Hugo speaks with Jason Liu, an independent AI consultant with experience at Meta and Stitch Fix. At Stitch Fix, Jason developed impactful AI systems, like a $50 million product similarity search and the widely adopted Flight recommendation framework. Now, he helps startups and enterprises design and deploy production-level AI applications, with a focus on retrieval-augmented generation (RAG) and scalable solutions.

This episode is a bit of an experiment. Instead of our usual technical deep dives, we’re focusing on the world of AI consulting and freelancing. We explore Jason’s consulting playbook, covering how he structures contracts to maximize value, strategies for moving from hourly billing to securing larger deals, and the mindset shift needed to align incentives with clients. We’ll also discuss the challenges of moving from deterministic software to probabilistic AI systems and even do a live role-playing session where Jason coaches me on client engagement and pricing pitfalls.

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#brunchtalk: Do Breakups Reveal Someone's True Character?