Supra Insider
A podcast for product leaders, inspired by discussions in the Supra product community. Hosted by Marc Baselga and Ben Erez, it explores topics relevant to product leadership. The show is part of the Supra Insider community on Substack, where listeners can find more content.
Episodes
#131: Inside comp negotiation for PM roles at top companies like OpenAI and Anthropic | Colin Lernell (Co-founder @ Valued)
What if the biggest mistake senior product leaders make in negotiation is countering too soon?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Colin Lernell, co-founder and CEO of Valued, a comp negotiation firm, and a former senior product leader. Colin explains why he coaches every client to hold off on the instant counter. Instead, they run due diligence and role alignm
#130: Inside the current executive recruiting market | Nolan Church (Founder @ Mafia Talent, ex-Carta, DoorDash)
What changes about hiring an executive when the best candidates suddenly have fifteen generational companies to choose from and no reason to pick up the phone?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Nolan Church, who was the first head of talent at DoorDash, then chief people officer at Carta, and who now runs executive searches for a small number of companies at
#129: The challenges of working with AI in single-player mode | Andrew Somervell (Co-founder @ Hamster)
When every individual on your team can suddenly move ten times faster, what stops them from moving ten times faster in ten different directions?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Andrew Somervell, co-founder of Hamster, an AI-native workspace for product teams. Andrew and his co-founder built Taskmaster, the open-source tool that shipped plan mode before the
#128: Inside the morning ritual that re-energized our podcast | Ben Erez & Marc Baselga (co-founders, Insider Loops)
What do you do when you’re putting in the same hours, running the same playbook, and the numbers stop moving?In this episode of Supra Insider, Marc Baselga and Ben Erez talk through the slowdown their business hit over the summer and how they worked their way out of it. They walk through the blockbuster April that became a false baseline, the moment in late June when the trend was undeniable, and
#127: What we learned from hiring dozens of people in this market | Jori Bell (VP, Core Experience @ Hampton)
What are hiring managers actually looking for right now, when everyone has a polished resume and nobody knows what the job will look like in a year?In this episode of Supra Insider, Marc Baselga and Ben Erez welcome back Jori Bell, VP of Core Experience at Hampton, where she runs the peer group experience for high-growth founders. Jori sits at an unusual intersection: she has spent the past year h
#126: How to approach PM takehomes for interviews | Ben Erez & Marc Baselga (co-founder, Insider Loops)
Why do so many strong candidates make it deep into an interview process and then quietly lose it on the take-home?In this episode of Supra Insider, Marc Baselga and Ben Erez record one of the morning writing blocks they usually have off the record. Ben has been coaching people through take-homes and noticed almost everyone approaches them the same way: clear the calendar, disappear into a cave, su
#125: How founders turn childhood wounds into superpowers | Dr. Gillian O'Shea Brown (Author & Psychotherapist)
What if part of the drive that built your company began as a childhood defense mechanism?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Dr. Gillian O’Shea Brown, a psychotherapist, complex trauma specialist, and NYU adjunct faculty member whose second book, Psyche’s Awakening, comes out in September. Founders started finding her without her ever setting out to work with
#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 fa
#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 expl
#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
#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.
