I come from the fuck you pay me school of equity.
Now the startups's got Paulie as a partner. Any problems, he goes to Paulie. Trouble with the bill? He can go to Paulie. Trouble with the cops, deliveries, Tommy, he can call Paulie. But now the guy's gotta come up with Paulie's money every week, no matter what. Business bad? "Fuck you, pay me." Oh, you had a fire? "Fuck you, pay me." Place got hit by lightning, huh? "Fuck you, pay me."
That said, I also don't care about business strategy, blah blah blah, that's up to the founders, I'm happy to add my 2cents but as a professional my job is to implement their vision. Not play venture capitalist with my time rather than my money.
Think about it, HN gets 5% for 20K, if you make $100 an hour, that's 200 hours. Imagine the typical first employee, 1-2% with a 4 year vest, that's over 8000 hours (assuming an 8 hour day, let alone the typical death march), and it's doubtful you'd come even close to $100 an hour. If you're working for equity you're paying close to 100 times the price for a much shittier class of shares.
Now on the otherhand if you take a convertible note at $20K and the founders can't raise anymore, just call your loan and grab the IP, or break even on the aquihire.