Ep 58: How to Create a Blockbuster Podcast (Part 1)

How do you create a blockbuster podcast? This episode explores the tips, tricks, and best practices of a master. My guest isAlex Blumberg http://gimletmedia.com/, who cut his teeth on the king of all radio shows (This American Life) and recently co-founded Gimlet Media http://gimletmedia.com/. Gimlet swiftly conquered the iTunes rankings with two blockbuster podcasts: Reply All and StartUp http://gimletmedia.com/. Podcasters everywhere asked: how the hell does he do it? This episode provides some answers. The discussion is split into two parts, and we cover a ton. Please listen to both parts, as they work together. We discuss what Alex learned from Ira Glass, his field recording gear, the nuts and bolts of producing world-class audio narrative, and much more. Part 2 also features a preview (5 min) of my episode with Arnold Schwarzenegger! Show notes and links mentioned can be found at fourhourworkweek.com/podcast http://www.fourhourworkweek.com/podcast

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  Alex, welcome to the show.

• 0:05Tim Ferriss?

  Alex?

• 0:08Speaker 01

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 0:12Speaker 02

  Can I ask you a personal question? No, we're just in an appropriate time.

• 0:18Speaker 02

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:29Tim Ferriss?

  This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where I deconstruct world-class performers of all sorts of types, ranging from billionaire investors, to chess prodigies, to actors, to writers, to athletes, and everything in between. In this episode, we have a real treat, and it's a two-part episode with Alex Blumberg, who is very well-known as a producer for This American Life, co-host of Planet Money, and also the co-founder of Gimlet Media, which has currently two blockbuster podcasts, Startup and Reply All. And in the first part, which you're currently listening to, we are going to talk to Alex about all sorts of aspects of the business of storytelling,

• 1:12Tim Ferriss?

  the art of storytelling, including gear that he uses, etc. The second part is going to be an excerpt from a class that he taught on creativelive.com. Normally costs about $100, and I advise that company, so I was able to pull out about a half hour of his teaching a class about the art of the interview, crafting the perfect question, etc. That is part two. I implore you to listen to both. I really enjoyed this. And without further ado, please enjoy Alex Blumberg.

• 1:44Tim Ferriss?

  Alex, welcome to the show. Great to be here. Thanks for having me. And I have to start off, because we have been scheduling, and I know you're racing to get a show out the door. Does it ever get any easier?

• 2:00Speaker 02

  I hope so. I really hope so. It has been, yeah, I mean, it's just been, I mean, it's sort of an insane project, what I'm doing, which is trying to, you know, create a regularly occurring documentary podcast about a company that's starting up, while at the same time trying to start that company. So it's been sort of like, it's, because both of them are sort of full-time jobs. So, yeah.

• 2:28Tim Ferriss?

  And how do you balance, because I've listened to every episode of Startup and have followed it very closely for a whole host of reasons, how do you balance the realtime documentary nature of the show with planning, say, an editorial calendar and actually having things locked and loaded and ready to go in advance?

• 2:48Speaker 02

  I don't balance it. That's the problem. Like, we don't have things locked and loaded and ready to go in advance. Like, we don't, we were editing the, we just finished editing this week's episode this morning, and then we just tracked it. That's why I was a little late with you. I was tracking it in the studio today, and then it'll go up tonight. So that's how close to the wire we are. I mean, we're just, we're, you know, things are, and you'll hear, this episode is all about, it's all about burnout.

• 3:20Tim Ferriss?

  I was wondering, I was wondering when that episode would come.

• 3:27Speaker 02

  Yeah, yeah. Because there's a period where, I think there's a period in a company's life where people are like, well, this is just a startup. This is the startup experience. And then there's a point at which maybe like, probably right about around where we are, four or five months into it, where you're like, it's a startup, but it shouldn't be this hard. And so, so we, sort of realizing like, we have to, we have to, we have to change some things. We have to add some more support. And part of it's just like, you just don't know, you know? Like, I didn't know, I mean, you know, you don't know what's possible. And so, so we started out, I think we just didn't have enough capacity to do what we were trying to do.

• 4:08Tim Ferriss?

  And what does your current team look like? Well, first question is, what is tracking? I'm still a novice at this, and I have a ton of questions.

• 4:15Speaker 02

  Oh.

• 4:16Tim Ferriss?

  But what is tracking exactly?

• 4:17Speaker 02

  Yeah, so tracking, so when you're doing sort of a documentary-style podcast, which is sort of the kinds that we do, where you're, we have a script. And so what I'll do is I'll go out and I'll gather tape in the field, and I'll record different conversations with people, and then I will edit those down. And so I have a bunch of, sort of like, basically selects tape that I've gathered, and I've edited down and cut. So it's like, you know, I'll have like, maybe like, you know, 25 minutes of edited tape. And then what I have to do is stitch that together with a script. And so I'll write the script, and then we'll do edits on that script. And so I'll read it aloud in the office. We'll all sit around a table, sort of like a table read, I guess. I'll sit around, I'll read my script, and I'll play the tape that I've cut from the

• 5:01Speaker 02

  computer where it's supposed to go in the story. And then people will give us notes on the script, and sort of say, "This part was dragging, and this part should come earlier, and this part you can just totally get rid of, it's boring," whatever. And then you rewrite, and rewrite, and rewrite, and then finally you get to the final script, and then you go into the studio and track it. And that's when you actually just lay down your voice tracks. And then those all get mixed together into the final product.

• 5:25Tim Ferriss?

  Got it. And the actual reviewing of the tapes, you capture a lot of interview, obviously. And in one of the episodes of Startup, you had one of your employees reviewing those tapes. Do you personally review those tapes, or do you have someone do a first pass and attempt to pull out the interesting stuff?

• 5:47Speaker 02

  It goes both ways. I mean, usually I've been the one getting the tape. So I have heard it, because I was there, you know, I was there

• 5:57Tim Ferriss?

  Right.

• 5:58Speaker 02

  You know, with the microphone and the recorder. But usually it's my producer who actually does a first pass-through and pulls all the selects.

• 6:09Tim Ferriss?

  Got it. And what are the criteria for pulling the selects? What is, what makes something worth being in the show?

• 6:17Speaker 02

  I think what you're asking, Tim, is what makes good tape?

• 6:20Tim Ferriss?

  That's right. That's exactly what I'm asking.

• 6:23Speaker 02

  That's the question that has consumed my, my life for the past 20 years. So I have an answer for you. So I think, I think when, you know, one of the things that, there's a couple of things that you're looking for when you're going through the tape. So because I have a script, because I'm narrating it, I can sort of say pretty much all the, all the basic information, usually better than anybody that I'm talking to. So what I'm going for are specific moments when I'm talking to people. I'm going for specific moments that have some kind of deep emotional resonance, or where something very live and unexpected has happened, or where there is just a very authentic emotion has been expressed. And those are the moments that I go for.

• 7:07Speaker 02

  It's almost sort of like, if I'm talking to somebody about whatever, I don't know. Just to borrow an example from my Planet Money days, bond prices. What I don't want is somebody talking about bond prices. I want somebody expressing some sort of emotion about it, if that's possible. You know, because I can do all the nuts and bolts, you know, sort of information transfer. And so what you're looking for in your interview subjects is something, something that, that you can't provide yourself. Some unique perspective. The other thing that you're going for, the other thing, so that's one whole category of good tape, is sort of like emotionally resonant, you know, emotionally authentic, or something where something interesting or unexpected has happened, sort of in the moment.

• 7:48Speaker 02

  The other category is somebody just telling you a really good yarn, like a really good narrative. And so that's the other thing that we look for, is sort of like, sort of, at This American Life, we had a term for this, we'd just call it an anecdote, but what we really meant was a little story. And so, like, like, just for an example, if I start to talk to you, and I say, you know, Tim, this morning I was leaving my house, I was walked out the door, and I was, like, I looked up in the sky, and I saw something that I couldn't believe.

• 8:23Speaker 02

  Like you want to hear what I said next, right?

• 8:25Tim Ferriss?

  Right, it's a very unfulfilling story, isn't it?

• 8:28Speaker 02

  So that's the story. Like, we are hardwired to be like, one sequence of action, another sequence of action, and it's going to build towards something. We want to hear what it's building toward. And if I say to you, "I saw something I couldn't believe, a cloud," you'd be like, "That's a boring-ass story." But if I said, you know, "A UFO," then you're like, "Oh, that's an interesting story." So, but the mechanics of it, the fact that it's a story and it has a beginning and it's sort of, and it has like, a narrative progression and sort of, you know, sort of rising action. Human beings, I think, are sort of hardwired to want to pay attention to that. That's what we've been telling each other for, you know, 40,000 years.

• 9:09Speaker 02

  And so, so those are the other things you're going for, is like, people telling you stories.

• 9:15Tim Ferriss?

  And the process, I'm so fascinated because I'm struggling with this myself, the process of putting together an episode, especially when you currently have the, the real-time aspect of it, which seems to complicate matters tremendously.

• 9:31Tim Ferriss?

  How many people do you currently have working on each episode of, let's just say, Startup? And what are their roles?

• 9:38Speaker 02

  Yeah, I mean, so that's the thing about this stuff, is that it's like, it's so much more time-consuming than, than, than the other sort of main kind of podcast, which is out there, which is a straight interview podcast, like, which we're doing, which is, which are also, like, all these elements can be possible in those kinds of podcasts as well. And so what we're doing is sort of, like, I go back and forth, like, is this insane to be spending all this time producing 20 minutes of one kind of podcast when another kind of podcast you could produce in 20 minutes? You know what I mean? And, uh, and so what we have is we have, um, so, right now, on Startup, it's just me and my producer, Caitlin, and then another employee, Lisa, who's, um, who's going to

• 10:23Speaker 02

  be producing the second season of Startup. That's not quite enough. Startup comes out every two weeks, so we can bear, and, and because I've been doing this for so long, and I've internalized so much of this stuff, like, I'm probably more productive at it than, than somebody else, but, so, we can bear, we're not quite getting by with that, but we would definitely need, you know, we need some more, we need another body or two, for sure.

• 10:50Tim Ferriss?

  And aside from the producer, you also have an engineer who does

• 10:53Speaker 02

  Yes.

• 10:54Tim Ferriss?

  post cleanup and that type of thing?

• 10:55Speaker 02

  Yes, all right. So we have, yeah, so on staff is it's me and Caitlin, our producer, and Lisa. And then we also have other people on staff who can help with the edit, which is a really, really important part of it. So there's other people. So then we'll usually have one or two other people sitting in to do the edit. So where I sit around and do the table read, they'll give me notes and sort of say this part was slow, this part wasn't. So that's a really important thing. And then we, and then we, we also outsource our transcripts. So we have people logging all that tape so that it's easier to go through. So we have people providing transcripts of the tape. And then we have an engineer who mixes the episode, which is, you know, basically everything from doing

• 11:39Speaker 02

  all sorts of things that I don't understand, like putting compression on it and making it sound really good, but also just sort of like putting it all together, making it sound good, making the levels right, all that stuff.

• 11:48Tim Ferriss?

  Got it. And the one thing that struck me about Reply All, the other show that I've been listening to from Gimlet Media, is was listening to the launch of that and how the hosts decided to join forces with you. And one of the things they mentioned was wanting you as an editor, or having you run to them, run to and from the two shows, working with them as an editor. Does that primarily mean that you're working on the script and reviewing the transcripts? Or what, what is, what are you doing as an editor?

