Skye Pillsbury Episode
[00:00:00] Skye Pillsbury: Hello,
[00:00:10] Chelsea Riffe: hello everyone and welcome back to In My Non Expert Opinion. It's your host Chelsea Reif and as you probably know, I love podcasting, right? I've had this podcast for almost seven years now. It has been my labor of love. It has been my first child. It has been the longest relationship I've ever committed to.
[00:00:29] Chelsea Riffe: I even turned it into my career, teaching people how to launch and monetize their podcasts. So I think, you know, podcasting and I are pretty much best friends. What's interesting about my job is I'm definitely up to date on trends and what podcasting is doing for people in the space and where investments are going into audio.
[00:00:47] Chelsea Riffe: But when it comes to like really behind the scenes of what's going on at these bigger tech companies and what's really happening with audio in the next three to five to ten years, those are things that I'm not as aware of. So as I started to think about the [00:01:00] next level of my podcast coaching and how I'm helping people, I was like, I want to be more on the insider baseball world, right?
[00:01:06] Chelsea Riffe: I want to know like what's really going on behind the scenes. So I started listening to this podcast called Shameless Acquisition Target. And it's by a producer that actually created this whole podcast. Basically, it was a bit meta, kind of comedic, but for real project of like, can my podcast get acquired?
[00:01:25] Chelsea Riffe: So she was showing all the behind the scenes of how the podcast actually get acquired, right? So you know how Dirty John, which was so popular on Wondery, became a show? Or how Call Her Daddy's Alex Cooper just launched a whole new media network with her fiancé called Trending? Like those are the things I really wanted to know.
[00:01:41] Chelsea Riffe: So that whole podcast, shameless acquisition target started to really prompt me to be like, this is really cool to understand how media companies make their investments to understand where the future of podcasting is going. Then through that podcast, I found this newsletter called the squeeze by Sky Pillsbury.
[00:01:58] Chelsea Riffe: Sky basically [00:02:00] is like the Barbara Walters investigative journalist of the podcasting world. And I thought it was so cool to see her insights and reporting as a real reporter, right? Not just like, oh, this is a fun trend I'm going to post about or here's some anecdotal evidence I'm using. She actually goes full like dateline with her podcast investigations.
[00:02:19] Chelsea Riffe: So she's emailing media companies for quotes, she's fact checking, she's asking sources, she's referencing her material, and I was like, this is really cool, I've never seen someone do this in the world of podcasting. So the more and more I read her newsletter, I was like, I have to have her on the podcast so she can talk about how she got into this and show that maybe sometimes being a podcast host isn't the thing that you want to do, but maybe being podcast adjacent, like being a reporter or behind the scenes could work for you.
[00:02:48] Chelsea Riffe: I think Sky does such an excellent job with the squeeze and shows you that. Sometimes being talent on air isn't the thing you want to do all the time. It could be that your love is for podcasting, but you like writing [00:03:00] about it. So today we actually discuss where her love of podcasts came from in pop culture, as well as how the squeeze was birthed.
[00:03:06] Chelsea Riffe: And we talk a lot about content creators putting their work out there. What excuses do we tell ourselves? What limiting beliefs do we have? What are all the reasons why we're not doing what we're doing, and how can we just start creating without that fear of being cancelled, or being seen, or being judged?
[00:03:23] Chelsea Riffe: We get really, really into that topic. And she also shares her desires outside of the podcasting world, and her love of media, and how she got into this specific niche. What's interesting too is you all know I've been teasing like a second podcast or a sub stack or a newsletter. Like I just don't know which platform I want to put this energy into.
[00:03:42] Chelsea Riffe: And since Sky has such a successful sub stack, I turned the tables on her a little bit and I was like, I need to know how you built your sub stack from scratch. She launched a paid channel and she has amazing dedicated subscribers. So if you're a content creator, that's really been trying to understand if sub stack could work for you.
[00:03:58] Chelsea Riffe: or any type of [00:04:00] exclusive content or paywalled content, then this is the episode for you. She breaks down numbers. She shares how much content she put out before she put up a paywall. And my favorite part about what she said about her paywall was I put out the disclaimer that I am not doing this under the guise of like, I'm going to put out four articles a week at 1500 words and that's what you can expect with this package.
[00:04:22] Chelsea Riffe: She put up the paywall to be like, you are supporting me as a content creator. And the amount of fact checking and research and journalistic integrity I have, I would like to be supported financially for the quality of content I'm putting out. So if you're someone who tends to look at money in exchange for time or pieces of content, like I can only put up a paywall if I deliver four pieces of content weekly, and you're trying to shift that perspective, then you'll definitely want to tune in to hear Sky's POV and how she made Substack work for her.
[00:04:51] Chelsea Riffe: I love this episode. It's very inside baseball. It's very meta. It's like two podcast people talking about podcasting on a podcast, [00:05:00] which, to be honest, is one of my favorite conversations these days. I like getting that meta. So if this piques your interest, then definitely keep listening. And just as a note, if you want to launch your own podcast and you're just like, I truly have no idea where to start.