Why Coaching Unicorn Founders Often Leads to Spirituality

The day Airbnb went public, Brian Chesky's net worth hit $10 billion. He'd built a $100 billion company and described this amazing exultation having gone to the mountaintop.

Then he woke up the next day.

"My life was exactly the same. I'm alone. I wake up. I put on my sweatpants. I go onto my iMac and I have 10 to 12 hours of Zoom meetings."

He'd spent his whole life chasing success because, if he dug deep, he thought it would make people love him. He reached one of the highest pinnacles of professional success and found it completely empty.

That post went viral because it hit home for a lot of people.

This is the arc I've seen many founders go through. They stop being victims of their circumstances, take ownership, build, achieve, hit the milestones, and then the deeper questions emerge. Why do I still feel like something's missing? Who am I, really?

I wasn't particularly "spiritual" myself until 2016, when I had my first profound experience. I felt the boundaries of myself dissolving, fully immersed in this beautiful white light energy that I can only describe as love.

But I've come to realize that building a startup is already a spiritual experience if you allow it to be.

I usually tell clients not to think of me as coaching them to support their startup's success, but instead supporting them to use their startup as a dojo for their personal and spiritual growth.

And in doing so, founders discover that this way of approaching it is actually the most efficient and direct path to what they're looking for.

Here's why...

How Founders Evolve Through Their Startup

There's a framework originally from Michael Beckwith that explains this progression: to me, by me, through me, as me.

To me: Victim consciousness. Life happens to me. The board is frustrating. The market shifted. My co-founder isn't pulling their weight. You're at the effect of circumstances, constantly reacting.

By me: Creator consciousness. You see yourself as the source of your experience (not as blame, but as empowerment). If I created this, I can create something different. This is where most typical coaching lives, and it's transformational.

Through me: The question shifts. Instead of what do I want to create? it becomes what's wanting to happen through me? You start relating to yourself as a vessel for something beyond your individual ego, like you're part of nature, and nature is trying to evolve through you.

As me: The recognition that we are awareness itself, oneness expressing through this particular human form. Not a concept to believe, but something that can be directly experienced.

When Success Stops Working

Most founders come to me stuck in "to me." The shift to "by me" is powerful: they stop being victims of their startups and start consciously creating outcomes.

But there's a natural arc where, at some point, the deeper questions arise. Sometimes through crisis. Sometimes through curiosity. And sometimes, like Chesky, because they've achieved the success they were chasing and hit the ceiling.

They get to the thing their mind said would make them happy. And they don't feel it. There's this asymptotic feeling: I got the money, I got the things I thought I wanted, but I don't feel that different.

Most people fool themselves at that point: okay, maybe it wasn't $3 million, maybe it's $10 million. They keep playing the game. But when you've built a hundred billion dollar company and still feel empty, it gets pretty hard to keep believing the illusion.

That's when the questions shift. Not how do I create more? but where do my desires even come from? Why do I want what I want? And ultimately: Who am I, really?

This is the doorway to "through me" and eventually "as me."

The More Efficient Path to What You Want

Here's what founders discover when they start asking those deeper questions.

Ask any founder what they want: money, scale, an exit. Then ask why five times.

Why do you want the exit? So I have financial freedom.

Why do you want financial freedom? So I'm not stressed about money.

Why does that matter? So I can feel at peace. Why do you want to feel at peace?

It always traces back to a feeling. Peace, joy, freedom, aliveness, love. The external conditions are just strategies to create an internal state.

But $10 billion doesn't create peace. The external strategy didn't work. Because those feelings don't actually come from the conditions; they come from inside us. They always have. And they're available now.

So if the goal is peace and freedom, why take the long way around? Why not go direct?

This is what makes the spiritual path the more efficient path: letting go of attachment, letting go of resistance, bringing curiosity to the question of who am I. You're no longer chasing external conditions hoping they'll create internal states. You go straight to the source.

And something interesting happens when you do.

The gap between how much you can feel a feeling now versus how much you think you'll feel it once you achieve the thing: that gap determines how attached you are to the outcome.

If you believe you can't feel confident until you raise your Series A, you'll be intensely attached to that raise. But if you can access confidence now (genuinely, not as a trick), the attachment loosens.

And here's the paradox: the less attached you are to an outcome, the easier it is to create.

When you're attached, you're grasping. You're not showing up as creatively or confidently or with as much energy. But when you can access peace now, you operate from presence, and presence is the most resourceful state there is.

You can't fake this. Believe me, I've tried. But when it's genuine, you get both: the inner experience you were chasing all along, and the outer results become easier to create.

Winning Twice

So why does coaching unicorn founders often lead to spirituality?

Because that's where the path naturally goes.

Chesky spent his whole life chasing an inner experience (feeling loved, feeling enough) through external success. A hundred billion dollar company couldn't give it to him. External conditions never could.

The founders who discover this stop taking the long way around. They go direct.

And they get to win twice.

They get the inner experience they were actually chasing all along: peace, freedom, aliveness, feeling enough. It was always available.

And because they're operating from those states, the outer results become easier to create. It's easier to lead. Easier to bring out the clean fuel: the healthy motivation, creativity, and collaboration in their teams.

This is the more efficient game that opens up when you treat your startup as a dojo.

With love,

- Dave Kashen

P.S. Want to ask me a question that will be answered in a future newsletter and/or youtube video? You can submit a question here: https://eulvx5p8j26.typeform.com/to/XgWoYLi7​

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