Your starting position has to be somewhat optimistic or you’ll talk yourself out of getting started. Believing in what you are about to do does not guarantee success, but a lack of belief can prevent it.
To run a company, you have to be comfortable making important, life-changing decisions at a speed that would astound the average person.
The person who focuses on one task and sees it through to completion—even if they work in a somewhat slow or outdated manner—beats the endless optimizer who jumps from tool to tool and always hopes a new piece of technology will help them finish what they start.
“If you want to teach people a new way of thinking, don't bother trying to teach them. Instead, give them a tool, the use of which will lead to new ways of thinking.”
— R. Buckminster Fuller
Think about risk the right way. Drew Houston gave a great commencement speech where he said you only have to be right once. That’s true. The risk is not getting on the path where you get to be right that one critical time.
One big pro for starting a company is that it’s usually the way to learn the most in the shortest amount of time. One big con is that it’s easy to start a company for the wrong reasons—usually so that you can say you’re starting a company—and this makes it easy to cloud your judgment.
Most people think about risk the wrong way—for example, staying in college seems like a non-risky path. However, getting nothing done for four of your most productive years is actually pretty risky. Starting a company that you’re in love with is the right kind of risk. Becoming employee number 50 at a company that still has a good chance of failure is the wrong kind of risk.