Supra Insider

• #66: How MCP enables AI to know you better | Mike Bal (Head of Product and AI @ David’s Bridal)

  Listen now: Spotify, Apple and YouTubeWhat if you had a personalized AI toolkit—not just a chatbot—that actually remembered your projects, your workflows, and even your family’s preferences?In this episode, Marc and Ben sit down with Mike Bal, a product leader experimenting at the frontier of AI tooling. Mike shares how he built a local memory system for Claude using Model Context Protocols (MCPs), enabling persistent knowledge graphs that connect everything from his product designs to his family’s vacation plans. They walk through how it works—step-by-step—including a live demo of Fleur (essentially a mini app marketplace to make it easy for non technical people to add MCPs to Claude), how Mike structures entities and relationships, and why this setup beats traditional RAG approaches for real-world usage.If you’ve ever wanted your AI to truly understand you and the work you do—or you're curious how a product leader uses AI to streamline everything from design reviews to family logistics—this episode is packed with real-world inspiration and actionable examples.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇In this episode, we covered the following topics:* (02:08) Why traditional RAG setups break down—and how knowledge graphs offer a more reliable foundation* (6:55) What MCPs actually are and why they’re more like a toolkit than an API reference* (11:45) Installing Fleur: the dead-simple way Mike connected Claude to a local memory system using MCPs* (15:30) Why traditional APIs fall short—and how MCPs give AI tools structured, usable context* (28:52) Live demo: How Claude pulls memory from a local knowledge graph—personal details, podcast history, and more* (35:28) A real-world example of how Mike planned a family trip using AI memory, including dietary needs and activity preferences* (44:10) How Claude’s memory MCP compares to project instructions and system prompts* (52:32) How Mike uses memory graphs for PRD reviews, user pain points, and feature validation* And more!Links:* Mike Bal: https://www.linkedin.com/in/mikebal/* Mike’s Newsletter: https://www.leadingproduct.link/* Mike’s YouTube: https://www.youtube.com/@thatmikebal* David’s Bridal Wedding Planner Demo: https://pearl.davidsbridal.com/* David’s Bridal’s Revival with AI: https://venturebeat.com/ai/retail-resurrection-davids-bridal-bets-its-future-on-ai-after-double-bankruptcy/* Fleur MCP App Store: https://www.fleurmcp.com/* Willow Voice (Get the first month free by using this link!): https://willowvoice.com/?ref=BEREZ64* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some early favorites:To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until October, his popular AI Copilot for interview practice is available here, where you can also see a live demo (ChatGPT support coming soon).* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

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• #65: How to build an AI career coach in 90 minutes | Kavita Anand (VP, Product & Design @ NewtonX)

  What if you could access a personalized career coach anytime—one who remembers your goals, understands your tendencies, and gives you thoughtful, actionable guidance?In this episode of Supra Insider, Marc and Ben sit down with Kavita Anand, a product leader at NewtonX, to explore how she built her own AI-based career coach using tools like Claude and ChatGPT—and then taught 30+ women at her company how to do the same. She breaks down the exact system she used: crafting a system prompt, running a kickoff conversation, and curating relevant context to create a truly helpful AI co-pilot.They also explore how to avoid common pitfalls like getting generic advice or triggering confirmation bias, and why voice-based AI interfaces are changing how people reflect and communicate with AI. Whether you’re a product leader, an early-career PM, or just AI-curious, this episode will show you how to start designing an AI coach that works the way you want—even if it takes a little tinkering.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇In this episode, we covered the following topics:* (02:38) Kavita shares how she adapted ideas from a Supra-led workshop to run a 90-minute session with 30+ women at NewtonX.* (06:01) The three components of an effective Claude-based co-pilot: system prompt, project knowledge, and chat threads.* (08:13) How participants personalized their AI coaches to reflect their needs, coaching preferences, and role-specific challenges.* (10:10) Kavita’s personal use case: how AI coaching gives her access and emotional freedom that human coaches can’t.* (14:29) Why the biggest limitation of AI coaching is often the user, not the model—and how to give better context.* (26:40) Prompt engineering tactics that dramatically improve AI outputs—like role prompting, decomposition, and self-critique.* (30:00) Building a Claude project from scratch: writing a system prompt and refining it with live feedback.* (45:38) Why adding too much unstructured project knowledge can harm output—and how to curate and index it effectively.* (49:38) Live demo: AI coach reacts to a real-world workplace challenge with thoughtful, adaptive follow-up questions.* (54:23) Designing workshops to ensure participants get to their “aha” moment and leave with a working AI copilot.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Kavita Anand: https://www.linkedin.com/in/kavitaanand05/* Willow Voice (Get the first month free by using this link!): https://willowvoice.com/?ref=BEREZ64* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting July 15th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

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• #64: How top companies evaluate PM candidates in 2025 | Nickey Skarstad (Duolingo), Stephanie J. Neill (Stripe), and Chantal Cox (LTK)

