Podcast appearances and mentions of lenny rachitsky

This episode contains some screen sharing so it's best watched on YouTubeWhat happens when one product leader decides to stop copy-pasting between chat windows and instead build an operating layer that puts coding agents in the hands of an entire company?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Kyler Ross, Head of Product at Cloaked, to walk through the internal “harness” he started building last Thanksgiving: an agent-friendly system of context files and scripts that lets agents read from and write to the team's real tools. Kyler explains how it gets installed on every company machine, why he treats each new agent session like onboarding an employee, and how a self-improving loop of skills and automated reviews keeps it getting better.They explore his day-to-day setup for running many agents at once, why worktrees and Claude Code hooks exist to make failure nearly impossible, a one-on-one prep skill that pulls context from every corner of the company, and the layered guardrails, including a nightly “librarian” agent, that keep confidential information from leaking.If you're a product or engineering leader trying to make your team more AI-native, someone wiring agents into real workflows, or anyone wrestling with how to run agents safely at scale, 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

What does it take to walk away from a decade in product, and a job most people would envy, to bet on yourself?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Peter Yang, who just left his product lead role at Roblox to go full-time on his newsletter and podcast, Behind the Craft and build his own projects. Peter talks through the trade-offs of solopreneur life, why his calendar is suddenly empty, and how he uses an AI personal advisor with three principles to decide what to say no to.They explore his day-to-day AI builder stack, from running Codex as a daily driver to using Hermes for his recurring scheduled tasks, his working definition of slop and why he guards against it, and what he's actually measuring as success now that nobody is handing him a promotion.If you're a PM weighing whether to leave a stable job to build on your own, a creator trying to scale output without sliding into slop, or anyone wiring AI agents into their daily work, 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

What does it take to bring AI into businesses that run on physical work, human judgment, and processes nobody has ever written down?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Noah Levin, founder of Serious People, to unpack what he calls being a “free-range AI consultant.” Noah explains why most of his work is business consulting from first principles rather than AI consulting, why agents still need humans to deliver real value, and how he groups AI for any company into three buckets: a coworker, an operator, and a product or engineering capability.They explore how AI is collapsing the distance between a conversation and a working prototype, why the new IP is business judgment instead of code, why he believes everything is becoming product management, and the humility it takes to solve problems on a client's terms inside companies that aren't, and shouldn't be, run like tech startups.If you're a product leader figuring out where AI actually creates leverage, an operator weighing whether to go independent, or a builder realizing that distribution now matters more than the thing you build, 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

Did you like the episode? Send me a text and let me know!!How to Scale From 0 to 100 Customers: The Startup Distribution GuideThe Zero-to-One Blueprint: How Startups Find Their First 100 UsersEpisode DescriptionIn this episode of Business Conversations with Pi and PIET 2.0, Scoob, Pi, and PIET tackle the ultimate "Zero-to-One" startup hurdle: Where and how do I find my very first 10 to 100 customers when I have zero brand awareness, no marketing budget, and an imperfect prototype?Pulling from the battle-tested playbooks of Y Combinator, Close CRM, and top digital growth experts, this masterclass breaks down why doing things that "spectacularly fail to scale" is the only reliable way to build a foundation for massive growth. If you are an early-stage founder trying to map out a clear customer acquisition strategy, this blueprint is built for you.⏱️ Episode Timestamps[00:00:00] — Introduction to Episode 2.0Scoob introduces AI co-hosts Pi and PIET 2.0 to tackle real-world entrepreneurial growth and user acquisition bottlenecks.[00:00:50] — The Counterintuitive 100 Fanatics RuleAn analysis of Airbnb co-founder Brian Chesky's core philosophy: Why it is infinitely better to have 100 people who absolutely love your product than a million who just sort of like it.[00:02:40] — The Archetype of the "Innovator"How to filter your Ideal Customer Profile (ICP) based on raw pain intensity. Why early adopters buy half-finished, buggy software to solve an acute workflow disruption.[00:04:15] — Case Studies in Pain-Point ValidationExamining the early go-to-market strategies of Notion (targeting tech-savvy power users) and Brooklinen (targeting young urban professionals priced out of luxury department stores).[00:05:30] — The Trap of Generic Cash FlowWhy casting too wide of a net on Day 1 breaks your product roadmap feedback loop and creates a "Frankenstein monster" product that serves no one well.[00:07:15] — The Apollo 13 Scaling ParadoxSteli Efti's crucial warning against premature scaling. Why building a marketing funnel for 10,000 users before you have 10 is an entrepreneurial trap.[00:08:30] — Brute Force Acquisition TacticsHow Close CRM co-founder Steli Efti secured his first 7 B2B clients with zero lines of code written by manually targeting newly funded seed startups on Crunchbase.[00:10:00] — The 50-Profile LinkedIn Direct Outreach FormulaThe mathematical breakdown of hyper-personalized, founder-to-professional cold messaging. How to systematically manufacture a warm network with a 10–20% response rate.[00:12:15] — Moving From 10 to 100: The Hub-and-Spoke Distribution ModelHow to stop hunting individual footprints in the desert and start borrowing existing digital ecosystems.[00:13:00] — Historical Guerilla Growth HacksHow Netflix embedded inside fringe DVD bulletin boards, Etsy traveled to physical arts and crafts fairs, and Morning Brew manually collected emails via physical clipboards in college lecture halls.[00:14:40] — Navigating Digital Watering Holes SafelyThe rules of community reciprocity: How to launch on platforms like Reddit, Discord, or Hacker News without looking like a spammer.[00:15:45] — Building the Repeatable Growth EngineAn in-depth look at Lenny Rachitsky's journey. Why long-term hockey-stick growth only happens after a linear trend line of relentless, high-quality content consistency.[00:18:30] — Paradigm Shift: Customers as Unsalaried Co-FoundersPi and PIET reframe the entire acquisition process as a collaborative product development exercise.

