Why every A-lister also has a side hustle

Summary

Podcast Summary: The Indicator from Planet Money
Episode Title: Why Every A-lister Also Has a Side Hustle
Release Date: August 14, 2025
Host: NPR (Darian Woods & Waylon Wong)
Guest: John Legend

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Introduction

In the episode titled "Why Every A-lister Also Has a Side Hustle," hosts Darian Woods and Waylon Wong explore the burgeoning trend of A-list celebrities diversifying their income streams beyond their primary careers. The discussion delves into the motivations behind this shift, the economic factors influencing it, and real-world examples that illustrate the phenomenon.

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The Evolution of Celebrity Branding

Historical Context of Celebrity Endorsements

Darian Woods begins by highlighting the longstanding tradition of celebrities endorsing products, citing iconic partnerships like Elizabeth Taylor with White Diamonds perfume and Michael Jordan with Nike (03:07). This establishes a foundation for understanding how celebrity endorsements have evolved over time.

Shift from Endorsements to Ownership

The hosts note a significant shift from mere endorsements to celebrities launching and owning their own brands. Waylon Wong points out that stars are now “front and center in promoting their own brands” (04:11). This transition signifies a move towards greater personal investment and control over business ventures.

Changing Economics of Celebrity Influence

Amanda Dobbins, a contributor covering movies and pop culture, explains that the economics of celebrity influence have transformed, especially in the age of blockbuster franchises like Marvel’s superhero films (04:25). The reliance on recognizable characters over individual actors has diminished the latter's leverage, prompting stars to seek alternative revenue streams.

Notable Example: David Corenswet as Superman

Darian Woods mentions David Corenswet's role as Superman, highlighting that despite being a high-profile character, actors in such franchises might not command the same salaries as standalone A-listers (04:59). Corenswet's situation exemplifies the new economic landscape where actors leverage roles to secure future, potentially larger earnings tied to box office performance (05:16).

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Celebrity Ventures: Levels of Involvement

Ari Bloom’s Framework

Ari Bloom, co-founder and CEO of a frame brands company, outlines the varying levels at which celebrities can engage in business ventures (06:11). These levels range from low-risk endorsement deals to high-risk brand ownership:

1. Endorsement Deals: Minimal investment where celebrities simply promote products without financial stakes (06:18).
2. Investments: Financial backing in existing companies or startups, offering potential returns without the responsibilities of ownership (06:36).
3. Brand Ownership: Establishing and managing personal brands, which can yield significant profits but come with increased risk, as evidenced by ventures like Dax Shepherd and Kristen Bell’s baby product company filing for bankruptcy in 2023 (06:55).

Risk and Reward

Ari Bloom emphasizes the importance of understanding and accepting the inherent risks, citing scenarios where celebrities might lose substantial investments (07:08). This candid discussion underscores that while the financial rewards can be substantial, the ventures are not without potential downsides (07:15).

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John Legend: A Case Study in Celebrity Entrepreneurship

Introduction of John Legend

The episode features John Legend, the first EGOT (Emmy, Grammy, Oscar, Tony) winner to appear on the show, who brings firsthand experience to the discussion on celebrity side hustles (07:38).

Diverse Business Ventures

John Legend has engaged in various business endeavors, including a wine brand, a travel recommendation app, and a skincare line named Loved One, launched in collaboration with Ari Bloom (08:08). His multifaceted approach exemplifies the modern A-lister's strategy to cultivate multiple income streams.

Inspiration and Motivation

Legend draws inspiration from hip-hop moguls like Jay-Z and Master P, who established their own record labels to gain control over their careers (08:29). He emphasizes the desire for ownership and a deeper connection with audiences as primary motivators behind starting his own brand (08:39).

Building Loved One

Loved One is a skincare brand tailored for melanated skin tones, aiming to be both affordable and accessible, with products predominantly priced under $25 (09:19). Legend shares his excitement upon seeing his products in retail stores, highlighting the tangible success of his entrepreneurial efforts (09:30).

