Founder of Hatteras Sky, UT alumna, speaks to student entrepreneurs about the art of career pivots
Amy Kelly pivoted from a successful law career into starting her own property development company, based out of Atlanta, Georgia.
When Amy Kelly first enrolled at the University of Tennessee, Knoxville (UTK), her aspirations were firmly rooted in a law career. Little did she imagine that one day she would be the Co-Founder and Principal of a thriving real estate development company based out of Atlanta. Her company, Hattaras Sky focuses on multi-family sites and boutique hotels in bustling artisan and cultural communities. One regional project is the Radical Hotel in Asheville, North Carolina.
“I’m not an inventor, and I always thought you had to be one to be an entrepreneur,” Kelly shared. “But that’s certainly not the case. In fact, the people who become the most well-respected are the ones who can take the idea and bring it to the masses in the most effective way.”
That’s pretty much exactly what she’s doing with Hatteras Sky. Kelly didn’t invent boutique hotels, but she’s commercializing them, making them accessible in new areas, and helping connect the public with local art and history as a result. Kelly and her team have expanded their reach across the country, with properties in Seattle, Asheville, Phoenix, and beyond.
“On a given day, we’re strategizing sites, sipping cocktails, and planning launch events for exciting new spaces,” Kelly said. “We pursue projects that pique our interest and fuel our passions.”
Kelly recently spoke to a room of aspiring entrepreneurs at UTK’s Anderson Center for Entrepreneurship and Innovation as part of the Spring semester’s Vol Court Speaker Series. Vol Court is a program that culminates in a business pitch competition, with the top winner walking away with $1,500 to bring their idea to life. Previous winners, including Mickey Napier, Tony Tuber, and Blake Hopkins, have since built thriving ventures of their own.
For Kelly, Hatteras Sky was born out of a leap of faith taken just before the COVID-19 pandemic—a challenge in itself. She invested her own money, took on entrepreneur debt, and navigated the complexities of an industry in flux. However, her law background proved a powerful tool. It gave her the knowledge to expertly negotiate deals, dissect contracts, and leverage valuable connections. Despite her qualifications, Kelly confessed to the students that she didn’t start as a real estate expert.
“My biggest piece of advice is to fake it until you make it… but don’t do anything irresponsible,” Kelly told the students. “You can offset your lack of experience by presenting yourself and your business effectively.”
She emphasized the importance of networking and attending events, pointing out that one of her largest clients came from a casual post-conference meeting that almost didn’t happen. This encounter underscored a key point in her journey — you never know where or when opportunities will arise.
As a business owner, Kelly also advised the students to be prepared to wear many hats, especially in the early stages. Recalling a personal story, she explained how she spent 20 hours assembling a chandelier for a launch event after her electricians canceled last minute.
“I had no idea what I was getting myself into,” she said. “I love the idea that every day of work is different, and I never know what to expect.”
Wrapping up her talk, Kelly shared an important insight on market dynamics, encouraging students to think carefully about where they decide to do business.
“In places like Washington D.C. and Atlanta, the approach is transactional—’What can you do for me? What can I do for you?’ But in Knoxville and Asheville, it’s about relationships—’I want to work with people I know and trust.’”
View the Vol Court Schedule here.
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