Inside the new venture from the tennis superstar and co-founder Stuart Duguid and how it’s redefining what the athlete entrepreneur looks like in 2022 and beyond.
Naomi Osaka is hard at work – or is she?
Since turning pro at 14, Osaka’s defeated the game’s GOAT and won four Grand Slams. On-court, she’s made more than $21 million in prize money despite being barely old enough to rent a car.
Still, around the world and across the internet, fans, critics, and commentators wonder what she’ll do next.
Or perhaps more pressingly, what she’s doing now.
Today, she’s modeling in Los Angeles’ legendary Milk Studios. As the sounds of Steve Lacy match the flowy shots showcasing Osaka in a monochromatic satin ‘fit akin to TLC’s “Creep” music video, she’s serving looks – not aces – yet still very much in her bag.
As she shifts into her role as an ascendant mogul, that bag is a briefcase.
Osaka topped all female-identifying athletes in earnings, bringing in an estimated $60 million in 2022 alone. For those keeping score, she went 14-9 on the court in ‘22, banking just over $1.1 million in prize money. Still, the superstar smashed the competition with regard to business endeavors. Therein lies the magic and merit of this “work day” in California.
Yes, Osaka is flexing different skills than those that brought her into the public eye. No, her tennis racquet is not collecting dust as she collects checks.
Rather, the 25-year-old multihyphenate is using an early window in her loaded day to take pictures for a new line of garments set to launch next spring as part of an ambitious collaboration she soon plans to reveal.
So, if you’re surprised that a tennis titan also managed to become a championship-level mogul after just a quarter-century on this earth, then you don’t know Naomi and you don’t know Evolve, the management agency she co-founded earlier this year.
“This is all Naomi’s own collection,” fellow Evolve co-founder Stuart Duguid told Boardroom at the shoot. “When we signed this deal, it certainly was not to be a model; it was to be [more] involved. It’s a business in itself and those are the things that get her excited.”
In its infancy, Evolve allows Osaka and her partners — Duguid and his wife, Carly — the opportunity to call their own plays. Today, this means meeting with apparel execs (and shooting their own Cover Story for Boardroom).
Sure, it might appear too glamorous on its face to feel like work – but it is.
Made in Japan
Launched in May 2022 by Osaka and Stuart Duguid, her longtime agent, Evolve is a venture only months in the making, but an idea that first began to take shape last year in Tokyo.
As both a tennis champion and an emerging entrepreneur in fashion and apparel, Osaka was always going to be more than an athlete in this equation; she’s a key business brain behind the agency.
“Naomi came to us,” Carly Duguid, co-founder of Evolve, told Boardroom of the company’s origin story.
As her husband Stuart recalls, the two were talking at the 2021 Summer Olympics in Osaka’s birthplace of Japan. At that time, the rising superstar was aware of the moment, yet focused on the future. She realized her current representation deal with IMG was coming to a close; more importantly, she realized her professional peers were not just endorsers, but entities unto themselves in regard to investment and ownership.
“Naomi looked around and saw LeBron, KD, and Tom Brady,” Stuart says. “She said, ‘Why can’t I be like all these male superstars?’”
Caught off guard, Stuart didn’t have a good answer. Equally, he didn’t have the desire to depart from the place that helped shape his own career. Nevertheless, he leaned into the desires of his client as any good agent would.
“It was never my ambition to start my own company,” says Stuart. “It’s not easy. The day-to-day management used to be a full-time job. Now, it’s probably 30% of what I do.”
Since starting Evolve in May, Stuart has transitioned from building the bolts of the business to making Osaka the highest-earning female athlete in a single-year span in history.
Even so, he’s quick to insist it’s ultimately about her, not him.
“She came to me and said, ‘I want to be in fashion,’” says Stuart. “It’s on me to make that a reality.”
As showcased by Osaka’s unprecedented earnings in 2022, that reality is clearer than ever . From namesake Nike collections to Levi’s looks, Evolve is the catalyst for a Naomi Osaka empire reaching across sport, apparel, lifestyle, and beyond.
“We’ve gotten to this point by really focusing on her,” says Carly. “Her world has completely opened up. She can do anything she wants.”
