Moms to Know: Jenny Hales, Vice President of Operations, Grateful Hospitality
Fifteen minutes before the doors of Hales Blackbrick open, the staff of the popular South Tampa restaurant gathers for a motivational meeting. “It’s really a pep talk before a busy dinner service,” says co-owner Jenny Hales. “We have something in our company called grateful armor, and we like to touch on that in those meetings. It helps keep everyone centered.”
Gratitude has been the primary guiding force for Jenny and her husband, celebrity chef Richard Hales, ever since 2011 when he was diagnosed with a benign brain tumor and later thyroid cancer. He had three surgeries in less than six months.
“Those health scares changed us deeply. They gave us an even greater sense of perspective and gratitude, and that is where the name Grateful Hospitality really comes from.”
What do you do in your role as VP of Operations for Grateful Hospitality?
Jenny Hales: I do a little bit of everything and then some. I’ve always been my husband’s right hand since our first restaurant opened in 2009.
I was always in more of a behind-the-scenes support role for the restaurants, handling administration, payroll, bookkeeping, human resources, special events and so much more.
When we moved to Tampa in 2020 and opened Blackbrick Tampa in 2022, I told Richard I wanted to take a real stab at helping inside the restaurant. He asked me if I was sure because I had seen over the years just how hard he worked and how many hours it took. But I didn’t hesitate. Since then, I’ve been involved in every aspect of our operations here in Tampa. I helped open both restaurant locations and run them, and I’ve been the acting GM since we opened.
And not just on the business side. You also serenade diners occasionally. When did you discover your singing talent?
Jenny Hales: I’ve been playing classical piano since I was about 8 years old, and I started singing a few years after that, once I discovered I could. I never pursued music as a career because I always knew I wanted to be a stay-at-home mom someday, and I felt that path would not really allow for that. But now I get to sing to our guests at the restaurant all the time. I’ve become known as the birthday and anniversary singer, and I do it with love because it brings me so much joy.
The restaurant business is known for being demanding. How do you meet those demands while still being the kind of mother you want to be to your teenagers, Lily and Violet?
Jenny Hales: I try to be very efficient with my time at the restaurant so I can be home as much as possible. During the week, I work Tuesday evenings while Richard stays home with the girls. We’re both home on Mondays and Wednesdays, and then we both work on the weekends. Sundays are our family day. We go to church together, eat together and spend the whole day with the girls. We do that consistently.
So we really do spend a lot more time with them now. These high school years are crazy because they are so busy, but I love it, and I’m trying to enjoy every second because I know it goes by way too quickly.
It’s obvious that you and Richard are very much a team — close at work and as spouses. Why is it so important to you?
Jenny Hales: We are more than a team. We are truly more like one person, and that is such a blessing because I know that is not the case for many spouses. But we wouldn’t have it any other way.
We have always been very close, but opening these businesses together and walking through difficult personal moments together has only brought us closer. We are Christians, and we have realized that putting God first in our marriage and in our relationship has made us closer than we have ever been.
So it is not just important to us, it is everything. It is the foundation of our lives, our marriage and our family unit.


