Winning by Tim Grover (BOOK REVIEW AND SUMMARY)

Winning is the 2nd book by Tim Grover, trainer to great athletes like Michael Jordan and Kobe Bryant. The man should know a thing or two about the mindset required to win. I enjoyed Grover’s first book immensely, and so decided to share a chapter by chapter summary of Winning. I have also shared my honest opinion of the book. Hopefully, this helps you to decide whether or not this book is worth your time and money. 

What I thought of the book

I enjoyed this book just as much as Grovers first. In an industry full of fake “success” Gurus, I will always have time to hear the wisdom of a man who has actually achieved greatness, on multiple occasions. The book goes outside the box and is full of personal stories and anecdotes about people like the great Kobe Bryant, which really set this book apart from other books in this genre. I would genuinely recommend you check out this book. (you can do so by clicking here)

Chapter By Chapter Summary


“Rest at the end, not in the middle”

Kobe Bryant

“Always chasing that win. Never done.”

Kobe Bryant

Everything Kobe did was about winning. Winning is everywhere. Every moment. You have the opportunity to win. Grover describes winning as brutal, neverending and relentless. Any book with a title like “10 easy steps to winning” is a fraud. There is nothing easy or simple or predictable about winning. 

The book doesn’t tell you what to do. You know what to do. Winning paints a picture of exactly what winning is, and the kind of attitude you will have to adopt if you want to win again and again and again.

Winners, or “cleaners”, never stop chasing greatness. There is always more.


Winning doesn’t bullshit. Grover isn’t about “motivation”. Anyone who really wants to win drives themselves. It is a given. Anyone who needs a book or a speech to give them temporary motivation is missing the point. 

The book isn’t here to tell you that “You got this!” or “everyone’s a winner!”. The book is about showing you the brutal, unforgiving, uncertain path that anyone who really wants to win must walk down. The unbearable loneliness, exhaustion and fear. 

There is nothing normal or typical about the lifestyle of a real winner. Normal people don’t stand out. Normal people go where everyone else has gone. Winning is in everyone, but for most people, it will never be shown because of all of the fear and worry and doubt. 

The way you talk about winning will show you where you are at with regard to actually winning.

“Look at these definitions of winning again. Uncivilised. Hard. Nasty. Unpolished. Dirty. Rough. Unforgiving. Unapologetic. Uninhibited.Everything. If that describes your journey, and how you attack your goals, we are speaking the same language.”

check out this powerful speech from the author, Tim Grover


Grover has thirteen definitions of winning, which make up the remaining chapters. Grover numbers everything in the list number 1, because he feels that normally with lists people consider the later items less important.

NUMBER 1) Winning makes you different, and different scares people.

Grover talks about the importance of knowing how to think for yourself, as opposed to being told what to do and accepting the norm. Every great development in humanity came as a result of someone thinking for themselves and not just accepting the world as they were given it. 

“Winning requires you to learn, and then question what you learn, and then learn more. You have to be willing to challenge what you’ve been taught”

Grover also talks about the concept of non-negotiables, and how they can hold you back in your journey if you are not careful. For him, the only non-negotiable is performance. Everything else is there to be looked at and scrutinized. Nothing is off-limits for people who really want to win.

NUMBER 1) Winning wages war on the battlefield in your mind.

“I don’t have a better way to say this. Winning F*cks with your mind. It just does”

The writer talks about the non-stop mental warfare that takes place in the mind of every winner. You are exhausted and impatient and on the edge all the time, even when you rest. The message of this chapter reminds me of a quote I came across once:

“Hustlers don’t sleep. They nap”

Your brain is like a minefield that is yours to dominate. You must be aware of your own insecurities, distractions and weaknesses if you are going to stay in control. 

“If you decide something is going to be a problem, then it’s going to be a problem”

This is a chapter about the mindset of a winner, but not in that positive rah rah self help sense. It is a real, honest look at the lengths we have to go to if we are to stay on the winning path.

Grover also talks of how winners control absolutely everything that they can, with the expectation that there will be plenty of unexpected challenges that they will have to overcome in the moment. 

NUMBER 1) Winning is the ultimate gamble on yourself.

This chapter is really about confidence. The chapter details the similarities and differences between Kobe Bryant and Michael Jordan. Grover knew these players personally probably better than anyone in basketball, and his insight is pretty cool. He talks of how for all of their differences, both Kobe and Michael shared unshakeable confidence in themselves and their ability to get the job done when the time came. They never buckled. Their ability to bounce back from a loss. Their ability to ignore the negativity of the media. Their ability not to be overpowered by more physical players. They always knew that they could come out on top. It defined their greatness. 

This belief went way beyond basketball. Michael became the first player to become the majority owner of a team after he retired. He started numerous business ventures. He competed on the golf course. Kobe learned 5 languages. 

“Everything he did was about his massive belief in himself”

Grover talks of how truly confident people cannot be broken. They have been beaten down and broken over and over by life and their goals, and they have ploughed through every obstacle that life has thrown at them. People like that truly back themselves when the pressure is on.

click here to check out Winning on amazon

NUMBER 1) Winning isn’t heartless, but you will use your heart less.

“Winning has a price, and that price is that your mind must be stronger than your feelings”

People talk about how brutal Michael Jordan was in training with his teammates. To the untrained eye, you might be forgiven for thinking that he was a bit of a c*nt. But think about it. He won 6 rings. He is etched in basketball history, and he bought his whole team with him. We all know about Scottie Pippen, and Steve Kerr, and Dennis Rodman, because of the rings that they won under the leadership of Michael Jordan. That kind of greatness doesn’t have the time to worry about your feelings and emotions.

Your mind knows exactly what to do. Your weakness often comes from your feelings. You know you need to work out. Your feelings get in the way. You know that you should consistently post. You feel exhausted. Self-control is all about controlling your thoughts, in order to control your emotions, in order to control your actions. Control what you can control. 

Michael wasn’t emotional when he was angry. He was cold and unemotional. He was aggressive, but he was absolutely in control. That is a dangerous combination.

NUMBER 1) Winning belongs to them, and it’s your job to take it.

This chapter is all about competition. Have you ever been accused of being overly competitive? Of having a competition problem? Grover wants to challenge you to be OK with that. The greats never stop. There is always another challenge. Why do you think all the great boxers keep fighting until they are a shell of their best selves? It is in them to fight and compete. There is nothing else like it.

Competition drives us all. To compete every day is to get the most out of every single day. 

We are all hard-wired to win. You cannot teach competitiveness, and you cannot make other people want to win. You may inspire it, but ultimately it is a completely internal and personal fight. You must want to win, with all of your being, for yourself over anyone else. 

Check out Grover talking about his approach to training Jordan back in the day:

NUMBER 1) Winning wants all of you; there is no balance.

“Time for everything equals time for nothing”

Winning wants all of you. It demands obsession. The whole work-life balance thing doesn’t really mean a lot to people who badly want to win. When you are obsessed with achieving greatness in one area, that usually comes at the expense of most of the things everyone considers normal and healthy. Being the best requires hard sacrifices, and it is never going to be easy. There is no perfect future where you can have greatness in your field, and a great family life, and great holidays, and loads of sleep, and loads of friends. 

Winning wants all of your time and attention. There is no balance for those who want to win. Stop looking for it, and stop feeling guilty about your lack of it. 

NUMBER 1) Winning is selfish

Why is it so wrong to be considered selfish? Self literally defines who you are. To invest in yourself, love yourself, be yourself, all sound like a great thing. To be selfish has such a negative ring to it. But what is the difference really? How is it a bad thing to be concerned with your own results and success? This chapter convinces us of the absolute necessity for someone who wants to win to be selfish.

The chapter also makes an important distinction; there is a difference between selfish winners and selfish losers. 

  • Selfish losers take from everyone, and everyone else is better off without them. If you are selfish but not concerned with winning, then you are just prioritising your own pleasure and impulses.
  • Selfish winners give to themselves first, so that they can ultimately give to the world. They give themselves the time, space and permission to achieve what they want to achieve because they know that their winning can lift up those around them. In order to be the most charitable person in the world, you first have to put some serious money behind you!

You can’t create your own wins without first prioritising your own goals and dreams. Separation is power. Separation is freedom. Winning is an investment. If you want to win, you must be selfish and invest. If you are not willing to invest in yourself, why should anyone else?

Click here: check out winning on Amazon

NUMBER 1) Winning takes you through hell; if you quit, that’s where you’ll stay.

People think of winning as this triumphant celebration that solves everything. According to Grover, that is true only for a moment. But stay in that moment too long, and it will be the last time you ever get to experience it. 

Winning takes a brutal trip from the bottom. You must toil, and grind, and think, and push relentlessly through mud and sacrifice. If you dont quit, you will win. It will feel incredible for a moment. 

Do you want to win again? Do you want more? You must go right back to the bottom. You’re not a “winner” now. Your next success must be earned, just like your last. It is relentless. Even when you do win, you are still scarred by all that you’ve had to go through to get there. The personal sacrifice. The lack of friends.The neglected family life. The lack of time off. The unidimensionality of your existence. The journey to winning is so brutal, that anyone who will manage it time and time again must be nothing short of addicted. 

NUMBER 1) Winning is a test, with no correct answers

Everyone experiences fear. It is a fact of life. But fear and doubt are very different. When you feel that fear, do you question your ability to get there in the end? Or do you think about how far you’ve come, about all the preparation you’ve put in, and do you stay confident in your ability to ultimately handle whatever’s coming your way? This is the difference between doubt and fear. 

“I have self-doubt. I have insecurity. I have fear of failure. I have nights when I show up at the arena and I’m like my back hurts. My feet hurt. My knees hurt. I dont have it. I just want to chill. We all have self-doubt. You dont deny it, but you also dont capitulate to it. You embrace it.”

Kobe Bryant

Fear is about playing to win. Doubt is about playing to not lose. Fear is pressure. Doubt is panic. Fear says you might win. Doubt says you might lose. Ultimately, winning is a terrifying leap of belief in yourself. 

According to Grover, there are 4 components that will determine your ability to handle fear. Talent, intelligence, competitiveness, and resilience. He goes into detail about the importance of all 4. Spoiler alert: talent is really common, and resilience is really rare. 

NUMBER 1) Winning knows all your secrets

One of Grover’s most popular ideas from his first book is the idea of the dark side. We all have that side of ourselves that the world doesn’t know about. When we are alone at night, there they are. All your mistakes, your fears, the voices in your head, all real and uninhibited. The writer talks about the genuine power that comes from completely incorporating your dark side and accepting your full self, rather than feeling bad or trying to change everything that isn’t completely spot on.

“Deep inside you, there’s an undeniable force that drives your actions. The piece of you that refuses to be ordinary, the piece that stays raw and untamed. Not just instinct, but killer instinct. The kind you keep in the dark, where you crave things you dont talk about. You don’t care about how it comes across to others because you know this is who you are and you wouldn’t change if you could. The dark side is your fuel. Your energy. It excites you. Keeps you on the edge. Recharges you. Fills your tank. Its an addiction as powerful as your addiction to success”

Kobe’s dark side was the black mamba. When he stepped onto the court, he wasn’t the Kobe Bryant that had legal issues and family problems. He was a cold-blooded killer that would dominate anyone stupid enough to play against him. 

NUMBER 1) Winning never lies.

Winning knows the truth, and it wants you to admit it. There is nothing subjective about winning. It is a score. An amount of money. A number on a scale. A decision. It doesn’t matter how hard you tried, how many people were with you, or how talented you are. Ultimately it is black and white. We love to lie to ourselves: 

“We deserve more”

“The score didn’t reflect the game”

“Next year is our year”

“We’re going in the right direction”

If these statements aren’t rooted in anything measurable or objective, they are usually just excuses for us not doing what it took to actually win. You can put your time into convincing yourself that you are a winner, or you can put your time into being honest with yourself, changing your course, taking the right actions and then actually winning. You cannot do both. 

