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We are firmly in the era of paid newsletters, so much so that you can’t open up Twitter without seeing an announcement from a prominent journalist that they’re launching one. It’s a media trend so ubiquitous that nearly every major web platform — from Twitter to Facebook to Google — is entering the newsletter space.

But what about the paid newsletters that predated the current craze? Some media companies were prescient enough to leverage the intimacy of the inbox to generate reader revenue, and in that sense, Crikey was about two decades ahead of the curve.

The Australian news site…


The onset of the pandemic shutdown in March 2020 dealt massive blows to the vast majority of NYC businesses, but it was especially bad timing for W42ST, a print magazine based in Hell’s Kitchen. “We were publishing our first best-of awards issue,” founder Phil O’Brien told me. “We had over a thousand people vote for their favorite bars and restaurants, and on March 30 we planned to hold a big event that invited 300 people and was sponsored by Wells Fargo.”

But by March 12, O’Brien had acknowledged to himself that his entire business model was about to collapse. On…


If you had to pick a Dutch TV show to discuss on a weekly podcast, there are few better candidates than Wie is de Mol, which translates to “Who is the Mole?”

For one, the show is incredibly popular in the Netherlands, as reflected by the fact that it’s been renewed for 21 straight seasons. But even better, it’s perfectly designed for group discussion. The show pits 10 contestants against each other, requiring them to complete weekly challenges with cash prizes. Lurking among the 10 is the “mole,” a person who’s been assigned to secretly sabotage the group’s success. …


Not many people know what it’s like to have their hopes and dreams crushed over the course of a single lunch meeting, but Jonathan Rick experienced it firsthand in 2004. That’s the year he got an internship at Time Magazine, a dream role for someone who wrote for his college newspaper and had long wanted to break into journalism.

One day Priscilla Painton, who was then an assistant managing editor at the magazine, took Rick out to lunch. “She asked me about my goals, and I told her that I wanted to be the next Joe Klein,” a veteran Time…


In 2010, Kent Anderson and his family traveled on vacation to Telluride, Colorado, a former mining town situated in the Rocky Mountains. Anderson was born in Colorado and loves visiting whenever he can. One day, Kent’s family decided to walk down to a gondola that would take them into town, and on their way there he struck up a conversation with a man who was walking in the same direction.

The man mentioned that he was a scientist, which prompted Anderson to reveal that he worked in scholarly publishing. “He asked about some details, and I mentioned I also wrote…


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Kevin Kaduk didn’t know in advance that he’d get laid off from Yahoo Sports, but he always understood that such an outcome was more than possible. After all, he’d spent pretty much the entirety of his career watching friends and colleagues lose their media jobs. “I think when you’re a modern day journalist, you’re always thinking one or two steps ahead,” he told me.

Kaduk’s focus at Yahoo spanned across all major sports, but he’d always been particularly obsessed with Chicago athletics, and over the years he toyed with the idea of launching a publication called Midway Minute — a…


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The founders of LendIt Fintech didn’t set out to build an events company focused on fintech; they only did so after their search for a fintech conference that fit their needs came up empty.

Back in 2013, Bo Brustkern and Jason Jones were running NSR Invest, a fintech platform that helped automate investment decisions. “I wanted to learn more about the space,” Brustkern told me. “We were an asset manager in a new asset class, and many of these securities we were investing in were brand new. The industry was kind of complex and confusing, and we needed to understand…


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One of the best ways to scale a bootstrapped media company is to cover an underserved niche, and Emmanuel Saint-Martin found one in the French expat community. There are about 300,000 such expats in the U.S. alone, and many have specific information needs that aren’t well served by either mainstream U.S. or French outlets.

In 2007, Saint-Martin launched French Morning, which he initially maintained in his free time while working in TV news. Today, the site employs a full time staff of 10 and about 20 freelancers, and it operates city specific verticals all across the U.S. …


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In a recent article, I noted that the year 2020 “saw the creation of a market for independent internet writing, one that allows journalists and essayists to make a full-time living without the aid of traditional media companies.” Though many factors played into this, including the Covid-19 recession, it’s probably not a coincidence that most of the successful indie writers monetize their work through Substack. The newsletter platform made charging for paywalled content incredibly easy, allowing its writers to focus most of their efforts on amassing their “1,000 true fans.”

But what if you were trying to launch a paid…


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If you launch a new publication today, chances are it’ll be online only. Print has its advantages, but it can be extremely expensive to produce, and digital publications tend to have much lower overhead.

And so when Innovation Leader, a $695-a-year subscription publisher focused on corporate innovation, launched in 2013, it went the digital-only route. But then in 2015, it changed course, launching a twice-yearly print magazine that it sent out to its already-existing subscribers and a list of prospects.

I interviewed the publication’s co-founder Scott Kirsner about why he went the print route, the role the magazine plays in…

Simon Owens

Tech and media journalist. Email me: simonowens@gmail.com

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