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Deborah McIncrow of Countryside on Life, Lessons & Legacy

We recently had the chance to connect with Deborah McIncrow and have shared our conversation below.

Hi Deborah, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What is something outside of work that is bringing you joy lately?
I absolutely adore dancing at a concert and it’s just not any old concert it is my favorite band ever, the Dave Matthews Band. I enjoy every single minute of my time at their shows and I just love to dance the night away. Other than the music, I totally am giddy when they walk out on stage and I hear the first twang of the guitar string ~ It’s my Disney World, it’s my night before Christmas and I wouldn’t change the experience for the world.

Can you briefly introduce yourself and share what makes you or your brand unique?
When I ruined a pillow on a journey and returned home determined to find a solution for my pillow while traveling and finding nothing… I was bent-on creating a solution for the problem… Welcome to PillowSak! PillowSak is a protective cover for your pillow while traveling so when you reach your destination, and it’s bedtime, your pillow is nice and clean. PillowSak is unique in its design and makeup. There is nothing on the market like it; design and utility patent pending. My number one competition is a garbage bag and when a customer tells me this after I’ve pitched the product, I say “welcome to your upgrade, a lot more environmentally friendly and certainly more attractive to travel with.” I began the journey with one sewing machine on my dining room table and three and a half years later I’ve grown into a fabulous company. Even though the majority of the sewing is done in house still, I also employ numerous ladies from the community to help, I’ve got three beautiful home schoolers learning the ropes of growing a business and my dad still makes all the straps for PillowSak. I’m in just over 50 retails stores, have six college licenses under my belt and I continue to travel around the south east exposing the world to PillowSak and I wouldn’t want it any other way!

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What was your earliest memory of feeling powerful?
My earliest memory of feeling powerful was when I was ten years old and organized a fund raising effort for our local church. I organized the donation drive, found helpers to staff the sale booth and sold the donations and in turn donated the funds to our local church for a rebuild.

If you could say one kind thing to your younger self, what would it be?
If I could say one kind thing to my younger self it would be to remember that you can do anything you put your mind to if you work hard enough and not give up.

Sure, so let’s go deeper into your values and how you think. Is the public version of you the real you?
Absolutely! I am bubbly, energetic and a go-getter. I love to be upbeat, positive, helpful and happy each and every day.

Okay, so before we go, let’s tackle one more area. What will you regret not doing? 
I have had two opportunities now to have PillowSak showcased on Good Morning America and I have turned each one of them down due to the fact that I am afraid I will not have enough product for the sales that ensue. In 2026 I will not say no again to them. I will make it work.

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