Skye Pillsbury

Skye Pillsbury writes the Inside Podcasting newsletter and also hosts the Inside Podcasting podcast. Follow her on Twitter here. Follow Inside Podcasting on Twitter here.

Hi, Skye! Kindly introduce yourself.
My name is Skye Pillsbury and I write the Inside Podcasting newsletter, which includes a mix of news about podcasts, creators, technologies, and industry developments. I also host a podcast of the same name, where creators are given a chance to talk about their craft. It’s kind of like “Inside the Actor’s Studio,” but for podcasts. Season one is available for binge-listening right now; we are working on season two.

How did you get into podcasting?
My background is in technology PR, mostly working with Internet startups. I loved it for a solid decade — it felt like I was part of something that was changing the world. I did things like help journalists see the web for the first time. It was exciting, but eventually, the vibe changed — scores of people moved to the SF Bay Area in pursuit of a quick IPO payout — and as a result, my feelings for the industry began to wane. Meanwhile, listening to podcasts was giving me the same rush I felt at the beginning of my tech career. So I was listening to podcasts and reading about the industry every spare moment I had. Eventually I was given the opportunity to write about podcasts for Inside.com and I jumped at it. [Inside Podcasting is part of the Inside.com network of newsletters.]

Talk about your Heavyweight episode. Was it hard to listen to? (Skye and her son Clark were the subjects of a Heavyweight episode that was nominated for “best audio documentary by The International Documentary Association. Dear reader, this is a must-listen!!!)
No, it was wonderful to listen to! At 5am on the day it dropped I grabbed my phone, ran down to Clark’s room, climbed up into his bunk bed and we listened to it together. It was magical to listen to it in the dark, before the world woke up. I’ll never forget it. Jonathan and Kalila and all the folks at Heavyweight did a wonderful thing for our family. I’m grateful to them.

What does your son think of podcasts and what you do?
Clark enjoys podcasts. His fave is Stuff You Should Know and we listen to it on the way to hockey practice every week. We listened to an episode about obsessive-compulsive disorder the other day and it led to an interesting family discussion.

Clark is subscribed to the newsletter but I’m always surprised by the fact that he never seems to remember anything I’ve written (hmm….). That said, I think he’s proud that I’m following my passion. He’s a fan of Everything is Alive and was impressed that I interviewed its creator — so that’s something.

Does he know how cool you are?
Ha! He’s thirteen now, so I’m definitely not cool. Actually, I was cool for a very brief moment this month, when I caught air while skiing through a terrain park. By the time we got to lunch, I was uncool again.

You have a podcast that interviews podcasters. I used to have a podcast about podcasts, but it never took off, and I’m kind of surprised to not see more podcasts about podcasts and podcasters. Why do you think that is? What are the challenges?
That’s a good question. I’ve listened to your podcast so I know how good it was and how hard you worked on it (the episode about the Mazda Reply All + Trader Joe’s had me in stitches). Your show deserved to take off. I guess the challenges are the same as the challenges with any show. Finding a loyal audience who is willing to invest time in you. It’s a big ask.

What are the secrets to running a great interview with a podcaster?
I wish I knew the answer to that question! Sometimes the chemistry just works, and you can’t really put your finger on why. That said, my best advice is to interview people you are supremely curious about, and immerse yourself in their work beforehand. I spend hours reading and listening to the work of my guests. I write my questions down but try not to look at them too much, so that I can really be present in the conversation. I interviewed Kara Swisher yesterday and she told me she never writes her questions down or really does any prep. Then again, she’s a (self-described) sparkly vampire with magical powers. How can I compete with that?

Many women in podcasting are criticized for their voices. What is your relationship to your voice?
When I was younger, I was embarrassed by my voice. It’s of the “husky” variety. But I have no problem with it now — in fact, I like it. Maybe that’s part of getting older and becoming more accepting of yourself.

Do you remember the first show you listened to?
I was part of the Serial wave of listeners. But the first show I really loved was Startup. It blended narrative audio with my fascination for startup culture and I just fell completely in love.

What was your favorite story that happened in podcasting in 2019?
I hope no one interprets this the wrong way, but I was absolutely fascinated by Luminary’s missteps during its launch. Not because I took pleasure in it, but by doing so many things wrong, Luminary illuminated how to do things right. I learned valuable lessons just from watching that debacle unfold. And despite my relentless coverage of their mistakes, I do want them to succeed. There should be room for everyone and there should be multiple ways to pay creators for ambitious work. I’m not going to throw shade.

What do you say to someone who says they don’t listen to podcasts?
If someone is truly uninterested, I’m not going to waste their (and my) time pushing a boulder uphill. They’ll figure it out when they’re ready. On the flip side, when someone is open to it, I don’t hold back. My son’s orthodontist said she was podcurious, so I took her phone and downloaded some shows and now she’s as addicted as me. Hearing how much she loves listening during her commute gives me a lot of pleasure.

Thanks, Skye!