Supra Insider

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 th...

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 l...

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...

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...

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...

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 ,...

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 Insi...

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 ma...

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...

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...

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 conve...

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...

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 buil...

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-mo...

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 fraction...

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...

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, sche...

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...

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+ int...

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...

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 syst...

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...

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. Mal...

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...

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 Ere...