Podcast
Lenny Rachitsky
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about: • The three elements of breakthrough startup ideas • Why you need to both think and act differently • How to avoid the “comparison trap” and “conformity trap” • The importance of movements, storytelling, and healthy disagreeableness in startup success • How to apply pattern-breaking principles within large companies • Mike’s one piece of advice for founders • Much more Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny. — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Webflow—The web experience platform — Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr — Where to find Mike Maples, Jr.: • X: https://x.com/m2jr • LinkedIn: https://www.linkedin.com/in/maples/ • Substack: https://greatness.substack.com/ • Website: https://www.floodgate.com/ — 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) Mike’s background (03:10) The inspiration behind Pattern Breakers (08:09) Uncovering startup insights (11:37) A quick summary of Pattern Breakers (13:52) Coming up with an idea (15:30) Inflections (17:03) Examples of inflections (28:02) Insights (36:49) The power of surprises (47:31) Founder-future fit (55:28) Advice for aspiring founders (56:33) Living in the future: valid opinions (58:32) Identifying lighthouse customers (01:00:45) The importance of desperation in customer needs (01:03:49) Creating movements and storytelling (01:24:14) The role of disagreeableness in startups (01:34:34) Applying these principles within a company (01:40:35) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed.
Jul 7
1 hr 49 min
Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about: • The three elements of breakthrough startup ideas • Why you need to both think and act differently • How to avoid the “comparison trap” and “conformity trap” • The importance of movements, storytelling, and healthy disagreeableness in startup success • How to apply pattern-breaking principles within large companies • Mike’s one piece of advice for founders • Much more Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny. — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Webflow—The web experience platform — Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr — Where to find Mike Maples, Jr.: • X: https://x.com/m2jr • LinkedIn: https://www.linkedin.com/in/maples/ • Substack: https://greatness.substack.com/ • Website: https://www.floodgate.com/ — 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) Mike’s background (03:10) The inspiration behind Pattern Breakers (08:09) Uncovering startup insights (11:37) A quick summary of Pattern Breakers (13:52) Coming up with an idea (15:30) Inflections (17:03) Examples of inflections (28:02) Insights (36:49) The power of surprises (47:31) Founder-future fit (55:28) Advice for aspiring founders (56:33) Living in the future: valid opinions (58:32) Identifying lighthouse customers (01:00:45) The importance of desperation in customer needs (01:03:49) Creating movements and storytelling (01:24:14) The role of disagreeableness in startups (01:34:34) Applying these principles within a company (01:40:35) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed.
Jul 7
1 hr 49 min
Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into: • How intuition and product taste drive Dylan’s decision-making • The challenge of keeping things simple • Dylan’s thoughts on the future of product management • Lessons from Figma’s early days • How Figma built their initial user base • Dylan’s journey from intern to CEO of a 1,000+-person company • The future of design tools and AI — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Anvil—The fastest way to build software for documents • User Testing—Human understanding. Human experiences. — Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config — Where to find Dylan Field: • X: https://x.com/zoink • LinkedIn: https://www.linkedin.com/in/dylanfield/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (01:11) Welcoming Dylan Field (02:36) Highlights and surprises from Config (06:58) The philosophy of design (08:01) Raccoon feet and muffin hands (09:57) Building and refining intuition and product taste (12:50) How to influence leadership (16:14) The role of product managers (21:12) The future of product management (22:20) The importance of simplicity in design (26:10) The long road to Figma’s launch (27:44) Advice for aspiring entrepreneurs (29:07) Knowing when it’s time to ship (30:39) Early user acquisition strategies (35:50) Spotting trends and future innovations (39:20) Reflections on leadership and growth (43:16) Lightning round — Referenced: • Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/ • Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w • Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages • Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o • An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/ • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/ • FigJam: https://www.figma.com/figjam/ • Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/ • Coda: https://coda.io/ • Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/ • Websim: https://websim.ai/ • eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed.
Jun 30
48 min 7 sec
Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss: • How Jessica gained the affectionate title of the “social radar” • Why defensive founders are a red flag • How to develop your social radar • What she looks for in founders during YC interviews • How YC’s early inexperience in angel investing led to the batch model • Her favorite stories from interviews with Airbnb, Rippling, and more • Lessons learned from hosting her own podcast • Much more — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Vanta—Automate compliance. Simplify security — Find the transcript and references at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston — Where to find Jessica Livingston: • X: https://x.com/jesslivingston • LinkedIn: https://www.linkedin.com/in/jessicalivingston1/ • Podcast: https://www.thesocialradars.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) Jessica’s background (02:42) Thoughts on being under-recognized (07:52) Jessica’s superpower: the social radar (15:11) Evaluating founders: key traits and red flags (21:00) The Airbnb story: a lesson in hustle and determination (25:57) A YC success story (28:26) The importance of earnestness (32:45) Confidence vs. defensiveness (34:43) Commitment and co-founder disputes (37:46) Relentless resourcefulness (40:00) Jessica’s social radar: origins and insights (43:24) Honing her social radar skills (45:44) Conviction and scams: a Y Combinator story (46:50) The interview process: challenges and insights (48:20) Operationalizing founder evaluation (49:38) Advice for building social radar skills (52:08) The “Reading the Mind in the Eyes” quiz (55:19) Jessica’s podcast: The Social Radars (01:00:34) Lessons from podcasting and interviewing (01:09:58) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed.
Jun 27
1 hr 24 min