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?

—

Brought to you by:

Eppo — Run reliable, impactful experiments

Airtable ProductCentral—Launch to new heights with a unified system for product development

LinkedIn Ads—Reach professionals and drive results for your business

—

Where to find Krithika Shankarraman:

• X: https://x.com/krithix

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

• Website: https://krithix.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 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

—

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/

—

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/

—

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.

Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda.

Learn:

1. How to find and focus on the highest-leverage problems

2. Why you shouldn’t optimize for compensation early in your career

3. Why you should optimize for strengths, not weaknesses

4. Why you need to decide if you truly want the C-suite path

5. Why working at a fintech company creates exceptional PMs

6. Strategy = hypothesis × experimentation velocity

7. Small, fast wins compound faster than big, slow bets

—

Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Paragon—Ship every SaaS integration your customers want

• Vanta—Automate compliance. Simplify security.

—

Where to find Mayur Kamat:

• X: https://x.com/5degreez

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

—

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 and Mayur’s background

(04:49) Working at Binance: An inside look

(18:18) Career advice for product managers

(27:00) PM career paths

(33:58) Understanding fintech customers

(36:00) Understanding your strengths

(44:46) Creating a culture of experimentation

(51:14) Hiring and developing top talent

(54:50) Building a diverse product portfolio

(57:08) Working in high talent density areas

(59:43) Personal and professional balance

(01:06:32) High-leverage opportunities and decision making

(01:14:28) AI tools in the workplace

(01:19:14) Failure corner

(01:25:11) Lightning round and final thoughts

—

Referenced:

• Binance: https://www.binance.us/

• Google: https://about.google/

• Microsoft: https://www.microsoft.com/

• Agoda: https://www.agoda.com

• N26: https://n26.com/

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

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

• Bezos Says Work-Life Balance is a “Debilitating” Phrase: https://www.investopedia.com/news/bezos-says-worklife-balance-debilitating-phrase/

• Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html

• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia

• Changpeng Zhao on LinkedIn: https://www.linkedin.com/in/cpzhao/

• Ray Dalio on LinkedIn: https://www.linkedin.com/in/raydalio/

• Porter’s five forces: https://en.wikipedia.org/wiki/Porter%27s_five_forces_analysis

• Jonathan Rosenberg on X: https://x.com/jjrosenberg

• Aura: https://buy.aura.com/

• Intercom: https://www.intercom.com/

• Palantir: https://www.palantir.com/

• Revolut: https://www.revolut.com/

• Chime: https://www.chime.com/

• Stripe: https://stripe.com/

• Dropbox: https://www.dropbox.com/

• Alex Algard on LinkedIn: https://www.linkedin.com/in/alexalgard

• Hiya: https://www.hiya.com/

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

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

• Writer: https://writer.com/

• Google Hangouts: https://en.wikipedia.org/wiki/Google_Hangouts

• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/

• Google Meet: https://meet.google.com/landing

• House on Hulu: https://www.hulu.com/series/ef39603f-eb90-4248-8237-f6168d7c1be1

• Big Bang Theory on Hulu: https://www.hulu.com/series/9bde5aeb-5297-4290-b173-19a4d59cc11d

• Adolescence on Netflix: https://www.netflix.com/title/81756069

• The White Lotus on HBO: https://www.hbo.com/the-white-lotus

• Robinhood: https://robinhood.com/us/en/

• Nikita Bier’s post on X about Bible Chat: https://x.com/nikitabier/status/1915252215507210349

• Bible Chat: https://apps.apple.com/us/app/bible-chat-daily-devotional/id6448849666?mt=8

• Suno: https://suno.com/home

• Disfrutar: https://www.disfrutarbarcelona.com/

—

Recommended books:

• StrengthsFinder 2.0: https://www.amazon.com/StrengthsFinder-2-0-Tom-Rath/dp/159562015X

• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X

—

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.

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.

What you’ll learn:

1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development

2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)

3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces

4. Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing

5. How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier

6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches

7. Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems)

8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone

9. A practical framework for evaluating zero-to-one product opportunities

—

Brought to you by:

Eppo—Run reliable, impactful experiments

Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications

Coda—The all-in-one collaborative workspace

—

Where to find Aparna Chennapragada:

• X: https://x.com/aparnacd

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

—

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 Aparna Chennapragada

(04:28) Aparna’s stand-up comedy journey

(07:29) Transition to Microsoft and enterprise insights

(10:00) The Frontier program and AI integration

(13:28) Understanding AI agents

(17:59) NLX is the new UX

(22:28) The future of product development

(31:16) Building a custom Chrome extension

(35:45) Leadership styles of Satya and Sundar

(37:47) Counterintuitive lessons in product building

(41:20) Inflection points for successful products

(45:16) GitHub Copilot and code generation

(48:34) Excel’s enduring success

(50:27) Pivotal career moments

(54:55) The future of human-agent collaboration

(56:25) Lightning round and final thoughts

—

Referenced:

• Google Lens: https://lens.google/

• Saturday Night Live: https://www.nbc.com/saturday-night-live

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Robinhood: https://robinhood.com/

• eBay: https://www.ebay.com/

• Capital One: https://www.capitalone.com/

• Microsoft: https://www.microsoft.com/

• Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/

• The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split

• AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/

• 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

• Deepseek: https://www.deepseek.com/

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• 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

• Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514

• GitHub Copilot: https://github.com/features/copilot

• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/

• South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17

• Google Home: https://home.google.com/welcome/

• Cursor: https://www.cursor.com/

• v0: https://v0.dev/

• Bolt: https://bolt.new/

• Lovable: https://lovable.dev/

• Replit: https://replit.com/

• 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

• 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

• 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

• 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

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/

• Google Now: https://en.wikipedia.org/wiki/Google_Now

• Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7

• Granola: https://www.granola.ai/

• Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831

• Sindhu Vee’s website: https://sindhuvee.com/

• Nate Bargatze’s website: https://natebargatze.com/

—

Recommended book:

• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351

—

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.

Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world’s top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut’s relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience.

What you’ll learn:

1. Revolut’s unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing power

2. How a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launches

3. How Revolut maintains quality while shipping hundreds of features across over 50 countries

4. Why Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company’s most successful product leaders

5. How Revolut’s founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovation

6. Their framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countries

7. The importance of treating products that are 99% done as closer to 0% done, vs. 100% done

—

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

—

Where to find Dmitry Zlokazov:

• X: https://x.com/Dzlokazov

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

—

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 Dmitry and Revolut

(03:41) Revolut’s unique approach to product management

(06:58) The role and responsibilities of product owners

(09:28) Types of product owners at Revolut

(15:50) Building “wow” products

(25:00) Hiring practices

(31:33) Managing teams and projects

(41:07) Revolut’s diverse product offerings

(44:40) Scaling new products successfully

(52:10) Attracting top talent

(58:43) Failure corner

(01:02:49) Lightning round and final thoughts

—

Referenced:

• Revolut: https://www.revolut.com/

• Intercom: https://www.intercom.com/

• Palantir: https://www.palantir.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

• Deliver WOW to our customers: https://www.revolut.com/blog/post/deliver-wow/

• Nik Storonsky on LinkedIn: https://www.linkedin.com/in/nstoronsky

• Vlad Yatsenko on LinkedIn: https://www.linkedin.com/in/yatsenko/

• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (entrepreneur and writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi

• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product

• Gokul Rajaram on X: https://x.com/gokulr

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

• Schlep blindness: https://www.paulgraham.com/schlep.html

• Revolut Launches RevPoints Loyalty Programme, Turning Daily Expenses into Exclusive Rewards: https://www.revolut.com/news/revolut_launches_revpoints_loyalty_programme_turning_daily_expenses_into_exclusive_rewards/

• Gemini: https://gemini.google.com/

• ChatGPT: https://chatgpt.com/

• Figma: https://www.figma.com/

• Oppenheimer: https://www.imdb.com/title/tt15398776/

• Manus: https://manus.im/

• Eisenhower quote: https://quoteinvestigator.com/2017/11/18/planning/

• Wealth protection: https://help.revolut.com/help/security-logging-in/wealth-protection/what-is-wealth-protection/

—

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

• Build: An Unorthodox Guide to Making Things Worth Making―Personal Journey from Product Designer to Mentor: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

—

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.

Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn.

