[5] He is also the cofounder and the Partner for Operations and Business Development at Black Airplane, an award-winning digital product company headquartered in Woodstock, Georgia.

Previously, Caldwell was a member of the founding team and partial owner at Python Safety, Inc. which specialized in "Fall Protection for Tools" and was acquired by 3M in 2015.

He authored the most widely adopted dropped object prevention procedure in the world and spent years traveling the globe speaking on this topic.

[citation needed] In August 2021, Michael Caldwell was the sole qualifying candidate to become the mayor of Woodstock, Georgia and became the mayor-elect.

[11] In the primary election that followed in July 2012, Caldwell defeated Byrd by winning 53.36% of the total vote to secure the Republican nomination.

[14] Michael Caldwell was well known for refusing to accept campaign contributions or gifts from registered lobbyists or individuals from outside the State of Georgia.