Gergely Orosz writes the #1 technology newsletter at Substack, called The Pragmatic Engineer. He started his career as a software developer in the U.K., spent three years at Skype, and followed that role with four years as an engineering manager at Uber before deciding to leave big tech and work for himself. Gergely began pursuing his newsletter full-time in September 2021 and in just one year has amassed 200,000 subscribers. He now makes more money than he did at his salaried tech job, and with freedom and flexibility. In today’s podcast, Gergely shares why he left his well-paying job at Uber, how he got his first 1,000 subscribers, why this kind of work can be stressful and lonely (but ultimately rewarding), and why it takes hard work to build authority and become a great writer. Working solo can be challenging, and in this episode, both Lenny and Gergely offer tips for structuring your unstructured time and finding your focus.—Find the full transcript here: https://www.lennysnewsletter.com/p/leaving-big-tech-to-build-the-1-technology—Where to find Gergely Orosz:• Website: https://www.pragmaticengineer.com/• Newsletter: https://newsletter.pragmaticengineer.com• Twitter: https://twitter.com/GergelyOrosz• LinkedIn: https://www.linkedin.com/in/gergelyorosz/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Lemon.io: https://lemon.io/lenny• Eppo: https://www.geteppo.com/• Vanta: https://vanta.com/lenny—Referenced:• Gergely’s books: https://blog.pragmaticengineer.com/books/• Centered: https://www.centered.app/• The Pomodoro technique: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/• Coding Horror: https://blog.codinghorror.com/• How to Achieve Ultimate Blog Success in One Easy Step: https://blog.codinghorror.com/how-to-achieve-ultimate-blog-success-in-one-easy-step/• A Comment Is an Invitation for Refactoring: https://blog.pragmaticengineer.com/a-comment-is-an-invitation-for-refactoring/• Kent Beck’s website: https://www.kentbeck.com/• Steve Yegge’s famous rant on Google vs. Amazon: https://www.alexanderjarvis.com/steve-yegges-famous-rant-on-google-vs-amazon/• Stevey’s Tech Talk: https://www.youtube.com/playlist?list=PLZfuUWMTtMcC1DZF6HxJhqsGrBXu8Jzi7—In this episode, we cover:(04:32) Gergely’s background(07:19) The Pragmatic Engineer, growth and current subscribers (08:59) Compensation with a subscription-based newsletter vs. his salaried position at Uber(10:55) How the onset of Covid and layoffs at Uber prompted Gergely to start his newsletter(23:10) What he did immediately after leaving Uber(25:41) The day-to-day of writing a newsletter(35:08) Tips for productivity(41:19) Gergely’s favorite parts of entrepreneurship (43:15) The downsides of solo work(50:39) Why Gergely stopped making long-term plans(54:30) How to get started writing a newsletter(1:04:48) Key advice on building a successful newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Alex Hardiman is Chief Product Officer at the New York Times, where she oversees the company’s news, cooking, games, audio and advertising products. Previously, Alex was Chief Business & Product Officer at The Atlantic, and before that she was Head of News Products at Facebook. We discuss how engineers and product people work with writers to create impactful stories, how teams build the incredible visualizations and experiences for NYTimes.com, how product teams are structured within the New York Times, and the good and bad about working at a company like the New York Times versus a FAANG tech company. We also talk about the details behind the New York Times’s acquisition of Wordle and uncover what the Times is dreaming up for its product over the next 10 years.