Regrets, mistakes, disasters

Gil Silberman
1 min readOct 17, 2022

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I’ve been thinking lately about these

Regrets

You could say I’ve accomplished a lot in business and life, I tell myself.

My cute little dog sniffs a change in breeze, stares over the penthouse railing at the ocean, waves, rainbow, mountains and sunset.

But I could have been so much… more.

Mistakes

I wasted time, didn’t take opportunities, loved the wrong people, let others down.

Procrastinated, got disorganized, lost motivation, let myself gain weight. Just didn’t focus.

Disasters

Not the silly ones like crashing a car, a plane, the bulldozer that tumbled down the hill, or burning down my boss’s office building.

I’ll tell those stories soon. Those were good disasters and people find them amusing. They involved things not loved ones and all had good outcomes.

It’s the private personal disasters that hurt.

Learning

Success, I think, is less about accomplishing things and more about overcoming failure.

My not-so-humble brag, I helped start five billion-dollar companies and at one point was 1/10th of a billionaire myself. I can play piano, I’ve run miles without missing a day for five years, and I once met Robin Williams.

But it’s about accumulating money, experiences, and achievements. More about making with what you have. Who you have.

I have a little dog.

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Gil Silberman
Gil Silberman

Written by Gil Silberman

Lawyer, founder, investor, software engineer. I helped start 300+ companies including 5 unicorns. Yours next?

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