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Jim's point is that you only need so much money, so waiting for (as an example) $20m instead of taking $10m now does not make sense.

I think that his argument can be turned around: founders of a successful company should be getting a good salary. If they invest some of their take home pay, they should fairly quickly own their own home and have diversified investments. Even on the downside that their company greatly decreases in value in 5 or 10 years, they still have had good income, diversified savings, and have skills with high market value.

The happiest people in the work force tend to be those with the most control over their work and lives. Owning your company (even if it is a small consulting shop, or a single consultant) offers a great deal of control over one's own fate.

On the other hand, if someone simply wants to cash out and not work anymore, then selling is a good idea.

This mismatch or risks is also what get's VC's and founders into trouble many times. They can both agree on what the risk is of not selling and come to correct but opposite decisions. What is too risky for the founder is just right for the VC. One of the solutions to this is letting a founder take some money off the table. This would align risk tolerance, but could also take some fire out of the founder's belly.

Selling certainly is a very tough decision and I think DHH may have oversimplified to make a point.