Tim O’Reilly: Fishing With Strawberries

Max Chafkin, The Oracle of Silicon Valley

Tim O’Reilly is Silicon Valley’s leading intellectual and the founder of O’Reilly Media, a steadily growing $100 million company. His life is a vivid demonstration that interesting things can happen when you are working for more than money.

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Over the years, O’Reilly has written many influential essays, which are available on his blog, O’Reilly Radar. There is “Watching the Alpha Geeks,” which argues that most important new ideas come from hobbyists rather than from companies or research labs; the essay helped to popularize the theory of user innovation. There is “Piracy Is Progressive Taxation,” an argument against the strict enforcement of intellectual property laws. There is “The Open Source Paradigm Shift,” which helped catalyze the movement toward free software.

These essays, and others like them, are interesting as artifacts, but the real wisdom in O’Reilly’s work is found in the company newsletters he wrote when O’Reilly Media was still small and its influence still slight. The best of these is a short meditation on the nature of business, published in February 1995, just as excitement about the Internet was heating up. Back then, everybody O’Reilly knew was getting rich, and he had been talking to investment bankers about a possible sale or initial public offering of GNN. During a particularly memorable meeting, a banker advised him to focus less on work that was interesting and more on work of the moneymaking kind.

As O’Reilly tells it, the banker chastises him with a metaphor. “You don’t fish with strawberries,” the banker says. “Even if that’s what you like, fish like worms, so that’s what you use.”

At first, O’Reilly accepts this advice. Who can argue with the idea that customers should get what they want? But as he thinks it over, he begins to see things differently. “[A] small voice within me said, with a mixture of dismay, wonder, and dawning delight: ‘But that’s just what we’ve always done: gone fishing with strawberries,’ ” he writes. ” ‘And it’s worked!’ “