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by Marc Baselga, Ben Erez
Conversations about hiring, interviews, and careers for product leaders. Hosted by Marc Baselga and Ben Erez (co-founders of Insider Loops). suprainsider.substack.com
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- Yesterday1h 36m
#135: Inside a live co-founder money therapy session | Jeff Greenberg (Executive & Founder Coach)
What happens when two co-founders sit down and talk honestly about money, not as a spreadsheet, but as fear, desire, and freedom?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Jeff Greenberg, an executive coach and therapist who spent a decade on Wall Street as a macroeconomist, for a live co-founder coaching session on their relationship with money. Jeff guides them through a short mindfulness practice and a structured exercise adapted from couples work. Marc and Ben ask each other what they fear when it comes to money, what they really want, and what they love about working together.They explore Jeff’s three pillars of financial lineage, intimacy, and agency, why both of them rank freedom above everything else, and how each of them slips into scarcity mode when things get hard. The conversation turns practical as they unpack why they’re comfortable betting their time but cautious with cash, and what it means to grow without hiring or raising money. They close with the agreements they want to write down together, from an “enough” number to a plan for hard months.If you’re a co-founder who’s never had a direct conversation about money with your partner, a bootstrapped founder wrestling with when to spend to grow, or curious what coaching looks like for a business partnership- 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, Netflix, 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 SUPRAINSIDER50In this episode, we covered the following topics:* Jeff opens with a short mindfulness practice and a felt sense of “enoughness” around money* The exercise: three questions on fear, desire, and love, and why co-founder and couples counseling are so similar* Ben’s answers: his money fears, the image of always having a ticket on the train, and what he loves about Marc* Marc’s answers: freedom, regret, the flexibility he wants money to buy, and what he loves about Ben* Jeff’s three pillars: financial lineage, financial intimacy, and financial agency* Where each co-founder could express more freedom, from fully disconnecting to creative work without a clear ROI* Ben’s “high wire” feeling and how both founders slip into scarcity mode under stress* Growing without hiring, raising, or compromising quality, plus Small Is Beautiful and the fisherman parable* Entrepreneurship as betting: why they underprice their time, overprice cash, and need an experimentation budget* What to codify in their partnership: an “enough” number, a “break the glass” plan for hard months, and scheduled appreciation* Where to find Jeff: LinkedIn, jeffgreenberg.co, coaching, men’s groups, and financial therapy workshops* Gratitude Corner: Jeff thanks three people:* his wife, Alessandra, for backing his move off Wall Street* his friends in Brooklyn* Seth, a mentor who also left Wall Street and started the weekly men’s group Jeff is part of* And more!Links: * Small Is Beautiful (E.F. Schumacher): https://www.goodrea
- 1 weeks ago1h 8m
#134: Why storytelling is still the most important skill for product leaders | Josh Elman (Partner @ a16z, ex-Apple, Robinhood, Twitter, LinkedIn)
What if the most important thing a product manager produces isn’t a roadmap, but a story?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Josh Elman, partner at Andreessen Horowitz and former product leader at Apple, Twitter, Robinhood, Facebook, and LinkedIn. Josh explains why storytelling is the real art of product management and why every good story starts with the customer rather than a business metric. He also explains how that same story has to be shaped for three audiences: your team, your users, and now the AI tools you work with.They explore why onboarding is part of the story, from Josh’s first Twitter spec changing “What are you doing?” to “What’s happening?” to the empty chat boxes in today’s AI products. Josh shares how Life360 and Robinhood turned user objections into stronger narratives and the “layup” interview question most PM candidates flub. He closes with how to build storytelling as a skill through reps, Apple keynotes, and reading fiction.If you’re a PM whose roadmap starts with metrics instead of customers, a founder trying to make your product’s value obvious from the first session, or a candidate who struggles to tell a compelling story about your 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, Netflix, 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 SUPRAINSIDER50In this episode, we covered the following topics:* Why storytelling is the real art of product management, and what Apple taught Josh about starting with the user’s story* One story, three audiences: your team, your customers, and the AI you feed context to* Metrics-first vs. customer-first: why the 78% who didn’t convert hold the big unlocks* B2B vs. consumer stories, and why products like Linear win on feel rather than features* Meta’s Muse, tuning a model to consumer use cases, and why a story can’t be everything to everyone* Empty chat boxes, Josh’s first Twitter spec, and why AI products need built-in social proof* The anatomy of a good story: a pithy description, specific examples, and how to get started* Why the best onboarding doesn’t feel like onboarding, and the person over your shoulder* Life360’s aha moment, objection handling, and Robinhood’s Social Security number wall* Josh’s “layup” interview question and why most PM candidates flub it* A storytelling bootcamp: Apple keynotes, reps, AI feedback, and reading fiction* Where to find Josh: X, the a16z newsletter, and Medium* Gratitude Corner: Josh thanks two groups of people:* Reid Hoffman and David Sze, who shaped how he thinks about consumer products at LinkedIn and later Greylock.* Kurt Knight and Ann Thai, his bosses at Apple, for what they taught him about storytelling and Apple’s culture.* And more!Links: * David Senra: Alexandr Wang episode: https://www.davidsenra.com/episode/alexandr-wang* Supra Insider #87: WTF is “Product Taste” (Sachin Rekhi): https://
- 2 weeks ago1h 12m
#133: Why you should transcribe your job interviews | Dan Wolchonok (Founder @ Work Coach, ex-Reforge, HubSpot)
What separates the job seekers who land great roles from the ones who stay stuck?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Dan Wolchonok, founder of Work Coach and former Reforge and HubSpot operator, to unpack how the most intentional candidates run their job search. Dan explains why the savviest people are ruthless about their process. He covers how smart candidates get in their own way through analysis paralysis and doom scrolling, and why talking to people is the fastest way to get unstuck.They explore candidate-market fit and running your search in “seasons.” They also get into why clear positioning gets you referrals you never asked for, and why AI-reviewed resumes keep coming out generic. Dan makes the case that job seekers face a feedback epidemic: he wants candidates to transcribe everything, listen to how they actually sound, and even ask permission to record real interviews. Marc and Ben push back on how far AI feedback can take you compared with a calibrated expert.If you’re in the middle of a job search that isn’t converting, struggling to explain why you’re the right fit for a role, or wondering how to use AI to get better feedback on your interviews- 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 SUPRAINSIDER50In this episode, we covered the following topics:* What separates the savviest job seekers: being ruthless about their goal and every step of the process* How smart people get in their own way, from analysis paralysis to doom scrolling instead of practicing* Getting unstuck by talking to people, and Ben on candidate-market fit and running your search in “seasons”* Why you don’t need a network, just conversations with people who have one* Why clear positioning makes you easy to refer, from Marc’s Asana elevator test to Ben’s unprompted intro* Why asking for help makes people like you more, and why self-awareness beats stretching for a fit* Why AI-reviewed resumes come out generic, and Dan’s sequence for positioning yourself around what the company needs* Why people struggle to sell themselves, and why storytelling is the universal skill for interviews and the job* The “feedback epidemic”: transcribing everything and asking permission to record real interviews* Why your voice matters, and why “I hate listening to myself” isn’t an excuse* AI feedback vs. expert feedback: Marc’s warning about the average and Dan’s case for starting with AI* Where to find Dan and how Work Coach helps beyond interviewing* Gratitude Corner: Dan thanks three people:* Dharmesh Shah, HubSpot’s co-founder and CTO, the reason he sold his company to HubSpot.* Brian Balfour, who helped turn his career around at HubSpot and worked with him for seven years at Reforge.* Buford Taylor, Reforge’s first engineer, who saved him after he deleted a production database table.* And more!Links: * Josh Herzig-Marx: <a target="_blank" href="https://www.linkedin.com/in/joshu
- 3 weeks ago1h 7m
#132: Inside the new breed of behavioral interviews at Anthropic and OpenAI | Austen McDonald (Behavioral Interview Coach, ex-Meta)
