Leadership articles.
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.
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SubscribeThe CEO's Firing Playbook: How to Handle Letting People Go
"You're fired." Two of the hardest words any CEO will have to say. I've fired…
Why Most CEOs Should Actually Be Paid More
Hot take: Most CEOs should be paid more. Most teams should be paid less. Pay…
Founder Mode is dead. Long live Founder Mode.
THE CEO'S ROLE IN THE AI ERA In 2024, Paul Graham wrote an essay that…
7 Lessons From Being CEO of an $80M/Year Company
I learned these lessons while scaling AppSumo from $3M to $80M a year. That period…
Architect Mode: The Three Eras of Leadership
VIEW FULL CONTENT HERE There's a line Peter Drucker wrote back in 1963 that still…
Why Trust Matters More Than Performance When Building Your Team
The hardest people decisions are rarely about performance alone. They're about performance plus trust. I've…
The Four Things Every CEO Actually Owes Their Team
Most CEOs think their job is vision and strategy. It's not. Your real mandate is…
5 Questions to Figure Out What Kind of CEO You Are
Not all CEOs are the same. And understanding what kind of leader you are can…
The Biggest Firing Mistake I've Made
The biggest firing mistake I've made is having the tough conversation on the day I…
Annual Plans Are Startup Suicide
I used to think annual plans were genius. Get cash upfront, lock in customers, and…
The Marketing Stack Mistake Killing Startups
I watched a founder spend one hundred thousand dollars on Salesforce at one million dollars…
Founder vs CEO vs President vs COO
Every startup has different leadership roles, but what do they actually mean? I see a…
Why Most $1M CEOs Fail at $10M
The journey from startup founder to successful CEO is not a straight line. After scaling…
Stop Being Your Startup's Superman
As founders, we often fall into a dangerous trap I call the “Superman Syndrome.” After…
Amplify What Works
Apple, a $3.8 trillion company, thrives with just a handful of products. This begs the…
AI and the CEO: 5 Tasks That Survived
I used to think being irreplaceable made me valuable . It turns out it just…
7 Green Flags of a $100M CEO
Everyone knows the red flags of a struggling leader. But after scaling AppSumo from $3…
How to Make Yourself Irreplaceable to a Founder
Landing a role where you report directly to a founder comes with unique expectations. These…
14-Step Guide to Scaling Your Business
I recently sat down with Greg Isenberg , host of The Startup Ideas podcast ,…
My CEO Story
CEO is a stressful job. Nobody really teaches you how to do it. Here's my story.