- TrueFoundry, founded by Nikunj Bajaj, is an AI infrastructure company building an "AI Gateway" that helps enterprises build, ship, and govern agentic AI applications, focusing on observability and governance for AI agents. - The company has raised over $22 million, with pre-seed investment from Sequoia and India Capital, and Series A led by Intel Capital; notable angel investors include Naval Ravikant, Anthony Goldblum, Gokul Rajaram, Sian Banister, and Lenny Rachitsky. - The founding team leveraged their experience at Meta and WorldQuant to identify a gap in the market: the need for a vertically integrated stack for machine learning and AI, similar to what large tech companies use internally. - TrueFoundry's go-to-market strategy focused on serving large enterprises from the start, building robust infrastructure before launching, and validating their approach through extensive primary market research and early customer conversations. - The company's north star metric is the proportion of an organization's compute running on TrueFoundry, and their key advice for founders is to balance short-term market needs with a clear long-term vision, maintaining transparency and adaptability within the team. Sponsored by Auth0 for Startups → 1-year free https://auth0.com/startups/vip Auth0 is an adaptable authentication and authorization platform that helps you secure your apps and AI agents. It delivers convenience, privacy, and security so you can focus on building a great UX. FOUNDER PROFILE: Nikunj Bajaj, Founder of TrueFoundry https://www.linkedin.com/in/nikunj-bajaj-10476824

What if the thing holding you back from posting isn't laziness or a lack of ideas, it's that nobody ever told you the cringe feeling goes away, and what it actually looks like to build trust with an audience without burning it?In this special episode of Supra Insider, Ben Erez sits down with Hilary Gridley, creator of the Maven course “How to Become a Supermanager with AI,” and Mallory Contois, former VP of Growth at Maven and founder of The Old Girls Club, for a candid conversation about self-promotion, audience building, and the surprisingly practical mechanics of showing up consistently online without losing yourself in the process. Hilary published a guest post on Lenny's Newsletter the same morning this was recorded, and that pipeline, from writing to course to full-time career, is exactly what the conversation unpacks.They cover why trust is the most durable professional asset you can build, how to think about the value exchange between creator and audience, why the psychology of “doing work in private and handing in the final product” makes content creation feel so unnatural, and what both of them actually do to stay consistent without spiraling into algorithm-chasing. Mallory drops a deceptively simple Apple Notes system for never running out of ideas. Hilary makes a sharp case for starting with a talk instead of a newsletter. And both of them are refreshingly honest about the fact that posting still feels mortifying sometimes, and why you should do it anyway.If you're a PM, operator, or founder who has been sitting on the sidelines of content creation because it feels cringe, trying to figure out which platform to start with, or building an audience and wondering how to grow it without compromising the thing that makes your voice worth following- 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

What does it actually mean to bet on yourself, and how do you know if the game you're playing is really the one you want to be in?In this special episode of Supra Insider, Marc Baselga and Ben Erez record together in person for the first time, sitting down at a studio in New York to have an honest, unscripted conversation about optionality, partnership, and what they've learned from building Insider Loops over the last seven months. They open with the question hanging over a lot of high-agency people right now: with AI making it easier than ever to go from idea to product, should you leave your job and bet on yourself? Marc names the only full-time role that genuinely tempts him, Anthropic, and then explains exactly why he still wouldn't take it. Ben unpacks why he accomplished 20% of what he was capable of during his full-time years, and what changed.They go deep on why bootstrapping is harder than raising VC money, but why the constraints force the kind of market discipline that most funded companies never develop. They map out their complementary skill sets, how they've shifted from long-term planning to weekly cadence, and why they now think planning more than a week ahead is mostly a waste of time. The conversation closes on the role of the podcast itself, why it has to stay separate from the business, why fun is an emergent property and not a frivolous goal, and why the relationship comes first.If you're weighing whether to leave a stable job and go off on your own, curious about what a bootstrapped partnership actually looks like day to day and what makes it work, or just want a rare honest conversation between two builders about what they'd do differently and what they wouldn't change, this episode is for you.A special thanks Alex Pavlou and the team at 28th & Park for the recording space!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

What if the most important skill for building AI products has nothing to do with evals, technical background, or knowing how to write a prompt? What if it is the ability to design systems that can handle what you never planned for?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Apurva Garware, who has built and scaled products across Amazon, Microsoft, and Upwork, to make the case that systems thinking is the defining skill of the next era of product management. Apurva explains why non-determinism forces PMs to stop thinking in features and start designing the guardrails, agent contracts, and escalation points that govern how a system behaves at runtime, when no one is watching. They explore a three-phase framework for governing AI systems across design, deployment, and production; heuristics for deciding what to hand to agents versus escalate to humans; and a sharp insight about the two products every AI-native company is actually building: the customer-facing product, and the internal operational system that drives margin and velocity. Marc and Ben also share their own experience calibrating an agentic workflow at Supra, grounding the conversation in practice.If you are a PM trying to find your footing in the AI era without a deeply technical background, a founder wrestling with when to reach for AI versus simpler deterministic automation, or a product leader who wants to build more discipline into how your team ships AI products, 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

What happens to the product development process when the lines between who builds, who designs, and who decides start to disappear?In this special episode of Supra Insider, recorded as part of the Blurring Lines series with Aster AI, Ben Erez sits down with Rishin Banker, VP of Product at Maven, to explore how a 25-person team is rethinking product development in real time. Rishin opens with a concrete shift: Maven went from two to three concurrent projects to five to six, same headcount, smaller pods, more decision-making at the team level. The unlock wasn't hiring. It was front-loading strategy so more people could move into the build phase at once.They explore how Maven's head of design shipped a full marketing page to production end-to-end, why months of foundational design system work made that possible, and where Figma still fits. Rishin also gets into the tensions he's navigating, unexpected handoffs, competing priorities when people build in silos, and the difference between projects that can live in their own container versus ones that need specialist input from the start.If you're a product leader restructuring your team for the current moment, a designer or PM excited about building more but unsure how to navigate the role blurring, or curious how a lean startup is actually operationalizing these changes day to day, this episode is for you.A special thanks Alex Pavlou and our friends at Aster AI for hosting this session!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

What if the reason you feel like you never have enough time isn't actually a time problem at all?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Molly Siemers, an executive coach for product leaders who spent over two decades building mission-driven products at companies like Kiva, Change.org, and Blurb before launching her coaching practice, Product Craft Works. Molly opens by naming what she's watching in real time: product leaders are running faster than ever, layoffs are everywhere, and the pressure to adopt AI on top of everything else is creating a new kind of cognitive overload. Coaching, she argues, has never been more necessary, not because people need tactics, but because most people are solving the wrong problem.They explore the difference between time and capacity, why the best senior leaders seem unflappable, and how personal capacity is something you build, not something you find by rearranging your calendar. Molly walks through the integral coaching methodology she trained in, the threshold practice she gives clients to start tapping into body and emotional intelligence, and the three-step framework she keeps returning to: notice, decide, act. The conversation then turns personal, with Marc and Ben reflecting on agency, identity, and what happens when you look around and realize you've built a job you hate, or, on the flip side, a life that actually works.If you're a product leader feeling overwhelmed and can't figure out why, someone navigating a career transition and struggling with identity, or a founder or operator who's curious whether coaching might actually be worth it, 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

