Meet Jennifer Dempsey, A Local #BossMom!

By Amanda Roland
jennifer dempsey

As a mom, you quite literally do it all! Between working and making sure your kiddo gets to school with a matching pair of shoes, it proves to be the toughest job anyone could do. Our Giggle moms have shared with us what makes them a #BossMom, and we are all for it! Meet Jennifer Dempsey to find our what makes her a #BossMom!

Jennifer Dempsey

Founder & CEO of PiesAbilities

Where do you work, what role do you play and what inspires you every day?

I’m the Founder and CEO of PiesAbilities, a small batch pie bakery with a mission to hire adults with disabilities. We don’t have a brick and mortar location (yet) but we deliver our delicious pies all over Gainesville. We are clients of “Working Food,” an awesome food business incubator here in Gainesville. I play nearly all the roles at PiesAbilities. I’m the head baker, CFO, Marketing Director and primary decision maker. Being an entrepreneur can feel overwhelming at times, but when I stay focused on our mission, creating meaningful employment for individuals with disabilities, I’m inspired to keep working toward that goal!

Tell us about your kiddos!

I’m the proud mother of five. My oldest son Marc is 28 and works in Systems Administration. At home, I have an 18-year-old son named Clayton who attends Santa Fe College and a 17-year- old son named Jackson who is a junior at Buchholz High School. My youngest daughter Joscelyn was the inspiration for PiesAbilities.

jennifer and sons

Joss was born with a condition called Hemimegalencephaly. The left side of her brain didn’t form properly, causing her to have life-threatening seizures as a baby. At 13 months old, we made the difficult decision to allow doctors to perform a hemispherectomy and surgically remove the entire malformed left half of her brain.

Joscelyn has made an incredible recovery in the last eight years and is healthy and happy. She is also one of the millions of Americans who live with a disability.

Like any parent, I want my daughter to develop her strengths and talents and to use those skills to support herself in the career of her choosing as she grows older, but the odds are not in her favor. Individuals with disabilities make up almost one-fifth of our population, but are unemployed at a rate that is twice that of people without disabilities. I started PiesAbilities so she would always have a place to work. I’m also a bereaved mom. We lost our 14-year-old son Nicholas in 2011. I’m inspired every day to live a life that would make him proud.

Jennifer and daughter

What is your favorite part / most rewarding part of being a mom?

Watching my children grow to be people I’m proud to know.

What gets you up in the morning?

The promise of coffee 🙂 I keep baker’s hours, so coffee is essential.

How do you balance it all?

That’s an ongoing challenge. My husband and I set aside time for regular date nights. On those nights, we get dressed up and leave the house and he holds my door for me. It’s really sweet!

I think self-care is super important, too. I’m in bed by 9 p.m.or 10 p.m.every night. I’m surrounded by delicious pies all day, so I try to balance that by eating a lot of veggies and working out on my rowing machine.

How do you relate to other #bossmoms?

I definitely understand the challenges that come with trying to be a good mom and a good businesswoman too. I’ve nursed my baby in client meetings, cancelled business appointments when my children were sick and wrestled with the guilt of spending long hours at work. It’s so hard to get the balance right! Now that they’re older, my children are my biggest cheerleaders and are so proud of me for following my dreams! That makes all the sacrifices worth it!

What is some advice you have for other #bossmoms trying to balance it all?

Stay flexible. What worked at one phase of your business (or the developmental stage of your child) may not work in another. That doesn’t mean you’re doing anything wrong, it just means you need to change your strategy. And don’t forget to take some guilt-free time for yourself now and then, too.


Jennifer’s Favorites!

Favorite Gainesville Restaurant?

Leonardo’s Pizza of Millhopper! It’s the only place you can get PiesAbilities’ Cannoli Pie! SO good!

Favorite Movie?

The Princess Bride

Favorite Thing to Collect? 

Pie books!

Fantasy Dinner Party Guest?

Martha Stewart, Neil Tyson, the Pope, David Sedaris, and Jerry Greenfield of Ben and Jerry’s

Go-to Fragrance?

Butter and cinnamon:)

Favorite Store?

World Market

Favorite Thing to Eat?


Favorite Thing You Do With Your Kids?

We love to visit theme parks and the beach. And, I love it when my 28-year-old comes to visit and I get to cook and bake for him.


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