Anna Taylor

By Alejandra Zilak

f you’ve been around the block long enough to remember Alanis Morissette’s music from the 90s, you know it is a universal truth that life does have a funny way of working things out.

In this month’s installment of “Women In Self-Storage,” we’re taking a look at the life of Anna Taylor, head of self-storage lending at Live Oak Bank in Wilmington, N.C. For the past 19 years, she’s worked in self-storage lending, and all she had to do to land herself in this industry was trust in signs and go with the flow to where life was taking her.

Taylor was born and raised in Wilmington, N.C. She’s the middle of three sisters, whom she calls her best friends: Laura and Mary Emma. They spent summers in Lake Michigan and had a series of three dachshunds, all named Tobey. While Laura and Mary Emma thrived as theater kids, often getting lead roles in their school’s plays, when she tried to follow suit, she was cast as a tree. “That’s when I decided drama wasn’t for me,” she says with a laugh.

Taylor gravitated towards sports, playing tennis, basketball, and golf with her dad. She continued being a sporty kid until it was time to go to college at the University of North Carolina in Chapel Hill. “I loved being a student there,” says Taylor. “It’s the quintessential college campus with beautiful quads and lots of trees, right in downtown Chapel Hill. It’s a really fun place to go to college. I loved the people, the classes, the sports—all of it! And when I was there, the basketball team won the national championship in 2009, which was a really memorable experience.”

She bounced around trying to find the right major, ultimately deciding on advertising. However, Taylor started her career trajectory while doing a minor in entrepreneurship. “We took business and economy classes,” she says, “and we could apply to an internship in New York City. Whoever was selected for the internship would be placed with a startup company.” Lo and behold, Taylor was selected for one of the spots, and she was paired with a tech startup called Loose Cubes.

“I loved moving to New York,” says Taylor. “Loose Cubes was in the DUMBO [Down Under the Manhattan Bridge Overpass] neighborhood in Brooklyn. I got to intern there the summer before my senior year, and I fell in love with the team and the company.”

The feeling was mutual, and they offered her a job when she graduated. “It was so exciting,” she says. “I think it should be mandatory that all young people live in a big city when young. I learned to be on my own, to have a budget, and getting out of my comfort zone to meet new people.”

Loose Cubes was ahead of its time, providing coworking spaces and renting out offices and extra desks to freelancers. “They could rent the space for the day, week, or month.” While the concept was novel at the time, it didn’t enjoy long-lasting success. “I got to see the hard times of startups,” says Taylor. “I didn’t realize that a lot of Series A investments were contingent on deliverables, and eventually, we lost our funding. One day, I walked in and realized that in two months, I would no longer have a job.”

Feeling dejected, Taylor called her boyfriend, Kurt, to give him the bad news. What she didn’t know was that at the time Kurt took her call, he was in New York City with his dad, secretly picking out her engagement ring. “His parents were from the city, and they went together to the same store where his dad had picked out the ring for his mom when he proposed.”

Soon after that, the couple went on vacation to Anguilla, a British overseas territory and island in the eastern Caribbean, where he got down on one knee and asked her to marry him. Happy and excited, they decided to move back to their hometown in North Carolina.

This is when Taylor’s story starts looking like a series of fortunate events. She had lost her job, got engaged, then moved back to North Carolina because she had lost her job in New York. Up next, she received a job offer to work at Live Oak Bank. “It’s one of the luckiest things to happen to me. And my first day on the job was on February 4^th, which is my birthday, so I took it as a sign that I should be there.”

That was 13 years ago, and she still loves working there. Ten of those years have been in the self-storage lending division. “We finance all across the country, and I do self-storage loans exclusively. It’s helped me become really good at my job, focusing on one thing.”

But getting good at what she does came with its share of challenges. “In the early days, I was trying to figure out what my style as a lender would be. You have to walk clients through all the financing options, how to structure loans, and prepare sales pitches the first time you meet with someone who’s interested in a loan.” At first, she’d listen to other people and try to mimic them, but she didn’t enjoy doing it that way because she didn’t sound like herself. “I had all this knowledge and I wanted to take this seemingly complicated process and make the path more smooth for customers. I then started taking the approach of explaining information to people instead of selling. That helped me set up relationships with customers.”

Taylor learned her craft thoroughly. When first becoming familiarized with the storage industry, she made a binder with two sections: one about self-storage and one about lending. “I had never heard of cap rates before, so I started learning the jargon.” That was 10 years ago; today she knows the industry like the back of her hand. At some point, she and her husband even bought two self-storage facilities. “That was one of my greatest accomplishments, because it was cool to tell customers that I was also in their shoes.” They’ve since sold those facilities, but she’d eventually like to become an owner-operator again.

As head of self-storage lending, now she has an entire team. Together, they get the word out that even though they have many small business customers, they also do financing for larger firms.

“Seeing my customers succeed is incredibly rewarding,” she says proudly. “I have so many stories of people who have used storage as a way to start a business, make money, then do good in the world. It’s not just about being financially successful but what you do with that money.”

That’s what she loves most about self-storage: the people. “I’ve been in the industry for a decade now, going to the same conferences every year and seeing the same familiar faces. And every single time I’ve had a question, needed recommendations, or I’ve wanted to make a connection, they’re always willing to help. It’s a very ‘I know a guy’ kind of industry.”

When asked what she’d say to women just getting started in self-storage, she mentions the good people again. “I would tell them that there’s so much opportunity here. I love seeing more and more women attending industry events. I’d tell everyone who’s new to not be afraid to reach out to people and learn from them. The industry is full of people willing to help. Ask for best practices, connections, or mentorship. You’ll get them.”

When she’s not working, Taylor still loves to do many of the things she enjoyed while growing up. “Tennis is my favorite hobby for sure, and I still play a little bit of golf. I also like mahjong and needlepoint. I have a lot of grandma hobbies,” she says. “I needlepoint my kids a Christmas ornament every year.”

She also loves to read; Pride and Prejudice is one of her all-time favorites. She loves French, Thai, and Mexican foods. She loves spending time with her kids, Marshall and Louise, and playing with their one-year-old golden retriever, Murphy. “He’s a bit of a handful, but he’s so sweet and just wants to be loved.”