I've personally interacted with many of these authors and orgs over the years, some are friends. I recommend supporting them as much as possible.
Blogs
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A Smart Bear
Jason Cohen's writing on startups, business, and entrepreneurship
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Andy Croll
Ruby development, entrepreneurship, and building software businesses
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Ben Curtis
Software development, entrepreneurship, and remote work
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Daring Fireball
John Gruber's commentary on technology and design with a focus on Apple
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Derek Sivers
Thoughts on life, business, philosophy, and programming
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Erin Kissane
Writing on networks, information design, and digital culture
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Hapgood
Mike Caulfield's blog on education, digital literacy, and online verification
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Joel Hooks
Software development, education, and building online businesses
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John Nunemaker
Ruby development, open source, and building software products
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Justin Jackson
SaaS marketing, building calm companies, and business ethics
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Maggie Appleton
Visual essays on programming, design, and digital anthropology
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Marc-André Argentino
Analysis of hybridized threats and counterterrorism research
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Mike Perham
Ruby development, open source, and building Sidekiq
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Pluralistic
Cory Doctorow's blog about technology, digital rights, and society
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Seth's Blog
Seth Godin on marketing, leadership, and creating change
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Stacking the Bricks
Amy Hoy and Alex Hillman on bootstrapping and building sustainable businesses
News
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404 Media
Independent tech journalism focused on media and the darker corners of the internet
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High Country News
Independent journalism covering the American West's environment and communities
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Range Media
Independent local news covering Spokane and the Inland Northwest
Newsletters
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Ben Thompson's Stratechery
Analysis of the strategy and business side of technology and media, and the impact of technology on society.
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Dina Litovsky's In the Flash
An ongoing dialogue about the art and craft of creating and thinking about images
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Erin Kissane's wreckage/salvage
Research projects and long-form explorations into networks and governance
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Flaming Hydra
A writer-owned newsletter collective covering media, culture, and society
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Leah Sottile's The Truth Does Not Change...
...According to Our Ability to Stomach It. Journalism and essays about writing and the American West
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Mike Caulfield's The End(s) of Argument
Researching information literacy, misinformation, and civic reasoning
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Molly White's Citation Needed
Critical coverage of tech and the cryptocurrency industry
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Patrick McKenzie's Bits about Money
Deep dives into financial technology, banking infrastructure, and how money moves around the world
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Seth Cotlar's Rightlandia
More than you ever wanted to know about Walter Huss
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Talia Lavin's The Sword and the Sandwich
Politics, religion, and the far-right (and sandwiches)
Nonprofit Organizations
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Coalition for Responsible Home Education
Advocating for responsible homeschooling practices and protecting homeschooled children
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Electronic Frontier Foundation
Defending civil liberties in the digital world
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Internet Archive
Building a digital library of Internet sites and cultural artifacts
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Ruby Central
Supporting and advocating for the Ruby programming community
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Wikipedia
The free encyclopedia that anyone can edit