Building roots: Real estate investor focuses on renovating Tupelo properties

By Zack Orsborn | via Daily Journal

At age 11, Chris Rakestraw (’10), Tupelo real estate investor, found himself flipping through real estate ads after moving to Tupelo in the 80s.

Growing up in Alpine, Miss., his mother raised three kids in a small two bedroom house.

He played in gardens, raised hogs and helped his mother cook mustard greens, corn and peas they picked the day before.

“We were just poor,” Rakestraw said. “My mom knew there was a better life for us, so she moved us to Tupelo. That’s where it all started. It was an awakening for her and myself, as well.”

Before his real estate career kicked off, Rakestraw worked as a banker in his early 20s. Wanting more, he left his job in 2004 to renovate his first house.

“My first house was a learning experience. It helped me realize that there could be a different story to my life,” he said. “As I worked on that house, I was working on myself, too. With the first house, second house, third house, I built confidence in myself.”

Since then, Rakestraw began adding his “eclectic transitional” style to flip older homes, inside and out.

He enjoyed the process of rebuilding structures and reconfiguring floor plans while also adding modern fixtures.

After Christmas, he helped move his mom into a new home he helped her renovate.

“I’ve done a lot of projects, and my mom has just commented on about everyone of them,” he said with a laugh. “She told me I was crazy at times, and she’s not the only one. Now, she understands. I know what she likes, and she let me go with it.”

His most notable project began three years ago, known as the Greensboro Cottages, where he renovated five apartments on the corner of Green and Jackson streets.

“That project was probably where I grew the most. It was a difficult project and stretched out well over a year to do the five apartments,” he said. “That’s one of the projects where people told me I was crazy and that I would never get the rent.”

But now, the cottages have a 100 percent occupancy. The interest from the cottages spurred his interest into revitalizing the West Jackson corridor.

He recognized the potential as the city and the Neighborhood Development Corporation began upgrading the infrastructure of the area.

“It is my hope to do more in that area,” he said. “If everything comes together, and I have a part in it, when you drive down West Jackson Street, it’s going to be like flipping the pages of Southern Living.”

Two months ago, Rakestraw finished his 1119 W. Jackson St. project, reconfiguring the floor plan from a two bedroom, one bath to a three bedroom, two bath and adding a front porch. The house sold recently.

Now, Rakestraw is converting the old Pizza Doctor building on 621 Joyner Ave. that was once a little neighborhood market called Booker’s Grocery Store.

Ten years ago, the building was converted into two apartments, and Rakestraw plans to transform them. He calls them Booker’s Condos.

“It’s a loft on the ground floor with 12-foot ceilings with a lot of modern finishes,” he said. “The facade has already undergone complete transformation. After months, I have gone in there and reconfigured the whole building and put a lot of money into to it to create two really super cool loft-style apartments.”

After living in Nashville for two years while also completing projects in Tupelo, Rakestraw said he’s ready to transition and concentrate on more properties in Tupelo. He gained inspiration from Nashville’s development renaissance and wants to bring that back to Tupelo.

To him, it’s his home.

“It has the potential to be really great, and of course, all of my family is here,” Rakestraw said. “The times I’ve been in Nashville, I’ve become disconnected with some people, and I really just wanted to get back to Tupelo.”