Three common Silicon Valley entrepreneur viewpoints:
Viewpoint #1: You’re young. The downside is low, typically 1-2 years in forgone salary and just your time if you’re moonlighting. You get great experience that can even enhance your resume of consulting, McKinsey, investment banking, finance, and business school with “in the trenches” experience.
[I owe it to myself to try, but corporate life is my backup especially once I get a family and other obligations.]
Viewpoint #2: I’m in love with working for myself. I’ll do whatever it takes to work in my pajamas: freelance gigs, affiliate marketing, Facebook apps, blogging. I understand that compensation may be lower, but lifestyle and freedom are worth quite a bit.
[I'm in love with this lifestyle. Sure I want to make it big, but I'd be happy even if I didn't.]
Viewpoint #3: I’m learning and growing along the way. I may jump between gigs at startups to learn the ropes from people who’ve done it successfully before, banking/finance/VC jobs to get exposure to big transactions and connections, and doing my own startups.
[I want to learn this process and master everything about it. Entrepreneurship is romanticized. There's nothing inherently different between your own startup and someone else's. All that matters is success.]
I’m simplifying the picture, but you’d be surprised how many people fit into these broad strokes.
You’ve got to have the skills to posit reasonable hypotheses. But you also have to realize that rarely is one shot enough. Give yourself enough chances to fail to get to success. Look at the every process scientifically: one failed direction means you’re closer to the correct direction. One failed marketing campaign means one campaign closer to the right.
Test, measure, adjust. Test, measure, adjust. Ian Ayres writes about this extensively in Super Crunchers. The most effective methods will combine informed hypotheses and intuition (the universe is too big to test everything) with systematic testing and measurement.
Speed means a lot because you get a lot more cycles in (1 to 2 years may be one shot for some, ten to twenty for others!). You’ve got one shot… not!
(I don’t always take this advice, but I resolve to always try to.)