Why I Chose Bridgeport For My Next Startup

by Michael Caldwell, marketplace entrepreneur

After selling my previous business which was based in South Norwalk, Connecticut, I found myself ready to start anew and begin work on my next venture, an online marketplace for pet services. The thought of returning to the starting line was daunting, and in order to mentally part ways with my old business, I needed a new backdrop, a fresh new location to begin this next journey.

Those that call Fairfield County home know well the bucolic towns dotting the coastline - from Greenwich to Darien to Westport and right on up. Sparkling streets, high end boutiques, fancy restaurants. One might reasonably ask me, why not choose one of these locations? Surely it would be lovely to hang your shingle in one of these storybook towns. Why not? The answer is easy. No, it's not just the high rent 🌝. It's that to me these towns represent success already achieved. These are the stomping grounds of those ready to enjoy the fruits of their success. That's simply not where I'm at in my journey. I'm at at the beginning, the starting line. Success on this next venture is nowhere yet in sight. For that reason, these scenic locations don't provide the right motivational message each day to be be hungry, to roll up my sleeves, to get my hands dirty (insert the metaphor of your choice!)

Gotta Have the Grittiness ...

Finding the right place to set up shop is a crucial decision when starting a business. It sets the tone, the mood, the mindset. I had a pretty good idea of what I was seeking - a city that had the perfect mix of grittiness and urban amenities. 

Why grittiness you ask? This was an important criterion for me. The hours would be long, the journey would be hard. And I needed somewhere that takes me out of my comfort zone and reminds me that this won't come easy - that hard work will be the order of every day. This will be the heavy lifting required to get a new business off the ground and I wanted the streets around me to remind me of that daily. 

... and the Urban Amenities!

And why the urban amenities? Well, this is where things needs to balance out. Not only for my own enjoyment, but for potential future employees, I wanted to be within walking distance from the urban essentials - a bustling coffee house, a tasty bagel shop, a hip taco joint, a solid pizza place. 

Leishas Bakeria, Bridgeport, CT

Source Coffeehouse, Bridgeport, CT

Grittiness plus urban amenities, the essential formula. I knew I was asking a lot to find this perfect juxtaposition. But with the bar set high, I began my search.

Finding Other Hustlers

I knew that working from home was not an option. I want to be surrounded by people. But not just any people - entrepreneurs! That special breed. Hustlers, like myself, determined to work for themselves at any cost. I began my research into co-working places that would give me the entrepreneurial environment I was seeking. 

I looked into several options from the Stamford Innovation Center to the The Danbury Hackerspace to SONO Spaces in South Norwalk to The Grove in New Haven. Each brought something unique and each very cool in its own way. But none had everything that I was looking for. My search led me to check out The B:Hive in Bridgeport. So one Saturday afternoon, I arrived for a free tour. Walking in my expectations were modest, but walking out I knew I had stumbled on exactly what I was looking for.

I Found My New Home

The B:Hive, Bridgeport, CT

Located on Fairfield Avenue in Bridgeport, The B:Hive is well situated near a variety of businesses - a deli/bagel shop, a wine store, a pizza place, a coffee shop around the corner, an old theatre (Bijou), and most recently a vintage record & book store. Within a few blocks are several other restaurants & bars.

Stepping inside of the B:Hive one immediately feels the creative, entrepreneurial vibe. Not the cliche of twenty-somethings drinking beer & playing pong, but serious entrepreneurs quietly pursuing their dreams. (Editors note: this is not a knock on drinking beer & playing pong, two passions of mine that those who know me can attest to!). 

Ferries, Trains and Automobiles

Amtrak Station, Bridgeport

One important lesson learned from my previous business is that once you get to the point in your evolution where you're hiring employees, more practical considerations take center stage. Having a funky coffee shop around the corner might be the single most important factor to a one person entrepreneur making his own hours, but being close to a train station is crucial to commuting employees on a tight schedule. Bridgeport definitely checks that off the list as a major hub on the Metro North and Amtrak train lines - as well as being right near both the Merritt Parkway and Interstate 95. Also nearby is the Bridgeport Ferry.

For this reason, Bridgeport became the logical choice for me, not only for the intangible motivational reasons I described earlier, but also for more tangible practical considerations related to the commute. It truly had it all. 

Hope, the essential ingredient

There is something that becomes immediately apparent when you become part of the Bridgeport community which is that there is a common thread of hope and determination to drive Bridgeport to its true potential. I found this collective hope very inspiring, and from it I draw inspiration to fulfill my own entrepreneurial vision.

So every morning that I emerge from the parking garage onto Fairfield Avenue in Bridgeport, I feel invigorated - by the street, by the city, by the people working on their dreams. It inspires and motivates me each and every day. Bridgeport is that new backdrop I was seeking. It is grittiness meets urban amenities. I have found the city to call home for my new venture. Now of course comes the hard part - growing the business to profitability and sustainability. It's going to take large doses of hard work and energy. In fact, maybe now is a good time for me to head around the corner for that coffee. Cheers to you, Bridgeport. Let's go get this done!

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About the Author:

Michael is a long-time Internet entrepreneur having previously founded the nationwide entertainment & events marketplace GigMasters (acquired in October of 2015). Michael's passion is building online marketplaces and his latest venture, Petmasters, focuses on the multi-billion dollar per year pet services industry. Recognizing the increasingly significant role pets play in people's lives, and tapping into his own life-long love of animals, Michael is building Petmasters with the goal of becoming the most comprehensive pet services marketplace in the U.S. Petmasters will help pet parents find and hire not only dog walkers & cat sitters but everything from pet trainers to pet portrait artists to pet grief counselors and more. The site will feature services for all animals including horse boarders, chicken coop builders, & aquarium cleaners. Michael lives with his wife, three boys, two cats, and rescue dog in nearby Redding, Connecticut. In addition to Petmasters, Michael also serves as strategic advisor to PopTop, a UK-based entertainment marketplace, and Funerals 360, an end of life marketplace based in northern California.