Meet the Entrepreneur - Dana Dubriwny

By Jamie Damato Migdal, CEO and Pet Industry Entrepreneur

One of the things I like most about CanineLink, and the pet industry in general, is that I get to meet inspiring entrepreneurs like Dana Dubriwny, the owner of Chicago Pet Sitters.

What is your background?

I received my bachelor’s of science in journalism at Southern Illinois University, then obtained my master’s degree in Public Affairs reporting from the University of Illinois. After graduation, I worked at a start-up dot-com writing obituaries. This was in the late 90s during the tech bubble, and it was great. Not only did I have to come up with the most creative way to discuss something grave (pun intended), our staff meetings were on beanbags and we had a constant Ping-Pong championship going on.

After a round of layoffs at the dot-com company, I found myself writing about commercial real estate. Beyond not having a passion for the industry, I loathed having to clock-in and clock-out every day. I would stare out the window from my cubicle feeling like a faceless character in Orwell’s 1984. While in this 9-5 position, I got my first dog. When my Chihuahua Miso first came home, he was a 4-pound funny, silly ball of fur that could fit in the palm of my hand. Leaving him in the morning was heartbreaking, and I would ache with guilt at my cubicle daily.

When I had the opportunity to work from home for an online company headquartered out of New York, I jumped at the chance. While the hours and demands were much more intense, the fact that I could work at home with my dog was well worth it.

How did Chicago Pet Sitters begin?

Despite working from home, I kept Miso’s dog walker and began asking questions about her industry. In 2005, there were only a handful of dog walking companies, and I knew exactly what I wanted out of my own service. A little research uncovered a market need for a quality dog walking service, and I was certain I could provide it.

It wasn’t easy. I still had my full-time job that was paying the bills while starting this service-oriented and physically demanding job. I did both jobs for about a year and a half – starting with running out during my lunch hour to walk dogs to conducting phone interviews, writing, and editing out of my car in between dogs walks and writing and editing at my overnights. By the end of that year and a half, I had saved $10,000 and was physically and mentally exhausted. I was working around the clock with very little sleep. In 2006, I officially took the leap from a conventional post-grad job to the unconventional career of dog walking.

How has your original plan for the company changed over time?

I never really had a plan for Chicago Pet Sitters other than wanting it to be the best service in the city. But that has certainly evolved. I have learned so much over the past 10 years, and now my plans include daycare, food, and a nonprofit.

Who are your mentors and inspiration?

Looking back, one of my biggest mentors was an editor I had at a commercial real estate magazine, Brian Sutton. He pushed me to study details, and that has stayed with me through the years. There are so many details in pet sitting, with so many moving parts. It’s imperative to have an attention to detail in this job. I also follow a lot of inspirational authors and songwriters who remind me what’s truly important in life, and my parents serve as a great source of knowledge and motivational wealth for me.

What are your top tips for finding, and keeping, quality staff?

Attracting good staff is tough because there’s no forum for specifically what we do. My most successful sitters have been friends of great sitters. Craigslist can be a scary place, and hiring an applicant who wasn’t a good fit has burned us. I wish there were a tried-and-true answer to this, but all I can say to new business owners is cross all your T’s and dot all your I’s. Do the background check. Call the references. Stalk the person’s Facebook and personal websites. Make the first month a trial period. It’s worth it.

What advice would you give to other people who want to start their own pet sitting business?

We’re in an industry that isn’t given the credit it deserves (considering we have access to clients’ homes and often we’re helping to shape a dog’s future behavior), and our sitters are asked to work in the elements for little pay and no benefits. For those reasons, we see a lot of turnover. The challenge is figuring out how to keep the staff we have while constantly recruiting more good people. The stars don’t always align that way, so when things go sour, we just have to keep our spirits up and keep trucking along.

For those looking to get into the industry, here are a few things I’ve learned:

• Write a business plan. I didn’t, but I wish I had. Having a road map to where you’re headed is much easier and a lot more rewarding than guessing where you’re going with no way of measuring how far you’ve come. In the past year, I finally wrote a business and growth plan. I’m constantly revising and updating it, and it’s invigorating. It helps to keep me going.

• Have support. Starting your own business can be very lonely. There are a lot of long, agonizing hours, and a lot of time spent away from your family. There are a lot of naysayers in the beginning, so surrounding yourself with encouraging people and reading about other entrepreneurs will help to fuel you when you’re feeling out of gas.

• Set rules for clients early on. When can your clients reach you? Where can they get hold of you? In the beginning, the idea of a small mom-and-pop shop is a romantic notion. Your clients feel special because they have a direct line to you and can text you at any hour. But once you get bigger, you will resent those clients for taking advantage of you, and they will feel left behind and ignored. Setting rules and expectations up front will help you avoid those pitfalls.

• Make your policies clear to staff. Every staff member should be following the same protocol. To that end, they should also feel like a team. Spend time sharing stories with the staff and discussing why policies are important. This can be a very isolated job, so ensuring that they know they are part of something bigger and all on the same page is great for morale.

• Hire internal people who are better than you. Get a bookkeeper and an accountant you trust to handle the numbers. Talk to an attorney about how to protect yourself. Employ a manager who can deliver the absolute best customer service, even when faced with adversity. Put people in place who can be a better version of you when you need to take time off.

• It’s not about the problem; it’s about the solution. I can thank my ex for this little nugget of wisdom. There will always be issues…we are in customer service, dealing with people’s homes and their four-legged babies. When a problem arises, deal with it immediately. Take ownership of it, and make sure your client – and sitter – feels heard.

My favorite parts of owning Chicago Pet Sitters have little to do with financial success. Clients can live their successfully complicated and demanding lives and have the freedom to travel because they trust that we’ll take care of their loved ones. I love that I get to handpick the staff and grow with them. I learn so much every day, and I continue to learn. Don’t get me wrong; this job has its challenges. But for me, the rewards far outweigh the drawbacks.

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