Craig Cannon is the Director of Marketing at Y Combinator. He usually hosts the YC podcast but today is the guest on this episode about podcasting.

Adora Cheung is a Partner at YC.

You can find Adora on Twitter at @nolimits and Craig at @craigcannon.

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Topics

00:00 – Adora’s intro

1:05 – Craig’s intro

3:45 – Starting the YC podcast

5:00 – Podcast metrics

6:00 – Tips on creating a podcast

8:10 – Picking episode topics

9:00 – Order of operations for finding guests

10:30 – Preparing for interviews

13:50 – How to keep an episode engaging

16:05 – Analytics

18:30 – Gear – Full list here

23:00 – Software

23:55 – Listening to your own voice

25:20 – Favorite interviews

26:20 – Most surprising things Craig’s learned about startups on the podcast

29:00 – What has Craig learned from guests that he’s put into practice?

31:40 – Non-consensus things about building startups

34:00 – If Craig had to start a podcast from scratch, how would he structure it?

36:40 – Clipping the show

42:00 – Monetizing podcasts

45:30 – Will podcasts become saturated?

46:00 – What’s missing in the podcast world?

48:00 – Influential podcasters

51:50 – Adora’s podcast picks

52:50 – Patrick Bender asks – What idea do you believe in that your social group would think is crazy?

57:50 – Zachary Canann asks – Please tell us about the time you most successfully hacked some (non-computer) system to your advantage.

59:50 – Being at YC, do Craig and Adora feel pressured to go start a company?

1:06:00 – When is an opportunity good enough to quit your current job?

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Transcript

Craig Cannon [00:00:00] – Hey, how’s it going? This is Craig Cannon, and you’re listening to Y Combinator’s Podcast. Today’s episode is a bit different. Adora Cheung, who’s a partner at YC, suggested we do an episode about podcasting. So in this one I’m actually the guest. You can find me on Twitter at @craigcannon and Adora at @nolimits. Alright, here we go.

Adora Cheung [00:00:20] – Welcome. I’m Adora Cheung, I’m a partner at Y Combinator, and I am here interviewing Craig Cannon.

Craig Cannon [00:00:27] – How’s it going?

Adora Cheung [00:00:27] – Good! How are you doing?

Craig Cannon [00:00:30] – I’m doing very well.

Adora Cheung [00:00:30] – Great, thanks for being here. Thanks for being on your own podcast.

Craig Cannon [00:00:33] – No problem, I had a great time setting it all up.

Adora Cheung [00:00:37] – Craig is the head of marketing at Y Combinator and also the extraordinary host of this great Y Combinator podcast. He actually asked me a few weeks ago on topics I was interested in in doing on a podcast, so I thought about things I wanted 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 you could start off with telling us, lots of people listen to you, what, two to three times a week?

Craig Cannon [00:01:14] – Yeah, it depends.

Adora Cheung [00:01:14] – I don’t think they know anything about you. So, why don’t you start off with, who’s Craig Cannon? Where are you from? What’s your background? How did learn about YC and how did you even end up here?

Craig Cannon [00:01:26] – Yeah, that’s a big question. I’ll do the quick version. So, yeah, hi, my name’s Craig. I’m from Boston, or near Boston. I went to school at NYU and I was an English major. So I was the guy all you people, all you CS engineers made fun of. I was about to graduate and I realized that I was 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.” So I just sent out an application and that was the one thing I got. So I started working there and while I was there, I actually started reading HN and programming on the side. After a few years there, I started this hackathon series called Comedy Hack Day, where developers and comedians made stuff together.

Adora Cheung [00:02:20] – Good, so it’s a hackathon. It was literally a hackathon. Oh, that’s funny.

Craig Cannon [00:02:22] – Yeah, ’cause I was going to hackathons and realizing that they were mostly presentation competitions, not really programming competitions.

Adora Cheung [00:02:29] – What’s an example of something that got produced during one of these things?

Craig Cannon [00:02:32] – One of the early ones was called Timesify. 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 The New York Times, but it would inject the article into it. And then you could click the ads and it would basically create a slideshow of all the images. So that was great. There were a ton of them.

Adora Cheung [00:02:55] – Cool.

Craig Cannon [00:02:56] – So I did that for four years with a few of my friends, and I had gotten into cycling when I was out here. I found this thing, this 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. I started feeling this pending doom of my youth and vitality fading away.

Adora Cheung [00:03:21] – What was the world record again?

Craig Cannon [00:03:23] – It was most elevation climbed in 48 hours.

Adora Cheung [00:03:25] – Oh wow, how much is that?

Craig Cannon [00:03:27] – Well, mine was 97,000 feet.

Adora Cheung [00:03:30] – Got it.

Craig Cannon [00:03:30] – Yeah. People were treating me differently and I was like, “Oh shit, I’m not going to be young forever.” So I quit and I went on a five-month bike tour.

Adora Cheung [00:03:41] – Oh wow.

Craig Cannon [00:03:42] – It was out of the country and I went to Japan and Vietnam and New Zealand. I came back and I had no job and I had no idea what I was going to do. And then Luke Eisman, who used to work here.

Adora Cheung [00:03:54] – Oh, that’s right.

Craig Cannon [00:03:55] – Called me up and asked me if I wanted to do a contract for the blog. So that started three years ago.

Adora Cheung [00:04:01] – Oh, okay. So you started with the blog. So what were the steps into how you eventually started the YC podcast and why even the podcast?

Craig Cannon [00:04:10] – Yeah. It should be said that Aaron did a YC podcast a few years ago called Startup School Radio. 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. 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 it all in a way that our founders get attention, stuff we want to talk about gets attention and, more importantly, it doesn’t fade away?” So I was like, “Well, podcast is a good way to do that.” We just started from there.

Adora Cheung [00:04:50] – Oh, so podcast is the way to get the content and then YouTube is the way to spread it.

Craig Cannon [00:04:56] – Well, ’cause we do both. But I think it was 2014 or 2015 when I started following Joe Rogan. I just saw this massive growth happening, and people were clipping his videos and creating fan channels. And now, I think, his YouTube channel gets as many views as his podcast gets downloads, which isn’t true for ours. But if you look for Adora Cheung online, I’m sure, if you Google yourself, you show up.

Adora Cheung [00:05:21] – Occasionally.

Craig Cannon [00:05:21] – Yeah, yeah, yeah.

Adora Cheung [00:05:23] – To calibrate us a little bit, so, the Y Combinator account, how many views do we get, or, how do you even calculate this, or what metric actually matters? Let’s talk about that.

Craig Cannon [00:05:34] – The thing that ultimately really matters is like, we kind of have two goals. One is to help educate founders and people who are in the startup game, and two, is to bring other founders in. The way we’re trying to calculate this, and it’s still pretty loose, is by driving applications. That’s the main thing. But, in terms of sheer metrics, we started out possibly a little bit bigger than other shows by having maybe two or 3,000 people automatically subscribe. Now we’re maybe 40-ish thousand, give or take five or 10,000 every episode, plus YouTube. YouTube can go from 1000 to 100,000, depending on who the person is.

Adora Cheung [00:06:21] – I wanted to get into how you create a podcast essentially, and your tips there. Let’s pretend I want to do a podcast. I have a topic that I want to do. How do I decide if that’s actually a good idea or not to even work on it?

Craig Cannon [00:06:39] – Do you have an idea in mind?

Adora Cheung [00:06:41] – I can come up with a theoretical idea. One I’ve always just joke around doing, which I think actually might be a good idea, is to do a podcast where I ask little kids deeply philosophical questions, just because I think they actually have great insight into the world and which we are unaware of.

Craig Cannon [00:07:02] – You’ve seen that show, right? Kids Say the Darndest Things.

Adora Cheung [00:07:05] – Yes, people have told me about that. I have not seen it, but I’ve see clips of it. I’ve seen little clips of it, yes, yes.

Craig Cannon [00:07:10] – Right off the bat, there’s clearly an audience already for this. Like, that show worked. The first question is, honestly, do you want to do the thing? I think another question that a lot of people don’t ask is, am I willing to even create a time box around this and say, I’m okay if I make 10 episodes. ‘Cause one of the hardest parts about podcasting, in particular if it’s not your job, like with YC, I’m just like, okay, we’ll just keep banging it out every week. If it’s not your job, it can become a real grind because those metrics don’t go up that quickly. Getting from 30,000 to 40,000 and 40,000 to 50,000 can take years for certain people. Assuming that you really want to do the thing, could I maybe make eight of these? Alexis Madrigal did that with The Container podcasts. I don’t know if you’ve listened to that one.

