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Leadership lessons from scaling AppSumo, coaching CEOs, and making a lot of mistakes along the way.

“Annual Plans Are Startup Suicide” reflects how I used to think annual plans were genius. I was wrong, and I explain why.

“The Marketing Stack Mistake Killing Startups” comes from watching a founder spend a hundred thousand dollars on Salesforce at one million dollars in annual recurring revenue. That kind of mistake sticks with you.

Then there is “Founder vs CEO vs President vs COO,” which breaks down what these leadership roles actually mean in practice. The titles get thrown around loosely, and that causes problems.

I also wrote “AI Changed Everything Except the CEO’s Job,” about a CEO I coach who tested an AI system in his 400-person call center. The results were not what you would expect.

With 14 posts, this is one of my biggest sections. Leadership is the thing I think about most.