OtherUncovering the Wild Near You: Member Chat with the Outdoor Project

So you have a hankering to take a break from the hustle and bustle of city living. You want to go somewhere exotic, breathtaking, pristine. But you can’t hop on the next flight to the Alps—in fact, you can only afford a Sunday and a tank of gas.

Luckily for you, the Outdoor Project is eagerly waiting to introduce you to a nearby outdoor adventure. With mouthwatering photos, detailed trail maps, user reviews, and other key information, Outdoor Project helps you discover, plan, and share trips that won’t cost you any vacation days, or the better part of your savings account. After all, in a state bursting with hidden natural gems, sometimes the challenge lies not in summiting the peak, but in finding the peak to summit.

Here, we sit down with Tyson Gillard, CEO and Co-Founder of the Outdoor Project, to learn more:

Tyson Gillard, Co-Founder and CEO of the Outdoor Project.
Tyson Gillard, Co-Founder and CEO of the Outdoor Project.

What was the spark that inspired the birth of Outdoor Project?

Like other intrepid travelers, I’ve visited many distant corners of the world for vacation and adventure. Though I’ve also visited many parts of Oregon, I only recently realized that in the process of seeking faraway adventures, I was missing out on all the amazing places to discover in my own backyard.

In talking to friends and colleagues, it became clear that far too many people were overlooking some of the planet’s most incredible attractions, mostly because they didn’t know enough about them. This was the spark that led to the creation of Outdoor Project.

Outdoor Project aims to help people through the before, during, and after of the outdoor and travel experience. More specifically:

  • Planning where to go before heading out (inspiration, planning info, gear and apparel, and education)
  • Everything you might need during an adventure (friends, maps and field guides, outfitters and guides, and accommodations)
  • Sharing after you return (photos, videos, trip reports, and reviews)

What sets you apart from other companies in your sector?

Until now, guidebooks and USGS maps have been the most trustworthy resources people can use to plan and execute an outdoor adventure, with most online resources being very limited geographically or by adventure type. No one else currently provides a holistic outdoor resource, and none has really made a focus of combining search with engaging and inspiring photography.

I doubt there is any job other than architecture that could have better prepared me for becoming an entrepreneur.” (Tweet this.)

What has been your biggest success story to date?

In general, starting something that others believe in and want to see come to fruition just as much as I do has been incredibly rewarding. The feedback and engagement we’ve seen from our users, individuals, our non-profit partners, and our retail partners, has been spectacular and has exceeded our expectations out of the gate.

Within a week of going live, Portland Monthly published a great article about Outdoor Project on their Tripster blog. Pro Photo Supply recently shot a community profile video that did a wonderful job sharing our story and visual approach to finding an adventure. The level of excitement and engagement has been wonderful!

Trail map of Unicorn Peak
The Outdoor Project provides detailed, printable trail maps for your next outdoor adventure.

When I was really young, I first envisioned becoming a tax attorney, but that was crazy. Starting in high school I planned to become an architect — I am actually still licensed as an architect. Architecture allowed me to combine my passions for design, nature, and sustainability with a job that required thinking practically, working together with others, and making ideas come to life.

Actually, I doubt there is any job other than architecture that could have better prepared me for becoming an entrepreneur. There are significant parallels. You have a complex challenge, always with real budget limitations, but step-by-step and with a talented and diverse group of people, you work through the challenges to see the project come to fruition. Moreover, I don’t know many professionals who work as tirelessly, on as fast-paced schedules, and are as committed to delivering on expectations, as those in the building industry, particularly those in the industrial sector.

What’s the best thing about being an entrepreneur?

I have found it to be incredibly rewarding to create a product from scratch in a way that hasn’t been done before, something amazing that people have always wanted but never had.

What keeps you up at night?

First, I get restless if and when things are incomplete, particularly great ideas. I’m eager to see the fully realized vision of Outdoor Project come out, and as a start-up we constantly have to make tradeoffs and set priorities and timelines based on our limited quantities of available time and money.

This leads to the second, which is knowing if we’ll have sufficient money to make the full vision of Outdoor Project a reality and if we’ll be able to raise the investment capital we’ll need to keep moving forward at full speed.

