The Intersection of Art and Community with Liv Roskos - Ep 38

This episode of the Social Enterprise Alliance Podcast aired on Tuesday, February 27th. This episode can be found on Apple Podcasts and Spotify.

0:00:00.0 Lauren: Hello everyone, and welcome to the Social Enterprise Alliance podcast. Liv Roskos is a creative entrepreneur and events producer with OAD Productions. Her passion is to create artistic environments and experiences where artists feel known, valued, and loved. As a musician herself, her music is birthed out of the everyday human experience. Please welcome to the podcast Liv Roskos.

0:00:52.9 Lauren: Hi, Liv. It's so great to have you on the Social Enterprise Alliance podcast.

0:00:57.5 Liv Roskos: Hey everybody. I'm so excited to be here with you all and just share what I've been working on this past year.

0:01:04.6 Lauren: Amazing. Yeah, we just can't wait to hear about it. And you and I met because you did a marketing and branding workshop with SEA earlier this year, and I just loved hearing about the mission, the vision that you have, the work that you do, and just your passion for it. So I'm really excited to dive into that today.

0:01:23.1 Liv Roskos: I'm excited to be here and share with everybody.

0:01:24.5 Lauren: Yay. Well, just to kick things off, we'd love to hear a little more about your story, how you first became connected to Social Enterprise through OAD Productions, and just a little bit more about the work that you do.

0:01:37.7 Liv Roskos: Yeah, so a little background about me is I have a degree in communications. I've always been very active and involved in the arts, entrepreneurship, leadership development, teaching, social emotional learning, the whole gamut of just really service industry, helping others. And OAD Productions is an event production company that's hosted at Overflow Coffee in the South Loop of Chicago. I'll get a little bit later to the history of the space and why it's so significant, but I think I'm connected with SEA through the founder of Entrenuity, which owns OAD Productions, just through the realm of entrepreneurship, resources for entrepreneurs and resources for leaders in the industry.

0:02:26.1 Liv Roskos: And came across the amazing marketing class that you all were putting on, and it was just so encouraging to know that there's other nonprofit leaders and other people in the industry. There's a community of people just looking to help each other, looking to share their resources and their wealth of knowledge. So it's just really encouraging to take that class and just have a space, just an authentic vulnerable space to be able to share our struggles and work with each other to find solutions. So I think that's how I got connected with you all.

0:03:00.6 Lauren: Yeah, yeah. That's so awesome. And just for our context and our listener's context, what is the link between, we have Entrenuity, we have Overflow, and then we have OAD Productions. So what do each of those entities do? And how are they all connected?

0:03:16.9 Liv Roskos: Yes. So this is a constant conversation. This is a constant question that's being asked, and it's always interesting trying to find a way to pitch it or to explain 'cause there's so much happening. But the way I like to explain it is Entrenuity is almost like the mother ship, and we are the alien babies of the mother ship. So Entrenuity was founded years ago, and its focus is to help Black/Brown women-owned businesses with leadership development, entrepreneurship, resources, mentoring, coaching. So Entrenuity is a nonprofit that owns a for-profit Overflow Coffee on the first floor, and also owns Mox.E Coworking, a coworking space on the second floor.

0:04:02.5 Liv Roskos: And then OAD Productions is the events and art side underneath Overflow Coffee downstairs. We also have SUN starting up now, which it talks about how to start your own business, grow and scaling your business. So we have so many things happening under one roof, and it's almost like an ecosystem of resources, community, connection, coworking. So a lot happening in the space, but everything is housed underneath Entrenuity, the Godfather [chuckle] or the mother ship as you will. So hopefully that makes sense.

0:04:37.0 David: Yeah, that's super amazing. And I love how ultimately… What it sounds like is you're creating just a hub for the community that you're in. So I heard the empowerment of minorities and those without resources. I've heard teaching entrepreneurship, I hear creating some event spaces and through coffee usually that is a space where people can connect. So to me, it does seem like there is this common thread of connection and uplifting each other. Are there specific events that you do at OAD that glue all those together? What does that look like?

0:05:15.4 Liv Roskos: Yeah, so I'll kind of tell you how OAD was started and where it's grown now and how it pulls everything together in this space. So OAD stands for Overflow After Dark, that's the OAD part, OAD Productions. And really it was originally named Overflow After Dark because we were just doing kind of evening concert series and I was coming alongside getting contracted to do just after dark events after the coffee shop was closed. And then it started to grow into, "Well, maybe we wanna have afternoon session, maybe we wanna do something that's more educational-based." So it kind of branched off from just being ticketed event series in the evening to creating almost a hub and connection for emerging artists and then seasoned artists. So something really beautiful about the space is Overflow Coffee itself is housed at 1449 South Michigan on Record Row, which is a significant historical street in Chicago.

