Scale has a way of revealing things leaders didn’t know they were relying on.
In the early days, that dependence is easy to miss. Small teams coordinate through instinct. Founders compensate for missing systems. Favorable market conditions can hide weak pricing, weak incentives, or weak discipline. But as the company grows, those gaps stop being manageable. They become structural—and they compound.
That’s the central idea Brett Hickey kept returning to in our most recent Strategy at Scale podcast episode.
Brett is the founder and CEO of Star Mountain Capital, a multi-billion-dollar investment firm focused on established U.S. lower middle market businesses. Today, working with hundreds of companies at different stages of growth gives him a rare lens on scale—where it stops acting like a tailwind and begins to function as a stress test, forcing clarity about what is truly driving results and whether those drivers were ever deliberately designed.
That view didn’t begin with Star Mountain. Earlier in his career, Brett invested in the energy sector, where returns could look strong. But over time, it became clear that outcomes were driven less by execution and more by external forces beyond the company’s control.
These experiences shaped how Brett thinks about scale. His point isn’t to avoid risk. It’s more precise: scale rewards strategies where outcomes are driven mainly by controllable decisions, not uncontrollable forces. He describes this as optimizing for “higher probability driven outcomes,” where effort, insight, and decision-making actually influence results.
That mindset helps explain the factors Brett believes matter once scale sets in.
1. Get the market right before optimizing execution
Most growth stories glamorize execution: hire great people, move fast, outwork competitors. Brett doesn’t dismiss that, but he’s blunt about the order of operations.
“A lot of people actually under-invest in understanding the industry and the marketplace,” he said.
Why does that matter for scale? Because the wrong market doesn’t just slow you down—it forces you into behaviors that look productive and still don’t work. You end up spending your best talent trying to overcome structural headwinds: concentrated competitors, customers with no urgency, weak willingness to pay, or value that’s hard to explain.
At small scale, you can muscle through. At larger scale, the cost of fighting the terrain becomes prohibitive.
Brett’s answer is to start with terrain you can build on. He leans toward markets where the pain is already obvious, budgets already exist, and differentiation doesn’t depend on educating customers from scratch. In those conditions, execution compounds because demand is already understood and reinforced as the organization grows. If you’re thinking about how to systematically evaluate where those opportunities might exist, we’ve also shared a practical tool you can use to identify and assess strategic opportunities that you can download here.
2. Understand the customer behind the customer
Brett suggests looking past the immediate customer to understand where demand actually originates—your customer’s customer.
For Brett, this is a direct way to manage revenue risk.
As he put it, “Costs you can usually manage. If revenue goes away, that’s a very different problem.”
When demand weakens at the far end of the chain, the impact moves quickly upstream—and the company feeling it often does so last. That’s why Brett emphasizes earlier signals: clarity on where demand truly comes from, what forces shape it, and what could cause it to contract.
This is also why he pays attention to indicators outside the company—like where new ventures are clustering. Not because every startup wins, but because the pattern shows where disruption is attempting to form. Once everyone agrees something is changing, you’re negotiating from behind.
3. Build internal systems that hold at scale
Market and demand clarity set the conditions for scale, but they don’t guarantee that growth will hold.
As companies scale, informal coordination breaks. People stop “just knowing” what matters. Incentives start shaping behavior more than intention.
This is where Brett is explicit about the limits of culture alone. Alignment, in his view, doesn’t come from language or intention; it comes from how the system is designed.
As he put it, “If you want somebody to act like an owner… it’s a lot easier to act like an owner if you actually are.”
When incentives, metrics, and decision rights are clear, the organization can scale without relying on a few people to hold everything together through force of will. When they aren’t, coordination breaks down and decisions slow as complexity increases.
Brett isn’t offering a framework to apply or a checklist to follow. He’s pointing to a different way of understanding scale: not as speed or size, but as whether the business can continue to produce results once complexity increases and favorable conditions fade.
His point is simple but demanding: scale doesn’t reward ambition or activity. It rewards businesses that have been deliberately designed to hold as complexity increases.
Which leads to the question leaders rarely ask early enough:
As your organization scales, what is still producing results because it was designed to—and what is quietly relying on conditions continuing to cooperate?