What you’ll learn:

• Why almost a third of all Palantir’s PMs go on to start companies

• How the “forward-deployed engineer” model works and why it creates exceptional product leaders

• How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins

• The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people

• Why the company intentionally avoids traditional titles and career ladders—and what they do instead

• Why they built an ontology-first data platform that LLMs love

• How Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent types

• The moral case for working at a company like Palantir

—

Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Attio—The powerful, flexible CRM for fast-growing startups

• OneSchema—Import CSV data 10x faster

—

Where to find Nabeel S. Qureshi:

• X: https://x.com/nabeelqu

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

• Website: https://nabeelqu.co/

—

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 Nabeel S. Qureshi

(05:10) Palantir’s unique culture and hiring

(13:29) What Palantir looks for in people

(16:14) Why they don't have titles

(19:11) Forward-deployed engineers at Palantir

(25:23) Key principles of Palantir's success

(30:00) Gotham and Foundry

(36:58) The ontology concept

(38:02) Life as a forward-deployed engineer

(41:36) Balancing custom solutions and product vision

(46:36) Advice on how to implement forward-deployed engineers

(50:41) The current state of forward-deployed engineers at Palantir

(53:15) The power of ingesting, cleaning and analyzing data

(59:25) Hiring for mission-driven startups

(01:05:30) What makes Palantir PMs different

(01:10:00) The moral question of Palantir

(01:16:03) Advice for new startups

(01:21:12) AI corner

(01:24:00) Contrarian corner

(01:25:42) Lightning round and final thoughts

—

Referenced:

• Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir

• Palantir: https://www.palantir.com/

• Intercom: https://www.intercom.com/

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

• Gotham: https://www.palantir.com/platforms/gotham/

• Foundry: https://www.palantir.com/platforms/foundry/

• Peter Thiel on X: https://x.com/peterthiel

• Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp

• Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur)

• Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/

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

• This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit

• Safe Superintelligence: https://ssi.inc/

• Mira Murati on X: https://x.com/miramurati

• Stripe: https://stripe.com/

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

• Airbus: https://www.airbus.com/en

• NIH: https://www.nih.gov/

• Jupyter Notebooks: https://jupyter.org/

• Shyam Sankar on LinkedIn: https://www.linkedin.com/in/shyamsankar/

• Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8

• Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms

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

• Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350

• SAP: https://www.sap.com/index.html

• Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/

• Understanding ‘Forward Deployed Engineering’ and Why Your Company Probably Shouldn’t Do It: https://www.barry.ooo/posts/fde-culture

• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

• Retool’s Path to Product-Market Fit—Lessons for Getting to 100 Happy Customers, Faster: https://review.firstround.com/retools-path-to-product-market-fit-lessons-for-getting-to-100-happy-customers-faster/

• How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe): https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big

• Looker: https://cloud.google.com/looker

• Sorry, that isn’t an FDE: https://tedmabrey.substack.com/p/sorry-that-isnt-an-fde

• Glean: https://www.glean.com/

• Limited Engagement: Is Tech Becoming More Diverse?: https://www.bkmag.com/2017/01/31/limited-engagement-creating-diversity-in-the-tech-industry/

• Operation Warp Speed: https://en.wikipedia.org/wiki/Operation_Warp_Speed

• Mark Zuckerberg testifies: https://www.businessinsider.com/facebook-ceo-mark-zuckerberg-testifies-congress-libra-cryptocurrency-2019-10

• Anduril: https://www.anduril.com/

• SpaceX: https://www.spacex.com/

• Principles: https://nabeelqu.co/principles

• Wispr Flow: https://wisprflow.ai/

• Claude code: https://docs.anthropic.com/en/docs/agents-and-tools/claude-code/overview

• Gemini Pro 2.5: https://deepmind.google/technologies/gemini/pro/

• DeepMind: https://deepmind.google/

• Latent Space newsletter: https://www.latent.space/

• Swyx on x: https://x.com/swyx

• Neural networks in chess programs: https://www.chessprogramming.org/Neural_Networks

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

• The top chess players in the world: https://www.chess.com/players

• Decision to Leave: https://www.imdb.com/title/tt12477480/

• Oldboy: https://www.imdb.com/title/tt0364569/

• Christopher Alexander: https://en.wikipedia.org/wiki/Christopher_Alexander

—

Recommended books:

• The Technological Republic: Hard Power, Soft Belief, and the Future of the West: https://www.amazon.com/Technological-Republic-Power-Belief-Future/dp/0593798694

• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296

• Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178/

• William Shakespeare: Histories: https://www.amazon.com/Histories-Everymans-Library-William-Shakespeare/dp/0679433120/

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

• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002

—

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.

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.