—Find the full transcript here: https://www.lennysnewsletter.com/p/an-inside-look-at-how-the-new-york—Where to find Alex Hardiman:• Twitter: https://twitter.com/alex_hardiman• LinkedIn: https://www.linkedin.com/in/alexandrahardiman/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Miro: https://miro.com/lenny• Athletic Greens: https://athleticgreens.com/lenny• Vanta: https://vanta.com/lenny—Referenced:• Jodi Kantor: https://www.nytimes.com/by/jodi-kantor• Wordle: https://www.nytimes.com/games/wordle/• Wordle Is a Love Story: https://www.nytimes.com/2022/01/03/technology/wordle-word-game-creator.html• Josh Wardle on Twitter: https://twitter.com/powerlanguish• Eric Kim’s recipes: https://cooking.nytimes.com/ourcooks/eric-kim/• Wirecutter: https://www.nytimes.com/wirecutter/• Framing Britney Spears: https://www.nytimes.com/article/framing-britney-spears.html• Hard Fork podcast: https://www.nytimes.com/2022/10/04/podcasts/hard-fork-technology.html• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100• An Elegant Puzzle: Systems of Engineering Management: https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186• The Revolt of the Public and the Crisis of Authority in the New Millennium: https://www.amazon.com/Revolt-Public-Crisis-Authority-Millennium/dp/1732265143• Giovanni’s Room: https://www.amazon.com/Giovannis-Room-James-Baldwin/dp/0345806565/r• The Daily podcast: https://www.nytimes.com/column/the-daily• The Wire on HBO: https://www.hbo.com/the-wire• Google Workspace: https://workspace.google.com/• Slack: slack.com• Figma: figma.com• Mode: https://mode.com/• GitHub: https://github.com/• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/—In this episode, we cover:(04:48) Alex’s background(07:37) How Alex fought disinformation on the news team at Facebook (11:11) How some product people thrive in chaos(14:13) Alex’s return to the New York Times(16:22) What product means at the New York Times(20:42) How the product team at the New York Times is structured(26:20) How the New York Times makes stories come alive with balanced creative and technical teams(33:15) The acquisition of Wordle (42:00) What it was like to work at the New York Times during the onset of Covid(47:11) How to avoid burnout on a product team(49:26) How the New York Times has set itself apart with its subscription package(52:21) How the New York Times’s products are rooted in helping in the real world(52:54) Lenny’s tips for improving Wirecutter(53:36) The differences and similarities on product teams in a news organization(59:58) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Matt Mochary, CEO of Mochary Method, is a full-time executive coach who has worked with some of the biggest names in tech and finance, including investor Naval Ravikant and the CEOs of Notion, OpenAI, Coinbase, Reddit, and many others. In today’s podcast, we talk about the skill of firing people, why it’s so important, and Matt’s framework for approaching layoffs. We go deep on recognizing emotions like anger and fear, and what to pay attention to when you feel angry or fearful. He also shares how to build new products within a larger company, important tips on how to make sure everyone in the organization feels valued and heard, carving out time for your top goal, and how an energy audit can help you eliminate tasks that are draining your energy.—Find the full transcript here: https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work—Where to find Matt Mochary:• Twitter: https://twitter.com/mattmochary• LinkedIn: https://www.linkedin.com/in/matt-mochary-34bb4/• Website: http://www.mochary.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• AssemblyAI: https://www.assemblyai.com/?utm_source=lennyspodcast&utm_medium=podcast&utm_campaign=nov10• Lemon.io: https://lemon.io/lenny• Vanta: https://vanta.com/lenny—Referenced:• The Great CEO Within: The Tactical Guide to Company Building: https://www.amazon.com/Great-CEO-Within-Tactical-Building-ebook/dp/B07ZLGQZYC• Mochary Method: https://mocharymethod.org/• Leo Polovets on Twitter: https://twitter.com/lpolovets• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205• Andrej Karpathy on Lex Fridman’s podcast: https://lexfridman.com/andrej-karpathy/• Wei Deng on LinkedIn: https://www.linkedin.com/in/dengwei/• Free Solo: https://films.nationalgeographic.com/free-solo• Ryan Hoover on Twitter: https://twitter.com/rrhoover• Essentialism: The Disciplined Pursuit of Less: https://gregmckeown.com/books/essentialism/• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422• Centered app: https://www.centered.app/• Diana Chapman at Conscious Leadership Group: https://conscious.is/team/diana-chapman• The Mochary Method curriculum doc: https://docs.google.com/document/d/18FiJbYn53fTtPmphfdCKT2TMWH-8Y2L-MLqDk-MFV4s/edit—In this episode, we cover:(04:43) Matt’s background(07:39) Areas where even very successful founders struggle(12:24) How to address people to minimize defensiveness(13:24) The destructive nature of anger and how to feel your feelings so you don’t hurt others(15:02) Which books led Matt to his coaching journey and software platform(19:03) When and how to let an employee go(31:47) How to make people feel heard(38:05) How Matt’s coaching has evolved to include psychological obstacles to success(39:41) What is “top goal,” and how can it help you make massive gains?(41:25) Why Matt has an accountability partner for his top goal time(43:44) How to approach mass layoffs humanely(53:21) Matt’s thoughts on the Twitter layoffs(54:10) How to innovate within a large company(1:01:53) How to do an energy audit—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Ben Williams is VP of Product at Snyk, an industry-leading security platform for developers, last valued at $8.5b. He’s also a product and growth advisor with over 20 years of experience building and scaling high-performing product and growth teams. Through product-led growth, product-led sales, and community, Snyk rapidly scaled and won over the lucrative developer audience. In today’s episode, Ben shares the successful growth levers that helped Snyk get started, all of the details of how Snyk has structured their growth, product, and marketing teams and set them up for success in terms of cross-collaboration—and also how their initial plan for self-serve monetization fell flat. We go into Ben’s many useful tips for product-led growth, including his thoughts on free vs. paid versions, trials, and how to build amazing growth teams.—Find the full transcript here: https://www.lennysnewsletter.com/p/how-snyk-built-a-product-led-growth—Where to find Ben Williams:• Twitter: https://twitter.com/semanticben• LinkedIn: https://www.linkedin.com/in/semanticben/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Coda: https://coda.io/lenny• Athletic Greens: https://athleticgreens.com/lenny• Vanta: https://vanta.com/lenny—Referenced:• Snyk: https://snyk.io/• Weekly Team Impact & Learnings Review Template: https://docs.google.com/document/d/1GibNaJ4aONgp5Kg824NCionr1citHIDk3FLvMdkpX_Q/edit?usp=share_link• Monthly Group Impact & Learnings Review Template: https://docs.google.com/presentation/d/1nQ18OTuRtc8urBnUWEObD_BlfdGDKlDDMFg8-G2GK7E/edit?usp=share_link• Experiment Plan Template: https://docs.google.com/document/d/18LiGXKphGe1tUpZCQA20i4bJqf-S3kDbYnY4Pls_9kQ/edit?usp=share_link• Vision & Mission Framework: https://docs.google.com/presentation/d/1CiRwscu-50lBr2c7yRLY_zXVzv5DCnYqNnS5Au83WC8/edit?usp=share_link• Ed Sim’s newsletter: https://whatshot.substack.com/• Tamar Yehoshua on Twitter: https://twitter.com/tyehoshua• Julian Shapiro on Lenny’s Podcast: https://www.lennyspodcast.com/growth-tactics-retention-strategies-and-becoming-a-better-writer-julian-shapiro-demand-curve-hyper-webflow-techcrunch/• Annie Duke’s website: https://www.annieduke.com/• Elena Verna on Lenny’s Podcast: https://www.lennyspodcast.com/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/• Growth loops: https://www.reforge.com/blog/growth-loops• Brian Balfour on using learnings: https://brianbalfour.com/growth-machine/maximize-learning• Adam Fishman on Lenny’s Podcast: https://www.lennyspodcast.com/videos/how-to-build-a-high-performing-growth-team-adam-fishman-patreon-lyft-imperfect-foods/• Amplitude: https://amplitude.com/• FullStory: https://www.fullstory.com/• User Interviews: https://www.userinterviews.com/• User Testing: https://www.usertesting.com/• Sprig: https://sprig.com/surveys• Airtable: https://www.airtable.com/home/toolkit• How to Measure Anything: Finding the Value of “Intangibles” in Business: https://www.amazon.com/dp/0470110120/• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-Solve-Problems-Test-Ideas/dp/150112174X• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/gp/product/B078QSCM3V/• This Is How They Tell Me the World Ends: The Cyberweapons Arms Race: https://www.amazon.com/This-They-Tell-World-Ends/dp/1635576059• Acquired podcast: https://www.acquired.fm/• Turning Red on Disney+: https://www.disneyplus.com/movies/turning-red/4mFPCXJi7N2m• Curb Your Enthusiasm on HBO: https://www.hbo.com/curb-your-enthusiasm• Christine Itwaru’s blog: https://prodops.blog/—In this episode, we cover:(04:44) Ben’s background(07:27) What is Snyk, and what’s the current scale?(08:45) Why Ben joined Snyk(09:29) How Snyk got their first 100 users(15:14) How Snyk used developer conferences and in-person meet-ups to launch(19:23) How Snyk used GitHub as a growth lever(23:50) Snyk Advisor, and other growth loops Snyk successfully used(26:56) Snyk’s failed attempt at self-serve monetization(31:21) How to win the hearts and minds of developers(33:38) How adding sales and marketing teams helped Snyk gain momentum(35:11) The evolution of Snyk’s growth team(37:26) Snyk’s key areas of growth and how Ben solved tension between teams(39:32) What is Snyk’s decision science team?(40:59) Why Snyk has a growth marketer embedded on each team(43:39) The importance of having an amazing SEO person(46:21) Advice on building growth teams(51:32) Ben’s vision and mission framework(53:53) More on the growth process and experimentation(56:04) Using learnings as a path to impact(57:32) Growth strategy(1:02:26) Data in growth teams(1:06:33) How Snyk socializes learnings(1:10:05) How Snyk structures their product org(1:13:15) Free vs. paid features and how to approach trials(1:18:57) Activation milestones at Snyk(1:23:05) The most valuable tools for Snyk’s growth team(1:25:21) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Lauren Ipsen is one of the most well-known and respected executive recruiters in the industry, having placed over 90 senior product leaders at companies including Twitter, Reddit, Opendoor, Postmates, Nextdoor, and many others. She is currently the Director of Executive Talent at General Catalyst, and prior to that was a senior leader at Daversa Partners. In today’s podcast, Lauren shares advice for founders on hiring senior product leaders, tips for product leaders on finding better opportunities, and the most common mistakes recruiters make. She talks about how to play the long game of networking to find the best talent and about recruiting best practices, and we also dive deep on market mapping, LinkedIn, and how to approach reference checks.—Find the full transcript here: https://www.lennysnewsletter.com/p/lessons-from-one-of-the-worlds-top—Where to find Lauren Ipsen:• LinkedIn: https://www.linkedin.com/in/lauren-ipsen-6a5a84113/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Retool: https://retool.com/lenny• Miro: https://miro.com/lenny• Vanta: https://vanta.com/lenny—Referenced:• Gokul Rajaram on Lenny’s podcast: https://www.lennyspodcast.com/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/• The Power of Now: A Guide to Spiritual Enlightenment:  https://www.amazon.com/Power-Now-Guide-Spiritual-Enlightenment/dp/1577314808• You Are Here: Discovering the Magic of the Present Moment: https://www.amazon.com/You-Are-Here-Discovering-Present/dp/1590308387/• Your Own Backyard podcast: https://www.yourownbackyardpodcast.com/• Top Gun: https://www.amazon.com/Top-Gun-Tom-Cruise/dp/B001K3K5MO• BeReal: https://apps.apple.com/us/app/bereal-your-friends-for-real/id1459645446• Strava: https://apps.apple.com/us/app/strava-run-ride-hike/id426826309• Spotify: https://apps.apple.com/us/app/spotify-music-and-podcasts/id324684580• Joe Suliman at Daversa Partners: https://www.daversapartners.com/team/joe-suliman/—In this episode, we cover:(04:46) Lauren’s background(07:52) Why the best recruiters seem to be migrating to VC funds(09:44) Mistakes founders make in searching for their first senior product leader(13:26) Questions for founders to ask when thinking about who to hire(16:07) The three main types of PMs(18:27) What do job titles mean, and why are they more susceptible to change in a startup environment?