517 - How to Turn Business Pressures into a Fun Creative Project with Yowei Shaw

32:07Like, even if it doesn't work, why don't you try for a year to like do your own thing? And so, yeah. So then I started making this show proxy. And at first I wasn't planning on going independent. I was planning on just like coming up with this concept and then pitching it to podcast companies, production companies, and then selling it. And then having some other company entity fund the entire operation. And I would have like, you know, a job with benefits or, you know, money coming in at a regular, at a regular interval. And I did that for a summer and it just it just didn't work you know like I did get some offers that were okay but basically everyone if they said they were interested they wanted IP they wanted intellectual property and I was just like I cannot let myself get into the same situation where like some company owns the feed, the podcast feed owns the idea.

33:14And then like, for whatever reason, some exec is like, we're shifting strategies, even if the show is doing well. So I guess I'm just going to try to do this on my own. And at that point, I knew nothing about how you make money in podcasts. Cause like before at MPRA, I was just like, I'm under a rock just making this little show and that's it. I don't, you know, business and advertising that was handled by like an entire department. And there was actually like a firewall where actually like journalists are not supposed to like handle talk about any of that stuff. And so, yeah, I basically was like, now I'm on the beat of, you know, now I'm a reporter who has to figure out how do you make a sustainable podcast in 2025 in a shitty podcast landscape when narrative podcasting is collapsing.

34:07And so I just like called. I made so many calls. I had so many meetings. I like really, really tried to learn like what was up. And then I came to the conclusion like, OK, so it's like advertising and some kind of subscription revenue membership program. and like ads are really you're not going to be able to like get to this scale you basically have to get something like 300 000 downloads within the first month for every episode to make the kind of money to support like a narrative podcast team and i was like well that like it just doesn't happen anymore because it's so crowded at this point um and also in podcasting audio first podcasts there is no good algorithm yeah so like discovery and growth is really like you you're just kind of like clawing your way up through word of mouth and like feed drops and cross promos and there's no there's no youtube algorithm that's gonna like make you viral you know um and help you find your audiences um and so it was like okay advertising and then there's subscription revenue like you know what they do on sub stack and patreon and there's a whole bunch of different services out there and those numbers made so much more sense to me i was like okay i need around 3 000 patreon members paying five dollars a month for me to be able to like pay myself pay other people make this show and like 3 000 versus 300 000 i was like okay i feel like i can i can maybe this feels doable and so yeah basically i have not really even paid attention to advertising and i have not really sold i've only sold one ad um and it's really just my my focus is really on patreon yeah um which is i learned later 3 000 is a lot of members to try to get to so it sounds like oh it's not that much but no it's actually really really hard um so that's sort of where i am which is like i'm trying to grow the audience to the place where there will be enough like basically it's all it's all about audience growth and also like how i'm making my patreon pitch um and yeah so my husband is very helpful and he like made some complicated excel formula thing where that like calculates like how big of an audience i need to try to get to to try to get like the number of patreon members that i want to get to yes um so yeah that makes tons of sense And obviously it's a percentage of the total listeners are usually the ones willing to support a show.

36:58It's very, very small. It's very small. It's like 1%. That's my guess. Yes. It's like 1 % to 3%. Yeah. That's my guess. And so there's so much stuff that's really interesting here that I want to pick out. One is this shift from – we talk about this on the show from time to time, the classic 1 ,000 true fans idea. shifting away from thinking, oh, I need to make these huge deals to, I just need this core group of people. And then also coming to terms with the fact that 1 ,000 true fans means, I don't know, a hundred thousand passive fans or whatever, but all good evolutions to how you think about your practice.

37:39I think it helps you zone in on who it's for, go deep with people instead of trying to go wide and appeal to everybody. So there's a lot of really, really relevant stuff to everybody listening to that. One piece that I want to zoom in on is this is what I want to try to get at what's good about being on your own. So there's a lot of talk and information, rightfully so, about how putting all the pressure on your creativity can get in the way of being creative. It can make it hard to access your creative self when everything feels do or die. I've experienced that. I know lots of people have experienced that.

