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When you’re as rich as he is what difference does it make?





Funny thing is his net worth is almost entirely tied in Automattic, and he is doing his very best to crater the company's value.

His sense of self importance and relevance seems to be especially crucial to him. He is losing both.

I'm trying to figure out what's the most loving thing to do for a person in his situation.

I've done my best not to pathologize him here, but...

Suggest therapy.


Sometimes, rock bottom is the only way to stop

+1, unfortunately counter-intuitive. A bit of a song comes to mind:

"A junkie won't bounce until he hits the ground" - Say Hey There, Atmosphere

My family and I all tried to help a sibling for something like 20 years. Nothing stuck [from us], they had to choose it. The ground helped. Trying to minimize harm just created more :/


If you’re a relative or friend, take them aside and have a frank conversation. If not, nothing you can do!

And accept that there’s a good chance this will accomplish nothing but getting you on their naysayers list.

People can continue behavior where all they really need to do is stop actively harming themselves for no gain at all for years. It’s bizarre to watch from the outside. In the best cases they haven’t roped anyone else into their delusion-bubble.


I think it's to try to help them by offering compassion, understanding, and trying to create harmony.

Try to look at it from an outside perspective instead of through the lens of our own preconception. Humans are subject to making terrible mistakes and lapses of judgment. Sometimes things spiral out of control. We all have our demons, so to speak.

It's very easy to judge a tech multimillionaire bro and saying he should know better, he deserves this, etc. And I mean easy as in cheap. It's the prevailing view and it feels "fair" to a lot of people who didn't get so lucky or so far ahead in life, so they don't feel the need to be sympathetic. But it adds no value to the situation, so it's a pretty useless take. And it's not like the world has a limited supply of sympathy, so it's OK to offer it even in these situations.

At this point I think the guy just needs help.


Ego doesn't go away just because you made a bunch of money.

If anything, experience suggests it's the opposite.

There's usually a crowd of hangers-on who are feeding the ego and enjoying the perks.

They need someone to whisper in their ear "remember you are mortal" [0]

[0] https://en.wikipedia.org/wiki/Memento_mori


Functionally infinite money seems to just not be enough in life for a lot of people. I honestly think if they weren't powerful it would be considered a serious mental illness.

Couldn’t have said it any better, thank you.



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