0:06:14.5 Liv Roskos: So in the 1950s through '70s, the coffee shop was home of the former VJ Records and Brunswick Records, which was one of the biggest Black-owned record labels in the United States. They were actually the first US record label to sign The Beatles and bring The Beatles to United States. Gladys Knight came through the space, Jerry Butler, Jean Chandler, The Chi-Lites, just a number of notable artists. So there's a lot of history in that space. So when you walk into the coffee shop on the left-hand side, you'll see a record wall paying homage to all of the artists. And then we have a big mural of the original exec team on the back where the stage is. So the vision in the space was to continue to give a platform to Black/Brown women-owned businesses, entrepreneurs and artists, and continue to tell the story of those artists in the space.

0:07:11.1 Liv Roskos: So we've been able to have a number of different events. We've actually been able to bring back some of the original artists that came through the space that are still touring or singing and put together… Kind of one of the first spaces in Chicago to put together cross-generational events. So for Black Music month in June, 2023, we had Barbara Acklin who came through the label. She's now passed on, but her daughter, Samotta Acklin is a singer, and she performed in the space and she remembers running in the halls when she was two and three. And some of her artists, a part of her band, had cut records in that space when they were 17, 18, and were on the bill. So we've had artists on the same bill from the age of like 18 to 70, 80 years old. It's all age inclusive space. So everything we do is for the community, ran by the community.

0:08:06.9 Liv Roskos: Everything is all age-inclusive. Anybody can come to an event which is unique in the city because often bars or clubs are 21-plus. But this is a safe space where if a grandparent wants to bring their grandchild and just have a great cup of coffee, listen to good music, they can come to the space for an event and then, hey, say they also own a small business and they're looking for a place to co-work, we'll give away free day passes to co-work upstairs, or maybe they wanna rent out the space for an event or just come back to the coffee shop during the week to work. So we've done a number of different events from themed events, celebrating different themes throughout the year, month to month, we've done a dance and drum event for youth, we've done book readings, we've done EP release parties, and then every other Friday we have community events called Acoustic Afternoons where those are really for newer artists to come, just have a platform if they've maybe never performed before.

0:09:11.4 Liv Roskos: We also have a connection with Columbia College right down the street, which focuses on the arts. And so there's just so much happening in this space on a day-to-day basis, on a week-to-week basis. And it's really become kind of a safe space for every type of artist, whether you're just getting started, you're a youth artist or you're a artist in your 70s and 80s, everyone's welcome to be in this space, perform in this space. So I think that's what has been kind of unique.

0:09:42.4 Lauren: Yeah, that's amazing. It sounds really busy, which is so exciting.

0:09:48.0 Liv Roskos: Yes, it is. [laughter] It is very busy.

0:09:48.8 Lauren: That's awesome. Yeah, it's just beautiful to hear about the way that you are creating this safe space and then using it to just promote these artists in all walks and stages of life. I just think that's really powerful. And you're right, it is very unique. I would love to hear, especially since OAD Productions is kind of part of this greater community that's invested in entrepreneurship and social enterprise and social impact in the community that you're living in. What is the link that you see between social enterprise and social impact and music and art and these other areas of creation?

0:10:30.5 Liv Roskos: That's a great question. I think artists are really the ones that push messages and are like the preachers of 2023 [laughter] There is so much power in art. I feel like if people don't listen to politicians or pastors or other type of leaders, they'll often listen to a song or they'll listen to an art form and it has a power to really move and change people's minds. And I think one of my goals this past year is oftentimes I think in the artist world, there's really a big disconnect between performance and education. And so what I was seeing is there's a lot of people that wanna perform, there's a lot of people that wanna get into the space, but there needs to be a better job from the Chicago Arts Community on linking resources for younger artists, emerging artists, of, "Hey, how do you make art a business? How do you market yourself as an artist? How do you make a greater impact? How do you build your brand?" There's not a lot of conversations always happening around that. And so I was really proud this year that we put on our first ever artist empowerment experience.

0:11:55.3 Liv Roskos: It's essentially a full day conference for artists, put on by artists. I think oftentimes a lot of business conferences really focus on small business owners, but it's not necessarily keeping the artists in mind. So we had 16 different collaborators, facilitators, come together, we talked about everything from social impact to branding, to marketing, to what is your unique value as an artist? To how to get booked as an artist. And it was just really incredible because I feel like that was the first time we've really fused the vision of the whole space. So you have Entrenuity, which is really focused on small business owners, entrepreneurship, and then the downstairs space with OAD, which is focused on really catering towards artists.

