I want to give back to the city and to the community it serves. Also, I want to help Overland realize the potential to grow and thrive. It is through the restoration, renovation, and growth of Overland that we will all realize our city’s true potential.

My father, Sherman, grew up here. He was a student in the Ritenour school system until his family moved away when he was 15. At the age of 19, he returned to live in the U.City-Overland area for the rest of his life. In the 1950’s, my mother, Frances Stiffelman, taught school at Ritenour. And, about 30 years ago, Sherman became a permanent fixture in Overland when he purchased a strip mall near the intersection of Lackland and Ashby roads to relocate the Stiffelman family business. Although Radio Communications Co. became Wired Technologies in 2008 and RoomReady in 2021, it has remained at that location for over 30 years and has no plans to leave.

I grew up not far from here, in Clayton, and I remember I was always in and around Overland. I watched as Clayton grew around me, the building of the Galleria, and I remember special events in the loop, watching Westport Plaza develop, and the tremendous growth of Olivette. I even remember when my father and I were among the first customers at Ms. Piggies BBQ on their opening day! Amazingly, Overland is remarkably close to the way it was in decades past, having grown some, but not in the impressive ways that the other cities have.

My career path took a different route from the family business, although I worked for my father in the mid 1990’s. I graduated from Mizzou with a degree in art and art history in 1986, and after graduating, I spent nine years in sales in the St. Louis area. I learned the art of building lasting relationships with businesses and clients. Around 1995 I returned to school, first at UMSL and then at Mizzou. In 1999 I earned degrees in biology and chemistry. As I was looking to steer my career toward relevant current events, I accepted a position as a Federal Agent with the United States Border Patrol in Sonoita, Arizona. Three years later, after 9/11, I applied for a position and was accepted into the elite ranks of the Federal Air Marshal Service. This new position allowed me to better serve our country by working on the front lines in the counterterrorism field. I learned how to navigate the federal system and gained valuable technical and administrative experience. I traveled to – and experienced spending time in – many countries all over the world. I became a team leader. And after 17 years based in the Chicago area, I retired as a Senior Federal Air Marshal. I chose to return to St. Louis, specifically to Overland, where I live here with Moose, my Irish Wolfhound service dog.

When I chose to return in 2018, I purchased the property next door to Skeeters on Lackland Road and started HDS Lackland II, LLC. In November 2019, I bought the 35,000-square-foot property referred to as “The Kimler Building” and spent the next two years renovating it. I’ve dubbed it “The Sherman” after my father. I chose to make these investments in Overland because I believe in this city. I know that substantial growth potential is here.

Throughout my life, I’ve proven my firm grasp of the concept of hard work and persistence. I also have the creativity and ingenuity needed to help advocate to solve Overland’s most challenging issues. Given a chance, I will be an advocate for the Overland community, promoting its growth, supporting fairness and transparency in our local government, and encouraging new businesses and citizens to move to our community.

Harold Stiffelman