How bad are bad fundraising terms?

The analysis is useful, but seems undermined by the fact that Square is now trading at $32, which would put you significantly in the money.

When you look at the table in the end, it seems like it's more important to pick the right company, than the exact deal terms. Square was much more overvalued than Theranos, but obviously people at Square did significantly better from their equity.

I also wonder what sorts of strike prices people see at these startups; I would think a company's fair market value analysis would take these deal terms into account and use that lower price for the strike price.