How to Fail at Almost Everything and Still Win Big

4.5 stars. I knew nothing about this book going in and really enjoyed it. It's an eclectic mix of good advice on a variety of topics, interspersed with personal stories. I think his concept of weighing your personal experience against the advice of others is particularly important. Could be a good introduction to a life hack mentality.

Warning, rant: I felt the need to leave 5 stars to offset the surprising number of 1 and 2 star reviews from people who apparently didn't bother actually reading this:

- he came from a small town and he (and I assume his siblings) were the first in his family to go to college.
- his parents didn't have the money for a private college; he had to help pay his way.
- his so-called dumb college stories were to reveal his lack of knowledge of what was acceptable in the business world (and lack of good advice from the people around him).
- the Dilbert characters stuck in cubicles? He was one of them for years. He got up at 4 am to work on Dilbert because at first it was a side hustle.
- many of his business failures were before Dilbert got big, and some involved hours of learning to code himself. Tell me that's not perseverance.
- he's had multiple serious health issues.

These are only the things he's chosen to write about, and only in this book.

Yes, he's rich and famous NOW, but the reviewers complaining about how “lucky” he is are missing the entire point of the book, not to mention skipping over what he actually wrote. It's clear he tried not to come across as out of touch. The general public assumes that an overnight success is actually a thing, simply because they don't see the blood, sweat and tears that an artist or entrepreneur pour into their work, or all failures that came before. He's trying to let you in on that and for some people, it didn't appear to work. I agree with him; your job is to make it easier for luck to find you, which is exactly what this book is about.

In my opinion, the only people with a right to complain that he's just lucky are the most disadvantaged among us, who could probably level that complaint against anyone on the low end of middle class.