We caught up with the brilliant and insightful Jack Delehey a few weeks ago and have shared our conversation below.

Jack, appreciate you joining us today. Alright, so we’d love to hear about how you got your first client or customer. What’s the story?

In 2015, we had an idea: why don’t people advertise on rooftops of buildings near airports, targeting eyes in the sky?

For about a year, the idea was just that, an idea. We needed to solve two problems: First, we needed rooftops. Second, we needed advertisers. At the time, we had neither…we just had an idea.

Then in 2016, we caught our first break. I had cold emailed dozens of the largest warehouse owners in the country, in essence asking them if they’d provide us access to their rooftops. One of them said yes, agreeing to a % of future sales as payment.

We had solved for step 1…we had our rooftops. The second step would be easy, right?

It wasn’t. We were close with several major brands but in every sales meeting we hit one major roadblock: “Cool, so how many of these have you done…and can you show us what one looks like?”

Our answers, as you can imagine were: “Zero” and “No, we can’t because we haven’t put one up yet…do you want to be the first?!”

This was too large of a hurdle for an advertiser to overcome.

So after 6 months of sales pitches, we went back to the drawing board. We needed an example rooftop sign and we needed to figure out how to fund it.

Then we had an idea: what if we could convince our building owner (the same one who gave us access to their rooftops) to be the first rooftop sign as well? We’d do it at-cost…and it would give us the example we needed in these sales pitches. We brought the idea to them…and they, amazingly, said yes.

So our first paying customer was not a major brand-name…it was a real estate company, advertising on their own rooftop. The expenses from the project gave us net-zero in profits but that was fine by us. We then used photos from the first campaign in future sales pitches and, 7 months later, won our first profitable paying customer: Anheuser-Busch.

Now, in 2022, we have worked with Anheuser-Busch, Netflix, Amazon, ABC-Disney, Paramount Pictures and more.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

Hey there! Jordan and Jack here, and we head up the flyby team. Our mission is to transform unused rooftop space into wonderfully epic advertising media–and we like to have a little fun along the way.

In the summer of 2015, we were flying an average of 200,000 miles and 180 flights per year in our consulting jobs. It was during the descent of one of these cross-country flights, peering out of our plane window when the flyby ads idea struck us. From then on, each flight became a recon mission, and though we both gave up our consulting gigs to pursue flyby ads’ development and success, we continue to keep our eyes open (and down) from the skies.

This is not the first time the two of us have joined forces. we were classmates and close friends at Vanderbilt University, travel mates during our semester exploring the world, and workmates at our previous consulting employer. our specialties are complementary, and our weaknesses are jabs at our home sports teams, craft beer, and rom-coms. you can find us slicing down the ski slopes, playing spike ball on the beach, or setting up pop-up offices around the country as we grow and expand FlyBy Ads.

Can you tell us about a time you’ve had to pivot?

When Covid hit in 2020, we learned how difficult it can be when you have a business based on air travel and huge events.

Our revenues dropped to nearly $0 and we learned two things:

1) How valuable it was that we had set up a lean company – we still to this day are the only two full time employees at FlyBy Ads. This allowed us to weather the storm so to speak.

2) We learned to pivot, transitioning our advertising model to a more typical billboard/wallscape model for 2020 & 2021. This pivot allowed us to remain profitable and wait for our real product–rooftop advertising–to return. Now in 2022, while we have largely transitioned back to the rooftop advertising model, our experiment with traditional advertising has given us yet another idea to pursue to make the traditional advertising world more efficient–perhaps if we get to do this interview again in 2023, we’ll be able to tell you more about it!

How did you put together the initial capital you needed to start your business?

This is a great question. When we first started business we heard grandiose ideas about million dollar funding rounds.

Our funding was $0. And we liked it that way. It allows us to have complete autonomy in the business. But because of that, we had to get creative. As I stated in the previous story about our first sale, we didn’t have the funds to actually build a rooftop sign…so we convinced our building owners to be that first sign! In essence this allowed us the example we needed to prove the concept. From there, our sales have funded the business to this day.

Contact Info:

• Website: https://flybyads.co
• Instagram: @flybyadvertisements
• Linkedin: https://www.linkedin.com/company/flyby-ads-llc
• Youtube: https://www.youtube.com/watch?v=1sZSFBzIHvs

Image Credits
FlyBy Ads, LLC