Melissa Zeman, BottlesUp! Chicago

[00:00:54] Sanjay Parekh: Back in 2009, Melissa Zeman said to herself, “Someday I’m going to open a wine shop that focuses on community.” She got to work and 10 years later, she opened Bottles Up!, a wine shop and experience in the Lakeview East neighborhood in Chicago. She believes in “retail-tainment,” which means creating, collaborating, educating, having fun, and most importantly, connecting. Here today to share the story of her business and how she thinks about business and community is Melissa Zeman. Melissa, welcome to the show! 

[00:01:27] Melissa Zeman: Thanks, Sanjay. Happy to be here.

[00:01:29] Sanjay Parekh: So, I'm excited to have you on the show because the idea of experience as a part of retail I think is something that we've been moving more and more into. But before we get into all of that, I'd love for you to share a little bit about your background and what got you to the point that you're at right now?

[00:01:47] Melissa Zeman: Sure. Gosh, once upon a time I was born in the suburbs of Chicago and then I actually went to school in San Antonio at Trinity University and focusing on communications and public relations. Started to go more into public relations and I really see a lot of overlap with PR and connecting people with the wine industry as a whole. And wine was my drink of choice. And so, I started to move that direction and as you said in my bio intro, which is beautiful, I just got it in my head that I wanted to open a shop someday that really tapped into that and worked in the industry for 10 years until that eventually happened in September of 2019.

[00:02:31] Sanjay Parekh: Awesome. Awesome. By the way I saw in your background, I didn't realize you were a native Chicagoan, but you spent time at the Chicago Bears and when I saw that, the only thing I could think of was a Saturday night live skit. You know, ‘Da Bears.’

[00:02:47] Melissa Zeman: Oh yeah.

[00:02:48] Sanjay Parekh: I don't know. Do they do that there a lot?

[00:02:48] Melissa Zeman: Oh, they do. Yes. Anything that is tapping into any sort of like bears reference that's been in the media or on entertainment platforms, it's been referenced for sure. We're proud. Even though we stink.

[00:03:04] Sanjay Parekh: That's funny. That's funny. So, let's talk about this entrepreneurial experience. So, you did this and recently and got started. Was this the first time you did something entrepreneurial? Did you do anything when you were younger or have there been entrepreneurs in the family that you've watched growing up?

[00:03:22] Melissa Zeman: I guess I never really thought about this until just now. My parents, my dad had his own law practice, and my mother has her own family counseling. She's a family counselor and has her own practice as well. But growing up there wasn't a girls soccer team at my high school, so I played on the boys’ team for three years until I led a petition and a movement to get the girls’ team founded at my high school, which eventually happened my junior year there. So that is very different. But it was something that I spearheaded, and it was a team effort. There were a lot of people involved with making that happen. But it was a cause that I believed in. And it's been really cool to watch that program go grow at my high school.

[00:04:13] Sanjay Parekh: The program's still going on, I'm assuming?

[00:04:15] Melissa Zeman: Oh yeah. They were, they've been regional champions and it's been really cool to say that I was part of the inaugural team.

[00:04:22] Sanjay Parekh: That is awesome. And definitely a very entrepreneurial experience there, as well as probably pretty challenging. I don't imagine it was an easy path to get that done.

[00:04:36] Melissa Zeman: No, but I think I'm grateful that other people saw the need and believed in it as well. Entrepreneurship is never about just you. There are always people that you require help from and advice and support in many different levels. And so that was an early lesson in that version.

[00:04:56] Sanjay Parekh: Yeah. And it's never easy, right? The thing that we see a lot about entrepreneurs that are successful, it just, when you read about it or look at it, it just seems like oh, it's just so easy. Like they decided to do it and done, it was a success. Oh, there's a lot between those two points.

[00:05:13] Melissa Zeman: Absolutely. No, it's very challenging. It's a lot of, I don't know what the heck I'm doing. It’s self-doubt. It's a lot of negative emotions too. But at the end of the day, if you're thinking about why you're doing this and what you want out of this, as an end goal, that's what motivates you and keeps you going. At the end of the day, it's okay to cry a little, drink a bottle of champagne, and then like onward, forward march.

