Self

Gambling My Startup on a Friendship

How a trusted mentor can easily become a villain.

Ash Jurberg
Corporate Underbelly
7 min readFeb 6, 2024

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Closeup portrait of a man crying
Adobe Libray Image

I tried to hold back the tears as I begged for empathy — an emotion not usually associated with customer service agents working for giant phone companies. The stares of people in my co-working office added to my anxiety. Trying to avoid embarrassment, I scurried around the office, desperate to find an empty room where my quivering voice wouldn't attract attention.

If this phone call didn't end with a favorable outcome, my entrepreneurial journey would be over before it even got going. My head pounded in sync with my heart, and I felt a wave of nausea coming on, forcing me to dash to the restroom, phone in hand.

Entering the first vacant stall, I took a few deep breaths and asked the agent if I could explain my story. I hate playing the victim, but I needed to tell him my story — one of betrayal by a trusted business partner and mentor played on a naive person swept up in the excitement of becoming an entrepreneur.

The naivety led to me making a big mistake — in the words of Julia Roberts from Pretty Woman, it was a "Big mistake. Big. Huge."

A perfect match

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