Lenny's Podcast: Product | Growth | Career

Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss: • 10 growth tactics that never work • Her 3 favorite growth frameworks • How to increase your career optionality — Brought to you by: • Sinch [https://sinch.com/lenny]—Build messaging, email, and calling into your product • Vanta [https://vanta.com/lenny]—Automate compliance. Simplify security • OneSchema [https://oneschema.co/lenny]—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna [https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna] — Where to find Elena Verna: • Newsletter: https://www.elenaverna.com/ [https://www.elenaverna.com/] • X: https://x.com/elenaverna [https://x.com/elenaverna] • LinkedIn: https://www.linkedin.com/in/elenaverna [https://www.linkedin.com/in/elenaverna] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [https://www.linkedin.com/in/lennyrachitsky/] — In this episode, we cover: (00:00) Welcome back, Elena! (06:02) Common mistakes growth teams make (08:31) #1: Hiring for growth roles too soon (15:09) #2: Hiring a head of growth to fix your problems (19:20) #3: Doing a rebrand to drive growth (25:11) #4: Obsessing over your competition (34:00) #5: Believing that your problems are unique (42:32) #6: Prioritizing other growth channels above earned channels (50:55) #7: Failing to evolve your growth model (01:01:06) #8: Not hiring advisors (01:05:55) #9: Over-experimenting (01:10:44) #10: Color optimizations, third-party signups, one-email wonders, and removing friction (01:15:00) Elena’s favorite growth frameworks (01:18:50) Contrarian corner: full-time jobs (01:26:05) Lightning round and final thoughts — Referenced: • 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 [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 [https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led] • Six rules of hiring for growth: https://www.lennysnewsletter.com/p/hiring-growth [https://www.lennysnewsletter.com/p/hiring-growth] • Figma: https://www.figma.com/ [https://www.figma.com/] • Miro: https://www.figma.com/ [https://www.figma.com/] • Notion: https://www.figma.com/ [https://www.figma.com/] • Carol Wong on LinkedIn: https://www.linkedin.com/in/carol-wong-14133927/ [https://www.linkedin.com/in/carol-wong-14133927/] • Dropbox: https://www.dropbox.com/ [https://www.dropbox.com/] • The Law of Shitty Clickthroughs: https://andrewchen.com/the-law-of-shitty-clickthroughs/ [https://andrewchen.com/the-law-of-shitty-clickthroughs/] • Miroverse: https://miro.com/miroverse/ [https://miro.com/miroverse/] • GitHub: https://github.com/ [https://github.com/] • My 9 Favorite Growth Frameworks: https://www.elenaverna.com/p/my-9-favorite-growth-frameworks [https://www.elenaverna.com/p/my-9-favorite-growth-frameworks] • Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loops [https://www.reforge.com/blog/growth-loops] • Racecar Growth Framework: https://www.reforge.com/blog/racecar-growth-framework [https://www.reforge.com/blog/racecar-growth-framework] • The Adjacent User: https://andrewchen.com/the-adjacent-user-theory/ [https://andrewchen.com/the-adjacent-user-theory/] • Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba [https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba] • Why I’m Unquitting Full-Time Roles: https://www.elenaverna.com/p/why-im-unquitting-full-time-roles [https://www.elenaverna.com/p/why-im-unquitting-full-time-roles] • Noah Smith’s newsletter: https://www.noahpinion.blog/ [https://www.noahpinion.blog/] • Beef on Netflix: https://www.netflix.com/title/81447461 [https://www.netflix.com/title/81447461] • Veep on Max: https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a [https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a] • The Last of Us on Max: https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a [https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a] • Heated boots: https://www.amazon.com/heated-boots/s?k=heated+boots [https://www.amazon.com/heated-boots/s?k=heated+boots] • Airpods Max: https://www.apple.com/airpods-max/ [https://www.apple.com/airpods-max/] • Memes by Elena: https://www.elenaverna.com/p/ten-funniest-growth-memes [https://www.elenaverna.com/p/ten-funniest-growth-memes] — Recommended books: • Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/ [https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/] • The Martian: https://www.amazon.com/Martian-Andy-Weir/dp/0553418025 [https://www.amazon.com/Martian-Andy-Weir/dp/0553418025] • We Are Legion (Bobiverse #1): https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587 [https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587] • Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285 [https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe [https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

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 [http://merge.dev/lenny]—A single API to add hundreds of integrations into your app • Persona [https://withpersona.com/lenny]—A global leader in digital identity verification • Liveblocks [https://liveblocks.io/lenny]—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 [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 [https://www.linkedin.com/in/graham-weaver-2b79] • Instagram: https://www.instagram.com/grahamcweaver [https://www.instagram.com/grahamcweaver] • YouTube: https://www.youtube.com/@grahamcweaver [https://www.youtube.com/@grahamcweaver] • Website: https://www.grahamweaver.com [https://www.grahamweaver.com] • TikTok: https://www.tiktok.com/@grahamcweaver [https://www.tiktok.com/@grahamcweaver] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://www.grahamweaver.com/blog/goals] • Tony Robbins’s website: https://www.tonyrobbins.com [https://www.tonyrobbins.com] • Alpine Investors: https://alpineinvestors.com [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 [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 [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 [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 [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 [https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G] • Eightsleep: https://www.eightsleep.com [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 [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 [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 [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 [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 [https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe [https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

