Mario Gabriele is the founder and writer of The Generalist, a long-form tech and venture newsletter with 163,000+ subscribers ranked among Substack's top business publications. Raised in England by an Italian father and American mother, he cut a nonlinear path through law, culinary school, fiction writing, and seed-stage VC before going full-time as a solo creator in 2020. His signature style - combining equity research depth with fiction-writer storytelling - earned him citations in the FT, WSJ, and Bloomberg and attracted a loyal paid following. In 2022, he launched Generalist Capital, a $12.25M solo GP fund, and by March 2026 he had joined Hummingbird Ventures as a full Partner.
Packy McCormick is the founder of Not Boring, a weekly newsletter with 250,000+ subscribers that covers technology, business strategy, and startups through long-form essays. He also runs Not Boring Capital, a solo-GP venture fund with two funds totaling ~$38M invested across 79+ companies. A former investment banker and startup operator, he turned a writing homework assignment into one of the most-read independent tech publications, pioneering a 'media flywheel' model where newsletter content and venture investing reinforce each other.
Steven Sinofsky spent 23 years at Microsoft building some of the most-used software in history - Office, Windows 7, Windows 8, and secretly, the Surface tablet. A meticulous operator who refused to promise features until they were ready, he rose to become President of the Windows Division and Microsoft's most likely successor to Steve Ballmer before his abrupt departure in 2012. Today he's a Board Partner at Andreessen Horowitz (a16z) and writes Hardcore Software, a serialized Substack memoir chronicling the rise and fall of the PC revolution from the inside.
Byrne Hobart is the founder and author of The Diff, a daily newsletter read by hedge fund managers, venture capitalists, and tech founders tracking inflection points in finance and technology. A self-taught investor who landed at SAC Capital without a college degree purely on the strength of his writing, Hobart now co-runs Anomaly, a frontier tech investment firm, and co-authored Boom: Bubbles and the End of Stagnation with Stripe Press. He writes roughly 500,000 words a year and counts 1.5% of the Forbes 400 among his readers.
David Perell is a writer, educator, and founder best known for Write of Passage, the online writing course that turned thousands of lurkers into published voices. Armed with 474,000+ Twitter followers and a newsletter empire, he spent six years teaching people to think and write better on the internet - then stopped cold in 2025 when AI upended his mental model of education. He is now figuring out what comes next, in public, as always.
Julian Shapiro is a Canadian-born entrepreneur, deeptech seed investor, and prolific writer who built a career that spans open-source animation engines, growth marketing agencies, and a Y Combinator-backed startup. He founded Demand Curve, the largest growth marketing education platform for startups, and now runs Julian.capital, a deeptech seed fund writing $500K-$2M checks into robotics, chips, energy, medtech, and biotech. His free handbooks at julian.com - covering writing, startups, fitness, and audio - are read by over a million people annually. He co-hosts the Brains Podcast with Courtland Allen and was previously VP of Marketing at Webflow.
Morgan Housel is a partner at Collaborative Fund and bestselling author of 'The Psychology of Money' (2020) and 'Same As Ever' (2023), with over 11 million copies sold globally across 60+ languages. A former Wall Street Journal contributor and two-time Best in Business award winner, he writes about the intersection of human behavior and money, arguing that financial success is less about intelligence and more about temperament. Housel sits on the board of Markel Corporation and is widely regarded as one of the most influential voices in behavioral finance today.
Tara McMullin is a writer, podcaster, and business philosopher who helps small business owners build sustainable, humane companies. Formerly known as Tara Gentile, she spent a decade building a formidable reputation before reclaiming her own name in 2018. She is the founder of What Works, a digital platform and podcast downloaded over 2 million times, co-founder of YellowHouse.Media, and author of books including 'What Works' (Wiley). Drawing on feminist theory, critical sociology, and media studies, she challenges conventional business wisdom with intellectual rigor and a sharp editorial voice.
Eugene Yan is a Principal Applied Scientist turned Member of Technical Staff at Anthropic, where he bridges cutting-edge AI research with production-scale systems. Formerly at Amazon for five years building real-time recommendation and LLM-powered systems for Kindle and Search, Eugene is equally well-known for his prolific writing: 209 blog posts, 420,000+ words published, and a newsletter with over 11,800 subscribers. His open-source repository applied-ml on GitHub has become a canonical reference for teams shipping machine learning in production. He lives in Seattle, snowboards on weekends, and writes like someone who actually wants you to understand.
Patrick McKenzie, known online as patio11, is a writer, software entrepreneur, and strategic advisor at Stripe who spent two decades bootstrapping software companies in Japan before becoming one of the internet's most influential voices on fintech, career development, and software business strategy. He writes Bits about Money, a deep-dive newsletter on the plumbing of financial systems, hosts the Complex Systems podcast, and co-led VaccinateCA - America's shadow COVID vaccine location infrastructure that likely saved thousands of lives. With 4.7 million words published since 2006, his essays on salary negotiation, software marketing, and financial infrastructure have shaped how a generation of engineers and entrepreneurs think about building and getting paid.
Robin Rendle is a British-born designer, writer, and developer currently working as a Software Designer at Apple. Known for his deeply humanistic approach to web design and typography, he has spent over a decade shaping how the web community thinks about CSS, type, and craft. He ran the CSS-Tricks newsletter for years, launched The Cascade - a member-supported blog about CSS - and maintains one of the web's most thoughtful personal sites with over 900 published notes. He holds an MA in Typography from the University of Reading and writes with a rare blend of technical precision and literary sensibility.