Adora Cheung [00:07:59] – No I haven’t.

Craig Cannon [00:07:59] – But it’s super cool, and it’s the short version. I thought that was a great idea. Would this be scripted in any way?

Adora Cheung [00:08:08] – Probably not, but I would have to probably edit a lot.

Craig Cannon [00:08:13] – Right, okay. What I would suggest doing then is just getting a basic, basic setup and then just going and recording a bunch. Like don’t even release.

Adora Cheung [00:08:21] – Got it. Cool. The YC podcast, every episode has its own topic. How do you come up with those topics?

Craig Cannon [00:08:32] – In many ways it’s about stuff I’m interested in. I don’t know, I hit this point where we hang out, you hang out with other people at YC and people who are in tech, and I just found that there wasn’t really any tech podcasts that interested me, ’cause it all feels very inside baseball. I was like, maybe other founders aren’t interested in this either, ’cause they talk about it all the time. So I thought, okay, perhaps we could focus on technology as a core, as a pillar, but also do art and science and entrepreneurship. And then it’s just been getting a mix of these people. So, yeah. A big driver is, obviously, if they have a following.

Adora Cheung [00:09:17] – Got it. So you have a topic for the episode, then you obviously needed to find someone to interview.

Craig Cannon [00:09:26] – It usually goes the other way.

Adora Cheung [00:09:27] – Oh, okay. Got it. So tell me the order of operations of how you put together a whole entire podcast.

Craig Cannon [00:09:32] – A common one is I ask someone at YC, like you, hey, who do you want to do a podcast with? Kevin Hale has done a few recently. That’s what that was. There are other ones. For instance, I did an episode with John Preskill who’s a quantum physicist at Caltech and he suggested other people. So he was like, “Oh man, you got to get like Scott Aaronson, Leonard Susskind, all those people.” So that’s a really common thing. It’s just finding trends, finding things that are interesting and going from there.

Adora Cheung [00:10:02] – Is booking guests easy, hard or, what are reasons why people don’t want to do it? ‘Cause I’m sure some people have said, “Uh, not really.”

Craig Cannon [00:10:09] – The more common no, is not replying.

Adora Cheung [00:10:12] – Got it, okay.

Craig Cannon [00:10:12] – Yeah. But there are some fringe runs, for sure, where people say, I don’t know if I want to be on the YC podcast.

Adora Cheung [00:10:20] – Interesting.

Craig Cannon [00:10:21] – ‘Cause there are sort of brand connotations.

Adora Cheung [00:10:23] – Ah, interesting. You’re making this actually… To do a podcast sounds like almost starting a startup. You need to validate your audience. There’s a lot of hard, long days of work to do. Maybe there’s a lot of cold emailing. Cold outreach, essentially, and just keep asking people to do it until they actually want to do it.

Craig Cannon [00:10:45] – Then keep learning too. I think thinking about content in the same way you think about product, is just like, great, there you go. You can apply all the same ideas.

Adora Cheung [00:10:52] – Cool. Alright, so how do you prepare for interviews? In particular, you have some interviews that involve topics which you’re probably not an expert in, like, I don’t know, quantum physics, these kind of things.

Craig Cannon [00:11:05] – Yeah, for sure.

Adora Cheung [00:11:06] – But you actually ask really good questions. So, how do you do that?

Craig Cannon [00:11:11] – I think I would probably break apart the episode types. There’s episodes like Office Hours with Adora. I know you, I know the kinds of questions that come in. I don’t really have to prep for that one. There’s a middle level, which is a founder of a company, say, Ryan Petersen at Flexport. I kind of know what Flexport does. I’ve seen Ryan talk before. In that instance, what I would do is, find every podcast he’s ever done and listen to all of them at 2X speed. So you’re like, “Okay, this is the stuff he’s excited about, these are the anecdotes he’s used a million times, avoid anything that he’s going to like have these really easy places to go.” The last category are the quantum physics-type episodes which, to confirm your belief, I’m not an expert in.

Adora Cheung [00:11:59] – How long does it take? For example, that episode itself, some of these you barely have to do any prep. For this one, did it take weeks, or days or?

Craig Cannon [00:12:09] – The first quantum physics episode with… Well, there was a hard one before that, too, with Rana Adhikari about gravitational waves. But the quantum one was more difficult. That probably took 2 1/2 days between listening to John’s talks and reading articles he’s written with other people. Scott Aaronson, I read his whole book. You just take notes and that kind of thing. But, ultimately, the goal is actually not to become an expert. The goal is to become informed enough that I know more than maybe the average listener, but not so informed that we fill it with jargon and talk about stuff that no one really knows about or cares about.

Adora Cheung [00:12:51] – That makes sense.

Craig Cannon [00:12:52] – There are examples, like the Susskind episode, which is one of the most popular ones, we had planned for months and then the week before, I hadn’t done any prep yet. The week before, I’m like, “Alright, we’re going to meet here da da da da da.” No reply.

Adora Cheung [00:13:06] – Oh no.

Craig Cannon [00:13:07] – Usually when that happens, it means that he’s ghosting me. I didn’t do any prep. I’m like, “Alright, he’s ghosting me, he’s ghosting me, he’s ghosting me.” We’re doing the interview on Monday. He emails me Sunday night. I’m like, “Oh shit.” It’s cram it in. So, possibly the YouTube comments reflect my level of preparedness.

Adora Cheung [00:13:25] – Oh no!

Craig Cannon [00:13:26] – Which is a separate thing to deal with.

Adora Cheung [00:13:28] – Got it. What was the most challenging one for you?

Craig Cannon [00:13:31] – I would say the, hmm. So John Preskill was particularly difficult ’cause he’s also very chill. So keeping it upbeat, keeping it interesting, keeping it fun. I would say the one I bombed hardest on was Jocko Willink and Mike Sarraille. I don’t know if you listened to that one.

Adora Cheung [00:13:49] – Oh the Navy SEAL guy.

Craig Cannon [00:13:50] – The Navy SEAL episode.

Adora Cheung [00:13:51] – Yes, I remember listening to it.

Craig Cannon [00:13:52] – Yeah, I think I was just too nervous. I have this thing where when I get nervous I laugh.

Adora Cheung [00:13:57] – Oh no.

Craig Cannon [00:13:58] – It was fine. We hung afterwards and it was like, ah, this is much better than before.

Adora Cheung [00:14:03] – Cool. On the topic of keeping a podcast or an episode engaging, how do you, like you said, some people are just really chill and maybe they’re monotonous or whatnot. How do you push them to keep it engaging?

Craig Cannon [00:14:16] – Usually, this doesn’t come out in the podcast, but we talk before we start recording. So you kind of feed them what they should think about, how they should act. Basically these are the norms of the show. Most of it’s just about making them really comfortable. We do a slight amount of editing, usually almost none, but, if I edit anything, it’s often the first five minutes. I’ll just cut the whole first five minutes off, because you’re like, “Oh, Adora really got warmed up and she was into it at this point.” I can mix in an intro. People think this matters, but the intro doesn’t really matter. I don’t know. It’s not a big thing that I care about. Actually, one of the best podcasters in this regard is Russ Roberts from EconTalk.

Adora Cheung [00:15:04] – Ooh, I love that one.

Craig Cannon [00:15:06] – If you pay attention to his show, he always starts with a, not a controversial question, but a question that’s not a softball. I think that’s a really great way to start the show.

Adora Cheung [00:15:16] – Got it.

Craig Cannon [00:15:17] – Because you want to give them something that’s interesting to them, but you don’t want to confront them. This is something that a lot of podcasters, and I fall prey to it too, you don’t want to offend someone and so you’re really nice. So you ask them all these softball questions.

Adora Cheung [00:15:31] – Got it.

Craig Cannon [00:15:32] – But you don’t really go anywhere. That’s how you end up with like the Joe Rogan Elon Musk episode. Did you see that one?

Adora Cheung [00:15:39] – Yeah I did.

Craig Cannon [00:15:40] – It was so bad. It was like, Joe Rogan’s great and Elon Musk is capable of giving good answers, but because he knows so much more than Rogan and Rogan didn’t prep that much, he just dodged him the whole time. And he was fanboying.

Adora Cheung [00:15:52] – Yeah, yeah. Those get obvious after the first 10 minutes. It’s like, okay, this is going down the, not going to learn much here.

Craig Cannon [00:16:00] – Do you listen to full episodes normally of any podcast?

Adora Cheung [00:16:03] – Joe Rogan? I try listening to Joe Rogan. I like those. Do I listen to the whole thing? Maybe once a week. I’ll listen to one a week.

