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

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, goto.com. 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.