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. 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 meant “we needed to do something different.” It was that evening we started talking about ideas for a profitable business that helped others. We agreed on one thing: we never wanted to work under fluorescents light again. Our idea had to involve outdoor living.

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 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 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 life.

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. Jen sold her house, I sold mine and we then set out to build a marketplace for recreational vehicles, but more importantly, we set out to do something that had never been done before; to give people to easy and economical access to experience the great outdoors.

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 to start talking with travelers and RV owners across the country 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 towards 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. 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 6 months with RV owners on Craigslist? Yet we learned so much about what people needed, and what they were thinking.

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

Jen, Ryan, Tyler, Spencer and I 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 May 2015, we flipped the switch, and Outdoorsy.co went live.

Our community began to grow…slowly. When we weren’t in the Airstream, we worked out of coffee shops and cafes. Ryan 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 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.

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 a 10 days in May, 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.

You can watch our brand anthem video here.



We’re building our dream team.

We got kicked out of enough cafes and coffee shops and eventually hotel lobbies. So Jen suggested we get an office. We rented a 1-room office in downtown San Francisco that came with no furniture, no office equipment, but 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, which we thought was pretty great.

We knew we had a business and our team needed to expand. With had hiring requirements: passion and creativity but no ego. The must-haves to work at Outdoorsy are a hard working attitude and passion for outdoor life. Those values brought us Meredith, Michael, Channing, Tom and Jonathon and Lucas.  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 7:00pm, we are finally leaving the office. We’d run to FedEx to send out insurance docs, brochures and insurance cards to our pro hosts.

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 July of 2016, it’s hard to believe that it’s been only 18 months since we started and 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 many thousands now
  • Our team has grown from 5 passionate souls wearing hiking boots and hoodies sitting in remote coffee shops and cafes, to a 12+ strong person working team and growing fast
  • We were invited to join the NFX Guild and we took capital from some of the best investors in Silicon Valley
  • 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 older building)
  • We launched a second 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’ve always dreamed 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 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 the Outdoorsy crew,



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.

P.P.P.S Want to join our team? We are hiring