Craig Cannon [00:16:15] – A whole one? And other shows? You listen to the whole thing?

Adora Cheung [00:16:18] – I listen to yours.

Craig Cannon [00:16:19] – Thanks.

Adora Cheung [00:16:20] – Those are maybe the only two where I regularly listen to the whole thing. I guess not much.

Craig Cannon [00:16:26] – ‘Cause this is something that I often think about, because the metrics, or not the metrics, the analytics are so bad, you don’t really know. Like, should I just be cutting this down or something. I think they’re just different audiences.

Adora Cheung [00:16:38] – It’s not YouTube where you can see where they just dropped off.

Craig Cannon [00:16:40] – Well, you have Apple analytics but they’re not very good.

Adora Cheung [00:16:42] – Oh really?

Craig Cannon [00:16:42] – And it’s only a percentage of the market.

Adora Cheung [00:16:45] – Okay. I want to talk about analytics in a second.

Craig Cannon [00:16:46] – Sure.

Adora Cheung [00:16:47] – But, actually, let’s just talk about analytics. So, Apple analytics, there’s nothing Mixpanel or Amplitude or any of these.

Craig Cannon [00:16:55] – It’s Google Analytics version 0.1, that’s where Apple analytics gets you. ‘Cause you, I think what might not be obvious to people, is that podcasts aren’t like YouTube videos. You don’t upload your podcast to iTunes. You upload your podcast to a host, and then the host serves the podcast from an RSS feed. Because that’s the way it works, what information you can get is serves, like it’s been downloaded basically, X amount of times. But you don’t have any kind of that retention data that you have, unless you’re using Apple, or you’re using an embedded player. So, if you listen for instance on the YC blog, in the embed thing, then I know.

Adora Cheung [00:17:35] – Got it.

Craig Cannon [00:17:36] – That’s it.

Adora Cheung [00:17:37] – Yeah, so really only these podcast players might know. Well, they will know it for that episode, I guess.

Craig Cannon [00:17:45] – Yes.

Adora Cheung [00:17:47] – That it’s actually played on their podcast. But I guess the players have, you’re seeing fragmentation amongst players now.

Craig Cannon [00:17:53] – I’ve heard something like 60% is Apple podcasts.

Adora Cheung [00:17:57] – Okay, got it.

Craig Cannon [00:17:58] – So it’s pretty big share.

Adora Cheung [00:17:58] – Yup.

Craig Cannon [00:18:00] – But then after that it’s just, I think that there’s a dominant player on Android. I don’t have an Android, I forget what it’s called. Then there’s a bunch of other ones.

Adora Cheung [00:18:07] – Yeah, there’s Castbox on Android.

Craig Cannon [00:18:08] – Oh, but it’s actually not that one.

Adora Cheung [00:18:10] – I just googled for that one.

Craig Cannon [00:18:12] – Well that was a YC company, and that was when they applied to us, like no way. The podcast app?

Adora Cheung [00:18:17] – There’s the podcast app, yes.

Craig Cannon [00:18:19] – I was like, such a great name. Yeah yeah such a good idea.

Adora Cheung [00:18:21] – Alright cool. So what are all their tools that are indispensable for the podcast? Maybe we’ll start with software and then you’ve got a lot of gear. But what I’ll say is, I did my research, and I listened to, before this, I listened to a lot of your first episodes.

Craig Cannon [00:18:38] – Oh no.

Adora Cheung [00:18:39] – And so you can… Which is actually pretty good quality. But then if you listen to the last 10 episodes that you just did.

Craig Cannon [00:18:44] – They’re way better.

Adora Cheung [00:18:46] – You can hear the sound quality like there’s less echo. You can hear the voice more clear. So can you walk me through what did you start with and what’s the gear that, like what’s the MVP gear you need to get going, and then what do you have today?

Craig Cannon [00:18:59] – The MVP gear is this. This is your phone you can record a podcast on your phone. Don’t let your gear disqualify you from doing it. That’s my main point. But what I started with back when… I did a podcast before YC too.

Adora Cheung [00:19:15] – Oh what was it?

Craig Cannon [00:19:16] – It was great. It was called Salt of the Earth. It’s still on iTunes. It was really funny in contrast the YC podcast, because it was in relation to tech entrepreneurs getting so much attention. My friend and I, we went to college together, and we both grew up in New England, and none of our role models were tech entrepreneurs. They were local electricians and stuff. So we said, “Why isn’t there a podcast with these guys and ladies who are often very funny?” So it was really hard to find these people but funny successful small business entrepreneurs. So we did that. We maxed out 2000 downloads an episode or something that but we had really simple gear. So that was a Zoom recorder so it has four inputs, totally great. Shure mics that were 50 bucks each. The Zoom recorder, I don’t know, was 100 bucks. So they’re also USB. There’s this thing called the Blue Yeti which you can just plug into your laptop and record.

Adora Cheung [00:20:18] – Got it cool.

Craig Cannon [00:20:20] – Oh yeah and the gear now. Oh yeah.

Adora Cheung [00:20:23] – If you’re listening to this on a podcast, Craig, when he does an episode, he actually has a lot of stuff. One of the things he does is he takes down our walls, these portable walls that are in another room, and then he drags them into a really small conference room. So I guess that’s for sound.

Craig Cannon [00:20:42] – Yeah. I think it actually ends up looking better too, in a weird way. So what happened there was I realized after I started doing this podcast in this room that this is not the best room in the world to record a podcast, but actually our office doesn’t have many great rooms for that ’cause you definitely don’t want a street window.

Adora Cheung [00:21:04] – Right.

Craig Cannon [00:21:05] – But it also needs to not be in use all the time. I was basically left with this room, so yeah. So I have these sound blocking things to eliminate echo, because my voice was getting picked up on your microphone. You still get it but it’s a little bit less, because we don’t do the headphones. You’ve probably seen that before.

Adora Cheung [00:21:23] – Yes, yes.

Craig Cannon [00:21:25] – I tried it and everyone freaked out.

Adora Cheung [00:21:26] – I hate headphones.

Craig Cannon [00:21:27] – Exactly.

Adora Cheung [00:21:28] – When I was in college I used to do a radio show.

Craig Cannon [00:21:30] – Really?

Adora Cheung [00:21:31] – Because you’re hearing yourself talking. I was the one who was the annoying one and just.

Craig Cannon [00:21:37] – You were the host?

Adora Cheung [00:21:38] – No no no no. Well it was a talk show. So it was just gabbing. It was old school podcast I guess.

Craig Cannon [00:21:45] – What was it about?

Adora Cheung [00:21:46] – It was just, we talked about news in the school and just regular politics and stuff like that. I really hope this was not recorded and does not exist anymore.

Craig Cannon [00:21:56] – That was my next question. Dude, that’s awesome.

Adora Cheung [00:21:58] – Well yeah it was a local college news station.

Craig Cannon [00:22:00] – Okay, cool. Yeah. Yeah. That’s hard. That’s a separate question that someone asked that we should talk about hearing your voice. But yeah, so now we use these are Shure SM7B mics. These are 300 bucks. The biggest upgrade was the recorder, which was actually from a YouTube comment. This is called the MixPre-6 Sound Devices. To make these Shure mics sound good, you need a bunch of what they call clean gain, and our Zoom recorder didn’t really do that. This thing does that, and then we record on Canon DSLRs. So they’re less than 1000 bucks each.

Adora Cheung [00:22:33] – Okay. So your suggestion is step one, just use an iPhone. That’s good quality anyway.

Craig Cannon [00:22:38] – Well I wouldn’t suggest iPhone as doing it. But I was like, you can conceivably do it with an iPhone.

Adora Cheung [00:22:44] – Got it.

Craig Cannon [00:22:45] – But what I would suggest is if you’re going to move around locations all the time, and even if you’re not, if you’re going to do the interviews in person, get a recorder like a Zoom H4N or something that, get Shure mics, SM58 whatever. They’re 60 bucks and XLR cables, the cables to plug them in, and you can take it anywhere. If you’re going to interview people remotely, get a USB mic, a Blue Yeti.

Adora Cheung [00:23:11] – And then do it over Skype?

Craig Cannon [00:23:12] – I’ve used it one time. I forget, can’t remember what it’s called. That’s podcasting software you can record online but if you just google it.

Adora Cheung [00:23:23] – Okay got it cool. Alright. And then how do you and then what’s that. Sorry. This is really noob questions but like, so you’re recording it, you’re editing it, do you use software to edit?

Craig Cannon [00:23:33] – Oh yeah. So we definitely use software to edit. There’s free software called Audacity. Again you can take the file from your iPhone put it into Audacity you’re good to go. We use, because we have video we actually just edit the video and then export the video audio to a podcast.

