The List

If you’re new to my writing, here’s the full list of essays that live on this blog.

My essays are a mix of theories, frameworks, and empirical ideas about what’s happening in the world and where things are headed—generally in 3 categories:

• Ambition: on modern work, life, & the culture of aspiration

• Attention: on modern media, communities, and how we spend time

• Creation: on the craft of building and investing in companies and people

Favorites

These are my top picks, based roughly on reach and resonance (listed in order of title length, because aesthetics matter). Some essays have been featured by Substack or other publications and magazines. P.S. the full list below includes more popular essays.

• Rise of the Silicon Valley Small Business

• Love the Mission or Love the Game

• The Rise of Software Creators

• Taste Is Eating Silicon Valley

• What I Learned at Clubhouse

• The Theory of the Cool Self

• Pursuits That Can’t Scale

• Companionship Content

• Early-Arriver Arbitrage

• One-Round Wonder

• Writer-Builders

• Social Utilities

• Status Limbo

• Ritual Social

• Trophy Jobs

(P.S. Some essays may be paywalled halfway through if they’re in the archive, but the first parts should be interesting enough on their own. // If you’re a paid sub and these links still say “private” — you can find all essays in the archive.)

Full List (76)

Popular essays are denoted with an asterisk.

• Digital Tug-of-War

• Writing Wrapped*

• Two Shticks*

• Invisible Duels*

• Thoughts For Sale*

• Taste Is Eating Silicon Valley*

• About Practice

• The Co-Sign That Changes Everything

• Notes on ‘Founder Mode’*

• When Founders Outgrow their Startups

• The Lost Sense

• 30 and Not Retired

• Second Nature Skills

• Tattoo Decisions

• The Theory of the Cool Self*

• The Prestige-Prosperity Gap

• Writers Block

• In Defense of Tarpit Ideas

• Ping Minimalism

• How to Be Like Derek Guy*

• The Rise of the Software Creator*

• Background Social

• Accountability as a Service*

• Baseline Fame

• What I Talk About When I Talk About Reading

• Writer-Builders*

• 3 Hours or Nothing*

• How to "Go Direct"

• The Taste Subsidy

• On Airchat

• "New Social App"

• New Media, New Standards

• Hands-On, Thumbs-Off*

• Placeholders of Life*

• Early-Arriver Arbitrage*

• Rabbitholes as Portals

• Second Encounters

• The Time-Boxed Startup

• The New Wordmark

• Great Products Have Great Premises*

• The Creator Search Fund

• Time-to-Lameness

• Pursuits That Can’t Scale*

• Love the Mission or Love the Game*

• Books Are the New Athleisure

• Crypto Social Games

• Companionship Content is King*

• “Healthy” Social Apps

• 5 Years of Angel Investing

• Status Limbo*

• The 20/20 Workweek

• Zero-Sum vs. Positive-Sum Products*

• 24 Working Theorys for 2024

• The Idea That Won't Go Away

• One-Round Wonder*

• How to Do Business School Right

• Don't Build a Social Network, Build a Social Utility*

• The "High Potential" Handicap*

• Big TAM Founders, Small TAM Startups*

• Why Are All the Public Intellectuals Men?

• Full-Stack Something

• The Brunch Test*

• Unbundling Cash & Equity

• Define the Game

• Trophy Jobs*

• The Generational Business Trap*

• Generalized AI Anxiety

• Product vs. Production

• Collective Experiences

• Rise of the Silicon Valley Small Business*

• What I Learned at Clubhouse*

• Ritual Social*

• Community Fission & Fusion

• The Group Chat Renaissance

• Group-Generated Content

• The Revival of Consumer Social

If an essay or two or more resonate, I’d appreciate if you subscribe & share with friends :)