Supra Insider

Afleveringen

• 
  #122: How to navigate team matching in big tech PM hiring | Ben Erez & Marc Baselga 10.08.2026 1u 15min

  What happens when you pass every interview, get approved for an offer, and then hear nothing for five months?In this episode of Supra Insider, Marc Baselga interviews Ben Erez about team matching, the stage at large companies where an approved candidate waits for a hiring manager to claim them. Ben walks through how the process actually works from the inside, drawing on his own path into Facebook and what he has since heard from people going through it now.They explore why hiring managers exhaust internal candidates first, what a company-wide reshuffle does to everyone waiting outside, the reported changes at Meta that have left candidates in silence, and the moves that are still within a candidate’s control, including how to see the roles that never get posted publicly and what to say when you reach out.If you’re sitting in team matching wondering whether to keep waiting, preparing for a generalist loop at a big company, or a leader trying to understand why your approved candidate pool keeps growing, 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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (00:56) What team matching is, and the difference between specialist and generalist interview loops* (07:19) Why you don’t get numbers or a written offer until a team claims you* (12:04) Inside the hiring manager’s head, and why internal candidates always come first* (15:35) How Meta’s reshuffle left external candidates behind a deep internal bench* (23:36) Ben’s own path at Facebook: a recruiter sending him roles and matching on the third manager* (27:33) The reported changes at Meta: capped conversations, limited “bullets,” recruiters pulled out* (31:55) A tale of two cities: the AI talent war versus the buyer’s market everyone else is in* (39:42) The controllable controllables, starting with the roles you can’t see from outside* (42:23) Working recruiters, insiders, and cold DMs to manufacture inbound interest* (49:49) What to actually say in the outreach message* (53:53) Be visible, then be legible, and why specificity beats generalist positioning* (1:01:33) Should this practice exist at all? Marc and Ben take opposite ends* (1:11:31) How people mess it up, and why staying stuck beats matching badly* And more!Links:* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% off some 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
• 
  #121: Why your side project should start with distribution | Colin Matthews (Head of Education @ Lenny’s Newsletter) 03.08.2026 41min

  As building gets easier and almost anyone can ship an app in an afternoon, what actually separates a product leader who creates leverage from one who doesn’t?In this special live episode of Supra Insider, recorded on stage at the Toronto Product Conference, Marc Baselga sits down with Colin Matthews, Head of Education for Lenny’s Newsletter and a former founder, PM, and longtime hobbyist builder. Marc lays out a thesis that the best way to prepare for the AI era is to build a real side project, one with actual users and ideally revenue, and Colin pressure-tests it with the framework he uses himself: start with distribution, then work backward to the customers and problems you can reach.They explore the blurring lines between product, engineering, and design, why the code review bar stays the same no matter who writes the code, when to ship a PR versus a prototype versus a spec, why Colin uses AI for comprehension rather than raw velocity, and the two distribution paths he has actually seen work for solo builders.If you’re a PM wondering which skills matter most next, a product leader trying to get your team building, or anyone who keeps starting side projects that never find users, this episode is for you.Huge thanks to Balaji Gopalan, Andrew Williams, and the team at The Toronto Product Conference for hosting us.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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:26) Marc kicks off Supra Insider’s first live podcast and sets up the thesis on side projects and the three judgments* (04:45) Colin on years of building side projects, a roughly 10% hit rate, and what actually counts as a real one* (06:27) His first project, a walk-in clinic reservation app, and the distribution lesson that stuck* (08:12) The distribution-first framework: start with the channel, then find the customers and problems* (10:25) How to bring distribution thinking into your day job, and the career risk of validating bets that fail* (14:09) The blurring lines between product, engineering, and design, and PMs shipping to production* (15:43) Why the code review bar stays the same no matter who submits the PR* (17:22) Colin’s fourth judgment: deciding whether to ship a PR, a prototype, or a spec* (18:40) The profile picture and Base64 example of a simple feature hiding real complexity* (20:26) Using AI for comprehension over velocity, and why he avoids Supabase on a learning project* (23:31) A beginner-friendly stack and the primitives to layer on one problem at a time* (24:50) The case for prototyping almost everything before writing a spec* (26:41) Design systems as leverage, through the Figma MCP or the codebase itself* (30:26) Where to start: learning versus business, and choosing your intention first* (34:22) The distribution sprint, the “meaningful rep,” and the two paths that work for solo builders* And more!Links:* Lenny’s Newsletter * “A guide to AI prototyping for product managers” * “How to get your entire team prototyping with AI”* Toronto Product Conference: https://www.tpma.ca/conference/toronto-product-conference* Toronto Product Con Association: https://www.tpma.ca/* https://www.tpma.ca/conference/toronto-product-conference* Colin Matthews: https://www.linkedin.com/in/colinmatthews-pm/* 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: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 can get up to 35% off some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #120: How to stop taking rejection personally | Ben Erez & Marc Baselga 27.07.2026 1u 37min

