Carlos Watson is a curious man.

By the age of six, he’d been booted from school for disruptive behavior and was sent to a psychologist for learning disability testing. Yet he graduated from Harvard and Stanford Law School and later became a political commentator and host for CNN and MSNBC. 

He credits his parents, both teachers, for instilled within him a sense of wonder and an appetite for learning.  

In 2013, Watson co-founded OZY Media, where he serves both as CEO and as on-air talent. Watson has led the company to raise more than $70 million from investors like Laurene Powell Jobs. The Emmy Award-winner has created partnerships with legacy media companies like A+E Networks, iHeartMedia and the BBC. 

OZY Media produces a digital magazine, as well as popular podcasts, festivals, and television programs, including daily interview program The Carlos Watson Show, which recently launched its third season.

This conversation has been edited for length and clarity.

In your show, you seem so full of optimism. 

I think the 2020s will be the new 1960s. For the first time in half a century, we will have big fundamental debates about the things that matter most in life: love, marriage, capitalism, war, race, gender, and technology. And not just millennials, but even Gen Zers, I think, will be hesitant to accept their parents’ norms for what work means, what love means, what travel means, and what entertainment means. 

That could lead to fresh reimagining of what could be. Like in the 60s, it could lead to a lot of debate and tumble, but maybe also to a healthier society.

A slogan for your show is “Dream fearlessly.” You come from a working-class background, your parents were immigrants from Jamaica but you graduated from two of the country’s most elite universities. How did you do it?

I struggled in school early on. I somehow managed to get kicked out of kindergarten. God bless my mom. When I was graduating from college, she wanted to throw a graduation party. I was being an unthoughtful 21-year-old, saying, “Mom, I don’t want a party.” 

“It’s not for you. It’s for me,” she said. “Anyone, who saw the first 10 years wouldn’t have believed your last 10. Only a mom would have stuck by you through all that.” I got an unusually good break in my mom, my dad and my three sisters. 

It’s hard for parents. My mom wrote something for Essence magazine before she passed away, trying to give encouragement. She’d have so many parents who’d come up to her at church and remember me in a much more troubled phase. My mom would say, “Don’t give up. I’m not saying it’s going to be easy, but don’t give up.”

Posters for the new season of your talk show are splashed all over New York City. A tagline at the bottom says The Carlos Watson Show is the only one dedicated to “intersectionality.” What does that word mean to you?

We’re not one thing. We’ve got multiple interests in multiple parts of us. Rather than try to simply mute and tamp that down, maybe there’s an opportunity.

I was talking to the chef Marcus Samuelsson recently. Here’s a guy who was born in Africa, adopted into a European family at age one, went off to train in Asia, and then moved to North America. Now he’s making tuna with Cuban coffee as the marinade. 

Imagine all the creative ways he could not only thrill your palate, but your mind, and what kind of businesses he could create and how he could think about policy. 

How does intersectionality come into play with your talk show? 

Talk shows have been a wonderful thing over the last 50 or 60 years. The country has had so many interesting versions from Dick Cavett and Merv Griffin to Oprah Winfrey and Larry King. Yet, in this transformational moment, I thought we needed a different kind of talk show. 

From Cardi B to LeBron James, from Bill Gates to Ta-Nehisi Coates, we wanted a space in which the fullness of Ava DuVernay or the fullness of Amanda Gorman is welcome, not just the way people are used to encountering this person. 

I hope that what’s different about The Carlos Watson Show is a broader set of guests, and a deeper and more varied set of conversations with those people.

OZY Media gave poet Amanda Gorman a Genius Award a few years ago. Her discovery is such a gift.

Think about it—if someone had asked us six months ago could a poet do something special for us in this moment, we would have said yes but not with the same enthusiasm. Now, having seen that five-foot-tall woman in a yellow coat on a cold blustery day, 14 days after a seditious insurrection, who knew that we needed this hope? She touched us. She broke through.

You know, when I met her, she had a severe stutter. Talk about intersectionality. 

It’s been exciting to help start OZY Media, from our earliest days as a daily newsletter to what we do today with TV shows, podcasts, the OZY Festival and special college student programs like the OZY Genius Award. It’s always been about the new and the next, about not just accepting what is—but imagining what could be.

OZY Fest returns on May 15-16, 2021, this year as a live streaming event. With the theme of “Reset America,” headliners include Chance the Rapper, Dr. Anthony Fauci, Condoleezza Rice, Mark Cuban, Malcolm Gladwell, Sevyn Streeter and Marc Rebillet. For a free streaming pass or $49 interactive VIP ticket, head to www.ozyfest.com. Proceeds from VIP sales will benefit the United Negro College Fund (UNCF.) 

Listen to the full interview of The Revolución Podcast episode featuring OZY Media CEO Carlos Watson with guest co-host Linda Lane Gonzalez (Ana Crandell took the day off), and co-hosts Diego Lastra and Court Stroud on Apple Podcasts, iHeartMedia, Spotify, Google Podcasts, Amazon Podcasts, Deezer or by clicking here.