I wish I could say that The Messenger’s failure came as a surprise

The Messenger, a news startup that Jimmy Finkelstein launched last spring with $50 million in funding and 175 journalists stationed in New York, Washington and Los Angeles, has shut down less than a year later, after running out of money. When it launched, the company said it would bring in more than $100 million in revenue this year, but by the end of 2023 it had less than $2 million of its initial funding left, and just $3 million in revenue. Earlier this month, Semafor reported that The Messenger‘s board of directors had considered shutting it down, since it was expected to run out of cash soon. And soon is now.

Coming as it does amidst a litany of layoffs and shutdowns in the media— including broad cuts at Time magazine, the Washington Post, the Los Angeles Times, and Business Insider —it’s tempting to see The Messenger‘s sudden shutdown as yet another symptom of a broader media decline. But this particular death is in a category by itself. Yes, the ad downturn and other macro effects no doubt had an impact, but The Messenger was doomed from birth. As I noted in a piece for CJR when it launched, its entire model felt like a blast from the past—and the past is about the only place where it might have survived.

From Finkelstein’s evocation of the glory days of Walter Cronkite and Vanity Fair to the hiring of Neetzan Zimmerman, a specialist in generating “viral” traffic, The Messenger seeemed almost prehistoric. As I wrote for CJR, the startup’s model seemed to be “harking to a time when social traffic from vast quantities of viral clickbait articles could bring in millions of dollars in advertising revenue.” Those days, as BuzzFeed could no doubt testify, are gone. And the route that The Messenger chose to get there clashed with its lofty goals. Jon Christian, the editor of Futurism, wrote that despite its talk about revolutionizing journalism, the site was “churning out viral dumpster juice” from day one.

Note: This was originally written for the Columbia Journalism School, where I am the chief digital writer.

Continue reading “I wish I could say that The Messenger’s failure came as a surprise”

The grift, the prince, the twist, and the truth (maybe)

If you read my daily email newsletter, When The Going Gets Weird (and if not, what is wrong with you?!) then you might recall a bizarre tale from Graydon Carter’s Air Mail entitled “The Grift, the Prince, and the Twist.” Written by Hannah Ghorashi and editor George Pendle, it told the story of Amar Singh, a descendant of a well-to-do Indian family (in other words, a “prince,” depending on your definition of that term) who said he was conned by a woman named Liza-Johanna Holgersson, who claimed to be from a rich Swedish family and took advantage of him. Pretty straightforward so far. But as the story continues, it gets more and more bizarre, until it’s almost impossible to tell what the real story is. And now there is an update, via an email to me — read on.

After giving Air Mail reams of documents and evidence of Holgersson’s scams, including her affairs with other men, some of whom also gave interviews to Air Mail, the only thing missing was a comment from Holgersson herself. Finally, the writer was able to get hold of Holgersson — who turned the tables on Singh, saying he wasn’t who he seemed, and that he had been threatening her, playing an audio tape of him making threats and calling her horrible names. Sure enough, there seemed to be some holes in Singh’s background as a philanthropist who had donated millions of dollars worth of paintings and art to support LGBTQ rights. One art dealer called him an outright fraud.

Continue reading “The grift, the prince, the twist, and the truth (maybe)”

Stewart Butterfield and Slack, his second accidental success story

I’ve been going through some archives of mine, and came across a story I wrote in February of 2014, almost exactly 10 years ago, when I was working for Gigaom in San Francisco. I interviewed a young Canadian guy named Stewart Butterfield about a new thing he had just launched called Slack — a kind of all-in-one chat and workflow discussion app. I freely admit that I was not sold on this app at first, despite Marc Andreessen’s excitement about its growth rate, and I blame that on my lack of interest in corporate productivity apps in general, which I’m sure are really important but in most cases are as boring as watching paint dry.

What really interested me about Stewart and Slack was that the development of Slack happened while Butterfield and his team were trying to launch an online game called Glitch — according to Stewart, they came up with Slack as a way of collaborating with each other while working on the game, because every other form of collaboration (email, MSN Messenger, etc.) didn’t have the features they were looking for. But the really interesting part of the story was that this was the second time Stewart had invented something successful seemingly by accident, while doing something completely unrelated.

The first time was a little app called Flickr, which more or less invented the online photo-sharing market. Flickr grew out of another attempt at an online game that Stewart and his partners (including Flickr co-founder and Butterfield’s wife at the time, Caterina Fake) were working on. This one was called Game Neverending, and it was a very cool exploratory open-world type of animated game — I played it a few times and quite liked it, but it never took off. As part of the game, you could upload an avatar of yourself, a picture or image of some kind, and that feature turned out to be really popular, so Stewart and the Flickr team wisely decided to focus on expanding that, and Flickr was born.

Continue reading “Stewart Butterfield and Slack, his second accidental success story”

It’s Torpenhow Hill, or Hill hill hill hill

Note: This has been kind of debunked — or at least 25 percent debunked 🙂 As a number of people pointed out on Mastodon, it seems there is no real place (in terms of being listed on a map) that is called Torpenhow Hill, as noted here, so that might be an embellishemnt just to make the whole story even more absurd sounding. Tom Scott also notes that in his video debunking on YouTube — however, he does mention that there is clearly a small rise near Torpenhow (which he walks up) and this could be considered a hill. So there.

The launch of the first Apple Mac

On January 24th in 1985, a little company called Apple launched a revolution in personal computing with the first Macintosh computer — a chunky-looking desktop with an equally clunky-looking mouse and a washed-out screen, which cost $2,495 US (the equivalent of about $7,000 today). It’s difficult to see this as revolutionary now, but in the mid-1980s it absolutely was. The only computers most people — including me — were familiar with were room-sized corporate servers with tape drives. The Mac made computers human-sized, and its graphical user interface with the trash can icon and file folders, and the mouse to navigate among them (both of which Steve Jobs borrowed from the Xerox PARC research lab) were unlike anything else on the market. No more typing DOS commands in green text on a black background!

I didn’t get one when they first came out — instead, I asked a friend who knew about such things what I should buy, and knowing of my interest in both drawing and music, he suggested the Atari 1040ST, because it had a better colour screen and a MIDI interface (which I never used). But I admired the Mac, and every Apple computer that came after it — especially the candy-coloured iMacs and the all-in-one desktops that succeeded them. I could never afford to actually buy one; I almost always wound up with some PC knockoff, which I liked in part because they were easier to take apart so you could upgrade the RAM, graphics card, etc. Also, PCs were better for playing games like Doom. But there’s no question Jobs and Apple were masters of marketing, especially the original Mac “1984” ad, which was created by Ridley Scott.