Chapter 2: Freetrail State of the Union

Share the trail love:
Dylan Bowman

By: Dylan Bowman

Head Freetrailer and co-founder.

Today marks the beginning of Chapter 2 of Freetrail’s existence. Chapter 1 was an exploratory and educational phase, discovering who we are as a business and what impact we want to have in the global trail running ecosystem. Chapter 2 is about self-awareness, embracing our strengths, and pushing forward with endurance.

We’ve made a lot of progress in the past 18 months. Sometimes it’s hard for me to step back and appreciate how far we’ve come. While there have been many wins, we’ve also made several painful mistakes, publicly struggled with our name and our brand, and had a few crucible moments of near-failure.

Nevertheless, we love what we’re doing and have never wavered in our commitment to persevere towards Freetrail’s business viability, hopefully justifying the immense work it has required to bootstrap. Though far from successful, we now feel secure in our identity as a company and are optimistic about our road map.

What follows is a list of things that are evolving in Chapter 2 along with a transparent articulation of our thought process and how these changes will hopefully support our business model.

Website Re-Launch

Chapter 2 coincides with the re-launch of freetrail.com, our home on the worldwide web. To this point, Freetrail’s web presence has been mostly non-existent, instead emphasizing third-party content platforms like YouTube, podcast players, and social media.

Of course, not having an internet presence has meant that we get the vast majority of our discoverability through content, with basically nothing through the web or search. For a while now we’ve understood that, if Freetrail is going to have the impact that we want it to, we need trail runners and aspiring trail runners to be able to find us easily on the internet. And when they find us, we want to serve them with a high volume of great content, information, and resources to accompany their journey in the sport.

We now have an internet home we’re proud of that will become the core of our business and home of our community. Quite frankly, it’s the biggest investment we’ve made to date and we’re thrilled with the finished product.

A big thank you to Freetrail community member Laura MacCarley of Heartfire Creative for building this beautiful new website for us. She has been a joy to work with. Beyond designing and developing the whole platform, Laura also challenged us to think about and understand our fundamental purpose for existing – a worthy exercise for any small business!

The site will be home to our media content and eventually Freetrail Experts – a marketplace we’ll be announcing in the near future.

Corrine Malcolm | Editor-In-Chief

The new and improved website also allows us to expand our content offering in a meaningful new direction – written publishing. To this point, our media has been almost exclusively audio and video, which we’ve developed very intentionally over the past two years. Both my podcast and Trail Society have established loyal listenerships and, we hope, provide valuable information, inspiration, and entertainment to trail runners around the world.

Similarly, Freetrail Co-Founder and Creative Director, Ryan Thrower, has refined his filmmaking skills, growing into one of the best video creators in the sport. Through Ryan, Freetrail is capable of producing incredible visual storytelling for commercial or in-house use – from short-form training tutorials to feature-length documentaries.

With our audio and video presence in a healthy spot, written publishing was the obvious opportunity for expansion, rounding out our media offering in a valuable way. The new website provides a platform for Freetrail to publish articles and essays from some of the great minds in the sport and across a variety of topics – training, racing, culture, environmentalism, editorial and more.

Leading the charge on this expansion will be Corrine Malcolm, whom I’m proud to announce has joined Freetrail as the Editor-In-Chief. My friend, collaborator, and often co-host, Corrine is one of the brightest and most influential voices in trail running. We are very proud to have her lead this new endeavor. Tomorrow, Corrine will publish her first Letter From the Editor, where she’ll talk more about her intentions and ambitions in this role. Don’t miss it.

Freetrail Pro

The third and potentially most significant development in Chapter 2 is the eventual folding of the Freetrail app and the launch of Freetrail Pro – a membership community of like-minded trail runners around the world.

Longtime Freetrailers will remember that our business actually started, under a different name, with the launch of a mobile app at the beginning of 2021. From where we are now, it feels like forever ago. The app has been a success commercially, but also a massive source of self-conscious insecurity for our small team. Quite simply, we’ve not grown into the type of business that our app was designed for. The result was that we were building community around a product that we weren’t confident about, nor had the bandwidth to meaningfully improve. Honestly, this has haunted me for months.

With this transition, the rest of 2022 and beyond for me is exclusively focused on building on the trust and loyalty of the established Freetrail community and delivering a membership service that we are confident provides immense value. This is the vision behind Freetrail Pro, which I’ll explain shortly.

But first, it’s important for me to be totally honest about Freetrail’s big picture.

Working on Freetrail has been the biggest joy of my professional life. I’m consumed by a deep sense of mission and determination and feel like we are in the early stages of building something special. When all is said and done, I expect to look back on Freetrail as my life’s work and my greatest contribution to the world.

But like all things, Freetrail will only be as good as the people we surround ourselves with. Quite simply, we won’t make it as a business without our community.

As a fledgling media entrepreneur with no experience and profound imposter syndrome, I’ve been learning as much as possible about the business from others who’ve been through the fire. I recently read an article in the Adventure Journal that crystallized my thinking about where community, membership, and subscription fit with Freetrail’s present and future. Speaking about the recent layoffs at Outside, the Author, Adventure Journal Founder, Stephen Casimiro wrote:

“What I do know about the media is two things. First and most important, publishers need to create products that people value enough to purchase. It’s that simple. Make something worth buying, full stop.”

What I do know about the media is two things. First and most important, publishers need to create products that people value enough to purchase. It’s that simple. Make something worth buying, full stop

Stephen Casimiro

A simple but elegant articulation of the challenge ahead for our business and for all media entities, especially those serving niche communities.

While we’ve been making steady progress towards viability, the reality is that we need to grow the Freetrail community in order to have a realistic shot at surviving as a business. And in order to grow the community, we need to provide a product worth paying for, not rely on the charity or generosity of people who simply enjoy what we do.

That’s where Freetrail Pro comes in.

With the shuttering of our mobile app, our membership community will now be folded into our shiny new website. Freetrail Pro members will get all the benefits of the old app subscription, plus a lot more, all at a lower price point.

For $10/month or $96/year, Freetrail Pro members will get the following benefits:

  • Complete access to all Freetrail training plans and how-to training materials
  • Complete access to all member-only content
    • Private RSS feed for Rest Day, our new member-only podcast
    • Audio version of written articles
    • Paywalled audio, video, and written content
  • Access to our community Slack channel for digital trail banter and member interaction
  • Access to weekly Office Hours Zoom call with Freetrail members and coaches
  • Access to member-only events
  • Early access registration to Gorge Waterfalls and other Freetrail events
  • 10% discount on Freetrail merch
  • Access to exclusive discounts with Freetrail brand partners
  • Knowledge that you are helping to keep us in business

So, in conclusion, this is not a call for support, but instead a sales pitch for a product worth paying for. Please consider subscribing to Freetrail Pro, join our amazing community, and be part of what we’re trying to build.

Chapter 2 starts now. Thanks for reading.


Keep exploring


A Woman’s Place is on The Start Line


A Very Merry Freetrailer’s Gift Guide


Trail Runner of The Year 2023

Become a Freetrail Pro member

Get exclusive access to premium content, our private trail community, and more. Just $10/month or $96/year.