I don't see this as an example of a bubble. With a track record of success with Vimeo, there's a good chance he'll succeed again in the future. Frankly this is probably a safer bet than a group of founders straight out of college that have some decent traction. He'll know the stumbling blocks and the connections to make things happen. The only thing I'd want to know as an investor is what the salary situation is like. Assuming its nothing or very low, I'd say good investment.