There’s a version of entrepreneurship that doesn’t get talked about enough. It’s not the startup grind or the highlight reel of scaling and exits. It’s what happens after you buy a business and wake up the next day realizing you don’t know how to run it.
One of my clients is living in that moment right now. He bought an HVAC company—solid industry, recurring revenue, strong margins. On paper, it was a smart move. But the reality he walked into was very different. He’s not an HVAC guy. Not even close. He couldn’t step into the field if he had to. The former owner took the check and retired to Florida, and it didn’t take long for the team to figure out who they were dealing with. The tone shifted. The questions changed. Then came the pressure—raises, more PTO, more control over decisions. It didn’t look like a coup at first, but it didn’t take long before it felt like one.
Now he’s sitting in a place most entrepreneurs never expect to find themselves. He has contracts to fulfill, a business to protect, and a team that knows something he doesn’t. And underneath all of that is a quiet, uncomfortable thought: I might be in over my head.
Here’s where I pushed him.
This didn’t start when the employees began pushing back. It started earlier, now he believed something a lot of successful entrepreneurs start to believe after a few wins: Because I’ve been successful before, I can operate any business. No one says it out loud, but it shows up in decisions. Buying outside your expertise. Moving quickly through diligence. Assuming leadership alone will carry the day. And sometimes it works just enough to reinforce the belief—until it doesn’t.
Jim Collins talks about confronting the brutal facts, and this is one of them: confidence without context is dangerous. Entrepreneurial success is often more domain-specific than we want to admit. Running a trades business like HVAC is fundamentally different from running an insurance agency or a staffing firm. The labor dynamics are different. The expectations are different. The pressure points are different. When you ignore that, you don’t just create a knowledge gap—you create a leadership vacuum.
And that vacuum doesn’t stay empty for long. When a team senses that the owner doesn’t understand the work, they start asking a simple question, whether they say it out loud or not: Who’s really in charge here? If that answer isn’t clear, people step in to fill the gap. Patrick Lencioni has said for years that when there’s a lack of trust or clarity, teams default to politics and self-interest. That’s not because they’re bad people. It’s because they’re looking for certainty.
If you step into their shoes for a moment, it makes sense. New owner. No technical credibility. Unclear direction. That creates fear. And fear drives behavior. So they push—not just for more money, but for more control. What looks like opportunism is often a reaction to ambiguity.
But there’s something deeper going on here, and this is where the real work is. My client isn’t just dealing with a business challenge. He’s dealing with an identity moment. It’s not just, Can I run this company? It’s, If I can’t lead this, what does that say about me as an entrepreneur? That question carries weight, and whether it’s spoken or not, it shows up in how he leads.
Tony Robbins says, “Where focus goes, energy flows.” Right now, his focus is on everything he can’t do, and that energy is leaking into the business. You can feel it in the hesitation, in the second-guessing, in the way decisions get delayed or softened. This is where most owners go sideways. They try to compensate. They talk bigger, act tougher, try to project certainty they don’t feel. But people can sense the difference between real confidence and compensation.
The move here isn’t to pretend. It’s to get honest—and then lead.
This is where the work of Brené Brown becomes practical. Vulnerability, in this context, isn’t about oversharing or stepping back. It’s about clarity. It sounds like, “I’m not the best technician in this room, but I am responsible for this business.” That kind of statement doesn’t weaken authority—it grounds it. But vulnerability on its own isn’t enough. Without structure, it creates chaos. With structure, it creates trust.
Leadership in this situation isn’t about learning how to install an HVAC system. It’s about defining what good looks like, understanding the economics of the business, and creating clear accountability. This is where frameworks like EOS or Scaling Up comes into play—everyone has a seat, and everyone has a number. Clarity replaces noise.
It also means bringing in the right operator—someone who understands the work and can lead the people doing it. And here’s the uncomfortable part for most serial entrepreneur’s: when you already feel out of control, trusting someone else can feel like the last thing you want to do. But that’s the shift. Letting go of control is not the same as losing control. It’s how you create it.
Then come the boundaries, and this is where leadership gets tested. If he gives in to pressure right now—raises, concessions, decisions driven by fear—he’s not solving a problem. He’s teaching his team how to lead him. A grounded response sounds more like this: “We’re going to take the next 90 days to evaluate the business before making any changes to compensation. Here’s what performance looks like, and here’s how decisions will be made moving forward.” Clear. Calm. Firm.
This is also where a lot of leaders misunderstand psychological safety. It doesn’t mean keeping everyone happy or avoiding tension. Project Aristotle showed that teams perform best when people feel safe to speak up, but that doesn’t mean they get to set the rules. It means they can challenge, contribute, and be heard within a structure the leader defines.
When you step back, the real risk here isn’t that my client doesn’t know HVAC. The real risk is that he believed he wouldn’t need to. That belief created the gap his team is now stepping into. Warren Buffett has always emphasized staying within your circle of competence—not because you’re limited, but because discipline beats ego.
That’s the shift every entrepreneur has to make at some point. Moving from “I can run anything” to “I can lead anything, but I need to understand what I’m leading.” That’s not weakness. That’s awareness. And awareness is what creates better decisions, stronger teams, and ultimately, better businesses.
So let me leave you with this. Where might your past success be creating overconfidence in an area you haven’t earned yet? And what’s one conversation or boundary you need to step into this week, even if you don’t feel ready?
That’s your next move.