38:16But what I don't think gets talked about very much is the positive side of this. And so when you were talking about earlier how at NPR, as the journalist, you're not really connected to the marketing of the show and these paths shouldn't cross. But then I thought, I've heard Ira Glass talk about how he attributes part of his success in becoming a great storyteller to having to sell his show and develop the ads for This American Life for all the different NPR stations. Yeah. Because it's so it's it's a yeah. So I'm not going to say anymore. What what do you how does that sit with you in terms of now that you are deeply connected to the selling of the show?

39:05Do you think it's changed your storytelling? Has it impacted it? Has it changed the way that you do the show? Yeah. I mean, I have a lot of positive things to say. I think it's been huge for my creative development. Let me list the ways. Let me count the ways. So number one is at Invisibilia, I was only reporting one or two stories a year. And at that time I was like bored. I was like, I can do more. Like I, I got lots of questions. Like I'm fast, let's go. And so having to make you know this new show where you know the more you make the better it is the more of a habit you can become and you know this is all the advice i got um the more ads you can sell um basically there is this huge uh push for more and more content which is you know every of course there are problems with that you can overwork but for me it's been really liberating to be like, okay, not everything has to be perfect.

40:09I think I had like a perfectionist, like a lot of people have this perfectionist issue, maybe more in the beginning of their careers. And for me, it was debilitating. And it like, you know, I think because I was operating from a place of fear. And now I'm operating from a place of play and experimentation, because there's always another there's I got to make another episode, you know, so it just lowers the stakes for like how good does this have to be which weirdly has I think made my work the strongest it's ever been you know and I mean that in all kinds of creative choices like my writing how I how I track you know um like doing these like silly I do this like silly bit with my husband who like mixes the podcast for free he's like the running gag is he's the bedraggled podcast spouse I'm always making him work on the weekend you know just like all of this stuff would never like first of all like like I just needed something and I was like what's like the first idea that comes to me okay let's try it okay oh that didn't work let's move on to the next thing so I think it helps with the experimentation piece um and then I also think that doing things on your own has allowed me to get away with stuff that I would not there's no way and like like I'm making the decisions here I have a great team I have like an amazing editor Tim Howard who used to be the editor of reply all my favorite podcast yeah and he's like I trust his taste over every Like I just he's the best editor.

41:51But at the end of the day, it's my decision. And also, it's just the two of us mostly making making these calls. And so things just happen so much faster. There's not a lot of no, I would get a lot of no when I was at NPR. And that really stifled creativity and experimentation. In terms of the selling of the show, I think that, I mean, frankly, it just has pushed me to try to solve new creative challenges. I find that it's most helpful for me personally whenever there's an issue I have. It's like, can I report my way out of this? And or can this be a creative challenge? Yeah. You know, because that just makes it like fun.

42:45Yes. Rather than like, oh, God, I need to like figure out, figure this out or like, you know, no more proxy and then I'm in debt. Like I don't like that's not helpful for me. Yeah. And so, I mean, I feel like the work that we do in narrative podcasting, it's all creative problem solving. Yes. Like that's just like every story is a new puzzle that you have to try to crack. um and like i'm good at that and it's fun for me so you know okay so i have to try to get this many patreon members okay well so like what if we try this like what if we tried that like you know it's just a lot of to me that is i i've had to reframe it as fun yeah um as like part of the art itself.

43:39Yeah, I totally agree. Yes. Otherwise it's bad. Yeah. The marketing, the business, all of that. I think it's interesting. When I had a brick wall early in my creative journey as an illustrator and I talk about my rock bottom being not drugs and alcohol, but marketing books and business magazines and, you know, really begrudgingly going into that zone. And there were so many different takeaways, but eventually I started to feel like, you know, when you're in the business world, I feel like they really want to downplay the variables and the level of creativity that is required for a business to be successful because they want to make it math, right?

44:27They want it to be, this is the taxes, this is the accounting. Once you got that, it's pretty much good. And you're like, that's almost nothing about what makes a business successful. And there's huge areas of creativity that are required. And once I saw that, yeah, I started to see it as a creative problem. I'm going to just really quick summarize that with a few points because I think, and then I want to ask you a follow-up question just because I think you said so many really great Can I just say, I love this summarizing move you're doing as a host. I'm learning from you right now. I'm like, oh, this is great what you're doing.

