Supra Insider

Hosted by Marc Baselga, Ben Erez

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124

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Aug 2026

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A podcast for product leaders inspired by discussions in the Supra product community, hosted by Marc Baselga and Ben Erez. suprainsider.substack.com

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August 24, 20261 hr 18 min

#124: Inside Anthropic's culture interview | Ben Erez & Marc Baselga (co-founders, Insider Loops)

What does it tell you about a company when every single person it hires, in every function, has to pass the same interview about culture? In this episode of Supra Insider, Marc Baselga and Ben Erez set the guest format aside for a conversation Marc started because he noticed something new. After two years of coaching people through interview loops, this was the first time he’d seen Ben genuinely fascinated by one specific interview at one specific company. Ben walks through what he’s pieced together about Anthropic’s culture interview: the no-exceptions policy, the rapid-fire format of ten or more questions in a single 45-minute slot, and the fact that anyone at the company, from marketing to IT, can be trained to run it. They explore the questions that actually get asked, what Ben believes is being evaluated underneath them, why “why Anthropic” demands more depth than the same question anywhere else, and whether the filter holds as the company gets hotter and more candidates learn to say the right things. Then they turn to the question Ben finds most interesting: why almost no other company does this, and what happens inside a company when employees are calibrated to evaluate culture. If you’re preparing for an interview at a frontier lab, thinking about how your own company screens for values, or just curious what a well-designed culture filter looks like from the outside, 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 SUPRAINSIDER50 In this episode, we covered the following topics: * (02:55) Anthropic’s no-exceptions policy: every candidate, every function, the same interview * (04:55) The format: ten to fifteen questions in 45 minutes, not two or three deep stories * (13:15) The two Dario Amodei essays candidates are pointed to, and the light and shade framing * (16:17) A sampling of the questions that actually get asked * (19:15) How Ben coaches the revenue versus safety question by first questioning the premise * (23:55) What he thinks they’re evaluating: communication, intellectual honesty, and authenticity * (26:59) Walking through Anthropic’s seven values and what each one signals * (31:39) Why “why Anthropic” demands more depth than the same question anywhere else * (39:40) The cult comparison, and why you mostly have to convince them you belong * (44:12) Missionaries versus mercenaries, and whether the filter holds as the company grows * (46:52) The bigger question: why doesn’t any other company do this? * (55:55) The flywheel: calibrating employees as interviewers reinforces culture internally * (1:13:49) Why the STAR method backfires here, and how to read the rapid-fire dynamic * And more! Links: * Two essays required for Anthropic’s Interview: * Machines of Loving Grace by Dario Amodei (2024): https://darioamodei.com/essay/machines-of-loving-grace * The Adolescence of Technology by Dario Amodei: https://darioamodei.com/essay/the-adolescence-of-technology * Anthropic’s values: https://www.anthropic.com/careers * Acquired on Sequoia Capital: https://www.acquired.fm/episodes/sequoia-capital-part-1 * Insider Loops: https://www.insiderloops.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: * 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

August 17, 20261 hr 14 min

#123: How a PM recruiter reads your LinkedIn profile | Chris Lee (Founder @ Product Scout, ex- Brex, Dropbox)

Note: this episode contains screen sharing, so it’s best watched on YouTube. What does a recruiter actually see in the ten seconds they spend on your LinkedIn profile, and what makes them scroll past? In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Chris Lee , founder of Product Scout , a boutique firm that helps early-stage founders make their first product hires. Chris explains the idea he calls candidate market fit, why he refuses to give profile feedback until he knows what role you’re aiming at, and why a profile built to appeal to everyone ends up resonating with no one. Then he opens his actual tooling and walks through a live search for a head of product role at an AI-native pharma startup, showing the rubrics his agents score against and why almost everything at the top of the funnel comes down to keywords. He finishes by reviewing Marc’s and Ben’s own profiles against that role, out loud and unfiltered, and passes on both. If you’re job searching and unsure whether your profile is working, weighing how specific to make your story, or a hiring manager curious how sourcing really happens now, 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 SUPRAINSIDER50 In this episode, we covered the following topics: * (02:46) Candidate market fit: why a profile built for everyone resonates with no one * (06:01) The dimensions Chris asks about first: company stage, level, and domain expertise * (08:26) Why he filters out anyone outside the metro for in-person roles, even if they’d relocate * (11:40) The ethics of setting your location to a city you haven’t moved to yet * (16:38) Multiple shots on goal: position for the dream role, test, iterate, then pivot * (19:58) Why a mixed bag of parallel interviews muddies your narrative * (23:08) The first two minutes, and what separates a crafted pitch from a life story * (27:37) The live search setup: a head of product role at an AI-native pharma startup * (34:36) How Chris sources: Claude for research, then his own agents to score profiles * (38:04) The five rubric dimensions his agents grade every profile against * (41:38) Director versus principal IC, and why four years as a director reads as too removed * (44:46) Why he almost never looks at resumes * (49:14) The review begins: Chris walks through Ben’s profile and explains his pass * (58:14) Marc’s turn, and the sub-one-year stint that gets skipped over * (1:05:30) Where Marc and Ben would actually be strong candidates * (1:06:41) Practical fixes: meaty bullets, real metrics, and narrative over recap * (1:11:35) Gratitude Corner: Chris thanks Colin Smith, Charlie Ruiz, and Marc * And more! Links: * Product Scout: https://product-scout.com/ * Charlie Ruiz: https://www.linkedin.com/in/charles-ruiz/ * Colin Smith: https://www.linkedin.com/in/execnow/ * Chris Lee: https://www.linkedin.com/in/thechrislee/ * 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

August 10, 20261 hr 15 min

#122: How to navigate team matching in big tech PM hiring | Ben Erez & Marc Baselga

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 SUPRAINSIDER50 In 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

August 3, 202641 min

#121: Why your side project should start with distribution | Colin Matthews (Head of Education @ Lenny’s Newsletter)

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 SUPRAINSIDER50 In 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

July 27, 20261 hr 37 min

#120: How to stop taking rejection personally | Ben Erez & Marc Baselga

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 SUPRAINSIDER50 In 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

July 20, 20261 hr 24 min

#119: How I landed a director role in six weeks | Eric Posen (Director of Product @ Super.com, ex- ZeroClick, Honey)

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 SUPRAINSIDER50 In 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

July 13, 20261 hr 20 min

#118: What a money coach learned from 200 conversations about wealth | Vaibhav Goel (Money Coach, ex-Doordash, Google, LinkedIn, Microsoft, Lyft)

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 SUPRAINSIDER50 In 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

July 6, 20261 hr 1 min

#117: How Gusto is turning every employee into an AI builder through hackathons | Alex Meyers (Principal Product Manager @ Gusto)

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 SUPRAINSIDER50 In 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

June 29, 20261 hr 19 min

#116: Lessons learned from hiring 4 AI PMs in seven months | Chris Gomes (VP of Product @ Conveyor)

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 SUPRAINSIDER50 In 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

June 22, 20261 hr 4 min

#115: This product leader built an AI brain that runs on every computer at his company | Kyler Ross (Head of Product @ Cloaked)

This episode contains some screen sharing so it’s best watched on YouTube What 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 SUPRAINSIDER50 In 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