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July 28, 2025 31 mins

Scaling a real estate portfolio is challenging enough—but doing it across multiple states while serving in the military takes a whole different level of strategy. 

Jefferson Calloway started investing in 2019 while stationed as a helicopter pilot in the U.S. Army, buying a townhome near Fort Rucker, Alabama.

Since then, he’s mastered creative financing and grown his portfolio to 27 doors across seven states with over $1 million in equity.

Jefferson is here to share how new investors can find and finance deals creatively, scale in high-interest markets, and why investing near military bases might be one of the best-kept secrets in real estate.

Find out more:
Jefferson@calcapital.us
Website - www.americanhomeconcepts.com
Instagram - https://www.instagram.com/jeffersoncalloway/
LinkedIn - https://www.linkedin.com/in/jefferson-calloway-2bb17381/

Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.

https://www.livegreenlocal.com

And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits.

https://www.rcbassociatesllc.com

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