Success, especially early success, can quietly shape the wrong habits.
It builds confidence, which is necessary. But it can also create a belief that what worked once will continue to work, even as the environment changes. That belief is where many scaling challenges begin.
Howard Chang experienced both sides of that equation. He launched his first business at 20 and saw rapid success. By his mid-twenties, he had built a lifestyle that reflected that momentum. Then the market shifted, pressure increased, and the assumptions that once felt like strengths began to break down.
Looking back, he described it simply.
“I started drinking my own Kool-Aid.”
What followed was not just a market correction. It was a leadership lesson that reshaped how he approaches building companies today.
The Hidden Cost Of Trying To Do Everything Yourself
One of the most common patterns among founders is the instinct to carry too much for too long. In the earliest stages, that instinct is useful. Scrappiness is often what gets a business off the ground.
But that same instinct becomes a liability as the company grows.
Howard saw this clearly in hindsight.
“I try to do too many things on my own. I didn’t ask for enough help.”
There is a moment in every company where the founder’s role needs to shift. What worked at the beginning no longer works at scale. The challenge is that this shift is not operational. It is psychological.
Letting go is not just about delegation. It requires trust, and more importantly, it requires a willingness to admit that someone else can do certain things better.
That is where many leaders hesitate.
Ego Is The Real Bottleneck
When Glenn and Howard discussed hiring, they quickly moved past tactics and into something more fundamental.
“As entrepreneurs, we’re guilty of ego and hubris… you kind of have to get over yourself a little bit.”
That statement lands because it is both honest and uncomfortable.
Most CEOs would agree, in theory, that they should surround themselves with people who are stronger in key areas. In practice, however, ego often creates subtle resistance. It shows up in delayed hires, in over-involvement, and in second-guessing people who were brought in to lead.
The shift that unlocks scale is not about finding better people. It is about becoming the kind of leader who can actually empower them.
This often means redefining success internally. Instead of being the person with the answers, the CEO becomes the person who builds the environment where the best answers can emerge.
From Selling Solutions To Understanding Problems
This mindset carries into how Howard approaches his work at theturnlab.
Rather than leading with ideas or solutions, he emphasizes something that sounds simple but is rarely practiced well.
“Our job is to first fall in love with the problem.”
That phrase reflects a deeper discipline. It requires slowing down long enough to understand what is actually happening inside a business before proposing a fix.
Too often, companies jump directly to execution. They assume they understand the issue, then invest time and resources into solving it. When the outcome falls short, they iterate on the solution rather than revisiting the original assumption.
Howard’s approach shifts that sequence.
By focusing on the problem first, his team builds a foundation that makes the eventual solution more relevant and more effective. It also changes how clients experience the relationship.
Instead of being pitched, they feel understood.
He described the contrast in a way that resonates across industries.
“Be a good date. Ask good questions. Show interest.”
It is a reminder that business, even at scale, is still fundamentally about human interaction.
Why Most Companies Miss The Mark With Customers
Howard shared a moment that highlights how easy it is to lose sight of this.
He advised several agencies preparing to pitch a client. The guidance was straightforward. Focus on the client’s business. Demonstrate insight. Show that you understand the problem.
Despite that, each agency defaulted to talking about themselves.
“They all talked about the awards they’ve won… didn’t show any insight in the client’s business.”
The client walked out shortly after.
This pattern is not limited to agencies. It appears in sales conversations, marketing strategies, and even product development.
When companies become too focused on what they offer, they lose connection with what the customer actually needs.
Re-centering on the problem is not just a strategic adjustment. It is a discipline that has to be maintained as the organization grows.
Building With A Broader Perspective
Another element that shapes Howard’s leadership is how he defines value.
While many businesses focus primarily on financial outcomes, he takes a broader view.
“I’m always thinking… how is this going to benefit my community, my staff, society?”
This perspective influences how decisions are made and which opportunities are pursued. It also creates a different internal dynamic.
When teams understand that the company is building something with a wider impact, engagement tends to deepen. People are not just contributing to revenue targets. They are contributing to something that feels more meaningful.
Over time, that alignment becomes a competitive advantage.
It shows up in how teams collaborate, how leaders make trade-offs, and how the company is perceived externally.
Letting The Business Evolve Beyond You
As Howard continued building, he eventually found himself leading two organizations simultaneously. That situation came about through a combination of intentional design and necessity.
He initially stepped back from theturnlab to focus on scaling Just Meeting Rooms, a platform that grew rapidly in a short period of time. Later, circumstances required him to step back into a more active role again.
What stands out is not just the complexity of managing both, but the willingness to adapt.
Scaling is rarely linear. Roles change. Structures evolve. What works at one stage may not work at the next.
The key is staying flexible without losing clarity on what matters most.
Using AI Without Losing Judgment
When the conversation turned to AI, Howard’s perspective remained consistent with the rest of his approach. He sees its value, but he does not overstate its reliability.
“I see AI as kind of like the useful idiot.”
It can accelerate thinking and provide useful starting points, but it still requires human judgment to validate and refine what it produces.
He shared a simple habit that reflects this.
“One of the most important prompts… is to ask, ‘Are you sure?’ And 50 percent of the time it changes the answer.”
That small step reinforces a broader principle.
Technology can enhance decision-making, but it should not replace critical thinking.
In his business, AI is used to reduce friction and improve efficiency, allowing the team to focus more on strategy and less on repetitive execution. In some cases, it even shifts work back to clients when it can be done faster and more effectively on their side.
That decision may reduce short-term revenue, but it strengthens long-term relationships.
“If this is about building the right business, not building a big business.”
Where Real Scale Comes From
When you step back from the details, a consistent theme emerges.
Scaling is not primarily about tactics. It is about mindset.
It requires a willingness to question your own assumptions, to bring in people who challenge you, and to stay grounded in the problems you are trying to solve.
It also requires something that does not always come naturally to successful founders.
Humility.
I’m Glenn Gow. I coach CEOs who are navigating exactly these transitions as their companies grow.
If you are finding that your business is hitting a ceiling, it may not be a market problem or a strategy problem. It may be a leadership shift that has not happened yet.
Get in touch to explore how to scale your leadership alongside your business.
