Today we’d like to introduce you to Deana Henderson.
Deana, we appreciate you taking the time to share your story with us today. Where does your story begin?
Hello! My name is Deana Henderson, but to make life easier, people call me Dee. DeliveredByDee was born on April 26, 2020, the day the idea for this business was created. On May 6, I created my Facebook and Instagram pages, as those would be the main platforms I’d use to advertise and showcase my work. Both are @deliveredbydee. On May 28, 2020, I got my first delivery ever to a Walmart in Fairview, TN. I was desperate, so I took the order after finally convincing someone to take a chance on me. Looking back, I probably shouldn’t have done that order, LOL. It wasn’t the greatest experience, but hey, you live and you learn.
The Backstory: A Passion for Delivery
A little backstory on all of this is actually neat. I graduated college in 2019 from the University of Tennessee at Chattanooga with a Bachelor’s degree in Communication. While in school, I started doing gig work called Instacart. It’s essentially where you deliver groceries from various stores to people in the area. One day while doing a batch, I remember thinking, “I could be happy doing this.” It was fun. I was constantly busy, going everywhere, being exposed to different things and different stores, and loving every minute of it. I’d get up early and be sad when it became dark because I can’t see in the dark, so I was forced to stop. Even better, I loved the customers I’d developed relationships with because most of them would ask me, “How can I request you next time?” or “You shop for me like I shop for myself.” I felt good about what I was doing. I felt like I made a difference.
They say if you love your job, it doesn’t feel like work, and that’s basically what this is for me. While yes, it is work, I truly enjoy it. I’m someone who gets bored and needs variety, so this is perfect, as every order I do is never exactly the same. I’m also never going to just one place to deliver. So, after I graduated, I lived in Clarksville with my mom and had to take a hiatus from Instacart to actually try to put my degree to use. I applied everywhere. I knew I eventually wanted to be in Nashville, so I focused on jobs there. I found something and worked there for a few months so I could save up and eventually move to Nashville. In December 2019, I moved into my first apartment in Nashville with my two cats. It was a scary start, but I knew I could do it. I worked at that job for a few more months until, honestly, I got tired of it. This was literally just before COVID-19 broke out and the world basically shut down. So, I decided to work at Amazon in the warehouse. I learned very quickly that it was not for me.
The Birth of DeliveredByDee
On my personal Facebook, I kept seeing ads for “start your own business with Dumpling.” It was essentially a platform that took care of everything for someone starting a grocery delivery business. You were in charge of everything—the stores you wanted to go to, the pricing you wanted to charge people, and everything in between. You just had to pay a monthly fee to use their platform. So, when the world finally shut down, I was in a bind, and I needed to pay rent somehow and get rid of Amazon because I couldn’t continue to work there. My boyfriend at the time encouraged me to take that leap and actually do it. So, in April 2020, DeliveredByDee was born.
DeliveredByDee operated on the Dumpling platform for about a year or so. I’d gained weekly clients that I delivered to on a weekly basis, mainly from Publix. I also shopped at Walmart, Kroger, and Target for those who wanted that. When I wasn’t busy with my deliveries, I did a little bit of Instacart to supplement my income when needed. I got by; it paid the bills. For most of COVID, from 2020 to 2021, I was delivering to locals. I had about 10-15 clients that I delivered to weekly. Then, when COVID started to fizzle out, I lost most of my clients because the world was starting to open back up little by little, and people wanted to have some normalcy again. I understand that, but I’d be lying if I said I didn’t miss them. I did, and still, in a way, do. I keep up with a few of them on social media.
Shifting Focus and Finding My Niche
Sometime in 2021, for about six months, DeliveredByDee shifted to Trader Joe’s deliveries. I advertised in a ton of groups on Facebook, and before I knew it, I was delivering everywhere in Nashville that Trader Joe’s wasn’t available in. I absolutely loved that time in my business—any excuse to shop at Trader Joe’s was just everything for me, LOL! So, similar to the local deliveries during COVID, I developed weekly clientele for Trader Joe’s. I went to Murfreesboro, Smyrna, and Mount Juliet areas mostly, sometimes even Franklin right before the location there opened up. That went on until it just wasn’t feasible for me income-wise, as I had a Dodge Charger back then eating up gas like crazy. So, I unfortunately had to shut that down. Sometime in the summer of 2021, I believe, I remember doing a BIG delivery for someone who was visiting Nashville, staying in an Airbnb over in Franklin, and they wanted a delivery. They wanted everything—all the groceries from Publix, Costco, and tons of liquor. I don’t remember how they found me, but I’m so happy they did. It led me to now…
In April 2022, I found a local Facebook group called “Nashville Visitors.” At the time, the group was still new with barely 2,000 followers. I eventually became one of their group sponsors, gaining tons of traction for my business where people visiting the city wanted groceries and alcohol delivered to their Airbnb or hotel. Before I knew it, I was a busy bee. I had deliveries coming out of my ears. I also quickly realized that this is where the money was. I was advertising in that group, I had word-of-mouth reaching out to me for deliveries, and I was probably booked up almost every Thursday-Sunday for several weeks until about the holidays came around, then I learned that my business started to slow down.
The Current Operation
I also no longer operate on Dumpling. They started to take a turn that wasn’t going to work with my business, so I started to just do my own thing. It took trial and error, but the way I do it now is how I’ve been doing it. The process is simple: clients submit a contact form that basically tells me what type of delivery they’re interested in, where I’m supposed to deliver (whether it’s to an Airbnb or hotel), contact info, and the best payment method that works for them. We operate mostly with Venmo.
From 2022 to now, I really just focus on deliveries to tourists in Downtown Nashville. I offer an array of services such as stocking the fridge in the Airbnb before they arrive, drop-offs to the hotel before they arrive, and if they’ve opted in, I can meet them at their home for the weekend. Along with groceries being delivered, we offer other services such as charcuterie boards, mimosa/Bloody Mary bars, gift baskets, and everything in between. There’s nothing I can think of off the top of my head that someone has asked for that I’ve said, “I’m so sorry, but we do not deliver that.” If it’s reasonable, we will deliver, and happily so.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I truly believe everything happens for a reason. My time in Chattanooga for school led me to Instacart, and the 2020 shutdown forced me to redefine my career path, ultimately leading to the creation and growth of DeliveredByDee. I live by the motto, “If He’s going to take me to it, He’ll take me through it.” That first year was incredibly tough; I considered giving up more times than I can count. I relentlessly advertised my services, knowing their value, and eventually, the clients came. It took immense effort, but it happened.
Just as I finally found comfort and stability in my business, the world began to reopen. I lost clients and was back to square one, desperate to keep my passion alive. I prayed for guidance, which led me to offer Trader Joe’s deliveries. This worked for a while, and I loved it. Trader Joe’s, with its unique offerings, became a second home. I developed genuine relationships with the employees, who felt like partners on my journey. While I still shop there occasionally, it’s not the same without those familiar faces, though the store still offers a comforting sense of familiarity.
Mid-2022, after discovering the niche of delivering to Nashville tourists, I was living my dream: a self-employed business owner, working on my own terms. My routine was perfect. Slower delivery days were dedicated to the unseen aspects of the business – advertising, scheduling, client communication, and more. I took this life for granted. By late summer 2023, my personal life was in shambles. Mentally, emotionally, and physically drained, I shut down and temporarily quit. Looking back, I regret that decision, as it feels like I’m now trying to find that cherished routine again. My income dwindled, and I ultimately had to move back to Clarksville with my mom, as my planned deliveries wouldn’t sustain me in Nashville.
Today, I’m in a much better place, happier and in a clearer headspace to revive my business. What a mess I’ve left to clean up, though! I let many clients down by stopping abruptly and not even announcing a shutdown. My heart couldn’t bear to say goodbye. I poured so much time, energy, and tears into this, and I refused to let it all go to waste. I promised myself it wasn’t a goodbye, but a “see you later.” Now, in 2025, I’m slowly but surely rebuilding. While everything has an end, it also marks a new beginning. I’m still handling Nashville deliveries from Clarksville, still discovering myself in this chaotic world, and embracing every step of this business journey. I’ve learned there’s beauty in struggle, and it always signifies a lesson to be learned. What lesson, you ask? I don’t know yet, but I’m determined to find out.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I’m a 29-year-old business owner who was born with a hearing impairment. Throughout my life, I’ve never relied on my disability to get ahead—instead, I’ve worked hard for everything I’ve achieved. That journey has taught me that the most meaningful accomplishments are the ones you fight for, and the reward is even greater when you reach the goals you’ve set for yourself.
I never imagined I’d one day be able to call myself a business owner, but I’m proud of what I’ve built and what my business represents. I have the opportunity to make people’s vacations to Nashville smoother and more memorable by ensuring their groceries are delivered and ready before they arrive. Whether they’re celebrating a birthday, anniversary, or simply enjoying time away, I get to play a small part in making their experience extra special. It’s incredibly fulfilling to know that the work I do makes a difference—and I feel proud, empowered, and inspired every day.
Do you any memories from childhood that you can share with us?
I was born in Miami, Florida, and around the year 2000—when I was about four or five years old—my family relocated to a small town just outside of Nashville. I can still remember being in Pre-K, preparing to start kindergarten the following year.
One of my favorite memories from my time in Miami is of a small banana tree we had in our backyard. It’s something that has always stayed with me. I remember how we would pick bananas straight from the tree and eat them right there. They didn’t taste like the bananas you buy in stores—they were sweeter, more flavorful, and somehow better. To this day, I still miss the taste of those bananas and the simplicity of those moments.
That memory also sparked a lighthearted connection in my mind as a child: I knew monkeys loved bananas, and since monkeys were (and still are) my favorite animal, I figured it only made sense that I should love bananas too. It was a silly thought, but it’s always stuck with me and made that memory even more special. It reminds me of where I come from and how the smallest things can leave a lasting impact
Pricing:
- Pricing for all services can be found on website
Contact Info:
- Website: https://deliveredbydee.squarespace.com
- Instagram: https://instagram.com/deliveredbydee
- Facebook: https://facebook.com/deliveredbydee
- Other: https://linktr.ee/deliveredbydee
