The Rebooting Show

On this week’s episode of The Rebooting Show, I spoke to Darren Samuelsohn, a longtime politician reporter who was most recently head of Insider’s ill-fated DC bureau. Darren and I spoke about his new newsletter devoted to journalism, the decision to t...

Bill Bishop likes to make clear he’s not a journalist. Instead, he’s a China analyst who brings his deep understanding of the country to an English-speaking language through his newsletter, Sinocism. In 2017, Bill became the “original Substacker” after...

The Dispatch is a three-year-old publication focused on bringing fact-based politics news and analysis from a center-right perspective. Steve Hayes, CEO of The Dispatch, joined the podcast to discuss how it's managed to climb to near 40,000 paying subs...

I had a conversation with Krystal Olivieri, global chief innovation officer at GroupM, about whether advertisers would conveniently forget all those promises they made during flush times to support local news. The takeaway: Advertisers will cut here an...

Substack’s Reid DeRamus talks about growing newsletter audiences. Reid and I have spoken for the past two years on this topic, going back to before Substack bought his company Yem, which was focused on building a growth engine for newsletter writers. T...

Scott Brodbeck got into local news a dozen years ago, after working in local broadcast news in Washington DC. “I looked at the direction of the industry and didn't love where local was going and ended up leaving and just on a total impulse to start my ...

In 2016, Max Kabat and Maise Crow moved to Marfa, a small arts town in west Texas, and a couple years later made a bold call. They bought the local newspaper, The Big Bend Sentinel. Ever since, they've been building out their take on a sustainable loca...

There’s the understandable urge to “do something” to fix the difficult situation the news business finds itself in. Government intervention in markets has historically been less common in the U.S., but we’re in a time of aggressive industrial policy be...

Joshi Herrmann is the founder of The Mill, a newsletter focused on Manchester – England, not New Hampshire, for those who call it “soccer” – as well as sister publications in Sheffield and Liverpool. Joshi started The Mill in June 2020, and across the ...

The Athletic started in 2015 with a simple proposition: It would produce the highest quality sports journalism with a subscription model that would align incentives with producing quality work vs chasing traffic. The approach wasn't without its flaws -...

Ari Paparo is a longtime ad tech veteran, not to mention holding the disputed title as Funniest Person in Ad Tech. Some highlights from our conversation: Innovation requires fragmentation. Ad tech’s complexity is a longtime talking point. And it is und...

Isaac Saul saw knee-jerk distrust in media firsthand as a political journalist at outlets like Huffington Post, where what he wrote would end up being distrusted based on the place it appeared rather than the substance. Three years ago, Isaac started T...

Alex Kantrowitz is the founder of Big Technology, an independent publication focused on he immense impact of tech companies on business, politics and society. A reporter covering tech for BuzzFeed News, he wrote a book on the tech industry called “ Alw...

Semafor, backed by $25 million in private investment, has (finally) launched, marking possibly the most ambitious attempt in recent years to build a new global news brand. At the heart of the effort is an attempt to restore trust in media by rethinking...

6am City is turning to the newsletter to build out a network of 25 local news publications it says have 1 million cumulative subscribers and an open rate around 50%. After starting in Greenville, South Carolina, in 2016, 6am has expanded to markets lik...

In 2014, Bonnie Kintzer was named CEO of Readers Digest Association, becoming its fourth CEO in three years as it emerged months earlier from its second bankruptcy. After renaming the company Trusted Media Brands, recently shortened to TMB, Bonnie set ...

Casey Newton, a former writer at The Verge, started Platformer to cover the societal impact of the most powerful tech platforms. He’s used a subscription model, charging $100 a year. With 75,000 free subscribers and what he’ll only call “thousands” of ...

This is a preview of a new weekly podcast I’m doing with Troy Young. The People vs Algorithms podcast will focus on patterns in media, business and culture. Each episode will revolve around themes. This week, we tackled the theme of whether media is be...

Flying, a 95-year-old magazine publisher focused on amateur pilots, is on this path. Craig Fuller, CEO of Freightwaves, bought Flying in July 2021 and a key part of the growth plan he and COO Preston Holland have begun is a massive bet on so-called air...

Future is a collection of over 200 specialist titles that range from gaming and tech (Tech Radar) to homes (Homes & Garden) to beauty and fashion (Who What Wear) to B2B (SmartBrief), Future has established itself as one of the UK’s most successful publ...

The business of hip hop is often overlooked, even though it's a massive business with outsized cultural influence. Dan Runcie saw this as an opportunity, starting Trapital in 2018. I wanted to talk to Dan about his approach to building an independent m...

Begun as a meme account in 2017, Litquidity has amassed 1 million social media followers across Instagram, Twitter, LinkedIn and TikTok, specializing in the dark arts of “dank memes” that poke fun at the weird world of finance. The account, run pseudon...

In February 2021, marketing software company HubSpot bought popular business newsletter The Hustle. Jordan DiPietro, a veteran of The Motley Fool, joined HubSpot to run The Hustle just after the acquisition, after having spent time advising the company...

One of the most solid areas of digital publishing is what’s become known as intent media. In the old days, we called this “SEO.” The basics are taking service content and applying it to algorithmic distribution (usually Google) and marrying it with per...

Adam Ryan, former president of The Hustle and cofounder of Workweek, wants to rethink the B2B model. Workweek is banking on finding individuals – creators, if you will – to build audiences around. The bet is that individuals, particularly but not exclu...