Grace Sampson, Real Estate Entrepreneur on Influential Women

Influential Woman · Prior Space Force Real Estate Military Spouse

Grace Sampson

Real Estate Entrepreneur, Sampson Properties

IL

Certifications · Degrees · Memberships

Degree Bachelor of Science in Business Management from Air Force Academy Degree Systems Engineering (started) Degree Spectre Space fellowship

Her Story

About Grace

Grace Sampson served 4 to 5 years on active duty in the United States Space Force after graduating from the Air Force Academy with a Bachelor of Science in Business Management. She initially studied systems engineering at the Academy, held leadership roles including gospel choir director, and completed a Spectre Space fellowship that bridged young officers with commercial technology and industry. As a dual-military spouse, she separated from service about a year ago to focus on real estate entrepreneurship and property management, building and operating a family portfolio that includes multiple Airbnbs. Her prior experience as an acquisitions and contracting officer informs daily operations such as tenant screening and credit reviews. She and her family are currently preparing their home for rental use ahead of a move to the Illinois area.

Her Interview

Ten minutes with Grace

01What do you attribute your success to?

I think that I've been through hard things like everyone else but resilience and perseverance have helped me tremendously. The reason I am resilient is because I believe that life has meaning and struggles are meant to build and refine you. I come from hard-working parents from Southside Chicago who went through really hard things so I do a lot of perspective-taking and live gratefully for the privileges I have.

02What’s the best career advice you’ve ever received?

The best career advice I received was to be humble and to be a sponge. Being genuinely curious and honest about what you don't know opens up so much and has made me successful in certain moments. It's good life advice too - being curious about people and new environments helps you grow as a person.

03What are the biggest challenges or opportunities in your field right now?

The biggest challenge in entrepreneurship is that school environments don't build entrepreneurs - they build people who follow a syllabus and perform to a certain area. It's a challenge to create your own structure without someone telling you to get up or clock in but it's also an opportunity to test your work ethic and character since you're your own boss and make calls on gray areas.

04What values are most important to you in your work and personal life?

People and community are most important - being able to mentor and not gatekeep knowledge. Faith is the underlying fuel to my passion. Authenticity, being honest and real and showing up in the moment are key values.

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