Reading Ambitiously 10.2.26 - Everyone wants a business like Windows

But as enterprises teach AI how they work, they may demand a different bargain over who owns the intelligence.

Oct 2

7

September 2026

Reading Ambitiously 9.25.26 - Agent Swarms & Machine Speed

AI already works at machine speed. Now imagine 10,000 AI agents working together. 🤯

Sep 25

11

1

Reading Ambitiously 9.18.26 - Run the business, change the business.

"You can't be getting there, you have to already be there." Five bets for 2026 on data, security, and redesigning the work with AI. 👋 from Base Camp…

Sep 18

5

Reading Ambitiously 9.11.26 - Meat proxy and AI slop

A meat proxy: someone who passes along AI-generated text without reading, understanding, or validating it.

Sep 11

5

Reading Ambitiously 9.4.26 - The Last S in SaaS

AI can build the software you’ve always wanted in an afternoon. Before your business depends on it, ask one question: Who carries the iceberg?

Sep 4

12

2

August 2026

Reading Ambitiously 8.28.26 - AI has an agency problem

Companies ask employees to reinvent work with AI without a clear share in the gain. Leaders who want change must let people play for the upside.

Aug 28

8

Reading Ambitiously 8.21.26 - Grok Bot is a glimpse of the future

When a product is truly great, the technology fades into the background. Grok Bot turns agents, tools, and routines into something familiar.

Aug 21

11

Reading Ambitiously 8.14.26 - Walking the dog. My new favorite way to use AI.

His name is Mac, and the lab runs on a Mac. Which one is better trained depends on the day.

Aug 14

11

Reading Ambitiously 8.7.26 - Your Margin Is My Opportunity

Anthropic may be on its way to $100 billion in revenue with gross margins approaching 80 percent on Claude’s API. Competing those margins away is…

Aug 7

10

July 2026

Reading Ambitiously 7.31.26 - The window was the way out

The human truth in anything you make rarely appears at the beginning. You have to go through the work to find it.

Jul 31

8

1

Reading Ambitiously 7.24.26 - AI Sovereignty

AI gets more useful every time we teach it how our business works. The question is whether we can take that learning with us.

Jul 24

9

Reading Ambitiously 7.17.26 - The Finished Product

Companies are buying AI faster than they are learning to use it.

Jul 17

8

1