EP. 237 — Re-Release: Sasheer Is Now the Sleepy One with Penn Badgley & Nava Kavelin

SASHEER: Hi, friends. It’s Sasheer.

NICOLE: And Nicole here. This holiday season, we’re taking some time off, so we’re sharing one of our favorite episodes, where actor Penn Badgley and Nava Kavelin play Besting Each Other.

SASHEER: It was such a pleasure to have them, and we hope you enjoy it!

NICOLE: Hi, Sasheer.

SASHEER: Hi, Nicole.

NICOLE: How are you today?

SASHEER: I’m good.

NICOLE: I don’t know. I feel like I came in too hot.

SASHEER: My energy levels are on a different plane right now.

NICOLE: I understand. Did you wrap super late last night?

SASHEER: I wrapped a few hours ago. I wrapped at 8:00 a.m.

NICOLE: Girl! No! Sasheer! My word. My friend is working hard. That’s wild.

SASHEER: It’s wild. Yeah. My body doesn’t know what’s happening. I don’t know what day it is. I, like, went to sleep at 11:00 and then woke up at 2:00 to go to work. And then I was like, “Is it the same night? Is it tomorrow? What is happening?”

NICOLE: This is like that time we recorded, and it sounded like I was in slow motion. But you don’t sound like you’re in slow motion. And then we did our live show, and I was like, “Did we record a podcast together?” And you’re like, “We sure did.” It was wild.

SASHEER: Yeah. Now I’m doing what you did; I’m doing night shoots, and it’s beautiful. Crazy.

NICOLE: It should be illegal. It’s just too crazy.

SASHEER: We’re also filming at Disneyland, and so there’s all these rules. And we had to take a million shuttles, and there’s, like, so many checkpoints because it’s just, like, crazy security there. So, a lot of the time it’s travel getting in there.

NICOLE: Have any of those mouse heads recognized you?

SASHEER: Yes. Some people have been, like, filming on the side, which is cute. Like, they get to see a show within a show, essentially.

NICOLE: Oh, that’s fun.

SASHEER: Yeah. It’s funny because it’s also like people are very sweet, but they’ll, like, scream while we’re filming. So, people have been like, “Carla!” on the side. And then we gotta, like, stop and restart. But it’s sweet.

NICOLE: That’s actually pretty funny. “Action.” “Carla!” “Please stop.”

SASHEER: Not only that, but then there’s also, like, just consistent sounds throughout the park. There’s just, like, music. It’s a Small World is playing in the background. There’s a train happening. They’re like, “Welcome to… In 15 minutes, the fireworks are going to–” There’s, like, a million announcements happening, so we have to stop a lot.

NICOLE: If the audio sounds fine–which it probably will–I will never hold for another airplane again. Do you know what I mean? When they’re like, “We can’t shoot that. There’s airplanes circling around. There’s a whole–” No. If you can shoot in fucking Disneyland where there’s a 100 million sounds, then why am I holding for one single plane?

SASHEER: Maybe we’re in a world where there’s no planes. Maybe they want to believe there’s no planes in whatever reality is in the show.

NICOLE: Interesting. It’s funny to think about TV. Like, once you’re in it, you’re like, “Oh, so in TV, there’s no airplanes. Also, there’s no logos. Or there’s very few logos.”

SASHEER: “No busy patterns.”

NICOLE: Yeah. You can’t wear any, like, wavy things because it morays.

SASHEER: Yeah. It is interesting.

NICOLE: Everyone has terrible wigs. I can’t get over the wigs on these big budget things. They’re terrible. Did you see the picture on Twitter of Chris Evans in a wig, where they cut it with what look like gardening shears or something? It was just, like, triangles. I was so confused. I was like, “Why did they do this? Why on earth?” I’ll find these. I’ll find it. And this is what people love about podcasting: me holding my phone up to the camera for a picture they cannot see. But I did retweet it, so you can find it real good. Okay, look.

SASHEER: I really don’t know what I’m looking at. Oh, my God! Oh, no, no, no, no.

NICOLE: Isn’t that wild.

SASHEER: Who did that?

NICOLE: I don’t know, but that’s the picture… Not up close. But isn’t that nuts? Why are we doing this to people?

SASHEER: It’s also like you could have edited that– They could have edited the photo. They shouldn’t have cut the lace like that on the wig. But also, they could have touched that up.

NICOLE: Not only did he anger the hair department, but he also angered post.

SASHEER: They are like, “We are not helping him at all.”

NICOLE: How do you do that? They were like, “Chris, no! We don’t like you here!”

SASHEER: Well, speaking of Hollywood and TV shows, we have a person from one of our favorite TV shows–the television show You.

NICOLE: Yes!

SASHEER: We have Penn Badgley and his best friend, Nava Kavelin, here to talk about their friendship and their production company and the work they’ve been doing together. And we’re going to be testing their friendship and their knowledge of each other in a little segment we call Besting Each Other.

NICOLE: Best Friends Today.

SASHEER: Yep. You know it. You love it. Best Friends Today.

NICOLE: I think we’re going to do Nava first.

SASHEER: Okay, so now we are going to do a segment called Besting Each Other, where we ask each best friend in the group about their other best friend. And first up we have Nava Kavelin, and she’s going to talk about her best friendship with Penn. Hi, Nava!

NAVA: Hello. Hi. Thanks for having me today.

SASHEER: Thank you for joining us.

NAVA: Thank you for being here.

SASHEER: Okay. Are you ready for these really intense questions?

NAVA: Let’s do it. I’m ready. I’m ready.

NICOLE: The first question is, how did you two meet?

NAVA: Penn and I met in New York City in my apartment. So, he was good friends–still is good friends with the girl I was living with named Martha. And he had gotten the offer for You. And he was really conflicted about taking the role. And I think he’s talked about this in the press. I don’t think I’m, like, outing him. And he basically had come over to, like, consult with her. He was getting different people’s opinions and was getting her opinion as well and sort of like, “Should I take it, or should I not?” And I had just gotten home from the gym, and my roommate Martha didn’t give me a heads up that, like, you know, a really cute celebrity was going to be in our kitchen. And I, like, walked into the kitchen, and there was Penn Badgley. And in my head, I was like, “Oh, my God.” But I didn’t pretend that I didn’t know him, but I also didn’t acknowledge that I did. I was just, like, cool. Like, “Hey, what’s up?” And then I went into my bedroom. I thought about it the whole time, like, “I really want to come back downstairs. I really want to talk to him.” But I didn’t. But then we kept sort of naturally meeting after that.

SASHEER: Okay. So, you’re, like, in the same friend group?

NAVA: Yes. We’re in the same friend group. And then we’re both members of the Baha’i Faith, which is a pretty small religious community. So, we, like, go to a lot of the same events. And we were involved in a similar, like, youth program–a mentorship program for youth. So, we would, like, see each other a lot through that.

SASHEER: Do you remember a moment where you went from just, like, casually being in group settings to being like, “You know what? I like this person,” and, like, clicking?

NAVA: We had a road trip to Maine. So, I worked at the UN when I was in New York, and I was a researcher for a UN organization. And one kind of quarter–like a three-month period–I was researching the impact of media on youth. And I convinced Penn to go to a conference with me mostly because he had a car and he’d drive me. And there would be producers and actors and people thinking about, like, the positive impacts of film, potentially. And so, we ended up driving to that together with my roommate Martha, who works at TED Talks. And on that car ride we were all going through something really difficult–really challenging. And we were all commiserating and, like, really bonding. And that’s when he and I became really good friends.

NICOLE: That’s cute. I love that. When you said “TED,” I was like, “Ooh. Who is this Ted?”

SASHEER: The Mark Wahlberg movie Ted.

NICOLE: “Oh, the teddy bear? Is that what you’re speaking of?”

SASHEER: So next question. What is your favorite memory of traveling together?

NAVA: It would be that road trip, but I kind of think there’s another one. So, Penn and I now have a production company together, and we do annual retreats. We do, like, two a year. And this year I flew to London for one because he’s in London filming You. It got cut short, so we just had, like, a… I know he’s not going to say this, but I’m going to say it anyway. We had, like, a half day together in London. And it was really cool just to see how people react to Penn in London. It was different than in the States. I felt like there was a bigger reaction, and it was, like, whispers through the crowd. And in the U.S., people are more straightforward. They either know who you are or don’t–and they acknowledge it, or they don’t. They’re not trying to, like, be secretive about it is my experience with him. You’re both famous, so you know what it’s like. But in the UK, it was like everything was whispers. And you could see, like, a whisper moving through the crowd. And I just thought that was, like, so fun and cute. And it was just really fun to have, like, a half day together in London, even though it was, like, shorter than what we’d planned. I loved that, so that’s probably my favorite.

SASHEER: Did you guys do anything with your half day?

NAVA: His wife was there and his kids. And my sister was there. And we all went to a really pretty park. And we went to a bakery. And we went to this, like, marketplace. We were in Notting Hill, and I think there’s, like, a famous marketplace. They sell, like, silver and China–a very UK marketplace. And we walked through that, and that’s where people were, like ,whispering and the crowd was forming.

NICOLE: That sounds like such a cute day.

NAVA: It was. It was really fun.

NICOLE: What’s your favorite thing about Penn?

NAVA: My favorite thing about Penn is that he’s super generous–to a degree that I haven’t seen in many people. I’m his business partner, so I also benefit from that in, like, a professional setting. But also, as a friend, he’s just incredibly generous. He’s incredibly giving. So that’s definitely my favorite thing about him. But another thing is that he’s really funny, which I think a lot of people don’t know and which for some reason he doesn’t show often. And I’m always like, “Man, you got to be funnier.” I think even before this, I texted him–I was like, “Could you please be funny today? You brought a non-famous. They probably wanted you to bring Chase Crawford, and you brought me, so you have to deliver.” We’ll see. We’ll see how he does. But he is actually very funny.

NICOLE: That’s so funny to text someone, “Can you be funny today?”

SASHEER: Okay, so if you could have to guess, what do you think Penn’s favorite thing is about you?

NAVA: This is either his favorite thing or his least favorite thing, and it might be both. But Penn has told me many times that I’m the most straightforward person he’s ever met. Like, you always know where you stand with me. If I’m happy with something you’ve done, you know it. And if I’m not, you also know it. And I don’t like to simulate how I feel. So, I think he admires that I’m straightforward, and I think it also really annoys him that I’m, like, really straightforward sometimes.

SASHEER: Can you think of a time where you were very straightforward and maybe he didn’t like that?

NAVA: Yeah, I can think of many things. But there’s one project where I feel like we haven’t met a deadline that we should. And I have sent him many notes about why I think that’s a problem–pretty, like, directly. And I know that that, like, annoys him because I think for him, in Hollywood, there’s a culture of like, “It’s casual. We say six months, but it’s really 12.” But I worked at the UN where it’s not a minute later THAN that. Getting used to each other’s different ways of handling that has been, like, a point of tension a few times. Yeah.

NICOLE: That’s funny to think about. Yeah. In the industry, the timeline is like, “Okay, we’ll get to you in six months.” And then two years later, the project is finished. Okay. What is something you do that drives Penn crazy?

NAVA: I text him incessantly. If he doesn’t respond to a text from me, I’ll just, like, keep following up. I don’t know if he’ll say that, but I know it drives him crazy. I don’t know if he’s ever admitted to me that it drives me crazy. That’s probably one. There’s probably so many. And maybe just, like, being too direct sometimes, I think. He’s like, “You could have sugarcoated that a little bit. Yeah.”

