Supra Insider

What does it take to walk away from a decade in product, and a job most people would envy, to bet on yourself?
In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Peter Yang, who just left his product lead role at Roblox to go full-time on his newsletter and podcast, Behind the Craft and build his own projects. Peter talks through the trade-offs of solopreneur life, why his calendar is suddenly empty, and how he uses an AI personal advisor with three principles to decide what to say no to.
They explore his day-to-day AI builder stack, from running Codex as a daily driver to using Hermes for his recurring scheduled tasks, his working definition of slop and why he guards against it, and what he’s actually measuring as success now that nobody is handing him a promotion.
If you’re a PM weighing whether to leave a stable job to build on your own, a creator trying to scale output without sliding into slop, or anyone wiring AI agents into their daily work, this episode is for you.
All episodes of the podcast are also available on Spotify, Apple and YouTube.
New to the pod? Subscribe below to get the next episode in your inbox 👇
Want company-specific interview intel?
If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.
Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50
In this episode, we covered the following topics:
* (01:21) Ben opens on the “unstructured abyss” of solopreneur life and what Peter’s most excited to build
* (05:56) Peter’s AI “personal advisor” and the three principles he uses to decide what to say no to
* (07:24) Choosing the identity of “builder” and building in public over polished talking-head content
* (21:38) How it started: bored at a fintech job, a four-hour OKR meeting, and his first Substack post
* (24:35) Why he left: not wanting the VP life of all-day meetings and a game he didn’t want to win
* (30:10) Accountability rituals: a content cadence plus AI-generated weekly business and health reports
* (32:03) Using AI to spot growth trends he’d have missed, like Substack notes and LinkedIn link posts
* (33:36) Codex as his daily driver and running cron jobs using Hermes
* (42:18) Symlinking skills so Codex and Claude Code share the same setup
* (47:02) Fighting bloat with a “skill that edits skills” and the kill-a-feature problem for AI systems
* (52:24) Defining slop and why he guards craft, with the “would my kids see this” test
* (58:54) What success looks like: around $1M a year and full control over his time
* (1:02:42) Treating a graveyard of dead vibe-coded projects as R&D for the thing with product-market fit
* (1:11:32) Where to find Peter and how to help, plus the Gratitude Corner thanking his wife and Ben
* And more!
Links:
* Peter Yang’s recent post: https://open.substack.com/pub/peteryang/p/i-quit-my-high-paying-product-job-to-bet-on-myself
* Peter Yang’s X: https://x.com/petergyang
* Peter Yang’s Substack: https://creatoreconomy.so/
* Peter Yang: https://www.linkedin.com/in/petergyang
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:
To support the podcast, please check out the links below:
* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).
* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.



