Tech founder Anna DeShawn is driven by her startup's mission to elevate the work of BIPOC and QTPOC creatives. But asking potential investors for support and capital makes her feel raw and vulnerable. Stevon breaks down how we can make key decisions and talk about money confidently when business feels personal.
Stevon Lewis is a licensed psychotherapist and coach. Learn more about his work here. If you loved this episode, be sure to listen to Asking for What You're Worth, And Meaning It and When Everything Feels Like a Personal Attack.
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Stevon Lewis:
What's up, everybody? Welcome to How to Talk to [High Achievers] About Anything. I'm Stevon Lewis, a licensed psychotherapist. Today, we welcome Anna. Anna is a tech founder who is passionate about her work, work that feels very personal to her. Her team is building a streaming platform that centers black, brown, and trans creators of color. When Anna's out there making pitches to potential funders, those conversations around money make her feel incredibly vulnerable. Let's get into it.
Anna: I'm Anna DeShawn. I'm the founder of E3 Radio, the co-founder of The Qube, and I create streaming platforms that center and celebrate BIPOC and QTPOC creatives. Growing up, I was very clear that I wanted to be the next Robin Roberts. I was going to be doing play by play announcing on ESPN just like her. Then I quickly realized that there weren't people like me, masculine-of-center women, on your television screens for news. Wearing makeup isn't my thing and wearing suits is. I pivoted and I started a radio station called E3 Radio in 2009 to tell the stories of LGBTQ folks here in Chicago and around the country.
But a few years ago, me and my team were having conversations around how we can increase listenership, how we can make it easier for folks to tune in. What if you could go to an app where you input your favorite podcasting topics and your identities? The app could then serve you up recommendations based upon both of those, and that's what we're building. I quit my job last February to pursue the radio station and to pursue The Qube full-time and to give it everything I had, because I didn't want to live life with any regrets. There's a lot of challenges when you decide to create an app, specifically around funding.
When you're out here asking for money for something you're passionate about, and because we all hold all of our own preconceived notions and feelings around money, those feelings come from how you were raised, how you were taught to think and feel about money, and you bring that along for the ride, you're going to need a lot of practice on how to make that ask. For me, one of the challenging parts about making those asks today is how I tell the story so that people understand the impact they can make with their investment. It's hard to get out of your own way to do that sometimes, because you do hold your own stuff.
It's a very personal thing. People say all the time like “business isn't personal.” I don't understand that. For me, business is very personal. Business is what keeps a roof over my head. It's what keeps food on my table. My business is that to me. When you're going out here making asks, knowing how much work, blood, sweat, and tears, I cry almost every day. Okay? Let's be clear. When you hear no all the time, it can really knock you down. Asking for money, and that is incredibly vulnerable. Literally every single one of my investor talks starts with a picture of a red pig surrounded by other blue pigs. Okay? The red pig is this only red pig.
The story goes like, I'm this red pig. I walk into rooms and I'm the only person of me in a space. My question to people is, have you ever felt that? Have you ever felt what that feels like to be the only one of you in a space? Because that's what it's like when you open up an app and you don't see anyone that looks like you in that app. It is lonely. You feel not seen. You feel not heard. And that's how I start every single pitch. If someone after that still doesn't get it and tells me no, it can knock the wind out of me because it is personal. For me, it goes deeper than just dropping me a check, because all money ain't good money, right?
For me, as a black queer woman, all of my identities come with me everywhere I go. If one of my identities does not align with your belief system, if you are investing in me and then also investing into anti-LGBTQ initiatives, this ain't going to work. I don't want to accept money and have people on my cap table who I can't trust to what I would consider to be doing the right thing. It is challenging to hold a firm stance because I do need the money. We need capital. I've got a wonderful team who deserves to be paid, right?
You need capital to get that done. You need funding to get that done. It is in those moments where you have to tap into, well, what's your moral and ethical fiber made of? I trust that my moral, ethical fiber is strong enough to withstand those tough conversations and being able to say no to the money that don't feel right and saying yes to those that do.
Lewis: Thanks for letting us in on your experience, Anna.
When I listened to Anna's story, the thing that stood out most is her level of insight. She's really aware that her process or her approach may not be what's accepted or envisioned by others. And that's not going to stop Anna from going out and continuing to accomplish and achieve and do things. Her business and what she's creating is a manifestation of who she is as a person. I think that that's really impressive because it's saying her driving force and her why is really clear. Her mission is rigid in a way that I think is very good and beneficial and will not be kind of thwarted by society's lack of evolution in this space.
We often think about rigidity as being inflexible and harmful to our growth and to our progression. I think that can be true most of the time. There are also instances of when we need to be strong and firm in order to expand or push or create change. What Anna's trying to do will not happen if she's too flexible or malleable. She has to be grounded and stand firm so that the area of entertainment that she wants to be in and has had a fascination for her since being a kid will have to develop and grow and evolve around her. That's really important because it says, "Here I am. I am a fixed rooted being." You're going to have to find a way to coexist and exist around that. I'm not going to change so much, you will and it will all be okay.
