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Lenny Rachitsky

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

Lenny's Podcast: Product | Growth | Career

Seth Godin is a legend. He’s a marketer, teacher, entrepreneur, and author of more than 20 books, including Purple Cow, Permission Marketing, and Linchpin. He also writes one of the most popular and longest-running blogs in the world (approaching publishing 10,000 in a row!) and continues to shape how we think about marketing, brand, product, and creating lasting change in the world. In our conversation, we discuss:

• How to build remarkable products that spread

• The four critical strategic choices that determine your future

• How to develop good taste and high standards

• The role of tension in great strategy

• How Seth used Claude to write his newest book

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

—

Where to find Seth Godin:

• Blog: http://seths.blog/

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

• Website: https://www.sethgodin.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) Seth’s background

(05:17) Understanding good taste and upholding high standards

(08:09) Become the best at whatever you do

(09:48) Seth’s journey as a product manager

(14:09) What people often get wrong when building products

(16:00) Building a brand in the age of AI

(19:04) Using AI to enhance writing

(22:40) Four critical elements for an effective strategy

(27:38) The role of tension in strategy

(29:15) The concept of the purple cow

(33:11) "Safe is risky"

(34:56) The power of systems

(37:07) Better waves make better surfers

(38:10) Rebranding vs. re-logoing

(43:07) Empathetic leadership

(44:14) Conclusion and farewell

—

Referenced:

• Seth Godin on the Tim Ferriss Show: https://tim.blog/2024/03/20/seth-godin-3/

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao

• Spinnaker: https://spinnaker.io

• Ray Bradbury: https://en.wikipedia.org/wiki/Ray_Bradbury

• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• Roger Zelazny: https://en.wikipedia.org/wiki/Roger_Zelazny

• Herbie Hancock: https://en.wikipedia.org/wiki/Herbie_Hancock

• Fahrenheit 451 (game): https://www.filfre.net/2013/09/fahrenheit-451-the-game/

• RTFM: https://en.wikipedia.org/wiki/RTFM#

• Intercom: https://www.intercom.com

• Claude: https://claude.ai

• ChatGPT: https://chatgpt.com

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

• Steam: https://store.steampowered.com

• P.F. Flyers: https://pfflyers.com

• Steve Blank’s website: https://steveblank.com

• Marissa Mayer on X: https://x.com/marissamayer

• Jaguar unveils new logo ahead of electric relaunch: https://www.bbc.com/news/articles/cgr0pw00n7qo

• IHOP Becomes IHOb, the International House of ... Burgers: https://www.npr.org/2018/06/11/618844977/ihop-becomes-ihob-the-international-house-of-burgers

• Oreo’s Super Bowl Power-Outage Tweet Was 18 Months in the Making: https://www.businessinsider.com/oreos-super-bowl-power-outage-tweet-was-18-months-in-the-making-2013-3

• Tesla’s New ‘Ludicrous Mode’ Makes the Model S a Supercar: https://www.wired.com/2015/07/teslas-new-ludicrous-mode-makes-model-s-supercar

—

Recommended books:

• This Is Strategy: Make Better Plans (Create a Strategy to Elevate Your Career, Community & Life): https://www.amazon.com/This-Strategy-Better-Elevate-Community/dp/B0D47T8S7N• Purple Cow: Transform Your Business by Being Remarkable: https://www.amazon.com/Purple-Cow-New-Transform-Remarkable/dp/1591843170

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Seth Godin's best tactics for building remarkable products, strategies, brands and more

Jackson Shuttleworth is a Group PM at Duolingo, where he leads the retention team and the powerful streak feature. The streak feature, which gamifies consecutive days of learning, has been Duolingo’s most important and innovative growth lever and a key driver of their growth to a $14 billion business with almost 600 million users. In our conversation, we dive deep into the history and lessons of this feature:

• The evolution of the streak feature

• Biggest insights from over 600 streak-related experiments

• Biggest specific wins and misses along the way

• Key principles for building effective streak mechanics

• How to operate a high-velocity product team

• Tips for building engaging notification systems

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-duolingo-streaks

—

Where to find Jackson Shuttleworth:• LinkedIn: https://www.linkedin.com/in/jackson-shuttleworth/

—

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) Jackson’s background and an overview of Duolingo’s streak feature

(06:00) The impact of streaks on Duolingo’s success

(09:58) The origin and evolution of streaks

(14:50) Key experiments and insights

(24:38) User psychology and engagement strategies

(28:36) Duolingo’s product review structure

(33:07) Designing for clarity and adaptability

(46:59) Developing the Streak Freeze feature

(50:47) Balancing monetization and retention

(54:08) Notification strategies

(58:15) The Perfect Streak feature

(01:00:40) Enhancing the user experience 

(01:04:47) Team operations and experimentation

(01:18:57) Who can benefit from streaks

(01:21:00) Lightning round

—

Referenced:

• Duolingo streaks: https://duolingo.fandom.com/wiki/Streak

• How to make learning as addictive as social media: https://www.ted.com/talks/luis_von_ahn_how_to_make_learning_as_addictive_as_social_media?subtitle=en

• Luis von Ahn on LinkedIn: https://www.linkedin.com/in/luis-von-ahn-duolingo/

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

• Royal Match: https://www.dreamgames.com/games/royal-match

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• You’re on fire! Or, how we brought the streak milestone to life: https://blog.duolingo.com/streak-milestone-design-animation/

• Duolingo Doubles Down on Design and Animation with Acquisition of Hobbes: https://investors.duolingo.com/news-releases/news-release-details/duolingo-doubles-down-design-and-animation-acquisition-hobbes

• Hobbes: https://www.hobbes.work/

• Jira: https://www.atlassian.com/software/jira

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

• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon/

• Peloton: https://www.onepeloton.com/

• Bluey on Disney+: https://www.disneyplus.com/series/bluey/1xy9TAOQ0M3r

• Emily in Paris on Netflix: https://www.netflix.com/title/81037371

• Multi-position ladders at Home Depot: https://www.homedepot.com/b/Building-Materials-Ladders-Multi-Position-Ladders/N-5yc1vZasew

—

Recommended books:

• A Guide to Midwestern Conversation: https://www.amazon.com/Guide-Midwestern-Conversation-Taylor-Phillips/dp/1984861336

• Fate Is the Hunter: A Pilot’s Memoir: https://www.amazon.com/Fate-Hunter-Ernest-K-Gann/dp/0671636030

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Behind the product: Duolingo streaks | Jackson Shuttleworth (Group PM, Retention Team)

Farhan Thawar is the head of engineering at Shopify, where he oversees more than 1,000 engineers and a platform that powers over 10% of all U.S. e-commerce. Before Shopify, he was VP of engineering at Pivotal Labs and Xtreme Labs, and co-founder of Helpful.com. In our conversation, Farhan shares:

• Why choosing the harder path leads to better outcomes

• How to create intensity within your org (without burnout)

• Why every company should be embracing pair programming

• How he hires without interviewing

• How he built the world’s largest internship program

• His mission to create a “crafter’s paradise” for engineers

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Persona—A global leader in digital identity verification

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawer

—

Where to find Farhan Thawar:

• X: https://x.com/fnthawar

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

—

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) Farhan’s background

(05:38) Choosing the hard path

(09:37) Getting comfortable with looking dumb

(13:20) Lessons from working with visionaries

(19:19) Creating intensity in organizations

(22:06) The power of pair programming

(29:18) Shopify’s culture of intensity

(37:18) Meeting Armageddon: revolutionizing company meetings

(39:46) Reducing distractions

(41:10) Deleting 1M+ lines of code

(49:05) Three buckets of building

(57:45) Remote work and trust battery

(01:00:29) Finding stability in uncomfortable times

(01:03:14) Hiring philosophy

(01:11:41) Internship programs and co-op systems

(01:15:32) Lessons from managing 120 direct reports

(01:20:40) Failure corner

(01:27:46) Lightning round and closing thoughts

—

Referenced:

• The Steve Jobs quote about connecting dots: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only

• Shopify: https://www.shopify.com/

• GitHub: https://github.com/

• Farhan’s “questions to ask” framework: https://x.com/fnthawar/status/1514193402828574721

• Palantir: https://www.palantir.com/

• Joe Liemandt: https://www.linkedin.com/in/liemandt

• Chamath Palihapitya: https://en.wikipedia.org/wiki/Chamath_Palihapitiya

• Xtreme Labs: https://www.xtremelabs.io

• Parkinson’s law: https://www.verywellmind.com/what-is-parkinsons-law-6674423

• Pair programming: https://dev.to/documatic/pair-programming-best-practices-and-tools-154j

• Cody Fauser on LinkedIn: https://www.linkedin.com/in/codyfauser

• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product

• Chaos Monkey: We look at Shopify’s new ‘culture of focus’: https://www.siliconrepublic.com/careers/shopify-chaos-monkey-meetings-culture-deann-evans

• Empowering devs with AI: How Shopify made GitHub Copilot core to its culture: https://www.youtube.com/watch?v=wVKBwcm5dbw&t=2318s

• Tobi Lütke of Shopify: Powering a Team with a ‘Trust Battery’: https://www.nytimes.com/2016/04/24/business/tobi-lutke-of-shopify-powering-a-team-with-a-trust-battery.html

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

• Stop Being Deceived by Interviews When You’re Hiring: https://www.forbes.com/sites/forbesleadershipforum/2012/02/07/stop-being-deceived-by-interviews-when-youre-hiring/

• Shopify’s made the Life Story a major part of their interview: https://news.ycombinator.com/item?id=39294140

• Internships at Shopify: https://internships.shopify.com

• Nick Adams on LinkedIn: https://www.linkedin.com/in/nick-adams-32b28139

• React Native: https://reactnative.dev

• Swift: https://www.swift.org

• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview

• The Power of Performance Reviews: Use This System to Become a Better Manager: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager

• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

• The Secret to a Great Planning Process—Lessons from Airbnb and Eventbrite: https://review.firstround.com/the-secret-to-a-great-planning-process-lessons-from-airbnb-and-eventbrite

• How to do great work: https://www.paulgraham.com/greatwork.html

• Challengers on Prime: https://www.amazon.com/Challengers-Luca-Guadagnino/dp/B0CX5MZ9M4

• Halt and Catch Fire on Prime: https://www.amazon.com/Halt-Catch-Fire-Season-1/dp/B0CKXZNT96

• Meta Ray-Bans: https://www.meta.com/smart-glasses/shop-all

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

—

Recommended books:

• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/Undoing-Project-Friendship-Changed-Minds/dp/0393254593

• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• Manna: Two Visions of Humanity’s Future: https://www.amazon.com/Manna-Two-Visions-Humanitys-Future-ebook/dp/B007HQH67U

• Business Adventures: Twelve Classic Tales from the World of Wall Street: https://www.amazon.com/Business-Adventures-Twelve-Classic-Street/dp/1504000021

—

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

—

Lenny may be an investor in the companies discussed.
 

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

How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng)

Marc Benioff is the co-founder and CEO of Salesforce, the second-largest software company in the world. He started programming at age 15, selling his first program for $75, and went on to build Salesforce into a company worth more than $300 billion that also owns Slack, Tableau, Quip, and MuleSoft. Marc is known as a marketing legend, and is now leading Salesforce into the era of AI agents. In our conversation, we discuss:

• The importance of maintaining a beginner’s mind

• His approach to product launches and marketing

• Managing through tough times and layoffs

• His relationship with Steve Jobs and lessons learned

• Why Salesforce is betting big on AI agents

• Many stories from his entrepreneurial roller coaster

• Much more

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• Enterpret—Transform customer feedback into product growth

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

—

Where to find Marc Benioff:

• X: https://x.com/benioff

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

—

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 Marc Benioff and Salesforce

(03:54) Marc’s early career and domain names

(05:59) The App Store story and lessons from Steve Jobs

(15:18) Lessons from launching Salesforce

(22:03) The importance of keeping a beginner’s mindset

(29:53) Why Marc calls Salesforce the “25-year startup”

(31:47) Agentforce

(36:09) Why Marc says AI is the defining technology of our lifetime

(40:12) AI’s impact on the workforce

(42:31) Entrepreneurs need to be like conductors

(46:02) Failure corner

(50:32) The future of AI agents

(56:34) Final thoughts and farewell

—

Referenced:

