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YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

The comedian, actress and author speaks candidly about everything from her most personal experiences to how much her videos make 'on a good day.'
Anna Akana

In this series, YouTube Icon, Entrepreneur speaks with the individuals behind popular YouTube channels to find out the secrets of their success.

From a young age, Anna Akana always had a specific career trajectory in mind. She’d follow in her dad’s footsteps and join the military, then become a veterinarian. Then the unthinkable happened. She lost her younger sister to bullying and suicide.

As she grieved, Akana says it took her a long time to laugh again, but the first source of humor and distraction she found after that experience was a Margaret Cho comedy special.

“I was like, this is so healing, and I'm watching a woman who looks like me do it,” Akana says. “Maybe I could do it.” She decided to pursue stand-up herself, and for the next four years, she hit the open mic circuit. But after a while, she says, she grew frustrated with that type of gig, where she’d struggle to engage apathetic, often drunk audiences.

Related: 20 Things You Should Know About What It's Really Like to Be a YouTuber

In 2010, her brother encouraged her to try YouTube, where she soon discovered its power -- and of filmmaking generally -- to deliver jokes via video editing. “You aren't limited to just your words and it just being you and a microphone onstage,” she says.

Over time, Akana found her niche on YouTube as a role model, sharing personal stories and offering advice, empowerment and self-improvement tips. After more than seven years, her channel has 1.9 million subscribers and has garnered more than 168 million views. She’s also the author of the 2017 memoir, So Much I Want to Tell You: Letters to My Little Sister, as well as the executive producer and star of the forthcoming YouTube Red series Youth & Consequences.

“Some people dubbed me as ‘The Older Sister of the Internet,’” Akana says, embracing the title. “It does feel like all of my videos have been an expression of things I want to relay to my sister, or things I wish I could talk to my sister about. I really try to embrace that and gear my videos to younger women who I would impart this advice to -- or impart this advice to a younger self.”

YouTube has also opened the door to acting, which Akana now considers her primary area of interest. She’s appeared in the Marvel movie, Ant-Man, and the MTV series Awkward. Entrepreneur spoke with Akana, who shared that starting out on YouTube as a “one-woman crew” gave her valuable technical experience acting, directing and filmmaking.

This interview has been edited for length and clarity.

1. How did you get your start with YouTube?
My younger brother introduced me to YouTube. I really loved the idea of being able to make something during the day, because I was such a night owl at the time, and have people watch it at their convenience, in the comfort of their own home.

When I first started, I really didn't know what to make. So I started off being like, “OK, what do people do here? I guess they vlog, I'll do that.” But I got dissatisfied with it. My life is quite boring, and I was like, “no one wants to watch me go to the grocery store.” So I started experimenting with monologues to camera, which were interrupted with sketch cutaways where I would act out all of the parts.

Empowerment messages and advice or self-improvement became what resonated most with people who would keep coming back to me. I've always been very interested in self-improvement. That area of life -- the self, your relationship to yourself, how you define yourself and what you do, by that definition, has always been something that I've been naturally curious about, wanted to talk about and wanted to share with people.

2. How much of your time do you spend on a video and what does that entail?
When I first started, it would take me anywhere from three to six days to make a video, because I was kind of a one-woman show. I would have to put a vacuum cleaner where I was going to stand, pull focus, roll sound and then jump in and do all of my lines.

Now I'm really lucky that I make a living off of my YouTube videos, so that I can hire a crew. One video typically takes me four hours. I can outsource editing to someone who can do VFX a lot better than me. I work well under pressure, and my brain's gotten to a point where it will only give me an idea while I'm talking it out with my best friend, who's my makeup artist. I've gotten to a point where I will write the video while I'm in the makeup chair and print it out the moment the crew arrives to film.

For someone just starting out, I think setting a deadline is so, so, so important, and holding yourself accountable to that deadline. Because it's so much work then you think it's going to be when you first start out. And if everyone could do it, they would. But it's incredibly easy to get burned out.