45:02You're like making sense of my jumble of thoughts. No, it's so good. I don't want people to miss it. And I also like to think about the utility of the show too. Like, you know, I'm constantly, um, cause I, a lot of the show is, and I'm talking about this, just like comparing notes, uh, because so much of the show is, uh, a monologue solo show where I can control everything. Um, I try to inject some of that energy, not without like taking over completely, just some of the like bullet point energy, bullet point energy. Okay. I'm, I, I like what you're putting down. I'm going to remember this. So I won't bore you, but I think the question was about like, what does embracing the sales marketing side of your creative practice do for you positively?

45:53Cause we've said so much about what it can do negatively. And I think you said, it gives you a bunch of at-bats when you start like this, this change helped you to like, just try things quickly, fail quickly. I think you see that in really successful creative people, like stand up people are constantly going out and trying things rather than just being perfect about it I think there's a cutting the ego thing that happens where you have to get no bullshit of like this either has to work or it doesn't yeah and I like the romantic side of creativity I'm all about it but sometimes I can overly romanticize and miss like this is a human connection and then it helps you with speed and perfectionism and the fourth thing was you get to see it as a creative problem in its own right, the business.

46:41Yeah. Yeah. And I also, this is maybe going to make me sound really not appealing, but like this whole process has also made me realize that I'm deeply competitive. Right. Like I play tennis too. Yeah. Okay. Here we go. Well, yeah. So like competition, being competitive is not seen as like generally a good trait in this culture because it's like, you know, capitalism, blah, blah, blah. And like, you know, I, I hate lots of things about capitalism. This is not what this podcast is about, but in terms of just like my own motivation, like I grew up playing tennis very competitively. I competed in everything.

47:22I competed in piano. I competed in tennis. I was a theater kid. We competed in Texas, weirdly in theater. They had one act play competitions, competed in debate. So I think just like I was trained to kind of compete and have that be fun. And so there's like, it taps into this kind of like, I'm, I'm a jock just trying to like hit a winner, you know, like really like hit the, you know, do an overhead shot that's going to win the match. You know, it's, it like makes it, I just makes it kind of game. Yeah. like yeah which is like you know again I guess these are all just like emotional mind tricks we're playing with ourselves to make us not be motivated to do the things that we need to do to try to survive um that's how I see it like I'm not I'm trying to like you know make myself feel too weird that I like competition but yeah it's an emotional mind trick and um I get to like inhabit a different persona, which is not normal for me.

48:26Like I'm, I'm a really nice person. I like making people feel good. I like saying yes. Like, I don't think it's a bad thing, you know? I mean, it gets me in trouble sometimes, but I, I'm like nice. Yeah. And so this is like, so this is fun for me to be like, oh, I'm going to be a fleas ball. Like, I'm going to be like, like, I'm going to be like Wolf of Wall Street right now. you know what I mean like it's just like yeah yeah it's like a character and energy that you can inhabit um and so like maybe that's one takeaway I'm gonna inhabit bullet point energy right now which is like looking for the personas and characters that motivate you I think that's very real I think about that a lot finding those like archetypal characters that they're like I need this energy right now.

49:17And I love that too, because, you know, you talking about the competitive side, this is something that I, I, I think about creative stuff a lot, like whole brain activity needing to oscillate between several different types of you. And I think when I do get the, we're so in this culture of like inhumane levels of competition. So I get why it gets the criticism that it gets. However, I think that in order to be like a successful human, you have to be like a cell in the body with your own nucleus. We're like, I'm going to survive and thrive. And I got to do what I got to do to do that and realize that you're part of the body.

50:05You know what I mean? So I think that, yeah, there's something to doing both of those things. I mean, you can be into playing video games and board games and like, like playing pickup basketball and not be an asshole, you know, but like in the actual container of the game, it's fun to like compete and like outdo yourself and outdo other people. And, you know, like, I don't know. I think, yeah. I think held intention is it's really important. to have an ego. It's important to be like, I'm an individual taking care of myself, trying to do the best I can do. And I'm part of a system that, you know, hopefully is cooperative and that kind of thing.

