The dramatic difference in price is really between pre-funding to post-funding. e.g. I know many companies where options were granted at 1c a piece, even as see

The dramatic difference in price is really between pre-funding to post-funding. e.g. I know many companies where options were granted at 1c a piece, even as seed notes and safes were given out, but as soon as the Series A equity round hits, the 409A & thus options grant went up to $0.50+. That's a huge difference. That said, your point about having 7 years to decide is entirely fair, and mostly negates that downside.