Not even a month into the pandemic, Alexis Gay was lost, confused, and pretty miserable like most people. Alone in her studio apartment in San Francisco, she turned to the same outlet to cope she always had: comedy. On the afternoon of April 11, 2020, she posted a short video to Twitter with the line “every party in San Francisco" with typical phrases heard in the city.
"Uber prices have been so high lately."
"I wish I could stay later but I have to get up early to hike."
"Oh, it's fine, they're poly."
Turns out, it was the levity people were craving. Quickly, she racked up more than 3 million views, and in three days, she went from 950 Twitter followers to more than 15,000. (Today, she’s closer to 102,000. Dang.)
“It was like I had been doing a stand-up show for an intimate group of 50 people, and I’m up there holding the mic and all of a sudden 10,000 people pour in, and they are just standing there staring at me blankly, waiting…. Like, ‘Ok, go ahead,” Gay told Worklife.
This follower spike, while stemming from one particular viral video, had been a long time coming. Gay had grown up wanting to be an actress and had been committed to comedy as a creative outlet on the side of her tech jobs for years. At the time she went viral, she was a manager at Patreon, but she was also posting videos to YouTube, doing stand-up, making jokes on Twitter, and performing on an improv team called Happy Medium.
“That same night the video took off, I forced myself to post a joke — to rip the band-aid off. That way, if everyone hated it, they could leave,” she joked. “Better to find out.”
Spoiler alert: They didn’t hate it. Gay then decided to post a short video every week of shelter-in-place. As her following continued to grow, as did the amount of time was spending on comedy, she had a realization: she wanted to do this type of creative work full-time. She needed to leave Patreon, a job she considered the best job she had ever had.
“I had a team of seven people, people I had made a commitment to, and when I realized I couldn’t hold up my end of the deal, I knew I needed to leave,” she said.
Gay came up with an exit strategy with her boss, which included starting her podcast, Non-Technical, in which she “interviews influential leaders from tech, business, media, and beyond about everything except their resumes.” Worklife helped sponsor the first season of the podcast to help her make the leap to full-time content creator.
“I knew it would help to keep me focused to have a weekly podcast that sponsors expected, because they paid me,” she said.
The podcast is now at over 40 episodes and has quickly gained a following. As a comedian who understands tech jargon and Silicon Valley culture, listeners love the fact that she can bring a more personal and interesting side out of Silicon Valley insiders that give more of a real glimpse into who they actually are as a person. Guests so far have included Snigdha Sur (founder, The Juggernaut), Musa Tariq (Chief Marketing Officer of GoFundMe), and Chris Sacca (investor).
Looking back at her early days, Gay never thought she’d get into tech, but credits her time in the industry for her current success in a creative field. After graduating from New York University in 2013, where she created her own major (the business of entertainment media and technology), she found herself in tech, “because honestly my friend Steve worked at a start-up, and Steve’s job seemed cool,” she said. “I thought ‘Steve is one of the smartest people I know, and Steve gets to wear camo pants to work and drink free beer with his friends, so he seems on to something.’”
Straight out of school, Gay took a paid, hourly internship at a 17-person tech start-up with the intent of using the money to pay the bills while she auditioned for acting roles.
“Tech was never something I saw for myself. I saw acting for myself, and I thought this opportunity would be a way for me to do that,” she said. “But I fell in love with entrepreneurship almost immediately. It was exhilarating to be in an environment that moved so quickly — somewhere an idea could be proposed at the 10 am meeting and exist by happy hour. Acting and that part of myself just became no longer what I wanted. And that was a weird experience, because that had been my thing since I was 5 in a Christmas pageant.”
Gay moved to San Francisco in 2016 to work for Twilio. Given her new fascination with hustle culture and Silicon Valley, it felt like the right move initially but quickly took a turn.
“Twilio is an amazing company and they continue to crush it, but I found myself unhappy at that job, so I took improv classes as a way to escape tech because it was so all consuming. You know, the guy I was dating worked in tech, all my friends worked in tech, and all their friends worked in tech, and when you’d go on a hike, you’re still somehow talking about tech, and I was like…where did this other part of me go.”
At a crossroad, Gay made a big move that went against her inner love for A Plan: she left and took time to figure out what she actually wanted to do.
“I had this big plan: move to San Francisco and work a big public tech company, and have the badge and everything. Then I didn’t like it, and I was like ‘That’s not part of the plan,” she said.
She took five months off, promising herself that she would take time and not just jump into another job. “I let myself be as creative as I wanted to be and sat with this idea of what do I want?” she said. “Comedy has been something I've turned to in times of uncertainty or times of personal crisis."
With that in mind, she came up with a creative challenge: make a one-minute video every day for 30 days. The project was inspired by vlolgger Nuseir Yassin who became known for his 1,000 daily one-minute-long videos, ‘Nas Daily’. (Full circle: Gay recently interviewed Yassin on Non-Technical and considers him a friend.)
Gay created a private Instagram account to post to. She only allowed two followers: her best friend and boyfriend at the time. “I did that as a way to keep myself from watching a full season of Bojack Horseman every day while unemployed, but it was also like, what if you just let yourself do whatever, what if it wasn’t just for LinkedIn, or for other people?"
As she made the videos, she wasn’t always happy with them — sometimes far from it — but she followed the rules she set for herself. Namely, post every day no matter what, getting rid of the need for perfectionism, and instead using the videos as way to learn new technical tricks and explore comedy freely. Once she started both gaining confidence and getting better at the videos, she opened the account to more friends, and eventually made it public. But the fear was real.
“The fear was — and I've heard this a lot from people who’ve thought about starting creative stuff — ‘What if so-and-so sees it, and they think it’s bad?’ ‘What if someone from my high school texts it to another person from my high school and they make fun of me?’” she said. “Which, who cares. But when you're about to hit post, that voice can be so loud, especially at the beginning.”
At the same time, she was meeting with anyone she could to learn more about content creation and jobs she could consider. Once she started both gaining confidence and getting better at the videos, she opened her project’s account to more friends, and eventually made it public. This random creative endeavor is what led her to Patreon, where she was the first creator partnerships hire to do business development.
“The reason I got that job was that I had biz/dev experience, but I also had experience as a creator, so whoa, my weird experiment helped me get the best job I ever had,” she said. “I feel fortunate that I did all that, because it was so unlike me at the time. I was so calculated and everything has to be perfect. And it just wasn’t going to be perfect, but it had to go up. That was the lesson of the 30 days.”
At Patreon, Gay built out the go-to-market business operations team, and led and grew the partnerships team. At the same time, she was taking every improv class she could sign up for, and put together a team of friends to do comedy that sold out shows. She also started a YouTube channel, which led her to do stand-up.
Then the pandemic hit, and again, she turned to comedy to cope. She forced herself to post three jokes to Twitter a day ("that was unhinged," she says) and wouldn't let herself check social media for fun until she did. She also stopped making the long YouTube videos that no longer felt like they worked — everyone had shorter attention spans and was downloading TikTok. She made the shorter videos that ended up sending her into virality on Twitter.
“When I started putting videos of my face on Twitter, where professional contacts follow me, it felt like admitting something. That I have a great blazer collection, but I also have this other side,” she said.
Gay left Patreon in December 2020 to do comedy full-time and run her podcast, where she talks with successful people in the tech industry about their non-work life. “Whenever I watch tech interviews, I’m more drawn to the moments where they accidentally pivoted to the personal, and I wanted to make a whole show that was that,” she said. “In Silicon Valley, there’s a culture of idolatry and heroism in a way that turns people into mythical creatures, but they are human beings who also squabble over how to load their dishwasher with their significant other. I think it’s fun to peek behind the curtain of someone’s LinkedIn.”
She’s also launched a talk show on Clubhouse where she gained a casual 3.5 million followers, and continues to post videos on social media. One recent one, “Every park hang in San Francisco,” took off, gaining more than 2 million views.
“I think that video, and a lot of what I do, landed because people see themselves or someone they know in it. I know it’s accurate, because that’s who I am. Almost all of my videos are me but worse,” she said.
Overall, she feels fortunate to be able to do creative work full-time and credits some of her artistic success to bringing a tech mentality.
“I’m a perfectionist that has learned because of my tech background that perfection is way overrated if it’s going to prevent you from doing the thing,” she said.
She also spends time helping other creators learn how to better monetize social media and other content, speaking on this topic and the lessons she learned at Patreon at Worklife’s annual meeting.
Now, Gay's biggest challenge is prioritization. “I currently believe I’m better at doing business than I am at doing comedy. That’s unusual for a comedian to say. The reason that’s a great thing is that I’m financially stable. I’m not making IPO money right now, but I’m fine. I’m very lucky. The double-edged sword is that sometimes I use my ability to do business as a crutch to stop me from doing creative stuff.”
To help with that, she’s now trying to build a sustainable business by hiring people to help on project and “not taking pride in doing it all myself” so she can focus more on writing and other creative aspects. One daily practice she has comes from a book she read during her time off before Patreon, The Artist's Way, which suggests writing three freehand pages every day to unlock creativity. She still does that most days, which leads to some of her best ideas, including her recent "park hang in SF" video.
All in all, even though she’s known for making fun of tech culture, she does it out of love.
“I’m very optimistic about tech — I don’t know if that’s controversial or not. But it’s true. Everything I have is because tech platforms have enabled me to do it. What’s exciting is that tech has become a better place to be for more people. We’re not there yet - but there is more opportunity for more people to participate.”