• Bill.com: https://www.bill.com

• App Store: https://www.apple.com/app-store/

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

• Oracle: https://www.oracle.com

• Larry Ellison on X: https://x.com/larryellison

• Siebel Systems: https://en.wikipedia.org/wiki/Siebel_Systems

• Saba Software: https://talentedlearning.com/lms-vendor-directory/saba-software

• Tom Siebel on LinkedIn: https://www.linkedin.com/in/thomassiebel

• Avon: https://www.avon.com

• Salesforce Chief Has Pulled Some Crazy Stunts: https://www.businessinsider.com/marc-benioff-salesforcecom-chief-has-pulled-some-crazy-stunts-2012-3

• Matthew McConaughey on Instagram: https://www.instagram.com/officiallymcconaughey

• Woody Harrelson on Instagram: https://www.instagram.com/woodyharrelson

• “Ask More of AI” with Matthew McConaughey: https://www.youtube.com/playlist?list=PLnobS_RgN7JaxOsLD8WH0I9E6osK3UrfI

• Marc’s tweet about the ad with McConaughey and Harrelson: https://x.com/Benioff/status/1866175950062239784

• Chris Rock on Instagram: https://www.instagram.com/chrisrock

• Sushi Iwa: http://www.sushiiwa.jp/en/

• Ryoanji Temple Rock Garden: https://www.japan.travel/en/spot/1145/

• Neil Young Archives on Instagram: https://www.instagram.com/neilyoungarchives

• Mount Tam: https://en.wikipedia.org/wiki/Mount_Tamalpais

• Spirit Rock: https://www.spiritrock.org

• Jack Kornfield: https://www.spiritrock.org/teachers/jack-kornfield

• Agentforce: https://www.salesforce.com/form/agentforce/demo

• Minority Report on Prime: https://www.amazon.com/Minority-Report-Tom-Cruise/dp/B00A2FSSHK

• Peter Schwartz on X: https://x.com/peterschwartz2

• UCSF Health: https://www.ucsfhealth.org

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• Does AI improve doctors’ diagnoses? Study puts it to the test: https://www.sciencedaily.com/releases/2024/11/241113123419.htm

• A.I. Will Transform the Global Economy—if Humans Let It: https://www.nytimes.com/2024/12/07/special-series/ai-transform-global-economy.html

• Wargames on Prime: https://www.amazon.com/Wargames-Dabney-Coleman/dp/B0011EQBOS

• Her on Prime: https://www.amazon.com/Her-Joaquin-Phoenix/dp/B00KATY250

• AI (Einstein) at Salesforce: https://www.salesforce.com/in/artificial-intelligence

• Salesforce Signs Definitive Agreement to Acquire Airkit.ai: https://www.salesforce.com/news/stories/salesforce-signs-definitive-agreement-to-acquire-airkit-ai

• Salesforce Buys Big Data Startup RelateIQ for Up to $390M: https://techcrunch.com/2014/07/11/salesforce-buys-big-data-startup-relateiq-for-up-to-390m

• Salesforce to cut workforce by 10% after hiring ‘too many people’ during the pandemic: https://techcrunch.com/2023/01/04/salesforce-to-cut-workforce-by-10-after-hiring-too-many-people-during-the-pandemic

• Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell

• Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor

• Akio Toyoda: https://en.wikipedia.org/wiki/Akio_Toyoda

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

• TRS-80: https://en.wikipedia.org/wiki/TRS-80

• CLOAD Magazine: https://archive.org/details/cload_newsletter

—

Recommended books:

• Ghost Fleet: A Novel of the Next World War: https://www.amazon.com/Ghost-Fleet-Novel-Next-World/dp/054470505X

• Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company—and Revolutionized an Industry: https://www.amazon.com/Behind-Cloud-Salesforce-com-Billion-Dollar-Company/dp/0470521163

• Trailblazer: The Power of Business as the Greatest Platform for Change: https://www.amazon.com/Trailblazer-Business-Greatest-Platform-Change/dp/1984825194