What if you could know whether your product change was going to work — before a single real user ever saw it?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Tom Charman, co-founder of Blok, a synthetic user simulation platform that lets product teams test interfaces, onboarding flows, and product changes against AI-powered behavioral personas, not just to predict conversion, but to model second and third order effects like churn, confusion, and long-term retention. Tom opens by naming what's changed: shipping is faster than ever, but the tools PMs use to decide what to build haven't kept up. AB tests still take two to three weeks. Traditional user research still skews toward power users. And as personalization gets more complex, getting to statistical significance gets harder. That's the gap Blok is trying to close.They explore how Blok's behavioral personas go beyond demographics to model psychographics, emotional state, and memory, including what happens when a user has a bad first experience and comes back to your product skeptical. Tom walks through the ICP trap that kills retention, why the “show don't tell” principle protects against confirmation bias, and why he thinks the biggest shift happening in product right now is the move from reactive to proactive, replacing AB tests and feature flags with pre-ship simulation that gets you to directional confidence in 12 minutes instead of three weeks.If you're a PM tired of going to battle in product reviews without data to back your intuition, a founder trying to understand how synthetic users actually work and whether they're worth it before Series A, or a product leader looking to understand how the entire feedback loop from idea to deployment is about to be rebuilt, 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

What happens to the PM, the designer, and the engineer when a single person with a great idea can take it all the way to market on their own?In this episode of Supra Insider, Ben Erez sits down with Tomer Cohen, former Chief Product Officer at LinkedIn, where he spent 14 years and led the company's product transformation through the AI era. Tomer unpacks the full stack builder mindset - not as a job title, but as a fundamental rethinking of how product development works when the bloated, process-heavy model of the last two decades gets collapsed back down to its original building blocks: idea, build, ship.They explore how Tomer actually rolled this out at LinkedIn across thousands of people, including replacing the traditional APM program with one where candidates submit a working product instead of a resume, and where the final interview is building something end to end in real time. He breaks down the three archetypes he sees emerging - system builders, full stack builders, and specialists - and what he observed clearly separating top performers from the rest: not their tooling, but their judgment. The conversation closes with a Q&A covering how to navigate interpersonal friction as roles blur, when you actually need a specialist to step in, and what skills will remain stubbornly human no matter what.If you're a PM, designer, or engineer trying to understand where your role is actually heading and what to do about it right now, trying to think clearly about how to future-proof your career without falling for hype, or curious how a CPO at one of the biggest tech companies in the world actually tried to operationalize this shift - 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

What if the cognitive overhead of constant context-switching, endless meetings, and deciding what to work on next could be offloaded to a system that actually knows how you think?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Michael Leibovich, a business unit leader at Adobe overseeing product, design, support, and business strategy, who spent his paternity leave building something most people only talk about: a fully personalized AI chief of staff, built on Claude Code, powered by nothing more than folders and markdown files.They explore the architecture behind Michael's system in detail, from session memory and mental models to a people file that auto-updates from meeting transcripts, a knowledge graph that grows over time, and scheduled tasks for daily meeting metabolization and weekly competitive intel. Michael walks through how he bootstrapped his minimum viable context by extracting from ChatGPT's memory in under ten minutes, why Obsidian became his visual interface of choice, and the moment he realized this was genuinely worth the investment: getting a suggested answer to “what is the highest leverage thing I should do right now?” in a 30-minute gap between meetings.If you're a non-technical operator overwhelmed by AI tooling and unsure where to start, a leader constantly context-switching between teams who struggles to protect time for deep work, or someone building out your own context infrastructure and looking for a real-world playbook, 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

What if the reason great talent keeps failing at your company has nothing to do with the talent — and everything to do with the environment you built around them?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Hiten Shah, serial entrepreneur and co-founder of Crazy Egg, who recently had his first-ever job as a PM at Dropbox after selling his company to them. That 15-month experience as an individual contributor — after a lifetime of being the one who owned the environment — completely changed how he thinks about leadership. Hiten unpacks the viral post that kicked off this conversation and introduces a framework most people have never articulated: vibe leads to environment, and environment leads to culture.They explore what happens when leaders lose ground-level visibility, why escalation is actually healthy in large organizations, and how Hiten's startup FYI built a concrete interview process to hire specifically for environment fit. The conversation moves through the Toby Lütke / Shopify story, the “nothing changes without fireworks” principle, and why most CEOs are outsourcing environment visibility to the wrong people — before pivoting into Hiten's current obsession: running OpenClaw bots inside Slack, pair prompting, and how a two-bot thread with 800 messages built an entire product without Hiten touching a line of code.If you're a founder who's started to feel like a prisoner in the company you built, a leader trying to figure out why strong people keep underperforming, or a non-engineer looking to get serious leverage from OpenClaw bots without using Claude Code — 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

