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Lyt når som helst, hvor som helst 

Lenny Rachitsky

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

Lenny's Podcast: Product | Growth | Career

Roman Ugarte helped incubate and build Grok Bot, the popular new knowledge-work agent from SpaceXAI. A small, isolated team took it from first line of code to a working internal product in four weeks, and to a hugely successful public launch just three weeks later. Before Grok Bot, Roman led Growth at Cursor, where he helped scale the company from 15 people to over 1,000 before its acquisition by SpaceX.

In our in-depth conversation, we discuss:

1. The origin story of Grok Bot

2. The key decision to build it from scratch instead of adding it to Cursor

3. Why the team personally onboarded nearly 300 of its first users

4. The two early product decisions that made Grok Bot so successful

5. Their “colleague-pilled” product philosophy

6. Roman’s advice on moats, and what has allowed Cursor to keep winning in the most competitive market in the world

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

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Where to find Roman Ugarte:

• X: https://x.com/romanugarte_

• LinkedIn: https://www.linkedin.com/in/romanugarte

• Website: https://x.ai

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:09) The origin story: building from scratch in one month

(08:40) Why Grok Bot was built as a separate product

(11:20) Manually onboarding a couple hundred people

(14:29) Hiding internal mechanics from users

(18:41) Timeline from beta to public launch

(19:14) Unshipping features and simplifying

(23:50) Early use cases and feedback

(26:50) Product philosophy: “Grok Bot can now”

(30:02) Cloud-first architecture

(33:12) The fresh-start advantage

(35:54) The vision: a true team of AI colleagues

(39:20) The “colleague-pilled” framework

(42:36) Work versus personal: one product or two?

(47:14) Long-lived agents, persistent memory, and the computer abstraction

(51:04) Grok Bot as an always-on infovore and chief of staff

(53:35) How fast the team moves and what preserves the startup feeling

(58:20) SpaceXAI pillars

(1:00:44) The first 90% vs. the last 10%

(1:03:30) Moving fast at scale

(1:06:40) How Cursor kept winning in the most competitive market in the world

(1:10:04) Company values: “deleting the product” and “just do the thing”

(1:11:45) Moats: discovered, not planned

(1:15:11) Tips for new users and power users

(1:18:00) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)

Anish Acharya is a General Partner at Andreessen Horowitz (a16z), where he has focused on consumer investing. Anish is one of the most insightful, thought-provoking, and in-the-weeds product investors I’ve met, and this conversation will get your mind buzzing. Before joining a16z, Anish was a serial founder and operator: he founded SocialDeck, which he sold to Google, then led multiple efforts inside Google before founding Snowball, which he sold to Credit Karma. At Credit Karma he rose to VP of Product and then GM of the consumer product and the broader credit card business.

In our in-depth conversation, we discuss:

1. Why you don’t have to worry about becoming part of the “permanent underclass”

2. Why company building will now involve creating a series of loops

3. What’s happening in consumer right now

4. Why the biggest opportunity in consumer is “/loop, make me happier”

5. Why moats are discovered, not designed

6. The rising importance of distribution as a moat

7. Being a model sommelier

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Anish Acharya:

• Andreessen Horowitz: https://a16z.com/author/anish-acharya/

• LinkedIn: https://www.linkedin.com/in/anishacharya/

• X: https://x.com/illscience

• SoundCloud: https://soundcloud.com/illscience

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:25) The fear of AI creating a permanent underclass

(05:25) Why AI takeoff may be slower than expected

(08:02) How companies are actually adopting AI

(11:25) Building AI products with loops

(15:25) Why human intuition still matters

(20:19) What the winners in AI are doing differently

(21:41) Generalists vs. specialists

(26:22) How to become a model sommelier

(32:03) /loop make me happier

(36:15) Why Anish is optimistic about the future of AI

(42:47) What happens when models become too dangerous

(46:29) How AI will change jobs and ambition

(51:34) The state of consumer AI

(54:30) How to build a durable moat in AI

(59:25) The power of distribution and word of mouth

(01:04:30) Making bigger bets and rethinking pricing

(01:09:17) Advice for product builders in the AI era

(01:11:48) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

Why companies are becoming a series of loops | Anish Acharya (a16z)

Tara Seshan leads product for Codex and ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders.

