This is simultaneously hilarious to watch and disheartening to be a part of (as the creators of the Cluetrain Manifesto have amusingly outlined). Young, smart people who have a choice -- and today this particularly means software engineers -- will instinctively shun the large organization for the small-company environment. There, they will work long hours and trade high salaries for stock stakes that could be worth a fortune -- and could be worth nothing. But they will not have to spend half their lives in meaningless meetings and watch helplessly as projects and ideas disappear into the corporate maw, never to be seen again.

Now here's the catch: All these smart young people filling out the ranks of small companies look over their shoulders, and what do they see? That long queue of executives and managers from the "big, dumb companies" -- the very people they hoped to escape! -- heading their way.

I have no doubt that there are plenty of execs in the Fortune 500 who would have a lot to offer a small company. I've never met Jake Winebaum, and for all I know his new "venture capital incubator" Ecompanies will mint a bevy of valuable infant start-ups. But the skills Winebaum and others in his shoes have honed in boardrooms at Disney-sized outfits are unlikely to matter in the Net marketplace.

Scott Rosenberg's column appears once a week in Technology + Biography + Archives

The Internet's biggest impact on business is to put front-line staff much more directly in touch with customers. Feedback from the Net is ferocious, immediate and impossible to ignore. Good managers at small Net companies know this in their bones -- while at the big companies they're still scratching their heads and wondering, "What are we supposed to do with all that e-mail?" As a result, the good managers at the big companies who "get" the Net gradually get frustrated with the roadblocks they face, and steadily defect -- leaving their big company even more out of touch with what's happening online.

Are the executives who are now bailing out of big media and technology companies for Net start-up-land in this group? Are they frustrated Net-savvy managers who've finally had enough? Or are they clueless corporate insiders who covet a fat wad of stock options in any old Internet "play" that will have them?

Probably, there are some of both. The trouble lies in telling them apart.

If you're working at a Net start-up and you see one of these people heading your way, how can you know what you're dealing with? Try sending him some e-mail. Watch to see whether she can connect her laptop to the Net. Or see if he's changed the default home page on his browser.

These litmus tests may not be foolproof. But they'll give you a fighting chance of telling whether you're dealing with a real Internet savant or an opportunistic corporate carpetbagger.
salon.com | June 11, 1999

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