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.We discuss:1. The exact step-by-step process to install and set up OpenClaw (it's easier than you think)2. How to avoid the biggest OpenClaw mistakes (don't install it on your main computer)3. Actual use cases that have changed Claire's life (e.g. family scheduling, inbound sales, podcast prep, and course management)4. Why multiple specialized agents beat one general-purpose agent5. The security risks everyone worries about—and how to handle them6. Browser limitations, memory issues, and practical workarounds—Brought to you by:Mercury—Radically different bankingOmni—AI analytics your customers can trustOrkes—The enterprise platform for reliable applications and agentic workflows—Where to find Claire Vo:• X: https://x.com/clairevo• LinkedIn: https://www.linkedin.com/in/clairevo• Podcast: https://www.youtube.com/@howiaipodcast• Website: https://clairevo.com• ChatPRD: https://www.chatprd.ai—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Claire and OpenClaw(08:00) The journey from OpenClaw skeptic to believer(11:50) What OpenClaw actually does that's useful(13:35) OpenClaw vs. other AI agent products(17:05) How to actually install OpenClaw: the basics(18:49) Setting up like you'd onboard a real assistant(20:41) Security and privacy considerations(24:53) Live demo: Installing OpenClaw step-by-step(28:47) Setting up Q: an agent for her kids' homework(34:08) Understanding “soul,” “identity,” and “memory”(40:40) The unlock: multiple agents, not just one(45:02) How to run multiple agents on one machine(47:28) Jesse Genet's homeschooling use case(49:58) Real examples and use cases(56:41) Finn, Claire's family agent(1:00:05) Sage the Course Bot(1:02:15) Common issues and workarounds(1:08:08) The Exa/Perplexity web search workaround(1:09:29) Memory management and context overload(1:12:09) Pro tip: Screen sharing to manage Mac Minis(1:14:18) Using Google Workspace for agent collaboration(1:16:24) What makes OpenClaw special(1:20:15) The “yappers API” and ramble mode(1:22:04) Using Claude Code as your OpenClaw brain surgeon(1:25:16) Bringing management skills to AI agents(1:29:32) Why this matters(1:32:37) Lightning round and final thoughts—Referenced:• OpenClaw: https://openclaw.ai• Claude Cowork: https://claude.com/product/cowork• Fry's Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete• Telegram: https://telegram.org• WhatsApp: https://www.whatsapp.com• Fin: https://fin.ai• Why OpenClaw feels alive even though it's not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/• ChatGPT Atlas: https://chatgpt.com/atlas• Perplexity Comet: https://www.perplexity.ai/comet• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser• Buffer: https://buffer.com• Brave: https://brave.com/search/api/• Exa: https://exa.ai• Hilary Gridley on X: https://x.com/yourgirlhils• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI• How to debug a team that isn't working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter• Age of Attraction on Netflix: https://www.netflix.com/title/81779095• Oura Ring: https://ouraring.com/• Eight Sleep: https://www.eightsleep.com• Hoopsalytics: https://hoopsalytics.com• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9• Marc Andreessen: The real AI boom hasn't even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom—Recommended books:• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400• Alice's Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

What does it actually take to make fractional work sustainable, not just for a few months, but as a real career path?In this special solo session, Ben Erez shares everything he's learned about fractional product work from two distinct perspectives: as Head of Product at Continuum (a Series A marketplace for fractional executives that eventually shut down) and from his own two years doing fractional work. He walks through the foundations that set you up for success, how to actually find work and structure engagements, and most importantly, how to make it sustainable and not die. Ben is ruthlessly honest about what worked, what failed, and why intentionality is the difference between loving fractional work and hating it.He covers the counterintuitive truth that narrow positioning beats broad positioning (using Phil Carter as a case study), why you need to learn to enjoy marketing yourself or you'll burn out, and the three non-negotiable requirements for any engagement (relevant expertise + urgent need + budget). Ben shares real revenue data showing the spiky, unsteady income reality, explains the “feast or famine” trap that kills most fractional careers, and why he's skeptical that demand aggregators will ever crack this market at scale. Plus, tactical advice on pricing, the transition from being helpful for free to asking for money, and why referrals beat every other channel.If you're exploring fractional work as a side hustle, between full-time roles after a layoff, or considering it as a long-term path—this session 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

What happens when everyone can build, but no one breaks through the noise?In this episode of Supra Insider, Ben Erez sits down with Elan Miller, founder and CEO of branding and design studio Off-Menu, for the podcast's first live in-person recording. Elan unpacks why this moment is uniquely challenging for brand storytelling—AI has made it easier than ever to build and ship products, but harder than ever to get people to care. He explains how the standard tech playbook (great product + clever go-to-market) no longer works when 10 competitors can copy you within a month, and why honorable points of view are the only sustainable moat.They explore Anthropic's Keep Thinking campaign and Super Bowl ads as a masterclass in positioning against OpenAI, discuss why successful positioning must repel people as much as it resonates, and unpack the Granola rebrand (including Ben's honest reaction as a customer). Elan shares why most rebrands fail (visual makeover without moving anything forward), the different reasons companies should rebrand (talent attraction, internal alignment, crossing the chasm), and his process for finding the “holy s**t insight” that makes people feel seen. Plus, how he's building AI tools that turn brand strategy into practical inputs for higher-quality outputs, and why strong point of view is the antidote to slop.If you're building in a crowded space and struggling to stand out, wondering whether a rebrand is the right move, or trying to articulate what makes you different in a way that actually resonates—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

People have been asking me to sit on the other side of the mic for a long time. With my wife's debut children's book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I've had on this podcast. Michelle asked things no one else would think to ask—and many things I've never shared publicly. You'll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.We discuss:1. The collection of moments that led me to what I do now2. When I added a paywall, and how I knew it was working3. The hidden treadmill behind shipping a newsletter post and podcast episode every week4. The most stressful moments I've had in business and in life5. How I think about stress, consistency, and keeping the business small—Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyDX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Michelle Rial:• X: https://x.com/TheRialMichelle• LinkedIn: https://www.linkedin.com/in/michellerial• Website: https://www.michellerial.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and role reversal(04:06) What would Lenny be doing without the newsletter?(07:20) The moments that led to starting the newsletter(09:58) Does Lenny still enjoy the work?(12:42) Stress management and misophonia(14:00) The psychedelic trip that changed everything(15:45) Online happiness course and baseline optimization(17:30) Thunder round: Lenny's misophonia worst sounds(20:20) What makes Michelle's charts so shareable(23:55) Where chart ideas come from (and why meditation helps)(26:59) Where does “Lenny” come from?(28:54) Being recognized in public(31:24) Early projects(36:30) Michelle and Lenny's yin and yang(37:49) Missing office culture (but not really)(39:37) Lenny's face blindness(40:47) The $100M fraud attack story(42:50) Michelle's childbirth emergency(47:22) Michelle's creative process(51:58) Lenny's favorite children's books(54:00) Product management lessons in parenting(55:31) Defining product management in five words(58:23) Why Michelle pivoted to children's books(01:01:30) The power of iteration and real experience—Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. To hear more, visit www.lennysnewsletter.com