In our in-depth conversation, we discuss:

1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution

2. How OpenAI thinks about building for model capabilities two to three months out

3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?”

4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job

5. Writing as thinking vs. writing as reporting

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Tara Seshan:

• X: https://x.com/tarstarr

• LinkedIn: https://www.linkedin.com/in/tarstarr

• Newsletter: https://substack.com/@taraseshan

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:18) What makes OpenAI’s culture so different

(06:42) Why AI product strategy is all about fast experimentation

(09:02) How the PM role is changing

(10:50) The shift from rowing to steering

(15:35) What changes when agents become coworkers

(20:05) Why ambition matters more than ever

(26:39) Building products for models that do not exist yet

(29:21) How ChatGPT’s Chat and Work modes differ

(34:01) How OpenAI ships so quickly at scale

(39:14) The vibe shift happening inside Codex

(42:20) Why traditional roles are beginning to blur

(45:59) Where humans will continue to provide unique value

(48:20) How Tara uses AI in her own work

(51:38) The magic of the /visualize command

(52:39) Writing to think versus writing to report

(57:10) How to use AI without losing your ability to think

(01:00:15) Tara’s biggest lesson from Sutter Hill

(01:04:16) ChatGPT’s site output

(01:05:01) Why knowledge work is becoming more like coding

(01:07:55) Lightning round and final thoughts

—

Referenced:

• Codex: https://chatgpt.com/codex

• ChatGPT Work: https://openai.com/chatgpt-work

• Stripe: https://stripe.com

• Watershed: https://watershed.com

• Thiel Fellowship: https://thielfellowship.org

• Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Andrew Ambrosino on X: https://x.com/ajambrosino

• Tyler Cowen’s website: https://tylercowen.com

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat

• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live

• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay

• Brie Wolfson on X: https://x.com/zebriez

• The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Sutter Hill Ventures: https://shv.com

• Snowflake: https://www.snowflake.com

• Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser

• Footnotes and Tangents: https://footnotesandtangents.substack.com

• The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book

• The Odyssey: https://www.imdb.com/title/tt33764258

• Rashomon: https://www.imdb.com/title/tt0042876

• Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa

• Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok

• The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are

• Ari Weinstein on X: https://x.com/AriX

• Sky: https://sky.app

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

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Recommended books:

• Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391

• Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421

• The Power Broker: https://www.amazon.com/dp/0394720245

• War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832

• Wolf Hall: https://www.amazon.com/dp/0312429983

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.

In our in-depth conversation, we discuss:

1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like

2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously

3. How to craft a two-to-three-sentence message around giving them “alpha”

4. How to run an intro call that extracts maximum intelligence before you ever show a demo

5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away

6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Jen Abel:

• X: https://x.com/jjen_abel

• LinkedIn: https://www.linkedin.com/in/earlystagesales

• Website: https://www.jjellyfish.com

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:49) Why Jen is giving away her enterprise sales playbook

(05:54) Example: selling AI legal tech to SpaceX

(09:11) Step 1: Landing the meeting

(18:44) Step 2: Running the intro call

(30:00) Step 3: Running a follow-up call

(36:30) Step 4: Prepping the pitch/frame for demo

(38:36) Step 5: Running the demo

(46:45) Step 6: Post-demo debrief

(48:59) Step 7 through 9: Preparing for and running the pilot

(01:03:44) Why the standard five-stage CRM pipeline doesn’t work

(01:04:49) Step 10: Post-pilot session

(01:07:48) What a healthy enterprise win rate looks like

(01:11:45) Steps 11 through 14: Navigating procurement and getting the signature

(01:18:01) How to think about expansion

(01:19:18) How buyers can say no without wasting everyone’s time

(01:21:53) Why enterprise sales is a lot like product management

(01:22:27) Closing thoughts

—

Referenced:

• State Affairs: https://stateaffairs.com

• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr

• SpaceX: https://www.spacex.com

• Lemlist: https://www.lemlist.com

• Palantir: https://www.palantir.com

• Jason Lemkin on X: https://x.com/jasonlk

• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

• Careers at State Affairs: https://stateaffairs.com/careers

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

How to close $100K+ enterprise deals, step by step | Jen Abel

Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI.

