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Benjamin's Substack

Benjamin Simkin

My personal Substack

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Substack
PricingOnly free issuesPublishesWeekly
Issues27Foundeda year agoLast Issue3 months ago
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Latest Issues

Every serious company will hire a CAIO in the next 24 months. Most will get it wrong.

Every Fortune 500 company has a CFO. Every one has a COO. Most have a CTO.

Almost none have a CAIO - Chief AI Officer. And most have never heard of this role.

That changes in the next twenty-four months. And most of them are going to hir...

3 months ago
7

One client paid 15 times more than the other. Same amount of work.

In the early days of my agency, I had a client paying $20,000 a month.

I didn’t think much of it at the time. I figured that’s just what this work was worth, because that’s roughly what it was worth to them.

Around the same time, I took o...

3 months ago
2

The better you get at AI, the more trapped you become

I had a conversation last week that’s been bothering me since.

A business owner, sharp operator, doing a bit over $4M a year, was showing me his AI setup. And honestly, it was impressive. Proposals that used to take his team two days now t...

3 months ago
3

The man who got rich the day he stopped working

Milo Jones worked a farm in Wisconsin for the better part of forty years.

He did everything you’re supposed to do. Up before the sun. Worked the land with his own two hands. Cheese, crops, a few hogs. Whatever the season asked of him. Hone...

4 months ago
3

Why do you go to work?

Why do you go to work?

A survey one time asked thousands of men why they got up in the morning and went to work. And 19 out of 20 didn’t know. 19 out of 20 working people didn’t have the foggiest notion of why they wake up in the morning a...

4 months ago
6

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  • Benjamin Simkin

    Benjamin Simkin is an entrepreneur, marketer, and technologist who builds systems that turn chaos into clarity. Founder of BusinessNET and creator of The Mastermind, he helps entrepreneurs scale with strategy, structure, and freedom.

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