Welcome to my series on OG NY Tech -- celebrating 30 years of NY tech ecosystem, from 1995 to now. Dennis Crowley tells us how he got to New York and the early internet culture in the media/Wall Street world: and how it all led to Foursquare -- the art of the game 🎙️ Episode Chapters — Dennis Crowley From Punk Zines to Foursquare: How New York Taught the Internet to Find Itself SECTION I — The Core Interview: Growing Up Inside the Internet 00:00 – Setting the frame: OG New York tech Why Dennis Crowley belongs in the canon of New York founders, and why 1995 feels like a plausible “Year Zero” for the consumer internet. 03:00 – Suburban modems and early online culture Dial-up life, BBS culture, AOL, Prodigy, and discovering the thrill of connecting machines to people before the web had pictures. 05:30 – Punk zines, skating, and DIY publishing Photocopied fanzines about video games and skate culture; disposable cameras as “screenshots”; learning layout, editing, and distribution before the word “creator economy” existed. 09:00 – Music as an operating system Native Tongues hip-hop, skating culture, and the aesthetics of the early ’90s shaping taste, rhythm, and community instincts. 11:30 – Syracuse and discovering the graphical web First Ethernet connections, Mosaic, Marc Andreessen in the newspaper, and realizing the web could become a mass medium. 13:30 – Early digital storytelling Scanning photos, building homepages, blink tags, animated GIFs, and using the web as a proto-blog long before social media had a name. 15:00 – Advertising school meets the internet Majoring in advertising, minor in information studies, and becoming the “internet kid” inside traditional agencies. 16:30 – Jupiter Media and the dot-com boom Moving to New York in 1998 as a research associate, learning how the internet economy actually worked, and living inside nonstop startup parties. 20:00 – Studying the plumbing of the web Infrastructure research: ecommerce systems, personalization engines, early customer-service analytics, and measuring how badly websites handled users. 23:00 – The crash arrives Dot-com collapse, layoffs, evaporating optimism, and the sense that the entire New York tech experiment might be over. SECTION II — Dodgeball: Inventing Location Before Smartphones 25:00 – Discovering Indigo and city software Falling in love with Palm Pilots, mobile city guides, and the idea that cities deserved real-time digital maps. 26:30 – Teaching himself to code “Learn to code in 30 days” books, hacking together early prototypes, and turning curiosity into functioning software. 28:00 – Layoffs, eviction, and personal collapse Job loss, housing instability, breakups — and how downturns compress life into creative pressure cookers. 29:00 – Montauk, Harry Potter, and the Marauder’s Map The idea spark: phones as real-time maps of where friends are, long before GPS or push notifications were normal. 30:30 – Building primitive location sharing Email hacks instead of SMS, self-reported locations, and inventing “check-ins” without calling them that. 31:30 – 9/11 and leaving the city Being in the West Village on September 11th, the emotional shock, and temporarily abandoning New York. 33:00 – Snowboarding exile and reflection Retreating to New Hampshire, teaching snowboarding, video games as therapy, and deciding what comes next. 35:00 – NYU ITP: art school for the internet Returning to New York through NYU’s Interactive Telecommunications Program — a collision of artists, hackers, designers, and urban technologists. 38:00 – Dodgeball reborn at ITP Partnering with Alex Rainert, remixing Friendster ideas into mobile social networking, and making phones socially alive. 41:00 – The Lower East Side as a living network Bars as incubators, bloggers as amplifiers, Dodgeball driving physical crowds in real time — a proto-network effect. 43:30 – Media flywheel Blog coverage → mainstream press → CNN → cultural legitimacy, all happening inside New York’s dense media ecosystem. 45:00 – Why venture capital didn’t show up yet Scarce funding, dismissive investors, and the feeling of building something culturally obvious but financially invisible. SECTION III — Google, Loss, and Reinvention 48:00 – Google acquires Dodgeball A chance lunch, repeated demos in one afternoon, and a long acquisition process that finally closes. 50:00 – Life inside early Google New York Watching Google scale the building footprint, seeing other acquisitions (Docs lineage), and learning how platforms actually grow. 53:00 – Identity crash after leaving Google Losing Dodgeball as a personal identity, feeling professionally unplaceable, and facing creative emptiness. 55:00 – The sunset press release Google announces Dodgeball will be shut down — triggering urgency and emotional ignition. 56:00 – Birthday party epiphany At Lockhart Steele’s party, deciding to rebuild — this time with a launch deadline: South by Southwest. 58:00 – Everyone says no (again) Investors skeptical, legal fears, déjà vu rejection, and the persistence muscle getting tested. 01:03:00 – The breakthrough: real-world rewards A San Francisco café accidentally invents the Foursquare business model — check-ins unlocking real benefits. 01:05:00 – Overnight momentum From ignored to oversubscribed almost instantly as the flywheel becomes visible. CLOSING — What This Episode Is Really About This isn’t just the origin of Foursquare. It’s a story about: how creative subcultures feed technical invention how cities shape product behavior how failure metabolizes into insight how timing matters more than genius how the internet learned to inhabit physical space And how New York — messy, artistic, media-dense, socially entangled — uniquely incubated a category that Silicon Valley later industrialized.
