I learned these lessons while scaling AppSumo from $3M to $80M a year. That period shaped how I think about leadership, growth, and what it really takes to build a company that scales. It also came with plenty of mistakes. Some were expensive. Some were avoidable. Most of them taught me something I still carry today.
Here are 7 Lessons I learned from being a CEO of an $80M/year company.
Define Success
Too many founders build toward goals they never chose. That's the fastest path to frustration. Pick a definition of success that makes sense for you and your team.
Play Offense
Too many companies keep operating from fear long after they've earned the right to get aggressive. When the foundation is strong, that's when you make the hires, investments, and moves that create separation.
Know Numbers
You can't lead well if you're guessing. When you know the numbers cold, you make faster decisions, ask better questions, and avoid emotional swings.
Change Minds
Weak leaders confuse consistency with strength. Strong leaders update fast when the facts change. Be willing to change your mind.
Overpay A-Players
The wrong person looks cheaper only on paper. The right person creates leverage, raises the standard, and makes everyone around them better. Testing your hiring process can help you identify these people.
Do Less
The CEO should do less as the company grows. That doesn't mean caring less. It means doing fewer things personally and making better decisions where it counts. It means empowering the leaders underneath you to make better decisions than you.
Remove Risk
It's fragile, exhausting, and impossible to scale when everything runs through one person. If the business only works when one person is always in the middle, it's weaker than it looks. Build redundancy the second you can afford it. This is why you need to stop being your startup's superman.
Final Thoughts
Here's the thing: these seven lessons won't prevent every mistake. But they might help you skip a few painful ones of your own.
Leadership, growth, and building a company that scales all come down to making better decisions. Define your success, know your numbers, and build a team that doesn't depend on any single person.
I hope these lessons serve you well on your journey.