At a time when only one in 10 startups go public, and only a few of those stay afloat, how do you know when you're ready to jump from safety to uncertainty? Here are some of Rippy's rules.
Distinguish between the company's survival risk and your risk.
What's your definition of a company's risk? Is it years to profitability? Years to IPO? And how does that risk affect your career? If you acquire new responsibilities and skills, a company's fate may not matter. Often, a company's failure is a badge of courage, because it shows that you were willing to take a chance -- and that you learned from it.
Identify the experience you expect to gain and how it meshes with your overall career plan.
Assume that you won't be promoted and that you won't get rich. But will a startup job be a career detour? You should be able to defend the logic of joining a startup to future employers. Set clear milestones about the kind of contributions that you want to make, and vigorously monitor them. It's more about learning than about having an important title.
Know which stage of a startup is right for your risk tolerance.
Former Microsoft group product manager Bill Demas joined Vividence Corp., an online customer-experience shop, only after the startup had put its platform technology in place. Had he joined even six months earlier, the company would have been too young to take full advantage of his skills. If you're hired prematurely, says Rippy, you'll spend less time on business development and more time on "administrivia."