B.J. Novak Interview (Full Episode) | The Tim Ferriss Show (Podcast) | Transcription

Transcription for the video titled "B.J. Novak Interview (Full Episode) | The Tim Ferriss Show (Podcast)".

1970-01-01T03:18:22.000Z

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Introduction

Intro (00:00)

At this altitude I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? No, what is the appropriate time? What if I did the opposite? I'm a cybernetic organism, living tissue over a metal entoskeleton. The Tim Ferriss Show. This episode is brought to you by Vimeo Pro, which is the ideal video hosting platform for entrepreneurs. And in fact, a bunch of my startups already use Vimeo Pro, including Wealthfront, who uses it to explain how Wealthfront works, TaskRabbit uses it to tell their company's story, and there are many other names you would recognize among their customers, AirBnB, Etsy, etc. Why do they use it? Well, Vimeo Pro provides enterprise-level video hosting for a fraction of the usual cost. Features include gorgeous high-quality playback with no ads, up to 20GB of video storage every week, unlimited plays and views, and a fully customizable video player, which can include your logo, custom outro, etc. You also get VIP support. And you get all of this for just $1.99 per year. That's $17 a month, with no complicated bandwidth calculations or hidden fees. And you can try it risk-free for 30 days. So check it out. Vimeo.com/business, that's V-I-M-E-O.com/business, and use promo code "TIM" to get 25% off. That's a special discount just for you guys. So check it out. Vimeo.com/business, promo code "TIM." Wealthfront This episode is brought to you by Wealthfront, and this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way, set-it-and-forget-it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last two years, and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley, have millions of their own money in Wealthfront. So the question is, why? Why is it so popular? Why is it unique? 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They wanted to sponsor this podcast, but because of SEC regulations, companies that invest your money are not allowed to use client testimonials. So I couldn't be a user and have them on the podcast. But I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now back to the recommendation. As a Tim Ferriss Show listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at Wealthfront.com/TIM. It's fast. It's free. There's no downside that I can think of. Now I do have to read a mandatory disclaimer. Wealthfront Inc. is an SEC registered investment advisor. Investing in securities involves risks, and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit Wealthfront.com to read their full disclosure. So check it out, guys. This is one of the hottest, most innovative companies coming out of Silicon Valley, and they're killing it. They've become massively popular. Just take a look, see what portfolio they would create for you, and you can use that information however you want. Wealthfront.com/TIM. B.J., welcome to the show. Thanks for having me here. It's very cool. Yeah, I appreciate it.


Career Journey And Success Stories

B.J. intercity travel, commuting the new old way. (04:46)

We are sitting in Venice at my friend's house, Devin and his friend Travis Brewer, who's on American Ninja Warrior. We have this incredible workout facility to the right, to my right, I guess, in the garage. You work in Venice, but you live an hour away. I live over an hour away, so I've been getting into podcasts. I actually enjoy. I was telling you on the way in. I enjoy getting to see this other part of town because LA is really like several different cities, and I've never really known the West Side. So it's worth it to me, at least for now, to spend that hour. And listening to podcasts on the drive, it's really like an extra hour of reading a day. Do you have any particular go-to podcasts at the moment? I just started getting into yours. What else do I like? I love this podcast called The Great Debates. It's a comedy debate podcast. People really at the top of their intelligence to Harvard friends of mine who are very well educated erudite comedy writers, just going at the most trivial and bizarre topics. One topic was, "It would be cool if the Pope had an affair with Maura Tierney." And one of them took the side, "The Catholic Church needs this sort of jolt and rebranding." And the other person saying, "What's the point of an institution like this?" So it's like debate club. And then there's one, "Intelligence Squared," which is sort of like the serious debate. The serious version of that. Yeah, the serious version of the comedy version of the serious thing. And that's been really interesting too. For those of you wondering what the whining is, it's not BJ.


The Harvard Lampoon. What it is and why its alums have Hollywood success. (06:26)

That's Molly, my dog. You mentioned two Harvard friends or fellow Harvard graduates. I have a question about Harvard. And you're a Princeton guy. I went to the lesser known with the P. But it seems like there is a rich history of people coming to Hollywood from Harvard that you don't associate with, say Yale, or maybe so, but I haven't come across it as much, or other Ivies. Why is that? Because it seems to go back quite a ways. My family at one point knew Henry Beard, who then helped create National Lampoon. And it just seems to go way, way back. And I'd love to hear why that is. I really don't know. The main correlation that I am familiar with is the Harvard Lampoon, which is a really one of a kind comedy magazine that has its own spectacular castle building in the middle of prime real estate in Harvard Square, William Randolph Hearst funded this incredibly bizarre and exciting old building. And that has fostered a lot of intelligent people trying to get into this building/magazine/party house. And those people sort of train each other really, I wouldn't quite say viciously, but really rigorously about comedy. This joke doesn't progress. This joke is predictable, and it's very rare that you'll get 19 year olds being hard on funny 18 year olds year after year. And so I think that is a training system that is unlike just about anything else you'd be exposed to at that age. So that has led to a lot of people falling in love with and becoming very good at comedy writing, which is, you know, a real building block of entertainment that can be put to you. And so people have traditionally graduated the Harvard Lampoon and gone on to write for The Simpsons or Saturday Night Live, or many, many other shows. And I think once you see graduates do that, you kind of think, oh, maybe I could do that. A big advantage, I think, of going to a fancy school, or my dad who did not go to fancy school but is a writer. A lot of people ask me, oh, did you have those advantages? Yes, of course, to an extent, but I find the biggest advantage is just not thinking that it's a crazy idea to try to be a comedy writer or to try to be a writer. Many people waste years working as a lawyer working, you know, whatever they do that they think of as, as a more reasonable choice before they finally get the courage to write. So I think that the huge advantage is, if you have the talent, no matter where you are, if you believe that it's a reasonable choice of action, you're extremely fortunate. And that, I think, is a main advantage of going to Harvard. It doesn't seem crazy. Right. I mean, you have these historical case studies of people who've done exactly what you might fantasize about doing. And the rigor and the training is very interesting to me because I was the graphics editor at the Princeton Tiger. So the satire magazine, cartoons, illustrations, that was my department. And I wanted that job partially because Jim Lee, who's sort of an iconic hero in the comic book world for me, had that previous post at Princeton. And I found a bunch of his drawings, actually, that did, when he was shit-faced drunk after going to a party on Nassau Street. But that's a separate story. The approach really was, do something funny. And there wasn't a lot of structure. I mean, there was feedback if something sucked, obviously, or just didn't get any type of laughs whatsoever. But where did that structure develop? I mean, did people come back from, say, industry and help instill that in some way? Or did it just develop organically among the students? The career path of it? Oh, no. I mean, the being hard on, say, underclassmen and looking at whether something progresses or not, et cetera. Yeah. I mean, I was simply imitative of other rigorous extracurriculars at a school like that where the ski club or rowing or the Harvard Crimson newspaper, whatever, probably it's more inherited from that because a lot of people want to do these activities. And you limit it to the people that you feel, and it's an incredibly subjective practice, but are the most talented at comedy writing. And so you put them through, "Well, can you do this? Can you do that?" And you have to write a number of pieces in order to get on the staff. So I think that everything at a place like that is very competitive. And so this is just that same rigor applied to this incredibly subjective and often thought to be trivial field of comedy writing. This does not lead to the best comedy writers by any means. That's one advantage, and the other advantage is that they believe they can do it. There are also huge disadvantages to coming from the Harvard Lampoon, which is a lack of life experience or being in touch with what real people actually find funny or a sense of cockiness that is very antithetical to comedy. So there's definitely advantages and disadvantages to coming from a place like that.


How did Gene land his gig as a writer for the Simpsons? (12:02)

At what point in your undergrad did you get involved with the Lampoon? Well, I tried to get on from the very beginning. So I tried, comp is the term for auditioning for it with your writing. So I tried three straight semesters, so I didn't get on until the middle of my sophomore year, but I wanted to be on from day one. What do you think changed between your first attempts and getting accepted? How did you improve, or was it just a lot? I have no idea. I probably just improved because I was older and had been doing it longer, but it's also incredibly subjective. If I had not gotten on, I had vowed to never try again and decided those people didn't know what the fuck they were talking about. Then I did get on. Actually, I did keep a healthy sense of this is not the be all, end all, but it's so subjective.


