Unlearning: The Overlooked Key to Scaling as a Founder

When you think about what it takes to scale a startup, you probably think about what you need to learn.

How to lead at scale.
How to build a high-performing team and culture.
How to hire and delegate effectively.
How to create a compelling vision and sell.
How to manage the pressures of investors, board members, and a growing team.

And yes, learning is crucial. But what’s often more important—and more difficult—is unlearning.

Because the very mindset, habits, and behaviors that got you here...

…are often the same things holding you back from what’s next.

Why Unlearning Matters More Than Learning

Every founder starts out in survival mode. In the early days, you had to do it all—close every deal, hire every team member, make every decision. Hustle, speed, and relentless execution were your superpowers.

But as your company scales, those same instincts start working against you:

• Your bias for speed turns into micromanaging and bottlenecking decisions.
• Your need for control prevents your team from stepping up.
• Your attachment to being the smartest problem-solver stops you from empowering others.

To build a company that scales without burning yourself out, you don’t just need to add more knowledge. You need to let go of what’s no longer serving you.

What Founders Need to Unlearn

Over the past 15 years coaching startup leaders, I’ve seen that nearly every successful founder must unlearn at least three things:

1. Unlearning “More Work = More Success”

In the beginning, grinding got you here. Late nights, endless emails, pushing through exhaustion. But scaling a company requires a shift from doing to leading.

The real game isn’t about squeezing more hours out of yourself—it’s about amplifying your impact through others.

What to Do Instead:

• Delegate before you feel ready. (You’ll never feel ready.)
• Trust your team to figure things out—don’t jump in and fix everything.
• Prioritize leverage over effort. If you’re working harder than your team, something is broken.

Reminder: The best founders don’t work the hardest. They build the best systems, teams, and cultures.

2. Unlearning the Need to Have All the Answers

As an early-stage founder, your ability to make quick, confident decisions kept the company alive. But as your startup grows, making every decision is a liability, not an asset.

If your team relies on you for all the answers, you’ve built a fragile system.

What to Do Instead:

• Replace giving answers with asking better questions.
• Create a culture where your team owns decisions (instead of waiting for you to weigh in).
• Stop overvaluing your own thinking—some of the best solutions will come from others.

Reminder: Your job isn’t to have the right answers. It’s to build a team that finds the right answers without you.

3. Unlearning That Pressure = Performance

Most founders are running on dirty fuel—fear, stress, and pressure. They think that if they let go of the stress, they’ll lose their edge.

I hear this all the time:

"If I stop stressing, won’t I get complacent?"

But here’s what I’ve learned coaching some of the world’s top founders:

High performance doesn’t come from pressure. It comes from clarity, presence, and focus.

What to Do Instead:

• Stop treating stress as a sign of productivity. It’s not.
• Shift from reactive problem-solving to proactive leadership.
• Redefine what “high standards” mean—holding your team accountable doesn’t mean overworking or operating from scarcity.

Reminder: Calm, focused leadership isn’t weak—it’s a competitive advantage.

What Got You Here Won’t Get You There

Every founder I’ve worked with who successfully scaled didn’t just learn new skills—they unlearned the behaviors that were keeping them stuck.

The founders who struggle? They cling to old patterns, believing that what worked at 10 people will still work at 100.

If you’re feeling stuck, overwhelmed, or like you’re constantly in firefighting mode, ask yourself:

"What do I need to unlearn?"

Because until you let go of what’s no longer serving you, you’ll keep hitting the same walls.

But here’s the thing—this is just the beginning.

Unlearning isn’t just about scaling your startup. It’s about scaling yourself.

If you keep going down this path—if you unlearn not just the habits and leadership patterns keeping you stuck, but the deeper assumptions about who you are and how reality works—you’ll start uncovering something far more profound.

At the deepest level, unlearning leads to The Truth—the realization that the self you’ve been protecting, proving, and pushing isn’t actually who or what you are.

You’ll realize that it takes mental effort to create an image of who you are (a process that’s been called “self-ing”), and that you’ve been spending most of your life trying to aggrandize and protect that image of self you made up. You’ll awaken to who you are without that mental construct of self.

This is what people call enlightenment.

And while that might feel far from hiring decisions and board meetings, I can tell you from experience—the more you unlearn, the more you operate as your essential self (your true nature), the more effortless your leadership and life becomes.

If you want me to write more on this, let me know.

And if this resonated, reply and tell me—what’s one thing you’re working on unlearning right now?

With love,

- Dave Kashen

P.S. We only have 6 spots left for the first round of founding members for the Inner Game group coaching program and community. Only the founding members will get exclusive lifetime access to everything. I’ve never offered something like this—so now is your opportunity. Connect with an amazing group of ambitious, heart-centered founders and learn to scale your startup from the inside out here.