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We are exploring how to make artificial intelligence experiences more encouraging and empathetic, aiming for more genuine interactions. The conversation focuses on designing an ai chatbot that fosters empathy in ai, which is crucial for building a deeper ai and human connection. This approach helps in getting more authentic information from both sides, shaping the future of AI interactions. In this episode of AI Inside San Francisco, Kevin Hsieh (CEO & Founder of MirWork) shares how he went from selling 300 custom gaming PCs as a teen, to building medical devices, to doing 200+ mock interviews to break into Meta, and why he’s now building an empathetic AI interview platform that helps humans connect more, not less. What you’ll learn • Why Kevin believes AI in hiring should be empathetic and human-first • How he used 200+ mock interviews to land a PM role at Meta • Why “compatibility” matters more than “perfect qualifications” • How Millwork’s AI interviewer actually works for recruiters and candidates • The biggest myth about AI hiring (and why rejection isn’t always bad) 🔗 Links Roan on LinkedIn: / -roan Full recap blog and resources: https://roanweigert.com/2026/02/ai-in... ⏱️ Chapters 00:00 – How empathetic AI interviews actually feel (ChatGPT-style, but human-centered) 01:21 – Welcome to AI Inside San Francisco + who is Kevin Hsieh 02:30 – One-way ticket from Taiwan: feeling lost and finding home in tech 03:52 – The math teacher and cranberry farm that changed everything 05:25 – Growing up with six computers at home and becoming “accidentally” technical 05:59 – Side hustle: building and selling 300 custom gaming PCs 08:05 – Learning early that real sales = empathy and creating value 09:13 – Wanting to be a doctor and discovering biomedical engineering 10:16 – Building ultrasound machines and medical tools for stroke patients 11:55 – Realizing product management is the bridge between tech and people 13:40 – From hospitals to Foxconn: seeing how products are built end to end 15:56 – The startup decade: smart home, autism screening, and FDA-approved AI tools 17:58 – Deciding to aim for big tech and why Meta came calling 19:22 – 200+ mock interviews and 400–500 hours of prep for Meta interviews 21:18 – Helping almost 200 people get into big tech with free PM coaching 24:52 – Why job search is so painful: noise, mismatch, and compatibility 25:16 – Qualification vs compatibility: hiring is more like dating than people admit 27:21 – Inside Millwork: how the AI interview works for recruiters and candidates 29:28 – Candidate experience: going beyond the resume and being truly heard 31:18 – Setting tone, depth, and empathy in AI-driven interviews 33:13 – Why culture, style, and flexibility matter in AI interview design 34:32 – The analytics layer: vibe checks, word choice, and structured evaluation 36:44 – Bias, fairness, and why human overrides still matter 38:41 – ATS vs AI-driven workflows: what changes and what stays 40:46 – Rapid fire: books, frameworks, and product sense questions (Uber for kids, YouTube on Mars) 43:54 – The biggest myth about AI hiring and why rejection can be a gift 46:24 – Final reflections + invitation to connect with Kevin #AIHiring #ProductManagement #JobSearch #BigTech #AIInterview #CareerAdvice #AIInsideSanFrancisco #millwork