Adora Cheung [00:23:53] – I see.

Craig Cannon [00:23:53] – And then if you’ve heard it before but I recorded an intro thing.

Adora Cheung [00:23:57] – Right. Got it. Yeah.

Craig Cannon [00:23:58] – Which is what I like but other people like songs, other people like little clips from the show whatever. Then you have to serve it and we use Backtracks

Adora Cheung [00:24:07] – Got it. Okay. Cool. Alright. So you mentioned voice. Do you think your voice sounds awful when you listen to it?

Craig Cannon [00:24:15] – Well I mean, you get used to it, that’s my answer.

Adora Cheung [00:24:19] – Okay. Yeah. Because you have to. Because you’re the one editing too, so have to play it back. Okay. So you just get used to it.

Craig Cannon [00:24:24] – Yeah. My answer to this question is actually well, how do you feel about your voice?

Adora Cheung [00:24:30] – I generally don’t like it. But it sounds different than when I’m hearing myself, I sound very different than when I hear it on a recorded version.

Craig Cannon [00:24:42] – Is it lower or higher? How does it sound here?

Adora Cheung [00:24:45] – It’s just not what I expected. It’s low. A little bit lower I think. I think, I don’t know.

Craig Cannon [00:24:52] – It’s tricky because actually some people have figured out ways to manipulate in post-production their voice to make it sound closer to what it sounds like in their head. I often think about this. I did an episode of another podcast and it was bassier then we normally record at. I was like, “Oh man, that sounds like more like my actual voice.” But yeah, I personally I don’t really like the NPR tone like really like soft. I don’t really it. So I’m okay with it. My voice in my head is lower. But as soon as you start recording yourself on video all the time, you’re like, “Oh man that’s what I look like?” Then you feel way worse about that. Yeah I got over it.

Adora Cheung [00:25:34] – Okay, cool. So let’s move to what you’ve learned from the YC podcast itself.

Craig Cannon [00:25:40] – Sure.

Adora Cheung [00:25:41] – Alright. So let’s start off with actually what’s been the best interview, your favorite interview so far?

Craig Cannon [00:25:47] – So my favorite interview? So the most popular one is Leonard Susskind. So that’s the most popular one. But I’ve actually learned a lot from different people. I really like the Michelle Kuo interview with Kat. So that was about art and technology.

Adora Cheung [00:26:05] – Oh that’s right.

Craig Cannon [00:26:06] – That was a fun one. She’s awesome. Then Ryan Peterson interview was a great one. He’s got this cool hustle but not annoying vibe which I really like. Rosalind Watts, the psilocybin the mushroom interview.

Adora Cheung [00:26:20] – That’s right.

Craig Cannon [00:26:21] – Because I mean I had heard about it but I didn’t know it in that detail. That was awesome. And then maybe some other ones with my friends have been really fun.

Adora Cheung [00:26:31] – Cool.

Craig Cannon [00:26:33] – Like my friend Matt Hackett started this company with Casey Neistat so I liked that one.

Adora Cheung [00:26:37] – Oh that was very cool.

Craig Cannon [00:26:37] – Yeah yeah yeah.

Adora Cheung [00:26:38] – Alright. And what’s the most surprising thing you’ve learned about startups after joining YC and interviewing so many founders like Ryan?

Craig Cannon [00:26:45] – I mean this is definitely one that you should answer too. But I think a core part of it that wasn’t obvious to me from the outside was how important confidence is, and how big of a role it plays in just doing the thing. A lot of people oftentimes when I meet them and they’re interested about YC they make up these things in their heads that disqualify themselves from starting. A lot of the successful founders don’t do that ever. Then they also have gotten into YC or some other thing, and they have a little bit of kind of wind behind them, and so they have just the confidence to do the thing. I would say that’s a learned trait, and that’s a skill that you can develop, and a lot of people might not think it is. But I really do think it is. So, I would just tell people, just do the thing and know that you’re good enough because they’re just normal. I don’t know, what would you say?

Adora Cheung [00:27:43] – No I think that’s a good observation. I think it’s hard to… You know one of the things I was working with startups now that I do is during office hours for example is just keep the optimism of where this could go at a realistic but high level. Meaning every day, the ground every day, you would not think it’s going anywhere fast. But so it’s always, I like to remind people like this is where you started this for for this reason. This reason could be bigger than what you even thought about what you thought it could be. But regardless you should always think about why you’re doing something.

Craig Cannon [00:28:34] – That’s a really good thing too, like bigger than you think it could be. This is a big… It’s a core thing in Silicon Valley that gets some criticism and because you could say like alright not everything is venture fundable. Nor should it be.

Adora Cheung [00:28:49] – Sure.

Craig Cannon [00:28:51] – But there’s another way to think about that which is it’s not as risky as you think it is. It’s actually often easier to find people to work with if you’re like, “I’m just going to build rockets now.” You really stand out. Whereas doing these, I don’t want to put it down, but hackathon level SaaS tools isn’t as compelling to people.

Adora Cheung [00:29:11] – Right.

Craig Cannon [00:29:11] – That has been a big takeaway for me as well.

Adora Cheung [00:29:13] – Alright. I’m just going through questions that Twitter has. Twitter was great. I don’t have to prepare much for this interview. So what have you learned from any of your guests that you’ve put into practice?

Craig Cannon [00:29:30] – Okay. I think the honest to god main thing is it’s just gotten me super anxious about doing my own thing.

Adora Cheung [00:29:41] – You must do a startup now.

Craig Cannon [00:29:43] – Or something. Because you can only interview so many people where you’re like… I mean this is fun to do but being the host, it kind of sinks into your mind. I mean kind of reviewing YC applications too as this observer of trends happening, of things happening, and you realize that you’re just this passing moment in someone else’s life. It’s cool when everything … But they’re getting right back to their thing. So I really admire that. That’s been a big thing. Sam encouraged me to just do the thing which was always good. He’s very helpful there. The mushroom interview, very interesting, and you can do your own research privately in different countries if you want to do that. Tim Hwang, he did the container book with me.

Adora Cheung [00:30:29] – Oh that’s right.

Craig Cannon [00:30:30] – Yeah. And he’s been on twice.

Adora Cheung [00:30:34] – He’s the AI policy guy? I remember. Okay. I’ve met him.

Craig Cannon [00:30:37] – Tim’s awesome and so Tim is one of the only people I know who has been able to maintain cool jobs, but also have all the little side hustle projects going on. His work ethic is unprecedented in my mind for that kind of thing. I think maybe the last one is just realizing, it doesn’t take that much to generate a pretty real following online by writing and communicating clearly. I think YC, that’s at the core of YC, like PG’s essays or content marketing. I mean they’re cool. They’re obviously valuable. Andrew Cortina from Venmo that’s how I found out about him and even Michael essays are great. It really helped him.

Adora Cheung [00:31:26] – I like them when they’re to the point.

Craig Cannon [00:31:28] – Yeah I mean this is tricky right? That’s just a style thing. Who are year favorite writers right now? I guess in that in that scene.

Adora Cheung [00:31:37] – In the tech scene?

Craig Cannon [00:31:38] – In the tech scene.

Adora Cheung [00:31:39] – I don’t …

Craig Cannon [00:31:40] – You don’t read them?

Adora Cheung [00:31:41] – Honestly, I don’t read them.

Craig Cannon [00:31:42] – That’s what I’m saying. This is a podcast too. Yeah exactly what I’m saying.

Adora Cheung [00:31:46] – I wish PG would write more essays is what I am secretly hinting at that, anyway. Alright. What are the most counterintuitive or maybe non consensus things you’ve learned about building successful startups after interviewing so many founders?

Craig Cannon [00:32:06] – Well I also, I want your answer on all of these. These are really really cool questions. There’s definitely no one model for a successful startup. They’re usually not riding some trend in the middle of the wave. They’re way early. So it seems weird. They’re not doing AI, blockchain, da da da right now. That’s definitely a thing. Then I think they often are more focused on finding these really big problems than they are on just focusing on doing a startup or a company. They’re definitely not attached to a solution. A lot of these people with that in mind in my experience there aren’t a lot of crazy pivots like 180 degree pivots. They come in and they’re like, “Hey I found this thing.” and then all of a sudden they realize that it’s quite large, where they change degree a little bit, you know but it’s not like a total turn. Then the last thing is, they’re just normal people, I don’t know. I think that they get built up so much.

Adora Cheung [00:33:04] – Yeah I agree with that. Cool.

Craig Cannon [00:33:09] – What’s your answer?