• 12:24Speaker 02

  Yeah, I mean, I think what I think of myself as, and I think one of the reasons that I started this company, I think my primary skill, like probably if I had to say, like, here's the thing that I am best at, it is at being an editor. And being an editor means

• 12:42Speaker 02

  That you like, and the way I think about it, it's sort of like from the beginning, it's basically being a collaborator with the hosts, with the talent, to getting, you know, the best show that you can get. And so I try to, so, you know, like, what that means is that when we have a weekly story meeting for Reply All, where we'll sit around for, you know, we'll talk for two hours, we'll talk for an hour about, you know, what are the stories that they want to pursue? And we'll think about interesting angles to go at that story with, we'll decide if they're, if it's worth it or not. And then we'll sort of plan, like, okay, who do we want to talk to? Who would be some interesting people to talk to in this story? What questions do we want to ask them? Like, the questions are really important. Like, if you go out and you ask, and you don't ask the right questions, you can come back with nothing. You can come back with no good tape.

• 13:27Speaker 02

  And so you have to sort of design your questions so that you're sort of giving yourself a higher chance than average of getting good tape. And then, so we do all that, and then when they do, when they come back and they write the script, then I'll go through the script with them. And usually we do at least one pass, but sometimes two and maybe even three passes, depending on how tricky a story is. Where we'll really dive in deep and sort of get into the language and sort of say, this, you know, you're saying this, but it's not quite right. And so, it's just, it's, I mean, it's, I think when people see it for the first time from the outside, it's like, they can't believe how much, how much actual work goes into, into the making of this stuff. And, I'm not sure, you know, and like, one of the big questions is sort of like, how

• 14:11Speaker 02

  much of that work is actually necessary work? And how much of that work is like, are we, are we spinning our wheels? But my contention has been that, like, to really, like, you know, if you look at the very top of the charts in iTunes, like, a lot of those shows have that, that amount of labor embedded in the programs that they're putting out. Like, I come from This American Life, which is where I learned all this stuff. And like, you know, there's even more sort of editing and production work that goes into making those shows. And I know certainly Serial, they were working on that for a year, at least. So, so, you know, so, you know, so I, so I think it's related, but I'm not, I'm not sure.

• 14:58Tim Ferriss?

  Oh, it's massive. I mean, I was blown away and not terribly surprised when I heard that Serial had a team working on it for a year.

• 15:07Speaker 02

  Yeah.

• 15:07Tim Ferriss?

  Prior to the launch. Didn't surprise me at all. I mean, as someone who's a very plodding writer himself, it didn't really surprise me. How did you decide? Well, actually, before I jump away from the editing, what do you do as an editor differently from other people?

• 15:26Speaker 02

  Well, I think-

• 15:26Tim Ferriss?

  Because you're clearly very good at it. I mean, the output of the shows reflects that. So the question is, you know, maybe why aren't other people better editors? Or what do you do differently?

• 15:37Speaker 02

  I think there's a bunch of things. So I first, I think This American Life was a real editing shop. And I think it's a pretty special place. Like, in that Ira is really, he's a really great editor, but he's also very encouraging to people to sort of do their own thing. Like, it's his show, but he really encourages you to do your own thing within that show. So when I worked there, every story that I thought I wanted to do that I could sort of make a good case for, I was able to do and I was able to write it myself. So I think part of being a good editor is being sort of, is wanting to encourage

• 16:22Speaker 02

  others to sort of, is having that feeling that like, if we're working on this together, I can take, my ego feels like I got some of the credit because I was in there from the beginning, but you're also happy to share the credit with the person who's doing the story. So I think part of it goes back to that. Sort of, how do I think of myself as an editor? And at This American Life, it was like, sort of, an elevated job. And then, I think partly, it's sort of like, when I got to NPR, I realized that like- The conception of the job was, you know, your reporter goes out, they come back, and then they play you a story and you're basically, it's not to time, it's to time. You know, you make a couple of suggestions. I didn't understand this part, I didn't understand

• 17:04Speaker 02

  that part. But you're not like, thinking big about like, well, what's the idea that we're trying to go towards with this story? What's the new thing we're trying to say? And so I think partly also what makes a good editor is getting in there from the beginning and talking with the reporters about, what are we trying to say? What, you know, what, what's the interesting thing? What's the new thing that we're going for here? If we're doing a story that's been done a lot, like, I don't know, politics or homelessness or whatever it is, like, something that you've heard about in the news a lot, race, like, how are we gonna talk about it in a different way, in a news way, in a surprising way? And a lot of, like, you know, half the, you know, a lot of the work that makes a story good goes in at the very beginning. And I think that's, a lot

• 17:49Speaker 02

  of editors don't think about their jobs that way. And I think that's, that's why it's, and so I think that's, that helps me. You know, if I'm in there from the beginning and sort of talking about it, it's easier. The other thing, one other thing that I think about, about editing, and just quickly, is that like, one of the biggest jobs of the editor is just being, paying attention to your own boredom. You know, I think people get into, people who get into journalism get in because like, I'm interested in the world and I have a natural curiosity and I want to satisfy that curiosity. But, you know, you gotta, you're still like, you've gotta keep, keep your audience interested. And, and the editor can help do that. Like, the editor, if you, you have to be curious

• 18:34Speaker 02

  about the world, but you also have to know, like, you have to have this sense and you're listening to your boredom. Something that I had to learn to do, but once I did, it's really helpful.

• 18:43Tim Ferriss?

  What are the symptoms of boredom? So, I know that might sound funny, but what are the thing, what are the symptoms of boredom that maybe you didn't listen to in the early days, as much?

• 18:56Speaker 02

  Well, I think you try to sort of like, if there's some, if somebody reads something that is like, if it's something that you like, that you work together, they're sitting across the table from you, and they read something that doesn't, is like, maybe like, sort of a boring sentence, or they've come through a boring thing, or somebody's talking on tape and you don't quite know what they're saying, or what the point is. Because you like the person, and because, you know, you're a human being with decent human emotions, you'll be trying to think to like, oh, well, probably what the person was saying was this, and so therefore, you know, though, that all makes sense, because I, you make up for the reporter who's doing the read. And it's, and that's good, like, that's decent human behavior, to try to like, sort of meet

• 19:39Speaker 02

  somebody halfway, and be understanding and empathetic to what they're saying. But there's something that happens on the radio, or on, in audio, when you're listening, you don't, the listener doesn't do that. And so you have to train yourself out of that instinct, to make up, to sort of fill in the gaps with what people are saying. So one, one sign is just this sort of glimmer of like, wait, I'm confused here. And it's a very, very, it's often at the back of your head, you don't quite get it, but you have to pay attention to it, because you sort of get what's going on, but there's like, some, like, there's some question in your mind, is like, is that the thing that's going on that I think is, I think it is? But it's a very, very slight, you have to train that to sort of come to the beginning of your brain, to the head, to the forefront of your brain, that feeling. Because the minute that feeling happens, you know, this is a spot that needs to be edited.

• 20:22Speaker 02

  And the other part is just sort of like, you know, you, you, you know, you find yourself drifting in an edit, and if you're drifting in an edit, it's not, it's not your fault, it's theirs. You know what I mean? That's harsh. But that's what you have to do. If I'm reading through, and somebody who's listening to my story is drifting, that is my fault. I have to keep you from drifting. So, and so the same thing is, if the shoe's on the other foot, then the same thing is true. You're the editor, your job is not to be engaged, their job is to engage you. And so, and so you, so the minute you feel yourself drifting, that's another section that needs to be edited.

• 20:59Tim Ferriss?

  No, definitely. And you brought up things being unclear or hard to understand. When I found as a writer, when I send things to my friends who are writers to have them proof a chapter, if I ask them to indicate, if I first ask them to indicate what they like and dislike, they might try to appease me or feel badly about hurting my feelings. So I always start with, just point out what isn't clear. And that usually yields a much better result because it's, they don't feel like they're being as judgmental towards me personally.

• 21:29Speaker 02

  Right.

• 21:30Tim Ferriss?

  So I always find that a really helpful place to start.

• 21:33Speaker 02

  And that's even more important in audio because audio is like, you can't go back and reread audio. You know what I mean? Well, now in the age of on-demand audio, you can go back. This is true back in the radio days when there was literally no mechanism to go back and re-listen. But, but, and so what happens is the minute you're listening, if you're confused, you're like, wait, what was that thing? And you've been trying, and you try to figure in your brain, what was the thing that was confusing you? And then your brain has taken its eye off the ball, basically, and then not listened to the next sentence that's coming out. And then it's like a train wreck, like you never catch up. You know what I mean? So one moment of confusion

• 22:06Tim Ferriss?

  Definitely.

• 22:07Speaker 02

  can utterly destroy an otherwise beautiful story, you know? And so you have to be on, you have to be on, you know, a special guard about that in audio, I think particularly.

• 22:17Tim Ferriss?

  What, what does a producer do? So this, this has come up quite a bit. You mentioned you have a producer, for instance. What, what is the, what does, what does, for startup in particular, what does the producer do? What is their job?

• 22:31Speaker 02

  I know. It's one of those jobs, it's one of those words like manager, which is like, wait, what's a manager? You know, you can, yeah. So a producer, I think, is like, also has many meanings. But in my case, what a producer does, so my producer helps me think through

• 22:50Speaker 02

  The interviews I'm going to do. Often we'll listen back through the tape, transcribe the tape sometimes, or make sure that it's transcribed. She will pull the interesting pieces of tape. Usually we'll consult about it, but then she'll go and actually produce a session in the editing software that we use that has the pulls that we want. She'll also think through like how to structure each episode. And all sorts of other things. When I was at This American Life, my job was producer. That was what I was called. And you basically help build the story with the reporter.

• 23:32Speaker 02

  You're really sort of like a partner in the creation of the story. And the reporter's voice is doing it, and the reporter's often sort of like writing, and in some cases finalizing the writing, in some cases really doing most of the writing. But really, you're a team. And structuring the story is so important, again, in audio especially, I think, just because you can get so confused easily. So generally, what the producers are in the audio world are their experts at sort of structuring the story. Like, how does the story begin? And what are the emotional moments that we're leading to? And how do we contextualize those moments with script? So often, when I was a producer at This American Life, we'd be working with writers,

• 24:16Speaker 02

  who were really good writers, who had not done that much audio. And often, what I would do is I would cut the tape, and then we would meet. And I would just sort of talk them through. So we would have gone out and done a bunch of interviews. I would cut down to the moments that we were going to use. And then we'd get back in the room. And I would tell them, like, okay, here's how I think you can start, and here's what I think you want to say to start it up. And then we're going to go to this piece of tape, and this is the first piece of tape we're going to use. And it introduces this character in the story. And then, from there, you're going to want to write something like this. And sometimes I would have dummy language in there. And I would basically provide a roadmap for the reporter, or the writer, that would sort of lead through the tape and get to a finished piece.

• 24:58Speaker 02

  So that's, that's, that's

• 24:59Tim Ferriss?

  Got it.

• 24:59Speaker 02

  That's what they do, yeah.

• 25:00Tim Ferriss?

  And, and at Gimlet Media, which is of course, a much smaller operation than This American Life, who's handling releases and all of that kind of stuff?

• 25:10Speaker 02

  Yeah, the producer would be doing that as well. So that's the funny, yeah, so producers sort of like do sort of the high level conceptual structuring stuff, and then they also sort of like transcribe tape, and they also sort of like handle all the details and make sure that the plane tickets are purchased, and you know, various people have been set up and booked into various studios and all that sort of stuff.

• 25:31Tim Ferriss?

  With, with, I know we're getting into some nitty gritty stuff, but I'm so fascinated by it, and then we're gonna go kind of broader picture. The, what type of editing software do you use?

• 25:40Speaker 02

  Pro Tools.

• 25:42Tim Ferriss?

  Pro Tools?

• 25:44Speaker 02

  Yeah.

• 25:45Tim Ferriss?

  And with, with Reply All, for instance, which is, is perhaps a little more, can be planned a little more in advance, how, from the initial idea pitch meeting to the finished episode, how long does that currently take? And how far out have you planned already? Not necessarily gathering all the info and doing the interviews, but decided on the subject matter for episodes?

• 26:09Speaker 02

  Well, I mean, we're not as far planned out as we want to be. You know, we have, we have, we're, we have things on the calendar going out maybe a month or two, month and a half. But, you know, it's, it's always a race every week to get everything done. So, especially as you'll hear in the next episode of Startup. But, but, but, and, and, and so some of those are just ideas, some of those are like, you know, there's, all the, all the tape is in, and it's been edited, and we, and we just have to sort of like wrangle it into shape.

• 26:50Speaker 02

  So, yeah, so, but I would say that we don't have anything, we've never had, our goal is to sort of get to a point where we can have everything, where we can have We can be a week ahead, like we can have next week's episode in the can this week, like done, recorded, the ads put in, everything done, mixed the music in. And I would say we're several months away from that goal. Like, we just, we just need to get better at it and build that muscle.

• 27:19Tim Ferriss?

  What tools do you guys currently use? I, of course, take, I'm an avid, sort of, hyper-graphic note-taker. I heard Chartbeat mentioned in one of the episodes. What type of tools do you guys use for organizing all this stuff besides Pro Tools? What are the, you know, the software or the whiteboard? I mean, what do you guys use?

• 27:42Speaker 02

  We use actual whiteboards. We use, we have, like, little whiteboards that float around the office that have the, sort of like, the checklist of everything that needs to be done every episode. You know, sort of like, just, sort of like, just the basic stuff that you forget. Like, you know, did we, did we get the ad copy correct? Did we get the, did we email all the people? Did we write the copy for the web? Did we, all that stuff, you know? Did we get the list of songs that we're using in the episodes that we can put them on the website? And then, and then we use, and then we, we have a lot of, we do a lot of collaboration. So, the, most of the stuff that we write, our scripts are all written in a Google Doc. And we have multiple people editing through the Google Doc.

• 28:27Speaker 02

  That really changed my world when that came around. And that's fantastic. You know, we use Slack at the office, like the younger guys do. I don't really know how to use it, really. We, we, but there's, I think those are the main ones. Like, the Google Docs are sort of the main thing that we use to sort of collaborate write on. And then, and then actual whiteboards. We schedule stuff through Google Calendar also.

• 28:59Tim Ferriss?

  Do you use any kind of project management software like Basecamp or Asana or Trello or anything like that?

• 29:04Speaker 02

  I have worked on projects where I've used Basecamp before. Like when we did our website design, we used Basecamp with the design team that was designing the website. And that was really useful. Like I find Basecamp to be useful for like distributed teams. When I was at Planet Money, we did this big sort of crazy project where we followed a T-shirt around the world as it got made and we did this sort of elaborate web, interactive website about the project where we had all these videos and stuff like that. And that was like a couple of different teams, one in New York, one in DC. And we used Basecamp for that project as well and that was really helpful. On a day-to-day basis, I don't use it as much just because, you know, it's pretty simple what we're doing.

• 29:47Speaker 02

  The bulk of our work is sort of like, you know, managing, you know, wrangling tape and writing scripts. That's sort of like, that's the day-to-day. That's what I'm doing every day is that essentially.

• 29:59Tim Ferriss?

  What do you, what do you guys currently use for capturing tape in the field?

• 30:03Speaker 02

  We use-

• 30:04Tim Ferriss?

  In terms of equipment?

• 30:06Speaker 02

  We use flash card recorders and, you know, nice, nice microphones. We use, we use these Tascam, Tascam recorders. Some of us use Sonys. But they're just, they're, you know, pretty nice, you know, broadcast quality, you know, sort of, they're not the nicest, but they're the pretty nice ones. And then we have nice mics.

• 30:27Tim Ferriss?

  Mm-hmm. Now, what type of, if you know offhand, and I'm involved with CreativeLive, so I managed to grab a PDF of your, some of your gear. I don't know if it's changed since then.

• 30:38Speaker 02

  Yeah.

• 30:39Tim Ferriss?

  But I'm an advisor for CreativeLive. And by the way, it's, I'm going to, I'll link to it in the show notes for everyone, but the, I've been very impressed with the class, so we'll come back to that.

• 30:49Speaker 02

  Oh, thanks.

• 30:50Tim Ferriss?

  But just, just the master class in asking questions, so of course I have performance anxiety right now.

• 30:58Speaker 02

  That's hilarious that you're anxious around me. Yeah.

• 31:06Tim Ferriss?

  Well, that's why I decided to swing completely the opposite direction and ask very boring, hyper-specific tactical questions.

• 31:12Speaker 02

  Well, no, but I think the concrete details, that's another one that people forget. People go too broad, and I think what's often interesting is the nuts and bolts of people's processes. So, I think often I'll ask these exact kind of questions, like on a day-to-day basis, like, what are you actually doing?

• 31:32Speaker 02

  Like, I do these Squarespace, I do these ads, right? Where I just interview somebody in the company about what their job is like and the company that's sponsoring us. I guess we're gonna do one of these ads later. But my goal there is just to try to find one, sort of like, I call it like a vivid moment. A moment where it's sort of like, you know, like, and so one time I found myself talking to a treasurer of one company, and I was like talking, and like, I wasn't getting very much vivid stuff. I was like, sort of like, what's it like to be a treasurer? And wasn't getting very much. And finally, I was like, do you actually sign your name on the checks? And he was like, we don't wanna sign her, but sometimes I actually sign the checks.

• 32:15Speaker 02

  And then we got into this whole discussion of sort of where he sits when he signs the checks, and how he signs them, and how much time he allocates.

• 32:22Tim Ferriss?

  And how long it takes.

• 32:23Speaker 02

  And does he block it off in his calendar? And that was like, by far, the best moment of the interview, because it felt, all of a sudden, you were like, you actually, it felt real, you know? And you got a real sense of sort of like, the details of this guy's life. So, I'm all for these kind of concrete questions.

• 32:36Tim Ferriss?

  Okay, well, I'm gonna follow on with some digging, then. I noticed in the list of equipment, and again, I'll link to all of this in the show notes for people, that you have a boom mic, and I have, for instance, a Zoom recorder, a H4N, and I have another model. So, two follow-up questions. Is there any reason you chose the Tascam over Zoom or anything else? And then the second is, what do you use the boom for? Because I'm just, when I'm sitting down with someone, I find the... These handheld, you know, the Zoom recorders, for instance, work quite well by themselves. They work even better with a lav mic or something like that, or just a handheld stage mic connected with XLRs. What do you use the boom mic for?

• 33:19Speaker 02

  I mean, I can give you a lot of BS about it, but the truth is, I don't, it's like habit, basically. Like, these are the microphones that we started using at This American Life. When I first got there, I didn't know anything about audio. I am not a super technically, like, I know a lot about, like, story structure. I don't know very, I don't know, I know exactly what I need to know about recording equipment. I'm not super tech savvy that way. And so, so partly, it's just sort of like, that's the, those are the ones we use. And I got used to them. And I can hear this, I like, now I understand. Like, when I'm out in the field, I know exactly what I need to do with that particular mic to get the exact sound that I want to get, and I don't have to, like, mess around with something new.

• 34:01Speaker 02

  The one thing that I will say, that I think the reason, so the Tascam, that was just, that was a recommendation that I read on a website, and I bought it, and it's worked for me, although there's certain things that I don't love about it. So, so, I feel like you're, you're fine, whatever works for you, you're fine, fine with there. The, so the, the mic is more important than the recorder. And, and my, so that was, so part of it is just sort of habit. Part of it, the real part, I guess, is, is that I, as long as it's a directional mic, what I'm trying to do often is get intimate sounding,

• 34:41Speaker 02

  you know, conversations. And so if you have an omnidirectional mic, which is the mics, the mics recording pattern is picking up from all around, the whole field of, you know, where you're recording.

• 34:55Speaker 02

  You know, you just have to be, you have to worry a little bit more about placement and you just, you sometimes don't get, it doesn't feel like they're as present. Whereas if you're using one of these sort of unidirectional boom mics, like the one I use, it's really weird. Like when you point it at somebody, you can hear them and when you point it away, you really don't hear them very well. It really drowns out all the surrounding sound. And so what that means is you get this pretty nice, very, very intimate sound. And then if you, and then if you're in a, in a place where lots of other stuff is happening around and you want to document the fact that you're out in the field and there's a rodeo going on behind you or whatever, you can just, when you're done with the interview, you just point the mic at the rodeo and get that ambience. And then you can just use

• 35:37Speaker 02

  it as an ambience bed. So, so I like, so I like the intimacy that you get with a, with a nice tight boom mic.

• 35:46Tim Ferriss?

  What, no, that makes perfect sense. What numbers do you check on a daily or weekly basis? And not to beat a dead horse, but this, do you guys use Chartbeat? Did you end up using that? And what other, what other numbers besides just straightforward kind of revenue numbers for sponsors? What kind of stuff do you guys check?

• 36:07Speaker 02

  I mean,

• 36:07Tim Ferriss?

  If anything?

• 36:08Speaker 02

  Again, I'm, I'm, I'm, I was obsessively checking our SoundCloud numbers because we, we host on SoundCloud. And so I could see, so, and SoundCloud feeds our iTunes. So every time somebody's, any time somebody who's subscribed to Startup, it downloads to their phone that registers as a play on SoundCloud. So SoundCloud was documenting, was sort of capturing both the, the people who are listening, streaming it through the web or through our website or whatever, and the people who are downloading it onto their phones through iTunes or some other podcatcher. So it was a one-stop shop for, for our listening numbers, basically. And so I would check that. And that was pretty much everything

• 36:53Speaker 02

  that I checked. I didn't, you know, I know PJ and Alex, the hosts of Reply All, are much more tech savvy and much more, you know, sort of aware of what's going on. And so every once in a while, I'll ask them, sort of like, what are they looking at? And they look at Chartbeat a lot. But, but we haven't, I don't look at that, that much.

• 37:15Tim Ferriss?

  Got it. So I want to rewind the clock a little bit and just, I'm looking at, I'm looking at your bio and it says you've worked as a social worker, a caterer, an eighth grade science teacher, and a graduate level journalism professor. Tell me the story of how you got to radio, if you could.

• 37:33Speaker 02

  Uh, yeah, the story, I guess the story starts, I was in, I was in, I was a teacher. I taught eighth grade science. And I was, I did that for four years and I, this was in Chicago.

• 37:50Tim Ferriss?

  How old were you, how old were you at the time?

• 37:53Speaker 02

  This is basically right after college.

• 37:54Tim Ferriss?

  Around what time was this?

