Essays

What we call 'venture capital' is actually four different things — seed investing, venture classic, supercharged growth, and private small caps. Continuing to pretend otherwise does a disservice to everyone involved.

Dissecting 300 years of fundraising fraud to reverse-engineer a playbook for founders building real things — from Gregor MacGregor's invented country to WeWork's Community Adjusted EBITDA.

The Glorious History of Productive Delusion, The Physics of a Bubble (A Scientific Framework), Genuine Benefits of Mass Technological Psychosis, and Why Everything Will Go According To Plan

A Soulful Parody of Will Manidis' 'Legible to capital'

"What is doubt but letting a traitor in the back door of your soul?"

An Epidemic of Unchecked Incompetence

The Great Founder Sifter

"When someone tells you who they are, believe them."

Our arguments suck. Nothing is convincing for any of the right reasons.

Make Me Believe You

Revolution Through Evolution

Revisiting My Own Ideas

Reshaping Capitalism, Epic World-Building, Collective Self vs. Self-Acceptance, & Mormon Apologetics

The Fibs That Fashion Our Families & Faculties

If You're Going To Rewire Your Brain, Rewire It For The Better

A Season of Storytelling

"Doing nothing is often the most important something."

YC’s Formula For Startup Manufacturing

The Missionary, The Mercenary, and The Minstrel

Our Version of “The Things They Carried”

Just as Reflective as Reactive

Poisoning The Well

"When everyone is super, no one will be."

Weaving Together Your Understanding of the Universe

Imagineering: A Prototype For Imagination

The Clash of Conviction vs. Consensus

“When people stop talking that’s when you get violence.” (Charlie Kirk)

A Schizophrenic Obligation

The Moral Imperative To Grind, The Social Safety Net, & The Mournful Middle Class

Dreaming Of The Global Knowledge Graph

Making The Case For Hope Maximalism

Building An American TSMC

Combating The Hypnotized Consent of The Majority

"And Know That I Am God."

Here We Are Again At The Twilight

Capital Allocation That a VC Could Never

An Ongoing Love Affair With The US of A

The First Principles of Being Useful, Circling Back, and Backing Outliers

Why Cluely Is The Dark Spirit of Venture Capital, Whether You Like It Or Not

A Return To Critical Thinking

Too busy languishing in regret to make room for hope

The Great Founder Sifter

Unpacking The Layers of Dependencies That Delay Deviance

"Biology is not an indecipherable black box; it’s living code that we can model and understand."

Reframing & Reflecting

The Currency of the Attention Economy Is Loudness

A Newfound Republic of Letters

Exploring Not Just WHAT Happened, But WHY

How VCs Are Picking Their Bets

Venture as a Thesis Delivery Mechanism

"Literal life force transmuted into shareholder value." (Augustus Doricko)

Building a Venture Firm With Authenticity

A Smorgasbord of Reactions

Stepping Back Again To Reflect

Defensibility Is For Dummies

Mapping The Systemic Flaws in the Venture Ecosystem

"We're Just People, Man"

Pushing Back Against The Loudest Models in Venture Capital

The Wisdom of Cycles & The Importance of Thinking For Yourself

Trade-Offs In Everything You Do

How The Venture Ecosystem Gets Pulled Towards The Loudest Actors

A Revolution Years In The Making

Perplexity's journey, plus an update on the evolution of Investing 101

Pondering The Future Form of My Writing Function

Revisiting Your Own Ideas

Defense Deep Dives, Intellectual Faith, and More

“Our very strength invites challenge.”

An Ode To Revisionist History

A Brief Repose From Investing To Reflect On Service

A Shortage of Founders, Funding, Foundations, or Guts?

Allocators, Agglomerators, and Absorbers

A Struggle At The Extremes

Fetishization of Performative Failure Creates a Phobia of Actual Failure

Sizing Up Each Fund's Strategy

Indexing Your Beliefs Before They Get Drowned Out

On Stewardship

Palmer Luckey's Perspective on Historical Futurism

Balancing Big Promises and Big Payoffs

Good Business vs. Business As Usual

The Unit of Underestimation

And... Not a Good Idea?

The Art of Convincing Me I’m Not Getting Played

The Math Behind Venture Fund AUM

Painting Two Dramatically Different Worlds in Our Collective Imaginations

"Singles and doubles win games, but home runs win hearts."

Career-Building Blindness in Venture

"Half the budget is a waste; we just don't know which half."

Storytelling, Chief Evangelists, and World Building on Vibes

"If you don't keep your feet, there's no knowing where you might be swept off to.”

An Investment Memo

Venture Capitalist’s Self-Loathing Mentality

"Once you start writing, you see things to write about everywhere."

"You can either run from it, or... learn from it!"

Miles To Go Before We Sleep

Constantia Prima

Why Are Mommy & Daddy Fighting About AI?

Defining What It Means To Be a Research-Driven Venture Firm

Imagination, Creation, Capture, Conversion

"Turning Startups Into Companies"

Science Fiction as a Product Roadmap

The Need For A Renaissance of Truth Seekers

The Endless Ebb And Flow

April Fool's, The Optimist's Christmas + Learning Is Good, Actually

Of Things That Matter Most

Two kinds of people in the world: Those who drive, and those who ride

Process, People, and Playbooks

Finding The Courage To Be Wrong

Distribution + Data Become Concentration Functions

Thinking Through The History & Evolution of Hard Investing

The Insecurities of VCs Who Desperately Want To Be Liked

The Rarest of Commodities, But The Furthest Reaching Impact

The Art of Not Slowing Down

Reinventing Your Information Input Systems

You Are What You Think About

Cottage Keepers vs. Capital Agglomerators

The Sound of Silence

Revisiting Your Own Ideas

Fiction, Playbooks, and a Call For Improvement

From A Four Year Old Essay To A New Theology

A Surprising Spike In Venture Fund Mortality

Featuring Bryce Roberts

Consolidation Is Upon Us

Reflecting On The Most Interesting Timeline

Becoming Unprogrammable

"Don't Euthanize Me"

Plus, an excerpt on Midjourney

When "Let Me Know How I Can Be Helpful" Fails

You Best Start Believing That Psychology Matters. Its All That Matters

Sharing a recent podcast appearance

And The VC "Back-Scratch" Circle

Defining Your Personal Bar

A 30,000 Foot View

Whatever You Are, Be A Good One

The Other End Of The Valuation Stick

A Model For Building Communities / Juntos / Cities / Holding Companies

Getting Off The Grid

Or Why Hopin Is Everything Wrong With Venture Capital

Capital Can Only Control So Much

Using Science Fiction to Invent the Future

"Where is the wisdom we have lost in knowledge? Where is the knowledge we have lost in information?" (T.S. Eliot)

A Deep Dive From Contrary Research

An Idea I Return To Again And Again

“So much of our lives is meaningless, a self-canceling vacillation and futility."

Acquisitions, Shutdowns, and Layoffs Oh My

Speed vs. Cost

Why It's Easier To Say No Than It Is To Ask "Why?"

Is Venture Capital Killing Itself?

Why Do People Hate Cathie Wood So Much?

Introducing Retrospection Into The Hype Cycle

A Conversation With Alexa Kayman

Trickle Down Hype-onomics

The Meritocracy of Venture Capital

The Memeification of Venture Capital

$1B Valuation < $1B ARR < $1B Cash Flow

Haaave you met so-and-so?

Working Hard, Or Hardly Working?

In Defense of Good Tech Companies

The Evolution of Interest

A Contrary Research Event

Defensibility Is For Dummies

The Best Starting Point To Understand Any Private Tech Company

Framing a Frame of Mind

The What Is Never As Important As The Why

The Collective Hallucination of Oncoming Capital

Reflecting on The AI Moment

Dependencies & Failure Points

The Culling of The Unicorns

Betting The Mouse To Save The House

Reinventing The Practice In The Process Of Learning It

Revisiting Your Own Ideas

Storytelling, Leadership, Predicting The Future, and Faithfully Asking Questions

Venture Capital Is The Name, AUM Collection Is The Game

Learn To Keep From Dying

And All The Responsibility That Goes With It

Consolidation Is Coming In 2023

Why We Never Ask The Right Questions

To Burn? Or Not To Burn?

Total Addressable Mirage? Or Miracle?

