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Recognizing 100 CEOs & C-level Executives
Michael Caldwell Black Airplane City Of Woodstock

Michael Caldwell

Managing Partner / Mayor

Black Airplane / City of Woodstock

Location: Woodstock

Industry: Technology

In his roles in both the public and private sectors, Michael Caldwell is endeavoring to build environments in which individuals and families can thrive and truly reach their potential. “If I am fortunate enough to leave a legacy that outlives me, I hope that it will take the form of organizations, institutions and communities that enable individuals to achieve a sense of adventure in their lives and to live in an attitude of abundance,” said Caldwell, managing partner of Black Airplane and a Titan 100 Hall of Famer.

Black Airplane is a creative software development firm that builds apps and websites for clients ranging from startups to Fortune 100 companies. Scaling companies and communities should see exponential growth in the opportunities available for every individual involved, according to Caldwell. “If I can help influence the places in which I live and work with an attitude that our best days always lie ahead, then I believe I will have achieved the best legacy any person can hope to leave,” he said.

Navigating dual roles as a business owner and the mayor of one of the largest, fastest-growing cities in Georgia has offered a unique opportunity to leverage these two past years and continue to grow as a leader, said Caldwell. Black Airplane surpassed the 30 full-time employee mark, and that milestone has created a scale upon which the future of the business is much more secure and from which it can scale to the next level.

“Throughout each of my roles, I am continually reminded that every individual is called to leadership and that good leaders prioritize their people,” said Caldwell.

Although Black Airplane has several stated values, Caldwell said the one every single employee can quote is “We invest in each other.” The firm invests in its colleagues, customers and every stakeholder. “Investing in one another isn’t limited to easy, feel-good conversations and actions,” he said. “True investment in another person means having the courage to have a hard conversation that you know can help them grow and expecting more from one another.”

Defining a focused vision and keeping that end in mind is also crucial to success, said Caldwell. “Scaling, growth and leadership in general should always be people- and purpose-driven,” he said. “Every generation has its leaders, but the generations and the leaders who achieve truly great feats are those who have a clear view of success and inspire others to join in the mission.”

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“Every generation has its leaders, but the generations and the leaders who achieve truly great feats are those who have a clear view of success and inspire others to join in the mission.”

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