Sometimes Working for Free Can Pay Really Well.

Imagine this: you’ve always wanted to be a painter, but you’ve never owned a paintbrush. Then one day, you met a friend who shared their paintbrush with you. You had no technical skills, no training, no experience using it, but what you did have was a very vibrant and very big imagination and no reason in the world to be self critical. You were just having fun! You were just painting what you wanted without trying too hard to be impressive or do things the “right” way for some audience who would judge you.

Okay I know! What if we just finger paint this picture of an airplane and give it to the airport to hang on their refrigerator! YEAH! LET’S DO IT!

In the summer of 2020 my friend Hilary and I decided to shoot our first video together. Her husband was a flight instructor at the flight school in town, and that seemed like an interesting enough subject to cover for us to tackle the big goal of just…doing what we said we wanted to do (shoot videos). It was also something we naturally had access to, which, when just starting out, is something you want to take advantage of when experience is really all you’re after.

This was really great idea for multiple reasons. 1) We just got to play. We weren’t interested in selling anything or trying to make any money, we just wanted to start telling stories and sharing experiences in a way that was brand new to both of us. So choosing to share a day in the life of a flight instructor was a really cool intro into getting to do that. 2) It turned out to be a very interested and enthusiastic audience!

The Break

The video itself is funny for us to watch back now that we’ve both been doing this for 3 years (and have gotten much better at what we’re doing). It’s amateur, for sure, so it’s a good thing I’m not a perfectionist or I’d probably cringe. But I don’t cringe…why would I cringe when watching the concrete start of everything good that has ever happened to me professionally?

We shot the video in an afternoon and took probably a week to edit it. Today that would take about a day but at the time we really didn’t know what we were doing, we had much slower and less efficient software. We’d planned the idea for a few weeks in advance, which I think was the real magic that we did right. The other, and arguable most right thing that we did was sending the video to the airport that hosts the flight school. I watched a lot of Gary Vaynerchuck at that time and basically just did whatever he said to do when starting a business, and he advocated for doing a lot of stuff for free. I know a lot of creative people are super against this but dude…that one decision is the reason I currently have an ongoing contract with a major car company doing video work that pays me to travel all over and do really fun things. Three years ago I didn’t know how to even turn a real camera on, and today I get paid by huge brands that respect my work and my mind. What does this have to do with our free little 5 minute video we shot in the summer of 2020? Well…

Like I said before, this audience turned out to be very enthusiastic. We posted the short to our personal instagram account and immediately several pilots sent us private messages about how incredible it was. We got messages from pilot wives about how it made their husbands cry. We also got an email back from the flight school asking if they could buy the video from us to post on their personal YouTube channel. We were stoked! They were stoked. We almost immediately set up a meeting with their marketing team to talk about future projects (which we did) and our first professional contract was born.

Now this is cool on it’s own…but the coolest part about it is how it brought us into the orbit (<– heh…) of an airplane manufacturer that shared space with the airport that hosts the flight school. Lucky for us there was a lot of crossover between the tight knit pilot community, and we ended up getting approached by an aerial pilot by the name of Christian Bolton who was working for the manufacturer about producing a video series for them to take to Osh Kosh. If you’ve never heard of Osh Kosh, think of it as the Coachella for pilots and airplanes. It’s a big deal. And Game Composite is an equally big deal – they’re the only domestic airplane manufacturer making some of the most arguably impressive aerobatic airplanes in the world.

To put it into perspective: this was insane. This is the kind of video work that would be on someone’s 5-10 year bucket list, and we were being approached to tackle it after working together for approximately 5 minutes, after making some very simple video about a day in the life of a pilot in the backcountry because we just wanted to do something fun one day.

Some fun BTS: