
Today we’d like to introduce you to Diandra Culver.
Hi Diandra, so excited to have you with us today. What can you tell us about your story?
I have been baking since an early age, always going over to my neighbor’s house to learn new tricks. When I was in college, I learned a lot working for a friend’s bakery. After college, I worked for Disney for seven years before deciding I wanted to go out on my own and continue doing what I have always loved as just a hobby. With the help of my husband, we searched for the perfect spot to have the Cupcakery.
At the time, we were building a home and had to pass Main Street when we would go visit to see the development. This is how we found our perfect little space for the bakery. From there, the rest was history. We now offer custom cakes, cupcakes, dog treats and also have a custom cupcake bar for guests to design their own cupcakes.
We all face challenges, but looking back, would you describe it as a relatively smooth road?
I opened four months prior to the pandemic, which ended up being a very scary couple of months but we survived with the help of the amazing Winter Garden community. At one point during the worst of it, I was running the bakery by myself. It made for some challenging moments trying to figure out how to get customers to continue coming in. We adapted by getting DoorDash and UberEats as well as started offering curbside delivery. When toilet paper was going through its shortages, we would have “sales” where if customers bought six or more cupcakes, they would receive a complimentary cupcake decorated like a roll of toilet paper. It made for a bit of light during a very dark time.
Appreciate you sharing that. What else should we know about what you do?
I worked in professional hockey during college as a Game Operations Coordinator for the Mississippi RiverKings while going to Ole Miss. My original plan was to work in professional sports before starting the Disney College Program in 2013. From there, I worked for Disney for seven years in Children’s Activities and planning special events for the Polynesian Village Resort. I left the company in 2019 to open Sweet Dee’s Cupcakery.
Can you tell us more about what you were like growing up?
I have always enjoyed baking from a young age. I used to have Cupcake Wars competitions with my friends every holiday season. My neighbor took all the Wilton classes and passed along a lot of what she learned to me.
Contact Info:
- Email: sweetdeesfl@gmail.com
- Website: www.sweetdeescupcakery.com
- Instagram: @sweetdeescupcakery
- Facebook: @sweetdeescupcakery

Image Credits
First 4 Photos – Eli Doss
