Think Like an Entrepreneur. Make Like an Artist: An Interview with Maryann Lombardi
Maryann Lombardi is a strategist and entrepreneur, building community and solving problems with a white board in one hand and a cocktail in the other. She believes many truths about business and life, but one thing she KNOWS: the only capital we can’t live without is Human Capital. Subscribe to the “Human Capital’ Newsletter to join in the conversation!
She currently works with DC Government, community partners, and entrepreneurs to build the creative ecosystem and grow the creative economy. Her background includes ten years in independent theater in New York City, both as a producer and as a jazz singer.
You can find Maryann at her website. She can also be reached by phone and welcomes reach outs by text! 225-362-8030
This interview was held on September 14, 2020 as part of DC Startup Week. The recording starts several minutes into the conversation.
Dana Ray: You are a startup consultant. You run the branch of the DC government focused on creative economy. You’ve been a jazz singer in New York City. You’ve produced off Broadway theater. What is the relationship between business and art?
Maryann Lombardi: I see them as the same. I'm creating and building something from scratch and that feels like art to me, even if it is business. I feel like often entrepreneurship is separated from arts because entrepreneurship is about business, right? It's about making money. It's about doing something that has commerce attached to it. And that's true, all of that is true.
But I have always found that when I think about my work as just being about business, it's less inspirational to me. I find the artistic process in all that I build whether or not there's money and commerce attached to it or not.
Dana Ray: Whether there's art, or whether there's commerce, there's this creative problem solving around the businesses and working with people and solving problems. This sounds like exactly what you did as a theater producer: you gather people in order to create an experience or to say something specific or to solve a problem? And now, in a sense, you are assembling the infrastructure to make different programs happen all the time.
Maryann Lombardi: I think it's often unfortunate when we separate out business and other skills. We think, “If you're going to do business and be an entrepreneur, you have to go to business school. You have to have certain kinds of training, and there's only certain kinds of training that will teach you the things that you need to know.” But that’s a lot of crap. I think all of our experiences come with us to bring us where we need to go. And when I look back, I think the best training I ever had to be an entrepreneur was to be a theater producer.
Because when you produce theater, you have to build something out of nothing. You have to find an audience for that thing, you have to sell that thing, you have to bring a bunch of people together who have different opinions and views, a lot of them very passionate and engaged in their way. And you have to build consensus with all of them. And you have to work to meet a common goal. That is the essence of entrepreneurship, right? And so every finance class, I've taken business class, yes, it's valuable and useful. But at the core, being a theatre producer and learning how to do that has been the most valuable thing that I think I have ever done to prepare me to do the kind of work that I do.
Dana Ray: I think that's a good segue for what is the work that you do right now, which I know is multifaceted.
Maryann Lombardi: I am at the helm of the DC creative affairs office, which the mayor launched back in September of 2019. And our focus really is on building sustainability of the creative economy. We're focusing on three very specific areas.
Policy is where we start. So not just the policies that exist and new policies that we can create, but also policy awareness, right, you can have a policy that nobody knows that exists or how to use it. It’s a translation issue. And you should understand this from a communication standpoint, but the translation of something into something else that people can understand and then utilize. What's the point of having resources nobody else understands, or knows how to use or take advantage of?
We're also looking at infrastructure. And we see infrastructure is not just about traditional physical infrastructure, like space, for instance, which is absolutely a valuable resource and necessary. But we also see infrastructure as a personal infrastructure. What do you as an individual need to have for you to be stable and solid in order to do your best work? Which is why we're doing a lot of work in mental health. We have a partnership with George Washington University that we launched a couple months ago that provides pay-what-you can mental health support for any creative or entrepreneur who needs it
And then the other side of the work is economic mobility. And we see that as a conversation between saving money and earning money. How exactly can you do everything that you need to do to be efficient and how you spend your money on your work? But then at the same point in time, how are we helping to prepare you to be able to earn more?
Dana Ray: So it sounds like you're working from both the individual’s experience of their creative professional lives, all the way up to communal and institutional structures that enable people to thrive.