SASHEER: What is something that Penn does that drives you crazy?

NAVA: He ignores my texts. Also, on a smaller note, he hardly ever uses exclamation points and emojis. And I know that’s so stupid, but sometimes it hurts my feelings. I’m like, “This was so sweet. It deserved a little heart emoji or something.”

NICOLE: No, I guess that. I love emojis. I use them so much. I use them randomly, too.

SASHEER: It was a point of contention with Nicole’s texting because… She’s better at it now, but for a while she would write in full sentences and add a period at the end of sentences. And that feels harsh. So sometimes you’d ask her a question, and she’d be like, “Yes.” And I’m like, “Oh, my God. What did I do?”

NICOLE: And I didn’t know it was a universal thing. Everyone had a problem with the way I texted.

NAVA: That’s really funny.

NICOLE: It was very hard to hear. And then sometimes I put a period at the end and then I’ll delete. I’m like, “I don’t want anyone to think I’m mad at them.”

NAVA: But then if you do it deliberately now, is it because you’re mad and you want them to know?

NICOLE: No, if I’m mad, I just, like, text a– I’ll do, like, a voice memo. I’ll be like, “I’m mad!” It’s like a full-blown cartoon character. Okay. Between you and Ben, who would do better on the CBS television series that has been running for 97 seasons called Survivor?

NAVA: Has it really been 97 seasons? That’s a joke. They do, like, four a year? For sure Penn. He’s, like, the famous, rich one, but I am way more high maintenance. Penn is so down to earth–so easygoing. And he is, like, handy and, I think, would do well on that show. And I would die on day one. Like, I would not make it out alive, I’m sure.

NICOLE: Have you ever watched Survivor?

NAVA: I… Was it the first season that there was some insane guy named Richard who was, like, quite evil or something? I probably shouldn’t say stuff like that.

NICOLE: Here’s the thing… Neither of us have watched it.

NAVA: I think I saw one episode because there was so much press about this guy being, like, awful. But that’s all I’ve seen.

SASHEER: Do you think you’d have any skill with the, like, social aspect of Survivor because there’s, like, surviving in the wilderness. But there’s also, like, a team thing going on. And coming from the UN, I would wonder if you maybe have some skills working with other people.

NAVA: Maybe. I can be diplomatic. And I can keep a secret. I have a good poker face, so maybe.

NICOLE: Boy, oh, boy. What’s it like to keep a secret? Doesn’t it eat you alive when you see someone you know who’s, like, a mutual friend? Don’t you just want to tell them?

NAVA: I mean, definitely. Definitely I want to. But if I have to keep the secret, I can.

NICOLE: Boy… I can keep some secrets. But sometimes I’m like, “Ahhh…”

NAVA: Oh, something Penn is really good at–he is a vault. I think sometimes he also just forgets. But with me, you have to tell me not to tell because I’m very, like, open. I’m not super private. So, you have to tell me not to tell other people. And then I won’t tell them if I know you don’t want me to. But if you don’t tell them, sometimes I just assume again. But Penn always assumes that it’s private, and he’s, like, really private. It’s really good.

SASHEER: Oh. That’s wonderful.

NICOLE: I tell Sasheer everything about everybody. And when people go, “Don’t tell anyone, I cross my fingers, and I go, ‘I won’t.’” And then in my head I’m like, “But I’m going to tell Sasheer.”

NAVA: Sasheer, do you tell Nicole everything?

SASHEER: Yeah. I do. It should just be understood, “Well, Nicole’s gonna get this information anyway.” Okay. We reached the end. What do you hope you’re both doing 20 years from now?

NAVA: I’ll start with Penn. I hope Penn is an award-winning director. I think that’s a path. I think he’d be really good at that. I hope he gets a star in one of the, like, superhero franchises. I think that’d be great for him. I hope our company is still around and successful. And I hope that he… He has two kids now. I hope he has one more. I think he wants one more. And I hope that one of his kids is a really talented classical musician. I have one more. And I hope that his side hustle is being a guest lecturer at USC because he got into USC, but he didn’t go. And sometimes I think he regrets it. And I think he’d be an amazing professor. I hope he has a very busy–

SASHEER: Full schedule.

NAVA: I hope he can pull that all off. And then for myself, I hope that I’m married and have kids. That’s my number one. This is probably gonna sound really strange, but I hope that I’m a really good neighbor. I’m, like, really obsessed with the idea of, like, neighbors getting to know each other and, like, bringing each other cookies when you live on the same block and, like, having each other’s numbers. So, I hope that our family would be a family that anyone in the neighborhood could come to. I really love that idea. And I hope that our production company is really successful.

NICOLE: That’s so sweet.

SASHEER: I love that. Can you be more specific about “successful”? What would happen in your production company?

NAVA: That’s a great question, Sasheer. Right now, we have a podcast out, and we have, like, two independent films that we’re working on. But I think we’d love to have sort of a little bit of everything, like movies and TV shows. And then part of our ethos is creating content that doesn’t have to be positive or upbeat. It can deal with heavy things, but it shows a bright side of human nature. And it’s really hard to sell that is what we found. And so, I hope that we’re, like, successful in that way–that we’re not just, like, making dark stuff because that’s what sells. So, I hope that we’re making, like, uplifting content that people enjoy and watch.

SASHEER: I love that.

NICOLE: I love that, too.

NAVA: Thank you.

NICOLE: Also, now I want to bring cookies to my neighbors.

NAVA: I’ve done it many times. Some are weirded out because it’s not normal. But for the most part I’ve, like, made friends out of it. They’re like, “What did you put in these cookies?” But I think people like it.

SASHEER: I should try that, too. I’m surrounded by a lot of older people.

NICOLE: They’ll love cookies.

NAVA: I love that.

