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Books On People Really Screwing Up Where They Had the Opportunity To Win?

Your Boy George

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Too often in our culture it seems like we glamorize success but completely ignore the reality of failure.

Musk, Bezos, Rockefeller, Gates, Ford, Walton, Zuckerberg, Jobs, etc. They all have biographies you can buy on Amazon and some even have movies made about them. Their stories are sexy, inspiring, and give you a nice cozy little feeling after hearing them that you can do great things too.

But what about the massive F*ckups? The people who could've won but who didn't because they were too lazy, too unmotivated, too arrogant, etc. I truly believe there's as much to learn from their stories as there is from the stories of the winners.

Jim Collins talks about in his non-fiction book "Great By Choice" that successful people/companies have a "productive paranoia" about failure. How the hell is one supposed to gain a productive paranoia about failure only reading about massive successes? I don't think you can.

Only thing I can find as the example of this massive failure I'm interested in studying is in the book/movie "Into the Wild" where a young kid eschews the corporate lifestyle to live in the wilderness of Alaska, vastly under-prepared, subsequently to die of poisoning by eating a wrong berry. Hitler and Napoleon's invasion of Russia is also a similar narrative of arrogant, under-preparedness, and lazy thinking causing a massive loss. These stories aren't pretty or leave you with little happy butterflies after reading but I feel like they're necessary medicine for preventing a similar fate happening to ourselves.

Any recommendations on books of this type?
 

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JAJT

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I truly believe there's as much to learn from their stories as there is from the stories of the winners.
I kind of disagree.

The folks who never succeeded can SAY that they could have won big "if...", but that's just purely based on hindsight, which is always 20/20.

I could tell you I'd be a millionaire right now if I invested my home's equity into bitcoin 5 years ago. I could tell you why it would have been a good idea based on market trends and the economy at the time and political this and that and entrepreneurial whatever and a million other great, great reasons. I could tell you why I almost got into it, why I didn't, and a million other things but at the end of the day it's all hindsight - I learned all the great reasonings post-event and colored my memory with my current understanding.

It's just not very valuable and doesn't make for a great book. It's just a fisherman's tale of the one that got away.

Most folks would rather learn about the failures of people who succeeded - because it shows that despite failure, they learned how to succeed, and can accurately post-mortem their failures through the lens of actual success.

Even better - the successful people can explain times they succeeded but SHOULDN'T HAVE, given what they know how. I heard about Daymond John from Shark Tank who said one of the most important deals of his life was one that he NEVER would have attempted to make today. It was foolish, arrogant, ignorant, insulting and ridiculous. But it worked, and if it hadn't have worked we may very well not know his name today. But now that he's successful he can look back at that success and explain how bad of an idea it was DESPITE it working at the time. That's super valuable.

This is my opinion of why you're having a hard time finding books like you suggest. Nobody wants to hear a fisherman's tale about the one that got away unless the story ends with an even bigger win.

Historically there's value in understanding the biggest failures of all time (wars, politics, businesses, etc...) but the only matter because of the success that preceded it. Hitler may have failed to win the war but he succeeded in MANY ways leading up to that point. That's why his failure is important - because he reached world-scale levels of power before that point.
 

MJ DeMarco

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But what about the massive F*ckups? The people who could've won but who didn't because they were too lazy, too unmotivated, too arrogant, etc. I truly believe there's as much to learn from their stories as there is from the stories of the winners.
It's just not very valuable and doesn't make for a great book. It's just a fisherman's tale of the one that got away.
I respectfully disagree. I for one, would be interested in this book. I think it would be a great teaching tool.

Of course it would have to be done in a manner that goes beyond the superficial and beyond "I should have bought 100 bitcoins when it was at 20 cents!"

Some ideas (beyond the "Into the Wild" story) could be decision points that clearly (in hindsight) were wrong, and why that decision was made incorrectly.
 

The-J

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Read a book on colossal military failures, such as Stalingrad, the Winter War, Russo-Japanese War, Battle of Waterloo, Rommel's North Africa campaign. Those failures were not only spectacular, but somewhat avoidable in hindsight with some different decisions.

I don't have recommendations for you because I have only watched videos and listened to podcasts on these, rather than read books.

You already mentioned Napoleon attacking Russia in the winter. There's tons of these stories from nearly every culture.
 

Get Right

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Lol, follow my thread(s). I even "F" up writing a book.

Movies: All is Lost (I love this movie), The Perfect Storm, Wolf on Wall Street (NSFW)
 

GoGetter24

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Selection bias + power law = that's the reason you only hear about the winners.

Keep in mind that even some of these famous guy's "screwed up". Peter Thiel, for instance, failed to invest in Facebook's Series B. As a result, he's only a billionaire, instead of a super billionaire :D

Then you have guys like Chris Gardner, who did screw up, but you only know about him because he then fixed it in a big way. Even guys like Jim Rogers, who is a rich & famous investor, was short oil just before Iraq invaded Iran. But they picked themselves up again.

A fairly good book on this is The Luck Factor: Changing Your Luck, Changing Your Life - The Four Essential Principles by Richard Wiseman, because the guy actually went looking for losers to interview, to learn how they'd failed at life. Some of the stories and his analysis of them were quite good.

But good look finding "famous losers". No one wants to look at them, let alone spread and remember their name.

This is why I prefer bio cases where the guy was just completely in the ditch, and then dragged himself out of it to become great. Sylvester Stallone is the classic case of this.
 

NanoDrake

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I would be SUPER interested into this book.

Furthermore, "you can only connect the dots afterwards" so a "success blueprint" is technically useless.
If it would avoid this bias, it should be a must read for everyone.

We kinda know more or less what is needed for success: great product that solve big problem, hard working ceo, world class team, disruptive distribution strategy, blabla, but where do we know these things? from the winners.

The lessons there were more eye opening for me than reading the bio's of who made it, were hearing the stories of other "failed" start uppers, yet they were doing all the "right things", content marketing, finding great talent, using MVP strategies... yet they haven't survived the test of time.

I'm a big believer of the Inverse model, hence, if you take care of the negative things, the good ones take care of themselves.


I would start reading the classics, since as noted by W. Durant, history is a mere reporter of the human behavior.
Also, this video might be a good starting point (please let's no value the form or the author, just the names he quotes and then do your own research)
View: https://www.youtube.com/watch?v=iG522u1wsr0
 

NanoDrake

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Read a book on colossal military failures, such as Stalingrad, the Winter War, Russo-Japanese War, Battle of Waterloo, Rommel's North Africa campaign. Those failures were not only spectacular, but somewhat avoidable in hindsight with some different decisions.
Go for the Cannae's battle, the worst defeat of the Roman empire.
 
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Your Boy George

Your Boy George

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I kind of disagree.

The folks who never succeeded can SAY that they could have won big "if...", but that's just purely based on hindsight, which is always 20/20.

I could tell you I'd be a millionaire right now if I invested my home's equity into bitcoin 5 years ago. I could tell you why it would have been a good idea based on market trends and the economy at the time and political this and that and entrepreneurial whatever and a million other great, great reasons. I could tell you why I almost got into it, why I didn't, and a million other things but at the end of the day it's all hindsight - I learned all the great reasonings post-event and colored my memory with my current understanding.

It's just not very valuable and doesn't make for a great book. It's just a fisherman's tale of the one that got away.

Most folks would rather learn about the failures of people who succeeded - because it shows that despite failure, they learned how to succeed, and can accurately post-mortem their failures through the lens of actual success.

Even better - the successful people can explain times they succeeded but SHOULDN'T HAVE, given what they know how. I heard about Daymond John from Shark Tank who said one of the most important deals of his life was one that he NEVER would have attempted to make today. It was foolish, arrogant, ignorant, insulting and ridiculous. But it worked, and if it hadn't have worked we may very well not know his name today. But now that he's successful he can look back at that success and explain how bad of an idea it was DESPITE it working at the time. That's super valuable.

This is my opinion of why you're having a hard time finding books like you suggest. Nobody wants to hear a fisherman's tale about the one that got away unless the story ends with an even bigger win.

Historically there's value in understanding the biggest failures of all time (wars, politics, businesses, etc...) but the only matter because of the success that preceded it. Hitler may have failed to win the war but he succeeded in MANY ways leading up to that point. That's why his failure is important - because he reached world-scale levels of power before that point.
This is an interesting point you make that it's only worth studying the failures of the winners.

Don't you think that perhaps a bit of a toxic over-optimism and arrogance can develop from studying people who lost big league and then came to win in the end?

Say for example you're losing shit right now and you're a total loser with everything going to shit. Or lets say you're going about your life/business and like any normal person, you're having a bit of a rough patch that has the potential to get precipitously worse. Well, if your only reference experiences for other people who were losing are Steve Jobs (kicked out of Apple) and Colonel Sanders (homeless), don't you think perhaps you can get arrogant and think to yourself (consciously or unconsciously) "It doesn't matter if I lose because look at Steve Jobs, he got kicked out of his own company but came back 10x stronger! I will do the same!"

Thus the arrogance, laziness, and over-confidence kicks in because if you can't lose in the end, like all these successful people who you've studied who failed hard but still won in the end, it takes a ton of positive and healthy pressure off your back that would otherwise be there to help you succeed.

@GoGetter24 mentioned power laws and selection bias contributing to people who died failures being relatively unknown. These massive losers do exist (albeit, still depending on what you define as a "loser"-- not all have to live under bridges necessarily). And these are perhaps some of the most helpful experiences to learn from lest we become prideful and arrogant of invincibility.

Historically there's value in understanding the biggest failures of all time (wars, politics, businesses, etc...) but the only matter because of the success that preceded it. Hitler may have failed to win the war but he succeeded in MANY ways leading up to that point. That's why his failure is important - because he reached world-scale levels of power before that point.
I think you're right in saying this. Perhaps the best way to study this scenario is through winners who died losers, not losers who died losers. There was no light at the end of the tunnel for Hitler, Napoleon, etc and in remembering that, the illusion of invincibility fades. Although, this is a surprisingly hard scenario to find in the business world (as explained in depth via books/movies at least).
 

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