After conquering podcasting, ‘Girls Gotta Eat’ co-host Rayna Greenberg is stepping into her biggest fear

When Rayna Greenberg takes the stage at the Hollywood Improv on Sunday, she will talk about sex, lots of sex, all kinds of sex, described gleefully, graphically and in detail.

But the effervescent co-host of the hit “Girls Gotta Eat” podcast will do more than just tell her “crazy, insane stories for an hour.” Taking the plunge into stand-up comedy for the first time at age 40 — she’s on a national tour that includes theaters that hold as many as 650 seats and will perform at the Netflix is a Joke festival in May — she made sure the show wasn’t just “a collection of nonsense.”

The show recaps a year of dating, which is fitting given that sex and relationships are at the heart of the podcast. “This was written very intentionally as a story with a beginning, middle, end,” Greenberg said in a recent video interview from her Los Angeles home. “The hour is full of b— jobs and anal sex but I definitely wanted to make commentary on dating and how it has changed in the last 20 years. I want to actually say something.”

Embarking on this undertaking may sound daunting but that’s what Greenberg thrives on. “I wanted another challenge. I want to do something that really scares me.”

But while her bubbly persona may at first make her seem simply freewheeling and free-spirited, she’s also savvy and thoughtful. Trying stand-up, like all her career moves, seems like a gamble but, she notes, it’s a “calculated risk.”

Raised in Pittsburgh, Greenberg graduated from Indiana University with a degree in marketing and advertising, and moved to New York the week the market crashed in 2008. “Everyone was getting fired and I couldn’t even get an internship where I’d work for free,” she recalls. But she’d worked in restaurants through high school and college and so she went back into that world. She eventually went to an abbreviated culinary school and managed restaurants for Danny Meyer, a renowned restaurateur.

Eventually she switched careers, tempted by the salaries and stability of tech startups. Working for Groupon and then Amazon had its obvious rewards — notably, a six-figure salary — but it didn’t suit Greenberg’s ebulliently wild personality. “There were so many guardrails and it was so restrictive,” she says, adding that she chafed at the hours, the dress and behavioral codes, and the lack of creativity.

It was the early days of Instagram and Greenberg had a food account on the platform, as well as a food blog, so she decided to quit her job and focus on what she knew and loved. “This was in the early days of Instagram, way before being a creator was ever a career, or you could make any money from that,” she says. “There was no ladder to the top.”

But Greenberg had $50,000 saved up to provide her some runway. And she had an intense work ethic. “It felt so fulfilling to wake up and think, ‘I’m going to outwork everybody around me and be more creative than them.’”

While she was building that career, she met a stand-up comedian, Ashley Hesseltine. “She was so funny and quick and unfiltered and we bonded immediately,” Hesseltine recalled in a phone interview. “She comes out of nowhere and you never know what she’s going to say.”

A few months later, she asked her new friend if she’d be comfortable sharing her stories about sex and dating with strangers. Unsurprisingly, Greenberg said yes and in 2018, the “Girls Gotta Eat” podcast was born.

The podcast was just an extension of what the women and their friends talked about — sex, dating, women’s health and issues like assault and politics, plus food. (They later added a second show each week about pop culture.)

“I wanted another challenge,” Greenberg said of her stand-up comedy. “I want to do something that really scares me.”

(Julien Gonzalez)

“We didn’t have a background in psychology or social work, we just had each other and a mic,” Greenberg recalls. But they constantly brought on experts and she read everything she could find. “We gave ourselves a mini-psychology degree just by doing this week after week. So we strike a balance between being relatable, normal girls and people who have been in the game for years.”

The podcast has earned more than 150 million downloads, a success Greenberg could not have imagined. “I hoped it would be great but back then it was like my food blogging — there weren’t a lot of examples of people who had gotten really huge and made all this money from podcasting,” she says. “I was so proud that I just bet on me.”

The duo used their popularity to their advantage in several ways. “When we poll our audience about dating or relationships we get 20,000 responses, which is an unbelievable sample size,” she says, noting that they not only use that data for their show but they’re planning a book based on it.

They also began touring a live version of the show even though Greenberg had never been on stage before, “not even for a talent show.” The shows — they’ve sold out 250 of them — feature strippers, dancers, T-shirt guns and plenty of banter between the women and with their audience.

“I found it very fulfilling,” Greenberg says. Still, over time, that itch to try something new returned. First, in 2022, she and Hesseltine launched Vibes Only, a company selling sex toys. Now she has created her one-woman show, seeking inspiration and influence from Hesseltine, Nikki Glaser, Hannah Berner and Taylor Tomlinson. “I was curious what would happen if I kind of removed that safety net of having Ashley by my side.”

The answer: “It was really terrifying.”

Hesseltine said that beyond Greenberg’s natural presence, the show is a product of her hard work. “She spent months writing this and it was impressive,” she says. “It’s raunchy, and hilarious without being just joke-punchline, and empowering, and you leave feeling like you got a glimpse into who she is.”

Greenberg is already thinking about her next hour of comedy and the duo are planning television and other projects. But she remains committed to “Girls Gotta Eat.” “That’s my dream and I’ll do it until the wheels fall off,” she says. “To have people’s ears for 60 minutes is such an honor.”