Kara Swisher was a reporter at the Washington Post in the early 1990s, where, at age 30, she was the “young” person in the newsroom, so she had to cover digital media:
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. The very worst thing that Graham — always apologetic for having interrupted me, as I strafed big retail advertisers in my stories about the sector’s decline locally — would say to me was “Ouch.” Then he would saunter away from my desk with a jaunty wave. And while Graham was interested when I talked about what Newmark was doing, he laughed when I told him that Craigslist would wipe out his classifieds business.
“You charge too much, the customer service sucks, it’s static, and most of all, it doesn’t work,” I lectured him about this business, which was crucial to his bottom line. “It will disappear as an analog product, since it is a perfect target for digital destruction. You’re going to die by the cell and not even know it until it’s over and you’re dead on the ground.”
Don smiled at me with a kindness I certainly did not deserve at that moment. “Ouch,” he said.
The Post, of course, is now owned by a tech mogul, Jeff Bezos, and other Silicon Valley machers have taken over or invested heavily in legacy media, but they have not prevented its relentless decline, or the hemorrhaging of thousands of jobs from the industry in just the past few years, as the digital world has both sucked up and diminished print business models.
The very few business that have overcome the digital revolution have the attitude, If you can’t lick ‘em join ‘em. The core of resistance comes from the corps of product specialists and engineers who have to be persuaded that the new tech is just as much geeky fun as the old.