Policies That Benefit the Community

We are a small city with a big heart where people want things to run smoothly and efficiently, a good place to live and work, and public services that work for the community. Harold Stiffelman wants to advocate for new and relevant issues for Overland to the current administration. As a long-time resident, he plans to be – and will continue to be – involved and represent the residents in Overland on issues they have told him are important.

Harold believes that Overland can be a city of opportunity for everyone and wants to ensure that the administration listens to all resident voices. Also, he believes that attracting businesses will increase services, grow the city’s income, and increase the tax base to benefit everyone working and living in Overland. The following are top issues that he will advocate for:

  • We want our administration to work to keep our taxes low.
  • We need to attract new businesses to Overland. For decades the Overland administration has been openly anti-business. We need to change this policy.
  • We need to encourage the administration to hire a full-time grant-writer to apply for and use every advantage possible for federal, state, county, and local programs and bring those funds to Overland.
  • We need our administration to clean up our streets. The roads have been in terrible disrepair for too long, and the residents want better roads.
  • We want proactive policing with increased community involvement and more contact between residents and police to ensure police officers become an integral part of the social fabric of our community.
  • We want our administration to hire a full-time advocate for civic engagement and digital media management. Our website and Facebook page are poorly coordinated and managed compared to other cities. Digital media is how cities communicate. We want more communication, better coordinated websites, and better social media, including the most popular platforms such as Twitter, Instagram, Facebook, LinkedIn, etc.
  • Residents want a student summer work program, a work-study program, an apprentice program, and other programs that can benefit the residents. These programs can serve as a ready labor force for the streets department and give youth who are just beginning to enter the workforce a step up in job experience.

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Meet Harold

He ran for mayor in 2022, and even though he lost, he still wants to advocate to the administration on behalf of the residents for the betterment of Overland.

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

Community Comes First


Encouraging growth in businesses throughout our community.


Supporting Overland businesses.


A family that knows Overland.

Neighborhood Support


Ethical & Dedicated

I have known Harold for several years. He is an honorable, honest, dedicated, ethical man. He knows how to get things done efficiently and quickly and has always been pleasant, friendly, and helpful. Over the past few years, Harold transformed a tired, dated-looking business building, inside and out, into an updated, beautiful building that is a credit to the City of Overland and our neighborhood. He will work tirelessly to benefit our city, and he will be straightforward with people and is trustworthy.

Janis Hoyt



I Feel Valued

I have known Harold since he helped me open my new salon location in Overland. He did everything he could to help with construction and even helped me get the right permits and paperwork from the city. He has gone out of his way to make me feel like a valued tenant and a friend.

Alice Garcia


He's a Hard Worker

I’ve been in Overland a long time, and I’ve known Harold since I moved over to Lackland. He’s a hard worker. And I like his dog. That dog is huge!

David Turner

It’s All About You.

I believe the incoming administration is made up of many good people and simply needs a new direction centered around “How can I help you establish your business in Overland?” and “How can I help you complete whatever it is you want to get done?” or “What can I do to support you?”  I hope to advocate for the new mayor to address this attitude adjustment and not represent more of the status quo.

Too often, in many cities, administrations act as roadblocks, preventing anyone from building, moving, or creating business. That’s what Overland has done. I want an administration that embraces growth, finds the best solutions to fix issues, and works for the people and not against them or only for a select few.

My agenda is all about the residents and what matters to you, your family, neighborhood, business, and livelihood. And I will continue my advocacy from outside the administration to hold their feet to the fire, so to speak.