Does Your Startup Measure Up?

Signing up with a young technology company need not be a leap of faith. Daniel Rippy got startup fever, left his job at Bristol-Myers Squibb — and had second thoughts. His new book helps you look before you leap.


Four years ago, overcome by high-tech wanderlust, Daniel Rippy headed west for Seattle. Then 28 years old and a senior analyst at Princeton, New Jersey-based Bristol-Myers Squibb, Rippy decided he was ready to move on to the uncertain world of technology startups. So he accepted a position at a health-information software firm, confident that the company would succeed in a growing industry.


But after a year with the company, things looked a lot less promising to Rippy. The startup had burned through $25 million in investor cash in three years and had little to show for it. Survival — never mind an IPO — was a dim prospect. It was time to bail out.

These days, tracking the rise and fall of technology startups can be dizzying. So if you’re thinking of ditching your old-line job for a startup, you should learn how to tell whether a company has a good chance of making it and whether the time is right for you to make the switch.

That’s what Rippy has set out to explain in “Sizing Up a Start-Up,” due out from Perseus Books next month. Rippy talked to many startup veterans, both during and after his stint in Seattle (he eventually took a business-development job at Johnson & Johnson, in Arlington, Texas), and was surprised to learn that many of them had encountered the same disappointments as he had. His discussions with those colleagues form the core of his book, which is both an operating manual and a cautionary tale for anyone contemplating a leap into the startup unknown. During an interview with Fast Company, Rippy laid out the fundamentals.

What’s the most important thing to look for in a startup?

An assurance that you’ll gain valuable experience. Have team members’ responsibilities increased over time? Since many startups have fewer employees and less management hierarchy to claw through than more-established companies do, the chance to shoulder new tasks should be a given. But make sure you’ll be gaining experience that will be useful in the future. Will you become an expert in ways that all companies, regardless of their particular market or focus, value? Will you be making decisions and striking deals that you weren’t involved in at your previous job? It may look good on your business card, but there’s no point in having a glamorous new title if you’re doing the same work that you were doing at your last job.


How can you tell if you’ll fit in with a startup’s culture?

Ask and listen. Ask who will do what when the staff grows from 5 people to 50. If you hear “I, me, my,” run! The founders have tunnel vision. But if you hear about “the team” and how everyone, even new hires, will contribute to important projects, then there’s a better chance that you will succeed there. An insular “founders’ syndrome” can kill a company. Make sure a tight-knit team won’t limit your contributions. And remember, startups go through stages. A company’s early adolescence may have come too soon after its infancy for its founders to have let go. Later on, there may be more opportunity for you to fill a larger role.

Also, make sure that the founders’ commitment to working hard doesn’t clash with working smart. When you visit the office in the evening, are people settling in for a second shift or wrapping things up? Is there a power divide along gender, generational, or other demographic lines? That’s how to tell if the workplace is right for you.

As a startup matures, how do leadership opportunities change?

Experienced managers are brought in, because they’ve been through the stage of growth that the startup is about to enter. They also know how to direct people to tasks that suit them. That means you can be sure that you’re working on the right projects and that your talents are being recognized. Are there people with a track record on staff? A chance to learn from someone with real management legs is a chance for mentorship.


When is it time to get out?

When you lose faith in the company’s ability to deliver its product or promise, then it’s time to leave. Of course, the early stages of a startup are notoriously chaotic. But is there a method to the madness? It’s one thing if sales are skyrocketing, and everyone is working seven days a week to cover the orders that are pouring in. It’s another if the company’s sinking, and people are working furiously to bail it out. Also, when you lose your passion for the project, there’s an opportunity cost to staying. You’re no longer improving your skills or contributing at your full potential.

A note of caution: If the company isn’t the market leader, that doesn’t mean that you should leave. If you’re driving key parts of the business, you can still trade on that experience. Focus on learning, not on winning.

Contact Daniel Rippy by email (


Sidebar: Risk Detector

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.”