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Mamba Mentor: Kobe Bryant’s Impact on Naomi Osaka & Evolve

In his second act as a storyteller, hear how the hardwood legend led by example off the court and in the office, molding minds by giving the gift of time.

From the jump, Kobe Bryant was an absolute sponge.

On an eternal quest for knowledge, the teenage talent ascended to all-time great by asking basketball’s best for advice. Like his play, he took off by being passionate and absolutely relentless.

photo by JEFF HAYNES/AFP via Getty Images

Coming up, Kobe would text Michael Jordan at 3 AM, inquiring about everything from footwork to turnaround jumpers.

At All-Star Weekend, he’d use the playful practices to pick Gary Payton‘s brain regarding defensive strategy.

In the summers, he’d challenge Reggie Miller to games of one-on-one as a means to learn his tendencies.

As a player, peers lovingly called Kobe a ‘nuisance,’ nodding to his constant questions about basketball and eventually business.

As an adult, he made it his mission to pay it all back.

Prior to his passing in 2020, Bryant became a mentor to heralded hoopers like Jayson Tatum and Sabrina Ionescu. As a coach, he taught his daughter Gigi’s team everything from fundamentals to mindset.

While Kobe’s connection to basketball’s best is well known, it’s less documented just how much help he gave to others outside of the hardwood.

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This list includes rising tennis star Naomi Osaka, who first met Kobe in the summer of 2019.

At the top of her game but down in the dumps, she needed guidance on how to stay winning with the world watching and competition coming from every angle.

“Naomi played the French Open and lost in the third round when she was No. 1,” Evolve co-founder and Osaka agent Stuart Duguid tells Boardroom.

“She said, ‘I was able to get to No. 1 relatively smoothly, but now I’m here and that’s what feels like the challenge. People want to beat me every single match.'”

This feeling was foreign to the recently rising icon Osaka, but not uncommon for athletes of her level.

“It’s like when teams against Manchester United or the Lakers,” explains Stuart. “They want to beat them just because of history. She felt like that was the case for her.” 

As an agent, Duguid dug deep in his contacts, searching for someone who understood what Naomi was feeling. After weighing the specifics of the situation, it was clear the person best equipped to offer advice was Kobe.

Playing overseas, Osaka struggled with the new spotlight. After losing at the French Open, she fell to No. 2. A few weeks later, she was upset in the opening round at Wimbledon.

Traveling back to Cali, the time had come to try Kobe.

“We got back from Wimbledon on a Tuesday afternoon and sent him an email,” Stuart says. “He got right back to us and said, ‘Be at my office at 9 AM tomorrow.'”

Much like Kobe used to tell teammates to meet him at the track before sunset to run sprints, he was equally pragmatic when it came to mentoring off the court, even if he’d lightened up a bit.

Sensing the moment, this opportunity was amazing for Stuart but he acknowledge it was perhaps overwhelming for his young client.

“Naomi was pretty shy at the time, so my wife and I went and picked her up and drove her to Orange County,” says Stuart. “When we got to the office we said, ‘Alright, on you go!’ She thought we were all gonna go together and sit down with him, but we knew if we told her in advance that it was a one-on-one she’d probably be too nervous.”

As Osaka opened the doors to Kobe Studios, Stuart and his wife Carly sat in the parking lot with baited breath. They waited. And waited.

Suddenly, the office doors opened back up.

“She came out and said, ‘That was the most fascinating hour and a half of my entire life,'” Stuart remembers.

What was assumed to be a ten-minute pep talk turned into an expansive conversation that was bigger than sports. More importantly, it created the space for an ongoing dialogue between the two.

“From that point, they became very close,” Stuart says. “He had a big impact on her and was such a generous individual with time and [demonstrated such a] willingness to help. He’d text her back in like five minutes; he was so awesome.”