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Behind the founder: Marc Benioff

Shaun Clowes is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversation, we discuss:

• Why most PMs are bad, and how to fix this

• Why great AI products are all about the data

• Why he changed his mind about being data-driven

• How to build your B2B growth team

• How to choose your next career stop

• Much more

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• BuildBetter—AI for product teams

• Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/why-great-ai-products-are-all-about-the-data-shaun-clowes

—

Where to find Shaun Clowes:

• X: https://x.com/ShaunMClowes

• LinkedIn: https://www.linkedin.com/in/shaun-clowes-80795014/

• Website: https://shaunclowes.com/about-shaun

• Reforge: https://www.reforge.com/profiles/shaun-clowes

—

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) Shaun’s background

(05:08) The state of product management

(09:33) Becoming a 10x product manager

(13:23) Specific ways to leverage AI in product management

(17:15) Feedback rivers

(19:20) AI's impact on data management

(24:35) The future of enterprise businesses with AI

(35:41) Data-driven decision-making

(45:50) Building effective growth teams

(50:18) The evolution of product-led growth

(56:16) Career insights and decision-making

(01:07:45) Failure corner

(01:12:32) Final thoughts and lightning round

—

Referenced:

• Steve Blank’s website: https://steveblank.com/

• Getting Out of the Building. 2 Minutes to See Why: https://www.youtube.com/watch?v=TbMgWr1YVfs

• OpenAI: https://openai.com/

• Claude: https://claude.ai/

• Sachin Rekhi on LinkedIn: https://www.linkedin.com/in/sachinrekhi/

• Video: Building Your Product Intuition with Feedback Rivers: https://www.sachinrekhi.com/video-building-your-product-intuition-with-feedback-rivers

• Confluent: https://www.confluent.io

• Workday: https://www.workday.com/

• Lenny and Friends Summit: https://lennyssummit.com/

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

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

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

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

• Jira: https://www.atlassian.com/software/jira

• Ashby: https://www.ashbyhq.com/

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

• Charlie Munger quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• Metromile: https://www.metromile.com/

• Tom Kennedy on LinkedIn: https://www.linkedin.com/in/tom-kennedy-37356b2b/

• 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

• Colin Powell’s 40-70 rule: https://www.42courses.com/blog/home/2019/12/10/colin-powells-40-70-rule

• Detroiters on Netflix: https://www.netflix.com/title/80165019

• Glean: https://www.glean.com/

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

• Listen: Five Simple Tools to Meet Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301

• Empress Falls Canyon and abseiling: https://bmac.com.au/blue-mountains-canyoning/empress-falls-canyon-and-abseiling

—

Recommended books:

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898

• Inspired: How to Create Products Customers Love: https://www.amazon.com/Inspired-Create-Products-Customers-Love/dp/0981690408

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Why great AI products are all about the data | Shaun Clowes (CPO Confluent, ex-Salesforce, Atlassian)

Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss:

• Gong’s unique approach to working with design partners

• Their unique pod model

• Why Eilon makes big decisions quickly

• Lessons learned from being early in AI

• The power of extreme focus

• His “spiral method” for learning complex topics quickly

• How to maintain quality while optimizing for speed

—

Brought to you by:

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

• Think Fast Talk Smart—Tools and techniques to help you communicate more effectively

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/inside-gong-eilon-reshef

—

Where to find Eilon Reshef:• LinkedIn: https://www.linkedin.com/in/eilonreshef

—

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) Eilon’s background

(04:20) The pod model

(06:33) Working with design partners

(09:13) Finding and coordinating design partners

(13:12) Balancing customer feedback and vision

(15:10) Gong's 95% feature adoption

(17:05) The importance of autonomy and trust

(23:30) How to implement this unique way of working

(27:15) Speed and decision-making

(31:47) Early AI adoption and lessons learned

(35:50) Building effective AI teams

(38:16) The spiral method for learning

(41:36) Narrowing down the initial customer profile

(44:24) Failure corner

(46:35) Lightning round

—

Referenced:

• Gong: https://www.gong.io

• Cisco: https://www.cisco.com/

• How Gong builds product: https://www.lennysnewsletter.com/p/how-gong-builds-product

