When you're starting out, you watch every dollar.

You bootstrap. You delay. You find the cheaper option. You invest whatever margin you have back into the business, whether it’s more people, better tools, another location or another capability. That discipline is how you survive the early stage. It's how most businesses make it past zero.

But somewhere in that discipline, a habit forms that's harder to see: you stop investing in yourself. And eventually, in the people around you.

In the startup stage, force gets you through. 

You outwork the problem. You figure it out as you go. The founder is the operating system. And don’t get me wrong, that works (for a while) because the business is still small enough to run on instinct and will. It might actually be what sets you apart from your competition.

And then the business grows. And your job changes.

More complexity. More people. More decisions with longer consequences. And here's the part I didn't fully anticipate at the speed I should have: the team that got you here isn't always the team that gets you to the next level. Not because they aren't talented or loyal. But because the capabilities required at the next stage are genuinely different.

The person who ran one location brilliantly may not be equipped to think across five. The manager who executed a single system may struggle to integrate an acquisition into a cohesive structure. 

The decisions stop being purely tactical and start needing to fit into a longer arc of strategy. That's a different kind of thinking. It’s also one where if you haven't planned for it, you're already behind when you need it most.

I saw this firsthand.

We were growing and rolling up acquisitions rapidly. Momentum was building and everything felt like it was working.

What I didn't see clearly enough was that the financial model didn't account for the talent gap we were quietly accumulating. Investments in leadership weren't prioritized the way they should have been. The business had evolved. I was slower than I should have been to recognize that the people around me, and I myself, needed to evolve with it.

Those were corners I should have peered around earlier.

Here's what makes this particularly hard to catch: momentum masks it. 

When a business has momentum, everything feels easier. Decisions move faster, energy is high, and the gaps are easier to paper over. But when momentum stalls — and if the foundation isn't keeping pace, it will — everything gets stickier. It gets slower and harder to move. What felt like friction-free growth starts to feel like pushing something uphill.

Protecting momentum isn't just about sales or market conditions. It's about making sure the people and capabilities inside the business grow alongside it.

That means planning for leadership investment before you feel the pain. It means being able to articulate that need — to yourself, to your board, to the people around you who will question the expense — with clarity, confidence and conviction. 

The specific investment is less important than the discipline of making it. What matters is that you're actively developing the capabilities the business needs next, before the gap between where you are and where you need to be becomes visible to everyone around you.

Yes, there's short-term pressure. There always is. But that's a hurdle worth crossing, and arguably, one you have to cross, to make it to the next level.

Because the alternative isn't standing still. It's a stall that starts quietly and gets expensive before most owners see it coming.

So here's what I'd ask you to sit with this week: Where is the gap between what your business needs from the people around you — and from you — right now, and what are you actively doing to close it before the momentum tells you that you should have started sooner?

I included a quick diagnostic☝️– grab it and take it. If you think it could help someone else, please send it to them. 

And of course, please feel free to hit reply and let me know what you think. Your responses are incredibly valuable and helpful, and deeply appreciated.

Until next week,
Cabot