• 37:55Speaker 02

  Yeah, this is in my, in my mid to late twenties. So, starting at like, maybe like 24 to the time I was 28 or something like that, 28, 29. I was a teacher. And, and I had, basically it starts like, I'd always been interested in this kind of, I guess what you'd call long form narrative nonfiction. You know, like, I had read, you know, a couple magazines since the time I was in high school. Like, I liked the New Yorker magazine and I liked Harper's magazine. And I liked these kind of, and I would read these books of like, you know, sort of like, you know, Joseph Mitchell, who's this sort of famous old, you

• 38:38Speaker 02

  know, nonfiction writer. And I would read, you know, E.B. White and stuff like that. John Hershey, you know, the guy who wrote Hiroshima. So, I, is it Hershey? Hershey, right? And, and so I was, I was into that kind of stuff. And then I would, but I never, for some reason, and I was, I was a pretty good student and I like, you know, I did, I did okay. But somehow it never occurred to me that I could actually do that as, for a living. I don't, and I don't know why. Like, I really don't know why. I thought, I just somehow thought that like, the people who did that were some sort of different

• 39:20Speaker 02

  world of people that, like, I would never be able to access that world. And like, now it's ridiculous, like, the thought that, like, you know, an upper middle class Jewish kid could ever make it in the media world. Like, you know, of course.

• 39:36Speaker 02

  How could that happen? I don't know why I was so, I don't know why I was so, I think it was just like a profound lack of, I didn't know anybody who'd ever done that. I grew up in Cincinnati, Ohio, which was like, you know, not, not super provincial, but just, you know, certainly not a media capital. And so, you know, people who succeeded became doctors and lawyers and that was sort of it. So, so anyway, so then, but then I started dating a girl from New York when I was in Chicago. And she, that was more of where media happened and she knew people who were actually getting jobs at magazines. I was like, oh, getting a job at a magazine is an actual thing.

• 40:21Speaker 02

  And then we dated for a while, we dated for like four or five years and then she eventually broke up with me, which was like one of the more profound experiences of my life. And that was really what kicked me in the ass and sort of was like, and that happened right, you know, in my late twenties and that was when I was like, okay, well, if, if you're gonna, like, I don't know what you're, you know, I was telling myself, like, it was basically spite, like, I was worried that her plan was to go back to New York and go to film school and I was just like terrified that she was gonna become a famous director and I was gonna be sitting around supervising recess. And so it was really that that was like, okay, you gotta, you gotta try to, you know,

• 41:03Speaker 02

  this has been this dream that you haven't really admitted to yourself, so you should just try to do it. So, so I started trying to freelance and I had an internship at Harper's Magazine that I, that I successfully applied to and got over the summer in between, in between one of those years when I was teaching. And, and then eventually through Harper's, I met, I got a, I got a job as the administrative assistant at This American Life, which was, you know, the public radio program and podcast that was just starting, this is back in the, like, I guess back in 97.

• 41:40Speaker 02

  October of ninety seven, when I got that internship, when I got the administrative assistant assistant job, and it had been on the air, I think, two years at that point, and had become, you know, had already made a name for itself, but wasn't, you know, the, you know, beast that it had, that it is today, the podcast kingmaker that it is today. So, so that's where, that's, that's, that got me started, you know, so I was an administrative assistant, I sort of learned on the job, it was like four of us back then, it was Ira, three producers and me, and

• 42:18Tim Ferriss?

  What a perfect, perfect timing, man.

• 42:21Speaker 02

  Yeah.

• 42:21Tim Ferriss?

  What a great job.

• 42:22Speaker 02

  Yeah.

• 42:23Tim Ferriss?

  Just the four of you, that's amazing.

• 42:24Speaker 02

  Yeah, and I learned a lot on the job, but then I eventually, but then, you know, eventually, so, but I was the administrative assistant, right, I was like the one writing, you know, answering the mail and sort of like running to the post office and doing all the stuff that needed to be done, and because we were so short-staffed back then, and because like, you know, Ira really had no idea what he was getting himself into, like a weekly hour of documentary radio, where like the standards are higher than anybody has ever had before, like he is a perfectionist, you know, and I learned a lot about the value of being a perfectionist from him, so, but like, you know, the fact that he was trying to produce that with, you know, three producers who didn't really know what they were doing, because nobody knew what they were doing, you know, like

• 43:07Speaker 02

  he was, he was trying to invent it, so, it was all hands on deck, and so occasionally I would get to produce stuff, or like help with the editorial side of things, and so I learned on the job, but then, there came a moment where I was like, I produced this, I'd actually produced semi, like, not what I would call producing now, but I'd assisted in the creation of one, of one of our big early shows, which was an hour-long documentary about Harold Washington, and the first black mayor of Chicago, and, and it was sort of a hit, you know, in the, in the early days, and, and I came in after, and I'd been, you know, just a bear to produce, and I was working all kinds of crazy hours, and I came in after it aired, the day, the Monday after it aired, and, fully expecting like, okay, now I've succeeded, I passed this test, and now I'm gonna be made a producer, and I said I wanted,

• 43:51Speaker 02

  you know, what, what did he think, was he gonna make me a producer, and he was like, no, I can't, I don't, I don't have money to make you a producer, I don't have a position open, and I need an administrative assistant, and I was like, oh, well, if you ever did have money And the position opened, would you hire me? And he was like, I don't know, probably not, because you don't have the experience still that I need, you know? There's other people now who have that experience. And I was like, well, what do I need to get that experience? And he said, I don't know, you probably should quit and start freelancing. And I don't think he thought, and now, as a CEO of my own company, I have this experience all the time where I'll sort of think out loud, and I don't realize that the people I'm talking to are like hanging on every word. I'm sure that was what happened with him.

• 44:34Speaker 02

  But to me, I was like, okay, well, you've just given me the map of how I want to get my dream job, so I'm going to quit. So I put in my notice, and I arranged like a loan from my parents to help me live for the year, like 10 grand. I was like, if you give me 10 grand in lieu of graduate school, I will get to make it as a freelance writer. And we, and I, you know, I did, I just tried to freelance, and I got stories in magazines and art and newspapers and stuff like that, and I continued to do radio. And then, a year and a half later, I'd sort of built a little freelance career for myself, which was going pretty well. And then there was finally an opening at This American Life, and things had been going so well that I actually was like, oh, I'm not going to apply for that, because now I'm doing this other thing.

• 45:18Speaker 02

  And then finally, somebody was like, this was your dream job, right? And I was like, yeah, I guess it was. And then I applied, and then immediately, I was like, I really want this job! So, and then I got it. So that was, that was, that was how that happened.

• 45:29Tim Ferriss?

  Wow. So when you were freelancing, the, how did the, let's see here, the writing that you were doing, did you find the writing took off more so than the radio? Were they taking off in tandem? Did the radio start to outpace the writing? How did that, how did that go during your year of freelancing?

• 45:50Speaker 02

  Well, one of the things that I learned at that, one of the biggest lessons I learned is never, ever return your key card. So, I still have my key card from WBEZ, the radio station where I'd been working in Salt Lake.

• 46:10Tim Ferriss?

  Coming up, why good radio doesn't necessarily apply to television, the value of perfectionism, and the good and bad habits that Alex picked up from This American Life and Ira Glass. But first, a word from our sponsors.

• 46:25Tim Ferriss?

  The Tim Ferriss Show is brought to you by Onnit. I have used Onnit products for years. If you look in my kitchen, in my garage, you will find AlphaBrain, chewable melatonin for resetting my clock when I'm traveling, kettlebells, battle ropes, maces, steel clubs. It sounds like a torture chamber, and it kind of is. It's a torture chamber for self-improvement. And you can see all of my favorite gear at onnit.com/tim. That's O-N-N-I-T dot com forward slash tim. And you can also get a discount on any supplements, food products. I like Hemp Force. I like AlphaBrain. Check it all out, onnit.com/tim.

• 47:05Tim Ferriss?

  The Tim Ferriss Show is also brought to you by 99designs. 99designs is your one-stop shop for anything graphic design-related. You need a logo, you need a website, you need a business card, or anything else. You get an original design from designers around the world who submit drafts for you to review. You are happy, or you get your money back. And I have used 99designs for book cover ideas, for The Four Hour Body, which went to number one New York Times, for banner ads. And you can check out some of my actual competitions at 99designs.com/tim. You can also get a free $99 upgrade if you want to give it a shot. That's 99designs.com/tim. And now, back to the show.

• 47:54Tim Ferriss?

  Were they taking off in tandem? Did the radio start to outpace the writing? How did that, how did that go during your year of freelancing?

• 48:02Speaker 02

  Well, one of the things that I learned, that, one of the biggest lessons I learned, is never, ever return your key card. So, I still have my key card from WBEZ.

• 48:15Speaker 02

  The radio station where I had been working. And so I would, I could come in and I was, I had some freelance projects that I was still working on at that, at that station. So they had hired me to help produce this like poetry series they were doing. And so I was picking up freelance work, both in radio and on the writing side. And it was pretty equal. Like I did a big radio documentary and I did something for a show called The Savvy Traveler, which was a travel show back then. So within the public radio world, there was like, there was enough stuff that needed to be done and not that many people who were like sort of free to do it, that I could pick up, you know, sort of work at that point as well. So it was about half and half.

• 48:58Tim Ferriss?

  Got it. And how did you come to then co-found Planet Money? Because, I mean, and what was the timeline between getting, landing that dream job as producer and getting to Planet Money?

• 49:13Speaker 02

  So that was, I guess there was a year. I mean, no, there was, there was a decade in between getting the job. I got the job in 99 and then Planet Money started in 2009. And one of the nice things about working at This American Life was that like the job was constantly changing as I was there. So I never had to like, I never got bored. Like, you know, I started and I sort of took a long time. The learning curve was pretty steep to get good at producing documentary radio. So for a couple of years, I was just trying to get my head above water and figure out how this stuff worked and what people were talking about in these edits and, you know, how to become better at recognizing good moments and all that stuff.

• 49:56Speaker 02

  And then, and then, and then, you know, 9/11 was, I mean, it sounds cheesy and trite to say, but like 9/11 sort of changed the focus of the show quite a bit. We became, you know, we did a couple of shows on 9/11 and then we, we just got, I think it, I think it made us a little bit more, I mean, we'd always been serious journalistically, but I think it like.

• 50:21Speaker 02

  Felt like we were able to tell kinds of stories that were both sort of journalistic and human in a way that felt like it filled a niche a little bit. So we did a lot of reporting on that and on the war and we went to an aircraft carrier. So that sort of changed. And then we did a TV show in there, too. So we did this big TV show for Showtime and I was an executive producer on the TV show. So then I was like spending, you know, three or four years learning how to do TV, which was a whole other huge learning curve. And man, did we get our asses handed to us there. Like, we thought we were storytelling experts and then we got into this new medium and we were like, nothing we know works.

• 51:01Tim Ferriss?

  Could you give some examples? Because, yeah, I'd love some examples.

• 51:07Speaker 02

  Yeah, well, I mean, it's like-

• 51:08Tim Ferriss?

  Or an explanation of why it doesn't work. Why didn't it translate?

