From Tech to Terroir
How Jess Outer Turned a Love of Wine into Ownership and Community
Want to follow Jess’s next chapter?
Follow her on IG, handle: @DCWineGal; and check out her website: www.unwinedva.com
What were you doing when you decided you wanted to get into wine?
I don’t know if I actually decided to get into wine. It’s more like I fell in love with wine and knew that I wanted to work with wine, with the farmers who make wine, and the wine community on some level. I also knew that I wanted to own a small business one day. I didn’t know why, nor did I know how, but I just knew that I had entrepreneurship in my blood and one day I would make it happen. My love of wine continued to grow as I traveled the world with friends on vacations. We would go wine tasting and meet with the wine makers and the farmers to really understand their wine-making processes. That’s when I really started to love the industry, and I knew I had to do something with it.
Was there a specific moment when you knew: “I want to own a wine shop and restaurant”? Or did the clarity come in pieces?
I was at IBM for 16 years. I did almost everything (consulting, marketing, sales, employee engagement, events, communications), and I absolutely loved my time there. I met many great, smart people, traveled to a lot of exciting places, and really learned how to build and run a business. However, I knew I needed something more. My entrepreneurship bug just kept biting away at me, and I knew that 2020 was the year I had to pursue it. In 2019, a friend introduced me to the owner of Unwined, a very well-respected wine shop in Alexandria, VA, and that’s how my journey began.
What made you brave enough to leap, especially after all that time in tech and consulting?
I can’t say that I was “brave” to “take the leap” after my years at IBM. I just knew it was my next chapter. It’s where I am meant to be. It’s what I am meant to do. I am bringing all of the same values, morals, and diversity of thought that I brought to IBM in a completely different capacity. Now I am simply bringing it to my own business and the community that my business serves. To pursue this dream, I worked part-time at Unwined while also working full-time at IBM. Fast forward four years, and I have left IBM to fully immerse myself in this dream, and I have officially bought the shop (Unwined) and the restaurant (Revel).
How did you wrestle with questions like, “What will people think?” or “Am I wasting my experience?”
I didn’t really wrestle with any questions like “What will people think?” or “Am I wasting my experience?”. I have never cared what people thought, and that never actually crossed my mind because it’s what I wanted to do. I knew it was right for me. I also knew I was not wasting my experience because, as a business owner, you have to juggle a lot of hats. You have to be your own HR business partner, your own communications team, your own leadership board, your own financial division. So, I definitely did not waste any of my prior experience. I’m still using it every day.
What parts of your diverse background have surprisingly helped you as a business owner?
I’d say the biggest things that have helped me along my business journey are my ability to build relationships and communicate effectively. There’s really no business without relationships, and if you can’t communicate with people, you won’t get far. That’s true no matter the industry or the person. Luckily, I got plenty of practice in both areas during my time at IBM, and it’s something I’ve carried with me ever since.
What skills or realities did you have to learn the hard way, through trial, error, or just by being in it?
One of the biggest lessons I had to learn was how to work in a restaurant. I’d never worked in one, and I’d never owned one, so I had to really dive in and understand how everything works. I made it a point to sit down with everyone who plays a part in our success — our chefs, cooks, dishwashers, hosts, GM, wine buyer, bussers, and even our guests. Listening to them helped me understand not only how we operate but also how each of them feels about the way we serve our community.
Who did you lean on during the hardest parts of the transition (emotionally, logistically, or financially)?
The purchasing process was a huge learning experience for me. It took almost two years and really pushed my negotiation and communication skills. I leaned on so many wonderful people along the way — it truly takes a village, and I’m so grateful for mine.
Did your relationship to success, ambition, or identity shift as you moved into this new season?
I don’t believe my relationship with success, ambition, or identity shifted as I moved into this new role. I’m still the same person I always was. I still treat everyone as I would like to be treated. I just see this as the next phase of my life.
What’s something people think this kind of transition looks like, but almost always get wrong?
I think people think that a life transition such as this is unattainable. People have big dreams, and they have no idea how to bring them to life. However, if you plan it out and surround yourself with people who believe in you and believe in what you wanna do, you will get there. It may not be pretty along the way (my journey certainly was not), but I had wonderful people to keep going. They continue to push me to keep going, because sometimes I’m like “Oh no, what did I do?” even though I love every second of my life. I truly believe that everyone can fulfill their dream, the dream they have thought of for many years. You can absolutely make it happen; there is always a way.
What advice would you give to someone who’s daydreaming about a completely different life?
Do it in baby steps. Make sure you’re financially stable for at least six months. Make a plan, write it down, and talk to people about it. Talk to people who are living your dream or maybe work alongside them like I did. I sacrificed nights and weekends, but it was really important for me to do that to get to where I wanted to be. If you really, really, really want something and it is truly your dream, you will do anything to make it happen.
Now that you’re on the other side, what has this new chapter taught you about what matters?
I don’t know if I’m really on the “other side”. Having just turned 50, I’ve totally moved past thinking of life as having an "other side." I’m fully in this chapter now - this is a period I plan to live vibrantly for the next 25 years, minimum! This journey has really clarified what matters most to me. It boils down to authenticity (knowing who you are and what you truly want), cultivating that "ride or die" support system that stays with you, and prioritizing experiences and knowledge over money. While we all need money to function, the real fuel for moving toward my personal and professional dreams comes from the people I surround myself with, the wisdom I’ve gained, and the meaningful experiences I collect. That clarity is exactly what helps me stay focused and follow my path every single day.
Want to follow Jess’s next chapter? Follow her on IG, handle: @DCWineGal; and check out her website: www.unwinedva.com