#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
#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 acro
#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 forme
#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
#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
#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 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 “h
#114: Why I quit my high-paying PM job to go all in as a solopreneur builder | Peter Yang (ex-Roblox, Reddit, Twitter)
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 ca
#113: Why free-range AI consulting is the best job in tech right now | Noah Levin (Founder @ Serious People, ex- Amazon & Honor)
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
#112: How to Self-Promote Without Burning Trust | Mallory Contois & Hilary Gridley
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, fo
#111: Why bootstrapping forces you to get better | Marc Baselga & Ben Erez
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 Insid
#110: Why AI makes systems thinking the most valuable skill for PMs | Apurva Garware (ex-VP Product at Upwork, ex-Amazon)
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
#109: Inside Maven's shift from EPD specialists to flexible builders | Rishin Banker (VP Product @ Maven)
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 con
#108: How to find clarity when your career path keeps shifting | Molly Siemers (Coach + Advisor for Senior Product Leaders, ex-Kiva, Change.org)
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 op
#107: How synthetic users are changing product decision making | Tom Charman (Co-founder @ Blok)
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 conversi
#106: The rise of the full stack builder | Tomer Cohen (Former Chief Product Officer @ LinkedIn)
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 j
#105: How I built my AI “chief of staff” | Michael Leibovich (GM, Behance + Adobe Portfolio @ Adobe)
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 buildi
#104: Why the best talent fails in the wrong environment | Hiten Shah (CEO @ Crazy Egg, ex- Dropbox)
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
#103: What senior product people should know about fractional work | Ben Erez
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 fractiona
#102: How to stand out in a crowded space | Elan Miller (Founder @ Off-Menu)
What happens when everyone can build, but no one breaks through the noise?In this episode of Supra Insider, Ben Erez sits down with Elan Miller, founder and CEO of branding and design studio Off-Menu, for the podcast’s first live in-person recording. Elan unpacks why this moment is uniquely challenging for brand storytelling—AI has made it easier than ever to build and ship products, but harder th
#101: Why everyone should have an AI-powered cloud computer | Ben Guo (Cofounder @ Zo)
What if your computer didn’t need a screen in front of you to get work done? That’s the shift Ben Guo, co-founder of Zo, is building toward, and this conversation gets into the specifics of what that actually looks like day to day.In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Ben Guo to explore Zo: a personal cloud computer with built-in AI agents, file storage, schedul
#100: Reflecting on two years and 100 podcast episodes | Marc Baselga & Ben Erez
What does it take to go from “1 out of 10 chance we hit 100 episodes” to actually getting there?In this special milestone episode, Marc Baselga and Ben Erez reflect on reaching 100 episodes of Supra Insider. They share the raw truth about early imposter syndrome—having a Google Doc with pre-written questions, worrying about sounding stupid, focusing more on optics than enjoyment. They discuss the
#99: How the air force prepared me for product management | Yaniv Fatal (Founding PM @ Blast Security, formerly @ Wiz)
What does it take to go from zero tech experience to founding PM at a cybersecurity startup in three years?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Yaniv Fatal, founding product manager at Blast Security, to unpack his remarkable journey from elite Israeli Air Force pilot to tech. After 13 years in the military and zero technical background, Yaniv failed 20+ interv
#98: Why mid-career people are doubling down on self-learning | Gagan Biyani (CEO and Co-Founder @ Maven)
What if the biggest barrier to learning AI isn’t the tools—it’s how we approach learning itself?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Gagan Biyani, CEO and co-founder of Maven, to unpack why this moment is critical for mid-career professionals to prioritize self-learning. Gagan shares lessons from running a cohort-based learning platform and conducting 30-50 int
#97: What it means to be a forward-deployed product leader | Chase Schwalbach (SVP Product & Technology @ Millie)
What if the best way to lead product is to build it yourself first?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Chase Schwalbach, SVP of Product and Technology at Millie, to unpack a radically different approach to product leadership. Despite his title, Chase spent months as an IC, rolling up his sleeves to build healthcare infrastructure, teach himself AI eval systems
#96: Inside Magic Patterns: Why frontend focus helps win over product teams | Alexander Danilowicz (CEO & Co-founder @ Magic Patterns)
What if the best product decision is saying “no” to what everyone else is building?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Alexander Danilowicz, founder and CEO of Magic Patterns, to unpack why his AI prototyping tool is the only one refusing to add backend features—even when competitors like Lovable, Bolt, and v0 are racing in that direction. Alex explains how fo
#95: How to find your authentic voice online without faking it | Mallory Contois (VP Growth @ Maven, Ex-Pinterest)
What if the thing holding you back from building a public presence is exactly what would make you stand out?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Mallory Contois, VP of Growth at Maven, to unpack why this is the perfect moment for product leaders to start sharing publicly—even if they don’t feel polished, interesting, or like they have it all figured out. Mallor
#94: How AI is enabling top operators to open-source their expertise | Casey Winters (Co-founder & CEO @ SuperMe, ex-Eventbrite & Pinterest)
What if AI didn’t just give you answers—but helped you understand how the best operators actually think?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Casey Winters, former growth leader at Pinterest and Eventbrite, to unpack why he’s building SuperMe, an AI-native professional network designed around perspective, not content or virality.Casey shares why meaningful exper
#93: Why a product marketing background is a PM superpower | Michael Chen (Product @ DoorDash, ex-Asana, Slack, LinkedIn)
Switching into product can feel like a one-way door, especially if you’re already successful in another function. But for Michael, the path from product marketing to product management wasn’t a leap of faith, it was a series of low-risk experiments, relationship-driven conversations, and intentional “spikes” he could bring to the PM role.In this episode of Supra Insider, Marc Baselga and Ben Erez
#92: Are universities failing to prepare students for jobs? | Stephen Cognetta (Co-founder @ Exponent, ex-Google)
What is the role of education when AI can explain, generate, and tutor instantly, and what does that mean for how we learn, teach, and evaluate understanding?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Stephen Cognetta to explore how education is evolving in the age of AI, and why many existing learning models are fundamentally misaligned with how people actually deve
#91: How pre-seed investors evaluate startup moats in the AI era | Itamar Novick (Founder & General Partner @ Recursive Ventures)
What actually makes a startup defensible anymore, especially when anyone can build a product overnight with AI?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Itamar Novick, founder of Recursive Ventures and longtime operator-turned-investor, to unpack how moats are changing in the AI era and what founders (and senior product leaders) need to internalize if they want to b
#90: How top PM candidates leverage recruiters to their advantage | Anneli Scopazzi (Founder @ Boulevard Recruiting, ex - Figma, Palantir, Notion)
Most candidates treat recruiter calls like a box-checking step. But the candidates who consistently land offers treat recruiters like strategic partners - and use them to get real leverage throughout the process.In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with our repeat guest, Anneli Scopazzi (Boulevard Talent; former recruiting leader across Palantir, Figma, and Notion)
#89: The hidden role of rituals in Duolingo's product culture | Nickey Skarstad (Director of Product @ Duolingo, ex-Airbnb, Etsy)
What does it take to build products that feel thoughtful, emotionally resonant, and unmistakably high-quality, especially inside a company that ships fast and experiments constantly?In this episode of Supra Insider, Marc and Ben sit down with Nickey Skarstad, Director of Product at Duolingo, to unpack how one of the world’s most beloved consumer apps maintains its bar for craft, clarity, and delig