• 51:12Speaker 02

  Well, everything that I laid out to you about like what's good tape, you know, what you're going for in a radio interview, like that stuff doesn't apply to TV. So like what I'm often, you know, you can make an amazing radio story out of one or two people telling a story that happened to them in the past. Like, you know, one of my first, I won a big award called the Third Coast Audio Award at This American Life, which was essentially two people, a brother and a sister, talking about a story that happened to them, you know, 60 years ago. And it was just the two of them talking and we intercut them and we put in a little bit of script. And it was like one of the most moving stories that I've ever produced. And like, that's death on television.

• 51:56Speaker 02

  You can't watch people telling a story about something that happened a long time ago. Something about it just does not work. And we would try to produce these things and we'd be watching them and we'd be like bored out of our skulls. Because there's just like, you just need so much more visual information than just watching people's, you know, watching people talk. So that was one of the big lessons, is sort of like, it made me realize like, oh, TV, that's why- That's why reality television is so, is so big. Like, you, you can do it. You can produce a story from the past, but it's, but to do it, you have to just feel, you have to give people something to watch.

• 52:36Speaker 02

  And so you have to invent an entire visual story to go along with the, the story that the person is telling. And that's just, and that's really expensive. So if you look at like an Errol Morris documentary or something like that, where like, there was that one where he- What would be an example of, of one of those documentaries? So like The Fog of War? The Fog of War was one that I thought about a lot. So that's the one where he interviews, um, who's the interview? Um, uh, what am I, what's his name? The guy from Vietnam? I haven't seen the movie. Okay. He interviews a famous, uh, general from Vietnam, who was one of the ones that sort of like was, came under a lot of criticism.

• 53:17Speaker 02

  He, and it's a lot about like what went on back then, you know, in Vietnam. And if you watch the movie now, and I watched that movie around this time, and I was like, oh, look at what he did. Like, he filled every second, every frame with like invented imagery that he had, that he had to invent and come up with. And it's so time consuming and so expensive versus- Sounds like, uh, sounds like Man on Wire. Yes, and Man on Wire, exactly. The same type of thing. And if you watch that movie now, they have to do so much work to keep the screen covered with interesting things to watch. Versus if you just take, you know, your average reality show where you've got like two family members fighting with each other, that's the, that's the narrative crack in visual terms.

• 54:02Speaker 02

  Like, we are hardwired to watch that stuff. And it's so much cheaper. You just turn the camera on and you watch two people fighting and you want to watch it. You know what I mean? And so, and so it made me realize, oh, that's why TV is the way it is, because that's what we want to watch. You know, we don't want to watch- Yeah. You know, we want to watch things moving on screen. So, so it was really, it was really hard. And so we had to think, we had to think entirely differently. We had to think entirely visually, like what's an interesting visual story versus an interesting audio story.

• 54:34Tim Ferriss?

  Yeah, and I suggest anyone listening who enjoys reality television not learn too much about how it's produced because it will it will shatter the veneer. I remember I was I was talking to this guy who's worked on a bunch of reality shows you would recognize and he said, have you ever noticed how many of the arguments happen with people standing up in the kitchen and someone's always mixing something? He's like, do you think that happens naturally? I thought it was like, that's a good point. They are always arguing in the kitchen and someone's just absentmindedly stirring something that we never really find out about.

• 55:08Speaker 02

  Right, exactly.

• 55:09Tim Ferriss?

  But I wanted to come back to perfectionism because you mentioned you you learned the benefits of working with a perfectionist, or maybe you said being a perfectionist. And you also mentioned The New Yorker. So I had a chance very, I was very fortunate to have the chance to study nonfiction writing for a semester with John McPhee, who's a staff writer for The New Yorker and just a phenomenal, phenomenal writer with the greatest attention to detail and structure of anyone I've ever met. But I'd be curious to hear sort of what, what did you learn from working with with Ira? What are the benefits of being a perfectionist or working for one?

• 55:52Speaker 02

  I think, I think it basically, it just, it, what I learned is that a lot of it is is just about the effort you put in and it's not about, like, you have to have, you know, you have to have a creative brain and like, part of it is that, you know, you're just, you're just sort of born with, I guess partly, you're, you're, you're sort of born with part of it at least. But like, watching Ira, like, sort of like, work, a lot of times he's just, he just keeps thinking about it longer than other people keep thinking about it. And then eventually he comes up with an idea that's good. And it just made me realize like, that's how people get to good ideas, is they go through a lot of bad ideas

• 56:33Speaker 02

  first. And that there's not really, like, occasionally a good idea comes to you first if you're lucky. But like, usually, it only comes after a lot of bad ideas. And so what being a perfectionist is, is sort of just like putting in a little bit more time to think through the level one or the level two ideas and try to get to something that's a little bit deeper.

• 56:57Speaker 02

  And I think that's why we do as many edits as we do, because often what happens in an edit is you'll take a bad idea and you'll make it into a good idea over the course of several edits. And you'll have an idea that's in a script that's sort of like, that's just getting you from one point to another point, and then you'll be like, you know what this is like, it's like this, and you'll come up with a good metaphor. And then you'll be able to like, oh, that's a good metaphor to put in this part of the script, it'll really make it sing. And then eventually you'll get to a part where you're like, oh, it feels like a revelation will now happen at this point in the piece, whereas before it was just moving from one, you know, from one thing that happened to the next. So, so I think that I learned that. And then...

• 57:37Tim Ferriss?

  Are there any examples? I'm sorry, go ahead.

• 57:40Speaker 02

  Yeah, go ahead.

• 57:41Tim Ferriss?

  I'm gonna come back. No, I was just gonna ask you, are there any examples of, perhaps from Startup and Reply All, but it could be from previous shows, of a specific bad idea that was turned into a good idea? Or that became a good idea?

• 57:54Speaker 02

  Yeah, I mean, it happens every single time. So, I'm trying to think of one that I could share that was like, that's like, that's easy enough to explain. Let me think for one more second. I don't know, this might be hard to do.

• 58:12Tim Ferriss?

  Sure. We can, we can, we can come back to it. I wanna, feel free to pick up where you left off, but maybe...

• 58:18Speaker 02

  Yeah, yeah, let me think about it for a second. I can come up with an example for you, but...

• 58:21Tim Ferriss?

  Okay. Are there any habits that you picked up from IRA or the This American Life team otherwise that you, you still have? Any particular, any particular working habits? But, either, either or both?

• 58:39Speaker 02

  So, the good habit that I picked out is, that I picked up is sort of like, like...

• 58:47Speaker 02

  Being committed to excellence, like that is something that I learned. And I learned it from Ira. Like, I think he really just hated to have something go out when it could have been better. And if he had an idea of how to make it better, he would always, almost always, try to make it better. And still does. And that's like, that was, and I was not that way. I was sort of like the kind of guy who was like, "Yeah, it's good enough," you know? And what I realized is that, and I, but I, that was sort of a, I think being that way is a little bit of a dodge, or rationalization, or an emotional sort of like thing you do to sort of like not actually try to make things good.

• 59:29Speaker 02

  You know, because trying to make things good is scary, and you might fail, and people might say it sucks. And we all know that, and so we all like find our ways of rationalizing with it. And of rationalizing, and that's what I was doing. I was like, "It doesn't matter, it's okay." And so, working with Ira, like, I was like, "Oh, no, this is a guy who really cares about making it good." And of all the things to care about in the world, that's one of the better ones, you know? Just to try to make something excellent, like, there's a lot of things you can care about, and that's a good thing to care about. So I learned that from him. And there's a certain comfort with crisis that he had that I'm afraid wore off on me also.

• 1:00:14Speaker 02

  But I don't think it's a good thing. I think that's a bad thing.

• 1:00:19Tim Ferriss?

  Can you give any, any particular moment come to mind? And, yeah, let's leave it at that.

• 1:00:26Speaker 02

  I mean, I think, I mean, he, just the show was always like, for the entire time I worked at This American Life, it was always like, up until the very last minute, it was, it was getting produced and edited, and, you know, it was always like, it was, you would be shocked, probably like 20 to 30% of the time, you were like, "Is it even gonna go up?" And that's crazy, you know, over like 15 years.

• 1:00:49Tim Ferriss?

  That's a lot.

• 1:00:50Speaker 02

  To be like, 20 to 30% of the time, "Are we gonna make it this time?" I mean, and then at a certain point, I was like, "Oh, yeah, we're always gonna make it, because we always make it." But still, it's like, it's always right up into the, right up into the last minute. And it's better now, it's way better now. And like, they've gotten like processes in place and stuff, but...

• 1:01:10Speaker 02

  And part of it is just audio is real time. So even if you've been doing it for a long time, you just can never quite get your head around how long it takes. But part of it is, but part of it is just sort of like, he's comfortable with that. And I think in a certain way, it focused his mind, I think. And I think it also focuses my mind, I think. Like, I've noticed myself doing, like, this, this episode recently, like, you know, I'm the one who's writing it. And I've got a whole bunch of other things that I have to do on top of writing the script for this week's episode. And it's like, I sit down, I try to think, but I'm like worried about this thing, and I'm worried about that thing. And I, and in the back of my mind, in this bad part that I learned, I think, is, I, but

• 1:01:54Speaker 02

  it's gonna, I'll, it'll, I still have, you know, you know, Monday morning at 5:00 a.m., I'll just get up early, you know? I still have that in my, in the back of my mind. And then, and at that point, I'll have no choice, and I will have to make it good. And so I'll just leave it till that moment. And I don't think, that's not good. And like, what it does is it drags everybody else into your crisis. And so my, you know, Caitlin, my producer, is like dragged into my way of dealing, my way of managing my time and my way of sort of trying to make things good. And that's, I don't think, I don't think she likes it. And I didn't like it when I was a producer. Like, I felt like, why is he saving everything till the last minute?

• 1:02:39Speaker 02

  And I'm doing my, I'm doing the exact same thing, you know, to my, just now.

• 1:02:44Tim Ferriss?

  Yeah.

• 1:02:45Speaker 02

  So I think that's because, that's because I learned all those, you know, I learned, I had 20 years of learning, like, yeah, it always comes out. You know, it's fine. So, it's bad, but it's bad, you know? So.

• 1:02:55Tim Ferriss?

  Yeah, I've, I've learned that that, I've developed a similar level of comfort with crisis and last-minute turnarounds. And I, from personal experience, learned the hard way that that is a very fast way to burn people out who haven't been conditioned. And how you can lose really good talent, unfortunately. The, the commitment to excellence, are there any stories that come to mind of particular time? For instance, you handed, you, you passed something on to Ira that you thought was good enough, and he was like, no, not good enough, and gave it back to you? Did that happen?

• 1:03:34Speaker 02

  Um, yeah, oh, I mean, all the time. Like, every single thing I ever read or did was, it was, I never, and this is not an exaggeration. I don't think anybody ever in the history of This American Life has ever had this happen, where they'll read a draft, even if it's the second or third draft, and it'll be like, and the answer is like, "All right, it's all done."

• 1:04:02Speaker 02

  There's always a new tweak, and there's always something that can make it better. And often, there's like, big thoughts. And so, and again, like, and in the beginning, it would sting a little bit. It would be like, "God, I just want to do one thing where it's like, done, and I did it right. I took it really personally, like, I'm not doing it right." And then, it was only over time that I realized that, like, no, you're not, nobody does it right. Like, the first draft always sucks, always, for everybody. And you've just got to get over yourself a little bit. Like, it's not about you and your ego, it's just about trying to make it better.

