The Fat Man and the Little Boy debate

>updated with vibier sound!<

Welcome to my series on OG NY Tech -- celebrating 30 years of NY tech ecosystem, from 1995 to now.

Fred Wilson's USV is kind of a 'nuff said, to borrow NYC comic book language. Hear the very early days and listen past through into the epilogue to hear Fred on music scenes and the process of discovery.

🎙️ Episode Chapters

SECTION I — The Core Interview: Building New York Tech (1990s → Now)

00:00 – Opening & framing OG New York tech

Why this conversation exists: 30 years of New York tech, the OGNY moment, and why Fred Wilson’s career offers a uniquely New York lens on venture, media, and culture. 

03:00 – Fred’s origin story (engineering → venture)

Growing up everywhere, landing in New York, fleeing engineering, and discovering venture capital as the overlap between money and technology. 

07:30 – Venture capital before the internet

What 1980s venture actually looked like: PCs, networking, and a financial world that barely knew what to do with software. 

10:30 – The 1995 New York “New Media” scene

Journalists, artists, media kids, and early internet builders collide—AOL, CD-ROMs, web artists, and why New York’s tech scene grew out of culture, not semiconductors. 

13:00 – Starting Flatiron Partners

Leaving Euclid, early internet bets, and the unlikely move that gave Flatiron real firepower: institutional backing from Chase and SoftBank before the bubble mentality fully arrived. 

18:00 – “You’re investing in a website?”

A defining venture lesson: the best investments often sound ridiculous at first. Why laughter and disbelief are leading indicators of outsized returns. 

21:00 – Three core investing principles

Contrarian ideas people hate, founders driven by obsession rather than business plans, and why it’s often a mistake to monetize too early. 

26:00 – Missionary founders (Etsy, Duolingo)

Accidental entrepreneurs, aesthetic conviction, and building scale before business models—why belief comes before revenue. 

30:00 – New York culture as an investing advantage

Why art, music, and creative subcultures shaped investments like Etsy, Kickstarter, and SoundCloud—and why Silicon Valley logic didn’t fully apply. 

34:00 – Blogging, influence, and burnout

The rise of AVC: daily writing, community, learning in public—and why politics and online toxicity eventually broke the spell. 

47:00 – Big funds vs. artisanal venture

A candid reassessment: mega-funds may have “won,” even if small, craft-driven venture remains more personally meaningful. 

52:00 – Cult classic vs. blockbuster

Impact, legacy, and why some investors (and companies) choose influence over maximum scale. 

SECTION II — Epilogue: Music, Taste, and Discovery (Pre-Game Chat)

55:00 – Music as a life pattern

Classic rock, indie, and the joy of discovering what’s next rather than replaying the canon. 

57:00 – Being early, not right

Why showing up to small shows, supporting emerging artists, and sharing discoveries mirrors great investing behavior. 

59:00 – Taste as practice

Curiosity, openness, and cultural participation—not optimization—as the quiet through-line connecting music fandom, blogging, and venture capital.