Bridging the Divide: Holly DeShields and the Misunderstood Art of Lobbying

In the milestone 10th episode of Uncharted: Your Sidekick for Life, we are introduced to Holly Deshields, a force in the world of lobbying whose career reflects a profound dedication to connection, strategy, and advocacy.

Holly, a Director of Consulting at McGuire Woods Consulting, embodies a balance of grace and determination that leaves a lasting impression—even on those skeptical of her profession.

Lobbyists don’t always get the best reputation, as Holly herself acknowledges with a laugh:

But what would society look like without them? Lobbyists are essential mediators between private sectors, public interest groups, and policymakers, translating complex needs into actionable legislation. Without lobbyists, the intricate bridge connecting industries, nonprofits, and government would crumble, leaving a vacuum in informed advocacy and specialized expertise.

Holly is here to prove that the reality is far from the cynical stereotypes.

From her childhood, it was clear Holly was destined to be a trailblazer.

“Politics has been in my blood since I was a kid,” she says, recalling her fourth-grade class election poll. She grew up in a family that was apolitical—her mom a teacher and her dad a used car salesman—but her early love for debate and policy marked her out as unique. While other kids were dreaming of summer vacations, Holly was plotting pathways to governance. “If you don’t vote, you can’t complain,” she says, encapsulating her no-nonsense ethos.

Her journey began at the University of Texas, where a chance encounter with a sorority sister landed her an internship at the state Capitol. That internship turned into a 12-year tenure with a state senator, during which she rose through the ranks to become his chief of staff—the youngest and only female in such a role at the time.

This period, she says, cemented her core values of respect, strategy, and collaboration.

“We’re not curing cancer,” she recalls a mentor once telling her, “but we’re still making a difference.” That difference, for Holly, has taken many forms, from securing $200 million in state incentive funding for the entertainment software industry to championing access to immunizations for children.

Her ability to solve problems—be it a zoning issue for a fire department or funding for a charitable pharmacy—reveals her knack for turning complex challenges into actionable solutions.

The episode also brought in fresh perspectives from Gen Z, including questions from Samarth and Mahi.

Mahi: 

To this Holly replies with

She recounted a recent experience with an 18-year-old shadowing her for a day, sharing how real-life exposure can ignite a passion that no classroom ever could.

“You can’t explain what I do until you see it,” Holly adds, highlighting the importance of learning through action.

Samarth: 

Holly addressed this with a forward-thinking perspective:

Throughout the episode, Holly shared her belief in the power of mentorship and vulnerability. Her advice to Gen Z listeners was clear: focus less on perfection and more on progress.

By the end of the episode, Holly's experience and personality had come through. 

Whether she’s fighting for industry funding, mentoring a young professional, or balancing her career with raising her ten-year-old son, Holly embodies what it means to lead with purpose.

So now, it’s your turn:

What risks are you willing to take to discover your passion?

Listen to Holly Deshields on Uncharted: Your Sidekick for Life – Episode 10, Season 1.

Holly Deshields: Holly is a Director of Consulting at McGuire Woods Consulting and a seasoned lobbyist with over 20 years of experience. Known for her strategic approach and dedication to advocacy, she has championed causes ranging from state incentives for the tech industry to expanding healthcare access. Starting as an intern at the Texas Capitol, Holly rose to become the youngest female chief of staff for a state senator, showcasing her leadership and drive. Beyond her professional accomplishments, she is a devoted mentor and single mother, embodying resilience and grace in all aspects of her life.

Natalie Peyton: Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program. If you would like to listen to her work, here it is: Snoriezzz

Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.

Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.

This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.

If you would like to join the conversation email us at anais@foundingup.com

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