I suspect there's no way ESR even got $1 million out of VA Linux.

1) ESR was on the Board of Directors of VA Linux and subject to the 180-day lockup so there is NO WAY he could sell under SEC regs until after 180 days so he couldn't get that $274/share ($36 million). I agree after 180 days his stake would be $6-7m "on paper" and 1 year out as you say ~$1million. However...

2) Per Wired article the day after the IPO covering Eric making foolish comments (actual comments: https://lwn.net/1999/1216/a/esr-rich.html Wired coverage: https://www.wired.com/1999/12/open-source-rich-opens-mouth/ ) ESR had options on 150k shares with a strike price of under 4 cents but there was a four year vesting schedule. I don't know his vesting schedule, but there's no way he had vested even half of that amount during the timeframe when the shares were still $40+. Per his resume (http://www.catb.org/~esr/resume.html) , he was a Director from November 1998 to April 2002 so not a full 4 years.

3) Confirming that further, per SEC filings required from insiders on the Board as he was, he has no registered sales while he was before he left the VA board, ie no sales in 1999-mid-2002:
https://web.archive.org/web/20030201132729/http://biz.yahoo....
https://web.archive.org/web/20010615000701/http://biz.yahoo....
https://web.archive.org/web/20000815055303/http://biz.yahoo....
He is shown in that last link as having, in addition to the 150,000 shares "Initial Direct Holdings Statement" as having on Dec 31, 1999 "Acquired via Exchange" 12,952 shares with a then-market-value of 2,676,207, but he is not shown as having sold any shares. I am not sure what the taxable implications of whatever happened in that "Exchange" (if there were some, then could actually have lost money on the whole thing!) but I don't see that he sold them while he was a Director. He rode the stock the way down. Purely speculatively, I wonder if the grief he got about his comments at IPO time made it harder for him to sell while he was a Director. His sales must have been on the open market after he wasn't a Director, ie post April 2002.

4) Let's say he sold on the open market post-April 2002 sometime within the following 5 years. Per LNUX stock charts at:
https://web.archive.org/web/20051208024613/http://finance.ya...
https://web.archive.org/web/20020223103417/http://finance.ya...
the stock bobbled between $1 and $6 from April 2001 to Jun 2007. $6 at (maybe) 162,952 shares is $977,712 max. Worst-case he had quarter vesting at IPO which he exchanged for 12,9k shares outright. And worst-case he had two more (but not the final year) years of options vested (75k) which he then sold for at a bad time for around $1 which was ~$87k. So somewhere between $100k and $1m (pre-tax!) seems likely to be what he made; the truth is somewhere in-between.

5) ESR has actually publicly answered some questions on this topic. Per http://esr.ibiblio.org/?p=556#comment-228165 :

"[Q:] If I remember correctly, you've made a fortune on VA Linux's IPO. Didn't you sell those stocks while they were up?

[A:] Nope. Didn’t sell before the bust. Too busy worrying about other things, like changing the world."

6) Some ironically less-connected open source contributors were able to put their own money at risk and buy up to 100 (or 140?) shares @ $30 each pre-IPO. They were able to sell on day 1. See Chris DiBona's comments at
https://slashdot.org/story/99/12/09/1324204/va-linux-systems... ("Everyone who was in the program and faxed in thier forms is by default confirmed for 100 at 30$. To change your share allotment to 50 or 140 , you must call and tell them. .... You can sell now if you like. " and bgdarnel quoting from the "VA Letter" describing how eligibility in the "friends and family" allocation to open source contributors worked. But the limits of that allocation limited the upside to < $30k. Nice if you got it (and kudos to VA for doing that!) but not making-you-rich.

7) Other clients of the IPO underwriter(s) (e.g. Deutsche Banc, etc) who got larger allocations were able to make more money... if they flipped quickly enough. There were SEC probes around oddities surrounding the IPO allocations back at the time: https://www.zdnet.com/article/sec-probes-ipo-of-va-linux-500...

Sorry for this long research project. I don't care that much but I got curious and I kept finding more tidbits as I dug.