Veteran Franchise Coaching

Watch the Vetrepreneur Franchise Bootcamp

Vetrepreneur Franchise Workshop   |   July 12

Watch the Vetrepreneur Franchise Bootcamp

Franchise Workshop   |   July 12

Vote for the Next Vetrepreneur® of the Year!

Vote for the Next Vetrepreneur® of the Year!

Lessons Learned: Navy Veteran Joe Calloway’s Rise in Real Estate

Joe Calloway 2021 Pittsburgh Vetrepreneur of the year

Sometimes you have to fail a few times before having success as a business owner. That was the case for Navy veteran Joe Calloway, who started flipping houses while serving as a recruiter in his hometown of Pittsburgh. His first two investments didn’t make him any money, but the projects led to a “light bulb moment” that paved the way for RE360, a successful real estate company. Calloway’s success since then has earned him numerous awards, including the 2021 Pittsburgh Vetrepreneur of the Year award from VIQTORY, the veteran-owned publisher of G.I. Jobs.

“I love Joe’s story,” said Chris Hale, VIQTORY’s co-founder, chairman and a Navy veteran. “Pittsburgh kid from Carrick High School. Joins the Navy. Learns how to sell as a Navy recruiter. Comes back to his hometown. Goes to Pitt on the GI Bill. Starts buying, renovating and renting real estate. Turns it into a great business where he owns and leases more than 300 properties and employs 40-plus people. Joe is a great representative of our city and the veteran business community. Congratulations Joe!”

Get Rich Quick

Like many successful entrepreneurs, Calloway’s path was hardly easy, fast or smooth. Calloway grew up near Allentown, a south Pittsburgh neighborhood that RE360 now calls home and helped to revitalize. He enlisted in the Navy and served first as an electrician’s mate, then as a recruiter.

Calloway used his 2001 reenlistment bonus to buy a house, intending to fix it up and sell it for a tidy profit. He taught himself construction—including wiring, drywall and tiling—and worked at night and on weekends for about a year to fix it up.

“That didn’t work out real well because I sold it and I made my money back, but no profit,” he said. 

That didn’t deter Calloway from trying again. Within a couple years of separating from the Navy in 2005, he bought another fixer upper to flip. He had plunked down several thousand dollars to take a “get rich quick” course, and dreamt of making tens of thousands of dollars flipping houses. 

“Instead, I rented the house and was making 50 bucks a month,” he said.

That’s when Calloway had his light bulb moment. He realized that the steady drip of income from buying fixer uppers and renting them instead of flipping the properties would eventually build into a lucrative portfolio. 

“That one didn’t go as planned, but it got me into the rental game and then from there on out I kept focusing on rentals versus trying to flip properties and get rich quick,” he said.

“Fort Pitt Capital Group believes the entire community benefits when a veteran integrates the values they learned during their service to build a business. Joe Calloway does just that as he restores properties using a team-driven approach through his company, RE360. We congratulate him as the 2021 Pittsburgh Vetrepreneur® of the Year.” 


Theodore M. Bovard, Managing Director, Fort Pitt Capital Group

Side Hustle

And the rest is history, right? Hardly. Buying, fixing and renting properties was Calloway’s side hustle as he worked on an MBA, then worked full time for a commercial real estate company—all the while starting a family.

In 2009, Calloway left his full-time job and started RE360 with a partner. When the original model of buying the debt behind commercial real estate didn’t work out, they shifted their focus to buying, fixing and renting single family homes. Calloway borrowed money from relatives, friends and investors to buy the properties. He lived humbly off the rents from the handful of units he’d purchased over the last few years. For two and a half years, he didn’t get paid. 

“That doesn’t go over well when you walk in the door at night after a year or two and say, ‘We still don’t make any money.’ So that ultimate early sacrifice was probably the most challenging thing that I look back on now with fondness,” Calloway said.

Turning the Corner

Eventually that steady drip of income grew as the rental portfolio increased. Still, there were struggles and growing pains, and it wasn’t until 2018 that Calloway finally felt like RE360 was successful.

“I would say it probably took 10 years to have a real, sustainable business,” he said.

RE360’s quirky office space is located in a historic building in the Allentown neighborhood, where the company began buying blighted business district properties in 2013. The business district was only 25% occupied then. Today it fluctuates between 88 and 95% occupied, including more than a dozen properties owned and rented by RE360.

“So we have all these different places now that the business district has been reactivated, which ultimately brings jobs,” Calloway said.

And accolades. Calloway was named to a “40 Under 40” list and earned an EY Entrepreneur of the Year award. RE360 has been named to the Inc. 5000 list of fastest-growing privately held companies in the nation and is a regular on the Pittsburgh Business Times’ Fast 50 list. But for Calloway, the 2021 Pittsburgh Vetrepreneur of the Year award is special because G.I. Jobs helped him navigate his transition from the Navy.

“My experience in the Navy was very formative to me as a leader, business person and entrepreneur,” Calloway said. “There is no other educational institute, job training program or experience that can come close to what the military has to offer for young men and women. Being the Pittsburgh Vetrepreneur of the Year is the highest honor I can receive as an entrepreneur, as it was the military that gave me the confidence, and tools and education to be a successful entrepreneur.” 

Photo by Rich Waters

Learn how to be your own boss with franchising!

Share on social

What To Read Next

How Vetrepreneur Franchise Coaching helped Jason Fish transition from military life to successful franchise ownership, empowering veterans with the tools for entrepreneurial success.
Discover how Vetrepreneur Franchise Coaching can help aspiring franchise owners overcome information overload and achieve their franchise ownership dreams with ease.
Discover how to access funding options and resources for veteran franchise ownership.