A Platform for Showcasing (12:53)

When you then did writing after college, well, actually, let's not fast forward too quickly, so I'm happy to jump around. The next step after graduating, what happened in the year after graduation? Well, I have a bizarre course of events. What it has in common with everyone else is that everyone who gets a job in Joe business, they have a story that's not replicable. That's the one constant, ironically. So what happened was, one of my main extracurriculars at Harvard was I put on a show called The BJ Show with another kid named BJ who was like a campus celebrity. He was like a reality show star before reality because he had stowed away on a plane to visit his family for Thanksgiving. This is before 9/11, so it wasn't quite as bad. But it still made the papers Harvard students stowed away on plane. He was the guy from the plane. I saw an opportunity here to hitch my fame to his. We put on this variety show. To get the plane guy attached to your project. Yeah. It's like, "I have the same name as the guy who was on the plane. Maybe we should do something together." We put on the show and I got some of my comedy friends. We wrote this. It was a variety show and parody of a variety show called The BJ Show. My senior year, I decided, "Let's invite Bob Saget to perform in this show," because I had heard that he was a really filthy stand-up comic, which he is. I knew that would surprise people. What was the timing on this? This was probably... This is 2001. 2001. Yeah. Okay. This is before America's Funniest Home Videos. No, no. This is after. I'm sorry. After. Yeah. He's well known as a family-friendly guy. But I have heard rumors that he's really filthy. I think maybe we can book him. Maybe we can honor him at the Harvard Lampoon. Because he'll want the award, he'll come and do the show, which worked perfectly. I approached his management. I cold-called his management and said, "I'm calling from Harvard. We want to give Bob Saget an award and feature him in this show." And the proceeds went to charity. It wasn't a scam for me. I just thought it would be a great show. By the way, that's a great thing. If you don't care about the money, always give the money to charity, because then everyone will do it. Often you just don't care about the money. You just want to put on something cool. That's something I learned in college that I'll probably use again if anytime I have some cool scheme. They're like, "Sure. Who cares?" So I cold-called his management. I asked my dad, "How do you think I get in touch with Bob Saget?" He said, "Call CAA." We're from Boston. I don't know how he does. He said, "Call 411. Get CAA's number and ask CAA. They'll probably know." I was like, "That's so smart." So I called CAA. One of the big agencies in town. Yeah. So I called CAA. I said, "Do you guys represent Bob Saget?" The receptionist says, "No." I said, "Do you know who does?" They say, "I think Brillstein Gray." So I look up Brillstein Gray. I call Brillstein Gray. They do represent Bob Saget. They put me through to a guy. I explain my case. He says, "Send the stuff you're writing for Bob. I'll take a look." This guy later becomes my manager. So the manager, Michael Price, likes the material, recommends that Bob does it. Bob comes out and does the show, which is a very highly scripted show. There's a parody of Full House called The Lost Episode of Full House in which Bob learns about sex from Uncle Jesse. Very dirty, very funny. Anyway, so after the show, Bob and he had brought his show's creator. He was doing a new show that never really went anywhere, but it lasted one season. It was called Raising Dad. Oddly, it starred Kat Dennings and Brie Larson, who are now both very, very successful as well. But they hired me. They were like, "Oh, cool. Young edgy writer, Harvard Lampoon. Perfect."


The Perfect Start (16:50)

They gave me a job on that staff while I was about to graduate. So I'm gradually – It was perfect. Set up. Perfect in a way. In a way. I mean, too good to be true on a career level. But again, I really had these fantasies of being a great artist, a great filmmaker, and sort of a family WB show. I didn't want to move to LA. I knew that I shouldn't say no to this, and I didn't say no to it. But it was – I actually wanted to be like a starving artist. I'm from a suburb. Starving artist means borrow a little money and live cheap. I have no real illusions. But I didn't – I had mixed feelings. It was sort of a dream come true and sort of career moving forward. But it was – I was – I don't know. What did you think you – What type of starving artist did you think you wanted to be when you were a sophomore or junior? I had read this book Easy Riders Raging Bulls about independent film. And I highly recommend it.


Choosing a Wannabe Sell-Out Project (17:55)

Easy Riders Raging Bulls? Easy Riders Raging Bulls about sort of filmmaking in the glory days of the '70s. And I wanted to be like that. And then there's a sequel about sort of the Miramax, like the '90s Tarantino Kevin Smith is also good. But I really – I wanted to write like a screenplay that would like blow Hollywood apart. It was so edgy and innovative, et cetera. And then demand to direct it. And that's – I think anyone who saw Pulp Fiction as a teenager, that was their fantasy. So that was very much my fantasy. And in my privileged wannabe artist mind, this was a sellout move. But I knew it would be even more like privileged and like eye-rolly to turn it down. I mean, so it's an interesting paradox. I've noticed this. When I was young, I thought, "Oh, I'll never be a sellout. If anyone ever offers me something sellouty, I'll always say no." Then you realize there's a huge integrity pull towards doing the sellout thing because you think, "Who am I to turn down all this money for something that someone else would struggle their whole lives to," et cetera, et cetera. And you actually feel very guilted into – towards at least doing what you would have considered a sellout thing. So that's – it's an interesting paradox that I've observed with a lot of successful people. They get offered a really lame movie for a ton of money and their thought isn't, "Fuck that. I'm an artist." Their thought is, "God, who am I? I want to make kids through college just to do a Christmas movie. Who am I to say no?" It's very surprising. I mean, it makes sense, but I'm surprised. It does make sense, but it's an incentive of guilt as opposed to sort of incentive of focus in a way. It's kind of like the Christmas story where it's like, "There are starving kids in China." You know, and you're like, "Oh, okay. I'll eat this food that you put in front of me." How did you then make decisions or what happened after you were offered that gig on the – I took it. You took it. You know, I took it. I moved to LA, started writing for it. And I looked around the room. It's interesting. I kept telling myself I'm making so much money because for a kid at that age, it's so much money. But any job I've had since then, I made more money on The Office, for example, and I never thought I'm making so much money. So anytime I'm telling myself I'm making so much money, I'm making so much money, that's a warning sign that you're doing the wrong thing. So I would tell myself that because I gradually realized this isn't the life I want. I'd look around this writer's room and think, "These are not the jobs I want." And I'm glad I did. I really had these dreams of doing something important and visible and exciting. And the only people in the room who I did aspire to be something like were Bob Saget, who would come by now and then in his fancy car and cool sunglasses and tell 10 jokes and leave and get to be the star of the show, and Jonathan Katz, who created the show and had previously created Dr. Katz on Comedy Central, a really cool show. And he also came by now and then, gave some words of wisdom and jokes and then left and was also celebrated for his own voice. And I thought, "Well, those are the guys I want to be." And they were both stand-ups. So I never thought of doing stand-up before then, but I realized, "Well, how insurmountable is this?" Being a stand-up is writing a joke and then saying the joke. And that is what I'm doing in this writer's room. I write a joke, I say it out loud to see if it goes in the script. I guess I could try that and try to be like them. And so as the show was winding down, I signed up for open mics around LA and I would start saying one-liners into a microphone and I was kind of doing stand-up comedy.


Jon's Early Stand-Up Attempts (21:44)

Dave: What was the… do you remember any of your early bits when you did it? Jon: Yeah. Well, the first time was a real disaster. And one of my most important pieces of advice to anyone doing stand-up is if you're really going to try stand-up, book your whole week of shows, your whole first week in advance. Dave So you can't quit. Jon So you can't quit because I got up all this courage to do my first show. It was at a youth hostel, the Hollywood Youth Hostel. It was October 10, 2001, so less than a month after 9/11. All my jokes were about 9/11 and I was not a good comic. And the crowd didn't speak much English. And I followed a guy who killed. He did an impression of Robert De Niro taking a dump. And I have to say it was great. It was a great impression and you didn't need to know English and it was completely opposite of what I was doing. And so I did this bit, it was horrible. And the host said after me to try to keep the show going, all he could muster for me was it takes a lot of courage to get up on this stage. And after that, I did not get on stage for three months. I had to work up the courage all over again because it had been such a disaster. And that time I was like, "You know what? Tuesday I'm going to this coffee shop. Wednesday I'm going to this bar, all these open mics." And the first night back, I did pretty well. And the second night, I didn't do well. You can't make each night a referendum on whether or not you should be doing it. You just have to do a bunch. And how did your approach change between that first bomb and the second collection of attempts? It was exactly that. It was the idea that I'm going to really do this night after night and I will evolve the act. I was really bad for a while. But let's say you do 20 jokes and three of them get pity laughs. Well, those are the three you keep. And then after a while, one of them always does well. Well, that's your opener. And now two of them do well. Well, now you have a closer. And you sense, "Oh, okay. When I do this kind of joke, it does well." It evolves that way. What did your parents do?


What Rashida's family thought of her ambitions and career. (24:00)

You mentioned your dad wrote. He also wrote some memoirs or Ghost wrote some memoirs for some big people. What are some sample…? The biggest one he did was Lee Iacocca. The biggest and first one he did. He also did the memoirs of Nancy Reagan, of Tip O'Neill, Magic Johnson, which was very exciting for me. He worked with Tim Russert on two books and George Stephanopoulos. So a lot of political people on both sides of the spectrum and a lot of just eclectic business leaders, various people. What did your mom do? My mom is a teacher now. She's done a bunch of things though. She's also kind of an eclectic career. What did they think of your move to stand up? To not start up, so that comes a little later. Stand up, similar sounding word. What did the… how did they… Well… Yeah, how did they feel about that? What were the conversations like? Yeah, I think they thought I wasn't very good. My dad also is the co-editor of a couple humor books that are very good, The Big Book of Jewish Humor and The Big Book of New American Humor. My family, comedy is a big deal to us. They watch Seinfeld every night. Seinfeld and Key and Peele are the only things my parents watch, which I think is very good taste. So I think they kind of just… they definitely supported me writing. I'd studied literature at Harvard. My dad's a writer. There was nothing, again, huge advantage for me that my parents thought writing was a good, a solid job. And then stand up was where they were like, "Okay, get it out of your system. This is not you, but whatever." You know, they never said this to me, but in retrospect, it's like, it's the same thing on stage when the audience is laughing and then you say something off the cuff and you get a huge laugh and you realize, "Oh, they weren't even laughing before." My parents were like, "Supportive, supportive, supportive." And then they really supported something different. You're like, "Okay." So you were not… Okay, you're just being polite, fair enough. But they were slow. They're supportive people. They came around and they supported the office.


