IN THE EARLY 1990S, I was a reporter at the Washington Post. Having just turned 30, I was the "young" person in the newsroom, so when the digital-media start-ups appeared, I got what many reporters looked at as the short end of the beat. They had no interest in understanding the massive changes that were happening. As I learned more, it often fell to me to explain what this newfangled internet was as if I were trying to explain a tree to a child.
The Post did give me the space to report on a broad range of digital topics, largely because no one else would-including the many come-and-gone technologies, like CD-ROMS, that were heralded as "multimedia killers" but would soon be killed themselves.
During that period, I made one prediction that started coming true much more quickly than even I expected. This was about the end of old media, starting with the destruction of one of its most important economic pillars: the classified ads in newspapers.
In 1995, a quirky programmer in San Francisco named Craig Newmark started emailing friends a list of local events, job opportunities, and things for sale. The next year, he turned Craigslist into a web-based service and eventually started expanding it all over the country and the world.
It was clear this list was a giant killer, and I told everyone who would listen to me at the Post that we needed to put all the money, all the people, and all the incentives into digital. I insisted that the bosses had to make readers feel like digital was the most important thing. But the bosses never did because the business they knew was the physical paper. I relayed my worries about the turtle pace of digital change many times to the Washington Post Company's affable CEO, Don Graham, the son of legendary publisher and surprisingly entertaining badass Katharine Graham. Don Graham was inexplicably humble and even sheepish about his power.
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