SASHEER: But I’m like, “I should probably know these people who are gonna be here forever.” I, like, forgot because I spent most of my adult years in New York in apartment buildings, where I’m like, “I’m gonna leave soon, so I don’t even know who these people are.” And then I moved into a house and then was, like, not making an effort to go meet people. And then I was like, “Oh, wait. I should probably know these people just–I don’t know–in case of emergency or whatever.”

NAVA: So, I actually lived in New York obviously before. And I lived in Brooklyn, and one of my roommates also was really into that idea. And we went down our whole block. I think we brought people Dough Doughnuts from that Bed-Stuy doughnut place.

SASHEER: That’s nice.

NAVA: So good. And we made friends. I had, like, just moved into that place, and then the pandemic hit. And we all, like, were able to rely on each other because we had exchanged numbers–we had a WhatsApp group. And, like, thank goodness we did that. We didn’t do that knowing that a global pandemic was going to hit. But we felt so much safer knowing our neighbors and knowing everyone on the block now. So, you just never know.

NICOLE: I love that. Well, we’re now going to quiz Penn on you!

NAVA: Alright. Excited. Nervous. Thank you.

NICOLE: You’re welcome.

SASHEER: Now we’re onto the second part of Besting Each Other. We just talked to Nava, and now we’re going to talk to her best friend, Penn Badgley. Hello!

PENN: Hello.

SASHEER: Welcome.

PENN: And thank you for having us.

NICOLE: Welcome. And thank you for doing this!

SASHEER: We’re going to ask you some really intense questions. I hope you’re ready.

PENN: That’s great. Those are the only kind I like.

NICOLE: Well, here’s the first intense question. How did you two meet?

PENN: Well, we both think that it’s likely we would have met at some point maybe preliminarily before this but, like, just very much in passing. But it was in her apartment because I was pretty close friends with her roommate at the time. And I was sitting actually, like, in this little couch thingy, talking to her roommate–a friend of ours named Martha–who is also very close with Nava Shoutout to Martha. She’s listening. And actually, I was having a very intense conversation with Martha because I was thinking about whether or not I was going to take this job that was coming up, and it was called You, which is the show I’m now on. And–yeah–a lot of factors to think about. And. And then Nava came in, and I think she just walked out–something along those lines. It was not much to think about. Then later I would see her again in that apartment because they would host these gatherings where they just pull people from all different kinds of backgrounds and conversations they’d had at work or whatever it is, and they called it “Meaningful Conversations.” And I remember the first time I really heard Nava speak I gathered that she was working at the UN. And everything she said was really sharp. And I just thought, “Oh, wow. Who’s this person?” And then it would snowball. I mean, to be honest, one thing I love about her… Well, you know, I won’t go on too much right now. I answered the question.

SASHEER: We’re going to get into what you love about her. Okay. The next question is, what is your favorite memory of traveling together?

PENN: I mean, real travel–we only have the one, which goes into actually what I was about to say. Our friendship really has always had, like, a purpose to it, you know? You know, a lot of people you meet circumstantially. We really traveled together for the first and only real significant time on our way to this conference. It was, like, a media gathering. And what she was doing at the UN at the time partly–not all she was doing–was researching the effects of… Is it research? It would have been gathering research because she wasn’t conducting the research herself. So, you know, she was researching the effects of media on youth. And this was a lot of what I was thinking about at the time because of the shows I come from. And so, our first conversations were all about that. And then it was, like, a six-hour drive, I think. And so, I don’t remember any of the conversations really. I think she played me some music by The 1975, I think. And I think maybe we listened to my music, too. And there were two other people in the car,

SASHEER: That’s funny. You’re like, “I really loved that she let me play my music in a six-hour car ride.”

PENN: I mean, it was on repeat. I don’t let anybody listen to anything else.

SASHEER: You’re like, “Listen to it again. Let me know how you really feel.”

PENN: “No, no, no, no, no. But I think what you didn’t appreciate about that one– Go back. Go back to the beginning. We got five hours.” No, I’m almost positive somebody in the car would have asked me because I do not offer that up. Yeah. You don’t believe me. All right, well, just carry on.

SASHEER: I want to go back to what you said about, like, “our friendship has a purpose.”

PENN: Oh, what do I mean?

SASHEER: Yeah.

PENN: Well, I mean, first of all we run a production company together and we have this podcast together, Podcrushed. And I just think that the reason that we’ve continued hanging out and working together is because it’s always had actually quite an explicit purpose–to make something of meaning. We started early on talking about a script that she was conceptualizing, and that was about her experience as a middle school director. She was not quite a teacher, but she was a director and kind of almost like a vice principal. And I was just fascinated. Like, she comes from a background where she’s so professional and competent in a way that I’ve never had to be. And I’m very professional and competent in my craft. But what it does not require is, like, organization and that sort of real-world kind of competency and responsibility. You know, you could say there’s a lot of responsibility on your shoulders if you’re, like, on camera and lifting up a show or whatever. Okay, fine. But I’m comfortable doing that. There’s stuff like being a director of a charter school or, like, working in an organization at the UN. That kind of professionalism–I’ve always just been like, “Wow.” And I really wanted to do something meaningful in media like make things of substance. And I just felt like this was… I feel like when she first started talking about this script and she was coming from no background in media, I was just like, “I’ve been working with showrunners and people in TV and film most of my life, really. The second she gets some experience, I know she can do that. And she should do that. She’s the kind of person who should do that. There aren’t enough people who are doing that.” And so that was kind of just the initial outset of us having, I think, any conversations past these gatherings where, you know, we were just amongst other friends. Does that make sense?

NICOLE: Yeah. Okay. So, what is your favorite thing about your friend?