Kobe Bryant watches a Women’s Singles second round match between Naomi Osaka of Japan Magda Linette of Poland on day four of the 2019 US Open at the USTA Billie Jean King National Tennis Center on August 29, 2019 in Queens borough of New York City. (Photo by Al Bello/Getty Images)

So, what role did Kobe play for Osaka during their time together?

“He was Naomi’s mentor for so many things from mental health to sportsmanship,” Evolve’s Carly Duguid tells Boardroom. “Stu and I learned so much from him, not just speaking to him, but hearing from Naomi based on conversations they had.”

Though the lessons Kobe’s best known for offering often accumulate to success on the court, those that got to know him later in life learned his mind was focused on much more than sports.

Behind the doors of his Newport Beach office, he was starting an equally impressive second act.

The Black Mamba Blueprint

Both in athletics and in life, all are aware of the Mamba Mentality mantra and what it means in regard to competing, conquering, and persevering.

As an icon, Kobe’s acumen for intensity was well documented. Entering his second act as a storyteller, the world was just getting to know what his business brain looked like.

“The last time we were with Kobe, he came to the US Open and he was promoting a kid’s book that was very Harry Potter style,” says Stuart.

That book was the first installment of Kobe’s The Wizenard Series, a hardcover children’s story set to teach lessons about overcoming obstacles through mystical tales tied to sports.

At the 2019 US Open – just months after Kobe first met Naomi and miles away from his Orange County office – Stuart sat next to the star who was busy supporting his new friend in Queens while also making the media tour stops for his new book.

“I was asking him about the book and the business,” says Stuart. “He said, ‘The book is absolutely not a revenue mission for me. I want the book to turn into a movie, to turn into characters.’ He was thinking five steps ahead of what it all could be.”

Retired from basketball – the game he obsessed with endlessly for over 30 years – Kobe was on his own transformation from superstar scorer to all-world storyteller. While this move may have come as a surprise to some fans, he’d been building his brand and preparing for his next act even in the latter days of his playing career.

“Kobe was directing his own commercials and was really ahead of the game,” Stuart praises of the legend’s additional endeavors. “That’s kind of what everybody is doing now – even if it’s not commercials – but it all dates back to that concept.”

A storyteller in the sense that Osaka occupies at her production company, Hana Kuma, Kobe called the shots on his own narrative while running the day-to-day duties at Kobe Studios.

“He was really operating the businesses,” Stuart notes. “I was so overwhelmed that one athlete had this structure. I’d heard that he had a production company and investment arms, but the size and scale were amazing.”

As an entrepreneur, the same spirit that led Bryant to learn everything that he could from the greats who came before him carried him creatively.

“The founder of Body Armor told me that Kobe would call him at 2 AM about an idea for bottle packaging,” says Stuart. “Kobe was doing everything, he was super hands-on. I wonder how he had the time?”

Since his untimely passing in 2020, many wonder just how he was able to accomplish so much in such a short window of time.

Productive people often have trouble engaging in the moment because their mind is always wandering to the next task. Ask any athlete, fan, or friend of Kobe about his level of love and companionship in the latter stages of his life and the glowing reviews bode the same.

“I’ve never met anyone like him on a personal level,” Carly says. “He had such a presence and made you feel like [your time together] was the only thing he was thinking about at that moment.”

Carly considers Kobe the blueprint for building a business as an athlete when it comes to breaking the mold on style and storytelling. Osaka and Stuart see his approach to creativity and innovation as a guiding light professionally.

More importantly, they all see his compassion for guiding the next greats as a mission all should aspire to.

“He was the most generous superstar athlete in regard to time,” Stuart says.


About The Author
Ian Stonebrook
Ian Stonebrook
Ian Stonebrook is a Staff Writer covering culture, sports, and fashion for Boardroom. Prior to signing on, Ian spent a decade at Nice Kicks as a writer and editor. Over the course of his career, he's been published by the likes of Complex, Jordan Brand, GOAT, Cali BBQ Media, SoleSavy, and 19Nine. Ian spends all his free time hooping and he's heard on multiple occasions that Drake and Nas have read his work, so that's pretty tight.
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