Supra Insider

What if the most important skill for building AI products has nothing to do with evals, technical background, or knowing how to write a prompt? What if it is the ability to design systems that can handle what you never planned for?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Apurva Garware, who has built and scaled products across Amazon, Microsoft, and Upwork, to make the case that systems thinking is the defining skill of the next era of product management. Apurva explains why non-determinism forces PMs to stop thinking in features and start designing the guardrails, agent contracts, and escalation points that govern how a system behaves at runtime, when no one is watching.

They explore a three-phase framework for governing AI systems across design, deployment, and production; heuristics for deciding what to hand to agents versus escalate to humans; and a sharp insight about the two products every AI-native company is actually building: the customer-facing product, and the internal operational system that drives margin and velocity. Marc and Ben also share their own experience calibrating an agentic workflow at Supra, grounding the conversation in practice.

If you are a PM trying to find your footing in the AI era without a deeply technical background, a founder wrestling with when to reach for AI versus simpler deterministic automation, or a product leader who wants to build more discipline into how your team ships AI products, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (02:13) Apurva’s Amazon story: the Beyoncé/Lemonade moment that exposed how a perfectly functioning algorithm failed due to missing broader context

* (03:47) Why linear thinking is not enough for AI products and why non-determinism requires a fundamentally different mindset

* (07:55) Ben’s working definition of systems thinking: never building anything in isolation, thinking in 3D maps, and setting the laws of physics that govern how a system operates

* (10:05) The NASA control room analogy: what it actually means to govern AI agents at scale with confidence

* (11:15) Three phases of AI system governance: design-time contracts, deployment benchmarks, and runtime production escalations

* (17:20) The 49/51 decision rule: a heuristic for knowing which decisions to escalate to humans and which to trust the system to handle

* (21:25) The “two products” insight: every AI-native company is simultaneously building a customer-facing product and an internal operational product, and most are treating the second one as an afterthought

* (26:26) Rule of thumb: if a deterministic automation can do the job, build that instead of reaching for an AI agent

* (32:33) How to start developing systems thinking: automate personal workflows, follow industry thought leaders, and stay curious even when your day job does not involve AI products

* (39:05) The biggest failure state: trying to build the entire system end-to-end from day one, and why scoping is more important than ever

* (41:00) The pre-mortem approach: scoping what good looks like, then mapping every way it could break before you build

* (51:00) Outsourcing thinking versus reasoning: why PMs must keep their own reasoning intact even as AI handles more of the execution

* (56:11) Gratitude corner: mentors, product communities including Supra, and past teams

* And more!

Links:

* Andrew Ng: https://www.linkedin.com/in/andrewyng/

* Dario Amodei: https://www.linkedin.com/in/dario-amodei-3934934/

* Sam Altman: https://x.com/sama?lang=en

* Aaron Levie: https://www.linkedin.com/in/boxaaron/

* Andrej Karpathy: https://www.linkedin.com/in/andrej-karpathy-9a650716/

* Ilya Sutskever: https://www.linkedin.com/in/ilya-sutskever/

* John Hegeman: https://www.linkedin.com/in/john-hegeman-02137b7/

* Supra: https://www.joinsupra.com/

* Products that count: https://productsthatcount.com/

* The Skip: https://theskip.substack.com/

* Apurva Garware: https://www.linkedin.com/in/apurvacg/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What happens to the product development process when the lines between who builds, who designs, and who decides start to disappear?

In this special episode of Supra Insider, recorded as part of the Blurring Lines series with Aster AI, Ben Erez sits down with Rishin Banker, VP of Product at Maven, to explore how a 25-person team is rethinking product development in real time. Rishin opens with a concrete shift: Maven went from two to three concurrent projects to five to six, same headcount, smaller pods, more decision-making at the team level. The unlock wasn’t hiring. It was front-loading strategy so more people could move into the build phase at once.

They explore how Maven’s head of design shipped a full marketing page to production end-to-end, why months of foundational design system work made that possible, and where Figma still fits. Rishin also gets into the tensions he’s navigating, unexpected handoffs, competing priorities when people build in silos, and the difference between projects that can live in their own container versus ones that need specialist input from the start.

