Robby has a candid chat with Chad Fowler, the General Partner & CTO at BlueYard Capital. They delve into the nuances of software maintenance, the evolution and challenges of managing software projects, and insights from Chad's tenure as CTO of Wunderlist. They discuss the importance of building software in small, manageable pieces to facilitate easy updates or replacements, the counterintuitive perspective on unit testing's impact on maintainability, and strategies for keeping software up-to-date by redeploying to new platforms.

Additionally, Chad shares his thoughts on the current industry layoff trends, emphasizing the value of adaptability and resilience. The conversation also touches on the relevance of mentoring in the tech industry and the potential implications of AI and large language models on software engineering careers. Chad's philosophy on software development, emphasizing pragmatism, adaptability, and the continuous reevaluation of problems to make them smaller and more manageable, permeates the discussion.

• The E-myth Revisited by Michael E. Gerber
• Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig

• Wunderlist
• The Passionate Programmer by Chad Fowler
• Chad on X/Twitter
• Chad on LinkedIn
• The Privacy Podcast
• BlueYard Capital

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