To be sure, this is an endlessly rehashed topic. Jeff Yee, a former Softie, moved to Red Fin recently and has posted his thoughts about the matter on his Red Fin blog. I think he has a number of interesting points that are worth considering.

Almost all the top engineers I know talk ad nauseum about starting their own company, with the caveat of, “I’ll stay at big company XYZ for 2-3 years, then I’ll go out on my own.” Well, it never made sense to me how they thought that they could make the transition from being so removed from the business and the end to end process of creating and shipping a product.