This is one of my favourite ideas from this whole book: Stop talking. When you win, you dont need to talk. If you win, that will do the talking for you. 

If fake it till you make it is your strategy for success, you aren’t going to get anywhere. Winning doesn’t buy your lies, and most people don’t either. 

Read also: How to become ambitious and motivated!

NUMBER 1) Winning is not a marathon, it’s a sprint with no finish line. 

Dont manage your time. Manage your focus. 

Think about the Olympic marathon. These are the worlds best athletes. When they are competing for the gold, do they chill for any 1 of those 26 miles? Is there ever a point where they just take it easy? They are patient, they aren’t stupid, but they squeeze every second that they can out of every mile of the race. 

Slow down. Take your time. Pace yourself. If your goal is to finish, this language makes sense. If your goal is to win, this language is stupid. 

“Rome wasn’t built in a day. No, it wasn’t. It was built every single day, for thousands and thousands of days”

Many people are intrigued by the massive success of someone like Kobe Bryant. How was he able to achieve just so much? According to Grover, it was mainly due to his rare ability to focus on whatever it was he wanted, unfalteringly, until the moment he got it. He didn’t party. He didn’t have hobbies. He trained, and then he recovered, and then he trained, all the way up to the last game of the finals. There was no slowing down. 

“I never lost a game, I just ran out of time”

Michael Jordan

Winning doesn’t care if you dont have time. Winning expects you to make time. If you’ve only got so much time to achieve what you want to achieve, all you can do is choose what you focus on. If you want to win that badly, all of your focus should be spent doing what it takes to win. 

NUMBER 1) Winning is everything

“Long term goals are great, but long term isn’t promised to anyone. Your skills have and energies have an expiration date. If you want something, go get it now.”

Grover talks in this chapter about the importance of a sense of urgency. He reckons it is ultimately the difference between those that win and those that watch others win. 

Kobes impatience was legendary. Zero tolerance. 

Ultimately, winning is your legacy. It is what you’ve done. It is the mark you’ve left on the world. Every day, your time grows shorter. The writer’s message is simple: Do everything. Experience everything you want. Go and achieve your goal. Do not settle or slow or pace yourself. Push. Life is a daily campaign against laziness and the urge to quit. 

We are all human. It would be so easy to just fit into normality. But if you are going to win, you must keep going. Every day, you keep going. The pursuit of winning is what life is about. It is the pursuit that costs everything but gives everything.

Click here: check out winning on amazon

Other books that you’ll like if you like this one

This book is a brutal, intense, unfiltered examination of what winning is. For people who enjoy this kind of content, there are three books that come straight to mind.

The first is Grover’s first book, Relentless. An international best-seller, the book is all about the three kinds of people in competition and life in general: Coolers, Closers and Cleaners. He put the book together after personally working with and analysing hundreds of top athletes and business people.

check out my full review and summary of relentless here

The second is my favourite biography: An Unsung Hero: Tom Crean- Antarctic survivor. You can basically look at this book as an account of a humble hardworking optimistic funny guy who saved loads of peoples lives on a number of occasions. He lived a bold life and was an incredible source of inspiration for everyone around him. You can find out more about the book here (link to amazon).

The third would be Can’t Hurt Me by David Goggins. To cut a long story short, Goggins is a man who was born into an incredibly abusive family in extremely troubling conditions. After being unsatisfied with the fat, uneducated, miserable man that he became in his twenties, He turned himself around in a major way. He went on to:

Go through hell week twice.

Run 100 miles on 2 broken legs.

Become the only member of the US armed forces to complete seal training, the US army ranger school and Air Force tactical air controller training (straight off his website)

Complete over 60 ultra marathons and endurance races.

Break the pull up world record after failing twice, once on live tv.

You leave this book seriously inspired to squeeze more out of your own life. Check out the book on Amazon here.

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