(21:50) What should product leaders do ahead of hiring senior product leaders?(23:14) How to network with great talent(27:37) Why the timetable for recruiting is variable(29:02) How to be productive with your time by tapping your network(30:27) Why recruiting via LinkedIn might not be the best use of your time(33:17) Lauren’s favorite placement of all time(37:30) The importance of diversifying your experience(40:16) The art and science of staying long enough to have a meaningful impact(43:23) The importance of creating real impact as a leader(47:57) Good questions to ask references and how to dig deeper(49:35) Resume red flags and the importance of honesty(53:39) Interview tips for product managers (57:29) Common mistakes recruiters make(1:00:57) Advice for founders looking for a recruiter(1:04:24) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Sachin Monga is the Head of Product at Substack, a platform that I personally use every day, and love. Before Substack, Sachin co-founded an app called Cocoon, which he ended up selling to Substack. Before that, he spent over seven years at Facebook as a PM working on video and camera products, building out the developer platform, and leading the ads growth team. In today’s episode, we dive deep on all things Substack. Sachin shares what it’s like transitioning from a large product team at Facebook to a small growth team. He discusses how to work with a hands-on founder and why you must be comfortable with rapid change in a PM role. He also shares unique features of Substack that make it an optimized experience for readers and writers, how he’d like to see it improved, and tips for anyone wanting to get started writing online.—Find the full transcript here: https://www.lennysnewsletter.com/p/building-substack-sachin-monga-substack—Where to find Sachin Monga:• Twitter: https://twitter.com/sachinmonga• LinkedIn: https://www.linkedin.com/in/sachinmonga/• Email: Sachin@substackinc.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Retool: https://retool.com/lenny• Stytch: https://stytch.com/lenny• Vanta: https://vanta.com/lenny—Referenced:• Substack: https://substack.com/• Matt Taibbi on Substack: https://taibbi.substack.com/• Bill Bishop on Substack: https://sinocism.com/• Jasper: https://www.jasper.ai/• DALL-E 2: https://openai.com/dall-e-2/• 1000 True Fans: https://www.amazon.com/1000-True-Fans-Kellys-Simple-ebook/dp/B01N9P9O4G• You Are Not Late: https://medium.com/message/you-are-not-late-b3d76f963142• The Timeless Way of Building: https://www.amazon.com/Timeless-Way-Building-Christopher-Alexander/dp/0195024028• Martyrmade podcast on Substack: https://martyrmade.substack.com/• Colin Meloy on Substack: https://colinmeloy.substack.com/• Ethan Strauss on Substack: https://houseofstrauss.substack.com/• Kareem Abdul-Jabbar on Substack: https://kareem.substack.com/• Dayne Rathbone: https://www.linkedin.com/in/daynerathbone/• For All Mankind on Apple TV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7—In this episode, we cover:(04:34) Sachin’s background(07:11) The evolution and structure of teams at Substack(10:11) What it’s like working at a smaller company with a hands-on founder(12:07) How to share in a founder’s vision(14:02) Why the rate of change is the most challenging aspect of the job(16:37) Why prioritization at Facebook worked differently than it does at Substack(20:03) How Substack thinks about prioritizing for writers and readers(22:17) Substack’s recommendation feature and how it came to be(27:13) How recommendations have led to an increase of millions of subscribers(31:34) Moving forward with network-driven discovery (32:17) The “build with” principle and the product lab at Substack(35:02) How Substack deals with negative press(36:45) The writer experience at Substack(39:13) The reader-focused experience on Substack(40:41) Advice for writers(44:45) Substack’s vision for