Adora Cheung [00:33:10] – It’s a good question. You know I actually agree with the whole… What did you just say about the AI blockchain thing?

Craig Cannon [00:33:24] – Oh they’re not in the middle of a big trendy wave. They’re early.

Adora Cheung [00:33:29] – Early. Oh okay. So know what I was thinking was, I think the best ideas are when you can explain the problem and even the solution without saying jargon, without saying AI or blockchain. So I think some investors are, when you say those words, They’re like, “I’m in.” I think if you can articulate it without actually describing the new tech you’re doing. That’s always the mechanism of which you’re solving the problem. I don’t think that’s the problem you’re solving, if that makes sense.

Craig Cannon [00:34:02] – I totally, I mean it is these questions like, “What mac do you need, man?” It’s a tools question.

Adora Cheung [00:34:06] – Right.

Craig Cannon [00:34:07] – It’s not a product question and that’s the answer. Like I said, content, product, same thing. Do you make a good podcast? Do you make a good app or whatever you might be making.

Adora Cheung [00:34:15] – Okay. So now that you’ve done podcasting for many years, if you had to start one again from scratch, how would you structure it?

Craig Cannon [00:34:26] – Okay, so I have a couple notes on this, but the thing is, I kind of did start this podcast from scratch, so in many ways it reflects my personal taste, and how I like shows to go. If I were to do my own thing, not YC related from scratch, to that, like the main constraint here has been, this is still my job, right? In that way I think in real life, I would have, in real life, in a non-YC podcast, I’d have more really strange people, weird, like definitely do not fit in this podcast.

Adora Cheung [00:35:03] – What’s an example of that?

Craig Cannon [00:35:04] – Okay so one friend comes to mind. He’s not actually weird, not that weird, but he is an off-the-grid guy in the middle of Vermont, and so he’s built his whole cabin in the woods. He’s homeschooled all his kids. He is solar powered, all that stuff, but he’s also a teacher at a college. He’s super smart but a sweetheart, and living this very weird different life that I think appeals to a lot of people. So stuff like that. There have been moments where I’m like, “Is this a YC episode?” eh, whatever. I mean even the Casey Neistat episode I was a little bit like, “I don’t know if this is going to fly.”

Adora Cheung [00:35:47] – So there’s a little bit of a branding thing you have to think about. Is that what you’re talking about?

Craig Cannon [00:35:52] – Well yeah, I mean this is a separate conversation, but given that the podcast is grown a little bit, you know I have like 18 bosses.

Adora Cheung [00:36:03] – Oh man, that sounds awful.

Craig Cannon [00:36:05] – Everyone at YC’s cool but at any given moment I can get emails from anyone. Like, “This is how I feel about the podcast.” Usually it’s an expression of personal taste. This is something that you have to get used to with creative work, right. It’s like differentiating, “Oh this is objectively good feedback”, even if it hurts versus “Oh they just have a personal opinion. They feel that way.” And both strategies can work, which is really hard.

Adora Cheung [00:36:31] – Got it.

Craig Cannon [00:36:32] – So to answer the question, I would make it more weird. I would have maybe sillier people on, but I would definitely still do YouTube, do transcripts, do the podcast, clip the show as much as you can. I’m really bad at that, clipping it for YouTube. And then pro tips. Big names still work. Trends still work. I don’t do a lot of trend stuff, but big names work.

Adora Cheung [00:36:58] – When you talk about clipping, do you see, does that in whole unique wise, unique listener wise anyway get you more listens than people just listening it from the audio stream?

Craig Cannon [00:37:12] – So what’s tricky. This is a learning. We have two YouTube channels, subscribe. We have Y Combinator and Y Combinator clips. Because what happened was initially I was like, “Oh I’ll just clip the show, because this is great.” It’s great for SEO. You title it like, Jessica Livingston on finding a co-founder, rather than Jessica Livingston with Sam Altman.

Adora Cheung [00:37:35] – Right.

Craig Cannon [00:37:36] – And then you can make five clips from one episode which is cool, but when I put out all seven videos on one day, everyone freaked out on the YouTube comments. Like, “What are you doing man? You’re clogging my feed.” So I was like, “Okay fine. I’ll make a clips channel.” The problem there is the clip channel doesn’t have that flywheel effect. So in the long run, you see this with Joe Rogan. There are in aggregate, like his show clipped out will do more than an individual episode, but you need an audience before.

Adora Cheung [00:38:06] – Right yeah.

Craig Cannon [00:38:07] – Which requires like, bigger names help in that way.

Adora Cheung [00:38:10] – Right. Makes sense. One question, why are more podcasts not actually videos on YouTube?

Craig Cannon [00:38:15] – Because people are dumb.

Adora Cheung [00:38:17] – By people you mean?

Craig Cannon [00:38:19] – Podcasters. No it’s more work, right? I think this is actually a fairly new revelation. Some people have been doing it for a while but I don’t think it’s been as obvious to people that you can even just upload a still image of you and then the audio and that would be a thing. Yeah.

Adora Cheung [00:38:42] – It’s interesting that you actually thought on reverse like, “I want to start a YouTube channel because that’s where the audience is.” And then podcasting is a excuse to get that content. That’s smart.

Craig Cannon [00:38:55] – Well the question was, I met with Michael in this room, when we were talking about it, and we were like, “Where are the youth hanging out?” You know what I mean? And I was like, “Man I don’t know.” A lot of these other mediums are kind of feel aging to me, whereas YouTube is just going to be young, or it still is young for a while.

Adora Cheung [00:39:12] – Oh then you guys started Instagram.

Craig Cannon [00:39:13] – Yeah. There’s another thing about that. Thanks for reminding me.

Adora Cheung [00:39:17] – Shall we do Snapchat too?

Craig Cannon [00:39:19] – We didn’t do Snapchat. I held out because people were like, “Oh you want to be the YC personality on Snapchat?” No fucking way.

Adora Cheung [00:39:26] – We’re adjusting for that.

Craig Cannon [00:39:27] – Yeah but we clip the podcast on YouTube, on Instagram and that actually does really well too. It just takes work.

Adora Cheung [00:39:33] – Alright. Yeah. Alright. So what patterns have you recognized just from YC. But when a YC podcast, when an episode gets popular, viral, what are the reasons for that? Besides big name.

Craig Cannon [00:39:49] – Yeah big name’s an easy one. Usually it’s some certain cohort of influencers grab it online, and then it just goes. This has been true, and I won’t go so far as to say any of the episodes have gone viral. Definitely not. But one of the strategies for the physics episodes was, we want more people to apply who are studying physics and there aren’t that many big names in those communities, therefore if we get the biggest names in those communities, we can get them to at least know about YC, right? So what I realized there was those communities, again not viral, but as soon as anything is shared within those communities, everyone shares it. So you have John Preskill will share it. But then Sean Carroll will share it, and then Scott Aaronson will share it. And it’s one, two, three, four, five, six. And so yeah, finding these small but really tightly networked communities works really well.

Adora Cheung [00:40:52] – It’s almost like you want guests that are maybe not within startup tech itself, but kind of adjacent.

Craig Cannon [00:40:59] – This is just my personal opinion. This is how I differentiate a show.

Adora Cheung [00:41:03] – Makes sense.

Craig Cannon [00:41:04] – Because I’m like, “Okay.” Actually a really good example of that is Mr. Money Mustache. Did you listen to that one?

Adora Cheung [00:41:10] – What was that one about?

Craig Cannon [00:41:11] – So that was about personal finance and saving money.

Adora Cheung [00:41:14] – Oh I don’t think so.

Craig Cannon [00:41:15] – Okay. So this has been a crazy trend happening in the past maybe 10 years about people saving high high high percentages of their income and quote retiring early. Right. So I think Pete, this guy Mr. Money Mustache saved something like 600K, and owned his house outright, and then he quote retired at 30. He’s become a figurehead and a cult leader. I mean yeah, the episode is called, Don’t start a blog, start a cult. This comes from one of his talks, and people at YC were like, “Dude, what are you talking about, start cults?” But he has this passionate following of in large part software engineers because they earn so much money, it’s very easy to save 50 percent of your income. I was like, “Oh this is tech adjacent. This physic thing is tech adjacent. People taking mushrooms, that’s tech adjacent.” That was more of a trend thing actually.

Adora Cheung [00:42:12] – Cool. Alright, in terms of the future of podcasting, it seems like it’s taking off now. One of the primary problems I guess is, it’s hard to make money. I mean it starts with it’s hard to measure, but one it’s hard to make money. What do you think is the future of podcasts monetization?