What if your computer didn't need a screen in front of you to get work done? That's the shift Ben Guo, co-founder of Zo, is building toward, and this conversation gets into the specifics of what that actually looks like day to day.In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Ben Guo to explore Zo: a personal cloud computer with built-in AI agents, file storage, scheduled tasks, and the ability to receive commands over text or email. Together, they unpack how Zo differs from the OpenClaw movement and why Ben thinks the personal cloud becomes a device category everyone eventually owns.The conversation goes deep on how the Zo team actually builds software: writing AI-generated markdown plans before touching any code, reviewing those plans as GitHub PRs, and largely abandoning the traditional to-do backlog in favor of just prompting something and letting it run. They also get into the real overhead that comes with this new way of working, including context management, delegation judgment, and figuring out what belongs where.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

What does it take to go from “1 out of 10 chance we hit 100 episodes” to actually getting there?In this special milestone episode, Marc Baselga and Ben Erez reflect on reaching 100 episodes of Supra Insider. They share the raw truth about early imposter syndrome—having a Google Doc with pre-written questions, worrying about sounding stupid, focusing more on optics than enjoyment. They discuss the key turning points that made the podcast sustainable: bringing in an editor (reducing their workload from 6-8 hours per week to just recording), stopping the intro recordings, and setting fixed “sacred” time slots that never move.They explore what they've learned about guest selection (intuition-based, not heavily strategic), the tension between timeless vs. timely content, and what successful podcasts have in common—regardless of format. Whether it's Acquired (catalog value, timeless deep dives) or TBPN (daily, day-of relevant), the common thread is two co-hosts who genuinely enjoy each other, are obsessed with making it better over time, stay authentic, and avoid inorganic pressures that force the show to be something it isn't.If you're thinking about starting a podcast, struggling to make one sustainable, or wondering how to build something meaningful that fits your life—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

What does it take to go from zero tech experience to founding PM at a cybersecurity startup in three years?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Yaniv Fatal, founding product manager at Blast Security, to unpack his remarkable journey from elite Israeli Air Force pilot to tech. After 13 years in the military and zero technical background, Yaniv failed 20+ interviews before landing at Wiz (later acquired by Google for $32B). He shares how he applied pilot debriefing methodology to each rejection, learned cloud security from absolute zero in weeks, and built credibility through relentless questioning and delivering results nobody else could.They explore Yaniv's philosophy on learning: mastering fundamentals first (no shortcuts), being comfortable asking “dumb questions,” and the belief that you don't really understand something until you can teach it. Plus, his approach to long-term goal setting—he and his wife keep a notebook with goals for where they want to be at age 45, including his aim to be CEO or C-level, which drives every decision he makes today. And why product management is his chosen path to that goal, inspired by the fact that CEOs of Google and Microsoft were all PMs first.If you're considering a major career transition, struggling with imposter syndrome while learning something completely new, or trying to figure out how to set goals that actually drive your daily decisions—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

What if the biggest barrier to learning AI isn't the tools—it's how we approach learning itself?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Gagan Biyani, CEO and co-founder of Maven, to unpack why this moment is critical for mid-career professionals to prioritize self-learning. Gagan shares lessons from running a cohort-based learning platform and conducting 30-50 interviews with companies struggling to adopt AI. He explains why AI is like witnessing the internet as a child—you can't afford not to learn it—and why building the learning habit matters more than what you learn first.They explore the five problems companies face with AI education: trying to generalize training when every role needs different tools, listening to tinkerers instead of bridge adopters, and delegating to chiefs of staff instead of having C-level sponsors run the trainings. Gagan shares Maven's own journey—why their design team needed to rebuild the design system before AI could be useful, how they're changing team ratios from 3-4 engineers per designer to just 2, and why social media is terrible for learning anything that requires weeks of dedication.If you're a mid-career professional feeling overwhelmed by AI, a leader trying to build a culture of self-learning at your company, or wondering how to actually integrate AI into your workflows—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

What if the thing holding you back from building a public presence is exactly what would make you stand out?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Mallory Contois, VP of Growth at Maven, to unpack why this is the perfect moment for product leaders to start sharing publicly—even if they don't feel polished, interesting, or like they have it all figured out. Mallory explains how we're leaving the era of glossy, aspirational influencer content and entering one where audiences crave authenticity, relatability, and actionable takeaways.They tackle the three biggest mindsets that hold people back: the “influencer hater” who rejects performative content, the person who doesn't think they're interesting enough, and the professional who believes their work should speak for itself. Mallory breaks down why good work alone isn't enough, why consistency beats virality, and how to find your authentic voice without trying to game algorithms or chase trends.If you're a product leader who's been holding back from sharing publicly, wondering whether anyone would find your perspective valuable, or questioning whether personal branding is worth the effort—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

