Simon Willison is a British software engineer, open source creator, and AI commentator best known for co-creating the Django web framework and building Datasette, the open-source data exploration tool. He coined the term 'prompt injection' in 2022 and popularized 'AI slop' in 2024 - a word later named Merriam-Webster's 2025 Word of the Year. Through his prolific blog (active since 2002), newsletter with 54,000+ subscribers, and 100+ open source tools, he is one of the most influential independent voices at the intersection of LLMs and open source software.
Ben Carlson is a CFA charterholder, Director of Institutional Asset Management at Ritholtz Wealth Management, and one of the most widely-read finance writers in the United States. Through his blog A Wealth of Common Sense, co-hosted podcast Animal Spirits, and six books, Carlson has built a reputation for translating Wall Street complexity into plain-English wisdom that ordinary investors can actually use - advocating for simplicity, patience, and behavioral discipline over market-timing and stock-picking.
Freddie deBoer is an American author, cultural critic, and PhD-wielding contrarian who has spent 17 years making everyone on the internet uncomfortable - including people who agree with him. A self-described Marxist who despises most of the left, his Substack newsletter 'cool but rude' has over 67,000 subscribers hungry for unvarnished takes on education, identity politics, media dysfunction, and mental illness. Author of three books - The Cult of Smart (2020), How Elites Ate the Social Justice Movement (2023), and debut novel The Mind Reels (2025) - deBoer writes with the conviction of someone who has nothing left to prove and everything left to say.
Leandra Medine Cohen is the New York-based fashion writer, cultural commentator, and founder of Man Repeller - the blog that coined a phrase and built a media empire around the radical idea that women dress for themselves. After shutting down Man Repeller in 2020, she re-emerged with The Cereal Aisle, a Substack newsletter now boasting 166,000+ subscribers and a top-5 ranking in Fashion & Beauty. Part sharp wit, part earnest diarist, she writes about getting dressed, motherhood, and everything in between with a voice that is unmistakably her own.
Mark Manson is a three-time #1 New York Times bestselling author, blogger, and podcaster whose books have sold approximately 20 million copies worldwide across 65+ languages. Known for his brutally honest, profanity-laced take on self-help, his breakout book 'The Subtle Art of Not Giving a F*ck' spent over 279 weeks on the NYT bestseller list and was adapted into a documentary by Universal Pictures in 2023. He runs a popular weekly newsletter, an AI-powered coaching app called Purpose, and the podcast 'SOLVED with Mark Manson.'
Michael Lynch is a bootstrapped solo founder who quit Google after seven years to build software and hardware businesses entirely on his own terms. He grew TinyPilot - a KVM-over-IP device built from a $100 Raspberry Pi kit - into a $1M/year business and sold it in 2024 for ~$600K. He writes with radical transparency about money, failure, and the craft of independent software development at mtlynch.io, and is now writing 'Refactoring English', a book on writing for software engineers.
Xe Iaso is a technical educator, open source founder, conference speaker, Twitch streamer, and VTuber based in Ottawa, Canada. The CEO of Techaro and creator of Anubis - the open-source anti-AI-scraper tool now protecting GNOME, FFmpeg, Linux kernel archives, and UNESCO - Xe built a cult following of 400+ blog posts that mix deep systems engineering with irreverent philosophy. Known for pioneering developer relations teams at Tailscale and Fly.io, and for coining their own title 'Archmage of Infrastructure,' Xe is the rare technologist who turned shitposting into a career strategy and made it work.