What if your job in a behavioral interview isn’t to answer the question at all?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Austen McDonald, former engineering manager and hiring committee chair at Meta and author of Mastering Behavioral Interviews. Austen explains why character is what predicts long-term performance. He covers why ownership and adaptability have become the signals companies care about most in the age of AI. And he argues that your real job as a candidate is to guide the interviewer toward the parts of your career that best predict how you’ll do the role.They explore every flavor of behavioral interview, from hiring manager screens and project deep dives to Anthropic’s culture round. Austen explains how to handle an inexperienced interviewer using his “decode, select, deliver” loop. He then walks through building a bank of core stories, structuring long stories so the takeaways are obvious, and matching the clock speed of your stories to the company you’re targeting. Marc and Ben share what they’re seeing on the PM side, from take-homes as the real test of AI fluency to Meta’s product sense with prototyping round. The three also debate whether conflict resolution matters more or less as teams flatten.If you’re a senior engineer or product leader with interviews coming up, haven’t interviewed in a few years and want to know what’s changed, or keep telling strong stories that don’t seem to land- 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 SUPRAINSIDER50In this episode, we covered the following topics:* Why Austen chose behavioral interviews after Meta, and why ownership and adaptability now matter most* Mapping every type of behavioral interview, from recruiter screens to team match and project deep dives* How Anthropic’s culture round changes the rules, and why Austen never let junior interviewers run behavioral rounds* “Your job is not to answer the questions”: the decode, select, deliver loop and how to handle an inexperienced interviewer* Ben’s story of a candidate who flipped the question, and why past behavior is more predictive than hypotheticals* How to prepare: know yourself, build a bank of core stories, and structure them so the takeaways are obvious* Matching the clock speed of your stories to the company, from big tech to the frontier labs* When to start preparing, why most people start too late, and keeping a “yay me” file off company servers* What’s changing: project deep dives at more levels, automated screens, and questions about how you use AI* Marc and Ben’s PM take: take-homes as the real AI fluency test and Meta’s product sense with prototyping round* Do conflict resolution skills matter more or less as teams flatten and building gets cheaper?* Where to find Austen: his book, his Substack, and coaching for senior candidates* Gratitude Corner: Austen thanks his wife Kokeb, a six-time author and coach for occupational therapists, for showing him the path to entrepreneurship. He also thanks Henry Cheung, a de
- 4 weeks ago1h 25m
#131: Inside comp negotiation for PM roles at top companies like OpenAI and Anthropic | Colin Lernell (Co-founder @ Valued)
What if the biggest mistake senior product leaders make in negotiation is countering too soon?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Colin Lernell, co-founder and CEO of Valued, a comp negotiation firm, and a former senior product leader. Colin explains why he coaches every client to hold off on the instant counter. Instead, they run due diligence and role alignment calls with the hiring manager and skip-level. Colin walks through how recency bias and loss aversion turn a candidate into a colleague the company is afraid to lose. He also explains why so many top performers undervalue themselves in a market where pay for elite talent has surged.They explore how OpenAI and Anthropic handle their no-negotiation stance and which competing offers actually move them. They get into when a lower level beats a bigger title, and whether sharing a number early helps or hurts. Colin shares his “ask for advice, get a job” tactic for building leverage overnight and the doc he has clients bring to every alignment call. Marc and Ben also debate whether negotiation belongs at the very start of interview prep.If you’re a product leader expecting an offer in the next few weeks, weighing a move into big tech or an AI lab, or unsure how to push for more without damaging the relationship—this episode is for you.Have or expect an offer? Book a free strategy call at feelvalued.co and tell them “INSIDER LOOPS” sent you for $500 off.