Starting Before Your Ready: Second Chances on the Trail

Jes and I got into trail running gear, sustainability, and what it actually looks like to start something without having everything figured out first. And honestly, this conversation felt bigger than just gear.

Jes is the founder of Take 2 Trail, a platform focused on keeping trail running gear out of landfills and making the sport more accessible. But what stood out most wasn’t just the concept, it was how it came to life. No perfect plan. No waiting until everything was dialed. Just an idea, some conversations, and figuring it out as she went.

We also talked about the reality of getting into trail running. It’s often framed as this low-barrier sport, just throw on a pair of shoes and go—but that’s not really the full picture. Between shoes, packs, hydration systems, and all the trial and error that comes with finding what actually works for you, it adds up quickly.

What Jess is building creates space for that process. A way for gear to have a second life. A way for people to try something new without the full price tag. And a way to rethink how we treat the things we use in the outdoors.

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What This Conversation Really Gets At

There were a few moments that stuck with me from this one. One of the biggest: you don’t need to have everything figured out before you start. Something I know well. Jes didn’t come from an e-commerce background. She didn’t have the entire business model mapped out from day one. She started by looking at her own gear, realizing how much of it was still usable, and asking a simple question—what if there was a better way to keep this stuff in circulation?

From there, it was conversations, small tests, showing up to races, collecting gear, and building it piece by piece. And that applies to more than just starting a business. It shows up in trying a new sport. In putting yourself in a new space. In doing something before you feel fully ready for it.

More Than Just Gear

At face value, Take 2 Trail is about buying and selling used gear, but it’s also about access.

Trail running gets labeled as “simple” or “cheap” compared to other outdoor sports—but once you’re actually in it, you realize how much goes into it. Shoes alone can run $150–$300, and it often takes multiple tries to find the right pair. Add in packs, layers, nutrition, lighting…it’s not nothing.

This creates a gap.

A gap between people who are curious about getting into the sport and what it actually takes to feel comfortable doing it.

And that’s where this kind of platform matters. It lowers the barrier. It gives people a way to try, adjust, and figure things out without committing to the full cost every time.

Second Chances—For Gear and Beyond

There’s also a bigger conversation here around how we treat gear in the outdoor industry. A lot of items get used once or twice and then sit. Or they miss a return window. Or they just don’t work for that specific person. That doesn’t mean they’re done—it just means they weren’t the right fit the first time.

Take 2 Trail gives those items another shot. And honestly, that idea carries over into a lot of areas. Not everything works on the first try. Not every decision is the right one right away. But that doesn’t mean it’s wasted—it just means there’s another way it can be used.

Connect with Jess + Take Two Trail

Website: https://take2trail.com/
Instagram: https://www.instagram.com/take2trail/
Jss: https://www.instagram.com/jesrunsalot/

Buy gear. Sell what’s not working. Recycle what’s done.

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