PENN: I would say I just have a real respect and admiration for her, for her mind, and for her soul. Again, it’s this thing of purpose. It seems like everything she’s done since she was able to be out in the world, making her own choices–she means it. She, like, does good things and means them. And that’s a really incredible thing. She’s incredibly consistent. You know what I mean? And she’s extremely honest. Like, if you’re reflecting on something that you’ve done together–let’s say it’s writing something or whatever it is… She actually describes herself as a word she uses–which I wouldn’t quite use–but it’s “ruthless.” And it gets there a little bit. But the more you get to know her, I don’t think it’s jarring or in any way negative because she’s so principled. And so therefore that kind of honesty and transparency, I think, is just a great thing.

SASHEER: I love that. If you could guess, what do you think Nava’s favorite thing is about you?

PENN: Well, it depends on which kind of… You know, there’s the flippant, funny things, and there’s the real things. She’s said on several occasions that she thinks that one of the things that’s best about me is that I’m “generous”?

SASHEER: You don’t like that?

NICOLE: That was very quizzical. “Generous?”

PENN: I’m a miser. I’m really just tight! No. The reason I remember this is because I’m like, “Oh, of all the things that I think are great about me, that’s not one of the things that I would have thought of.” And that stuck out, you know? And it’s kind of nice when people can reflect back to you something maybe you don’t see as much about yourself. Yeah. I’ll go with that.

NICOLE: All right. What is something that you do that drives Nava crazy?

PENN: Oh, probably my lack of responsiveness on text. That’s got to be number one. I mean, that’s got to be it. There’s a number of things. But I would say that’s number one probably.

NICOLE: And do you just look at the text and go, “Ooh, I’ll just do it later”? Or you don’t have alerts, or you don’t look at your phone?

PENN: It’s a confluence of things.

NICOLE: Ooh, that’s a good word.

PENN: I’d say over the last year it has been genuine, like, maxed out bandwidth. And if there’s anybody I’m responding to, she’s in the top, you know, five. It’s just, like, between having a kid and… When I work on this show, it’s a really, really full-on kind of thing because I’m in, like, every scene. And I directed an episode this season. So, it’s just full, full, full-on. And she’s pretty understanding.

NICOLE: Wait, how many episodes do we get?

PENN: Ten. But I directed one. I directed one episode.

NICOLE: Oooh, fun, fun, fun.

PENN: And then also this Do Not Disturb function now that everybody gets to use. I just leave that thing on for 37 hours.

SASHEER: Yeah, I’ve been seeing that where it’s like, “So-and-so silenced their phone.” But is it like, “Do Not Disturb”? Or is it just putting their phone on silent?

PENN: No, it’s Do Not Disturb.

NICOLE: It’s Do Not Disturb. So, you don’t get alerted. There’s no vibration. You don’t get phone calls. But then it’ll just show you that someone called or someone texted. You have to, like, look for it.

PENN: I used to put my phone on Airplane a lot, and then I realized–I don’t know–that I was maybe too disconnected.

NICOLE: Well, yeah, because then it just goes straight to voicemail. Even the texts–you don’t get them till way, way later.

PENN: I heard you guys talking about leaving each other voicemails. See, nobody that I know leaves voicemails anymore really.

NICOLE: Oh, I love a voicemail. Her mailbox is currently full and is not receiving any more messages.

SASHEER: It’s full because it’s full of your voicemails.

PENN: What about voice notes? Do you use voice…? Do you know what I mean?

SASHEER: Sometimes.

NICOLE: I had to resort to that because I need to say things sometimes.

PENN: Another podcast. You need another podcast.

SASHEER: True. She has so much to say. She has 16 podcasts. She has a message to give. Okay. What is something that Nava does that drives you crazy?

PENN: See, she’s on the opposite end of something with responsiveness. I think when she was working with the UN they had, like, a three-hour kind of window that they needed to reply to, like, all things. You know, there was rigor there. And sometimes I’m just like, “Damn, I mean, come on. Hey, what were we going to do if we didn’t have phones, guys? People used to go to war, you know what I mean? They didn’t hear from each other for months. Family members.” I suppose we balance each other out in that sense–one would hope.

SASHEER: That’s a funny thing to think about. Yeah. How did everyone know when we were going to war?

PENN: And if you were on Do Not Disturb, did you get drafted? That’s so weird. That’s not really a great joke, but…

SASHEER: The government was like, “Notify anyway.”

NICOLE: Okay, Penn. Which of you would do better on the TV show Survivor?

PENN: I think I’m the easy answer. But I think upon further investigation, it could be her. I mean, you know what? She’s actually… So, if we’re talking about, like, hanging out in the woods, I think I’m a little more built for that. But if we’re talking about competing, I think she’s very competitive. She’s, like, quietly very competitive, I think. And I’m not. Like, if I’m engaged in a competition, I start to shut down. And I just like, “Fine. You can have it. Whatever. It’s fine. It’s really okay.”

NICOLE: You don’t like to win?

PENN: I think the concept of losing is, like, incapacitating for me or intimidating to me. So, I just sort of opt out of the competition, you know what I mean? I love a bit of sportsmanship between men. I could play a friendly game or something. But I think there’s a threshold beyond which I’m like, “Whoa, whoa, whoa.” But I think Nava is actually quite competitive.

SASHEER: That makes sense. I like that. All right. We’ve reached the end. What do you hope you’re both doing 20 years from now?

PENN: Well, you know, the good answer would be we’re making things. We’re making content. We’re making movies, making shows, making things– Podcasts. Well, do you think podcasts will still be a thing?

SASHEER: It’s been longer than I thought it would be.

NICOLE: I think so, yeah.

PENN: Yeah. I mean, because we started out to do something of real purpose… And it’s not in terms of scale–just in terms of meaning and substance. I hope we’re still making things, you know? The thing is when you work together… We’ve been friends for a short period of time–six years or so–but then, like, working together for just about three. But you know, when you’re working together, different things happen. And we’ve really been friends for that period of time mostly; that’s where our real relationship has been. And I think the things that we’ve gone through so far–we could probably go through a lot more things. And if we don’t have a company, I’d like to say that we learned a lot and we just have mad respect for one another and our kids hang out. You know what I mean?

NICOLE: Yeah, I like that.

SASHEER: I like that, too.

NICOLE: Okay, now we’re going to bring Nava back. And we’re going to compare these–

PENN: You compare notes?

NICOLE: Yes. And then you guys log off and decide whether you continue.

PENN: We’ll debrief. So, do you, like, paraphrase what we said, or do you play it back?

NICOLE: It’s paraphrased. Sasheer and I will read it. And you can add if you want.

PENN: Okay. This is the fun part.

SASHEER: The whole thing’s been the fun part.

NICOLE: No, no. This part is the fun part, where we get to see how right or wrong you are about each other. And so, the first question we asked was, how did you two meet? Nava said you met in New York City in her apartment. Penn was consulting with Nava’s roommate, Martha–who he was very good friends with at the time–whether he should take the job on You. And they would also see each other around while working in a faith youth group. Penn said– Do you want to do this one, Sasheer?

SASHEER: Oh, we’ve never done that before.

NICOLE: We haven’t? This is a fun thing about me. I’ll never remember how we do anything. Penn said he met Nava in her apartment. He went to see her roommate, Martha.

PENN: Ding, ding, ding, ding, ding!

NICOLE: And he was having an intense convo with Martha about taking You. And then Martha and Nava would host Meaningful Conversations in their apartment that he would attend. So, you guys got that one right.

SASHEER: Yes.

NAVA: Woohoo.

PENN: All right. One for one.

SASHEER: Next, we asked, “What’s your favorite memory of traveling together?” And you both talked about the road trip that you took to this conference. But Nava also talked about the half day that you had together in London during your biannual retreat. And you went to a park. You went to a marketplace together in Notting Hill. Penn described the road trip with more detail, saying that Nava played music from The 1975. He played his old music. He swears that someone asked him to play it. We’re not quite sure if that’s true or not.

NAVA: That’s right. Yeah.

PENN: Is that true? Isn’t that true? Wasn’t it The 1975?

NAVA: It was. But that was our trip in DC with Ryan. I don’t think that was Rhode Island because remember the one to Maine–we were also sad? I was sad about, like, a heartbreak. You and Domino… Yeah, yeah, yeah. That was a lot.

PENN: That really… No. So, when we went to DC, that was actually a really fun trip. Neither of us mentioned that.

NAVA: Can we change our answer?

PENN: That was the most fun trip. Nava, do you remember that–? The most memorable moment was when we were all talking about aliens. And we’re, like, walking just on the street at night, and Ryan goes, “Guys, you know the best thing about aliens?” And then we look at him, and he’s just like, “What do you think they’re doing right now?” And then he does that thing where you put your hands on your knees and then you cross them back and forth. He just did this dance. And then we just watched him do this dance.

NAVA: And we, like, lost it because it was so random. Yes! I think we both changed our answer. That was the best one. And that’s when he played Mother and I played The 1975.

SASHEER: Oh, I love that.

NICOLE: I love that, too. “What do you think aliens are doing right now?” Just dancing.

SASHEER: Just dancing.

PENN: Just dancing. It was a very human dance–obviously a human dance from the early ’90s.

NICOLE: The next question we asked was, what’s your favorite thing about your friend? Nava said, “Penn is super generous and giving. Also, he’s funny. Sometimes I’ll text him, ‘Hey, be funny today.’” Penn said he has a real respect and admiration for Nava’s mind and soul. She has a consistent, meaningful purpose. She’s direct. “‘Ruthless’ is the word she uses, which sounds a little harsh, but, you know, I think it’s good.”

NAVA: Aww. That’s so sweet.

SASHEER: We also asked, “What is your friend’s favorite thing about you?” And when we asked Nava, she said that Penn says Nava is the most straightforward person he’s ever met. And she’s like, “He might also hate that. I can’t tell.”

PENN: It’s a double-edged sword as any sword is.

SASHEER: Yeah. She reminds him when he doesn’t meet deadlines–

PENN: Which is virtually every single deadline I’ve ever looked at of any kind really.

SASHEER: Yeah. Both of you talked about how Hollywood has loose deadlines and loose timelines.

PENN: I was raised in the jungle! I was raised in the shadows… Super loose, you know?

SASHEER: And then Penn said that Nava thinks that Penn is very generous. That’s something that he would not put on his own list of things that he sees as good qualities about himself, but he likes that you said that.

NICOLE: Then we asked, “What’s something you do that drives your friend crazy?” Nava said that she persistently calls, texts, and is very direct with Penn. Penn says that she can, you know, sugarcoat things sometimes. Penn said his lack of responsiveness to texts.

PENN: But you look at it as, like, the percentage is bad because of the persistence, but I’d say it’s still regular because of the persistence. So, you know what I mean?

NAVA: If you just responded the first time, there’d be no persistence.

PENN: Yeah, that’s true.

SASHEER: I also wonder if this would be… Well, I was gonna say, “I wonder if this would be an issue if you guys weren’t working together.”

PENN: Yeah. No, I mean, that’s what I said at some point. I was like, “You know, a working relationship is an added full dimension.” When you’re just hanging out–whatever–that’s its own thing. But we’re trying to make moves–trying to make money! It’s a capitalist system! What do you expect?

NAVA: Penn has literally never said that. And actually, I would say that we’re doing the opposite. We, like, turned down lucrative opportunities like, “Well, let’s just do this other thing where we don’t make any money.”

PENN: Don’t tell people that. Tell people that we are out here making cash.

SASHEER: We asked, “Which of you would do better on the TV show Survivor?” Nava said, “Penn. He’s the famous rich one, but he’s better at the nature stuff.” But Nava does believe that she would be diplomatic and keep a secret.

PENN: How does that work on Survivor?

SASHEER: Because there’s, like, conniving strategy that happens.

PENN: Diplomacy?

NICOLE: Yeah.

PENN: Okay.

NICOLE: And you have to, like, do alliances and stuff.

PENN: Wow.

NICOLE: We don’t actually know. We’ve never seen an episode.

SASHEER: We’ve gathered information from what other people have said about Survivor. We just like this question a lot even though we don’t know much about Survivor.

PENN: I like that. I like that honesty.

SASHEER: And then Penn actually said basically the same thing. He’s built for the woods, but Nava is very competitive.

NAVA: That’s funny.

SASHEER: Do you agree?

PENN: See, I don’t experience her competitiveness as a friend. I just feel like you’ve said that you’re very competitive.

NAVA: Yeah, I think I’m different. Yeah, I’m not, like, athletic at all. I just have the feelings of someone who is. Like, I want to be competing, but I will always lose. But I’m, like, hurt by it even though it’s very predictable if that makes sense.

NICOLE: I think we skipped one. “What’s something your friend does that drives you crazy?” Nava said, “Penn ignores my texts. He never uses emojis and exclamation marks.”

SASHEER: You gotta beef up those social graces.

PENN: That’s so true. No, you know what I did, though? On her birthday, I sent her a bunch of emojis and then with, like, a laser effect. I was just, like, really laying it on thick.

NAVA: It was appreciated.

NICOLE: That’s pretty funny because, like, I love that kind of stuff. So, I’d be like, “Well, this is the new standard!”

SASHEER: “I guess we’re always doing lasers now.”

NICOLE: And then Penn said that she’s the opposite of Penn’s responsiveness. Yes, yes, yes. Okay. Now, the final question, Sasheer.

SASHEER: Okay. We asked, “What do you hope you’re both doing 20 years from now?” And Nava says that she hopes Penn is an award-winning director and he gets to star in a superhero franchise.

PENN: 40 years of superhero franchises.

SASHEER: Yeah. She hopes that he has one more kid and one of his kids is a great classical musician and that Penn becomes a professor at USC.

PENN: Wow. Oh, you went in deep. Thank you. I was very general.

NAVA: We know who the better friend is.

SASHEER: And Nava hopes for herself that she’s married, has a family, and is a good neighbor. And she hopes that your production company is successful and that you’re doing movies and TV shows that show a brighter side of human nature. And then Penn said that he hopes that you’re making movies and content, TV shows, podcasts, and that sort of thing and that if the company isn’t a thing, that you still have respect for each other and that you’re still friends and your kids still hang out and you’re in each other’s lives. And I think that’s nice. So honestly, I think you guys did a really good job.

PENN: We passed?

NICOLE: I think you did a really good job as well. You passed with flying colors. I personally think your friendship can continue.

PENN: Has anybody ever failed?

SASHEER: No one’s ever failed. No.

PENN: If they did, would you tell them?

NICOLE: I absolutely would be like, “You’ve never met before.”

SASHEER: “Why did you agree to do this show?”

PENN: “What are you here to promote? You have never even met! What superhero franchise are you a part of? How have we been tricked? Marvel? Ugh.”

NAVA: Penn, I can’t believe you didn’t wish for me to be married in 20 years.

PENN: I did! No, I said “kids.” No, she broke up. She said that I said for our kids to be hanging out.

NAVA: Oh, okay. Okay. I was going to say, “Come on, man! Come on.”

NICOLE: Nava, I love that. “Why didn’t you say I’d be married? That’s what I want!”

SASHEER: “Don’t you want me to be married?”

NAVA: “Don’t not manifest that for me.” I’m also constantly asking Penn to set me up with someone, and he never has!

PENN: Hold on. Hold on. First of all, it’s been a long pandemic, guys. I’m also not a matchmaker. I don’t think I’ve ever… There’s one friend. And I would like to be. But, you know, I’m not good at it. I’m not good at it.

NICOLE: That’s what everyone says who’s with someone. They’re like, “I couldn’t possibly.” I was like, “Well, how did you get what you have?”

NAVA: Exactly.

NICOLE: I identify with you, Nava.

NAVA: Thanks, Nicole.

NICOLE: Once Sasheer asked me, “What’s the first thing I would see if I could time travel?” And I was like, “I’d go see who my husband is!”

NAVA: I love that!

SASHEER: She was like, “That’s the first thing you would do?” I was like, “Oh. Um… I guess see other stuff, too.”

NICOLE: “Uh… Kill Hitler! Kill Hitler.”

SASHEER: Yeah, I was like, “You’re not gonna save something in history or, like, look at where we are as a society. You’re gonna go find your husband?”

NICOLE: “I gotta go see him. What does he look like? Is he nice?”

SASHEER: You guys should listen to the episode back because you both said really nice things about each other that we didn’t repeat. But you guys clearly love each other, and that’s very sweet.

NAVA: So sweet. Thank you. We should bring you guys onto our podcast if you’re open to it.

SASHEER: Absolutely.

PENN: If you’re open to it. No pressure. See, Nava always puts pressure on it. Guys, it’s okay. You don’t have to do it.

SASHEER: “This is recording. Promise me you’re going to do it.”

PENN: This is on record. We’re live tweeting this interview.

SASHEER: Well, what are you guys working on next with your company? What’s happening?

PENN: So, when you’re trying to really make things, you’re making a lot of things at the same time to see if anything sticks, you know what I mean? So, there’s quite a list. Nava actually just recently came with a really great idea that I can’t mention.

NAVA: Yeah, if you say that, I will actually kill you.

PENN: Yeah. So, she just came up with a really great idea. We’ll see.

NICOLE: Well, now I want to know!

SASHEER: Can’t wait to see it.

PENN: Yeah. You’ll just have to wait about seven years, probably.

NAVA: When you come on our podcast, I’ll tell you our thing.

NICOLE: Ooh, okay.

PENN: See? She’s a negotiator.

NICOLE: I was like, “Well, now we have to set that up because I would like to know!” Nava, you’re very good.

PENN: We would actually love to have you on.

NAVA: But we have, like, a couple of independent films and a kids family series that are the most immediate things in the works.

NICOLE: That’s fun. I love that. Yeah, I like your friendship. It seems really nice and chill. Sasheer said “loving,” and I agree.

NAVA: Thank you.

PENN: It’s many things. You know, “chill” is not the word I’d use.

SASHEER: He’s like, “I’m not feeling the chill energy in here.”

NAVA: I think if you take the company out of it, it would be. Like, when we were friends for three years before–yeah.

PENN: Completely. No, totally chill. It’s just that what we’ve been trying to do with this company is, like, the least chill thing, which is, like, succeed in a cutthroat industry and try to make something of substance. And so, we’re always… I think when we laugh the most is when we’re talking about, like, if we were just cool with buying into the whole just nihilism sheen of, you know, the Hollywood moviemaking industry. There’s so many just, like, out of left field, crazy, dumb ideas that we know would sell. And so, we, like, just laugh about the crazy things we could pitch that people would be like, “Huh. Tell me more.” Whereas we’re like, “Now, here’s something we want to do. We want to make something that’s, like, morals and principles for children.” People are like, “You know, that sounds great, but… It’s a tough, tough business out there.”

NAVA: I won’t say who. I won’t say which network. But the very first pitch meeting Penn and I ever had, we took two concepts: a family show and, like, a strictly kid show. And the kid’s show was, like, educational–no two ways around it. And we didn’t take it to PBS, which we should have. And so, the very first meeting we had, someone in a very senior position who was there for the kids pitch, I guess, hadn’t read the brief on what the concept was but took the meeting and was making a joke about how, in their network, they never make anything educational. And he was like, “If you have something educational, you take that shit to PBS. Don’t bring it here.” And literally right after that, he was like, “All right, what did you guys bring us?” And we all– I think there was five of us on the team. We all looked at each other like, “What do we do?” It was such a, like, “wow.” Yeah. And needless to say, it did not sell.

NICOLE: How wild. That executive is nuts. Some of them are truly–

PENN: Well, he was just honest.

NAVA: He was honest. Yeah.

PENN: He was just being honest.

SASHEER: “We do just like smart kids. We want them dumb.”

NICOLE: “We want dummies!”

SASHEER: “We don’t want them learning anything.”

NAVA: It was funny.

SASHEER: Can you talk about the conception of Podcrushed?

NAVA: Yeah. Penn, you want to take that one? I feel like I always answer that one.

PENN: Sure. Yeah. You’re really good. So, Nava’s also incredible– Because of the work she’s done, she’ll hear, like, 17 different perspectives and then summarize them all and everybody’s like, “Yeah. Yeah, that is what I said. Yeah. That was really good.” So, she’s just really good at summarizing even ideas that I come up with. And then I’m like, “Nava, you get that? Yeah, you pitch that.” So Podcrushed basically is… See this? I’m already like, “Hmm. What am I doing all of my extra time with?” It’s about middle school. Like, we’re telling middle school stories, and we’re using those as a portal to, like, actually really meaningful conversations just about all things–often identity and just a lot of what that incorporates. But, you know, in the beginning we had, like, these user-submitted stories. We’d start with those, and I narrate them. But we’ve now put them at the end because people are here for the celebrity interviews, you know what I mean? But they’re still there. And they’re still good. And we have a few animated clues to go along with them. Like I was saying, some of our earliest conversations were about this age period and how meaningful it is for people in their lives in just forming who they are–you know, 12 or 15 or around that. I mean, it was Nava’s idea. She had this idea that she basically had heard somebody’s middle school story and just basically was just dying laughing, I guess. Nava was in tears. And her gut reaction was, like, “What if there was a podcast where you just had people submitting some of their cringiest, worst, or most embarrassing stories from school?” And that was really the germ of it. And then she told me about it. I was third in line, too. She went to sour friend Sophie and David because Sophie animates and David makes music. And she was just thinking it was going to be this, like, small little podcast and not the giant success that it is now–the juggernaut that need not be named because of its omnipresence now. But, you know, the second somebody like me gets involved in something it kind of shifts things. So, she mentioned it to me. I thought, “Oh, that’s cool.” And then I wanted to contribute in some way. We talked about me maybe narrating the stories. And then eventually I became a host of the thing. And then because I have reps, they all wanted to be involved.

NAVA: And then eventually it’s just like, “It’s Penn Badgley’s podcast!”

PENN: “Penn Badgley’s podcast about middle school with two people we–”

NAVA: “Have never heard of, who bring down his value…”

PENN: So that’s the genesis of Podcrushed. You know, I think what’s cool is that, like, when you guys come on, for instance, you’ll see that it’s… I think it is uplifting. I think we have really uplifting conversations. That’s something that we’ve wanted to do since we met. You know, to me, we’ve been exploring the dark side of things for a while. And there was a point in time where that was really brave and new and interesting. And I think it’s maybe just not as new and interesting as it used to be. And so, to make something that is uplifting but also mature and complex–I think that’s something we see less of. And, you know, that’s what we’re trying to do.

SASHEER: Well, I can’t wait to do it.

NICOLE: Yeah. I’m excited. O

SASHEER: Well, thank you so much for being on this show! This was so wonderful to hear about the work that you’re doing together and your friendship.

NAVA: Thank you. Thanks so much for having us. This was so fun.

NICOLE: Well, that’s it. Bye-bye!

PENN: Bye!

NAVA: Bye.

SASHEER: Bye!