Recently, Marc Andreessen joined Lenny Rachitsky on Lenny's Podcast. They talked about why 2025 may be the most significant year in tech history, how AI is reshaping the future of product managers, designers, and engineers, and what founders need to understand about building in this moment—from where moats actually exist in AI to what the most AI-native companies are doing differently to the skills Marc is teaching his own kids to thrive in what comes next. Resources:Follow Marc Andreessen on X: https://twitter.com/pmarcaFollow Lenny Rachitsky on X: https://twitter.com/lennysanCheck out Lenny's Podcast: https://www.lennysnewsletter.com/podcast Stay Updated:If you enjoyed this episode, be sure to like, subscribe, and share with your friends!Find a16z on X: https://twitter.com/a16zFind a16z on LinkedIn: https://www.linkedin.com/company/a16zListen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYXListen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711Follow our host: https://x.com/eriktorenbergPlease note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures. Stay Updated:Find a16z on XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On this episode of Christopher Lochhead: Follow Your Different, we sail with the Category Pirates to unpack why career success in the coming years hinges on moving beyond using AI as just another productivity tool and embracing it as a co-founder and thought partner. The insights aren't just for techies or founders, they are relevant for anyone who wants to future-proof their career and unlock uncommon leverage in a world being remade by generative AI. As we find ourselves deep in the rise of artificial intelligence, the ways people define their careers and generate value are evolving rapidly. This episode dives into two key research reports that uncover a powerful trend shaping the very foundation of work and entrepreneurship. You're listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let's go.   LinkedIn and Lenny: Two Data Sets Signal a Seismic Shift Very recently, two independent research efforts converged on a striking insight. LinkedIn, with its enormous database tracking millions of real career moves, revealed the fastest-rising roles: founder, AI engineer, independent advisor, and AI strategist and consultant. The title “founder” alone is up 60 percent year-over-year and has nearly tripled since 2022. This isn’t just a startup wave; it’s a broad career escape pattern: a mass migration away from conventional jobs towards agency, creativity, and ownership. Meanwhile, the renowned Lenny Rachitsky, together with Noam Segal, surveyed 1750 tech workers who are already deep in the trenches of AI adoption. Their data not only reinforced the LinkedIn findings but made something even clearer. The workers getting the greatest value from AI weren’t simply using it to write faster emails or crank out code a bit quicker. Founders (those who saw themselves as owners) were extracting exponentially more value, driving higher ROI, more time savings, and better work quality by leveraging AI not just to improve execution, but to reimagine strategy and decision making.   Moving Beyond Tool: AI as Your Career's Co-Founder What's the real difference between the “founders” in these studies and many other professionals? It's not intelligence or technical skill. It's mindset and operational practice. Founders use AI as a co-founder rather than a generic tool. They treat their careers as if they are companies, and AI is their essential collaborator. While engineers, managers, and designers may use AI to automate tests, generate presentations, or speed up research, founders leverage AI for decision making, vision, and strategic moves. The approach goes even deeper. Top performers are building their own custom AIs, trained on their unique intellectual property: their notes, writing, frameworks, and research. This isn't about using a public ChatGPT prompt or borrowing from generic knowledge bases. The new class of “creator capitalists” construct a persistent AI thought partner that challenges their assumptions, remembers everything they’ve produced, and becomes an always-on collaborator for new ideas, product invention, and critical thinking. At Category Pirates, for example, their internal “Lucy” AI has become the sharpest mind on their team: always ready to spark new value, and even surpassing the domain expertise of its human creators in key areas.   From Execution Labor to Creator Capitalists: The New Career Divide This transformation signals a far deeper change in the job market. The traditional divide of technical versus non-technical roles, or employed versus unemployed, is becoming less relevant. Instead, the real split now is between execution labor and creator capitalists. AI is driving the cost of accessing knowledge and automating rote tasks toward zero. Execution labor (those who focus on applying known inputs to familiar problems) can use AI to go faster but are still replaceable. In contrast, creator capitalists use AI to design new futures, develop judgment, and build intellectual capital that compounds over time. The LinkedIn and Lenny data make it clear: career value is migrating from mere knowledge and execution to originating new insight and value. The people outpacing the pack aren't simply working harder or faster. They've redrawn the boundaries of their roles, shifted from employee to owner in mindset, and made AI their partner in creation, decision-making, and value extraction. The future belongs to those who build and train their own custom AIs, transforming themselves into categories of one, and compounding their expertise every single day. If you want to move from knowledge worker to creator capitalist, and from user to AI collaborator, the playbook is already available and the evidence is hiding in plain sight. The choice is yours: stick with generic tools and returns, or invent the future side by side with your own AI co-founder. If you want to hear more from the Founding Category Pirates themselves, download and listen to this episode.    Links Check out the latest Category Pirates posts and discussions about The Secret to Success in 2026!  Want to join in the conversation? Check out the Category Pirates newsletter and feel free to share your thoughts with the crowd!    We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, X (formerly Twitter), Instagram, and subscribe on Apple Podcast / Spotify!  

Listen now: Spotify, Apple and YouTubeHow do you disagree with your CEO, especially a visionary founder, without putting your job or credibility at risk?In this episode of Supra Insider, Marc and Ben sit down with Elena Luneva (CPO, advisor, and executive coach) to unpack one of the most common, emotionally fraught challenges in product leadership: what to do when your CEO wants to change direction based on a gut instinct, and you disagree?Drawing from Elena's coaching experience and her own time leading product at high-growth companies, the conversation explores how to navigate power dynamics, set boundaries without losing trust, and protect team momentum amid constant change. They also share tactical frameworks for managing roadmap pivots, setting expectations with execs, and negotiating trade-offs when the team is already stretched thin.Whether you're a PM, product leader, or founder, you'll walk away with practical strategies for navigating tough conversations, advocating for your team, and growing your influence, without losing your job or your sanity.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

Listen now: Spotify, Apple and YouTubeIf you've ever considered turning your expertise into a scalable product—or wondered what it actually takes to build and sell a useful AI copilot—this episode is for you.In this episode, Ben shares the full behind-the-scenes story of how he packaged his product management knowledge into a sellable, high-leverage AI Practice Copilot. From initial validation to prototyping in Claude to vibe coding in Cursor and shipping using various AI tools, he walks through every decision point in the journey. You'll learn how to pick the right use case, what tools to use at each step, and the key insights that helped him turn his ideas into a real product in the market.Whether you're a founder, PM, coach, or subject matter expert, this conversation is packed with actionable tactics to help you create, position, and monetize your own AI-native product.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

Listen now: Spotify, Apple and YouTubeWhat does it mean to truly be an “AI-native” company? And how are product roles evolving when PMs are expected to both execute faster and make sharper strategic decisions?In this episode of Supra Insider, Marc and Ben sit down with Adam Fishman—host of the Startup Dad podcast and longtime product leader and advisor —to unpack the key themes from Reforge's recent AI Product Summit in San Francisco. Adam shares insights from conversations with leaders at OpenAI, Anthropic, Shopify, Zapier, and LinkedIn on how organizations are tackling AI adoption, redefining PM expectations, and navigating cultural change.The discussion ranges from Zapier's live prototyping interviews for new hires, to LinkedIn's shift from “product managers” to “product builders,” to the tension PMs face between increased executional leverage and the need for sharper strategic taste.Whether you're a PM figuring out how to stay relevant, a product leader navigating culture change, or just curious how AI is transforming product organizations, this episode is packed with lessons you can apply today.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

Listen now: Spotify, Apple and YouTubeWhat if interviewing for a PM job at Stripe, Uber, or Figma didn't feel like walking into the unknown?In this episode of Supra Insider, Marc and Ben take you behind the scenes of building Insider Loops—a new set of interview prep guides designed to give candidates the inside track at some of tech's most competitive companies. They break down why they saw the opportunity, how they rapidly prototyped and shipped their first guides, and what they learned from dozens of conversations with PMs and hiring managers.From uncovering hidden disconnects between great PMs and great interviewees, to the surprising differences in how Uber, Figma, and Stripe run their loops, this episode blends entrepreneurship, product thinking, and tactical job-search insights. Whether you're preparing for your next role or just curious about how Marc and Ben collaborated async to launch a new product, you'll walk away with practical takeaways and fresh perspective.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

