The main reason he failed is because the industries he picked - first publishing and second sitcoms - were declining industries. And no matter how smart or hardworking you are - and this dude was smart and prudent and hardworking - you can't fight against larger macroeconomic forces.
Was this an obvious consequence at the time? I think he took a big risk and it paid off. Props to him! It could have just as easily tanked his company as a result of an economic downturn.
I have to agree. It's not that he 'failed' in many respects he was wildly successful.
You can do a whole lot of things right but if their is something rotten at the core that undermines everything.
Groupon was rotten. The accounting was shady [1], in my view inexcusable so. I profited handsomely from shorting it, they sold the market what can only be described as a lie. The smoking guns were lying all over the place. Maybe if you tell yourself something loud enough often enough you can come to believe it, that doesn't make it true / right.
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.
We always need to keep in mind the bigger picture. Sure he made some poor decisions wrt business and relationships, but he probably always had a roof over his head and never went hungry. In first world countries if your startup fails, you can always go get some corporate job. If your crops fail in some poorer nations, you'd starve.
Suddenly it seems a lot harder to truly "screw up"...
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.
In his shoes, I would definitely call it a complete failure. It was certainly very educational, but failure nonetheless. I think his failure lies in equating making money with success.
The purpose of commerce is to help us create value for one another. But there is a bunch of activity that uses the same tools that is essentially parasitic. The reason his income streams kept blowing up was that people eventually decided that they were better off without him involved.
He could have spent 10 years building products that were creating value. He could have spent 10 years learning the tools and techniques necessary to make the sorts of thing where customers can't get enough. Instead, he spent a decade as a leech on the ankle of the economy, getting scratched off and reattaching himself.
I could have gone the same way. In high school I had a job doing telephone fundraising. It turned out to be basically a scam, with ~12% of the money collected even going to the non-profit, and therefore even less being spent on actual beneficial work. There was a lot that was appealing in the work: smart, funny people; great challenges; getting paid in cash. But eventually I came to realize how morally bankrupt it was. I got lucky in that it was much easier to see how what I was doing was worthless.
So now he's basically starting over. And good for him, I say. I think this post is incredibly brave, and I wish him the best of luck in making something so useful that customers are clamoring to hand over their money.
Furthermore, his plan didn't fail per-se. I am sure he was aware that he may have to go back to work if life threw him curveballs. It did, so he did. He had some of the best years of his life, he had some bad years. He is still doing financially well. That's as good as most people get working or not.
Because he was trying to build one of the biggest/most successful companies ever? Some things are just hard regardless of how smart you are, building a mega company is one of those.
He didnt figure out the concept of online subscription and ads. It shows he wasnt that revolutionary. Just lucky, born at the right time to the right family and lived in right neighborhood/country.
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