Everyone knows the red flags of a struggling leader. But after scaling AppSumo from $3 million to over $80 million and driving more than $500 million in growth for my clients, I learned to spot the green ones.
These are the subtle signs that predict success before it even happens.
They Prioritize High-Value Work
The most effective CEOs are lazier than their team. This isn’t lazy like sitting on a beach; it’s lazy like refusing to do $50/hour work when they could be doing $5,000/hour thinking.
The best CEOs I know are allergic to busy work. They understand that their primary role is to focus on the few critical decisions that will move the needle, not to get lost in the operational weeds.
This connects to ideas I shared in Pursue A+ Players.
They Embrace Failure As a Teacher
Many leaders are quick to highlight their successes, but a $100M CEO will talk about their failures more than their wins.
Ask them about a success, and they’ll give you two minutes. Ask them about their failures, and you’d better pull up a chair. They have internalized every lesson because they know that pain is the best teacher, and those hard-won lessons are the foundation of future growth.
They Practice Voluntary Suffering
They have hobbies that look like torture to the average person: Brazilian Jiu-Jitsu, ultra-marathons, and daily cold plunges. They actively seek out voluntary suffering.
Why? Because they know involuntary suffering is an inevitable part of business and life. They want to be mentally and physically ready when it arrives.
They Hire People Smarter Than Them
Most CEOs hire down to protect their ego. In contrast, $100M CEOs hire up.
They are not afraid to build a team of experts who challenge them. If they’re not slightly intimidated by their executive team, they know they’re building a kingdom of mediocrity instead of a powerhouse of talent.
Their Calendar Is Mostly Empty
While everyone else is stuck in back-to-back meetings, the most effective leaders protect their time for deep thought. They are focused on thinking three quarters ahead, not just reacting to the current week.
A full calendar means you’re still operating like a founder. An empty one means you’re finally thinking like a CEO.
They Obsess Over Retention
They are obsessed with retention, not just growth. They understand the fundamental math of a sustainable business:
- A 5% improvement in customer retention can lead to a 25-95% increase in profits.
- Keeping an existing customer costs five times less than acquiring a new one.
Is it unsexy? Yes. Is it profitable? Always.
They Confidently Say “I Don’t Know”
Insecure CEOs feel they need to have all the answers. The $100M CEOs have all the questions.
They say “I don’t know” without flinching because they aren’t trying to be the smartest person in the room. They’re trying to build the smartest room. Their goal is to foster an environment of inquiry and discovery, not to be the sole source of wisdom.
Conclusion
The pattern is simple. $100M CEOs consistently do the opposite of what feels natural or easy.
Here is the 7 Green Flags recap:
- They prioritize high-value work
- They embrace failure as a teacher
- They practice voluntary suffering
- They hire people smarter than them
- Their calendar is mostly empty
- They obsess over retention
- They confidently say “I don’t know”
The ones who make it to the top are the ones willing to burn their old playbook. Every. Single. Time.
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