In this earlier stage, the Evolve team consists of the Duguids and talent manager Alexandria Boston. For her part, Osaka plays an integral role not just as a co-founder, but as the face of its growth and development.
Because of her accomplishments, the tennis trailblazer always had the clout and credibility to attract a compelling cast of athletes, but taking the leap to actually start Evolve has sharpened her confidence. It’s also given her an ideal place to grow where work outside of tennis and design are concerned.
“The most interesting aspect of the business for me is investing,” Osaka told Boardroom. “I’ve learned a ton in the last 18 months. That’s probably the area where I’m most engaged.”
Since that trip to Tokyo in 2021, Osaka’s mission to start an agency has suddenly put her in direct contact with fellow founders and entrepreneurs. Her financial situation speaks to such success but it all means more than simply her own earnings.
In Osaka, Evolve has a global figurehead who elicits interest from execs while remaining revered by the best across global athletics. She’s already a superstar in sport, fashion, and business in both hemispheres, making her one of the most distinctly marketable athletes ever.
As a result, Naomi and Stuart Duguid are uniquely positioned to sign the sporting world’s next superstar set on shifting culture.
The Evolve Athlete
Of course, not everyone can be Naomi Osaka.
More than an athlete and ascending as such, she has risen in the ranks from Nissin Noodle endorsements to appearing on awnings as an ambassador for Louis Vuitton.
As a face for the fashion house – one that represents the front half of the LVMH empire worth over $175 billion – Evolve is leveraging Osaka’s tennis talents and the worldwide appeal that goes with it to flourish in fashion. Still, deals with partners like Louis Vuitton aren’t all about making millions, or even exposure.
Rather, they’re affording Osaka a paid master class in design.
“Her ultimate goal is to one day have her own brand,” says Carly Duguid. “Our recommendation was to do as many collaborations as we could within each category.”
This all bolsters a vision meant to carry Naomi far past her playing days.
“I’ve really been a sponge,” Osaka says. “And have tried to absorb a wealth of knowledge.”
This duality – a four-time Grand Slam champion essentially taking night classes in couture – may be the best early example of what an Evolve athlete is (or what one could be).
Since starting the agency alongside Osaka, the rest of the Evolve team has been selective in who they add to the fold. Today, there is exactly one Evolve signee: Australian tennis rockstar Nick Kyrgios.
In attitude and aesthetic, he’s the perfect fit.
“I always like to do things my way,” Kyrgios told Boardroom. “And I don’t care too much for the status quo. Evolve shares that vision.”
Currently ranked No. 22 in ATP, the incandescent Aussie is ascending in both exposure and endorsements due in no small part to Evolve’s ethos.
“What they achieved with Naomi over the past few years is unprecedented,” Kyrgios says. “Since working with Stu, my business has grown tremendously.”
Essentially, the Evolve model seeks to magnify personality and align interests for dynamic deals.
These deals often include equity and always allow the client to learn and grow rather than simply collect a succession of checks.
“When we think about partnerships, it’s not about money, it’s what feels like a good fit,” Carly says. “We really lean into things that make sense for their personalities on and off the court.”
It’s critical to note that Nick and Naomi’s personalities are almost polar opposites.
Just the same, each has a level of sheer individuality that proves massively influential where fans and brand partners alike are concerned.
“They push the boundaries,” says Stuart. “They have more to them than tennis. They’re outspoken, but they’re quite different. They’re probably two of the most talented players of their generation”
So, when electing Evolve’s next signee, it needs to be as much about substance as sizzle.
“Our next athlete would be someone who’s at the top or has the potential to get to the top of the sport,” says Stuart. “Someone who’s thinking, ‘Who do I align myself with to take advantage of this opportunity?
“That opportunity could be wanting to invest in companies, or that opportunity could be wanting to build a safari in Africa. Anything that is a creative and uncharted path. Anything that’s above and beyond what’s been done before interests me.”
In 2022, Stuart and Carly can connect with decision-makers at LVMH or Sweetgreen in a matter of minutes. Still, signing new talent at Evolve isn’t solely focused on aligning endorsers and as agents it’s not all about getting a cut.
