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Well, for one, he's not that kind of entrepreneur. He made his fortune by starting off extremely wealthy, and then expanded it by defrauding people and going deeply into debt, rather than producing anything of value.


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He got rich. His own reputation pretty much stays intact as genius visionary founder.

It's not much of a learning experience if all you get is rewards. Even if he's bitter that the rewards weren't as much as he wanted.


There are a lot of people out there who inherited a family business and failed, It's never easy to grow a business whether you inherited it or started from scratch. He took his business from 3 to 60 million dollars, I don't think that's easy.

Most startups fail, so it's not surprising many of his initiatives have also failed. Regardless of his career path, at least he's now trying to do something worthwhile with his wealth.

Presumably said CEO wasn't in much danger of poverty though. The entrepreneurship caused his troubles. That other things also could is beside the point.

He claimed to know things about the economy and raised $8 billion to capitalize on his ideas. Turns out he was full of shit. He had no idea what he was doing and lost huge amounts of money over years. He wasn't just bad he was arrogantly clueless.

Now he's claiming to know things about the economy again.


If this really had anything to do with it, why did he keep going at all? After all, what's the point in trying to start a company if you already have a wealthy family and a safety net?

"The entrepreneurship caused his troubles."

Did it, though? That sort of misfortune can and does happen even without entrepreneurship, and might well have happened to him anyway.


To be fair, he made money largely because he was well connected. His ability to steer a large enterprise and maintain a vision has made him a horrible excuse for a CEO. Doesn't surprise me that this all comes down to money and not real value.

one thing he did wrong like losing his company multiple times? sounds like hes bad at business

He started 500 businesses, 6 went bankrupt.

So what you are saying is he's brought some cool-sounding businesses and founded some business failures? It's not very impressive tbh.

I don’t really see why it’s his fault investors over valued his company — he believed in his own spin and was phenomenally successful at building a large, real business. This was not like Theranos where he was straight up lying about a product working — anyone could analyze the business based on the fundamentals, and investors seemed ever willing to invest at high valuations.

The self dealing was reprehensible and evidence of low morals in my view, but none of those events actually materially impact the value of the business. Instead, overnight, investors just came to their senses about what kind of value this type of business is worth. Definitely a strategic misstep on his part, but it’s not like he stole billions of value away from the company. The drop in value is more like what happened to Uber or Blue Apron post IPO, except, unfortunately for the employees, it happened before they could exit.


He tried to leverage his notoriety in another startup but apparently that wasn't enough.

That's only because he succeeded. A lot of "visionaries" have become irrationally attached to failed ventures and drove themselves bankrupt.

It's not necessarily a good idea to get too attached to a business. The whole point of finance is calculated risk taking.


My issue is that before his consulting career, he was lauded as a business god, when in reality his main business couldn‘t pay the bills for a single person in most parts of the US.

He worked his ass off in an I.T firm, became good friends with the CEO...and helped grow that company. He made Director in 2 years. I think what bothers him is that he busted his ass to make that company big, and made his boss SUPER wealthy. So although he's making good money, if it was his own firm, he would've been a millionaire by now.

It seems he latched onto a great business opportunity, and if he'd been able to resist scamming people, he could have become very wealthy.

A guy who has more money than he could ever spend in a dozen lifetimes. He could have kept these afloat indefinitely while trying to find a workable business model. This was pure spite and greed. He probably has no problem working with other wealthy people to bring benefits to wealthy people, yet he has a problem with his own workers, trying to join together to represent themselves. It says a lot about where we are as a culture that we need to place the delicate feelings of a man who's every material need and more is catered to while ignoring the needs (food, shelter, health care, etc) of his workers.

Maybe "entrepreneurial success" would have been a better phrase (as douchey as that word can be). While his licensing, branding, and endorsement income has been huge, his attempts to start up businesses of his own have been less than noteworthy successes.
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