Kobe & Jordan’s Trainer Tim Grover on the Dark Side of Winning and What It Really Takes to Be Great (Fan Fav)

Tim Grover, renowned trainer to Michael Jordan, Kobe Bryant, Dwyane Wade, and other elite athletes, joins Tom Bilyeu to discuss his book 'Winning: The Unforgiving Race to Greatness.' Grover opens by redefining winning not as a trophy or accolade, but as the obsessive, grinding pursuit of improvement — a cycle that must be continuously restarted after each victory.

Grover challenges the conventional wisdom of 'bouncing back' from losses quickly. He argues that when knocked down, one should stay down and deeply analyze the reasons for failure before standing back up. Each time he stayed down and rose again, he became smarter, more confident, and more resilient. He distinguishes between weaknesses and flaws, asserting that what society labels as flaws — obsession, intensity, relentless competition — are actually gifts that enable sustained winning. He uses Michael Jordan's self-described 'competition problem' and Kobe's obsessiveness as examples of flaws that were actually core strengths.

Grover recounts how Michael Jordan was the only player on the Chicago Bulls to respond to his outreach letter, identifying Jordan's willingness to acknowledge and address his weaknesses as a defining characteristic of greatness. He emphasizes that most people refuse to acknowledge their weaknesses because they become emotionally defensive, and he notes that those who point out weaknesses often share the same ones.

On the topic of process, Grover reframes the popular idea of 'loving the process,' arguing instead that the process is non-negotiable — something that must simply be done regardless of emotional state. He describes his meticulous habit of counting Michael Jordan's steps during games, then using that data to tailor the next day's training, as an example of taking process to an obsessive extreme. He stresses that winning has no loyalty — someone less rigorous may still win — but that this is never a reason to abandon the process.

Grover introduces the concept of the 'dark side' as a misunderstood but essential tool for winning. He distinguishes anger (a reactive emotion triggered by others) from controlled rage (a harnessed internal force). He argues that the dark side is not evil — it is the energy that sustains people when nothing else will. He uses the metaphor that every new day begins at midnight, in the dark, to argue that new beginnings themselves emerge from darkness. He contends that every great winner has tapped into this dark energy, even if they don't publicly acknowledge it.

Grover shares a deeply personal story about his daughter asking him, while he was packing for a trip, 'Daddy, if I eat less, will you stay home more?' — and he kept packing anyway. He frames this not as a failure of parenting but as a deliberate choice to model for his daughter what genuine commitment to one's craft requires. He notes that his daughter later told him she understood, having seen both the results and the dedication.

The conversation closes with Grover urging the next generation to stop looking for step-by-step guides to winning and instead find their own path, trusting that the steps exist even when they can't be seen. He echoes Kobe Bryant's philosophy that 'winning is everything' — not in a materialistic sense, but in terms of the profound emotional impact it has on oneself and the people around them.