[00:05:44] Sanjay Parekh: Yeah. So, let's dive into that. You decided like a while ago that you wanted to do this, and you spent time in the wine industry. Why did you feel like that was the right approach for you? Instead of just going headfirst and opening your shop right out of the gate?

[00:06:02] Melissa Zeman: Another good question, and again, I go back to sports a lot. Athletics was a really big part of my life and still is. I played basketball in high school as well, and there was a time when I got moved up to varsity as a sophomore.

Instead of playing on the sophomore team. And I just didn't feel ready, and I actually requested to be moved back down to the sophomore team to learn more, to get more experience, and I feel the same way in my journey in wine. I didn't know anything, and I needed that time to build connections and learn. See what other people were doing that I respected. I had my first job in the industry was a little shop in the suburbs of Chicago. Owned by a husband and wife, and they taught me so much. And we can go back to that later, but that learning period is a very important time to, again, your end goal. And then those connections, I'm still connected with those people in the Chicago wine industry that I met way back then, I still work with today.

[00:07:12] Sanjay Parekh: Yeah. So, that's interesting and fascinating that you were like, okay I know I'm missing these pieces, so let me go get those pieces. Just like you did in basketball. When you started this out, what did you discover that, like what were the unknown, unknowns for you? Because I'm sure there were some things that you went into it, thought you knew all of it, but then you discovered things that you didn't know that you didn't know.

[00:07:39] Melissa Zeman: Yeah, it was, generally, it was all unknown because this was the first time that I was doing it where it was me. It was like I was the owner. And granted, I have a wonderful accountant and my husband is, he has his own job as a civil engineer, but he helps out with a lot of the accounting as well. I am right brain, not left brain. I know my place in life. So being able to work with people who can fill that piece is very important, but it's understanding. I don't have an MBA. I was a communications major, so understanding the business side of things was a big unknown to me. QuickBooks 101, cash flow, like understanding the needs and managing that. That was a very intimidating part of opening your own business for sure. But again, with the right team and the right support and the people to help you along and teach you, you can do anything.

[00:08:38] Sanjay Parekh: And to be clear, you don't need an MBA to start a company. I started mine before I had an MBA. I do have an MBA now. It helps you level up, I'm sure, and round out some of the things, but tons of people that do this without any kind of business degree or education. I think you just have to have the drive for it, and it sounds like you have had the drive for it. But in starting this, and you touched on this before, I think one of the things that often happens that prevents people from being entrepreneurs is that they're scared and fearful of the things that they don't know about or they think that they don't know enough or they don't have the capabilities or the experience or the abilities or whatever it is. How did you deal with that for yourself? What fears did you have and, or what fears do you still have today and how do you drive through all of those and keep moving forward?

[00:09:36] Melissa Zeman: I think my biggest fear and what really drives me well, there's always the fear of unknown or doing something that you didn't like, making a big mistake and mistakes are going to happen and it's going to be okay. Like you're going to learn from it. You're going to move forward like. Or maybe you'll have to apologize for it or whatever. It will be okay as long as you tap into your moral code and do what is right. But the fear for me is to become stagnant. I put a lot of pressure on myself to come up with new ideas and new classes and events. Now that we can do that again, which is a big part of my business plan, is to, again, tapping into retail-tainment. Giving people things to do as a part of a retail store. So, I am just, I don't know, there's this weird fear that I'm just going to run out of ideas, but then, again, I drink a bottle of champagne and then I have all these ideas. So, it ends up, champagne is the answer here. But it's really just getting out of your own head sometimes of all the bad things that can happen and just keeping an open mind and staying creative.

[00:10:51] Sanjay Parekh: Yeah, my, my guiding principle has always been as long as you don't do something that's going to land you in jail, everything else is fine. Right?

[00:10:59] Melissa Zeman: Absolutely. I agree.

[00:11:00] Sanjay Parekh: So, make sure you just don't make the government mad, don't steal money, make sure you pay your taxes on time and all that kind stuff. Everything other than that, it's fine. You'll figure it out.

[00:11:13] Melissa Zeman: Yeah. That was another thing, not paying, messing something up with taxes was another fear of mine. But that's why my accountant... I love my husband, my dad, my brother, and my accountant. Those are the four men in my life! He's the best.

