Michael Caldwell

Meet Michael! Michael has served as the Republican member of the Georgia House of Representatives from Georgia’s 20th district since January 2013, and he is currently running for state senate. He serves as a member of the Regulated Industries, Economic Development, Code Revision Committee (tasked with repeal of law), Budget & Fiscal Affairs Oversight, Interstate Cooperation and State Planning & Community Affairs Committees. He is also the Chairman of the Cherokee County Legislative Delegation.

In the private sector, Michael is a Managing Partner at Black Airplane where he and his team build enterprise solutions in digital applications and websites. In the two and a half years since Michael and his business partner, best friend and former college roommate David Leggett acquired and launched Black Airplane, the team has grown from three to seventeen full-time employed Georgians

He has climbed Mt. Kilimanjaro (the highest peak in Africa and tallest freestanding mountain in the world), hand-copied the New Testament, and he finished his undergraduate degree in less than three years.

Michael married his high school sweetheart Katie shortly after graduating with his BBA in Finance from Kennesaw State University. They are the parents of Oliver (Ollie, 5 years) and Elizabeth (Eliza, 1 year). Michael, Katie, Ollie, Eliza and their two Great Danes “Liberty” and “Justice” live in downtown Woodstock. Our host, Susan Guda, caught up with Michael prior to the pandemic in February 2020.

 How long have you lived or worked in Woodstock?

We came here when I was in the first grade. I married my high school sweetheart; I went to Kennesaw State. This is home.

When I got elected, I was the youngest state legislator in the United States for whatever that’s worth, and it’s been an adventure. The private sector has been good to me, so serving in public office here was never about building a career. Woodstock is where I grew up, has been a great place to build a business, to give back in public service, and Katie and I are proud to call it home.

Michael with his wife Katie and their two children Eliza and Ollie.

What inspired you or led you to your public service?

For me, I was always a history buff and I fell in love with the history of this country. In high school and college, I used to go sit in the gallery at the Georgia House of Representatives because our General Assembly is older than the United States Congress. We have one of the oldest continually meeting legislatures in the world here in Georgia. I used to go to sit and watch because I thought that history was awesome. This was before I ever thought I would run for office. I was this weird Republican who believed in a conservative agenda, but also felt lobbyists had too much financial interest in the capitol, which meant neither side wanted to sit at my lunch table.

Ten years ago, I ran against a six-year incumbent when I was in college. I sat in a room with my fiancé now my wife, and my college roommate now my business partner, and we brainstormed. At the time I just knew that I had a belief about lobbyists that was different than the incumbent. We ran that race in 2010. We didn’t win so I went and got my career started, I got married. Two years later everything looked the same, so I ran again. We knocked on thousands of doors and vastly underspent the incumbent but won with 55 percent of the vote. I was sworn in in 2013.


Tell us about Black Airplane.

I am a co-owner of a Woodstock-based website and application design and development agency called Black Airplane with David Leggett. We are 50/50 partners. David has been a friend since we were kids. He was my college roommate. David is one of those tremendously talented software developers that you would never expect to be right here in our backyard. It was March 2017 when we bought the company, and we’ve gone from the three of us to 17 full-time employees now.


As a millennial, what is your perspective on the collaboration between older and younger generations?

 I think one of the biggest tricks Americans play on themselves in every generation since this country was founded, is that we pretend like everything we’re going through is the first time it’s ever happened. Right now we’re watching the shift from Millennials being the punching bag to Generation Z being the punching bag. We always act like young people are dumb and old people don’t get it, but in reality, they’re not that far off from one another when it comes to issues. One of the biggest things we need to make sure of when we are thinking generationally and trying to make policies around that is to avoid assumptions. The reality is we’re together on so much more than we are apart.


What is your favorite restaurant in Woodstock, and what do you love there?

We’re sitting in it. I got to know these guys and their story early. The CEO Spencer was my pastor before he went full-time into Reformation Brewery. I love this place because I feel like I got to play a small part in their story and I’m just really proud of these guys.

They built something worth building. Reformation has helped build the culture in Woodstock in so many ways, and I’m so grateful it’s a brewery like this because breweries take on all kinds of flavors. This is such a neat family-focused small-town feel to it.

Michael Caldwell at Reformation Brewery in Woodstock, GA

Who is the most interesting person you’ve met here in Woodstock?  Who would you like to see nominated as a Face of Woodstock? 

There are so many people here who contribute in so many different ways. Woodstock is full of so many interesting people. I’ve lived here since I was six years old, so If I have to pick somebody, my wife is it. As for the second question, you’ll have to ask my wife. She’s a Woodstocker at heart, always giving back behind the scenes. Well, she’s certainly my favorite person. Another person for me is David Leggett. He is a brother to me in every possible way. He constantly surprises me and holds me accountable.


If you could travel anywhere in the world right now, where would it be and why?

Any country I haven’t been to. I was on a thousand planes in seven years. Traveling to new places is one of my favorite things.


What has been your favorite experience?

I climbed Mount Kilimanjaro in October of ‘16. That was really cool. It’s an eight-day climb. At the top, it was negative 20F and the oxygen level is 20 percent of what it is here. We went through every environment Africa offers. It was just amazing.

