Tech workers can be rigorous at work and surprisingly loose with their own money. After more than 200 coaching sessions, Vaibhav Goel keeps seeing the same patterns: too much wealth tied up in one company’s stock, excess cash sitting idle, missed tax-advantaged accounts, and generic advice that does not fit high earners.

In this episode, Marc Baselga and Ben Erez sit down with Vaibhav Goel, a former product leader at DoorDash, Google, Lyft, LinkedIn, and Microsoft who now coaches tech professionals on their finances. They unpack what changes at different net-worth levels, how to think about 529s and concentrated equity, why traditional advisor models can miss this group, and what a more practical financial plan can look like.

They explore the most common money mistakes he sees, how priorities shift at different net-worth levels, plain-English breakdowns of things like 529 accounts and long-short investing, why traditional advisor incentives leave a lot of tech workers underserved, and how to think about diversifying a portfolio that has become dangerously concentrated in one stock.

If you’re a tech worker who optimizes everything at work but defaults on your own finances, someone sitting on concentrated company stock and unsure what to do next, or anyone curious how the newly wealthy actually handle sudden money, this episode is for you.This conversation is for education only and is not personal financial, investment, or tax advice.

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

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

Want company-specific interview intel?

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

Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50

In this episode, we covered the following topics:

* (01:05) Why VB left a dream PM career at Doordash, Google, Lyft, and LinkedIn to become a money coach

* (03:35) The Shopify side business that gave him his first real taste of fulfillment

* (05:39) A decade as his friends’ informal money guy, and the awkward shift to charging

* (08:34) Ben’s counterpoint: charging can actually free friends to ask for more help

* (11:07) What 200-plus sessions reveal about his clients and how personal money really is

* (13:10) The client who is 100% in Tesla, and why people come to him for a second opinion

* (16:36) His coaching process: a financial one-pager, then action items every two weeks

* (19:05) A plain-English breakdown of 529 accounts

* (29:35) The most common mistakes: too much cash, over-concentration, and skipped tax accounts

* (32:18) What to focus on at each net-worth level, starting under $1M

* (44:18) Why advisor incentives leave the “mass affluent” tier underserved

* (01:00:07) The QQQ game: big single-tech stocks underperforming the index

* (01:06:25) Diversifying concentrated stock with exchange funds and buy-borrow-die

* (01:10:06) Why tech workers optimize everything at work but not their own money

* (01:16:48) Gratitude Corner: VB thanks his grandparents, a teacher, an anonymous donor, and his wife

* And more!

Links:

* Vaibhav Goel: https://www.linkedin.com/in/govaibhav/

* Vaibhav’s Calendar: https://calendly.com/simple-money/intro-call

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

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

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

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

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

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

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

What does it actually take to move an entire company from handwriting PRDs to shipping features with agents in two years?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Alex Meyers, Principal Product Manager at Gusto, to trace how the company became AI-native from the inside. Alex shares how his own quiet tool use turned into a C-suite demo, why that demo made clear that you cannot simply mandate “be AI native,” and how PM AI hackathons became the ritual that moved the org forward.

They explore why dedicated, uninterrupted build time beats an hour here and there, why the ritual has to recur as the tools keep changing, how roughly three-quarters of the PM org now merges pull requests, and where Alex thinks the work is heading as loops and goals let PMs spend more time on customers and taste.

If you’re a product leader trying to raise your team’s AI fluency, a founder deciding how much structure to put around learning, or an operator wondering what the PM role becomes when agents handle the busywork, this episode is for you.

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

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

Want company-specific interview intel?

