Craig Cannon on Podcasting with Adora Cheung

Welcome! I am Adore Chun. I'm a partner at Y Combinator, and I am here interviewing Craig Kenan.

How's it going?

Good, how are you doing?

I'm doing very well, great! Thanks for being here and for being on your own podcast.

No problem! I had a great time sitting in a lot.

So, Craig is the head of marketing at Y Combinator, and also the extraordinaire host of this great Y Combinator podcast. He actually asked me a few weeks ago on topics I was interested in doing on a podcast. So, I thought about things I want to learn more about, and one of those things is actually podcasting itself. It's hitting its stride, I think, and who better to ask than someone like yourself?

So, I want to spend most of the time talking about podcasting trends, what you think about it, how to do it correctly, things like that, and about the Y Combinator podcast itself. But maybe we can start off with telling us, you know, people—lots of people listen to you, you know, what, two to three times a week? Know anything about you.

So why don't you start off with: Who's Craig Kenan? Where are you from? You know, how did you—what's your background? How did you learn about YC, and how did you even end up here?

Yeah, that's a big question. I'll do the quick version.

So yeah, hi! My name is Craig. I'm from Boston or near Boston. I went to school at NYU, and I was an English major, so I was like the guy. All you people, all you CS engineers made fun of. And I was about to graduate, and I realized that I was like moderately unemployable. I didn't have very many skills, but I was running the comedy magazine at NYU.

So I was like, well, maybe I can get a job at this place called The Onion. And so I just sent out an application, and like, that was the one thing I got. So, I started working there, and while I was there, I actually started reading HÑ and programming on the side.

After a few years there, I started this hackathon series called Comedy Hack Day, where developers and engineers—our developers and comedians made stuff together.

Yeah, yeah, because I was going to hackathons and realizing that they were mostly presentation competitions, not really programming competitions.

What's an example of something that—so, one of them was called Times Fi, and it was a Chrome extension that would allow you to turn any website—usually a junk news website like BuzzFeed—into a site that looked like The New York Times, but it would inject the article into it.

And then, like, you could click the ads, and it would basically create a slideshow of all the images.

Yeah, that was great. And there were a ton of them.

Um, yeah, so we did that for like four years with a few of my friends. I had gotten into cycling when I was out here, and I found this thing—this, like, world record that I wanted to go for, and I did it, and it worked out. People started treating me differently, and it was really weird.

And I like started feeling this, like, pending doom of my youth and vitality fading away. It was the most elevation climbed in 48 hours.

Oh wow, so is that—well, mine was like 97 thousand feet.

Got it, yeah. So, yeah, people were treating me differently, and I was like, oh [ __ ] I’m not gonna be young forever. And so, I quit, and I went on like a five-month bike tour out of the country.

And I went to Japan and Vietnam and New Zealand, and I came back, and I had no job and I had no idea what I was gonna do. And then Luke Iseman, who used to work here, called me up and asked me if I wanted to do a contract for the blog.

And so that started, you know, three years ago.

Okay, oh okay, so you started with the blog. And then, so what were the steps into how you eventually started this—the YC podcast? And why even the podcast?

Yeah, so it should be said that Aaron did a YC podcast a few years ago called Startup School Radio.

And yeah, I wanted—actually, I didn't care as much about making a podcast; I wanted to make a YouTube channel because YouTube, I think a lot of people know now, has great SEO, and podcasts have terrible SEO.

And so, I was like, alright, what's the easiest way for us to create a ton of content for a YouTube channel and then title...