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Services & Experiences
17 min read

The Realities of Running a Small Pet Business

Three founders running very different service businesses - dog walking, pet transportation, and dog training - break down the operating detail most founder interviews skip. Joseph Merrill on why Hamilton Bark pays walkers hourly, moved clients to prepaid subscriptions, and built its own software rather than renting margin from Rover. DeAnna Andrews on why refusing to expand beyond transport made The Pet Taxi referable, and how veterinary partnerships became 40 percent of revenue. Emily Stoddard on narrowing services and buying a brick-and-mortar facility after nearly 18 years.

Written by
The Underbite
Published on
October 7, 2026
Three founders on the realities of running a small pet business

Every successful pet business looks different on the surface, but beneath it are the same questions every founder has to answer: How do you win customers? How do you build efficient systems? And how do you keep growing without losing what made the business work in the first place?

This week, we speak with 3 founders with 3 very different pet businesses:

They share candid insights into their daily operations, biggest growth decisions, marketing strategies, and the lessons they've learned building sustainable businesses in one of the fastest-growing industries

Joseph Merrill and Kerry Chomic, co-owners of Hamilton Bark
Joseph Merrill & Kerry Chomic

Walk us through a typical day at Hamilton Bark. From the first walk of the morning to the last, what does running the business actually look like?

We have three key racks on the wall just inside our apartment and a fleet of 6 scooters for our staff. The day usually starts with our walkers coming in to say hi and grab their scooter and keys for the day. The day ends the same way - when their shift is done, they come back, drop off their keys, and drop off their scooter for charging.

The day itself is filled with the logistics of dog walking. Sometimes walkers get behind, sometimes clients forget to leave the key in the lockbox; you never know in advance what that day is going to bring! We schedule Kerry and I to half of our capacity though. This builds in the ability to respond in real time if emergencies happen. This has saved us more than once. Last Christmas Eve I was walking a beautiful German Shepherd who started to limp badly, with a head tilted at about 30 degrees to the side - she kept vomiting. Fortunately, the vet was literally around the corner.

They weren’t emergency care, but they knew us. After contacting her family (who were in Manhattan and couldn’t come home immediately), it was agreed that I’d take her to the ER. We were able to give the rest of my walks to Kerry, and I stayed with her all day until her humans could come and take over. It turns out she had a double ear infection.

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