#88: How to accelerate your company's AI adoption with a 5-day hackathon | Gaurav Hardikar (VP Product & Growth @ HomeLight)
Listen now: Spotify, Apple and YouTubeWhat actually changes inside a product and engineering org when a company commits to becoming AI-native—not as a side project, but as the new operating system?In this episode of Supra Insider, Marc and Ben sit down with Gaurav Hardikar, VP of Product at HomeLight, to unpack the company’s ambitious transformation: an executive team hackathon, ten AI initiatives
#87: WTF is "Product Taste" and unpacking the PM hype around it | Sachin Rekhi (AI course creator, founder, ex-LinkedIn product leader)
Listen now: Spotify, Apple and YouTubeIf you’ve been hearing phrases like “taste is the only thing that will matter for PMs in the AI era” but aren’t sure what that actually means—or more importantly, how to build it—this episode is for you.In this conversation, Marc and Ben sit down with Sachin Rekhi, founder, former LinkedIn product leader, and creator of LinkedIn Sales Navigator, to unpack the
#86: How senior PMs get 10x leverage by “hiring” AI agents | Jacob Bank (Founder/CEO @ Relay.app)
Listen now: Spotify, Apple and YouTubeIn the first-ever live recording of Supra Insider, Marc and Ben sat down with Jacob Bank, founder of Relay.app, to unpack one of the most urgent questions facing product leaders today: How do AI agents actually change the way we work? Instead of abstract predictions, Jacob shares the very real workflows, failures, and breakthroughs behind running a 10-person c
#85: How to decide whether to start a course | Claire Chen (Growth @ Maven)
Listen now: Spotify, Apple and YouTubeIf you’ve ever wondered whether you could teach a course, how to validate demand for your expertise, or how AI is reshaping learning and personal brand building, this episode is for you.In this conversation, Marc and Ben sit down with Claire Chen, leading Growth at Maven and the person who originally recruited Ben to teach on the platform. Together, they unpac
#84: How Reforge launched 5 AI products in 9 months with just 25 people | Brian Balfour (Founder/CEO @ Reforge)
Listen now: Spotify, Apple and YouTubeIf you’re a product leader trying to navigate the shift from single-product focus to a broader portfolio—or wondering how AI is reshaping execution, team design, and strategic planning—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Brian Balfour, CEO of Reforge, to explore how product orgs can expand into multi-product por
#83: The scariest episode we’ve ever recorded: Marc & Ben’s live coaching session with Josh Herzig-Marx
Listen now: Spotify, Apple and YouTubeWhat happens when a creative side project starts to gain traction—but the founders have different ideas about how far to take it?In this unusually raw episode of Supra Insider, Marc and Ben invite their longtime friend and coach Josh Herzig-Marx to facilitate a live coaching session—on the podcast. Together, they explore the tension between friendship and busi
#82: Inside the new recruiting reality: fewer hires, higher bars | Anneli Scopazzi (Founder @ Boulevard Recruiting, ex - Figma & Notion)
Listen now: Spotify, Apple and YouTubeWhether you’re searching for your next role or hiring in a market where talent is scarce and expectations are sky-high—this episode is for you.Marc and Ben sit down with Anneli Scopazzi, founder of Boulevard Recruiting and former recruiting leader at Figma, Notion, and Palantir, to unpack how recruiting dynamics have shifted in early-stage startups. From the p
#81: I spent 3 months at an AI-native startup where every role ships code | James Dillard (Product Leader, ex-Stripe & YouTube)
Listen now: Spotify, Apple and YouTubeWhat does “AI-native” actually look like inside a company — not in theory, but in practice?In this episode of Supra Insider, Marc and Ben sit down with James Dillard, former YouTube and Stripe PM, who recently spent three months embedded at Roo Code, an AI-native startup building coding agents that can write and review production code.James shares what it was
#80: Becoming an IC again is how products leaders will stay relevant in the AI era | Gokul Rajaram (Investor and Company Helper; ex-Google, ex-Facebook)
Listen now: Spotify, Apple and YouTubeIf you’re a product leader wondering whether climbing the ladder is still the best path - or sensing a shift in where the real leverage is in the age of AI - this episode will change how you think about your role.Gokul Rajaram (DoorDash board member, ex-Square, Google, Facebook) joins Marc and Ben for a powerful conversation about why many senior product leade
#79: The art of disagreeing with your CEO without putting your career at risk | Elena Luneva (CPO & Advisor, Ex-Braintrust, Nextdoor)
Listen now: Spotify, Apple and YouTubeHow do you disagree with your CEO, especially a visionary founder, without putting your job or credibility at risk?In this episode of Supra Insider, Marc and Ben sit down with Elena Luneva (CPO, advisor, and executive coach) to unpack one of the most common, emotionally fraught challenges in product leadership: what to do when your CEO wants to change directio
#78: How to package and monetize your expertise with AI | Ben breaks down the complete workflow creating his interview prep copilot
Listen now: Spotify, Apple and YouTubeIf you’ve ever considered turning your expertise into a scalable product—or wondered what it actually takes to build and sell a useful AI copilot—this episode is for you.In this episode, Ben shares the full behind-the-scenes story of how he packaged his product management knowledge into a sellable, high-leverage AI Practice Copilot. From initial validation to
#77: How AI is eliminating the PM handoff tax | Adam Fishman (Product & Growth Advisor)
Listen now: Spotify, Apple and YouTubeWhat does it mean to truly be an “AI-native” company? And how are product roles evolving when PMs are expected to both execute faster and make sharper strategic decisions?In this episode of Supra Insider, Marc and Ben sit down with Adam Fishman—host of the Startup Dad podcast and longtime product leader and advisor —to unpack the key themes from Reforge’s rece
#76: A special look at Insider Loops
Listen now: Spotify, Apple and YouTubeWhat if interviewing for a PM job at Stripe, Uber, or Figma didn’t feel like walking into the unknown?In this episode of Supra Insider, Marc and Ben take you behind the scenes of building Insider Loops—a new set of interview prep guides designed to give candidates the inside track at some of tech’s most competitive companies. They break down why they saw the o
#75: Aligning personal finance with your values and life satisfaction | Zach Teutsch (Founder @ Values Added Financial)
Listen now: Spotify, Apple and YouTubeWhat if personal finance wasn’t just about saving more or investing better—but about designing a life that feels meaningful, intentional, and aligned with your values?In this episode of Supra Insider, Marc and Ben sit down with Zach Teutsch, founder of Values Added Financial, to explore a radically human approach to wealth management. Instead of fixating solel
#74: How experienced engineers actually use AI coding tools | Nick Meehan (Senior Software Engineer @ Ontra)
Listen now: Spotify, Apple and YouTubeIf you’ve wondered how much AI is really helping engineers - or feared it might replace them - this episode is for you.In this conversation, Marc and Ben sit down with Nick Meehan, a senior engineer and longtime collaborator, to explore how AI coding tools like Cursor, Claude, and Codex are reshaping day-to-day engineering work. Nick shares how his process evo
#73: The Portfolio Career That Made Him a Better Parent | Ben's Episode on the Startup Dad Podcast
Listen now: Spotify, Apple and YouTubeThink a “portfolio career” makes family life chaotic? Ben argues the opposite.In this special episode of Supra Insider, Ben shares a more personal side of his journey in a conversation originally recorded on the Startup Dad podcast with Adam Fishman.From raising his daughter Gaia (with help from George, the family’s golden retriever) to navigating solo parenti
#72: How to scale your team's intuition with AI-powered research | Aaron Cannon (Cofounder & CEO @ Outset)
Listen now: Spotify, Apple and YouTubeAI is transforming the way product teams approach customer research—but what should remain human, and what can be handed off to AI agents? In this episode, Marc and Ben sit down with Aaron Cannon, co-founder of Outset, to explore the evolving role of AI in discovery and usability testing. Aaron unpacks how AI-moderated research enables unprecedented speed and
#71: How PMs can get leverage via agents and MCPs in Cursor | Amir M (Cofounder @ Humblytics)
Listen now: Spotify, Apple and YouTubeWhat if you could cut your QA cycles from days to minutes—and draft PRDs that actually update themselves as your product evolves?In this episode of Supra Insider, Marc and Ben sit down with Amir M, cofounder of Humblytics, to explore how he’s running a two-person startup across engineering, QA, and product using Cursor and Model Context Protocols (MCPs). Amir
#70: How to capture the AI integration opportunity with MCP | Reid Robinson (Lead AI Product Manager @ Zapier)
Listen now: Spotify, Apple and YouTubeAs AI agents become the new interface for work, a major question looms: how will your product connect into this ecosystem?In this episode of Supra Insider, Marc and Ben sat down with Reid Robinson, product manager leading AI at Zapier. They talked about the rise of Model Context Protocols (MCPs) — the new standard for connecting AI agents to tools and data sou
#69: Why product leaders should embrace politics instead of avoiding it | Rich Mironov (Product Management Veteran & Coach)
Listen now: Spotify, Apple and YouTubeWhat happens to product management when building becomes nearly frictionless—and AI threatens to replace the “busy work” PMs have traditionally done?In this episode of Supra Insider, Marc and Ben sit down with legendary product coach Rich Mironov to explore the shifting value of product leadership in the AI era. They unpack why great PMs must now double down o
#68: Why authentic storytelling beats credentials | Charles Ruiz (Keynote Speaker, Founder & Executive Coach)
Listen now: Spotify, Apple and YouTubeWhat if the key to showing up as a great leader had nothing to do with your title, metrics, or credentials—and everything to do with knowing who you are outside of work?In this episode of Supra Insider, Marc and Ben sit down with executive coach Charles Ruiz to explore how leaders can shift from external validation to authentic presence. Charles shares the ori
#67: Untangling identity from job title | Jori Bell (VP Core Experience @ Hampton, ex-Spotify, SoundCloud, Audible)
Listen now: Spotify, Apple and YouTubeWhat if walking away from your polished product career was the exact move you needed to grow?In this episode of Supra Insider, Marc and Ben sit down with Jori Bell to explore her unconventional journey from PM roles at Spotify, SoundCloud, and Audible to building a coaching practice, curating intimate community spaces, and teaching at Cornell Tech. After two y
#66: How MCP enables AI to know you better | Mike Bal (Head of Product and AI @ David’s Bridal)
Listen now: Spotify, Apple and YouTubeWhat if you had a personalized AI toolkit—not just a chatbot—that actually remembered your projects, your workflows, and even your family’s preferences?In this episode, Marc and Ben sit down with Mike Bal, a product leader experimenting at the frontier of AI tooling. Mike shares how he built a local memory system for Claude using Model Context Protocols (MCPs)
#65: How to build an AI career coach in 90 minutes | Kavita Anand (VP, Product & Design @ NewtonX)
What if you could access a personalized career coach anytime—one who remembers your goals, understands your tendencies, and gives you thoughtful, actionable guidance?In this episode of Supra Insider, Marc and Ben sit down with Kavita Anand, a product leader at NewtonX, to explore how she built her own AI-based career coach using tools like Claude and ChatGPT—and then taught 30+ women at her compan
#64: How top companies evaluate PM candidates in 2025 | Nickey Skarstad (Duolingo), Stephanie J. Neill (Stripe), and Chantal Cox (LTK)
If you’re navigating today’s brutally competitive PM job market and wondering what “good” looks like, this episode will become your playbook. In this episode, Ben moderates a candid panel with three veteran product hiring managers:Nickey Skarstad – Director of Product, Duolingo (now leading Duolingo Math)Stephanie J. Neill – Head of Product, Stripe TaxChantal Cox – Director of Product, LTK (Liketo
#63: How PMs can bring predictability to AI products | Aman Khan (Head of Product @ Arize AI, ex-Spotify, ex-Apple)
If you’ve ever launched an AI feature and later realized it wasn’t quite ready—or struggled to define what “quality” even looks like in an AI product—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Aman Khan, Head of Product of Arize AI and a leading voice in AI product evaluation. Aman has helped dozens of teams—from scrappy startups to massive consumer platfo
#62: Why the future belongs to spiky PMs who use AI to magnify their strengths | Hilary Gridley (Head of Core Product @ WHOOP)
What actually sets you apart in a world where AI can do more and more of your job? In this episode, Marc and Ben are joined by Hilary Gridley—Head of Core Product at WHOOP and instructor of the Maven course How to Be a Supermanager with AI—to unpack how great product leaders can use AI to magnify their strengths instead of dulling them.Hilary breaks down her approach to time allocation, sharing ho
#61: How jobs-to-be-done (JTBD) nearly killed our startup | Troy Sultan and Austin Cooley (Co-founders @ Guide)