In our conversation, we cover:

1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”

2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience

3. Why teams most often fail (hint: it’s not lack of talent or strategy)

4. How busyness often masks deeper issues of self-worth

5. Why a “growth mindset” can be problematic

6. The importance of legacy and what it means to live a meaningful life

7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots

8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity

—

Brought to you by:

Eppo—Run reliable, impactful experiments

Contentsquare—Create better digital experiences

OneSchema—Import CSV data 10x faster

—

Where to find Jerry Colonna:

• X: https://x.com/jerrycolonna

• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/

• Website: https://reunion.reboot.io/

—

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 Jerry Colonna

(04:12) Jerry’s key question

(06:55) The equation for great leadership

(09:37) The big lie of success and happiness

(12:12) The consciousness hack

(15:56) Getting over the fear of consequences

(20:23) The problem with bypassing our childhood baggage

(23:22) Radical self-inquiry: asking the tough questions

(27:05) Shared experiences: the power of community

(30:25) The trap of busyness and attachment

(40:45) Understanding our own intentions

(46:58) Legacy and purpose

(55:43) Writing for self-discovery

(57:12) The impact of AI on humanity

(01:05:00) Turning a growth mindset into a fixed mindset

(01:11:30) The role of radical self-inquiry in leadership

(01:19:24) Final thoughts and reflections

—

Referenced:

• Naropa University: https://www.naropa.edu/

• Fitler Club: https://fitlerclub.com

• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/

• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830

• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism

• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821

• Simon Sinek’s website: https://simonsinek.com/

• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/

• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318

• Evernote: https://evernote.com/

• Claude: https://claude.ai

• Peter Senge on X: https://x.com/petersenge

• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your

• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/

• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living

—

Recommended books:

• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536

• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139

• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511

• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431

• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586

• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/

—

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.

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott’s background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you’ll learn:

1. How a team of “Devins” are already producing 25% of Cognition’s pull requests, and they are on track to hit 50% by year’s end

2. How each engineer on Cognition’s 15-person engineering team works with about five Devins each

3. How Devin has evolved from a “high school CS student” to a “junior engineer” over the past year

4. Why engineering will shift from “bricklayers” to “architects”

5. Why AI tools will lead to more engineering jobs rather than fewer

6. How Devin creates its own wiki to understand and document complex codebases

7. The eight pivots Cognition went through before landing on their current approach

8. The cultural shifts required to successfully adopt AI engineers

—

Brought to you by:

Enterpret—Transform customer feedback into product growth

Paragon—Ship every SaaS integration your customers want

Attio—The powerful, flexible CRM for fast-growing startups

—

Where to find Scott Wu:

• X: https://x.com/scottwu46

• LinkedIn: https://www.linkedin.com/in/scott-wu-8b94ab96/

—

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 Scott Wu and Devin

(09:13) Scaling and future prospects

(10:23) Devin's origin story

(17:26) The idea of Devin as a person

(22:19) How a team of “Devins” are already producing 25% of Cognition’s pull requests

(25:17) Important skills in the AI era

(30:21) How Cognition’s engineering team works with Devin's

(34:37) Live demo

(42:20) Devin’s codebase integration

(44:50) Automation with Linear

(46:53) What Devin does best

(52:56) The future of AI in software engineering

(57:13) Moats and stickiness in AI

(01:01:57) The tech that enables Devin

(01:04:14) AI will be the biggest technology shift of our lives

(01:07:25) Adopting Devin in your company

(01:15:13) Startup wisdom and hiring practices

(01:22:32) Lightning round and final thoughts

—

Referenced:

• Devin: https://devin.ai/

• GitHub: https://github.com/

• Linear: https://linear.app/

• Waymo: https://waymo.com/

• GitHub Copilot: https://github.com/features/copilot

• Cursor: https://www.cursor.com/

• Anysphere: https://anysphere.inc/

• Bolt: https://bolt.new/

• StackBlitz: https://stackblitz.com/

• Cognition: https://cognition.ai/

• v0: https://v0.dev/

• Vercel: https://vercel.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

• 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

• Assembly: https://en.wikipedia.org/wiki/Assembly_language

• Pascal: https://en.wikipedia.org/wiki/Pascal_(programming_language)

• Python: https://www.python.org/

• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox

• Datadog: https://www.datadoghq.com/

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

• 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

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Windsurf: https://windsurf.com/

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

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

• Magic the Gathering: https://magic.wizards.com/en

• Aura frames: https://auraframes.com/

• AirPods: https://www.apple.com/airpods/

• Steven Hao on LinkedIn: https://www.linkedin.com/in/steven-hao-160b9638/

• Walden Yan on LinkedIn: https://www.linkedin.com/in/waldenyan/

—

Recommended books:

• How to Win Friends & Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

• The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X

• The Great Gatsby: https://www.amazon.com/Great-Gatsby-F-Scott-Fitzgerald/dp/0743273567

—

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.

Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future.

What you’ll learn:

• Cursor's early pivot from automating CAD to automating code

• Michael’s vision for “what comes after code” and how programming will evolve

• Why Cursor built their own custom AI models despite not starting there

• Key lessons from Cursor’s rapid growth

• Why “taste” and logic design will become more valuable engineering skills than technical coding ability

• Why the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winner

• Michael’s advice for engineers and product teams preparing for the AI future

—

Brought to you by:

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security

OneSchema—Import CSV data 10x faster

—

Where to find Michael Truell:

• X: https://x.com/mntruell

• LinkedIn: https://www.linkedin.com/in/michael-t-5b1bbb122/

• Website: https://mntruell.com/

—

In this episode, we cover:

(00:00) Introduction to Michael Truell and Cursor

(04:20) What comes after code

(08:32) The importance of taste

(12:39) Cursor’s origin story

(18:31) Why they chose to build an IDE

(22:39) Will everyone become engineering managers?

(24:31) How they decided it was time to ship

(26:45) Reflecting on Cursor's success

(32:03) Counterintuitive lessons on building AI products

(34:02) Inside Cursor's stack

(38:42) Defensibility and market dynamics in AI

(46:13) Tips for using Cursor

(51:25) Hiring and building a strong team

(59:10) Staying focused amid rapid AI advancements

(01:02:31) Final thoughts and advice for aspiring AI innovators

—

Referenced:

• Cursor: https://www.cursor.com/

• Microsoft Copilot: https://copilot.microsoft.com/

• Scaling laws for neural language models: https://openai.com/index/scaling-laws-for-neural-language-models/

• MIT: https://www.mit.edu/

• Telegram: https://telegram.org/

• Signal: https://signal.org/

• WhatsApp: https://www.whatsapp.com/

• Devin: https://devin.ai/

• Visual Studio Code: https://code.visualstudio.com/

• Chromium: https://chromium.googlesource.com/chromium/src/base/

• Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: https://learnprompting.org/blog/gpt_wrappers

• 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

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• DALL-E 3: https://openai.com/index/dall-e-3/

• Stable Diffusion 3: https://stability.ai/news/stable-diffusion-3

—

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.

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.

What you’ll learn:

1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team

2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment

3. How focusing on impact, rather than just shipping features, has transformed the company’s culture

4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning

5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster

6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Airtable ProductCentral—Launch to new heights with a unified system for product development

• Vanta—Automate compliance. Simplify security

—

Where to find Daniel Lereya:

• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/

—

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 Daniel and monday.com

(04:20) The pivotal moment: competitors shipping faster

(08:50) Setting ambitious goals

(17:44) Focusing on impact rather than features

(27:07) Transforming your product quarterly

(32:07) Scaling monday.com: challenges and strategies

(39:14) How monday.com maintains transparency as a public company

(45:40) The importance of taking risks

(51:02) Counterintuitive lessons in product development

(54:33) The value of timeboxing and deadlines

(57:28) Embracing user feedback

(59:54) Adapting leadership styles

(01:04:43) Personal reflections on leadership

(01:10:41) Handling crises and strategic planning

(01:17:28) The role of AI in work and personal life

(01:22:13) Final thoughts and lightning round

—

Referenced:

• Monday.com: https://monday.com/

• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board

• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/

• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/

• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer

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

• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

• SpaceX: https://www.spacex.com/

• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/

• ChatGPT: https://chatgpt.com/

• Cursor: https://www.cursor.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• FIFA 22: https://store.playstation.com/en-us/concept/10002538/

• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890

• Google Photos: https://photos.google.com/

—

Recommended books:

• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860

• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/

—

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.

AI is rapidly changing how we live and work. It’s exciting, but also overwhelming. If you’re struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I’m thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny’s Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they’ve learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just looking to level up your AI skills, How I AI is for you.

—

SUBSCRIBE TO THE SHOW

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→ Apple: https://podcasts.apple.com/us/podcast/how-i-ai/id1809663079