Comedian, writer, and actress Phoebe Robinson, 34, certainly doesn’t seem like she’d be hurting for paychecks. Her podcast, 2 Dope Queens, was turned into an HBO special in 2018, she’s written two books (one of which became a New York Times best seller), and her international comedy show tour, “Sorry, Harriet Tubman,” is sold out through mid-July. But even though her career has been taking off for a while, she only recently got out of debt — and struggled to pay the bills for years, working as an office assistant during the day and performing stand-up at night. Here, she talks about dodging debt collectors, what it felt like to finally “make it,” and buying an apartment with her HBO money.
You had some dicey moments with money when you were in your 20s. When were you most worried about how things were going?
Yeah, when I had to go to housing court because I was behind on rent. I think it was in 2009. You know when you’re young and you’re like, “I can still figure my way out of this, with some smooth talking or shortcuts or the skin of my teeth”? Getting a summons because I hadn’t paid rent in months because I had been laid off from my job is not something I could just talk my way out of. That was tricky because A) it was stressful to think about what I would do if I got evicted, and B) there is a lot of shame attached to it. I felt like maybe I had chosen the wrong life path, and suddenly had a lot of self doubt. I was frustrated by the recession, frustrated about being laid off, frustrated by a million things. That was probably the hardest financial point for me. I got to stay in my apartment, but I really had to enact a plan and stick with it.
When did your career successes translate into you feeling okay, financially?
I finally got out of credit card debt in 2016, when I got the last part of my advance for my first book. Then, in 2017, I got the writing job for Portlandia. It would have been nice to celebrate that with a shopping spree or whatever, but I basically just took everything that I earned from that job and used it to pay off the rest of my student debt. So I was at a clean slate two years ago. I can’t believe it was only two years ago! I paid off the last bill in May of 2017, and then a few months later I got a letter from the student loan people saying, “Your debt has been paid in full.” I still have the letter. It was the coolest fucking thing I’ve ever gotten in the mail. I was like, “I did it! I paid it off!”
Did you really feel different? How did it affect your life?
I felt like I stopped carrying so much tension in my body. I’m a to-do list person, so every month I would write down how much my student loans were, how much I paid off that month, and how much I had left, and then I’d see how I could divvy that up over however many months in the future. I always assumed that I was going to be saddled with this massive debt until my early- to mid-40s — which is a failure of the financial, educational, and student-loan systems in this country. When I realized I had the opportunity to break free of that cycle, I thought, “Why not?” I wanted to give myself financial freedom for the first time in my life. That was important to me, not only as an adult, but as a woman, because I think there’s still an element in our society where if you marry up, and you marry the right person, that could be your financial security — and I really wanted my financial security to come from me. And that felt really good. I stopped staying up every night until 2 a.m. thinking about how much money I owed. I set up auto pay for my electric bill and my cable for the first time. I never had auto pay before, so that was cool.
Meaning, you couldn’t do autopay because you were juggling money around to pay each bill?
Yeah, exactly. I was always looking at which bill I could pay on time and which one I could let slide for now. Or I’d pay on time for a couple of months and then have a couple of months where I’d get behind. Because I was a freelancer, there was never a strong sense of security. Sure, I had gotten to a place where I had steady money — like, the podcasts were steady money. But working on Portlandia was another level. I finally felt like I wasn’t constantly getting to the 30th of every month and being like, “I don’t know what I’m going to do next month.”
I think this happens to a lot of people who get famous on the internet, where your career is going really well but it doesn’t necessarily mean you’re making tons of money. What was that like for you?
When 2 Dope Queens became the No. 1 podcast, Jessica and I were like, “Holy shit. That’s not what we thought was going to happen. This is really cool.” But I didn’t go like, “Oh, I’m famous.” I don’t get stopped in airports. No one was like, “Hey, what’s up girl?” on the street. It didn’t feel that much different. People do assume that if you have some sort of career success, that it comes with a financial windfall, but podcasting does not pay you a lot of money. It leads to other opportunities that might, but it’s not like we were getting millions of dollars or even thousands of dollars for the podcast. At the same time, it was nice to see that our hard work was paying off in career gains, even if not financially. Jessica had The Daily Show, so she was in a much different financial situation than me. I don’t know if I necessarily felt a disconnect. I felt like I was a working comic and the podcast was just one piece of a larger puzzle.
Wasn’t there a time when Oprah was trying to call you because she liked your book and you didn’t pick up because you thought it was a debt collector?
Yeah, I got a lot of those calls, especially for the student loans. If I didn’t recognize a number, I for damn sure was not picking up my phone. Of course, when Oprah was calling me and I was screening her calls by mistake, I was like, “Oh girl, you need to get your life together. If you are so terrified of answering your phone that you miss Oprah, you’ve got to pay some bills now.”
What does your money situation look like these days?
Things are looking much better. And now that I have some money, this is the most I’ve ever been concerned with saving money. When I used to have office jobs, I would contribute to my 401(k), but I was an assistant in my 20s — it’s not like I was rolling in the dough. I was like, “Okay, I don’t know what this 40 bucks per paycheck is doing in my 401(k). Whatever.” These days, I wouldn’t say that I’ve become an aggressive saver, but I’m monitoring my money a lot more. I used to avoid looking at my checking account. Now I’m very much like, “Oh, seems like you’ve been eating out a lot this month, so eat out less next month.” Or, “You’ve been taking too many Lyfts, so take fewer Lyfts.” I’ve become very conscious.
What kinds of things do you spend your money on?
I’m spending it less on physical material things and more on experiences. Part of that is just getting older. Also, my boyfriend is British, and he’s always pointing out how much consumerism we have here. The level of advertising and constantly getting people addicted to just spending money all the time — he’s like, “They don’t do that so much overseas.” I’m like, “Oh, there’s a sale at Macy’s, it’s 20 percent off!” And he was like, “You get so duped by a sale!” So now I am more mindful of it. Like, if I could get a cool leather jacket, that’s awesome, but what if I used that money to go upstate and stay in a cabin for a long weekend and go hiking and try different activities? It costs the same as going on a shopping spree to Zara, but it’s ultimately more enriching. So I’ve been getting out of that cycle of just constantly spending money, and it’s making me appreciate money more.
What was the real moment when you had a lot of money, more money than you’ve ever seen before? Like, “I can buy my own apartment in New York” money?
It was when Jess and I did the season of 2 Dope Queens for HBO. I love New York and I’ve always wanted to own property here, and that paycheck gave me the ability to do that. Again, it was like, “I could buy a cool handbag, but what is going to be a good investment for the future, if I want to retire at 65 or 70?” So I decided to invest in some real estate.
What did you buy?
It was funny to see the different tiers of what I could and couldn’t afford. I was like, “Oh, I can get a two-bedroom apartment, but I can’t get a two-bedroom apartment with a balcony.” It adds so much just to have a tiny little balcony, and I was not going to pay that. But buying my own place by myself, and seeing that it was in my name, and I own it — that was cool. If anything happens, I have this place to protect me. I’ve been very mindful of making sure money can be fun, but also be a way to safeguard my future.
What was the moment when you actually saw those numbers? Did you freak out?
My agent over at UTA told me over the phone. And I was very excited because, especially in stand-up, you make little to no money for so long, years and years and years. I wasn’t consistently making money from stand-up until 2017, and I started in 2008. That’s almost ten years. To work for that long, and then to finally see that money, it was amazing. There were a lot of moments, like when I was 27 and thinking, “Other people are 27 and they can pay their rent on time. What am I doing wrong?” And I stayed the course. So it was payment for the HBO show, but it also felt like payment for the almost ten years where I was making no money trying to get here. It all eventually came through. I earned these gray hairs and that paycheck.