[00:11:27] Sanjay Parekh: They make sure that you're not going to go to jail. That's a good thing. That's a good safety net to have. So, let's talk, and you just touched on this a little bit. The story of Bottles Up! is about building not just a wine shop, but also building community. Talk a little bit more about that and how that influences the operations of the store and the things that you're doing to make sure that you're building not just a valuable and viable business, but also community.

[00:11:57] Melissa Zeman: Yeah, it has become this, just this beast of just a revolving door. Like we focus on community, which drives some of the products that we have on our shelf, and we do events. And it just it just keeps going in a circle. And community is why I wanted to dive into this industry more. I think about wine. You're sharing with friends, you're sharing with family. Even if you're just sharing a bottle with yourself, you're connecting with yourself. There's a lot of the stories and history and a lot of corny stuff that I can talk about when it comes to the wine industry. And I love that, and I love tapping into that and using it as a vessel to bring people together and create memories. I also have a very weird obsession with memories and creating good times. So, that as a part of the business model was always important. And like I said, we have an event, we get to connect with winemakers that come to town and producers and from all over the place and bring in people from all over Chicago or people who are visiting Chicago and hear about us because of an event, and they come into the store. And not to mention the collaborations that we do with other fellow business in Chicago. There are so many wonderful entrepreneurs out there, and I also feel like this, as an entrepreneur, you have a unique opportunity to connect with others and create collaborations and more things for people to do.

[00:13:34] Sanjay Parekh: So, I've got in my notes that you've got something called Crosstown Tuesdays. What is that? How did that come about?

[00:13:41] Melissa Zeman: Okay. It started selfishly because during the pandemic it was insane in retail, and I had zero life. I woke up, I went to bed. And in between that time, because it was very scary and I cut like my part-timers, I didn't, whatever. I was the only one basically working from sunup to sundown. And everyone was talking about some, working from home or some people moved to the mountains, and they were working from the mountains and now that hybrid or work remote has become a permanent thing. People are still doing that kind of stuff. And I was always a little, this is weird to say because I know it was a terrible time, jealous of the opportunity to work from somewhere else. So, I decided to do Crosstown Tuesdays as a way for me to get admin stuff done for the shop and work on things without constant interruption of the door opening with customers. Not that I hate that, I love that. But also going to support other businesses in Chicago that I'm friends with or that I love, or that I've heard about and want to check out. We obviously carry a lot of different beers and there are micro-breweries in town that have taprooms. So going there and just bringing my computer and getting work done. So Tuesday's been my day to get out of the neighborhood and go support other neighborhoods and other businesses and then, creating new collaborations for the future too.

[00:14:59] Sanjay Parekh: Okay, so it's every Tuesday you just get out of the shop? Somebody else is manning the store, I take it.

[00:15:07] Melissa Zeman: I have a wonderful team.

[00:15:09] Sanjay Parekh: Okay. And so, then you're out there. So, these places that you go I'm assuming you know the people there. Do they ask you like, hey, why aren't you at your store?

[00:15:21] Melissa Zeman: Sometimes I know them and sometimes I don't. But I've been doing it now for a while. A lot of, even sometimes a lot of the reps that I work with are, will text me and be like, hey, where are you at today? Can I meet up with you? Or something like that. So now I've been doing it for long enough, now where it's okay. And I think it's, anytime I tell people and my customers, when I first started doing it and my customers were saying, I came to the shop, and you weren't there. Good for you. I'm so happy for you. When your customers are saying that to you, it's an indication that maybe you need to get out more.

[00:16:00] Sanjay Parekh: So, I'm wondering, has this inspired any of the other business owners of the places that you end up frequenting to start doing the same thing?

[00:16:08] Melissa Zeman: I don't know. Everybody has, going back to my team, I love my team. I'm very lucky to have a really good team who I trust a hundred percent, and who enjoy working. Not everybody has that right now. There are big time staffing problems, so some people aren't as fortunate to get away. Other people are closed one day a week. We're open, we're only closed four days a year, so it's a little bit different. And so, some places that do close, maybe they use that as their day to go explore. Every business is different, but the staffing issues that are prevalent a lot across the country are very real for sure.

