Lenny's Podcast: Product | Growth | Career Lenny Rachitsky

Roger Martin is one of the world’s leading experts on strategy and the author of Playing to Win, one of the most beloved books on strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books. In our conversation, we discuss:
• The five key questions you need to answer to develop an effective strategy
• Why most companies get strategy wrong
• How to avoid “playing to play” instead of playing to win
• Real-world strategy examples from Procter & Gamble, Southwest Airlines, Lego, and Figma
• How to think about differentiation vs. low cost
• Shortcomings of current strategy education
• Much more
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• Webflow—The web experience platform
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Cycle—Your feedback hub, on autopilot
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Find the transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin
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Where to find Roger Martin:
• X: https://x.com/RogerLMartin
• LinkedIn: https://www.linkedin.com/in/roger-martin-9916911a9/
• Website: https://rogerlmartin.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) Roger’s background
(02:20) The importance of strategy
(07:00) Challenges in developing strategy
(08:30) Critique of modern strategy education
(14:00) Hamilton Helmer and Richard Rumelt
(17:40) Defining strategy
(19:12) The Strategy Choice Cascade
(23:20) Playing to win vs. playing to play
(24:57) Examples of strategic success
(30:49) Differentiation and moats
(40:23) Applying strategy to real-world scenarios
(43:47) Customer-centric strategy
(44:45) Defining the market and product
(45:59) Value chain and distribution
(48:28) Cost leadership vs. differentiation
(53:16) Capabilities and management systems
(57:14) Competitive advantage and market positioning
(01:02:41) Counterpositioning and fault lines
(01:05:53) Adapting to AI and market changes
(01:14:11) Betterment over perfection
(01:18:42) Final thoughts on strategy
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Referenced:
• Nearly 10% of S&P 500 CEOs are alumni of Procter & Gamble: https://www.bizjournals.com/cincinnati/news/2023/02/06/10-of-s-p-500-ceos-pg.html
• FigJam: https://www.figma.com/figjam/
• Figma: https://www.figma.com/
• What Is Resource-Based Theory?: https://www.igi-global.com/dictionary/the-impact-of-technological-governance-and-political-capabilities-on-firms-performances-under-economic-turbulence/67915
• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/
• Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487
• VRIO Framework Explained: https://strategicmanagementinsight.com/tools/vrio/
• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer
• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard
• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319
• Boston Consulting Group: https://www.bcg.com/
• Bruce Henderson: https://en.wikipedia.org/wiki/Bruce_Henderson
• Lego: https://www.lego.com
• Vanguard: https://investor.vanguard.com/
• Southwest Airlines: https://www.southwest.com/
• How Amazon Managed to Dethrone Walmart: https://www.nytimes.com/interactive/2021/08/20/technology/how-amazon-beat-walmart.html
• GM Lost a 10-Year Battle with Tesla, Pulling the Plug on a Long Line of EVs: https://www.forbes.com/sites/brookecrothers/2023/07/09/gm-killed-its-electric-cars-and-lost-a-10-year-battle-with-tesla/
• Westlaw: https://www.westlawinte

Rory Sutherland is widely regarded as one of the most influential (and most entertaining) thinkers in marketing and behavioral science. He’s the vice chairman of Ogilvy UK, the author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life, and the founder of Nudgestock, the world’s biggest festival of behavioral science and creativity. He champions thinking from first principles and using human psychology—what he calls “thinking psycho-logically”—over mere logic. In our conversation, we cover:
• Why good products don’t always succeed, and bad ones don’t necessarily fail
• Why less functionality can sometimes be more valuable
• The importance of fame in building successful brands
• The importance of timing in product success
• The concept of “most advanced, yet acceptable”
• Why metrics-driven workplaces can be demotivating
• Lots of real-world case studies
• Much more

