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The Rebooting Show

The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses.

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Dynamo's Nicholas Carlson on finding content-market fit

Dynamo's Nicholas Carlson on finding content-market fit

A year after its launch, Dynamo’s Nich Carlson joined me to discuss what he’s learned in starting a YouTube-first video programmer. Dynamo is home to “Business Explains the World ( https://www.youtube.com/@BusinessExplainsTheWorld ),” a documentary-sty...

Jun 9, 2026

The new social with Rachel Karten

The new social with Rachel Karten

TikTok broke social media's original contract — grow followers, followers see content — and replaced it with algorithmic sorting that rewards entertaining strangers over satisfying your loyal audience. Link in Bio's Rachel Karten joins The Rebooting Sh...

Jun 2, 2026

The Dow Jones recipe for growth

The Dow Jones recipe for growth

In the wreckage of the scale era, The Wall Street Journal is one of the winners. It has 4.5 million paid subscriptions and the broader Dow Jones portfolio has 6.3 million with a foothold in B2B data assets like OPIS and Risk & Compliance. The Journal h...

May 26, 2026

The revenge of brand

The revenge of brand

Markets in the midst of technological change tend to have two camps. One is the legacy incumbents that have strengths in their brands and the other in upstarts that are nimbler. In digital media, it turned out brand won. At Possible, The Rebooting held...

May 19, 2026

Inside Politico’s franchise playbook for Playbook

Inside Politico’s franchise playbook for Playbook

At nearly two decades old, Politico's Playbook was an innovator in the now-familiar daily agenda-setting newsletter. Playbook is now more than a DC staple. It has editions in five countries with two more on the way. And it is looking to adopt a franchi...

May 12, 2026

TV advertising has decentralized

TV advertising has decentralized

The decentralization of digital media has arrived for TV. The TV advertising system is being remade in the image of the data-focused, automated ad systems that came to dominate the internet. TV was always the holdout, thanks to scarcity. That’s changed...

May 5, 2026

The Rebooting

Exploring the reinvention of media in a time of great change.

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