How a new generation of sports and entertainment stars are changing the narrative when it comes to wealth

By Stephen O'Kane

A new breed of high-profile athletes and entertainers are now effectively becoming their own CEOs, with stakes in a range of business and investment activities. Working with a trusted wealth partner means they can aim higher for longer, says Stephen O’Kane, Director at AlTi.

A subtle but significant shift is underway in how many of the world’s leading athletes and entertainers are managing their careers. Their access, strategies, and outlook are starting to evolve as they have increasing exposure to platforms and investment opportunities that allow them to follow their passions and embark on successful new ventures.

Athletes are looking to extend their earning opportunities, as their on-field career is often limited to little more than a decade. Entertainers, meanwhile, can have much longer earning spans from their primary careers – for example, potentially being able to sustain high incomes from royalties – so may have different motivations.

However, as they look to expand, diversify, and extend their primary income streams, they usually have one thing in common: They are driven by the entrepreneurial spirit that has helped to deliver their self-made success. The upshot is that they are starting to gather some best-in-class teams around them to maximize such opportunities, mirroring the way they would seek to access the best people to help them deliver elite performances on the field, on stage, or in front of the cameras. 

Well-researched investments, coupled with sound financial advice, are enabling them to successfully enter a range of markets. There is often a draw to physical assets such as residential real estate, which is easy to access and understand. But as careers expand and incomes increase, their investment strategies tend to evolve and mature – expanding to other sectors.

Indeed, you could say that there has never been a better time for them to be in this entrepreneurial space. These individuals are wielding a new power, no longer constrained by the traditional agency or studio model. Elite athletes might use their sport as their “shop window,” but look inside and it’s an array of clever, brand-aligned investments that say much about these talented “CEOs.” They are energized, empowered, and enthusiastic about the opportunities they are creating. They think big and aren’t afraid to take advantage of what their unique position offers them.

Consider, for example, actors Ryan Reynolds and Reese Witherspoon. Reynolds, already a successful television and movie star, has used his business platform, Maximum Effort – originally a movie production and digital marketing agency, but now much more than that – to stretch beyond front-of-camera performances. That has included investing in UK soccer club Wrexham AFC, the Alpine Formula 1 racing team, spirits brands such as Aviation Gin, telecommunications, online investment platform Wealthsimple, and more. In 2023, Mint Mobile, a budget wireless provider backed by Reynolds, sold for $1.3 billion¹, demonstrating that these endeavors are not “just for fun,” but are in fact generating real value.

Meanwhile, Witherspoon, despite being an Oscar-winning Hollywood success, was unimpressed by what the film industry had to offer women and decided to take matters into her own hands. In 2016 she launched Hello Sunshine, a multiplatform media brand and content company, to drive the creation of female-centered stories. It has produced hits such as “Big Little Lies” and “The Morning Show,” and in 2021, when Witherspoon sold a majority stake in the company, it was valued at $900 million². This year, Forbes named her the world’s richest self-made female actor (with an estimated net worth of $440 million)³.

Other notable celebrity entrepreneurs include rapper Snoop Dogg, who founded Casa Verde Capital in 2015, and actress Priyanka Chopra-Jones, who helped launch dating app Bumble to the Indian market in 2018.⁴

By strategically investing – including in businesses aligned with their values – many high-profile personalities are taking control of their wealth, and with the proper guidance they are creating lasting legacies that go far further than the field, court, or stage.

In the sporting arena, the Williams sisters epitomize this divergent success. Tennis may have made Venus and Serena household names, but they’ve since stretched into fashion, entertainment, investing, and philanthropy. 

In March 2022, five months before retiring from the court, 23-time grand slam singles champion Serena raised $111 million for her new early-stage venture capital firm, Serena Ventures⁵. The company has backed fintechs Propel and Cointracker, and edtech Masterclass, and in 2019, Serena participated in a funding round for nursing tech startup Mahmee.

We’re seeing more and more people considering the impact of their investments alongside their desire to achieve financial returns, aligning their wealth with their deeply held values. Serena is just one example of an investor purposefully channeling her resources to enable positive change – her firm tends to back founders from historically underrepresented backgrounds.

Another example is actor and climate activist Leonardo DiCaprio. He founded the Leonardo DiCaprio Foundation in 1998, at 24 years old, to support conservation projects around the world. In the years since, he has successfully continued to leverage his fame, and subsequently his wealth, in support of his passion. His formidable green portfolio ranges from plant-based meat (Beyond Meat) and vegan footwear (LØCI) to a biotech company (VitroLabs) that aims to produce environmentally friendly, sustainable leather made from the cells of cows (crucially without harming them⁶. What he does with his money has an impact, and he has transformed from being “just” an actor into someone who makes a difference.

Meanwhile, Grammy-Award-winning singer-songwriter Ciara offers a similar example from the world of music. In partnership with her husband, NFL athlete Russell Wilson, the pair are committed philanthropists, as well as entrepreneurs. Among other ventures, the couple have a fashion retail company called House of LR&C (Love, Respect, and Care) and donate a percentage of the profits to their Why Not You Foundation, which encourages equal opportunities in education and raises funds for children’s health. 

Elevating earnings and status 

The ubiquity of social media has further accelerated the shift in the way celebrities evolve their careers, dismantling traditional power structures and opening new avenues to build wealth. Connectivity is allowing these individuals to nurture direct relationships with fans and craft their own narratives. If leveraged strategically, these digital tools can also drive earning power to new heights.

In the sports world, Tiger Woods, Cristiano Ronaldo, LeBron James, Lionel Messi, and Roger Federer have all surpassed the billion-dollar mark, according to Forbes⁷. Alongside their normal salaries, Ronaldo reportedly earns around $3.2 million, and Messi $2.6 million, for each Instagram post⁸.

Entertainers are also using their social media presence as an additional wealth creation tool. Pop star Ariana Grande, singer-turned-actress Selena Gomez, and actor Dwayne Johnson reportedly each earn between $2.2 million and $2.5 million for an Instagram post, while the Kardashian-Jenner family dominate Hopper HQ’s 2023 Instagram rich list as three of the top 10 most highly paid per post. At number eight is singer, songwriter, and businesswoman Beyoncé – whose net worth is an estimated $540 million⁹ – who can command $1.9 million per post.

What’s more, Beyoncé can confidently be described as a global brand, with sources of wealth that go far beyond her singing career. Her company, Parkwood Entertainment, produces music and movies, and has also branched out into fashion. Meanwhile, in partnership with her husband, rapper and entrepreneur Jay-Z, she has multiple real estate investments. Together, the pair is widely regarded as the music industry’s first billionaire couple.

There has never been a better time for such individuals to take advantage of the powerful combination of wealth and access that is available to them.

And, in the coming years, a significant number of younger people who, like Beyoncé and Jay-Z, do not come from super-wealthy or privileged backgrounds are set to join this group. (Read more about the motivations of the “Rising Gen” in our recent article.)

Consider the NFL’s highest earner, 26-year-old quarterback Lamar Jackson, who signed a five-year, $260 million contract with the Baltimore Ravens this season¹⁰. His counterpart at the Kansas City Chiefs, 28-year-old Patrick Mahomes, has a 10-year contract worth over $500 million¹¹. Meanwhile, 27-year-old NBA player Jaylen Brown signed a record-breaking $303.7 million supermax extension to his contract with the Boston Celtics this summer¹².

Social media influencers – across Instagram, TikTok, and YouTube – are also becoming famous in their own right, accumulating wealth at an unprecedented rate¹³. This relatively new type of modern celebrity has found that they can elevate their earnings and status by retaining ownership over their personal brands, converting online followings into fortune.

New model for success

What’s driving more elite athletes and entertainers to take the reins of their careers and investments? For many, it stems from a desire to create an enduring legacy, transitioning what can often be short-term fame into positive impact and multigenerational wealth. While for others, especially athletes whose careers can be short, it’s a question of maximizing their income during and after their years on the field.

NBA legend LeBron James, for example, is still excelling on the court, but at 38 he is also broadening his remit to encompass roles in media and business, investing in start-ups and using his influence to push for social justice.

In addition to co-owning a production company, he’s an investor in the Blaze Pizza chain, has minority stakes in several American and European sports teams, and in 2020 helped form a voting rights organization to fight Black voter suppression. His family foundation supports educational initiatives for children in his hometown.

But branching out and plotting a new course requires input from trusted advisors who can provide invaluable guidance around smart investments, tax strategies, estate planning, and sustaining wealth. Ideally, it means forging these relationships and building that crucial element of trust as early as possible in their journey, enabling these dynamic individuals to invest and enjoy an exciting and engaging experience that allows them to expand their knowledge and opportunities – but without it becoming a distraction from their primary careers. Then, ultimately, everything should be in place for when they’re ready to take more control of their business or investments.

To make this happen, we use all our deep-rooted experience and knowledge gained from working with other families and generations – from a variety of backgrounds – and tailor it to create bespoke plans to help this new breed of entrepreneur accelerate and grow in the wealth space. We are dedicated to understanding their needs and priorities, striving to create the best off-field/stage/screen team that works for them, and drawing on the unique depth of insight that AlTi can offer to open the doors to rewarding and impactful success.