Eddie Shleyner is a conversion copywriter and the founder of VeryGoodCopy, a newsletter of short 'micro-lessons' on writing, persuasion, and creativity read by millions of people a year. A former Copy Chief at the software-review company G2, he turned a private Google Doc of notes-to-self into one of the most-followed copywriting brands on the internet, a HackerNoon 'Email Newsletter of the Year,' and a 2024 book collecting 207 of his lessons. He works and lives in Chicago.
John Gruber is the writer behind Daring Fireball, the long-running Apple-focused weblog he launched in 2002 and turned into a full-time, ad-and-membership-funded one-person media business by 2006. He co-created Markdown with Aaron Swartz in 2004, hosts the popular podcast The Talk Show, and co-hosts Dithering with Ben Thompson. Equal parts UI obsessive and sharp-tongued critic, Gruber has become one of the most influential independent voices covering Apple and Mac culture.
Justin Welsh is a writer and solopreneur who turned a 2019 burnout into one of the internet's most-studied one-person businesses. After scaling SaaS sales teams to nine figures, he walked away, moved to the Catskills, and started writing online daily. His business - powered by The Saturday Solopreneur newsletter, the LinkedIn Operating System, and a stack of self-serve digital products - has crossed roughly $10M+ in cumulative revenue at an ~89% margin with zero employees and zero ads.
Kevin Lee is an executive at Substack, the subscription newsletter and media platform based in San Francisco that reached unicorn status with a $1.1 billion valuation in 2025 after raising a $100 million Series C. Substack has grown to host over 50,000 paid publications, with creators collectively earning more than $600 million annually and 20+ million monthly active subscribers on the platform.
Substack is a subscription publishing platform that lets writers, podcasters, and video creators run paid newsletters and own the direct relationship with their readers. Founded in 2017, the company hosts thousands of paid publications, processes hundreds of millions in subscription revenue annually, and has become the default home for independent media on the internet.
Stephanie Zinn is Editorial Partner at Andreessen Horowitz (a16z), where she leads editorial strategy and audience growth across Substack, X, YouTube, and search. With over a decade in tech editorial, she previously built editorial teams from scratch at Coinbase and GitHub - generating 15M newsletter subscribers at Coinbase and launching GitHub's influential ReadME Project. She is one of the rare operators who treats clear writing not as a nice-to-have but as a core business asset.
David Gaughran is an Irish author, self-publishing strategist, and indie author advocate who turned 18 months of rejection letters into a career dismantling the gatekeeping machinery of traditional publishing. Through his 'Let's Get Publishing' series of books, a free 27-lesson course, a weekly newsletter, and relentless watchdog journalism exposing predatory vanity presses, he has helped tens of thousands of writers navigate the digital publishing revolution. A nomad by habit — Dublin, Prague, London, Lisbon, southern France — and a storyteller at heart, he writes historical adventure fiction under David M. Gaughran and was awarded the 2020 Kate Wilhelm Solstice Award by SFWA for distinguished contributions to the science fiction and fantasy community.
Jane Friedman is one of publishing's most trusted independent voices - a Cincinnati-based author, educator, and industry analyst who has spent two decades demystifying the business of writing. Through her newsletters Electric Speed (30,000+ subscribers, running since 2009) and The Bottom Line (8,000+ paid subscribers), her book The Business of Being a Writer, and her widely-read site janefriedman.com, she helps authors navigate a publishing landscape that keeps reinventing itself. She came to prominence beyond publishing circles in 2023 when AI-generated fake books appeared on Amazon under her name, making her an unlikely but authoritative voice on AI, authorship, and copyright.
Nate Kontny is a Chicago-based serial founder, engineer, and writer who went from chemical engineering at UIUC to co-founding two Y Combinator companies (Inkling W06, Cityposh S11), running Highrise as CEO for Jason Fried, writing prolifically across Medium, HuffPost, and Fast Company, and building a suite of solo products - most recently AlliHat, a Safari extension embedding Claude AI directly in the browser. Currently Staff Engineer at Fivetran (post-Census acquisition), he is known for his radical transparency about failure, his 250-words-a-day writing discipline, and a philosophy that shipping imperfect work beats endless polishing.
Benn Stancil is a co-founder of Mode Analytics (acquired by ThoughtSpot for $200M in 2023), one of the most widely read voices in the data and analytics world, and an angel investor. He writes the popular newsletter at benn.substack.com - known for its witty, intellectually honest takes on the modern data stack, BI, AI, and startup culture. After a stint as Field CTO at ThoughtSpot post-acquisition, he now runs independently via benn.company, investing and writing with signature Friday dispatches that open with 'it's friday, and...' - a ritual his thousands of subscribers recognize instantly.
Dan Shipper and Nathan Baschez are the co-founders of Every (every.to), a subscription-based AI media and product company that bills itself as 'the only subscription you need to stay at the edge of AI.' Dan serves as CEO, writing the weekly 'Chain of Thought' column and hosting the 'AI & I' podcast, while Nathan spun out Lex, an AI-powered word processor, as a separate venture. Together they merged their respective newsletters - Dan's Superorganizers and Nathan's Divinations - in April 2020, and have since built Every into a 25-person company with 7-figure annual revenue, five software products, and a daily newsletter reaching 70,000+ subscribers.
Jack Raines is a writer, investor, and author who turned a $150,000 trading loss into a media career and a Penguin Random House book deal. He writes Young Money, a newsletter with 61,000+ subscribers covering behavioral finance, career philosophy, and what your twenties are actually for. He's now an investment associate at Slow Ventures, where he works on their $63M Creator Fund. Known for viral LinkedIn satire that got him reported to Columbia Business School as the 'Bacon Bandit of Hell's Kitchen,' he combines intellectual rigor with a refusal to take himself too seriously.
Sam Corcos is a four-time founder and the co-founder and former CEO of Levels Health, a $300M metabolic health company that pairs continuous glucose monitors with a software layer to help people understand how food affects their blood sugar. He co-founded CarDash (Y Combinator S17, acquired 2020), Sightline Maps, and LearnPhoenix before building Levels into a category-defining health company with $67M raised from a16z and a community of 1,400+ member-investors. In 2025, he joined the Department of Government Efficiency (DOGE) and was appointed U.S. Treasury Chief Information Officer. He is also known for extreme minimalism (one pair of pants, one backpack), tracking time in 15-minute increments, and hosting 100+ intellectual salon dinners in New York and San Francisco.
Steph Smith is a Canadian writer, podcaster, and growth operator who went from chemical engineering to becoming one of tech's most respected content voices. She grew The Hustle's Trends newsletter to 15,000+ paying subscribers (contributing to an 8-figure acquisition), hosted the flagship a16z Podcast at Andreessen Horowitz, sold $250K+ worth of her book 'Doing Content Right', and launched Internet Pipes - a community of 2,700+ people learning to extract business insights from internet data. She's currently at NVIDIA after transitioning from Groq following Nvidia's $20B deal.
David Kadavy is a bestselling author, designer, and creative productivity expert who reverse-engineered design principles for developers, advised a startup that Google acquired, and built a location-independent career from a Nebraska cubicle. His books - including Design for Hackers, Mind Management Not Time Management, and Digital Zettelkasten - have sold 100,000+ copies in 13 languages. He lives in a cabin outside Medellín, Colombia, publishes his income reports publicly, and argues that creativity is about managing your mind, not your calendar.
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.