Michael at the summit of Mount Kilimanjaro in Oct. 2016.

What advice would you give a crowd of people?

Take ownership. If we stop asking how we got where we are and start asking where we want to be tomorrow, there is no limit to what we can do.


You are so public and accessible, what do you do to unplug?

 My family is my way to unplug in a lot of ways, my wife has been my best friend since I was sixteen years old. So, time with my family, even if we’re working, is my safe place. I know that my wife and my kids are not judging me. I can make a ‘dad joke.’ And I’ve got good friends like that too. My friends David and Katy are a safe place for me. My unplug is sitting with people that I know and trust. I don’t have to worry about saying something dumb. But there is no on or off switch with me, so I’ll make my super cheesy dad jokes and they will still have to hear my policy conversations because I don’t turn that off either, it’s just me.  


What makes you the most nostalgic about Woodstock?

Sitting in a Woodstock city council meeting is a real throwback to old America. They literally still meet in an old church building. Anyone can go in and speak, I think our city council does a really good job of being accessible. Although we are a growing city of over 30,000 people, we’ve still got that sort of old town council feel to it.

I love going into town and voting. We used to vote at the library right downtown here. I have gotten to know all the council members, and anyone here can know all of them. So, going in to vote for someone I know and know why I’m voting for them, that’s what this country is supposed to be about. It’s about going in and picking your neighbor to serve for a time, so it makes me think of America.

Michael has been serving the Georgia House of Representatives for the 20th district since 2013.

Choosing anyone alive and a non-relative: with whom would you love to have lunch?  Why?  Where in Woodstock would you have lunch?

I am a die-hard Taylor Swift fan. That could be a fun lunch. We’d probably disagree on every political point there is, but she’s a millennial who in so many ways got to where she is by working really hard, hit success early, and redefined the music industry. She just strikes me as a tremendously interesting person and that could be a really fun lunch.


What is your favorite thing or something unique about Woodstock?

 It is the biggest little city in America. We have everything here. I really do believe from a political standpoint that we’re coming up on a leadership mantle nationwide that we will never see again. We are walkable; we have a council and a mayor that care about the town, we have a business community that is thriving, we have people who are lining up to live here. In every metric, we are winning. Every bit of what you would want in a town is here. I don’t have to leave, and yet when I want to, I’m 45 minutes from Atlanta. Woodstock is a perfect balance.


Where do you see yourself in 5 or 10 years?

 Here. Five years from now I hope I will be serving in the state senate. I hope that Black Airplane is thriving and employing more Woodstockers. In five years, my kids will be 10 and 6, I don’t know if we’ll have more. Ten years from now I just want to be serving, I want to be here, and I want to be making it better. And I am 100 percent okay if my name isn’t on a ballot. There are so many ways to serve this town and I want to be wherever I can best serve.

Michael is a Managing Partner of Black Airplane, the Woodstock-based website and application design and development agency.

(Even for friends or family), what is something interesting that most people don’t know about you?

 I don’t know, I just told you I’m a huge Taylor Swift fan [laughs].  Oh, here’s one. When I was two or three years old, apple juice rotted all four of my front teeth out, and so I didn’t just have crowns until I lost all my baby teeth, I had silver crowns. So, until I was nine years old, it looked like I was wearing a grill every day [laughs].


What three words or phrases come to mind when you think of the word HOME?

 Welcoming, open, exciting.


How do you think we can find balance in the growth of Woodstock while keeping it affordable for the people who live here? 

The challenge of the marketplace at large is that it exists in friction. I think that downtown Woodstock is going to grow, and it will grow outward, it will have to. Part of the problem right now is that if you really look at downtown Woodstock, we haven’t expanded. And I say that meaning the private sector, the city doesn’t do this itself.

The private sector hasn’t expanded downtown Woodstock geographically since ten years ago when we really started developing. What that means is that we have a limited pool of people who are going to open things and we have a significantly smaller downtown area than some others in our region, even smaller than Canton. We’re going to have to start moving north on Main, we’re going to have to start moving south, and as we do, I think you’ll see those rents come back down again.

The challenge right now is convincing developers that they don’t only have to build just townhomes. There is a demand for office space and for commercial space. But they know they’re going to make money on townhomes. There is no ‘build it and they will come.’ We have to prove they’re coming and then they’ll build it. Having a conference center downtown will change things. It is the next evolution.


What is your favorite movie OR what is the first movie you remember seeing in a theater?

The original Mary Poppins. I love Disney. The company changed the American viewpoint, it got us dreaming again. I feel like Mary Poppins was the peak of Walt’s time. I just love everything about it.


Michael and his family take a photo with Mary Poppins at Disney’s Epcot resort.

If you had a full-time staff member that was fully paid for, who would you choose?

Chef, Housekeeper, Driver, Coach, Physical Fitness Trainer, or Nanny?

Physical trainer. It’s the one thing that’s going to pay dividends the longest. If I’m looking for the best bang for my buck, that’s it.  

Katie and Michael after completing a Disney half-marathon.

Michael in Community 

Michael can be reached through the Georgia House of Representatives, through his Woodstock company, Black Airplane, and on social media.





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