I spent some time with a very impressive entrepreneur today. Within the last 5 years, he started a company in the email space, sold it to a larger company, became the CTO of the combined entity, took risk off the table personally and kept substantial upside potential at the same time, then helped sell the combined company on to Microsoft.
He is now starting a new company with fundamental technology that solves a large problem, but is aiming at a more modest and carefully-scaled initial application. This is certainly a well-planned strategy.
I was particularly impressed by the way in which, with his first company, he had identified and addressed a specific niche opportunity and executed successfully during a period that was counter-cyclical in terms of large Internet trends (e.g. video startup mania).
This one will be exciting to follow. I would tell you more, but then I would have to kill you :)
I will say that this entrepreneur discovered and reached out to me through LinkedIn and Mattishness.com which in and of itself demonstrates uncommon initiative in my experience.