From her early career to joining the cast of "The Office". (26:06)

So when did the… what happened between that startup… I really want to say startup. This is why I'm taking a break from startups because I'm just like completely brainwashed. You took a… from that first… You have a title that's in there from standup to startup. I could. That could be your memoir. That could be. I'm not my dad right now. From that point to the office, what happened between those? From that point to the office, well, raising dad got canceled. I continued doing standup. I ran out of all the money that I had saved on my big money year in about a year and a half, two years of doing open mics and gradually getting better to the point where at the end of sort of after a year and a half, which is a long time when you are a kid from the suburbs. It's a long time. It's a long time, but compared to most standups, you know, I got very lucky, of course, but it did feel like a very long time because I had been working. After about a year and a half, I got decent, definitely decent at standup and I was starting to get booked at respected alternative rooms at the improv. And you know, there's a lot of people in Hollywood that are always looking for anyone half promising to sign or to put on showcases. And I was becoming that comic that people would say, oh, there's a new guy. He's pretty good. You know, that kind of guy. And at the end of that, a bunch of things, the end of that sort of two year stretch, a lot of things kind of happened at once. I got cast on the show Punk'd. I replaced Dax Shepard as the new guy, which I thought that, oh, that's what I'll be famous for for the rest of my life. I'm the guy from Punk'd. So I did pranks on Hilary Duff and Usher and people like that. Incredibly fun. And I got booked on Conan. I got booked on Comedy Central. Was the Usher prank, I have a big memory of this, was this when his brother was set up to steal jewelry? And then I tell him, Usher handled that so well. He was great. And then I tell Usher, you know, we can let this go if you record a radio ad for our store and do this rap that I wrote. They wrote a really funny rap and I have to rap this to Usher. So hard to keep a straight face. And one of the brilliant touches the writers have put in is that in the rap Usher refers to himself as Ice. And then I apologize that we originally wrote this for Vanilla Ice, who passed. So I got to do really funny, clever things. And around this time I was on a showcase. A standup showcase for a network. And now I had booked Punk'd and stuff like that. And that's when Greg Daniels, who was creating the American Office, saw me and thought he was already looking for people that could write and act. And my jokes were very clearly like clever writing. They weren't like a raw personality or anything. So he thought, oh, maybe you can do. And I had a writing job. Maybe you could be a writer actor, which at the time was it was a very experimental idea. I was going to ask you why he was looking for that. Because he had worked at Saturday Night Live and he had a good experience. Where there was a small gang of people who were writing their own things. And also the British office had been a small… Ricky Gervais had written so much of it. So he was totally right. Let's not have a corporate feeling show with a writing staff and a cast. Let's cast funny people who can do it as a little unit. And what was the very beginning of the office like for you? The beginning of the office was very exciting, creatively especially. Because it was not thought to be a show that… This is now I got to feel like that starving artist, like, you know, the actual integrity. This was not considered a successful show with any chance for success. It was a very drab. There's no laugh track. There's no colors. It's bleak. It's not a pretty cast. It's the jokes are very slow and dry. And it's a remake of a British show that NBC had a track record of disastrous remakes. So it was a six episode mid-season order. It was a really… Actually, no, it was just a pilot order. And then we squeaked into six episodes. So the beginning was, you know, but it was the people working on it were brilliant. Steve Carell's improvisations and Greg Daniels sort of joke pitches and story outlines and pretty soon this very lean writing staff of Mindy Kaling and Paul Lieberstein, who played Toby on the show, and a bunch of other, you know, real Larry Wilmore, who now hosts the Nightly Show on Comedy Central, you know, real, real lean group. And you know, so creatively, it was extremely exciting. And then it was bizarre when it became successful, because we had come to think of it as the show that for the rest of our lives, we'd meet one or two comedy fans who were like, "That's a classic." You know, that's what we're going for, for like Mr. Show, like cult status.


The Tipping Point (31:11)

And when did it… When did you feel the tipping point? Was there a particular event or moment or time when you're like, "Holy shit, this thing is actually going to be successful or is successful?" The beginning of the second season was around December, I think. So we'd been out for like over a year, but only a few episodes. And they moved us from… two things happened. They moved us from Tuesday to Thursday, which I felt was very important because now, you know, the night you're on doesn't matter so much in the DVR era. But back then, my theory was that you wouldn't want to watch a show about an office at the beginning of your workweek. It's not funny on Tuesday. It's like a fair assumption. It's funny on Thursday, it's almost over. So there was that. And the big thing was that the Apple iTunes store process began. And we… because our cult audience was very young and tech savvy, they made us a very big hit on the iTunes store, even though we were not a hit on NBC. And then people were walking around with like video iPods with the office on it, and they were sending each other, you know, links to download it and stuff. And so it was really one of the first shows to be a hit, like an online hit in that way. And that really was this viral, you know, proto-viral way that the word spread about the show. And so I have to ask a question that I've always wanted to ask somebody involved with the office because I have no idea how this came to pass. But a fan sent me a link to a clip at one point. The four-hour workweek came up in an episode of The Office where there's this big debate going on amongst everyone. And someone says, "What do you mean? I sent you an email," pointing to Daryl. And Daryl says, "I don't check email until 12 noon." Yeah. Four-hour workweek. And then it zooms out of his face. Do you have any idea how that happened? I… I mean, it's a very specific question. I was in the room when that was pitched. I don't remember whose it was. It was just… I thank you for being part of that joke. Working backwards from what we must have meant, it was just funny. Like every little thing is going wrong for Michael on this episode. It was really hilarious and really made my week. That was… Awesome. I was very surprised to come across it. The Office, what are some lessons learned through your experience at The Office? What did you get better at and why? Lessons learned. And we could talk about… I mean, you could have a particular person in mind if that helps. Yeah. Well, one lesson that I learned from that as well as from stand-up was that you really never know how something's going to play until you test it. Scenes that felt like they were just airtight, winter, hilarious scenes in the writer's room sometimes just would not work on set.


Learning this writing lesson in the writers room of The Office (34:17)

And you had to learn to not be angry at it for not working. You had to learn to listen to the audience. And that's a major, major lesson. There's no one smarter than the audience. So this is actually something that… So it was filmed in front of a live audience? No, but there's a crew. But you just feel it. You just feel it. If it's flat, it's flat. First, you do a table read of each episode so you have a big room of people laughing or not laughing. Then when you take it down, if it's like a rewrite scene or something, Steve Carell says it and you're just there. Even just you and the cameraman, you're smiling or you're not. Or then you edit it and it works or it doesn't. And that was, I think, a humbling lesson for someone who thought of himself as a real writer because writing is really… it's just a guess. And there's no penalty for doing your homework. So if you want to test your standup at a thousand rooms before you do it on TV or if you want to test the stuff you're writing for the office in as many groups as you can, do it because you're not smarter than the audience. It's for the audience. Would you test your material you're working on for the office in other environments? In little rooms, yeah. Everyone had their own office. So Mindy and I would read scenes out loud and just see if they sounded right. You either see someone smile or not. Yeah, yeah. What about Steve Carell? Did you observe anything particular? Oh, well, I learned something from him, which was one time I wrote a bunch of jokes because the scene wasn't working and I was the guy in charge of bringing alts, as we call them, other versions. So I'd bring alts to the set and he looked at all of them and he said, "I don't know, these just feel like jokes to me." And I was like, "Well, yeah, they're jokes. That's what I do. That's what we do." But for him, comedy was a byproduct of authenticity. I would compare it to the difference between a kid who knows he's cute and a kid who doesn't. A kid who knows he's cute is not cute. A kid who just says something without realizing he's cute is hilarious. And that's what he wanted the office to feel like. Like these people don't even know how funny they are. So that was important. I'm sure I'll come up with a lot more lessons because I learned more on that than anything. We could, let me- I can talk about the writing process. I would love for you to write about it. Yeah, I'd love for you to talk about that. Well, the way that we would start a season, and I've adapted this to many things I've done since, we'd start with what we would call a blue sky period, which was my favorite part of every year. For two, three, four weeks sometimes if we had long time. Every single day in the writer's room was just, what if? There's no penalty. There's no, maybe we can't, there's no, but this one conflicts with that one. What if Dwight goes to the moon?


