Field notes on building a company that outgrows 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 One Hill Doctrine: Why Working on Too Many Things Is Killing Your Business
The biggest reason your business doesn't move forward? You're working on too many things. When…
AI Is Cutting Entire Job Categories, Not Just Bad Companies
I've never seen more layoffs than the last 12 months. Not even close. Not even…
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…
Entrepreneurship Is Often a Trauma Response
Entrepreneurship is often a trauma response. Almost everyone who is in the seat of a…
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…
Why Your Best Salesperson Might Be Your Worst Sales Manager
One of the biggest mistakes CEOs make is assuming their top performers will make good…
Pursue A+ Players
Hate to break it to you: A+ players will never apply to your job posting.…
How We Beat Apple, Google, and Amazon on Revenue Per Employee
We beat Apple, Google, and Amazon on one metric at AppSumo. Revenue per employee (RPE).…
The Michael Dell Strategy
Imagine you're 16 years old. Selling newspaper subscriptions door to door. Competing against salespeople in…
My Annual Ritual: Setting Up My Brand New MacBook Pro
Every year, I do something that might seem extreme to some: I start fresh with…
Win Sunday, Win the Week
Eight-figure companies are built on Sundays. I learned this while leading an $80M business .…
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…
Why Energy Management Beats Time Management
I used to worship my calendar. Every minute was color-coded, time-blocked, and optimized. I had…
Founder vs CEO vs President vs COO
Every startup has different leadership roles, but what do they actually mean? I see a…
Why Keeping Wrong People Kills Teams
In 2001, Netflix faced a moment that would redefine how we think about team building.…
The $150,000 Lesson That Changed Everything
I paid Tony Robbins $150,000 for coaching. His advice changed how I build companies. 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…
6 Things I Should Have Done Sooner as a CEO
Things I should have done sooner as a CEO: Hosted dinners with inspiring founders Hired…
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…
My 4-Question Test for Hiring
Here is my four-question litmus test that I use before hiring anyone. The Average Do…
The Most Critical Hire That Shaped AppSumo
Ilona was one of the most critical hires we ever made at AppSumo . Full…
The Permissionless Approach
I’ve hired over 100 people. Worked with 9-figure entrepreneurs. Built teams at one of the…
The Ultimate Guide to Hiring an Executive Assistant
Most founders wait too long to hire an Executive Assistant. They say, “I’m not ready”…
14-Step Guide to Scaling Your Business
I recently sat down with Greg Isenberg , host of The Startup Ideas podcast ,…
A Journey of Sacrifice and Opportunity
40 years ago, a young man left a small village in Iraq in search of…
New Money Talks Podcast
I recently sat down with John Melizanis and Kyle Russell on their New Money Talks…
My CEO Story
CEO is a stressful job. Nobody really teaches you how to do it. Here's my story.
Live Workshops
Last year I was forced to make a tough decision… You see my 1:1 coaching…
Interesting People 2024
In June 2024, I received this email from Andrew Wilkinson. “Every year, I invite 100…
My Guesting on Kopywriting Kourse Podcast
I recently sat down with Neville Medhora for a conversation about scaling companies and navigating…
The Futur Podcast: The Key to Big Profits
When I was CEO of AppSumo, I discovered something that transformed our business: the power…