Unfortunately, I know of a startup that did exactly this and made out like a bandit.
An acquaintance of mine started some Java/Web startup when the web and Java were just taking off (1998? 1999?). He made a lot of noise. Then he hired a top B-school alumnus to specifically get his company bought out, and promised him a large chunk (30%? I don't remember) of the company if it went for more than $X million. Well, lo and behold, the B-school guy found a sucker and the company sold for close to $50M. This guy retired right away, and now cruises around as an "angel investor".
An acquaintance of mine started some Java/Web startup when the web and Java were just taking off (1998? 1999?). He made a lot of noise. Then he hired a top B-school alumnus to specifically get his company bought out, and promised him a large chunk (30%? I don't remember) of the company if it went for more than $X million. Well, lo and behold, the B-school guy found a sucker and the company sold for close to $50M. This guy retired right away, and now cruises around as an "angel investor".