Inside Podcasting - August 14th, 2019

Inside Podcasting (Aug 14th, 2019)

* Special Issue: Transcript of the first episode of Inside Podcasting *

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Hello Readers!

Today I uploaded the very first episode of the Inside Podcasting podcast! I was alone in an Orlando hotel room but I dropped that sucker into my feed and off it went. Nothing short of MAGIC, people.

In this first installment, managing editor Kim Lyons interviews me about the making of this podcast. We discuss how the show came about, why I had a crisis of confidence during a family vacation, the rookie mistakes I made, and when I’ll feel like I’m an actual podcaster.

I’ve included a transcript of our first episode below, but I do hope you'll check it out in podcast form, too. I would love to hear what you think of this episode. Please tweet your feedback to me @SkyePillsbury or email me at

Thank you! Our readers RULE!


Note: This interview has been lightly edited for brevity Managing Editor Kim Lyons: 
So, Skye, you've been working on this Inside Podcasting podcast for a long time it feels like. You've finally got the episodes wrapped. The interviews are done. Everything's polished. You're ready to launch these episodes into the world. How are you feeling about everything? Are you excited to see the reaction? How are you feeling right now?

Inside Podcasting writer and host Skye Pillsbury:  
I am. It feels, I have to admit, a little surreal. I think that when I very first had the idea to do this podcast it felt very theoretical. I mentioned it to someone that we work with, and he mentioned it to Jason Calacanis — who's our boss. Within 24 hours of mentioning it, it was a real thing. But, even at that point it didn't quite feel like it was actually going to happen. So, it feels — at this stage when we've recorded all the episodes, and we're still in production mode — but, it feels a little crazy. I still can't quite believe that it's going to happen.

KL: Yeah. Well, I think once you get Jason involved it goes from 0 to 100 pretty quickly. Once he's on it, it's going to happen.  

SP: He's made a decision.

KL: He made a decision, and execute! Do it. 

KL:  Let's talk a little bit about how Inside Podcasting the podcast came about.  So, you had this idea.  You wanted to interview podcast hosts about podcasting.


KL: What were you envisioning, what the conversations were going to be like, because having listened to them, every one's different. There's not one uniform interview. It feels like everyone's got a really distinct personality. They obviously bring different things to the table. Tell me a little bit about how it came together — how the idea came together, and sort of what you were envisioning before you got started, what it was going to be like.

SP: Yeah, well I agree with you that every episode feels really different. And, in a way they all feel like a completely different baby that we're producing. Every episode is that way, but, that's what I was hoping for. I'm so glad to hear you say that because I really wanted it to feel like a range of different voices. I made sort of my dream list of who we would bring on the show, and that was what I did right after those 24 hours in which Jason said, "Yes.  You can go ahead and do this." I made this list, and I started reaching out to people. I think it says something about this industry that almost everyone I reached out to said, "Yes.”  

The people who didn't say yes had good reasons for it, and one of the people from one of those podcasts has actually come back to me now and is interested in moving forward. Everyone was really open to it, and wanted to be taken along on this ride. They knew I was new. That also was scary because once you've booked Madeleine Baran from In The Dark — you can't really go back on it.


SPThere's no turning back. 

SP:  There was actually a moment after I had booked a few of the hosts, and I was thinking about this earlier today — I was with my husband. It was spring break. We'd gone somewhere for the weekend with our kids, and I was reading this book by Terry Gross, which is all about how to interview people. It's also just a transcript of a lot of her interviews. So, I was reading that as part of my nerdy homework and trying to figure out how to do a good interview.

There was one moment when I just looked over at Don, my husband, and I said — I literally had tears in my eyes — and I said, "I'm not sure I can do this."  I want to be able to do it, but it's such a high bar — to know how to bring people out of their shell. I just had this moment of... really, it's fear.  I would think that a lot of podcasters can probably relate to that.

KLFor sure.  

SP: Once you decide to do it, it sounds exciting. But, then when you're actually on the eve of sitting down in front of a microphone and talking to another person who you've never met — and, in my case they were all remote except for Jason — it feels scary.

KL: How did you prep for those?  I mean, you were feeling maybe a little bit intimidated or a little bit wary. Obviously everyone's on board, and they're interested in doing the interview.  It's not like you had to chase people down, right? But, how did you prepare for the interviews? Was there something that you did to get comfortable? I know whenever I do an interview, I try to get familiar with the person, but not over-prepared. You just want it to sound like a conversation, right? So, how did you get ready? Other than having an almost-meltdown on spring break?  How did you prep for the conversations?

SP: You know, it's funny you should say that, because I have thought to myself that I think I over-prepared a little bit. While I was doing this, that was the one thing that I felt like I could control. It was like, okay, I can't control necessarily what happens in the interview; but, I can control how prepared I am. So, I read everything.

KL: You think you can control it.

SP: Exactly. I was up to my knees in YouTube videos — and, of course listening to their podcast. That's a necessary thing, which I wanted to do anyway, of course, if I hadn't listened to every episode. Then I would write down my questions, though, especially towards the end I wasn't always looking at my questions. That felt like a security blanket.

