Five Things We Hate about You: How Main Street Managers Can Work Better with Business Owners

I recently spent a few days at a conference celebrating the good work being done in hometowns across Pennsylvania. These conferences are always fun. Downtown managers are a special breed—scrappy grassroots changemakers fighting overwhelming odds with maverick ingenuity, drawing deep from Pennsylvania’s roots: “You gotta roll up your sleeves, give the neighbors a call, and rig up a fix.” Never was that spirit more apparent than at this particular conference.

During the worst heat wave of the summer, with well over 300 attendees and dozens of sessions running each day, the electric went out in both the hotel and the conference center. While there was limited power from emergency generators, there was no air conditioning, no projectors, only one elevator, and limited appliances for most of the day.

Others might have cancelled, but not downtown folk. Nope, instead they rolled up their sleeves (or discarded the long sleeves all together) and pitched in how and where they could, regardless of their role, title, or affiliation. They devised ways of sharing presentations—QR codes and bitlys were hastily created so attendees could follow on their devices, presenters uploaded slides to their websites, flip charts and markers were found, programs were converted to personal fans, laptops and phones were shared to conserve power. Not one session was missed or even poorly attended. I happened to be one of the presenters during that time. I completely abandoned the presentation and used a flip chart and small-group discussions. It was one of the best sessions I have ever done because we looked at each other instead of a screen.

In at least one session, we also had difficult conversations by design. The ability to openly confront conflict, share viewpoints, and speak their experience to those in power are other traits I admire in downtown managers. That conversation was needed and healthy, and new ideas and understanding came from it. And it was that conversation, that ability to deal honestly and productively with friction, that was the catalyst to finally release this letter that I wrote some time ago. I had feared it would be too harsh for the Main Street set and risk valued friendships. Having just witnessed the true resilience of this group, I happily admit I was wrong.

I live at the intersection of business ownership and Main Street America. I am an entrepreneur myself, in my 10th year of business. And for most of those years, my business has worked closely with Main Street organizations. That cross section—having a front row seat to both business ownership and Main Streets—leads me to have a few ideas about how Main Streets and business owners can tweak their communications to create the kind of egoless synergy needed to build up Pennsylvania’s hometowns.

So here it is: “Five Things We Hate about You, a Letter from Business Owners to Main Street, with Love.”

Dear Main Street Manager,

We need to have a conversation about a few things. We as business owners see the value of Main Street organizations, and we understand how important you are to the downtown economy. We see how hard you work. We see you moving parade barriers at 7 AM and showing up at town council at 7 PM. We hear your board members sharing “great ideas” without giving you the time or people or money to accomplish them. We see your personal car filled with tables and popcorn machines. We read the mean and unfair Facebook comments of naysayers. You are the closest thing to we business owners one can get without actually being a business owner—you have all the passion, all the good will, many of the same pressure points, the crazy work schedule, and the dedication. And, truly, we love you for it. You are kin.

But there are certain things you do that drive us crazy. We know you are trying to help and think it might be valuable if you learn from us what help actually looks like:

1. Stop assuming that downtown revitalization is our main mission. Feeding our family, treating our employees well, caring for the longevity of our business—those are the missions of our business. We understand and appreciate interconnectedness and community, but they are not at the top of our priority list. If staying open on a Friday night “to build an afterhours scene” means missing our kids’ turn at bat, cue “Sweet Caroline.” By assuming that your primary mission is also our primary mission, you are starting the conversation from a disadvantaged viewpoint. We need to find the overlap between our missions (and there are plenty!) and give grace when our priorities don’t exactly align with yours.

2. Stop lecturing us on how to own a business if you’ve never owned a business. Have you gone without pay to ensure your employees were paid? Do you spend Saturday nights studying tax laws and insurance riders? And perhaps the most important question: Whose money are you spending? We know you are dedicated, work insane hours, sacrifice time with your family, and haul around banners and movie screens in your car. But no matter how dedicated a downtown manager you are, you can walk away from your job much more easily than we can walk away from ours. We love it when you highlight opportunities, make connections, encourage and support small businesses, but, please, stop short of pressuring, lecturing, and “main-splaining” how to run our business when you have never done so.

3. Resist pressure to deprioritize diversity. According to the US Small Business Association, 45% of small businesses in the United States are women-owned, and 20% are minority owned. Women-owned business ownership jumped 20% from 2017 to 2023. With small businesses making up 99.9% of all businesses (no, that is not a typo), you are losing an enormous potential of investors if you are not being purposeful in creating a welcoming downtown. My guess is that I don’t need to tell you this—you know it to be true by looking at your own community. You may be put in the unenviable position of walking the line between the current political landscape and the long-term effects of policies and cultures that disenfranchise your most prolific and solid base of business owners: women and minorities. And business owners who feel unwelcome come to distrust not just one offender or political group but the entire community. They won’t come back. They don’t need to (see #4). We know it can be difficult and delicate to speak up, especially when so much of your work is dependent on collaborations within your town. We are not asking you to be radical, but we are asking you to calmly speak truth. Women and minorities are the current and future foundation of downtowns. That is not a political statement. That is a data-backed reality.
   

4. Acknowledging the power shift (and helping others do the same). Main Street managers, who spend so much time on the ground, generally understand there has been a power shift. Some of the other institutions, especially in small towns, do not. The days of businesses relying on a particular location in a particular town for success are gone. Online sales and remote work have caused massive shifts in downtowns. Even brick-and-mortar businesses increasingly rely on online sales. But too often the thinking on Main Streets hasn’t shifted, continuing to operate as though it’s still the 1950s: small circles of unquestioned individuals calling the shots and engaging in local (and personal) politics that fewer and fewer people are interested in. “If you want to be successful in this town, you have to play ball.” Yes, people still stay that. I have had it said to me. And to other business owners. Entrepreneurs stand at the intersection of remote work, highly specialized skills, and an unlimited customer base. We don’t need to play ball in this town. We don’t even need a field. We can be successful anywhere, without your help. In towns where there are more empty storefronts than residents willing or able to use them, entrepreneurs have far more power than in past decades to decide in which location, if any, they invest. Towns whose official and unofficial governance continue acting as if they hold the same influence they once did drive away the very people they need. Main Street managers are in pivotal positions to bridge this gap—they understand that reality and are also connected to and able to speak truth to the establishment.

5. Stop asking us for free stuff. Refer to #1. Building a downtown economy by soliciting free stuff from the businesses whose economy you are claiming to develop seems counterproductive and weakens your legitimacy as an economic developer. It forces us to ask: Exactly whose economy are you developing? This expressly includes artists and musicians, who find it difficult to buy canvasses and new strings with “exposure.” Build your value rather than asking us to give products and services away. As Main Street managers, you have plenty of value—you have connections, resources, social media clout, and control of downtown events. Sponsorships and creative partnerships with shared investments and clear exchanges of value feel far better than being asked for giveaways.

These are all said with earnest affection and kinship, like long-time neighbors who have a hole in the fence, with a dog on one side and chickens on the other. We are just givin’ ya a call, ready to roll up our sleeves, and find a solution.

What would you add to the list? What do business owners do that drive Main Street managers crazy?