- Adora Chung interviews Craig Cannon, the head of marketing at Y Combinator, on podcasting trends and the Y Combinator podcast.
- Craig Cannon shares his background, including working at The Onion and starting a hackathon series called Comedy Hack Day.
- He also talks about his world record in cycling and how he ended up at Y Combinator.
- The Y Combinator podcast aims to educate founders and drive applications to Y Combinator.
- Craig Cannon discusses the process of creating a podcast, including coming up with topics and booking guests.

The speaker discusses the process of starting a podcast and preparing for interviews. They mention different types of episodes and how they approach each one. They also talk about the challenges of interviewing experts in unfamiliar topics. The speaker emphasizes the importance of making guests comfortable and keeping the conversation engaging. They also touch on podcast analytics and the gear needed to start a podcast.

- The speaker discusses the setup of their podcast recording room and the equipment they use.
- They recommend using a Zoom H4N recorder and Shure mics for in-person interviews, and a Blue Yeti USB mic for remote interviews.
- They mention using Audacity for editing and Backtracks for serving the podcast.
- The speaker talks about their own voice and how they have gotten used to it through editing.
- They mention their favorite interviews from the YC podcast, including Leonard Suskins, Michelle Kuo, Ryan Peterson, and Rosalynn Watts.
- The speaker highlights the importance of confidence in starting a startup and how it plays a role in success.
- They discuss the optimism and potential for growth in startups and the value of standing out in the industry.
- The speaker mentions feeling anxious about doing their own startup after interviewing successful founders.
- They mention the mushroom interview and the ability to conduct private research in different countries.

- The speaker discusses their admiration for Tim Wong's ability to balance multiple jobs and side projects.
- They believe that clear communication is key to building a following online.
- Successful startups often focus on solving big problems and are not attached to a specific solution.
- The speaker mentions that successful founders are just normal people and not as extraordinary as they are often portrayed.
- They believe that the best ideas can be explained without using jargon like AI or blockchain.
- If the speaker were to start a podcast from scratch, they would include more diverse and unconventional guests.
- They discuss the importance of using YouTube to reach a younger audience and the challenges of managing multiple YouTube channels.
- The speaker believes that episodes with big names and influential individuals tend to be more popular.
- They mention a strategy they used to attract more applicants from the physics community.

- The strategy for the physics episodes was to attract more people studying physics by getting big names in those communities to know about YC.
- Small but tightly networked communities work well for sharing content.
- Adjacent guests, such as Mr. Money Mustache, who retired early and has a passionate following of software engineers, are valuable for the show.
- The future of podcast monetization could involve contracts with big companies like Spotify, Patreon models, tipping, and expensive podcasts.
- There is potential for a market in educational content where people are willing to pay a lot of money for high-quality teaching.
- Commitment and basic income salaries from platforms like Spotify could help podcasters succeed.
- Influential podcasts include Econ Talk, Joe Rogan, Seventh Avenue Projects, Barbell Medicine, and surprisingly interesting dead authors podcast.

- The speaker discusses various podcasts they listen to, including the Dead Author Podcast, Berkshire Hathaway, The 9 Club, Prepared, and Startup School Podcast.
- They mention that podcast discovery is broken and suggest that a podcast app resembling YouTube clipping would be beneficial.
- The speaker also shares their belief that cushy internet jobs are bad for innovation and suggests implementing term limits and forced sabbaticals.
- They mention an application question for YC about hacking a non-computer system and share their experience of Everesting in cycling.

- The speaker created a spreadsheet of hills in the East Bay to find the best location for his goal
- He achieved his goal and then had a quarter-life crisis before leaving the country
- Working at YC can make one feel pressure to start a company
- The speaker is interested in creating a product in the space of providing people with freer lives, potentially in the housing sector
- The speaker is also interested in remote collaboration and replicating the serendipitous nature of living in a city
- He is starting to look into brain computers and emerging markets for potential opportunities
- The speaker wants to work on a compelling problem with the right team and not get easily distracted by new ideas

