Leo thinks the future of Microsoft is dim, and that the Microsoft acquisition of Nokia was a hail mary play. Microsoft's profits are still high, revenue is still billions of dollars a quarter, so the company isn't going away anytime soon. However, he doesn't think its a company to watch in the 21st century.
Matt thinks Microsoft has a lot of talented people and so much money, but its being wasted on things that aren't all that exciting. Leo says all of those bright minds want to work for a company with a stock price going up, and they also have pride and want to work for an exciting company. However, a lot of the new talent coming out of school are creating their own companies instead of going to a major company like Google or Facebook.
Microsoft may have bought Nokia for better hardware innovation, while Microsoft is more focused on software innovation. The only question mark at this point is whether or not Microsoft can get a CEO who can reverse the trend. It's happened before to many other companies, but it isn't easy. Things move fast, and success in one decade almost guarantees failure in the next.