I will say that a lot of the people that I have talked to, even people that I interviewed on this podcast, said they write down their questions. I think Jessi Hempel said she writes down her questions because that helps her think through what she's going to ask, but then she never looks at them during the interview. 

I'm probably not quite at that stage where I don't look at them at all, but I did get comfortable with it — more comfortable with it toward the end. It's this fine line where you want to be prepared, but you don't want to feel rehearsed. And, you want there to be surprises in the discussion — things you didn't know.

KL: Right.

SP: That's the whole point. And, I also think that there's a different dynamic when you go into an interview, and you're looking at your questions versus going into an interview and just knowing, trusting your own curiosity. I think I might be stealing those words directly from something that Jessi said to me. Trusting your own instincts. You are genuinely interested in this person. If you're not interested in them, don't interview them.

KL: Right. Why are you interviewing them if you're not interested?

SP: Yeah, why are you interviewing them? So, I definitely only brought people onto the podcast who I knew I would be excited to talk to anyway. Hopefully, that comes through.  

KL: Talk a little about — you know, this all came about because you've been writing the Inside Podcasting newsletter for a while now, and you've built up an audience. You have a really nice rapport with readers. So, do you think that gave you a sense of what this was going to be like? Or was it completely not even close to helping you prepare for actually doing the podcasting? You can only absorb so much from reading. You actually have to sometimes do things. So, how much of writing the Inside Podcasting newsletter and having a handle on, "Okay, this is what podcasters go through, and this is what podcasting is like?" How much of that helped you prepare? Do you feel like maybe it was even just a sliver of what it's really like to do podcasting?

SP: That is a really good question. The answer for me is that it didn't help that much.  Having written about podcasts did not help. It's not the same at all. Of course, there were certain things that I knew I wanted to do because I had read articles. And, attended events too, where I would learn things — like, I think we're going to make audiograms, which we haven't even made at this point, but I think we're going to make those for our episodes. That's something I learned about because I was writing about them.

Things like that. But it's so theoretical. Actually doing it — I made so many mistakes — I'm hoping the listeners enjoy those mistakes. For me, part of this podcast is bringing the listeners along on this journey where I was not — you know, I'm a brand new podcaster.  Just because I write about it does not mean that I know how to do it. I did things like — I interrupted people. I made all these rookie mistakes. I interrupted people. My questions were way too long, especially my very first episode. I tried really hard to fix it after that. I actually re-recorded a bunch of the questions so that hopefully it won't drive the listeners too crazy to hear that. I also just wasn't —learning how to find your voice is something you cannot do by writing about podcasts. One thing I did in that first episode that I recorded with Madeleine Baran of In The Dark, I was trying — consciously or not — to sound like Terry Gross.

KL: Aren't we all though?  Aren't we all trying to be Terry Gross.  I mean, that's a good thing to aspire to, for sure.

SP: That's right. And, I think that you can hear that. I think that listeners will hopefully get a kick out of me trying to sound like her.  

KL: I think that you can hear that, Skye. But, honestly I feel that you are selling yourself short.  You've done a really nice job in a really short time of getting up to speed. You can tell in the interviews that you're really interested in the guests.  When you're a guest on a podcast, you can also tell. When the host is interested, it makes a difference. I think the interviews are really interesting and fun to listen to. 

KL: What I want to know from you is when are you going to feel like you're a podcaster? You've done all this work. You realize how much goes into it.  What's going to be your measure of success for this? When are you going to be able to say, "I'm a podcaster too"? Because I feel like you're still not quite there. You still feel like you're a rookie, but I feel like you've got a lot of experience under your belt now.  

SP: That’s great to hear.  You're right.  I'm not — I don't — I can't wear that mantle yet.  I do still feel I have a little bit of imposter syndrome, but I think that once it's out there and people have heard it — and hopefully people have gotten something out of it. Once I've made a difference to one person who tweets at me, that will feel like "Oh, maybe I am this."  Maybe I can say that I'm actually doing this. I don't think I'm going to feel that way until it's out in the world. I'm so excited for that to happen. That's going to feel huge.

KL: So, this is great. I can't wait to hear the episodes in their finished version and to hear what the reception is. I'm really excited for you. I know this has been a long and winding road, but it's finally happening. And, I can't wait to hear them in their entirety and to have them out in the world.

SP:  Me too. I'm so, so looking forward to that. And, again, I hope people get something from them that's useful. Thanks to you, Kim, for all your help, and, Michael, who's our producer.  And, the whole team, who of course I'll be talking about this season.  I'm really proud to work with everyone.  I can't wait to get the episodes out there!

This newsletter was written and curated by podcast junkie and recovered publicist, Skye Pillsbury. Over the years, Skye has crafted digital media strategies for brands like Yahoo! and Microsoft and worked regularly with media outlets such as the New York Times, Rolling Stone and NPR. Skye was famous for 49 minutes when she and her son were featured in an episode of Gimlet Media’s Heavyweight podcast. Follow her on Twitter @SkyePillsbury.

Editor: Kim Lyons (Pittsburgh-based journalist and managing editor at Inside).

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