[00:16:52] Sanjay Parekh: Yeah. Yeah, I can imagine.

[00:16:55] Adam Walker: Support for this podcast comes from Hiscox committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available. At Hiscox.com. Hiscox, the business insurance experts.

[00:17:17] Sanjay Parekh: Let's shift gears into talking about stress, because that's obviously a stress too the staffing side of it. How are you managing the stress of owning a business and then all the other stuff that is in life, right? Like family, friends, all of those things. How do you balance all of that?

[00:17:35] Melissa Zeman: Oh, champagne.

[00:17:36] Sanjay Parekh: You're always invited to the parties because we know you're bringing the champagne.

[00:17:42] Melissa Zeman: If you think I'm not drinking champagne right now, you are very wrong. So, I don't, not well, honestly, it's hard. You always feel guilty in some way, and I think even in, no matter what you're doing, whether you own your own business or not, sometimes there's always a category of your life that you feel like you're neglecting. And I've tried to get better at, even when I'm just thinking about a friend I haven't seen in a while or something, or maybe haven't seen my family in a little bit or whatever, sending a letter. Let's bring snail mail back. Or just shooting them a text or planning a like a date, even if it's three months in advance just to get something on the calendar. It's difficult, that kind of balance, but it's very important and I feel like it, it has been a silver lining of the pandemic is resetting that and people understanding that that is okay. When you see a business owner taking the time to be with family or friends or doing, even just being by yourself and not speaking to another human for 24 hours, because I talk to people every day, all day. So, it takes work. Not working, takes work. But it's important work for sure. To do your work correctly.

[00:19:11] Sanjay Parekh: So, before you opened this shop up, did you think of yourself as an introvert or an extrovert?

[00:19:17] Melissa Zeman: I am an extrovert, definitely. However, I love my introvert days. Like I don't, I'm not one of those people who, when I'm home by myself, I'm like, oh my gosh, I need to do some, I need to do something. No, I will enjoy the time, not speaking to people and watching a romantic comedy or reading a book or just sitting there sometimes because I'm in a very customer facing business. You are, you're on. All the time. And that can be exhausting, even though it is a natural part of who I am. I do shut down sometimes. And then, and I enjoy that time and God bless my husband. He lets me have that time.

[00:20:08] Sanjay Parekh: I was just doing the math. You said you're closed four days a year, and then you're out on Tuesday, so that's 52 days a year. So, 56 days of the year you're not in the shop. But that's a lot of days that you're in the shop and you're dealing with people and having to be on, and that even if you're an extrovert, that's a lot of ‘on.’

[00:20:28] Melissa Zeman: Yeah, but it's, you know what, it's wonderful. This community that I'm in is amazing and I know there's a lot to be said about terrible humans these days, but man, there are some great ones out there. And I'm remindied of it every day, and I'm very grateful for that to be in a customer facing business, to see that and have connections with people and meaningful ones as well. And I, at the end of the day, it's just alcohol. I'm not saving lives. I'm very quick to check myself as I'm not doing the Lord's work or whatever. But it is a very wonderful work to me for sure.

[00:21:06] Sanjay Parekh: So, let's keep going down this path a little bit. Do you have an exercise routine? And if you do, how do you fit that into your day?

[00:21:15] Melissa Zeman: So, Tuesdays are my work remote day where I'm still working. I have, again, thanks to my team, been able to take Sundays as my like day of my truly day of rest where I try not to do any work. And sometimes it's not always possible. And that doesn't mean that my phone isn't on me because I need to just be aware of what's happening or available. But I play soccer on Sundays and have played rec soccer in Chicago since I graduated in 2007. And it's a wonderful outlet, and obviously my sport of choice and has been my whole life. It's fun. My team has been together since about 2008. So, we've been together playing for a long time and we're 90% hungover a hundred percent of the time, but it's still great. And we just go out there to run around and connect and play a game we love. So that's been fun.

[00:22:13] Sanjay Parekh: Okay. So, if you're playing those games on Sunday, are you keeping in shape the rest of the week because the soccer's not a sport, you just pick up like, oh, I'm just going to do this one day a month and then not do anything the rest of the time. You're going to hurt yourself and be exhausted.