• What is Montessori education?: https://amshq.org/About-Montessori/What-Is-Montessori

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• Amit Bendov on LinkedIn: https://www.linkedin.com/in/amitbendov/

• Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the

• Nvidia: https://www.nvidia.com

• Figma: https://www.figma.com

• The Spiral Method: https://www.gong.io/blog/using-the-spiral-method/

• Webex: https://www.webex.com/

• L’Oréal: https://www.lorealparisusa.com/

• American Express: https://www.americanexpress.com/

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Dishwasher basket: https://www.amazon.com/Munchkin-High-Capacity-Dishwasher-Basket/dp/B07ZPMYKKS/

• What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Hanlon’s razor: https://en.wikipedia.org/wiki/Hanlon%27s_razor

• Sabich: https://en.wikipedia.org/wiki/Sabich#Ingredients_and_description

• Careers at Gong: https://www.gong.io/careers

—

Recommended books:

• Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM

• “The Machine That Won the War”: https://www.goodreads.com/book/show/18402398-the-machine-that-won-the-war

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• The Ideal Executive: https://www.amazon.com/Ideal-Executive-Ichak-Kalderon-Adizes/dp/0937120030/

• Crucial Conversations: Tools for Talking when Stakes Are High: https://www.amazon.com/Crucial-Conversations-Tools-Talking-Stakes/dp/1260474186/

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Inside Gong: How teams work with design partners, their pod structure, autonomy, trust, and more | Eilon Reshef (co-founder and CPO)

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss:

• The psychology behind why we avoid difficult conversations

• Specific scripts for having five common difficult conversations

• How to handle defensive reactions in the moment

• The three questions you should end every meeting with

• “The founder prenup” that every founding team should work through

• Common leadership myths

• Stories of failure from Alisa’s career

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Rippling—Automate HR, IT, and finance so you can scale faster

• Liveblocks—Ready-made collaborative features to drop into your product

—

Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn

—

Where to find Alisa Cohn:

• X: https://x.com/AlisaCohn

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

• Website: https://www.alisacohn.com

• Podcast: https://www.alisacohn.com/podcast

—

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) Alisa’s background

(04:48) Having difficult conversations

(12:48) Scripts for performance feedback

(20:20) How to respond when someone is defensive or upset

(25:07) Scripts for handling promotion disappointments

(31:00) Scripts for handling terminations

(35:44) The importance of positive feedback

(38:49) Understanding your job as a leader

(44:55) Recognizing your own blind spots

(49:38) Three vital questions to ask in every meeting

(55:57) The founder prenup

(01:08:24) Failure corner

(01:13:00) Final thoughts and lightning round

—

Referenced:

• Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/

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

• Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf

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

• How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

• Joe Gebbia on X: https://x.com/jgebbia

• Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425

• Core Values List: https://jamesclear.com/core-values

• How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing

• Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii

• Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ

• Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on

—

Recommended books:

• From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

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

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

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about:

• The three eras of Dropbox’s growth and evolution

• The challenges he’s faced over the past 18 years

• What he learned about himself

• How he’s been able to manage his psychology as a founder

• The importance of maintaining your learning curve

• Finding purpose beyond metrics and growth

• The micro, macro, and meta aspects of building companies

• Much more

—

Brought to you by:

• Paragon—Ship every SaaS integration your customers want

• Explo—Embed customer-facing analytics in your product

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

—

Where to find Drew Houston:

• X: https://x.com/drewhouston

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

—

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 Drew and Dropbox

(04:44) The three eras of Dropbox

(07:53) The first era: Viral growth and early success

(14:19) The second era: Challenges and competition

(20:49) Strategic shifts and refocusing

(29:36) Personal reflections and leadership lessons

(40:19) Unlocking mindfulness and building support systems

(43:14) The Enneagram test

(50:35) The challenges of being a founder CEO

(58:11) The third era: Rebooting the team and core business

(01:22:41) Lessons and advice for aspiring founders

(01:27:46) Balancing personal and professional growth

(01:42:38) Final reflections and future outlook

—

Referenced:

• Dropbox: https://www.dropbox.com/

• Y Combinator: https://www.ycombinator.com/

• Paul Graham’s website: https://www.paulgraham.com/

• Hacker News: https://news.ycombinator.com/

• Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

• Sequoia Capital: https://www.sequoiacap.com/

• Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/

• Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/

• TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/

• Dropbox viral demo: https://youtu.be/7QmCUDHpNzE

• Digg: https://digg.com/

• Reddit: https://www.reddit.com/

• Hadi and Ali Partovi: https://www.partovi.org/

• Zynga: https://www.zynga.com/

• Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc

• Dropbox Carousel: https://en.wikipedia.org/wiki/Dropbox_Carousel

• Dropbox Is Buying Mega-Hyped Email Startup Mailbox: https://www.businessinsider.com/dropbox-is-buying-mega-hyped-email-startup-mailbox-2013-3

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• Intel: https://www.intel.com/

• Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore

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

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

• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)

• Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/

• The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs

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

• Ben Horowitz on X: https://x.com/bhorowitz

• Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker

• GitLab: https://about.gitlab.com/

• Automattic: https://automattic.com/

• Dropbox Dash: https://www.dash.dropbox.com/

• Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/welcome-command-e-to-dropbox-

• StarCraft: https://en.wikipedia.org/wiki/StarCraft_(video_game)

• Procter & Gamble and the Beauty of Small Wins: https://hbr.org/2009/10/the-beauty-of-small-wins

• Teaching Smart People How to Learn: https://hbr.org/1991/05/teaching-smart-people-how-to-learn

—

Recommended books:

• Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business: https://www.amazon.com/Guerilla-Marketing-Inexpensive-Strategies-Business/dp/0618785914

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

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

• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821

• Zone to Win: Organizing to Compete in an Age of Disruption: https://www.amazon.com/Zone-Win-Organizing-Compete-Disruption/dp/1682302113

• Warren Buffett’s books: https://www.amazon.com/warren-buffett-Books/s?k=warren+buffett&rh=n%3A283155

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239

• Invent and Wander: The Collected Writings of Jeff Bezos: https://www.amazon.com/Invent-Wander-Collected-Writings-Introduction/dp/1647820715/

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

—

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

—

Lenny may be an investor in the companies discussed.
 

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

Behind the founder: Drew Houston (Dropbox)

Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss:

• Key indicators that it’s time to hire PMs

• How to build your early PM team

• Why founders should initially take on the product manager role themselves

• How to attract top PM talent

• What she’s learned about going multi-product

• A case for investing in quality

• More

—

Skip the Mercury Personal waitlist: https://mercurytechnologies.typeform.com/lenny

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• OneSchema—Import CSV data 10x faster

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-build-your-product-team-from-scratch-rohini-pandhi

—

Where to find Rohini Pandhi:

• X: https://x.com/rohinip

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

—

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) Rohini’s background

(05:00) The role of product managers at Mercury

(09:51) Key indicators that it’s time to hire PMs

(13:18) Building the product team at Mercury

(19:53) Why you should avoid hiring PMs too early

(22:26) The different flavors of product management

(26:15) How to attract top talent

(35:59) Advocating for quality in product development

(44:10) Going multi-product

(46:37) Organizational structure for multi-product success

(50:57) Organizational culture for multi-product success

(52:07) Customer obsession and product development

(57:36) More lessons from going multi-product

(01:05:57) Transparent Collective: supporting underrepresented founders

(01:09:54) Lightning round

—

Referenced:

• Immad Akhund on X: https://x.com/immad

• Mercury: https://mercury.com

• Square: https://squareup.com

• Product management career ladders: https://www.lennysnewsletter.com/p/product-management-career-ladders

• Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7

• Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860

• What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Mercury Bill Pay: https://mercury.com/bill-pay

• Zip: https://zip.co

• Jira: https://www.atlassian.com/software/jira

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

• 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

• Transparent Collective: https://www.transparentcollective.com

• 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/16-reading-tips-from-naval-ravikant

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking

• Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses

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

• Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent

• Waymo: https://waymo.com

• Adam Robinson on X: https://x.com/IAmAdamRobinson

• Cyan Banister—From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More): https://tim.blog/2024/11/28/cyan-banister

• Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson

• Jobs at Mercury: https://mercury.com/jobs

—

Recommended books:

• Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890

• The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927

• Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367

• The Song of Achilles: https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627

—

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

—

Lenny may be an investor in the companies discussed.
 

