Are You Actually Cut Out to Be a Founder?

"I don't think I'm cut out to be a founder," a client told me, eyes looking down.

I could feel the weight in his voice – that combination of exhaustion and quiet shame.

As he spoke, I noticed the familiar heaviness and knot in my own stomach, because I've had that exact thought myself countless times when I was building my startups.

Too difficult. Too stressful. Too competitive. Maybe I should just throw in the towel.

It's a thought nearly every founder I've coached has had – and one I've whispered to myself at 2 AM staring at my ceiling.

The crazy part?

Even the most successful founders we admire wrestle with that same thought.

Think about it: was anyone actually born "cut out" for this?

Was Mark Zuckerberg, at 23, automatically equipped to run a global company? No way. And yet, our minds project this myth that everyone else knows what they're doing, while we're the only ones stumbling in the dark.

The truth is: doubt doesn't mean you're not cut out. Doubt means you're in the arena, stretching beyond what you know – which is the very thing that shapes great founders.

Because the question isn't whether you're cut out for this. The question is whether you're willing to welcome the discomfort to grow into the leader your company needs.

The Real Reason You Think You're Not Cut Out For This

Here's what I've discovered after years of coaching the world’s most successful founders: when founders avoid feeling helpless, they get trapped in needing to be right and having all the answers.

This blocks their curiosity and openness to learning – the very qualities they need to grow into the leaders their companies require. Paradoxically, avoiding helplessness keeps them helpless.

Think about it. The voice that says "I'm not cut out for this" is really your mind trying to avoid feeling incompetent or out of your depth. So what do you do? You hustle harder to prove you know what you're doing. You avoid asking for help. You resist admitting when you're uncertain.

But here's the trap: the very behaviors you use to avoid feeling helpless are what keep you from developing the skills and support systems that would actually make you effective.

The Three Core Capacities That Make You "Cut Out" For This

From my experience, being "cut out" for entrepreneurship comes down to three core capacities:

1. Resourcefulness Over Resources: As Tony Robbins says, "Success is never a matter of resources but of resourcefulness." Every founder starts with nothing – no team, no capital, no customers. What separates successful founders isn't what they have; it's how creatively they approach what they lack.

When you tell yourself "I don't have enough time/money/experience," you're operating from scarcity. When you ask "How can I solve this with what's available?" you're being resourceful.

Because you never start with all the resources. You didn't learn how to walk already knowing how to walk. And if you don't already know how to do something, chances are, you do know the first step in finding out how to do it.

2. Willingness to Welcome Helplessness: Here's the paradox I see repeatedly: when founders start to welcome the feeling of helplessness – because it's actually there – they begin to feel more empowered versus trying to push it away.

Most founders resist acknowledging what they can't control. But there's beauty in powerlessness. It's like floating down a stream instead of trying to paddle upriver. When you stop trying to control things outside your control, you free up enormous energy for what you can actually influence.

3. Capacity for Discomfort: Self-doubt, fear, and impostor feelings aren't bugs in the system – they're features of your nervous system attempting to protect you. But they're signs you're growing, stretching into new territory.

The founders who thrive aren't the ones who never feel these emotions. They're the ones who can feel fear without letting it dictate their choices. They can sit with uncertainty without needing to immediately fix it. And they can recognize that just because their inner voice says something, doesn't mean it's true.

When You Stop Fighting the Doubt

Six months after that conversation with my client, he closed his Series A. But the transformation didn't happen because he suddenly became a "natural born" founder.

It happened when he stopped fighting his sense of not knowing and started getting curious about what he could learn.

Instead of needing to have all the answers, he began asking better questions. Instead of avoiding the feeling of being out of his depth, he welcomed it as a sign he was growing. He learned to distinguish between the voice in his head and the truth of his capabilities.

Most importantly, he discovered that admitting "I don't know" didn't make him look weak – it made him more resourceful. When he stopped pretending to have everything figured out, his team stepped up. When he asked for help instead of struggling alone, solutions appeared.

The doubt didn't disappear. But it stopped running his life.

I've watched this pattern play out hundreds of times. The founders who ultimately succeed aren't the ones who never question themselves. They're the ones who feel the doubt, welcome it as information, and keep building anyway.

Because here's what being "cut out" for entrepreneurship actually means: you're willing to stay present with whatever arises – the excitement and the terror, the breakthroughs and the setbacks – without needing any of it to be different than it is.

You don't need to be born ready. You just need to be willing to grow into readiness. And that willingness? You already have it. Otherwise, you wouldn't be here.

With love,

- Dave Kashen

P.S. The next time that voice whispers "I'm not cut out for this," try this: Welcome the feeling completely. Let yourself feel the powerlessness, the fear, the uncertainty. Notice what happens when you stop fighting it. Often, you'll find that the very feeling you were avoiding contains exactly the clarity you needed.