From the beginning, we designed OpenAirplane to be failsafe. This timing will give us time to process payments, and provide for the orderly shutdown of the platform. We’ve always done our best to ensure vendors got paid before we did. We built that into our system from day one. We’re taking care to protect everyone’s data, just as we have since we started back in 2012. We hope we leave the aviation world maybe just a little bit better than we found it.

We Tried To Make Aviation More Valuable For Everyone

In 2011, I started thinking about what could help make aviation more valuable. At the time, others were working to make learning to fly better, but few were talking about how pilots could use their hard-earned privileges. That conversation sparked the idea that maybe we could make renting an airplane as easy as renting a car. Inspired by the sharing economy, the idea became an itch that I needed to scratch. I knew that if I didn’t get the idea off the whiteboard and into the world, I would regret it forever.

We set about solving two problems with OpenAirplane. We wanted to make it easy to find aircraft. We also wanted to take the hassle and the expense out of renting an airplane. Spending half a day and hundreds of dollars to get checked out to fly the same model of an aircraft we fly at home always seemed silly, and thousands of pilots we surveyed told us they would fly more if such a service existed.

I had found a great technical co-founder in Adam, and we started hinting to friends that I was working on something new codenamed, “Project Awesome.” Once we had the idea formulated to the point where we could explain it to people without tripping over ourselves, we started signing up fans. By the time we launched OpenAirplane.com in May of 2013, we had more than 5,000 pilots who had signed up to get updates. We started the service with a couple of dozen operators across the country. We eventually grew the network to include more than a hundred locations, with hundreds of aircraft available to rent across the US. At last count, 67% of the pilots who joined the service had an OpenAirplane operator based within 25 nautical miles from their home.

We bootstrapped the business for three years. We worked on it for about a year and a half before we launched, just nights and weekends. I left the corporate job three days after the beta went live. In early 2016 we raised a seed round with some pretty excellent angel investors. Those investors all came back to keep supporting us in a bridge round in 2017, where more folks just as passionate about what we were doing joined in.

As we grew OpenAirplane, renting airplanes to pilots, we discovered how broken the charter marketplace was as well. Charter brokers created a race to the bottom, yet kept between five and fifty percent of the charter booking, with zero transparency. We put the investments in the OpenAirplane platform and network to work, and in late 2016, launched FlyOtto.

We built FlyOtto.com to match travelers with pilots and planes, on-demand. We focused on delivering real-time pricing, a smoother booking experience, and book trips on more efficient piston and turboprop aircraft to make flying private possible for a fraction of the cost of chartering a jet. The charter platform quickly ramped up to bring in far more revenue than our rental business.

At last count, more than 25,000 people had signed up to fly with us across the two platforms.

There is a Fine Line Between Passionate and Pollyanna

General aviation is a bit like teenage sex. Lots of people talk about it, even when few are doing it. Survey data is not anywhere close to being as valuable as being in the market and following real money. Consumers are fickle, and humans are terrible at estimating utilization. Long before we launched OpenAirplane, we surveyed thousands of pilots. They told us they would fly an average of 10 hours a year more than they do today. That did not come to pass. Demonstrating to us at least that surveys are a terrible way to capture intent. While the idea of OpenAirplane won us praise, fans, and even super fans, the reality is that too few pilots took to the skies to make the operation sustainable.

If there’s one thing that we learned the hard way, it is that it’s tough to get pilots off the couch and into the cockpit.

The charter business is no walk in the park either. We learned a lot operating a true marketplace. The technology we built really did allow us to break away from being just brokers. But we measured everything we did. That data showed us how getting to sustainability would require much more capital than we first assumed. We were able to model an ambitious plan to scale into a big profitable business. It was a good plan. But without access to growth capital, it became impossible to get there. Round-trip economics is a bitch.

Some of What We Learned Along The Way

If your idea is important to you, go talk to the person who is supposed to tell you no. In our case, pilots we spoke with got very excited about the concept of OpenAirplane, but most were quick to tell us how the insurance industry would never support us. It took crashing an Aviation Insurance Association event to meet the folks who eventually enabled us to move forward. If there was one thing new and novel that allowed us to do what so many told us was impossible, it was the simple act of asking for permission even when everyone already knows the answer will be no. (Have a good plan.)

The smartest thing I ever learned about fundraising was, “If you want money, ask for advice. When you ask for money, you’ll get advice.”

Marketplace businesses have a chicken or the egg problem. Only by building relationships across the industry for years did we manage to avoid a cold start. We worked so hard on building the supply side that it was easy to convince ourselves that the demand side of the equation would be easy.

Software and automation will only get you so far. Aviation is an industry that relies on the experience and talents of people. Maybe one day, pilots will go the way of elevator operators, but not anytime soon. We found that the technology we built made people better at serving travelers, but that trying to take humans out of the loop is ultimately not a good idea.

The definition of a startup is an organization in search of a viable new business model. Sometimes a startup’s contributions aren’t just monetary. It is that search that can create lasting value for the ecosystem. In our case, we’re immensely proud to have created value for a number of our partners, who include names like Cessna, Cirrus, NASA, and Boeing. It’s exciting that our work will live on in what comes next for aviation.

Here’s What I Wish We Did Differently

Not. A. Damn. Thing. 97% of seed-stage funded startups fail. They raise an average of $1.3MM before they die. (Check.) On average, they survive for 20 months. (We lasted 91!) We made plenty of mistakes, but we always put our partners, our community, and our team first. OpenAirplane enabled many pilots with bucket-list experiences. FlyOtto opened up access to aviation to travelers in a new way. I’ll never forget how important the mission was to our team. I’ll always be grateful to our investors who dared to give us the chance to build something pretty great. I’m better for having taken this journey, and I am thankful to all of you who came along for the ride.

See you at the airport.