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

How to build your product team from scratch, attract top product talent, go multi-product, and more | Rohini Pandhi (Mercury, Square)

Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss:

• Why everything worthwhile requires suffering

• Why most people operate on autopilot, and how to break free

• The “genie methodology” for discovering your true path

• The Nine Lives exercise for exploring different life possibilities

• How to overcome limiting beliefs that hold you back

• Why “not now” is often just another way of saying “never”

• More

—

Brought to you by:

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

• Persona—A global leader in digital identity verification

• Liveblocks—Ready-made collaborative features to drop into your product

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver

—

Where to find Graham Weaver:

• LinkedIn: https://www.linkedin.com/in/graham-weaver-2b79

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

• YouTube: https://www.youtube.com/@grahamcweaver

• Website: https://www.grahamweaver.com

• TikTok: https://www.tiktok.com/@grahamcweaver

—

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) Graham’s background

(05:30) Helping students find their true path

(07:40) The genie methodology

(12:36) Breaking free from autopilot mode

(17:54) Identifying and overcoming limiting beliefs

(20:33) Teaching entrepreneurship and personal fulfillment

(22:53) The reality of long-term success

(35:14) The role of accountability and executive coaching

(40:22) Daily goal setting for success

(43:11) The Nine Lives framework

(48:01) The dangers of the “not now” mentality

(55:27) Navigating life’s transitions

(57:19) Failure corner

(01:00:24) When to quit and when to persevere

(01:02:18) Final thoughts and lightning round

—

Referenced:

• Setting Goals: Demystified: https://www.grahamweaver.com/blog/goals

• Tony Robbins’s website: https://www.tonyrobbins.com

• Alpine Investors: https://alpineinvestors.com

• Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: https://www.grahamweaver.com/blog/stanford-graduate-business-school-last-lecture-2024

• I turned 50 today. Here is the most important thing I learned in my first half century: https://www.grahamweaver.com/blog/turning-50

• Where the Crawdads Sing on Prime Video: https://www.amazon.com/Where-Crawdads-Sing-Daisy-Edgar-Jones/dp/B0B5KBKDNL

• Chilipad Cube Bed Cooling System: https://www.amazon.com/Chilipad-Cube-Bed-Cooling-System/dp/B07GT9MYRW

• Sleepme OOLER Sleep System: https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G

• Eightsleep: https://www.eightsleep.com

• Howard Thurman’s quote: https://www.goodreads.com/quotes/6273-don-t-ask-what-the-world-needs-ask-what-makes-you

—

Recommended books:

• Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752

• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379

• Don’t Believe Everything You Think: Why Your Thinking Is the Beginning and End of Suffering: https://www.amazon.com/Dont-Believe-Everything-Think-Expanded/dp/B0D47VYQMY

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

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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.
 

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

How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors)

In this special compilation episode, we delve into failure—an overlooked source of wisdom. From freezing onstage in front of thousands of people, to coworkers staging an intervention, to huge product investments that went to zero, we’ve pulled our favorite stories of failure from 100+ podcast episodes. I hope these stories serve as a gentle nudge to view failure not as a setback but as a crucial detour toward growth.

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

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Find the full transcript at: https://www.lennysnewsletter.com/p/failure

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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, you’ll hear from:

(00:00) Lenny: Why I’m focusing on failure

(03:25) Katie Dill: The single meeting that changed how Katie leads forever

(08:03) Paul Adams: Freezing onstage in front of thousands of people

(18:38) Tom Conrad: Lessons from Pets.com and Quibi—two of the most famous product disasters of all time

(33:19) Sri Batchu: When you fail, make sure you fail conclusively

(39:00) Jiaona Zhang (JZ): One of the biggest product misses at Airbnb

(44:32) Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more

(57:57) Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure

(1:00:33) Thanks for listening

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

—

Lenny may be an investor in the companies discussed.
 

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

Failure

Lyt når som helst, hvor som helst

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