Understanding Risks and Rewards

John Legend candidly discusses the balance between leveraging his reputation and managing the risks associated with brand ownership. He acknowledges the absence of the scale that large companies possess but leverages his name and reputation to establish a meaningful connection with consumers (09:02).

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The Influence of Social Media and Influencer Culture

Normalization of Personal Branding

The hosts argue that the rise of social media and influencer culture has democratized personal branding, making it commonplace for individuals, including celebrities, to market products directly to their fanbases (05:32). This cultural shift has lowered the barriers for A-listers to establish and promote their own brands without being perceived as "selling out" (05:44).

Financial Incentives

Waylon Wong cites successful examples like George Clooney’s tequila brand, sold for a billion dollars, and Ryan Reynolds’ Aviation Gin, sold in 2020 for a significant sum (05:44). These high-profile sales demonstrate the lucrative potential of celebrity-owned brands, enticing more stars to embark on similar ventures.

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Challenges and Failures in Celebrity Entrepreneurship

Potential for Failure

The discussion also touches upon the volatility of business ventures. Examples include Dax Shepherd and Kristen Bell's baby product company filing for bankruptcy and Jennifer Lopez's restaurant closing after a few years (06:55). These instances underscore that even high-profile entrepreneurs can face setbacks.

Financial Preparedness

Ari Bloom advises celebrities to be prepared for potential financial losses, revealing candidly that losing substantial sums, such as $5 million, is a realistic possibility (07:11). This honesty serves as a cautionary reminder of the financial risks involved in entrepreneurial pursuits.

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Conclusion

The episode effectively illustrates the multifaceted reasons why A-list celebrities are increasingly engaging in side hustles and entrepreneurial ventures. Driven by changing economic landscapes, the influence of social media, and the desire for greater personal and financial autonomy, stars like John Legend exemplify the modern approach to celebrity branding. While the rewards can be substantial, the risks and challenges serve as critical considerations for those navigating this space.

Notable Quotes:

• Amanda Dobbins (04:25): “The idea that you would go see a movie because a movie star whose name you recognized was in it has changed... those characters, those IP, are the 'movie stars' now.”

• Ari Bloom (06:18): “There are different levels of involvement. So on the lowest risk end, there's the standard endorsement deal... But the trade-off is that the ultimate payday might be lower.”

• John Legend (09:02): “You don't have the scale that these huge companies have, but you do have your name and whatever that means, your reputation.”

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Additional Resources

For more insights into the economics of celebrity entrepreneurship and related topics, listeners are encouraged to explore other episodes of The Indicator from Planet Money.

Transcript

[NPR]

Npr.

[Darian Woods]

This is the Indicator from Planet Money. I'm Darian Woods.

[Waylon Wong]

And I'm Waylon Wong. Lisa Loeb is the singer songwriter behind the 90s Billboard hit Stay. I have belted this song many times.

[Darian Woods]

Is today gonna be one of those days, Waylon?

[Waylon Wong]

Uh, no, I'm not gonna sing on this show.

[Darian Woods]

Well, I only hear what I want, and so I heard you singing in my head. Lisa is known for her signature look, which is cat eye glasses.

[Lisa Loeb]

Not the cat eye of my grandmother, which is sort of that grandma pointy, very pointy pinched look. But it was a little bit more of kind of a sexy librarian. And I just realized it was a really flattering shape and it was one that I really gravitated towards.

[Waylon Wong]

Lisa said people would often say to her, you should have your own line of eyewear. And she initially resisted this idea.

[Lisa Loeb]

I think people were seen as dilettantes when you were just as interested in the T shirts you were making as the music that you were making.

[Darian Woods]

But as the music industry changed, so did Lisa's thinking, and she launched her first collection of glasses frames in 2010.

[Lisa Loeb]

I think now people see somebody's lipstick brand as a creative outlet, just like they might see a song.

[Waylon Wong]

These days, celebrity brands are more than creative outlets. They're also big business.

[Darian Woods]

Stars are starting their own companies and marketing products directly to their fans. So what is fueling this celebrity business bonanza? Today on the show, we hear from people following and making these deals, including another legendary singer.

[Waylon Wong]

It's John Legend. Guys, we got John Legend on the shelf.

[Darian Woods]

You just bled it out.

[Capital One]

This message comes from Capital One with the Venture X card. Earn unlimited double miles on everything you buy. Plus get premium benefits at a collection of hotels when booking through Capital One Travel. What's in your wallet terms? Apply [e-mail] support for NPR and the following message come from Edward Jones. A rich life isn't always a straight line. Unexpected turns can bring new possibilities. With a hundred years of experience navigating ups and downs, Edward Jones can help guide you. Let's find your rich together. Edward Jones.

[NPR]

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[Darian Woods]

Famous people have been endorsing products for generations. Think about actress Elizabeth Taylor with her White Diamonds perfume or Michael Jordan's blockbuster partnership with Nike.

[Waylon Wong]

And yet there was a time when a list movie stars were often reluctant to be the face of a brand. Amanda Dobbins covers movies and pop culture for the Ringer Podcast network, and she says one of her favorite films is Lost in Translation. In it, Bill Murray plays a movie star who goes to Japan to shoot a commercial for Suntory Whiskey.

[Darian Woods]

For relaxing times, make it Suntory time.

[Waylon Wong]

Amanda says this movie's premise reflects celebrity culture in the early 2000s.

[Amanda Dobbins]

At the time, it was seen as a little gauche for highfalutin actors to do commercials. So they wouldn't do them in the United States, but they would do them abroad.

[Darian Woods]

Fast forward to today and the super bowl ads break is just full of celebrities. And stars have also gone beyond endorsement deals to launch their own companies selling everything from liquor to baby products to cosmetics.

[Waylon Wong]

So how do we go from stars quietly doing commercials overseas to being front and center in promoting their own brands? Amanda says one big reason is the changing economics of being a celebrity, especially a movie star.

[Amanda Dobbins]

This idea that you would go see a movie because a movie star whose name you recognized was in it has changed, especially with Marvel and the superhero era. And so you're going because you're seeing a comic book or a comic character that you recognize or, you know, dinosaurs or a video game. And so those characters, those ip, are the quote unquote movie stars now. And as a result, the actual actors aren't as big of a draw and so they are not paid as much as they were.

[Darian Woods]

To be clear, a listers are doing just fine. But for something like a superhero, movie stars aren't always making millions of dollars. Up and comer David Corenswet reportedly got paid $750,000 to play Superman in the new movie that premiered.

[Waylon Wong]

And again, Superman. David Corenswet. He will be okay. He could earn bonuses based on box office performance, and his future paychecks likely will be much bigger. But Amanda says celebrities are eager to find income streams outside of show business.

[Darian Woods]

And it's not considered selling out anymore. The rise of social media and influencer culture has normalized the idea that everyone can have a personal brand and be selling something.

[Waylon Wong]

Also, the money can be really good. Back in 2017, George Clooney and his two business partners sold their tequila brand to a multinational spirits company for a billion dollars. In 2020, that same multinational company bought Aviation Gin, a brand partially owned by actor Ryan Reynolds.

[Darian Woods]

Ari Bloom is the co founder and CEO of a frame brands. He is the guy that celebrities call to make their business mogul dreams come true.

[Ari Bloom]

We started getting a lot of calls because there were a lot of celebrities saying, well, look, ryan just made $600 million on Aviation Gin. Why can't I do that?

[Waylon Wong]

And Ari says there are different levels of involvement. So on the lowest risk end, there's the standard endorsement deal. Show up and shoot a commercial, or maybe sign a contract for an ongoing deal. In these cases, the celebrity doesn't have to put in their own money. But the trade off is that the ultimate payday might be lower.

[Darian Woods]

The next level is investing in a company that could be a tech startup or it could be something less flashy like a fast food franchise.