[00:22:27] Melissa Zeman: Thankfully in Chicago there are leagues every day of the week, and so I am like the late-night sub for a lot of my friends because the shop closes at eight. But there are games in Chicago that start at 9, 10, 11 pm. So, when they need subs for those games, I'm like, I'm up. Call me. So, I'll actually get to play a few more games during the week and then just working things in the morning, doing quick little workouts that seems to do the job. There's just so many apps out there that make it quick. Like how much time do you have? I have 10 minutes. Great. Kick my ass for 10 minutes and then we'll call it a day.

[00:23:10] Sanjay Parekh: So, what, let's since you mentioned app, let's talk about technology and apps and systems that you use. You're working out of the shop one day a week, so you've obviously implemented some things or are using some things. What are some of your favorite tools that help you be able to manage the business even while you're there or remotely?

[00:23:29] Melissa Zeman: Gosh, we're a pretty simple business. We don't do e-commerce. For some reason I'm just can't tap into that yet. Don't really want to. So, I really just use email outside of the business to do, and I'm obviously, I have access to our inventory, our POS system and things like that to track that kind of stuff and enter items or change things. But really when I'm not in the office, I use that as time – or the shop – to be creative and write the newsletter, write the wine club, come up with social media posts, craft the text for upcoming events or plan those events. I wear a lot of hats for the shop. And a lot of it has to do with kind of content creation and event creation. So, I don't really need too many technological tools to do that, except for my brain and champagne.

[00:24:31] Sanjay Parekh: Yeah, so you're planning the calendar of both social media as well as social events, just one day a week essentially. That gives you enough time to be able to build out that calendar?

[00:24:47] Melissa Zeman: Yeah, I think, I guess now we're getting into it because I am very atypical. We're a small business. Like I am the only full-time and I have a wonderful team of five part-timers. And if you think that I have a planning meeting and map out my social media posts, I do not. I haven't. I am of a weird mindset with social media. Oh man, I love it and I appreciate it, but I'm also exhausted by it. And so, anything I put out, I try to just be very genuine and relevant. Usually it's just a, it's a post to be to be uplifting, to be humorous or to promote an event, or recap an event or do some sort of a shout out to somebody I've collabed with. So those are my markers for social media posting, but I don't have a plan.

[00:25:41] Sanjay Parekh: Yeah. How do you think about those events? Is it, hey, this would be a fun event for me to be at. So, I'm going to do it. Or are you thinking people have told me they want this kind of event. Like how do you think about figuring out what event is next?

[00:25:55] Melissa Zeman: Yeah, it's a combination, honestly. And I love working with, and even taking customer requests. I've had a lot of ideas that we've implemented. We do a Run for Rose 5K every year, at the end of April which has been wonderful. This will be our third year doing it next year. We do, we always do a trolley crawl around to different other businesses in Chicago. But the one, the new one we did last summer was a Shuck Yourself event, and we actually did an oyster shucking and champagne, like DIY thing at the shop, which was a customer idea.

And I've learned to become a yes woman, especially during the pandemic. And that's the fun part about being an entrepreneur is you can be like yeah, let's try it. I don't know, like maybe it'll work and maybe we'll do it again and maybe it'll be a disaster. We're never going to know so let's see. And again, like you said earlier, if you don't end up in jail, it's okay. So that's what's been fun and we've gotten the reputation of that as being an events place where anything goes, or anything is possible.

[00:27:05] Sanjay Parekh: I like that a lot. It's very interesting. So, it's making me think about and obviously I'm not in Chicago, so I don't know what kind of your setup is in the store and the neighbors you have. What do the neighbors think about the events that you have? Do you pull them in as well?

[00:27:25] Melissa Zeman: I'm on the Chamber of Commerce on the board. So, business neighbors I try to collaborate a lot with, and partner with. Residential neighbors. A lot of them are customers. I haven't had anybody call the police on me if that's what you’re asking.

[00:27:45] Sanjay Parekh: So, I was assuming that wasn't true. I was thinking more your business neighbors and like, how do they view the shop that you've built there?

