Title: Sizing Up a Start-Up: Decoding the New Frontier of Career Opportunities
author Daniel S. Rippy
publisher Perseus Publishing
ISBN 0-7382-0353-X
pages 275
rating 2/10 for experts, 7/10 for novices
summary How to tell if that dotcom is a dog
reviewer Stern

Stern is the president of Information Markets Corp.
Where Gray Matters

Michael Wolff founded Wolff New Media; it cratered; he wrote "Burn Rate". Jerry Kaplan founded Go Corp.; it cratered; he wrote "Startup". Adam Osborne founded Osborne Computer Company; it cratered; he wrote "Hypergrowth". You know the old story,

"If you can, do. If you crater, write a book."

You can understand their motivation. The book gives you the chance to make a few bucks off a failed venture, occupies some time while your emotions cool, and gives you a chance to blame the failure on somebody else. I have to guess that some rudimentary form of this effect drove Daniel Rippy to write "Sizing Up a Start-Up". He tells us only a little about his own professional background, except that he was a product manager for a "software start-up" in Seattle that burned through $25 million in investor cash and "had little to show for it."

Rippy's employer seems to have fallen apart with less drama than the almost tectonic failures engineered by Osborne, Kaplan and friends, and his book is somewhat more modest as well. He attempts to explain the rudiments of evaluating startups for others who might want to work in one but who lack the ability to identify a good one. He also provides basic advice on stock options, startup lifestyles, and other topics of interest to anybody contemplating joining an early-stage company.

Though Rippy's advice applies to any young company, he concentrates on technology start-ups, especially software and dotcom. As such, he talks a lot more about identifying a good venture capitalist (which a nice dotcom will have), as opposed to measuring positive net margins (which no dotcom has). High tech startups also provide most of his examples and quotes. Rippy quotes executives of a number of technology companies on topics ranging from sizing up a management team to evaluating your own tolerance for risk.

Most of his advice is quite general. He explains that earlier stage companies are riskier, and that you'll probably work long hours. In a few places, he becomes quite specific, for example, analyzing the strengths of different venture capitalists. He missed a trick, I think, in failing to discuss some of the specific data most valuable to people who have adopted a start-up lifestyle. Where's the table of startup filled neighborhoods in New York City, San Francisco, and Austin, cross referenced by nearby all-night restaurants and gyms?

What's Good?

The best things in this book are also the most basic and practical. If you don't know how to value a stock option, you should figure it out before starting at a dotcom. If your potential employer hasn't actually shipped a product yet, you should probably remember to ask how many months of cash they have in the bank. Of course, these topics are more obvious to most people now than they were in the giddy days before April's collapse in NASDAQ.

The quotes from other people were generally insightful, though Rippy's stable of experts is smaller than it looks at first. He returns to the same people over and over again for more quotes.

What's Silly?

Rippy presents a spreadsheet for calculating your "tolerance for career risk". It's a bit like a spreadsheet designed to determine, in strict mathematical terms, precisely how much prettier you think Boston is than Springfield. The question is fuzzy; the inputs are fuzzy; the output is fuzzy; don't pretend it's physics.

Worst Bad?

His half-baked theories of organizational evolution and some of the space-filling material. Rippy spends chapters on the difference between "organizational infancy" and "adolescence," etc. The filler is quite obvious, and sometimes laughable. To bulk out what is essentially a brief comendium of common sense, he includes lines like "Your base salary must be at some acceptable level because you need to cover your living expenses on a day-to-day basis." (Really!?!? Oh no!)

Is it for you?

Are you thinking about maybe joining a startup? Do you know the difference between qualified and nonqualified stock options? If not, buy the book.

buy it

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