In 2019, Frank and John were real estate investors at a crossroads. Over the past six years, they bought rentals and flipped homes. During that time, they experienced wins and losses, but most importantly, they gained a lot of experience. They dreamed of pursuing their passion for real estate full-time, but like so many other investors, they were struggling to find high-quality investments.


Frank and John, being West Point graduates in the same class (2009), had been in touch over the years and frequently discussed real estate. Eventually, John recognized the shared challenge of finding deeply discounted homes. He knew that together he and Frank would be unstoppable. So he suggested they join forces and try acquisition techniques used by successful house flippers. They banded together with the shared goal of acquiring 10 off-market rentals by the end of the year.


Gray Line Investments was born.


The first market they chose was Lawton, OK. They pulled their first list of leads, divided it between them, and began manually cold-texting potential sellers offering owners a cash purchase and a two-week closing. They quickly realized it was going to be harder than expected.


In fact, it was a disaster. They struggled to manage the hundreds of text messages they sent. They didn’t have a way of tracking potential leads, and they didn’t live in the market and couldn’t meet sellers face-to-face. They found themselves in dire straits.


A decision had to be made. Realize their ineptitude and abandon the dream, or bear down, grit their teeth, and commit to figuring it out. They chose the latter. After intense brainstorming, they realized their biggest opportunity was to leverage technology and systems to streamline the process.


While working full-time jobs, Frank and John fought and scratched their way to building a system capable of acquiring multiple off-market, deeply discounted homes each month. The business quickly grew to the point where they had more deals than they could service with their own funds. So they adopted a wholesaling business model and began selling contracts to other investors.


Seemingly overnight, Gray Line grew from acquiring a single off-market property in Oklahoma to consistently acquiring more than ten off-market opportunities a month. Gray Line doubled down on their efforts, hired more amazing team members, and put their foot on the gas.


Today, Gray Line Investments is a real estate machine. We offer 15-20 off-market opportunities to investors each month. We flip homes. We raise money from partners. And, now, we are teaching others to do the same.


Our mission is to become the premier buyer, seller and thought leader of off-market real estate in the United States. Our dream is to build a community that improves people’s lives through real estate investing, education, mentorship, and giving back to veterans.