- Adora Chung interviews Craig Cannon, head of marketing at Y Combinator, on podcasting trends and the Y Combinator podcast.
- Craig Cannon discusses his background, including his work at The Onion and starting Comedy Hack Day.
- He talks about his world record in cycling and how he ended up at Y Combinator.
- The Y Combinator podcast aims to educate founders and attract applications to Y Combinator.
- Cannon explains the process of creating a podcast, including topic selection and guest booking.
- He discusses the equipment used for podcasting, including recommended recorders and microphones.
- Cannon mentions using Audacity for editing and Backtracks for serving the podcast.
- He shares his favorite interviews from the YC podcast.
- Cannon emphasizes the importance of confidence in starting a startup and standing out in the industry.
- He mentions feeling anxious about starting his own startup after interviewing successful founders.
- Cannon believes in clear communication and the ability to explain ideas without jargon.
- If he were to start a podcast from scratch, he would include more diverse and unconventional guests.
- Cannon discusses the challenges of managing multiple YouTube channels and the importance of using YouTube to reach a younger audience.
- He believes that episodes with influential individuals tend to be more popular.
- Cannon mentions a strategy used to attract applicants from the physics community.
- He discusses the potential future of podcast monetization, including contracts with big companies like Spotify and Patreon models.
- Cannon shares podcasts he listens to and suggests improvements for podcast discovery.
- He believes cushy internet jobs are bad for innovation and suggests implementing term limits and forced sabbaticals.
- Cannon shares his experience of Everesting in cycling and his interest in creating a product for providing people with freer lives, potentially in the housing sector.
- He is also interested in remote collaboration and exploring brain computers and emerging markets for potential opportunities.
- Cannon wants to work on a compelling problem with the right team and avoid getting easily distracted by new ideas.

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.

https://twitter.com/craigcannon

Adora Cheung is a Partner at YC.

https://twitter.com/nolimits

***

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

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?

And so Craig is the head of marketing at Y Combinator and also the extraordinary host of this great Y Combinator podcast.

And he actually asked me a few weeks ago on topics I was interested in and doing on a podcast.

So I thought about things I wanted to learn more about.

And 1 of those things is actually podcasting itself.

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, 2 to 3 times a week?

So why don't you start off with, who's Craig Cannon?

How did you learn about YC and how did you even end up here?

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.

And 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 that was the 1 thing I got.

So I started working there, and while I was there, I actually started reading HN and programming on the side.

And after a few years there, I started this hackathon series called Comedy Hack Day, where developers and comedians made stuff together.

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 got pretty strong on these things?

Paul Matzkoff So 1 of the early ones was called Timesify, 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 you could click the ads and it would basically create a slideshow of all the images.

Yeah, so I did that for like 4 years with a few of my friends.

And I had gotten into cycling when I was out here.

And I found this thing, this world record that I wanted to go for, and I did it, and it worked out.

And people started treating me differently, and it was really weird.

And I started feeling this pending doom of my youth and vitality fading away.

It was most elevation climbed in 48 hours.

So, people were treating me differently and I was like,

And so I quit and I went on a 5 month bike tour.

And I was 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 Isman, who used to work here,

me up and asked me if I wanted to do a contract for the blog.

So you started with the blog and then, so what were the steps into how you eventually started this YC podcast?

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.

Because YouTube, I think a lot of people know now, has great SEO and podcasts have terrible SEO.

And so I was like, all right, 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 you know like our founders get attention like stuff we want to talk about gets attention and more importantly it doesn't fade away.

And so I was like well podcast is a good way to do that and yeah we just started from there.

Oh so podcast is the way to get the content and then YouTube is the way to spread it.

Well, because we do both, but I think it was like 2014 or 2015 when I started following Joe Rogan

I just saw this like massive growth happening and people were like clipping his videos and creating like 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 yeah, if you look for Adora Chung online, I'm sure if you Google yourself, you

So 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?

Yeah, so The thing that ultimately really matters is we kind of have 2 goals.

So 1 is to help educate founders and people who are in the startup game, and 2 is to bring other founders in.

So the way we're trying to calculate this, and it's still pretty loose, is by driving applications.

But in terms of like sheer metrics, you know, we started out just like possibly a little bit bigger than other shows by having like maybe 2 or 3,000 people automatically subscribe.

And now we're maybe like 40-ish thousand, give or take, you know, 5 or 10000 every episode, plus YouTube.

So YouTube can go from like a thousand to a hundred thousand, depending on who the person

So, alright, so I wanted to get into how you create a podcast essentially and your tips there.

So let's pretend I'm I want to do a podcast.

How do I decide if that's actually a good idea or not?

Well, I can come up with a theoretical idea.

So 1 I've always just joked 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 will, they actually have great insight into the world in which we are unaware of.

I have not seen it, but I've seen clips of it.

So right off the bat, there's clearly an audience already for this.

The first question is honestly, do you want to do the thing?

And I think another question that a lot of people don't ask is, am I willing to even create like a time box around this and say, I'm okay if I make 10 episodes?

