Friends, 

On February 4, Lionel Messi committed the unthinkable crime of being injured. As the result of a groin strain, the 36-year-old (!) star missed a friendly (!) match between his Inter Miami and a “Hong Kong XI.” The absence of the world’s greatest-ever footballer created immediate drama, which only increased after he played 30 minutes in another friendly a few days later. 

Infuriated, China’s sporting entity canceled two friendly matches against Messi’s Argentina, fans demanded refunds, conspiracy theories abounded, and Hong Kong lawmakers even joined the fray with one saying, “Hong Kong people hate Messi, Inter-Miami, and the black hand behind them.”

Though it would hardly have been the welcome Messi had hoped for from his Chinese fans, it indicated his influence. When straining your adductor is enough to spark a geopolitical controversy, you know you’re in elite company as an athlete.

Messi has reached the pinnacle of the world’s most popular sport thanks to his formidable influence on the pitch. At least in modern memory, no other player has boasted as reliable or powerful an impact as the pint-sized magician from Rosario, Argentina. 

But it’s his growing power off the pitch that is increasingly interesting. Perhaps more than any other athlete, Messi’s unique abilities and recent moves position him to build a level of wealth that far outstrips even other legends. In particular, his move to America in 2022 and the launch of the holding company Play Time have opened up new monetization opportunities that reveal much about contemporary stardom, technological shifts, and the incredible leverage of tech startups.

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Actionable insights

If you only have a few minutes to spare, here’s what investors, operators, and founders should know about Messi, the businessman.

• It’s good to be the GOAT. Being among the greatest of all time in a given sport can be lucrative. Michael Jordan leads the way in monetizing athletic excellence, with an estimated worth of $3 billion. Remarkably, MJ accumulated approximately 97% of his wealth after he hung up his high-tops. 

• A new game. The world has changed since Jordan dominated the NBA. In the forty years since his seminal partnership with Nike, social media has risen to the fore, fundamentally changing how athletes interact with their audience and leverage them financially. Additionally, the rise of the tech sector has created a high-leverage wealth-building opportunity, attracting greats like Serena Williams, Shaquille O’Neal, and many others to venture capital. 

• Messi’s money. Though Messi lags behind the Chicago Bulls legend in the financial rankings, he nevertheless monetizes like a thriving enterprise. Over his career, he’s pulled in over $1 billion in earnings, enough for a net worth pegged around $500 million. The Argentine has made his money via his sporting salary and sponsorships. He’s also undertaken several business ventures, though it’s unclear if they’ve paid off financially yet. 

• Welcome to America. In 2022, Messi traded the Champs-Élysées for South Beach, signing for Inter Miami. Though that deal made him the MLS’s highest-paid player, Messi’s additional compensation is what’s most interesting. Apple, Adidas, and Inter Miami provided special inducements to tempt the Argentine to the United States. Messi’s arrival also allows him to grow his commercial presence in the world’s most lucrative market. 

• State of play. If Messi’s wealth outstrips Michael Jordan’s in the coming years, it will be because of Play Time. Less than two years ago, Messi launched the holding company with serial entrepreneur Razmig Hovaghimian. Although they are still keeping a low profile, the $200 million vehicle has begun incubating companies and making investments.

Toward the end of the movie Air, Nike marketer Sonny Vaccaro (played by Matt Damon) turns to an off-screen Michael Jordan and asks: “Who are you, Michael?”

It is the crescendo in the film’s plot and Vaccaro’s rousing pitch, a segue between the ad-man’s narration of Jordan’s future and the commercial matters at hand. “I think you already know the answer, and that’s why we’re all here,” Vaccaro continues. “A shoe is just a shoe until somebody steps into it. Then it has meaning.”

That a film about a brand partnership was made at all is another illustration of Hollywood’s addiction to established IP, from shoes to dolls. It is also a testament to the fundamental truth in Air’s script. If we cannot be great ourselves, we aspire to be as close to it as possible, to ally ourselves with it, to adopt its trappings. In even manufactured proximity, meaning emerges. 

To Nike’s credit, its executives recognized the strength of this desire and its commercial potential. In the 40 years since MJ lent his leaping likeness to the Almighty Swoosh, “Jordan Brand” has grown into a global franchise, with Nike’s 2023 annual report attributing $6.6 billion in gross revenue to the sub-division.

In many respects, it is a brand that has eclipsed its inspiration, extending beyond basketball into other sports and the broader public consciousness. Around the world, millions rep the latest high-tops or hoodies but may only have a passing familiarity with the athlete that galvanized their creation. “Jumpman,” the brand’s iconic logo, will outlive Jordan.

In addition to securing Michael Jordan’s legacy, the apparel brand has made him a very wealthy man. Estimates suggest Air Jordan directly added $1.5 billion to Jordan’s coffers thanks to his 5% share of royalties. That figure doesn’t include the ancillary opportunities a broad, persistent brand presence affords. According to Forbes, it has helped Jordan become one of America’s 400 wealthiest people and the richest athlete on the planet, with a net worth of $3 billion. Jordan’s sale of his majority stake in the NBA’s Charlotte Hornets has been another key driver. The franchise was valued at $3 billion in its 2023 transaction, which saw GameStop short-seller Gabe Plotkin among the buyers. 

In a decade or two, we may look back on Jordan’s current wealth as a rounding error compared to modern athletes’ affluence. The rise of social media and software allows players to monetize directly, cut out intermediaries, and build extraordinary wealth. Rather than relying on executives like Sonny Vaccaro and Nike founder Phil Knight, today’s Air Jordan would run on Shopify, collect payments through Stripe, and advertise over Instagram and TikTok. Its titular star wouldn’t have just 5% royalties but 100% ownership.

More than any other athlete, Lionel Messi is best placed to capitalize on these changing dynamics. The greatest footballer of all time is a singular talent entering his second act in the richest country in the world. While Messi’s move to America’s Major League Soccer has attracted more attention, his holding company “Play Time” – which SEC filings suggest is raising $200 million in capital – may illustrate the true scale of his commercial aspirations. Through public statements and conversations between The Generalist and Play Time’s co-founder Razmig Hovaghimian, a clearer image emerges: Messi doesn’t want to simply sell sneakers – he wants to build and invest in the great software and media companies of the next generation. It’s an ambitious plan that, if successful, offers much higher upside. The business of being the GOAT looks more lucrative than ever before.

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The GOAT

The best place to begin is by tweaking Vaccaro’s question to ask: “Who are you, Lionel?” 

Even if you have the most severe sporting allergies, you will know the name Lionel Messi, but you may not appreciate his influence. In simple terms, Lionel Messi is the greatest player of the world’s most popular sport. He is the most singularly gifted footballer to grace a game loved by billions of fans across every continent and country. That he is the third-most-popular account on Instagram with approximately 500 million followers, behind rival Cristiano Ronaldo and Instagram’s own handle, indicates his celebrity. 

One of the frustrating aspects of debating whether an athlete is the “greatest of all time” (GOAT) in their respective discipline is the inherent haziness of the rubric. At this very moment, people are engaged in one of these frazzling contests. In a pub or bar, on a long road trip, or in heavy traffic, someone is saying, “OK, but greatest, how exactly? Are we comparing peaks or averages? How important is longevity? Are we basing this on the numbers, or do aesthetics matter?”

This debate makes sense for many sports: Tennis has its “Big Three,” basketball has Jordan and LeBron, and boxing imagines matchups between Ali and Tyson. 

Football’s GOAT is beyond debate. Though that statement sounds like a provocation to fans of Pele, Maradona, Cruyff, and both Ronaldos, it shouldn’t be. The remarkable aspect of Messi’s career is that he is the greatest to play the game by any meaningful measure. He has won everything individually and as part of a team, recorded goals and assists at a ludicrous rate, maintained exceptional standards for twenty years, and produced hundreds of moments of jaw-dropping genius. If you are a stats wonk, his quantitative output will astonish. If you’re an aesthete, simply watch him glide over tackles, caress a pass through the eye of a needle, or loft a chip just beyond a keeper’s reach. Rather than asking whether Messi is the greatest footballer of all time, the better question may be whether he is the greatest male athlete of all time, as suggested by ESPN’s Ryan O’Hanlon.

Far from being parochial score-settling, the question of Messi’s greatness matters when considering his commercial ceiling. Football’s history is full of many great players, a few legends, and precisely one GOAT. Holding an unparalleled position in the sporting landscape gives Messi leverage that even other absurdly talented athletes may be unable to match.

Messi’s move to Inter Miami is a manifestation of what such influence looks like in practice. In the summer of 2022, Apple paid $2.5 billion for the ten-year rights to broadcast the MLS and the associated Leagues Cup. While you can still catch games on terrestrial networks like ESPN and Univision, Apple is now the definitive destination for the domestic league. 

That deal put Tim Cook’s company in an intriguing position when Messi’s Inter Miami deal was being negotiated. Knowing that Messi’s presence in the MLS would immediately increase viewership – and potentially help it grow its smartphone share in Latin America, a geography in which it lags players like Samsung, Motorola, and Xiaomi – Apple offered an inducement. Messi receives a cut for every new MLS Season Pass purchased via Apple TV. Though the exact terms have not been disclosed, the fact that the world’s largest company (depending on the day) ceded to an individual athlete indicates Messi’s power. There’s a reason an industry expert referred to the partnership as “unprecedented.” Messi reportedly struck a similar revenue-sharing agreement with Adidas and was granted partial equity rights to Inter Miami. 

Athletes and wealth

Before focusing on Messi’s particular opportunity, let’s examine how other athletes have accumulated multi-generational wealth. 

Across his 15 seasons as an NBA player, Michael Jordan’s salary totaled $94 million. Given he is worth $3 billion today, he accumulated roughly 97% of his net worth after he left the basketball court. While many athletes struggle to make their salaries last into retirement, outliers like Jordan have succeeded in growing their earnings by leveraging their fame to strike partnerships and make lucrative investments. Often, the investments these athletes make are ones in which their star power can deliver outsized impact, lending credibility and improving customer acquisition. 

Beyond Jordan and Messi, five athletes are worth paying attention to. It should be said that these are not necessarily the highest-paid or richest athletes. Saudi Arabia’s entry into football, golf, and other arenas has allowed many sports people to earn astonishingly high base salaries. Cristiano Ronaldo, for example, makes $213 million per year playing for Al Nassr. Meanwhile, golfer Dustin Johnson secured $125 million for joining the Kingdom’s breakaway LIV tour. 

Rather than providing a high-to-low wealth ranking, we’ve focused on athletes who have been particularly creative in building wealth beyond their playing careers. 

1. LeBron James, $1 billion. One of the challengers to Jordan’s title as the NBA’s greatest ever has reached $1 billion in net worth while still competing for championships. In addition to clipping high salaries, James has taken equity in brands like Beats by Dre and Blaze Pizza. He has also spearheaded a holding company of his own, SpringHill Entertainment. That vehicle has spawned movies, game shows, and talk shows and is about to launch a men’s grooming line called “The Shop.”

2. Serena Williams, $290 million. The GOAT of women’s tennis is a prolific venture investor. As an angel, Williams backed Zipline, Masterclass, Daily Harvest, and many others. A dedicated $111 million fund, Serena Ventures, debuted in 2022 and has started capitalizing a slew of other startups. Alongside her venture activities, Williams has launched (and seemingly shuttered) two fashion brands and taken minority positions in the Miami Dolphins and UFC. Forbes estimated her 2023 net worth at $290 million.  

3. Shaquille O’Neal, $400 million. The man better known as “Shaq” has an impressive and extensive track record as an investor. At one point, O’Neal owned 155 Five Guy’s burger restaurants, approximately 10% of the brand’s total. He also owned 17 Auntie Annie’s pretzel stores, 40 fitness centers, 150 car washes, 9 Papa John’s, and a smattering of Krispy Kremes. In 2018, he launched his own franchise, Big Chicken. Shaq also has a string of venture hits that would make many managers jealous, bagging Google, Lyft, and Ring early in their lives. O’Neal is estimated to be worth $400 million. 

4. Maria Sharapova, $220 million. The retired tennis star has grown her confectionary brand, Sugarpova, into a viable business, earning a reported $20 million annual revenue. Sharapova capitalized the business herself and still owns 100% of it. She has also invested in Public.com, Supergoop, and MoonPay. Her net worth is pegged at $220 million. 

5. George Foreman, $300 million. Under its original name, “The Fajita Express,” the sloped indoor grill devised by a Midwestern inventor attracted little interest. Only after boxer George Foreman came aboard, supplying his name and star power, did the “George Foreman Grill” become a home cooking sensation. Foreman earned 40% of profits for his part until his partners bought out his share for $138 million, contributing to his $300 million net worth.

By investing savvily, especially in sports franchises or mass-market consumer brands, athletes can earn far more in retirement than they ever did as athletes. 

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A different game

Despite the transformative effect of the Nike partnership, it’s hard not to believe that Jordan was underpaid. Nike’s market cap sits at approximately 3.4x of annual revenue – applying that same multiple would value Jordan Brand at $22.4 billion. If, instead of 5% royalties, Jordan had been afforded 50% equity, his holdings would be worth $11.2 billion with room to run. 

Although Michael Jordan may not have spent late nights grinding at Nike HQ, it seems clear he delivered much more than the 5% in value he has been able to capture. Jordan Brand could not exist without him and would never have reached its current scale without his on-court brilliance and cultural cache. Though its success undoubtedly rested on the work of Nike’s employees, the one irreplaceable ingredient is the man whose name is printed on the leather.

If Jordan created the brand today, he could drive a much harder bargain. Over the last forty years, the sports, media, and technology industries have all radically changed. The result is that more power than ever rests in the hands of superstar athletes. Three shifts are particularly profound:

1. Social media has eaten traditional media. Historically, athletes had no way to communicate with their fans directly, at scale. Social media changed the equation, allowing talent to talk to an audience intimately, repeatedly, and on a global scale. If you want to sell a face cream or a pair of sneakers, you don’t need to buy a slot on NBC or take out a page in USA Today. You can simply post a picture and reach hundreds of millions of feeds. Traditional gatekeepers no longer have the same leverage – athletes have greater control than ever over their story and its distribution.

2. Superstar athletes are paid more than ever. In 1995, Jordan led the Chicago Bulls to a record-setting 72-10 season. The average NBA salary stood at $2.2 million. Today, the average is $9.5 million, heavily skewed toward the league’s best players. Stars like Stephen Curry, for example, earn over $50 million per annum. Popular leagues like the NBA have found ways to grow their appeal, deepen their connection, and increase their earnings – with part of that surplus reaching the talent. The result is that athletes have more money earlier in their lives and can better invest in external business endeavors. When Maria Sharapova decided to launch her candy brand, she didn’t need to go to outside investors; she simply funded the project herself. Athlete entrepreneurs are more financially able to use their money as risk capital.

3. Technology has reduced startup costs, abstracted complexity, and increased upside. It is cheaper than ever to start a company. It is also, at least in many respects, easier. To launch an e-commerce brand, you can use a platform like Shopify. If you want to test out a new media property, you can use tools like Anchor to launch a podcast and YouTube to distribute videos. Today’s superstars not only have the ability to leverage these products but invest in them, too. Venture investing has become increasingly mainstream, drawing interest from athletes. Though picking winning startups is difficult, celebrities have unique, differentiated advantages in building brand affinity and attracting customers. As a result, athletes can often choose from a highly competitive pool of companies, maximizing their chances of finding the next big winner. 

Taken together, these shifts have made superstar athletes the owners of their particular intellectual property. Each great player like LeBron James, Serena Williams, or Lionel Messi is the author and proprietor of their story and has greater financial and technological flexibility to monetize it. As a result, it is increasingly possible for an athlete to think of surpassing $10 billion in net worth. 

Messi’s money

Messi’s first salary at Barcelona paid him €120,000 a year, enough to support the young player and his family. He has come a long way since then. Though Messi’s precise net worth is unknown, a 2022 article estimated it at $400 million. Given this predated his game-changing move to Inter Miami, it’s likely considerably higher. By 2025, Messi’s career earnings (not net worth) are projected to hit $1.6 billion, taking into account on-and-off-field revenue. 

So, how has football’s GOAT earned his money? And how can he multiply it in the years to come?

Keep reading

Puzzler

Respond to this email for a hint. 

What has 13 hearts but no other organs?

Well done to Bruce G, Kelly O, Shashwat N, Michael O, and F Dak for answering our last riddle correctly:

I add seven to eleven, and get six. How?

The answer? Add 7 hours to 11 o’clock and you get 6 o’clock. 

Until next time,

Mario