Lindsay Smith of Flight Cleveland


What do you get when you take a solo female entrepreneur and combine with wine? Flight Cleveland! Lindsay Smith took an idea from a trip to Bordeaux with friends and turned it into a wine bar in Gordon Square, perfect for wine nerds and newbies alike. Flight Cleveland offers 29 wines on tap, 12 different wine flights, and more than 400 bottles of wine on their  shelves. So how did Lindsay come up with this idea and single-handedly transform it into the bar you can visit today? Read on to find out.

HM: What were you doing before you started flight Cleveland?

LS: So my background is in hospitality. I worked in catering and events primarily. Both in special event venues and restaurants. Most recently I was with the Cleveland Museum of Art, I was running their sales department. We sold all of the parties that were happening in the atrium and all their smaller event spaces and then planned and managed those from start to finish.

HM: How did you come up with the idea for Flight Cleveland?

LS: It started years ago, I was traveling with some friends and we were sitting in a cafe in Bordeaux (France) having a really great experience. They did blind flights, where they asked you what you wanted to drink and they brought you three things that sort of represented what you said. At the end you go could go into the shop and find out what you’d drank and choose to buy a bottle if you wanted to. I loved that whole concept and at that moment I started thinking about how it would be amazing to work in wine. That was probably like six years ago, and then the idea kind of simmered and evolved over time.

It was 2017, or maybe the end of 2016 that I started to get more serious about switching everything around and leaving the event world to do something on my own. Last year at the end of February, I left my job and I moved to Milwaukee  - which is where my sister lives. I lived with her family for a little while and I worked in a bar. I started developing the idea for Flight and hammering out the details, working on a very detailed business plan, and all of those things to sort of vet out the idea.

HM: What would you say was the catalyst that moved you forward?

LS: I think there is just that moment in your life where you realize that there is no time like the present. I certainly am not getting any younger but there's always a reason to stay doing what you're doing. I wasn't unhappy; I really liked my job, I liked the people I worked with and the people I worked for and the organization. I kind of had that moment where I was like, ‘I love doing all of this but I think I could love something more. It’s time I’m just going to take the leap and go for it! Scary, but totally worth it!

HM: How did you land on this location?

LS: I wrote the whole plan in Milwaukee knowing from the very beginning that I was coming back to Cleveland. As soon as I left Cleveland I missed it. Not only the people but just the infrastructure, the city, the enthusiasm that Clevelanders have for their city. I never really considered myself a Clevelander because I had transplanted from Chicago 10 years ago, but as soon as I left I realized I was a Clevelander. There was never a doubt in my mind that I wanted to be in the Gordon Square/Detroit Shoreway neighborhood. The whole plan was written with the intention of being here. As soon as I had something worthwhile to show people I came right over to the Detroit Shoreway Community Development Organization and said, “Hey! I have a business that I’d like to bring to your neighborhood, how can you help me? And are you interested?” They were, and they were extremely helpful and they were the ones who helped me find me this location. Their organization is amazing and just super supportive from the beginning. Even now, I’m still very involved in what they are doing and they include me in what they are up to. It’s a really awesome community to be a part of not only from a business perspective but the residential neighbors as well. Its a very close-knit group and they’ve welcomed me with open arms which is pretty amazing!

HM: What is your favorite thing about having a business in Cleveland so far?

LS: Truthfully it’s what I was just alluding to, it’s the support. Clevelanders love their local businesses. I have been completely floored and amazed every single day with the volume of people that have been coming through our doors, and the excitement they arrive with. It’s incredible! People come in here ready for a wine experience and are really trying to utilize every aspect of what we have to offer. Then, they come back and bring friends and family. It's a very supportive town to open a small business in. That's been really fun. We are a wine-focused concept which is a little different then what is going on in the neighborhood, and around the city. The fact that Flight is a little bit different really was well received.

HM: I agree! I was very excited to learn about it and then come and visit. You can try a ton of beers in Cleveland, but there aren’t as many spaces to try wine.

LS: Totally. I’ve heard that a lot and we love our brew buddies as well. We choose to put three of our local friends on draft. We’ve been working with Brick & Barrel, Hansa, Fat Heads, Forest City Brewery - everyone’s been very excited to put the local beers on draft here so we do have something for the beer drinker in your group. We have a little bit for everybody!