Maryann Lombardi: At the end of the day, the end user is who I work for. The person who is getting those services is the person that we serve is the District resident who needs resources. We have to make sure that all of that upstream work, all of that systems work, has to generate downstream to the support that the individual needs. If we say a bunch of interesting things, that never actually helps the person, then all of that doesn't matter. So it's a constant conversation between making sure your goals and your mission and your systems and your structures are actually benefiting the people that they're supposed to serve. And so there's always that check in process and you build a partnership, you build a strategy, you build a program, just making sure you're always connecting back to who's the person it serves. Because if it doesn't serve that person, then we need to readjust.
Dana Ray: YES! What are some of the major needs that you see in the individuals and the smaller communities and pockets of creatives? Right now? What is that challenge? And how would you dream of solving it?
Maryann Lombardi: There are challenges of different scale but the core of them is the connection between people. And this is a pre COVID and a post COVID challenge. The connections and the community that you build and that you make, and the people that you connect with, will lead you to everything else that you need.
I see people skip over the process of building their community and making their networks in order to get money or resources or space or all of those things. And when they leap over the process and finding the people, they make the rest of it that much harder. People don't give money to businesses, people give money to people. Anytime you get any real money from anybody, people are giving money to people; that is the core of fundraising. That is the core of anything that you're doing when it comes to money is that people like to give money to people. Knowing the right resource for you, requires you to do the work to get to know people to ask what resources did they use and how did it work for them.
The process of building a community, the process of connecting to each other, not only helps you on your business side, but it helps you also build that personal infrastructure. Because this work is hard. This work is lonely and isolating. And exhilarating, powerful, and inspiring. Being able to share all of that range of experiences and emotions requires you to be connected with people who understand what the heck you do. There’s a lot of people who don't get it, and that's okay. There's nothing wrong with the fact that they don't get it. But it does mean that you need to build community. You need people who get it.
Dana Ray: I just had a conversation with a client of mine about this. She was talking about how no one understands her work as an illustrator. And asked, “Are you hanging out with other illustrators?” She said no and that people think she doesn’t really work when she does! It’s an example of getting the right person to mirror back to you, “I see your work. I understand your struggles.” This is about what it means to be an entrepreneur, to be a creative, to be an artist.
Maryann Lombardi: The simple act of having that conversation with somebody to reflect back to you that you matter, that you're seen, that somebody else gets it, that can sustain you for quite some time. So finding the right people should be at the beginning of everything. And it's a consistent process that you have to work to build community and have those conversations with people who get it. And then from there, it leads you to all of those other things that you need to support your work.
Dana Ray: This also seems to me to tie back to the services you've been able to generate for creatives in the mental health space. To not be isolated and having community with people who are willing to support you and to see you engineer to you. That is fundamental to any stable mental health, going from like a therapeutic relationship on to your peers--
Maryann Lombardi: --or a conversation like this one. What’s even better about this is that the program was created because of those kinds of conversations. I get in conversations all the time with creatives who are talking about, aside from resources and support like money and all this kind of stuff, the main thing they want to talk about is that they just feel like they need support in the mental health space.
I recognize our expertise is not in the mental health space. But it's always been sitting there. And once COVID happened, I was talking with two creatives who I talked to all the time a filmmaker, as well as a musician, and they mentioned it yet again, about how important it was. And literally the next day, I was talking with a friend of mine who runs the counseling program over at GW. And she's talking about her students don't have anybody to see. And the artists are telling me that they need to see people and it's like, here we go!
But none of that would have happened if I wasn't having those conversations, if it wasn't a safe space for those two creatives to tell me what they needed. That's why I think it's so powerful to be able to develop relationships with people in order for them to tell me what they need, and then me to go figure out how do I help that happen? If I didn't know those people, none of that would have happened.
Dana Ray: This is why I call you the fairy godmother. And so you are someone who is in those conversations and is able to connect me to resources or most beautifully, two different needs that together saw something.
Maryann Lombardi: The Win win.
Dana Ray: What does it look like to build those networks? How do we do it?
Maryann Lombardi: I wish I could have a more profound answer to this. But I think it’s saying yes to the conversation. Be a really good listener. A lot of times, people listen in order to figure out what they're gonna say as opposed to listen in order to actually hear what somebody else is saying. And so I think this process of being a really good listener, and being available to talk to people, and to listen to them is how this happens.
