When do founders get to feel safe?

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This morning I was sitting with a CEO who runs a very large company. From the outside, many people would assume he has made it.

What many people don't understand about venture-backed startups is that there is rarely a feeling of permanence. There is almost always a fear that the company could run out of money, that growth could stall, that access to capital could disappear, or that years of work could ultimately amount to far less than anyone hoped.

I am reminded of this nearly every day in conversations with founders.

What we explored this morning, and what has stayed with me since, is that building a venture-backed company is not about finding your way to permanent peace. It is about earning your way to the next stage.

Each year is a puzzle.

Each round of capital is a puzzle.

Each stage of growth is a puzzle.

You work your way through one challenge only to discover a new set of opportunities, constraints, and complexities waiting on the other side.

The trap many founders fall into is believing that when the next level feels harder, something must be wrong. That perhaps we are not capable enough. Not experienced enough. Not prepared enough.

But the very fact that we have arrived at that level suggests otherwise.

We have already moved through enough uncertainty, enough difficult decisions, enough setbacks, enough growth to earn our way here.

That does not mean it will be easy.

There will still be days when we question ourselves. Days when we question our teams. Days when quitting sounds surprisingly attractive.

But difficulty is not evidence that we are in the wrong place. Often it is evidence that we are exactly where growth happens.

If you are anything like me, the biggest obstacle is often not the market, the competition, or even the challenge itself.

It is your own mind.

For me, it was often the self-criticism. The belief that if this phase felt this hard, I must be doing something wrong. That perhaps everyone else had figured something out that I hadn't.

One of the privileges of sitting in the coaching seat is getting to see behind the curtain.

The founders everyone admires feel this way.

The CEOs on magazine covers feel this way.

The leaders running companies much larger than the one you are building feel this way.

I remember sitting at a CEO dinner years ago with founders leading companies far larger than my own. After a glass of wine or two, I finally worked up the courage to ask the question I had secretly been carrying for years.

"When does it happen?"

"When do you finally get to relax a little?"

"When do you stop worrying about survival?"

The two founders sitting next to me looked at each other and burst out laughing.

Then they kindly explained that the feeling never arrives.

The challenges change shape.

The stakes get larger.

The puzzles become more complex.

But what struck me was that neither of them seemed particularly distressed by this reality. In fact, they seemed more at peace than many founders I knew running much smaller companies.

Over time I came to understand why.

They had stopped expecting the company to provide something it could never provide.

The company could create wealth. It could create impact. It could create opportunities. It could create meaning. But it could not create lasting peace.

That had to come from somewhere else.

Time and again, what I witness in the leaders I most admire is a willingness to turn inward. To do the deeper work of finding steadiness that is independent of the company, the valuation, the revenue, or the next milestone.

They learn to find their footing somewhere deeper.

The company continues to change. The market continues to change. Life continues to change.

But there is a growing sense of solidity underneath it all.

A place that does not rise and fall with every board meeting, product launch, customer loss, or fundraising conversation.

And from that place, they are able to lead with far more creativity, courage, and resilience.

The feeling never arrives.

At least not from the company.

The invitation, perhaps, is to stop looking for it there.

If you are feeling a deep desire to finally find some ease in your own entrepreneurial journey, you are not alone. If I can support you in any way, please reach out.

In the meantime, sending a big hug from my backyard sofa in LA.

Matt

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Looking for some support? If now is the time to consider coaching, reach out here.