The Rebooting memberships

Join today for just $200 per year or $20 per month

I'm excited to launch The Rebooting's membership program. We dive into the details behind the new membership tiers below. To join, click the button below:

When I started The Rebooting in October 2020, I chose the awkward name because I believed the media industry was on the cusp of wholesale change.

The mission of The Rebooting is to foster a more sustainable, equitable and resilient media ecosystem that aligns incentives and rewards those creating real value. Too much of the last era was built on nonsense, and that’s unfortunately being washed away now. I think new models will emerge and new brands, and forms of media that will replace what’s lost, and the essential job of existing media companies is to reinforce their business models for a changed environment.

The Rebooting membership program is for those working in media, marketing and tech the insights and high-value connections to help them do their jobs better and foster the creation of a sustainable media ecosystem. I know it’s an overused term, but I hope this can become a community since I know from the many emails I exchange that there is a common cause.

TRB Pro ($200 annually or $20 monthly) is designed for those working in media and related industries. The benefits are:

  • Access to everything The Rebooting publishes
  • Participate in virtual events with experts
  • Participate in regular in-person events like live podcasts and happy hours 

TRB Insider ($1,000 annually) is built for top executives who want to support The Rebooting’s mission and connect with peers at exclusive, private events. The benefits are all of those in TRB Pro plus:

  • Invites to private in-person dinners
  • Invites to TRB events at industry tentpole events like CES, Possible, Cannes, Advertising Week and more
  • Quarterly business update 
  • My undying gratitude 

I'm being somewhat vague about the benefits because I want to take a test-and-learn approach with experimenting on what types of newsletters to make member-only and what convening benefits are offered based on member feedback.

Memberships will allow for the expansion the depth of The Rebooting’s analysis by investing more of my time and focus. They’ll also fund bringing on collaborators to expand coverage and analysis into new areas of the media ecosystem to cover more closely the buy side (brands and agencies) and specific media categories like streaming.

I appreciate your support. That’s been the best part of taking the independent path. Sign up now.

Also, if you’re between jobs or a student or have some circumstance where you cannot afford the $200, shoot me a note and we can figure something out. My email is

Thinking through subscriptions

On this week’s episode of The Rebooting Show, I explain the thinking behind The Rebooting’s memberships program and how it fits with the other aspects of the business. I’m joined by Reid DeRamus, founder of Caddie Labs, which supports individuals and small teams building media businesses, acting as their full-time tech and growth team. 

Reid and I have talked about these issues for years, going back to his startup Yem and then his time as a PM at Substack. Caddie Labs has partnered with The Rebooting to launch memberships. Reid and I cover:

  • Why sequencing your business is important – and realizing your “unfair advantages” is critical in that
  • The importance of first-party data in a niche media business
  • Orienting subscriptions for specific audience segments rather than the entire audience
  • Figuring out pricing
  • The challenge of “getting to start”

Listen to The Rebooting Show on Apple | Spotify | Other platforms

Thanks so much for reading. I hope you’ll become a member. Send me a note with your feedback: