After a Career of Entrepreneurship, a Chicago Dog Walker Seeks Adventure in Retirement

After a career spanning manufacturing, ecommerce, and international management, Verifly customer Jon Berman is taking his dog walking business to the streets (and parks!) of suburban Chicago.

Customer Name:
Jon Berman

Retired Businessman, Current Dog Walker

Oak Park, Illinois

Policies to Date:
7 and counting!

Thimble: You’ve had an interesting journey from a more traditional business career to your part-time job in retirement. Could you tell us a bit about your life before dog walking?

Jon Berman: After earning my master’s degree in international management, I worked for a large multinational company for eight years. I was stationed in London for the majority of that time. I had always wanted to start my own business, so when I returned stateside, I founded a manufacturing company specializing in high-end kitchen and bath products for the hospitality industry.

After ten years, I saw an opportunity in the early days of ecommerce to start an online marketplace selling bath fixtures and accessories. I was one of the first 50 companies to sign up with Google’s predecessor, After another ten years, I started a new business with a friend selling products for seniors to remain independent in their homes. Over the course of my career, I’ve also invested in a number of startups, mainly in the consumer product arena.

T: Of all the part-time jobs for retired people, how did you decide to break into dog walking?

JB: After building and selling several multimillion dollar businesses over my 35-year career, I eased into “semi-retirement.” About two years ago, I started walking dogs as a way to stay active, both physically and mentally. It’s also given me the opportunity to spend more time outdoors while affording me flexibility to work on my schedule. I love it, because I’m basically being paid to get exercise and spend time with dogs.

Over time, I’ve developed my own clientele. I found my first few customers on online dog walking platforms, then further developed my local clientele through word-of-mouth.

T: What’s the best advice you received when you were getting your dog walking business off the ground?

JB: The best advice I received was simply to respect the dog owner’s wishes and communicate that you’ve followed their instructions when caring for their pet. This kind of transparency gives them a sense of security in your services. Another valuable lesson that can be applied to any job is this: take ownership for your errors and don’t blame others for a mistake you made, even if it was exacerbated by the actions of others.

T: Any bad advice you’ve received?

JB: I think a lot of dog walkers, in their eagerness for new business, will take a dog out even if they’ve caught on to warning signs about the animal’s behavior. You should always trust your gut when it comes to animals: if you sense that something’s wrong, listen to your instincts and put safety first.

T: What led you to Thimble in your search for General Liability insurance?

JB: As the number of dog owners I work with has grown, I felt it was necessary to invest in General Liability insurance. There’s always the risk of something happening on the job, especially when you’re dealing with animals and don’t have 100% control over their behavior—for example, a dog could bite someone while we’re out on a walk or do damage to someone’s property.

Once I made the decision to purchase insurance, I looked online and found Thimble. My main concern was that the underwriter would be some fly-by-nighter, but in reality it’s quite the opposite: the fact that the policies are underwritten by an insurance company as reputable as Markel gave me a high level of comfort and security.

When it came to actually purchasing insurance, I found it extremely easy to get the policy issued. I thought the rates were very reasonable, and the flexibility of having coverage either hourly, daily, or monthly met the exact criteria I wanted. Because the General Liability coverage arranged by Thimble was so competitively priced, I decided to opt for a higher liability limit.

Another thing I liked about the insurance is that, while my company is just me at the moment, if I have the opportunity to expand, I’ll have the easy ability to add crew members or Additional Insureds. Essentially, the coverage can grow with my business.

Our editorial content is intended for informational purposes only and is not written by a licensed insurance agent. Terms and conditions for rate and coverage may vary by class of business and state.

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