  What separates the people who get stronger after a rejection from the people who stay stuck on it?In this episode of Supra Insider, Marc Baselga and Ben Erez drop the guest format for a one-on-one conversation, with Marc interviewing Ben about a piece he started writing on vacation. The trigger was an email from someone who prepared hard, didn’t get the role, and said it was impossible not to take it personally. Ben explains why that reaction revealed the real subject was resilience, what he notices when debriefing candidates who bounce back versus those who don’t, and why he tells people to transcribe their interviews rather than trust their memories.They explore the four ingredients Ben believes actually cultivate resilience, the one situation where sending a hiring manager more than a thank-you note can swing a decision, and the step-by-step protocol he runs when something falls apart, drawn from three layoffs, a long run of rejections before his Facebook offer, and a torn ACL.If you’re coming off a rejection and trying to make sense of it, preparing for interviews and looking for a better way to debrief yourself, or just curious how two operators think about setbacks, 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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (03:08) The email that sparked the episode: a candidate who couldn’t help taking a rejection personally* (08:50) Why how someone reacts to rejection tells Ben so much about their resilience* (10:03) What resilient job seekers do differently: a learning loop and getting better at calling their shots* (13:20) Ben’s definition: bounce back, recover, and adapt positively when faced with adversity* (14:58) Marc on the “irrational optimists” who brush off rejection but never actually adapt* (20:08) Why you shouldn’t trust your memory of an interview, and the case for transcribing* (22:31) What AI catches in a transcript, from conversational arc to defensive language, and what it misses* (27:12) Why people are bad at judging their own interviews, and what a light post-interview protocol looks like* (28:31) The exception: a candidate who sent proof of work after a live working session and swung the decision* (36:15) Why not to schedule full onsites with two companies in the same week* (43:48) The four ingredients: abundance, growth, experimentation, and high agency, Marc’s addition to the framework* (53:52) Ben’s own record: three layoffs, a long run of rejections before Facebook, and a torn ACL* (56:55) The protocol starts with acceptance, and why rational acceptance comes before emotional acceptance* (1:07:58) Why you can’t move forward without an honest story, with a detour through therapy and PTSD* (1:28:32) Trying on decisions before making them, and how this podcast came out of one* And more!Links:* Ben’s post about how he handles rejection: https://benerez.substack.com/p/how-i-handle-setbacks-and-coach-resilience* Tim Urban on Life’s Paths: https://x.com/waitbutwhy/status/1367871165319049221* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% off some 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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  #119: How I landed a director role in six weeks | Eric Posen (Director of Product @ Super.com, ex- ZeroClick, Honey) 20.07.2026 1u 24min

  After an unexpected layoff, Eric Posen went from day-one outreach to three offers and a director role at Super.com in six weeks.In this episode, Eric breaks down the search in detail: how he mobilized his network, why he thinks cold applications are dead in this market, what made a referral effective, and the Claude tools he built to track roles and tailor his résumé.The biggest surprise came across seven interview processes: not one interviewer asked how he used AI. Eric, Marc, and Ben unpack why, along with take-home assignments, taste, negotiating scope and level, and choosing between three offers.This episode will be useful if you’re searching for a role, preparing for interviews, or rebuilding your hiring process for the AI era.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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (02:09) Eric on being laid off and searching for a job while unemployed for the first time* (07:01) Why he chose a full-time role over founding again, consulting, or fractional work* (09:30) Day one: casting a wide net across his network and vibe-coding a job tracking funnel* (14:55) The “trust bank” metaphor he learned from an old boss* (15:58) Marc breaks down why Eric’s outreach message made him want to help* (18:44) Why Eric thinks cold applying is dead in this market* (22:14) What makes the best referral: someone who works directly with the hiring manager* (25:40) Building a resume builder with Claude to tailor his story to each role* (34:35) The big surprise: across seven processes, nobody asked how he uses AI* (40:25) Ben’s theory: hiring managers now assume baseline AI proficiency* (50:41) Evaluating the work product instead, and the line between taste and slop* (56:20) Landing at Super.com and getting up-leveled from senior group PM to director* (1:04:50) Choosing between three offers, and why level beat name brand* (1:08:29) The Pie to ZeroClick resume problem after Google’s policy reinterpretation* (1:22:07) Gratitude Corner: Eric thanks the founders of Mucker Labs and his wife Amanda* And more!Links:* Supra Insider Episode with Anneli Scopazzi: https://suprainsider.substack.com/p/90-how-top-pm-candidates-leverage* Eric Posen Breakfast Burrito Review site: https://labreakfastburrito.com/* Erik Rannala: https://www.linkedin.com/in/erikr/* William Hsu: https://www.linkedin.com/in/william-hsu-032273/* Eric Posen: https://www.linkedin.com/in/goeric/* 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: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 can get up to 35% off some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #118: What a money coach learned from 200 conversations about wealth | Vaibhav Goel (Money Coach, ex-Doordash, Google, LinkedIn, Microsoft, Lyft) 13.07.2026 1u 20min

  Tech workers can be rigorous at work and surprisingly loose with their own money. After more than 200 coaching sessions, Vaibhav Goel keeps seeing the same patterns: too much wealth tied up in one company’s stock, excess cash sitting idle, missed tax-advantaged accounts, and generic advice that does not fit high earners.In this episode, Marc Baselga and Ben Erez sit down with Vaibhav Goel, a former product leader at DoorDash, Google, Lyft, LinkedIn, and Microsoft who now coaches tech professionals on their finances. They unpack what changes at different net-worth levels, how to think about 529s and concentrated equity, why traditional advisor models can miss this group, and what a more practical financial plan can look like.They explore the most common money mistakes he sees, how priorities shift at different net-worth levels, plain-English breakdowns of things like 529 accounts and long-short investing, why traditional advisor incentives leave a lot of tech workers underserved, and how to think about diversifying a portfolio that has become dangerously concentrated in one stock.If you’re a tech worker who optimizes everything at work but defaults on your own finances, someone sitting on concentrated company stock and unsure what to do next, or anyone curious how the newly wealthy actually handle sudden money, this episode is for you.This conversation is for education only and is not personal financial, investment, or tax advice.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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:05) Why VB left a dream PM career at Doordash, Google, Lyft, and LinkedIn to become a money coach* (03:35) The Shopify side business that gave him his first real taste of fulfillment* (05:39) A decade as his friends’ informal money guy, and the awkward shift to charging* (08:34) Ben’s counterpoint: charging can actually free friends to ask for more help* (11:07) What 200-plus sessions reveal about his clients and how personal money really is* (13:10) The client who is 100% in Tesla, and why people come to him for a second opinion* (16:36) His coaching process: a financial one-pager, then action items every two weeks* (19:05) A plain-English breakdown of 529 accounts* (29:35) The most common mistakes: too much cash, over-concentration, and skipped tax accounts* (32:18) What to focus on at each net-worth level, starting under $1M* (44:18) Why advisor incentives leave the “mass affluent” tier underserved* (01:00:07) The QQQ game: big single-tech stocks underperforming the index* (01:06:25) Diversifying concentrated stock with exchange funds and buy-borrow-die* (01:10:06) Why tech workers optimize everything at work but not their own money* (01:16:48) Gratitude Corner: VB thanks his grandparents, a teacher, an anonymous donor, and his wife* And more!Links:* Vaibhav Goel: https://www.linkedin.com/in/govaibhav/* Vaibhav’s Calendar: https://calendly.com/simple-money/intro-call* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% off some 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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  #117: How Gusto is turning every employee into an AI builder through hackathons | Alex Meyers (Principal Product Manager @ Gusto) 06.07.2026 1u 1min

  What does it actually take to move an entire company from handwriting PRDs to shipping features with agents in two years?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Alex Meyers, Principal Product Manager at Gusto, to trace how the company became AI-native from the inside. Alex shares how his own quiet tool use turned into a C-suite demo, why that demo made clear that you cannot simply mandate “be AI native,” and how PM AI hackathons became the ritual that moved the org forward.They explore why dedicated, uninterrupted build time beats an hour here and there, why the ritual has to recur as the tools keep changing, how roughly three-quarters of the PM org now merges pull requests, and where Alex thinks the work is heading as loops and goals let PMs spend more time on customers and taste.If you’re a product leader trying to raise your team’s AI fluency, a founder deciding how much structure to put around learning, or an operator wondering what the PM role becomes when agents handle the busywork, 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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (00:30) Alex on Gusto’s two-year shift from few AI subscriptions to fully AI-native* (03:57) How adoption spread: his own tool use, the CPO noticing, and early show-and-tell* (07:06) The pivotal C-suite Cursor demo and the aha that you must create time and structure* (09:50) The secret sauce: long uninterrupted build blocks over an hour a day* (12:41) The two big levers: shared access with connected data, plus dedicated space and resources* (15:00) Why hackathons have to recur as tools change, from prompting to loops* (22:49) The confidence jump: 11% of PMs to 83% around the hackathons* (24:44) Working on the business versus in the business, with outputs that ship to customers* (31:09) The spicy topic: PMs merging PRs, and starting small with tight review gates* (38:54) A Cursor case study where a PM shipped a feature end to end* (42:37) Loops versus cron jobs, and the shift to think-and-judge tasks* (47:15) The CEO founder-mode analogy: humans infusing taste into their own systems* (52:40) The emerging skill of killing loops, notifications, and artifacts that no longer serve you* (57:32) Where to find Alex and how listeners can help* (58:47) Gratitude Corner: Alex thanks his eBay and Gusto bosses, and Marc* And more!Links:* Claire Vo: https://www.linkedin.com/in/clairevo/* Boris Cherny: https://www.linkedin.com/in/bcherny/* Peter Steinberger: https://www.linkedin.com/in/steipete/* Bradford Shellhammer: https://www.linkedin.com/in/bradfordshellhammer/* Cyrus Mansoor: https://www.linkedin.com/in/cyrusmansoor/* Katya Fuks: https://www.linkedin.com/in/katya-fuks-58b4272/* Albert Hsu: https://www.linkedin.com/in/alberthsu5/* Jasper Malcolmson: https://www.linkedin.com/in/jaspermalcolmson/* Alex Meyers Website: https://www.alexjmeyers.com/* Alex Meyers: https://www.linkedin.com/in/alexjmeyers/* 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: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 can get up to 35% off some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #116: Lessons learned from hiring 4 AI PMs in seven months | Chris Gomes (VP of Product @ Conveyor) 29.06.2026 1u 19min

  Chris Gomes set out to hire four AI product managers. Seven months later, his biggest lesson was not about AI at all.In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Chris Gomes, VP of Product at Conveyor, the Series B startup that automates responses to security questionnaires and RFPs. Chris walks through the seven months he spent hiring four AI PMs, why he spent so long defining what an “AI product manager” even means, and the realization that culture fit, not AI skill, was the thing that actually predicted success.They explore how he rebuilt a stalled interview process by pulling the most important screens to the front, the MOC framework he uses to map each interview step to specific competencies, his case for work trials and customer role-plays, how he treats references and back-channels, and why the gut-level question of whether you’d enjoy working with someone deserves more weight than most rubrics give it.If you’re a hiring manager trying to run a tighter, higher-signal process, a founder thinking about your first product hires, or a PM preparing for interviews and wondering what teams are really evaluating, 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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (03:47) Chris sets the scene: hiring four AI PMs at Conveyor after their Series B* (05:09) The big realization: culture fit matters far more than AI skills, and most of the AI part is teachable* (06:42) How to actually interview for culture by naming what’s genuinely different about yours* (08:25) Conveyor’s specifics: hungry, humble, smart, plus customer discovery and the honesty-versus-decisiveness balance* (12:33) Why they were whiffing, and bringing in recruiter Chris Lee to fix the process* (13:35) Treating hiring like a product: pull the most important screens forward and de-risk the riskiest parts first* (19:44) Respecting candidates’ time by cutting performative steps that generate mixed signal* (21:49) Closing with transparency: walking finalists through the board deck, good, bad, and ugly* (24:16) The work-trial dream, and a more interactive take-home as a middle ground* (30:27) Their take-home plus a live customer role-play that proved the most predictive step* (35:56) The MOC framework: mission, outcomes, and stack-ranked competencies mapped to each step* (40:23) Taking references seriously, the “Who” method, and where back-channels actually help* (51:02) The vibes question: can you capture whether you’d enjoy working with someone* (59:30) Meeting finalists in person, even for remote roles, and the jerk-to-the-waiter signal* (1:03:38) How much to share with candidates upfront, and valuing thinking on your feet* (1:11:08) Evaluating AI depth without chasing the flavor of the day, plus what they under-tested* (1:18:53) Gratitude Corner: Chris thanks Chris Lee, Sydney, and Chas* And more!Links:* Chris Gomes on hiring AI PMs:* https://www.linkedin.com/posts/gomeschris_over-the-past-7-months-ive-hired-4-product-share-7401947584958787584-O9Um/* https://www.linkedin.com/posts/gomeschris_takeaway-2-from-hiring-four-pms-w-ai-depth-share-7440043809100484608-ziTH/* Conveyor: https://www.conveyor.com/* Chris Lee: https://www.linkedin.com/in/thechrislee/* Sydney Shea: https://www.linkedin.com/in/sydneyfshea/* Chas Ballew: https://www.linkedin.com/in/chasballew/* Chris Gomes: https://www.linkedin.com/in/gomeschris/* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #115: This product leader built an AI brain that runs on every computer at his company | Kyler Ross (Head of Product @ Cloaked) 22.06.2026 1u 4min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:15) The Thanksgiving origin: copy-pasting between chat windows and losing prompts pushed Kyler to build a harness* (02:32) What the harness is: an agent-friendly directory of context plus scripts that give the agent hands to read and write* (06:18) How Cloaked deploys it: installed by default on every company machine, with nearly everyone using it* (07:07) Why he owns ~80% of the code, treating it as a nights-and-weekends hobby separate from his day job* (08:52) The self-improving loop: anyone can trigger a skill to fix a bad session and submit a PR* (12:23) Using the harness as a testing ground for a more AI-native way to ship code* (15:17) Why Slack agents, not Claude Code for everyone, democratize access for non-technical roles* (16:21) Branding it “PMAI” and the Start Cloaked app that onboards employees* (30:04) His iTerm2 setup and a keyboard shortcut that launches Claude Code in the right place* (35:48) Maximizing concurrent agents, and the “infinite canvas” he wishes existed* (39:14) Why running many agents at once becomes a key skill differentiator, and its fatigue tax* (44:33) Worktrees and Claude Code hooks as deterministic guardrails that make failure nearly impossible* (50:44) A one-on-one prep skill that pulls Slack, Granola notes, tickets, and docs into one place* (54:53) Layered confidentiality guardrails and the nightly “librarian” agent, plus the 50,000-line PR story* (1:01:20) Gratitude Corner: Kyler thanks Mike Carafa and Aashima Ratti* And more!Links:* Cloaked: https://www.cloaked.com/* Cloaked Job Board: https://jobs.ashbyhq.com/cloaked* Sr. Product Manager opening: https://jobs.ashbyhq.com/cloaked/f1b12f94-a114-4d4b-a78e-5a6a2b6ee1fe* Mike Carafa: https://www.linkedin.com/in/michaelcarafa/* Aashima Ratti: https://www.linkedin.com/in/akratti/* Kyler Ross: https://www.linkedin.com/in/kyler-ross-63552595/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #114: Why I quit my high-paying PM job to go all in as a solopreneur builder | Peter Yang (ex-Roblox, Reddit, Twitter) 15.06.2026 1u 14min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:21) Ben opens on the “unstructured abyss” of solopreneur life and what Peter’s most excited to build* (05:56) Peter’s AI “personal advisor” and the three principles he uses to decide what to say no to* (07:24) Choosing the identity of “builder” and building in public over polished talking-head content* (21:38) How it started: bored at a fintech job, a four-hour OKR meeting, and his first Substack post* (24:35) Why he left: not wanting the VP life of all-day meetings and a game he didn’t want to win* (30:10) Accountability rituals: a content cadence plus AI-generated weekly business and health reports* (32:03) Using AI to spot growth trends he’d have missed, like Substack notes and LinkedIn link posts* (33:36) Codex as his daily driver and running cron jobs using Hermes* (42:18) Symlinking skills so Codex and Claude Code share the same setup* (47:02) Fighting bloat with a “skill that edits skills” and the kill-a-feature problem for AI systems* (52:24) Defining slop and why he guards craft, with the “would my kids see this” test* (58:54) What success looks like: around $1M a year and full control over his time* (1:02:42) Treating a graveyard of dead vibe-coded projects as R&D for the thing with product-market fit* (1:11:32) Where to find Peter and how to help, plus the Gratitude Corner thanking his wife and Ben* And more!Links:* Peter Yang’s recent post: https://open.substack.com/pub/peteryang/p/i-quit-my-high-paying-product-job-to-bet-on-myself* Peter Yang’s X: https://x.com/petergyang* Peter Yang’s Substack: https://creatoreconomy.so/* Peter Yang: https://www.linkedin.com/in/petergyang* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #113: Why free-range AI consulting is the best job in tech right now | Noah Levin (Founder @ Serious People, ex- Amazon & Honor) 08.06.2026 1u 22min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:33) Noah defines the “free-range AI consultant”: applying AI with no fixed stack or playbook, adapting to whatever the business needs* (02:32) Why most of the work is business consulting from first principles, with AI as a tool in service of the goals* (09:55) Why this need exists at all: forward deployed engineer postings up 700%, and Dan Shipper’s point that every agent needs a human* (16:20) The three buckets every company should think about: AI as coworker, AI as operator, and AI as product/engineering* (19:05) The gym, Granola, and Claude Code story: a 20-minute conversation becomes a research report and a working prototype before the meeting ends* (22:17) The floor went up, but raw model output isn’t a finished product; baking work into reusable skills so IP compounds* (27:07) Why the new IP is business judgment, not code, and why you shouldn’t automate a process until you know it’s the right one* (29:30) Why everything is becoming product management, and why PMs get the most leverage from AI* (35:31) “Life is a series of prompts”: every conversation is a prompt for the next task* (40:18) The optimization trap: the unopened Mac Mini and balancing system-building against actual leverage* (48:25) Why not every company is a tech company: McDonald’s three-legged stool and the humility to solve on a client’s terms* (1:04:33) Distribution over building: in a world where anyone can build anything, market choice matters more than the product* (1:08:50) Why the real opportunity is making contact with the world outside tech* (1:13:31) Where to find Noah, plus the Serious People Podcast launching in July* (1:19:27) Gratitude Corner: Noah thanks his first boss, Rick Boultinghouse, from his Navy Pier days* And more!Links and Resources:* Lenny’s podcast with Dan Shipper: https://www.youtube.com/watch?v=4D3hDmGhFhA* Matt Van Horn: https://x.com/mvanhorn/articles* Something big is happening: https://x.com/mattshumer_/status/2021256989876109403* Something small is happening: https://myriadperspectives.com/p/something-small-is-happening* Serious People: https://seriouspeople.ai/* Serious People AI Podcast: https://seriouspeople.ai/podcast* Rick Boultinghouse: https://www.linkedin.com/in/rick-boultinghouse-435a813/* Noah Levin: https://www.linkedin.com/in/noahlevin/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #112: How to Self-Promote Without Burning Trust | Mallory Contois & Hilary Gridley 25.05.2026 52min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (03:35) Hilary’s background: from music blogging to Maven to going full-time after maternity leave* (06:18) Mallory’s background: The Old Girls’ Club, being an 87% introvert, and experimenting without a grand plan* (15:15) Why trust is the most durable professional asset, and how content creation builds it at scale* (18:44) The value exchange principle: give more than you ask for, measured across a year not a single post* (20:47) “You wanna be a magnet for the people you most want to work with” — Hilary on her core motivation* (23:22) Overcoming cringe: why it still feels mortifying every time, and why that doesn’t go away* (27:00) Mallory’s framework: why we were trained to do work in private and why that makes content feel unnatural* (29:47) What happens when you post publicly: the community you find by being brave enough to start* (31:26) Hilary on being misunderstood: simplify, accept the trade-off, and learn from the rude comments* (36:31) Mallory’s Apple Notes system: the messy backlog that keeps content ideas authentic* (39:12) Live Q&A: which platform to start with? Hilary on using Substack as hub and LinkedIn as distribution* (43:06) “Please, for the good of society, change the composition of voices on these platforms”* (48:00) Live Q&A: Hilary’s advice on starting with a talk as your first content format* (49:01) Live Q&A: networking as a byproduct — content as a bat signal for the right people* And more!Links:* Mallory’s Substack: https://www.readgoodwork.com/* The Old Girls Club by Mallory: https://www.jointheogc.com/* Building a Personal Brand (Course by Mallory): https://maven.com/mallory/building-a-personal-brand* Hilary’s AI Guide: https://couchto5k.ai/* Hilary’s Substack: https://hils.substack.com/* How to Become a Supermanager with AI by Hilary: https://maven.com/hilary-gridley/ai-powered-people-management* Mallory Contois: https://www.linkedin.com/in/mallorycontois/* Hilary Gridley: https://www.linkedin.com/in/hilarygridley/* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #111: Why bootstrapping forces you to get better | Marc Baselga & Ben Erez 18.05.2026 1u 30min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (04:30) The optionality question: what paths are Marc and Ben actually considering?