Listen now: Spotify, Apple and YouTubeWhat if personal finance wasn't just about saving more or investing better—but about designing a life that feels meaningful, intentional, and aligned with your values?In this episode of Supra Insider, Marc and Ben sit down with Zach Teutsch, founder of Values Added Financial, to explore a radically human approach to wealth management. Instead of fixating solely on net worth, Zach helps high earners and tech professionals reframe their relationship with money, starting with life satisfaction and working backwards from there.They dive into the core questions that drive meaningful financial management, from how to balance ambition and family, to navigating equity compensation, sabbaticals, early-stage investing, and building a diversified “life portfolio.” Zach also shares tactical frameworks for spiky income years, Roth conversions, QSBS tax planning, and setting up estate plans that reflect your real priorities.Whether you're in tech, product leadership, or just rethinking how you manage money, this conversation will shift how you think about personal finance—from accumulation to alignment.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

Listen now: Spotify, Apple and YouTubeIf you've wondered how much AI is really helping engineers - or feared it might replace them - this episode is for you.In this conversation, Marc and Ben sit down with Nick Meehan, a senior engineer and longtime collaborator, to explore how AI coding tools like Cursor, Claude, and Codex are reshaping day-to-day engineering work. Nick shares how his process evolved from copy-pasting into ChatGPT to using AI as a debugging partner, thought collaborator, and junior developer moving at superhuman speed.They cover the productivity gains, the pitfalls of vibe coding entire products, the new skills engineers need (critical thinking, architecture, team coordination), and what might never be replaced by AI. Nick also reflects on job security, how satisfaction in engineering is shifting, and where he sees the field heading over the next five years.Whether you're an engineer experimenting with coding agents, a product leader trying to understand their impact, or simply curious about how AI is changing the craft of engineering, you'll walk away with an insider's perspective on what's actually happening on the ground.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

Listen now: Spotify, Apple and YouTubeThink a “portfolio career” makes family life chaotic? Ben argues the opposite.In this special episode of Supra Insider, Ben shares a more personal side of his journey in a conversation originally recorded on the Startup Dad podcast with Adam Fishman.From raising his daughter Gaia (with help from George, the family's golden retriever) to navigating solo parenting in New York without nearby family, Ben opens up about the joys and challenges of fatherhood. He reflects on why a portfolio career actually feels more stable than a full-time job, how intentional routines have transformed his days, and the lessons learned from mistakes, community, and the chaos of parenting.If you're a parent balancing an ambitious career, curious about the realities of raising kids in a big city, or simply want to hear a more personal side of Ben outside of product leadership, this episode offers candid stories, practical takeaways, and a heartfelt look at family life.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

Listen now: Spotify, Apple and YouTubeAI is transforming the way product teams approach customer research—but what should remain human, and what can be handed off to AI agents? In this episode, Marc and Ben sit down with Aaron Cannon, co-founder of Outset, to explore the evolving role of AI in discovery and usability testing. Aaron unpacks how AI-moderated research enables unprecedented speed and scale while preserving depth, why intuition remains critical for building great products, and how research teams can shift from execution to framing the right questions and telling better stories. The conversation also dives into the future of PM and UXR roles, collective intuition at companies, and the career paths that might emerge as AI takes on more “entry-level” tasks.Whether you're a PM, designer, or researcher wondering how to integrate AI without losing the magic of human insight, this episode offers practical frameworks and a forward-looking perspective on what's next.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

Ex-Product Manager chez Airbnb, il gagne aujourd'hui plusieurs millions par an en écrivant une newsletter :Lenny Rachitsky prouve qu'on peut transformer son expertise professionnelle en empire digital sans perdre son authenticité. Son approche révèle comment traiter sa newsletter comme un vrai produit tech.Tu découvriras comment il a transformé un article viral en business à plusieurs millions, pourquoi il traite sa newsletter comme un laboratoire pour comprendre son marché, et comment il a construit un écosystème complet autour de son expertise.

Listen now: Spotify, Apple and YouTubeWhat if you could cut your QA cycles from days to minutes—and draft PRDs that actually update themselves as your product evolves?In this episode of Supra Insider, Marc and Ben sit down with Amir M, cofounder of Humblytics, to explore how he's running a two-person startup across engineering, QA, and product using Cursor and Model Context Protocols (MCPs). Amir shares how he builds context-rich workflows, turns documentation into living systems, and uses agentic tools like Firecrawl and Playwright to automate the “boring” but critical parts of product development.If you've been curious about how to bring AI deeper into your product org—not just for brainstorming but for end-to-end execution—this conversation is packed with practical demos and mindsets you can apply today.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

Listen now: Spotify, Apple and YouTubeAs AI agents become the new interface for work, a major question looms: how will your product connect into this ecosystem?In this episode of Supra Insider, Marc and Ben sat down with Reid Robinson, product manager leading AI at Zapier. They talked about the rise of Model Context Protocols (MCPs) — the new standard for connecting AI agents to tools and data sources.Reid explains the fundamentals of MCP clients vs. servers, why the standard is gaining traction across players like Anthropic, OpenAI, and Atlassian, and how product leaders can decide where to start. He also shares concrete examples, from personal productivity hacks to enterprise integrations, showing what's possible when you combine MCP with Zapier's 8,000+ app ecosystem.Whether you're building your first AI copilot, figuring out how to expose your product's data to agents, or just want to understand where this ecosystem is headed, this episode will give you a front-row seat to the future of AI interoperability.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

Listen now: Spotify, Apple and YouTubeWhat happens to product management when building becomes nearly frictionless—and AI threatens to replace the “busy work” PMs have traditionally done?In this episode of Supra Insider, Marc and Ben sit down with legendary product coach Rich Mironov to explore the shifting value of product leadership in the AI era. They unpack why great PMs must now double down on customer insights, business understanding, and organizational influence rather than execution—and how this shift impacts hiring, mentorship, and career paths.From the dangers of AI-washing and backlog bloat to the rise of lifestyle businesses and the blurred line between product and business leadership, this conversation is packed with perspective for Product Leaders, aspiring founders, and anyone navigating today's chaotic tech landscape.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

