

20VC: What are the World's Tech Leaders Running From? Fear? Insecurity? Poverty? What Drives the Best with Orlando Bravo, Bill Ackman, Dara Khosrowshahi, Parker Conrad, Tobi Luttke, Brian Armstrong and more..
12 snips Jun 9, 2023
Tech leaders share their personal journeys, revealing what they strive to escape—fear, insecurity, and stagnation. They discuss the psychological motivations behind their career choices and the transition from fear to joy. The impact of family history on ambition is explored, alongside insights on innovation within tech giants. Personal experiences highlight overcoming self-doubt while fostering team efficiency in startups. The conversation emphasizes the importance of continuous learning and adapting in an ever-evolving landscape.
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Orlando Bravo's Fear of Stagnation
- Orlando Bravo fears stagnation and isolation, stemming from growing up on an island.
- He felt his career was failing in 1999, close to being fired, but persevered like in a tennis match.
Brian Armstrong's Shifting Motivations
- Brian Armstrong initially felt driven by fear of not achieving something important, tied to his shyness.
- He later found motivation in building technology, learning, and impacting the world at scale.
Parker Conrad's Motivation After Zenefits
- After leaving Zenefits, Parker Conrad faced negative press and restrictions.
- He channeled this into building Rippling, aiming for a $100 billion outcome to tell his story.