Winning’s Structure

Good advice is hard. Our This Time is Different series is built around asking: Are these the correct lessons?

Part of the uncertainty is the truth and fit between the big idea and the story. Start with No is an example. The big idea is our ego, the story is sales, and the fit is that good salespeople have the right ego. Do people have egos? Are people in sales? Does the right ego for sales still matter? Yes – so the book is good advice. 

Wanting by Luke Burgis is an example too. The big idea is network types. The story is about mimetics. The fit is that we are mimetic because of our network structure. That checks out too (though I had my doubts about the effect size). 

Winning by Tim Grover follows this pattern. The big idea is intentionality told through the story of competition. Winning like Jordan or Kobe requires intentional actions. That checks out too. An opposite story but the same big idea is Early Retirement Extreme. The big idea is still intentionality but the story is financial philosophy. 

Grover focuses on intentionality in two ways: wants and outsider status.

For Grover, wants like winning are preceded by actions. Kobe and Jordan wanted to win so they had to take actions that lead to that.  “If you don’t get on the same level,” Michael Jordan told one teammate, “It’s going to be hell for you.” Jordan was one of the first players to switch from carb heavy meals to eating steak before games. Before Jordan, few players trained during and before the season. For Kobe the actions were learning Slovenian to trash talk Luca Donic. In 2008, preparing for the Olympic Games, Kobe was going to the gym when the rest of the team came back from a party at five in the morning. 

Intentional living requires wants which require actions.

Grover’s second point is how it feels to be an outsider. Howard Marks popularized the idea that outperformance means being different and being right. Easy to say, hard to do. 

Investors, like Marks, can be different and right with good stakeholders. If limited partners don’t ‘get it’ the business plan can’t work. Investors then look for LPs who will ‘stick with’ a plan. It’s easier to be an outsider when surrounded by a (small) group of insiders. 

Grover’s clients are in the entertainment business so the ‘get it’ is social. Why succeed unconventionally when you can fail traditionally? 

There are ways to deal with outsider status. Have a plan and stick with it rather than stick your finger in the wind. “No,” Grover writes, “is a complete sentence.” Build up the don’t give a fuck muscle too. Some think it’s weird? Who cares! 

Successful outsiders design easier paths. We are wired to not stand out. Kobe Bryant had the most ingenious form and LARPed as the Black Mamba. Winning wasn’t a great book. I hoped for more insider stories. But the big idea was a good reminder.

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