0:12:46.0 Liv Roskos: So we brought it all together at Mox.E our coworking space upstairs to just fuse both of those worlds together. And I was nervous 'cause I was like, "I don't know what the interest is. I don't know how many people are gonna show up. Is this something artists even want?" And I'm happy to say that we had about 60 attendees. It was packed. It was a great response. And at least hearing from different industry leaders, this is kind of the first time something has happened on this scale in Chicago. So I was really happy and proud to have a team that was able to spearhead that and put that together and be a catalyst for future events. So that's something that I'm really proud of, that brought all of that together this year.

0:13:37.3 Lauren: That's amazing. I think there's something really cool that I'm hearing too, which is I feel like social enterprises and nonprofits can get a lot of criticism sometimes for trying to do too much. And in some cases, especially if you're not well-resourced or if you're maybe in your earlier stages, it's important to focus or hone in on one or two things that you do and do them really well. But I just love hearing about the work that you're doing because I feel like y'all are just kind of past that criticism and that critique and just you have found a way to do all of the things that you do really well and have them all connect and work together. And that takes a lot of intention, that takes a lot of effort and hard work and just cohesion of a team. So I'm just really encouraged to hear that as just an aspect of the work that you all do that… Wow, you can do a lot of things and do them well. It's just really cool.

0:14:32.1 Liv Roskos: Thank you. And I think that to that point, it's like sometimes you will lose sight of your vision because you're doing so much. And this was really the first year that OAD Productions… It was our first full year, so we did a lot in one year. I realized that we did about 60 events this past year. It is literally me and one other partner putting together these events. And I think the reason that we were able to do that many events and they were actually able to happen and be cohesive is because I really pulled hard on community partners and collaboration. And I think when you're a startup or you're just starting a program for the first time, you really have to think through what are the nonprofits or what are the entities or collaborators that are already doing this and how can they join alongside what you are doing and build that community?

0:15:29.1 Liv Roskos: And I think that's one of the biggest reasons we were able to do so much this year, is because I knew so many collaborators or nonprofits that were already doing this, and I asked them like, "Hey, can you join this event?" Or, "Can you join this team for this project?" And it was a way for us to be promoted and to grow, but also for them to be promoted and grow. And that would be my advice to people really starting, especially when you're starting with a team of like one, two people, how do you actually put on these events and make them amazing? It's like, look within your community, look within collaborations that are already happening and bring them into the space as it makes sense. So I definitely will be scaling back for next year. And now that I have, we were able to get through this year and I was able to navigate "What's realistic? What's too much? What's not enough?" Now I feel like I have a rhythm and a cadence to say, "Okay, I'm gonna scale back from 60 events and do maybe 30 events and have more time for follow-up and have better work-life balance." So it's just a process of figuring it out, I guess.

0:16:38.8 David: Yeah, and I mean that's definitely part of the entrepreneurship journey, is throw everything at the wall, see what sticks, see what has the deepest impact. And again, as Lauren mentioned, there just seems to be a really good glue between all of the things that you're doing. So while you're doing a lot, there is this cohesiveness in it that makes sense to me. I think one of the things I love hearing the most is there's all these empowerment components and uplifting components, but you touched on it briefly, but the ability to also elevate the voice. It's very rare or it's becoming more and more common, thankfully, but so many people that have been in the margins for such a long time, their voice has never really been valued or elevated in a way that it needs to be. And art is definitely a way to bring that about.

0:17:30.5 David: So that's one of the things, to me, it feels like a ripple effect that we're not even gonna be able to see yet. So you're here, you are empowering that artist, but to see their art get into the world and to hear that voice now become amplified is something, I think, that's really cool. And I think related to that, it's my understanding that you're an artist as well.

0:17:51.3 Liv Roskos: Yes.

0:17:52.3 David: So I know that that's one thing that we share in common, the three of us, so Lauren writes and creates her own music, a singer-songwriter. I play in a band, so I'm not the creative side on that end, but I teach a lot of music and do a lot of fun, creative, things in a '80s cover band. But would love to hear about your art and how this also kind of ties in. 'cause I'm sure that there's a story there.

0:18:17.6 Liv Roskos: Yeah, so I think I was actually just having a conversation with another artist this week who also is in curation, has his own business as an artist himself. And I think one important thing that we were talking about is I think sometimes where the disconnect is with venues and with curation on the side of a venue is that they want to uplift the artist and they want to help artists and empower artists, but they don't understand the artist. And I think the incredible privilege that I've had in this position is that I've been an artist myself my whole life. And so a lot of the way that I customize and format events and format that feeling of the minute you step into a space, I want you to feel valued. I want you to feel cared for. I want you to get paid as an artist.