* (09:20) Marc’s three paths: full-time job, venture-backed, bootstrapped, and why Anthropic is the only real temptation* (12:04) Full agency over your environment: the real reason the bootstrapped path feels different* (15:54) Ben: “I accomplished 20% of what I was capable of during full-time employment”* (20:00) Playing the same game: why co-founder alignment is everything and corporate environments make it hard* (26:00) Bootstrapping is harder than raising VC, and why that’s actually the advantage* (32:32) Constraints lead to creativity: time as the most precious resource* (36:00) Fun is an emergent property, why finding work that feels fun is harder than it sounds* (44:30) Opportunity-founder fit: how Marc and Ben’s complementary skill sets became clear through action* (01:00:00) The Insider Loops story: from Gamma presentations to a native code base in a week* (01:04:40) Why they stopped planning more than a week out, and why it works* (01:13:00) A year from now: what they each hope to be feeling* (01:22:20) The role of the podcast vs. Insider Loops, and why they have to stay separate* (01:28:28) Thanks to the studio: 28th and Park, NYC (Alex Pavlou and team)* And more!Links:* Alex Pavlou: https://www.linkedin.com/in/alexpavlou/* 28th & Park: https://28thandpark.podyx.com/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #110: Why AI makes systems thinking the most valuable skill for PMs | Apurva Garware (ex-VP Product at Upwork, ex-Amazon) 11.05.2026 58min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (02:13) Apurva’s Amazon story: the Beyoncé/Lemonade moment that exposed how a perfectly functioning algorithm failed due to missing broader context* (03:47) Why linear thinking is not enough for AI products and why non-determinism requires a fundamentally different mindset* (07:55) Ben’s working definition of systems thinking: never building anything in isolation, thinking in 3D maps, and setting the laws of physics that govern how a system operates* (10:05) The NASA control room analogy: what it actually means to govern AI agents at scale with confidence* (11:15) Three phases of AI system governance: design-time contracts, deployment benchmarks, and runtime production escalations* (17:20) The 49/51 decision rule: a heuristic for knowing which decisions to escalate to humans and which to trust the system to handle* (21:25) The “two products” insight: every AI-native company is simultaneously building a customer-facing product and an internal operational product, and most are treating the second one as an afterthought* (26:26) Rule of thumb: if a deterministic automation can do the job, build that instead of reaching for an AI agent* (32:33) How to start developing systems thinking: automate personal workflows, follow industry thought leaders, and stay curious even when your day job does not involve AI products* (39:05) The biggest failure state: trying to build the entire system end-to-end from day one, and why scoping is more important than ever* (41:00) The pre-mortem approach: scoping what good looks like, then mapping every way it could break before you build* (51:00) Outsourcing thinking versus reasoning: why PMs must keep their own reasoning intact even as AI handles more of the execution* (56:11) Gratitude corner: mentors, product communities including Supra, and past teams* And more!Links:* Andrew Ng: https://www.linkedin.com/in/andrewyng/* Dario Amodei: https://www.linkedin.com/in/dario-amodei-3934934/* Sam Altman: https://x.com/sama?lang=en* Aaron Levie: https://www.linkedin.com/in/boxaaron/* Andrej Karpathy: https://www.linkedin.com/in/andrej-karpathy-9a650716/* Ilya Sutskever: https://www.linkedin.com/in/ilya-sutskever/* John Hegeman: https://www.linkedin.com/in/john-hegeman-02137b7/* Supra: https://www.joinsupra.com/* Products that count: https://productsthatcount.com/* The Skip: https://theskip.substack.com/* Apurva Garware: https://www.linkedin.com/in/apurvacg/* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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
• 
  #109: Inside Maven's shift from EPD specialists to flexible builders | Rishin Banker (VP Product @ Maven) 04.05.2026 38min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (01:05) Intro to the Blurring Lines series and what Maven’s team structure looks like today* (03:17) From 2-3 to 5-6 concurrent projects: how Maven restructured into smaller pods* (05:23) Front-loading strategy to unlock parallel building, why the bottleneck definition is shifting* (07:47) Non-EPD team members becoming builders: the marketing lead vibe-coding a landing page* (09:24) The designer who shipped end-to-end to production, and why that required foundational work first* (12:23) Why good engineering hygiene (clean APIs, design systems) matters even more in the AI era* (17:40) Where Figma still fits, and where clickable prototypes are replacing it* (21:35) How the team replaced standing meetings with live reviews and more frequent huddles* (22:53) CEO office hours replacing the weekly design review, and the Duolingo daily review comparison* (26:00) Change management: what PMs, designers, and engineers are each feeling right now* (27:50) The real tensions: unexpected handoffs and mismatched ownership between silo builders* (33:45) How to manage up and bring your CEO along in the current moment* (34:25) Friday demos: Maven’s favorite meeting of the week and why it’s almost always an AI showcase* (36:47) Closing thoughts: the silo vs. collaboration tension Rishin is still working through* And more!Links:* Rishin Banker: https://www.linkedin.com/in/rishinbanker/* Maven: https://maven.com/* Our episode with Gagan Biyani (CEO of Maven): https://suprainsider.substack.com/p/98-why-mid-career-people-are-doubling?r=486xld* Aster AI: https://www.asterhq.com/* Alex Pavlou (Co-founder, Aster AI): https://www.linkedin.com/in/alexpavlou/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #108: How to find clarity when your career path keeps shifting | Molly Siemers (Coach + Advisor for Senior Product Leaders, ex-Kiva, Change.org) 27.04.2026 1u 6min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (00:01:34) Why coaching intensity has spiked in the last six weeks: AI acceleration, layoff anxiety, and cognitive overload* (00:03:17) Who