Note: We encountered some technical difficulties that led to less than ideal video quality for this episode, but the lessons from this conversation made it impossible for me to not publish it anyway. Thanks for your understanding and for bearing with the less-than-ideal video quality. 
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Brought to you by:
• Pendo—The only all-in-one product experience platform for any type of application
• Cycle—Your feedback hub, on autopilot
• Coda—The all-in-one collaborative workspace
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Find the transcript at: https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing
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Where to find Rory Sutherland:
• X: https://x.com/rorysutherland
• LinkedIn: https://www.linkedin.com/in/rorysutherland
• Book: Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X
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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) Rory’s background
(02:37) The success and failure of products
(04:08) Why the urge to appear serious can be a disaster in marketing
(08:05) The role of distinctiveness in product design
(12:29) The MAYA principle
(15:50) How thinking irrationally can be advantageous
(17:40) The fault of multiple-choice tests
(21:31) Companies that have successfully implemented out-of-the-box thinking
(30:31) “Psycho-logical” thinking
(31:45) The hare and the dog metaphor
(38:51) Marketing’s crucial role in product adoption
(49:21) The quirks of Google Glass
(55:44) Survivorship bias
(56:09) Balancing rational ideas with irrational ideas
(01:06:19) The rise and fall of tech innovations
(01:09:54) Consistency, distinctiveness, and clarity
(01:21:12) Considering psychological, technological, and economic factors in parallel
(01:23:35) Where to find Rory
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Referenced:
• Google Glass: https://en.wikipedia.org/wiki/Google_Glass
• Meta Portal TV: https://www.meta.com/portal/products/portal-tv/
• Rory’s quote in a LinkedIn post: https://www.linkedin.com/posts/brad-jackson-04766642_the-urge-to-appear-serious-is-a-disaster-activity-7093497742710210560-1LYN/
• The MAYA Principle: Design for the Future, but Balance It with Your Users’ Present: https://www.interaction-design.org/literature/article/design-for-the-future-but-balance-it-with-your-users-present
• Ogilvy: https://www.ogilvy.com/
• MCI: https://www.mci.world/
• Veuve Clicquot: https://en.wikipedia.org/wiki/Veuve_Clicquot
• Why do the French call the British ‘the roast beefs’?: http://news.bbc.co.uk/2/hi/2913151.stm
• The Killing on Hulu: https://www.hulu.com/series/the-killing-f5da5c2d-4626-4ba9-bcf3-ff5f891771fb
• Original The Killing on BBC: https://www.bbc.co.uk/programmes/b017h7m1
• The Mandarin Oriental, Hong Kong: https://www.mandarinoriental.com/en/hong-kong/victoria-harbour
• SAT: https://satsuite.collegeboard.org/sat

Jessica Lachs is the global head of analytics and data science at DoorDash, where she’s built one of the largest and most respected data organizations in tech. In her more than 10 years at DoorDash, she has served as the first general manager, responsible for launching new markets; the head of business ops and analytics; and the VP of analytics and data science. Previously, Jessica founded GiftSimple, a social gifting startup, and started her career at Lehman Brothers as an investment banking analyst. In our conversation, she shares:
• How to structure and scale a high-impact analytics organization
• Centralized vs. decentralized data teams
• How to pick the right metric and aligning incentives
• Advice for data people on how and when to push back
• Lessons learned from building a global data team
• How to foster a culture of extreme ownership
• The role of AI in improving analytics team productivity
• Advice for aspiring data leaders without formal training
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Brought to you by:
• Webflow—The web experience platform
• Anvil—The fastest way to build software for documents
• Attio—The powerful, flexible CRM for fast-growing startups
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Find the transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-data-org-jessica-lachs
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Where to find Jessica Lachs:
• X: https://x.com/jesslachs
• LinkedIn: https://www.linkedin.com/in/jessica-lachs/
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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) Jessica’s background
(04:59) Centralized vs. embedded analytics teams
(10:52) The benefits of a centralized analytics team
(15:10) Balancing proactive and reactive work
(20:45) Advice on how to push back effectively
(24:20) Hiring for curiosity and problem solving
(28:57) Coming from a non-traditional background
(34:40) The early days and culture at DoorDash
(40:39) Encouraging cross-functional roles
(44:39) Defining effective metrics
(46:30) Simplifying metrics for better outcomes
(55:28) Focusing on edge cases and fail states
(01:00:12) Managing a global data organization
(01:02:31) Leveraging AI for productivity
(01:05:25) Building diverse and skilled data teams
(01:08:40) Lightning round
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Referenced:
• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence
• Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/
• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/
• Imposter Syndrome: Why You May Feel Like a Fraud: https://www.verywellmind.com/imposter-syndrome-and-social-anxiety-disorder-4156469
• Stanley Tang on LinkedIn: https://www.linkedin.com/in/stanleytang/
• Andy Fang on LinkedIn: https://www.linkedin.com/in/fangsterr/
• Evan Moore on LinkedIn: https://www.linkedin.com/in/evanmoore/
• How WeDash became the flagship employee program for DoorDash: https://careers.doordash.com/blog/wedash-doordash-employee-program-how-does-it-work
• Leading with empathy | Keith Yandell (DoorDash, Uber): https://www.lennysnewsletter.com/p/leading-with-empathy-keith-yandell
• The Rose Code: https://www.amazon.com/Rose-Code-Novel-Kate-Quinn/dp/006305941X
• Libby app: https://libbyapp.com/
• The West Wing on Prime: https://www.amazon.com/West-Wing-Complete-First-Season/dp/B000KZPG04
• Alias on Prime: https://www.amazon.com/Alias-Season-1/dp/B00748O13S
• Joseon sunscreens: https://beautyofjoseon.com/
• Innisfree sunscreens: https://us.innisfree.com/
• John Steinbeck quote: https://www.brainyquote.com/quotes/john_steinbeck_103825
• Vanessa Roberts on LinkedIn: https://www.linkedin.com/in/vanessa-roberts-b8a509a/
• Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/
• Elizabeth Jarvis-Shean on LinkedIn: https://www.linkedin.com/in/elizabeth-jarvis-shean-141a7966/
• Regina (Gina) T

Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss:
• The power of customer obsession and how to operationalize it in the product development process
• How to pick the right metrics and use them to drive impact
• Techniques for getting things done at big companies
• A group practice Jeff started to uplevel product craft, called Study Group
• The story behind Stripe Atlas and its mission to increase entrepreneurship globally
• Lessons from working with the founders of Stripe
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Brought to you by:
• Pendo—The only all-in-one product experience platform for any type of application
• Cycle—Your feedback hub, on autopilot
• Anvil—The fastest way to build software for documents
—
Find the transcript at: https://www.lennysnewsletter.com/p/creating-a-culture-of-excellence
—
Where to find Jeff Weinstein:
• X: https://x.com/jeff_weinstein
• LinkedIn: https://www.linkedin.com/in/jeffwweinstein/
• Email: jweinstein@gmail.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) Jeff’s background 
(10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach
(15:38) The importance of craft and quality
(24:15) Effective customer communication strategies
(28:57) The importance of speed in customer interactions 
(33:19) Narrowing your focus
(36:53) Why you should pay attention only to paying-customer feedback
(40:24) Practicing silence when communicating 
(45:33) The role of metrics in product success
(54:08) Empowering teams with a single metric
(58:23) Picking the right metric for your audience
(01:05:10) The importance of metric hygiene
(01:11:33) How Stripe uses “study groups” for product improvement
(01:37:20) Stripe’s Atlas: simplifying company formation
(01:50:38) Automation and operational efficiency
(01:55:13) Diversity and team building
(02:03:09) Building new products within a large company
(02:21:10) Lightning round
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Referenced:
• Atlas: https://stripe.com/atlas
• Stripe: https://stripe.com/
• SQL: https://en.wikipedia.org/wiki/SQL
• GitHub: https://github.com/
• Linear: https://linear.app/
• Figma: https://www.figma.com/
• Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300
• The “Collison installation”: https://news.ycombinator.com/item?id=18400504
• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p
• Fidelity: https://www.fidelity.com/
• 83(b) election: https://docs.stripe.com/atlas/83b-election
• Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638
• What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation
• Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained
• 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them
• Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/
• Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/
• AngelList: https://www.angellist.com/
• Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/
• Stripe Atlas perks partners: https://suppor

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:
• The three elements of breakthrough startup ideas
• Why you need to both think and act differently
• How to avoid the “comparison trap” and “conformity trap”
• The importance of movements, storytelling, and healthy disagreeableness in startup success
• How to apply pattern-breaking principles within large companies
• Mike’s one piece of advice for founders
• Much more

Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.
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Brought to you by:
• Enterpret—Transform customer feedback into product growth
• Anvil—The fastest way to build software for documents
• Webflow—The web experience platform
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Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr
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Where to find Mike Maples, Jr.:
• X: https://x.com/m2jr
• LinkedIn: https://www.linkedin.com/in/maples/
• Substack: https://greatness.substack.com/
• Website: https://www.floodgate.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) Mike’s background
(03:10) The inspiration behind Pattern Breakers
(08:09) Uncovering startup insights
(11:37) A quick summary of Pattern Breakers
(13:52) Coming up with an idea
(15:30) Inflections
(17:09) Examples of inflections
(28:10) Insights
(36:58) The power of surprises
(47:36) Founder-future fit
(55:33) Advice for aspiring founders
(56:41) Living in the future: valid opinions
(55:34) Case study: Maddie Hall and Living Carbon
(58:40) Identifying lighthouse customers
(01:00:53) The importance of desperation in customer needs
(01:03:57) Creating movements and storytelling
(01:24:22) The role of disagreeableness in startups
(01:34:42) Applying these principles within a company
(01:40:43) Lightning round
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Referenced:
• Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355
• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv
• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354
• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/
• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/
• The Craigslist Killers: https://www.gq.com/story/craigslist-killers
• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-so

Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:
• How intuition and product taste drive Dylan’s decision-making
• The challenge of keeping things simple
• Dylan’s thoughts on the future of product management
• Lessons from Figma’s early days
• How Figma built their initial user base
• Dylan’s journey from intern to CEO of a 1,000+-person company
• The future of design tools and AI
—
Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Anvil—The fastest way to build software for documents
• User Testing—Human understanding. Human experiences.
—
Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config
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Where to find Dylan Field:
• X: https://x.com/zoink?lang=en
• LinkedIn: https://www.linkedin.com/in/dylanfield/
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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
(01:11) Welcoming Dylan Field
(02:36) Highlights and surprises from Config
(06:58) The philosophy of design
(08:01) Raccoon feet and muffin hands
(09:57) Building and refining intuition and product taste
(12:50) How to influence leadership
(16:14) The role of product managers
(21:12) The future of product management
(22:20) The importance of simplicity in design
(26:10) The long road to Figma’s launch
(27:44) Advice for aspiring entrepreneurs
(29:07) Knowing when it’s time to ship
(30:39) Early user acquisition strategies
(35:50) Spotting trends and future innovations
(39:20) Reflections on leadership and growth
(43:16) Lightning round
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Referenced:
• Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/
• Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w
• Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages
• Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o
• An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds
• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor
• An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
• Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/
• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/
• FigJam: https://www.figma.com/figjam/
• Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/
• Coda: https://coda.io/
• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/
• Websim: https://websim.ai/
• eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.


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