Trey Kennedy Reveals Where ‘Basic White Girls’ Viral Bit Originated. Now He’s Got a Wine Brand Just for Them (Exclusive)

Trey Kennedy was just a teenager when he started creating content on social media, but his charisma and humor have carried him over a decade into the future and its exciting new ways to go viral.

While speaking to PEOPLE about his new wine brand, Basic Cellars, Kennedy looked back on his career, which started by making singing videos on the now-defunct video-sharing platform, Vine. His starting point is the same as many other successful creators, like Shawn Mendes.

In fact, back in their Vine days, Kennedy says he used to collaborate with the Grammy nominee on “six-second covers,” as they were called in reference to the time limit on shared videos.

“It was like, ‘What’s up, man? What you singing today?'” Kennedy recalls of his interactions with Mendes. “We didn’t remain good buddies over the past 12 years or whatever, but I’m glad he’s doing well.”

While singing online “worked out better” for Mendes, notes Kennedy, comedy videos became a better avenue for the now-32-year-old creator, who has continued to make people laugh online after Vine shut down in 2017. “I just kept following it,” he says.

Not every Viner found further success after the app folded, though. Some of Kennedy’s digital contemporaries “fizzled out,” he notes.

“I can’t really figure out what it is,” he says of those who didn’t find new audiences. “But the few that are still going from those Vine days, I think we chalk it up to pivoting … You really do have to have an open mind.”

Even reflecting on his own switch from singing clips to comedy videos, Kennedy figured out early on that “you can’t be too proud to beat your head against the wall to do one vision,” he shares. “You kind of really have to flow with what the people want.”

That philosophy has garnered Kennedy an Instagram following of 3 million, and the term “followers” seems to genuinely fit the trajectory of his career and life. His fans have watched him become a husband, and then a dad of two. He shares son Thomas, 20 months, and daughter Eva, 1 month, with his wife, Katie, whom he married in 2020.

Throughout the milestone changes in his life, Kennedy has continued some of his most loved bits, like his famed impression of a typical mom: lovingly critical of her kids, keen to chat (loudly) on the phone with friends and not-so-tech-savvy, but eager nonetheless. Since becoming a father, however, he has also folded in some fresh schticks that newer audiences and his all-grown-up original viewers might both find just as hilarious.

“A couple of the comments that I’ve made [are] speaking to that. I did a bit where, when you catch yourself saying your dad’s phrases or something. ‘It’s a hair past a freckle,’ or something, it’s just coming out of me,” he tells PEOPLE.

And it’s part of the fun, or in Kennedy’s words, it’s part of the “humbling process of being a comedian and having these hot takes over the years.”

“I used to do jokes on stage about how like, ‘Parenting’s not that bad, right?’ before I was a parent. I can’t believe anyone stayed in their seats,” says the social media star. “You just live life and you kind of reveal like, ‘Okay, maybe that bit I’ve learned I don’t agree with that anymore.'”

He continues, “But that’s part of the journey. You got to stick your hole in the ground on a lot of things, and it might turn out to be wrong, but as long as it’s funny, it’s okay.”

One thing that seems to keep sticking with his audience? Kennedy’s comical references to wine. He’s gone viral with videos about “the five stages of wine night” and what it’s like to hear his wife recapping a “wine night.” Over time, Kennedy says he found himself enjoying wine with the same enthusiasm as his characters, and he leaned into that inspiration to launch Basic Cellars.

“I love drinking wine, and being the audience that I have, I’d go to shows, I get tagged in stories. like, ‘We’re on our way to the Trey show,’ and they’re drinking wine,” he says, noting that he’s always leaned into joking about women and their most “basic” tendencies.

“Basic white girls is kind of my thing. I say that unashamedly,” he says. “I grew up around that. I grew up around a sister and a big group of female cousins. They’re all in sororities. They’re all doing the thing. And so I come by it honestly, and people really resonate with it. And it is been great to see my career grow from that core audience.”

The viral sensation says his career blossomed beyond the female demographic because women started to bring their male partners to his comedy shows. “The dudes show up and they’re like, ‘Hey, I kind of like this guy too.’ That whole idea of being basic, I’ve just noticed my fanbase, they gravitate towards it.”

But “basic” has another meaning when it comes to Kennedy’s new line of wine. He wanted to unravel the product and let it serve consumers’ simplest needs: good taste, and branding that “screams, ‘This is just a good time,'” he explains.

“In the wine store … they start peppering me with like, ‘What are you pairing it with? And what’s it for?’ I’m like, ‘My mouth. I don’t know how to answer this,'” he quips. “It’s just a good wine … It doesn’t have all this fancy cursive on it or this and that. It’s meant to just be uncomplicated.”

With the single-serve bottles and current varieties, a California Pinot Noir and an Italian white wine, the comedian aiming it directly at the wine lovers he knows best: his audience.

“You share it with your friends. If you want a glass by yourself, drink it out of the bottle, pour it in a styrofoam cup,” says Kennedy. “Hopefully it just slides right into what I already do, which is hopefully bring people together through my content, through my shows, through anything else, and now hopefully sharing some wine.”