Also, investors help with accountability, pushing through tough spots, connections, advice, etc. Investors also add credibility that 'rich white guy throws money at project' doesn't give.
I also wonder how much success he's going to get selling to enterprise customers. Any company with over 200 employees already has a calendar system (Outlook or some cloud equivalent).
If you hire 20 people for the first year, that's going to cost three million dollars (if you're lucky) for everything all-in, without calculating potentially high customer acquisition costs early on.
Writing the calendar app is the least expensive, least difficult and least time consuming part of building a large scale business around it.
If you wanted to go big, and had three years to do it, you could easily burn through $10 or $15 million trying to get there before generating your first quarterly profit.
Heh. That's putting it mildly. Yes, he's hedging his bets. He has some Dilbert money he doesn't want to lose in case CalendarTree tanks. This is antithetical to a typical image of an entrepreneur who goes all in, and is a fanatical believer in the success of his or her product. A cynical angel may look at his start-up from that perspective.