  If you’re navigating today’s brutally competitive PM job market and wondering what “good” looks like, this episode will become your playbook. In this episode, Ben moderates a candid panel with three veteran product hiring managers:Nickey Skarstad – Director of Product, Duolingo (now leading Duolingo Math)Stephanie J. Neill – Head of Product, Stripe TaxChantal Cox – Director of Product, LTK (LiketoKnow.it creator platform)Together, they reverse-engineer every stage of their 2025 hiring funnels—from 30-second resume scans to offer debriefs—and spell out the signals that turn an applicant into a hire. You’ll hear why product-sense interviews have moved to earlier in the process, how AI prototypes are becoming table-stakes, and the red flags (LLM-generated answers, recycled stories etc.) that get instant no-hires. Whether you’re an aspiring PM or a manager revamping your own process, you’ll leave with concrete, immediately applicable tactics for landing—or giving—an offer.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting July 15th.* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.In this episode, we covered the following topics:* (01:40) Guest intros: Nickey (Duolingo), Stephanie (Stripe), Chantal (LTK).* (08:00) Chantal details LTK’s funnel—recruiter screen, hiring-manager call, AI feature exercise, leadership loop.* (11:30) Stephanie explains Stripe’s flow and why Product Sense now precedes the full loop.* (13:20) Nickey walks through Duolingo’s four rounds and the new interactive prototype requirement.* (17:50) What wins a résumé review: tight one-page metrics, LinkedIn consistency, warm referrals.* (24:40) Hiring-manager screens: confirming skill fit, probing AI curiosity, expecting candidates to have used the product.* (31:00) Offer debriefs—looking for “spikes” in key areas, guarding against bias, zero tolerance for failed rounds at Duolingo.* (43:40) How candidates should and should not use Gen-AI; interview-prep bots, friction logs, lightweight prototypes.* (50:20) Early-career advice: move internally, start in customer-facing roles, ship side-project AI apps, network before you need it.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Nickey Skarstad: https://www.linkedin.com/in/nickeyskarstad/* Stephanie J. Neill: https://www.linkedin.com/in/stephanieneill/* Chantal Cox: https://www.linkedin.com/in/chantalcoxsf/* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

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• #63: How PMs can bring predictability to AI products | Aman Khan (Head of Product @ Arize AI, ex-Spotify, ex-Apple)

  If you’ve ever launched an AI feature and later realized it wasn’t quite ready—or struggled to define what “quality” even looks like in an AI product—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Aman Khan, Head of Product of Arize AI and a leading voice in AI product evaluation. Aman has helped dozens of teams—from scrappy startups to massive consumer platforms—build systematic approaches for evaluating LLM-powered features. Together, they explore the dangers of “vibe coding” your way to production, how to define and operationalize evals across different layers of your product, and why even “good” outputs can still lead to bad outcomes without proper measurement.Whether you’re a PM under pressure to ship AI features fast, or a product leader figuring out how to instill quality and reliability into your development process, this conversation is packed with frameworks, analogies (like self-driving cars), and hard-won lessons you can use to build smarter and ship more confidently.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇To support the podcast, please check out the links below:* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN. Aman’s course is part of the partnership 🚀* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting July 15th.In this episode, we covered the following topics:* (00:00) The danger of launching AI features without proper evaluation—and why trust is hard to rebuild* (04:12) “Vibe coding” explained: when teams ship based on gut feel instead of structured validation* (09:07) Real-world example: a travel chatbot gets great engagement—until users start jailbreaking it* (15:36) Defining “good enough”: how to set AI quality metrics across tone, latency, hallucinations, and risk* (19:58) What PMs can learn from self-driving car evals—and how to build iterative test sets for reliability* (23:04) How LLM-as-a-judge works: using one model to grade another, and when to rely on human labels* (34:14) Spotting dangerous “false positives”: when outputs seem right but come from flawed reasoning* (42:22) What to do when your evals say “good” but the business metrics drop—and who’s responsible* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Aman Khan Website: http://amank.ai* Aman Khan: https://www.linkedin.com/in/amanberkeley/* Aman Khan X: https://x.com/_amankhan* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

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• #62: Why the future belongs to spiky PMs who use AI to magnify their strengths | Hilary Gridley (Head of Core Product @ WHOOP)

  What actually sets you apart in a world where AI can do more and more of your job? In this episode, Marc and Ben are joined by Hilary Gridley—Head of Core Product at WHOOP and instructor of the Maven course How to Be a Supermanager with AI—to unpack how great product leaders can use AI to magnify their strengths instead of dulling them.Hilary breaks down her approach to time allocation, sharing how she dissects messy, ambiguous work into its component parts and uses AI as a thinking partner—not a crutch. They explore how to identify high-leverage tasks, when investing time is essential for clarity, and why doing something the hard way is sometimes the point. The conversation also touches on how PMs can design their roles around their superpowers, what good taste really means in product, and how managers can help their team grow by doubling down on what makes them exceptional.If you're trying to become more intentional with how you spend your time, use AI more thoughtfully, or lead a team of PMs in this new era—this episode is for you.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.In this episode, we covered the following topics:* (00:00) Hilary’s approach to identifying and doubling down on her spikes as a product leader—and how AI helps magnify them.* (04:00) How she breaks down ambiguous product work into sub-skills to better allocate time and energy.* (11:30) The tradeoff between leverage and clarity—and why doing something the hard way can be the right call.* (17:00) Frameworks Hilary uses to decide when to delegate, when to coach, and when to go deep herself.* (22:00) How she uses AI tools like Claude as thinking partners to sharpen ideas and move faster.* (27:00) Why “taste” in product is hard to teach—but essential to develop as a PM.* (32:30) The biggest mistake new managers make when trying to “round out” their team—and how to coach for spikes instead.* (38:00) How to build a team with differentiated strengths that complement each other instead of copying one another.* (44:00) What Hilary learned from teaching 100+ managers in her Maven course on using AI to lead more effectively.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Hilary Gridley: https://www.linkedin.com/in/hilarygridley/* Hilary’s Substack: https://hils.substack.com/* How to Become a Supermanager with AI: https://maven.com/hilary-gridley/ai-powered-people-management* Hilary’s recent episode on “How I AI” with Claire Vo* Superpowers by SYPartners: https://apps.apple.com/us/app/superpowers-by-sypartners/id1309752471* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

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