Kevin Ryan, Alleycorp + MongoDB ++ Doubleclick, Dilbert

Welcome to my series on OG NY Tech

Celebrating 30 years of the New York tech ecosystem, from 1995 to now.

Kevin Ryan joined DoubleClick in 1996, just months after it was founded—and helped turn it into the most important New York technology company of the internet era. From there, he went on to co-found or incubate a generation of defining NYC companies: MongoDB, Business Insider, Gilt Groupe, and dozens more through AlleyCorp.

This conversation is about how New York tech actually formed: not in garages, not via hype cycles, but through media, advertising, distribution, discipline—and people who stayed when it got ugly.

🎙️ Episode Chapters — Kevin Ryan

DoubleClick, the Internet Crash, and Building New York’s Second Tech Act

SECTION I — Before “New York Tech” Existed

00:00 – Books, tapes, and recording everything The conversation opens not with startups, but with New York itself—books about the city, recording devices, and the instinct to document moments that don’t yet feel historic. A fitting entry point for someone who repeatedly found himself early to structural change.

03:00 – From Europe to Yale to Wall Street A childhood split between Rome, Geneva, and Ohio. Yale economics and art history. Investment banking. Business school at INSEAD. Disney Paris during the launch of Euro Disney—scaling from 1,000 to 20,000 employees in under two years. Operations before tech. Execution before mythology.

SECTION II — Media, Cartoons, and the Pre-Browser Internet

07:30 – Running Dilbert… before browsers existed At United Media (a division of E.W. Scripps), Kevin builds one of the earliest commercial websites—for Dilbert and other syndicated content—before Netscape, before Mosaic adoption, before “the web” meant anything to most people.

09:30 – Why this mattered Syndication economics are collapsing. Newspapers are consolidating. The internet quietly offers a way to bypass gatekeepers and go direct to audiences—if anyone can figure out how to monetize it.

11:30 – The first banner ads Ads are hard-coded. Prices are invented on the spot. Netscape and IBM buy week-long placements. Measurement barely exists. But something clicks: distribution plus software beats content alone.

SECTION III — 1995–1996: Silicon Alley, Barely

15:30 – How small it really was In 1995 New York internet events fit in a room. Everyone knows everyone. Media companies flirt with AOL, Prodigy, and Pathfinder. Most incumbents wait for “the next internet.”

16:30 – The innovator’s dilemma, live Kevin proposes building a real internet division inside United Media. Leadership declines—too small, too uncertain, too reminiscent of the CD-ROM bust. A textbook example, unfolding in real time.

SECTION IV — DoubleClick: The Right Abstraction

18:00 – Meeting the founders Kevin meets Dwight Merriman and Kevin O’Connor—recent arrivals from Atlanta with a radical idea: dynamic ad serving. Smarter, measurable, programmable advertising.

19:30 – Knowing what you don’t know Kevin immediately understands the business importance—and immediately knows he can’t build it himself. The partnership works because the abstraction is right and the roles are clear.

21:00 – From CFO to President to CEO Joined in mid-1996 as CFO. Becomes President within months. Later CEO. The company grows from 10 people to 2,000 in four years. IPO in 1998—just 24 months after founding.

SECTION V — The Boom, Then the Collapse

24:30 – 1998–2000: Peak Silicon Alley DoubleClick becomes New York’s most valuable tech company. Tens of billions in valuation. The center of gravity for online advertising globally.

25:30 – The crash everyone misremembers In 2000–2001, 70% of DoubleClick’s customers go bankrupt. Competitors give away product to survive. Markets panic.

Kevin’s contrarian take: The market wasn’t wrong in 2000—it was wrong in 2001. Buying the leaders at the peak would still have paid off long-term.

28:30 – Survival math Half the staff is laid off. Businesses are sold. But ad volume keeps doubling. Product quality compounds. Competitors die. The “fat get thin; the thin die.”

SECTION VI — Why He Stayed

31:00 – The CEO decision Kevin becomes CEO as conditions worsen—not improve. Morale is low. The job is brutal. But the fundamentals are undeniable: internet advertising isn’t going away.

33:00 – Looking past the stock price If you ignore the ticker and look only at usage, share, and technical advantage, the outcome is obvious. That conviction carries the company through.

SECTION VII — Leaving, Then Starting Again

35:00 – Exiting DoubleClick After nine years, DoubleClick is sold to private equity (and later to Google). Kevin leaves—not out of failure, but boredom. Ad tech is solved.

36:00 – AlleyCorp: Incubation as craft From 2005 to 2008, Kevin and Dwight incubate six companies at once, investing their own capital, acting as chair and technical backstop.

37:30 – The hits

• MongoDB — open source, enterprise software, ten-year overnight success
• Business Insider — hiring Henry Blodget, betting on redemption and velocity
• Gilt Groupe — fashion, logistics, and scale at internet speed

Also: Panther, ShopWiki, Music Nation—some wins, some misses. The math still works.

SECTION VIII — MongoDB and the New York Enterprise Myth

44:00 – “You can’t build enterprise software in NYC” MongoDB disproves it. Slowly. Painfully. No revenue for years. Then compounding takes over.

46:00 – The long curve After 10+ years, MongoDB goes public at ~$100M revenue. The vast majority of value is created after year eleven.

47:30 – What people get wrong New York doesn’t lack technical talent. It lacks patience myths. Enterprise outcomes reward persistence more than hype.

SECTION IX — From Builder to Platform

50:00 – After 2013 AlleyCorp evolves from pure incubation to investing at scale. One LP becomes many. Fifteen to twenty investments per year. Fewer incubations. More pattern recognition.

52:00 – Having good ideas Good ideas aren’t brainstorms. They’re friction noticed repeatedly: Business news that doesn’t update. Wedding registries that sell plates instead of experiences. Databases that don’t match modern data.

CLOSING — The Actual Arc of New York Tech

54:00 – What this story really shows New York tech didn’t emerge from imitation. It emerged from media, ads, logistics, finance, and people willing to stay through down cycles.

55:00 – The hidden continuity From Dilbert on pre-browser internet to MongoDB at $30B+, this is one continuous story—not reinvention, but accumulation.