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

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.