When Anna makes that statement about for her business is very personal, she's showing up and saying that, "I bring all of me into my work." I think that's true for most high achievers or entrepreneurs or creatives, that a version or a portion of themselves is put into what they are putting out into the world. That's the driving force. I think when people say business isn't personal, what they're trying to say is “don't be emotional about it.” Let's remove the emotions because it'll cloud your decision making and maybe cause someone to make decisions that wouldn't be in their best interest because they're operating from an emotional place. I don't know that I agree 100%. We’ve got to be specific about what emotions and when. It needs more context around it. What happens for creatives and other high achievers and entrepreneurs is that there's strong emotion. There's a passion there causing them to venture out into the areas that they've decided. And so, when we talk about “we’ll take the emotion out of it,” it's, “well…this thing exists because I have emotion. I don't know how to separate from that.”
What we're saying is don't make rash decisions because you felt upset or angry or you were overly excited and happy about this instance. Be more objective and have a little bit more evaluation as you make decisions about your business. I don't think we need to remove emotion. I think we need to use emotion for what it is, as a cue. A cue to say, "Let me inspect and investigate this further and find out what's going on."
Anna made a really good observation, not all money is good money. Already having this, I guess, vulnerability and asking for money, there's also the part of her values and morals that really drive why she's doing or why she's creating what she has. And that people who are going to be in support need to be in full support, not just financial support because they can make a buck off of this idea.
They also have to be, how we like to say, kind of ‘bout that life, right? It's a really tough place to say, "Hey, I need money, and also I might have to walk away from it." Even talking about how she's going to pitch or her idea to the funders and investors or potential investors and potential funders, she leads with herself. Here's the clip of something that really stood out to me.
Anna Clip: Literally every single one of my investor talks starts with a picture of a red pig surrounded by other blue pigs. Okay? The red pig is this only red pig. The story goes like, I'm this red pig. I walk into rooms and I'm the only person of me in a space. My question to people is, have you ever felt that? Have you ever felt what that feels like to be the only one of you in a space?
Lewis: I really like the idea that she is aware and brings her full self to asking for funds and she leads with that as part of her pitch. Also, I think the way to make it easier when we have our own personal kind of history with money and hang ups about being vulnerable and asking for help is to make it bigger than ourselves.
Part of Anna's passion is to have more representation, inclusivity, acceptance of BIPOC and QTPOC folks in the space of podcasting and apps and streaming services. Then it's not about Anna so much. The driving force is bigger than Anna herself.
It makes it easier for us to do things when it's not so much just for me, especially when it's something big like this, like we're trying to create change in an already established space or environment, then I'm not doing it for me because I can go and live life and be just fine without having to do this. I don't need other people's money in order to have my bills paid, but to do this thing I do. I've got to take a step back and say, "This is not about me," and let go of some of those things. That's I think the way to make it a little bit easier.
When we're looking to do something new and different, part of the risk of asking for support and being open and vulnerable when requesting help is that people can say no, and that doesn't always feel good. How do we interpret that when part of what we're trying to do we are so passionate and connected to personally? For Anna and folks like her, sometimes we can't expect other people to have the same vision and passion and understanding as we do, and that maybe their “no” isn't really a rejection of you and your idea, it might be based on a limited understanding of what you are trying to do and accomplish.
The analogy I use is that if we're looking at a parade and someone is in the helicopter looking at the parade versus someone in the stands, they're looking at the same event. The perspective is very different. For the person that's super passionate and it's their baby and they are personally connected to it and they are pitching it, they're in the helicopter, they see everything that it could be. They see it from the beginning to the end, and they understand its purpose. The person in the stands that maybe they're requesting funds for can only see one float ahead.
They won't make decisions or be able to understand why something might be beneficial or good to do now because it hasn't gotten to that point for them. I'm in the helicopter and I'm pointing out things to be aware of or saying, "Hey, we need to move like this." It will not make sense to the person that's in the stands.
The idea is to find someone who either can come up in the helicopter with you or adjust our patience or frustration level so that we can be a little bit more patient to say, "Well, I can come back and revisit this with you maybe in six months when you recognize that this shift needs to happen and you need to be at the forefront of whatever this movement is." Don't see the rejection as a full rejection of, "I hate you, I don't support anything you're doing." It might be based on a limited understanding of what's going on and what's happening in the world.
The last thing I'll mention is to be mindful of the speed of your trajectory. You might have to slow down in order to accomplish what you want to accomplish in the way that you do. If you have strong morals and strong values and you aren't wanting to have to compromise those things in order to bring your vision and your dream to fruition, then it might take longer to find that specific person that aligns with you, that can support you, and that is motivated to support you in the way that you want. Being realistic about that. Not that it won't happen, but that it might not happen at the speed at which we want it to.
And that's a wrap. Thank you so much for listening to How to Talk to High Achievers about Anything. We have really big plans for our show, and we want you to be a part of it. We want to hear about your successes and challenges, your sacrifices, the ways you've celebrated, and what's ahead as you grow. Send our producer Virginia an email, and we'll get your story on the show. She's at virginia@lwcstudios.com.
How to Talk to High Achievers about Anything is an original production of LWC Studios. Virginia Lora is the show's producer. Kojin Tashiro is our mixer. Juleyka Lantigua is the creator and executive producer. I'm Stevon Lewis. On Twitter and Instagram, we're @talktoachievers. Bye, everybody.
CITATION:
Lewis, Stevon, host. “Managing the Emotional Risk of Pitching Your Passion.”
How to Talk to [High Achievers] about Anything,
LWC Studios., October 17, 2022. Talktohighachievers.com