Outdoorsy: Where It All Began

Team OutdoorsyAugust 1, 2016

Outdoorsy: Where It All Began

In January 2014, Jen and I were sitting in a conference room listening to complex company updates from the executives we were working with, Jen as a marketing contractor and me as a board member. Jen and I had been inseparable for years, in business and life and we had developed our own non-verbal communication. In the middle of the presentation, we looked at each other at the same time and nodded in our familiar way that communicated “we needed to do something different.” It was that evening we started talking about ideas for a profitable business that helped others and that would have a positive impact. We also agreed on one thing: we wanted to get away from life under fluorescents lights. Our idea had to involve the outdoors and authentic experiences.

So, we decided to go for it.

Looking back, we didn’t exactly know what it would be, but we knew exactly what it wouldn’t be: cranking out marketing and business plans in an office, 90 hours a week for the rest of our lives. Still, gaining the courage to leave our safe life wasn’t easy. Jen had moved from New York after a high octane marketing career to be closer to family. I had just left a Silicon Valley company I had led for six years. We wanted to do something profound yet simple to understand and fun. And we wanted it to be great for users. We wanted to do something that fit Jim Collins’ tenant: “the essence of profound insight is simplicity.” It had to serve our passionate interest in outdoor experiences.

Having discussed our ideas over countless hours with select insiders, family and friends and of course with our co-founders, we knew in our gut that connecting people with outdoor travel was what we needed to do. Outdoorsy was born.


The open road now open for business.

So in the fall of 2014, we invested our life savings to form Outdoorsy. We downsized. Jen sold her house, I sold mine and we then set out to build a marketplace for recreational vehicles and experiential travel, but more importantly, we set out to do something that had never been done before; to give people easy and economical access to experience the great outdoors by taking their lodging with them.

We chose the name Outdoorsy because we thought Outdoorsy was the perfect emblem for the spirit of adventure that we wanted our brand to embody. (It also helped that Outdoorsy.co was available on GoDaddy for $15.98)

We purchased an Airstream Eddie Bauer Edition 27″ Trailer, a GMC Denali truck, and hit the road traveling all across America to start talking with travelers and RV owners and hone our vision. Many people chuckled when they looked at our self-designed business cards, smiling with amusement and said that they loved the idea of Outdoorsy. Many were willing to list their RVs with us not because of where we were, but because of where we were going.


Inspired by Github and Tableau Software, we decided to not pursue venture capital. We wanted to build our business on our terms. We wanted to build something around being Captains of our own ship and away from the VC-fueled boom-or-bust businesses that litter the landscape.

So we hustled our butts off.

We moved from Vancouver to Washington to San Francisco, into the Airstream and then all across America, criss-crossing through small towns that most have never heard of. Along the way we made over 1,200 personal phone calls to RV owners we found on Craigslist and we walked up to campers, knocked on their doors and sat with them for hours interviewing them to learn as much as we could. “Can you imagine what it was like to sit on the phone for over 7 months with RV owners on Craigslist? We visited people in their homes and met their families and relatives and we talked about our concept. We learned so much about what people needed, their love for experiential travel, for sharing, the hassle of renting and the hassle of owning recreational vehicles. We learned what they were thinking and we saw a phenomenon staring us right in the eyes; a massive and growing consumer movement was happening and among people from all over the world who crave outdoor experiences.

Jeff Cavins with Chris Eckrich, one of our first RV Pro Hosts
Jeff Cavins with Chris Eckrich, one of our first RV Pro Hosts

Along with our partners, we created Outdoorsy 1.0. Our first website wasn’t pretty, but it worked. If you are not completely embarrassed by your first release, then you released too late. And we were embarrassed.

In late 2015, we flipped the switch, and Outdoorsy.com went live.

Our community began to grow…slowly at first. When we weren’t in the Airstream, we worked out of coffee shops and cafes. Ryan, our co-founder, and his wife, Melissa, sold their home in Colorado and bought a conversion van, lovingly referred to as The Vansion. While Melissa drove, Ryan wrote code. Spencer started calling RV owners on Craigslist and landed our first lister. Tyler, also a co-founder, began configuring servers from his living room.

The day our site went live, we got our first renter. We had no RVs for her to rent in her area, but she was insistent that we take her credit card. She wanted to be the first customer on our site. We will never forget her and the excitement that she conveyed.  RV owners began to call in to ask Spencer how they could earn a second income listing their RVs on Outdoorsy.

