights into consumer journeys,” Outside said in a statement that did not discuss the financial details of the acquisition.

Inntopia fits with Outside CEO Robin Thurston’s overarching vision to “inspire, activate and celebrate” outdoor adventurers by creating a sort of Amazon Prime for the outdoors. He calls it “one-stop shop for outdoor adventure travel” that marries Outside’s content, registration and mapping apps with Inntopia’s booking systems. 

“It really fits into a space that will be helpful for a lot of our partners,” Thurston said in an interview with The Sun. 

Thurston is an entrepreneur who five years ago began consolidating outdoor magazines and online mapping tools.

Outside’s online registration systems — skireg.com, runreg.com and bikereg.com — fill 7,000 events. 

“Today, after somebody registers, we don’t really help them in the rest of that journey,” Thurston said. “Where will they book a hotel and go eat? Will they book any excursions? Now with Inntopia, we do something no one else is doing with our combined platforms.”

The acquisition of Inntopia grows Outside to about 450 employees, up from 370, but the deal included layoffs of about 20 workers last week, marking the third round of layoffs for the company since 2022. 

Thurston said the layoffs included employees in Outside’s editorial, product, marketing, sales and finance teams and are part of “getting the company in a stable position.” A source with the company said the layoffs include Christopher Keyes, who served as the editor in chief of Outside magazine from 2007 to 2022 before taking over all of Outside’s outdoor magazines, eight editors, the head of sustainability, a group creative director, a social media analyst, a director of sales, a director of search engine optimization, a manager of digital production, a worker in advertising operations, a senior brand director and a vice president of data and analytics. Many of the editors worked for Outside magazine. One source said Thurston has laid off all but a couple Outside magazine employees who were with the publication before he acquired it in 2021. 

Outside reaches as many as 300 million unique visitors a year through its magazines, Outside TV, podcasts, movies and social media, Thurston said. 

The second largest source of ads on the Outside network comes from the travel and tourism industry, and the Inntopia deal gives those advertisers access to a treasure trove of travel research. 

“Whether it’s mountain towns or these communities where they are holding these cycling or running or skiing events, there is not a lot of economic data around these events,” Thurston said. “We really want a lot more of these events to happen and we believe that can happen if there is better understanding of what is happening on the ground. We think this will help event directors with the big goal of ensuring that these types of events can keep going.”

More than $150 million in venture capital funding

Four years ago the expanding Pocket Outdoor Media acquired Outside magazine and the New Mexico-based magazine’s television and video company as well as the Gaia GPS mobile mapping app, event registration company athleteReg and Peloton magazine. The acquisitions formed Outside Inc., which rebranded to Outside Interactive Inc., with magazines like Backpacker, Climbing, Pinkbike, Ski and Velo. 

Thurston has been aggressively raising capital to back his vision. The 2021 Outside deal grew from a second round of startup funding of $150 million from three Bay Area venture capital firms — Sequoia, Jazz Ventures and Zone 5 Ventures — and global technology recruitment firm Next Ventures. 

Last year Outside acquired the MapMyFitness app from Under Armour in a sort of full circle for Thurston. In 2013 Thurston sold the then Denver-based MapMyFitness to Under Armour for $150 million. The company moved to Austin and expanded with MapMyRide, MapMyRun and MapMyWalk, growing to 85 million users. MapMyFitness is now returning to Denver, joining  tracking platforms like Outside’s Trailforks mountain biking trail mapping app and Gaia GPS, which offers satellite mapping of all sorts of trails. The acquisition of MapMyFitness pushed the Outside stable to more than 1 million subscribers. 

The company’s inaugural Outside Festival drew 18,000 visitors to Denver’s Civic Center park in June last year, building a possible model for a consumer-friendly gathering for the nation’s outdoor industry. The Outside Festival returns to Denver in June, with industry events, films, speakers and concerts. 

There are no more Outside acquisitions on the immediate horizon, Thurston said, noting the company is going to have “a lot of focus internally” in the coming years. 

“I’m very, very committed to not only continue to grow, but be self-sustaining without the need for more external capital and extra funding,” he said. 

International growth is a high priority as the company translates its existing content into different languages, Thurston said. About 40% of the traffic visiting Outside’s media and websites is coming from outside the U.S., he said, and the company has investors in the United Kingdom and Australia.

“I’m extremely bullish on the international opportunity for Outside,” he said. 

When Thurston first began assembling outdoor magazines in 2019 and 2020, the businesses were solely dependent on ad revenue. The paid print subscriptions to those magazines were losing money, he said. At the end of 2025, only 40% of Outside’s revenue will come from ads while the other 60% is split between Outside Plus subscriptions and the service software like GaiaGPS, MapMyFitness, Inntopia and athlete registration apps. 

There have been bumps in the road on Thurston’s mission to roll up outdoor media into a single entity. In 2022 and 2023, Thurston divested from some businesses, reduced print magazine content and cut more than 20% of the company’s jobs as he tightened budgets. 

He said the company “was definitely challenged” by the advertising market retraction coming out of the pandemic as he transitioned Outside from a dependency on ad revenue. 

