RIP To Another Outlet That Didn't Hire Me

Another media company bites the dust in familiar yet farcical fashion.

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Photo by Art Institute of Chicago on Unsplash

I got laid off from Uproxx back in April (I’ll stop bringing this up eventually, I promise). I managed to score a temporary editing gig at GQ soon after, but otherwise the next few weeks and months after that were, as you might imagine, a mad scramble for potential landing places. Many outlets were considered. I researched. I networked. By which I mean I mostly sent a series of plaintive emails and DMs to people who seemed like they might have the line on a new job while trying not to sound too pathetic. “Who books that?” as the old comedian joke goes.

At some point I heard from Jordan Hoffman, who I’ve known from the small world of film critics and entertainment writers for a long time. He suggested checking out The Messenger, an outlet I’d never heard of at the time. That I’d never heard of it made sense, because it was new. I’d later learn that it was founded by a guy named Jimmy Finkelstein, who had $50 million and a plan to build something “recalling great journalism institutions like 60 Minutes and Vanity Fair.”

I don’t really know what that means, but in the media business, not understanding what someone is talking about is often considered evidence of their genius. This was a guy who had apparently made lots of money running The Hill, another site I didn’t read. The important thing was that they were hiring. Hoffman had only started working there in June, but he knew they had a number of positions open, said I seemed like an obvious fit, and even said he’d put in a good word for me if I applied (good guy, Jordan Hoffman).

So of course I applied. Even for jobs there that would’ve been a clear step down and that I didn’t really want, like a night and weekend editor. At worst, I figured I’d get an answer to the proverbial “who books that” and cajole them into a position more befitting my talents. And yet with each application (which are a pain even when you’re half assing it, which I wasn’t), I’d get a form rejection letter 48-72 hours later. These are somehow even worse than not hearing back at all (which is what usually happenes), because it means someone actually saw my resume (which includes helping found a media brand and 15+ years writing at what I thought was a pretty okay level) and thought, “This guy? Blech! No way!”

Anyway, if you saw the subject line you can guess what happened next. The Messenger is dead in less than a year, and Hoffman has a piece in the Intelligencer today about the farce that was working there (a ONE DAY turnaround! I would kill for this guy’s networking and deadline skills!).

Some bits from that:

A text time-stamped 1:19 a.m. early Wednesday read, “I think it’s over, man.” It was a Los Angeles–based colleague at The Messenger. He’d received an unanticipated direct deposit and the sum totaled his unused vacation days. I guess in addition to good weather they have some solid labor laws in California. In New York City, I was laid off without additional pay. Plus it was raining.

When I got laid off and none of my editors could figure why, one of them wondered aloud, “Maybe it was because you’re in California. I know they’ve been bitching about dealing with California labor laws.” Who can even say what’s an asset anymore, really. I did get paid out on my vacation days, which is nice, and even got a severance (based on the five years I had worked under that parent company, for a division for whom I had actually been working for 15 years).

Five years before that, I’d gotten a shadow demotion, cut to 50% of my previous salary in the hopes of lowering company costs to attract a new buyer. When I got paid out on those accrued vacation days, it was at my new, 50% salary. Later when we actually found a buyer, I was shadow rehired at about 84% of my previous salary. I was up to about 95% when I got laid off again.

Hoffman goes on to recount a story about how he’d received a breathless note that Toni Collette was trending:

I’ll never forget the day I was told, breathlessly, by the then-head of the entertainment channel that Toni Collette was trending. (Trending, I say, trending! Do you hear me? Toni Collette is trending!!! I believe it was her birthday.)

He went on to work up a listicle about Toni Collette’s eight best performances, and by the time he was finished (and I think the existence of this article proves that Hoffman works fast), surprise surprise, Toni Collette was no longer trending. Virtually all ad-supported outlets have been attempting to employ this chasing-trending-topics strategy. As Amos Posner wrote (skeeted) on BlueSky the other day:

Conservative pundits are coming after Taylor Swift for the same reason they went after the Barbie movie. They're just adding SEO keywords to their culture war content, feeding off the scraps of attention from something that's actually popular. Clout remoras doing what they do.

