Supra Insider

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