I don't know why you're post the same advice
that, apparently, you know gets circulated
here continually
Because prospective startup employees get dazzled by promises of riches that, if they were to stop and do some basic arithmetic, they would know are highly unlikely. I hope that if I beat this drum long enough, more people will hear it. All that said, I'm glad that things worked out for Cliff.
If he had followed your advice who knows where he'd be.
He wouldn't have worked for "well below market rate" wages. That's for sure.
Also, it seems somewhat disingenuous, given this topic, that you don't mention you work for Greylock.
Well, that's a rather passive-aggressive way of saying nothing at all, but insinuating anything.
It's irrelevant is why, I do work for Greylock but I'm not advocating that people should work below market rates, or even saying your advice is universally wrong. I'm saying that you are posting this advice on a story which literally contradicts what you are saying. The "I left the money" story would have been a much more sensible place to leave your comment.
Speaking of arithmetic though:
He received 80% of a $300k payout over two years: $120/year. On top of that he received a salary of, maybe, $60-80k. I think he did fine, and has landed well
Your advice doesn't make sense for this story. It's like posting "and this is why I don't fly" on a story about an utterly mundane flight.
Since you are working for Greylock, which is a VC, your are directly vested into clueless/naive programmers accepting below market offers, working long hours for a false promise. It is usually the VCs and founders that make the most out of a startup. Hence your advice is misleading at best.
Also, as an engineer I'd like to see this cycle stop. It creates an exploitative environment akin to some of the bad stories you hear in the gaming industry, where young engineers are often taken advantage and burnt out the industry.
According to linkedin, he worked at powerset for 3 years at "well below market rate". He got 240K in bonus money from the acquisition. So the question is, how far below market rate? If he was making 60-80K as you suggest, that's about 60-80K below market rate. Which would mean that he took a huge risk for very little actual gain, especially since the bonus was probably taxed as regular income rather than capital gains.
Part of that was sunk costs. Presumably he was gambling on Powerset being a much higher exit. This store and the "I left $300k for github" are two sides to the question of what do you do when you are facing a soft landing rather than launching into orbit.
If the bonus had come in the form of a more lucrative cash buyout, it likely would have ended up being short term capital gains as options were cashed out, so there isn't even a tax difference.
The $300K payout was not a foregone conclusion, in most cases, the bonus does not come through.
What I'm really interested in, is where you came up with that "Salary of $60-$80K" - what is that number supposed to represent? It certainly doesn't correlate with any engineering salary in the bay area I've seen in 15+ years. I.E. That isn't "below market salary" - it's what most companies pay their interns/summer students doing Desktop Support for IT the first couple years. ($65K is actually my very first salary in the Bay Area - doing Windows 95 Desktop suport back in 1996.)
I made $80k out of college, as did many of my peers -- $80-100 was the range. And most engineers I know are making approximately double that at the 3-5 year mark. $80k is absolutely below market for an engineer with more than a little experience -- I don't know about the pay ranges for desktop support techs.
If the story is about someone achieving a rare but desirable outcome, and there's a common perception that the outcome isn't rare, then it makes sense to post a comment like the GP's. It may help prevent availability-biased readers from improperly "confirming" their belief that the event is actually not rare.
Also, it seems somewhat disingenuous, given this topic, that you don't mention you work for Greylock.