“The layoffs were painful,” he said. “2022 and 2023 were tough years.”

This year, Thurston said, the company’s highest goal is to not only grow revenue, but have positive earnings and cash flow. 

“I cannot emphasize how much we need to put this profitability in our position,” he said. 

Thurston said he hopes Outside will be strong enough to make an initial public offering in the next three to four years. 

“But we have a lot of work to do,” he said. 

The growing emergence of “retail media”

Outside said the layoffs last week covered workers in editorial, product, marketing, sales and finance and included eight employees in Colorado. 

“Our editorial team across all of the Outside Inc. brands remains one of our largest groups of full-time employees, in addition to freelancers and contributors who support our beloved content and storytelling,” a statement from the company reads. 

Several employees who lost their jobs in the latest round said they signed nondisclosure agreements connected to severance packages and declined to comment. 

James Huang was a tech editor for Outside’s Bike Radar in 2023 when he quit to join a group of Outside refugees at a startup cycling outlet called Escape Collective. He’s watched the ebbs and flows of Thurston’s strategy for several years. 

“He’s definitely not a traditional media guy. He’s more of a tech guy. And he’s following that tech model of building to scale. He does not seem particularly interested in Outside as a media company. He’s using media as a piece of a puzzle he’s putting together,” said Huang who left the Escape Collective last year to create his own bike tech review site on Substack called n-1. “I’m not saying that’s a bad thing. Media is a weird business that often does not make sense on paper. Robin obviously makes a pretty compelling pitch or he would not be able to get all this funding. I see his goal, but these venture capital people are going to want a return on their investment and I’m not sure how that works.”

Andrew Lipsman is an e-commerce analyst whose Media, Ads + Commerce Substack looks at the emerging convergence of media and commerce. It’s a growing business strategy as retailers and advertisers acquire digital media companies to marry branding and selling stuff with original storytelling.

“The right publisher can deliver advertising to a larger audience and ultimately lower acquisition costs for customers who become more interested in brands through relevant content,” Lipsman said. “Commerce is a very interesting monetization model that most publishers are going to need to participate in in some way.”

Lipsman understands the angst as outdoor adventurers watch their beloved storytelling venues swallowed by venture capital and a big-ideas entrepreneur. 

“A lot of publishing is under duress right now and we all would love to have a certain purity remain in our beloved media brands,” Lipsman said. “Introducing commerce to the equation does not have to diminish that purity.”

Lipsman said Outside’s revenue, with 40% coming from advertisers and the rest split between commerce and subscriptions, is “a healthy balance.”

“Look, you can’t be a purist about this. If you want these things to exist, they have to make money and it’s all about striking the right balance,” he said. “Some publishers swing too far the wrong way, with low-quality content and a pummeling by advertisers. But appreciating the optimism of an entrepreneur and a journalist’s natural skepticism, I’d say (Thurston’s) direction is right and he’s headed where a business like this needs to go.”

Traditionally, it has been retailers moving into the publishing world. Thurston’s strategy flips that script, with a publisher taking over retail. Bryan said if he was Thurston, he’d be scheming to buy the All Trails tracking app as well as outdoor retail giants REI and Backcountry. 

“Retail media can rescue the publishing industry,” Bryan said. “Commerce media can be the salvation for speciality publishing writ large.”

Three possible outcomes when you borrow more than $150 million

There are three outcomes when you borrow a bunch of money from outside investors, Thurston said. You go bust, you sell to a competitor or you go public and sell shares on the open market. 

It’s not likely there’s another buyer with upwards of $200 million to buy Outside’s assets if Thurston’s plan does not work. So Thurston is navigating a do-or-die scenario. And what about that going-bust outcome? There are a lot of investor dollars, livelihoods and historic magazine titles depending on his dream. 

“I don’t want to be naive and say I don’t think about that. I have had a vision of what is possible about bringing all these things together since the very beginning: moving to membership, diversifying with (software service) revenue and thinking about how to curate our media audiences and help them — and monetize them — in different ways.”

Thurston said some of the magazines and brands he has acquired “would not be in existence” if Outside had not stepped in and consolidated them into the Outside Plus subscription program. 

One editor who lost their job last week said the white knight rescuing struggling drowning magazines is “a false narrative.” Many of the magazines Thurston’s acquired were making  money, just not enough to support a return on venture capital-level investment, the editor said. Another editor who lost their job last week said Thurston’s vision does not match the vibe at  the company, where outdoor-oriented writers and editors are being replaced with financiers.

“He pirated all of these legacy brands – some of which were admittedly at the end of their business cycles in the demise of the era of print media – and killed or consolidated them, pulling them away from the core communities, for the sole purpose of a huge financial play. Nothing more, nothing less,” said one editor, who asked not to be named, citing the guidelines of the company’s termination agreement.

Thurston said he’s confident his acquisitions will continue to give value to readers and Outside Plus subscribers. 

“We have new things coming for Outside Plus,” he said. “I would say I’m an optimistic entrepreneur and I’m very bullish on our vision.”