[Waylon Wong]

And then the final level is starting a brand from scratch, something that becomes part of the celebrity's public profile. This kind of investment can really pay off, but it also carries more risk.

[Darian Woods]

Yeah. So for example, Dax shepherd and Kristen Bell's baby product company filed for Chapter 11 bankruptcy in 2023. Jennifer Lopez had a restaurant in California that closed after a few years in.

[Ari Bloom]

I've told a lot of celebrities, are you ready to lose $5 million?

[Waylon Wong]

Really? I mean, is that like a realistic number?

[Ari Bloom]

Absolutely.

[Waylon Wong]

Wow.

[Ari Bloom]

The thing that comes with ownership sometimes is like, if the business needs some capital, a lot of times the celebrities are investing, and that's great. It's a great signal if you want other investors. They also want to see that the celebrities are investing. That's actually a really important question that they always ask. But it can be a cash suck for folks. And so just getting people ready for the fact that there will be ups and downs. It's not a straight line. And, you know, not everybody's. Everybody's good with that.

[Darian Woods]

You know who is good with that?

[Waylon Wong]

Can you just start off by introducing yourself, saying what your name is and what you do?

[John Legend]

My name is John Legend. I'm an artist, I'm a songwriter, I'm an entrepreneur. And I'm excited to speak with you.

[Darian Woods]

I would be too, William. I would be excited to speak with you.

[Waylon Wong]

You know that John Legend is the first EGOT winner we've had on the show, hopefully not the last.

[Darian Woods]

That is the Emmy, Grammy, Oscar and Tony.

[Waylon Wong]

Exactly.

[Darian Woods]

And he missed out one title that he used to have, which is actually management consultant at Boston Consulting Group.

[Waylon Wong]

His first job out of college.

[Darian Woods]

So business is not new to him. And he has business ventures that have included a wine brand and an app that gives food and travel recommendations. He also worked with Ari Bloom to launch a skincare line called Loved One.

[Waylon Wong]

John told us that he takes inspiration from hip hop artists like Jay Z and Master P. They started their own record labels and showed what it looked like to have ownership over their careers.

[John Legend]

We founded Loved One as a skincare company, and before that, I had done those traditional kind of brand sponsorships, and I saw what that relationship was like. And, you know, you get a check and you do your thing and then you move on. And I decided I wanted to take more ownership and start something of my own.

[Waylon Wong]

And John says he understands the risks.

[John Legend]

You don't have the scale that these huge companies have, but you do have your name and whatever that means, your reputation. And then you try to parlay that into building a brand that will connect with the audience. And that's what we're trying to do with Loved One.

[Darian Woods]

John's skincare brand is designed for people with melanated skin that is darker skin tones, and he wanted it to be affordable. Virtually all the products are under $25.

[Waylon Wong]

Do you remember the first time you saw one of your products out in the wild?

[John Legend]

Oh, yeah, it was so cool. I think it was at cvs and, you know, it was so exciting to actually go into one of those stores and see a loved one on the shelves.

[Waylon Wong]

Yeah. Were you like, I don't want this locked up?

[John Legend]

We never locked it up, thankfully.

[Darian Woods]

Let the people have their celebrity skincare products.

[Waylon Wong]

Listen, I have the makeup from Selena Gomez's brand. I own a top from Kate Hudson's Athleisure line. Darian, I know you are a customer of Mint Mobile, which Ryan Reynolds used to be a part owner in before he sold it to T Mobile.

[Darian Woods]

Yeah, only because of Ryan Reynolds.

[Waylon Wong]

Is that why you said Ryan Reynolds? Well, you know the actors who do the Smart List podcast, They're launching their own cell phone company.

[Darian Woods]

All right, where do I sign up?

[Waylon Wong]

This episode was produced by Cooper Katzman Kim and engineered by Jimmy Keighley. It was fact checked by Cierra Juarez. Kate Concannon is our editor, and the indicator is a production of npr.

[NPR]

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