Napkin Math

Profit and power in technology.

Sep 17, 2020

How Chegg Grew Their Share Price 20x In Four Years

Chegg grew their stock price from under $10 to over $85. They did it by changing their business model from the ground up and investing in digital media content.

Feb 4, 2021

Revenue: It’s Simple, Until It Isn’t

Finally, a clear explanation of bookings, billings and revenue

Dec 4, 2024

The Religion of Ramp

How the fintech became one of the fastest-growing startups—ever

Jun 5, 2023

The Bugman Cometh

My sick, unexplainable desire to buy a face computer

Dec 13, 2023

Want to Build? Technical Excellence Won’t Be Enough.

This new era of startups requires a founder baptized in the humanities

Feb 15, 2023

Bada Bing: Why Microsoft Wants Google to Dance

Surely nothing bad will happen with an AI hooked up to the internet

Oct 13, 2022

Who Wins the AI Value Chain?

It's A Brave New World

Aug 3, 2022

The Meh-taverse

A Book Review

Sep 21, 2022

The AI Writer

How tech is changing what it means to be an author

Sep 25, 2020

Substack Rhymes With Medium

Substack can't decide if it's a CMS or a media brand. Neither could Medium. Their indecision will likely lead to similar outcomes.

Jun 9, 2022

Software is Eating the Individual

The Embedded Human

Dec 7, 2022

The Primary Trends I’m Investing In Next Year

China, boring AI, vertical SaaS, and Apple's power

May 10, 2023

Why Are Republicans Better at Making Money on the Internet?

What consumer tech and media got wrong

Jun 15, 2022

Selective Optimism

People who promise high returns forever are liars

Jul 14, 2022

Has Venture Lost Its Soul?

A Book Review of The Power Law

Nov 21, 2022

6 New Theories About AI

Software with superpowers

Feb 14, 2024

Autonomous Vehicles Have a Problem of Narrative

The tech industry needs to be honest about the trade-offs of risk

Jul 14, 2020

How Costco Convinces Brands to Cannibalize Themselves

An unlikely marriage where both sides win

Aug 16, 2023

The Internet Is Still Early

Neither hellscape nor utopia—the internet makes society anew

May 4, 2022

The Empire Stripes Back

A $100B Bet on Two Brothers

Oct 5, 2022

The Face That AI Built

My explorations in image generation

Mar 27, 2024

What Are AI Agents—And Who Profits From Them?

The newest wave of AI research is changing everything

Sep 18, 2024

Live Fuller, Not Bigger

You must escape the shallow joy of more

Mar 29, 2022

Twitter’s Probably Screwed

The Rugged Landscape of Digital Advertising