If you’ve ever found yourself torn between chasing a long-term product vision and urgently responding to customer demands—or wondered how to strike the right balance between innovation and pragmatism—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Troy Sultan and Austin Cooley, co-founders of Guide, to explore how they transformed their entire product philosoph
#60: What PM candidates get wrong about behavioral interviews | Robert Hamilton (PM interview coach, ex-Meta, ex-Google)
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Robert Hamilton, executive coach and former Meta and Google PM, to unpack the art and science of behavioral interviews. If you’ve ever struggled with the infamous “leadership and drive” loop or wondered why your best stories aren’t landing, this episode is a must-listen.They explore why behavioral interviews are oft
#59: How this AI-powered duo found PMF by building 3 products in 9 months | Andy Keil & Kyle Ledbetter
Welcome to another episode of Supra Insider. This time, Marc sat down with Kyle Ledbetter and Andy Keil, the co-founders of Dreambase—an AI-native toolset built on top of Supabase. Despite not having formal engineering backgrounds, Kyle and Andy have built and launched three fully functional products in just nine months.They unpack their unique zero-to-one process—from jamming on whiteboards to bu
#58: Why PM hiring is broken (and how to fix it) | Mike Curti & Joshua Herzig-Marx
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Mike Curti, a recently hired product leader, and Joshua Herzig-Marx, a trusted advisor to early-stage startups and product teams. Together, they unpack one of the most mission-critical and misunderstood topics in product leadership: hiring.They break down what’s broken in today’s interview processes, especially for
#57: What product leaders get wrong about strategy | Melissa Perri (board member, author of Escaping The Build Trap)
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Melissa Perri, author of Escaping the Build Trap and one of the world’s leading product strategy experts. Melissa shares lessons from advising CEOs, founders, and product leaders on how to build strategy that works, scale from VP to CPO, and navigate the often tricky dynamic between founder-CEOs and product leaders.
#56: How to find work you love | Troy Sultan (Co-Founder & CEO @ Guide)
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Troy Sultan, co-founder and CEO of Guide, to unpack the state of job searching and recruiting in the AI era.Troy shares a compelling behind-the-scenes look at what’s really going on inside recruiting teams today—and why the typical candidate experience is often so broken. He also explains how AI and modern tooling a
#55: How v0 has changed the way we build product | Sanket Kavishwar (Director of Product @ Relyance AI)
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Sanket Kavishwar, Director of Product at Relyance AI. Sanket is one of the most active members in Supra’s AI workflows Slack channel, and in this episode, we explore how he’s transforming his company’s product development process with AI prototyping tools like V0.We dive into how Relyance AI shifted from traditional
#54: How leading designers are riding the AI prototyping wave | Will Newton (Principal Product Architect @ Amplitude)
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Will Newton, Principal Product Architect at Amplitude—and one of our most popular past guests—for a follow-up conversation on the fast-evolving world of AI tooling in product design and development.In just a few weeks since our last chat, Amplitude has gone from early AI experimentation to giving Bolt licenses to ev
#53: The state of AI prototyping for product managers | Colin Matthews & Tal Raviv
Welcome to another episode of Supra Insider. This time, Ben and Marc sat down with Tal Raviv and Colin Matthews for a candid conversation about how AI is reshaping the work and mindset of modern product managers.They unpack insights from Tal’s recent survey on AI prototyping adoption, common challenges for PMs using AI tools, and the importance of learning how to experiment effectively. Colin shar
#52: The beautiful mess of organizational context | John Cutler & Joshua Herzig-Marx
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with John Cutler and Joshua Herzig-Marx for a wide-ranging conversation about how AI is transforming the way product teams build, collaborate, and scale. John shares why he joined a new early-stage startup as Head of Product and how the team is breaking the traditional rules of product development—starting with a platfor
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