I am not going to shed a tear for ESR. He turned out to be a massive turd.

ESR was always somewhat controversial. People trolled him at the time for what they saw as faux humility and virtue signaling.

> ESR

That's a name I haven't heard in a long time. I'd almost forgotten about the webcomic.

https://geekz.co.uk/lovesraymond/

I recall this. But I didn't know he nevet made real money

To make money he would have needed to sell his shares, and they became worthless before the post-IPO lockup period ended.

they shouldn't have been.

From wikipedia

The company raised $132 million, offering shares at $30/share, but the shares opened for trading at $299/share, before closing at $239.25/share, or 698% above the IPO price, breaking a record for the largest first day gain.[7][8][9][10][11][12][13][14] Larry Augustin, the 38-year old founder and chief executive officer of the company, became a billionaire on paper and a 26-year old web developer at the company said she was worth $10 million on paper.[2] By August 2000, the shares were trading at $40 each[2] and only 24 mutual funds held the stock.[15] On December 8, 2000, one year later, after the bursting of the dot com bubble, shares traded at $8.49/share.[16]

per his essay he was given 150K shares. Even at the IPO price of $30 a share, that's 4.5 million. Do we not think the investment bank handling his shares would have been willing to take his whole stake at $30 a share?

But even if they wouldn't more than 6 months later it was still north of $40 a share (so $6mil or so) and even a year or so after the IPO, after the bubble popped, it was still north of $8 a share (so $1+mil).

I could be wrong! It seems to me like the terms of his options and his trade restrictions (he was a director of the company, he couldn't sell his shares willy-nilly) are important here, but I don't know the specifics.

He has, ahem, never exuded a "man of leisure" vibe. More power to him if he's actually loaded, I guess.

I'm not arguing that he's loaded, just that if he didn't make millions off VA, its more due to his own decisions than anything else. I could also be wrong, but it seems he had the opportunity to unload his stake if he really wanted to.

ISTR that the lockup period extended well after the delisting.

a year+ lockup seems insane.

90-180 days would be normal and was still trading above ipo price (not opening price) 180 days after ipo as i documented above.

with that said perhaps directors have a different form of lockup, can't say I have any experience with that.