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

Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50

In this episode, we covered the following topics:

* (00:30) Alex on Gusto’s two-year shift from few AI subscriptions to fully AI-native

* (03:57) How adoption spread: his own tool use, the CPO noticing, and early show-and-tell

* (07:06) The pivotal C-suite Cursor demo and the aha that you must create time and structure

* (09:50) The secret sauce: long uninterrupted build blocks over an hour a day

* (12:41) The two big levers: shared access with connected data, plus dedicated space and resources

* (15:00) Why hackathons have to recur as tools change, from prompting to loops

* (22:49) The confidence jump: 11% of PMs to 83% around the hackathons

* (24:44) Working on the business versus in the business, with outputs that ship to customers

* (31:09) The spicy topic: PMs merging PRs, and starting small with tight review gates

* (38:54) A Cursor case study where a PM shipped a feature end to end

* (42:37) Loops versus cron jobs, and the shift to think-and-judge tasks

* (47:15) The CEO founder-mode analogy: humans infusing taste into their own systems

* (52:40) The emerging skill of killing loops, notifications, and artifacts that no longer serve you

* (57:32) Where to find Alex and how listeners can help

* (58:47) Gratitude Corner: Alex thanks his eBay and Gusto bosses, and Marc

* And more!

Links:

* Claire Vo: https://www.linkedin.com/in/clairevo/

* Boris Cherny: https://www.linkedin.com/in/bcherny/

* Peter Steinberger: https://www.linkedin.com/in/steipete/

* Bradford Shellhammer: https://www.linkedin.com/in/bradfordshellhammer/

* Cyrus Mansoor: https://www.linkedin.com/in/cyrusmansoor/

* Katya Fuks: https://www.linkedin.com/in/katya-fuks-58b4272/

* Albert Hsu: https://www.linkedin.com/in/alberthsu5/

* Jasper Malcolmson: https://www.linkedin.com/in/jaspermalcolmson/

* Alex Meyers Website: https://www.alexjmeyers.com/

* Alex Meyers: https://www.linkedin.com/in/alexjmeyers/

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

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

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

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

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

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

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

Chris Gomes set out to hire four AI product managers. Seven months later, his biggest lesson was not about AI at all.

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Chris Gomes, VP of Product at Conveyor, the Series B startup that automates responses to security questionnaires and RFPs. Chris walks through the seven months he spent hiring four AI PMs, why he spent so long defining what an “AI product manager” even means, and the realization that culture fit, not AI skill, was the thing that actually predicted success.

They explore how he rebuilt a stalled interview process by pulling the most important screens to the front, the MOC framework he uses to map each interview step to specific competencies, his case for work trials and customer role-plays, how he treats references and back-channels, and why the gut-level question of whether you’d enjoy working with someone deserves more weight than most rubrics give it.

If you’re a hiring manager trying to run a tighter, higher-signal process, a founder thinking about your first product hires, or a PM preparing for interviews and wondering what teams are really evaluating, this episode is for you.

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

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

Want company-specific interview intel?

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

Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50

In this episode, we covered the following topics:

* (03:47) Chris sets the scene: hiring four AI PMs at Conveyor after their Series B

* (05:09) The big realization: culture fit matters far more than AI skills, and most of the AI part is teachable

* (06:42) How to actually interview for culture by naming what’s genuinely different about yours

* (08:25) Conveyor’s specifics: hungry, humble, smart, plus customer discovery and the honesty-versus-decisiveness balance

* (12:33) Why they were whiffing, and bringing in recruiter Chris Lee to fix the process

* (13:35) Treating hiring like a product: pull the most important screens forward and de-risk the riskiest parts first

* (19:44) Respecting candidates’ time by cutting performative steps that generate mixed signal

* (21:49) Closing with transparency: walking finalists through the board deck, good, bad, and ugly

* (24:16) The work-trial dream, and a more interactive take-home as a middle ground

* (30:27) Their take-home plus a live customer role-play that proved the most predictive step

* (35:56) The MOC framework: mission, outcomes, and stack-ranked competencies mapped to each step

* (40:23) Taking references seriously, the “Who” method, and where back-channels actually help

* (51:02) The vibes question: can you capture whether you’d enjoy working with someone

* (59:30) Meeting finalists in person, even for remote roles, and the jerk-to-the-waiter signal

* (1:03:38) How much to share with candidates upfront, and valuing thinking on your feet

* (1:11:08) Evaluating AI depth without chasing the flavor of the day, plus what they under-tested

* (1:18:53) Gratitude Corner: Chris thanks Chris Lee, Sydney, and Chas

* And more!

