Kobe & Jordan’s Trainer Tim Grover on the Dark Side of Winning and What It Really Takes to Be Great (Fan Fav)
Tim Grover, trainer to Michael Jordan and Kobe Bryant, discusses his philosophy on winning, losing, and greatness with host Tom Bilyeu. Grover argues that winning is not about trophies but about the obsessive pursuit of improvement, and that tapping into one's 'dark side' is essential to sustained excellence. He shares personal stories and frameworks that define what separates elite performers from everyone else.
Summary
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.
About this episode
<p>This is a fan fav episode. As you reflect on your business, career, and personal life; where are you winning, and where have you been losing lately? Whether you choose to see the pursuit of success and greatness as a game or not, the reality is there is a cost to play. In this episode, I’m joined by the legendary and iconic trainer, Tim Grover. He authored one of my favorite books, Relentless, and is releasing another book that will change your life called, Winning. He redefines winning in a way that embraces the discomfort of sitting with your losses. If you’re in it to win it, the hard truths Tim drops here about embracing the dark side and making sure your mind is stronger than your feelings will leave you supercharged and ready to attack winning with a new perspective. Order Tim Grover’s newest book, Winning: The Unforgiving Race to Greatness: https://www.amazon.com/Winning-Unforgiving-Race-Greatness-Grover/dp/1982168862/ </p> <p><br /></p> <p>Original air date: 5-18-2021</p> <p><br /></p> <p><strong>SHOW NOTES:</strong></p> <p>Winning | Tim dispels what winning is and why you need to know how to lose to win [2:09]</p> <p>Seeing Inside | Tim on looking internally for the truth stopping your wins [6:07]</p> <p>Winning Flaws | Tim reveals the difference between flaws and weaknesses [7:27]</p> <p>Weakness | Tim on how to leverage and identify your weaknesses to get better [10:38]</p> <p>The Process | Time on why the process is not about emotion, it’s about getting it done [14:41]</p> <p>Pursue the Win | Tim on why not pursuing or seeing the wins every day is an illness [19:49]</p> <p>Confidence | Tim breaks down how winning plays a role in increasing confidence [23:43]</p> <p>Dark Side | Tim explains how using every tool available includes using the dark side [30:54]</p> <p>Fear of Success | Tim on what happens when your feelings are stronger than your mind [42:02]</p> <p>Cost of Great | Tim reveals the pain that playing to win can cost you and loved ones [45:45]</p> <p>Becoming Great | Tim’s tips for finding your own path to winning and trusting yourself [51:45] </p> <p><br /></p><p> </p><p>Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" target="_blank">megaphone.fm/adchoices</a></p><p>See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.</p>
Key Insights
- Grover argues that when knocked down, one should stay down and deeply understand the reason for the loss before rising again — jumping up too quickly without changing leads to repeating the same failures.
- Grover distinguishes between weaknesses (things to fix) and flaws (unique traits like obsession or intensity that society mislabels as problems but are actually the source of elite performance).
- Grover contends that the 'illness' is not pursuing winning obsessively — it is the failure to pursue improvement daily, which he frames as a form of mental and spiritual decay.
- Grover defines the dark side not as evil, but as the internal energy that sustains people when external support, light, and optimism are unavailable — and argues that every great winner uses it.
- Grover draws a sharp distinction between anger (a reactive emotion caused by others) and controlled rage (an internally directed force that the individual commands), arguing the latter is what elite performers harness.
- Grover argues that winning has no loyalty to anyone — people who work less or are less qualified sometimes win — and that this reality should make serious competitors more maniacal about their process, not less.
- Grover kept packing for a work trip after his daughter asked if she ate less whether he would stay home more, framing this as deliberately modeling for his child what genuine commitment to craft requires.
- Grover claims that those who are most uncomfortable when the dark side is discussed are typically the ones with the darkest energy themselves — they feel exposed because they have been hiding it rather than harnessing it.
Topics
Transcript
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