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

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.

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).

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).

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).

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.

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.

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.”

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.