50:47And the system is imperfect and flawed and we need to collectively work to try to make things more equitable and accessible for everyone. Absolutely. I recently read this memoir by Kara Swisher. Do you know who Kara Swisher is? I know that name, but I can't Huge tech, like the most famous tech journalist there ever was. And she, you know, has a bunch of podcasts and blah, blah, blah. She covered the tech industry from like early on to like she's she like was on. She's like on a texting basis with like all like Elon and all the people. She's covered them for years. She is hugely successful. And when I read her memoir, she used this phrase that I was like, oh, my God, this is I've never heard this.

51:32But she would say all the time, like, I'm going to kill you. And I was like, what is she saying? Like, is this normal? Like, is that normal? Have you heard people? Maybe it is in like the tech and business world. I've never heard anyone, but it was just a reframe. Like, oh, I'm going to kill that person. I'm going to kill you. I'm going to bury you. I'm going to defeat you. Like in a competitive way. In a competitive, playful way. It was a playful, like she's not actually going to murder people, you know, I was like, wow. We're going to find out one day from another journalist that she's got tons of skeletons literally in her basement.

52:11Yeah. So I was like, wow, that kind of energy. Like, I mean, that's maybe taking it like I don't really want to kill anyone to kill people. But I was like, oh, OK, maybe that's the kind of like energy. I mean, she's very successful. I don't know. We're not endorsing murder here. No, absolutely not. I don't want that to be confused whatsoever. But I think being a grown up, being good in your creative practice, I think requires you to hold a lot of tension, like being able to have two energies or at least switch between them. All right. So I've got one more question for you. I have a thousand more, but it'll have to be another time.

52:54But my last question is about, so we always end the show with what I call, it's a CTA, but it's a different, it's a more fun one. It's call to adventure instead of call to action. And it's about taking some of these ideas from the show and putting them to practice in your creative practice. And so I thought it would be great to learn. I thought you did this incredible thing where you really did take a marketing effort and you turned it into a creative project, part of the show. Can you, do you know what I'm talking about? Can you speak to that? Yeah. The four-part series. Yes. Fundraising campaign.

53:35I love this. I think this is kind of incredible. So could you tell us a little bit about that? And then maybe we can talk about how people could try something like this. Yeah. So basically last summer I did a four part series about what the heck is a proxy conversation and why do they work? And so that was like the narrative series. It was an, it was like a four part series where I was like on a quest to try to figure out how to explain my show because I was running into this issue with sources and listeners where like I had trouble convincing experts to come on the show because they just like I just was not able to explain it adequately to them.

54:21That is like the the content. But it really also was a four-part, month-long quest to get to 1 ,000 Patreon members. Yeah. And spoiler, we did not make our number. So, like, you know, it's interesting that you call this a success. I mean, it was a success in that we doubled our number of Patreon members. So it was, like, the biggest jump that we'd seen. And it was also fun. And I learned things about how now I know how to like explain my show better. So, you know, win, win, win with a little, you know, minus of not making our goal. But really, like the genesis of it is like it's one of the oldest storytelling tricks, I think, in the narrative podcast world.

55:12You know, startup, if anyone remembers that podcast, Alex Bloomberg is like starting a podcast company and trying to get venture capital, which later became, you know, he started Gimlet, which, you know, got bought by. Spotify and then flamed out like you know he documented the process and made that part of the narrative like he was the hero the protagonist trying to like get rich yeah just kidding um and so like that was the model I was like okay so I'm the protagonist here trying to like make it to this goal so that we can like hire get more hours for my producer and like continue making the show So that's like already like there's a narrative cliffhanger built in of like, will they or won't they?

55:59And so so there's like there's that. And there's also just kind of I think there's something fun about pointing at the thing you're doing, like pointing at the selling. Yeah. Like, otherwise, like, it'd be very difficult for me to make these pitches, because for me, it's like it is kind of it's kind of ridiculous what we have to do, you know, to be like, please pay like, please, like, convince people to think we're worth spending money on, you know, is kind of a ridiculous prop. It's a ridiculous quest. And so for me to like be able to do that full heartedly, I have to like, I don't know, I need to point at the thing and kind of like have fun with it.

