Greenspun has interesting things to say on occasion. It's a pity he feels the need to be such an ass:

"The folks who work at a non-profit organization are very interested in drawing a salary higher than their skills and working hours would command at a for-profit enterprise subject to competition. They are not especially interested in efficiency or accomplishment. "

I know several people who work at Cambridge nonprofits. They all earn about 1/3 what they could at comparable for-profit jobs. They do so out of a sense of passion for the mission of the nonprofit. Their lives have more purpose than, say, tooling around in airplanes.

Timing was bizarre - I just wrote a column about why entrepreneurs should NEVER retire!

http://www.gobignetwork.com/wil/2007/4/16/3-reasons-entrepreneurs-should-never-retire/10133/view.aspx

I think there'd be some period of 6-18 months where I'd truly do nothing but relax. Learn a new programming language really well. Travel and visit friends/family scattered across the globe. Then I think I'd end up doing some kind of startup hackery like Joe Kraus or PG.

To paraphrase a famous college saying:

"Read the five posts above yours; read the five posts below yours; only one of you will have a successful company."

Do what I do. Don't worry about retiring :) But if I did hit it big, I'd probably do astronomical research.

1) start another company 2) start angel investing 3) start coaching younger entrepreneurs how to change the world

This is what i want to do after i've started and exited my first startup

Same here. Also finding a way of showing students in the UK that they can create startups when they graduate rather than join a banking grad scheme in the city.

he didn't sell the company. he sued the company and they settled out of court. he made his money via legal action, not business or programming acumen. the sale was for pennies and was only done so that the VCs wouldn't look completely retarded for investing in the first place.

he didn't really have any choice but to retire. no investor will give him money and no programmer with any sense would work for him.

Greenspun had other companies before Ars Digita. He took ICAD/Concentra public and also co-founded ConSolve and Isosonics.

It may be true that no programmer with any sense would work for him - I don't know him personally. But given how cheaply you can start a company nowadays, he certainly doesn't need investors. And as I understand it, he's not entirely retired: doesn't he teach a course at MIT?

"It may be true that no programmer with any sense would work for him". Why? Did he do anything particular?

I don't know - "may be true" is just conceding the point to the grandparent, because I have no personal knowledge of Greenspun, and from his username, it appears that the grandparent worked at Ars Digita. I've heard that Greenspun's management-style was pretty abrasive and he could very egotistical, but this is all hearsay.

I don't know. Back in 1999 ACS was considered pretty ok. And his writings were the Joel/Paul back then.

This website seems to cover what you asked..

http://www.ryancool.com/

Well, one obvious solution would be to do something else, not to retire. Is retiring really what people aspire to, these days?