making creation easier(46:39) Common mistakes creators make, and how product improvements could help in some cases (49:57) Why you’re not too late to join the game(52:52) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Barbra Gago is the founder and CEO of Pando, where she’s democratizing career progression. Previously she worked as the Chief Marketing Officer and Global Head of Marketing at Miro, where she helped create an entirely new software category for the space, and also served as VP of Marketing at Greenhouse, where she led go-to-market strategy. In today’s episode, we cover three main topics: category creation, branding and rebranding, and building opinionated software. Barbra discusses how she was able to rebrand Miro and launch a whole new category—and why her attempt to do that at Greenhouse failed. We cover the benefits of building your own category, and when it makes sense to do so and when it doesn’t. She also shares the importance of getting to know your users, why a great brand is informed by its values, and why Pando is built in an opinionated way.—Find the full transcript here: https://www.lennyspodcast.com/category-creation-and-brand-building-barbra-gago-pando-miro-greenhouse-culture-amp/#transcript—Where to find Barbra Gago:• Twitter: https://twitter.com/barbragago• LinkedIn: https://www.linkedin.com/in/barbragago• Pando: https://www.pando.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• AssemblyAI: https://www.assemblyai.com/?utm_source=lennyspodcast&utm_medium=podcast&utm_campaign=oct27• Stytch: https://stytch.com/lenny• Vanta: https://vanta.com/lenny—Referenced:• G2: https://g2.com/• Software Advice: https://www.softwareadvice.com/• Marketo: https://www.marketo.com/• HubSpot: https://www.hubspot.com/• Gainsight: https://www.gainsight.com/• Greenhouse: https://www.greenhouse.io/• Miro: https://miro.com/• Gartner: https://www.gartner.com/• Forrester: https://www.forrester.com/research/product-management/• Oyster: https://www.oysterhr.com/• Deel: https://www.deel.com/• Atlassian: https://www.atlassian.com/• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375• The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1590302257• Kafka on the Shore: https://www.amazon.com/Kafka-Shore-Haruki-Murakami/dp/0099458322• Cautionary Tales podcast: https://timharford.com/articles/cautionarytales/• The Sandman on Netflix: https://www.netflix.com/title/81150303• Nancy Duarte on LinkedIn: https://www.linkedin.com/in/nancyduarte/• Al Gore’s TED Talk: https://www.ted.com/talks/al_gore_the_new_urgency_of_climate_change—In this episode, we cover:(04:04) Barbra’s background(05:06) Barbra’s startup(06:07) Category creation vs. winning in existing categories(07:49) What is an applicant tracking system, and why have they been problematic?(09:57) What is a product category?(13:06) Examples of product categories(14:05) Greenhouse as an example of failed category creation (16:46) How Miro successfully created a new category(18:37) Utilizing user feedback(21:15) The mechanics of category creation(21:22) How to advocate for your new category with directory sites(25:53) The middle ground between new and existing categories(29:37) When is it time to rebrand?(38:51) How to create a lasting, global brand(41:18) How values inform brands(43:13) Insights into developing company values(44:24) The elements of a brand(46:37) What is opinionated software?(47:57) The benefits of opinionated software, and why Barbra’s software is opinionated(51:23) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Fareed Mosavat is Chief Development Officer at Reforge, where he leads production, content, and new-product experiences. Previously, he led growth and product teams at Slack and Instacart, was a GM at Zynga, and also served as VP of Product at RunKeeper. Before all of that, Fareed’s fascinating career began in engineering for Pixar, where he learned the art of storytelling and collaboration. In today’s episode, we talk about how his time at Pixar influenced the way he thinks about product, why it’s so difficult to become a better PM, and how to avoid the “manager death spiral.” Fareed shares important insights on how to earn the trust of your manager and coworkers, the four types of product work—and why you need to understand all four. He also provides solid examples of how to generalize your learnings and explains why this will expand your options, make you a better PM, and boost your chances of moving into a leadership role. —Find the full transcript here: https://www.lennysnewsletter.com/p/how-to-establish-credibility-and—Where to find Fareed Mosavat:• Twitter: https://twitter.com/far33d• LinkedIn: https://www.linkedin.com/in/fareed/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Coda: http://coda.io/lenny• Amplitude: https://amplitude.com/• Vanta: https://vanta.com/lenny—Referenced:• Naval Ravikant’s Twitter thread about specific knowledge: https://twitter.com/naval/status/1002104865919664128• Merci Grace on Lenny’s podcast: https://www.lennyspodcast.com/merci-grace-ex-head-of-growth-at-slack-on-plg-interviewing-storytelling-building-a-diverse-team-hiring-salespeople-building-a-growth-team-and-much-more/• “Crossing the Canyon: Product Manager to Product Leader,” by Fareed Mosavat and Casey Winters: https://www.reforge.com/blog/crossing-the-canyon-product-manager-to-product-leader• Casey Winters on Lenny’s podcast: https://www.podpage.com/lennys-podcast/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/• Reforge: https://www.reforge.com/—In this episode, we cover:(00:38) Fareed’s background(03:55) Lessons from Pixar(09:07) What Fareed does at Reforge(11:57) The scale of Reforge at this time(13:51) Why it’s so difficult to become a better PM(18:03) A PM pie chart—execution, generalizing your solutions, communication, and scaling(23:00) How creating trust helped Fareed’s career grow(26:24) How to gain trust by leveraging your curiosity and communication skills(33:50) How to move from PM to Product Lead(36:43) The manager death spiral and how to avoid it(40:43) The four types of product work(44:13) Moving from IC to product manager (47:15) How to ask for the proper resources(50:00) The trend of senior PMs diversifying into advising, teaching, and angel investing(57:20) The downsides of being your own boss(01:00:45) Advice for breaking into advising—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Adriel Frederick is VP of Product Management at Reddit X, where he helps incubate and scale new products. He is a former Product Lead at Facebook, as well as a former PM and Director of Product at Lyft. In today’s episode, we focus on what it takes to become a better product leader. Adriel shares anecdotes from his time at Lyft and Facebook, insights about how to lead through tough times, why there isn’t an algorithmic solution to everything, why R&D teams need to be a part of the core mission, the tangible benefits of working on diverse teams, and his thoughts on the future of AI. He also introduces the concept of cannonballs, why you should focus on the marginal user, why organization and empathy are the most important PM skills, and so much more.—Find the full transcript here: https://www.podpage.com/lennys-podcast/humanizing-product-development-adriel-frederick-reddit-lyft-facebook/#transcript—Where to find Adriel Frederick:• Twitter: https://twitter.com/drellf• LinkedIn: https://www.linkedin.com/in/adrielfrederick/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Linear: https://linear.app/lenny• Flatfile: https://www.flatfile.com/lenny• Eppo: https://www.geteppo.com/—Referenced:• Jules Walter on Twitter: https://twitter.com/julesdwalt• Jules Walter’s guest post on Lenny’s newsletter: https://www.lennysnewsletter.com/p/product-sense• Mark Zuckerberg on The Joe Rogan Experience: https://open.spotify.com/episode/51gxrAActH18RGhKNza598• Sam Harris’s TED Talk on AI: https://www.youtube.com/watch?v=8nt3edWLgIg• Facebook’s 7 friends in 10 days: https://www.linkedin.com/pulse/how-chamath-palihapitya-dramatically-improved-user-malinda-senanayake/• The Prize: The Epic Quest for Oil, Money & Power: https://www.amazon.com/Prize-Epic-Quest-Money-Power/dp/1439110123/• The