“It’s more, ‘can we make an impact outside of the sport?’” says Stuart. “If it’s just doing an endemic Nike deal and a Wilson racket, I’m probably not the right guy. But if you want to influence culture, build a business, invest in businesses, and you’re an athlete on a scale and platform that can do that? I think we can be very helpful.”
Not everyone is meant to be an Evolve athlete.
And that’s by design.
The New Model
When asked about his approach to representing an athlete, Stuart’s response is succinct.
“I give an opinion, but I’ve never wanted to steer someone’s career in a certain direction,” he says. “I see myself as additive.”
His additive approach has allowed Osaka to grow as a person, player, and mogul. The trust in the Duguids permits her the freedom to excel in her growing portfolio of ventures.
“I still rely heavily on my team to conduct the core business,” Osaka says. “I’m more involved on the big-picture strategic side.”
That big picture is still painted by a small team. Aside from Stuart and Carly, Naomi’s squad features Alex Cohen, who handles her financial advising and plays a part in all equity and investment decisions at Evolve.
The business of Naomi Osaka is one of massive in earnings, yet small in terms of labor force. Around the industry, this is not the standard model in tennis or for the majority of talent at such heights.
“At a big agency, you might have a whole team of 10 people working on your account,” says Stuart. “But they’re probably working on 30 other accounts. It’s not always what it seems.”
For Naomi, this lean and mean model is particularly ideal.
“In her case, a small team is better,” Stuart says. “Her hair stylist and makeup artists are part of her small family. She uses the same people every shoot. That’s also more efficient because they know exactly what she likes.”
Because of this, even when Naomi is working on a photoshoot, she’s working smart. Stuart could take credit for this small business bright spot, but it’s Osaka’s orbit – but make no mistake – this is not tyranny. The Evolve approach spearheaded by Stuart is all about what works best for his client. For Nick and Naomi, this means intently engaging in their specific interests as a means to grow their portfolios organically.
Day in and day out, Stuart and Carly listen to their clients and potential partners. The goal is always making sure each move Naomi and Nick make off the court is in sync with their ethos and energy.
“A lot of my job is being Naomi when she can’t be there,” says Carly. “Because she still has her day job and still plays tennis.”
Osaka’s day job involves winning Grand Slams, while her side-gig had her presenting at New York Fashion Week. These are big wins in big arenas, but it’s still all about amplifying every opportunity an athlete aspires to while treating their authenticity as sacred.
“They just want me to be me,” Kyrgios says.
From a scale standpoint, Nick’s business is not yet as big as Naomi’s but it’s every bit as personalized. Evolve negotiated his Nike deals that present him in basketball-inspired looks untied to tennis. It’s all aided by the help of Daniel Horsfal, Nick’s childhood best friend who also serves as a day-to-day manager.
Still, on the agency side, it’s just Stuart, Carly, Alexandria, and Naomi. And what they lack in sheer numbers, they make up for in mentorship.
“Rich Kleiman has been super helpful from advice to opinions,” says Carly. “Rich Paul has been amazing and a really good friend to us. Maverick Carter has been huge as he’s a partner in Naomi’s production company. He’s been a beacon for us every step along the way.”
Separately, Stuart and Naomi’s production company, Hana Kuma, is a partnership in tandem with LeBron James and Carter’s SpringHill Company. The arrangement allows all parties to learn from the best and be backed by them at the same time.
Even in its earlier days, Hana Kuma already boasts a couple of key investors helping the mission of aligning a fledgling production powerhouse with the culture’s biggest brands.
“Stuart, Carly, and Naomi work very smart and very hard,” Maverick Carter told Boardroom. “Their approach is always about collaboration, which in this sports marketing space is key because partnership is the way to build one plus one equals three relationships.”
These cross-category partnerships are not only key; they’re increasingly amplified by speed, scale, and funding. At an agency of the grandest global scale, launching an athlete-led venture would take something close to forever due to the challenges and inefficiencies of the corporate totem poll.
At Evolve, the Duguids and Osaka are instead partnering directly with James and Carter while learning from the likes of Kleiman and Paul. Each entrepreneur has firsthand intel on what it’s like to leave the safety net of a big agency to branch out and start their own enterprise.
