Most startups flame out or just muddle along. Your chances of spotting a unicorn, pre-horn, are incalculably small. But if, knowing that, you still want to toss aside your cushy job, at least listen to corporate vets who have made the transition.
Can anyone create an enduring business on the Web, where it's easy to build new companies, and when survival depends on the whims of fickle users? The big lesson of 'Digg' may be simply this: if someone offers you a ridiculous amount of money for a company that wasn't that hard to build, don't think twice. Take the money and run.
A startup job is an investment, after all: Venture capitalists may wager money, but you're staking something more precious - your time. And unlike VCs, you can't spread your risk by betting on a bunch of companies at once. Start with TAM. That's 'total addressable market,' and if it's not big enough, there's no point in talking.
The iPod wasn't the first MP3 player. Nor were the iPhone and iPad the first in their categories. The real reason for the success of these devices - the true unsung hero at Apple - is the iTunes software and iTunes Store. Because Apple provided them, it wasn't just selling hardware.
Conventional companies try to find new uses for capabilities they already have. Transformers look at what the market needs and then go build it, hiring new people and/or taking people off other jobs.
With digital attacks becoming rampant, the computer nerds who work for the good guys to thwart such incursions have become the new Navy SEALs - elite commandos who can carry out sophisticated operations on the battlefield of cyberspace.