Most of the intrinsic value in companies is usually created in its formative years. If you are productive in the early years of corporate evolution and less productive or interested in more mature operations, you could earn more money by starting and selling many different early-stage companies. On the other hand, switching could have consequences too: like paying extra taxes, possibly needing to learn a new business, and definitely having to re-orientate yourself to new players in new markets, i.e., lost leverage.
Another potential problem is that you could have a non-compete agreement, which would prevent you from competing with your former employer, the company to whom you sold out, and thus require you to start in a completely new industry or territory.
