Lenny's Podcast: Product | Growth | Career Podcast

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.

What you’ll learn:

• Why design should report to engineering, not product

• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60

• How to create design tenets vs. principles (with real examples)

• The counterintuitive reason to delay drawing or prototyping as long as possible

• Why software is fundamentally a medium, like film or music (not just a tool)

• Why Bob “bounced off the culture” at Pinterest, and lessons from failure

• The lunar landing story that teaches us about championing radical ideas

• How to evaluate if a company truly values design before joining

• The moral obligation of software makers to build great products

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This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.

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Where to find Bob Baxley:

• Instagram: https://www.instagram.com/baxley/

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

• Website: http://www.bobbaxley.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) Introduction to Bob Baxley

(03:52) Apple's lasting culture

(06:15) Navigating unique company cultures

(13:19) Finding a company that truly values your role

(15:46) What is design?

(17:17) How to help founders understand the value of design

(23:08) How to align product managers and designers

(26:31) Design reporting to engineering

(30:54) Integrating engineers early in the design process

(33:43) The maker mindset

(35:14) Challenging the assumption that design is time-intensive

(38:04) Design tenets vs. design principles

(45:25) The moral obligation of great design

(51:48) Understanding software as a medium

(01:01:20) Reducing ambiguity for product teams

(01:07:04) Giving designers space for creativity

(01:08:48) The "primal mark" concept

(01:12:05) AI prototyping tools: benefits and risks

(01:17:00) AI as a life coach

(01:21:22) Life lessons from the Apollo program

(01:28:24) Lightning round and final thoughts

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Referenced:

• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs

• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney

• Pinterest: https://www.pinterest.com/

• X: https://x.com/

• Uber: https://www.uber.com/

• Airbnb: https://www.airbnb.com/

• Slack: https://slack.com/

• Ed Catmull on X: https://x.com/edcatmull

• John Lasseter on X: https://x.com/johnlasseter5

• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on

• Humane: https://en.wikipedia.org/wiki/Humane_Inc.

• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive

• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/

• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/

• Tim Cook on X: https://x.com/tim_cook

• ThoughtSpot: https://www.thoughtspot.com/

• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/

• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/

• Honeywell: https://www.honeywell.com

• IDEO: https://www.ideo.com/

• Nutanix: https://www.nutanix.com/

• Lego: https://www.lego.com/

• Leica: https://leica-camera.com/

• Porsche: https://www.porsche.com/

• Patagonia: https://www.patagonia.com

• Brian Eno’s website: https://www.brian-eno.net/

• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/

• The Beatles website: https://www.thebeatles.com/

• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/

• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/

• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more

• Larry Page: https://en.wikipedia.org/wiki/Larry_Page

• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin

• Design Principles: https://principles.design/

• Tableau: https://www.tableau.com/

• Figma: https://www.figma.com/

• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• eBay: https://www.ebay.com/

• Williams Sonoma: https://www.williams-sonoma.com/

• Amazon: https://www.amazon.com/

• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974

• Toast: https://pos.toasttab.com/

• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas

• The Plant: https://pixar.fandom.com/wiki/The_Plant

• Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai

• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna

• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/

• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/

• The Apollo program: https://www.nasa.gov/the-apollo-program/

• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k

• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\

• Blue Origin: https://www.blueorigin.com/

• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin

• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun

• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk

• John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU

• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6

• Habitica: https://habitica.com/static/home

• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a

• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made

• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035

• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb

• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/

• Perplexity: https://www.perplexity.ai/

• Golden State Warriors: https://www.nba.com/warriors/

• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry

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Recommended books:

• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423

• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414

• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326

• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469

• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox.

What you’ll learn:

• Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works)

• How to maintain product quality with 30,000 daily deployments and distributed ownership

• The weekly email system Sebastian uses to maintain alignment with leadership

• How to build a culture of radical candor and direct feedback in a traditionally hierarchical region

• The counterintuitive approach to product reviews that keeps 18,000 engineers aligned

• How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative

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Brought to you by:

Merge—A single API to add hundreds of integrations into your app

Vanta—Automate compliance. Simplify security

LinkedIn Ads—Reach professionals and drive results for your business

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Where to find Sebastian Barrios:

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

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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 to Sebastian Barrios and Mercado Libre

(05:03) Mercado Libre’s scale and unique ways of operating

(14:48) AI’s impact on operations

(19:19) Empowering teams and reducing fear of failure

(34:20) The importance of radical candor

(38:26) Weekly updates

(41:03) Avoiding hype cycles

(44:24) When Steve Jobs personally called 17-year-old Sebastian

(49:00) Building successful app businesses

(55:33) Unique personal habits

(01:04:00) Raising independent children

(01:07:15) Lightning round and final thoughts

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Referenced:

• Mercado Libre: https://www.mercadolibre.com/

• Claude: https://claude.ai/

• Salesforce: https://www.salesforce.com/

• Nvidia: https://www.nvidia.com/

• TikTok: https://www.tiktok.com/

• Adobe: https://www.adobe.com/

• Uber: https://www.uber.com/

• OpenAI: https://openai.com/

• Marcos Galperin on LinkedIn: https://www.linkedin.com/in/marcosgalperin/

• Cursor: https://www.cursor.com/

• Windsurf: https://windsurf.com/

• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best

• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm

• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers

• Intercom: https://www.intercom.com/

• Atlassian: https://www.atlassian.com/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Managing up: https://www.lennysnewsletter.com/p/managing-up

• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Everything Everywhere All at Once: https://www.imdb.com/title/tt6710474/

• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

• Bluey on Disney+: https://www.disneyplus.com/browse/entity-fa6973b9-e7cf-49fb-81a2-d4908e4bf694

• Mentava: https://www.mentava.com/

• Matt Bateman’s website: https://mattbateman.xyz/

• Beast Academy: https://beastacademy.com/

• David protein bars: https://davidprotein.com/

• Marc Andreessen on X: https://x.com/pmarca

• Tatami mats: https://en.wikipedia.org/wiki/Tatami

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Recommended books:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/

• The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0140268863

• The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119/

• Dune: https://www.amazon.com/Dune-Chronicles-Book-1/dp/0441013597/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024.

In this episode, you'll learn:

• How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates

• Why embedding product managers with AI researchers yields 10x the impact of traditional product development

• The three areas where product teams can still add massive value as AI gets smarter

• How Anthropic plans to compete with OpenAI long-term

• How to use Claude as your product strategy partner (with specific prompting techniques)

• Why Mike shut down Artifact despite loving the product, and what founders can learn from it

• Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google

• Why MCP (Model Context Protocol) might reshape how all software works

• The counterintuitive product metrics that matter for AI

• How to evaluate whether your company is maximizing AI’s potential or just scratching the surface

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Brought to you by:

Productboard—Make products that matter

Stripe—Helping companies of all sizes grow revenue

OneSchema—Import CSV data 10x faster

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Where to find Mike Krieger:

• X: https://x.com/mikeyk

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

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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 to Mike Krieger

(04:20) What Mike has changed his mind about regarding AI capabilities

(07:38) How to avoid scary AI scenarios

(08:55) Skills kids will need in an AI world

(11:53) How product development changes when 90% of code is written by AI

(17:07) Claude helping with product strategy

(21:16) A new way of working

(23:55) The future value of product teams in an AI world

(27:18) Prompting tricks to get more out of Claude

(29:52) The Rick Rubin collaboration on “vibe coding”

(32:42) How Mike was recruited to Anthropic

(35:55) Why Mike shut down Artifact

(42:41) Anthropic vs. OpenAI

(47:11) Where AI founders should play to avoid getting squashed

(51:58) How companies can best leverage Anthropic’s models and APIs

(54:29) The role of MCPs (Model Context Protocols)

(58:25) Claude’s questions for Mike

(01:03:15) Claude’s heartfelt message to Mike

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Referenced:

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

• Claude Opus 4: https://www.anthropic.com/claude/opus

• Dario Amodei on X: https://x.com/darioamodei

• AI 2027: https://ai-2027.com/

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon

• Information theory: https://en.wikipedia.org/wiki/Information_theory

• TypeScript: https://www.typescriptlang.org/

• Python: https://www.python.org/

• Rust: https://www.rust-lang.org/

• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor

• Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how

• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k

• Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/

• Artifact: https://en.wikipedia.org/wiki/Artifact_(app)

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

• Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/

• Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/

• Gunnar Gray on LinkedIn: https://www.linkedin.com/in/gunnargray/

• The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol

• 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

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Jimmy Kimmel Live: https://www.youtube.com/user/JimmyKimmelLive

• ChatGPT: https://chatgpt.com/

• Gemini: https://gemini.google.com/app

• 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

• Windsurf: https://windsurf.com/

• Menlo Ventures: https://menlovc.com/

• Harvey: https://www.harvey.ai/

• Manus: https://manus.im/

• Bench: https://www.bench-ai.com/

• Strategy Letter V: https://www.joelonsoftware.com/2002/06/12/strategy-letter-v/

• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/

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Recommended books:

• The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

• The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/

• 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/Hard-Thing-About-Things-Building/dp/0062273205

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams.

What you will learn:

1. Dogfooding at scale

2. “Ship, ship, ship” as a cultural mantra

3. Obsession with inputs over outputs

4. Uber’s hybrid marketplace vision for autonomy

5. How Uber changed its culture to focus on profitability

6. What to do when data says “no” but your gut says “yes”

7. Career advice: maximize cycles

8. AI as a research assistant, not an oracle

9. Uber rider etiquette tips

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Brought to you by:

• Paragon—Ship every SaaS integration your customers want

• Stripe—Financial infrastructure to grow your revenue

• Coda—The all-in-one collaborative workspace

—

Where to find Sachin Kansal:

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

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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) Sachin’s background

(05:00) Dogfooding in practice

(11:24) Empathy and understanding drivers

(20:18) Balancing metrics and user experience

(22:04) Operationalizing dogfooding

(24:26) Challenges and solutions in dogfooding

(29:49) The motto: “ship, ship, ship”

(36:37) Product announcements and live demos

(40:49) Career advice for product managers

(43:51) The evolution of product management with AI

(46:55) Collaboration between engineers and product managers

(49:36) Uber’s vision for self-driving cars

(55:59) Uber’s path to profitability

(01:01:58) Balancing data and gut decisions

(01:07:21) AI tools in product management

(01:10:14) Failure corner

(01:13:48) Lightning round and final thoughts

—

Referenced:

• Uber: https://www.uber.com/

• Oracle: https://www.oracle.com/

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

• Fivetran: https://go.fivetran.com/

• Uber for Business: https://www.uber.com/us/en/business

• McDonald’s: https://www.mcdonalds.com/

• Domino’s: https://www.dominos.com

• PalmPilot: https://en.wikipedia.org/wiki/PalmPilot

• Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/

• May Mobility: https://maymobility.com/

• Uber strikes deal with May Mobility to deploy ‘thousands’ of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership

• Waymo: https://waymo.com/

• WeRide: https://www.weride.ai/

• Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx

• Dara Khosrowshahi on X: https://x.com/dkhos

• Uber Elevate: https://www.uber.com/us/en/elevate/vision/

• Uber AV: https://www.uber.com/us/en/autonomous/

• Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/

• Uber for teens: https://www.uber.com/us/en/ride/teens/

• Flywheel: https://www.flywheel.com/

• ChatGPT: https://chatgpt.com/

• Gemini: https://gemini.google.com/app

• NotebookLM: https://notebooklm.google/

• Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin

• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry

• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479

• Deep research: https://openai.com/index/introducing-deep-research/

—

Recommended books:

• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419

• Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI

• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537

• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281

• 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/Hard-Thing-About-Things-Building/dp/0062273205

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.

What you will learn:

1. Why do most marketing playbooks often fail, and what’s a better way?

2. Which marketing lever should I pull first?

3. Why is trying to be better than competitors usually a losing strategy?

4. How do I craft positioning that actually converts?

5. What makes messaging stick with developers, enterprises, and consumers?

6. What pricing experiments actually move revenue?

7. What is working at OpenAI really like?

8. Why does consistency and quality matter more than speed?

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Brought to you by:

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Where to find Krithika Shankarraman:

• X: https://x.com/krithix

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

• Website: https://krithix.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) Introduction to Krithika

(04:22) Early marketing lessons from OpenAI

(11:17) Diagnosing marketing needs

(15:06) The DATE framework and why being cheaper is a race to the bottom

(17:11) Marketing strategies at Retool

(22:29) Insights from marketing at Stripe

(32:33) The importance of consistent marketing communication

(39:55) Criteria for hiring a marketing expert

(41:43) “Capital M” vs. “lowercase m” marketing

(43:05) ChatGPT vs. Claude: market dominance

(45:31) The future of AI and its societal impact

(47:09) Work-life balance

(48:41) Transitioning to Thrive

(52:35) Career advice for marketers

(55:00) The importance of taste and creativity in the AI era

(01:00:04) AI product pricing

(01:03:21) AI tools in marketing

(01:05:17) Failure corner

(01:08:46) Lightning round and final thoughts

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Referenced:

• OpenAI: https://openai.com/

• Stripe: https://stripe.com/

• Retool: https://retool.com/

• Dropbox: https://www.dropbox.com/

• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy

• Netflix: https://www.netflix.com/

• Stripe Connect: https://stripe.com/connect

• John Collison on X: https://x.com/collision

• Patrick Collison on X: https://x.com/patrickc

• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/

• Hackpad: https://en.wikipedia.org/wiki/Hackpad

• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg

• Wiz: https://www.wiz.io/

• Thrive Capital: https://thrivecap.com/

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

• Claude: https://claude.ai/new

• ChatGPT: https://chatgpt.com/

• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

• Databricks: https://www.databricks.com/

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• 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

• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/

• Granola: https://www.granola.ai/

• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/

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Recommended books:

• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005

• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

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Lenny may be an investor in the companies discussed.