In our in-depth conversation, we discuss:

1. Why Ian believes this is the best time in history to be a product designer

2. Why engineers 10x’d with AI but design teams haven’t

3. What OpenAI looks for when hiring designers

4. “Just do less”: Ian’s counterintuitive advice to his designers

5. The future of ChatGPT as a super app

6. Where humans still win: user understanding, invention, and point of view

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Ian Silber:

• X: https://x.com/iansilber

• LinkedIn: https://www.linkedin.com/in/iansilber

• Website: https://iansilber.com

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Ian Silber

(02:14) Why designers in general feel anxious about AI

(09:01) What makes specific designers thrive in the AI era

(13:41) Why Ian says it’s the best time in history to be a designer

(17:13) How product roles are converging

(22:24) Can AI design great products?

(23:54) Where human judgment still matters

(27:34) What Ian looks for when hiring designers

(30:20) Why systems thinking matters

(32:53) Balancing speed and craft

(38:05) Designing for vastly different audiences

(41:57) Solving the blank-box problem

(43:31) How ChatGPT is evolving beyond chat

(46:07) The vision for Codex

(49:07) What Ian wishes he knew on day one

(51:40) Why humility matters in AI

(53:41) Advice for designers who are feeling overwhelmed

(55:16) AI corner

(57:43) Failure corner

(01:00:45) Lightning round and final thoughts

(01:05:52) Lessons from Groupon

—

Referenced:

• OpenAI: https://openai.com

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template

• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape

• Notion: https://www.notion.com

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• ChatGPT Work: https://openai.com/chatgpt-work

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• Maybe Happy Ending: https://www.maybehappyending.com

• The Invite: https://www.imdb.com/title/tt14173636

• Rivian: https://rivian.com

• Waymo: https://waymo.com

• Groupon: https://www.groupon.com

• How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used

• Andrew Mason on X: https://x.com/andrewmason

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom

• Sam Altman on X: https://x.com/sama

—

Recommended book:

• The Design of Everyday Things: https://www.amazon.com/dp/0465050654

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech.

In our in-depth conversation, we discuss:

1. Inside today’s “tale of two cities” talent market

2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires

3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit

4. The worst question to ask when sourcing great talent

5. The rise of the forward deployed engineer—and how to become one

6. The biggest mistake founders make when hiring their first recruiter

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Adam Ward

• X: https://x.com/wardadamp

• LinkedIn: https://www.linkedin.com/in/adampward

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(03:01) The state of the hiring market

(06:41) What roles are trending up and what roles are trending down

(11:25) The three-step hiring framework that changes everything

(21:58) Getting the right people to actually respond

(25:42) Keeping talent a top priority

(29:16) Inside Cursor’s recruiting operation

(32:19) How to relentlessly pursue top talent

(35:42) “Caring is free”

(38:33) The conversation most companies underestimate

(39:19) Rethinking the atomic unit of a search

(40:12) Other recruiting tactics

(45:04) What the on-site is really for

(49:35) The importance of work trials

(53:10) The offer stage

(57:53) Negotiations and comp

(01:01:50) The details that actually close the deal

(01:07:23) What it’s like working with an exec team who values recruiting

(01:09:42) Talent density

(01:11:18) The first recruiting hire most founders get wrong

(01:15:00) Building incredible teams

(01:18:12) The time between offer and acceptance

(01:19:48) What’s next for the recruiting function

(01:21:00) Lightning round

—

Referenced:

• Cursor: https://cursor.com

• Trilogy: https://trilogy.com

• Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724

• Inside Cursor: https://colossus.com/article/inside-cursor

• SpaceX: https://www.spacex.com

• Joe Gebbia’s website: https://joegebbia.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Granola: https://www.granola.ai

• Wispr Flow: https://wisprflow.ai

• 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch

• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

—

Recommended books:

• Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor

Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history).

In our in-depth conversation, we discuss:

1. Why Whatnot’s product team was founded on the premise “we regret that product management exists”

2. How AI is reshaping the PM role

3. What Tom looks for when hiring PMs

4. The shift toward senior ICs doing the work

5. How AI has transformed data science at Whatnot

6. Tom’s “play the accordion” mental model

7. Why “hire great people and get out of their way” fails

8. His biggest lessons from his time at Twitter

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Tom Verrilli:

• X: https://x.com/tdrobbo

• LinkedIn: https://www.linkedin.com/in/tom-robertson-042

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:40) “We regret that product management exists”: what it means and why

(08:30) When specialization makes sense, and when it doesn’t

(15:20) How Whatnot structures its PM org

(17:28) What 31,832 PM applications revealed about the function

(19:40) How to develop systems thinking

(22:10) The shift to senior ICs doing IC work

(32:26) Advice for PMs struggling in today’s market

(35:22) How AI has transformed work at Whatnot

(41:14) The data scientist problem

(42:48) Which roles are trending up and down

(44:48) What the product team of the future looks like

(46:29) Why core PM skills are the most durable in an AI world

(49:23) How to get the most out of the people you hire

(53:32) Navigating the CPO-founder relationship

(57:34) Advice for aspiring CPO’s

(59:16) How to know when to stand firm and when to step back

(01:01:38) Play the accordion: balancing strategic vision with fast iteration

(01:06:35) Agentic commerce vs. live commerce

(01:09:46) Lessons from Twitter

(01:13:07) Failure corner

(01:15:45) Lightning round and final thoughts

—

Referenced:

• Whatnot: https://www.whatnot.com

• Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc

• Twitch: https://www.twitch.tv

• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future

• Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis

• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus

• Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th

• Hex Threads: https://hex.tech/product/threads

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine

• Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head

• Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear

• Kara Swisher on X: https://x.com/karaswisher

• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1

• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

• Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app

• Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling

• E-fish.com: https://www.e-fish.com

—

Recommended books:

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205

• The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063

• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase.

In our in-depth conversation, we discuss:

1. What Anthropic’s early days were like

2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history

3. How exactly Claude got so good at coding

4. The eval-driven development loop her team is pioneering

5. How to find joy in AI when everything is moving this fast

6. Why Claude’s willingness to push back is key to its success

7. Where human judgment remains irreplaceable

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Dianne Penn:

• LinkedIn: linkedin.com/in/dianne-na-penn

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:31) Early Anthropic days

(08:55) Big milestones

(13:50) Inside the exponential

(20:02) Token maxing

(23:30) Anthropic Labs and the incubation model

(27:30) How the research role works

(31:35) How to become a top researcher

(35:18) Frontier model safeguards

(39:38) Hiring in the AI era

(44:16) Building an eval set

(47:48) Evals vs PRDs

(49:55) The importance of hands-on leadership

(52:46) Finding joy in AI

(58:10) How Dianne uses Claude

(01:01:05) Avoiding overreliance on AI

(01:03:50) The constitution that makes Claude better

(01:07:11) AI writing and verification

(01:11:40) Where human brains will continue to be valuable

(01:14:10) Navigating AI with kids

(01:16:26) Alignment, the future of the PM role, and burnout

(01:21:54) Lightning round and final thoughts

—

Referenced:

• Anthropic: https://www.anthropic.com

• Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude

• Dario Amodei’s website: https://darioamodei.com

• Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data

• Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers

• Garry Tan on X: https://x.com/garrytan

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs

• Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs

• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering

• The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b

• How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands

• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2

• Fallout (video game): https://fallout.bethesda.net

• Claude Tag: https://www.anthropic.com/news/introducing-claude-tag

—

Recommended books:

• Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328

• How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779

• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch.

In our in-depth conversation, we discuss:

1. Why “systems thinking” is now the most important skill she looks for

2. How to manage the flood of AI-generated output without losing quality or signal

3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill

4. What “excellence as an operating system” means

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign

—

Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction

(02:25) AI and role confusion: the storming phase before the forming phase

(07:36) How roles have changed in the past two and a half years

(11:55) Will functions survive? The case for craft specialism

(13:26) What Netflix is hiring more of—and less of

(17:22) Why systems thinking is the rising skill across every function

(20:20) Is the design process dead?

(22:08) Skills trending down

(28:33) AI fluency and Netflix’s career ladder overlay

(31:00) AI use cases beyond coding

(35:12) Netflix’s AI history

(38:36) Excellence as an operating system

(41:11) The pillars of the excellence OS

(46:41) The keeper’s test—and why it’s mostly a positive conversation

(50:21) Attracting top talent in the age of frontier AI labs

(52:54) Junior talent, craft mastery, and the mentorship question

(56:25) Where engineering goes in 5 to 10 years

(59:45) The future of entertainment: beyond film and TV

(1:02:18) AI in Hollywood: Netflix’s creator-enablement position

(1:06:15) Lightning round and final thoughts

—

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Claude Code: https://www.anthropic.com/product/claude-code

• Claude Cowork: https://www.anthropic.com/product/claude-cowork

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it

• Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix

• InterPositive: https://weareinterpositive.com

• Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize

• Quarterback on Netflix: https://www.netflix.com/title/81482895

• The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214

• Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt

• Salman Rushdie’s Substack: https://salmanrushdie.substack.com

• Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351

• Eight Sleep: https://www.eightsleep.com

• Tour de France: https://www.letour.fr/en

—

Recommended books:

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785

• Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)

Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking.

In our in-depth conversation, we discuss:

1. Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken

2. The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful)

3. Why burnout has jumped an alarming 11 points in a single year

4. Why nobody in tech would recommend their job to someone entering the industry today

5. The #1 fear in tech right now (it’s not job loss to AI)

6. Why managers are the single biggest lever for employee well-being

7. Concrete advice for what employees and leaders can do right now

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign

—

Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Noam Segal:

• X: https://x.com/noamseg

• LinkedIn: https://www.linkedin.com/in/noamsegal

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Noam Segal

(02:34) About the survey: methodology and scope

(06:04) The core finding: AI has split the tech workforce in half

(13:03) The AI identity stance

(14:40) The four archetypes: Energized, Conflicted, Disoriented, Resentful

(19:35) Burnout is surging (and why shipping faster is making it worse)

(22:53) A glimmer of hope

(24:55) Layoff worries

(29:15) The career recommendation NPS score

(36:45) The ladder metaphor: rungs disappearing beneath our feet

(45:14) AI is making us faster, not better

(52:53) The #1 fear: being squeezed to do more for the same pay

(55:55) The emotional landscape and “smiling exhaustion”

(01:01:02) Designers and researchers: the most negative group two years running

(01:06:27) Who’s happiest

(01:12:18) Managers: the single biggest lever on well-being

(01:18:47) The industry is “chaotic”

(01:24:53) What employees and leaders can do right now

(01:31:32) AI guilt and closing thoughts

—

Referenced:

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• How tech’s most resilient workers handle burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers

• Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• NPS Is The Worst: https://www.npsistheworst.com

• The Terminator: https://www.imdb.com/title/tt0088247

• Skynet: https://terminator.fandom.com/wiki/Skynet

• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

• Devin: https://devin.ai

• An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

• Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5

• Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape

• Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

To hear more, visit www.lennysnewsletter.com

How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)

This is a special episode of the podcast where I’ve curated my favorite interview questions that guests have shared, among over 100 podcast guests. Whether you’re a hiring manager, currently interviewing, or simply intrigued by the creative and perceptive questions that top product leaders rely on to find top talent, these questions offer unique insights into the strategies and philosophies that shape successful interviews.

—

Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps | Eppo—Run reliable, impactful experiments

—

Find the transcript at: ⁠https://www.lennysnewsletter.com/p/my-favorite-interview-questions-from

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, you’ll hear from:

(00:00) Lenny

(03:21) Eeke De Miliano

(03:57) Geoff Charles

(04:31) Shishir Mehrotra

(08:44) Yuhki Yamashita

(09:56) Katie Dill

(10:36) Karri Saarinen

(11:02) Camille Hearst

(11:28) Jiaona Zhang

(12:43) Noah Weiss

(13:10) Ben Williams

(14:41) Meltem Kuran Berkowitz

(15:29) Paige Costello

(16:13) Nikhyl Singhal

(17:51) Ayo Omojola

(18:20) Scott Belsky

(19:17) Lauryn Isford

(19:46) Paul Adams

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.
 

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

My favorite interview questions from 100+ guests

Lyt når som helst, hvor som helst

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