The podcast about how publishers create, distribute, and monetize digital content.
Do people want longform Twitter content?
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If there’s one thing Twitter’s known for, it’s character limits. It famously only allowed 140 of them and then later expanded to 280. In some ways, that forced brevity made Twitter what it is today: a real-time commentary on what’s going on in the world.
But for years, Twitter has been trying to expand beyond its own character limits, first by launching features like photos, gifs, and videos. It launched a threading tool that allows you to string several tweets together. In 2021, it acquired newsletter platform Revue.
And then just recently, it debuted a new tool called Notes. Though it’s still in the testing phase, Notes will allow users to publish longer blog posts within their Twitter feed.
But is this something users actually want? Or will it eventually join the very large graveyard of social media features that never caught on?
To answer this question, I brought on Ernie Smith. Not only is Ernie one of the foremost experts on publishing platforms and newsletters, he also got early access to Twitter Notes and tested them out for himself. He gave me his initial reactions to the tool and we discussed whether it would usher in an era of longform writing to Twitter.
He transformed a B2B sports magazine into a thriving media company
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When Nick Meacham first joined SportsPro in 2010, it mainly existed as a B2B print magazine that monetized through advertising. The editorial staff was tiny and it didn’t have much of a web presence.
But after taking over the business operations, he rapidly expanded it into new ventures – first by launching a series of lucrative conferences that targeted multiple industries within pro sports, and then by rapidly building out its digital operations.
In an interview, Nick explained to me why he made such a big bet on events, how the company adapted during the pandemic shutdown, and where he sees more opportunities to monetize the outlet’s digital content – including his plans to launch a subscription paywall.
Why two star WSJ reporters left to launch their own media company
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During their combined 20 years at The Wall Street Journal, Bradley Hope and Tom Wright covered some of the most momentous stories to hit the financial world, but none were as consequential to their personal careers as their reporting on Jho Low, a Wharton grad who was caught stealing billions of dollars from investment funds. Their dogged investigation led to the publication of the book Billion Dollar Whale, an instant bestseller that transformed them into A-list writers, on par with Michael Lewis and Malcolm Gladwell.
Rather than simply returning to their newspaper jobs, they partnered on a new media entity called Project Brazen. Unlike most digital media companies, Project Brazen has no ambitions to churn out large quantities of web content. Instead, it only focuses on ambitious, investigative storytelling that can be adapted into multiple mediums that include podcasts, books, film, and television.
How does Project Brazen go about vetting and staffing these projects, and what are the best ways to monetize serialized storytelling? Those are some of the questions I put to co-founder Bradley Hope in today’s interview.
How Payload became the leading space industry newsletter
When everyday people hear about space-related news, it’s usually in association with an organization like NASA or SpaceX. But while Elon Musk is great at grabbing headlines, the space industry actually comprises a vast constellation of companies that generate hundreds of billions of dollars a year. And it’s only set to expand; Morgan Stanley projects it’ll reach $1.25 trillion by 2040.
Given the size and growth of this industry, it’s probably a surprise to no one who listens to this podcast that there’s an enormous opportunity for the B2B media outlets that cover it. One of the most exciting entrants into that space is Payload, a daily newsletter that launched in 2021.
Though Payload was bootstrapped for its first several months, it announced a $650,000 seed round last year that was led by Winklevoss Capital, the venture firm run by Cameron and Tyler Winklevoss. It’s since hired an editorial staff and landed its first major sponsors.
Payload was founded by Mo Islam and Ari Lewis, and in December 2021 I interviewed Mo about the newsletter’s origin, its audience development strategy, and its plans to monetize its influential readership.
How Pop Up Magazine survived the pandemic
There were a lot of media companies that were vulnerable to the pandemic shutdown, but perhaps none more so than Pop Up Magazine. Not only was its content delivered through live performances, but the hosts made special care during each event to tell the audience that nothing that night would be recorded. Part of the magic, in other words, was the show’s ephemerality.
Of course, there was no way Pop Up Magazine could continue delivering on that promise once all in-person events went away. Instead, it had to adapt by somehow taking the magic of a live performance and delivering it over the internet.
Not only did the magazine succeed in this endeavor, but the new restraints forced it to diversify revenue and expand its audience. With live events now returning, it’s arguably stronger than ever.
How did its staff accomplish this? In an interview last year, founder Chas Edwards walked me through Pop Up Magazine’s pivot, from the hellish first weeks of the pandemic to its recent return to live events.
Why a bestselling author moved to Substack
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David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.
But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.
Simon is brilliant and thorough. This podcast is full of value. Very important resource for people who want to get better at what they do.
The host is excellent
So are his guests. I really appreciate where Simon steers the conversations, the topics he chooses and how raw and genuine these talks are. I’d suggest every J school in the country to listen to this one (actually recommended some of my former professors..) while they all are pondering on where the journalism is headed, this podcast actually shows where it currently is with all the changing landscape of content production.
Questions are awesome.... the whole vibe is awesome
Great questions.... I like every episode so far....never heard of some these businesses until now....