Omi
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You’re juggling so many cool projects right now. I love how you likened your career to ‘juggling a couple of boyfriends.’

Yeah it is, because everything requires a different part of me.

How is each boyfriend doing?

Well, my main boyfriend right now is definitely my book tour, so I’m traveling a lot. Everything is focused on the tour. I haven’t really done much stand-up in the past three weeks. I’ve been doing [my podcast] stuff. I’m flying back to do a couple of shows next week and I’m leaving town again. So, I’m making time for that. That feels like my mistress right now. I’m like, “I got you baby. I’m still gonna see you. Here are some flowers. Don’t be mad.”

Congrats on your book, “You Can’t Touch My Hair: And Other Things I Still Have to Explain.” I love how you said, ‘Certain things were planned and other things were unplanned’ in your career. Was the book always something you wanted to do?

I always wanted to write a book. I studied screenwriting at Pratt Institute in Brooklyn and then when I graduated I said, “I’ll just focus on working at a film company and going through the producer route.” Then I realized I missed writing so I got back into writing and started blogging in 2012. I thought, “I definitely want to do a book.” Two years later, my current agent emailed me and I was like, “Oh this is a sign.” I was so close to quitting in 2014.

Quitting what?

Comedy! I couldn’t book anything and it was really hard and I was really broke. It was tough.

Phoebe RobinsonPhoebe Robinson

Thank goodness you didn’t quit. Is stand-up something that can be taught?

I took a class on a whim at Carolines on Broadway, but I never thought I’d be a stand-up comedian. This is all a happy surprise. I think they kind of teach you the basics of standing on stage and not freaking out. I think you do have to have some natural ability, but I feel like everyone kind of sucks in the beginning. Then you slowly get better and better. You can definitely learn it, but you can kind of tell the people who are very natural and others who have to work at it. I think you can learn it.

Would you consider yourself someone who has to work at stand-up?

I think I always had natural stage presence; that was never my problem. It was more about being confident in a very male-dominated industry. I used to be in my head a lot when doing shows in front of certain guys and feeling stressed out if I did well or weird if I did badly. I had to really get out of my head and it took me a really long time to do that. That has been the hardest thing for me to overcome.

How do you overcome that?

The more you do it. I think in the beginning it’s very scary. Everyone underestimates you if you’re a woman. They don’t think you’re going to be funny. Or they don’t take you as seriously and you really have to work hard and prove yourself. A lot of my comedian friends and I say, around year eight and ten you kind of just go, “Fuck it, I don’t care. I’m good.” You get to that place where you just stop being so worried all the time. You really enjoy it. “I’m doing this for me. I don’t give a crap if this guy over there doesn’t think I’m funny.” There’s a lot of perseverance involved. There’s a lot of talking to your girlfriends who are comics and just being like, “Yo, am I crazy?” And they’re like, “No we went through it too.”

Phoebe Robinson

Along the way, did people tell you that you were funny?

I don’t want to paint it like everyone thought I was terrible and that I was sitting in my room writing jokes. I definitely had people who were encouraging. I did “Late Night with Seth Meyers” last year, and that was year seven. I really wanted to do a “Late Night” set. I think every stand-up comedian wants to do that because of the whole Johnny Carson tradition. When I did “Seth,” I was like, “I got the stamp of approval. I’m funny.” A bunch of people saw it. It felt really cool.

Were you nervous before the show?

I always get really nervous before shows. I always say, “Why did I do this? This is the worst. Can I bail?” But Seth was so great. He came backstage and I had brought a bunch of my friends to the green room. I brought the maximum amount of people you could bring. He was so sweet. He talked to all of my friends and said, “I’m so happy you’re here.” He left and I said, “I should’ve gotten a picture with him.” So one of the writers tracked him down and he said, “Let’s do a group selfie with your friends. This is a party. You should have fun. So, just go out there and kick butt.” He really put me at ease. Then I had a great time and it gave me the confidence to say, “He thinks I’m funny and that I’m going to do a good job.” Then he introduces you, and you take a big breath. They open the curtains and you just have to walk out.

A lot of performers say those nerves never go away.

Yeah, it makes you hungry and want to do well. I cried after I was done. After it happened, it was a relief.

Did you get a lot of rejection from gatekeepers in the industry?

Yeah, you go on auditions and you don’t get a callback, or you send out a writing pack. I think I submitted to write for “Saturday Night Live” for three years in a row and didn’t hear anything. It’s a lot of that kind of stuff. You kind of go, “Okay I can keep trying to fit within what someone else wants, or I can keep going out for auditions and keep going with things that make me happy.” That’s how “2 Dope Queens,” the blog and stand-up originally started.

Phoebe Robinson2 Dope Queens

“Soooo Many White Guys” is your interview podcast. What is your favorite question to ask your guest?

I try to tailor all of the questions to the person for the show. It was great when I was talking to Gina Rodriguez – she’s so wonderful – but she’s really passionate. She has these points she wants to get out about Hollywood, diversity and equality. It’s just nice to be like, “Let’s talk about a virginity story,” because of “Jane the Virgin.” She said, “Great, let’s talk about it.” She was so open and it was a really great sex-positive conversation. I lost mine later in life and I think she lost her’s a little bit later too, so it was just nice to have a frank conversation with another women. It wasn’t creepy. Sometimes if a male host were to talk about that, it could become weird. This was just two girls connecting saying, “Yeah, this is what it’s like for women.” That was a super fun question to ask.

Were there any major turning points in your career?

I think doing “2 Dope Queens” with Jessica Williams was great. It started as a spoof. I met her two years ago when I did background on a “The Daily Show” piece she did about black hair. Black hair is a running theme in my life, apparently, because of my book and everything. We just hit it off. We had always wanted to meet each other and we just hadn’t yet. I asked her to co-host a show with me as a spoof. We really hit it off and had a great time. We were like, “Let’s turn this into a podcast. Maybe we could do it ourselves and just upload it.” She knew some people at WNYC because she did an event with them and then it just kind of snowballed from there. I think we sensed that people were going to like the show, but we didn’t know it was going to explode the way that it did.

It was the number one podcast on iTunes, right?

Yeah, it was number one the first week that it premiered. I think it was number one for two or three weeks. We didn’t expect that. It was really nice to get that feedback from people who listened to the show.

Phoebe Robinson

If someone wanted to start their own podcast, what advice would you give them?

I think you kind of have to base your podcast around what you’re really excited to talk about. With “2 Dope Queens,” we love hanging out, we love celebrating comics of color, women and queer comics, so it was a very easy thing for us to do. For “Soooo Many White Guys,” I love interviewing other performers and writers and just trying to figure out what they do and just get to know them as people. I love connecting one-on-one. If you’re a woman and you love video games, it’s a great hook. You could just have a podcast talking about different video games.

With so much content out there, what’s the trick to standing out?

I think through marketing. WNYC definitely did a great job with marketing to get people to notice us. That really helped. The product was also good on its own. I think having that marriage between word of mouth and marketing.

Have you ever not connected with an interview guest?

I’d say, “No.” I only did 10 [interviews] in the first season. I think we’re going to get a second season, so it might be 10 to 12 [interviews]. We’re very particular about who we want to have on the show. I just want to pick people that I was huge fans of. I’m obsessed with Roxane Gay, Janet Mock and Hasan Minhaj– these are all people I highly respect who I’m obsessed with. We say, “I love your work.” Who is going to be a grump after you’re like, “I think you’re brilliant?” I think that’s been really helpful. I can imagine that if I had to do that show every single day, it might get kind of boring.

Phoebe Robinson

What’s the biggest risk you’ve taken?

I guess it would be when I quit my day job in 2013 to work on a pilot for VH1. The show didn’t end up happening, so I thought, “Alright, well, I guess I’m going to have to freelance and figure out how to make money.” That’s why in 2014 I thought, “I don’t know if I can do this.” It was a really hard year struggling to make ends meet.

