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These are all good points. To play Devil's advocate - the argument against this is that when you raise money you can sometimes take money off the table. Meaning you sell of a portion of your ownership for cash to you personally and not the business.

This is not always in the best interests of the company, because it doesn't incentivize the founder to stay as much. But it can be healthy for the founder's psyche to not have to have all of their net worth tied up in illiquid startup stock.

Also, I don't think this is as frequent as the crazy days of 2021. Where you could retire off of a Series A with not much revenue



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