Phoebe Robinson Is Done Being a Girl Boss

Summary

Good One: A Podcast About Jokes

Episode: Phoebe Robinson Is Done Being a Girl Boss

Host: Jesse David Fox
Guest: Phoebe Robinson
Date: October 16, 2025

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Episode Overview

In this episode, Jesse David Fox sits down with comedian, writer, and producer Phoebe Robinson to delve into her new YouTube special, "I Don’t Wanna Work Anymore," and her journey from self-proclaimed "girl boss" to a more content, self-aware creative. The conversation is wide-ranging, covering Phoebe’s standup origins, reflections on hustle culture, lessons from her time as a boss, the impact of 2 Dope Queens, personal relationships, and the current state of comedy and podcasting.

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Key Discussion Points & Insights

1. Standup, Validation, and Ambition

• Phoebe reflects on her changing relationship to standup:

  “I think I needed standup in a way that I don’t need it now. And I think a lot of it was the sort of, like, external validation...Now I’m in a much more peaceful place where it’s like, I know I’m funny.” (00:40)

• Standup as initial identity: Phoebe describes how, early on, the grind and hustle culture felt normal and was “just a part of the culture” growing up and starting out in New York. (07:06)

2. The "Girl Boss" Reckoning

• Departing from the ‘girl boss’ identity

  “I’m 39, and I don’t want to be a girl boss anymore.” (06:19)

  • Phoebe shares how the girl boss era rooted in the early aughts encouraged overwork, especially for women of color feeling pressure to be twice as good.
  • Tina Fey’s “Bossypants” is cited as a key text that made bosshood appealing and accessible for women in comedy. (08:35–09:38)

3. The Cost of Hustle and Work-Life Balance

• Personal impacts of workaholism:
  – Phoebe looks back at times when her sense of worth was deeply intertwined with professional results, especially during the COVID-19 pandemic.
  – Therapy and introspection have helped her focus on a fuller life:

  “During COVID...I was 100% a workaholic...Now I’m like, there should be layers to my life...I went into therapy and had to do the work on that.” (26:19–27:38)

• The myth of hustling for fulfillment:

  “We were sort of, like, sold a bill of goods that this was going to set us free...We’re just all tired.” (14:35)

4. On Being a Boss

• Positive lesson:

  “I learned about being a boss is it requires a lot of different parts of you...vulnerability, tenderness...those things are feminine qualities and not celebrated as boss attributes. And I think a lot of them actually are.” (23:59–24:58)

• Hardest part:

  “Learning how to fire people...As a Libra, Scorpio moon and Pisces rising, I never want to be the bearer of bad news.” (24:59–25:49)

5. The Burnout and Anti-"Content" Stance

• Treadmill of productivity:

  “It was like a treadmill that you could not get off…I can’t slow down...if I stop, what happens?” (30:49–32:13)

• Exhaustion and boundaries: Her experiences dovetailed with the decline of "girl boss" as an aspirational brand and the rise of creative burnout.

• Phoebe’s anti-content sentiment:

  “Which is why I’m just so anti-content these days. Because I just don’t think that that is how you make good things.” (31:47)

6. Blending Writing and Performing

• Writer first:

  “I think I’m a writer first...I just love language so much. Any comic does.” (18:22–19:58)

  • Phoebe’s distinctive voice carries from her books to her standup.

7. Relationships, Breakups, and Parasocial Dynamics

• Being publicly in a relationship:
  – On her breakup and how the public processed it:

  “Even when we broke up and people were like, ‘You guys broke up?’ I go, I don’t know you, why you thought…I was going to DM every person who follows me and say, ‘I broke up.’” (33:16)

• Standup preceding self-awareness:
  – Previous jokes about her ex contained truths she didn’t fully process until later.
  – “I did love this guy...But in this latest special, it is me taking stock of, like, this person was kind of a hot mess and I was carrying him for too long.” (35:28–38:05)

• Buying her ex teeth (‘reverse colonizing’) and comedic self-deprecation
  – Memorable joke and listener resonance:

  “I bought it. So listen, I wouldn’t do that again...it was a good lesson to learn.” (38:08)

8. On Michelle Obama, Being Starstruck, and the Arena Tour

• Hosting for Michelle Obama and the joke about not farting in front of her:

  “I just held it in till I got back to my hotel room...just the longest fart into my toilet bowl.” (39:41–40:34)

• Responding to Bill Burr’s comments on Michelle Obama’s book tour:

  “I just find it interesting how easily men dismiss the contributions of women if it’s not tied to money...that is work.” (41:44–42:48)

9. Podcasting and the Shift in the Comedy Landscape

• Phoebe and the podcasting boom:

  “Everyone has a microphone...Most of these opinions are ass...You need to take a test before you can have a podcast.” (43:05–45:05)

• Intentionality behind 2 Dope Queens:
  – Started as a live show in 2015 at UCB East, grew organically with intention to spotlight overlooked talent, especially women and comics of color. (46:21–49:13) – Phoebe takes pride in how 2 Dope Queens opened doors:

  “It should be a platform for people who I think are brilliant and don’t have as much attention as they should.” (50:25)

• Relationship with Jessica Williams now:

  “We’re both, like, on our grind...But I have nothing but positive feelings.” (51:30)

10. The Comedy Industry’s Current State

• Cultural change and industry fear:

  “People are scared...They don’t want to do creatively left-of-center things.” (52:02) – Phoebe bemoans streaming culture’s impact and the pressure for continual output.

11. Contentment Over Success

• Redefining ambition:

  “If I don’t want to be a girl boss, what do I want to be? I want to be content.” (58:49)

• Pride and reframing independence:
  – Phoebe is proud of her self-reliance (buying her own apartment) and the impact of her book imprint, Tiny Reparations. (55:31–57:57)

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Notable Quotes & Memorable Moments

• “I matched with this guy Kristoff in Berlin...He pulls out his phone to check the rate of the Westin Grand Berlin...This was in the first seven minutes. I’m just like, even if you’re like, ‘Wow, she’s fancy’, keep it on the inside!” – Phoebe (01:38–04:11)
• “If Michelle [Obama] can respond within five minutes, these dudes taking hours? Absolutely not.” – Phoebe (40:49)
• “I’m so voice driven I wouldn’t want to steal anyone else’s joke. But I love watching comics who are totally different from me, like Tig Notaro.” – Phoebe (67:11)
• “Lazy crowd work...If you aren’t going to put the effort in to the time you’re spending at your job, you are essentially wasting your time.” – Phoebe (71:48)
• “What I love about standup is it’s so much like life...It’s not focusing on, I gotta kill, it’s the process of doing it and figuring out what you learn about yourself.” – Phoebe (77:40)
• “Enough of this content. Enough of every year I gotta have a new hour. No, you don’t. Let us miss you. Let us fucking not hear from you for nine months. It’s great.” – Phoebe (77:40–79:29)

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Timestamps for Key Segments

• On validation and outgrowing hustle: 00:40–01:11
• Defining ‘girl boss’ and its history: 06:19–09:38
• Impact of COVID and work addiction: 26:19–27:38
• Advice for bosses: 23:49–24:58
• Content burnout—‘treadmill you can’t get off’: 30:49–32:13
• Public relationships and breakups in standup: 33:16–38:05
• Podcasting and 2 Dope Queens’ origins: 43:05–49:13
• Reflections on the industry now: 52:02–53:51
• Contentment over ambition: 58:49–60:26

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The Laughing Round (Q&A Lightning Round Highlights)

• Comedic influences: Janine Garofalo, Patrice O’Neal, Chris Rock, Wanda Sykes, Bill Burr (64:47)
• Best time you bombed: “Did standup between stripper acts. The men did not want to hear a woman talk. But it’s worth doing those shows…Now, if I have a bad show, it doesn’t faze me.” (74:45–77:40)
• Favorite YouTube song (funniest): “Vertigo—because they just count Spanish incorrectly!” (70:49–71:19)
• Comedy pet peeves: Lazy crowd work, content for content’s sake, lack of intentionality. (71:48–73:55)
• On allowing yourself to fail: “You don’t get good by always being good. What is that? Doesn’t make any sense.” (79:29)

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Episode Takeaways

Phoebe Robinson provides a candid, hilarious, and introspective look at shedding the “girl boss” identity, choosing fulfillment and intentionality over external validation and hustle culture. She reflects on her pioneering work with 2 Dope Queens, her evolution as a performer and boss, and her desire for the comedy industry to slow down and value quality over quantity. Throughout, her distinctive comedic voice and commitment to honesty, both with herself and her audience, stand out.

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For listeners new and old, Phoebe’s episode is a rich exploration of ambition, authenticity, and the cost of keeping up with culture’s relentless pace. It’s both a love letter to standup and a rallying cry for contentment and intentional creation.

Transcript

[Phoebe Robinson]

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[Phoebe Robinson]

I think I needed standup in a way that I don't need it now. And I think a lot of it was the sort of like, external validation of like, oh, I'm on the right path. I'm doing this thing. I am funny, I can do this and I work twice as hard to get this thing and blah, blah, blah. And I think a lot of that fueled my ambition. And now I'm in a much more peaceful place where it's like, I know I'm funny.

[Jesse David Fox]

This is good one. I am Jesse David Fox, senior writer, Vulture and author of Comedy Book. My guest today is Phoebe Robinson. We talk about her new YouTube special, I don't Wanna Work Anymore. And being a recovering girl boss, we also discuss which is harder, texting Michelle Obama or not farting in front of Michelle Obama. So here is Phoebe Robinson. I'm here with Phoebe Robinson. Thank you for joining me. So what is the funniest thing that happened to you this week?

[Phoebe Robinson]

Gosh. Okay, so I was in Berlin running the Berlin marathon. Not to brag, but I am an athlete, an unpaid one. And I would like a sponsorship and one. Nike Asics.

[Jesse David Fox]

You want and you want an and one. They're gonna restart the company.

[Phoebe Robinson]

Yeah, but I was, I was on, I was in Berlin and I was, you know, I'm on these streets, I'm single. And I was like, I'll. I've never, like, done a dating app overseas. So I was like, okay, let's see what's going on, Bumble. So I matched with this guy, Kristoff. He was very nice. I mean, of course that's his name. He was 41. Super nice. We texted a little bit and I was like, let's like, you know, he, he was texting me about something. I go, so when are you going to call me so I can make sure that the vibe is right? And he called Immediately. And I'm not going to lie, that did kind of make me hard. I was like. I was like, okay, he likes direction. So I was like, this is cute. So lovely. Phone call. We go out for a day, meet up for a kebab, and then we, like, grab a drink. But he was just like, oh, I hope this, like, wasn't, like, too difficult to get to. And I was like, oh, no, no worries. I took an Uber. I'm staying at the Westin Grand Berlin. And he was like, you stand at the West End. And I was like, yeah. And he was like, that's like, a really nice hotel. And I was like. Because, like, I like, listen, I love a Westin. Thank you so much for the Marriott Bonvoy points. But, like, he was acting like I stayed at the Ritz.

[Jesse David Fox]

Yeah, yeah, yeah.

[Phoebe Robinson]

Or the Four Seasons. I was like, oh, yeah, yeah, I guess. Yeah, yeah, my room is fine. And he goes, the. The west in Grand Berlin. And I was like, yeah, yeah. And he was like, I feel like I've been to, like, a. A business conference there. I was like, okay. So anyway, I'm, like, trying to talk. And he pulls out his phone to check the rate of the Weston Grand Berlin.

[Jesse David Fox]

Mm.

[Phoebe Robinson]

And he goes, yeah, that is a nice hotel. And I go, well, this is a series wrap on Kristoff. Please return your clothes to wardrobe. Literally, this was it, Jesse. This was in the first seven minutes. And I'm just like, even if you're like, wow, this chick is fancy. Keep it on the inside. Okay. And then, like, Google at home. But to pull out your phone to check the rate of the hotel I'm.

[Jesse David Fox]

Staying at, it would be literally, like, you go over to a friend's place and look up how much that place costs.

[Phoebe Robinson]

Yeah.

[Jesse David Fox]

In front of them. Yeah. Not when you go home, like everybody else would.

[Phoebe Robinson]

It's too much.

[Jesse David Fox]

It's too much.

[Phoebe Robinson]

Have you been to the Western Grand Berlin? Has anyone been to Not. It is fine. They have, like, a little robot cleaners on the. The carpet.

[Jesse David Fox]

That's what it is.

[Phoebe Robinson]

But I was like, girl, you gotta. Men are very stressed out. That's what I've noticed. Men are stressed and straight. Straight single guys are stressed.

[Jesse David Fox]

Maybe it's a German thing. Maybe all the German. German. Maybe all the German people are going to sound off in the comments being like, literally. That's a famous German tradition to look up the rates of rooms if you meet people.

[Phoebe Robinson]

It was just so wild. So I was like, yeah, this date is over. And then he was like. He was Like, I looked you up and he's like, I read your Wikipedia. I'm like, I'm not like, this isn't a Gotcha, Kristoff. What the is going on?

[Jesse David Fox]

And it's Christoph Waltz.

[Phoebe Robinson]

No, it was. If it was Christoph Waltz, I would. I would have been fine with it because he'd be paying for my life.

[Jesse David Fox]

Yeah.

[Phoebe Robinson]

I would stop working.

[Jesse David Fox]

The entire story is imagining it being Christoph Waltz, at least, because I. His voice is so distinct.

[Phoebe Robinson]

I know. We love a little Chris. What is he doing these days? What's going on?

[Jesse David Fox]

I just saw he was around. He is in something.

[Phoebe Robinson]

Okay.

[Jesse David Fox]

I love that he's working in something, because I was like, great. Can I reach out to Christoph Waltz? He's in something.

[Phoebe Robinson]

You can reach out to him.

[Jesse David Fox]

No, Like, I was like, oh, maybe I can have Kristoff Waltz on the podcast 100. And then he wasn't in New York press doing press for whatever the thing he currently is in.

[Phoebe Robinson]

Got it. Well, Kristoff Waltz, if you're listening, if you have any single friends, let me. Because he's married with kids. Right. I could pull up my phone, but my phone's on airplane mode because I respect podcasts. Okay. Are you happy I'm here?

[Jesse David Fox]

Yeah. I'm so happy. I'm excited to see you.

[Phoebe Robinson]

I'm excited to see you too. It's been so long since the standup show that we did. Yeah, the Padma Lakshmi show. Yeah.

[Jesse David Fox]

So the special opens, and you say, I'm 39, and I don't want to be a girl boss anymore.

[Phoebe Robinson]

I don't.

[Jesse David Fox]

And I want to really unpack this, because I feel like the last few years, girl bosses and inspiring girl bosses are having a reckoning with themselves being like, what is this thing that I sign up to do? And I. And I you. It's really the backbone of the special, so I really want to get a sense of it. So I want to start at the beginning, because I feel like there are young people who, like, literally only have heard the girl. That term girl boss as, like, like a joke. And not knowing that, like, for a while, people were, like, out here aspiring to be bosses that are women. Do you remember when you first, like, heard or conceived of the concept, regardless if you've heard of the term?

[Phoebe Robinson]

I mean, I was always. I just hit my lip. Is my lipstick okay?

[Jesse David Fox]

It's great.

[Phoebe Robinson]

Okay. Thank you. I mean, I always. I feel like my publicist, Beth, is like, what the is going on with. Oh, no, she's doing email. She's not listening. That's great. That's great. She's a Microsoft Outlook honey. I feel like I've always, I've gotten my work ethic from my parents and they were all like growing up, like, they were always like, you know, saying like, take a sense of pride in like what you do. And so I think even though I was a slacker in high school, I really found myself in college when I moved to New York, I went to Pratt Institute in Brooklyn. And so I really just always was very diligent about like your woman, your personal color. You just have to work super, super duper hard to get what you want. So I, I didn't. It didn't necessarily the girl bl. The girl boss thing didn't like click in my head. I just always held myself to the standard of like, you just have to work twice as hard to get anything. And also the early odds. Cuz I graduate 2006, that was just, that's like, wait, everyone was doing that. Everyone was on the grind. Everyone's hustling. Like it just was a part of the culture, you know what I mean? So it didn't feel, it just felt normal, if that makes sense. You're like, yeah, I'm doing this, I'm doing that, I'm doing this. I'm trying to get cashier, I'm trying to do this, go on vacation. Like, it just felt regular.

[Jesse David Fox]

I think the thing that I was thinking back on it, I feel like Tina Fey's book was like a real pivotal moment.

[Phoebe Robinson]

I loved her book.

[Jesse David Fox]

So good Bossy pants. And I feel like the idea of centralizing being a boss in terms of your personal narrative and to say nothing effect of like what it then did for comedy books, I feel like it really was like, oh, like being a boss and a woman is a thing that must be reckoned with. Do you remember reading it?

[Phoebe Robinson]

Yeah, it was a great book. I loved it. I remember I lent it out. I won't say who I lent it out to, but I never got the fucking book back.

[Jesse David Fox]

Are they famous now?

[Phoebe Robinson]

No, they're not famous. But I was like, okay. So I had to buy a second copy, but I did paperback because listen, the first time it was hardback. Tina has enough money, you know what I mean? Love it, girl. I'm tech of AIL for season two of four Seasons. So if you, you killed off Steve Carell, you could get me for a third of his. His pet. His rate. What is his rate per episode? 200. I would do, I would do 85,000. And my agents at UTA are like, bitch, why are you negotiating?

[Jesse David Fox]

You already talked yourself, talked yourself down.

[Phoebe Robinson]

Okay, no, I'll do for 125. Tina, thank you so much. But I loved her book. I thought it was so funny. It was so interesting. I, I, you know, when I was younger, I was definitely like, oh, I'm going to. My dream was like, to be in a power couple. Like, I just felt like, that's like so cool. Like, he's doing his thing, I'm doing my thing. So I think I was just always like, I like the idea of high achieving people who are charming. I used to be like, oh, I'm gonna, you know, be on Jay Leno. I'm like, have funny anecdotes about, like, my great husband. And now I have anecdotes about Kristoff. So how the mighty have fallen. But I, what I really did love about her book is that she made, you know, I think just being like, especially a woman in comedy and being like your own boss and being in charge of things, like, she just made it feel very appealing, very accessible, and very much like, if you work hard, you can achieve these things. Like, maybe you won't be the head writer of snl, but like, your version of that is possible for you. And not in like, you got this girl, but it was just like through like her life story. You're like, oh, yeah, I could do these things. I could take a stand up class, I could take an improv class. I could start my own blog. Like, I could be a self starter. I think was the main takeaway from her book that I absolutely love and cherish.

[Jesse David Fox]

And I feel like you were a self starter as soon as. Do you remember, like, you started doing comedy. I believe the story is that you went with a friend and then you're like, oh, this is like a thing for me. Did you remember how quickly you went from starting to doing it to being like, I now have ambitions through this art form?

[Phoebe Robinson]

Yeah. So I took a class at Caroline's on Broadway, RIP. This was 2008, I believe it was June or July and had so much fun. Did the class, did the graduation show. I was like, oh, this is really cool. And then October of 2008, this indie film company I was working at got shut down. The recession was just rough and I was just like, this is a sign from the universe. Like, I should just go all in on this. Like, I don't know what that means. Like, just get, you know, some day jobs like temping or whatever. And then it was Just like I was doing open mics, I was writing. I would, you know, I would go do like stand up at like, you know, biker bars in Staten Island. Go do Oprah, Micah, at like 11:00pm Like, I just became so obsessed with it and I became such a student. And this was back when Comedy Central, they used to air their old half hours in the morning. So I would like DVR them. I'm 41. This really, I. This is, this is harrowing for me to say dvr, but the sounds very old.

[Jesse David Fox]

But you watched it on Paramount.

[Phoebe Robinson]

Plus right after the Matlock reboot, that is what I did. I watch an episode of Mobland and then a gym gaffing in half hour. But no, I would watch all of those and I was like, that was great. And then I would watch like HBO half hours. And I just became such a student. Like, I really like to nerd out on things. And I just was like, I don't know where this path is gonna lead me, but I think I should just follow it. Cause it felt, you know, when you like buy a pair of jeans and it just fits. Like the first time you try it on, just slips on. Like, that's how I felt. I was like, this just makes sense. I don't know what this is gonna turn into, but I'm like, this fits.

[Jesse David Fox]

Yeah. Yeah. In the special, you blame Destiny's Child for your ambitions. Can you explain the sort of basically premise of that?

[Phoebe Robinson]

You know what I blame? I blame Destiny's Child. I blame my dad. My dad is very. I love you, dad. He's the best man I know. But he would always be like, I want you to be like Oprah and be like independent and like financially, like secure and all these things. And I just am like, I am so tired. I don't. Honestly, working is so fucking ghetto. Like, it is so ghetto. I am like, please, I don't want to file any more taxes. It's a mess. It is truly a mess. And I just, you know, as much as I do enjoy creating is a part of me where it's like, I've just been hustling and grinding so hard and being independent and all that stuff. Like, it's cool. But also it would be nice for someone to just like take care of stuff for me. It would be nice for like some old ass man to like pay the bills in exchange for my company, you know, which, listen, that's where I'm at.

[Jesse David Fox]

That's where you're at.

[Phoebe Robinson]

But I still believe in true love, you guys.

[Jesse David Fox]

The also the other joke in this section I'm curious about is. So you have the Mad Men joke. You talk about. It's a documentary and you talk about. For those who haven't seen yet. Can you explain the general premise? I have a question about it.

[Phoebe Robinson]

Yes. So I basically a lot of this special outside of sort of kind of talking about the concept of like this notion of being a girl boss or being like independent and doing all these things, like we were sort of like sold a bill of goods, that this was kind of going to be a thing that was going to like set us free. Like if women can like participate in capitalism the way that men have been doing forever, like, this is. You're. You're going to be so happy and then it's like we're just all tired, you know what I mean? And so there's a crux of that. And then within that I talk about other things and sort of just kind of like how like, female sexuality has been so, like, undervalued and like not paid attention to. So when I bring up Mad Men, I talk about this episode. I remember the first time I saw the scene, I was like, this is crazy. But dodge wife Betty, she is literally so sexually dissatisfied that she puts on a load of laundry and then puts her cooch up to it to fill the vibrations. And that's how she like basically jerks off. And I was like, you know, I thought the 1960s were hard because of what like, you know, I have my dream, but I was like, nobody's talking about this. None of these women were busting nuts and like that. I think we should also talk about in terms of. In addition to civil rights.

[Jesse David Fox]

Yes, yes, I was curious.

[Phoebe Robinson]

Cause so that Jesse.

[Jesse David Fox]

No, I asked about that joke also is in your last book or that idea is in your last book. And I was curious how yourself as an author and yourself as a standup and how the ideas cross pollinate or don't sort of how these examples come together.

[Phoebe Robinson]

Yeah, I mean, I think for me with that example in particular, I think we're going to. Are still sort of like in this phase of like sort of the general population understanding that sex doesn't happen to women, but that we are active participants in our own sexuality. And so I feel like that is like a theme that I don't think will ever go away in my work. Because I just think that it's important to joke about these things, to talk about these things, to talk about them unabashedly. Like, I don't want there to be Any like, oh, I don't know if I should. It's just like, no. Like, we're going to talk about it comfortably and confidently. And so sometimes I think things will work their way and in terms of my writing a book, sometimes stand up and that. To me, I think I like that joke because I get to, like, act things out a little bit. But, yeah, I just. I always want women to feel empowered and feel confident and be regardless as to what other people think about it. Like, not centering, like, other people's reaction, just being like, yeah, I'm comfortable in my body.

[Jesse David Fox]

Do you think of the book writing part of yourself and the performer as different? Like, are they extensions of the same part of you? Like, are you. I'm a writer first, and then, like, I can perform it, and that's a fun thing to do. Or, like, ultimately, you think of performance.

[Phoebe Robinson]

Yeah, I am. By the way, you're doing such a great job already.

[Jesse David Fox]

We just started.

[Phoebe Robinson]

I'm like, okay. I'm like James Lipton, okay. And saw the Actor Studio. Where's your. Where's your deck of blue cards? That's all we need.

[Jesse David Fox]

I like a long piece of paper.

[Phoebe Robinson]

You like a long piece of paper. You like the. I'm liking a whole vibe this is giving mean, like, just young Brooklyn. Dad, I'm here for the fantasy. What was your question?

[Jesse David Fox]

What was my question? Oh, though you as a writer, you as a performer, in so much as the. It remind me of the thing of, like, partly also because your writing is so voicey, it feels like a person talking. And when you're talking, you know, and there's a writerly quality to your performing. So, like, I'm trying to think of, like, where do you locate itself? Is it the same part of you? Are you, like, a writer? Who else performs? Are you a performer who writes? How do you locate it all?

[Phoebe Robinson]

I think I'm a writer first. Like, I've always loved books. I always used to read a lot when I was a kid, and I write, you know, short stories and stuff. So I think everything is sort of born out of me being a writer. And I really worked hard, sort of honing my voice through, like, college. And then also with my blog that I have, Blaria, which still for Black Daria, I just really wanted to be like, if someone, like, read this or they could, they would know it was me. And I think I have accomplished that, and I'm very proud of that. And I think there's just, like, I used to, like, I'm from the Midwest. I'm from Ohio. I'm like, oh. I used to always think, like, there wasn't, like, a musicality to my. My voice or rhythm, but I'm like, that's actually, like, false. There's a lot of, like, playful things that I like to do, writing wise, standup wise. And so usually if I come up with something that, like, makes me laugh, I will figure out what form it makes the most sense. I think with this special. I don't want to work anymore because I had the thesis statement. I sort of knew, like, okay, these are the topics that I want to touch on. Anything that doesn't fit under those umbrellas, like, that gets put somewhere else. So that kind of made it easier for me. But, yeah, I think I just. I just love language so much. I think any comic does. There's just. Just, like, the sounds and the syllables and, like, the rhythms you can build. So I just. I am. I'm a writer first, for sure, if.

[Jesse David Fox]

I told you this, but, like, there was a point in writing my book that I reread some. I can't remember which one of your books because I. The thing that you're able to do is the. The active talking. It's like, it's. It's. Lots of people try to write how they speak, and I try to do that, but it's literally like, it is in the moment, you're having a conversation that I was just like, how does it sound? What does it look like on the page? And I remember reread being like, obviously, I'm not going to do it like this, but, like, there's definitely an aspect of that. And, like, there's reviews and people who said, like, my book sounds like you're having a conversation with it. And I was like, it literally was. Your book was the thing that reminded me how to do it.

[Phoebe Robinson]

You guys, it's 2025, and a white man is giving a black woman her flowers for her contribution professionally. I'm going to take a sip. Thank you so much for that.

[Jesse David Fox]

Do you remember your. Your Girl Boss peak? Like, what was the moment where you're like. And not in a negative way, where you were like, I am doing it. I am at the top of whatever this is. You running production companies and, you know, imprints, and you're this. And this. When did you feel like, okay, I'm at the top of Girl Boss mountain.

[Phoebe Robinson]

I. I love Girl Boss mountain. I'm thinking. I think there are a few moments. I think the first one that comes to mind probably, what, 2019, I think. But when I moderated on Michelle Obama's book tour, and I did, like, five cities, and that was just sort of like, okay. It's sort of like just like, lol. Like, what is going on? Like, it just felt very wild. I just, you know, I highly respect her. I loved her book so much, and to be asked to be a part of that, it just really felt like a wow. I'm just been thoroughly myself and her and her team get it. So that felt, like, really cool, especially because it's like she was doing Arena. So it's like 20, 000 people are showing up to listen to someone talk about their book. That's probably not gonna happen again in our lifetime. Unless, like, I don't know, maybe Beyonce, like, maybe. You know what I mean? But it just felt, like, really, really cool. And I was just kind of. It didn't feel real until, like, it was over. And then I was just like, huh, Wow. I, like, did that thing that I wasn't even, like, aspiring towards doing, and that was just like, a very, like, happy accident, I think. Another moment when I felt like I was girl boss and he was probably, you know, when I had my beloved show Everything's Trash, just because, you know, while I was making that show, I, like, broke up with my ex, and there was just a lot going on. There's a lot happening. It was my first time, like, starring and creating, producing, and writing on a show that was all, like, I was wearing all those hats and, like, it just really felt so, like, natural and really fun. And I'm, like, friends with all the people on the cast still. A lot of the writers, like, it just felt like I just knew what I was doing. You know what I mean? And I know sometimes it can be hard because you're like, what's going. I can't predict the future. I don't know if I'm, like, ready. And I'm just like, if you just, like, do the work, when you step into a moment, like, you got it. Like, I'm sure when you started this, you were like, oh, I'm doing a podcast. Like, I never done that before. But, like, you're great at it. You know what you're doing.

[Jesse David Fox]

In your last book, you have some advice for bosses. Can you share at least one piece of advice that you do before we talk about how bad it's being a boss? I want to at least give you a moment where you're like, I was a boss, and I learned valuable lessons for future bosses.

[Phoebe Robinson]

Yes. I was Gonna say something was kind of, like, negative.

[Jesse David Fox]

Well, that'll be. Say the positive thing first and the negative thing second. It'll be a nice transition.

[Phoebe Robinson]

I think one of the things that I learned about being a boss is it, like, requires a lot of different parts of you. You know, you think you just sort of have to be the person who has all the answers, or, like, you have to be the person that says no. Like, so people, like, don't cross boundaries. And then you realize, like, it requires, like, you know, vulnerability requires tenderness. It requires, like, all these things, I think are great qualities in me as a performer, as a writer. They're absolutely applicable to me being a boss. But those aren't things that, like, we're told when you become a CEO, like, learn. You should be a great listener. You should be vulnerable with your, like, all these things that are, I think, feminine qualities are not sort of, like, celebrated as boss attributes. And I'm like, I think that a lot of them actually are so.

[Jesse David Fox]

And then what was the negative thing you were gonna say?

[Phoebe Robinson]

The negative thing I was gonna say was learning how to fire people. Learning how to say goodbye.

[Jesse David Fox]

Is that how. That's how you said it? Is that what it.

[Phoebe Robinson]

No. But it's like, you never want to be as someone who's a Libra, as a Scorpio moon and Pisces rising. Like, I never wanna be the bearer of bad news, but it's also, like, it's not my job if someone's not doing their job to just be like, oh, well, it's okay, because I don't want them to be mad at me. It's like, pull. Like, you know, pull up your britches and just say, hey, like, I appreciate what you've done, but this isn't working out, and I wish you all the best. And it's uncomfortable, but I just think you gotta just do the uncomfortable stuff.

[Jesse David Fox]

Did you have a moment where you felt like, as Taylor Swift says on her current album, you, girl boss, too close to the sun?

[Phoebe Robinson]

I'm just not. I'm. We're not even gonna touch that lyric because that sounds stupid as hell. Okay, girl. Okay. Okay, girl boss Icarus. Okay.

[Jesse David Fox]

But you know what I mean. Like, was there a time you were like, this is act that being a boss overcame essentially your whoever, whatever else of your identity?

[Phoebe Robinson]

Oh, for sure. I think definitely. Like, during COVID I was just like, everything's stopping. What do I do? Like, oh, my God, what's going on? Like, my. I was 100% a workaholic, and it Was that it was. Just mattered more than anything else. And, like, I took the losses hard. I took the. You know what I mean? Like, it just was like, so much of my identity. And then during COVID it was just sort of like, okay, well, like, what else to. Is there to your life? Like, I had no hobbies. I didn't really hang out with my friends that much. I didn't, like, see my family as much as I should. And so it was like all these things. I was just sort of in a place where I was like, you're kind of like, too old to not have a full life. You know, Like, I understand you're in your 20s. You got to be in your grind. But what was Covid?

[Jesse David Fox]

Covid was what, 20, 19 through whatever. Oh, so horrible.

[Phoebe Robinson]

But I was like, old enough to be like, there should be layers to my life. There should be other facets of my identity and who I am as a person I'm. I'm tapping into and that I'm having joy with. That's not based on monetary gain. And that just felt to me like, I felt like I. Maybe I wasn't living my life as well as I could have. And so I really. I went into therapy and I really had to do the work on that.

[Jesse David Fox]

To talk about specifically the work life balance.

[Phoebe Robinson]

Yeah. And just be like, I think I was. And Dr. Monica Johnson would agree with this, but I think I was very much tying myself to the results of things where I'd be like, okay, I do abc. So def is exactly what should happen. And then if it didn't happen, I would just crash out. And it was just sort of like, well, you can't. You can't control the outcome. All you can control is just doing what you think is good and what is valuable to you and then hope for the rest. And I think I was just so frustrated, and I think I spent so much time trying to be like, well, this is how things should be, rather than accepting the reality of what things are. And that was like, my own sort of misery that I was bringing into it. So I think that. And then also I was very much the queen of, like, oh, there's too much work on. On my plate. Then, like, I will just. I won't go see my friends or, oh, I won't rest. Like, anything that was actually healthy for me and good for me. I would say, well, I won't do that to make more room for. And you're like, well, that's just dumb.

[Jesse David Fox]

Yeah. What are you working for?

[Phoebe Robinson]

Yeah, exactly. So there was a lot of that. Yeah.

[Jesse David Fox]

This is also around the time where like, girl boss became a punchline that people made fun of it. Were you aware of that? Did you have a moment where you're like, looking in the mirror go, am I a girl boss? Am I what they're. Am I what they're saying on Twitter?

[Phoebe Robinson]

No, I never felt it to that degree. I mean, I did read that book Girl Boss by what was Sophia. Whatever.

[Jesse David Fox]

I don't remember if I just remember that. I forgot. I like to forget that a person like legitimately was like, that is my who I am. I'm gonna like, push that as a brand.

[Phoebe Robinson]

I think it was just more when that. I think I just sort of like felt a sense with like my other girlfriends. Like, we were all just like tired and we're all sort of feeling like we're not getting back enough based on what we're putting out. And so I think that was more the thing that I felt at that time was sort of a kind of like, this kind of sucks. This isn't as fun as I thought it was going to be. This isn't like, I'm not as happy as I thought I was going to be with all of these things going on. And that really led to this special. I remember this. It was like 2023, so I was like moving out of my old apartment into this apartment that I bought. My brother was like, in town. I had to go for a work thing. The. The day that I moved, I had to get on a train to go to D.C. and then come back and then go to LA and then come back and go to. And. And I was like, this is crazy. I remember texting my. My best friend. I was like, her name is Karen, but she's Italian, so she's a spicy white. Okay. But I remember texting her. I was like, I would suck a 72 year old stick if I did not have to get on this flight. And she was like, baby, you're being crazy. I go, I mean this in the depths of my soul. If I could get out of this, I would. And I was like, light bulb. I'm like, I think that is sort of like maybe could be the thesis of my. My special. Like, having fun with that.

[Jesse David Fox]

Yeah. Because I think you say you thought it was going to set you free in many ways. It was like a treadmill that you could not get off.

[Phoebe Robinson]

Absolutely. And it just felt, you know, that is like actually really a great. Someone wrote a book. But no, that. That is exactly how it Felt where it's like, I can't slow down. I have these employees, I have like, like, you know, my lifestyle. I have this career that I'm doing, like, if I stop, blah, blah, blah. And so it just really, it goes from being like, I love doing stand up and I love writing, I love acting, I love producing. To be like, well, I have to keep doing all of these things and juggling all these balls in the air because I can't stop. Because then what's going to happen if I do? And that's just like, not. I think as a creative person, that's just not the place we want to be. Which is why I'm just so anti content these days. Because I just don't think that that is how you make good things.

[Jesse David Fox]

Yeah. I mean, I also think there's sort of a generational quality to it where as a generation who was like raised to both, like, work hard, but also to aspire to sort of like a dream job where it made it feel like, well, it's my dream job, so it's like actually fun, so I actually don't need to take breaks. And then I do think a lot of people in that, like many girl bosses I know or just generally creative people, I think are at a point where they're like, like, wait, this is work this whole time?

[Phoebe Robinson]

Oh, yeah. I've always felt that whenever people say that, like, if you. If you do what you love, you never work a day in your life. That is so not true. You are working and you love what you do, but you are working. It's effort and it's. You're really like, excavating yourself to create these things. So I just. It's all working. You just have to have balance and you just have to. I think for me, I just was always like, I don't have to feel beholden to these things. Like, I can actually take control of what I want to do or not.

[Jesse David Fox]

Want to do in. In the special. You know, part of it was the breakup that you went through around this time, which was a long relationship. It was also a very public relationship. It became what is now called parasocial. You sort of like, we're a trend center in terms of like, what a type of relationship would look like. When you look back upon that aspect of your relationship, the fact of how public is. How do you think about it?

[Phoebe Robinson]

You know, I guess it was public, I guess, for me, because I'm always like, I'm like, not a list, you know, I'm like, not Zendaya. But I think looking back on was fun being public the way we are because I feel like we were very jokey and it was never like guys, this is how you do a relationship. Like we were just being people who are just both funny. And I think that going forward I probably would be more private just because I think like even when we broke up and people are like, you guys broke up, I didn't know. And I go, I don't know you, why you thought like, you think I'm going dme every person who follows me to be like, I broke up with my boyfriend. So I think, I think people just need to calm down and take a step back and, and go like, you don't know people that you follow that entertain you. Like you really don't know them. But I don't think the us being public was, was any. Was one of the issues in our relationship.

[Jesse David Fox]

Sure. Yeah. I was just curious about because I do think as you're saying you're don't like this sort of content thing. I do feel like the way you had that relationship beeps just part of your brand as kids today would say does feel like a content version of a relationship. But you were before that became so normalized.

[Phoebe Robinson]

Yeah. And it was just really like I would just post whenever. Like it never felt like we were trying to be like, oh, this could be a thing that's funnier. This could go viral. It was really like we were just being ourselves.

[Jesse David Fox]

Yeah.

[Phoebe Robinson]

And I think now people like, like expect that from everyone. So it makes me be like, I don't want to participate in that.

[Jesse David Fox]

In your pre, your last special, you talk about that relationship a good amount. And there are jokes that were negative about living with him during COVID that at. In this, that special was framed as like, but it's great. Like it's all positive. Do you now look back on those jokes differently that you're like, oh, actually this was, I was voicing an opinion. Like it's almost like my stand up self was ahead of how I was.

[Phoebe Robinson]

I think it's more and I'm trying to be careful because I don't want to, you know, I've moved on. He has moved on. I think living together during COVID was fun in a lot of ways, but it was also tricky and I think it also sort of rack focus things about the relationship that I think I saw sides of him that I don't think I would have seen if it weren't for Covet. And I, you know, I, I think like one of the things, like, I think everyone, like, sort of, like, deals with stress and trauma and all those things in different ways. And I think he was. I don't know what he's like now, but he very much was a person. Like, when I get down, I kind of have to, like, bring you down with me. And I'm a person where, like, okay, I will allow myself a day or two to, like, feel sad, but, like, let's get out of this. And I think those are just two different approaches to life and, like, how you handle adversity. But I do think being in a relationship with someone who is refusing to help themselves. So you are trying to help them. I fell into that trap that, you know, Nicole, Kim and I are similar.

[Jesse David Fox]

In that way on the many ways.

[Phoebe Robinson]

Girl. I'm one of many. No, but that, that instinct to help. I don't always think that when some men are at their lowest, their partner being helpful and supportive, they end up resenting you for that because it's like you're. You're seeing them at their lowest, and it's like they punish you for liking them when they are in a moment when they don't like themselves. And so I think because I was so busy and, like, trying to keep the relationship together and being like, the sunshine, I think I didn't really. I wasn't present in all the ways that the relationship probably should have just wrapped up sooner than it did. And so I think that is what was the takeaway from that. But the jokes, I do feel like I meant them with love. I was like, I, I, I did love this guy. Like, even though he was annoying at times, I was annoying too. So it felt like that's part of being a couple. You're annoying. But I think in this latest special, it is sort of me taking stock of, like, this person was kind of a hot mess and I was carrying him for too long.

[Jesse David Fox]

Yeah. So the joke is hinge on. You bought him teeth.

[Phoebe Robinson]

I bought it. So listen, I wouldn't do that again. And I'm sure if I called my business manager, Scott, before I did that he had been like, you are not buying this white man teeth. Now, he probably would have said the white man part. But. But I think that was a thing where it's like, I just loved him so much and I wanted to help. And, and the special, I'm just sort of like, no, that's, like, kind of ridiculous to, like, go and do that. But it was a, it was a good lesson to learn. And I've had people Multiple people be like, I did that too.

[Jesse David Fox]

So you call it reverse colonizing. But my favorite part, maybe my favorite joke in the special is you go, it's. It's like the Upside down where Millie. Bobby Brown's name is Millie Whitney Houston. Yeah. That's so stupid.

[Phoebe Robinson]

It's so stupid, right?

[Jesse David Fox]

I was like, it's nice that that guy snuck into this special.

[Phoebe Robinson]

Thank you.

[Jesse David Fox]

Do you give a person a heads up? Like, would you be like, hey, just, you know, I talk about you in the special. I don't know if you talk, like, to my ex.

[Phoebe Robinson]

No. Why?

[Jesse David Fox]

I don't know. That's why I asked the question.

[Phoebe Robinson]

Absolutely not. Okay. Okay. I need to send him a bill for how much money I helped him.

[Jesse David Fox]

Out with tangentially, but they're related. In your last special, you tell you. We just talked. We mentioned Michelle Obama. In the last special. You do talk about that experience, and you tell a specific story about that time. For those of you. Can you share the general experience of that you talk about in that last special?

[Phoebe Robinson]

Yes. I mean, again, Michelle Obama is everything. And, you know, I hung out with her and some peeps afterwards, like, people on her team, you know, the people who are with me. It's really fun. It's great. You know, I was out here eating cheese. Like, I'm not lactose intolerant because I'm just like C.C. pueda. You know what I mean? I'm still that yes, we can moment. And, you know, your girl had gas. And I was like, well, what we're not gonna do is fart around Michelle Obama because she's been through enough. And so I just held it in till I got back to my hotel room. And I just, like, it was just the longest fart into my toilet bowl. It was so much butt jazz. I was like. I was like, how much blue cheese did I have?

[Jesse David Fox]

Did you think about her? Did she have you? Do you know if she saw that special?

[Phoebe Robinson]

I. I think she's busy.

[Jesse David Fox]

I don't know. She had a few years.

[Phoebe Robinson]

I don't know if she saw the special. But her. And I text occasionally. She's just always very lovely.

[Jesse David Fox]

You'd be like, don't watch the special.

[Phoebe Robinson]

Well, no, what I did learn from her is, like, whenever I text her, she, like, literally text responds within five minutes. So I'm like, when men are like. I was talking to this one guy on Bumble, and he. He was like, oh, I didn't. I didn't call because I. I fell asleep. And I go, you fell as, like, no one fall. At our age, we don't fall asleep. Like, it takes a lot to power down our computers. And I go, if Michelle can respond within five minutes, these dudes taking hours. Absolutely not. So that was what one thing I learned from her was.

[Jesse David Fox]

Yeah, I know Bill Burr is one of your favorite comedians around this time. You know, he did material about her arena tour. Yeah, it was basically about. She basically was like, she's playing arenas, she's not playing comedy clubs. Like, the idea of, how is she playing arenas? I mean, he's also arena act, so, like, he shouldn't be bitter. And essentially it goes. She wrote a book about not having a job. I didn't know if you had opinions about it.

[Phoebe Robinson]

I mean, I remember that, and I go, listen, I know he's a contrarian. I'm just like, sometimes it's just gonna be like, you can just not have a tape that, like, it's also cool to, like, shut the fuck up if you want. But I love him. He's great. I wouldn't tell him to STFU his face, but it just felt like. I know he's, like, trying to be funny, but I do also. I just find it interesting how easily men in society dismiss the contributions of women if it's not tied to money, when actually things would not run if women weren't doing the emotional labor, the domestic labor, raising kids, making sure that men have their. You know, how many times, like, Michelle probably like, oh, Barack. Oh, I know. Babe Hardy, we're on Keep Barack. You know how much she had. You know how draining that was that she had to do that. Like, oh, come here, Babe. Like, that's a lot. That's. That is work.

[Jesse David Fox]

Yeah.

[Phoebe Robinson]

So to me, I'm like, she was working hard, Bill. You do your thing. Let. Let Mish do her thing.

[Jesse David Fox]

I think that's a good transition to. I want to talk to you about podcasting. Yes. Because you were so associated with the form for a few years, and I was curious, what do you think of the state of comedy podcasting?

[Phoebe Robinson]

That's too much. I can't. Everyone has a microphone. It's really. When Jessica and I did it, it was like a lot of people weren't doing it. You know what I mean? And so it felt sort of like. And there was always intention behind our shows to, like, be funny, to showcase people that we thought were really talented who weren't doing, you know, sets on late night television. So it always had a purpose. And now everyone's just sort of like, well, I could get in front of a microphone and I can, I can share my opinions. And I'm like, most of these opinions are ass. Most of these opinions and these hot takes are terrible. They're not interesting. And I think you need to take a test before you can have a podcast. You need to listen. It's too much. It's too much noise pollution.

[Jesse David Fox]

What will be on the test? I need to study up.

[Phoebe Robinson]

God. I mean, some of it is just like, are you, are you dumb as like, and write, write an essay proving that you're not like. And just like, I don't know, I just. There's so much to this, the space of podcasting right now where I think, because, oh, we're just hanging. I'm just saying things. I'm just. Whatever. There's a cavalier ness to it. When people are saying some of the most unhinged, inappropriate, sexist, racist things that I'm just like, why are we all so casual about things that are actually quite hateful? That is the part that I don't love. And I really feel when I was podcasting it was really like, you're trying to do something fun or creative or you're going to be weird or you want to be whatever. And now I feel like so much of it's like, what is the. What are the things that I can say that A will get the most attention, will get me the most sort of fans and make me the most amount of money. And I just go, it doesn't feel interesting or sexy or weird or left of center the way that it did when I was doing it.

[Jesse David Fox]

Would you return?

[Phoebe Robinson]

Oh, yeah, I think I would. Because I especially, I think I will want to do an interview podcast next. Cause I like interviewing people and listening to them. I just think people are really fascinating and I think I take a lot of preparation when I interview people. Like I remember when I interviewed Michelle, that was about, it was about four days of prep where I was just like nonstop highlighting, trying to figure out what's the arc of this conversation. Like all those things that are like really fun and deliciously nerdy. Like, like, I miss that part.

[Jesse David Fox]

So I believe it's the 10 year anniversary of when you started doing 2 Dope Queens as a live show, give or take.

[Phoebe Robinson]

Yeah, yeah.

[Jesse David Fox]

So what you co hosted with Jessica Williams, that was then turned into a popular podcast, an HBO show. And it, it was a, you know, you came to it with intention. And it changed comedy, definitely, especially in New York. It changed who went up where, who went to shows where. And so I want to talk about it a little bit, because I think there's probably a lot of people who just go to shows and they're like, oh, this is what comedy always was like. And it was not like this before. Two Dope queen. So for those who aren't familiar, how did it start and what were your hopes as you were developing it, Especially the. As it became a thing you and Jessica were doing together?

[Phoebe Robinson]

Yeah, it really was. It happened organically. So 2015, I. God, there was a post on Craigslist. I'm young, you guys. I swear. I'm. I am. I'm a youth. But it was to do background for a piece for the Daily show, and it's. This piece was black women's hair in the Military. So I was like, sure. Like, that'll be cool. And then when I go, like, do these, like, standup shows, I could be like, oh, as seen on the Daily show, you know, you need to have a credit. Back then, it was very important to have a credit so you could feel worthy of being on the show. And so her and I met and we sort of, like, hit it off between setups, and she was just, like, really nice and funny. And I was like, oh, you know, I have this podcast I tape out of my apartment. Would you ever want to come and be a guest on it? She was like, yeah, that sounds cool. So she did it. We had so much fun. And one of the things that I think she said her birthday was coming up, and I go, oh, what would you want to do for your birthday? And she's like, oh, I've always wanted to try stand up. And I was like, oh, that'd be fun. I was like, what if we just like, I have this show. What if we just co host it together? And then you could say, like, oh, I tried it. Maybe I want to do it some more. And she said, okay. And so she was busy doing Daily show stuff, and I was. I don't know, I was probably doing, like, day job stuff and then stand up at night. So we didn't get a chance to, like, really meet up and talk about what we're going to do. So when we got to UCB East, I was like, here are three things that happened to me this week. And she was like, okay, here are three things that happened to me this week. And I was like, great. We'll just, like, talk about it and figure it out. Because she had done improv, I'd done improv. I'm like, it'll be fine. And that truly was sort of, like, the genesis of 2 Dope Queens, where Jessica and I, a lot of what we did was off the cuff. And the UCBE show was, like, just such a success. It was really fun. It felt really natural. And we're like, like, oh, like, yeah, maybe we should do that again. Like, it felt like a good first date, you know, and so then we did it again, and then the second show sold out the way the first show sold out. We did a third show that sold out, a fourth one. And I was just kind of like, maybe we could move this somewhere where we could actually, like, make money from, you know, the. The ticket sales. Yeah. I won't say anything, but I'm also like, amy, girl, I need some money.

[Jesse David Fox]

You know, Dina are watching this together.

[Phoebe Robinson]

And so then we moved it to Union hall, then it grew, and then we did. Oh, God, what's the bigger venue? Bellhouse Bell House. Thank you. And it just became this thing, and it was super fun. I was like, I feel like this could be a podcast. And she was already doing stuff with wnyc, so just all really happened organically and just grew from there.

[Jesse David Fox]

Do you have a definitive 2 dope queens memory?

[Phoebe Robinson]

Oh, oh, you know what's a fun one? It's not a definitive one, but it's a fun one, is Jon Hamm had reached out to my manager at the time and was like, I really like two dope queens. Like, like, you know, I would love to do it sometimes. So that I was like, oh, that's nice. Because you never know who listens. Like, we're just. I don't say we, because I don't know. But for me, I'm very much like, I just do what I do. I create what I create, and I don't know who likes it or how. So I'm always pleasantly surprised and moved when people like my stuff.

[Jesse David Fox]

What was the. We talked about a little bit, which is, like, getting different people up on stage than when we're being there. Or just like, up on Union hall stage, where we was once thought of as alternative comedy. But, like, you did that, and then especially, like, I think with the TV show, you gave a lot of people the first late night spots or just TV spots in general. When you look back upon it, like, how do you think about it? How do you process what it meant?

[Phoebe Robinson]

Oh, I'm so proud of it. I'm so proud of it. It was very much a direct line in certainly my brain of, like, this is what this show should be, should be a platform for people who I think are brilliant and don't have as much attention as they should. And it really just came out that way. And HBO got what we were doing. They said they didn't want us to change anything. They were like. Like, keep this for the show. And I just. I feel like when I started doing standup, when I started getting into publishing, like, just so much you're just told, like, you don't fit, you don't belong, you can't do. Like, the number of times people told me that I would never make it in Hollywood, I would never have a career in comedy, just for laughs. Told my manager that I didn't forget all these things. You know, I just was, like, teed up queens. Like, we accomplished what we set out to do, and that's not always the case when you do something creatively.

[Jesse David Fox]

Yeah. What's your relationship with Jessica like now?

[Phoebe Robinson]

I think it's more like we're both, like, on our grind, which I know it's gross, but now we have to be on our grind because the industry is falling apart. So we're both, like, you know, booked and busy and doing what we're doing. But I think what she's doing is amazing. She thinks what I'm doing is amazing, and I'm so happy for her. And I think it was just such a. It was like one of those things that was just like, it came along at the right time in both of our lives and we got out what we wanted from it. And, yeah, I have nothing but positive feelings.

[Jesse David Fox]

You. You mentioned the industry falling apart. Can you talk a little bit more about that?

[Phoebe Robinson]

I just feel like we're in such a weir state where some of it is affected by social media, where it's just about content and constantly pumping things out and not, like, giving anything room to breathe or to grow. And then also, you know, with Streamy, we're just in a place where there's just too many distractions. So the way that we all, like, watch TV is different. Like, we're not all watching stuff at the same time, really. And so I think right now there are a lot of cool things happening, but I think there's also a lot of things where people are scared, like, they don't want to do, left to center things they don't want to do things are creatively going to push the envelope. And that's the thing that I think is a bummer, because I'm like, if you look at stuff like fleabag or centers or, you know, what have you, like, those things just have such a Unique voice and point of view. And that's part and parcel why it's successful, like why people resin like it resonates with people because of that.

[Jesse David Fox]

I was curious. So you with two dope queens and then the success of your books, you had a thing that happens to comedians where it's like there's this heat and momentum of just sort of like, okay, you're just gonna keep on doing the thing and then you'll get the show and then you do whatever and it just sort of builds and builds and like I'll say even like I experienced experience a much smaller version of like I had the podcast and then that builds to a book and then I did a TV version of the podcast and then you sort of are. You do the things that are the first thing you do from it and then you have to still have a career, but it's not the sort of specific momentum. I was curious how that has felt for you being in the stage of like you were still working, you're still producing, but like it's not as a linear of a path from like where your genesis.

[Phoebe Robinson]

Yeah, sometimes it's frustrating because I do think I'm really talented. I'm like, someone just give me a shot to do these crazy ideas that I have in my head. But I think the other thing that's come out of it, which I think is actually as equally important is I think when I started doing st. Now I think I know when I started doing standup, I was 23, going on 24. You know, I was an insecure person who isn't in their 20s. And I think I needed stand up in a way that I don't need it now. And I, I think a lot of it was the sort of like external validation of like, oh, I'm on the right path, I'm doing this thing, I am funny, I can do this. And I work twice as hard to get this thing and blah, blah, blah. And I think a lot of that fueled my ambition. And now I'm, I'm in a much more peaceful place where it's like I, I know I'm funny. I'm like, okay, I didn't book that movie. I know I'm good. And I think there is more internal peace now. Don't get me wrong, Will I probably cry this weekend if something doesn't work out? Work wise, of course. But I think there's an element of unshakability. I think I'm more rooted within myself than I was before.

[Jesse David Fox]

You're still doing many Things the imprint is doing quite well.

[Phoebe Robinson]

Yeah, five years.

[Jesse David Fox]

No, it's wild in books. Of the many industries that are, you know, having trouble. But. And you know, of the things, what are you most proud of?

[Phoebe Robinson]

Of everything I done. Oh my gosh. I think Tito Queens, obviously what you touched on, I think the imprint as well because you know, especially when you meet like for like for nonfiction, you write like a book proposal. Okay. And you sell it off of that and you go write the book. But with fiction you have to write the whole, whole thing. So these are people who. This one author, Jess Gutierrez, she will work all day, she has kids, go home, hang out with her wife, do the kids stuff, everybody went to sleep and then she would get out her notes app in her phone and that's how she would write her book. And I go, that level of dedication when no one is giving you a dime is remarkable. And so when her book came out and you know it was well received as all those things, you just feel sort of like yes, like believing in yourself and working hard when there's like no proof that it's going to work out. I love like, I love things where it's like, it's about proving yourself right rather than proving others wrong. Cuz like I don't want to center other people, I want to center myself. So I think I'm really proud of that. You know, as much as like, like complain about not wanting to work. I visited my girlfriend and when I was in London for my birthday and we're hanging out and I was just sort of playing like oh, you know, I just really thought I'd find my person by now and da da da. And like, like you know, sometimes just feel sad about it. Cuz you, you do kind of have to, you know like mourn the ways in which your life is not what you thought it was going to be. And you know, she's brilliant. PhD as a teacher and now she's a stay at home mom. And you know that's like a massive undertaking. And her, her house is so beautiful. And she was like, but Phoebe, you did it. She was like, you worked your ass off and bought your own apartment. And I go, you have, I was like, you have your house. She goes, I did not buy this house. She goes, you bought your apartment. Like you could say that you did it yourself. And I was just sort of like sort of reframing like I have to do this myself more in like I get to do this myself. That's like how I get through like workouts sometimes. Where I'm like, I don't have to run. Run 18 miles today, which. Shudder. It's like, I get to run those 18 miles. I know, Jesse. No, you should be your marathon.

[Jesse David Fox]

But I'm happy for you. It's just, I find to me, it's like running was always the punishment in, like, any sports I played. So I just cannot be like, let me run as the. I tried it one time, I just, like, moved to la and I go, I'm gonna run because it's nice out. And truly, let's say four minutes in, I was like, this is so boring. To say nothing about track. Where it's like, literally. Yeah, Yeah. I mean, the thing that's sort of interesting, it's like, this is sort of. I guess the upside of being a girl boss is, like, you went, you had intentions. Be both personal, you bought your place, but also, like, 2 Dope Queens was a thing created with intention to change a business structure. And, like, the same thing with tiny reparations as an imprint. Like, these people are not getting their books published. I hope to be able to help do that. And, like, bunch of people were able to get books published that probably would not have been otherwise. Been published.

[Phoebe Robinson]

Yeah.

[Jesse David Fox]

If you don't want to be a girl boss, what do you want to be?

[Phoebe Robinson]

Oh, okay. That feels like a Barbara Walters question. I'm here for it. We're channeling all the interview gods. If I don't want to be a girl boss, what do I want to be? I want to be content. I think I have my moments where I feel content and I feel happiness. But I think I also have, you know, sometimes a little, like, narrative that's running on loop that doesn't always say the nicest things to me if I get stressed out. And so I think becoming more standard and, like, not allowing myself to sort of, like, beat myself up, I think would be good. But if I couldn't be a girl boss, the other thing I would probably want to be is, you know, in another life, I was like, I think I would have loved being a music producer just because I really, like. If you look at, like, Beach Boys, like, Pet Sounds, like, the way they layer the harmonies. Like, I love, love putting things together, whether it's IKEA furniture or, like, writing a book or putting together a TV show. Like, I really just love the nuts and bolts of, like, okay, I have an idea, it's in my head, and then I can work to build it and make it a real thing. So I think if I weren't A girl boss. I'd be a music producer.

[Jesse David Fox]

I liked how. I really like how special looked and I was very interested. There's all the zooming. Can you. Was there an idea behind that?

[Phoebe Robinson]

So that was directed by the fabulous Sharza Devani, who, you know, has done. She's directed like St. Denis, Abbott elementary, like a lot of great, like, sitcom. She also did a couple episodes of Everything's trash. And I had just had a great experience with her and what I liked about working with her on this is what I saw. And Everything's trash is I think sometimes when something is a comedy, people are like, oh, you don't really have to care about how it looks. And I'm just like, no, you can make it a little bit cinematic and make interesting choices and still get the jokes across. And I thought she did a great job of that. And so with the special, she was just like, I met with her and I was like, I want to meet with some other people to do my due diligence. And she was like, yeah, you know, I've like, I've heard the hour and, you know, I want to see it in person. But she was like, I have this great idea for this backdrop and like, like, you know, you talk about, like so much being a girl boss. And then she was like, I think we should do something that's like really, like, feminine. And then she was like, you could wear like a suit that's like, masculine. So I was playing with all these sort of like, ideas and she was like, you're so expressive. So she's like, I want to make sure I get like a lot of, like, zooms to capture your face and then get some wide shots. So I think she was just really intentional about hearing the material and making sure that we're not just going to be standing in front of like a red curtain with a microphone and that it just has like a little. A little zhuzh to it, which I thought was great. Morning, Zoe. Jeff Bridges. Why are you still living above our garage? I want to be in a T mobile commercial like you. Teach me. So, Dana, I couldn't possibly at T Mobile get the new iPhone 17 Pro on them. It's designed to be the most powerful iPhone yet and has the ultimate pro camera system. Impressive. Let me try at T Mobile. You can save up to 20% versus.

[Jesse David Fox]

The other big guys. You heard them. T mobile is, is the best place to get the new iPhone 17 Pro on us with eligible traded in any condition.

[Phoebe Robinson]

Check them out.

[Jesse David Fox]

See how much you could save versus the other big guys@t mobile.com switch support.

[Phoebe Robinson]

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[Jesse David Fox]

So now it's time for our final segment. It's called the laughing round. It's like a lightning round.

[Phoebe Robinson]

Jesse, I want to just keep hanging out.

[Jesse David Fox]

Well, you take as long as you need these questions.

[Phoebe Robinson]

Okay?

[Jesse David Fox]

Honestly, all these questions are actually take longer answers than many of the other questions. I don't know. It's too late. I can't change the name of the segment. But that's it just means we're resetting. And anyway, so in the grand tradition of WTF with Marc Marin, I ask people who are your guys? So who are your guys? As in the comedians that influence you or are the greats?

[Phoebe Robinson]

Gosh, I Janine Garofalo, she's wonderful in her and I've become friendly over the years which I didn't always. I mean it's just like how do you expect that to ever happen? So for her for sure. I really loved Patrice o' Neal so much. So funny.

[Jesse David Fox]

You met him?

[Phoebe Robinson]

I met him. Gosh. This was probably, oh, 2010. It was like, at Caroline's. And I, I, I forget I was wearing something, but he was, like, roasting me based on what I was wearing and was, like, so funny. And he was so spot on. I, like, loved it, but he was just, he was just so brilliant. I got to see him at a few different places, and he was just really good about using the audience as, like, another instrument and weaving in and out of material. Like, he was just so. He was so brilliant. He really was brilliant. Of course. Chris Rock, obviously amazing. Wanda Sykes. Love her so much. So talented. Bill Burr, I like a lot. Yeah. Those are probably the people at the top of my head where I'm just like, you're there. You're amazing.

[Jesse David Fox]

Have you met Wanda?

[Phoebe Robinson]

Yes. She's great.

[Jesse David Fox]

Yeah. Do your favorite joke. Joke, Like a street joke or dad joke.

[Phoebe Robinson]

Oh, I don't, I don't have those. I know. I saw this on the, on the, the, Like, I was, I knew this question was coming. I was like, I don't do that.

[Jesse David Fox]

Okay. I guess the difference between this section is you could pass on questions. Yeah.

[Phoebe Robinson]

Yeah. I feel like Noah Wy, when he was on Jennifer Hudson show, and he was like, I'm not going to do the spirit tunnel. I don't have. I don't have a dance.

[Jesse David Fox]

I don't know that's allowed.

[Phoebe Robinson]

Yeah. He was just like, I don't dance. He's like, I'm just, I'm not gonna.

[Jesse David Fox]

Do it now that I know that.

[Phoebe Robinson]

Yeah, you could turn it down.

[Jesse David Fox]

Because I see the spirit tunnel and it makes me feel so nervous. Like, it's like, it'd be like what I would have stress dreams about. Be like, you wake up and you're unprepared to do the spirit tunnel. The idea that you can say no means that now when I see everyone, that means they all said they said yes to doing it. So they're not like, literally, that's how you have to go on the show. Thank you so much for that.

[Phoebe Robinson]

Oh, cool.

[Jesse David Fox]

Is there a joke you wish you conceal? Another comedian joke that you wish you were able to tell and it's your joke.

[Phoebe Robinson]

But it's so hard because I think because I'm so voice driven that I wouldn't want to steal anyone else's joke because I don't think I could do it the same way they could do it. But what I do like is watching comedians who I could never, like. Like, watching Tig Notaro, I'm like, I can't do anything that she does. And I find it so fascinating. Like, I know some people get, like, very, like, a little, like, oh, well, I'm not gonna give. It's like, everyone's different.

[Jesse David Fox]

Yeah.

[Phoebe Robinson]

Like, so I. I like that kind of stuff.

[Jesse David Fox]

Do you have a short story of an interaction with a legendary comedian, living or dead, you're willing to share with us?

