You can be on Entrepreneur’s cover!

Wyclef On Staying Creative in the Pandemic, and Why He Loves Working With Women The multi-platinum, Grammy-winning rapper, producer and entrepreneur is housebound but keeping busier than ever.

By Kenny Herzog

entrepreneur daily
Courtesy of Siren's Call PR

Wyclef Jean likes to feel comfortable. This much is evident from the shag pillows piled atop the white sofa in his New Jersey home, where he's hanging out for our Zoom chat on a recent Thursday afternoon. In a custom Soíremaín hoodie, he lounges deeper into said sofa throughout our conversation, occasionally springing forward mid-thought for emphasis.

Jean's penchant for getting comfy and talking things through isn't news to fans who've been listening to or watching the former Fugee's pandemic-era podcast Run That Back, which will be dropping new episodes through the end of October. The show features the multi-platinum solo artist and producer's musings on life and art, plus virtual conversations and low-key peformance sidebars with everyone from Clive Davis to Lena Waithe. It's essentially the world's most chill variety series.

Run That Back, like similar celebrity livestreams since lockdown, was borne of creative restlesness and entreprenurial necessity (see: a weekly segment sponsored by Bacardi). And it's just one element of Jean's current projects outside his recording career, which saw its latest installment in last year's Wyclef Goes Back to School Vol. 1. He's also venturing into the cannabiz. That's in addition to investing in and advising for his business partner Madeline Nelson's women-driven label/management firm, Heads Music.

Over the course of a spirited half-hour back-and-forth, Jean elaborated on a number of topics, including why female-driven projects function better and what he's learned from Run That Back about compassion and creativity.

Related: Soulja Boy Is the OG Growth Hacker

At what point did the light bulb go off that you could stay engaged with fans while in lockdown?

When this happened, I was in the middle of scoring my Netflix movie and in the process of building my app [Sodo Mood Lab], and I was bringing people to the crib to start jamming. Then I noticed that ain't nobody moving, everything is online. So I figured, let's just try and start this thing off with the technology. I was bummed, but I was like, what I really can do is produce and remix records for a lot of our guests and still give them the shock factor without them being there. So this is where this started. That's why I say it's not really an interview, it's a conversation. In the studio, this is how I talk, but the public doesn't really know how I am with peers when a peer is within their space.

Did you take notes on other artists' livestreams and podcasts before starting Run That Back?

My note is it looks like we're going into another 12 months of this. So how do you connect the livestream more? The idea of going on livestream because you're playing music, no one really cares. You have to figure out how you put it in script form. At the end of the day, you're like: I have to give a piece of myself to somebody. If somebody gives you 30 years, and they know all your songs and videos, this is your give-back time, so you have to be in a super-creative space.

Image Credit: Courtesy of Siren's Call PR

It's a time for giving back, sure, but isn't it also a time for clever marketing?

The part of it that's the give-back is you're putting content on platforms you don't necessarily own the back-data for. The person making money as you put this content up is the person who owns the IPO. But a lot of us are thinking and creating situations within our own IPO, and in order to do this, we have to use these big platforms and stay consistent. If you're invisible now, in 24 months, no one will give a fuck what you're talking about. They're like, where the fuck were you when we needed you as a person? I call it the Gary Vee syndrome: We fully understand where we have to go in the sense of staying relevant, and at the same time making it exciting and creating something that doesn't exist that people will look forward to going into the future.

Given how nimble musicians have had to be since the industry started convulsing 20 years ago, you guys should be well-suited to this moment.

That's so good you say that. Every person has lome kind of love for some kind of music, and then we look at the plethora of information on YouTube, Spotify, iTunes, Tidal, and as everything stopped [in the pandemic], now people are paying attention. So the playing field gets leveled, right? As musicians, there's a great awakening. So within this great awakening, you could present to people what's called a friendly reminder. I call this period the Great Reminder, because as musicians, it gives us an opportunity of a reinvention once again through the technology.

I'm curious what you've observed about how a woman like Madeline Nelson runs her business compared to the more traditional male executives you've worked with?

They actually care. There's a real emotion there. They'll let you know too much perks is going to kill you. You know what I'm saying? They let you know you're going to rehab, and they will pick you up and bring you. Then they'll pick you up when you're out. They'll show up in the dressing room and be like, "Do you have your condoms?" A male-dominated business, we're like, "One plus one equals two. Two plus two equals four. OK. This is hot. Let's get this." We don't give a fuck. You want to kill yourself, do what you do, but how much we made this year? But if it was a female, they'd be like, "Are you happy? What's going on? Are you depressed?" I've noticed with Heads Music how they deal with depression. They treat depression like it's a disease and will pick up the phone, call the artists [and ask], "Are you okay? What's going on?" I'm like, are you guys running a psychiatrist lab here or a label? For me, that's one of the strong points, wanting to see the artist do good on the charts, but wanting them to do better with their individual health and spirituality, which I find amazing.

Related: If the Black Crowes Adapted to Ecommerce During the Pandemic, So Can You

Is there anyone you've interviewed on Run That Back who you found particularly amazing?

Lena Waithe is a successful, award-winning director, has one of the one number-one shows on Showtime, The Chi, which is incredibly written, and she [wrote] Queen & Slim. It blew me away because she said that she did Queen & Slim because she didn't feel like her voice was being heard on The Chi. So you have a number-one show, but you feel like your voice is not being heard. And that's the thing, like why settle when you are in that space where you could constantly keep climbing? It's like, I have all these Grammys, let me just let me be comfortable. Why? So what I learned from Lena Waithe was the idea of comfortability and saying I'm content with this. You should never do that. She said if she did that when she was doing The Chi, she would have never did Queen & Slim. And you can imagine what the next movie is going to be.

Is there a throughline in the stories these artists and business figures have shared on the show?

One thing I noticed from everybody is I don't care who the celebrity is or what the success is, the most important thing to them is the person who picks up the goddamn telephone. They aren't asking for a pitch. They don't have shit to say but, "Are you OK?" The idea of, shit, if we pass away, the world keeps moving, and to think Covid had to happen for us to realize that makes us understand further, "Did we pick up the phone?"

Kenny Herzog

Entrepreneur Staff

Digital Content Director

Kenny Herzog is currently Digital Content Director at Entrepreneur Media. Previously, he has served as Editor in Chief or Managing Editor for several online and print publications, and contributed his byline to outlets including Rolling Stone, New York Magazine/Vulture, Esquire, The Ringer, Men's Health, TimeOut New York, A.V. Club, Men's Journal, Mic, Mel, Nylon and many more.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

James Clear Explains Why the 'Two Minute Rule' Is the Key to Long-Term Habit Building

The hardest step is usually the first one, he says. So make it short.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Business Solutions

Grab Microsoft Project Professional 2021 for $20 During This Flash Sale

This small investment is well worth the time it will save your team in organizing and monitoring project work.

Business News

Microsoft's New AI Can Make Photographs Sing and Talk — and It Already Has the Mona Lisa Lip-Syncing

The VASA-1 AI model was not trained on the Mona Lisa but could animate it anyway.

Data & Recovery

This File Backup Tool Subscription Is $25 for Life for One Week Only

AOEMI Backupper Professional is designed to protect, store, and transfer user's files for them.