What does it mean to live a satisfying life?

Kunal Gupta

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I experiment with life and share what I find.

ENTREPRENEUR ·AUTHOR ·INVESTOR
Kunal Gupta

The short version.

I built a tech company at twenty-one ran it for fifteen years across thirty countries; then, one morning in Toronto, sun hitting my screen, I realized I'd spent a decade building toward a feeling that never arrived.

That silence started everything that followed. I sold what I owned, moved to Lisbon on three days' notice, and began running experiments on the only subject I couldn't outsource: my own life.

Now I live here with my wife, writing every week, building with AI, and still inside the question. I don't have it figured out. The experiments keep going.

Now I live here with my wife, writing every week, building things with AI, and still trying to figure out what a satisfying life actually looks like. I don't have it solved. But the experiments keep going.

What is work for?What does the body know?What does love require?What’s real and what’s inherited?What does technology make possible? What is work for?What does the body know?What does love require?What’s real and what’s inherited?What does technology make possible? What is work for?What does the body know?What does love require?What’s real and what’s inherited?What does technology make possible?

Reflections

Books

Each one started as a question that wouldn't leave me alone.

Builder, seeker, fellow traveler.

I started my first business at thirteen and haven’t stopped building since. I founded a global technology company at twenty-one and ran it for fifteen years. I was named EY Entrepreneur of the Year. I studied AI at Oxford. Somewhere in the middle of all that, I started meditating in boardrooms and questioning everything I’d been taught to want.

That questioning became its own body of work. Four books across four genres. A weekly essay for over a decade. A move to Lisbon on three days’ notice. And now, building software tools for writers and running Portugal’s AI community.

The through-line is one question: what does it mean to live a satisfying life?

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