2 Years (Nearly) of People Doing Things


On Nov 15th, 2014 I sat down with my friend and neighbor, Ryan Caron, to chat about art and life. I recorded the whole meandering conversation and posted it the next morning as the first episode of my podcast. I’d had a desperate epiphany a few weeks earlier: that I was good at talking to people and I loved hearing stories. If I was going to pull myself out of the rut I was in, the best option was probably to combine something I thought I was good at with something I enjoyed. I had no idea what format the podcast would take- merely that I wanted to force myself to have weekly conversations with interesting people and then share those conversations in case any little nugget was relevant to someone.

It’s now been almost two years and roughly 100 “chats” with interesting folks from all different disciplines and I can categorically say: I think I’m beginning to get the hang of it. I always knew it would be at least a year of learning and experimenting but what I didn’t realize is that my early fixation on format would ultimately not matter at all- the thing people connected with was the stories- whether that was me whinging about a stupid movie, having a panic attack during an episode, or talking to someone who deals with dead people for a living. I’ve learned a lot, probably a few things I haven’t even fully realized yet, but here’s a few lessons I’ve learned in the last two years:

1. Prepare as much as you need to. In the beginning I was adamant that I didn’t want to do research on guests. I wanted to “preserve the integrity of the conversation” so to have pre-arranged questions would fundamentally ruin the spontaneity of the show. Turns out that doesn’t really matter.You need a hook, or a way in, so if I’m talking to a total stranger, I read as a little bit about who they are, what they’ve done and maybe why they do it. I don’t write anything down, or try to do an exhaustive search, I just try to load up my brain with a few ideas that I can maybe come back to. Nobody is going to give you an award for putting no effort in.

2. Trust your original idea. I like being flexible and spontaneous but I always knew there were a few things about the show that I didn’t want to compromise on. The biggest one was that I wanted to do a long-format interview show. I had a lot of people tell me early on that no one would listen to an hour plus show. I knew they might be right but I also knew that the only thing that would keep me wanting to do the show beyond a few episodes was to do a long format podcast. I’d probably still have more listeners if I did a shorter show. But that was never important to me and two years in, I’m still interested in doing the show because it’s long format.

3. Don’t take things personally. After the first fifty episodes, I had to start reaching out to folks I didn’t know to try and harangue them into coming on the show. Generally speaking, people are pretty keen to talk and rarely does someone just say ‘no.’ But often you do get complete radio silence. In the early days (and still sometimes) I took this really personally, projecting a condescending attitude onto some local artist who thought they were somehow too good for my lowly little podcast. This wasn’t just immature, it often meant that I’d totally write someone off and then a few months later when they had the brain space, they’d reach out to me to do the show. Yeah, of course there’s people that are condescending and view themselves as too important to do the show. And that’s fine. Some of them probably are. And even if they just don’t get it, that’s okay. It frees up room for someone else to be on the show who actually wants to talk. I don’t keep a mental blacklist anymore. Just don’t expect Ryan Guldemond to be on the show anytime soon.

Alright, we good? Yeah, we’re good. Do the thing!

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