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Founder bottleneck

Why decisions pile up on the founder's desk at a growing company, and what it takes to move that work onto other people.

Founder bottleneck

The sixth day

Aug 5, 2026

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8 min read

The sixth day

Tech's loudest investors are demanding six-day weeks. The country that invented the schedule outlawed it, and the man who built the five-day week did it for output.

Jason Jackson
Jason Jackson

Founder bottleneck

You've never watched yourself sell

Jul 22, 2026

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9 min read

You've never watched yourself sell

Your best sales skill went automatic years ago. This week you get to watch it work.

Jason Jackson
Jason Jackson

Founder bottleneck

Your $250,000 hire is interviewing you

Jul 15, 2026

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8 min read

Your $250,000 hire is interviewing you

You brought in an operator to take the company off your plate. Three months in, you're more buried than before, and it looks like you picked the wrong person.

Jason Jackson
Jason Jackson

Founder bottleneck

Why Your Team Brings You Every Decision

Jun 24, 2026

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8 min read

Why Your Team Brings You Every Decision

Your team ran the company for two weeks without you. Then you came home, and by Tuesday they'd forgotten how.

Jason Jackson
Jason Jackson

AI adoption

+1

You Are the Middle Manager

May 13, 2026

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9 min read

You Are the Middle Manager

The big-company AI playbook is making the founder bottleneck worse.

Jason Jackson
Jason Jackson

Founder bottleneck

Seven Books About Goats

Mar 18, 2026

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7 min read

Seven Books About Goats

What nobody tells you about the founder breaking point

Jason Jackson
Jason Jackson

Founder bottleneck

How to Become Unnecessary (and Not Go Crazy in the Process)

Jan 14, 2026

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8 min read

How to Become Unnecessary (and Not Go Crazy in the Process)

The founder's guide to getting out of your own way

Jason Jackson
Jason Jackson
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