In June 2018, I had the privilege of participating in a Wisconsin Main Street program (housed in Wisconsin Economic Development Corporation) resource team visit to Milwaukee’s historic King Drive Business Improvement District (BID). The team came together to guide local revitalization efforts, highlighting initiatives and projects that aligned with the Main Street Approach.

I joined an impressive team of economic development practitioners: Darrin Wasniewski, then-state coordinator; Errin Welty, downtown development program manager who is now state coordinator; Jay Schlinsog from the downtown professional network; and J. Todd Scott from the King County Historic Preservation program. 

At the time, Deshea Agee served as the executive director at the King Drive BID, and Ray Hill was the Associate Director. Ray left shortly after and spent a few years working in property management and fundraising. But circumstances brought her back to Main Street, and her insights and perspective have had a tremendous impact on the King Drive BID.

The Transformation: When Development Takes Time

One of the most important lessons from King Drive’s journey is this: meaningful development takes time. Their achievements required patience, persistence, and unwavering commitment to the community’s vision. But today, those discussions have evolved into tangible projects that are reshaping the district.

Several large-scale developments have moved forward to support affordable housing. One particularly innovative project features a 4‑story mixed-use development with a 17,400 square-foot library on the ground floor, including a maker space and community rooms, topped by 93 mixed-income apartment units. The Gimbels and Schuster’s Building — a 455,000 square-foot space that had been underutilized for storage for many years — is now home to ThriveOn Collaboration, including office space, programming for early childhood education, health and wellness, and affordable apartments. The Bader Foundation, one of southeastern Wisconsin’s largest foundations, moved its headquarters to the Historic King Drive BID and renovated a 1927 two-story building; the facility now has 22,000 square feet of office space. 

But perhaps most exciting are the businesses creating authentic experiences that reflect the community’s culture and heritage. Spinn MKE — a Black-owned spin studio with classes specifically designed around the owner’s love for hip hop music (and they throw in some gospel for good measure on some days), making it the only one of its kind in Wisconsin — brings a unique concept to the district. Niche Book Bar offers something you won’t find anywhere else: a place where you can read a book and enjoy a drink. These businesses are bringing density and drawing people to the corridor while reflecting the community’s authenticity.

Ray Hill’s Leadership Journey

Ray Hill’s path to the role wasn’t straightforward, and that’s what makes her story so compelling. After serving as the associate director for a year and a half, Ray left the BID for CommonBond Communities, a Minnesota-based affordable housing organization where she led the property management division and later moved into fundraising. She thought her chapter with King Drive was closed.

But when the King Drive executive director position opened up, calls started coming in. First, Alderwoman Milele Coggs reached out directly. Ray was flattered but didn’t pursue it. Then, a property owner in the district who knew Ray’s work in housing called. Finally, a recruiter reached out. Over two months, three different people sought her out for the executive director role. The entire process took six months. 

Ray nearly withdrew her name. Another role was strongly recruiting — more visible, better pay. She thought about Deshea, who had been in the role for five years and had great technical expertise in development, city-level connections, and economic development work. She wasn’t sure if she could fill those big shoes. But the recruiter encouraged her to continue.

When Ray finally accepted the position, she made a critical decision: she would take time to listen, learn, and understand what had been going on. Her first task from the board was to evaluate the benefits of Main Street membership. Through that evaluation, Ray realized the BID wasn’t fully utilizing Main Street’s resources or leaning into the six-year-old resource team visit Wisconsin Main Street had sponsored. She began deepening relationships with the state coordinator, Errin Welty, and Main Street America staff. 

Ray’s insights into the Main Street model adapting to neighborhood contexts are crucial. The Four-Point Approach — Organization, Promotion, Design, and Economic Vitality — remains constant, but how each point manifests in a neighborhood district differs from traditional downtown districts.

Under Ray’s leadership, King Drive BID has become a shining example, prompting other Milwaukee BIDs to ask how they can become Main Street communities. Ray has encouraged local communities to become connected communities, and State Coordinator Errin Welty has been a champion of this work. 

Ray’s vision for the district is about balance. She wants to ensure developments are catapulting local small businesses forward and serving existing residents. When large-scale mixed-use developments come to the district, first-floor commercial conversations center on what belongs in the district and what businesses are unique to Historic King Drive. Experience is what drives people. These aren’t cookie-cutter retail spaces — they’re venues creating authentic experiences that reflect the community’s culture and heritage.

Leading into the Next Ten Years

As Ray enters her fifth year as executive director, the BID is looking to establish its vision for the next 5 – 10 years. They are starting work on a corridor plan with the City of Milwaukee, including continuation of streetscape improvements. BID has also turned its focus to serving in a supportive capacity, providing visibility and support for commercial activation, ensuring local businesses are marketed, and helping them prepare for the density coming to the neighborhood through streamlined menus, improved customer service, and strategic growth planning. This also means showing up for community meetings and engagements and often being brought in to communicate with the community or educate developers on how to engage effectively.

The BID plays a key role in supporting local developers by connecting them to resources, identifying spaces, supporting community meetings, and amplifying project details to the entire community. Residents and small businesses benefit from the BID’s work through improved safety, walkability, activations, and graffiti removal throughout the corridor. 

But Ray’s approach goes deeper than physical improvements. This means supporting local events and cultivating relationships with developers so both developers and the community can sit at the table together. It means building relationships strong enough to have hard conversations when things go south. The BID’s tagline captures their holistic approach: ​“Together we carry progress, history, promise, pride, wealth, legacy, and culture.”

Ray sees tremendous potential for more growth in commercial ownership. When businesses own their buildings, it affects how properties are maintained and creates a more neighborly environment. Ownership gives business owners control of their destiny; they’re not making sunk-in costs in properties they don’t own.

How does the BID measure success? Visibility and the circular economy — dollars staying in the community. Success means residents don’t have to leave the community to get what they need. It means another property owner or business choosing to invest in the district because they see what’s happening.

The BID has strong existing partnerships: Alderwoman Coggs, various city departments, and housing community developers who understand the work from multiple angles. Although geographically specific, the BID relies on partnerships from outside the district, including bringing in Chicago’s local historian Dilla; connecting with Bronzeville in Chicago; collaborating with Main Street peers across the country in big cities; and partnering with local Milwaukee BIDs.

Looking ahead, Ray is intentional about building more regional and national partnerships. She sees the mindset of being bound by geography as nonsensical and views this as an opportunity for broader collaboration and learning.

The Heart of the Work

At the core of Ray’s philosophy is this: put people first. She understands the BID exists to serve people — these are their businesses, their livelihoods, their pride. Most businesses in the BID are small: some are generational, some were born out of COVID as a necessity to put food on the table, and others were started by people who knew how to do something well and wanted to move themselves forward while supporting local hiring.

What strikes me most about Historic King Drive BID is the connection and authenticity among the business community. Every business knows the others, supports each other, and lifts each other to succeed. Ray Hill’s leadership exemplifies what happens when someone deeply understands both the technical aspects of economic development and the human elements of community building

Eight years after that initial resource team visit, the lessons are clear: meaningful development takes time, the Main Street model adapts beautifully to neighborhood contexts when leadership understands the community, and success is about creating authentic places where culture, heritage, and economic vitality thrive together.

For Main Street communities across the country, Historic King Drive BID offers a powerful model: embrace the time development takes, lean fully into the Main Street approach adapted to your context, build genuine partnerships with all stakeholders, and always, always put people first. That’s how transformation happens.