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 [https://mercurytechnologies.typeform.com/lenny] — Brought to you by: • Cloudinary [http://cloudinary.com/lenny]—The foundational technology for all images and video on the internet • OneSchema [https://oneschema.co/lenny]—Import CSV data 10x faster • Airtable ProductCentral [https://www.airtable.com/lenny]—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 [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 [https://x.com/rohinip] • LinkedIn: https://www.linkedin.com/in/rohinipandhi [https://www.linkedin.com/in/rohinipandhi] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://x.com/immad] • Mercury: https://mercury.com [https://mercury.com] • Square: https://squareup.com [https://squareup.com] • Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7 [https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7] • Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860 [https://www.linkedin.com/in/jason-zhang-5645a860/] • What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html [https://www.nytimes.com/2022/11/14/business/dogfooding.html] • Mercury Bill Pay: https://mercury.com/bill-pay [https://mercury.com/bill-pay] • Zip: https://zip.co [https://zip.co] • Jira: https://www.atlassian.com/software/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 [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 [https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product] • Gokul Rajaram on X: https://x.com/gokulr [https://x.com/gokulr] • Transparent Collective: https://www.transparentcollective.com [https://www.transparentcollective.com] • 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/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 [https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs] • Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters [https://tv.apple.com/us/show/bad-sisters/umc.cmc.14kr4vv65unannh7doqgvlh20] • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses [https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o] • Severance on AppleTV+: https://tv.apple.com/us/show/severance [https://tv.apple.com/us/show/severance] • Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent [https://tv.apple.com/us/show/presumed-innocent] • Waymo: https://waymo.com [https://waymo.com] • Adam Robinson on X: https://x.com/IAmAdamRobinson [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 [https://tim.blog/2024/11/28/cyan-banister/] • Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson [https://www.linkedin.com/in/bobbymatson] • Jobs at Mercury: https://mercury.com/jobs [https://mercury.com/jobs] — Recommended books: • Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890 [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 [https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314] • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 [https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/] • Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367 [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 [https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627/] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe [https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

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 [https://www.useparagon.com/lenny]—Ship every SaaS integration your customers want • Explo [https://explo.co/lenny]—Embed customer-facing analytics in your product • Vanta [https://vanta.com/lenny]—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox [https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox] — Where to find Drew Houston: • X: https://x.com/drewhouston [https://x.com/drewhouston] • LinkedIn: https://www.linkedin.com/in/drewhouston/ [https://www.linkedin.com/in/drewhouston/] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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/ [https://www.dropbox.com/] • Y Combinator: https://www.ycombinator.com/ [https://www.ycombinator.com/] • Paul Graham’s website: https://www.paulgraham.com/ [https://www.paulgraham.com/] • Hacker News: https://news.ycombinator.com/ [https://news.ycombinator.com/] • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/ [https://www.linkedin.com/in/arashferdowsi/] • Sequoia Capital: https://www.sequoiacap.com/ [https://www.sequoiacap.com/] • Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/ [https://www.linkedin.com/in/pejman/] • Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/ [https://www.linkedin.com/in/michaelmoritz/] • TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/ [https://techcrunch.com/events/tc-disrupt-2024/] • Dropbox viral demo: https://youtu.be/7QmCUDHpNzE [https://youtu.be/7QmCUDHpNzE] • Digg: https://digg.com/ [https://digg.com/] • Reddit: https://www.reddit.com/ [https://www.reddit.com/] • Hadi and Ali Partovi: https://www.partovi.org/ [https://www.partovi.org/] • Zynga: https://www.zynga.com/ [https://www.zynga.com/] • Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc [https://www.youtube.com/watch?v=ilnfUa_-Rbc] • Dropbox Carousel: https://en.wikipedia.org/wiki/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 [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 [https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin] • Intel: https://www.intel.com/ [https://www.intel.com/] • Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore [https://en.wikipedia.org/wiki/Gordon_Moore] • Netscape: https://en.wikipedia.org/wiki/Netscape [https://en.wikipedia.org/wiki/Netscape] • Myspace: https://en.wikipedia.org/wiki/Myspace [https://en.wikipedia.org/wiki/Myspace] • Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) [https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)] • Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/ [https://www.enneagraminstitute.com/type-descriptions/] • The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs [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 [https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach] • Ben Horowitz on X: https://x.com/bhorowitz [https://x.com/bhorowitz] • Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker [https://hbr.org/2009/11/why-read-peter-drucker] • GitLab: https://about.gitlab.com/ [https://about.gitlab.com/] • Automattic: https://automattic.com/ [https://automattic.com/] • Dropbox Dash: https://www.dash.dropbox.com/ [https://www.dash.dropbox.com/] • Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/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) [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 [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 [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 [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 [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/ [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 [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 [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 [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 [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/ [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 [https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe [https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

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 [https://www.alisacohn.com/start-up/], [https://www.alisacohn.com/start-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 [https://www.alisacohn.com/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 [https://www.geteppo.com/]—Run reliable, impactful experiments • Rippling [http://www.rippling.com/lenny]—Automate HR, IT, and finance so you can scale faster • Liveblocks [https://liveblocks.io/lenny]—Ready-made collaborative features to drop into your product — Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn [https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn] — Where to find Alisa Cohn: • X: https://x.com/AlisaCohn [https://x.com/AlisaCohn] • LinkedIn: https://www.linkedin.com/in/alisacohn [https://www.linkedin.com/in/alisacohn] • Website: https://www.alisacohn.com [https://www.alisacohn.com] • Podcast: https://www.alisacohn.com/podcast [https://www.alisacohn.com/podcast] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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/ [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 [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 [https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf] • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 [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 [https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson] • Joe Gebbia on X: https://x.com/jgebbia [https://x.com/jgebbia] • Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425 [https://www.linkedin.com/in/noam-wasserman-462425] • Core Values List: https://jamesclear.com/core-values [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 [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 [https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii] • Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ [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 [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 [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 [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 [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 [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 [https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe [https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]