Dennis Crowley, Foursquare and Dodgeball

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.