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From Setback to Success: Aaron Chiles’ Real Estate Origin Story
Thursday, November 12, 2026
Doors Open: 6:30 PM | Meeting Starts: 7:00 PM
VFW in Evans
4290 Triangle Industrial Dr, Evans, GA 30809
Real estate success rarely follows a perfectly straight path.
This month, Augusta REIA welcomes Aaron Chiles, Professional Engineer, real estate investor, entrepreneur, and founder of Prepared Space LLC, for an honest discussion about his real estate origin story—from early setbacks and stepping away from investing to rebuilding and developing a growing rental business while maintaining a full-time professional career.
Starting Again
Aaron’s first experience with real estate investing did not end the way he had hoped. After experiencing significant setbacks early in his investing career, he stepped away from real estate for more than a decade.
In 2021, he made the decision to try again.
Rather than waiting until he had every answer, Aaron returned with a renewed mindset centered around intentional learning, better preparation, systems, and a willingness to take imperfect action.
Today, Aaron owns long-term and short-term rental properties and manages a portfolio of 12 short- and mid-term rentals throughout the Augusta–Aiken area, including properties operated on behalf of other investors.
What Aaron Will Share
During this meeting, Aaron will discuss:
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How he originally entered real estate investing
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The setbacks that caused him to step away
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Why he ultimately decided to return
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What he changed when starting over
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Lessons learned from building his rental portfolio
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Balancing real estate with a full-time engineering career
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Using systems, technology, and automation to operate more efficiently
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The importance of taking action instead of waiting for perfect conditions
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How relationships and community have influenced his growth
About Aaron Chiles
Aaron Chiles is a registered Professional Engineer with more than 20 years of engineering experience and the founder of Prepared Space LLC.
Through Prepared Space, Aaron specializes in rental management, co-hosting, property setup, and guest-experience optimization. His approach combines practical investing experience with data-driven decision-making, technology, systems, and automation.
Aaron also hosts regular short- and mid-term rental investor meetups and is helping launch the CSRA STR Alliance, an initiative focused on education, responsible rental practices, and advocating for fair short-term rental regulations for local hosts and property owners.
Aaron and his wife, Octavia, have three children. Guided by his faith and his desire to build a lasting legacy for his family, Aaron views real estate as more than acquiring properties—it is an opportunity to create value, serve others, and build something meaningful.
Who Should Attend?
This meeting is especially valuable if you:
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Want to begin investing but are hesitant to take the first step
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Have experienced a setback or unsuccessful deal
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Are balancing investing with a full-time career
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Are interested in long-, mid-, or short-term rentals
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Want to learn how another local investor built systems around his business
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Want to connect with other investors throughout the CSRA
Come early for networking and stay after the presentation to meet fellow investors and continue the conversation.
Your first attempt does not have to determine the rest of your real estate journey.