Based on your comment elsewhere[0], I seem to be among the crowd you believe is throwing around irrelevant moral arguments when in fact I did not and 3pt14159[1] to whom you’re replying here did not. I was discussing valuation and 3pt14159 probability.
The founder owns a chunk of equity, an asset with some value. Given the ups and downs of reaching a point where people are kvetching about equity allocation — and 3pt14159 reminded us about survivorship bias — the founder may overvalue her stake. If bad news has recently hit, she may undervalue. Regardless, the question is what will persuade the founder to give up a piece of what she owns, and what will she accept in exchange?
Looking backward does not generally make for wise business transactions. The entrepreneur’s role in the market economy is looking ahead to make forecasts and allocate capital accordingly. Comparing past exposure to loss is a pointless exercise. Giving away resources with no hope of repayment or increase is gifting. Spending with the expectation of regaining what was paid plus an additional return is investing. This is still not a moral question but one of philosophy.
Many people miss this when looking at the situation as though it were an undeserved windfall for the founder, a gift from Santa Claus. Assuming the founder is primarily interested in increasing the value of her equity, accepting a smaller percentage of the pie will not achieve this purpose unless the individual slices become more valuable because the grant of equity was an investment, and “Well, I’m going to continue doing the same job I’ve been doing for the compensation I already agreed to” is not a strong business case.
Looking at it from the employee side, of course don’t agree to below-market pay with zero or insufficient equity on the mere hope that big blocks of equity will fall out of the sky later. (This would be an opportunity cost for the employee, but that is still different from out of pocket cash loss to which the founder may have been exposed.) Employees who want more have to either negotiate for it up front or increase their value to the business. On this, I will make a moral argument: yes means yes. Ask for what you want, and agree to what is acceptable. No one is a mind reader.
[0]: https://news.ycombinator.com/item?id=17553940
[1]: https://news.ycombinator.com/item?id=17553645