The Reboot Podcast #140 - From Heartbreak, Through Resilience, To Equanimity - with Chad Dickerson & Jerry Colonna
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Jan 25, 2021 Chad Dickerson, former CEO of Etsy and executive coach, shares his transformative journey from CTO to CEO, tackling anxiety and leadership challenges. He discusses the emotional turmoil of his departure from Etsy, emphasizing the importance of integrity and compassion in leadership. The conversation touches on resilience shaped by heartbreak and the need for personal authenticity amidst societal pressures. With insights on mentorship and personal growth, Chad illustrates how aligning one's inner self with their career can foster genuine happiness.
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Clearing the Detritus
- Chad Dickerson's first day as CTO of Etsy was met with a cold reception, his desk covered in remnants of a party.
- He cleared the mess and focused on building a strong engineering team, despite initial hostility.
Code as Craft
- Etsy's early engineering team had talent, but lacked connection to the company's mission of craft.
- Dickerson used "Code as Craft" to bridge this gap, aligning engineering with Etsy's values.
Hackathon Attitude
- At Yahoo, Dickerson implemented large-scale hackathons to foster innovation and collaboration.
- These events unleashed creativity and helped engineers form informal networks, boosting product development.