Napkin Math

Profit and power in technology.

Feb 13, 2025

Does OpenAI’s Deep Research Put Me Out of a Job?

An investigation into a Sam Altman tweet

Jul 9, 2021

Pricing Strategy is Product Strategy

How Technology Enables Companies to Charge More

Feb 17, 2022

The Future of Netflix

When everyone’s a streamer, nobody is.

Apr 30, 2024

The AI Wars Have Begun

OpenAI, Meta, and the $120 billion battle for the future of intelligence

Aug 7, 2020

New York Times: Investing In The Long Term

A review of the Q2 earnings: growth in digital subscriptions, a fall in advertising, and a decline in APRU due to long-term investing.

Jan 7, 2021

My Favorite Company Deep Dives of 2020

Taking a look at the best companies deep dives of the past year, including posts on Fiverr/Upwork, Carta, Tyler Corporation, CostCo and more

May 15, 2024

Google Goes All In on AI

The company has every possible advantage, but can they use it?

Nov 6, 2020

Your Uncle Is Still Your Uncle: Ant Pulls Its IPO

Ant's IPO has been taken down. What happened, what do you need to know and what should we expect to see next?

Sep 23, 2021

Toast—a Vision of Software’s Future

Hints to why their shares popped 60% in their first day

Oct 14, 2021

Who is Making Money in Space?

Exploring the SPAC Frontier

Aug 6, 2024

Here’s a Million-dollar Software Idea

Welcoming the dawn of a new era in computing

Sep 9, 2020

First Steps to Buy A School Bus Company

Last week I pitched the idea of buying a school bus operator. This week I tell you how to do it.

Mar 6, 2025

AI Has Learned How to Capture Our Emotional Metadata

What happens when our computers know us better than we know ourselves?

Nov 19, 2021

iBuy, iRent, iLose My Investors Money

The Murky Future of American Housing

Jun 10, 2020

Crash: Pitch a Company, Get a Job

Candidates earn jobs by putting in more work than their competition

May 29, 2020

The Jet.com Obituary

The brand couldn’t compete against Amazon, but the acquihire was worth it for Walmart

Aug 29, 2024

Welcome to the Era of the Gritty Startup

The age of glut is over. Here are three lessons to navigate through leaner times.

Jan 30, 2021

A Local News Revival

How product, marketing, and cost innovations create a massive opportunity

Apr 2, 2025

OpenAI Is a Once-in-a-lifetime Startup

This newest funding round means this company has either a trillion-dollar outcome—or nothing at all.

Apr 10, 2025

How to Write Online

It’s less about capturing attention, and more about deserving it

Mar 20, 2025

Can the Startup Mindset Fix America?

Only if buttressed with smart policy, Ezra Klein and Derek Thompson argue in their new book, 'Abundance'

Jun 17, 2021

Finance is Broken But Don’t Worry, This Has Happened Before

Net Income and the Refactoring of Our Financial Ideology

May 23, 2024

Microsoft’s Boring but Profitable Future

The PC giant is making Windows exciting again

Mar 13, 2025

AI Is Breaking Media. Here’s How Publishers Can Survive.

Content is cheaper than ever to produce. That will bring devastation—and a new wave of opportunity.