It was 2005 and I was sharing office space with Fred Wilson when I met a young man who changed my life.
Fred and I had been friends since 1996 when we’d started Flatiron Partners. In 2001, we parted ways as partners but remained friends. I joined JP Morgan in 2002 and, within months, was miserable. The existential questions that had been haunting me for years were so loud, so relentless that I had no choice but to pay attention.
When I told my colleagues I was leaving, I said I wanted a business card with no company name, no title. I wanted to understand who I was stripped of any persona.
And so for the next few years, I sat on boards of directors, consulted here and there but mostly, I read, and sat, and learned to be still. I learned to listen.
Derek Walcott’s poem Love After Love comes to mind; I learned to love again the stranger who was my self who had loved me all my life, whom I ignored for another, who knows me by heart.
Then one day a young man came to see me. He wanted to leave his law practice and join a startup. Someone suggested that seeing the former VC would be a good first step. After asking him why he’d become a lawyer in the first place, especially considering he obviously hated his job, he began sobbing. I realized then that, through the act of listening, I had found my own way. Those years of sitting still began to pay off; I had to coach. And I’ve been coaching ever since.