Making a Living (3Clips)

Making a Living (3Clips)
Making a Living (3Clips)

May 05 2022 | 00:50:37

Episode May 05, 2022 00:50:37

Hosted By

Stuart Barefoot

Show Notes

On this episode of the Audience podcast, we’re diving into the archives to show you an older but important episode of the 3 Clips Podcast called, “Making a Living in Podcasting.” This episode was hosted by the 3 Clips original host, Jay Acunzo with business partners Kinsey Grant and Josh Kaplan as guests. 

3 Clips is a show that focuses on the craft of podcasting. It showcases specific podcasts in each episode and breaks down their processes, three clips at a time. 

In this episode, Jay talks with Kinsey and Grant about what it takes to turn your podcasting passion into a successful career. Instead of dissecting their podcast and the process they use to create the show, Jay talks with them about their passion and career and how they’ve melded those things together. 

If you have any questions about this episode or want to get some of the resources we mentioned, head over to Interested in private podcasting? Check out Castos’ private podcasting service at And as always, if you’re enjoying the show please share it with someone who you think would enjoy it as well. It is your continued support that will help us continue to help others. Thank you so much! Never miss another show by subscribing at

Today you’ll learn about:

  • Individual strengths and weaknesses as podcasters
  • The myth of the solo creator
  • The development of the Thinking is Cool podcast
  • How they leveraged their brand for sponsorships
  • Showcasing ad content and sponsors through various mediums (including podcasting)
  • Finding a healthy balance between selling everything to being too discriminatory with ads
  • Disagreements with partners
    • Strengths and weaknesses as partners
  • Vetting creative (behind the scenes) people and building a great team
  • Self-worth as a podcaster and putting your ambitions into perspective
  • The difference between a creator and an entrepreneur



Castos Integrations:

3-Clips, “Making a Living in Podcasting”: 

Castos Academy: 

Castos, private podcast:

Castos, website:

Castos, YouTube:  

Clubhouse video: 