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

What does it take to bring AI into businesses that run on physical work, human judgment, and processes nobody has ever written down?
In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Noah Levin, founder of Serious People, to unpack what he calls being a “free-range AI consultant.” Noah explains why most of his work is business consulting from first principles rather than AI consulting, why agents still need humans to deliver real value, and how he groups AI for any company into three buckets: a coworker, an operator, and a product or engineering capability.
They explore how AI is collapsing the distance between a conversation and a working prototype, why the new IP is business judgment instead of code, why he believes everything is becoming product management, and the humility it takes to solve problems on a client’s terms inside companies that aren’t, and shouldn’t be, run like tech startups.
If you’re a product leader figuring out where AI actually creates leverage, an operator weighing whether to go independent, or a builder realizing that distribution now matters more than the thing you build, this episode is for you.
All episodes of the podcast are also available on Spotify, Apple and YouTube.
New to the pod? Subscribe below to get the next episode in your inbox 👇
Want company-specific interview intel?
If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.
Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50
In this episode, we covered the following topics:
* (01:33) Noah defines the “free-range AI consultant”: applying AI with no fixed stack or playbook, adapting to whatever the business needs
* (02:32) Why most of the work is business consulting from first principles, with AI as a tool in service of the goals
* (09:55) Why this need exists at all: forward deployed engineer postings up 700%, and Dan Shipper’s point that every agent needs a human
* (16:20) The three buckets every company should think about: AI as coworker, AI as operator, and AI as product/engineering
* (19:05) The gym, Granola, and Claude Code story: a 20-minute conversation becomes a research report and a working prototype before the meeting ends
* (22:17) The floor went up, but raw model output isn’t a finished product; baking work into reusable skills so IP compounds
* (27:07) Why the new IP is business judgment, not code, and why you shouldn’t automate a process until you know it’s the right one
* (29:30) Why everything is becoming product management, and why PMs get the most leverage from AI
* (35:31) “Life is a series of prompts”: every conversation is a prompt for the next task
* (40:18) The optimization trap: the unopened Mac Mini and balancing system-building against actual leverage
* (48:25) Why not every company is a tech company: McDonald’s three-legged stool and the humility to solve on a client’s terms
* (1:04:33) Distribution over building: in a world where anyone can build anything, market choice matters more than the product
* (1:08:50) Why the real opportunity is making contact with the world outside tech
* (1:13:31) Where to find Noah, plus the Serious People Podcast launching in July
* (1:19:27) Gratitude Corner: Noah thanks his first boss, Rick Boultinghouse, from his Navy Pier days
* And more!
Links and Resources:
* Lenny’s podcast with Dan Shipper: https://www.youtube.com/watch?v=4D3hDmGhFhA
* Matt Van Horn: https://x.com/mvanhorn/articles
* Something big is happening: https://x.com/mattshumer_/status/2021256989876109403
* Something small is happening:
https://myriadperspectives.com/p/something-small-is-happening
* Serious People: https://seriouspeople.ai/
* Serious People AI Podcast: https://seriouspeople.ai/podcast
* Rick Boultinghouse: https://www.linkedin.com/in/rick-boultinghouse-435a813/
* Noah Levin: https://www.linkedin.com/in/noahlevin/
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:
To support the podcast, please check out the links below:
* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.
* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).



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

What if the thing holding you back from posting isn’t laziness or a lack of ideas, it’s that nobody ever told you the cringe feeling goes away, and what it actually looks like to build trust with an audience without burning it?
In this special episode of Supra Insider, Ben Erez sits down with Hilary Gridley, creator of the Maven course “How to Become a Supermanager with AI,” and Mallory Contois, former VP of Growth at Maven and founder of The Old Girls Club, for a candid conversation about self-promotion, audience building, and the surprisingly practical mechanics of showing up consistently online without losing yourself in the process. Hilary published a guest post on Lenny’s Newsletter the same morning this was recorded, and that pipeline, from writing to course to full-time career, is exactly what the conversation unpacks.
They cover why trust is the most durable professional asset you can build, how to think about the value exchange between creator and audience, why the psychology of “doing work in private and handing in the final product” makes content creation feel so unnatural, and what both of them actually do to stay consistent without spiraling into algorithm-chasing. Mallory drops a deceptively simple Apple Notes system for never running out of ideas. Hilary makes a sharp case for starting with a talk instead of a newsletter. And both of them are refreshingly honest about the fact that posting still feels mortifying sometimes, and why you should do it anyway.
If you’re a PM, operator, or founder who has been sitting on the sidelines of content creation because it feels cringe, trying to figure out which platform to start with, or building an audience and wondering how to grow it without compromising the thing that makes your voice worth following- this episode is for you.
All episodes of the podcast are also available on Spotify, Apple and YouTube.
New to the pod? Subscribe below to get the next episode in your inbox 👇
Want company-specific interview intel?
If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.
In this episode, we covered the following topics:
* (03:35) Hilary’s background: from music blogging to Maven to going full-time after maternity leave
* (06:18) Mallory’s background: The Old Girls’ Club, being an 87% introvert, and experimenting without a grand plan
* (15:15) Why trust is the most durable professional asset, and how content creation builds it at scale
* (18:44) The value exchange principle: give more than you ask for, measured across a year not a single post
* (20:47) “You wanna be a magnet for the people you most want to work with” — Hilary on her core motivation
* (23:22) Overcoming cringe: why it still feels mortifying every time, and why that doesn’t go away
* (27:00) Mallory’s framework: why we were trained to do work in private and why that makes content feel unnatural
* (29:47) What happens when you post publicly: the community you find by being brave enough to start
* (31:26) Hilary on being misunderstood: simplify, accept the trade-off, and learn from the rude comments
* (36:31) Mallory’s Apple Notes system: the messy backlog that keeps content ideas authentic
* (39:12) Live Q&A: which platform to start with? Hilary on using Substack as hub and LinkedIn as distribution
* (43:06) “Please, for the good of society, change the composition of voices on these platforms”
* (48:00) Live Q&A: Hilary’s advice on starting with a talk as your first content format
* (49:01) Live Q&A: networking as a byproduct — content as a bat signal for the right people
* And more!
Links:
* Mallory’s Substack: https://www.readgoodwork.com/
* The Old Girls Club by Mallory: https://www.jointheogc.com/
* Building a Personal Brand (Course by Mallory): https://maven.com/mallory/building-a-personal-brand
* Hilary’s AI Guide: https://couchto5k.ai/
* Hilary’s Substack: https://hils.substack.com/
* How to Become a Supermanager with AI by Hilary: https://maven.com/hilary-gridley/ai-powered-people-management
* Mallory Contois: https://www.linkedin.com/in/mallorycontois/
* Hilary Gridley: https://www.linkedin.com/in/hilarygridley/
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:
To support the podcast, please check out the links below:
* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).
* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.


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

What does it actually mean to bet on yourself, and how do you know if the game you’re playing is really the one you want to be in?
In this special episode of Supra Insider, Marc Baselga and Ben Erez record together in person for the first time, sitting down at a studio in New York to have an honest, unscripted conversation about optionality, partnership, and what they’ve learned from building Insider Loops over the last seven months. They open with the question hanging over a lot of high-agency people right now: with AI making it easier than ever to go from idea to product, should you leave your job and bet on yourself? Marc names the only full-time role that genuinely tempts him, Anthropic, and then explains exactly why he still wouldn’t take it. Ben unpacks why he accomplished 20% of what he was capable of during his full-time years, and what changed.
They go deep on why bootstrapping is harder than raising VC money, but why the constraints force the kind of market discipline that most funded companies never develop. They map out their complementary skill sets, how they’ve shifted from long-term planning to weekly cadence, and why they now think planning more than a week ahead is mostly a waste of time. The conversation closes on the role of the podcast itself, why it has to stay separate from the business, why fun is an emergent property and not a frivolous goal, and why the relationship comes first.
If you’re weighing whether to leave a stable job and go off on your own, curious about what a bootstrapped partnership actually looks like day to day and what makes it work, or just want a rare honest conversation between two builders about what they’d do differently and what they wouldn’t change, this episode is for you.
A special thanks Alex Pavlou and the team at 28th & Park for the recording space!
All episodes of the podcast are also available on Spotify, Apple and YouTube.
New to the pod? Subscribe below to get the next episode in your inbox 👇
Want company-specific interview intel?
If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.
In this episode, we covered the following topics:
* (04:30) The optionality question: what paths are Marc and Ben actually considering?
* (09:20) Marc’s three paths: full-time job, venture-backed, bootstrapped, and why Anthropic is the only real temptation
* (12:04) Full agency over your environment: the real reason the bootstrapped path feels different
* (15:54) Ben: “I accomplished 20% of what I was capable of during full-time employment”
* (20:00) Playing the same game: why co-founder alignment is everything and corporate environments make it hard
* (26:00) Bootstrapping is harder than raising VC, and why that’s actually the advantage
* (32:32) Constraints lead to creativity: time as the most precious resource
* (36:00) Fun is an emergent property, why finding work that feels fun is harder than it sounds
* (44:30) Opportunity-founder fit: how Marc and Ben’s complementary skill sets became clear through action
* (01:00:00) The Insider Loops story: from Gamma presentations to a native code base in a week
* (01:04:40) Why they stopped planning more than a week out, and why it works
* (01:13:00) A year from now: what they each hope to be feeling
* (01:22:20) The role of the podcast vs. Insider Loops, and why they have to stay separate
* (01:28:28) Thanks to the studio: 28th and Park, NYC (Alex Pavlou and team)
* And more!
Links:
* Alex Pavlou: https://www.linkedin.com/in/alexpavlou/
* 28th & Park: https://28thandpark.podyx.com/
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:
To support the podcast, please check out the links below:
* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.
* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).


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

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