Now more than ever, Stuart knows this space intimately, and he’s bullish about putting his knowledge to work despite the daunting nature of going independent.
“It’s not easy,” he says. “It’s really tough having worked at a company that was the No. 1 tennis agency for many years and continues to be.”
Leaving IMG and starting Evolve, however, has made Stuart busier than ever. On top of that, it’s made friends and former colleagues into competitors.
“I really believe that a lot of people want me to fail,” admits Stuart. “Personally, if any of my friends took the risk to start their own business? I’d be so proud of them and ask what I could do to help. We’re in a competitive space and I’m not expecting miracles, but it’s upsetting how many people root for you to fail.”
He takes a pause.
“On the other hand, it gives really great motivation,” Stuart says. “I really want to fucking crush it.”
Closing the Gap
Tireless work manifesting as early success is intended to be part and parcel to the brand at Evolve.
Right on cue, Naomi Osaka is already outpacing her own male sports heroes. When considering KD, LeBron, or even Kobe, Osaka’s achieved more in regard to earnings and agency at an equivalent stage of life.
However, while Osaka ranks as the top-earning female athlete of 2022, a stark contrast still exists with her male peers. According to Forbes, the 10 highest-earning athletes of 2022 were all men.
Inside Evolve, there’s a feeling that the tide is turning – but that only changes with hard work.
“We believe that women should be paid equally, full stop,” Carly Duguid says. “We’re trying to close the gap.”
While the stuffier critics may question the extent of Naomi’s emphasis on entrepreneurship, legends see the body of work that she’s putting together quite differently.
“Naomi has really done a lot to break down barriers for female athletes,” Billie Jean King told Boardroom. “In terms of business, [Evolve] has set a very high bar.”
At the agency, Osaka’s excellence as a business partner may not look like hard work to those more accustomed to seeing her sprint between the painted lines on the court. However, her earning acumen has the potential to be a rising tide that lifts all ships in rapidly changing times.
“The gap is definitely closing and I think it’s going to keep going in that direction because female sports are so on the rise,” says Stuart.
“It’s going to take a while, but women’s soccer is getting there and so is the WNBA.”
Only six months in, Evolve is doing its own part and striving to live up to its name simply by doing what Osaka’s sporting predecessors did to lay so much groundwork for her: the work.
In the months ahead, both she and Kyrgios will be active on the court and expressive through an ever-growing omnibus of endeavors.
And though exploring opportunities outside of tennis makes them marketable, focusing on winning is principal to athletes – and their agents.
“Nothing gives me a greater buzz than sitting in the box of a Grand Slam final,” says Stuart. “No deal concluded will ever replicate that for me. I still love being at the cutting edge of elite sports or being able to help someone who could get there even if they can’t.”
Looking ahead, as an agency unbound by a behemoth’s bureaucracy, Stuart sees Evolve expanding – but at his own pace. At present, daily duties of maximizing opportunities for Nick and Naomi are keeping him plenty busy.
“We have two of what we think are the most marketable athletes ever, so we don’t desperately need to add,” Stuart says. “But if the right opportunity came around, I would definitely love to do it.”
Heading into 2023, the bar for what constitutes an Evolve athlete remains high. Next year, Kyrgios will make his Netflix debut as the star of the tennis reality show inspired by the success of Drive to Survive, while Osaka continues to make moves in fashion as a designer and dealmaker.
These opportunities naturally bode well for the athletes as such. They also excite the agent who left his dream job to build an agency off of a single ask.
“It’s a cool place to be,” says Stuart. “I don’t have to fly out to an under-14 tournament in Florida to recruit the next Naomi. That’s not the model.”
Rather, at Evolve, the model is giving the world’s most interesting tennis talent the space to make waves and create change.
“It’s another step in taking control of my own destiny,” Osaka says. “To be involved in helping other athletes achieve their goals and learn from my experiences.”
Make no mistake, Naomi Osaka is working.
Whether on call or on-court, Evolve’s excellence is very much hard work for all involved – even if at first glance it doesn’t always appear that way.
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