Craig Cannon [00:42:34] – I think there are a few possible avenues. I tweeted this out recently, but with the Spotify Gimlet, Anchor deal right? It’s conceivable that a lot of these podcasters get on contracts with big companies like Spotify, and are just paid, because for the majority of them, they’re not making more than 1000 bucks a month off of ads. Like if you’re not a big podcaster, a lot of them aren’t making any money, and actually don’t care all that much about having maximum distribution, which is different than Rogan because Rogan wants to sell comedy shows. He’s monetized his podcast. This is why comedians dominate podcasts. They have a business plan right here. This is all marketing, and their content’s super interesting, so they’ve figured it out. The people who have had products on the side have figured this out for a long time. I think we’re going to see a decrease in CPM around podcast advertising because it’s been a racket, and now it’s I think it’s really thinned out.

Adora Cheung [00:43:36] – As in it was…

Craig Cannon [00:43:38] – More lucrative than it is now.

Adora Cheung [00:43:39] – I see it was higher than what it actually performed.

Craig Cannon [00:43:44] – Because it was just made up, right? So you’re like, “Hey MailChimp I want 20 grand.”

Adora Cheung [00:43:47] – I see.

Craig Cannon [00:43:48] – And they’re like, “Okay, fine.” That’s how it goes. So yeah, so I think that’ll be a trend. I think we’re going to see some kind of Patreon model work out in some way. I wouldn’t be surprised if we saw more tipping happening, that will probably be a new app. Stuff like Himalaya in China for sure. Tons of education content.

Adora Cheung [00:44:06] – Yeah. That’s a good one.

Craig Cannon [00:44:07] – One thing that I’ve really been surprised that doesn’t exist yet is super expensive podcasts.

Adora Cheung [00:44:12] – Huh. Like $10 an episode type expensive or?

Craig Cannon [00:44:16] – More. So you listen to Hardcore History?

Adora Cheung [00:44:19] – I have, yes. It’s free.

Craig Cannon [00:44:21] – That could be 50 bucks an episode easily. Like you see this stuff Masterclass happen. Why isn’t Hardcore History expensive?

Adora Cheung [00:44:28] – What’s the… Right, and then you’re seeing more, I guess we pay for audio books. So I guess you’re saying there’s something in the middle between audio books, which we pay a lot for and free podcasts.

Craig Cannon [00:44:40] – I heard this stuff last year, but I’m not sure that it’s totally true, but last year or whenever it was quoted, the audio book market was $3 billion. In the same year, the podcast market advertising was $300 million, and then when I talked to my friends like, “Wait a second. There’s this huge gap here.” Because most people are actually listening to your podcast not audio books. So there has to be some kind of thing in the middle, especially around educational content, where people pay a lot of money to have you, and teaching them, educating them, because I think there probably is a definitively best American history teacher, and a definitively best Mandarin teacher.

Adora Cheung [00:45:19] – Right.

Craig Cannon [00:45:20] – I don’t know, I’d pay $1000 a year for their podcast or whatever.

Adora Cheung [00:45:24] – Have you heard of the Great Courses? That seems kind of in that spectrum.

Craig Cannon [00:45:28] – But it’s like internet 2.0 though. I think there’s a new a bigger version that will happen.

Adora Cheung [00:45:34] – Cool. The Himalaya is actually I think…

Craig Cannon [00:45:37] – Crazy.

Adora Cheung [00:45:38] – If you don’t know about it, you should check it out. Chinese.

Craig Cannon [00:45:42] – I’m trying to get the YC podcast on it right now.

Adora Cheung [00:45:44] – Oh, I really? Awesome.

Craig Cannon [00:45:46] – But it’s this big complicated thing.

Adora Cheung [00:45:47] – Alright. Okay so there are so many podcasts out there. Do you think it will become saturated like the music industry, or do you think the music industry is saturated?

Craig Cannon [00:46:03] – No. I thought that question was a false premise. I don’t think music, or is YouTube saturated? I don’t think so. Is blogging saturated? I mean there’s a lot, but that doesn’t mean like, you know, like you said, like PG doesn’t write an essay a day for you. Yeah. And would that be enough? Maybe not even.

Adora Cheung [00:46:22] – What do you think is missing in the podcast world? I guess we talked about educational content.

Craig Cannon [00:46:27] – I mean there’s a lot of missing stuff around monetization for sure but I think in many ways it’s going to be about people committing. A lot of people do it on the side, or they’ve already had a product, right? So I think shifting that model to be like, “Hey this is valuable. You should pay for it. I’m making really great content.” That might require some kind of basic income salary from Spotify. So if I’m like, “Hey Adora, you want to make Kids Say the Darndest Things? Here’s whatever, 30 grand a year.” That’s enough for you to get really motivated to make all this stuff. Because oftentimes you don’t see it because iTunes doesn’t make it obvious, but iTunes has hundreds of thousands of dead podcasts, and they just never get it going enough to commit.

Adora Cheung [00:47:13] – Right. It’s after three or four and then it just kind of doesn’t go anywhere.

Craig Cannon [00:47:17] – Yeah and then you’re done. And then you quit.

Adora Cheung [00:47:20] – That’s a good idea. So what you’re saying is Spotify might do the Netflix model of, or what you would hope is that the Netflix model, where they can get you to a certain number of episodes, and then you just go for it. Then if it does well, you just redo.

Craig Cannon [00:47:34] – Because, think about it, right. So I heard that Jerry Seinfeld signed $100 million deal with Netflix for Comedians in Cars plus some other stuff. Okay, how much could Netflix or Spotify sign Adora for? Probably less than $100 million. So you could imagine a world where they hire 100 podcasters at 30 grand a year. They all work from anywhere in the world and they just make stuff that people are really into.

Adora Cheung [00:48:02] – Right.

Craig Cannon [00:48:03] – For Spotify. Because at 30 grand per person, that’s actually not nearly as much as paying for all of the, I don’t know, Lady Gaga royalties. So yeah, I could see that happening.

Adora Cheung [00:48:15] – In terms of podcasters, so you obviously you listen to lots of podcasts. What has been, you talked a lot about Joe Rogan, but who else has been the most influential for you?

Craig Cannon [00:48:29] – I think Russ Roberts is great. When I started the YC podcast, I had just heard about EconTalk.

Adora Cheung [00:48:36] – He’s been doing it for a long while.

Craig Cannon [00:48:37] – Forever. I still don’t know why that show is not bigger. Like it’s pretty big but it could be bigger. I wanted to do a combination of EconTalk and Rogan, where it’s interesting people who are technical, but it’s also fun, because EconTalk can be a little dry sometimes. I really like those, but I have this whole list I wrote down of other shows I listen to.

Adora Cheung [00:48:57] – Sure.

Craig Cannon [00:48:58] – So there are a ton of dead podcasts that are still good. There’s one called Seventh Avenue projects. So this is by this guy Robert Polley who lives in SF, somewhere nearby SF. It’s basically like an NPR Science Show and the interviews are great. They’re like an hour long. It’s got the NPR vibe. But if you can get past that, it’s cool. There’s another podcasts I listen to called Barbell Medicine. So have you ever gotten into lifting weights at all?

Adora Cheung [00:49:25] – Not really.

Craig Cannon [00:49:26] – Okay. So I got into it last year, because I hurt my back and I was like, “How do I fix this?” And people said, “Well you should lift.” And I was like, “Okay cool.” So there’s this podcast called Barbell Medicine. It’s two doctors who talk about medical research as it relates to exercise.

Adora Cheung [00:49:42] – Oh.

Craig Cannon [00:49:42] – And so they read a bunch of papers, and say like, “Oh you know, creatine is good.” Or like this protein’s garbage, and this type of exercise does nothing, and this is why you should train three sets of five versus something else.

Adora Cheung [00:49:55] – Got it.

Craig Cannon [00:49:56] – Surprisingly interesting. Dead authors podcast, you listen to that one?

Adora Cheung [00:50:01] – Mm-mm.

Craig Cannon [00:50:01] – This one’s also dead. It’s Paul F. Tompkins bringing on comedians who imitate dead authors. It’s like an interview show.

Adora Cheung [00:50:10] – Do they do it in their voice too? That’s hilarious.

Craig Cannon [00:50:12] – Yeah. Yeah. But I mean it’s all goofy. Oftentimes you don’t really know what their voice sounds like. The Borges one with Nick Kroll is amazing, if you want to check it out.

Adora Cheung [00:50:21] – I will.

Craig Cannon [00:50:22] – Berkshire Hathaway, so Yahoo got the rights to the Berkshire Hathaway board meeting, or not the board meeting, the conference.

Adora Cheung [00:50:29] – The shareholder meeting, yeah.

Craig Cannon [00:50:30] – The shareholder meeting. That’s a podcast.

Adora Cheung [00:50:31] – Oh wow.

Craig Cannon [00:50:32] – Which is awesome. I have a couple more. The Nine Club. If you were into skateboarding growing up, Nine Club is amazing.

Craig Cannon [00:50:41] – They interview a bunch of skateboarders from back in the day, it’s fucking awesome. My buddy Spencer does one called Prepared, that’s about manufacturing. I did an episode on that. And Startup School podcast by Seth Godin. Did you ever hear of that one?

Adora Cheung [00:50:55] – No.

Craig Cannon [00:50:56] – Same name.

Adora Cheung [00:50:57] – Yeah yeah.

Craig Cannon [00:50:58] – Like 2012. It’s actually really good.

Adora Cheung [00:51:03] – Cool. Alright.

Craig Cannon [00:51:03] – That’s my list.

Adora Cheung [00:51:04] – I’ll check out all of those. How did you discover the Dead Podcast?

Craig Cannon [00:51:08] – Dead Author Podcast? I subscribed when it was still active.

Adora Cheung [00:51:11] – I mean the dead, because I have a topic that I’m interested in, I’ll go and search for it, and then that’s how I discover.

Craig Cannon [00:51:19] – Oh yeah.

Adora Cheung [00:51:19] – Some of these podcasts that don’t really exist anymore.

Craig Cannon [00:51:22] – So what ones are you into that are dead?

Adora Cheung [00:51:24] – Well I’m not into it. I just listened to that one episode.

Craig Cannon [00:51:27] – Yeah. Okay.

Adora Cheung [00:51:28] – I don’t actually.

Craig Cannon [00:51:29] – Have you checked out Listen Notes?

Adora Cheung [00:51:31] – Yes that one’s a good one.

Craig Cannon [00:51:32] – Listen Notes is awesome because they index everything. That’s a big thing but I mean it should be said discovery’s totally broken. Which is why the clipping. This is what I think will happen. There will be some version of a podcast app that resembles YouTube clipping. That’s a podcast app. So what happens with YouTube clipping is you’re just getting this five to ten minute clip one after the next after the next. And Himalaya is much more like that than the standard model of feeds and stuff.

Adora Cheung [00:52:01] – Yeah. More Twitter questions. These are trying to get unrelated, but we’ll just finish off with some unrelated ones.

Craig Cannon [00:52:10] – What podcast you listen to? YC?

Adora Cheung [00:52:12] – Yeah. The YC one.

Craig Cannon [00:52:15] – Joe Rogan?

Adora Cheung [00:52:16] – I listen Joe Rogan. I do listen EconTalk. I listen to Tyler…

Craig Cannon [00:52:19] – Cohen?

Adora Cheung [00:52:20] – Cohen, yeah, has a good one. I listen to Recode Decode, that one.

Craig Cannon [00:52:28] – Why do you listen to podcasts?

Adora Cheung [00:52:30] – What? Well, I will preface, what I actually listen to audiobooks much more.

Craig Cannon [00:52:37] – Oh okay.

Adora Cheung [00:52:38] – So when I’m kind of tired of listening to the audiobook, I will either switch to music or podcasts. So it’s kind of my other thing that I listen to.

Craig Cannon [00:52:46] – But you’re kind of tuned out when you’re listening? You’re doing something else?

Adora Cheung [00:52:49] – No, if I’m doing something else, I listen to music. Like it’s hard to listen audiobooks especially, but also podcasts, when you’re tuned out. The tech ones are actually… Yeah I guess I’m not learning anything entirely new, and so you can just listen to it while you’re doing something else. So that’s what I do.

Craig Cannon [00:53:10] – Okay. Yeah. I’m similar.

Adora Cheung [00:53:11] – Patrick Bender asks. What idea do you believe in that your social group would think is crazy?

Craig Cannon [00:53:17] – So this is why I’m glad we got this question beforehand, I had a moment to think about it. I think cushy Internet jobs are bad for innovation.

Adora Cheung [00:53:30] – Okay. Like what’s an example of that?

Craig Cannon [00:53:33] – Any FANG job, where you show up and kind of do work.

Adora Cheung [00:53:39] – Got it.

Craig Cannon [00:53:40] – And for that reason I think jobs should have term limits on them unless you’re the founder. So basically reverse vesting. So it’s like, “Hey Adora, you’ve been a partner at YC for five years, see you later.”

Adora Cheung [00:53:54] – Yep. That’s actually not a bad idea.

Craig Cannon [00:53:56] – It’s kind of implied that if you go join Sequoia or something, like okay fine. Yeah. Because it’s related to this early retirement thing but I see a lot of people maximizing that, and just staying on at big companies, and it makes me mad because they have so much talent, and they have safety nets. They could go do stuff.

Adora Cheung [00:54:21] – Interesting. I think maybe somewhat related to that, I think there should be forced sabbaticals.

Craig Cannon [00:54:31] – Totally.

Adora Cheung [00:54:32] – After you work for so many years you should take time off to just do something else. ‘Cause I think if you work at a company especially if it’s just one position and on one team you just kind of get stuck and you lack that creativity flow and just thinking outside the box gets a little bit harder after some time.

Craig Cannon [00:54:54] – I’ve been surprised that that’s not like a bigger employee retention thing. I know some companies do it but it’s after quite a while. Kat did one last year.

Adora Cheung [00:55:05] – Yes, Kat who is also a YC partner.

Craig Cannon [00:55:07] – Yeah. Yeah. She came back because she had all these thoughts, right? Then she came back and she was super excited and really happy. And was like, “You know what? I kind of didn’t feel like doing anything.” And that was okay too. I got off my phone. To her point, that’s totally fair. But I do feel that the forced sabbatical would need to be longer than the company one.

Adora Cheung [00:55:31] – Yes. I haven’t thought about how long it should be. At least six months. Three months, six months?

Craig Cannon [00:55:39] – I think it’s such a good idea. If there is an even greater incentive for them to… Basically what I’m saying is I want people to leave their jobs, if they’re, “We will decrease your salary if you return.” Or we’ll give you some seed funding or something, but then you see this stuff happening at Google, where they’re funding internal startupy things. It just feels like employee retention.

Adora Cheung [00:56:02] – Right. Yeah, I don’t know. Yeah I haven’t thought through what the right mechanism for that it is.

Craig Cannon [00:56:10] – Because I’m curious about you. How long have you been at YC?

Adora Cheung [00:56:13] – Two and a half, almost three years.

Craig Cannon [00:56:16] – Yeah we started roughly around the same time.

Adora Cheung [00:56:18] – Probably around the same time.

Craig Cannon [00:56:19] – Yeah. Like how much time do you think you would want to really consider?

Adora Cheung [00:56:23] – Three to six months is probably I think, because then I think it lets you just focus on other things. That again will help you with your job actually.

Craig Cannon [00:56:36] – But yeah. This is the thing. A lot of people don’t know this about you at YC, but you’ve jumped around between a bunch of stuff.

Adora Cheung [00:56:42] – Within YC.

Craig Cannon [00:56:42] – Within YC.

Adora Cheung [00:56:43] – That’s right.

Craig Cannon [00:56:44] – Whereas some other people haven’t.

Adora Cheung [00:56:46] – Right.

Craig Cannon [00:56:47] – Right? And so you’re kind of always looking for it.

Adora Cheung [00:56:46] – Right. That’s my version of ADD.

Craig Cannon [00:56:50] – Yeah totally. Is that also in the back of your head, like maybe I want to start a city, or maybe I want to do this on my own?

Adora Cheung [00:56:58] – Yeah. We’ll see. In the back of my head is always what’s the next startup?

Craig Cannon [00:57:04] – Sure.

Adora Cheung [00:57:05] – So that’s always, and I think we talk about this in our episode.

Craig Cannon [00:57:09] – Probably.

Adora Cheung [00:57:10] – Maybe on one hand being at YC is great, because you’re with all these founders, and you’re motivated about startups in general, and there’s so many ideas. On the other hand it’s like, one week I’m obsessed with this one idea, and then I talk to another founder, then I just ping pong around ideas. So it’s very hard to stay focused on your own stuff.

Craig Cannon [00:57:36] – It’s tricky right because I can see you going both ways, because with all of this stuff, it’s all good. There’s no objective right answer, but I can see that intellectual game being really compelling.

Adora Cheung [00:57:48] – Yes. It’s addictive too.

Craig Cannon [00:57:49] – Totally. But you’re also a maker right?

Adora Cheung [00:57:52] – Exactly.