What is the best entrepreneurial advice you have received (and from whom)?

“Most entrepreneurs fail because they give up too soon, not because they don’t have a good idea,” from my friend Jonathan Rickert (CEO of Array Health). Patience isn’t my strong suit, so this was great early advice for me.

What song best describes your work ethic?

Good question.  Anything from Les Miserables. I’ve always identified with Jean Valjean’s character… what a strong, dedicated, honest, and mission-driven individual. (I even considered getting a “24601” tattoo at one point.) I was also listening to the Last of the Mohicans theme song a few weeks back, and that got me pretty pumped up.

Most entrepreneurs fail because they give up too soon, not because they don’t have a good idea.” (Tweet this.)

Imagine your venture becomes wildly successful. What does that look like?

It looks really good! At Outdoor Project, we want to be the catalysts for a global outdoor revolution. We want everyone to be more in-touch with nature, where people get satisfaction out of finding amazing things to do outdoors, discovering new places, and living in a sustainable synergy with the rest of the natural world. We like the thought of everyone knowing, caring, understanding, sharing and becoming stewards of the land and wildlife around them.

It’s something in-between the outdoor movement in the United States of the 1930’s (including the Civilian Conservation Corp, Works Project Administration, creation of countless National Parks) and the incredible balance with which the Na’vi culture coexisted with nature on planet Pandora from the movie Avatar. Excuse the rough analogies, but hopefully it gives you a sense of what we’re after.

Can you describe your typical day?

Oregon’s Neskowin Ghost Forest is just one of many breathtaking local destinations featured on the Outdoor Project. Photo by Outdoor Project Contributor Race Jones.

As the CEO, I have to wear a lot of hats, so my typical day changes all the time. At the beginning, to build the content that would seed the website, it was waking up at the break of dawn to go out on as many adventures as possible. I documented 250 outdoor adventures in six months. Considering that each has inspiring photos, detailed adventure data, a write-up and a map, that’s a lot of adventures! It was absolutely incredible getting to know our region, but it was much harder and less glamorous than most people might imagine.

More recently, as our focus has shifted to working with contributors and developing the next version of Outdoor Project, the days are much more deskbound. In addition to the normal business email and phone calls, a typical day involves working with the various team members, map makers, and contributors on content development and quality, reaching out to investors and business partners, working with our web development team to refine and improve the website, and engaging in our various marketing efforts. However, I still generally get outdoors on an adventure at least once a week with larger trips planned whenever I can.

What’s your favorite local business and why?

I have always been impressed with McMenamins (other than the occasional subpar service). They have been able to create a fun, extremely welcoming, and unique experience for visitors, while establishing a great model for historic preservation and making it financially successful. I am also consistently impressed with the culture and workforce loyalty that New Seasons Market has established.

It’s an exciting time to be a Portland-based start-up with large aspirations.” (Tweet this.)

Do you think Oregon is a good place to start a business? How has it helped you, and what challenges have you faced?

Oregon is a wonderful place to start a business, especially in the outdoor industry. Portland has an amazing array of talented and well-educated people who are eager to participate in design-focused enterprises. The lower cost of living compared to the larger cities on the West Coast means you can do more with the limited cash on hand with which all early stage start-ups are challenged.

The traditional bias against Oregon as a great place to start a business is that there are fewer wealthy individuals, investment funds and incubators than some of the more established markets, but it has been encouraging to see and hear how much this is changing. It’s an exciting time to be a Portland-based start-up with large aspirations.

The Outdoor Project team. Left to right: Jared Kennedy, COO; Tim Rasmussen, CTO; Tyson Gillard, CEO; and Aron Bosworth, CAO (Chief Adventure Officer).

Any other tidbits or fun facts to share?

My wife often gets mad if she catches me on the website during our together time, or what’s supposed to be non-working time, but I really like using it, planning new trips, and seeing the work and photography of our contributors as it gets published.

What advice do you have for aspiring entrepreneurs?

I have certainly learned and have been reminded that you are only as strong as the rest of your team, so you better have a great team!


Learn more: Follow Outdoor Project on Twitter, like on Facebook, or visit outdoorproject.com.


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