A year of The Rebooting and what’s next

A little more than a year ago, when I signed off Slack after nearly a decade at Digiday, my focus wasn’t on what was next. I knew I’d want to take time to figure out what path was best for me, what new opportunities were opened by the unbundling trends in publishing, and the reality that I had a one-year non-compete that would prevent me from taking a job even if I wanted one, unless I pivoted to paddleboard instructor. I spent more time reading, running and going to the beach to think. I don’t regret it.

The Rebooting began as a placeholder, a newsletter I set up in under 10 minutes as an outlet for exploring what’s next in media, processing what I learned over 9+ years as president and editor-in-chief at Digiday, and became an experiment in building a different type of publishing brand that’s more personal. Over the course of the last year, it evolved from a personal project to what I considered a minimally viable product to what I hope now is the seed to grow something more ambitious and my Main Thing.

My goal for The Rebooting is to establish a new publishing brand focused on how to build more sustainable media businesses. I want to develop a place where the focus is squarely on how to execute on business models that can support a new crop of digital publishers built on sturdier foundations.

I’ve long felt the promises of digital media – an explosion of content options, without gatekeepers, backed by good business models – fell woefully short. Instead, we got the domination of technology platforms, a digital ad system dominated by scooping up as much data as possible for ad targeting, horrific user experiences, a race to the bottom as publishers chased virality, and a business culture that too often excuses corner cutting and dishonesty, giving rise to the shenanigans most recently exposed at Ozy Media but common, to a degree, across the industry. The reason I called the newsletter The Rebooting is I believe the Covid era – and it’s going to be an era, not a crisis – will result in much lasting change across our economies and societies. This will take time to play out, but the macro trends are clear.