The most successful trail sponsorships happen when brands stop asking "what can this athlete do for us?" and start asking "what can we build together that neither could create alone?"

Alyssa Clark embodies this shift. The professional trail runner sponsored by On, Hyperlight, and Gnarly doesn't just show up on start lines—she builds partnerships through proactive engagement, strategic introductions, and genuine care. She also coaches for Everyday Ultra, hosts their podcast, and works with agent Kelly Newland to professionalize the athlete side of the sport.

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When Alyssa explained that Everyday Ultra founder Joe Corcione is trying to create "the Disney experience for ultra runners," it clicked immediately. This isn't a training program—it's an entire ecosystem designed to make people feel magic.

When someone joins the coaching program, they receive a welcome email, a personalized video from Joe, a handwritten note, a welcome gift, access to group calls, and integration into a Discord community that Alyssa manages.

"I have heard with clients is that they feel very seen and they don't feel like just another face compared to sometimes some other coaching organizations," Alyssa told me.

I've brokered several partnerships for Everyday Ultra, and they consistently perform because people genuinely feel connected.

The concept comes from Will Guidara's book Unreasonable Hospitality, which Alyssa finished in three days. The book's core principle is going absurdly above and beyond to create memorable experiences.

What makes Everyday Ultra particularly interesting is that Joe comes from a business background with a master's degree, not an athlete background.

"I think having both kind of Joe coming from the business world, and then I'm more of athlete creative," Alyssa explained. "I think it creates a very interesting and special ecosystem of yes, we have the feelings and the athlete side, but we also have the business side of how do we make this an effective company."

"I think it was very realistic that often there would be contracts for five, 10, 15,000 for very strong athletes that were a few years ago," Alyssa explained. "And now the starting salary is like 40, 50, 60, and then it's not uncommon to be seen closer to seventies, eighties."

Add in nutrition sponsors, watch sponsors, and bonus structures, and you start to see sustainability. This growth creates space for agents like Kelly Newland.

But not everyone needs an agent yet. "There is no point in hiring an agent to negotiate a $20,000 contract," she said. For athletes commanding $60k+ with multiple brands, representation makes sense.

When I asked Alyssa for her top advice for athletes wanting to become professionals, she didn't lead with training or results.

"Be a good person, run fast, but those in that order," she said. "So much of it is the person. Does the personality fit on the team? Do you have a good reputation? Do people like being around you? Ultimately, we are marketing tools. A professional athlete is a marketing tool to sell product."

Trail running is a small world. How you treat race volunteers, other athletes, and brand reps matters.

Alyssa regularly sets up meetings with sponsors to pitch ideas. "I'll often ask to set up a meeting and be like, 'Hey, I have these ideas. What do you think would be possible?' And they're always kind of shocked. They're like, 'Wow, I wish more athletes did this.'"

With Hyperlight, she wants them to look back and say "Wow, partnering with Alyssa brought so many opportunities to the brand, from friendships to product opportunities to partnerships."

This proactive engagement effectively makes her a part-time employee. The athletes who understand this shift from "what can you do for me" to "what can we build together" are the ones who'll thrive.

The On Cloud Ultrapro uses a nylon plate instead of carbon. Carbon plates can cause discomfort over hundred-milers, but this nylon plate delivers speed without the problems.

On holds annual summits in Portland where athletes see the next year's product line and meet with designers. About 200 On employees attend, creating overlap between the people making products and the people testing them.

"You have to have a company culture where everyone as much as possible believes in the storytelling component, believes in the mission," Alyssa explained.

There are massive opportunities for non-endemic brands in trail running. Alyssa mentioned solar panels, car leases, Airbnb credits—anything expensive that athletes would be buying anyway. Airlines sponsoring runners in their hub cities would be incredibly authentic.

The key is authenticity. In my Substack "Why Fit Compounds," I wrote about saying no to things that aren't genuine fits so the things you do promote actually land. Trust is built in droplets and lost in buckets.

Alyssa is 32 and entering her 11th year of running ultras. Her dream role after racing? Team captain for a brand like On, helping other athletes get project ideas visible, suggesting new team members, and supporting teammates. She pointed to Hillary Nielsen's time with The North Face as the model.

There are also challenger brands entering the US market like KIPP Run, Mount to Coast, and Norda that could use someone who understands both sides.

The brands and athletes winning right now are building something together that neither could create alone. That's the secret: unreasonable levels of care at every touchpoint. Make people feel magic, and they'll run up mountains for you.

Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

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