Glen Anderson couldn’t quite believe it when the woman he stopped on the street in Dublin city centre turned out to be the best friend of Oprah Winfrey.
The 18-year-old from Coolock, north Dublin, had spent some time waiting outside the five-star Merrion Hotel in the hopes of meeting Winfrey herself and asking her to appear on his podcast, Back of the Class, which he started two years ago with his friend, Ben Hanlon.
But when Gayle King – who is, in her own right, a big media star in the US – walked by, Anderson took his chance. “I didn’t know she was part of Oprah’s crew at first, but I think I’d seen her before so it kind of clicked in my mind,” Anderson said.
He pleaded with King to ask Winfrey to appear on their podcast. But she had a better idea: ask her yourself.
She recorded only a few seconds of Anderson’s pitch, and his approach was direct: “It’ll only be a two-minute interview, five questions, but it’s our dream, honestly,” he said.
“The thing is, I know if you met me, you’d like me – because I’m from the same area you’re from. I don’t come from money, I don’t come from anything. It’s just a backpack and a dream,” he went on.
And the dream came true. Winfrey’s security team messaged the podcasters on Instagram to tell them to return to the Merrion Hotel for 7pm.
Anderson and Hanlon arrived on time and were promptly escorted through the hotel. “All of a sudden, Oprah is standing there in front of us,” Hanlon said. “It was just surreal, we couldn’t believe it.”
Hanlon began the interview: “If you knew all the steps that it took to be successful, and you had to restart and take them all over again, would you take the same steps?”
Anderson continued: “Where do you get your confidence from?” Hanlon finished with, “What’s the best advice you’ve ever received?”
The podcasting duo asked only three questions, but the interview lasted more than 10 minutes. “Oprah ran with it … it was really just like having a chat with your mate,” Anderson said.
The episode is to be released on Sunday, but the pair’s work is only just beginning. “We want to go worldwide with the podcast and we want to immerse ourselves in different people’s cultures,” Anderson said.