Kirby Atwell didn’t start his real estate career with a grand plan, just a desire for something beyond his day-to-day duties in the Army. In 2006, stationed in El Paso, Texas, he picked up “Rich Dad Poor Dad,” and, within a week, bought his first rental property. That single step set him on a path that would eventually lead to a portfolio of 39 short-term rentals and the financial freedom he had envisioned from the start.
After leaving the Army, Kirby jumped into house flipping, completing about 75 projects between 2011 and 2016. While the business looked impressive from the outside, the reality was a constant grind. Overhead costs, multiple contractors, and marketing expenses left little profit at the end of each cycle. Kirby realized he had traded his military schedule for a different kind of treadmill, and it wasn’t the life he wanted.
A turning point came when he and his wife renovated the basement of their home into a one-bedroom Airbnb. That summer, the space brought in $22,000, more than some of his long-term rentals earned in a year. Seeing the potential, he shifted his focus entirely to short-term rentals, starting with budget-friendly multi-unit properties in Northwest Indiana. The key was risk management: each property could operate as a long-term rental if needed.
By clustering his rentals in one area, Kirby built economies of scale. Supplies are stored in a central location, cleaners can handle multiple turnovers in a day, and his knowledge of the local market gives him a competitive edge when acquiring new properties. Today, his portfolio also includes properties in southwest Florida, but his primary base remains in Indiana.
Kirby’s strategy isn’t about chasing the highest possible nightly rate or buying luxury vacation homes. It’s about balancing steady cash flow with long-term security. His rule of thumb is clear. Net monthly income should equal about 1% of the property’s purchase price. That approach, paired with conservative financing and flexible use options, allows him to sleep well at night, knowing his investments are resilient.
Through his Living Off Rentals coaching program, Kirby now teaches other investors how to build portfolios that support their lifestyle goals. For him, success isn’t measured by how many deals you close. It’s about creating a business that works for you, not the other way around.
If you want to learn more about Zen and the Art of Real Estate Investing Podcast, check out https://zenandtheartofrealestateinvesting.com/podcast/269/.