And also being endlessly curious. I like being around people who know things. I prefer to be the one who knows the least about the subject in the room most of the time, because then I learn the most that way. And I think being able to foster that kind of curiosity makes you show up in rooms that you may not have previously thought you would be in because you're looking at your your life, your goals, too linearly. And I'm wondering what's happening over there? I'm gonna go over there and find out and listen to those people and talk to them for a little bit. That was cool. That's interesting.
I really enjoy talking to people. I love to listen to their stories. That’s the core of it. Because once you do that, then it's just about putting the pieces together. My brain loves to play the puzzle. And to be like, Oh, well, that's that. And then that's over there. And they're a little slow on the uptake. But I bet if we put them over here, we can like, bring them in the back end. And then they can do that, right? Like I could do that till the day is done. So it's just the matching game really requires me to listen to people.
Dana Ray: What's something you're curious about right now?
Maryann Lombardi: Well, I'm wildly curious about systems. This is going to be so boring. I'm sorry. But I'm wildly curious about system development. I'm wildly curious about upstream work. And the process of how you take your downstream work, and you jump it up to the source. And so I'm constantly thinking to myself, right, the work that we are doing, is this getting at a system level? How do we get to the system level of the challenge and the problem and the structures around the creative economy? And specifically, I think in the nonprofit arts sector, there's a lot of system challenges and so I've been spending a lot of time, listening and reading and learning about how to get at the problems. So like, the nerd in me, is digging into that.
Dana Ray: You one of the things that you had said about how do we build these connections, which was to be open to the conversations and to be curious, those were kind of the two points that I heard. And I immediately thought of how I got connected with you which is someone suggested I meet you. And I cold emailed and did not expect to hear from you, honestly. And you wrote back and said, “I'd love to meet you come down to my office, we'll have a conversation.” You were an open door to me. I think we ended up talking for an hour. Your generosity opened so many doors for me on a personal and relational basis in DC. How did you even decide to say yes to that, like, what made what made that a YES for you? What makes it easy for you to say yes to connection?
Maryann Lombardi: Well, because you're a priority. We all wake up one in the morning, and we prioritize what it is that matters to us during the day. I try very hard to do that as much actively as I can. And so when I prioritize what matters to me, talking to you matters to me. And that's always the case when it comes to talking to creative people, entrepreneurs, any of that kind of stuff, partly because you guys are endlessly fascinating and I love you and partly because I learned an enormous amount. I learned as much from you as that you may get back from me because I can't do my job if I don't know you. It's a continuous relationship. But I think the reason is that you matter. You're a higher priority than other things. Anybody who reaches out like that, you bump up to the top of my list.
Dana Ray: Fourth wall break! I hope for everyone on this call this encourages you to reach out to strangers. Not because they have something that you need. I didn't know what Maryann did at all. And that reach-out has been endlessly delightful for me. And so I hope you can imagine that someone on the other end of their email might have you as a priority. So that's an aside.
Maryann: What was in your email?
Dana Ray: I think it was “Hello, I live here. I do this thing. Can I meet you?”
Maryann Lombardi: A lot of people don't reach out for whatever reason. So when people do reach out, I'm always really excited about that. This is why I give my cell phone out to everybody, because the amount of people who actually take me up on the offer to text me or email me or whatever is quite, quite small. Maybe it's because I'm scary, maybe it's because it's government, maybe it's because it whatever it is. But when people reach out, I’m all game!
Dana Ray: And I would add that the reach doesn't have to be a pitch. It wasn't saying, “Can you get behind this thing that I'm doing?” It was simply out of curiosity on my end.
Maryann Lombardi: Yeah, we ended up having a great conversation.
Dana Ray: So what are your biggest challenges that you see on the individual level? Is this like connecting with people? Speaking specifically to artists and creatives in COVID time. What does it mean to build community right now?
Maryann Lombardi: It means the same thing it meant before. Building community often felt like it had to include some big huge networking event and people had to come together around an event. One of the things that Covid has shown us is that when you strip all of that down, the work is really one-on-one. And that's slow. And people don't like it, because it's slow. Even if it's if it's literally just saying, “Once a week, I'm going to find and connect with somebody that I haven't really talked to before or I'm going to reconnect with somebody” and make that a part of your workflow. That's how you build real relationships.
