Reynolds, Witherspoon, Jenner: The biggest celeb deals
Hey Contrarians,
From Michael Jackson to Val Kilmer, and Mike Tyson to Nick Cage, celebrities are typically not known for their financial smarts.
BUT...
Today’s celebrities are wising up and cashing out while leveraging their beauty and brains.
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For now, let’s dive into the best celebrity deals of the last 20 years.
Today in 10 minutes or less, you'll learn:
✔️ Ryan Reynolds’ brilliant contrarian marketing framework
✔️ What Clooney, The Rock, Jay-Z, and Frankel have in common
✔️ The rap icon who made a $3B deal
✔️ How Reese turned books into billions
✔️ The Kardashian not named ‘Kim’ who built a $600M cosmetics empire
✔️ How the world’s best basketball player scores paydays off-court
When fame isn't enough: The unexpected business moves by celebs to build their empires
Celebrities used to die with no cash.
They were victims of bad managers, predatory industries, and fraud. After all, they were supposed to focus on their “art”… Not the 100s of millions of dollars in value they created.
Let’s take Mike Tyson. One of the greatest heavyweight boxers of all time, he made over $300Million throughout his career. But by 2003? He was filing for bankruptcy.
“Well, if I had Oscars, a championship title, or millions of followers, I’d be making huge money moves.” Maybe. Probably not.
Today we’re covering some of the most lucrative celebrity deals ever. Some you’ve probably never heard of but could learn a lot from.
These deals are ones where celebs negotiated above and beyond any of their peers to get gigantic returns – and probably really happy kids, grandkids, and great-grandkids.
Let’s dig in.
Ryan Reynolds
His brilliant contrarian marketing framework: “Fastvertising”
Quick timeline of Reynolds’ three biggest deals:
- 2018: Purchased a majority stake in Aviation Gin, a craft gin company. He sold it for $610Million to European alcohol company Diageo in 2020.
- 2019: Became owner of Mint Mobile, a low-cost wireless provider. He sold Mint to T-Mobile for around $1.35B in March 2023 – earning a payout of more than $300M from his stake.
- 2020: Purchased Welsh football club Wrexham AFC with Rob McElhenney for $2.5M. They turned it into $4M with the FX documentary “Welcome to Wrexham.” (Season 2 spoiler: The club will continue to rise in value after being crowned National League Champions and earning a promotion to the next league.)
Not bad for a guy who got his start on a show called "Two Girls, A Guy, And a Pizza Place."
So, how does he do it?
He uses his digital marketing agency, Maximum Effort, and their framework called “fastvertising.”
This strategy leverages our short attention spans and news cycles.
They take whatever is trending in news or pop culture and immediately create ads on it for Ryan’s companies.
Like his recent one for Mint Mobile starring Ronald Gladden of the hit series “Jury Duty.” Or that time Peloton put out an ad where a husband gifted his wife an exercise bike and everyone freaked out, so Aviation Gin hired the actress.
You can’t be Ryan Reynolds, so settle for the next best thing by stealing his marketing strategy.
George Clooney
Cheers to The billion-dollar tequila brand "Casamigos"
There’s something about celebrities and alcohol that creates bulletproof brands.
Mr. Danny Ocean himself was one of the pioneers.
In 2013, Clooney co-founded ‘Casamigos Tequila’ with his friends Rande Gerber and Mike Meldman. In 2017, the trio sold the brand to Diageo for $1Billion.
Dwayne “The Rock” Johnson
On the cusp of billionaire status witH Termana Tequila
Despite his high Hollywood status, Dwayne is a bright businessman with successful ventures, including XFL, Zoa, and Acorns.
But one of his most lucrative is Termana Tequila. (I’m telling you… something about celebs and liquor.)
In 2021, the brand sold over 600,000 cases and was reportedly worth $3.5Billion, of which Johnson owns a 30% stake. Based on the approximate valuation and his equity, the billionaire club is calling.
Bethenny Frankel
The 'SkinnyGirl' who sold for $120M
In the spirit of spirits, let’s look at another intoxicating success story.
Bethenny Frankel, well-known for “Real Housewives of New York,” is quite the businesswoman. She’s a NY Times Bestseller and founder of the Skinnygirl brand, which offers low-calorie cocktails, snacks, and clothing (well, the clothing isn’t low-calorie).
In 2011, Frankel sold the cocktail line to Beam Suntory for $120 million.
But she’s not one to sell the farm and call it quits. We’re talking about the woman who once proudly said, “What’s the point of being on TV if you don’t have something to sell?”
In the Beam deal, she negotiated to keep the rights to the name “Skinnygirl.” She gets a payout for every alcohol sale, every branded shotglass, and any other licensing opportunity she dreams up.
