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!
36:25
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Quick takeaways
- The relationship between David Moon and CEO Andrew Ray emphasizes how trust and familiarity can create unique opportunities in startups.
- David’s role as Chief of Staff highlights the necessity of adaptability and proactive problem-solving across diverse responsibilities in early-stage companies.
Deep dives
David Moon's Journey to Chief of Staff
David Moon became the Chief of Staff at TaxWire after cultivating a long-standing relationship with CEO Andrew Ray. Their connection, which spanned five years, began when they met through mutual friends, allowing them to discuss innovative ideas related to tax compliance. David initially approached Andrew with a product prototype aimed at addressing issues within the sales tax industry, which sparked interest and led to further discussions about collaboration. Ultimately, this organic relationship evolved into a role that neither party had formally defined initially, showcasing how trust and familiarity can lead to creating unique job opportunities.