And quite honestly, that's the way it worked before. Because you would go to those big events, and you would meet 800 people, and then you would come home and feel really crappy because you didn't make a connection. And then you would follow up with one or two people who stood out. So you don't necessarily need the 800 to follow up with the one or two. So I think there's an opportunity here to just start putting that process in your workflow and see and see where it leads you.
And don’t put too many restrictions on the follow-up. It's great to have goals. I'm not suggesting that you shouldn't have goals and a mission because I'm a highly mission oriented animal. But I do think when you're meeting people it needs to be a little looser with that. Just try to find people that you think are interesting.
Dana Ray: Amen! Reaching out to people I don't know, is my favorite thing to do. I know that it's hard for some people. And I'm like, that they might be cool.
Maryann Lombardi: Well, it is hard, right? I am not suggesting that it's a simple process. But I do think that more often than not, the people who respond want to hear from you. We want you to succeed! And that is actually something I really like about DC is that I find that there is a really honest feeling that people want you to succeed here. And I've lived in work environments that have not been like that.
Oh and please get it out of the social media space. Get it into an actual face-to-face conversation with somebody or getting on the phone or something like that.
Dana Ray: How do you stay in touch with both what you need and what your community networks are in need of?
Maryann Lombardi: Once we know that that's a need, then then the process is making sure that our partners are still getting served the way they need to get served in order to like move that thing forward making staying connected with the community that that we've been talking to, to make sure that that service is still needed. That's just a constant process of staying connected with people.
Relationship and partnership building requires you to keep in touch. If you have a customer, you sell them a product. And you're keeping in touch to see whether it's of service, to see whether or not that that customer is still utilizing your product or your service. And if that customer isn't utilizing your product or service, you want to know why you want to reach back out to them and say, “Hey, what's going on? Is there a way I can help you? Do you have a question?” Maybe they've grown out of that service and are moving on to something else, and that's fine. Or maybe the service is just not quite tailored to them, and there's something you can do to adjust to help them.
That's what we do: we need to be in touch with people to make this thing work. You can't just push play and be done. This work is a relationship between you, the business owner, you the service and the customer. In theater, it’s a constant feedback loop: you're putting something in front of an audience, the audience is going to have an opinion about that, and you're gonna have a reaction to that opinion, sometimes you'll adjust and sometimes you won't. Because you're having a relationship with your audience.
Dana Ray: I heard this line that “Change moves at the speed of relationships, and relationships move at the speed of trust.” So in some ways, what we're talking about is the slow and the building of trust between individuals and networks and communities and systems. To do meaningful work, to do creative work, and to keep our heads above water financially--it’s intertwined. How do we build trust with people outside of our spheres? For example, someone like an engineer who might think very technically or systematically, you have very adaptable thinking structures, but for creative who might be in a more, you'd be stereotypical creative thinking pattern. What does that trust look like when there's so much difference between our industries?
Maryann Lombardi: I think the first part of it is to stop seeing people as a representation of their industry and seeing people as a representation of themselves. Engineers can be wildly creative. And Science People or Policy People are fascinated by talking to people who think differently. I think we suffer a lot from categorization where you say, “I am an artist, so therefore, only artists understand who I am and understand how I think” and that's just not true. So that's the first step of it is to stop seeing people as labels and see people as people.
There’s this painting that's behind me that is a reproduction of a classic Renaissance work that was done by a bunch of science students at the University of Massachusetts Amherst. They were in an art class taught to science students. The point of it was to get them out of their science brain and into their creative brain, and to help them see things from a different side. And it was wildly successful. All of the feedback after these classes was that the students felt it unlocked something for them in their work. And I think that's always potential when you connect people who seem like they have differing ways of looking at the world. We all need to be talking to people who don't just think like us. We all need to be open to having broader conversations beyond the labels.
Dana Ray: Broader conversations beyond the labels. Wow. This leads to another question that someone asked which was how do we find investors as artists and creatives? The startup world has the VC culture. What does it look like to look for funding and support and investors? Is that a thing we should be pursuing?
Maryann Lombardi: Well, it's always a thing we can be pursuing. But there is a reason why it starts with a friend and families round.
Dana Ray: There's also a lot of accessibility and equity issues that surround this idea of friends and family round up. What did your parents do for a living? What if your friends aren’t deep pockets people?
Maryann Lombardi: True, but the relationships that you build can lead you there, right? Just because just because mom and dad don't, you know, aren't coming with the you know, with the change doesn't mean that your process in developing relationships with people won't lead you to somebody who's interested and excited about you and what you do.
You know, it can't it can't be a not not having parents who are wealthy can't be the excuse to not develop relationships with other people who are excited about what you do. You know, there's lots of systems and networks, especially here in DC, to connect around meeting people, you know, and expanding the venture capital space, and you know, whether it's through the pitch environment, whether it's through other organizations, whether it's through networks. So I think that that friends can be broadly speaking, it's just networks, right? Like it's building those networks in order to lead you to those places.
And then on the system side of it, we absolutely need system change. It's the responsibility of those smaller organizations and those startup folks to start building he networks that helped lead them to what would could be the friends and family round.
There’s a lot there's a lot of equity and access issues within the startup space, especially for Women Founders and Founders of Color. It's not great. But that still means we still have to get in there and try to build the relationships that help us get past that.
Dana Ray: Okay, this is next question is spicy.
Maryann Lombardi: Bring it on.
Dana Ray: How do you balance creating the art that you want to be making and making your art a profitable business?
Maryann Lombardi: The first thing I always ask people, which they often try to skip over, is Do you actually want to sell the art you're making? Some art isn't meant to be sold. Right? Your relationship with that art doesn't always have to turn into a business.
There is a little bit of pressure that exists that somehow you have less value as an artist or creative if you're not out there, you know, hustling and grinding your way to sell your stuff. And the reality is, you actually can choose to do your work and not sell it. That is just as valuable a choice as taking your work and selling the shit out of it.
Make sure that you actually want to [sell the work]. Because if you don't want to do it, you're going to find ways to fail.
Then the second piece is to find your audience. That’s another thing that often gets skipped: is there an audience for what you're trying to sell? Just because you love it doesn't necessarily mean there is a market for that thing.
And if there is, then there's a whole other set of steps to go down to sell and figure out your ideal customer and get a business plan and you know, do all of the things that you need to do. But you can't jump over those two steps to start: do I actually want to sell it? And is there actually a market to sell it?
Dana Ray: Another way of asking that question: What does success mean for me? What does meaningful art making look like? For me? And selling is one expression of that but it's one facet of that larger question of “What is this work actually for? What is my work actually about?”
By the way, people are like falling over in the chat from the line: “If you don't want to do it, you will find ways to fail.”
Maryann Lombardi: It's not a bad idea to find to distill it to that. Often we think too romantically about it, it's very easy to miss the core. Distilling it this way kind of helps you knock yourself in a little bit and be like, okay, like, what do I really want? Because you can't get to what you're talking about, if you don't know what you want.
Dana Ray: Helen just asked in the chat, “If there is a market, if you do want to sell it, how do you find your people?” Which is another way of talking about like that relationship building.
Maryann Lombardi: There’s two kinds of people. There's your people, which are the community that are going to support you on this journey. And then there are your customers. And there will be some overlap between those two communities, but it's good to recognize that they are different. As you are building out a business, it's good to have your community, your network of people that will support you as you go through that journey that you're not also trying to sell to. Because that changes the dynamic a little bit. You’lll have a hard time seeing who your actual customer is if you're only selling to your friends.
And then when it comes to figuring out who your customer is, that's a whole other process. The first thing that you need to figure out is your why, who, what, where, how. You need to figure out the answers to those questions. And then you do need to figure out a business plan. And you do need to have revenue streams, and you do need to figure out what my multiple revenue streams are. It's a pretty standard process of figuring out, like, what I do, who's my customer? How am I marketing to them? What's my story?
Thank you to DC Startup Week for hosting this conversation. You can find other DC Startup Week talks at their youtube channel.