HM: What was the biggest challenge in getting the business up and running?

LS: Because I’ve never started a business from scratch before, I think that was one of the things that delayed the actual start of it. I didn’t know where to start. There is not a checklist out there that tells you what to do. You really have to start bit by bit and talk to as many people as you can and get input. Then things start to unfold. In the very beginning, once I had the business plan, once I was starting to look at spaces, for me, the hardest part was not knowing who to engage first in terms of building a team. When do I start looking for contractors? When do I bring on an architect? What licenses do I need? Where do I go to find all of those things? I’ve been really lucky to have a great pool of resources here in Cleveland of other business owners and folks that have come onto the team to kind of help guide me through some of that stuff. Also, I would say that that the organizations that I had to reach out to for all of these things were really helpful, including the State of Ohio and the City of Cleveland. It’s a mountain of work to open a business, it is an incredible amount of stuff to do and in this scenario, I was sort of a one-woman show so I was really grateful that I had some great people on my team to help frame my thoughts and point me in the right direction. I feel very lucky about that. I was a little nervous coming into this whole project solo but as I kind of worked my way through it and now looking back at the building and construction of it - it’s a pretty fun accomplishment. It feels really good to have been able to figure all of that out and have a business that's open and doing pretty well. It feels like I conquered a big challenge in my life. That's something that also inspired me to do all of this. I’m a very curious person, I like to work hard, and I’m always up for a challenge. This was probably one of the biggest challenges I’ve ever had but in the very best way.

HM: The pay-off is great to be able to be here and enjoy it!

LS: Yeah, to look around and be like, look at how this all came together.

HM: It’s definitely something to be proud of!

LS: It is. I feel really good about it. The logistics were definitely the hardest part. There were definitely days when I was like, “Oh, man, I wish I had someone to help me get through all of this or make this decision.” Ultimately, I worked very instinctually, and my gut led me a lot of the way. You really have to lean on your instincts and stay really focused on what's right for the business and keep making decisions with that in the background at all times. That really helps set the compass of where you need to go.

HM: You have one last meal in Cleveland, what is it and where is it?

LS: Do I have to pick one or can I pick two?

HM: It’s such a hard question - I don’t think I have an answer but I love making other people answer. You can pick two!

LS: I would probably do IL Rione for pizza because I think that everything they do is brilliant. Their food is amazing, they have a really great wine list, the vibe is incredible and the people there are super nice. They do no wrong in my eyes - I think they are brilliant at what they do. So I would go there and then I think I’d also, because I’m obsessed with this right now, go to LJ Shanghai for soup dumplings because they are amazing and their food is incredible top to bottom.

HM: Where is your favorite place to take visitors to Cleveland?

LS: Usually, my rounds are food focused. I do love to bring people to the Cleveland Museum of Art because it really is one of the most fabulous museums that we have in the whole country. Having spent four years working there I got to know the space pretty intimately and I got really familiar with their collection. It is unbelievable that they have the collection that they do and they operate the museum at such a high level AND it’s free! It’s outstanding. To me, that's something that's really special. It's definitely a gem in the city. Usually, I like to do the neighborhood rounds and show folks Tremont, Ohio City, and Detroit Shoreway. My go-to every time my family comes in is eating at Le Petit Triangle Cafe. I’m sneaking in another last meal in Cleveland here! I think that their food is consistently amazing. They are so authentic in what they do and are so true to themselves. I love that they don't deviate from that. I love that they are so focused on their concept and what they are trying to bring to the table and you get that every single time from them.

HM: Is there anything else you want TCBL readers to know about Flight Cleveland?

LS: In the same vein that I was talking about IL Rione, one of the things that has been really important to me and our philosophy here at Flight is that we want people to immediately feel welcomed and engaged and taken care of. The design of the place was intended to make guests feel like you’ve walked into somebody's living room and you’re hanging out for the evening. For anyone who’s not been or people who have been - we want to make that happen for you and you feel like you are a part of what we’re doing and that our team is engaging and educating you. If you walked out and you’re like, ‘Hey I learned something and I had fun and I laughed and I was super comfortable and I was engaged visually and from a taste and flavor perspective,’ I feel like that to me is a big win!

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