If you’re a product leader restructuring your team for the current moment, a designer or PM excited about building more but unsure how to navigate the role blurring, or curious how a lean startup is actually operationalizing these changes day to day, this episode is for you.

A special thanks Alex Pavlou and our friends at Aster AI for hosting this session!

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (01:05) Intro to the Blurring Lines series and what Maven’s team structure looks like today

* (03:17) From 2-3 to 5-6 concurrent projects: how Maven restructured into smaller pods

* (05:23) Front-loading strategy to unlock parallel building, why the bottleneck definition is shifting

* (07:47) Non-EPD team members becoming builders: the marketing lead vibe-coding a landing page

* (09:24) The designer who shipped end-to-end to production, and why that required foundational work first

* (12:23) Why good engineering hygiene (clean APIs, design systems) matters even more in the AI era

* (17:40) Where Figma still fits, and where clickable prototypes are replacing it

* (21:35) How the team replaced standing meetings with live reviews and more frequent huddles

* (22:53) CEO office hours replacing the weekly design review, and the Duolingo daily review comparison

* (26:00) Change management: what PMs, designers, and engineers are each feeling right now

* (27:50) The real tensions: unexpected handoffs and mismatched ownership between silo builders

* (33:45) How to manage up and bring your CEO along in the current moment

* (34:25) Friday demos: Maven’s favorite meeting of the week and why it’s almost always an AI showcase

* (36:47) Closing thoughts: the silo vs. collaboration tension Rishin is still working through

* And more!

Links:

* Rishin Banker: https://www.linkedin.com/in/rishinbanker/

* Maven: https://maven.com/

* Our episode with Gagan Biyani (CEO of Maven): https://suprainsider.substack.com/p/98-why-mid-career-people-are-doubling?r=486xld

* Aster AI: https://www.asterhq.com/

* Alex Pavlou (Co-founder, Aster AI): https://www.linkedin.com/in/alexpavlou/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What if the reason you feel like you never have enough time isn’t actually a time problem at all?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Molly Siemers, an executive coach for product leaders who spent over two decades building mission-driven products at companies like Kiva, Change.org, and Blurb before launching her coaching practice, Product Craft Works. Molly opens by naming what she's watching in real time: product leaders are running faster than ever, layoffs are everywhere, and the pressure to adopt AI on top of everything else is creating a new kind of cognitive overload. Coaching, she argues, has never been more necessary, not because people need tactics, but because most people are solving the wrong problem.

They explore the difference between time and capacity, why the best senior leaders seem unflappable, and how personal capacity is something you build, not something you find by rearranging your calendar. Molly walks through the integral coaching methodology she trained in, the threshold practice she gives clients to start tapping into body and emotional intelligence, and the three-step framework she keeps returning to: notice, decide, act. The conversation then turns personal, with Marc and Ben reflecting on agency, identity, and what happens when you look around and realize you’ve built a job you hate, or, on the flip side, a life that actually works.

If you’re a product leader feeling overwhelmed and can’t figure out why, someone navigating a career transition and struggling with identity, or a founder or operator who’s curious whether coaching might actually be worth it, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (00:01:34) Why coaching intensity has spiked in the last six weeks: AI acceleration, layoff anxiety, and cognitive overload

* (00:03:17) Who Molly coaches and what makes someone a great coaching client

* (00:05:25) What pulled Molly from product leadership into coaching — and why she always should have been one

* (00:07:04) Does experience matter for coaches? The cold start problem and shared language

* (00:12:54) Coaching fit is about vibes, not credentials — how Molly evaluates both sides of a first conversation

* (00:14:30) “Real time modulation of therapeutic alliance” — Ben’s framework for what makes coaching actually work

* (00:20:36) Assignments as AB tests on your operating system

* (00:22:44) The threshold practice: how to start tapping into emotional intelligence between sessions

* (00:27:56) The three-step coaching framework: notice, decide, act

* (00:37:35) It’s never a time problem — it’s a capacity problem, and why that distinction matters

* (00:40:12) How capacity feels as a concept and how to start building it

* (00:41:23) Agency and capacity go hand in hand — and why Marc does more now than in any full-time role

* (00:57:07) The broken career ladder: what happens when you reach SVP and realize you hate it

* (00:58:50) Why coaching is more important than ever: anchoring to internal signals in a world that changes weekly

* (01:02:15) Where to find Molly and how the audience can be helpful

* (01:03:40) Gratitude Corner: Noah and Mariah DeLeon

* And more!

Links:

* Molly’s Coaching website: https://productcraft.works/

* Molly’s Substack: https://productcraftworks.substack.com/

* Molly Siemers: https://www.linkedin.com/in/mollysiemers/

* Noah Richardson: https://www.linkedin.com/in/noahrichardson/

* Mariah DeLeon: https://www.linkedin.com/in/mariahdeleonhr/

* Island by Aldous Huxley: https://a.co/d/0ek7GmpB

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What if you could know whether your product change was going to work — before a single real user ever saw it?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Tom Charman, co-founder of Blok, a synthetic user simulation platform that lets product teams test interfaces, onboarding flows, and product changes against AI-powered behavioral personas, not just to predict conversion, but to model second and third order effects like churn, confusion, and long-term retention. Tom opens by naming what’s changed: shipping is faster than ever, but the tools PMs use to decide what to build haven’t kept up. AB tests still take two to three weeks. Traditional user research still skews toward power users. And as personalization gets more complex, getting to statistical significance gets harder. That’s the gap Blok is trying to close.

They explore how Blok’s behavioral personas go beyond demographics to model psychographics, emotional state, and memory, including what happens when a user has a bad first experience and comes back to your product skeptical. Tom walks through the ICP trap that kills retention, why the “show don’t tell” principle protects against confirmation bias, and why he thinks the biggest shift happening in product right now is the move from reactive to proactive, replacing AB tests and feature flags with pre-ship simulation that gets you to directional confidence in 12 minutes instead of three weeks.

If you’re a PM tired of going to battle in product reviews without data to back your intuition, a founder trying to understand how synthetic users actually work and whether they’re worth it before Series A, or a product leader looking to understand how the entire feedback loop from idea to deployment is about to be rebuilt, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (01:40) Why PMs are becoming the bottleneck: shipping is fast, deciding what to ship isn’t

* (04:00) The two problems with traditional user research: paid participants and sampling bias

* (08:19) Ben’s summary of Blok: how synthetic users work at a high level

* (11:04) Tom’s “show don’t tell” principle and how Blok actually simulates behavior vs. just asking questions

* (13:32) The four layers of a behavioral persona: demographics, psychographics, emotion, and memory

* (16:21) The anxious user example: how emotional state changes conversion behavior step by step

* (20:00) Second and third order effects: why optimizing conversion can quietly kill retention

* (21:52) The ICP trap: why the lower-converting variant might actually be the right call

* (28:05) The agentic loop: how the full product development stack is being rebuilt

* (33:27) Confirmation bias: how Blok’s chat interface helps remove it from the experiment design

* (42:19) Who should be using this: Tom’s honest answer on post-Series A timing

* (46:26) Scrappy alternative vs. Blok: 30–60% accuracy with Claude versus 87% with purpose-built models

* (53:15) How to build trust with skeptical stakeholders: run Blok alongside a real AB test

* (55:41) The biggest shift in product: proactive vs. reactive, and why feature flags may become obsolete

* (58:53) Where to find Tom and how to be helpful to Blok

* (01:00:48) Gratitude Corner: Olivia (co-founder), the team, and investors Hannah, Ashkan, Marlon, Kevin, and Brendan

* And more!

Links:

* Blok: https://www.joinblok.co/

* Tom Charman: https://www.linkedin.com/in/tcharman/

* Olivia Higgs (Tom’s Co-founder): https://www.linkedin.com/in/oliviahiggs/

* Hannah Chelkowski: https://www.linkedin.com/in/hannahchelkowski/

* Ashkan Mizani: https://www.linkedin.com/in/ashkanmizani/

* Marlon Nichols: https://www.linkedin.com/in/marloncnichols/

* Kevin Novak: https://www.linkedin.com/in/novakkm/

* Brendan Baker: https://www.linkedin.com/in/brendanbaker/

* Chris Neumann: https://www.linkedin.com/in/ckneumann/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What happens to the PM, the designer, and the engineer when a single person with a great idea can take it all the way to market on their own?

In this episode of Supra Insider, Ben Erez sits down with Tomer Cohen, former Chief Product Officer at LinkedIn, where he spent 14 years and led the company’s product transformation through the AI era. Tomer unpacks the full stack builder mindset - not as a job title, but as a fundamental rethinking of how product development works when the bloated, process-heavy model of the last two decades gets collapsed back down to its original building blocks: idea, build, ship.

They explore how Tomer actually rolled this out at LinkedIn across thousands of people, including replacing the traditional APM program with one where candidates submit a working product instead of a resume, and where the final interview is building something end to end in real time. He breaks down the three archetypes he sees emerging - system builders, full stack builders, and specialists - and what he observed clearly separating top performers from the rest: not their tooling, but their judgment. The conversation closes with a Q&A covering how to navigate interpersonal friction as roles blur, when you actually need a specialist to step in, and what skills will remain stubbornly human no matter what.

If you’re a PM, designer, or engineer trying to understand where your role is actually heading and what to do about it right now, trying to think clearly about how to future-proof your career without falling for hype, or curious how a CPO at one of the biggest tech companies in the world actually tried to operationalize this shift - this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (03:18) What the full stack builder mindset actually is and why now

* (04:00) How product development became a “massive behemoth” of process and org complexity

* (06:15) Collapsing the stack back to its original building blocks: idea to market

* (09:05) The GPT-4 moment: how Tomer’s team saw it coming and rewrote the LinkedIn roadmap overnight

* (13:00) How Tomer rolled this out at LinkedIn — from executive leadership first to the APB program

* (16:35) The new hiring process: submit a working product instead of a resume

* (20:07) What actually separated great candidates from good ones: judgment, not tooling

* (25:42) The three archetypes: system builders, full stack builders, and specialists

* (30:00) Your role is changing whether you want it to or not — and what to do about it

* (33:11) Why top talent at LinkedIn leaned in and everyone else didn’t — the growth mindset framing

* (035:55) The leadership hackathon: mandatory vibe coding for LinkedIn’s top R&D leaders

* (38:10) The role of human mentorship when AI can teach you almost anything

* (43:48) Q&A: when do you actually need a specialist to step in?

* (46:33) Q&A: navigating interpersonal friction as roles and lanes blur

* And more!

Links:

* Tomer Cohen’s Podcast: https://www.linkedin.com/newsletters/building-one-7160766300821069824/

* Tomer Cohen: https://www.linkedin.com/in/tomercohen/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What if the cognitive overhead of constant context-switching, endless meetings, and deciding what to work on next could be offloaded to a system that actually knows how you think?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Michael Leibovich, a business unit leader at Adobe overseeing product, design, support, and business strategy, who spent his paternity leave building something most people only talk about: a fully personalized AI chief of staff, built on Claude Code, powered by nothing more than folders and markdown files.

They explore the architecture behind Michael’s system in detail, from session memory and mental models to a people file that auto-updates from meeting transcripts, a knowledge graph that grows over time, and scheduled tasks for daily meeting metabolization and weekly competitive intel. Michael walks through how he bootstrapped his minimum viable context by extracting from ChatGPT’s memory in under ten minutes, why Obsidian became his visual interface of choice, and the moment he realized this was genuinely worth the investment: getting a suggested answer to “what is the highest leverage thing I should do right now?” in a 30-minute gap between meetings.

If you’re a non-technical operator overwhelmed by AI tooling and unsure where to start, a leader constantly context-switching between teams who struggles to protect time for deep work, or someone building out your own context infrastructure and looking for a real-world playbook, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (00:02:08) Why Michael built this: context overload, starting over every time, and the desire for an AI that actually knows him

* (00:13:44) The architecture: just folders and markdown files, no code required

* (00:15:00) The four layers: personal wiki, mental models, voice calibration, and operating protocol

* (00:17:47) Claude Code in the desktop app vs. terminal — and why the app removes the biggest barrier to entry

* (00:21:32) Local storage vs. GitHub: backup anxiety, security tradeoffs, and why GitHub unlocks cloud-based scheduled tasks

* (00:22:37) Earmark for real-time meeting transcription and how it feeds the system

* (00:27:45) Minimum viable context: extracting three pages of foundational context from ChatGPT memory in ten minutes

* (00:30:00) The aha moment: “What is the highest leverage thing I should do in the next 30 minutes?”

* (00:33:50) Obsidian as the visual interface for the Claude folder system

* (00:37:10) The knowledge graph: beliefs, decisions, and a people file that auto-updates from meeting notes

* (00:49:00) Calendar ingestion and the one-pager Michael wishes everyone brought to meetings

* (00:56:01) Where to find Michael and how the audience can be helpful

* (00:57:08) Gratitude Corner: Thanking ex-bosses (Amanda, Wendy, Zoe, Beth), his wife and a dear friend, Will

* And more!

Links:

* Michael Leibovich’s Startup Dad episode:

https://startupdadpod.substack.com/p/create-your-parent-advisory-board-michael-leibovich-adobe

* Earmark (notetaking tool for PMs): https://www.tryearmark.com/

* Obsidian: https://obsidian.md/

* Helpful resources to get started with Claude Code and Obsidian:

* Claude Cowork: The Definitive Setup Guide (works for Code interchangeably): https://x.com/witcheer/status/2027759832523051263

* Claude + Obsidian: The Memory Stack: https://x.cosssm/nyk_builderz/status/2030904887186514336

* CC Chief of Staff Setup Guide (github link): https://github.com/jimprosser/claude-code-cos

* Michael’s post: How I Built My AI Chief of Staff

* Zoe Black: https://www.linkedin.com/in/zoeblack1/

* Wendy Baker: https://www.linkedin.com/in/wendymbaker/

* Amanda Patterson: https://www.linkedin.com/in/amandawpatterson/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What if the reason great talent keeps failing at your company has nothing to do with the talent — and everything to do with the environment you built around them?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Hiten Shah, serial entrepreneur and co-founder of Crazy Egg, who recently had his first-ever job as a PM at Dropbox after selling his company to them. That 15-month experience as an individual contributor — after a lifetime of being the one who owned the environment — completely changed how he thinks about leadership. Hiten unpacks the viral post that kicked off this conversation and introduces a framework most people have never articulated: vibe leads to environment, and environment leads to culture.

They explore what happens when leaders lose ground-level visibility, why escalation is actually healthy in large organizations, and how Hiten’s startup FYI built a concrete interview process to hire specifically for environment fit. The conversation moves through the Toby Lütke / Shopify story, the “nothing changes without fireworks” principle, and why most CEOs are outsourcing environment visibility to the wrong people — before pivoting into Hiten’s current obsession: running OpenClaw bots inside Slack, pair prompting, and how a two-bot thread with 800 messages built an entire product without Hiten touching a line of code.

If you’re a founder who’s started to feel like a prisoner in the company you built, a leader trying to figure out why strong people keep underperforming, or a non-engineer looking to get serious leverage from OpenClaw bots without using Claude Code — this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (02:07) What inspired Hiten’s post: years of work and his first-ever job at Dropbox

* (05:57) “There are no shitty people at work, only shitty environments”

* (16:48) The vibe-environment-culture sequence: why vibe comes before everything

* (23:15) The leadership secret nobody says out loud: leaders make people work their way

* (27:04) Toby Lutke, Shopify, and the cost of cosplaying as a public company CEO

* (32:10) “Nothing changes without fireworks”: the DOD uncle anecdote and Brian Chesky

* (35:30) How to recruit for environment fit: Hiten’s concrete interview process at FYI/Nira

* (39:10) The WHO method for hiring executives and why it works

* (44:35) What triggers an environment reset: when you’re off-goal or moving too slowly

* (57:11) Why bots belong inside Slack, not outside it

* (01:00:50) Pair prompting: humans and bots in the same channel, and the 800-message two-bot thread

* (01:05:30) Giving bots access to your codebase and why it feels like magic

* (01:12:05) Where to find Hiten and what he wants from the audience

* (01:13:33) Gratitude Corner: Morgan Brown and how he helped Hiten through his first job

* And more!

Links:

* Hiten Shah’s post: https://x.com/hnshah/status/1954577790063558665?s=20

* Hiten Shah Website: https://www.hiten.com/

* Hiten Shah X: https://x.com/hnshah

* Hiten Shah: https://www.linkedin.com/in/hnshah/

* Morgan Brown: https://www.linkedin.com/in/morganb/

* Courage to be Disliked (book mentioned by Ben and Hiten): https://www.amazon.com/dp/1501197274

* Who is Michael Ovitz (Biography): https://www.amazon.com/dp/1591845548

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What does it actually take to make fractional work sustainable, not just for a few months, but as a real career path?

In this special solo session, Ben Erez shares everything he’s learned about fractional product work from two distinct perspectives: as Head of Product at Continuum (a Series A marketplace for fractional executives that eventually shut down) and from his own two years doing fractional work. He walks through the foundations that set you up for success, how to actually find work and structure engagements, and most importantly, how to make it sustainable and not die. Ben is ruthlessly honest about what worked, what failed, and why intentionality is the difference between loving fractional work and hating it.

He covers the counterintuitive truth that narrow positioning beats broad positioning (using Phil Carter as a case study), why you need to learn to enjoy marketing yourself or you’ll burn out, and the three non-negotiable requirements for any engagement (relevant expertise + urgent need + budget). Ben shares real revenue data showing the spiky, unsteady income reality, explains the “feast or famine” trap that kills most fractional careers, and why he’s skeptical that demand aggregators will ever crack this market at scale. Plus, tactical advice on pricing, the transition from being helpful for free to asking for money, and why referrals beat every other channel.

If you’re exploring fractional work as a side hustle, between full-time roles after a layoff, or considering it as a long-term path—this session is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (01:35) Why fractional work is popular now but requires extreme intentionality to avoid hating it

* (05:45) Ben’s background: Head of Product at Continuum (fractional marketplace) then 2 years of fractional work

* (08:10) Ben’s journey: lots of experiments and failures (product design studio, part-time PM gigs, advisories, Maven course)

* (22:30) Learning to ask for money, transitioning from being helpful for free to paid engagements

* (23:55) Critical insight: narrow positioning beats broad positioning, you must specialize

* (26:05) Phil Carter case study: hyper-specific positioning (consumer subscription growth, seed to Series C)

* (28:30) Where to find work: referrals/word-of-mouth beat aggregators, why Continuum learned this

* (31:20) The 3 requirements for a good fit: relevant expertise + urgent need + budget

* (32:05) Why to avoid early stage startups, budget mismatch stories ($50K quote → $5K offer)

* (33:45) You need to learn to enjoy marketing yourself, can’t just be comfortable with it

* (43:45) The feast/famine trap: going 100% into “impact cave” kills your pipeline

* (45:25) Real revenue data: 24-month chart showing spiky, unsteady income reality

* (48:10) Advising as low-risk entry point, putting toes in water, not a life raft

* (1:12:30) How to close engagements: leave a great first impression, make it about them, ask for second session

* (1:14:15) Ben’s AI co-pilot for interview prep, productizing what he used to do one-on-one

* And more!

Links:

* Post-lesson feedback survey: https://forms.gle/VhGhkWsAfEL2aX6d9

* Elena Verna’s post: https://www.elenaverna.com/p/is-solopreneurship-right-for-you

* Ben’s LinkedIn post that helped him land his first fractional engagement: https://www.linkedin.com/posts/benerez_ive-been-the-first-pm-at-3-different-startups-activity-7165765316168368129-aPTq

* Phil Carter’s website - great positioning example: https://www.philgcarter.com/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

What happens when everyone can build, but no one breaks through the noise?

In this episode of Supra Insider, Ben Erez sits down with Elan Miller, founder and CEO of branding and design studio Off-Menu, for the podcast’s first live in-person recording. Elan unpacks why this moment is uniquely challenging for brand storytelling—AI has made it easier than ever to build and ship products, but harder than ever to get people to care. He explains how the standard tech playbook (great product + clever go-to-market) no longer works when 10 competitors can copy you within a month, and why honorable points of view are the only sustainable moat.

They explore Anthropic’s Keep Thinking campaign and Super Bowl ads as a masterclass in positioning against OpenAI, discuss why successful positioning must repel people as much as it resonates, and unpack the Granola rebrand (including Ben’s honest reaction as a customer). Elan shares why most rebrands fail (visual makeover without moving anything forward), the different reasons companies should rebrand (talent attraction, internal alignment, crossing the chasm), and his process for finding the “holy s**t insight” that makes people feel seen. Plus, how he’s building AI tools that turn brand strategy into practical inputs for higher-quality outputs, and why strong point of view is the antidote to slop.

If you’re building in a crowded space and struggling to stand out, wondering whether a rebrand is the right move, or trying to articulate what makes you different in a way that actually resonates—this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (02:25) Never been easier to build with AI, never been harder to get people to care

* (03:20) If your product works, 10 people copy you within a month—honorable POV is the only moat

* (05:00) Anthropic/Claude case study: Keep Thinking campaign, NYC popup, Super Bowl ads

* (10:10) The enemy question: if your brand had an enemy, who would it be and why?

* (18:30) Granola rebrand discussion: Ben’s honest reaction as a customer

* (29:20) When is a rebrand the right move? Start with the problem you’re trying to solve

* (30:20) The process: what do we believe that nobody else believes? Why should anybody care?

* (38:00) AI opportunity: strong point of view as input for better outputs—antidote to slop

* (50:15) Who Off Menu turns away vs. who they’re perfect for: big bets to reach inflection points

* (1:02:25) Tech world about to operate like CPG: best story wins, not best product

* (1:12:50) Rubric-based coaching: working backwards from what interviewers actually evaluate

* (1:17:20) Personal trainer analogy: not doing reps for you, showing form and pacing

* (1:29:10) When things are fun, nobody can compete with you

* (1:31:10) Gratitude Corner: thanking his parents and anyone who’s taken a bet on him

* And more!

Links:

* Off-Menu: https://www.off-menu.com/

* Off-Menu Newsletter: offmenu.substack.com

* Elan’s X: https://x.com/elanmiller

* Elan Miller: https://www.linkedin.com/in/elanmiller/

* 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

What if your computer didn’t need a screen in front of you to get work done? That’s the shift Ben Guo, co-founder of Zo, is building toward, and this conversation gets into the specifics of what that actually looks like day to day.

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Ben Guo to explore Zo: a personal cloud computer with built-in AI agents, file storage, scheduled tasks, and the ability to receive commands over text or email. Together, they unpack how Zo differs from the OpenClaw movement and why Ben thinks the personal cloud becomes a device category everyone eventually owns.

The conversation goes deep on how the Zo team actually builds software: writing AI-generated markdown plans before touching any code, reviewing those plans as GitHub PRs, and largely abandoning the traditional to-do backlog in favor of just prompting something and letting it run. They also get into the real overhead that comes with this new way of working, including context management, delegation judgment, and figuring out what belongs where.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (01:50) What Zo is: a computer in the cloud with file storage, AI chat, skills, memory, scheduled tasks

* (06:00) Zo’s origin story: started as an inference platform in 2023, before agents were a thing

* (09:10) OpenClaw appealed to tinkerer/hacker audience, like the Home Brew Computer Club

* (15:20) Zo is designed for people who want to get stuff done, not necessarily tinker all day

* (27:45) The future: we’ll interact with multiple AI computers in our day-to-day

* (30:20) Back to old-school computing: peer-to-peer, FTP, SSH—protocols mostly used by engineers now

* (36:45) Could Zo eventually become the default messaging interface? Text Zo instead of friends?

* (41:00) The workflow: write PRD, ask Zo to translate to Linear tickets, Zo updates them as work progresses

* (46:20) Coding now feels more like managing a team—firing off things, checking back later

* (56:45) Ben Erez’s fanboy moment: Zo is his favorite new product of the year so far

* (59:15) Gratitude Corner: Thanking Tiff Huang (Ben’s girlfriend) for being supportive through 2.5 years of building

* And more!

Links:

* Zo: https://www.zo.computer/

* Tiff Huang: https://bytheophana.substack.com/

* Ben Guo: https://www.linkedin.com/in/0thernet

* 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