Links:

* Chris Gomes on hiring AI PMs:

* https://www.linkedin.com/posts/gomeschris_over-the-past-7-months-ive-hired-4-product-share-7401947584958787584-O9Um/

* https://www.linkedin.com/posts/gomeschris_takeaway-2-from-hiring-four-pms-w-ai-depth-share-7440043809100484608-ziTH/

* Conveyor: https://www.conveyor.com/

* Chris Lee: https://www.linkedin.com/in/thechrislee/

* Sydney Shea: https://www.linkedin.com/in/sydneyfshea/

* Chas Ballew: https://www.linkedin.com/in/chasballew/

* Chris Gomes: https://www.linkedin.com/in/gomeschris/

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

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

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

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

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

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

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

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

What happens when one product leader decides to stop copy-pasting between chat windows and instead build an operating layer that puts coding agents in the hands of an entire company?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Kyler Ross, Head of Product at Cloaked, to walk through the internal “harness” he started building last Thanksgiving: an agent-friendly system of context files and scripts that lets agents read from and write to the team’s real tools. Kyler explains how it gets installed on every company machine, why he treats each new agent session like onboarding an employee, and how a self-improving loop of skills and automated reviews keeps it getting better.

They explore his day-to-day setup for running many agents at once, why worktrees and Claude Code hooks exist to make failure nearly impossible, a one-on-one prep skill that pulls context from every corner of the company, and the layered guardrails, including a nightly “librarian” agent, that keep confidential information from leaking.

If you’re a product or engineering leader trying to make your team more AI-native, someone wiring agents into real workflows, or anyone wrestling with how to run agents safely at scale, this episode is for you.

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

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

Want company-specific interview intel?

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

Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50

In this episode, we covered the following topics:

* (01:15) The Thanksgiving origin: copy-pasting between chat windows and losing prompts pushed Kyler to build a harness

* (02:32) What the harness is: an agent-friendly directory of context plus scripts that give the agent hands to read and write

* (06:18) How Cloaked deploys it: installed by default on every company machine, with nearly everyone using it

* (07:07) Why he owns ~80% of the code, treating it as a nights-and-weekends hobby separate from his day job

* (08:52) The self-improving loop: anyone can trigger a skill to fix a bad session and submit a PR

* (12:23) Using the harness as a testing ground for a more AI-native way to ship code

* (15:17) Why Slack agents, not Claude Code for everyone, democratize access for non-technical roles

* (16:21) Branding it “PMAI” and the Start Cloaked app that onboards employees

* (30:04) His iTerm2 setup and a keyboard shortcut that launches Claude Code in the right place

* (35:48) Maximizing concurrent agents, and the “infinite canvas” he wishes existed

* (39:14) Why running many agents at once becomes a key skill differentiator, and its fatigue tax

* (44:33) Worktrees and Claude Code hooks as deterministic guardrails that make failure nearly impossible

* (50:44) A one-on-one prep skill that pulls Slack, Granola notes, tickets, and docs into one place

* (54:53) Layered confidentiality guardrails and the nightly “librarian” agent, plus the 50,000-line PR story

* (1:01:20) Gratitude Corner: Kyler thanks Mike Carafa and Aashima Ratti

* And more!

Links:

* Cloaked: https://www.cloaked.com/

* Cloaked Job Board: https://jobs.ashbyhq.com/cloaked

* Sr. Product Manager opening: https://jobs.ashbyhq.com/cloaked/f1b12f94-a114-4d4b-a78e-5a6a2b6ee1fe

* Mike Carafa: https://www.linkedin.com/in/michaelcarafa/

* Aashima Ratti: https://www.linkedin.com/in/akratti/

* Kyler Ross: https://www.linkedin.com/in/kyler-ross-63552595/

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

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

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

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

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

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

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

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

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