Fool Me Once? Shame On Me. Fool Me Twice? I'll Lead Your Round

The Art of the Outreach

Dreaming The Dream Takes Practice

The Human Element of Investing

Is The Juice Worth The Squeeze?

My Figma Surprise

Announcing Contrary Research

An Allocator of Time

The Hard Truth About Soft Truths

But for what purpose?

A Case Study On The Venture Process

Does "Everyone Is An Investor" Still Hold in a Recession?

An Exploration of "How Can I Be Helpful?"

"The universe is made of stories, not of atoms." (Muriel Rukeyser)

In other words? “The ends rewrite the means.”

Transparency in Talent Data

The Pursuit of "Venture Scale"

Building a Better Venture Firm

A examination of when cash can anoint a market winner

The world of venture capital is changing dramatically. Over the last few months I've spent a lot of time thinking and writing about the forces driving that change. The two most significant I've seen a...

Talk of "The Great Resignation" is everywhere. 70 million people changed jobs in 2021 and 70% of that was voluntary. People choosing to quit. "Two out of every five office workers are planning to resi...

The world of venture capital is changing dramatically. Over the last few months I've spent a lot of time thinking and writing about the forces driving that change. The two most significant I've seen a...

Frameworks for Reflection

Process, People, and Playbooks

In the late 80s, early 90s my Dad was in almost exactly the same phase of life as I am now. We're both in our 30s and about to have our 3rd kids. In just that generation the world has changed dramatic...

The Bifurcation of Investable Companies

As everyone with a brokerage account braces for emotional trauma they've rarely if ever experienced before it has been interesting to watch public and private investors react. There are aspects of pub...

When Everyone is Special Nobody is

I'm a big fan of thinking about the history of things. To understand why you do something today you sometimes need only look at how it got started. Humans are creatures of habit, so a lot of times we ...

Power of the People

Anyone who is invested in public tech stocks has been feeling a lot of pain over the last few weeks. High growth software has seen a ~50%+ correction and the businesses with the highest multiples have...

A lot of you haven't lost a fortune and it shows

Investors hear tons and tons of pitches. They pass much more often than they fund a company so they have to think of a way to maintain a relationship without being able to invest.

In a previous life, I briefly lived in Seattle, and I was a big fan of the city. I grew up in New Mexico, so I’ve had about as much sun as I need for one lifetime. Seattle’s rainy streets were a respi...

If you've been reading my writing for a while, you'll know that I'm far from a venture capital stan. I'm a pragmatic observer of my own craft, and as much as you can learn from success, there is also ...

I'm not a sports guy. We are not a sports family. Growing up, my parents loved sports, and watched them a lot. But it wasn't my thing. That has reflected in my children. A few years ago when my oldest...

Investing, in simplest terms, is taking one finite resource and trying to allocate it to maximize for an ideal outcome. Whether you're allocating money, time, energy, or attention. Everyone is an allo...

Roam + Investing

This essay first appeared on the RoamBrain blog.

This article is a result of the intellectual rigor of a Junto, inspired by Benjamin Franklin’s club for mutual improvement of the same name, between the author, Tim Riser, Minna Wang, Nikita Singaredd...

This article was written by Kyle Harrison, as a result of the intellectual rigor of a Junto, with Clark Brimhall, Erik Hansen, Megumi DeMond, and Christina Muhlestein

Appreciation is a funny thing. People say “the squeaky wheel gets the grease,” and that basically emphasizes that the things that call attention to themselves are the most successful in getting attent...

When I got to college, I knew just about nothing. I was going to major in film because I liked making stupid videos with my friends. I thought girls would like me for my “personality.” I took Beginnin...

This semester, I’ve had the opportunity to work as a co-instructor in an instructional psychology & technology class focused on EdTech startups. The class is broken up into three parts, (1) intro to c...

In September 2014, I had just declared my major. Accounting. What did I want to do with that? Who knows, but it sure sounded stable. I was sitting in one of my business classes, desperately trying to ...

Here’s the thing. I don’t profess to be an economist (or a zoologist, but that’s for a different reason). I don’t know every issue that is wrong with education, but I think a conversation I had last w...

I want to make sure I offer this disclaimer, the things talked about in the conference were off the record and I’m just sharing some interesting thoughts that I had without any specific details from t...