What was your full-time job?

I was an administrative assistant at an Internet company. I assisted a couple of lawyers. Then I was just freelance writing, doing TV recaps and branded web shoots that pay like $500, scraping together my rent every month.

What’s the craziest thing that you did to save money?

I did a lot of couch surfing. Now I finally stay in a hotel, but for the longest time, whenever I went on the road, I would stay on a person’s couch. I would take a Megabus, which is fine, but at a certain point I was tired of taking a Megabus. You could take an 11:59 p.m. bus back to New York for like two dollars and I’d be like, “Score!” Now when I travel I will take Amtrak business class.  “Hello, fancy!” It’s every once in a while, not every time. It’s very quiet. You can sleep, read and get work done. When I was working on my book, I went upstate so I took the train and it was really nice.

2 Dope Queens

Where did you write your book and how long did it take?

I met my lit agent in 2014 and we hit it off and I told him about the idea for my book– an essay collection about race, gender and pop culture. We were going to call it, “You Can’t Touch My Hair.” He thought the title was so catchy. I worked on a proposal and then sold it in January 2015 and then started writing in May 2015. I finished it – my final pass – in mid-June of 2016. So it took 12 or 13 months. I was going through a breakup at the time. You get a lot done when you’re recently single. “I’m going to kick ass at life.” I moved out and I got this two bedroom apartment deep in Brooklyn. I would wake up every day and turn off my Wi-Fi and put my cell phone in another room. I would write and then take breaks and go back and write, and that’s how I was able to get it done. If I didn’t have it [together], I would write a good sentence and then go on Facebook for an hour. I had to force myself to turn it all off. Sometimes I would go to coffee shops and write too. That helps. Most of it was in my room. When I visited my parents for Christmas vacation I would hang out with them all day and stay up from like 11 p.m. to 5 a.m. and write. Then I would sleep in, hang out with them and then write again.

Are you dating anyone now?

No, I’m single.

Are you on any dating apps?

I’m on Tinder and it’s terrible, so I think I’m going to quit it. I just want to meet someone in real life. I don’t know.

What’s the worst date you’ve been on?

I haven’t had any horrible dates, it’s just more like, “There’s no chemistry here.” There’s been that sort of awkwardness, but I haven’t had a horrific experience. One guy, after sex, kind of told me that he thought I needed to workout. Fuck that guy. He sucks. So, that was shitty. I love how I’m like, “Everyone’s been great, but, oh wait, PTSD. That happened.”

What your ideal first date?

Gosh, I’m 32 now. I feel like I’m so boring. The Cloisters museum in New York and then a Broadway play. What am I, 65? But that’s what I want to do. I just want to do really nice, autumn things. I also love going to concerts. If I can do a Broadway play or a concert that would be badass.

2 Dope Queens

If you could have a drink with anyone, who would it be?

Can I do group happy hour? It would be Oprah number one, obviously. She’s amazing. She’s everything to me. Then Prince – the hologram of Prince – I would be totally fine with that. I love Malala [Yousafzai]; I think she’s so brilliant. She’s smarter than I will ever be, so I’m like, “Teach me your ways.” And then Michelle Obama. It’s a who’s who of amazing women.

Have you talked to Oprah yet?

I heard that she has my book.

What would you want to ask her?

Oh my gosh, I mean, I don’t know what I would ask. I would just tell her to talk, and then I pull out a notebook and take notes. I think she’s just so brilliant, inspiring and empowering. I had a major flight delay during the book tour so I just watched this speech she gave at Essence Music Festival. It was like 50 minutes and it was so empowering and she was funny and smart and just like, “You have everything you need to achieve whatever you want. You just need to believe in yourself.” I’m thinking, “Yeah I do, yeah I do!” as I’m flying coach in United. “Yeah, I do!”

Phoebe Robinson

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Omi