Why putting my phone on silent was a $100 million mistake

Gil Silberman
1 min readOct 29, 2022

Burning down my boss’s office was the third most costly mistake I made in business.

Second worst was not answering the phone when one of my CEO clients called, shortly after he merged his company with his closest competitor. I can’t tell you who it is, but an earlier company he helped start is now valued at more than $1 trillion.

Seriously, a trillion dollars.

As most corporate transactions go, there were some bumpy spots, and frustration dealing with a new Board of Directors that was no longer in his pocket. After a particularly contentious board meeting he called me wondering what to do. The call went to voice mail.

I quit… Oops, no, I un-quit!

Next message I got, he had quit and asked what’s next.

The Board, sensing the opportunity, quickly drafted him a letter accepting his resignation and informing him that per the retention incentive terms of the merger agreement he would be forfeiting most of hist stock.

Had we spoken I would have told him let them fire you, or threaten to, but whatever you do, don’t quit. But we didn’t, and he did, and that was that.

Total loss was about $100 million. Plus another $100,000 in legal fees litigating in vain that the resignation was ineffective or there was a flaw in the stock repurchase. Grasping at straws really.

Moral of the story, answer the damn phone.

Read this post and more on my Typeshare Social Blog

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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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