Sheila Duncan – An entrepreneur who brings hope to children

February 17, 2021

Trouble the Dog interview on Enterprise League

While we were scouting for the Top 100 female entrepreneurs list, we had the privilege to meet hundreds of women with inspiring entrepreneurial stories. While all of them genius in their own right, only a few of them were truly heartwarming and wholesome. And Trouble the Dog lead the pack.

We’re delighted to introduce you to Sheila Duncan, the person who believed in Trouble’s magic ever since the first time it appeared on her niece’s drawing. She went above and beyond to find an American manufacturer that will bring Kendra’s vision to life. Thanks to her resilience, now thousands of children find hope in trouble.

Read her story.

Feeling under-appreciated as an employee, a nonexistent work-life balance, financial struggles, getting out of bad relationships – these are the most common triggers that push women to become entrepreneurs. Tell us about your trigger?

I actually had more of an inspiration than a trigger. My dad was a very successful restauranteur and I realized after working in a corporate environment that being an entrepreneur was much more my style. Hard work didn’t scare me as long as I could enjoy the process and run my own show. I ultimately went to work with him and once he was diagnosed with cancer wound up being in charge.

Sheila Duncan quote

How did you come up with your business idea?

In 2006, my then 12-year-old niece, Kendra, was at my home one winter’s evening. We had recently experienced a number of family cancer losses and she was just drawing at my coffee table. A telethon came on for children with cancer. Kendra looked up and said, “I’ve got to help those kids”. 

She instantly drew a little dog – like one of those divinely inspired moments you hear about – and dubbed him “Trouble”. She then drew a very simple comic strip about a pup that was abandoned, rescued by a kindly Nonnie (based on her own grandmother who had passed away) and Trouble, in turn, pays it forward and rescues other pups. 

I saw the magic in this character and took a leap of faith to turn him into what he is today. Trouble is a global children’s character helping kids through the bumps in the road of life gently and with humor. He is an American made plush pup and we have just launched our third book in a series.

Have you had support from someone, even if just encouragement? Who was that and how did it help you?

I have had support from so many along this journey. Three women in particular – Carrie Schluter, Melanie Fleming and Sue Byors – have all stepped up in a variety of roles from creative to PR to bookkeeping to encourage me and keep me on track. 

People see not only the magic of Trouble but also the inspiration he elicits in kids which is why so very many have stepped up to help.

Female entrepreneurs are often underestimated and overlooked. Have you ever felt at a disadvantage?

Way back in the restaurant industry there were times I felt I was perhaps not being heard right away. But I have to say in this journey with Trouble The Dog I’ve really not experienced the same difficulty. Maybe I’m just stronger.

Some say it’s hard work, others say it’s talent and resourcefulness that play a crucial role for success in entrepreneurship? Which traits have been instrumental for your success so far? And why?

I say the most important trait to have an entrepreneur is to trust your gut. What is most detrimental would be not to follow that instinct.

What excites you the most about being an entrepreneur?

What is most exciting to me is the creative process as well as knowing how Trouble The Dog is inspiring kids to help other kids. 

As an example, a boy adopted from foster care after a very rough start in life receives so much comfort from Trouble that he’s started a campaign to get 185 Trouble Dogs into the arms of other kids still in foster care because he knows what it’s like. 

Share with us some of the worst business advice you’ve ever received?

The worst business advice I’ve ever received was to forget having Trouble made in America stating “people don’t care”. They do!

You’ve got a high stake investment opportunity. Pitch your business in 150 words.

Trouble The Dog is a character created from the pure heart of a child wishing to help other kids be their “troubles” big or small. Trouble inspires children to open up about their emotions as well as pay it forward for other kids. Trouble enchants kids who ask that he be turned into a cartoon character. This concept is different, engaging and we have the television pitch to prove it to the right partner.

What’s the best piece of advice you’d give to inspire aspiring entrepreneurs?

I’d advise aspiring entrepreneurs to realize they have a lot of hard and wonderful work ahead. And if the passion is truly there to never, ever give up on their dreams.

What are your goals for the upcoming year?

My goal for the coming year is to turn Trouble The Dog and his posse into a cartoon series.

Any final words to end this interview?

I’d love to share how breathtakingly difficult it was to have Trouble manufactured here in America. It took me six months, all day, every day, to find the right partner in American Bear Factory. I had many who wouldn’t give me the time of day, others who said: “you can’t afford to have us make your product”. 

And ultimately I persevered and Trouble is one of the very few plush pups made right here in America. We’re very proud of that accomplishment.


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