56:47But yeah, that's how I make sense of it. So, yeah, in this series, I talked to I found I discovered that proxy conversations have a history in restorative justice where, you know, victims and offenders, if they don't if they can't talk to each other for that healing conversation or they don't want to, maybe it's too triggering. maybe someone has died maybe someone's not remorseful whatever the reason um there's this tradition of like you can talk to a proxy victim or offender for that like healing conversation which is sort of like the most important piece of restorative justice um and there's been research on this and they found that like oh yeah it actually works and can actually be more effective um and then i also learned i talked to this um psychodramatist i learned that like oh actually like there's this whole therapy where role-playing is huge and it feels similar to what I'm doing.

57:50And then I got him to explain like what he thinks is happening on a neurobiological level. So I don't know. I think that like, I got a lot of good feedback from that series. I think the lesson that I learned from that is you have to make your pitch entertaining. like it has to be fun and informative like people listeners you know your audience they have to be getting something out of this otherwise when you make the pitch it's just going to be a chore yeah and that's really what I want to avoid is like I don't want you know when I start to make the Patreon pitch everyone to be like oh this again another NPR fundraising try yeah I what I I call it a success because I think you have a – I know it's not completely arbitrary.

58:37I know there's like numbers behind what the goal was, but it's still an arbitrary metric of whether this thing succeeded or not. The fact that you doubled your patrons and for me what was successful is you made great episodes. And so for me, it's like this really interesting thing where you were able to do, where you were able to hold the tension of the left brain goals versus the right brain goals and do that at the same time. And so I think it's an interesting challenge for the creative call to adventure today to think about what would it look like to create a creative project that also meets a business goal and see if I think it's even a challenge.

59:23I know this is possible. You've done it. I've done things in this realm, but the challenge is to see how you can do two things at once and what can be cool about that and interesting about that. And also you can be transparent about that, like you were, which I think is another layer. I want to say, I wanted to add one more thing. The other thing I really love about your journey here is that you have taken an obstacle and used it as a constraint to be an opportunity creatively where, like you've said, narrative podcasting, traditional narrative podcasting, which traditional podcasting is kind of a weird term in the first place, but narrative radio doesn't have the funding it used to have.

1:00:13And lots of people in that scenario see that purely as an obstacle, whereas you turned it into a creative prompt and said, how could we take some of what's great about this and do it in a way that works in how people are consuming this media as companion, more passive stuff? Were you aware of that? Yes. That's what you were doing? Yeah. Absolutely. Thank you for bringing this up. Yes, absolutely. The main issue with narrative radio why it's dying is because it costs too much to make um it takes too long costs too much to make the number of episodes you need to make to get to sell the ads and get the audience you want and so this like idea of like what is a light lift way to make narrative audio like it will if you say those words light lift to a narrative podcaster they will roll their eyes because this is like what is talked about all the time.

1:01:12But for me, I was always like, oh, this is like a fun creative challenge. Yeah. Like, cause I'm honestly, I'm sick of making the honkers of stories. Like I was like, oh, and honestly, I don't know if listeners are getting always more out of the experience. Mainly the reporting, like let's not, you know, the reporting takes time and that's, you know, something that I've had to dial back on my show. But anyway, so what I did was I decided, okay, how can I like lean into the like chat that people like and that honestly I like as a listener. I don't listen to any narrative podcast now. I only listen to chat.

1:01:54So like the warmth, the depth, the spontaneity, how can I like do that but with like a narrative lens, which is like narrative lens. It's like high stakes. There's structure. There's character development. And so that's how that really is the reason why I came up with this format of like segment A is narrative in its traditional form of like, here's the story of this person's problem. Sets up the stakes. You get character development. It's only it's usually around eight minutes to 12 minutes. And I found that these are so easy to make. There's it's just like I'm just like, wow, I can write that in like a day or two.

1:02:37Wow. That is bananas to me. And then the rest of the show is this proxy conversation that I prep and produce, you know, for sure. I spend time figuring out how to make it so that there's a flow, that there's like, you know, an arc. But it feels like just a conversation that we have heavily produced and prepped. And the idea there is like, how can I make this? How can we feel the drama of a conversation? Like, how can we tap into the highs, the lows, the awkwardness, the reveals? Like, how can we feel narrative change and like release and tension and stakes, but like in a conversation? because to me that was something that like narrative podcasts didn't do enough of because we always use like short pieces of tape or like at the most two minutes or three minutes you know but every encounter like right now we're having this encounter yeah there is like maybe it's not high drama but there there is a beginning middle and end here there are like insights, there are discoveries, you know, there's bullet points, bullet point energy, like, you know, things can happen, things happen in a conversation.