We realized that we had a major problem – we needed an insurance offering to protect our owners and renters.  After more than 30 meetings with insurance companies, where we were told “no, that product does not exist and we can’t help you”, we got to W.R. Berkley in Jersey City, where the COO said, “my wife and I are avid RV’ers and come to think of it, there should be an insurance product that would make your marketplace truly legitimate”.  Two months passed and when we all got back together at the insurance firm, they had good news and bad news.  The good news was that they would build an insurance product with us. The bad news was that they required a large sum of money up front.  When they told us the amount, we choked.  The amount was the total sum of my life savings. The team and I met that week and we discussed it. It was a scary moment and the biggest decision we ever had to make.  The team said that they would support not going forward with the business as it was just too much to ask.  But having lived in an Airstream for over 7 months, and truly finding that peace that comes from eliminating all materialism from our lives, I looked at Jen and said why not?  Let’s roll the dice.  If it works, we have something big.  If it doesn’t, then we can always go find jobs.  Jen and I agreed that we did not want to live with the regret of not going for it.  So, we emptied out our life savings and we rolled the dice.

The Vansion
The Vansion

And then we set off for an expedition in content capture

We couldn’t afford to advertise so we got creative and partnered with a crew of filmmakers and storytellers who Jen knew from her years at Ogilvy. For 12 days in the summer, we set out on the open road along the coast of California to reveal the world of RVing in a way never before seen. This was an expedition in content capture that would put a stake in the ground for the Outdoorsy brand.


It wasn’t about making a corporate video, but we felt that a video was the best way to tell the story and we put it on social media. We made many improvised stops along the route where adventure took over: much like the experience of RVing itself.

We’re building our dream team.

We got kicked out of enough cafes and coffee shops and eventually hotel lobbies. So Jen suggested that it was time that we get an office. We rented a 1-room office in downtown San Francisco that came with no furniture, no office equipment and was being used as a file storage room. It did feel like we were starting to take off; it didn’t matter that our office was an empty space. It did include a bathroom down the hall, which we thought was pretty great.

We knew we had a business and our team needed to expand. With had hiring requirements: passion, drive and creativity…. but no ego. The must-haves to work at Outdoorsy are a hard-working attitude and passion for outdoor experiences. Those values brought us Meredith, Michael, Jess, JB, Horst, Jack, Lucas, Ken, Ryan L., Logan, Hannah, Dave, Marcelo, Pam, Suzie and more.  Every day starting at 6:30am, the team is on intercom or the phones talking with users who need help or have questions about how it all works. By 8:30pm, we are finally leaving the office. We’d run to FedEx and UPS to send out insurance docs, brochures, bumper stickers, T-shirts and insurance cards to our users.

Still, the important things remain the same. As Marc Benioff, founder of Salesforce said “You have chosen the wrong path if it’s not fun. And you are probably not taking enough risk if it’s not hard and rocky sometimes.”

We did anything possible just to get users and revenues so that we could grow and be a real business.

Thank you.

So in perhaps one of the greatest understatements of all-time, we’d like to say thank you for supporting us on this journey. For bearing with us through our growing pains, false starts, and the time Ryan had to transfer money out of his personal bank account to pay for a renters first rental on the platform as we could not process a credit card.

I think we now realize when we decided to go for it that day in Vancouver, it would be an adventure. That is for us, everything about the Outdoorsy experience — the vehicles, the users, their beautiful stories and unique experiences — is getting radically better.

Writing this in January of 2017, it’s hard to believe that it’s been only 18 months since we started with the idea and then those first lines of code were written. It feels like yesterday, yet it feels like 5 years ago.

So much has changed for the better

  • The few initial RV owners now add up to hundreds of thousands now
  • Our team has grown from 5 passionate souls wearing hiking boots and hoodies working from remote coffee shops and cafes, to a 275+ strong persons working team in California, Florida, Utah, Indiana, Texas, New York, Canada, France, the U.K. and Australia and growing fast
  • We upgraded offices in SOMA, just down the street from Airbnb (and we’re still carrying and assembling furniture up flights of stairs. There are no elevators in our new newer building)
  • We launched our Pro product called Wheelbase that was made specifically for professional users; we launched our Pro Host program for owners of multiple vehicles, built new integrations into all DMV databases and improved insurance programs for US, Canada as well as international renters.
  • We then moved our HQ to Austin

We’ve always dreamed that life is not to be lived solely in an office building, that we all are Outdoorsy, and stewards of the nature all around us. There is something so tangibly American about the wide open road. It’s the best way to see, truly see, the country and many vehicles in all their forms, are baked into the American landscape. Road travel is the great connector, both literally and figuratively. Symbolically, it takes a country so rich in diverse topography and people and unites them. Our road ahead is unpaved but open and vast, and we can’t wait to share the journey with you. See you out there.

Keep on rollin from Team Outdoorsy,


P.S. Want to read more about our team, check us out here.

P.P.S Not signed up for Outdoorsy yet? Sign up here – we deliver a great service that brings private and unique vehicles to would be travelers from all over the globe, inspirational stories, and a hell of a lot more to your inbox every week.

Team Outdoorsy, Outdoorsy Author

Ready to get started.

Be the first to get doses of destination inspiration, and discount codes.

We care about the protection of your data. Read our privacy policy