Lessons from Local Leaders:

Jessica Winesett

Building from the Inside Out: Jessica Winesett and Expansive Development

Jessica Winesett is an entrepreneur whose work spans physical construction and spiritual guidance. Her company, Expansive Development, specializes in high-end, complex residential construction in the DC area, including multi-unit buildings, additions, and full gut renovations. Complementing this is her mission-driven business, Expand the Soul, which helps people connect to their inner calling and live a life of true expansion.

Jessica’s journey began with grit. Rising from a difficult childhood, she was an electrician for 10 years, even working as high as 200 feet in the air at a shipyard. Her pivot to development began organically when she started fixing up her own home. This led to overseeing flips for an investor, where she was hands-on in every task, from tiling to managing contractors. This background provides Expansive Development with a foundation of deep, ground-up technical expertise.

Technical Mastery and Client Peace

Expansive Development shines by bringing tenacity, technical knowledge, and peace to complex projects. Jessica’s background means she is fluent in building science and code, allowing her to confidently guide clients through challenges that would otherwise overwhelm them, such as complex underpinning (building a new floor beneath an existing structure) or permitting issues

Shutterstock

Explore

“I love code and building science… I am very passionate about what I do and I think that really shows and it helps people feel comfortable with what they’re doing.”

Her philosophy on the job site is defined by integrity and communication. She emphasizes that she works to eliminate client stress, allowing them to enjoy the experience of watching their vision come to life. Her goal is simple: to make sure people “love where they live” and “feel expansive” in their own space.

The Resilience of Self-Building

Jessica’s difficult childhood forged her resilience and ambition. With everything in her life being self-made, she embodies a solution-based problem-solving mindset, always pushing forward instead of “tapping out.” This drive is what allows her to be highly reliable and deeply hands-on, skills she directly translates to her client work.

“Everything I have in my life is self-made. I’m self-built. And I guess I also like to build physical buildings too.”

Her personal journey informs her desire to help others find that inner strength, which is the mission of her parallel venture, Expand the Soul. This work encourages people—especially those in the fast-paced DMV area—to drop out of their heads and listen to their inner voice, intuition, and heart’s calling.

The Contractor Caring Network

Driven by a desire to help those who fall through the cracks of existing programs, Jessica recently launched the Contractor Caring Network.

Recognizing that contractors are the backbone of society, this network brings together professionals, investors, and contractors who want to give back their time and skills to homeowners in need. These needs can be as simple as fixing a broken toilet or window in a community that is often overlooked.

“I think the world is built on contractors from the roads to this… office that we’re sitting in to your home and they take care of us.”

This initiative is a reflection of Expansive Development’s brand, which has grown purely through reputation and word of mouth. Now, as Jessica is ready to step out from behind the scenes, she wants the world to understand that their brand is built on quality, care, and community impact.

A Legacy of Expansion

Jessica’s greatest wish for anyone listening is that they “follow their heart” and take the leap toward their inner calling, whether that’s starting a business or simply improving their home.

As a single mother, legacy is crucial. Her vision for Expansive Development is to reach and help more people, drive community impact through the Contractor Caring Network, and continue building a life of abundance so her daughter never has to worry about things. Ultimately, she wants to help people feel better on multiple levels: in their work, in their heart, and in their home.

Reach Jessica Winesett Below