Molly coaches and what makes someone a great coaching client* (00:05:25) What pulled Molly from product leadership into coaching — and why she always should have been one* (00:07:04) Does experience matter for coaches? The cold start problem and shared language* (00:12:54) Coaching fit is about vibes, not credentials — how Molly evaluates both sides of a first conversation* (00:14:30) “Real time modulation of therapeutic alliance” — Ben’s framework for what makes coaching actually work* (00:20:36) Assignments as AB tests on your operating system* (00:22:44) The threshold practice: how to start tapping into emotional intelligence between sessions* (00:27:56) The three-step coaching framework: notice, decide, act* (00:37:35) It’s never a time problem — it’s a capacity problem, and why that distinction matters* (00:40:12) How capacity feels as a concept and how to start building it* (00:41:23) Agency and capacity go hand in hand — and why Marc does more now than in any full-time role* (00:57:07) The broken career ladder: what happens when you reach SVP and realize you hate it* (00:58:50) Why coaching is more important than ever: anchoring to internal signals in a world that changes weekly* (01:02:15) Where to find Molly and how the audience can be helpful* (01:03:40) Gratitude Corner: Noah and Mariah DeLeon* And more!Links:* Molly’s Coaching website: https://productcraft.works/* Molly’s Substack: https://productcraftworks.substack.com/* Molly Siemers: https://www.linkedin.com/in/mollysiemers/* Noah Richardson: https://www.linkedin.com/in/noahrichardson/* Mariah DeLeon: https://www.linkedin.com/in/mariahdeleonhr/* Island by Aldous Huxley: https://a.co/d/0ek7GmpB* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #107: How synthetic users are changing product decision making | Tom Charman (Co-founder @ Blok) 20.04.2026 1u 3min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (01:40) Why PMs are becoming the bottleneck: shipping is fast, deciding what to ship isn’t* (04:00) The two problems with traditional user research: paid participants and sampling bias* (08:19) Ben’s summary of Blok: how synthetic users work at a high level* (11:04) Tom’s “show don’t tell” principle and how Blok actually simulates behavior vs. just asking questions* (13:32) The four layers of a behavioral persona: demographics, psychographics, emotion, and memory* (16:21) The anxious user example: how emotional state changes conversion behavior step by step* (20:00) Second and third order effects: why optimizing conversion can quietly kill retention* (21:52) The ICP trap: why the lower-converting variant might actually be the right call* (28:05) The agentic loop: how the full product development stack is being rebuilt* (33:27) Confirmation bias: how Blok’s chat interface helps remove it from the experiment design* (42:19) Who should be using this: Tom’s honest answer on post-Series A timing* (46:26) Scrappy alternative vs. Blok: 30–60% accuracy with Claude versus 87% with purpose-built models* (53:15) How to build trust with skeptical stakeholders: run Blok alongside a real AB test* (55:41) The biggest shift in product: proactive vs. reactive, and why feature flags may become obsolete* (58:53) Where to find Tom and how to be helpful to Blok* (01:00:48) Gratitude Corner: Olivia (co-founder), the team, and investors Hannah, Ashkan, Marlon, Kevin, and Brendan* And more!Links:* Blok: https://www.joinblok.co/* Tom Charman: https://www.linkedin.com/in/tcharman/* Olivia Higgs (Tom’s Co-founder): https://www.linkedin.com/in/oliviahiggs/* Hannah Chelkowski: https://www.linkedin.com/in/hannahchelkowski/* Ashkan Mizani: https://www.linkedin.com/in/ashkanmizani/* Marlon Nichols: https://www.linkedin.com/in/marloncnichols/* Kevin Novak: https://www.linkedin.com/in/novakkm/* Brendan Baker: https://www.linkedin.com/in/brendanbaker/* Chris Neumann: https://www.linkedin.com/in/ckneumann/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #106: The rise of the full stack builder | Tomer Cohen (Former Chief Product Officer @ LinkedIn) 13.04.2026 51min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (03:18) What the full stack builder mindset actually is and why now* (04:00) How product development became a “massive behemoth” of process and org complexity* (06:15) Collapsing the stack back to its original building blocks: idea to market* (09:05) The GPT-4 moment: how Tomer’s team saw it coming and rewrote the LinkedIn roadmap overnight* (13:00) How Tomer rolled this out at LinkedIn — from executive leadership first to the APB program* (16:35) The new hiring process: submit a working product instead of a resume* (20:07) What actually separated great candidates from good ones: judgment, not tooling* (25:42) The three archetypes: system builders, full stack builders, and specialists* (30:00) Your role is changing whether you want it to or not — and what to do about it* (33:11) Why top talent at LinkedIn leaned in and everyone else didn’t — the growth mindset framing* (035:55) The leadership hackathon: mandatory vibe coding for LinkedIn’s top R&D leaders* (38:10) The role of human mentorship when AI can teach you almost anything* (43:48) Q&A: when do you actually need a specialist to step in?* (46:33) Q&A: navigating interpersonal friction as roles and lanes blur* And more!Links:* Tomer Cohen’s Podcast: https://www.linkedin.com/newsletters/building-one-7160766300821069824/* Tomer Cohen: https://www.linkedin.com/in/tomercohen/* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #105: How I built my AI “chief of staff” | Michael Leibovich (GM, Behance + Adobe Portfolio @ Adobe) 06.04.2026 1u 1min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (00:02:08) Why Michael built this: context overload, starting over every time, and the desire for an AI that actually knows him* (00:13:44) The architecture: just folders and markdown files, no code required* (00:15:00) The four layers: personal wiki, mental models, voice calibration, and operating protocol* (00:17:47) Claude Code in the desktop app vs. terminal — and why the app removes the biggest barrier to entry* (00:21:32) Local storage vs. GitHub: backup anxiety, security tradeoffs, and why GitHub unlocks cloud-based scheduled tasks* (00:22:37) Earmark for real-time meeting transcription and how it feeds the system* (00:27:45) Minimum viable context: extracting three pages of foundational context from ChatGPT memory in ten minutes* (00:30:00) The aha moment: “What is the highest leverage thing I should do in the next 30 minutes?”