• 1:04:42Speaker 02

  And then, and then I realized that it was like, that's really useful, to be able to have that muscle of like, sort of like, "Okay, I trust myself enough that I'm not a complete idiot,

• 1:04:57Speaker 02

  but that it's always, you know, and I can be made better by other people's input and ideas." That's essentially what an edit is. And that's also a really good way of going through the world, you know? Is to try to be open to what people are telling you. So, that was a really, I think that's, you know, the commitment to excellence means being comfortable hurting people's feelings, and being comfortable having your feelings hurt. And to try to take the feelings out of it. And just talk about like, what the thing you're trying to do is. And that was really useful to learn.

• 1:05:39Tim Ferriss?

  And would Ira ever just say, "This isn't good enough, give it another shot," or was it always very specific feedback?

• 1:05:48Speaker 02

  Always very specific feedback, always very specific.

• 1:05:51Tim Ferriss?

  Got it.

• 1:05:51Speaker 02

  Not "do it again better," like that's sort of like.

• 1:05:54Tim Ferriss?

  Yeah.

• 1:05:54Speaker 02

  And that's also, I think, what being a good editor is, because he's such a, he was such a master of like the form, that he could tell you what was wrong, and he could tell you like, "This isn't working for this reason." And often, it's like, it's like really stupid little things. Like, so for example, I can give you an example of this. Like, from this current episode of Startup that we just did, we, it's all about burnout. And basically, we made the stupid decision to, it's coming out today, I think it'll be up by the time this posts, so you can, people can listen to it. But it's, it was, it, basically, we, you know, we, we had this, we had this situation where like, the hosts of Reply All were working, they ended up, they were working late, sort

• 1:06:39Speaker 02

  of like, every day, for like, weeks. And this was over the holidays, when we made the stupid decision to try to put up a show on Christmas and on New Year's Eve. I don't know why we didn't take the week off, but we didn't, I think we felt like we were just new, we were just starting, so it wasn't, was too early to take time off or something. So, they were crashing, trying to get these shows up on Christmas Eve and on New Year's Eve, and the shows weren't coming together very well, and they were just working really, really late. And then, one of our, when Lisa started recording conversations with them, about like, how they were feeling. They were feeling super burned out, and it was, "It's really good, it's really good tape." And so, that's what the episode is about.

• 1:07:22Speaker 02

  And we were scripting the episode, and I started by, and this all happened, it came to a head when I was out of town. I was in San Francisco, where my, where my wife's family lives. And we brought the kids out there, over the holidays, but I was like, it was supposed to be sort of a vacation, but I was basically working the whole time. But there was a day or two that I didn't work. And so, I started the story by saying, like, all this happened while I was on vacation. It was just like, one line. But that one line put this whole, like, and the story was pretty good. And we were just telling the story and we were like, we were playing all this pretty entertaining tape of people talking about how burnt out they were and how their whole feelings about their jobs had changed.

• 1:08:03Speaker 02

  And it's all very real, very raw, very entertaining. But something about me saying that I was on vacation had this whole scoldy tone all the way through it, which is sort of like, I leave for one day and the whole place goes to hell, sort of, which was not intended at all. It had that feeling. It sort of cast the entire episode in this sort of like unpleasant light. And so that's what I'm saying. It was, and we were doing these edits and we were like, this should be good, like the tape should be good. But when we were listening, we were like, I have this, I don't like it. It's making me feel bad, not good. And it wasn't until I was like, one of our, Starlee put, I think, one of our other employees put, put her finger on it.

• 1:08:48Speaker 02

  She was like, it's that, that's, that's the thing that's making it feel bad, is that, just that line in the beginning where you just sort of, it colors the whole way you're hearing this thing. And so we just re-crafted the beginning to be about like, this transition in a startup's life, where you go from trying to raise the money to all of a sudden you're running the, running the organization, right? And they're two totally different jobs. And like, this is an episode about how we were trying to manage the second phase of actually running the company and dealing with our employees. And so that gave it a much better context, basically, to listen to the story in.

• 1:09:23Tim Ferriss?

  How far into the episode did you put your finger on that and fix it? So from the, from the first kind of pitch meeting or decision to make the episode about burnout, what amount of time elapsed before you were like, oh, okay, that's, that's this issue we need to fix?

• 1:09:42Speaker 02

  Uh, it was probably like, we did the first, we did this edit and we actually put together a rough mix, which we all listened to over the weekend. And that was the one we were all like freaking out because it wasn't working at all. And we were like, oh my God, this is a stinker.

• 1:09:54Tim Ferriss?

  Hmm.

• 1:09:55Speaker 02

  Uh, and...

• 1:09:56Tim Ferriss?

  And the rough mix is like missing music, it's just a bunch of tapes strung together?

• 1:10:00Speaker 02

  Yeah, yeah, it's, I mean, it's a little bit more than that because it was like, we had a really good guy doing it. But yes, it was like, uh, the levels weren't all mastered and everything like that. We knew that we were gonna come back.

• 1:10:09Tim Ferriss?

  Do you do scratch, do you do like, scratch audio for the script as well, or no?

• 1:10:12Speaker 02

  We, we had recorded the script. We had recorded the script. So we'd done the whole thing. Like, we'd, it was, it was, this was actually more work than we normally do. Normally, this would have been a second edit, but we were like, sort of behind the guns. We were like, well, maybe this'll work. So, but it didn't. So, so it was essentially like a second edit. And we did the second edit. And we realized that it wasn't working. And then it was over the weekend, basically, that we were thinking about it. And then this morning was when we sort of, like, I came in and rewrote, rewrote the, the top, based on sort of notes that Starlee had given me last night, at ten. And there was a couple of other things that were happening in the episode that were also sort of like robbing it of, of its, of its power, uh, that we changed as well.

• 1:10:55Speaker 02

  But, uh, but yeah, it took, it was probably like a couple of days of sort of like sitting and thinking with it. That's the other thing that I learned from Ira also about excellence. Like, excellence is just tricks. You know, it's just managing your time and your expectations. Because there's this panic where you do, like, when I first heard the rough mix, I was panicked. Because I was like, this is bad. This is a bad show. But like, but I have seen, but then I had to remember, like, okay, but you thought some part of it was good in the beginning. And you have to go back and remember, what was the part that was good? And there's some reason that something that was good has not become bad.

• 1:11:39Speaker 02

  There's something that you're doing wrong that you have to fix. It's not a crisis, you know what I mean? It's just sort of like it's a problem to solve. And it's just hard to remember that sometimes. Like you just get, and I think that's what, with experience, you start to realize. Like you've done it enough times, like you've taken something that was bad and you've made it good, that you realize like it's not the end of the world, or it's not even, it's not like something that can't be fixed. Because that's the feeling. You feel like, oh my god, there's nothing to be done. Like the thing that I thought was good is bad.

• 1:12:11Tim Ferriss?

  So I'd love to talk about, ask just a few more long-form questions, a couple of fast ones, and then we can wrap up. But I want to talk about turning a bad situation into a good one. Very specifically, I'd love to chat about startup episode number nine, "We Made a Mistake." And about being attacked and villainized. So maybe just for context, if you could explain to people what that mistake was? And then I'd love to dig into that a little bit.

• 1:12:41Speaker 02

  Yeah, so we do these ads on the show. We have two ads in the middle of the show. And we produce our ads documentary style. So what we try to do is we just try to interview people either in the company or users of the company about their own real experiences. And we turn those into little 45-to-minute-long segments as our advertisements. And one of our sponsors was Squarespace, and the website company. And what we were doing is we were talking to different Squarespace users about their Squarespace sites. And we'd found this kid, this lovely charming little boy who had a Squarespace site that

• 1:13:25Speaker 02

  he used for Minecraft. And we'd done this interview with him, and it had been lovely. And then we put it up, and we realized that we had never told him or his mother that it was for an ad. And she had the impression that this kid was going to be on This American Life, like that her son was going to be on This American Life. And then she got, and then she heard from a friend that it was actually used in this ad, and then she got very upset, and she went on Twitter and was talking about it on Twitter. And she had a large Twitter following, and so a lot of her Twitter followers were... You know, upset as well. And then we started digging into the details and it was like a little bit even worse because like it turned out that the email that we'd sent

• 1:14:09Speaker 02

  to her had sort of, you know, given the impression that I did still work at This American Life, which was, made it seem even sleazier. I don't know, it was just a, it was like a really bad screw up on our part that, that seemed to her quite logically and rightfully that had been on purpose and an intentional deception.

• 1:14:30Tim Ferriss?

  And I enjoyed the episode for a host of reasons, but I mean, the first of, first of which is we all make mistakes. The second of which is how quickly things can spiral or seemingly spiral out of control with the internet.

• 1:14:44Speaker 02

  Yes.

• 1:14:45Tim Ferriss?

  And social media and how much of a crisis it can seem like. And just like you working as a producer, you know, I've been sort of on the front lines online for a good period of time now. So when, when someone's like, oh, like this, this like parody piece came out about your book in the New York Times. And now I'm just like, huh, interesting. I guess I should take a look at it later this afternoon. I don't have the like, oh my God, the sky is falling. Everything is over.

• 1:15:11Speaker 02

  Right.

• 1:15:12Tim Ferriss?

  Response.

• 1:15:13Speaker 02

  Which we very much had.

• 1:15:14Tim Ferriss?

  Not always.

• 1:15:15Speaker 02

  Which we very much had. I definitely realize that now. Like, it was like, sort of like, and there was a couple of people who were sort of visiting the office around that time and they were like, we think you're overreacting. And it was like, it just, which we definitely were, I think. But it definitely, it did feel like this, like the company was so new and so young and we, and, you know, we've managed to do this thing, which, which I wasn't sure I was going to be able to pull off, which was sort of like to document making all these mistakes, you know, and still have people like along for the ride with you. You know what I mean?

• 1:15:50Tim Ferriss?

  Right.

• 1:15:51Speaker 02

  And like, because a lot of times when you, a lot of times when you make mistakes, you're not at your best, you're at your worst, you know, it's your sort of, your unpleasant side or the part of you that's sort of a dick or whatever is sort of coming forward. And to sort of air all that and still have people sort of on our side and supporting the company and supporting the show, we felt like we were already walking a tightrope and this felt like this was going to be the thing that knocked us off.

• 1:16:13Tim Ferriss?

  And, no, definitely. And what I was curious to ask you is, As someone who's been on the documenting side for so long, looking at different situations, documenting other people's lives, perhaps painting them, not in a negative light, but in a neutral or comprehensive light, if you went back to, say, interviewing people and covering people for hard-hitting news or something like that, like, has your viewpoint changed or your feelings about that? Because a lot of journalists absolve themselves of the damage they might do to someone if it gets a lot of clicks or a lot of views or a lot of listens.

• 1:16:54Tim Ferriss?

  And I'm just, I know that This American Life is, at least all the episodes I've heard, are very constructive, but I'm just wondering how your feeling about, how your feelings as a journalist or documentarian changed as a result of becoming a target yourself?

• 1:17:12Speaker 02

  Well, I think I definitely, you know, I definitely have changed from where I was in the very beginning, when I first started. I, you know, I was never like a gotcha journalist, like, I was never like out for the expose.

• 1:17:34Tim Ferriss?

  Right.

