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August 26, 2025 42 mins

First, there was vibe coding. Now, get ready for "vibe entrepreneurship." 

Andrew McNamara, Director of Applied Machine Learning at Shopify, joins us to explain how his team is making this new era of business a reality. He shares the vision behind Shopify Sidekick, an AI co-founder designed to empower merchants by acting as their on-demand e-commerce expert. Drawing on his 16-year journey building AI assistants, Andrew reveals what it truly takes to create an AI tool that customers can trust with their livelihood.

He shares a critical insight from his applied research background: the hardest and most important part of building production-ready AI isn't the model, but the evaluation ("eval") system. Andrew breaks down Shopify's innovative approach of using an LLM-as-a-judge to measure how well they're fulfilling user goals, not just executing features. This conversation is a definitive guide to creating high-trust AI systems and offers a powerful glimpse into the future of commerce.

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