The Chief of Staff Podcast

Eating Glass: How A CoS Helps Build A Startup

May 8, 2025
In this discussion, Andrew Rea, the Co-founder and CEO of Taxwire, and David Moon, the Chief of Staff, reveal the gritty reality of startup life. Andrew emphasizes the need for constant communication and a deep understanding of a CEO's priorities. David shares insights on cold starting processes and systemizing strategies vital for market entry. They highlight the importance of trust and adaptability in early-stage startups, illustrating how tackling varied tasks shapes a successful venture. Get ready to learn what it really means to 'eat glass' in the startup world!
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ANECDOTE

David's Organic CoS Start

  • David Moon initiated the Chief of Staff role by prototyping a product idea and reaching out to CEO Andrew Rea directly.
  • Their friendship and mutual trust led to David joining initially as a contractor, evolving organically into the CoS role.
INSIGHT

Early Startup Versatility

  • Early-stage startups require everyone to be individual contributors, handling multiple roles.
  • Andrew was juggling all non-engineering tasks, showing the need for versatile support.
ADVICE

Be an Effective Individual Contributor

  • Assess your ability to contribute as an individual contributor before joining an early-stage startup.
  • Ensure you bring tangible value and won’t be a burden in a lean team environment.
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