The title alone is enough to give me pause. "Lean In" refers to the antiquated idea that the reason why so few women succeed in the workplace is because they "lean back" instead of "in" during meetings. Right, because all you need to do to wring a few more dollars out of a stingy, psychopathic billionaire institution that would throw you out on the street if it saw profit in it, is a little more work on your posturing. Keep an acute angle between your spine and your pelvis and everything else will follow.
Reality: most people who are successful have no insight into how they got there, and the system's supposed to work that way; the elevator up is made of glass, but the people allowed into it were deliberately picked not to look anywhere but at the digital red numbers that say what floor they are on. Of course, most people who fail (and that's most people) have little insight either, which is why these books sell so well.
Also, let's talk about Small Data, the realm not of normal distributions but of Poisson distributions on discrete events. Reputations are a Small Data problem. So are introductions, resumes, and all of the other mechanical rat-traps that make up the career game. You can control serendipity to some degree. If you know a disgusting secret on a Harvard MBA alumnus (which is not that hard, because as unethical people become increasingly arrogant, they get worse at hiding it) you can use it to get a powerful recommendation, get in to Harvard Business School, and make influential friends. Sure, there are things like that that you can control. Then there are things that you can't.
Filthy secret: the workplace is full of extortionist thugs, bullies, and generally horrible people. I'd estimate that horrid people are 1-in-10 in the general population (but you rarely see them in daily life, because there isn't money involved) but they are 1-in-5 co-workers at the most competitive companies, and 1-in-3 bosses. Okay. Let's just get that on the table. Unless you have extreme luck that makes you independent in your first 5 years, you will meet horrible people who will fuck up your career, damage your reputation, gaslight you until you embarrass yourself in a major way, steal credit that you needed to get out of corporate hell, possibly even give you PTSD (that's rare, but if you have the condition pre-existing, it can flare up again). One such encounter takes you out of the running for those COO/Facebook jobs that require a flawless career history, but you can still be modestly successful. Two hits and you will never raise VC. You're too damaged for that. Three and you're barely holding on to the upper-middle-class. Four, and you're lucky to stay in the middle class. Now, some people manage to get hit zero times. Look up Poisson distributions if you don't believe me. It's not many of them, but it happens. Good for them.
Why do so few women succeed in the workplace? This "they stop leaning in!!!111" bullshit is useless, because it glosses over the real problem. It's because bullies (including workplace bullies) prey on the people they consider to be weakest, and those are disproportionately going to be women. It's not that they're sexist. Not all bad people are everything bad (i.e. not all psychopaths are sexist or racist). They're just opportunists. They hit women disproportionately because they presume them to be weak.
You can really tell what kind of career (in a corporate context, and VC-istan is corporate because of the king-making around funding) someone will have based on one integer number: how many times that person has been attacked by a workplace thug. You will never be a Sheryl Sandberg if you've dealt with a true workplace bully, and at least 90% of people get hit at least once in the first 10 years. Your reputation and career history are too damaged, and you really can't "start over" because every achievement is age-graded.
It's great that some people like Sandberg are able to enjoy legitimate careers, but the fact of never having been bullied or attacked (they might have been laid off once or twice, but never robbed or extorted) makes them extreme statistical anomalies. They end up with these rosy-eyed half-picture views of the workplace, and they're able to sell it in business books and TED talks, because most of the proles want to believe there's something different out there, and that they're just missing one easy insight (i.e. just "lean in" during meetings!)
Success Crack presents a view of the workplace that is so non-repeatable and often self-serving as to be indistinguishable from a fantasy novel-- but with a less inspiring setting and worse writing.