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 with PEOPLE about his new wine brand, Basic Cellars, Kennedy looked back on his career, which began by making song videos on the now-defunct video-sharing platform, Wine. His starting point is the same as many other successful creators, such as Shawn Mendes.

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

“It was like, ‘What is it, man? What are you singing today?” Kennedy recalled of his interaction with Mendes. “We haven’t been good buddies for the last 12 years or whatever, but I’m glad he’s doing well.”

While singing online did better for Mendes, Kennedy notes, 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 that,” he says.

Not all Viners found further success after the app was merged. Some of Kennedy’s digital contemporaries “fizzled out,” he notes.

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

Even reflecting on his own switch from singing clips to comedy videos, Kennedy learned early on that “you can’t be too proud to bang your head against the wall to make a vision,” he shares. “You really have to go with what the people want.”

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

During the milestone changes in his life, Kennedy has continued some of his most beloved things, such as his famous impression of a typical mother: lovingly critical of their children, eager to chat (loudly) on the phone with friends, and not so tech-savvy, but eager nonetheless. Since becoming a father, however, he’s also folded in some fresh schticks for a newer audience and his adult original viewers might find both equally funny.

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

And that’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 tags over the years.”

“I used to joke on stage about how ‘parenting isn’t so bad, is it?’ before I was a parent I can’t believe anyone stayed in their seats,” the social media star says. “You’re just living life and you kind of reveal, ‘Okay, maybe I’ve learned that I don’t agree with that anymore.'”

He continues, “But it’s part of the journey. You have to poke fun at a lot of things, and it might turn out wrong, but as long as it’s fun, it’s okay.”

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

“I love to drink wine, and like the audience I have, I’d go to shows, I get tagged in stories. like, ‘We’re going to the Trey show,’ and they’re drinking wine.” he says, noting that he’s always leaned toward making jokes about women and their most “base” tendencies.

“Basic white girls are kind of my thing. I say that unashamedly,” he says. “I grew up around it. 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 across it honestly, and people really resonate with it. And it’s been great to see my career grow from that core audience.”

The viral sensation says his career flourished beyond the female demographic as women began bringing their male partners to his comedy shows. “The guys show up and they’re like, ‘Hey, I like this guy too.’ That whole idea of ​​being basic, I just noticed my fan base, they gravitate to that.”

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

“At the wine store … they start peppering me with ‘what are you going to pair it with?’ And what’s it for?” I say “My mouth I don’t know how to answer this,” he says. “It’s just a good wine … It doesn’t have fancy cursive on it or this and that . It’s just meant to be straightforward.”

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

“You share it with your friends. If you want a glass yourself, drink it out of the bottle, pour it into a styrofoam cup,” says Kennedy. “Hopefully it just flows into what I’m already doing, which is hopefully bringing people together through my content, through my shows, through everything else, and now hopefully sharing some wine.”