Supra Insider

What separates the people who get stronger after a rejection from the people who stay stuck on it?
In this episode of Supra Insider, Marc Baselga and Ben Erez drop the guest format for a one-on-one conversation, with Marc interviewing Ben about a piece he started writing on vacation. The trigger was an email from someone who prepared hard, didn’t get the role, and said it was impossible not to take it personally. Ben explains why that reaction revealed the real subject was resilience, what he notices when debriefing candidates who bounce back versus those who don’t, and why he tells people to transcribe their interviews rather than trust their memories.
They explore the four ingredients Ben believes actually cultivate resilience, the one situation where sending a hiring manager more than a thank-you note can swing a decision, and the step-by-step protocol he runs when something falls apart, drawn from three layoffs, a long run of rejections before his Facebook offer, and a torn ACL.
If you’re coming off a rejection and trying to make sense of it, preparing for interviews and looking for a better way to debrief yourself, or just curious how two operators think about setbacks, 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:
* (03:08) The email that sparked the episode: a candidate who couldn’t help taking a rejection personally
* (08:50) Why how someone reacts to rejection tells Ben so much about their resilience
* (10:03) What resilient job seekers do differently: a learning loop and getting better at calling their shots
* (13:20) Ben’s definition: bounce back, recover, and adapt positively when faced with adversity
* (14:58) Marc on the “irrational optimists” who brush off rejection but never actually adapt
* (20:08) Why you shouldn’t trust your memory of an interview, and the case for transcribing
* (22:31) What AI catches in a transcript, from conversational arc to defensive language, and what it misses
* (27:12) Why people are bad at judging their own interviews, and what a light post-interview protocol looks like
* (28:31) The exception: a candidate who sent proof of work after a live working session and swung the decision
* (36:15) Why not to schedule full onsites with two companies in the same week
* (43:48) The four ingredients: abundance, growth, experimentation, and high agency, Marc’s addition to the framework
* (53:52) Ben’s own record: three layoffs, a long run of rejections before Facebook, and a torn ACL
* (56:55) The protocol starts with acceptance, and why rational acceptance comes before emotional acceptance
* (1:07:58) Why you can’t move forward without an honest story, with a detour through therapy and PTSD
* (1:28:32) Trying on decisions before making them, and how this podcast came out of one
* And more!
Links:
* Ben’s post about how he handles rejection:
https://benerez.substack.com/p/how-i-handle-setbacks-and-coach-resilience
* Tim Urban on Life’s Paths: https://x.com/waitbutwhy/status/1367871165319049221
* 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

After an unexpected layoff, Eric Posen went from day-one outreach to three offers and a director role at Super.com in six weeks.
In this episode, Eric breaks down the search in detail: how he mobilized his network, why he thinks cold applications are dead in this market, what made a referral effective, and the Claude tools he built to track roles and tailor his résumé.
The biggest surprise came across seven interview processes: not one interviewer asked how he used AI. Eric, Marc, and Ben unpack why, along with take-home assignments, taste, negotiating scope and level, and choosing between three offers.
This episode will be useful if you’re searching for a role, preparing for interviews, or rebuilding your hiring process for the AI era.
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:
* (02:09) Eric on being laid off and searching for a job while unemployed for the first time
* (07:01) Why he chose a full-time role over founding again, consulting, or fractional work
* (09:30) Day one: casting a wide net across his network and vibe-coding a job tracking funnel
* (14:55) The “trust bank” metaphor he learned from an old boss
* (15:58) Marc breaks down why Eric’s outreach message made him want to help
* (18:44) Why Eric thinks cold applying is dead in this market
* (22:14) What makes the best referral: someone who works directly with the hiring manager
* (25:40) Building a resume builder with Claude to tailor his story to each role
* (34:35) The big surprise: across seven processes, nobody asked how he uses AI
* (40:25) Ben’s theory: hiring managers now assume baseline AI proficiency
* (50:41) Evaluating the work product instead, and the line between taste and slop
* (56:20) Landing at Super.com and getting up-leveled from senior group PM to director
* (1:04:50) Choosing between three offers, and why level beat name brand
* (1:08:29) The Pie to ZeroClick resume problem after Google’s policy reinterpretation
* (1:22:07) Gratitude Corner: Eric thanks the founders of Mucker Labs and his wife Amanda
* And more!
Links:
* Supra Insider Episode with Anneli Scopazzi: https://suprainsider.substack.com/p/90-how-top-pm-candidates-leverage
* Eric Posen Breakfast Burrito Review site: https://labreakfastburrito.com/
* Erik Rannala: https://www.linkedin.com/in/erikr/
* William Hsu: https://www.linkedin.com/in/william-hsu-032273/
* Eric Posen: https://www.linkedin.com/in/goeric/
* 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

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