He wasn't walking away from anything. He would have been fine if it didn't work.
The reality is he had a safety net to fall back on. 99% of people do not.
I'm no expert on any of this, but as far as I understand it, homelessness is usually 1. transitory, and 2. usually tied to other serious issues like mental health issues, drug abuse etc. It's usually not a "lack of resources".
Like, common. And beyond homeless, you have people one paycheck away from being homeless. And people unable to pay for drugs they need - like insuline.
Yes, if all you know about West is what you see in movies, then everyone is rich.
Which really reflects to how most people's parents/family/society is pathetic.
Now I'm not merely talking about a safely net after one burns up millions in a startup but I'm taking about say a safety net after loosing a job etc. I think most people (like me) would be just happy to have stability in life rather than yearn for being financially successful. The precarious existence is depressing.
I suppose it shouldn't be terribly surprising as being successful requires hard work & a good idea. But it REALLY REALLY HELPS to also have a risk appetite, capital, and connections.. which are what coming from even moderate wealth provides.
I graduated in 2008, and I watched classmates make the 'insane' decision to risk it all and go off and try to found startups. Inevitably, some failed, but to my shock it wasn't the end of the world for them? In one case the 'bank of mom and dad' paid rent until they got back on their feet, and in the other, they moved into an ADU in their parent's back yard.
That's when it hit me that those folks took risks because they could afford to. I was worried about winding up sleeping under a bridge. That concern was as foreign to them as the thought of having a safety net to fall back on was to me.
"Entrepreneurship is like one of those carnival games where you throw darts or something.
Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on.
Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good about themselves. Some keep going until they hit the center bullseye, then they give speeches or write blog posts about "meritocracy" and the salutary effects of hard work.
Poor kids aren't visiting the carnival. They're the ones working it."
For years, Amazon enabled everybody to bypass sales tax which gave Amazon a 4-8% advantage on books over brick and mortar that had to pay both rent and sales tax.
Quite a few of the "successful" tech companies followed this pattern: Uber, Lyft, AirBnB, etc. all engaged in blatantly illegal behavior to become big.
If you or I aided and abetted widespread tax evasion, we would get our asses handed to us in court.
The 5-4 majority in 2018 included two justices who were part of the unanimous holding in 1992 (Anthony Kennedy and Clarence Thomas), voting to overturn their own decision from a quarter century before.
In 1992, SCOTUS ruled in Quill vs. North Dakota[0] that a business must have a "nexus" in a particular state to be required to collect sales taxes. I'd note that Amazon was founded in 1994.
And so, yes Amazon did have an advantage WRT sales taxes. But it wasn't, as you said, "outright illegal" until 2018 with SCOTUS' ruling in South Dakota vs. Wayfair Inc.[1] At which time, IIRC, Amazon continued collecting sales taxes that it had already been collecting in many states, as already it had nexuses (warehouses, distribution centers, etc.) in many places.
I'd note that I'm not "defending" Amazon here. They do plenty of shady stuff WRT pricing, as well as abusing their employees, suppliers and third-party sellers.
Why don't we take them to task for that stuff instead of making stuff up? Just sayin'
[0] https://en.wikipedia.org/wiki/Quill_Corp._v._North_Dakota
[1] https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair%2C_Inc.
Why doing something that is merely illegal deserves a punishment, in YOUR books?
Why don't you see that many laws are the in place serve some cartel or other, to be outright unjust?
See also: PayPal, OpenAI, ...