Lenny's Podcast: Product | Career | Growth

Molly Graham is back for round two, and this one is even more powerful. Molly has spent more than 20 years helping organizations and the humans inside them navigate growth and change. She’s held leadership roles at Google, Facebook, Quip, and the Chan Zuckerberg Initiative and is the host of TED’s WorkLife podcast (which she took over from Adam Grant). She also runs Glue Club, a leadership community for senior operators, and writes a popular newsletter called Lessons.

In our in-depth conversation, we discuss:
1. Why Molly’s famous “give away your Legos” career advice no longer holds true in an AI world
2. The grief, loneliness, and burnout sweeping through the tech industry right now
3. Why delegating to AI is fundamentally different from delegating to a human
4. The fear narrative around AI job displacement, and why it’s overblown
5. Which Legos you should never give to AI
6. What the best managers are doing right now
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
DX—Engineering intelligence for the AI era
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Episode transcript: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
Highlights: https://lennyspodcast.com/mostreplayedmoments
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Where to find Molly Graham
• X: https://x.com/molly_g
• LinkedIn: https://www.linkedin.com/in/mograham
• Substack: https://mollyg.substack.com
• Website: https://glueclub.com
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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/
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In this episode, we cover:
(00:00) Molly Graham returns
(03:34) What is “Give away your Legos”?
(05:44) The origin story: Google, Facebook, and rapid scale
(11:27) What still holds true in an AI world
(18:13) Engineering’s identity shift: from rowing to steering
(22:09) Loneliness and the collapse of team structure
(24:06) The centaur and the reverse centaur
(25:36) The fear narrative: AI-branded layoffs and overblown doom
(29:20) Survey data: burnout is up to 55%, but half of people are thriving
(35:07) Cleaning up AI slop
(40:01) What’s actually different: delegating to AI vs. giving Legos to a human
(42:02) Why every worker is now a manager, whether they want to be or not
(49:07) Why giving things away creates space for new opportunities
(55:27) Advice for people in the age of AI
(59:38) What Legos you should never give away
(01:03:12) The human sandwich: vision at the top, AI in the middle, humans at the end
(01:05:00) Holding on to the things you love: grief, funerals, and what comes next
(01:09:39) Slow takeoff: why you’re not too late
(01:13:32) The most important skill to build right now
(01:18:58) A message for managers and leaders
(01:24:17) Key takeaways
(01:31:42) Final thoughts
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References: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout
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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

Peter Sellis was the first product manager at Snapchat, where he spent seven years building one of the most beloved consumer products in history. He went on to serve as Head of Product at Discord, where he helped drive some of the fastest user growth the platform had seen. Having left his role at Discord, he gets to be especially real and unfiltered — nothing to promote, no PR, no comms team.

In our in-depth conversation, we discuss:
1. Why Peter designs teams like . . . terrorist organizations
2. What it was really like to manage Nikita Bier
3. Why the median PM is so bad
4. Why Snapchat’s ads business never reached its potential
5. Why growth almost always comes from the core product
6. Peter’s three “oxymorons” of great product management
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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/90-minutes-of-unfiltered-product
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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 Peter Sellis:
• X: https://x.com/petersellis
• LinkedIn: https://www.linkedin.com/in/disgruntled
• Website: https://pjs.lol
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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/
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In this episode, we cover:
(00:00) Introduction
(02:48) Why Peter avoided podcasts until now
(05:44) Designing teams like terrorist organizations
(10:35) Cult versus terrorist org: the key distinction
(11:19) Managing Nikita Bier
(12:56) Building orgs that handle spiky talent
(15:16) Why the median PM is probably bad
(18:28) Is the PM profession getting better?
(20:49) Snap’s three ads monetization challenges
(25:03) Snap’s underrated product track record
(27:57) Systems thinking
(32:19) Instagram copying Snapchat’s worst features
(33:32) Software moats
(35:27) Taste, museum curators, and the art of saying no
(40:05) OpenAI, ads, and the trust auction mechanism
(46:25) Counterintuitive lesson: ride your best people hard
(50:13) Why collaboration is often overrated
(50:50) Growth lives in the core product
(57:50) When to bet on something genuinely new
(01:02:18) SpaceX and sunsetting the Falcon 9
(01:07:01) Ambition as a learnable muscle
(01:10:26) Long-term greedy: the ads philosophy
(01:13:36) The Core Product Value framework
(01:16:33) The three oxymorons of a great PM
(01:20:29) Contrarian corner
(01:26:00) Lightning round and final thoughts
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References: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product
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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

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

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

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
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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
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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/
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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
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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
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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