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 SUPRAINSIDER50In this episode, we covered the following topics:* Why a skeptical product leader called Valued “the best money I’ll spend” within days of signing* Colin’s own mistake: losing his cool on an offer call while holding a $2M competing offer* The executive playbook Colin reverse-engineered at Udacity: due diligence before any counter* How recency bias and loss aversion turn you from a candidate into a colleague the company can’t afford to lose* Why top-talent comp has surged and why even the most senior candidates still under-ask* Marc’s devil’s advocate question: does negotiating a big offer put you under a microscope?* When a lower level is the smarter move, from Meta’s freeze on external director hires to the L7-to-L8 trap* How to negotiate with OpenAI and Anthropic despite their no-negotiation policies* Should you share a number on the first recruiter call? A listener’s doubled offer vs. Colin’s counterpoint* When to bring in a negotiator, and how five LinkedIn messages created three Mag 7 processes overnight* Marc and Ben debate whether salary negotiation should be step zero of interview prep* What goes in the role alignment doc, and how an Apple candidate unlocked double equity* Where to find Colin: free workshops, guides, and consult calls at feelvalued.co* Gratitude Corner: Colin thanks his first manager in Silicon Valley for showing him how to
- Oct 5, 20261h 12m
#130: Inside the current executive recruiting market | Nolan Church (Founder @ Mafia Talent, ex-Carta, DoorDash)
What changes about hiring an executive when the best candidates suddenly have fifteen generational companies to choose from and no reason to pick up the phone?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Nolan Church, who was the first head of talent at DoorDash, then chief people officer at Carta, and who now runs executive searches for a small number of companies at a time. Ben worked for him directly at Continuum, and the two of them walk through what has actually shifted in the executive market: why the clearing price for a great hire is no longer about compensation, why the executive who talks a lot and does nothing has seen demand for their services collapse, and what founders are really buying when they bring in an outside recruiter.They explore the framework Nolan builds every search around, how he gets almost anyone on the phone cold, why he treats relationship building and assessment as separate modes that companies routinely collapse too early, and what he thinks great executive assessment looks like given that structured interviews are only so predictive.If you’re hiring your first executives, thinking about your own next move at that level, or curious how the top of the talent market actually works, 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 SUPRAINSIDER50In this episode, we covered the following topics:* Why Nolan calls this the craziest moment in tech history for executive hiring* The clearing price isn’t just comp, it’s life design* “I don’t believe in work-life balance, I just believe in life,” and where 996 actually fits* The three things an executive is really hired to do* The empty suit, and why demand for that kind of executive has gone to zero* Why Elon never pays for an outside recruiter, and what VCs now have to offer instead* What counts as a successful executive hire, and hiring for the next nine to twelve months* Why the best executive search is about removing asymmetry* The MOC framework: mission, outcome, competency, and why it beats a job description* Executives are like flowers in the spring, and why speed at all costs is a fail state* His secret sauce: 98% of the people he talks to start as cold outreach* Why he thinks really good recruiting is a moral good, and the tax that comes with it* What executive assessment actually looks like, and why interviews give weaker signal than people assume* Gratitude Corner: Nolan thanks his parents, his wife, and the people who bet on him early* And more!Links:* “The Empty Suit Executive” by Tyler Hogge: https://www.tylerhogge.com/blog/the-empty-suit-executive/* Who: The A Method for Hiring by Geoff Smart and Randy Street: https://www.goodreads.com/book/show/4989687-who* Andreessen Horowitz executive hiring guide: <a target="_blank" href="https://a16z.com/executive-hiri
- Sep 28, 20261h 7m
#129: The challenges of working with AI in single-player mode | Andrew Somervell (Co-founder @ Hamster)
