The Art of Growing Wise | Jerry Colonna

Career Start

Jerry Colonna's journey into the publishing world was marked by an unexpected turn of events. Initially an English major with dreams of writing poetry, he found himself working at a technology magazine company due to a scholarship and internship opportunity. This path led him to rise from a summer job on the copy desk to becoming the editor of a major publication. His early love for poetry, influenced by childhood readings, played a significant role in shaping his relationship with words and storytelling.

My relationship to words and poetry goes back to the earliest memories that I have, and I think that I always took comfort in words. Words matter.

--- Jerry Colonna

This foundation in language and expression would later influence his approach to leadership and communication in his career 1 2.

   

Venture Shift

Jerry's transition from publishing to venture capital marked a significant shift in his career. As editor of Information Week, he focused on the human side of technology, which eventually led him to explore the intersection of technology and human interaction in venture capital. Partnering with Fred Wilson, they founded Flatiron Partners during a time of rapid growth in the tech industry. Their partnership was built on shared values, as demonstrated by Fred's prioritization of family over business meetings.

He canceled the lunch at the last minute because he wanted to attend his daughter's kindergarten graduation. And that meant a lot to me.

--- Jerry Colonna

This decision to enter venture capital was driven by Jerry's curiosity about how technology could enhance human experiences 3 4.

   

Dot-Com Challenges

The dot-com bubble burst presented significant challenges for Jerry Colonna and his venture capital endeavors. As the market crashed, the once-thriving investments began to falter, leading to a period of introspection and personal struggle for him. This period coincided with Jerry facing midlife questions and a resurgence of depression, compounded by the events of September 11, 2001.

The music stopped. There weren't enough chairs for everybody to sit down, and a bunch of people sat down on the floor.

--- Jerry Colonna

These challenges forced Jerry to confront his vulnerabilities and reevaluate his life's direction, ultimately leading to a profound personal transformation 5.