• 1:17:35Speaker 02

  You know, and so, like, that wasn't, and at This American Life in particular, that's one of the other things that I think I learned a lot from Ira, is that he really didn't, like, he didn't want to just do the story where you didn't get the comment from the person who was supposed to be the villain in the story or whatever. Like, he really was trying to understand everybody's point of view. And that's what makes that show great, and I feel like that was an amazing lesson to learn. But it was, you know, in the beginning, I didn't take it that, I didn't take it as seriously as I do now. Like, I don't think I've ever, I don't think I've ever left anybody, there's one story that I regret, where I was doing, it was a story about testing in North Carolina, about standardized testing.

• 1:18:20Speaker 02

  And I interviewed a bunch of different people in North Carolina who were sort of pushing this, you know, pretty heavy standardized test thing in the state. And I ended up interviewing one of the main guys who was behind the testing thing, and it got into this really testy interview, and... Testing in a bad way, not about testing. And I think, you know, and he accused me of having an agenda. And I did. Like, I didn't, I was a teacher. I didn't like standardized tests. And I was, I told myself at the time that I was an open-minded person. I was trying to like, I was trying to be, you know, I was trying to do this in an open-minded way. But I think, looking back on it now, I would have, I wouldn't have, I would have done

• 1:19:05Speaker 02

  it differently. I would have tried to find every side of it, you know, instead of just trying to tell the side that I wanted to. Which isn't to say that you don't, if you have a point of view that you, that you believe to be true, you can't tell that point of view. But it's just, it's always a better story when you're trying to understand the other side. And in fact, the other, yeah. So, and I, and I feel like now that I am, you know, and that, you know, getting it back to your question of sort of like, being on the other side of this whole sort of Twitter thing, that's how I felt. I felt like totally misunderstood and that like, people had not bothered to figure out like, what had gone on with me, even though, I mean, I didn't feel misunderstood because

• 1:19:46Speaker 02

  I felt like, once I understood what was going on, I, I totally got why they thought what was happening was happening. And it did look really fishy, so, so I, I get it. But, but you do feel like, wait, I just, this is just a mistake and there's no way to convince people of that, you know? It's really scary. And so, yeah, so I have a lot of, and I, I see that happening in the news a lot, I think, where like, you know, journalists take it, you know, sort of take it out on somebody. And where I feel like-

• 1:20:16Tim Ferriss?

  Oh, all the, all the time.

• 1:20:17Speaker 02

  There's another story there, yeah.

• 1:20:18Tim Ferriss?

  No, definitely. And I, you know, I made a decision early on not to attack people on my blog, for instance, which was really the first sort of property that, that I focused on. And partially because I felt like it, to, to attack people and tear things down is kind of cheap applause, it's going for cheap applause. It's like, you know, it's like doing a, it's like doing a bit on, you know, George W. Bush with a series of jokes as a stand-up comedian. It's like, okay, like, at, at the worst point in his presidency, it's like, of course you're gonna get some claps. But it's like, you can do better than that. I feel like you can- So I'd love to, I've been just very impressed with the shows that you've done so far.

• 1:21:02Tim Ferriss?

  I really look forward to what's coming down the pike, but I'd love to ask you some sort of rapid fire questions. And by rapid fire, it just means I'm asking them in short form, but you can feel free to expand if you'd like. Is there a particular book, or what is the book that you've gifted to other people most often, given as a gift?

• 1:21:23Speaker 02

  Oh, man. What is the, God, I don't, I don't even know. It's been like, so here's the horrible thing. I am so bad now about reading. You know, I think, and I blame my, my young children, which is also bad. But you know, but seriously, ever since I had, I had two, two, two children, so I have a two year old and a four year old, and you know, I'm doing this job now, and my wife has this really demanding job, and we just literally have no time to, to read. So to me, books are almost oppressive because all they are are just sort of guilt and reminders that I don't have any free time.

• 1:22:07Speaker 02

  So I can't, I don't, I don't even see them as gifts anymore. All I have is negative associations with them.

• 1:22:15Tim Ferriss?

  Their homework assignments.

• 1:22:16Speaker 02

  Yeah, they're just, I just feel guilty and sad. I'm hoping, and I've heard that that changes. And I actually, it's funny, I had this experience yesterday or two days ago where I like actually, like I, like I read, I had a free moment and I read something that a friend of mine recommended on, on Twitter, and it was this blog called The Tusk. And it was this, just this really lovely essay by this woman who was working in San Francisco. And it was the first real sort of like time that I'd sat and just read, done the thing that I love doing, which is like reading a really nicely crafted piece of writing. And I was like, oh, maybe things are starting to turn now. And it was just so foreign.

• 1:23:01Speaker 02

  I hadn't done it in like four years. And, and I was like, I think, I was like, okay, I think I'm gonna start to be able to get my life of the mind back soon. But like, it's one of the more ironic things about, you know, one of the more paradoxical things about producing all this content is that like, I don't, I don't, I don't, like the amount that my diet of what I, what I read and listen to myself has just gone so shriveled. Yeah, so sad.

• 1:23:26Tim Ferriss?

  Is, does any favorite documentary or documentaries come to mind?

• 1:23:30Speaker 02

  Yes, documentaries are easier, are an easier answer. I, I, well, I loved, loved Man on Wire. That was like one of my favorite, favorite things that I've ever seen.

• 1:23:43Tim Ferriss?

  Yeah.

• 1:23:45Speaker 02

  Oh, you know, the book that I read, though, there was a book that I read that I thought was just unbelievably fantastic, which was called On the Run.

• 1:23:55Tim Ferriss?

  On the Run?

• 1:23:56Speaker 02

  Yeah, Alice Goffman. And it's, she's a sociologist and it was just sort of like, basically, she, she ended up sort of like living in this black neighborhood in Philly. She's a white sociologist. She ended up living in a black neighborhood in Philly for like 10 years. Just, it started as like a sociology assignment and then just became her life. And she became friends with these three guys who were sort of like, who lived in the neighborhood and had rap sheets and were, and just sort of like fully, just sort of like, just, it's this book that I haven't really, like, I haven't read before, where like, she totally

• 1:24:35Speaker 02

  became to, she totally lived life through, through their eyes and sort of internalized everything about what it was like to be sort of like a poor black man in Philly in sort of an increasingly police presence neighborhood. And it was just, it was just devastating and amazing and like, it just made me like, understand everything that's happening in the country in a different way. You know, so, because I like, a lot of white people, I think, had this feeling of like, sort of like, however you feel, like, there's always this feeling of like, why, you know, like, well, whatever.

• 1:25:17Speaker 02

  It's like, it was just, it was an amazing, it was an amazing book.

• 1:25:21Tim Ferriss?

  Great, On the Run. All right, wrote that down. The, when you think of the word, or when you hear the word successful, who do you, who's the first person who comes to mind and why?

• 1:25:39Speaker 02

  Yeah, it's a funny, success is a funny thing. You know, like Barack Obama is a very successful person. I mean, like, I feel like there's like, like, when I think of success, I feel like there's two layers of success. There's a sort of the outsized success that is like, you know, we're just sort of like amazing sort of people who don't, who I feel like are like, have skills and abilities far outside my own succeed. And, you know, and that's your like, you know, sort of like Barack Obama is like that. Sort of like, wow, how did, you know, how did that guy become president? Like, somebody, you know, sort of like Bill Clinton, same kind of thing, like, sort of like where you come from, like, you know, not a background of privilege necessarily,

• 1:26:23Speaker 02

  and you've, and you're just, you've got these rhetorical skills and you do, you know. So that's one thing. But then other, you know, there's other people who just sort of like have managed to like carve out a nice life for themselves, which I feel like also is just sort of like, is successful, where they have like, you know, they have like, you know, they have people that they love and they're, they have, you know, they have friends and family nearby and they've arranged their lives so that it's, you know, they have like time to actually take pleasure in the things that give them pleasure. And by that standard, I'm not very successful myself.

• 1:27:07Speaker 02

  Like, I'm worried about that.

• 1:27:09Tim Ferriss?

  Who do you, who do you, who would you like to emulate more? Are there any particular people in your life or people you know of that you'd like to emulate to sort of carve out that type of, the life that you want for yourself?

• 1:27:24Speaker 02

  You know, I don't think about that stuff very much. Like, I really wanted, like, when I, when I was younger, I really wanted a mentor. You know, I really wanted somebody who I could learn from and learn how to, what my life would be like and like, learn a skill and learn, you know, something that would give me meaning in the world. And, and when I started working in This American Life, that's what I felt like I found I got, like, I was like, okay, now I have a path that I'm on and I'm going to be on that path. But once I was on that path, it was like, now I'm just sort of like, pretty consumed by it, by it, you know? And I don't...

• 1:28:00Speaker 02

  Who am I trying to emulate? I'm not really trying to emulate anybody, I don't think. Maybe I'm not being honest with myself, but I feel like it's like I have a very particular thing I'm trying to do and I feel like sort of too busy with that thing and I'm too focused on that thing to look around for other people that I would be emulating here. You know what I mean? Like, I'm pretty, I've always been a little tunnel vision that way. Like, I'm just like, I just sort of dive into the project that's before me.

• 1:28:27Tim Ferriss?

  Are there any, now that you're a co-founder yourself of a startup, are there any particular founders or CEOs that you admire?

• 1:28:39Speaker 02

  Um, I, yeah.

• 1:28:43Tim Ferriss?

  Who might not be the Barack Obamas in their respective fields, right? So not necessarily a Zuckerberg or someone like that, but someone where you're like, okay, that person is handling things in a way that I might want to at some point. Or anyone who particularly impresses you or that you admire?

• 1:29:03Speaker 02

  You know, I don't, I don't, I don't, I'm not that, I don't know that many entrepreneurs. You know, like, I come out of public radio, most of my colleagues are still in the world of audio. And I don't, I haven't met very many people, so I don't even know how to answer that question. Like, I think, the more, the one thing I will say is that the more I have started running my own operation, the more things that I've realized, the more things I like about the way, the more things I learned from Ira that I think are useful, from Ira Glass at This American Life.

• 1:29:44Speaker 02

  Like, I think, like, I do, like, the ability, like, he really was, like, the thing that he did really well was he made people excited about the mission. And he did that by caring about the quality of the thing that you were, the thing that we were putting together, and he made it feel meaningful. And I think that's really important. And so, so that's one of the things that I've held with me. I think that was really, really important, and I try to do that as well.

• 1:30:17Tim Ferriss?

  If you don't have any co-founders or CEOs, next time you're in San Francisco to visit the in-laws or the wife's family, we should put together a dinner of some type just for the hell of it. I think that'd be a good time.

• 1:30:31Speaker 02

  I mean, do you have people like that that you're like, "Oh, that guy's doing it well. She's really got to go on"?

• 1:30:39Tim Ferriss?

  I do. I do. And, you know, one of them is a close friend of mine who was in your first episode. That's Chris Sacca. So as an investor, I've been an early-stage investor in a lot of companies, like whether it be Twitter or advisor to Uber, et cetera, Evernote. And Chris was one of the very early mentors I had. And he's a close friend, but he also is very, very good, obviously, at the early-stage startup game. So it was really Mike Maples Jr. initially, and then Chris Sacca, and also a guy named Naval Ravikant, who are spectacularly

• 1:31:18Tim Ferriss?

  good at what they do. And they have a methodical way of dissecting certain types of problems. And so I try to, I enjoy learning their respective recipes, you know, their kind of algorithms that they use for evaluating things, because they're all clearly effective, but they're also sometimes very different, which I find fascinating. So in the startup world, since I'm not, there are people, just because I'm running, you know, I have my own fledgling podcast, and then the blog, which is much more established and so on, there are people in the, and I don't really love the content creation label, but people in

• 1:32:00Tim Ferriss?

  the content sphere, whether it be audio or written word, or even video and television, that I really respect a lot. You know, I find what Morgan Spurlock does very fascinating, for instance, who was kind of in front of the camera and behind the camera, but now does both, including things that make him very much behind the scenes. So, yeah, I mean, I guess I've been on my own... I'm sorry, go ahead.

