Issa Rae on Failure, The Old Hollywood Boys Club & Throwing Chairs

When Issa Rae joined us on stage at Create & Cultivate Seattle as keynote conversation with CEO founder Jaclyn Johnson there was a fair amount of fan-girling that went on. Which, fair. The self-made YouTube star has made moves since Awkward Black Girl, creating and starring in HBO's Insecure, as well as landing in Time Magazine's "Firsts" issue, credited as the "First black woman to create and star in a premium cable series." 

Here's what she shared with the audience. 

On the old boys club: 

"You’re constantly getting excuses from higher-ups that they can’t find people.. But they’re not trying hard enough. 

Sometimes you have to take a risk on people that have no experience, so they can work. There is an old boys club at the end of the day. They’re recycling people and they are risk-averse. But when you have black and Latino people supporting a black show, the results are clear and it feels authentic. For us it was making sure that we’re doing our part to give other people the spotlight." 

On your ‘one shot': 

"During Awkward Black Girl... I was producing that out of pocket, and my pockets were empty. That was hard. I produced it with 25 dollars. We set a Kickstarter goal of 30k and ended up raising 60k. And then Pharrell [Williams] contacted us in the middle of our season and asked if he could fund the second season. That changed the game from there."

Shonda Rhimes and co ended up reaching out to Issa. 

"I was producing Awkward Black Girl out of pocket. And my pockets were empty." 

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"I pitched them a show called I Hate LA Dudes. It was something true to my heart and true to their hearts too. I developed that with them. I felt like it was my one shot. I was extremely eager to please. Shonda was great at hand-holding but where I fell short was navigating network notes. When the studio and network would give notes I was a 'yes woman' and I lost what I was trying to say in the process. At the end of the day they want you to funnel their notes through your voice. I didn’t get that at the time. They ended up passing on the series. I thought that was my one shot. So when HBO called and I knew that I should never dilute my voice again." 

On failure: 

"I can’t go a day without failing. I think where I thrive is knowing I’m not gonna make that mistake the same way again." 

On bringing up other people: 

"Too often we try to find people that are established or go the star route and networks encourage that. But I’d been following Yvonne’s [Orji] career for such a long time, just via Facebook. She was one of the random people I had friended post election when she had posted a video trying to claim Obama as a family member after the election. I thought it was the funniest shit ever. I just friended her. When we got picked up I hit her up and said, ‘Hey will you audition for this?’ 

The web is where you can be the most free. It’s your pure unfiltered voice. And it’s where you can highlight other content creators. Which is what Issa Rae Productions is about. It’s about building a pipeline to get people into television and film. It’s been super exciting as a genuine fan of dope artists. 

Everyone on the Insecure team is all about that. Elevating other content creators. That’s what it’s going to take to shift the industry and shift the crazy excuses as to why there aren’t relatable shows of color." 

On first mini-viral moments:

"Me and my girlfriends were sitting around drinking Moscato one night. Because we heard Lil' Kim talk about it in a song. And we could afford it. We had a freestyle session where I thought, I need to record this. We are killing it. We weren’t. I used Windows Movie Maker and turned it into a music video. It spread around our campus." 

On breaking into the industry:

"At the same time [as the viral videos] I was trying to break into the industry traditionally. I came to LA to try and sell a spec script I wrote with a partner. I was told by executives that there was no audience for the kind of work we we’re trying to do. I had a lightbulb moment when I thought I am such an avid user of Facebook, it would be so cool to do a mocumentary about what it’s like to be black at Stanford and just upload it. And did it. It started spreading to other schools. For me that was an epiphany that I had direct access to an audience. But I graduated and didn’t do it again until about two years later. Awkward Black Girl was my third web series. It blew up from there." 

On being ‘Insecure’

For Awkward Black Girl I was 100% nervous. I had never put my own face out there. I wanted another friend to star in it, but by the time I actually went through with it she was like, ‘Girl I’m in law school.’ I knew I was running out of time. And I knew the character and that I could play it. That took a lot of pumping up. I know how ruthless people are, but I had to get over it. I had my best friend come over and showed her the first edit and watched her genuine feedback and laughter. Then I closed my eyes, uploaded it, and went to sleep. By the time I woke up, it had spread beyond my network, which I thought was just incredible." 

"I can’t go a day without failing."

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On representation:

"I was a fan of television shows that had a specific type of humor. But I never saw people of color representing that humor. Sometimes they were being laughed at or the butt of the joke, but they weren’t cracking the jokes." 

At the time Issa had a film blog where she would vent her frustrations. 

"On the blog I would talk about what I wanted to see. And I would talk shit a lot. And one commenter was like, ‘Bitch you talk a lot of shit, why don’t you do it?’ And I was like, 'Oh maybe I can.' So I really created Awkward Black Girl so I could continue to talk shit." 

On the start of her career:

"There is someone who should have equity and is the reason I put out the show. Commenter ShyWeb18 is responsible for my entire career. Shoutout to her."

On female friendships: 

"When I was in in college I loved watched the reality shows for the drama and the ignorance and the ridiculousness of it. But then I thought this is all we have depicting black female friends. We’re constantly battling each other, we’re conniving. We’re throwing chairs and wine bottles at each other. And I’ve never thrown chairs in my life.. at my friends. We wouldn’t be friends after that. I wanted to depict the real friendships that I knew. Yvonne’s character Molly is based off of one of my best friends. 

I love women. Some of my best friends are women. There’s just a comfort and a shorthand and a support system. For me it comes from being around dope active women. There’s a narrative that we don’t support each other, that we’re catty, that we tear each other down. That’s never been my experience. It’s so rewarding to grow with so many different women. "

Photo credit: Smith House Photography

Arianna Schioldager is editor-in-chief at Create & Cultivate. You can find her @ariannawrotethis. 

MORE FROM OUR BLOG

Celebrating #WorldKindnessDay with the Founders of The Kind Campaign

Killing it with kindness.

Kindness Day was born when a collection of humanitarian groups came together on November 13, 1997 and made a “Declaration of Kindness”. Donating books, food or clothes to your local community is a great way to celebrate. However, these boss ladies went even further and launched an entire campaign.

Both Lauren Paul and Molly Thompson, co-founders of The Kind Campaign experienced bullying in middle and high school. Experiences that shaped who they are and gave them the first-hand knowledge needed when they launched Kind Campaign. 

While attending Pepperdine University, Lauren had the opportunity to intern for Tom Shadyac on his documentary project, I Am. Wanting to do something since being "severely bullied" in middle school, Lauren shares that the experience working on a documentary gave her the idea to work on a documentary of her own. One that specifically addressed the issues of bullying. 

Lunch in the Broadway Cafe at Pepperdine was the starting point, when both Molly and Lauren enthusiastically said, “YES” to an “uncharted adventure.” 

“It was during that life-changing lunch,” shares Lauren, “that I pitched the idea about creating a documentary.” Molly was all-in. “From that moment on,” she says, “we dove head first into everything. The moment we turned on the cameras and held our first interview for the film, we both knew there was a huge potential for something greater.” 

That was in 2008. Bullying wasn’t the hot-button topic it is now. They didn’t know if people would be willing to open up about their experiences. But the moment women and girls started talking it was clear that the issue had been swept under the rug for too long. Like Lauren, Molly had her own share of bullying experiences in high school. “Bullying specifically between females,” shares Molly, “was not addressed. It was almost expected and accepted as a rite of passage.”

The college seniors were about to launch a movement. 

Those initial interviews for Finding Kind, paved the road toward Kind Campaign, which officially launched in February, 2009. Since inception, Molly and Lauren have spoken at over 400 schools in North American and the UK, activated 390 Kind Clubs across the globe, and Lauren shares that “Kind Campaign Assemblies are now hosted by faculty and volunteers almost every day of the school year.” The co-founders are getting ready to head out on their 12th Founders Assembly Tour. 

It’s been an incredible journey for both. Lauren grew up in Orange County and Molly in Dallas, but after sharing a laugh over a YouTube video their junior year of college the two became “fast friends.” 

“It feels very surreal looking back on the last several years,” shares Molly who gave birth to daughter Lyla last August and understands the power of the messaging more than ever. “When we first started Kind Campaign, we were running on passion and adrenaline, pulling all nighters and barely scraping by with enough funds to keep going and spreading the movement.” Now the goal of offering free global programming is a reality. 

Lauren knows that more than ever young women need to know “that they matter, they are heard and they are equal. That no one can tell them who they are and what they can and can't accomplish.” She also brings up the power of social media and the influence it has over girls’ self-esteem. “There needs to be more conversation about how to have a healthy relationship with your phone. To remind girls that their worth is not determined by how many likes or followers they have.” Adding, “This is something we ALL need to hear and think about.” 

More from the co-founders below. 

What do you think young women and girls need to hear now more than ever?

Molly: That they are strong, powerful, beautiful, inspiring, unique, and more than capable of accomplishing anything that they put their minds to. And then remind them of this over and over and over again in order to combat the mixed messages that women and girls are fed by the media, by what is going on in our world today, by the experience that they have at school or in the workplace, and by the things that they start to tell themselves because it has become so ingrained within them. I think more than anything they need to be encouraged and allowed to be whoever it is they truly are, rather than to be told what it is they can or can't do, or be put in a box. Now, more than ever, I think we need to remind ourselves and our peers that we are enough, more than enough; and no one can take away our intellect, our self-respect, our beauty, our talents, our voice, or our worth

How can we each carry kindness into the world?

Lauren: Serving others doesn’t necessarily mean starting your own non-profit or dedicating your whole life to community service. One of my favorite quotes was said by Howard Thurman. It reads: “Don't ask yourself what the world needs; ask yourself what makes you come alive. And then go and do that. Because what the world needs is people who have come alive.”

I deeply believe in that motto. There is nothing better than a person who comes alive when they tell or show you what they do or what they’re passionate about, whether that’s being a teacher, sailing, owning a bakery, being a lawyer, singing or being a mom. You will be the best you if you find a way to do what you love and love what you do.

Molly: Every single person has the ability to change the course of someone else's life, just by being awake, being aware, and being kind. We truly do not know the battles that others face in their day-to-day lives, so if we just focus on ourselves and our ability to carry kindness into the world, and we are a light in someone else's life (however small it may be), we have the chance to make someone's day and even save their life.

What is a time in your life when you thought, 'I can't do this anymore?'

Lauren: When I went through my experience being bullied in middle school I remember waking up every morning and thinking that there was no way I was going to make it through another day of school.  I went to bed every night not wanting to wake up in the morning. I truly lost myself.  But with the support of one friend and my family, I was able to dig myself out of that depression and now I look back and that dark time and know that it all happened for a reason.  Without that experience, I would not be doing the work I am doing. I am now able to stand in front of hundreds of girls in our assemblies and remind them that their school experience is just one chapter of their story.  That no matter how dark the chapter is that you are in, there is a whole life ahead of you, waiting to be lived, filled with love and adventure.

What's a surprising story you heard during a school assembly that's stuck with you?

Lauren: Rachel is a girl we met during our last Spring tour while in Utah. At the end of all of our assemblies, we take a picture with the group of girls we are speaking to and post the picture on Kind Campaign’s social media. We were scrolling through the girls comments on her school’s photo and came across this comment from Rachel:

“I was at the Kind Campaign assembly at Draper Park. You guys really changed my point of view on everything. I can relate to everyone in the film. Every girlfriend I've had, I have lost.This morning when I woke up I was thinking about committing suicide. I came to school today on the verge of tears. Once I got in and sat down I wasn't really paying attention but once I watched the movie and I was in tears. I came up and shared my Kind Card. It was about one of my best friends. He stood by me through all my hard times. Once I got home I realized that even though some girls can be rude and don't understand what their words can do that it shouldn't be worth dying over. I called my best friend and talked to him for an hour. I was just crying my eyes out. Your assembly today? Yeah, it saved my life.”

We were really moved after reading that and immediately connected with her through Instagram and offered further support with our in-house counselor. Our on-call therapist counsels girls and parents who write to Kind Campaign and need extra conversation and support. This service is free of charge. I still keep in touch with Rachel and she is happy, healthy and doing so well!

What does female empowerment mean to you?

Molly: Everything. Female empowerment is everything. Celebrating each other, our accomplishments, our differences, our failures and our victories so that we feel emboldened and proud of who we are with the knowledge that we are good enough. It has taken on a new meaning since having Lyla. Even though it's always been important to me, now it's even more personal. Not just for myself, not even for all of the incredible young women we meet through our work, but for her - my little heartbeat. She needs to know her worth and feel supported and celebrated. Not judged and picked a part, scrutinized under a more harsh microscope than others.

"Female empowerment is everything."

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Lauren: It means getting to know yourself. Loving and respecting your body, heart and mind. It means doing your best to let go of those female insecurities we all harbor. It means feeling genuinely happy for other women and celebrating their beauty, uniqueness and accomplishments without going to a jealous or competitive place. Don’t be a part of drama and gossip.

What’s on your career bucket list?

Lauren: I’ve always dreamt of writing a book. I would also love to continue speaking in other countries.  Molly and I took our Kind Campaign Founders Assemblies to the UK last year and I would love to see our programming continue to spread globally.

Molly: Honestly, in so many ways I feel like I've already exceeded what any bucket list could capture. Not to sound cheesy, but I really do feel so unbelievably lucky to be in the position I am and do what we do. We have always said, "If we can just impact one person, then it has all been worth it." And thanks to social media for making this world seem so small and allowing us to see Kind Campaign's impact, we have the opportunity to hear from that "one person" who has been impacted on a regular basis. So I guess my career bucket list would be to keep Kind Campaign's messaging current enough as time goes on to continue to have such a profound impact on people. And to meet Oprah.