We were lucky to catch up with Hilarey Leonard recently and have shared our conversation below.
Hi Hilarey, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?
Early on, I got my work ethic from watching my grandfather. He owned a manufacturing company that made metal products like wash tubs and file cabinets. He worked very hard and fought through very difficult obstacles to achieve success. My father worked for him out of college, and my grandfather made him work his way up like any of his other employees. He treated his employees very fairly, advocated for them, and created a safe workplace. I used to love going to visit him in his office and seeing how things worked at the company. My first career was in television production and at that time, jobs were coveted and hard to get. Most positions were freelance, which meant after your show wrapped, you were not guaranteed work on the next one. The fact that you had to earn a new job basically every six months, made you work extremely hard. I genuinely loved the work, so I was happy to pull extra hours or go above and beyond daily. It was also so amazing to be able to learn and improve watching my co-workers and bosses. It made me extremely thankful to be at work and have a job, and never take things for granted, something I have carried into my new career as a business owner today.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
I am a co-owner of three hospitality businesses in the DMV with my husband, Brian. Our first bar is Lost & Found in Shaw, and it specializes in craft beer and whiskey. Our second place is Free State in Chinatown, DC and we specialize in local spirits, wine and craft beer. Our third just opened this year and it’s a farm to table restaurant and bar called Leo, located in Annapolis, MD. My husband has always worked in hospitality, and climbed the ranks with a local restaurant group. I had served at several restaurants in between jobs and worked for some friends when they opened their first restaurant in DC, but my day job was always in TV production. When we opened our first place in 2014, I was still working full time and would bartend on nights and weekends. When we opened our second in 2017, I left my career to manage it, and haven’t really looked back!
I kind of took my organizational skills from the production world and applied them to booking and planning events at the bars. When social media became more popular and a necessary way to promote your business, I took that on as well. I also started learning more about wine and ended up studying for my Sommelier certification. During the pandemic, one of the ways we tried to stay afloat was virtual wine and cocktail classes, which I taught. Right now, I’m loving curating the wine list for Leo. Since the menu changes seasonally, I’m able to change the pairings quite a bit, which is a lot of fun. I’ve also enjoyed talking to the customers to learn what they’re drinking or traveling to in order to find good wine and taking their suggestions.
What I like most about my job is giving our employees a supportive place to work, hearing/seeing our guests have a great time, partnering with other small business owners, and cultivating friendships along the way. Our main focus is supporting local with our product list and elevating service for our guests. We also feel strongly about being a part of our communities, in DC and Annapolis. We love serving our neighbors, giving back, and taking care of our people,
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
I think being good problem solver is one of the most important qualities in a business owner. Not losing it when something goes wrong, but rather sit back and think of possible solutions and how you can make that happen, often very quickly! Doing good research on important products is also key- like your point of sale, vendors, etc.. The cheapest option is not always a great choice for good reason! (We learned that the hard way a few times.). Be flexible and not rigid, things constantly change and it’s good to go with the flow, rather than be closed minded. For us, setting up processes for inventory, scheduling, financial tracking etc.. was very important in freeing up our time to do other more important things. And resilience is also a wonderful skill, which I think we all learned during the pandemic. Thinking creatively and out of the box about ways to solve problems is how you will get through it! Lastly, asking for help. I joined a local restaurant owner’s women’s group and we have monthly calls to just talk about what’s going on in the industry, what challenges we are facing and lending a helping hand. We also hired a consultant to help us set up our kitchen and get processes set up for back of house for our new restaurant. It was invaluable in so many ways, and helped us so much gain skills and confidence.
Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?
Without a doubt my husband and partner, Brian, has been the most helpful to me. He is a wealth of knowledge about the hospitality industry, managing people and keeping things on track financially. He is also very handy and can fix about anything! I appreciate his patience in teaching me throughout the years. (Because it’s not always easy to work with your wife!) Now that we’re both a little more seasoned, we can work problems out together, run new ideas by each other, and commiserate after a bad day. I truly think we are better together, and can handle challenges so much better than we did almost 10 years ago when we started. We have learned so much from our mistakes and have grown a lot from these experiences.
Contact Info:
- Website: https://www.freestatebar.com
https://www.lostandfounddc.com
https://www.leoannapolis.com - Instagram: @Freestatebar, @LostNFoundDC, @LeoAnnapolis
Image Credits
Jesse Lee Ray (Bar photos, drink photo) Steve Vilnit (food photos, Leo photo with neon sign)
