The investor doesn't sound very sophisticated (sounds pretty stupid actually). The company is about to clear a hurdle that most startups don't, so the investor

The investor doesn't sound very sophisticated (sounds pretty stupid actually). The company is about to clear a hurdle that most startups don't, so the investor decides to be greedy and potentially throw a wrench into the whole deal to maximize his short term gain. I would throw him a bone by creating an option for seed investors to cash out in future rounds of funding, or create some sort of compensation plan if his concern is about his time commitment. Otherwise, suck on it. If he doesn't like the risks associated with startup finance, he can put his money in an index fund and go play shuffleboard.