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Oliver Buchannon
Jason Jackson

Jason helps founders scale companies. 20+ years leading product and ops at high-growth startups.

"AI Made Me Do It!"

Mar 25, 2026

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10 min read

"AI Made Me Do It!"

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

Jason Jackson
Jason Jackson
Seven Books About Goats

Mar 18, 2026

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12 min read

Seven Books About Goats

What nobody tells you about the founder breaking point

Jason Jackson
Jason Jackson
The Code You Built in the Garage Is Holding You Hostage

Mar 11, 2026

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13 min read

The Code You Built in the Garage Is Holding You Hostage

Your product works. It just can't grow.

Jason Jackson
Jason Jackson
The Efficiency Trap

Mar 4, 2026

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10 min read

The Efficiency Trap

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

Jason Jackson
Jason Jackson
Your Runway Math Is Wrong

Feb 18, 2026

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10 min read

Your Runway Math Is Wrong

The fundraising timeline doubled. Your plan didn't.

Jason Jackson
Jason Jackson
Your Culture Happened By Accident. Now You Have to Fix It On Purpose.

Feb 11, 2026

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9 min read

Your Culture Happened By Accident. Now You Have to Fix It On Purpose.

You hired people to bring fresh perspectives. Are you actually listening?

Jason Jackson
Jason Jackson
Stop Hiring for the Company You Want to Be

Feb 4, 2026

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8 min read

Stop Hiring for the Company You Want to Be

Some hires need infrastructure. Some hires build it. Know which one you're getting.

Jason Jackson
Jason Jackson
Your Dashboard Is Lying to You

Jan 28, 2026

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8 min read

Your Dashboard Is Lying to You

Most of what you're tracking is noise. Here's what to watch instead.

Jason Jackson
Jason Jackson
The Three Conversations You’re Avoiding (That Are Keeping You Small)

Jan 21, 2026

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15 min read

The Three Conversations You’re Avoiding (That Are Keeping You Small)

Your roadmap isn't the problem.

Jason Jackson
Jason Jackson
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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