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A Bird’s-Eye View of the Boston Business & Startup Scene: Making Work Work, CEO Series Vol. 8

This year, I’m doubling down on a topic that matters deeply to me: Workbar's home, Boston. Not expansion. Not shiny new markets. Boston.  

Let’s play a game. Tell me the first three things that come to mind when you think about Boston (there’s no wrong answer here). 

You might come up with: Fenway Park, universities, history. Or maybe you think of Ben Affleck, Matt Damon, and Dunkin. 

But when I think of Boston, I find myself thinking about the vibrancy of the Boston business community. From solopreneurs to local businesses, regional companies, and national and international enterprises, Greater Boston is home to some of the most innovative, imaginative, and trailblazing companies in the world. And Workbar is home to so many of these companies. 

I constantly hear from our members some version of: “One of the reasons I feel lucky to be in Boston… is because Workbar is here.”

And right now, no other city (for now 😉) has Workbar.

That matters.

It tells me the ecosystem we’re building is real.
It tells me people see Workbar as part of why Boston works.
And that’s something I don’t take lightly.

A bird’s-eye view of Boston right now

Zoom in, and it’s easy to fall into the doom-and-gloom trap of conflicting news and headlines. But zoom out, and Boston’s business scene looks healthier than the headlines would have you believe.

Yes, funding has tightened, hiring has slowed, and the real estate office market is evolving. Those challenges are very real. 

But from 30,000 feet? Boston is still doing what it has always done best: Building forward-thinking companies that solve real problems for customers. 

Let’s look on the bright side:

Boston’s business reputation was never built on buzz; it’s part of our DNA. Despite the challenges, founders are still doing what it takes to make work work for their employees. 

When I open LinkedIn and see people around the world venting about unrealistic employers, it reminds me how lucky I am to run Workbar in Boston.

The part I care most about

There is no doubt that Boston is the launchpad for world-changing startups. 

Boston is home to world-class universities. MIT, Harvard, Worcester Polytechnic Institute (WPI), Boston University, just to name a few.

Techstars Boston Accelerator was launched in 2009, the same year that Workbar was founded and since then, they’ve graduated 240 companies, had 2 $1B+ exits, and 900+ mentors. 

I still remember when we opened Workbar Back Bay in early 2018 and Techstars had an entire cohort working out of a section of our space. They were building anti-drone technology, and you’d walk in at any time to see people in military uniforms flying drones overhead. Being in the middle of it, you couldn’t help but feel like you were part of something bigger than yourself. 

We have always attracted incredible talent — but there are downsides to doing business in Boston that we can no longer ignore.

Great talent is being pushed out of the area by:

  • High costs of living
  • Long commutes that lead to burn out
  • Public transit limitations

And when that happens, entire talent pools leave the region altogether. Which means Boston also loses future founders, operators, leaders, and investors. 

That breaks my heart. Talent shouldn’t have to live downtown to stay connected to opportunity.

Why I’m (still) betting on Boston

I’m still betting on Boston for business, and I’m not the only one. 

Whoop just announced the launch of the Massachusetts AI Coalition, bringing together leading companies headquartered here or deeply rooted in the Commonwealth to collaborate and push AI forward right here in Boston. It’s incredibly satisfying to see so many leaders aligned around this vision of keeping talent in the Bay State!

But I’m betting on Boston because I know that Boston is more than just Downtown Boston – it’s the suburbs and communities that make up Greater Boston. (Maybe you can even say access to the ‘burbs is part of what makes a…greater Boston 🥁)

Boston is stronger when its business ecosystem extends beyond the urban core. 

This is what Workbar is solving for. This is what I’m deeply passionate about. Our communities deserve places where young professionals can work close to home, meet their future co-founder, and build ambitious companies where they can thrive. And they should be able to do all of this without a 90-minute (or longer) commute. 

Believe me, this city knows how to adapt — and Workbar is ready to help.
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