Lenny's Podcast: Product | Career | Growth

Lenny Rachitsky
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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.

  1. The future of AI-powered sales with Vercel COO, Jeanne DeWitt

    2 NGÀY TRƯỚC

    The future of AI-powered sales with Vercel COO, Jeanne DeWitt

    Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. We discuss: 1. Why GTM is becoming more strategically important in the AI era 2. The rise of the GTM engineer 3. A primer on segmentation 4. How to build a sales org that engineers and product teams respect 5. The changing calculus of build vs. buy for go-to-market tools in the AI era 6. Why most customers buy to avoid pain rather than to gain upside — Brought to you by: Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Lovable—Build apps by simply chatting with AI: https://lovable.dev/ Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ — Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation — Where to find Jeanne DeWitt Grosser: • X: https://x.com/jdewitt29 • LinkedIn: https://www.linkedin.com/in/jeannedewitt — 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 Jeanne DeWitt Grosser (05:26) Defining go-to-market (08:43) The evolution of go-to-market roles (11:23) The rise of the go-to-market engineer (14:21) Implementing AI in sales processes (15:28) Optimizing sales with AI agents (23:47) Defining sales roles: SDRs and AEs (26:04) When to hire a GTM engineer (29:04) Hiring and scaling sales teams (30:50) The ideal go-to-market engineer (34:24) The go-to-market tool stack (40:39) Advice on building a great sales bot (44:34) Vercel’s unfair advantage (46:37) Go-to-market as a product (47:04) Innovative sales tactics at Stripe (52:38) Effective go-to-market tactics (01:00:37) Segmentation strategies (01:09:31) Building a sales org that engineers love (01:14:00) Thoughts on PLG and pricing (01:16:44) Sales compensation and hiring (01:19:24) Lightning round and final thoughts — Referenced: • Vercel: https://vercel.com • Stripe: https://stripe.com • Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin • Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman • SDK: https://ai-sdk.dev/docs/introduction • Gong: https://www.gong.io • Lyft: https://www.lyft.com • Instacart: https://www.instacart.com • DoorDash: https://www.instacart.com • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Atlassian: atlassian.com — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 26 phút
  2. A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett

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    A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett

    Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me. We discuss: * When to coach and when to just tell people what to do [09:00] * The GROW technique for helping people figure out a solution for themselves [18:37] * Techniques for making difficult conversations less difficult [01:20:28] * Avoiding burnout and designing a more energizing career [41:55] * Building and sustaining a healthy co-founder relationship [01:06:50] * Creating a one-page plan that aligns your entire company [01:31:47] * Practical ways AI is transforming executive coaching and leadership development [01:36:50] * Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55] Also on Spotify and Apple Podcasts Brought to you by: Stripe—Helping companies of all sizes grow revenue Vanta—Automate compliance. Simplify security. Persona—A global leader in digital identity verification Where to find Rachel Lockett: • LinkedIn: https://www.linkedin.com/in/rhlockett/ • Website: https://www.lockettcoaching.com Referenced: • One-page plan template: https://www.lockettcoaching.com/#resources • Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0 • Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/ • First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0 • Coinbase: https://www.coinbase.com • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to • Patrick Collison on X: https://x.com/patrickc • Stripe: https://stripe.com • Remind: https://www.remind.com • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams • Brex: https://www.brex.com • Bridge: https://www.bridge.xyz • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • The Enneagram Institute: https://www.enneagraminstitute.com • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst • How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver • Granola: https://www.granola.ai • KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621 • Loom: https://www.loom.com • Joseph Campbell’s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front • Wes Anderson’s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-films Recommended books: • Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904 • Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321 • Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293 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. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

    1 giờ 45 phút
  3. Slack founder: Mental models for building products people love ft. Stewart Butterfield

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    Slack founder: Mental models for building products people love ft. Stewart Butterfield

    Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams. We discuss: 1. Hyper-realistic work-like activities 2. The owner’s delusion 3. Utility curves 4. “Don’t make me think” 5. “We don’t sell saddles here” 6. Tilting your umbrella 7. When to pivot — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Metronome—Monetization infrastructure for modern software companies Lovable—Build apps by simply chatting with AI — Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation — Where to find Stewart Butterfield: • X: https://x.com/stewart • LinkedIn: https://www.linkedin.com/in/butterfield — 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 Stewart Butterfield (04:58) Stewart’s current life and reflections (06:44) Understanding utility curves (10:13) The concept of divine discontent (15:11) The importance of taste in product design (19:03) Tilting your umbrella (28:32) Balancing friction and comprehension (45:07) The value of constant dissatisfaction (47:06) Embracing continuous improvement (50:03) The complexity of making things work (54:27) Parkinson’s law and organizational growth (01:03:17) Hyper-realistic work-like activities (01:13:23) Advice on when to pivot (01:18:36) The importance of generosity in leadership (01:26:34) The owner’s delusion — Referenced: • Slack: https://slack.com • Flickr: https://www.flickr.com • Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal • Blok: https://blok.so • Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b • Magic Link: https://en.wikipedia.org/wiki/Magic_Link • Ticketmaster: https://www.ticketmaster.com • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai • Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo • Six Sigma: https://www.6sigma.us • What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system • John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976 • Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law • We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • IRC: https://en.wikipedia.org/wiki/IRC • This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke • The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva • Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma • Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little • Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg • Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224 — Recommended books: • Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021 • Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996 — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 31 phút
  4. The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li

    16 THG 11

    The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li

    Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely told history of how we got here—including the wild fact that just nine years ago, calling yourself an AI company was basically a death sentence. We discuss: 1. How ImageNet helped spark the AI explosion we’re living through 2. Why world models and spatial intelligence represent the next frontier in AI, beyond large language models 3. Why Fei-Fei believes AI won’t replace humans but will require us to take responsibility for ourselves 4. The surprising applications of Marble, from movie production to psychological research 5. Why robotics faces unique challenges compared with language models and what’s needed to overcome them 6. How to participate in AI regardless of your role — Brought to you by: Figma Make—A prompt-to-code tool for making ideas real Justworks—The all-in-one HR solution for managing your small business with confidence Sinch—Build messaging, email, and calling into your product — Transcript: https://www.lennysnewsletter.com/p/the-godmother-of-ai — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178223233/my-biggest-takeaways-from-this-conversation — Where to find Dr. Fei-Fei Li • X: https://x.com/drfeifei • LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247 • World Labs: https://www.worldlabs.ai — 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 Dr. Fei-Fei Li (05:31) The evolution of AI (09:37) The birth of ImageNet (17:25) The rise of deep learning (23:53) The future of AI and AGI (29:51) Introduction to world models (40:45) The bitter lesson in AI and robotics (48:02) Introducing Marble, a revolutionary product (51:00) Applications and use cases of Marble (01:01:01) The founder’s journey and insights (01:10:05) Human-centered AI at Stanford (01:14:24) The role of AI in various professions (01:18:16) Conclusion and final thoughts — References: https://www.lennysnewsletter.com/p/the-godmother-of-ai — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 20 phút
  5. “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO)

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    “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO)

    Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive business in a category most investors dismissed. In fact, one investor told Grant his idea was “the dumbest idea he had ever heard.” We discuss: • How Gamma found product-market fit by rethinking their onboarding • Their process for building a “word-of-mouth machine” • How they leveraged more than 1,000 micro-influencers instead of big names • Why focusing on the “first 30 seconds” transformed their business • Their approach to pricing that led to profitability within months • How Grant thinks about building a durable “GPT wrapper” business — Brought to you by: Vanta—Automate compliance. Simplify security. Justworks—The all-in-one HR solution for managing your small business with confidence Miro—A collaborative visual platform where your best work comes to life — Where to find Grant Lee: • X: https://x.com/thisisgrantlee • LinkedIn: https://www.linkedin.com/in/grantslee — 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 Grant Lee and Gamma (05:59) The founding story of Gamma (09:52) Achieving product-market fit (15:43) Self-awareness as a founder (17:17) The power of onboarding (20:41) The original insight that led to Gamma (22:42) Founder-led marketing and growth tactics (29:20) Sharing online (37:40) Getting to $100M ARR (41:19) Influencer marketing as a growth strategy (54:08) Virality is not an accident (58:30) Investing in brand before paid ads (01:02:04) Tips for getting started with performance marketing (01:04:49) Prototyping and user feedback (01:16:12) Adapting and moving quickly (01:19:21) The concept of GPT wrapper companies (01:22:16) Deep dive into workflow and model utilization (01:29:06) Pricing strategies (01:34:53) Hiring philosophy and practices (01:43:24) Betting big on high performers (01:45:03) Final thoughts and lightning round — References: https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1 giờ 54 phút
  6. "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

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    "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

    Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR. We discuss: 1. Why the “mid-market” doesn’t exist 2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers 3. The dangers of pricing your product at $10K-$20K 4. Why you need to vision-cast instead of problem-solve to win enterprise deals 5. Why services are the fastest way to get your foot in the door with enterprises 6. How to find and work with design partners 7. When to hire your first salesperson and what profile to look for — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Lovable—Build apps by simply chatting with AI Coda—The all-in-one collaborative workspace — Where to find Jen Abel: • X: https://x.com/jjen_abel • LinkedIn: https://www.linkedin.com/in/earlystagesales • Website: https://www.jjellyfish.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) Welcome back, Jen! (04:38) The myth of the mid-market (08:08) Targeting tier-one logos (10:50) Vision-casting vs. problem-selling (15:35) The importance of high ACVs (20:45)  Don’t play the small business game with an enterprise company (25:09) Design partners: the double-edged sword (28:11) Finding the right company (36:55) Enterprise sales: the art of the deal (43:21) The problem with channel partnerships (44:41) Quick summary (50:24) Hiring the right enterprise salespeople (56:49) Structuring sales compensation (01:01:01) Building relationships in enterprise sales (01:02:07) The art of cold outreach (01:07:31) Outbound tooling and AI (01:14:08) Lightning round and final thoughts — Referenced: • The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel • Mario meme: https://www.linkedin.com/pulse/missing-meme-led-me-woman-johann-van-tonder-im6df • Kathy Sierra: https://en.wikipedia.org/wiki/Kathy_Sierra • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Justin Lawson on X: https://x.com/jjustin_lawson • Stripe: https://stripe.com • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Linear: https://linear.app • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Gemini: https://gemini.google.com • Microsoft Copilot: https://copilot.microsoft.com • How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi • McKinsey & Company: https://www.mckinsey.com • Deloitte: https://www.deloitte.com • Accenture: https://www.accenture.com • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • Peter Dedene on X: https://x.com/peterdedene • Hang Huang on X: https://x.com/HH_HangHuang • Hugo Alves on X: https://x.com/Ugo_alves • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Clay: https://www.clay.com • Apollo: https://www.apollo.io • Jason Lemkin on X: https://x.com/jasonlk • Gavin Baker on X: https://x.com/GavinSBaker • Jason Cohen on X: https://x.com/asmartbear • Baywatch on Prime Video: https://www.primevideo.com/detail/Baywatch/0NU9YS8WWRNQO1NZD5DOQ3I8W6 • Playground: https://www.tryplayground.com • ClassDojo: https://www.classdojo.com • Jason Lemkin’s post about Replit: https://x.com/jasonlk/status/1946069562723897802 — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 22 phút
  7. The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins

    2 THG 11

    The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins

    Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you. We discuss: 1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints 2. The power of setting “crazy big goals” 3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase 4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch 5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible 6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world — Brought to you by: Vanta—Automate compliance. Simplify security. https://vanta.com/lenny Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com — Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠ — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation — Where to find Melanie Perkins: • X: https://x.com/melaniecanva • LinkedIn: https://www.linkedin.com/in/melanieperkins/ — 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 Melanie Perkins and Canva (04:44) Building a “column B” company (06:36) Operationalizing big visions (13:13) Crazy big goals and celebrations (22:00) Challenges and setbacks in Canva’s journey (26:30) Fundraising and investor rejections (29:36) Leadership and growth lessons (34:38) Canva’s goal-driven structure (35:46) Balancing work and personal life (38:02) Community-driven product development (40:37) The two-step plan for global impact (45:04) Canva’s biggest launch yet (48:10) How Canva approaches product expansion (52:37) AI integration in Canva (53:56) AI corner (55:22) Melanie’s vision for 2050 and beyond (01:00:07) Lightning round and final thoughts — Referenced: • Canva: https://www.canva.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa • UserTesting: https://www.usertesting.com/ • Figma: https://www.figma.com/ • Adobe: https://www.adobe.com/ • Calm: https://www.calm.com/ • Gandhi’s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593 • Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/ — Recommended books: • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/ • 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/ • The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765 • Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855 — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 6 phút
  8. How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

    26 THG 10

    How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

    Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO). We discuss: 1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly 2. How the company measures AI productivity gains across technical and non-technical teams 3. Which teams are benefiting most from AI (it’s not engineering) 4. The boring organizational change that boosted productivity even more than AI tools 5. Why code quality has almost nothing to do with product success 6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily) 7. Lessons from building Google Wave, Google+, and other failed products — Brought to you by: Sinch—Build messaging, email, and calling into your product: https://sinch.com/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Persona—A global leader in digital identity verification: https://withpersona.com/lenny — Where to find Dhanji R. Prasanna: • LinkedIn: https://www.linkedin.com/in/dhanji/ — 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 Dhanji (05:26) The AI manifesto: convincing Jack Dorsey (07:33) Transforming into a more AI-native company (12:05) How engineering teams work differently today (15:24) Goose: Block’s open-source AI agent (20:18) Measuring AI productivity gains across teams (21:38) What Goose is and how it works (32:15) The future of AI in engineering and productivity (37:42) The importance of human taste (40:10) Building vs. buying software (44:08) How AI is changing hiring and team structure (53:45) The importance of using AI tools yourself before deploying them (55:13) How Goose helped solve a personal problem with receipts (58:01) What makes Goose unique (59:57) What Dhanji wishes he knew before becoming CTO (01:01:49) Counterintuitive lessons in product development (01:04:56) Why controlled chaos can be good for engineering teams (01:08:07) Core leadership lessons (01:13:36) Failure corner (01:15:50) Lightning round and final thoughts — Referenced: • Jack Dorsey on X: https://x.com/jack • Block: https://block.xyz/ • Square: https://squareup.com/ • Cash App: https://cash.app/ • What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law# • Goose: https://github.com/block/goose • Gosling: https://github.com/block/goose-mobile • Salesforce: https://www.salesforce.com/ • Snowflake: https://www.snowflake.com/ • Claude: https://claude.ai/ • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • OpenAI: https://openai.com/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Llama: https://www.llama.com/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Top Gun: https://www.imdb.com/title/tt0092099/ • Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/ • Afterpay: https://github.com/afterpay • Bitkey: https://bitkey.world/ • Proto: https://github.com/proto-at-block • Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/ • Databricks: https://www.databricks.com/ • Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch • Google Wave: https://en.wikipedia.org/wiki/Google_Wave • Google Video: https://en.wikipedia.org/wiki/Google_Video • Secret: https://en.wikipedia.org/wiki/Secret_(app) • Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M • Steam Deck OLED display: https://www.steamdeck.com/en/oled • Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown — Recommended books: • The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119 • Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/ — 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. To hear more, visit www.lennysnewsletter.com

    1 giờ 27 phút
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