I also think you should focus on quantity if you don't know what your voice is yet. I think it took me anywhere from 40 to 60 videos -- at one a week, that was about a year making stuff -- until I felt like, “I know what my voice is. I know what my brand is. I know what my end goals are in terms of how I can communicate to people and what I have to offer people.”

3. What's your content strategy? How do you decide what and when to post?
My content strategy is always honesty. Whether or not it's funny, whether or not it's thought provoking, as long as I'm being honest, I feel good about what I put out. In terms of time and upload dates and all that jazz, I used to put out Mondays at 9 a.m., and then one of my YouTube friends was like, actually Thursdays at 9 a.m. is the best time to upload content. So I was like, "OK!" So from that point on, I've been doing Thursdays at 9. I should be better at understanding the analytics and analyzing my demographics and stuff like that, but I've never been very good at being interested in those kinds of numbers. A lot of my focus is on what I am actually putting out.

These days, I've gotten to a weird point, where -- I mean, I've been doing it for like, seven years, so I sometimes feel like I have nothing left to say. So, now when I have to create a video, I'm like, “OK, what is something that I can communicate that I haven't communicated in any way before that is still authentic, I'm passionate about it and it's interesting?” After you've gone through all of your stories from your past, and after you've talked about everything that you've dealt with, now you have to go live life and accumulate more things to talk about. These days, I try to journal a lot, and I try to draw ideas from my life.

I typically can't make a video about something until I have emotional closure in my real life. Otherwise, I'm just making a video about me going through the process of something. My videos almost feel like a diary, where it's closing a chapter on a thing, and I've preached this advice, so I better follow it, otherwise I'm a hypocrite.

4. How do you leverage your YouTube channels and to what extent do you monetize them?
I used to put up once a week, but now I only put out a video if it's branded, because otherwise I cannot physically sustain my business with the amount of crew I hire and the amount of post people I hire. I love Squarespace. They really let me just be free and have fun with it. I think one of my favorite ads with them was, I made a video about getting sent dick pics on Snapchat and Twitter and like, “how do people expect you to react to that?” I never thought I'd love doing branded content or commercial work, but because the script is set and you can just go crazy with what the visuals are, it's been super fulfilling.

As far charitable partnerships, Crisis Text Line has been awesome. I've used them myself when I've been very, very depressed and felt suicidal, and I've been trying to be a big spokesperson for them, because I know the idea of calling someone on the phone must be so foreign to a teenager. You can text someone and ask for advice and resources. That's a partnership I've been really proud of.

I try to leverage YouTube as much as possible as an actor and as a director for opportunities in the traditional world. First and foremost, I'm an actor, and as much as I love content creation, there's something about taking on a different role and playing a different person that I find so creatively fulfilling and fun. I try to use the numbers that I have digitally as a marketing strategy and a promotional tool, so when casting comes down to me and a few other actors, hopefully if I have a big enough digital presence, I can use that to be like, “hey, look at me, I'm also a built-in marketing house.” And also with YouTube Red, I’m getting into the narrative game now.

5. What advice do you have for other people who want to build brands on the platform?
Know your motivation for why you're doing it, and chase art, not fame. Because everyone on YouTube has a shelf life. There was a period of time where I was coming up with Lily Singh. She went the route of the comedy of "what girls do to get ready" or blanket general gender-type stuff. She's still very funny at it, but I sort of rejected that. I was like, "No, I'm going to do sketch comedy." Her channel soared, and my channel tanked. I spent a good two years feeling like, I've made a horrible mistake, and that I should have cashed in when I had the opportunity to and made more general content. You know, she's huge now. Her and Liza Koshy and all of these other people who have followed the content in that vein are ginormous. I think only in the past year or so, I've been like, no, everyone has their own journey, and they're doing their own thing.

If you want to be a quote-unquote YouTube star, that's fine, go that route, but also know you shouldn't be chasing something for the sake of what that thing will achieve for you. You should be doing it because you really love it. And if you have amazing stuff that resonates with people, people are going to remember how that made them feel and who you are to them.