Craig Cannon [00:57:53] – And so that just might happen.

Adora Cheung [00:57:55] – Yeah. Watching people build and you’re on the sideline not building is really rough. So you have to come up with at least hobbies, side projects that often go uncompleted unfortunately. Alright. So Zachary Cannon asks. So this is one of the application questions for YC. Please tell us about the time you most successfully hacked some non computer system to your advantage.

Craig Cannon [00:58:24] – So I kind of mulled over this one for a while, and I think that the silly world record actually might be the best one because it had the largest outcome. So basically what happened was there was this trend in cycling whenever it was like four years ago where people were climbing the height of Everest on their bike and they called it Everesting, and I was like I can probably do that. Meanwhile I’m not, I mean I’m heavier now than I was then. But even then I was one 170 pounds which in cycling is heavy, like you’re the fattest cyclist if you’re 170 pounds.

Adora Cheung [00:58:59] – 170? What’s the typical weight?

Craig Cannon [00:59:00] – I mean the guys who win are 135, 140 and they’re taller than me.

Adora Cheung [00:59:07] – Wow.

Craig Cannon [00:59:08] – So they’re stronger than me too.

Adora Cheung [00:59:09] – They all look very tall and skinny.

Craig Cannon [00:59:11] – They look like skeletons. Yeah. So you’re looking at probably 5’11, 137 pounds something like that, and they’re stronger than me. So I’m 170 pounds and not not that skinny. So basically what I did is, I did that Everesting thing and it worked. I was like, “I could do more of this.” Then I created a spreadsheet of all the hills in the East Bay, where I could maximize how much elevation I could get in the shortest distance while also being close to a bathroom also not having too much traffic something that my friends could get to so they could help me out. Through that spreadsheet, I unlocked this place that just worked for me. So that’s basically how it happened.

Adora Cheung [00:59:55] – Oh, wow. Yeah that’s pretty cool.

Craig Cannon [00:59:57] – It was pretty cool.

Adora Cheung [00:59:58] – You achieved your goal.

Craig Cannon [00:59:59] – I achieved my goal.

Adora Cheung [01:00:00] – Of Everesting.

Craig Cannon [01:00:01] – Exactly. And then my life was over ever after. Yeah basically and then I left the country.

Adora Cheung [01:00:09] – Alright. Cool. So last question. You obviously talk to a lot of founders being at YC similar to myself. Do you ever feel the pressure to just go start a company and if you’re going to start a company, what would the problem be that you want to solve?

Craig Cannon [01:00:28] – Do you have an answer for this one for yourself? Okay. I’ll answer it first.

Adora Cheung [01:00:31] – The answer is yes I do feel.

Craig Cannon [01:00:34] – Oh yeah. Okay. So yes the answer, that’s a leading question totally. Of course. That’s another thing that’s not really talked about much on the podcast or in public at all. But working at YC and managing at YC is a weird kind of cat wrangling where the default personality type is solo founder kind of vibe, and everyone just wants to be doing their own thing all the time. It’s boxing people kind of.

Adora Cheung [01:00:58] – You’re a bunch of CEOs, former CEOs basically.

Craig Cannon [01:01:01] – With very different styles, which is actually kind of interesting, like it hasn’t been selected for one vibe. Anyway I think the answer is definitely yes. Where I’m kind of focusing right now is I’m getting this impression that people want freer lives. I think you see this with early retirement. But I also think you see it on the other side with basic income. Then I think you see it in the middle with like Marie Kondo and so there’s just this vibe that people want potentially less stuff, potentially simpler lives, potentially more freedom. So I think I would probably develop a product in that space around one of the things that’s most expensive. So probably a housing thing, where it’s a ton of your income goes into this but it’s this aspirational thing that leads you to living a freer life.

Adora Cheung [01:01:59] – Interesting. Okay, I think I understand.

Craig Cannon [01:02:05] – Well I mean I’m a little vague, because I think I might end up doing it.

Adora Cheung [01:02:10] – Cool. Alright. Anything else?

Craig Cannon [01:02:16] – What about you? There’s tons of Adora knowledge that hasn’t been on the podcast. You’ve only done it twice.

Adora Cheung [01:02:20] – Yeah I think I’ve done it twice.

Craig Cannon [01:02:23] – Three times?

Adora Cheung [01:02:23] – I did it once talking about start up school and then once random questions from the Internet. Yeah. Yeah I probably should do more podcasts or do more writing or something.

Craig Cannon [01:02:32] – If you want. What attracts you as an idea right now? Like a market, I don’t know.

Adora Cheung [01:02:38] – It’s a good question. There are a bunch of things I think anything related to making life in a city better. Anything from starting new cities to just mobility and housing and stuff like that I’m interested in. So we’re funding more of those things at YC.

Craig Cannon [01:03:00] – Cool.

Adora Cheung [01:03:01] – I’m very on the other polar opposite, so it’s kind of ironic I’m also interested in this is remote collaboration and remote work stuff. Trying to figure out what are the tools that can help kind of replicate the… I think a lot of Slack and video and stuff like that that’s all well and good but the thing that you still don’t get is the serendipitous nature of living in a city. And is that possible when you’re not actually physically together? I think if we can get, if we build something and get there then maybe cities aren’t as needed. But yeah anyway that would go in the face of 2000 years of why cities are great and why it spurs innovation.

Craig Cannon [01:03:52] – No, they totally do. If an alien showed up it would be, “Oh humans build these things.” Like that’s our one goal build these things.

Adora Cheung [01:04:03] – Yeah. So those are two topics. I’m starting looking to brain computers, and stuff like that.

Craig Cannon [01:04:11] – Oh like Neuralink type stuff?

Adora Cheung [01:04:12] – Yeah yeah stuff like that, but I’m just starting.

Craig Cannon [01:04:16] – Is there anything cool happening right now, like anything working?

Adora Cheung [01:04:19] – I’m such a beginner.

Craig Cannon [01:04:21] – Total noob, yeah.

Adora Cheung [01:04:22] – Yeah. Yeah but what else? Then a lot of stuff in emerging markets. There’s just a lot of good engineers that are, like good engineering talent that’s popping up obviously in India and China are the obvious ones, but places like Jakarta. We have a company in Iraq. This batch. They’re just building a lot of basic, I mean it’s probably to us in America it’s kind of basic digital infrastructure stuff. But I think it’s what’s going to spur innovation and spur the economy of a lot of these places. So I’m really excited.

Craig Cannon [01:05:06] – Yeah. I mean I think it’s cool obviously there’s a lot of arbitrage stuff people can do with so much engineering talent. But would you build Homejoy in Iraq? Would you be excited to do a thing again?

Adora Cheung [01:05:18] – I don’t think that would work there. But I’ve pretty much decided I don’t think I want to work, like the next company I build is not going to be in the O2O space like heavy operations. It’s going to be more in software and stuff that. Yeah but I don’t know. It depends. I want to work on a really good problem though first and foremost and how I go about solving it. It’s whatever. If it ends up being that then it ends up being that. So my mind doesn’t first go to that, and also I think it requires local talent to get that stuff right. I’m more interested in the position I’m in now, which is helping them start things and thinking about how to go about setting up operations and how to think about metrics and stuff like that and getting off the ground. But yeah. So I prefer to work on that level in emerging markets.

Craig Cannon [01:06:16] – Interesting.

Adora Cheung [01:06:17] – But it’s fascinating to me.

Craig Cannon [01:06:18] – So when is an opportunity going to be good enough for you to feel that it’s right?

Adora Cheung [01:06:25] – I think on two levels, one is people you work with, and so finding the right team to work with again and then to the problem. Again, it’s something that where I don’t get distracted from so it has to be really compelling to me, right? Like if I can come up with this while I’m at YC, that’d be amazing because I get distracted very often with new cool ideas. I think those are the two criteria for me.

Craig Cannon [01:06:50] – I want for you a lot of things.

Adora Cheung [01:06:59] – Thanks.

Craig Cannon [01:07:00] – I’m not going to go full Luke Eisman and scream at you, pressure you to quit your job but it’s always a thing. It’s something I care about.

Adora Cheung [01:07:10] – Yes. Alright. Well that has been a fun long podcast. Thank you very much for doing this.

Craig Cannon [01:07:18] – Thank you.

Adora Cheung [01:07:19] – And I hope others have learned.

Craig Cannon [01:07:20] – Okay thanks.

Adora Cheung [01:07:21] – Alright. Alright. Thanks for listening. So as always, you can find the transcript and the video at blog.ycombinator.com. If you have a second it would be awesome to give us a rating and review wherever you find your podcast. See you next time.