Because 1 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 out every week.

If it's not your job, it can become a real grind because those metrics don't go up that quickly.

You know, getting from like 30,000 to 40,000 and 40,000, 50,000 can take years for certain people.

So, assuming that you really want to do the thing, think what could I maybe make like 8 of these like Alexis Madrigal did that with a container podcast I don't know if you listen to that 1

it's super cool and it's like the short version I thought that was a great idea.

So then I would Would this be scripted in any way?

Probably not, but I would have to probably edit a lot.

So what I would suggest doing then is just getting like a basic, basic setup and then just going and recording a bunch.

And so the YC podcast has every episode has its own topics.

So in many ways it's about like stuff I'm interested in.

I don't know, I hit this point where 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 podcast that interested me, because it all feels very inside baseball.

And I was like, maybe other founders aren't interested in this either because they talk about it all the time.

So I thought, okay, perhaps we could focus on technology as a core, as like a pillar, but also do art and science and entrepreneurship.

And then it's just been like getting a mix of these people.

So yeah, a big driver is obviously if they have a following.

So you have a topic for the episode, then you obviously need to find someone to interview.

So tell me the order of operations of how you put together a whole entire podcast.

So a common 1 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.

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 Aronson, Leonard Suskin, all those people.

Yeah, it's just finding trends, finding things that are interesting.

Or are there what are reasons why people don't want to do it?

Because I'm sure some people said, not really.

Yeah, but there are there are some fringe ones for sure where people say, I don't know if I want to be on a YC podcast.

Because there are certain brand connotations.

You're making this actually to do a podcast sounds like almost like starting a startup.

You know, there's a lot of hard, long days of work to do.

And you know, maybe there's a lot of cold emailing.

Cold outreach essentially, and just keep asking people to do it until they actually do

I think thinking about content in the same way you think about product is just like, great, there you go.

All right, 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 quantum physics, these kind of things.

But you actually ask really good questions.

So, I think I would probably break apart the episode types.

So there's episodes like Office Hours with Adora.

Okay, I know you, I know the kinds of questions that come in.

There's a middle level, which is a founder of a company, like say, Ryan Peterson at Flexport.

In that instance, what I would do is find every podcast he's ever done and listen to all of them at like 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.

And the last category are the quantum physics type episodes, which yeah, to confirm your belief I'm not an expert in.

For example, that episode itself, did you, like some of these you don't have, you barely have to do any prep.

For this 1, like, did it take weeks or days or…?

The first quantum physics episode with… Well, there was a hard 1 before that too with Ron Adhikari about gravitational waves.

That probably took 2 and a half days between listening to John's talks and reading articles he's written, you know, with other people.

you just like take notes on 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 like no 1 really knows about or cares about.

But there are examples like the Susskind episode which is 1 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 all right you know we're gonna meet here no reply usually when that happens it means that he's ghosting me And so I didn't do any prep.

And so I'm like, all right, he's ghosting me, he's ghosting

So possibly the YouTube comments reflect my level of preparedness.

Was that the most, what was the most challenging 1

I would say the, So John Preskill was particularly difficult because he's also very chill.

And so keeping it upbeat, keeping it interesting, keeping it fun.

But I would say the 1 I bombed hardest on was Jocko Willink and Mike Cirelli I don't know if you listen to

I have this thing where when I get nervous, I laugh.

It was fine, but we hung out afterwards and

Edith Warren So 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?

So usually there's, this doesn't come out in the podcast, but we talk before we start recording.

And so you kind of feed them what they should think about, how they should act.

Basically, these are the norms of the show, and most of it's just about making them really comfortable.

And we do a slight amount of editing, usually almost none.

But if I edit anything, it's often the first 5 minutes.

I'll just cut the whole first 5 minutes off because you're like, oh, Adora really got warmed up and she was into it at this point.

People think this matters, but the intro doesn't really matter.

And actually, 1 of the best podcasters in this regard is Russ Roberts from Econ Talk.

So if you pay attention to his show, he always starts with not a controversial question, but a question that's not a softball.

I think that's a really great way to start the show.

Because you wanna give them something that's interesting to them, but you don't want to confront them.

And this is something that a lot of podcast hosts, and I fall prey to it too, you don't want to offend someone,

So you ask them all these softball questions, but you don't really go anywhere.

And that's how you end up with the Joe Rogan, Elon Musk episode.

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.

See all Y Combinator transcripts on Youtube

Craig Cannon on Podcasting with Adora Cheung