THE (EASY) WHITEBOARD EXERCISE (37:14)

What if Jim and Pam get divorced? Just every idea is valid for a while. That was just an amazing period. And then- How long would that last? That would last if we didn't have much time because we had different pre-production schedules between two weeks and four weeks. That's a decent stretch of time. And was there structure to the what ifs? Was there somebody on a whiteboard taking down the favorites? But it was sort of improvised day to day, like the showrunner would say, "All right, we don't have anything for Dwight." Or like, "How about everyone split up and come up with 10 ideas for Ryan?" Or "Let's come up with more ensemble stories." There would be sort of a leadership that way. It wasn't just all sitting around, but- What is an ensemble story? I feel like I know what both words mean separately, but I don't. The whole cast is involved in one thing rather than- I see. A story, B story. So that was incredible. And it really was creatively important. And I try to replicate that in everything I do. Just not shut down any ideas for a period. Just generate and not edit. Yeah. And then the best ideas will fuel you past the problems. After a few weeks of Blue Sky, we would love some ideas so much, it would be obvious what the best... Let's say we were going to start with six stories, right? It was obvious what the best 15 were. And then we'd start talking more seriously. And then we'd look which ones do our love for the story carry us through the inevitable. "Well, how could Dwight be here if he's also there?" Stuff like that. But finding the love first and then letting that carry you through the problem. Do you explain what you mean by that? Yeah. You find what you love about an episode or in other things I've done, a story idea or a standup bit. You've got to just indulge, develop what you love about it so that when you then come up with, "Oh, but then we couldn't show this on TV," or "It is kind of contrived," or whatever it is, you'll love it so much that you will have the inspiration to fix it. Got it. So you're developing the piece that you've fallen in love with enough so that you can handle all the inevitable... Yeah. ...fixer-upper issues. I do that with my other writing too. I always start with what I love. And if I'm stuck on a story and I approach it the next day, I never go to the heart. I do the hard part first. Some writers probably do. I go to, "What's the one thing I'm proud of in the story?" Could you give an example? Not off the top of my head, but there might just be a... Or hypothetically, yeah. ...joker, a phrase or a beautiful line that I'm proud of that I'm just so certain everyone's going to think I'm brilliant. So I started that and I get excited and then I want everything else to live up to that rather than start at the problem. That's a personal thing. I am very motivated by positive thinking.


Writing Tools And Techniques

FIND A GOOD MOOD (40:06)

Were there any other... An ego, positive ego. Use your own ego to fuel yourself rather than be an obstacle. What other approaches do you take in your work life or personal life to maintain positivity or use positivity? I consider being in a good mood the most important part of my creative process. So right or wrong, I personally don't get up early unless I'm awake early if I'm where I have somewhere to be. I've read the book. We talked about daily rituals, which I love. Yeah, Mason Curry. Great book. I'm demoralized by how many great people start their day very early. Were you also... I tried to go to bed. Were you encouraged or demoralized by how many of them were drug addicts? That was encouraged. It's like 90% who use methamphetamine. Right. This venti Starbucks in front of me, who's to say that doesn't have the same stimulation that they used back then? I try to go to bed early and wake up early, but if I need to sleep late or take a walk in the morning or whatever, I find that being in a good mood for creative work is worth the hours it takes to get in a good mood.


THE CUP OF FEAR (41:08)

So often when I was writing my books, someone would check in, send me a text at like 1130, like, "How are you doing? What's up?" And I'd say, "Powering up." I just feel the first few hours are just getting into a good mood until I think, "All right, all right. I have an idea I'm excited about," or I have so much self-loathing and caffeine that I'm like, "Got to do something." The self-loathing plus caffeine is a hell of a thing. One of my friends, Kelly Starrett, who's a very well-known athletic trainer, calls it "cup of fear." So you take the self-loathing and then you drink a cup of fear. I'll tell you my number one while we're on this, my number one creative productivity advice to anyone, I mean, anyone if it works for you. I carry around a notebook, and if I don't have a little notebook, I have my phone, you know, but I really divide my creative work into two distinct phases, which is the idea phase and the execution phase, and I do not let either interrupt the other. Or yeah, that's the best way to say it. So if I'm taking a walk or I'm having a drink with a friend and just some funny idea comes up, something that makes me smile or some other impulse, I write it down and I never judge, "Well, what would you do with this idea?" or "How would you end that joke?" Never. I mean, I feel like the richest man in the world in terms of ideas. Just fill it up, feel great, never question it. Then on a separate day, I sit down, you know, 9 or 10 a.m. with a big cup of coffee at my desk, go through the notebook, and I do my best with every idea in the book. So I never am intimidated. When you say do your best, you're developing each one on a separate piece of paper or something like that? Yeah, yeah, on my computer usually, or continue an idea on the computer that I left off the previous day. But first I'll check my notebook, "Oh, did I have any ideas for solutions?" or whatever. So the idea, to me, everything is idea and execution. And if you separate idea and execution, you don't put too much pressure on either of them. I was reading an article by Isaac Asimov about creativity in groups versus solo creativity and a very similar conclusion that he came to, just keeping them separate.


Creativity in groups versus solo (43:31)

Now when you – do you have a particular type of notebook, particular type of pen that you like?


Yeah, I use the Moleskine Cahir, is that how you say it? I have no idea. How's it spelled? You can buy them, C-A-H-I-E-R. You can go on Amazon and buy these three packs. So they're much thinner than the typical Moleskine notebook, so you can really – you can keep them in your pocket easier and you finish them so you feel more productive. You feel like you've accomplished something. Yeah, you fill them up in a couple weeks. And then I have a huge box of them. But I use that and I use the Uni-Ball Vision pen generally. How do you – do you date them? How do you keep track of these notebooks? What I do, I order different colors and mix up the colors that I order and then I buy on Amazon these huge batches of stickers, shape stickers that teachers use to put on reports and stuff like stars and circles and blue rectangles and stuff. And every time I start a new notebook, I write my phone number in the first page in case anyone finds it. Super important. Yeah. And then I put a sticker in the top left corner of the book. That lets me know which one I'm on currently. And then I have a yellow – I'm sorry. I have a red box for – I have a white box for untranscribed notebooks because then I transcribe them on my computer and a red box for transcribed notebooks. And I don't date them and I always tell myself I should date them. This is crazy because when I go through the white box, I'm jumping around six months ago, four months ago. I'm not going in order. But I guess just I'm not going to question it because something about the creative process, I just don't want to date them. I just don't know. Interesting. What – I mean maybe that would create some bias against older material. I mean for the same reason that I take dates on my blog posts and I moved them from the top to – as a small italicized line at the bottom and my traffic jumped like 20, 30 percent because people are no longer biased against older material. That's very interesting. That's something on the list app too. We keep an eye on. What – and we're going to talk a lot about lists. Not trying to rush you. No, no, no. We're going to get there. The – I love the red box and white box. When you develop these or do your best with them as you said on the computer, are you doing this in a particular app or program or is it limited to whatever your current focus is, say a book or a screenplay or filmable? I use Microsoft Word.


Same reason my dad used WordStar. It's just what I learned and got in the habit of. And I use Final Draft for screenplays because everyone does. I would like – I know there's other software out there. I would like something that kind of combines the two because often I would like to kind of write a paragraph and then kind of throw in dialogue easily. But it's not worth it to me to investigate and switch. Yeah. There's a tool that I've used for my last few books that I found extremely helpful. It's not as focused on screenwriting as say Final Draft, although people do use it for that, called Scrivener.


On cofounder, software developer, and writer Blake Ross (46:53)

I don't know if you've ever seen this. Yeah, I've heard of it. Yeah. I've used it for my last two books. I think it's really helpful for that format. I think it's mostly used by playwrights, I want to say, but there are screenwriters who use it. When you see – Blake Ross, I was going to mention, who invented Firefox. Yeah. He's an investor in the List app and I've been trying to get him for years to develop with me like a screenplay writing software because he's actually a terrific writer and he wrote the Silicon Valley spec script that he put on Twitter, which is such a tech way to get your spec out there. But it was great. And I think he would be the guy to crack it because he's the writer and also the software developer. I think he'd do it like an afternoon. Where is he based? Is he still in the Bay Area or is he – yeah. I need to actually spend some time with him at some point. Oh, he's the best. He was very, very kind when – I think it was 2007 – gave me a quote for the 4-Hour Workweek and I feel very indebted to him. Oh, he's awesome. So if you're hearing this, thank you so much. I really owe you a coffee and dinner and a bottle of wine and probably more. But when you – how do you think of yourself?


Comedy Writing And Technology

On identifying with writing (48:00)

I mean I guess it depends on perhaps what project you're working on. But which of these many activities and artistic projects, crafts that you've attempted do you most identify with? Writer. Writer. Yeah. Any particular type or is it just across the board writer? Probably comedy writer to be honest for two reasons. One is just it's the identity I come from. I think it was Woody Allen who said if you – I do these different things but if you woke me up and shook me in the middle of the night and said, "What are you?" I'd say writer. I definitely feel like that. That's a good – I should rephrase my question to mimic Woody Allen's wording. Yeah. Ask everyone that. If someone woke you up in the middle of the night and shook you and said, "What's your job?" What would you say? I guess the simpler way is what do you put on your passport or your customs declaration. I always put writer. But I think that everything I do is sort of a version of writing. Even if I'm acting, I'm sort of writing the way that I think this character would act. Do you know what I mean? Of course. Or if I have an idea, I really feel like idea and execution, that to me is writing. If you were teaching a – let's see, freshman seminar at Harvard on comedy writing, what would the curriculum look like? Oh, great, great question. Well, P.J. O'Rourke, who was one of the big National Lampoon editors, said that if he taught writing – It was the Confederacy of Dunces. Did he write that? No. Am I making that up? But he might have written the introduction to it or something. All right. So he said that if he ever taught English, he would assign parodies because that's when you really learn something is to parody it. So I would probably assign parodies of literature. I would – Are there any particular parodies that – Just sort of whatever you're studying in your other classes, parody that. And it really, I think, would open you up. I think mischief is just so important in comedy. It's really – there's just something like, "Am I really allowed to say that?" You know, that's just the cool thing. Am I really allowed to hear that? I could pontificate. I know a couple of things that I feel I have discovered about comedy. One is that the perfect – first of all, the most important thing is it is sort of a – it's like a physical – it's like sex in that it's about whether the other person is enjoying it or not or you're enjoying it. You know, like you could say, "Do this and that," and then if neither of you has a good time, you couldn't insist to me like, "But I had good sex." No, you didn't. Like that – I gave you my best advice like, "Touch her here and take your time and whisper this." You're not going to do that, but you'll know if it's good sex or not.


Observation is the currency of comedy. (50:50)

These are just tips. Like it's a physical reaction that you're going for. So there's that – you know, whatever you teach, it's like, "Hey, you'll feel it. You'll feel it or you'll hear it. You'll know." So do it a lot and probably don't take this class too seriously. One thing I've definitely learned about comedy – I don't know how it applies to what – maybe it applies to editing more than it does to writing or finding what's good comedy. But I believe that a good comedy operates the exact same way a good mystery operates, which is the punchline should be something that was right in front of your face the whole time and you never would have put your finger on it. It's like the red doorknobs and the success. Oh, the red doorknob. Yeah, exactly. Of course. He was dead the whole time. You know, like how did I not get that? That excitement, that elation, or like it was the butler, it was the narrator, you know, whatever it was, that's the best comedy. When someone points out something, you're like, "Oh, my God, that was so obvious. I never would have gotten it." Another thing is that observations are really the currency of comedy. Anything you do, if you observe something that touches a chord with somebody and that has not been expressed right, you can turn that into a movie, you can turn that into a plot, you can turn that into a one-liner. But anytime you observe something that a good new observation, that's what fuels 99% of comedy and the other 1% is just people falling down or whatever. And are there any particular comics or comedy writers who are very good in your mind at the red doorknob effect? So hitting you with punchlines that have kind of been there all along, but they do a good kick. Well, Aziz Ansari has a bit about marriage that I find brilliant. I think it was one or two specials ago on Netflix where he's like, "If we invented marriage now, if no one had heard of marriage and you proposed it to a girl, you would freak her out beyond belief. I want a vow that will never ever sleep with anyone else and I want rings on our fingers to symbolize it and I want a priest to be there and everyone we've ever met and there'll be a ceremony, it'll be in the newspaper." That is so funny to me because it's completely true, never would have noticed it. Louis CK is brilliant at pointing this stuff out, saying things that is kind of how you felt, but you never would have thought of it. But even an abstract one-liner comic like Zach Galifianakis, who I tried to see whenever I could when I moved to LA, even those are like, "Right, that phrase could mean that." Even that is an observation, even that's just about language. That's true, right. Like 24-hour banking, who has time for that? The Stephen Wright kind of approach. Right. You could look at it that way. You know who's really, really good at that is, now that I'm getting sort of a finer feel for what you meant, is perhaps the majority of really good stand-up comics are good at this, I don't know, but why am I playing? Dimitri Martin.


Cinephilia and screenwriting. (54:06)

Oh, yeah. Dimitri Martin is really good at the wordplay. You mentioned movies. We've mentioned ListApp a few times and I feel like we should dig into that because my next question would be related to, and maybe by means of example we can get into ListApp. I was going to ask you for screenwriters, what would your curriculum look like? And you put up a list recently and maybe you can explain the app as well, but you put up a list of some of your favorite movies. So you had Adaptation, you had Naked Gun down towards the bottom. And the bottom of the top five though. Yeah, it's the top five. It was Adaptation, Ferris Bueller's Day Off, Pulp Fiction, Casablanca, The Naked Gun. It's just personal. If I were really going to die tomorrow and they said you could play a couple of movies. I'm not trying to impress anybody. It's not film history, it's just me. Would those films correspond to the five screenplays that you would suggest people read if you were signing them? Yeah, probably. Probably the writing is front and center for all of them. Now Adaptation is brilliant because it breaks all the rules and comments on all the rules. So maybe I wouldn't teach that first. Also if anybody says I want to be a writer, at least for me, I would say watch that movie. Yeah, I'll talk you out of it. Yeah, I should really use a donut. God, I'm so hungry. I guess all of these movies break the form and maybe that's why, you know, Casablanca probably I don't know enough about film history, but it probably broke the form. Now it is the form. So maybe I would, but there are weird things in that. Pulp Fiction obviously completely breaks the form chronologically. Ferris Bueller, he narrates the movie to camera. The Naked Gun is just, they'll do anything for a laugh. I guess that's kind of formal in a way. Adaptation completely commenting on itself. So yeah, maybe I think one lesson in all of that is it's not about the rules. It's about you and the audience. Everything that you do. So here's a quote. This is maybe out of the field a little bit. Do you like, have you seen Memento? Yeah. Did you enjoy that movie? I thought it was okay. So when I saw it, I really enjoyed it. But that, a lot of people hold that up as an example of a movie that broke the rules where it didn't work. Or it was trying too hard to break the rules or something like that. I think it's a great, if I were him, if I were Nolan, and that was my first big movie, I'd be very proud that I got everyone's attention. It's extremely clever as an idea. And if that's enough to give you pleasure watching it, or if that's enough to get your attention to watch it and then you got pleasure watching it, I agree that premise is fantastically clever. I just wasn't personally especially moved watching the story. And I, you know, he's so big it won't matter if I criticize him. But I have a real problem with the Chris Nolan worship in cinema. I think that's a screenplay. That's a writer I would never teach if I were teaching screenwriting. Why is that? Says the guy who's never written a screenplay. Because a movie should be a pleasurable experience. That is my one sentence answer. And I find his movies cold and formal. And I find his demeanor as a public director cold and formal. And please, I make this a headline. If someone listens all the way here, they can see everyone's opinions. But I find his movies completely unpleasurable. Exclusive to TMZ.


Tech. (58:01)

And I feel that the formality has conned people into reverence, when in fact, no one was smiling in any of these Batman movies that everyone gave such a claim to. And no one was smiling at inception. And no one understood Interstellar. I am a well-educated guy. I have a real interest in science. I write screen stories for a living. And I could not follow this. So who is following this? You know, a movie should be entertaining you and inviting you in. So that's a screenwriter I would not teach. Got it. How did you get into tech and why tech? I find tech, and again, this is sort of the formal rules of anything. First of all, tech is the best field at being the first to tell you that there are no rules. It's about what you make and how people respond to it, which I really love. And I think tech is leading the way for entertainment. And you realize, oh, everything is about, very soon on the Apple TV, you'll be able to say, the Midi project. And you won't have any idea what network it's on. It's all about whether Mindy Kaling, full disclosure, a good friend of mine, it's all about whether Mindy Kaling has made a good show, gotten the budget, gotten the cast, convinced them to do it, that's a big deal, and made it well, that's a very big deal, and gotten enough publicity for it that you are curious about it, but that's it. And there has been a lot of bullshit in terms of what night is it on and what's the competition like? And who picked it up and why and who funded it and how much do they get and is it going to make syndication?


Tech's vision of less is more (59:44)

And that noise has nothing to do with the product and the audience. And I think tech is leading the way in removing that. And I think tech is really, the reason I've always been drawn to it and always pitched every idea I ever had in tech to my friends in tech is because it seemed like a utopian version of you have an idea and you see if it's a good idea. Just like with stand-up, just like with writing scenes for the office, I think this is a great idea but I won't know until it goes to the set and it succeeds or fails or I bring it on stage and no one laughs or everyone does laugh. That to me is the biggest pleasure is having an idea and seeing if you're right. And so tech seemed to me you could have a huge idea and it could be right, whereas in other fields, a huge idea, you need to be at a huge scale to even try it out. So that's why I always had like, you know, that's why I met Blake Ross because in 2006 or 7, you know, I had a friend Charlie Cheever who worked at Facebook and I said, "Can I see Facebook? You know, can I have a tour?" So and I would cultivate these friendships and these guys to me, that was I think what a lot of people looked at show business in the world I was in and thought that's so creative and I would look at this world and think, "Wow, you can have an idea and then if it works it works? That's so beautiful." Yeah, there's a… And of course like everything, it turns out to be way more complicated but I think less complicated than other fields. And less and less complicated from the standpoint of testing ideas, right? Because you have cheaper and cheaper rentable infrastructure whether it's Amazon Web Services or otherwise, you have global talent market where you can use people remotely or locally or in some distributed fashion like automatic which I advise and the guys who do WordPress.com and whatnot. I mean they have 400 plus people who are all distributed. And then you have the Kickstarters and other means of funding that weren't available 5, 10 years ago. So… If you had an idea for a store 20 years ago, that's… You really put your whole life on hold to pursue that compromise of a compromise of that idea for a store. And now, you can make that store. Yeah, you can do it in an afternoon and then see how it goes. Can you describe then what it is that you're working on right now? So this is… I've tried to get you on and I know we'll get you on when we have the Android. This is the List app and it's as simple as it sounds. It's li.st is our domain. So eventually when we have web, we'll probably just want to be known as List. But it's really that simple and we aim to be that universal just to place four lists socially. So that my original idea was we all have these lists in our phones, in our notebooks, in our minds of what are the good restaurants in LA, etc. I wish I could see those lists on the phones or whatever of the people I care about or occasionally a celebrity or a publication that I would turn to for this type of thing. And I wanted a place. It seemed so simple to me. Why hasn't it been done? I thought a place where you could put these lists and everyone would put them and then you could search them and read them. And that is essentially what we built. So in this case, yeah, like I think I'm right. You know, I'm not saying I'm a genius or anything at all.


Introducing Pete's ListApp (01:03:16)

It seemed like this was something worth testing. And if you do it right and someone shows you an idea and you say, oh, not that, but yes, that. And like anything else, the most important thing is who you partner with. And so I knew I didn't know this field and I hired a company to make screenshots because everyone I pitched this to treated me the way I would treat them. If a tech person pitched me a good idea for a TV show, I'd say, that sounds like a good idea. I don't think you understand what it takes to do. You have a director, do you have funding, do you have a cast, do you know how to do a rewrite? You know, no, no. I mean, just an idea. Shouldn't someone make, you know, so that's how they treated me. And I thought, well, I need to show that I'm serious and that it would be good. So I asked friend after friend, do you know anyone who could make mockups for me? So I hired this great company called Two Toasters. And apparently it's named after coincidentally an office reference where Stanley ends up with two toasters because he bought one for Phyllis's wedding. But I didn't know that when I met. I didn't even remember the reference when I met them. So I drew up, I'm not a good artist, but I drew very simply, you know, again, this is not anything innovative. I drew up what a list would look like very similar to Twitter, to Instagram, to Tumblr, you know, a very vertical feed of lists and how you'd search for them and how you'd add a suggestion to someone else's and how you'd compose. And I asked, can you make a sort of a nice mockup of each of these main screens? So I paid them to make them and then I would walk around and tell people the idea and they'd say, yeah, it sounds good. I'd show them and they would try to tap and they couldn't because it was just a mockup. And that's how I knew, okay, they want to be using this. I showed them that I'm serious. They know what it feels like to want to see the next screen. And I showed, then I went to, then the guy at Two Toasters, Simon, said, I host a tech breakfast in New York once a month. I was going to be in town for that tech breakfast. So I went to it, talked to everyone. I'd say about 49% of the people were way too nice to me because I was a celebrity. About 49% of the people were way too hard on me because I was a celebrity and what am I doing here? Then there was one guy who took me seriously, who met me at my level and said, I like it for these reasons. I think these are my concerns. And his name was Matt Whithiler and he was a VC at Flybridge, which doesn't do this kind of thing generally, but he was interested. So I asked if I could have lunch with him. I almost canceled. I was hungover. I'm like, what am I doing? I'm here to do press for a TV show. Why am I pursuing this crazy tech thing? Everyone wants to do a startup. I almost canceled, but I didn't. I show up to meet him and he says, I know the co-founder for you. I don't think you can get him, but it's worth a try. I've been trying to convince this guy to leave his job forever, but I think he might like this because he's done stuff like this before. And his name was Dev Flaherty. He ran product at Fab. He had previously worked for a sort of a map based travel startup. And the original idea for this was travel lists, of course, would be big. So I said, let me try. I was leaving the next day. I emailed Dev, had dinner with him at the Ace Hotel in New York, the Breslin.


Success And Personal Insights

First meeting with Devin after the Jimmy Kimmel Show (01:06:33)

And we sat down. Lots of fatty food. Yeah. Right away, I was like, I'm doing what this guy, I'm not doing it. We wore the exact same watch, an IWC pilot. So a nice, simple watch with great design, great classic design. We ordered a bullet bourbon, each of us. So we have the same taste. And just like Matt Whithiler, he was hard on the idea and respected the idea, asking all the right questions. And he could talk. His wife was a television writer, and he was interested in what I was interested in. He was, tellingly, he was a Parks and Recreation fan, but not an office fan. So he liked the kinds of things I liked, but he was not impressed by me, my celebrity. He heard I was somebody, but he didn't care. He cared about Ron Swanson. So he was like adjacent. He was the perfect match. And he said, "Lena, let me think about it. Let me think about it." And then his wife kept getting up for jobs in Hallie Gross, who's a fantastic writer. I think she's a fantastic writer, fantastic talker and thinker, and she's on great shows. So I assume she's a great writer. So she kept getting more and more attention in LA, and then she was up for this huge writing job in LA on an HBO show. And no one was rooting for that job harder than me. I'm praying that Hallie gets hired because I know if Dev moves to LA, I'm sure he'll do this. And sure enough, she got the job and he finally committed to doing this. And he's really been leading the overall, why I think this is so good is because of Dev. I have a lot to do with the community. I obviously have a lot to do with the conception. And I argue for all my tastes all the time, but 90 plus percent of the time, Dev has already arrived there and added more things that I should have thought of. What are some of the more popular lists that have popped up?


Well, I can look at the trending lists right now. And I'll mention one to people. And just because I found this actually very, very cool and helpful, which was a list which you put on Twitter or retweeted, I think it was Cheryl Strayed and a writer of Wild, which was made into a movie. And she put out a list of writing prompts, so assignments or I think there were more sentences or questions that you could use for writing exercises. And what is your Twitter handle? @BJ Novak. So very simple @BJ Novak. So download the app and also follow BJ on Twitter because he highlights also quite a few different lists. But that list in and of itself. Yeah, that was great. And she also did a list that was very moving, which is objects found in my mother's car at the moment of her death or the time of her death. You know, just like a pen, you know, lipstick, tickets to this play. I don't remember exactly what it was. But I remember being just so stunned by the simplicity of that power in list form. And, you know, there's a lot of writers on it. So that, you know, there's a literary thing. But I'm looking here. You know, it's a mix of publications doing lists, celebrities doing lists, and, of course, mostly just regular folks. But trending right now, the Washington Post made a list of the things Donald Trump has called on America to boycott. He's called for a lot of boycotts over the years. It's very interesting, including the company that makes his clothing line, which he didn't realize. Vox made a list what NASA picked to explain our world to aliens. So what they put on Voyager 1 and 2, just, you know, a cool list. A girl named Jenna Martin I know made a list favorite Howard Stern interviews. And that's an open list. So you can make a suggestion on that list. And if she likes it, she double taps it. What is what are the top what are the top on the Howard Stern interviews Lady Gaga, Bill Hader, Billy Joel, which was a great one. I heard that one. Jonah Hill, Jerry Seinfeld, great interviewer. James Taylor, I did not know that. Although I've seen him be dark and funny. Chris Martin, apparently. So you know, some of them are very helpful recommendations, a lot of books lists. And some of them are very funny. Now, correct me if I have a faulty memory here, but I remember we were chatting on the phone a few months ago. Was it Lena Dunham who had dead people I'd have sex with? Am I making that up? Yes, she did. And I'm looking right now. Anthony Bourdain made one that I thought was really funny. This was, what was that? Four spy novels, three written by spies, one by non-spy. Yeah, he did that. He's a big reader and writer, obviously. His most recent one is called Hotel Slut. That's me. And you know, it's very much his writing style, but it's the hotels that he will stay. He will make an excuse to go to that town if he can stay in the following hotels, including one in Port-au-Prince, Haiti, Chateau-Mermont here in LA, the Raleigh in Miami. So his lists are great. Anything in New York? Let me see what his New York choice is. I'm headed to New York shortly, so maybe I'll try. There's a lot of lists of New York hotels. There's also a list of, if you ever say, the Bowery, which is my favorite hotel there. Bowery's great. There's two people, at least, have made lists of the best rooms at the Bowery. 1403 has this and 1401 has that. That's very useful. Very useful. I tried to stay at the Bowery. They were sold out for this upcoming trip, unfortunately. So it's very useful and also very creative. There's great people behind it. For someone who downloads the app, what would you suggest to get them a very good taste of the types of content? What would you suggest they do? I would suggest just, it's a very quick sign-up flow. Just sign up and there's a recommended follow menu. They'll take you to that screen automatically. One of the things you can do is you can hit follow all. It's our top 100 diverse accounts. So I'll read them right now. Not all 100, but the first batch. Lena Dunham, Mindy Kaling, The New York Times, Jimmy Fallon, The Onion, Anthony Bourdain, The New Yorker, CNN, Andy Cohen, Vogue, Snoop, Cheryl Strayed, Rachael Ray, People. Not everyone's John Mayer, Wired, TED Talks. Not everyone's going to like all of these, but then just unfollow because it will give you a real assortment. And there's a lot of civilians on there too, just people that are making crazy personal or advice lists. I would just say sign up, hit recommended, hit follow all recommended, and just see what you like. Very cool. Do you have, as we have a plane zooming overhead, do you have a little bit more time for some rapid fire questions? Yeah, sure.


When you hear the word successful... ? (01:13:28)

So we're going to shift gears just a little bit. Successful. When you hear the word successful, who's the first person who comes to mind and why? Shakespeare. Why? Because he made things that were both moving and permanent and popular.


BJs senior thesis (01:13:53)

What was your- Both three things. It shows you how far I am from that. What was your thesis on? Did you write a senior thesis? Whoa, you did your homework. Yeah, I did one on, mine was on, it's very specific, in the films of Hamlet, how they treat the line to be or not to be. Because that line already has a lot of mystery within the play, exactly what it means. But then you add all the culture. Like if you pay to see a movie of Hamlet, you're waiting for it to be or not to be the whole time. So how do the cultural expectations affect the interpretation of that line? Got it. Yeah, the bard. I mean, there are a lot of people who make me want to cry and do a pillow. As a writer who's trying to improve, that's certainly way up at the top of the list.


Most Often Given Books (01:14:42)

What book or books do you give most often as gifts? There's a book called The Oxford Book of Aphorisms, which I love. It's just the most well edited, brilliant one-liners from history. And you can spend hours on a page, or you can just flip through it. I give that one a lot. The Oxford Book of Aphorisms. And I'm going to give Daily Rituals, that book we mentioned a lot too. Anyone who's creative or ambitious, you take so much solace in seeing all the different processes people just do. What does Charles Dickens do every day? What did he do every day? What did Darwin do every day? What did Steve Jobs do every day? It's just so reassuring to see everyone's got their own system. It also is very reassuring to see how dysfunctional so many of them are. Yes. Depressing. Yeah, depressing in some cases. Great book. I actually produce the audiobook for people who want to try the audio. If you could change one thing about yourself, what would it be? I'd love to be great looking. You're not a bad looking guy. I'm not terrible looking, thank you. But I look at James Franco and he does all the things he does. And I'm like, man. James Franco. Well, look at his brother. I mean, they're like... No, I'm saying... It's a handsome family. Tim, if I could have whatever I wanted, I could lie and say, "Oh, I'd learn to be better at empathy." No, I'd be like fucking awesome looking. And then I would like... If you're James Franco, you could do anything. And people are like, "Well, it's pretty interesting." Anything. And I wish I had that extra level. I'm just answering this. No, no. I appreciate the honesty. Fucking awesome looking. This is good. Do you have any bad habits that you're currently working on? Yeah, of course. I zone out. Any conversation. I'm not holding a microphone. I zone out easily. I just love daydreaming and I think it's so indulgent in a good way to the creative process, but then you get used to that indulgence when someone else deserves your attention. So I try to be better at that. How do you go about trying to become better at that? Is it just a conscious decision not to zone out? Good question. I don't have a process yet. I'm just always berating myself. I do the same thing. So if you come up with anything, please let me know. Words or phrases that you overuse? Pretty. That's my one too. Really? Oh, I hate it. I started trying to fix it by saying... How do you use it as an adverb or an adjective? How do you use it? Adverb. See, I use it as an adjective. Oh, okay. But I don't mind using it. Okay. Yeah, I say, "Oh, that's pretty interesting. Oh, that's pretty... That's pretty..." And I tried to fix it at one point by forcing myself to say "fucking" afterwards. So I'd say, "That's pretty fucking interesting. That's fucking smart." And eventually it short-circuited for a while. It's definitely... I overuse "like," which is so embarrassing because it's not a very masculine word to overuse but I do. Like as a verb or like as a... I don't even know what it is. It's a stutter, really. Like. Oh, I see. I see. Do you have anything in writing, long form, let's say in a book? One of mine is, for instance, like, "That having been said," or something. Sure. I overwrite a lot and I need to pare it down. Got it. Just too many revisions. I don't know any one phrase. But... No, no. I just... I do stuff like that because it sounds... I don't know. It kind of... It gives extra elegance to a stupid idea. And then I need to go back and be like, "You know what?" Put some monkey in a suit. Yeah. It's something I learned on The Office too. If you're... If a scene should be two pages and it's four pages, it's a bad scene. It's just you... Because you keep writing when you haven't hit it. So if it's a great scene, it might just be a two-line exchange. I love you. I don't love you. Like, "Whoa, that's a scene." But if the scene is like, "So I was thinking the other day, my feelings," that's not a scene. You know it's not working. Yeah. So if you overwrite, it's often a sign that you have not hit it and you're still looking for it. What is the best purchase that you've made in recent memory for less than $100?


Best Recent Purchase (01:18:54)

An ice cube tray that has giant ice cubes in it. Anytime I'm at a bar and they have a big ice cube, I feel like, "Oh, this should cost like $100. This is so nice." And then I thought, "Well, wait. The rubber ice cube tray shouldn't be any more expensive. It's just a different shape mold." So I go on Amazon and sure enough, Tivolo, I think is the company, for like $7, it's six huge ice cubes. And if anyone comes over and I make them a drink, they have one huge ice cube in their glass and it's like I have a fancy bar. Do you have any favorite documentaries?


Comedy Writing Advice And Personal Reflections

Favorite Documentaries (01:19:35)

You know what? Do you mind if I look at the List app? I don't mind if you look at the List app. What are my favorite documentaries on the List app? I love documentaries. I'll throw… I'll just buy it sometime. I'll throw one out. Well, I loved Man on Wire when it came out. Okay. Very uniquely put together. And the same team made a documentary subsequent to that called Project Nim, which was about a chimpanzee, this was in the '70s, effectively raised as a human child to see if Nim, in this case, could… I think it was Nome… No, Nim Chomsky or Chimpsky, they called him in any case, could acquire language. And just a fascinating documentary on human thought, human interaction with this chimp and so on. On my list, Catfish. It's a cliché, but Catfish is a brilliant documentary. I still haven't seen it. It's brilliant. It's mind-defining and it's just become a term, but it earned that term. Brilliant movie. To Be and To Have is on my list. A beautiful, simple film about a one-room schoolhouse in France. And just what happens over the course of a year. There's really little story, but it really holds your attention and gives you a spirit of a place. And if I choose one more… Oh, you know what's a really cool one? It's called The Overnighters and it's about the oil fields in North Dakota. Came out a couple years ago on this pastor who has a church there. The Bakken oil fields, which is probably bigger than the gold rush in the 1800s. And just like, now that you can frack, there's so much oil in North Dakota that a whole culture… You can rent a garage in North Dakota for $250,000. There's so much money there and such a rush to be close to it. That's a really interesting documentary. The Overnighters.


How to power up to get into the zone. (01:21:36)

So, I usually ask about morning routines, but I want to ask about… And you can feel free to answer that, but I'm so curious to dig a little bit into your powering up. How would you power up to get into the zone? I have Venti Pike Place coffee from Starbucks. I find that… How is it made? Just black? Yep, black. So, brewing my own coffee at home is so unpredictable. It's like getting artisanal Tylenol. I want to know what my dose is. You wouldn't be like, "Oh, I made some Tylenol for you." No, give me two Tylenol. So I want a standard dose of caffeine. You want your standard loading dose of caffeine. So I have a Venti from Starbucks. When you have it, you mean you purchase it or do you just down the thing like a shot of tequila? I either drive to the Starbucks. It takes an hour because I will sometimes read the paper, the Wall Street Journal or the recently the Wall Street Journal, which I find really good, especially on weekends, or the New York Times is my favorite. And I often read that, usually read that online. And just emails and I turn on music. I usually listen to Morning Becomes Eclectic on KCRW. Morning Becomes Eclectic? Yeah. It's this great show from 9 to 12 every weekday. Commercial-free, just cool new music. I also have a list on the app of music that I work to. And they have a 24-hour station. Do you have another one that you can pull from memory? Yeah, yeah. I will often do Pandora of early blues, which I find good to just… So yeah, I listen to music. We're serious. XM 35 is like indie music that I like. So you just listen to music. It's just about being in a good mood. I slowly drink that Starbucks. I sometimes take a walk around Runyon Canyon or my neighborhood. You know, text, email. If there's a book, I'm kind of reading a couple chapters. And then eventually I'm just like, "All right, either I'm excited by an idea or I'm… It's like 3.30 and I'm like… This powering up turned into lunch, turned into a workout." You know, and I'm like, "God damn it." I cleared out my whole day and it's 3 fucking 30 and I haven't written anything. You know, then I just start looking at my files and then I finally get going. So yeah, the power up can have a happy or sad ending. Is there a particular time of day that you find you tend to do your best writing? For me, it's always been super late night. I don't know why that is. For synthesis, for note taking, for interviewing, I can do that whenever. But for synthesis, I've always been kind of a 10 p.m. to 5 a.m. kind of guy for whatever reason. It's hard for me to get myself to work later in the day. So probably my most productive time is like 11 to 2. But the creative ideas can come anytime. I never know when those are coming. Let's see here.


One or two shows for good comedy writing? (01:24:39)

If people wanted to watch, besides The Office, one or two TV shows for good comedy writing, any particular recommendations? I love the show right now called The Grinder with Rob Lowe and Fred Savage. That's very, very good writing. Season four of Mr. Show is brilliant sketch writing. Could you explain what you mean by sketch? I apologize. Oh, sketch like SNL. Yeah, I'd say those are pretty great ones. Cool.


Historical figure Rainn identifies with most. (01:25:16)

Just a few more questions. What historical figure do you must identify with? In my hopes, Ben Franklin, because he started in comedy. And then I make a joke about this in my standup act. He really took it to the next level. He wrote Poor Richard's Almanac and he was known as a comedy writer. And then he ended up discovering electricity and having his face on money. And he remained a witty guy. My hope is that I could do some shadow where I can have ambitious, positive-spirited ideas, but it won't be like, "Oh, now he lost his sense of humor." Ben Franklin always had a sense of humor and he wasn't ashamed to experiment with lightning. That's really cool. Even in my most egotistical, I don't actually identify with him. He's just like, "If I'm sussing myself off…" Aspirational. Yeah, yeah, aspirational role model.


Advice for aspiring comedy writers. (01:26:22)

Probably someone more funny and dark. For someone recognizing that no path is quite the same for people, certainly, that I've met in entertainment or comedy or whatnot, from going from school to the industry of – if we could call it one industry – of entertainment, let's just say you had a promising high school senior who's a gifted writer and they think they want to be in comedy writing. What advice would you give them? A bunch of things. One piece of advice that I stand by, that I've given to a bunch of people, is really think of it as two things. You need to get people's attention and you need to be able to back it up. This is especially for getting – I feel like most people who want to get into comedy, what they want to do these days is get a staff job on a TV comedy show. To do that, you need – think like the person hiring you. If you were giving your own show, you'd panic. This is my one big shot. It's got to be hilarious. You hire your most loyal funniest friends first. Then you'd ask around, "Who worked on my favorite shows? Who's the best, best, best person?" Those names would come to you through an agent or something. Then you'd like anyone that you saw or heard or you were at a stand-up show and this guy was hilarious or someone sent you this internet video or you just don't know. Or you'd ask around and someone would send you something. The first thing is get their attention. That could mean be friends with somebody or have collaborated with somebody. Another thing is you might want to make something. For me, it was stand-up but I don't know what it is for anyone else. It could be probably some internet video. I feel like that's the best way to – you can be completely wild and get seen. Make something truly great that could be anything, absolutely anything. Then, once you have someone's attention, they're going to want to be sure that they're not taking a crazy bet on some kid who made some funny video who then gets in the writer's room and doesn't know what to do. That generally means have a spec script which is a speculative script that could be for a TV show. You write an episode of The Office or The Simpsons or whatever just to show that if you were on that stuff, you'd be able to know the voices. You'd know how to format it. You'd know how to craft the story. You can write hard jokes. Have a spec script and it will probably take you a few to get a really good one but back it up and get their attention. Now, that's for anyone starting out. I don't know if I'd advise a high school senior to go right into TV writing. This advice is probably more for someone who just graduated college or someone – whatever stage of life they're just ready to start this. If you're really going to go to college, I'd say stay funny. Be around funny people. Come up with funny ideas.


Advice for B J 's 30 year old self (01:29:40)

Make your friends laugh. Be mischievous. Yeah, be mischievous. Now, you are – I think it's up to 36. What advice would you give your 30-year-old self and where were you? What were you doing at 30? At 30, I was on The Office. I wish I had told myself on The Office and this might be specific to me. The whole time I was on The Office, I thought, "Well, this is my best shot at whatever I'd ever want to do. So I better not waste a second. I better write a screenplay. I better make a avant-garde film. I better get cast in something. I better do my big thing while I'm still in The Office because I don't want to be that guy who used to be on The Office." But I didn't have time. I had two jobs on The Office. Either one of them should take up your focus. Now, at one point, you had three, right? Was it writer, producer, actor? Well, producer tends to just be high-level writer. So I take that. That was the same job. But it's important. Writing is really – for the whole show is part of your responsibility. So I wish I could tell – and now people ask me, "What was it like working at The Office? Was it so much fun? Was it a time?" Yeah, but I have to admit, that's buried under. I was so anxious and always trying to write some extra thing on the side that I never finished and never had time for. And I really didn't just enjoy this incredible once-in-a-lifetime thing. And as soon as The Office ended, I was talented enough to write a book and I'm proud of the book. And I made the app and I worked really hard and I was able to pull it off. If you can do it, you can do it. You're not really on someone else's schedule ever. And I also tell people all the time, if Will Smith isn't in a movie for three years, you're not walking around saying, "Where's Will Smith?" No one is paying attention to anybody else at all. You think everyone is, but they're not. So take as long as you want if you're talented. It's not really – you'll get their attention again if you have reason to. And so I do wish I had told myself back then, this is very, very special. Own it. Be in it. Enjoy it instead of being so nervous. All for nothing. None of the things I tried to do on the side of The Office ever got anywhere because I just didn't have time. I think that's good advice for a lot of people in a lot of places. That was the advice also that Stephen King gave to Neil Gaiman, one of my favorite fiction writers. Really? What was the advice? Well, I think it was because Neil was sitting at – I think it was a book signing for Sandman, which was just this incredible canon of work that redefined what was possible in the graphic novel genre. Yeah, I know of that book. It's just incredible. And he's used that, of course, as a stepping stone to write novels that have been turned into movies and so on. But he was sitting there with this huge line of people as I remember it, and he said, "Enjoy this."


Closing Remarks

Parting Questions (01:32:45)

And that's my laptop sliding, but he didn't. He had a lot of trouble enjoying it. And I think that's a constant battle. Well, I don't want to take up any more of your time. This has been a blast. It's getting so great. It's getting dark and probably time for some food. Where can people find you and what you're up to online? Where are the best places to go? I think the best place is the List app because that's where I am. So I would say download the List app on the App Store or it'll be on Android and web soon. And that's just three words of the List app. Or go to li.st. And my profile there is all my favorites and ideas and thoughts on this and that. I'm also on Twitter. Yeah. @BJNovec. @BJNovec. And that's me on the List app too. Cool. Well, this has been great fun. Maybe we'll do a round two sometime. And thanks so much again. Thanks, man. I really appreciate it. So cool. And to everybody listening, you can find the show notes, links to all the books, shows, apps, et cetera that were mentioned at 4hourworkweek.com/podcast, or you can just go to 4hourworkweek.com and click on Podcast.


Outro (01:33:54)

It has show notes for this episode and every other episode. And as always, until next time, thank you for listening.


FIVE BULLET FRIDAY (01:34:08)

Hey, guys. This is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it.


WEALTHFRONT (01:35:17)

This episode is brought to you by Wealthfront and this is a very unique sponsor. Wealthfront is a massively disruptive in a good way, set it and forget it investing service led by technologists from places like Apple and world famous investors. It has exploded in popularity in the last two years and they now have more than two and a half billion dollars under management. In fact, some of my very good friends, investors in Silicon Valley have millions of their own money in Wealthfront. So the question is why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra wealthy but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams etc. And I'll come back to that in a second. I suggest you check out wealthfront.com/tim. Take the risk assessment quiz which only takes two to five minutes and they'll show you for free exactly the portfolio they put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis but normally aren't. Great investing is a marathon, not a sprint and little things that you may or may not be familiar with like automatic tax loss harvesting, rebalancing your portfolio across more than 10 asset classes and dividend reinvestment add up to very large amounts of money over longer periods of time. Wealthfront as I mentioned since it's using software instead of retail locations etc. Can offer all of this at low cost that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything they charge 0.25% per year on assets above the first 15,000 which is managed for free if you use my link, wealthfront.com/tim. That is less than $5 a month to invest a $30,000 account for instance. Now normally when I have a sponsor on this show it's because I use them and recommend them. In this case it's a little different. I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast but because of SEC regulations, companies that invest your money are not allowed to use client testimonials. So I couldn't be a user and have them on the podcast. But I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now back to the recommendation. As a Tim Ferriss show listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at wealthfront.com/tim. It's fast, it's free. There's no downside that I can think of. Now I do have to read a mandatory disclaimer. Wealthfront Inc. is an SEC registered investment advisor. Wealthfront in securities involves risks and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit wealthfront.com to read their full disclosure. So check it out guys. This is one of the hottest, most innovative companies coming out of Silicon Valley and they're killing it. They've become massively popular. Just take a look, see what portfolio they would create for you and you can use that information however you want. Wealthfront.com/tim.


Additional Resources

VIMEO PRO (01:38:24)

This episode is brought to you by Vimeo Pro, which is the ideal video hosting platform for entrepreneurs. And in fact, a bunch of my startups already use Vimeo Pro, including Wealthfront, who uses it to explain how Wealthfront works. TaskRabbit uses it to tell their company's story. And there are many other names you would recognize among their customers, Airbnb, Etsy, et cetera. Why do they use it? Vimeo Pro provides enterprise level video hosting for a fraction of the usual cost. Features include gorgeous high quality playback with no ads, up to 20 gigabytes of video storage every week, unlimited plays and views, and a fully customizable video player, which can include your logo, custom outro, et cetera. You also get VIP support. And you get all of this for just $1.99 per year. That's $17 a month with no complicated bandwidth calculations or hidden fees. And you can try it risk-free for 30 days. So check it out. Vimeo.com/business. That's V-I-M-E-O.com/business. And use promo code TIM to get 25% off. That's a special discount just for you guys. So check it out. Vimeo.com/business, promo code TIM. And until next time, thank you for listening.


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