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.