Familiar with the lore of Y Combinator? Then you'll know Jessica Livingston — one of the original co-founders who started YC back in 2005. On a recent visit to our SF headquarters, she shared with the Lightcone hosts the stories and decisions of the early days that would form the foundations of YC as we know it today.
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 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 — Referenced: • Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html • Paul Graham on X: https://x.com/paulg • Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris • Trevor Blackwell on X: https://x.com/tlbtlbtlb • Y Combinator: https://www.ycombinator.com/ • “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal • Patrick Collison on X: https://x.com/patrickc • John Collison on X: https://x.com/collision • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/ • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/ • Zenefits: https://connect.trinet.com/hr-platform • Goat: https://www.goat.com/ • Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/ • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/ • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/ • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups •Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html • Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691 • SmartLess podcast: https://www.smartless.com • Jason Bateman on X: https://x.com/batemanjason • Will Arnett on X: https://x.com/arnettwill • Sean Hayes on X: https://x.com/seanhayes • The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash • The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb • The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe • The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase • The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch • The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb • The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab • Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788 • Startup School: https://www.startupschool.org/ • The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling • Rippling: https://www.rippling.com/ • Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957 • Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06 • Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/ • Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/ • My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522 • Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R • Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273 • Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone • Sam Altman on X: https://x.com/sama • Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/ • Alexis Ohanian on X: https://x.com/alexisohanian • Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/ • Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/ • Charles River Venture: https://www.crv.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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe