Big Money and Big Tech: Outdoor Get's Sold Out

I did something today I thought I never would.

In the silence of my windowless office, I opened a new browser, and clicked over to Black Diamond Equipment’s site. I renewed my industry discount, received their boilerplate Welcome Back! email, and bought two rechargeable headlamps. After checking a few work emails I then headed over to a large outdoor deal site, perused countless options in grid layout, and purchased a few LifeStraw water bottles and a new Katadyn pump-action water filter.

I then clicked ‘check-out’ on a four week supply of emergency freeze-dried meals.

I was prepping; something I had always laughed at, something I never thought I would do. But after weeks of startling news on the AI front, it seemed apt to use my outdoor industry pro deals to stock up on essentials as the specter of machine doom ran its course through the news.

For a writer, it was in certain ways nothing new. “What we are witnessing is the wealthiest companies in history…unilaterally seizing the sum total of human knowledge that exists in digital, scrapable form and walling it off inside proprietary products,” activist and author Naomi Klein wrote in The Guardian back in May of 2023. “Many of which will take direct aim at the humans whose lifetime of labor trained the machines without giving permission or consent.”

But artificial intelligence wasn’t just coming for creative pursuits anymore; it had finally become an existential threat. From Bill Gates to Anthropic’s chief executive Dario Amodei, calls for reining in the technology while we still could became the cause of the moment, covered by The New York Times, The Washington Post, then coursing through social media at viral speeds.

Long after AI had sold out what it could.

In early 2021, long after digitization had upended how media was consumed, but years before AI search engines and business models would largely dismantle the online reading paradigm, something was afoot at Outside Magazine.

Based in the high desert oasis of Santa Fe, Outside had enjoyed decades as the thought center of the outdoor world—a literary giant whose stories by the likes of Barry Lopez, Jon Krakauer, and more framed the very culture. News now circulated that the publication was acquired by a mysterious conglomerate then known as Pocket Outdoor Media, helmed by MapMyFitness creator Robin Thurston. He had acquired nearly two dozen titles over the preceding few years, and in the aftermath of his latest purchase, rebranded his outfit to Outside Inc.

From the beginning, Thurston was preoccupied with something outside of content creation. “I would say the investment—we being Outside, in my view, we are a product and technology company first,” he told Alejandro Cremades on the Dealmakers podcast a few months later.

The avid cyclist and entrepreneur then outlined what he saw next.

“My future vision is that all of this stuff is much easier for the consumer and that it’s helping guide their next decision. Think about how good a job Netflix does in putting the right content in front of you through AI as you go and watch one program after the next,” he said. “They understand that here’s what they might want to watch next.” The fit and stylish businessman even audaciously hoped that Outside could garner twenty-million subscribers in just five years.

But the execution of Thurston’s techy, corporate vision would soon embody something far less optimistic.

In 2022 Outside Inc. cut 15% of its staff, shuttered a slew of acquired titles, and reduced the volume of its physical titles. Thurston continued acquiring other outdoor companies, many outside of the media sphere, only to further lay off several editorial staffers in February of 2025. Several prominent critiques of the company were published that spring, including one by past Outside contributor Rachel Monroe (whose piece ran in The New Yorker). Weeks later, thirty-five former contributors signed a letter to Thurston demanding that their names be removed from the magazine’s masthead, including legendary ski writers Megan Michelson and Marc Peruzzi. The letter criticized Outside for “undue strain on the hardworking staff that remain” and “the company’s leadership asking editors to refrain from investigative journalism and political coverage.”

Caley Fretz—formerly employed at the Outside-acquired CyclingTips before co-founding Escape Collective—noted in a sweeping piece that venture capital-funded consortiums like Outside Inc. had entered the outdoor media space in hopes of scaling legacy titles. “But their strategies of rapid expansion, cost-cutting, and a relentless pursuit of scale often left the core product weakened. By that I mean the content sucked,” Fretz wrote. “Which is what happens when you remove all the people making it.”

The outdoor world seemed to cry out all at once that Outside had gone astray.

But by late 2025, from core outdoors people to casual clickers; skiers and backpackers to Front Range weekend-warriors, OutsideOnline was still garnering over 4 million views a month per page view estimators, an order of magnitude more than any independent outdoor title.

“To me, [the] lack of direct accountability to friends, community and subcultures has led to a place where Selling Out isn’t even a thing anymore,” Cody Townsend, the most iconic freeride skier of the generation, lamented on his Fifty+ blog in 2024. In a subculture where digital advertising had become the lifeblood of not only brands, but athletes, all that mattered, it seemed, was the online hustle.

So ubiquitous and influential is Townsend—a skiing, writing, and social media-mainlining polymath in his own right—that his look of long blonde locks spilling out from under a flipped flat brim hat and huge sunglasses has become its own trend amongst skiers.

But he is more than an image or a hustle culture scion. Townsend has also become a leader amongst snow sports cognoscenti, with articles running in places such as The High Route and Mountain Gazette. And his opinion pieces on his own blog cement a world view on skiing that touches on land use, the ski industry. And authenticity and legitimacy.

“While sponsors will likely always be a part of my job, my teenage self cringes every time I sign a contract with a predetermined amount of Instagram posts that include the words #ad or #paidpromotion,” Townsend continued before pivoting and asking himself a hypothetical question no sane skier would ever answer in the negative.

“I also know how my teenage self would answer if I went back in time and asked, ‘Would you trade ‘Selling Out’ for a lifetime of skiing?”

Looking at my friend Jeff, I started apologizing. Awash in the sepia of an old lamp, we were splitting a beer in his unfinished basement, a space I knew well. The immaculate ping pong table still anchored the space, and the walls—just studs and insulation—were adorned with braided garlic bulbs from his garden.

What I was sorry about was my new job.

Jeff, a spindly, almost seventy-year-old hustler whose tanned face and deep-set wrinkles spoke to years of toiling in the sun, shrugged it off. He had spent decades as a painter, a ski instructor, a handyman. Work was work. And he and I had washed golf clubs together for ten years at a tidy country club in town complete with tacky ranch decor where we pined for tips from a membership that saw us as bums. We were far from ascetics.

Still, Jeff always eschewed the nine-to-five, and cobbled jobs together to save enough to build a house when that was still possible here. It all seemed to be on his terms. And I wasn’t sure I could say the same about myself and my new gig, a $15 an hour entry-level desk job at a fledgling energy food company. I would forsake powder mornings; my hundred days a year of skiing would surely be halved. Jeff asked me if I was still thinking about writing. I wasn’t.

Now years later I sit at my computer screen, my face and its growing lines awash in a computer’s fluorescent light. I was writing about skiing, but only when I could between the tasks of my day job, which are soon to be optimized by machine learning. Just like my previous ski writing gig was. So I left.

Looking past my silent coworker, I see the ski area through their window, towering and green in the afternoon summer light. I think of skiing with my son there last winter; I remember that I haven’t ridden my mountain bike on it since the snow melted. And I remember why I apologized to Jeff.

I remember the trade.