Simon Owens's Media Newsletter

Simon Owens's Media Newsletter

This former Amazon executive generates over $200,000 a year from a newsletter he sends just once a week

Dave Anderson retired in 2021 and now writes about tech leadership part time.

Simon Owens
Sep 24, 2025
∙ Paid

If you ask Dave Anderson what he does for a living, he might say he’s retired. Technically, that’s true—he left his full-time job at Amazon in 2020 and has no interest in ever working 60-hour weeks again. But in reality, Anderson spends his days writing a newsletter on Substack that now boasts more than 2,000 paid subscribers and generates over $200,000 annually. For someone who insists he isn’t trying to build a media outlet, he’s done exactly that.

This is the story of how Anderson transitioned from two decades in the tech industry, including twelve years at Amazon, to becoming one of the most respected voices in tech leadership writing today.

A Career Forged at Amazon

Anderson began his professional life in the Midwest as a software engineer before joining Amazon in 2007. Over the next twelve years, he rotated through an unusually wide variety of divisions: global payments, Marketplace, AWS networking, devices, and even the video games group. Each stop gave him fresh perspectives on different types of businesses.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Simon Owens · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture