Cherokee Office of Economic Development · Cherokee by Choice.

From Freelancer to Managing Partner—David Leggett Shares His Journey 

October 22, 2018

“I was fascinated with building and programming computers when I was younger. I started developing websites when I was 10 or 11 and started selling advertisement space on them. Back then my parents restricted electronics to one hour a day but when a $1,000 check from Google arrived in the mail, they reconsidered the rule,” said David Leggett as he shared the story of how he fell into the website development industry to the Lunch Circuit audience.  

The Lunch Circuit had the opportunity to host a founding member of The Circuit as the featured entrepreneur for the October gathering. David Leggett of Black Airplane sat down with Jonathan Chambers of the Cherokee Office of Economic Development (COED) and shared his transition from freelancer to now a managing partner at Black Airplane, a website development agency.  

David Leggett is a textbook example of an entrepreneur, but his journey through entrepreneurship has been anything but ordinary. Leggett taught himself how to code, launched an internationally recognized publication, and managed a political campaign all before 21.  Leggett credits his success to the values his parents taught him over the years, the importance of working hard, and staying true to himself.  

Shortly after the success of the websites, Leggett went on to launch UX Booth, a publication for the user experience community, with a few friends he met during the Georgia Governor’s Honors Program—a summer long intensive hosted for sophomores and juniors in high school. From there, Leggett began classes at Kennesaw State University and became roommates with childhood friend Michael Caldwell. Leggett took a break from UX Booth to help launch Caldwell’s campaign as a State Representative. “I don’t have the statistics on this, but if Caldwell was the youngest State Representative in the country that makes David the youngest campaign manager, right?” joked Chambers. “I don’t know about that, but it was a pretty wild time having everyone tell you that it couldn’t be done and then we did, and we turned the system around on its head,” replied Leggett.  

Tell us about Black Airplane 

Black Airplane is a design and development agency that builds apps and websites that win. That is a fancy way of saying that we are a very objective oriented business and rather than creating the prettiest website, we focus on a website that will increase sales and reduce costs.  

Michael and I had worked together a few times before and when Python Safety was acquired by 3M, I suggested starting a website development agency. As we were building the team, I asked John Howard to come on as our lead designer. It was then I found out he had a company called Black Airplane and the three of us decided it would make more sense to acquire Black Airplane instead. We added on the development capability and a sales team and moved the headquarters from Atlanta to Woodstock which is how we ended up at The Circuit.  

The Circuit was our launch pad. If we didn’t have a space like The Circuit to start the business from, I don’t think we would have really gotten it off the ground like we did in the first month or two.  

How did being in a coworking space help you with your day to day operations? 

The face to face. I’ve been a part of agencies that were fully remote. Working remotely can work, but having the ability for face-to-face time helps grow a company culture and speed up production. It was important for us to have a place to call home and over time we saw that we really liked seeing everyone on a daily basis.  

How do you keep the culture of Black Airplane while adding more employees?  

The culture changes every time you hire a new person, but that’s a good thing. We have a list of company values and number 11 is “always win.” Another that is most important to our team is making an effort to invest in each other and to expect to be invested in. Something that our team does very well is that everyone makes sure everyone else is succeeding and getting better every day. This has led us to launch an apprenticeship program where we bring in people who may have never touched a line of code in their lives and teach them how to become a developer. By the end of the program, hopefully we have someone who has bought into Black Airplane as a company, and they feel like it’s their turn to help the company succeed. That’s the core of the Black Airplane company culture.  

Tell us about a major loss and win when it comes to your entrepreneurship career 

Pain is definitely a catalyst for change. We had a project we were working on last year. We thought we had a good handle on things and before we knew it half the team was working 12 hour days and halfway through the client refused to pay us. It was a nightmare for everyone on board. It was certainly a huge loss for us and the time it took from our families was awful. We didn’t get paid for it either and that threw salt on the wound.  

The product that we are selling is so vague and ambiguous that sometimes when the client is signing the paperwork they are just signing a big list of “I have no idea what this is going to end up looking like but I sure hope it’s what I actually need.” If you don’t have processes and clear communication channels in place, it will become a disaster down the road.  

Other losses have been the many websites that I launched that did not generate a dime after months of work, but I have also created sites that have done very well so I’ve come out ahead.  

A major win that Black Airplane had recently is with a company we have been working with since day one. We were working on a small project for them and wanted to do more work, but they saw us as a small fry. We went above and beyond with the project and showed them what we were capable of and, because of that, they walked away from another agency and booked us for the rest of the year.  

How do you define an entrepreneur and why did you decide to stick to it rather than going down the corporate path?  

For me, the decision was easier because I became an entrepreneur at an early age. I think it’s all about risk management. At one point, I learned that salary is the worst money you can make out there and if you really want to do well, you have to put skin in the game. If you want to make a lot of money, the best way to do that is by starting your own business and being willing to lose everything. I’ve lost before but I’ve also had some great opportunities. I look for opportunities and make calculated decisions based on the risk and reward. The only thing that really matters is working harder than everyone else around you. It’s not hard to be an entrepreneur but it’s hard work.  

You are a member of the Woodstock Downtown Development Authority Board. Tell me more about being a local leader.  

 I didn’t even know that was a thing so I was never trying to get on the Downtown Development authority board. David Potts reached out to me and asked if I would like to join. My initial response was that I had no idea what I would be doing and they probably didn’t want me, but my wife encouraged me to go for it. I think that’s something Woodstock does well, we try to have a very diverse group of people on leadership teams so more perspectives are brought to the table, which is neat because other cities only want bankers and lawyers on the board. I think adding other business leaders into the equation only helps bring different ideas and opinions.  

 Why Woodstock?  

All of the other agencies like us are in Atlanta, but that means everyone spends two hours on the commute to work every day. We wanted to build something in Woodstock that was close to home and give people the place to have an agency life but have less time on the commute and more time at home with their families. It’s a great fit all around.  

I moved to Woodstock 25 years ago and back then it was mostly trees. It’s my home and I think it’s the best place for my family to grow. There is so much community and opportunity that I can’t imagine living anywhere else. I love traveling, but this is home. 


 The Circuit would like to thank Leggett for his contribution to the vision of creating a space for Cherokee’s entrepreneurial community. We know he has a bright future ahead of him, and we are so thankful he has chosen Woodstock as his home. 


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