Sheri is the owner of Winding Road Reading, a personalized learning service providing one-on-one reading support for children who haven’t been successful with traditional reading instruction. Using science-backed strategies and a gentle, individualized approach, she helps children build critical reading skills and lasting confidence.
Knowing that reading challenges impact more than just the child, she provides educational coaching and homeschool guidance to help parents feel informed, supported, and confident.
AZF: What is your “life motto”?
Meet people where they are, including yourself. Growth doesn’t happen through pressure or shame. It happens through patience, understanding, and support that begins where you are. This comes naturally in my work with others, and I’m learning to extend that same kindness to myself.
AZF: Did you always know that you wanted to be an entrepreneur? If not, when did you realize that it was the right path right for you?
For most of my life, I wanted to be a teacher. I loved working with children and believed deeply in their potential. But I was watching kids who were bright, curious, and capable be forced into molds they didn’t fit in. It was painful to watch students try their hardest and still feel like they were falling short. They deserved to be taught in a way that worked with their brains, honored their personalities, and gave them space to grow.
I realized this path was right for me when I stopped trying to make small changes from inside the system and started imagining what support could look like if it was built around each learner. Entrepreneurship gave me the freedom to create that support and show up for families in a way that felt aligned and impactful.
AZF: How do you feel best supported?
I feel most supported in relationships that value authenticity and prioritize thoughtful communication. Growth and creativity happen in spaces where people can speak freely, ask thoughtful questions, and respectfully challenge one another. Let me share my wild, unformed idea and trust that you’ll help me shape it!
AZF: What motivates you to keep going amidst the challenges that come with being an entrepreneur?
Knowing that I have a skill set that can genuinely change lives. Reading affects everything. It shapes confidence, creates opportunities, and influences how a person moves through the world. It can change the story someone tells themselves, and I get to be a part of that.
I get to be there when a child’s face lights up and they say, “Oh, I can read!” For so many children, learning to read is about more than academics. It’s about feeling capable and believing in themselves.
AZF: Describe your perfect Saturday morning.
This day starts with cinnamon rolls and hot tea. Since it’s only 70 degrees on this perfect Saturday, I can go for a hike after breakfast. Tuckered out from all that exercise, the rest of the morning would be spent reading under a blanket. At least until my husband interrupts me, desperate to talk about feelings. Couldn’t ask for more!
AZF: What’s one piece of advice you’d give to a young entrepreneur who is just starting out?
This one is easier said than done, but make the big ask. Reach out to people you admire, to the experts in your field. Ask for a meeting and you may be surprised by who agrees. Connect with people across all parts of your industry and stay curious. You never know what you’ll learn or how you might support each other.
AZF: What excites you most about being an entrepreneur?
The freedom to support meaningful change without being limited by rigid structures or outdated thinking. With years of experience, empathy, and a deep belief that every child is capable of growth, I’m able to create learning experiences that are personal, effective, and truly life changing.
Learn more about Winding Road Reading by visiting windingroadreading.com or by following along on Instagram @windingroadreading
About the Foundress
The Foundress is a creative community of female entrepreneurs established by Coley Arnold. The women-led networking group currently has over 120 members who receive exclusive access to mentorship from experienced female entrepreneurs and industry leaders; community gatherings that feature expert speakers and the opportunity to connect with like-minded women; as well as monthly Mastermind Groups where members can brainstorm and collaborate together.
Every Friday, AZF will spotlight a member of The Foundress and her business in the Foundress Fridays online series. Learn more about The Foundress and join the community at foundress.co.