• 1:32:29Speaker 02

  No, I know a couple of people who are working with his company, and he seems to, yeah, it seems like a great, you know, he seems like he's doing a really good job running, making it a nice hub for where, you know, where cool things can happen.

• 1:32:44Tim Ferriss?

  Yeah, he's very good at establishing rapport with just any, any group you can imagine. So with, you know, Inside, Inside Man, I think it is. I don't think it's Inside Job, Inside Man. It's really, yeah, it's just incredible to see how quickly he can establish rapport with, with people. So I'm going to ask you the, perhaps the, the opposite of the word successful, not failure, but what's the first face that comes to mind when you think of the, and you're a very nice guy, so this might be hard to, hard to answer, but what's, what's the first face that comes to mind when you think of the word punchable?

• 1:33:22Speaker 02

  Punchable?

• 1:33:28Speaker 02

  Oh, Tim.

• 1:33:34Tim Ferriss?

  That could be your answer, too.

• 1:33:36Speaker 02

  Yeah, no, I, I'm just trying to decide. So I will tell you this, like, I feel like coming from, I guess, coming from the not, like, the nonprofit world, like, where I, I never had, this is the first, this is my first full-time job in, in the for-profit sector, is being the CEO of my own company, since I was like a-

• 1:34:04Tim Ferriss?

  It's a hell of a way, a hell of a way to start.

• 1:34:09Speaker 02

  And I think, and coming from the public radio world and the, and the nonprofit world at large, like, I do think there is a, a way that we, we conceive of, we, we conceive of ourselves as punchable in that world, like, that we're like not, that we need, that like, we need to be shielded from this, this world of profit and like somehow that there's like a, that it's, that it's, that it's dangerous and it's filled with people who will sort of eat you for breakfast. And, and I think, you know, I mean, that's like a gross exaggeration. Lots, lots of people in the nonprofit world are like, you know, like, this is like, this is a gigantic, gigantic overgeneralization, just so you

• 1:34:50Speaker 02

  know. But like, but I do think there's like a slight attitude that I ran into at, at public radio and other places that like- That we're shielded in this world from having to do, you know, from like some sort of like, you know, angry or sort of like, you know, macho or malevolent forces in the for-profit world. And that's like, you know, and that's been one of the nice things. And maybe, you know, who knows, maybe I'm gonna like, get like, my ass kicked soon. I probably will. And like, I'll be like, you know, God, I wish I was still in the nonprofit sector or whatever. But there was like, there's something about like, just sort of going out and being part

• 1:35:33Speaker 02

  of this sort of, you know, market economy in a really, really straightforward way that's freeing and doesn't feel like, it doesn't, you know, doesn't, it feels like the way it should be and not scary. You know? Does that make sense?

• 1:35:50Tim Ferriss?

  Yeah, well, yeah, no, it makes, it makes perfect sense. I mean, I think that it gives you, I've, you know, I work with a number of nonprofits, like Donors Choose in New York, which is run really leanly, actually, very much like a for-profit in that way. But the for-profit word gives you some metrics that are very clear to play with, that I think can be freeing in a way, because there's very little ambiguity about it.

• 1:36:15Speaker 02

  No, that metric thing was huge for me. Yeah, that we didn't have, like, it was like, sort of decisions, you didn't, it's a very, you make decisions for, then you end up making decisions for all sorts of other weird sort of arbitrary reasons, which like, does the director like it, or do our donors like it, or, you know, rather than that, like, do people like it? This is something that should exist in the world, you know, that people value enough to pay for. Yeah.

• 1:36:38Tim Ferriss?

  Yeah, definitely. If, now, on that point, you've, you've, you've kind of, not switched teams, it's not like they're opposing teams, but you've, you've done a lot since you, you were, you were first teaching eighth grade science, obviously. What would the old, what would the old you say to the new you? Or what would the old you think of the new you?

• 1:36:59Speaker 02

  Uh, the old me would think of the new me. I think it depends on which, which stage you go to, but like,

• 1:37:11Speaker 02

  You know, going back to like, you know, sort of the college and post-college, like, the old me would think, would probably think the new me was some kind of sellout, maybe. I was never that, like, sort of like, that strident, ever. But I was definitely more strident than I am now. And I definitely would have, you know, and I was definitely sort of a little bit more suspicious of the profit motive when I was younger. So I would probably be like, what, you know, like, what have you done with your life? I mean, the old me would also be like, you're an old man and all you do is like, go and, you have like, these two kids that are just, you know, I would have looked at myself with horror, I'm sure. Like, my life, I never, I haven't seen a movie in god knows how long. I don't travel anymore. You know, so.

• 1:37:57Tim Ferriss?

  All right, one more question for you. So if, if you could give your 20-year-old self one piece of advice, what would it be?

• 1:38:07Speaker 02

  This is gonna sound corny, but, uh, don't be, I don't be so afraid. You know, I think, I think I organized a lot of my choices based on sort of what I thought I could do, rather than what I wanted to do. And I did that because I didn't want to try to do the things that I wanted to do,

• 1:38:27Speaker 02

  because I was afraid I would fail at them. So, I think I organized a lot of my life around fear for this first, you know, that first decade after college. And I would tell myself, don't, don't be afraid, you know, go out and just like, fall on your face a little bit more. It's all right.

• 1:38:45Tim Ferriss?

  That's good advice. So Alex, just in closing, I know you have to run, where can people find more about you, about what you're up to?

• 1:38:53Speaker 02

  Well, you can listen to the Startup Podcast, it's all right there. And that's, that's at our website, gimletmedia.com. Both our shows are there, Startup and Reply All, and, you know, all sorts of stuff about our company and about me.

• 1:39:09Tim Ferriss?

  Wonderful. All right, Alex, I will let you get going. I really enjoyed the, the masterclass. I will put tons of links in the show notes for everybody, including links to the shows, to Gimlet Media, to the gear that you use in the field, to CreativeLiveClass, and, and much more. So thanks so much for the time.

• 1:39:31Tim Ferriss?

  And don't forget, this is a two-part episode with Alex. And we're going to give you a sample of that next part, the art of the interview, which is a class of his. It is fantastic. So we'll give you a few minutes of that, and please continue listening. But first, just a short word from our sponsors. The Tim Ferriss Show is brought to you by Onnit. I have used Onnit products for years. If you look in my kitchen, in my garage, you will find AlphaBrain, chewable melatonin for resetting my clock when I'm traveling, kettlebells, battle ropes, maces, steel clubs. It sounds like a torture chamber, and it kind of is. It's a torture chamber for self-improvement.

• 1:40:12Tim Ferriss?

  And you can see all of my favorite gear at onnit.com/tim. That's O-N-N-I-T dot com forward slash tim. And you can also get a discount on any supplements, food products. I like Hemp Force. I like AlphaBrain. Check it all out, onnit.com/tim. The Tim Ferriss Show is also brought to you by 99designs. 99designs is your one-stop shop for anything graphic design-related. You need a logo, you need a website, you need a business card, or anything else. You get an original design from designers around the world who submit drafts for you to review. You are happy, or you get your money back. And I have used 99designs for book cover ideas, for The 4-Hour Body, which went to number one New York Times, for banner ads.

• 1:40:56Tim Ferriss?

  And you can check out some of my actual competitions at 99designs.com/tim. You can also get a free $99 upgrade if you want to give it a shot. That's 99designs.com/tim. And now, back to the show.

• 1:41:15Speaker 02

  So this is a story that was on This American Life a while ago. And, um...

• 1:41:20Speaker 02

  The setup is that it's this actor Tate Donovan. And Tate Donovan was a sort of a character actor. He'd been, you know, sort of on a couple of different shows, but he didn't get recognized very much. And then he had like a stint on Friends. And all of a sudden, he was starting to get recognized. And it was really exciting for him to be recognized because he finally got to be the celebrity that he always wished that he could be. The celebrity that he would have wanted to meet before he was famous. So when he got recognized, and so one, and this story happens when, one night, he was out at this Broadway show. And a lot of people were coming up to him and being like, "Hey, I saw you." And he was able to like, talk to people and be very magnanimous and say, "Thank you so much, it really means a lot." And he was like posing for pictures for people.

• 1:42:03Speaker 02

  And it was at the show, it was happening over and over and over again.

• 1:42:08Speaker 01

  I was, I was, I was exactly how I wanted to be. I was doing it, I was doing great. And then, the kid with the camera came along.

• 1:42:21Speaker 01

  This nervous kid, I don't know, he must have been 16 years old. He's in a rented tuxedo, unbelievably like shy and awkward. And he's got like acne. And he's got a camera in his hand. And underneath the marquee is his date, who is literally like a prom dress. And she's got a corsage. And she's really, you know, nervous and sort of clutching her hands. And he sort of comes up to me and he sort of mumbles, you know, something like, you know, something about a picture. And I'm like, I just feel for him. So I'm like, "Oh, absolutely, my gosh, sure, I have no problem." "My god, you poor thing." And, and I go up to his, to his girlfriend, I wrap my arms around her. And I'm like, "Hey, where are you from?

• 1:43:05Speaker 01

  Fantastic, are you going to see the play? That's great." And the guy is sort of not taking the photograph very quickly. He's just sort of staring at me and he's got his camera in his hands. And it's down by his like chin, you know. And, and she's very stiff and awkward. And I, you know, I don't know what to do, so I just lean across and I, I kiss her on the cheek. And I'm like, "All right, come on, take the picture, hurry up."

• 1:43:30Speaker 02

  Do you guys want to find out what happens next?

• 1:43:34Speaker 02

  That's a story.

• 1:43:36Speaker 02

  When you want to... So, what... That is the power of a good narrative. So, when I talk about... I'm talking about like those two basic things you're going for. Emotion and narrative. We, as humans, are hardwired, I believe, to listen to narrative. And it's a very simple... Sort of the mechanics of narrative are very simple. There's like a sequence of actions and there's sort of rising action and it's culminating in something.

• 1:44:05Speaker 02

  And you are in the middle of that sequence of actions and you were about to get to the culmination and I stopped it. And it's frustrating. And you really want to know what happens next. And you would never, if you were listening to this, have turned off that podcast or that radio story at that moment. And that is a good story. And that's why you want to operate in stories. That's why when you're interviewing people, you want to get their stories out of them and you want to get them talking in stories. Because stories are what we want to hear.

• 1:44:38Tim Ferriss?

  If you enjoyed this episode, you are going to love what I have coming. All sorts of crazy experiments, incredible guests, and you can very easily not miss any of it. Just subscribe on iTunes or you can check out all of my guests, as well as my blog that has 1 to 2 million readers per month at 4hourworkweek.com. All spelled out, 4hourworkweek.com. That's where I chronicle all of my insane self-experimentation. And I would love to hear from you. So, please, reach out to me on Twitter, twitter.com/TFerriss, T-F-E-R-R-I-S-S, or on Facebook at facebook.com/TimFerriss, with 2 R's and 2 S's, of course. And until next time, thank you so much for listening.