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Episode Transcript

Speaker 0 00:00:00 Making a living as an independent creator, or even as a small organization is challenging. So to help with that, we're gonna pull from our archives and listen in on an old episode of three clips. Another Casto original. The episode is titled making a living and podcasting. See don't even bury the lead. It was first public in September of 2021 and was hosted by J Azo, the series creator. It was produced by Andrea kin. You'll hear that episode in its entirety next, before we listen in on that episode, I wanna let you know about a way to create a private subscription based podcast with Casto. You can easily create a private pod cast for your membership site, online course, or community. The best part you can integrate it with the tools you already use through our direct integrations, learn or click on the link in the show notes. All right, let's listen in on the conversation. Speaker 2 00:01:01 Hey, it's Jay three clips is a show about the craft of podcasting of seeing the work better and differently, honing your taste and your intuition, and ultimately creating something more, resonant, more original, more you, but I'm very aware that the vast majority of podcasters and a lot of our listeners don't make a ton at this stuff. At least not yet. I've gone through this personally and only recently figured out a few things that seem to work, but after you fall in love with the craft and then work hard to master it, how do you make a career out of it? So today we're doing something a little different, an experiment of sorts. We're gonna try this on and see how it feels. We may or may not continue this, but it's a series about our livelihood. It won't be prescriptive with seven steps to profitability or ultimate guides to advertising or Patreon for podcasters, nothing like that. Instead, we want to hear the stories and the ideas of some of the brightest minds in this space and pick out one or two very specific things they do well and go really deep into that. Speaker 2 00:02:31 Welcome to three clips where podcasters take us inside their process. A few pieces at a time. Typically today, podcasters take us inside their livelihood. I'm Jay a Kenzo, and this is a Casto original series. We wanna inspire you not only to create better things, but to earn a living at it, to fund your art, your work, your message. And so today to help us, we're gonna talk to Kinsey grant and Josh Kaplan, Kenzie and Josh both came out of the business media startup morning brew, which is now part of business insider. Kenzie's actually a repeat guest here on three clips. She previously joined us to break down the show. She hosted for the brew business casual today. She occupies two different jobs. She's the host of thinking is cool. She takes listeners deep into the key topics affecting their work and their lives to encourage us all to stop and think a little bit more critically about the nuances inside those ideas. Speaker 2 00:03:29 So she's done episodes about drugs and why we do them billionaires, and whether they should exist the concept of the girl boss, the political system in the us and how we might fix. And of course, porn Kinzie is also the chief content officer of the startup that she co-founded smooth operations and creator services. It's also known as smooth ops. And that brings me to Josh Kaplan. Our second guest today in addition to working with Kinzie on thinking is cool. Josh is the co-founder and CEO of smooth, which helps run the business backend and revenue generating projects for independent creators. Plenty of those creators by the way, are podcasters. And I think Kinsey's was kind of a test show for Josh and the rest of the team at smooth ops. And now they work with other creators to build their businesses. So the creators themselves can focus on what they do best create both content and relationships for and with their audiences in this new type of episode, we won't be dissecting any clips at all. So let's get into the conversation with Kinzie and Josh Let's start here. So Kinsey, Josh, you guys are complimentary partners, ostensibly, uh, Kinzie. What's something Josh loves doing or does well that you never wanna do, or you're not good at doing. And Josh what's something Kinsey does well or loves doing that. You wanna avoid. Let's start with you. Kinsey Speaker 4 00:05:01 Ex Microsoft Excel. Uh, Josh is definitely a numbers Wiz and somebody who understands how to make models, how to run models. And they are really, really useful in valuable to a business, but I simply do not understand it. So that is something that he is incredible at that I have no interest in learning how to do <laugh> Speaker 2 00:05:21 Fair enough. Josh Speaker 5 00:05:23 Kenzie starts with blank pages, nothing that I ever do starts with an open Google doc or empty. I use templates from other projects or from other people. And the way she can start a story with a blank page, I'm just like, I, I don't even know where I would start that it I'm constantly amazed by her and by the other creators we work with, but it's just like, I, I don't get it Speaker 2 00:05:43 In sort of the trusting of the gut. Maybe it's like, I'm confident with my impulses that I don't need the, the guardrails. Maybe I don't know something in there. Um, when you both worked for morning brew and Kinzie, I know you are a journalist first and foremost, but so the two of you have both seen this kind of like very specialized division of the work where you have edit roles, creative roles, you have operations roles, business, side roles, and then <laugh>, if you're like me or, you know, uh, anybody in the creator economy, then you leave a media company or you've never seen what you two saw. And it's like, oh, all of those specialized full-time jobs, I'm now doing all of that myself. And so you talk, you hear burnout all the time in this niche. You, you know, people struggle to produce a plus creative work, cuz they're stretch too thin. Josh, I'll start with you on this. There's this myth of the solo creator. Is that not the right label for this? Is it impossible to actually be solo and build a creator business? Speaker 5 00:06:46 You can't do anything alone. That, that to me is a, a concept I've never really wanted to be a part of. And, and we've always had help. And whether it's full time or software or freelancers or something like there's always something helping you. Like if you're really doing it by yourself, you just can't be that productive. And I think there's a big difference between being a solo creator and being independent. And to me being independent means that you own your content. You own your strategy. You, you get to make decisions on, on your own turf and in independence is what we all want. Uh, so, so to work toward that, but get to do it with a team or with other people that support you is what I believe in not the solo creator. We do all different parts. You know, I, I do everything that I have to do by myself. Speaker 2 00:07:33 Right. I don't know why indie didn't stick. Maybe it's starting to, but like, so I came out of the SAS industry with company. He like HubSpot and I worked in VC. Um, and so everybody talked about indie sass or indie makers and it was very tech focused. And then I get into the creator world, everyone's saying solo, uh, you know, and it's like, or it's so focused on a personality. You forget there might actually be others involved for the ones that you admire. Um, Kenzie, are there things that now that you're doing us full time, you're not as a part of a media company that, um, it was sort of like welcome to indie mode. Like what is your indoctrination into having to do it all yourself from the Speaker 4 00:08:09 Day? Yeah, I mean, certainly it's been part of the process and it's been a, a decently steep learning curve, but I will say that the one big benefit that I think Josh and I brought to this whole independent creator and adventure that we've started over the last couple of months is that we worked for a company, but we've worked for a pretty scrappy startup. When we were at morning brew, we were still expected to do a lot of the jobs that weren't necessarily in our job description when they looked at us and said, go start a podcast. That was essentially all we got, right? So we had to figure out product management stuff. We had to figure out content strategy up. And we had people to help sell ads and do all of that stuff. But it was, it was not necessarily, um, you know, you only had one sole responsibility. Speaker 4 00:08:48 And I think that that prepared us really well for starting our own show and starting our own company or, or rather companies, uh, because we were really willing to take on jobs that maybe we had not figured out before. Uh, the best part of being an independent creator right now is that everybody wants to be an independent creator. And I think that that has created this community, this broader ecosystem of people really willing to share information. So if you don't know how to do something, you can pretty easily figure it out. And I've really admired that about other creators who are, are now labeled as, uh, indie podcasters or Indy YouTubers or anything like that. They're typically willing to help you out, which I think is, is really cool. And not necessarily something that happens when you are in a more traditional media business position. Um, you know, we talk about like trade secrets between media companies, especially when we were in email. And that just, that really happened with podcasting, um, in my experience. So there are inevitably things that crop up that you don't know how to do on your own, but I think the fact that you can ask the internet for help and get that help is really, really cool. Speaker 2 00:09:48 Tell me about developing thinking is cool. You know, where did the idea start or did the idea come after the need or the desire to be an independent creator? So how did that start and how did you start to develop it behind the scenes? Like what are the things that you both had to work through to say, you know what this seems viable? Let's, let's at least try it. Speaker 4 00:10:05 I think the beauty of the, the Genesis of thinking is cool is that it all kind of happened at the same time, which is awesome. You know, Josh and I had kind of toyed with the idea of going independent for a while, and we didn't really know when was the right time and what were the right circumstances. And it's, it's the paralysis that so many people face, right? When you're considering leaving something that's pretty comfortable is when is the right time to do it. We eventually got to the point where we had a, a product that we were really excited about. And it just so happens that during all of those months that we had kind of Hemed and hawed and tried to figure out what we wanna do. We'd all been thinking and talking and Josh and I have this really great relationship. You know, I think that like, he's one of the people I can talk to and think with in a really meaningful way, um, an intellectual sparring partner, if you will, and throughout all of these months of trying to figure out what we wanna do next and what comes next and when and why and where, and all of these big questions, we were still having those kinds of conversations. Speaker 4 00:10:58 And eventually it got to the point where we thought, you know, maybe, maybe this is the podcast, right? Maybe this is what we should talk about. We have been really, really privileged to have experienced what it's like to be a quote unquote, like online person. We have the benefit of making all of these connections with really smart people, either through work or through Twitter or through mutual for, and connections. And, um, those were really meaningful relationships to us. And so we wanted to create something that would extend the beneficial aspects of having these relationships to anybody who wanted them, right. The advantages of surrounding yourself with smart people. Shouldn't just be based on proximity. You should be able to have smart conversations, regardless of who the other person on the opposite side of the table is that you're having that conversation with. So that was, uh, kind of the core impetus behind creating the concept thinking is cool, but the idea to start a show on our own, uh, with kind of me in the creative seat, Josh and the business strategy off seat has been boiling for a while, simmering for a while. And then all of a sudden we had this great idea, um, and it just made a lot of sense to suddenly run with it. Uh, and I'll let, I mean, if Josh wants to share too, he, he kind of is behind the whole idea of like the name thinking is cool. Speaker 2 00:12:07 See, this is the, this is the beauty of doing a show with other people who are on shows all the time is I don't even have to tee it up. I can just be like, okay, Kenzie, you're the guest. But like also, you're also a host. So like just, I'm just gonna mute and I'll let the rest of the episode unfold. Perfect. Speaker 4 00:12:19 <laugh> Speaker 5 00:12:21 Faking is cool. Was something that I had played around with before morning brew and then Kenzie and I did a bit of it together where we would send an email to a bunch of friends, everybody in the two fields with the one line question, what do you think about this? And then people would reply all. And it would just become like 12 different threads and people agreeing and disagreeing and adding links and whatever it might be. And so there's always this very casual email chain called thinking is cool. And Kenzie, and I then had all these conversations that she just described. And there were so many other topics that we wanted to explore a storytelling perspective. If you look at season one, and if you look at what we're about to do at season two, there are so many really interesting topics, whether they're taboo or they're inaccesible right now that we didn't feel like we're being told in the way that we wanted to anywhere else that we could find. Speaker 5 00:13:09 And so we've done this incredible job. I love listening to the show. I there's so much of my, my heart into it, but I love seeing Kenzie create this new format. That's more narrative driven. That's less of an interview based show. Um, and, and it's just been really, really fun, but that's a bit about the backstory of thinking of school and how it's developed, but it's got a whole life of its own. Now, like seeing how Kenzie comes up with ideas for the episodes, for the different formats, for where we could go seasons and years from now, uh, it it's become a whole different beast of its own. Yeah. Speaker 2 00:13:39 Yeah. I, I mentioned, uh, before we started recording, I host two shows listeners to three clips will have heard me mention unthinkable. That's kind of like my digital baby. It's been the show I've been doing the longest. It's the one that sort of showed me what this medium could do and allowed me to play. And it's always been narrative and Kinzie when you started doing thinking is cool. You know, I, I, I started listening, not only cuz you came on three clips before, um, for your morning brew show, but also I just, you know, I appreciate your craft as an interviewer and good interviewing is a craft. It's really hard. Now you're adding this new layer, which is narrative. So let's go into this. Um, this always turns into like podcast for therapy, but creating a narrative show. Is it once more fulfilling in some ways, if you're that kind of creator and also the most maddening thing ever, cuz you're like, why am I doing this to myself? Having to add narration, having to parse the story in the tape? Like why can't I just do a straight ahead interview, which again is still in and of itself hard, but now you're adding a second art and narration. So I'll ask you, are you nuts? Speaker 4 00:14:40 <laugh> yes. <laugh> next question. No, I mean, yes. I, you know, I, I ran an interview show for a really long time and yeah, I often found myself putting too much prep into going into these interviews. You know, I'd spend too much time, I would know too much. And, and it would sometimes hamper your curiosity, right? If you have too much information, you fail to recognize the position that the listener is in. And that was a, a weird difficulty that I had to kind of wrestle with when I was hosting an interview. And, and I say, interview solely interview show. There was really no narrative, no scripting, no anything. And then I suddenly realized, you know, I love interviewing people. I'm good at interviewing people. It's something I want to continue to do, but that's only one aspect of my creativity. And I was really excited with the, the opportunity to go independent and do thinking is cool to show something else that I love to do, which is writing. Speaker 4 00:15:28 I, I love doing it. Like it's something that I have always done and not necessarily showcase in a creative way. And so to get the opportunity to showcase that has been really incredible and been really creatively fulfilling for me personally, but it is really, really time consuming the <laugh> issue with an interview show, really, you know, like the number one is booking and asking good questions and getting a good guest. If you can get a good guest, who's willing to answer your questions in a thoughtful away, you're pretty much set as long as you do your job. Right. But with the narrative, it's also getting the guest, figuring out the storyboard, trying to set aside 10 hours to write a script, doing the recording. Like there are so many other time consuming steps, but for me personally, it has been worth it because I find that I think a lot more critically when I give myself all of that time to consider the issue at hand, you know, if it's just an interview, you might not have time to think through something really complicated while you're waiting to ask your next question. And so that's what I really love about the narrative concept is that I get the time and space to talk about it and to think through it, even change my mind in the middle of writing an episode, I think that's really cool. Um, so it's been worth it for me, Speaker 2 00:16:39 That form, you know, narrative does sort of bring out a more premium feel to the show. Josh, is that something that you guys were trying to use to sell your launch sponsor when there are no downloads to the feed? Are, you know, what are you talking about? You know, you ended up with ATM Bradley as your launch sponsor. What are you going out and discussing and offering that makes a partnership worth it for a brand when it's not, you know, a massive show yet. And it, you don't have a newsletter as big as say the morning brew to entice somebody. Speaker 5 00:17:14 Oh my, my secret sauce on selling, uh, Kenzie grant Kenzie had built a brand for herself that when she announced she was going independent before saying exactly what she was gonna do, people said, Kenzie, we, we love you. How can we work with you? And that's incredibly fortunate, but it's due to Kenzie going about living online and producing content, the way that she had been over the past couple years. So with ATM Bradley, we had a warm introduction. Kenzie already had a relationship there. Uh, they, they wanted to invest in us. They knew that it was gonna take some time for the show to lift off. Uh, we also sold a pretty dynamic package of some stuff on social media, of other types of content, of bespoke content, the integrations into the show, the premium placement on the show cover art and, and it became a lot more than selling media inventory and a lot more about brand ambassador. Speaker 5 00:18:09 And that to me is another big movement that we're seeing that you gotta know what you're selling and, and within the context of Kinzie and thinking is cool. It allows us to make just a handful of really integrated partnerships with partners that really align with what we're doing and who Kinzie appeals to. And that makes it very easy. Cuz then you a couple people to say, we get it, we value you at a premium. And we know that we're gonna get a lot of value back out of this. And it's not the LinkedIn jobs at, it's not the Brooklyn ends it's brands that really, really make sense. And for season two, we've got four new partners that are, are also incredible. And what we've been again, fortunate where it's not a lot of saying about, Hey, you should work with us for X, Y, and Z. It's okay. There's already some common ground that we see value. Let's get creative with what packages we put together. So everyone feels like they're getting their fair share out of it in return. Speaker 2 00:19:02 Right? Right. And you can sell the story there's momentum or there will be, or you know, like selling, not just the totals, but also advertising to two year potential sponsors who these people are, you know, it's a premium slash niche audience, how engaged they are. I, I, I am just dumbfounded by how few podcasters seem to capture and save nice things. People are saying outside the reviews, right? Like on social media, in your inbox, like the paragraphs you are sent as a podcaster, if you're doing this right, is so incredibly impossible for most brands to, to get. It's so rare and, and creators are able to get that. Um, when you're talking about that story and you're saying, by the way, given this depth of engagement and trust that Kenzie's been able to build, we are going to help you participate in that you're saying custom content is a part of that. These bespoke things that aren't just ad spots that you sell, you know, on and on and on added infinitum, what are the custom things or are you saying we're open to custom, let's discuss, Speaker 5 00:20:04 But we separate the standard inventory from the custom ideas, but it's all wrapped into one campaign. Uh, uh, Kenzie, should I use examples for the upcoming season? Oh yeah. Okay. We are working with a company called Pluto pillow, which is a pillow company. What would've thought, uh, Susanna founded this company. She was on shark tank. They're blowing up right now and you take a quiz and you get a custom pillow. So when she story tells to us, her brand, we go, okay, cool. We've got the podcast, but the pillow's a pretty visual product. Can we do AMAs with Kinzie while she's lying on her pillow, answering questions and talking about the pillow at the same time, there's a custom quiz. So you can get that custom pillow. Can we incentivize quiz completions with our merch with a special bedtime gift basket? Can we get collateral on the actual webpages? Speaker 5 00:20:55 So I, I look at it, I kind of move the puzzle around and I go, all right, like we understand what you're trying to do as a pillow company. And there's all these interesting attributes, Hey, you're on shark tank. Should we, you know, do another piece of content around at and how you're pitching the company for our thinking as cool audience. We're not doing that in particular, but I, you, I start to have fun putting these things together and understanding what can we do? What's in the realm of possibilities. We're not gonna go crazy because we're, we're still making journalism. Kenzie's gotta focus the majority of her time on creating her stories and not just being a creative studio for the ad partners, but that that's the song and dance. And when it's only four partners, we're able to actually get some really good stuff going. Speaker 5 00:21:33 Um, so that, that's how I expand it from there. And, and we also have to understand that the podcasting medium is great for that visual billboard for that intimate advertisement. That's read by Kinsey, but we have our newsletter. So we get to see better. Clickthrough there. We have social. So we can actually drive people and comment and bring them in and get a little bit more attribution through those areas instead of putting so much pressure on, Hey, can we track how the podcast ad performed? Right? I'd much rather say, Hey, how did our campaign perform overall? Did we get the results that we wanted? Speaker 2 00:22:05 Is there a blurring of the line in your mind, not out in the world, Kinsey, but when you're, you know, thinking about your role in all this, your business, your desire to be, uh, to have an impact, uh, you know, clearly you're doing this because you have a love of the craft. You have a love of creativity and you're trying to help people. Um, how do you make sense of like how close it becomes to, you know, on one extreme, this is not you, but on one extreme, you can become a total shell. And it's like, I will sell anything and everything, including my name and the logo I wear to, you know, any kind of video appearance all the time on my chest. That's one extreme. Uh, another extreme is I'm a reporter, I'm a journalist. And I happen to be reading ads for part of this inventory. How do you start to navigate that middle ground? Where it's like, you know, Josh just said, we're not just selling the audience. We're in a way selling Kinsey. Speaker 4 00:22:52 I don't think we give journalists enough credit. And, and I mean that, so sincerely, you know, I think people are obviously flawed. There are outlier situations where you see moral lines blurred and that's a problem. I, I don't disagree with that. It's I think we can all agree that like insider trade is bad, right? But I think the idea that journalists can't do anything that is capitalistic or even just business minded is really flawed and, and really messed up. I, my first job outta school, I was a reporter breaking news reporter. And I remember so clearly signing paperwork saying I wasn't allowed to invest in anything other than the stock of the company, for which I worked. And that's a pretty commonplace requirement for a lot of newsrooms across the country. And I think that, yes, you know, there, there are crooked journalists out there. Speaker 4 00:23:38 There's crooked everyone out there, but I think we need to give people a little more credit. I am capable of com compartmentalizing. I can recognize when I'm in journalism mode, I am trying to seek the truth. I have a different relationship with truth than most everyday people. And then I can also recognize the times when I am doing something that is for money, right? When I am hosting something for money, when I'm doing branded content, when I'm writing an ad, those are different experiences. And I think to suggest that journal us who are incredibly bright people for the most part and curious people and thoughtful people to suggest that they're incapable of doing that is just kind of a backwards way of looking at it. And I also think that the idea of a journalist only being a journalist is also a little outdated. People are dynamic and we are evolving all the time. Speaker 4 00:24:22 Journalist is certainly the first descriptor that I would give myself. It's the one that I care the most deeply about. I am just a naturally curious person that has what, what led me to this career path in the first place. But I'm also a lot of other things I am running business. I am trying to make myself a solid living. I am trying to help other people to make their own businesses and empower them to ask questions and start their own thing and go independent. And all of those things don't have to be mutually exclusive. I can be all of that at once. Um, just like any business person can be whatever they want at once. I think journalists have often kind of been typecast into this one specific barrel, right. And that's not necessarily fair. So that is the, the attitude that I take into running a business. It also has some journalism a minute. I don't think you have to only be one thing at a time. Speaker 2 00:25:10 I showed up to the brand world because they said I could create for a living. I wanted to be a sports journalist. Everything in my collegiate career was orienting around that every internship, every side project was I was heading down that path. And then when I got into marketing, um, you know, I, I felt like in some ways I started to thinking, well, maybe I sold out. And then another voice in my head, crept in maybe through great mentors who said, you can believe in the company you work for and write on their behalf and view the world through the editorial lens that they have. And they're selling a product or service instead of ad space. Like it is possible to be a capitalist and be a journalist or a creator or an essayist, you know? And I think a lot of what we're doing now is, is what I'd bucket as creative nonfiction. Yeah. It's, it's a perspective that we carry of the world, but we're not making it up either right there. You cannot separate the creator from the created work. Um, you're not just an empty vessel, collecting facts and distributing those facts around the world. And so that applies everywhere. That applies to the commercial side that applies to the editorial side. It's like, if you trust me to bring you a story through this angle, then you are also hopeful. Hopefully trusting me to bring you messages from sponsors or custom content through those sponsors. Speaker 4 00:26:19 Yeah. I, I completely agree. And I think that as long as you're really transparent about where you are in your relationship with the people who are consuming your content, they're going to you to trust you. People know when I'm reading an ad. There are, there are sound cues, there are visual cues. There are indications that this is something different than my traditional reporting. So as long as you're really transparent about that, I see no problem with it. Speaker 2 00:26:50 What's something that you both have disagreed on as partners. Um, there's been a lot of like, I completely agree down the line, which is great, cuz you are partners, um, being complimentary players, of course you're supposed to help to kick at ideas and solutions and improve them in some ways. So, um, you're both interested in the creator economy. You're both trying to build thinking as cool. And we're gonna talk about smooth operations and creator services in a moment where you're trying to serve other creators. Where do you diverge and, and how have you come at that disagreement? Speaker 5 00:27:24 We, we disagree on, on some of the creative stuff. Yeah. Which then allows Kenzie, I think, to make a better journalism product. Speaker 2 00:27:32 Like, like what, what do you mean? Well, Speaker 5 00:27:33 One example was like the billionaires episode should billionaires exist, which is a much like flashier question than the nuance of what she put out. Um, but we, we had some disagreements about that and then we still do we talk about it publicly and behind the scenes and it's really fun. And that that's where we get to have fun. And just talk about the topics we're focusing on within thinking is cool. And then at an operating level, yeah. We, I think the last big disagreement was, should we send two newsletters a week or one <laugh> and then we had a thoughtful conversation around that. Kenzie put up a Twitter poll and I, and I was right and I really happy about it. I love being right. No, no, but that, that was one of like the more tactical disagreements and we have disagreements all the time, uh, like frequently, like there's a lot of friction that is the whole point. Like that is why we have different perspectives on things. But when we come to like an interview or something like that, we know that like showing United front is better, but I, I would say by and large, like we're not always just like saying the same thing to each other and, and it's also good. Like that way we're not just like believing our own smoke. Speaker 4 00:28:34 Yeah. Getting high. It, I would, I would also add to that, that getting good at disagreeing with people, for whom you care deeply is a really underrated skill. Speaker 2 00:28:43 Oh, amen. Speaker 4 00:28:44 I think we often equate disagree agreement with some sort of like vitriol or like a, a thorn in the side of your relationship, like a thorn in the side of this friendship. And that's not what it is like Josh and I have gotten good at disagreeing with each other and getting past it because we do it all the time. But we do it all the time on a scale where it's really manageable when we say like, I don't think billionaires should exist. And Josh says, well, I do. That's a disagreement. Each have the evidence that we have to, to back up that claim that we're making. And we've gotten good at getting through those conversations in a way that leaves us both walking away from the conversation smarter. Even if you are wrong about something like I was wrong about the newsletters, or I think I was wrong about the newsletters. Now we had the, the time and space to think through that, uh, in a meaningful and thoughtful way. Uh, and that's like kind of at the core of what we're doing with this entire project with thinking is cool in General's just making people feel more comfortable with having a hot take disagreeing with someone that you care about and walking away from it thinking, wow, I'm so glad that we had that conversation. I feel smarter even if I was wrong. Speaker 5 00:29:43 Yeah. And there's another type of disagreement, which is, is marginal disagreements. That's saying, Hey, you know, this is the partnership I wanna propose to that brand. Here's what I think. And Kenzie's like, actually like, no, like I don't wanna do it that way. I wanna do it this way. I'm like, oh, you're right. That's a much better idea. I'm glad I got your hands on that. Or your eyes on that. And <affirmative> that, that makes our output significantly better to say, I'm gonna put what I think is best. Get somebody to critique it. And then when you keep on going forward, doesn't have to be completely opposite directions. Speaker 2 00:30:12 Yeah. There's a necessary tension that a partnership brings that I think is even healthier than in some ways than like a mastermind group. You know, like I don't have an operations partner. I do have a mastermind group and it's like, these people are awesome allies in helping me improve my thinking in poke holes in it, cuz otherwise alone. It's just every idea I have is the best idea I've ever had or the worst idea I've ever had. It's just no middle ground. And, and it's binary I'll do it or I won't do it. And then having someone who can vet stuff with you, you know, improves the work. It, it helps you serve your audience, helps you build your business, but there's a level of accountability and ownership that a partner brings that a mastermind group does not. And what I've seen as a, as an individual creator over the last say five years is this movement from I'm truly alone. Speaker 2 00:30:54 And maybe have some mentors that I talk to once in a while to this movement, to community, community groups, mastermind groups, cohort based courses to now, now everyone's well, not everyone, a lot more people are talking about operator partners. And you know, I mentioned, I worked in VC. This was the question that everybody kind of shrugged and gave basic advice for people would go, how do I find a co-founder? And the answers seemed to be like, you get lucky because you were surrounded by folks for years in your network that you already trust. Or you have to go on a really long dating period, even though, you know, you need a co-founder right now. And so again, I, I acknowledge it's a bit of authority question, but if you're a creator and you're aware, I kind of need an operations partner, what is your recourse? How do you come at that problem? Speaker 4 00:31:40 I think that part of it is just recognizing what your and your weaknesses are. Uh, Josh and I were lucky to have worked together for a while before we wanted to do something on our own. And in that time we both got really good at recognizing not a, not only what we're good at, but I think more importantly, what we're not good at. And we really lucked out that those were kind of like complimentary forces. Um, but that is also just part of the, the name of the game that we were talking about before with independent versus, um, you know, like solo creators. You don't have to do all of these things by yourself. There are now ample resources for whatever you need to get done as an independent creator, like so many places to go startups and, and like accelerators and writer groups and things like that. So I think it's, it's just recognizing what you would consider to be your own shortcomings and trying to find people who will give you honest feedback on what you need to work on, uh, whether that's operationally or creatively and seeking it out, uh, based on like those, the list of whatever those things are, um, or you can go to smooth operations and creator services <laugh>, uh, which, uh, we are, we're happy to help out with, uh, all of your creator needs. Speaker 2 00:32:48 <laugh> Josh. Same question. Like if you're trying to push forward, uh, you know, short of, let's say you do end up eventually going to creator services. What are all your fail? The temps that you're gonna have to go through, uh, before I realize, oh, I actually need smooth ops. No I'm but in, in, in seriousness, how would you advise a creator start to think about what they offload and how they find someone else? Cause it's, it's maddening you, your fingerprints are all over everything and you're not sure what to keep and what to offload. Speaker 5 00:33:17 Oh, it's a, it's really hard. And it depends on the stage that you're in. I I'm really big about knowing what your strategy is, cuz then you can graph other opportunities and things on your to-do list against it and say, does this help my strategy? And then you look at it and say, okay, here are the three most important things. Number one. And number two, create content, engage with my audience. I'm amazing at that. I don't want anybody's help I'm things are going great. The third thing, which is monetizing, I just don't really know who to go to, how to do it. So then you've identified the whole, and maybe you need an ad agency. Maybe you need to turn a different service on digitally who, and then you say, okay, I did that for, for two to four months, whatever it might be now I'm ready to add the next part to my content, offering to my business, whatever you want to call it. Speaker 5 00:34:11 So I, I want to go through things like that, very tangibly and specifically, and understand what you're focusing on, especially in this creator world, when you have so many options, which platform, which story to tell which thing to do, you gotta boil it down to a couple things that you really, really prioritize and then build on over time and then find the partner that has a particular affinity or specialty in filling that gap. So it, as much as that might be like a non-answer and, and I can tell you what we like to do it smooth operations as an example, but it it's, it's really that type of thinking that I would apply to anybody or see if they can simulate and say, oh, okay, I'm scratched it enough. It's not just that I need help. It's that I need help with this. Speaker 2 00:34:55 Right. Well, well, let's talk about vetting the other side, so to speak. So, uh, first time I built a team of writers and, and creatives was in-house at a startup. I had done the job a while and then so I had the advantage of having to do it. And then slowly as the startup grew, became the head of the team. So I started to hire for it and I'll never forget the first writer I tried to hire. I almost didn't. And I had a great boss who set me straight. The, the mistake I almost made was I looked at their resume and they, you know, they didn't have a fancy cut, all these things that my prior job at Google taught me to look for. I was looking for, and the guy basically said, okay, put aside the resume. Here's the writing sample that this person submitted, just read it, just start there. Speaker 2 00:35:36 And I was like, oh my God, this person is amazing. Like they're bartending in Florida. And they don't, they have a G E D, but like unbelievable writer hired one of the best decisions I ever made. Almost one of the biggest mistakes I ever made. Thank God for my boss at the time. And so I was bad at vetting creative people for a while and then got better at it. And, you know, moving to projects quicker in the process than conversations like these kinds of things. Um, Kenzie, you've now worked with Josh for a little while. You have an idea of like how he's been helpful to you. And so you, if you were to go out on your own, again, would be better at this. Ostensibly, what do you ask someone who would like to work with you as an operator partner? How do you vet the person whose work is not so public where you can read a writing sample, for example? Speaker 4 00:36:22 Well, I think that number one, it's just evaluating this person based on potential is a big part of trying to figure out with whom you would wanna work in the future, regardless of what you're doing. We're obviously approaching things from the creator economy side of the conversation. So typical, the people with whom we would work have some sort of portfolio, right. They have either an online presence or a really good idea. And they're great. Speaker 2 00:36:44 Oh, no, I'm sorry. Yeah. I'm sorry about that. I, I meant if you had to hire, if you were the solo creator, you were the indie creator and you wanted to hire an op partner. Speaker 4 00:36:52 Okay. So what am I looking for in a Josh? Speaker 2 00:36:55 <laugh> how do you even, yeah. How do you even vet someone if Josh was an independent and you were an independent and you cross each other's pass and you're like, you know, there might be something here and Josh is like, yeah. Kinsey, I've listened to your shows. You're awesome. And you're like, yeah, Josh, um, you're behind the scenes. How the hell do you have that, that Speaker 4 00:37:11 Person? Right. Okay. I think the greatest question to ask is where do you see this going? And I, I don't mean like where do you see this part in going and think, where do you see my brand Kinsey grant? And my show thinking is cool. Going, what is the, the number one thing that I should be doing to get in front of the right people, based on my specific personal goals that tells you a lot about a person in terms of strategic creativity and imagination. And that is, you know, a lot of the conversations that we've had building smooth ops is trying to figure out where can we take creators based on the experience that we've already had. We've built newsletters, we've built podcasts, we've worked with YouTube thing and we've done, we've done all of this stuff. How can we get as imaginative as possible with other creators to think about where they might go next based on their, if they're really, really good at X, what can we do to get them to Y and that's been, been really important. Speaker 4 00:38:06 So I think if I were coming across somebody who certainly does not have any sort of a, a digital portfolio or online presence or anything like that, I would ask where do you see this going? And then how do you get there? How do you get me there? How does bringing you onto this team get me or faster, or in a more strategic way. That would be the number one question. Um, and I would just look for imagination and look for creativity and look for somebody who thinks outside of the box, because it's really easy to get like a freelancer to handle your bills and stuff, right? Like that, that's relatively easy to figure out what I need is somebody who can compliment my vision, my ambition, in a way that will get me where I wanna be in a, in the right way. Speaker 2 00:38:45 Josh, when you're looking at a creator, uh, aside from maybe the size of their audience, what are the other things you're looking for that makes you think they actually would be a perfect fit for smooth ops or in general? They're just somebody that you would bet on. Speaker 5 00:38:58 We're we're trying to figure that out right now. We launched smooth ops last Monday, which seems like a decade ago. Um, and we've been thinking about it for a while for, for the majority of this year, but it's a really hard question to be like, what is your methodology for generally believing in a creator? And then more are specifically for smooth operations as a small team with, with, that's not trying to take on the entire creator economy at once. And, and I actually don't really care about the size of the audience when it comes down to it, because right now things can grow so fast. And, and I wanna look at things over a longer time horizon. To me, it's are you a truly talented storyteller? That's really actually hard. And again, I, I admire Kenzie greatly for being in this category. Um, the barrier to entry to creating content is so low, which is incredible, which is awesome that anybody can have a shot at this, but it is still a craft that you have to hone and that you have to really, and, and day in and day out get better at. Speaker 5 00:39:59 So it's, are you obsessive about your storytelling? And then the second is, are, are you in it for the right reasons? Like, are you here to work hard and to show up? And if you've got a to-do list and I've got a to-do list, or we both going to follow through and hold ourselves accountable and are we gonna have fun doing it together? <affirmative> to me, those are the most important things right now. Uh, there's another question around, what is your content about who is your audience? Um, that really depends again, uh, as far as is it a niche that can become very, very valuable? Is it a really random and obscure and might not be that targeted to focus that that doesn't happen that often? Cuz the internet like every niche is massive. Uh, but, but I do like to look at that and just understand like what is the content arena that they're playing in? Are there other really big competitors? Can they be the best at what they do? So those are the questions that I started to ask myself. But I think if, if you asked me again in a couple months, I'd have a, a completely different answer. Speaker 4 00:40:57 Yeah. I think that it's important to point out that there are a lot of pretty granular questions you can ask when you're preparing to enter into a potential partnership with somebody. But I, I would also say like, just to add on to what Josh said, and I think also what I said, like trust that is, is so easy to forget. You know, if you're trying to think about just what comes next, what your next big strategy is like, what your next big meeting is, what your next big sales pitch is. You have to trust that the person with whom you're entering into a partnership is going to have your best interests at heart, whether you're the creator or the operator. And I think that that is often, um, undervalued. When we think about evaluating business partnerships, trust should be at the center of all of these conversations. Speaker 2 00:41:46 What in your estimation would you tell podcasters specifically? So now we're speaking solely to the audio audience of three clips here, what do they bring or how do they figure out what they bring when they're not just able to cite a giant download total? Because I think everybody suffers from a little bit of like kid brother syndrome, kid, sister syndrome is like, I'm the little sibling, but I wish I was the big one. I wish I was bill Simmons. I wish I had that level audience or even folks looking up, you know, at what you're doing Kinsey. It's like, I wish I worked where she worked and has, have, have the personality that you have, have the audience and the follower account that you have. A lot of people are starting a little bit further down the ladder where they're looking up at others and they're like, I wish. And I think that causes them to maybe focus on the wrong things. They're all trying to be mass market products and we can't all be, and shouldn't all be how would you help a podcaster start to sort of analyze their work and look for what they're actually doing? Well, cuz I don't think we're able to do that on our own. Speaker 4 00:42:42 Yeah. I would say if your sole ambition as a podcaster is to be another podcaster, then you should probably get out of podcasting. Uh <laugh> that that's not the reason to do it. You know, it's, this is not necessarily an easy line of work. And I know that everybody says their job is not an easy line of work and they're probably right. Nothing is easy, but podcasting is tough. Like it's, it's doggy dog out there. It's really hard to gain traction. It's really hard to get what you want out of this world. And I think that if you're only ambition is just to emulate someone else's success or their pathway to instead of carving your own, it's probably not gonna be a worthwhile pursuit for you. You're probably going to be disappointed. You're setting yourself up for disappointment. So my advice would just be to focus on the reasons why you're creating content. Speaker 4 00:43:28 This was being my advice to anybody, whatever it is that you're creating, but podcasting, especially it's a crowded field there, lot of podcasts out there, but the thing is there aren't that many good podcasts, you know, like if you are really, really focused on what you're bringing to the table that is new and that is interesting and that has never been done before. That's what's going to set you apart. So take the time to really address what you're doing. And if you say, you know what, I'm creating, whatever the Joe row experience 2.0, at least be honest with yourself about it and say, what can I do differently? What can I do to set myself apart? That's going to be a really useful evaluation. Um, but just think about it. Like what are you bringing that no one else has heard before? If you haven't answer to that question, you're probably doing something right. And if you don't then maybe you should reconsider. Um, and also just be specific, the more specific the possible or the more specific, the better, um, has kind of been like my, my guiding mantra <laugh> in recent years because it never hurts to offer specificity, especially when you're trying to talk to potential operating partners or sponsors or anybody who doesn't understand what your creative pathway has been. If you can be specific about where you've been and more importantly, where you're going, where you see your potential, that's going to help you so so much. Speaker 2 00:44:44 When you think about the future of smooth ops of the audience, you're trying to serve of, you know, your work in this, uh, creator economy, whatever you wanna call it. Maybe you could each pick one here, but as we close Kinsey, what's something that you feel is currently broken or is a myth that you're out to solve that if, if your work is a success among other creators, that this will get better or go away. Speaker 4 00:45:08 Ooh, I love this question. Uh, I think that the, the number one piece of wisdom that I would hope to impart upon the creator economy is that it's okay to not have it figured out, but it's not okay to not have a plan to figure it out. I think a lot of people kind of blindly stumble into the creator economy because they see all of the shiny parts of it. You know, you see the Instagram, I going on these lavish sponsored trips and getting free PR packages. And you see these really famous writers who suddenly have thousands and thousands of subscribers on sub stack, but that's not necessarily what it's like in reality. It doesn't mean that you are never going to get to that point. But I think having kind of no, no strategic idea of where you wanna go. I, as a creative is not gonna do you any favors. Speaker 4 00:45:54 And that doesn't mean that you need to have a business degree. And to, like I said about Josh before, figure out everything on Excel and build out all of these financial models. But it does mean that you need to have an idea of where you wanna be, where you wanna go and some semblance of how you're gonna get there, find people to help you get there by all means I a million per percent encourage that. But I would just say to all creators, you need to have some sort of an idea of where you wanna go and how you wanna get there because it's important. You're not just gonna all of a sudden become bill Simmons overnight. You're not gonna become, I don't know, insert any fashion influencer here, right? Like overnight, you're not gonna be Mr. Beast overnight. It takes a lot of time and a lot of effort and a lot of strategy. So be prepared to take that strategy into account and be prepared to be an active participant in figuring all of that out. You, you are in the driver's seat. That is the number one best part about the creator economy. So take it to your advantage and, uh, kind of carve your own path. Speaker 2 00:46:49 The difference between a creator and an entrepreneur perhaps is the difference between working sole in the business and also working on the business. Um, Josh, same question as we close out here, what's something you see a lot you're frustrated by you think is wildly broken. That it's it's time to address and solve Speaker 5 00:47:06 It. It's central to the smooth operations idea that all of the VC back software, all of the nice Ts from these big social media platforms is not going to totally transform the creator economy. This is a very new space with different org charts, with different types of partnerships and it makes it incredibly exciting to be a part of it. And we all need to bring different creativity and understand how we all look after our own ends and, and come up with a really good business model for these types of businesses where Kinsey can be the CEO and the creator and, and continue to do all the things that we preach. So that that's why we're starting this business. We don't know where it's going to be in 5, 10, 15 years, but I really believe that instead of the creator being a cost to the media company or being completely taken advantage of by the Facebooks of the world, that that we can create sustainable businesses that are on different platforms that have different revenue streams. Speaker 5 00:48:07 And, and there's a lot of work that needs to be done to actually fulfill that idea. Uh, and right now it still could be considered a myth or, or just an idea. But if we can build a couple of these businesses with a couple really talented people, I'll say we, we were right about something and we know how to make the internet, and we know how to make these tools work for us rather than the creators working for them. Uh, so that, that's what I wanna see come true. That's the hypothesis that we're working toward and, and it's gonna be really fun to play it out and get to talk to people like you and get, you know, you got no idea where it's gonna go and we might change along the way, but I wanna see that come true right now. Speaker 2 00:48:48 Thank you so much for listening. You can find all episodes on our website and support the show by sending a friend to that site at three clips, This episode was produced by Andrea Moskin. Our music was created by Tyler Litwin. My work can be, including my narrative podcast about creativity unthinkable, along with my books, newsletter and other projects, three clips is a Casto original series. As a tech company. Casto believes that podcasts are about going deeper in a world. Trending shallow, deeper with your topics, with your stories, and of course, with your audience. So they provide tools to help podcasters do just that. Most notably they have tools to help you private podcast. Maybe you are an independent creator and you'd like to charge for some bonus content or just create something for your subscribers alone via your email. Well, you can create a private podcast just for them, or maybe you work in house as a marketer or head of communication. You can create something solely for your VIP customers or just your internal. You can learn more about all the tools provided to podcasters from Casto, including their private podcasting suite of That's CAS And as always every link I'm mentioning is found in your show notes. Speaker 2 00:50:08 All right, that's it for this episode, I'm Jay Kenzo and I believe making meaningful work is not about who arrives it's about who stays. So thank you so, so much for staying with me and I'll talk to you every Monday with a brand new episode of the show until then keep making what matters. See you.

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