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May 6, 2026

The Four Jobs of Outbound

Three of them belong to AI. The fourth never should.

Jason Jackson
Jason Jackson
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Apr 29, 2026

The Renewal You're Walking Into Blind

Your biggest customer is about to ask to pay you less. They're going to win.

Jason Jackson
Jason Jackson
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Apr 22, 2026

The Loyalty Tax

The customers you're protecting with a grandfathered rate are halfway out the door.

Jason Jackson
Jason Jackson
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Apr 15, 2026

Two Sets of Books

Every founder has two sets of numbers. Most pretend they don't.

Jason Jackson
Jason Jackson
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Apr 8, 2026

The Fight You Had in the Garage

Your co-founder relationship didn't break. It just got an audience.

Jason Jackson
Jason Jackson
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Apr 1, 2026

The SaaSpocalypse Is Coming for You

Your product works, but does it have a reason to exist?

Jason Jackson
Jason Jackson
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Mar 25, 2026

"AI Made Me Do It!"

Your team knows why you really made those cuts. And it wasn't artificial intelligence.

Jason Jackson
Jason Jackson
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Mar 18, 2026

Seven Books About Goats

What nobody tells you about the founder breaking point

Jason Jackson
Jason Jackson
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Mar 11, 2026

The Code You Built in the Garage Is Holding You Hostage

Your product works. It just can't grow.

Jason Jackson
Jason Jackson
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Mar 4, 2026

The Efficiency Trap

When "lean" stops being a strategy and starts being a coffin

Jason Jackson
Jason Jackson
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