This Week in Startups Jerry Colonna on 'Reunion': sustaining founder drive, enlightened leadership, and more! | E1864
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Dec 13, 2023 
Jerry Colonna, founder coach and author of "Reboot" and "Reunion," discusses his transformative journey from venture capitalist to guiding entrepreneurs through their challenges. He shares insights on the emotional complexities of leadership, the struggle for true fulfillment beyond wealth, and the significance of mental health in startups. Jerry highlights the critical transition from founder to CEO and critiques the glamorization of entrepreneurship, advocating for a culture that embraces vulnerability and meaningful connections.
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Early Internet Friendship
- Jerry Colonna and Jason Calacanis' friendship began in the early internet days of the 1990s.
- Calacanis sought advice from Colonna, who was working at Lycos and later became an investor in it.
From VC to Coach
- Jerry Colonna transitioned from a venture capitalist at Flatiron Partners to a founder coach.
- He now helps founders without directly investing in their companies.
Cyber Surfer Beginnings
- Jason Calacanis started his career by creating and distributing the magazine "Cyber Surfer".
- He later worked for Colonna and Fred Wilson, reviewing business plans.
