Where brands fail

A musing on the gap between winning and losing in the brand world

As I sit here on my laptop in a small hostel in Maine, the first thing I do is open my email. I’m spending two weeks training on the hardest, most rugged sections of the Appalachian Trail. And yes, my laptop is along for the ride. Because if I’m taking 45(ish) days off to attempt an Appalachian Trail FKT, I can’t exactly afford to take any more time off work. So I balance things—reviewing workouts for athletes, jumping on pre-FKT calls, and editing podcast episodes (seriously), all while racking up training miles in the mountains.

Today, I opened an email with an offer to shoot some product ads while I’m out here on the East Coast. A quick afternoon session for some FKT funding. Sounds simple enough—but it brought me back to a bigger question I’ve been thinking about for years:

Is this what the brand-athlete relationship should look like?

I don’t think so.

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The Current Landscape

The athlete’s dream is simple—do something big. Something hard. Something meaningful. That could be a race, an FKT, a new route, or a journey few have attempted. The brand’s dream? Sales. Growth. Exposure. Those aren’t bad goals, and they don’t need to be in conflict. But more and more, it feels like they’re at odds.

When a brand sees an athlete only as a billboard—or only activates them for tightly scripted content shoots—they’re missing the deeper value. The athlete’s real story, their motivations, their process, their struggles and triumphs—that’s the stuff that builds genuine connection.

And that’s the stuff that sells, long term.

I will be frank: brands need ads. Product-focused content works. It drives conversions, it feeds the algorithm, it gives clean, easy-to-read metrics. Clicks, views, ROI. It is safe and easy to tell if it works. Ads should be part of the picture.

But when ads become the only picture? That’s a problem.

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Why Storytelling Should Be the Foundation

Take John Kelly’s Appalachian Trail attempt. His raw videos combined with La Sportiva’s polished content struck a nerve. It reached ultrarunners, FKT junkies, and even casual hikers—people who wouldn’t normally follow a long-distance record attempt. I’ve been training in Maine, and multiple people on the trail have brought it up. They followed the updates. They were inspired, intrigued, and captivated.

That’s reach you can’t buy through traditional ad strategy.

Here’s the key: the gear wasn’t the focus of the story, but it was present. And because it was part of something compelling—something emotional, relatable, and real—it created trust and recognition. That’s what modern marketing should look like. Not gear screaming for attention in a 30-second Instagram ad. But gear supporting a bigger journey, like it does in real life.

That’s the type of content that sticks.

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Support the Athlete, Not Just the Outcome

If brands want to maximize their investment in athletes, they need to do more than fund the finish line photo. They need to support the process—trainings, setbacks, mental struggles, tiny wins, the boring middle. The whole arc of the story, not just the climax.

If you believe in the athlete, show up when the story is still unwritten.

Too often, the only time a brand steps in is for a shoot—with clean gear, a shot list, and a tightly scripted voiceover. But what makes athletes compelling isn’t just how they look on camera. It’s what they overcome. It’s who they are when the weather turns, when plans fail, when they dig deep, when they keep going anyway.

This is the difference between a photographer tagging along on a workout verse a scripted shoot.

Athletes aren’t actors. However, they have amazing stories and deeply entrenched reasons. Help them tell them.

Give them space to pursue their goals, and trust and resources that the story that comes from that pursuit is worth more than any ad you could storyboard in a boardroom. We need longer-form stories or more 8-part mini-series to know the people and why they do what they do.

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Marketing with a Human Touch

I’ve heard brands complain that people assume they’re way bigger than they are. That they’ve lost the “small business feel.” Well… look at your marketing. If you only show up in paid placements and glossy campaigns, of course you look like a faceless big company.

Marketing is more than selling—it’s identity. When you only show polished ads, you lose the ability to connect on a human level. And once people stop seeing you as human, you better have the best damn product on the market. Because loyalty won’t save you anymore.

What creates loyalty is alignment. If I see someone like me—or someone I want to be—using a product in a real, meaningful way, that’s when I care. That’s when I remember a brand. And that’s when I buy.

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So, What’s the Answer?

It’s balance.

Yes, run ads. Showcase your gear. Highlight your bestsellers. But don’t stop there. Build long-term trust by building long-term stories. Invest in athletes not just as content creators, but as people with depth, purpose, and ambition. Show how your gear supports their wild goals—and let them tell the rest; or pair them with one of the many talented creators and let them organically tell the story.

Every adventure, race, and FKT starts with a reason. A why. That’s where the connection lives. Brands should meet athletes there—not just at the finish line or the campaign shoot, but at the messy, meaningful beginning.

Because when people connect to the story, they remember the gear that helped write it.