Napkin Math

Profit and power in technology.

Oct 7, 2021

The End of Software, Again

The impending doom of horizontal SaaS

Feb 10, 2022

Is YC the Monopoly It Thinks It Is?

The Pricing Power Flex

Sep 5, 2024

Vibes-based Search

The next big disruption in software is here, and it understands what you’re looking for better than you do

Jul 23, 2024

Vibes Are a Legitimate Economic Indicator

In her debut book, Kyla Scanlon makes the case for feeling the numbers

May 13, 2021

In Defense of WeWork’s Community-Adjusted EBITDA

Clarifying the murky middle ground between Gross Profits and Net Income

Aug 13, 2020

Sometimes You’re The Datadog, Sometimes You’re The Hydrant

The history of cloud computing, how DevOps and Observability became so big, and the fate of Datadog

Apr 3, 2024

The One-person Billion-dollar Company

Can AI agents make you a billionaire?

Aug 28, 2020

Uber and Lyft Live Once Again

What drivers think of AB 5, why it was written, and the pricing differences between services

Aug 22, 2024

Copy Rights and Wrongs

Who owns the output of AI—the machines or the creators?

Mar 23, 2022

BIG announcement incoming

I'm going full time on Napkin Math

Sep 24, 2024

The One-person Billion-dollar Company

Can AI agents make you a billionaire?

Apr 29, 2021

Gross Margin: An Indicator of Market Power

What America's Oldest Jeweler Can Teach Us About the Value of Bling

Jul 28, 2021

Twilio’s Second Act

Twilio rode its API to a $66B valuation. Now it’s trying to become the Universal Switchboard for the internet.

Apr 11, 2024

Can the Truly Moral Billionaire Please Stand Up?

My quest to find Jesus Christ with a Gulfstream

Jun 18, 2020

Explaining the Hertz Situation

A layman’s guide to bankruptcy

Sep 2, 2021

Content Moderation Double-Bind Theory

The market failures damning content to ever increasing sensationalism

Jan 13, 2022

3 Thoughts On Justworks

The newest SaaS company to hit the public markets

Aug 12, 2022

A Tale Of Two Acquisitions

The Unity Conundrum

Nov 4, 2020

Can Political Betting Markets Predict Election Outcomes?

Polls and pundits don't do a good job of predicting election results. But what about prediction markets? In this post, we discuss what makes a good market and what could cause it to be wrong.

Aug 16, 2024

Feasting at the Trough of AI Slop

AI imagery is more popular, more powerful, and less harmful than you think

Feb 28, 2025

Playing ‘Civilization 7’ Is Like Being a Ruthless Corporate Consultant

Let’s talk about the tech world’s relationship with video games

Sep 23, 2024

What Are AI Agents—And Who Profits From Them?

The newest wave of AI research is changing everything

Aug 20, 2021

How a Climate Tech Startup Closed 5+ Enterprise Deals Before Even Launching

Remora, The Bureaucracy Buster

Oct 28, 2021

The Creator Power Scale: A Formula to Determine if Platforms are Ripping You Off

An examination of the Twitch Hack data