Listen now: Spotify, Apple and YouTubeWhat if the key to showing up as a great leader had nothing to do with your title, metrics, or credentials—and everything to do with knowing who you are outside of work?In this episode of Supra Insider, Marc and Ben sit down with executive coach Charles Ruiz to explore how leaders can shift from external validation to authentic presence. Charles shares the origins of his mantra “Presence over Preference,” his Four Cs framework (Core, Craft, Community, Creativity) and the transformative practice of running an “identity marathon” through meaningful places from his past.You'll hear benefits of executives ditching scripted presentations for personal anecdotes (including burrito orders), reframing failure as fuel, and designing your own “games” and “seasons” of life instead of playing someone else's. Whether you're climbing the corporate ladder, pivoting careers or just questioning who you are beyond your job, this conversation will help you reconnect with your story—and turn it into your superpower.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

Listen now: Spotify, Apple and YouTubeWhat if walking away from your polished product career was the exact move you needed to grow?In this episode of Supra Insider, Marc and Ben sit down with Jori Bell to explore her unconventional journey from PM roles at Spotify, SoundCloud, and Audible to building a coaching practice, curating intimate community spaces, and teaching at Cornell Tech. After two years of self-exploration and reinvention, Jori is now bringing her rediscovered superpowers—curiosity, empathy, and intuition—into her new role at Hampton, helping founders and CEOs cultivate meaningful peer connections.This conversation is a must-listen for anyone considering a career pivot, rethinking their relationship with work, or exploring how product skills can show up in unexpected, high-impact ways.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

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

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

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

Today's read is by one of my favorite startup creators, Lenny Rachitsky. The essay, How To Kickstart & Scale a Consumer Business, breaks down the seven proven strategies to acquire your first 1,000 users as a B2C startup. I'm going to read through each of the strategies, share some examples that Lenny provides, and provide some of my own thoughts on early growth. Original essay: https://www.lennysnewsletter.com/p/consumer-business-find-first-users — Thanks to our presenting sponsor, Gusto. Head to www.gusto.com/alex — Check Out Alex's Stuff: • storyarb - https://www.storyarb.com/ • growthpair - https://www.growthpair.com/ • distro - https://youdistro.com/  • X - https://x.com/businessbarista • Linkedin - https://www.linkedin.com/in/alex-lieberman/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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

If you've ever found yourself torn between chasing a long-term product vision and urgently responding to customer demands—or wondered how to strike the right balance between innovation and pragmatism—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Troy Sultan and Austin Cooley, co-founders of Guide, to explore how they transformed their entire product philosophy from idealistic "big bets" into rapid, incremental solutions based on direct customer feedback. Over eight years as co-founders, Troy and Austin have navigated the common pitfalls of visionary product building, learning to validate product ideas faster, communicate clearly with customers, and shift their strategy to achieve real, measurable results.Whether you're a founder trying to align your product roadmap with sales insights, a product leader collaborating closely with visionary executives, or simply want to sharpen your ability to translate customer feedback into actionable decisions, you'll walk away from this conversation with practical insights you can use immediately to build products that customers genuinely love.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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Robert Hamilton, executive coach and former Meta and Google PM, to unpack the art and science of behavioral interviews. If you've ever struggled with the infamous “leadership and drive” loop or wondered why your best stories aren't landing, this episode is a must-listen.They explore why behavioral interviews are often harder to prepare for than case-style interviews, how to identify the signal behind the questions, and why storytelling, self-awareness, and emotional authenticity are so critical. Robert shares actionable tactics like the STARLU framework (Situation, Task, Action, Result, Learning, Upgrade) and explains how to build a versatile story bank that reveals your growth mindset and values.Whether you're actively interviewing, coaching others, or just want to improve how you tell your story as a PM, this episode is packed with practical wisdom.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

Welcome to another episode of Supra Insider. This time, Marc sat down with Kyle Ledbetter and Andy Keil, the co-founders of Dreambase—an AI-native toolset built on top of Supabase. Despite not having formal engineering backgrounds, Kyle and Andy have built and launched three fully functional products in just nine months.They unpack their unique zero-to-one process—from jamming on whiteboards to building multimodal prompts, doing bake-offs across V0, Bolt, and Lovable, and validating with real users in days, not months.This episode is packed with insights on collaboration, prototyping workflows, and why the best AI builders might not be engineers.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

Jonny Miller is the creator of Nervous System Mastery. It teaches evidence-backed protocols to cultivate calm, build resilience, and increase aliveness in 45 days. It's a five-week, cohort-based course that is just wrapping up its sixth cohort in the last three years. In those six cohorts, Jonny has served nearly 1,000 students and earned more than $800,000. Here's the best part – Jonny doesn't have a massive audience. When he launched Nervous System Mastery, he had a couple thousand followers on Twitter and a small email list. This is the magic of a well-designed Signature Product – and Jonny is the perfect example. In this episode, we get into the weeds about how he's grown NSM – what's worked well, what hasn't, and how he's found himself on large podcasts with people like Lenny Rachitsky, Ali Abdaal, Chris Williamson, and more. → Join Nervous System Mastery Full transcript and show notes Jonny's Website / Twitter / Instagram / LinkedIn *** RECOMMENDED NEXT EPISODE → #221: Ryan Hawk – Anatomy of a $12,500 membership earning $400,000+ per year *** ASK CREATOR SCIENCE → Submit your question here *** WHEN YOU'RE READY

Jonny Miller is the creator of Nervous System Mastery. It teaches evidence-backed protocols to cultivate calm, build resilience, and increase aliveness in 45 days. It's a five-week, cohort-based course that is just wrapping up its sixth cohort in the last three years. In those six cohorts, Jonny has served nearly 1,000 students and earned more than $800,000. Here's the best part – Jonny doesn't have a massive audience. When he launched Nervous System Mastery, he had a couple thousand followers on Twitter and a small email list. This is the magic of a well-designed Signature Product – and Jonny is the perfect example. In this episode, we get into the weeds about how he's grown NSM – what's worked well, what hasn't, and how he's found himself on large podcasts with people like Lenny Rachitsky, Ali Abdaal, Chris Williamson, and more. → Join Nervous System Mastery Full transcript and show notes Jonny's Website / Twitter / Instagram / LinkedIn *** RECOMMENDED NEXT EPISODE → #221: Ryan Hawk – Anatomy of a $12,500 membership earning $400,000+ per year *** ASK CREATOR SCIENCE → Submit your question here *** WHEN YOU'RE READY