The girl may be skinny, but the wallet’s fat.
Jay-Z
rapPer to $600M champagne tycoon
Jay-Z the rapper is arguably the greatest of all time.
Jay-Z the entrepreneur earned a net worth of over $1B, making him one of the wealthiest celebrities in the world.
On his resume:
- Founder of Roc Nation Sports, a sports agency that represents professional athletes.
- Tidal, a music streaming service that he acquired and relaunched in 2015.
- The champagne brand Armand de Brignac, valued around $600M, of which he sold 50% to luxury goods company LVMH in 2021.
When you become famous, they must make you sign something that obligates you to build an alcohol empire.
Dr. Dre
The rap icon who made a $3B deal
In May 2014, Apple announced it was acquiring Beats Electronics, the company co-founded by rapper and producer Dr. Dre and music executive Jimmy Iovine – for a whopping $3B.
At the time, it was the largest acquisition in Apple's history. It included the Beats by Dre brand of headphones and speakers, as well as the company's streaming service, Beats Music.
It was a strategic move by Apple, during the upswing of streaming’s domination of the industry and the pre-Airpod era.
Also a strategic move by Dr. Dre because, well, $3Billion.
Reese Witherspoon
How to turn books into billions
The numbers of this deal are good, but the strategy behind them is absolutely brilliant.
Reese Witherspoon founded Hello Sunshine, a media company focused on female-driven storytelling, in 2016. It sold to a newly-formed co backed by Blackstone in 2021.
The deal valued Hello Sunshine at about $900Million, with Witherspoon and other execs retaining significant ownership stakes and joining the new company's board.
Now, the strategy:
- Reese has a book club with nearly 2.5M subscribers.
- She makes deals with publishers to feature books in the club in return for gaining the rights to turn the IP into TV shows/movies.
- She shops the series to studios like Netflix, Apple TV, and HBO.
- Her media company produces it into Emmy award winners.
She's got a cycle going: gain access to content, validate it with subscribers, and distribute it on a higher scale.
It's the best kind of deal because everyone wins: The publishers get book revenue. The streaming companies get great content. Witherspoon gets licensing $, funds production on the streaming companies' dime, and cycles profits back into the book club.
Take a page out of Reese’s book.
Kylie Jenner
The Kardashian not named ‘Kim’ who built a $600M cosmetics empire
Kylie Jenner founded Kylie Cosmetics in 2015 with just a few products, including a "lip kit" that quickly became a viral sensation. (Lest we forget that one challenge that completely sucked…)
The brand's early success was largely driven by Jenner's social media following and personal brand, creating millions of built-in dedicated fans.
In 2018, Kylie Cosmetics was valued at $800Million, making Jenner the youngest self-made billionaire in history at the time (She is reported not to be in the billionaire club anymore as sales slowed since 2020).
Coty Inc., a global beauty conglomerate, acquired a 51% stake in Kylie Cosmetics for $600Million in 2019. This valued the company at $1.2Billion. As part of the deal, Jenner remained the public face of Kylie Cosmetics and retained a 49% ownership stake in the company.
LeBron James
How the world’s best basketball player scores paydays off-court
His basketball talent alone made him over $400M in his 20+ year career.
Then you throw in his income from endorsements and business ventures, and you get LeBron, the billionaire.
These deals include:
- Minority ownership of the Liverpool football club through its parent company, Fenway Sports Group (his 2% stake is worth over $30M).
- 19 franchises of Blaze Pizza, a fast-casual chain that’s growing blazing fast (sorry, I had to).
- His production company, SpringHill Entertainment, signing a deal with Universal Pictures in 2020 (Space Jam 2).
These strategic business decisions have not only made him one of the wealthiest athletes in the world but paved the way for him to continue to generate income and create opportunities for himself and future generations. A true baller, if you will.
How You Can Replicate This
My challenge to you this week:
Star in a superhero movie, become a reality TV star, or gain 5M IG followers.
Not really.
Truth is, you don’t need any of this to build an empire of your own. So many celebs end up washed up and spit out, regardless of their stardom.
It’s not the fame that makes these deals successful – it’s the smarts.
My true challenge to you:
Find a piece in one of these deals that’s replicable on your scale.
Start a content flywheel. Get a licensing deal. Build around a growing trend for a big exit.
Let’s build your empire.
I want you to be a builder in a world of users.
- Codie
⚔️ New Zelda sold 10M copies in 3 days (last game sold 30M in 6yrs)
🗽 Hm, it’s probably nothing: NYC is sinking around 1-2mm per year
🏴☠️ Twitter is the new Netflix, as far as pirates are concerned
📊 I know this is what all of you are thinking when you go to Disney
☕ Mindf*ck: caffeine just loans energy you pay back with interest
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