[00:27:55] Melissa Zeman: Ah, the ones that we collaborate with frequently we have a great relationship and are constantly kind of rah rah, let's support the neighborhood. I am very invested in the neighborhood and the success of the neighborhood, so I want to tap into everybody especially the businesses that are here. And there's constantly new ones opening up. There's so much and sometimes I'm, being a solo entrepreneur I almost feel sometimes that I do need to hire someone to help me reach out to other businesses and make those connections and do more stuff. So, maybe I'll be better at that in the New Year — resolution.

[00:28:36] Sanjay Parekh: Yeah, there you go. New Year's resolution right here. Okay. Last question for you. Actually, I've got two questions for you. So, first what would you tell somebody that's thinking about taking a leap and starting a side hustle or turning their side hustle into a full-time business?

[00:28:54] Melissa Zeman: It's funny, I have a lot of friends who are doing the exactly that right now. Keep. Going. I think it's just one of those things you have to remind yourself is, good days, bad days, just to keep going. It's going to be okay. You're going to have a bad day, and then you're going to go to bed, you're going to wake up, you're going to start over. Reminding yourself that, what's the sports quote, like pain is temporary and something is forever. I'm forgetting, I'm butchering that. But pain is temporary. So just kind of keep with it. Keep your moral code and keep it in your head of why you're doing this. And if you keep thinking about your end, what you really want at the end of the day, that's going to get you through everything.

[00:29:44] Sanjay Parekh: Yeah. Okay. So, last question. This is now a drink tip for our listeners.

[00:29:53] Melissa Zeman: Champagne! I'm just kidding.

[00:29:56] Sanjay Parekh: I think people know champagne, so I'm going to dig in a little bit deeper than that. What's the drink that you think is the best, but nobody knows about it, nobody really talks about. Like that hidden gem of a drink that people should go out and try? Alcoholic or non-alcoholic whatever it is.

[00:30:16] Melissa Zeman: Wow. Oh my gosh. My mind just went so many different directions. And that's the hard part about being in this industry and being exposed to different things. There's no way I can just say one. And so, what I will say is, that drink that you think you hate? You actually haven't had every single expression of that drink that you think you hate. So, keep tasting it. I've had so many people say they hate Chardonnay, but then I blind them on a Chardonnay, and they love it. So, get out of your own head when you're drinking and that's going to make your life so much more fascinating and enjoyable. Don't pigeonhole yourself, keep trying new things. Terribly vague answer, but really that's the one thing I try to teach people and we try to teach people in the shop. Wine is an intimidating category, but it doesn't have to be. So just keep tasting stuff.

[00:31:13] Sanjay Parekh: So, ask your local wine connoisseur at the local shop and maybe get advice about it.

[00:31:18] Melissa Zeman: Yeah, there's so many wonderful, small, independent shops all over the country. You guys have some great ones in Atlanta. Three Parks, I'm pretty sure is in Atlanta. It's another woman owned shop. But so do the research and try to support the little guys. The big guys are going to be fine no matter what, so try to support the little guys.

[00:31:39] Sanjay Parekh: There you go. Well listen, Melissa, this has been awesome having you on. Where can our listeners find and connect with you online?

[00:31:46] Melissa Zeman: Instagram, I'd say is the most active. It's just Bottles_Up_Chicago. If you go to our website at bottlesupchicago.com there's a popup that will have you sign up for our newsletter. I hate bombarding people, so I only send it out like once a month, if that. Again, I'm very atypical marketing and public communications major. So those are the two biggest ways for people to keep in touch with us. I'm also pretty much an open book, so come visit me.

[00:32:24] Sanjay Parekh: And now we all know that all that work that you do on the social and emails are all done on Tuesday.

[00:32:31] Melissa Zeman: Or at midnight. It's a 24-7-365 operation.

[00:32:39] Sanjay Parekh: There you. Well, thanks again for coming on the show, Melissa.

[00:32:42] Melissa Zeman: Thank you, Sanjay. This was awesome.

[00:32:46] Sanjay Parekh: Thank you for listening to this week's episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit www.hiscox.com/shareyourstory. I'm your host Sanjay Parekh. You can find me on Twitter @sanjay or on my website at www.sanjayparekh.com.