Alright – so today we’ve got the honor of introducing you to Jessica Shepard. We think you’ll enjoy our conversation, we’ve shared it below.

Alright, Jessica thanks for taking the time to share your stories and insights with us today. What do you think it takes to be successful?

For the first 10 years of owning The Uproot Pie Company, I didn’t really think of myself as a business owner at all. It felt more like a place I went to hang out with friends, making food outside in a wood-fired oven in some of the most idyllic locations on the coast of Maine. It almost felt like I was playing at being a business owner. Even now, as I’ve expanded into my new “restaurant” space at the Carriage House, it still doesn’t feel like a traditional business. Every night when we open, I feel like I’m setting up a beautiful space and lighting candles for friends to gather, rather than running a business. It’s always felt more like an experience I’m creating for the people I care about.
So, when I was asked to host a workshop this past fall at the Carriage House on the topic of “What is Success?” I realized I’d never really thought about whether or not I was successful. I’ve just been enjoying the journey, and I guess that’s always been enough for me. But when the question was posed, I finally stopped to wonder: What really is success?

I called my childhood best friend—who, by all outward measures, is the picture of success. She’s self-employed, makes a comfortable living, travels freely, and works in environmental protection, which is something she’s passionate about. I assumed her answer to the question would be an obvious “yes.” But when I asked, “Do you think you’re successful?” she answered with a resounding “No.” And that answer has stuck with me ever since.
She said, “Do you think your 80-year-old self would be proud of you?” It was a simple question, but it stopped me in my tracks. I said, “Yeah, I think she’d be pretty proud of what I’ve created.” But when I asked her the same question, her response was different. “No, I think she’d be disappointed in the direction I’ve taken. I don’t give back to my community, and I live a pretty selfish life. I’m climbing, traveling, doing what I want when I want—but I’m not connected to something bigger than myself.”
Despite her work protecting nesting eagles and baby turtles, she felt disconnected from the deeper purpose of her work, especially when it was motivated by money and an environment that often felt toxic. That conversation made me realize that success isn’t about how much you accomplish or what you achieve on your own—

After my conversation with Sam, I was more clear on what success means to me – it’s about community. It’s about grit, passion, and loving what you do. It’s about waking up excited to create something meaningful. Money, fame, and social media likes might be markers that others use to measure success, but they don’t define it for me.

Success is something that comes from within. It’s about the joy I feel when I see people connecting in our communal space over wood-fired pizza and a glass of wine made by a woman owned vinyard in Croatia , when I’m able to build relationships with the folks in my community, and when I can offer an experience that brings people together. And at the end of the day, that’s the kind of success that sticks.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

To inspire, connect, and share through food and craft.

I hail from a small village on a small peninsula in mid-coast Maine, a place where there was one store (Fales), an elementary school, and a charming old library. My graduating class? Just 60 people. Growing up there, I thought, “You couldn’t pay me a million dollars to return.” The closest town, Rockland, felt run down, with a boarded-up Main Street that smelled like fish when the temperature reached 70 degrees. I left thinking I’d never return.

But life has a funny way of pulling you back. Over the years, I traveled across the country, looking for a more magical place. I visited Europe, New Zealand, Fiji, and Hawaii, all the while daydreaming about opening a community coffee shop and bakery. Then, in 2019, my mother sent me a picture of a cottage on an island in Maine that her friend was renting. I packed up my car in Oregon and headed east, sourdough starter in the passenger seat.

I helped open a small shop in town and started Squash Blossom Bakery, where I made scones and bagels in my cottage and dropped them off at the local corner store to sell. A couple of years passed, and my desire to have a space of my own grew stronger.

In 2011, I founded The Uproot Pie Company. At that time, the cost of buying and renovating a space felt out of reach, and I didn’t want to incur that kind of debt. My original idea was to open a wood-fired bakery that would double as a community hub for artists and local folks to gather and share ideas. But instead, I built a mobile wood-fired oven to start small and bring the pizza to the people. I took my oven to farmers’ markets, catered local events, and connected with creative, tight-knit communities. What I thought would be a side hustle quickly grew into my full-time business.

Over the next five years, business continued to grow. I added a second oven and kept my eyes on an 1850s carriage house in Thomaston. The moment I saw it, I knew it would be the perfect home for The Uproot Pie Company. In 2018, I cold-called the owner to see if they’d consider selling. At first, the price was too steep, but I patiently waited a year and revisited the idea. In January 2020, the sale went through, and I began renovations.

What followed were long, grueling days of demo, insulating, drywalling, sanding, and painting all the while going through a deep personal heartbreak. In December of 2023, I opened the doors to The Carriage House. We now serve wood-fired pizzas, host workshops, hold community events, and run fundraisers. Looking back, I can honestly say that some of my most beautiful and creative work came out of some of the darkest times of my life.

Through it all, I’ve been fortunate to have built an incredible team of women around me. My team is my greatest pride and accomplishment. These women are strong, smart, creative, kind, and communicative. They’ve supported me through the hardest days and believed in me when I lost sight of my vision. The Uproot team is not just a group of people who make pizza together—we create a space that’s warm, welcoming, and kind to all. When you walk into the Carriage House, you immediately feel that. It’s a place where everyone is invited, where laughter and care fill the air.

I’m incredibly proud of this business—it means everything to be able to share it with the people who walk through our doors.

And we make the best wood-fired pizza I’ve ever eaten to this day. That’s still the heart of it all.

Any advice for managing a team?

I get asked this a lot by other business owners because the Uproot team is enviable. Not only is everyone really good at what they do they are kind, sincere, and super capable and we are all genuinely friends. Following this big brag what advice do I have? I always wonder how I got so “lucky” but what has been pointed out is that I attract this type of person and I feel like at the root of it, I lead by example. There is no toxic positivity or avoiding hard conversations. We deal with challenging situations right away and if now is not the appropriate time, let’s take a moment to gather data and more information to help us through this conversation. I’m also a very hard worker and pride myself on taking everyone into consideration. We’re a pretty small team and everyone means a lot to me. Clarity in intention is a foundation I like to work from.

What’s been the best source of new clients for you?

The local farmers’ markets have been an integral part to gaining clients whether its for catering, or advertising that we are open at our new brick and mortar or to let people know about our upcoming workshops. It’s our local community connection and we feel so very lucky to be a part of them.
Recently, I have hired a social media manager that has become a huge part of building our our online presence and that has contributed greatly to our increase in sales revenue and workshop attendance.

Contact Info:

• Website: https://theuprootpieco.com
• Instagram: theuprootpieco
• Facebook: The Uproot Pie Co.

Image Credits

Hannah Hogat
Brittney Fairfield