I understand what Jason is saying here...but to be honest, it's hard to tell someone that is used to living on $40k/year, that they shouldn't take an offer of $20M - that instantly makes them a millionaire.
Ofcourse, once you make that first sale and have the FU money to fall back on, it makes gambling (i.e. growing to IPO) much easier.
You say it's not 'as good as it sounds', it all depends on your perspective.
If you are earning $40k - $60k/year - which many young founders were likely earning before joining YC - even if after multiple dilutive rounds of financing you end up with 10% of the company, in a $20M exit....that's still $2M.
Sure, you can't buy Fiji....but you are literally going from a bank account with a few hundred/thousand/tens of thousands, to literally hundreds of thousands/millions.
That is VERY major the first time it happens.
I guess the point I am making is, the jump from having $10K in the bank to $1M in the bank, is SOOOO much bigger than from $1M to $100M - because it impacts your life much more.