Also, this wasn't a job like, 10 years ago. If you had told me, your job is going to be just filming yourself talking about stuff, I would have been like, that's crazy. For people who are interested in being in digital, embrace whatever the new platforms are. I feel like there's always such a sense of resistance when a new thing comes out, like Twitch came out, and we were all like, that's ridiculous, or Periscope or even all of the VR stuff with Oculus and Vive. But it's the people who get on those platforms first, who see the potential and who are open to the possibility, that end up becoming the O.G.s on that platform.

6. What's a misconception many people have about YouTube?
I think there's a misconception about how much money we make. It's fallen so dramatically. Like, on a good day, my videos make maybe $500, and that doesn't even pay for two crew members on my shoot. People think, you have 2 million followers, you must be making $2 million every year, and that's certainly not the case. I mean, there's the upper echelon of YouTubers who definitely make millions and millions of dollars a month. But it's like any other industry, at the mid-tier, you're making a living, but it's not super amazing. Sometimes I want to communicate that to people, because I'm like, no, I'm not super rich.

Click through the slideshow to see five of Akana’s favorite posts.

YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

1. ‘Pregnapocalypse’

“In this video, all of the women get pregnant from an alien invasion. It was a weird, horrifying dream that I had, and I couldn't stop thinking about it. I was like, I just need to make a short about it so it goes away.

“When I directed that one, I forgot to wear a dress. One of the plot points of that short is that I give birth to the baby alien. I was like, 'all I have are pants, we're in Culver City, I live in Silver Lake, there's no opportunity.' So we just had to work it into the short that one of the girls had to rip off my pants, and the camera blocked the view of my crotch with a honey jar. It turned out to be one of the funniest moments of the entire short. I love that video so much just because it's so absurd and tickles me in a way that I'm sure it doesn't tickle anyone else.”

YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

2. ‘Women Can Be Dicks Too’

“It was a fun look at swapping gender roles and harassment in the workplace. I love it so much, because we're so over the top in objectifying men. One of the lines is like, ‘look at that candy dick!’ A lot of men in the comments are like, ‘no one talks this way,’ and the women are like, ‘yes, I got yelled at in the street yesterday, and someone called me soy sauce!’ So I love that video, because it's so satirical and over the top, but it also started a real conversation.”

YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

3. ‘Take Your Birth Control’

“This is a short I did about three months ago. It was a book adaptation of one of the chapters of my book, and it's the very personal story of me going through an abortion. But what I love about that story is that, it's completely my fault. I mean, I was terrible with my birth control. I was dating a guy who openly told me many times, ‘I don't believe in monogamy,’ and then I got upset when he cheated. So I loved being able to present that story, yes I went through this horrible thing. But it's my fault. And I learned from it. And it's still a fun, ridiculous story.”

YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

4. ‘Why Women Are Crazy’

“I've been on birth control since I was like, 15, but I went off for like a six-month period, and I was so much calmer. I was like, ‘This is amazing!’ But then I got my period, and I was like, ‘oh no, don't ever want to deal with this. I'm being pumped full of hormones. This makes so much sense as to why I feel insane all the time.’

“There's a cutaway in there -- it's like, one of the proudest jokes I've ever written -- where I'm like, ‘I have bouts of irrationality sometimes.’ And then it cuts to me yelling at a guitar, like, ‘why aren't you a violin?’ I love the dumb lines!”

YouTube Star and 'The Older Sister of the Internet' Anna Akana Explains How She Found Her Honest Voice

5. ‘Please Don't Kill Yourself.’

“That was the hardest video for me to ever upload, because I was like, ‘I don't want people to think I'm seeking attention. I don't know if this is the right thing to do.’ It's something I'd never talked about. But because I felt scared to put it up, I felt like, oh, that's why I should put it up, because this is the real thing to me. This is vulnerability. And who cares if a couple of people think I'm being an attention whore for talking about this in such a real way if it actually does help change a few minds?

“Since then, I've met young girls at meet-and-greets, or I've run into people, and they're like, ‘that video actually made me reconsider killing myself, or made me stop self-harming, because I have an older sister and I would hate to put her through that,’ or whatever it might be. Those are the ones where I was like, oh my God, that just makes me feel like my whole life is validated.”