The Story Behind Our Small Business Grant: Making Work Work, CEO Series Vol. 6
When COVID hit in March 2020, one thought kept running through my head: If small businesses don’t make it, neither will we. At the time, 75% of the businesses using our spaces were solopreneurs and small teams. It wasn’t a theory, it was math. I knew if they couldn’t survive the months ahead, we wouldn’t either.
That realization led to the creation of something that has since become one of my favorite initiatives we’ve ever launched: the Workbar Small Business Grant.
The Grant’s Origins: A Simple Idea in a Chaotic Time
Everyday during the pandemic, small business owners would have to make impossible decisions. And as one of those small businesses ourselves, I understood the reality of it all.
Not long ago, a CMO of a local company said to me, point blank, “I’m surprised your company is still around.” I knew exactly what he meant. I told him honestly, we were fortunate to go into COVID with no debt, and because we’re a local company, we leaned on our landlords as true partners. No one wanted to see us fail.
These weren’t just faces across the table in a lawyer’s office, they were people I’d built real relationships with. People I saw at our kids’ lacrosse games. People I grabbed lunch with. That trust and proximity made all the difference when I called them asking for help.
At the same time, we had unused space and the ability to offer it in a way that could actually make a difference. So, even though we didn’t have a nickel to spare, we created a grant program to give Boston-area small businesses $5,000 in funding and, more importantly, free access to our spaces for a full year.
It wasn’t a marketing stunt. It was an ecosystem strategy. We knew that if we could remove some of their overhead and keep them connected to a professional community, they’d be better positioned to recover, and in turn, so would we.
It All Comes Back to Small Businesses
America runs on small businesses (and Dunkin). According to the Small Business Administration, since the late 1990's, small businesses have accounted for between 43.5% and 50.7% of the United States' GDP.
They’re also powerful engines of local economic circulation. The Institute for Local Self-Reliance found that for every $100 spent at a local business, $48 stays in the community, compared to just $14 at a national chain source.
The data made it clear: supporting small businesses wasn’t just good citizenship, it was a strategic imperative for long-term resilience.
How the Program Works
Each year, we invite Boston-area entrepreneurs to apply for one of three annual grants, which provide both a cash prize and free access to Workbar for a full year.
We put together a panel of local business leaders as judges. This group is deeply embedded in Boston’s startup ecosystem, and they help spread the stories of finalists and winners through their own networks, extending the impact well beyond ours.
A Flywheel Effect
In the last five years, I’ve watched our grant winners hire their first employees, bring new products to market, and spark local demand. Their impact doesn’t exist in a silo, by becoming part of our community, they strengthen the broader business ecosystem. That collective momentum keeps our spaces vibrant, expands local networks, and fuels the regional economy.
Boston produces world-class graduates every year, but many leave because the math of staying, between housing costs and transportation challenges, doesn’t work. My mission is to develop workspaces that anchor innovative ecosystems in the communities outside the city, so more graduates choose to build their careers here. The Small Business Grant supports that vision in a powerful way.
Over the years, we’ve questioned whether to keep the grant going. But the reality is, small businesses face new challenges every day, tariffs, inflation, AI, changing consumer behavior, and that makes this program more relevant than ever.
A Model for Resilience
Harvard researchers have found that communities with more small, locally owned businesses experience higher income growth, lower poverty rates, and stronger civic engagement over time. That’s exactly the kind of environment where companies like ours thrive.
This kind of program doesn’t depend on large budgets or complex systems, we had none of that at the beginning. What it depends on is intention and a simple premise, when we invest in each other, we’re part of something bigger than ourselves.
A Call to Other Leaders
I share this story not because I think we’ve found the only answer, but because I believe more companies can play a role like this. You don’t have to replicate our grant program exactly. But you can ask yourself:
- What underused assets could you offer to small businesses in your orbit?
- How could you create opportunities for connection, visibility, or shared infrastructure?
- How might investing in your local ecosystem ultimately strengthen your own organization?
When small businesses win, we all win. That’s not just a tagline. It’s a strategy that helped us navigate a crisis, and continues to shape how we grow today.