When every individual on your team can suddenly move ten times faster, what stops them from moving ten times faster in ten different directions?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Andrew Somervell, co-founder of Hamster, an AI-native workspace for product teams. Andrew and his co-founder built Taskmaster, the open-source tool that shipped plan mode before the major coding tools had it, and the question that kept coming back from users was how to take it to work. He explains why that pointed at a team problem rather than a tooling problem, and why he doesn’t believe PMs want to live in a CLI.They explore the artifacts Andrew thinks a team actually needs, why he killed the PRD and what he ended up building in its place, the three meetings his team runs every week, and Ben’s repeated pressing on the harder question underneath all of it: what genuinely changes when AI becomes multiplayer rather than a set of people each working alone with it.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 SUPRAINSIDER50In this episode, we covered the following topics:* How Taskmaster led to Hamster: solving context locally, then hearing “how do I take this to work?”* The Cursor Cafe conversation, and why he let go of the open-source moat* Marc and Ben walk through their own clunky brief workflow, and Andrew’s verdict* The three artifacts: a brief for stakeholders, a spec for engineering, a plan for delivery* Killing the PRD, and the graveyard of draft briefs that followed* Their three meetings a week, and why discovery is the one he loves* Treating ideas like pets, and what happens when anyone can ship a huge PR* Direction setting: strategy on a page, tied to live metrics* Ben presses on what’s actually different about multiplayer versus single-player* Andrew’s answer: alignment first, then speed and cohesion* The nine challenges that surfaced from 70-plus calls with product leaders* Ben’s takeaway on why two co-founders stay aligned, and what breaks when you add people* Gratitude Corner: Andrew thanks his co-founder Eyal and his Supra group* And more!Links:* Hamster: https://tryhamster.com/* Hamster community Slack: https://tryhamster.com/slack* Eyal Toledano: https://www.linkedin.com/in/eyaltoledano* Andrew Somervell: https://www.linkedin.com/in/andrewsomervell/* 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 Be
- Sep 21, 20261h 20m
#128: Inside the morning ritual that re-energized our podcast | Ben Erez & Marc Baselga (co-founders, Insider Loops)
What do you do when you’re putting in the same hours, running the same playbook, and the numbers stop moving?In this episode of Supra Insider, Marc Baselga and Ben Erez talk through the slowdown their business hit over the summer and how they worked their way out of it. They walk through the blockbuster April that became a false baseline, the moment in late June when the trend was undeniable, and what the analytics revealed once they finally looked properly: traffic was down, and the traffic they had wasn’t converting.They explore why Marc thinks burnout comes from inputs not matching outputs rather than from working hard, what momentum actually is and why losing it is so hard to shake, the content system they built that produced consistently bad posts, and the realization that no amount of good execution rescues a weak idea. They also lay out the protocol they’d use the next time one of them stops having fun.If you’re running a business through a flat stretch, building a content engine that isn’t landing, or working with a partner and wondering how to say the hard thing out loud, 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 SUPRAINSIDER50In this episode, we covered the following topics:* Marc on the first signal: more hours going in, and the numbers refusing to move* The blockbuster April they mistook for a new baseline* What the analytics showed once they looked properly: traffic down, conversion worse* Why Marc thinks burnout comes from inputs not matching outputs* Naming it out loud, and why that gave them permission to change things* Ben defines momentum, and why he couldn’t enjoy a beach vacation without it* Why paid acquisition was premature, and how go-to-market became a content problem* The system they built to draft posts end to end, and why the output was bad* Spending zero time at the idea level, and executing ten out of ten on a two out of ten* Morning writing blocks: using their most productive hours on the actual bottleneck* How a LinkedIn post about rejection turned into an episode booked on the spot* Why “why are you interested in this?” produced a post ten times better* Working up the leverage ladder, and the co-founder benefits they didn’t expect* The protocol for next time: name it, check in, find ground truth, scope a step* And more!Links:* Ben’s post about how he handles rejection: https://benerez.substack.com/p/how-i-handle-setbacks-and-coach-resilience* Episode about Rejection: https://suprainsider.substack.com/p/120-how-to-stop-taking-rejection* Insider Loops: https://www.insiderloops.com/* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com
About Supra Insider
Conversations about hiring, interviews, and careers for product leaders. Hosted by Marc Baselga and Ben Erez (co-founders of Insider Loops). suprainsider.substack.com
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