[Phoebe Robinson]

Yes. So I. Especially for this last hour, I used to work out a lot at Eastville Comedy Club in Brooklyn because it was, like, near me, so I could always just, like, pop over, do, like, 15, 20 minutes and bounce. And Marco's a great booker there. He would always. Jeannie and I did, like, a lot of shows, and so he would always put me on after her because, like, oh, it's Jeanine. And then from 2 Dope Queens and, like, blah, blah, blah, whatever. And I was just always like, okay. I just am always following Janine. I was like, all right, I guess. And so, you know, I would, like, get there early so I could, like, watch her set in the back. And then she just was always so free and so funny and fluid, like, amazing. And she should go off stage, shake hands, and then she would watch my set. And so the first time she did that, I'm sure it was just sort of like, oh, I hadn't seen this person live. I just want to see, like, what's up? And I was like, oh, that's cool. And then, like, if she didn't have another spot, almost every single time, she would just stay and watch my set. And I was like, why she keep watching my set? I was like, janine, Reality Bites. Janine. Romeo and Michelle, Janine. And so one time I came off stage and, you know, I went to, like, my notebook to, like, sort of, like, make notes on, like, oh, whatever. And she goes, you were just. Just so. She's like, you're just. You do the work. She was like, I always see you. You have, like, your little notebook. You're working on it beforehand, and afterwards you go off, and she's like, you really get a lot done in a day. And, like, she was just like. She was just aware of, like, the things that I do, which is just, like, really nice. And, like, we really just have, like, a lovely interaction. Like, we would go for tea sometimes, and then we were hanging out, and I was just like, oh, yeah, blah, blah, my birthday's coming up. Up. And she goes, oh, my birthday's coming up. And I was like, oh, okay, cool. I was born in September. She goes, I was born in September. And I go, okay, September 28th. She goes, that's my birthday. And I go, what? And she goes, I knew there was always a reason I felt a little maternal towards you, and it's because we have the exact same birthday. So it was really sweet and really lovely and she was always complimentary and she's just. Just has the funniest stories and she's so smart and so brilliant. So I'm just always like, if you ever feel slightly intimidated that someone you respect is watching, you take that as, like, respect.

[Jesse David Fox]

Yeah.

[Phoebe Robinson]

You know, Is that cute?

[Jesse David Fox]

Is very cute. I thought, like. And then we threw a joyed birthday party.

[Phoebe Robinson]

No, I. Oh, my God, I wish.

[Jesse David Fox]

What is the funniest YouTube song?

[Phoebe Robinson]

The funniest one? Oh, God. There are a couple where I'm like, girl, why you write that lyric there?

[Jesse David Fox]

One of the ones where he's like dancing around like a little devil guy.

[Phoebe Robinson]

Oh, gosh, I love my boys so much. I always think Vertigo is funny just because they just count Spanish just incorrectly. You're like, okay, this is.

[Jesse David Fox]

As a person who's seen you two at the Sphere, I always think about the sphere. And if a comedian can ever play the sphere, can you think of any comedian that you think would use this fear correctly? No. Okay. Asked an answer. What is something that some people think is comedy that you think is not comedy?

[Phoebe Robinson]

Can I name a person? I'm just kidding. Do it as we speak.

[Jesse David Fox]

A. A clip of one. A past guest naming a specific person is doing quite well, so feel free.

[Phoebe Robinson]

One thing that is comedy that I don't think is comedy, you know, lazy crowd work. I just don't like it. I just don't like it. I just. And I like crowd work. I've seen it done really well, where you're like, oh, this is amazing. This is brilliant. But when it's so lazy and it's so, like, I'm just gonna fall on stereotypes, or like, you could tell, like, oh, this person only had like 20 minutes material, and you're just gonna pad the rest with like 40 minutes of crowd work, I just. I just go. We spend so much time at our job jobs that if you aren't going to put the effort in to the time that you're spending your job, then you are essentially wasting your time. And so for me, I just hate that. And I'm like, there's so many, like, I think it's such a privilege and a joy to do Standup and to, like, have an idea and figure it out and, like, be a doctor with, like, all the word choices. And so to just. Just not be a participant in that and take the easy way out. I'm just like, why the are you doing this? I don't like it.

[Jesse David Fox]

When you said, we spend so much time at our jobs, I thought you were gonna say, no one wants to be reminded of their job when they come to come show. Stop asking people what they do for a living.

[Phoebe Robinson]

Yeah. It's like, what do you do for a living? Are you single?

[Jesse David Fox]

I came here not to think about work.

[Phoebe Robinson]

Yes. And by all means, like, but this is what I loved about Patrice. I always feel like there was an intentionality behind his. His, like, crowd work. He wasn't like, oh, what? What's your day job? He would never ask something so pedestrian. Like, it was always, like, in the context of how he was viewing male, female relationships, race relations, like, society. Like, there's always something highly intellectual that he was doing. And then he was able to use that moment of, you know, sort of crowd work as a way to distill it into something, like, easily digestible to the service point.

[Jesse David Fox]

Yeah. Do you have a joke that never worked that you'll go to your grave being like, I was right there. Wrong. That is funny.

[Phoebe Robinson]

Oh, no. And here's. Here's why I say no, because I'm like. I'm very much a firm believer. Like, there are some funny jokes where you're like, oh, this is so cute, even it doesn't get a big laugh. But ultimately, if a joke truly is not working, like, no one's laughing, and you do it, like, for 20 different shows, it's not funny. And it's okay to be like, yeah, that joke was ass. I won't. I have. I have those jokes where I'm like, not gonna do that again.

[Jesse David Fox]

Last one. What is the best time? You bombed.

[Phoebe Robinson]

Best. Because, you know, if there are a few, there are a few. I did this show, and these are things you do when you're just hungry for a stage time. You're like, yes, I got five minutes. I can do seven minutes here. Sure. I did this show where it was, like, standups would go between stripper acts. And the thing about that is the men really are like, the last thing you want to hear is a woman talk right now. Know you on stage going, I don't want to hear that. So, oh, I got cooked doing that show. Oh, they just want to see titties. So that was rough. So I Would say, but it's worth doing those shows because I think where I'm at now, what is it, 20, 25? So was that 2008? Was that 17 years? I absolutely do not care if I have a bad set. It's a weird. And I, I have talked about this in other things in my life. I can have emotional detachment to certain things. And with standup, I'm like, none of it matters until I want to tape it. And everything else is going to the gym, experimenting, figuring out, making, like, just tightening everything. So if I have a bad show, I'm just always like, like, oh, it's okay. Like, it doesn't feel great all the time, but I'm like, it's okay. Like, and I will tell the audience sometimes I'll be like, you know, this set is going to work in the future and I hope you're at that show and you can see the progress that was made. And that's what it is. I think it's a very. What I love about standup, I know we got to go, but what I love about standup is I think it's so much like life in that it's not focusing on, like, I gotta kill, I gotta get this, I gotta go. This destination, it's really truly the process of doing it and figuring out what you learn about yourself. And so I don't know, I just like, if I have a bad show, I'm just like, the world continues, the world goes on. It doesn't mean I'm not a great person. It doesn't mean that my parents don't love me. It just means I had a bad set.

[Jesse David Fox]

That.

[Phoebe Robinson]

And sometimes you get your ass handed to you. That's just how life goes. And then people forget. You remember it more like, I can't. Like, I truly can't remember. And I've seen bad stand up shows. I can't remember anyone who was bad because you delete out of your mind.

[Jesse David Fox]

Or you're like, I saw Chris Rock and he bombed. Like, yeah, you're like, that's a better story than like, I saw Chris Rock and like, he was fine.

[Phoebe Robinson]

Yeah, yeah, yeah, exactly. So I don't know, I say, just embrace. This is the other thing. And then we're going to leave. But this last question.

[Jesse David Fox]

So you can take 30 minutes on this one thing.

[Phoebe Robinson]

No, but I think one of the things I don't love. There are many things I don't like about this whole pumping up content. But what I don't like about it is if you're Always at the ready to film, to post. You're never in the moment, and so you're always in the back of your mind going, how is this going to look? Is this gonna go viral? And I think it restricts you from making mistakes that actually in the long run will serve your hour. And so if you're constantly, like, looking at it but not being in it and performing it and process, taking time to process it when it's. Once it's done, I think you're doing yourself a disservice. So I'm like, enough of this content. Enough of, like, every year I gotta have a new hour. No, you don't. Let us miss you. Let us fucking not hear from you for nine months. Like, it's great. It is so great when I don't hear from a comic and they drop a special mystery. Oh, I missed you. I missed you. I don't want to go. Yeah, I saw you, like, far out your mouth on Tuesday on Instagram and now you're dry. It's too much. So I just, I want people who are doing stand up, who are starting out to forget, cringe. I don't care. Okay. Oh, I said something funny. It didn't work. Big whoop, who cares? Like, just really be open to the process and don't restrict yourself and allow yourself to fail, because that's how you get good. You don't get good by always being good. What is that? Doesn't make any sense.

[Jesse David Fox]

Well, I missed you.

[Phoebe Robinson]

I missed you too. Even though I felt like I talked so much. You said very little. It was really a delight to hang out with you.

[Jesse David Fox]

You as well. Thank you so much.

[Phoebe Robinson]

Thank you.

[Jesse David Fox]

That's it for another episode of Good One. Good One is produced by myself, Zachary Mac, Neil Janowitz and Ann Victoria Clark. Music composed by Brandon McFarland. Write a review and rate the show on Apple Podcasts. Five stars, please. I'm Jesse David Fox and you can follow me at Jesse David Fox. Buy my book, comedy book, wherever books are sold. Thanks for listening to Good One from New York magazine. You can subscribe to the [e-mail] pod we're back with a new episode next week. Have a good one.

[Phoebe Robinson]

Arc Raiders, a multiplayer extraction adventure video game set in a lethal yet vibrant future earth. As a raider scavenging the remnants of a derelict world, you settle into an underground settlement. Hoping to thrive, you jump on the chance to start over. But doing so means you must return to the surface where ark machines roam and survivors motives remain dangerously unclear. But if you're brave enough, who knows what you might find? Play the Server Slam open test from 10-17-19 on PlayStation 5, Xbox Series XS and PC.