Meet Jennifer Mccloud

We recently connected with Jennifer Mccloud and have shared our conversation below.

Jennifer, thank you so much for making time for us. We’ve always admired your ability to take risks and so maybe we can kick things off with a discussion around how you developed your ability to take and bear risk?

I have developed a strong tolerance for risk because I’ve experienced the deep sense of accomplishment that comes from overcoming obstacles to achieve meaningful goals. This has been true in many areas of my life, particularly in my success as an entrepreneur. The greatest rewards often come from pursuing challenges that carry the greatest risks. While overcoming small risks can be satisfying, it is conquering what once seemed insurmountable that brings the most profound sense of achievement.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I’ve been a serial entrepreneur since my early 20s, building several successful businesses—though, like any entrepreneur, I’ve also had a few that didn’t pan out. My 12th venture was the real breakthrough, providing me with the means to acquire 412 acres of beautiful, historically significant agricultural land—now home to Chrysalis Vineyards, Locksley Farmstead Cheese Company, and the Little River Bakehouse. This became the foundation for the Ag District, a hub of agricultural innovation and a shining example of rural enterprise.

Too young to retire and always driven by ambitious goals, I came to Virginia with the initial intent of growing grapes, particularly the state’s native Norton grape. That endeavor quickly evolved beyond cultivation into winemaking. As I became more immersed in the agricultural community, I recognized additional opportunities to support and expand local food production. This led to the creation of Locksley Farmstead Cheese Company—a true farmstead creamery where we raise our own dairy herd and craft artisanal cheeses—and the Little River Bakehouse, which produces farm-to-table offerings sourced from local ingredients.

By integrating winemaking, cheesemaking, and food production, I have worked to build a thriving agricultural ecosystem that preserves tradition while embracing innovation. Through the formation of The Ag District (A Virginia-Registered Agricultural and Forrestal District), I’ve created a model for thriving rural enterprise—one that celebrates the land, supports local agriculture, and showcases the endless possibilities of a diversified farm.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

– Effective Communication & Passion
>>>To succeed, you must be able to communicate your passion clearly and persuasively.
>>>Inspire others to embrace your vision and rally support for your goals.
– Versatility & Problem-Solving
>>>Being a jack-of-all-trades is essential—many tasks won’t have a professional on hand to solve them.
>>>Developing a diverse skill set allows you to adapt, troubleshoot, and keep things moving forward.
– Perseverance & Optimistic Focus
>>>Challenges are inevitable, but maintaining a positive outlook and unwavering determination is key.
>>>Resilience separates those who push through from those who give up.
– Lifelong Learning & Adaptability
>>>Cultivate an unquenchable thirst for knowledge—always be willing to learn and grow.
>>>When faced with obstacles, draw on your inner strength to figure things out and keep progressing.

Okay, so before we go, is there anyone you’d like to shoutout for the role they’ve played in helping you develop the essential skills or overcome challenges along the way?

L. Ron Hubbard, the author of numerous Scientology texts, played a significant role in shaping my professional development. His writings provided valuable insights that influenced both my personal growth and business practices, which I believe contributed to my success. Additionally, my experiences within the Scientology community helped instill in me the confidence and resilience needed to navigate the challenges and rewards that come with success.

Contact Info:

• Website: https://www.chrysaliswine.com/ & https://locksleycheese.com/
• Instagram: chrysalisvineyards & locksleycheese
• Facebook: https://www.facebook.com/ChrysalisVineyards & https://www.facebook.com/profile.php?id=100054326899736
• Linkedin: www.linkedin.com/company/chrysalis-vineyards & www.linkedin.com/company/locksley-farmstead-cheese-co