0:19:11.9 Liv Roskos: I want you to come back into this space and go upstairs and have a place to work. Is really because I channel a lot of how I felt walking into spaces where I was setting up my own sound, the show was starting an hour late, I didn't know who the point person was to talk to, there was no marketing on behalf of the venue. There was just so much disorganization and unprofessionalism that I told myself, "If I'm ever in a position of leadership or event curation, I want to keep the artist in mind." Because when you keep the artist in mind as an event curator, you're going to have a better performance, which is going to be a better experience for the audience, which is gonna create a feeling of, or a sense of community and connection. People are gonna want to come back into the space, whether it's to perform or tell their friends about a show.

0:20:14.4 Liv Roskos: And so I think a lot of my personal journey as an artist has impacted my professional journey as a curator. And a lot of change that I'm seeing in the city of Chicago when it comes to art is because you have artists in position of curation. And I think that's really vital and really important. And when you don't have that, it really lacks and you can see the lack in the community. I think what's been really amazing to see is it's hard to find that balance as a curator, being a full-time curator and working on your career and building that out and then working on all your side projects as an artist. But what's been really cool to see is, even being in this position, I've gotten a lot more opportunities this year to perform because people know that I'm in event curation.

0:21:09.5 Liv Roskos: They're like, "Oh, you're an artist as well." And I'm meeting more booking agents or curators and collaborating with more spaces that are looking for artists. And I always love to say, "Hey, I'm an artist as well, here's my music." So that's been just really cool to see that as I'm booking other artists in this position, I'm also getting a chance to perform more than I ever have. And last Friday I just finished the recording of my EP, which will be coming out this summer, and I'm going to be renting the space downstairs for my EP release party, which I'm really excited about and working with a lot of the artists that have come through OAD. So it's kind of cool to see it all coming full circle.

0:21:58.7 Lauren: Yeah, that's amazing. Very cool. A very cool cohesion between your personal passions and then the work that you get to do on a day-to-day basis. That's, yeah, just so exciting and congrats on finishing the EP. That's such a huge endeavor. A lot of work, a lot of heart goes into that.

0:22:14.6 Liv Roskos: You have no idea how long I've taken [laughter] even four or five song EP or album takes it's just so much work. So it's been a couple years in the making and a lot of back and forth, seasons of rest or stopping and picking it back up. But I'm so excited that it's almost done. We're almost there.

0:22:35.2 Lauren: That's so exciting. Well, as we wrap up, would love to hear about where OAD Productions is headed in this next year. You've touched on that a little bit. And then where can our listeners support the work that you're doing?

0:22:49.6 Liv Roskos: Yeah, so I think in 2024, the first part of the year is really gonna be just restructuring, finding that balance, that work-life balance as a small team of what's realistic for our team, and putting together really well-thought-out, really planned out events, and also giving us space and time to think through follow-up for events and having the space and time to really market out, well, the next event. So the best way to follow along is to go to our website, And then we're really active on Instagram, starting to be more active on LinkedIn as well, so you can follow at oadproductions on LinkedIn and Instagram, we will be having events for Black History Month, Black Music Month. We also have some really exciting, I'm not sure if I'm able to disclose them yet, but we have some really exciting partnerships for 2024 that we're hoping to talk about soon as it's public knowledge, but just some really exciting events coming up.

0:24:03.6 Liv Roskos: And then this is our 25th year anniversary as Entrenuity, so OAD Productions will be involved with that as well, and a lot of celebration around that happening in October. So just some really great things happening within Entrenuity and collaborations with Entrenuity and Mox.E, as well as just our monthly collaborations. So yes, please follow along with what we're doing. We also, starting February, we'll be able to livestream all of our shows and have tickets available for livestream. So we have a collaboration with Live Bash. If you're able to check them out, they're a virtual stage, they're awesome. So you can go to, and even if you're not in Chicago, you can catch a show, buy a ticket starting February and just see what we have going on in this space as well. And then me personally, you can follow me at, so And then the same on Instagram. I have all my music and everything there. I do a lot of cross posting as well [chuckle]

0:25:11.5 David: Yeah. Well definitely we wanna get everybody to sign up, hear all about the secret events that are coming up soon, and as well, I'm sure what your EP release date and all that is too. So thank you so much.

0:25:24.8 Liv Roskos: Yeah, of course.

0:25:27.0 Lauren: Yeah. Thanks Liv. This has been awesome.

0:25:29.6 Liv Roskos: This is awesome you guys. Thank you so much and hopefully catch you guys soon.