1:03:59And so my challenge was like, how do I make it as like entertaining as possible? Yeah. And I, the thing that I hear there that I feel like is really useful for me is there's again, these two ways of being in your journey, where you are, there are times when, you know, when you're voting, when you're on a panel, when you're speaking to this, when you're in part of the decision-making process, you can think about how the system might need to change. You can think about how, oh, it'd be better if we had bigger budgets for these types of shows. There's a time and space to think about the circumstance.

1:04:45But then a lot of your creative energy, you have to channel in what is the circumstance that you find yourself in and making the most out of it and using it as a creative prompt. And I think what you're doing is super interesting in that way. So thanks for that. Thanks for sharing all that. Thank you. I mean, we are, we love, who doesn't love a creative constraint? Oh, yeah. Right? Like, absolutely. They're so fun. As soon as you can recognize it as that, that's a difficult thing, especially when you're laid off. That doesn't feel like a constraint. No, no, no. But it is. It was. And it produced something really interesting.

1:05:27And I'm excited to see where it goes. Thank you so much for spending all this time. Thank you. I got so much out of it. And I'm sure the listeners will too. Tell people where to start with proxy. Okay. Well, I think you should start with the Layoff Trilogy, which were the first three episodes, which is about the mental health toll of layoffs. And we also do our first proxy conversation. And then from there, I would maybe skip ahead to the most recent episodes, maybe go to Bisexual Wife Guy next. I've heard that's a top popular episode. Yeah. Yeah. And that's basically about this guy, this listener who wrote in whose wife came out as bi and then divorced him.

1:06:12And we pair him with a woman who also did that to her husband as his proxy to just sort of like get some of that perspective. And that person happens to be my former boss. that's juicy that's great I haven't heard that episode yet I need to go listen to that one thank you so much for spending so much time here and I hope we get to chat again soon yeah thanks for having me this was so fun

1:06:59All right. I absolutely loved that conversation. I had so many more things that I could ask or places I could have took it. It was just super, super rich. I hope you loved it. If you did, you're going to love YoA's show Proxy. Go check it out wherever you listen to podcasts. It's super good. Just, yeah, really different and both emotional and I just feel like you get a lot from it. So thank you so much for being on the show, Yo-A, and hope to have you back sometime. Just quickly, I'm not going to go deep into this because I think we pretty much explored it in the conversation, but the CTA we're calling Creative Campaign.

1:07:41And the idea put simply is what would it look like for you to do a project or a series of work where you're creating the artwork, music, podcasts, images, whatever your medium is, but the project is to meet your business goals, whether that is to get Patreon backers like Proxy was doing, or whether it's to sell what you do to clients. What would it look like if you tried to do both at the same time? If you tried to make selling yourself an art? I think that some really interesting things could come of that, Especially if, I don't think, I think there are a lot of scenarios where you wouldn't have to be super explicit that that's what you are doing.

1:08:27But I think it could be interesting to explore that too. How can you tell people like, hey, this is a project that's trying to be a campaign for my creative business. I think that is an interesting thing. And we're gonna explore that. I think it's such a good prompt. I'm gonna do it. We're gonna do it with a podcast. I think we're gonna do a Patreon campaign, Substack campaign, something of that nature. because I think it was so successful and interesting as a creative prompt. So hope you loved it. Go check out Proxy. Massive thanks to Sophie Miller for being a producer and editor on the show.

1:09:00Thanks to Connor Jones of Pending Beautiful for being an audio editor, a video editor, an animator, and a sound designer for Creative Pep Talk. Thanks to Yoni Wolf and the band Y for our theme song and soundtrack. Thanks to all of you for listening. Until we speak again, stay pepped up.

1:09:35Hello, this is Jack Wilson, the host of the History of Literature podcast. For the past 10 years, I've been talking to novelists, biographers, and scholars about the greatest books in the history of the world and the men and women who wrote them. like our recent episodes on Dante and Love, a starter pack of 10 Indian classics, the pop culture that influenced Sylvia Plath, and a talk with scientist and novelist Alan Lightman about the wonders of nature. Join us at the History of Literature podcast wherever you get your podcasts.