New Map: Energy, Climate, and the Clash of Nations: https://www.amazon.com/New-Map-Energy-Climate-Nations/dp/0143111159/• Revisionist History podcast: https://podcasts.apple.com/us/podcast/revisionist-history/id1119389968• Tuned In podcast: https://www.hpacademy.com/blog/tuned-in-high-performance-academy-podcast/• Mo on Netflix: https://www.netflix.com/title/81134264• Radiant Nuclear: https://www.radiantnuclear.com/—In this episode, we cover:(00:40) Adriel’s background(06:13) What he does at Reddit X(07:27) Reddit X’s avatar marketplace and NFTs(08:33) Why R&D teams need to be a part of the core mission(11:12) What it’s like to be the first black PM at Facebook(14:58) How to foster diversity(19:40) Being a PM at controversial companies, and how to evaluate criticism(28:25) Adriel’s most stressful time at Lyft(30:35) The importance of operational control and what it means(32:35) Why there isn’t always an algorithmic solution to everything(37:47) Thoughts on AI(42:42) Growth hacking and algorithms at Facebook(48:18) Cannonballs in growth—fundamental changes in the product for optimization(49:07) Facebook’s “7 friends in 10 days” push(51:30) What is a marginal user, and what can you learn from their experience?(56:06) How to think about doing experiments(59:10) Why organization and empathy are the most important skills (1:02:59) Lightning round —Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Janna Bastow is a former product manager, and currently the CEO and co-founder of ProdPad. She also co-founded Mind the Product, a community for PMs, which has grown to 300,000 members across the world. In today’s podcast, Janna discusses the limitations of timeline-based Gantt charts and her “Now/Next/Later” framework. She also shares stories about hosting conferences and gives some great tips on how to improve your presentation skills and cope with performance anxiety.—Find the full transcript here: https://www.lennyspodcast.com/building-better-product-roadmaps-janna-bastow-mind-the-product-prodpad/#transcript—Where to find Janna Bastow:• Twitter: https://twitter.com/simplybastow• LinkedIn: https://www.linkedin.com/in/jannabastow• The ProdPad newsletter: https://www.prodpad.com/newsletter/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Formsort: https://formsort.com/lenny• Coda: http://coda.io/lenny• Amplitude: https://amplitude.com/—Referenced:• Mind the Product: https://www.mindtheproduct.com/• The Trouble with Traditional Roadmaps: https://www.prodpad.com/resources/guides/ditch-the-timeline-roadmap/the-trouble-with-traditional-timeline-roadmaps/• ProdPad’s Sandbox: https://www.prodpad.com/sandbox/• Geoffrey Moore’s product vision template: https://www.prodpad.com/blog/product-vision-template/• The Art of Profitability: https://www.amazon.com/Art-Profitability-Adrian-Slywotzky/dp/0446692271• The Sandman on Netflix: https://www.netflix.com/title/81150303• Startups for the Rest of Us podcast: https://www.startupsfortherestofus.com/• Christina Wodtke on Twitter: https://twitter.com/cwodtke—In this episode, we cover:(01:10) Janna’s background(05:28) How the community evolved at Mind the Product(08:22) The tricky logistics of putting together a conference(10:48) Are conferences profitable?(13:00) How Janna developed her storytelling and presentation skills(16:44) How to fight performance anxiety(19:25) Mistakes are humanizing—how to power through and deliver your presentation(22:11) The limitations of traditional timeline roadmaps(25:00) Janna’s Now/Next/Later framework(28:08) How to work without the structure of dated timelines, and why soft launches are important(32:57) What great product teams are doing well(35:05) The importance of retrospectives(36:45) How to shift the culture at larger companies(39:43) How ProdPad creates better product management practices(42:04) How to learn the Now/Next/Later framework(46:59) Geoffrey Moore’s product vision template(48:36) Lessons for PMs interested in becoming founders(50:48) Lightning round—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe