Alexis Gay left a career in tech to be a comedy creator. Perfect timing

It’s been two years since Alexis Gay quit her career in tech to plunge headfirst into comedy, and, if she’s being honest, that reckless confidence you feel pivoting away from something practical toward your passion has “a different vibe” now. “When there was nothing to lose, it was much easier. I was worse at it, but it was much easier,” Gay says. “I have to almost re-break through the same fear and vulnerability that I had to when I first started because now I have something to lose.”

Gay’s comedic videos riffing on tech culture and everyday situations earned her a decent social media following, which she’s parlayed into live stand-up gigs as well as her weekly podcast, Non-Technical, where she interviews influential figures, including Alexis Ohanian, Kara Swisher, and Mark Cuban, about everything but their résumés.

It’s certainly not a bad position to be in after two years of hustling. But growing a platform has made Gay very aware that she has one. With a bigger audience comes more scrutiny, which, as a self-proclaimed type-A person, has become an exercise in giving herself permission to fail.

“People in general, especially ambitious people, feel like they can’t be bad at something, so they shouldn’t even try it. But in order to be good at comedy, you first have to be bad at comedy,” Gay says. “There’s no direct path to being good at comedy. Or at least it’s not the one I took. I’m over here on the local train, trust me”—a local that’s had quite a few transfers.

Growing up, Gay’s sole ambition was to be an actor. But the thought of finding an agent and going on casting calls fresh out of college in 2013 was a bit overwhelming. To bide time and bring in some money, she started working at the e-commerce startup Fevo (formerly known as Host Committee).

“I immediately fell in love with entrepreneurship,” Gay says. “It was my first exposure to a professional life where if I wanted more responsibility, I just had to raise my hand and say, ‘Oh yeah, I’ll do that.’ What it was giving me was this tremendous sense of agency over my future based on how hard I worked.”

Gay left acting further behind as she moved from Fevo to Twilio, which also meant moving from New York City to San Francisco. As all-in as she was working at tech companies, being inundated in Silicon Valley culture became too much. All of her friends worked in tech. Her boyfriend at the time also worked at Twilio.

“It started to feel pretty overwhelming how much of my life was wrapped up in my job and in tech because unfortunately I started—plot twist—not liking my job,” she says. “I needed some kind of escape.”

That getaway became improv. “I realized how much of myself I had left back in New York by moving away from acting, moving away from creativity,” Gay says. “Tech is a very creative industry, especially if you’re at a young company. But it’s a very different kind of creativity.”

Gay left Twilio in 2017. She explored improv, and also rekindled her love of video editing while making a birthday greeting for her best friend that featured all of her loved ones lip-synching to the Spice Girls’ “Wannabe.”

“I made silly videos as a kid, but it had never occurred to me to do it as an adult,” she says.

Gay laid down a challenge for herself: make one-minute sketches every day for 30 days. In doing so, she realized two things: “I really love this,” she says. “And I absolutely do not wanna do it full time because I love it so much.”

Gay took a job at Patreon in 2018 running creator partnerships, which was the perfect mix of her skill sets across partnerships, operations, and now being something of a creator herself.

Despite Patreon being “the best job I’ve ever had,” she says, Gay couldn’t shake what she’d been building online with her comedy sketches. So she left—at the end of 2020, no less—and went against her initial instinct of not going full time with comedy.

“We don’t know when we’re going to be in person again. We don’t know when comedy’s coming back again. And I’m telling everybody I’m gonna leave my job and be a comedian,” Gay says. “My mom was like, ‘I don’t understand what that means. Can you explain it?’ And I would have to be like, I really can’t, but I know that it will work or it won’t. And that’s okay.”

Gay’s gamble has been working out—a little too much, to her chagrin, as she’s relearning how to let go of what people may think of her.

“My biggest fear when I started putting stuff online—this is kind of pathetic—but I was like, what if someone from my high school sees one of the videos I made and then texts it to someone else we went to high school with and says, ‘lol! look what Alexis Gay is doing,’” she says. “That was holding me back because I was not popular in high school at all. Not even a little bit. I just can’t underscore it enough. I feel that I must be very clear about this point. Trust me, if there’s a fact-checker on this story, it’ll come through.”

Gay admits her woeful lack of popularity was due to caring too much about everything she does, which is ironic now as she’s learning to let go of perfection and redefine success during the next phase of her career as a comedian.

“I look at what I’m doing right now as success. Staying in tech and not doing it? Failure,” Gay says. “Success is saying these jokes into the microphone, period. Failure is not doing it because what do I have control over? I have control over writing the jokes, getting to the stage, and delivering my best performance possible. I have no control over how the audience showed up that day, what kind of mood they’re in, whether they think I look like their ex-girlfriend so they immediately hate me.

“It’s super relevant to everything I do,” she continues, “and it’s particularly relevant to how I’m going to get myself through this moment. I try to focus on output over outcome.”