* (00:33:50) Obsidian as the visual interface for the Claude folder system* (00:37:10) The knowledge graph: beliefs, decisions, and a people file that auto-updates from meeting notes* (00:49:00) Calendar ingestion and the one-pager Michael wishes everyone brought to meetings* (00:56:01) Where to find Michael and how the audience can be helpful* (00:57:08) Gratitude Corner: Thanking ex-bosses (Amanda, Wendy, Zoe, Beth), his wife and a dear friend, Will* And more!Links:* Michael Leibovich’s Startup Dad episode: https://startupdadpod.substack.com/p/create-your-parent-advisory-board-michael-leibovich-adobe* Earmark (notetaking tool for PMs): https://www.tryearmark.com/* Obsidian: https://obsidian.md/* Helpful resources to get started with Claude Code and Obsidian:* Claude Cowork: The Definitive Setup Guide (works for Code interchangeably): https://x.com/witcheer/status/2027759832523051263* Claude + Obsidian: The Memory Stack: https://x.cosssm/nyk_builderz/status/2030904887186514336* CC Chief of Staff Setup Guide (github link): https://github.com/jimprosser/claude-code-cos* Michael’s post: How I Built My AI Chief of Staff* Zoe Black: https://www.linkedin.com/in/zoeblack1/* Wendy Baker: https://www.linkedin.com/in/wendymbaker/* Amanda Patterson: https://www.linkedin.com/in/amandawpatterson/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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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  #104: Why the best talent fails in the wrong environment | Hiten Shah (CEO @ Crazy Egg, ex- Dropbox) 30.03.2026 1u 16min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (02:07) What inspired Hiten’s post: years of work and his first-ever job at Dropbox* (05:57) “There are no shitty people at work, only shitty environments”* (16:48) The vibe-environment-culture sequence: why vibe comes before everything* (23:15) The leadership secret nobody says out loud: leaders make people work their way* (27:04) Toby Lutke, Shopify, and the cost of cosplaying as a public company CEO* (32:10) “Nothing changes without fireworks”: the DOD uncle anecdote and Brian Chesky* (35:30) How to recruit for environment fit: Hiten’s concrete interview process at FYI/Nira* (39:10) The WHO method for hiring executives and why it works* (44:35) What triggers an environment reset: when you’re off-goal or moving too slowly* (57:11) Why bots belong inside Slack, not outside it* (01:00:50) Pair prompting: humans and bots in the same channel, and the 800-message two-bot thread* (01:05:30) Giving bots access to your codebase and why it feels like magic* (01:12:05) Where to find Hiten and what he wants from the audience* (01:13:33) Gratitude Corner: Morgan Brown and how he helped Hiten through his first job* And more!Links:* Hiten Shah’s post: https://x.com/hnshah/status/1954577790063558665?s=20* Hiten Shah Website: https://www.hiten.com/* Hiten Shah X: https://x.com/hnshah* Hiten Shah: https://www.linkedin.com/in/hnshah/* Morgan Brown: https://www.linkedin.com/in/morganb/* Courage to be Disliked (book mentioned by Ben and Hiten): https://www.amazon.com/dp/1501197274* Who is Michael Ovitz (Biography): https://www.amazon.com/dp/1591845548* 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:To support the podcast, please check out the links below:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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 can get up to 35% in some 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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  #103: What senior product people should know about fractional work | Ben Erez 23.03.2026 1u 15min

  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 👇Want company-specific interview intel?If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.In this episode, we covered the following topics:* (01:35) Why fractional work is popular now but requires extreme intentionality to avoid hating it* (05:45) Ben’s background: Head of Product at Continuum (fractional marketplace) then 2 years of fractional work* (08:10) Ben’s journey: lots of experiments and failures (product design studio, part-time PM gigs, advisories, Maven course)* (22:30) Learning to ask for money, transitioning from being helpful for free to paid engagements* (23:55) Critical insight: narrow positioning beats broad positioning, you must specialize* (26:05) Phil Carter case study: hyper-specific positioning (consumer subscription growth, seed to Series C)* (28:30) Where to find work: referrals/word-of-mouth beat aggregators, why Continuum learned this* (31:20) The 3 requirements for a good fit: relevant expertise + urgent need + budget* (32:05) Why to avoid early stage startups, budget mismatch stories ($50K quote → $5K offer)* (33:45) You need to learn to enjoy marketing yourself, can’t just be comfortable with it* (43:45) The feast/famine trap: going 100% into “impact cave” kills your pipeline* (45:25) Real revenue data: 24-month chart showing spiky, unsteady income reality* (48:10) Advising as low-risk entry point, putting toes in water, not a life raft* (1:12:30) How to close engagements: leave a great first impression, make it about them, ask for second session* (1:14:15) Ben’s AI co-pilot for interview prep, productizing what he used to do one-on-one* And more!Links:* Post-lesson feedback survey: https://forms.gle/VhGhkWsAfEL2aX6d9* Elena Verna’s post: https://www.elenaverna.com/p/is-solopreneurship-right-for-you* Ben’s LinkedIn post that helped him land his first fractional engagement: https://www.linkedin.com/posts/benerez_ive-been-the-first-pm-at-3-different-startups-activity-7165765316168368129-aPTq* Phil Carter’s website - great positioning example: https://www.philgcarter.com/* 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: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 can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). 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