My first job in media didn’t pay a thing. In the summer of 1997, I was an unpaid intern at CNN, a recent McGill University grad living in my older cousin’s spare bedroom on the Lower East Side in Manhattan. Each morning, I took the subway to 5 Penn Plaza, just a short walk from the always-busy Penn Station and Madison Square Garden.
This was three years before AOL bought Time Warner, the owner of CNN, in what is still widely seen as the worst business deal in history. Back then, CNN had a sterling reputation and was the unquestioned worldwide leader for breaking news.
I was hired to work in the PR department on the 19th floor. My primary job was to read through a stack of newspapers each morning and physically cut out any article that mentioned CNN. It was two hours a day with scissors and newsprint. The clippings were filed in folders and given to my boss, who passed along anything interesting to her boss. It was the kind of work that would eventually be automated.
On my third day, I wandered down to the 18th floor, where CNNfn was based. CNNfn was CNN’s dedicated financial news channel, now called CNN Business. They filmed live all day. There were cameras, lights, and producers with clipboards. It was considerably more interesting than the 19th floor.
I started spending most of my time down there.
CNNfn had a show called “It’s Only Money” that featured young entrepreneurs building dot-com businesses. It was mostly people in their twenties who had started e-commerce sites and had theories about how the internet would change everything.
I was given the job of pre-interviewing the guests. I’d call whoever was scheduled to appear and ask about their business and their background. I’d take notes and pass them to my producer and host so they’d know what to ask during the live segment.
It was the closest thing to journalism I’d ever done, and I found it thrilling. You’re trying to figure out whether someone will be interesting on camera. You’re looking for the specific details and stories that make a segment feel real rather than rehearsed. Most guests were happy to talk. They were getting free airtime on CNN to promote their startups. They didn’t care that I was an intern.
I don’t remember most of the companies or founders. They’ve blurred together. A few probably survived what came next, but most definitely didn’t.
I made one notable mistake. I pre-interviewed a guest whose business was interesting but who was painfully dull on the phone. His voice was monotone, he had no energy, and his answers went nowhere. I should have flagged this for my producer. I didn’t. The segment aired, and the guest was a disaster. There were awkward pauses, one-word answers, and the host struggled to salvage it.
The producer asked me afterwards if I’d picked up on this during the pre-interview. I froze. Either answer was bad. If I said yes, I should have warned him. If I said no, I was incompetent at the one task I’d been given. I mumbled something about not having noticed. I don’t think he believed me.
At the end of the summer, I found out they were cancelling the show. The producer lost his job. I still wonder if this was partly my fault.
On the 20th floor, Lou Dobbs filmed “Moneyline,” the flagship business show that had made him one of the most recognizable faces at CNN. Dobbs had the kind of casual authority that came from being really good at your job and knowing everyone knew it. I was intimidated by him. He had no idea I existed.
Larry King also filmed at 5 Penn Plaza. He was someone who’d built a career on being curious and letting famous people talk. He was good at it. His questions sounded simple, but gave people room to say interesting things.
The elevators at 5 Penn Plaza were always interesting. The building’s hierarchies temporarily dissolved in there. I’d ride up with producers, hosts, executives, and other interns, and occasionally with someone famous who was there for an interview. The unspoken rule was to pretend not to recognize famous people. Everyone acted like it was normal to share an elevator with someone who’d been on a magazine cover or run a Fortune 500 company.
I rode the elevator with Donald Trump on July 23, 1997. He was there for Larry King. He didn’t talk to anyone. We all pretended not to notice him. You can still read the transcript of the interview online.
I didn’t think much of it at the time. Trump was famous for being famous. In 1997, that meant he was famous for having money, putting his name on buildings, and occasionally going bankrupt and recovering. He wasn’t politically relevant. He was a tabloid fixture, someone who’d married models and built casinos and had a cameo in “Home Alone 2.” The idea of him becoming president would have seemed ridiculous.
The other celebrities I saw in elevators have faded from memory. There were lots of them. 5 Penn Plaza was a high-traffic spot for anyone doing media in New York, and Larry King’s guest list was eclectic. I maintained my policy of studied nonchalance. I never tried to start conversations and never asked for autographs. I treated famous people like they were regular people who happened to be in the elevator, which is probably what they wanted.
The internship was unpaid, which was standard for the industry and completely unsustainable unless you had a second job or, in my case, a cousin with a spare bedroom. The apartment was small and overlooked a highway, but it was free, and I was grateful for the place to stay and the opportunity to experience a full summer in New York.
There was one unexpected perk at CNN. Boxes of review copies from book publishers were always lying around the office, sent to various shows in the hope of coverage that would almost certainly never happen. The books were free to take, so I started taking them.
Barnes & Noble had a generous return policy in 1997. You could bring back books without a receipt and receive store credit equal to the cover price. I realized that this policy, presumably designed for unwanted gifts, worked equally well for free review copies acquired from a CNN internship.
I got strategic about it. I’d rotate between different Barnes & Noble locations around Manhattan, never hitting the same one twice in a row, walking in with a stack of hardcovers and walking out with store credit that I’d immediately spend on whatever I actually wanted to read. I must have visited every Barnes & Noble in the city that summer. This was before Amazon reshaped the book business, when bookstores were still everywhere.
I read more that summer than any summer since.
My time at CNN ended because I didn’t have a work visa. I returned to Toronto and landed a job at a consulting firm specializing in implementing SAP software for clients like Nokia, Panasonic and JVC. SAP is enterprise resource planning software, which is a boring way of saying it’s the plumbing that makes large corporations function. It was technical and tedious, but paid way better than any media job would have.
I was competent at it. Not passionate, but competent. The work was project-based: several months embedded with a client, long hours, then on to the next one.
I kept thinking about CNN, but not because the internship had been glamorous. I thought about it because it was the first time work had felt interesting. Calling entrepreneurs, figuring out whether they’d be good on camera, looking for the details that made a story worth telling. That had engaged me in a way that enterprise software never would.
I didn’t know yet that I’d end up back in media or that I’d start a publication and spend two decades building it.
CNNfn no longer exists. Lou Dobbs went on to become a far-right commentator before CNN cut ties with him. Larry King continued his show for another 13 years. We all know what happened to Donald Trump.
And I went back to Toronto, worked in enterprise software, and then moved to San Francisco just as the dot-com boom was getting overheated.
That’s the story for the next post.
Love the Barnes & Noble scam!