The Orlando Magic had just knocked the Chicago Bulls out of the 1995 playoffs, and much of the criticism landed on Michael Jordan. When his trainer, Tim Grover, told him he’d see him, Jordan didn’t wait for a schedule. “I’ll see you tomorrow,” he said, as Grover later recalled to Sports Illustrated.
That reflex, losing and showing up the next morning, is the product Grover now sells. The CEO of Attack Athletics, which he founded in 1989, has turned decades of work with Jordan, Kobe Bryant, and other NBA stars into books, an online training platform, and a pitch to executives that treats winning as a discipline.
Business leaders have long borrowed from the locker room. Fortune has profiled CEOs who credit high school sports for the discipline and accountability they bring to the boardroom. Grover’s version is harsher, and it comes with a price tag.
Coolers, Closers, and Cleaners
Grover’s framework starts with his 2013 book, Relentless: From Good to Great to Unstoppable, written with Shari Lesser Wenk. It sorts competitors into three types, and Grover describes the tiers in terms any manager would recognize.
Coolers are steady but unremarkable. “The individual that shows up at 9:00 and leaves at 5:00…their work is okay,” Grover said on The Art of Charm podcast. They deliver what they’re asked, and little more.
Closers perform well when conditions are clear. “The closer can deliver the end result as long as too many variables are not thrown at them,” he said. Give them a plan and they will execute it.
Cleaners sit at the top. In Grover’s words, a Cleaner is “an individual that’s going to get you that end result no matter what’s thrown at them.”
His 2021 follow-up, Winning: The Unforgiving Race to Greatness, published by Scribner, returns to that hierarchy. “But there is one thing all Cleaners have in common: the ability to achieve the end result over and over,” he writes.
A $599 course built on the books
The same categories anchor The Relentless System, Grover’s online training platform. It sells for $599 with lifetime access and includes a module titled “Are you a cleaner?” alongside lessons such as “Don’t Think” and “Decide. Commit. Act. Succeed. Repeat.” Buyers also get a guide that tells them which of the three types they are.
A newer online series, Breakthrough, is organized around ten themes, including obsession, pressure, and fear and doubt. Grover pitches all of it as action over reflection.
“I don’t teach mindset,” Grover says in a video on his website. “It’s too many thoughts, ideas in your head that have you overthinking with no action.”
Why Grover keeps returning to The Last Dance
Much of Grover’s material leans on The Last Dance, ESPN’s 2020 docuseries on the Bulls’ final championship season. It became ESPN’s most-watched documentary ever, and Netflix distributed it internationally.
Episode 8 revisits the 1995 series. Jordan had returned from baseball that spring, and the Magic, led by Shaquille O’Neal and Penny Hardaway, eliminated the Bulls in six games in the Eastern Conference semifinals.
Hardaway later said the win backfired. “The respect was always there, but my thing was you had to attack him before he attacked us. But all we did was piss him off,” he told Sports Illustrated. The following season, the Bulls swept Orlando in the Eastern Conference finals on the way to the title.
In Winning, Grover quotes Jordan’s defense, from the series, of how hard he drove his teammates: “Look, I don’t have to do this. I’m only doing it because it is who I am. That’s how I played the game. That was my mentality.”
That mentality has critics. A 2024 Fortune commentary on “the rise of the jerk” described the Jordan of The Last Dance as “Petty. Mean. Kind of angry.” and warned that leaders who display their flaws with pride teach others that being a jerk is the price of success.
Grover sells the other half of the story. For him, the lesson of 1995 was never the loss. It was what Jordan said next.