This is true as it goes, but most media outlets have become clout remoras in the same way. Grab something popular, and try to ride the coattails. It’s kind of what AI does, to some degree. Find things already written about and cannibalize them. The ouroboros ring gets smaller and smaller as the content keeps devouring itself. I think this partly explains why it only ever seems like there are three or four news stories anymore. Taylor Swift! Travis Kelce! MAGA people are mad! It’s hard to blame conservatives for thinking Taylor Swift is “an op.” We all end up hearing about her seemingly out of all proportion to how important whatever story is or even how much we’ve sought her out. Probably a lot of the explanation is that we fired all the people who write new news and forced their replacements to regurgitate trending topics.

Anyway, Hoffman goes on to detail his ground level view of The Messenger’s business strategy:

The Messenger’s executives — masters at long-term thinking — rented the entire 26th floor of a skyscraper downtown. It is an enormous space and, the few times I visited, was nine-tenths empty. Just rows and rows of spotless, expensive-looking desks that could rise to a standing work station with the push of a button.

This is exactly what happened to Uproxx back in the mid aughts, when we’d suddenly doubled our staff and had expensive offices in New York and LA even though no one I knew who worked there lived in those places. As far as I can tell, it’s a process of taking money from investors and blowing it on dumb shit to make yourself look legit in order to attract new investors. Eventually the money just runs out and all the guys who wanted to buy that stuff disappear (floating away on generous compensation packages, most likely), and to reduce all that overhead they fire the people who make the actual product.

That was standard practice in 2015. the funny thing about The Messenger was that they were still doing it in 2023, long after everyone else had figured out that it didn’t work, leaving everyone to wonder if The Messenger knew something everyone else didn’t.

As Josh Marshall describes it at TPM:

The Messenger was launched, built and run entirely on that old premise and model. It was like watching someone jump out of an airplane with no parachute totally confident they had some new angle on controlled descent no one knew about.

Back to Hoffman, realizing the facade was crumbling:

Now, we all knew the company was in trouble. There’d been plenty of stories and we even had channel-specific Zooms with Finkelstein. (Though never a town-hall-style address. Not once, ever.) Our editor-in-chief, Dan Wakeford, even emerged from the shadows to appear at these Zooms. Not that he talked much. I can’t offer a real opinion of this man I’ve never formally met.

Oddly, I did meet Finkelstein once. We had the saddest Christmas party — some hummus tubs from Fresh Direct in the break room. He shambled over like Boris Karloff to shake my hand. I mentioned something about the hummus and someone else mentioned that hummus was topical that day because of the Israel-Hamas war (actually couscous was in the news), and then Finkelstein barked that he would never let his kids go to an Ivy League school today, an apparent reference to the antisemitism controversies. This represents the entirety of my interaction with Jimmy Finkelstein, a very wealthy man who decided not to give his employees severance.

Yesterday afternoon, the New York Times reported that The Messenger would be shutting down. The editor in chief showed up in the company Slack a few minutes later to say “I am not in the loop.”

Soon thereafter, we were shut out of Slack. An email arrived afterward from “CEO Communications” in which Finkelstein apologized to us for failing to raise more capital. Later, all our work was deleted. Thousands of stories and hundreds of my own. Some of them were great.

The Messenger’s main page now goes to a blank white page.

I wish I could take some satisfaction in having my gut reaction to The Messenger be proven correct, or take some solace in not having been hired there only to be fired via email six months later and have all my work there summarily deleted.

Mostly though, I’m just worried about this impromptu experiment we’re performing on the national psyche. A story in the Atlantic recently describes how the Denver market, for example, had 600 journalists covering it as of 2009. Now there are 59.

I wish I had some nice way to wrap this up. It’s almost boring at this point to say that the rich guys who came up with The Messenger’s business plan are going to be fine, and the journalists those guys made big promises to are walking around asking each other “who books that?”

Maybe the fact that we all knew The Messenger was working off an already dead model offers some faint hope that a new model will spring up in its place. Probably that’s a little lazy, but it’ll have to do for now. I have some plaintive emails to write.