Courtesy of HBO, Getty Images, E! IllustrationWelcome to E!'s Tales From the Top, our series on women who are leaders in their fields and masters of their craft. Spanning industries and experiences, these powerhouse women answer all the questions you've ever had about how they got to where they are today—and what they overcame to get there. Read along as they bring their resumés to life.
If you thought Phoebe Robinson's story began with a young girl dreaming of a comedy career, think again.
"I really had no interest or desire to do comedy," Robinson revealed to E! News in an exclusive interview. Yes, this is stand-up comic Phoebe Robinson we're talking about, one half of 2 Dope Queens who has her debut comedy special, Sorry, Harriet Tubman, coming out on HBO Max in just a few days.
Instead, save for doing improv in college, Robinson thought her future was in screenwriting. Then, one request from a friend shifted the direction of her fate forever. "In 2008, she was like, 'Hey, I want to just take this stand-up class for fun,' and I was like, 'Stand-up is dumb.' I didn't really watch it or care about it," she recalled. "And she was like, 'Just take the class. It's only eight weeks.' And so, I said, 'OK'...And that completely changed my life."
"Looking at it now," she added, "it's like, 'Girl, what else should I be doing but comedy?' But, at the time, I just didn't think of it that way."
Just over a decade later, the 37-year-old Ohio native went from working at film companies to studying comedy to co-starring in eight episodes of 2 Dope Queens, based on the hit podcast she and The Daily Show's Jessica Williams launched in 2016. Of course there were plenty of steps in between, but it's still only part of Robinson's wide-ranging career. There's been bylines, acting credits, other podcasts and more recently, her own book imprint, Tiny Reparations—the same name as her production company. She's authored three books, including the just-released Please Don't Sit on My Bed in Your Outside Clothes, and helmed her own interview show, Doing the Most, on Comedy Central.
While that's only a brief summary of everything currently piled atop her plate, the list begs the ultimate question of this true multi-hyphenate: How does she do it all? Robinson answered that and plenty more about her one-of-a-kind career in her chat with E! News. So buckle up, because much like her comedy, she did not hold back.
E!: I'm looking at all the stuff that you've got going on right now—your third book, Freeform adapting your second book Everything's Trash, which you're also executive producing through your production company. You have your own book imprint. You've got the Doing the Most series. You've got your debut comedy special. How does that feel to know that you're at this point now where you've got all of these things?
PR: It's really exciting. It's still like, I can't fully process that it's all happening to me. I guess I shouldn't say happened to me, but just this is what my life is looking like at the moment and I'm really excited. I think because I've had so much rejection along the way—like I've been trying to have my own scripted half-hour comedy since 2015. It's been a long road, so I feel so grateful, so excited. I'm just like, this might be the peak of my career, so let me enjoy. I feel like it's really cool to see the hard work pay off. I don't want to take any of this for granted, not even one second of it.
E!: Within a year you had launched both a production company and your imprint and took on a bunch of employees. Did you feel ready to take it all on? How does one prepare to handle all of that at once? Or is it possible to prepare?
PR: I think I definitely felt ready. Of course, I'm not going, "Oh, I have all the answers or I know everything." Each new endeavor, you help put a team together to help it run smoothly. Knowing that you're collaborating with other people in order to build anything makes it that much easier. I think all those different things of hustling to do stand-up and working at film companies, seeing that kind of stuff happen, and freelance writing, and doing the podcast stuff. I think it's just like building it brick by brick, and so each thing, you sort of pick up skills that you realize you're picking them up in the moment and stuff that you don't even realize until later down the line where you're like, "Oh, that's why that thing happened." I had a couple almost maybes with getting my own show, my own scripted half-hour, and it didn't happen. I was like, "I can't understand why it didn't happen," but now it's just like I had to go through that heartbreak and that experience and writing pilots and pitching and stuff. Now that I'm at this place with Everything's Trash, I just feel like, "OK, yeah. I'm ready to handle this and take this on and do more things that I haven't done before."
E!: Having been through this process of being a boss for two years now, what's the one piece of advice that you think other women need to know?
PR: This is easier said than done, but really don't focus on are people going to like me if I do the things that are required of a boss? When you run your own company or you're managing a team, you're not going to be able to appease everyone all the time and just say yes to whatever people want. You have to just slowly not be so fearful of if I say no or if I guide us in a different direction or if I want to take the lead on something, someone might be annoyed about it, but they might not. That's really the truth of it. A lot of times we get so scared because we're so fearful of the outcome and then more than half the time, the people, they want the guidance, they want you to be the leader so they can best succeed in their job position. I know the prevailing thought is people hate women once they get into leadership roles. I understand that and that may be true for some folks, but you're there to do a job and you're there to show off what your talents are as a leader. You just have to dive into that completely and not allow the stereotype of if you're a woman and you say a thing in a way that someone doesn't like, you're going to be labeled a bitch. You can't let that guide how you operate.
E!: Now that you've been on the other side and have a seat at tables that you didn't have early on in your career, was there anything that surprised you about how things are done that a lot of people aren't privy to?
PR: My main thing, and I think this is applicable to most fields, is you think that you're not going to be ready for something or that everyone has secret information you don't, and then you get in these rooms and you're like, "This mothaf--ka's dumb as hell and he's in charge." You know what I mean? Then it just makes you go, "Oh, I know what I'm doing. I'm smart. I'm prepared. I can handle this." And then you sort of realize so many people are faking it until they make it. So many people are figuring out as they go, which is normal. There's things within the production company that I had to figure out in the moment and that's just part of what having a job is, but this notion that everyone's got all the information and you're the one who's behind—it's just really not true. Everyone's trying to figure it out. A lot of men are just loud. They're just confidently loud and that is the difference.
E!: What's your advice for other women who are trying to ask for a raise or a promotion?
PR: I think, especially if you're going to ask for a raise, I always like to go into those meetings prepared, so I would say make a list of, explicitly, I worked on this project which yielded this sort of result, I oversaw this person, that person—be as detailed as possible and go in with a number in mind that you have. Ask above that number. That way you can meet in the middle, which will be your true number. Hopefully, if that conversation goes well and you're respected, that's great. If it doesn't and it makes you feel like you're undervalued and you are thinking maybe I should leave if they're not going to compensate me with extra perks or they're not going to nurture me financially with a huge pay increase, you can do one of two things. You can either look for another job and leave, or you can go in and be like, "OK, so you can't give me an $8,000 raise. OK. So, how about you give me a $5,000 raise and I want to take this course at night...Will you pay for that?" Or like, "Will you offer mentorships?" There are many ways to get the employer to help build your career and help you build your skill set that's outside of pay. I think pay should be the number one thing you ask for, but if there are other things you want that are going to be outside of money, but really will help you feel like you're growing your skill set and you're making an investment in your career, certainly ask for those things, too, because people say yes to that because that sounds great to see someone have that much drive.
E!: What's the best business advice you've been given that stuck with you?
PR: Years ago when I was a baby comic, I was doing this show and I was the newest comic on there. There was this after-party and people were hanging out and John Hodgman, who was on The Daily Show, was one of the comics doing it...He just asked me what I wanted to do out of my career, and I'm like, "Male comics have never asked me that before." I was just like, "Oh, well I want to do this and I want to do that, but I'm not sure. Sometimes people act like that's not being a real stand-up comedian if you want to do these other things." And he was like, "Don't worry about that. Don't pay attention to what other people are saying." He was like, "This is a fun career. This is a fun job. Build it how you want it," as opposed to being like, Well, I have to do it exactly how this white guy stand-up was doing it. He was like, "Just do it the way that you want to do it and it'll all work out. You'll have fun. You'll make money. You'll have great friends, but don't fall for the lie that you have to do everything like everyone else."
E!: What would you tell your younger self just starting out if you could tell her anything today?
PR: I would just say it's all going to make sense. It's going to feel like chaos and all the times you're told no and all the debt you had to go through, it's all going to make sense. You have everything that you need to get to where you want to go, so just hone in on that. It's OK to be frustrated, but just remember that it's all going to work out and you'll be exactly where you need to be, and all those nos were helping you to create the life that you actually want.
E!: Do you have any secret in managing all of these facets of your life? Or are you just taking it one day at a time like the rest of us? How do you do it all, essentially?
PR: I just think this whole notion of balance—it doesn't seem particularly realistic to me. I think rather than thinking work is over here and play is over there, I think it's about just having a good combination of things, and what you need this year is going to be different than what you needed three years ago. You know what I mean? I think certainly living through a pandemic, it's like, "Oh, I want to make sure I am...I'm back and I really want to make sure I spend time with my friends." I met up with a friend of mine a couple of weeks ago and we ended up having a four-hour lunch. Is that something I would've done three years ago? I'd be like, "Oh no, I got to go bop around, do this, do that..." What I need right now is to have that concentrated time with friends and really be fully present, so I think it's always just rotating between what do you need now, in six months, a year from now, and then prioritizing that and moving other things to the background a little bit. That's really how I look at it, as opposed to this work-life balance, because I just think making it two opposing things can just make it tricky.
(This interview has been edited and condensed for clarity.)
Phoebe Robinson: Sorry, Harriet Tubman debuts on HBO Max on Oct. 14.