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6x founder and Shopify Principal Engineer on AI, Rails, and pairing with Obie Fernandez

Jun 19, 2025
Obie Fernandez, Principal Engineer at Shopify and a six-time founder, shares his journey from Java to Ruby. He discusses how he revolutionized Rails’ adoption at ThoughtWorks and the significance of AI in enhancing developer experiences at Shopify. Obie highlights the critical role of pair programming in fostering mentorship, while also pondering the future of software development amidst AI advancements. The conversation sheds light on balancing speed with code quality, making it a fascinating listen for tech enthusiasts.
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ANECDOTE

Obie's Shift to Ruby on Rails

  • Obie initially hated Ruby due to poor tooling and unstable process control on Windows.
  • Later, he embraced Rails for its simplicity and full-stack conventions, unlike Java.
ANECDOTE

Leading ThoughtWorks' Ruby Practice

  • Obie led ThoughtWorks' Ruby practice amid internal resistance and lack of recognition.
  • Feeling unappreciated, he quit to start Hashrocket influenced by his book success.
ANECDOTE

Shopify Developer Experience AI Work

  • At Shopify, Obie works on developer experience using AI, focusing on structured AI workflows.
  • He contrasts deterministic workflows with more unpredictable agent-based AI models.
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