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

Albert Wenger tells me about his 20 years at USV, and how NY went from apps-mostly to deep and infra.

🎙️ In the Know — OG NY Tech

Guest: Albert Wenger (Union Square Ventures) Theme: 30 years of New York tech — personal origin story, early ecosystem formation, iconic USV bets, and future-facing frameworks (crypto + AI).

00:00–03:00 — Cold Open & Framing

Playful cold open bumping into Fred Wilson; teasing a broader oral history of OG New York tech.
Framing: 2025 ≈ 30 years since the “start” of modern tech (1995 milestones: Netscape IPO, Amazon founded, Yahoo incorporates, etc.).
Establishes the podcast arc: reconstructing how New York became a real tech ecosystem.

03:00–07:30 — Discovering the Web (MIT Years)

Albert discovers the web via Mosaic browser in an MIT lab.
Describes the visceral “I’ve seen the future” moment and early intuition that newspapers would be disrupted (timing optimistic, direction correct).
Nice color on early internet UX and accidental discovery.

07:30–10:00 — First Startup: W3 Health

Doing a startup and a PhD simultaneously (strongly not recommended).
W3 Health tackled patient data interoperability — still largely unsolved today.
Learns he’s not a great CEO; brings in operators.
Finishes dissertation, graduates MIT (1999), moves permanently to NYC.

10:00–13:30 — Fintech Detour + Bubble-Era Incubation

Joins internet bank (Telebank → E*Trade Bank).
Raises $25M for incubator LC39 at the peak of the dot-com bubble.
Near-merger with a European internet vehicle collapses when the bubble bursts.
Returns ~90¢ on the dollar to investors — rare mercy in that era.
Early relationship with Brad Burnham (board member).

13:30–18:30 — Nuclear Winter & Almost Buying a Trucking Software Company

Post-bubble funding freeze (2000–2002).
Almost acquires TMW Systems (trucking software in Cleveland); deal collapses over tax issues.
In retrospect, a lucky escape.
Meanwhile Brad + Fred form Union Square Ventures (first fund raised ~2003–2004).

18:30–28:30 — Delicious: Social Tagging, Early Web Culture

Meets Joshua Schachter; Delicious becomes one of USV’s earliest investments.
Social bookmarking + tagging as foundational internet primitives (proto-hashtags).
Yahoo acquisition happens quickly; secondaries didn’t exist yet, forcing early exit.
Pushback on Yahoo bureaucracy; avoids west-coast relocation; first real liquidity moment.
Theme: influence vs financial outcome — cultural impact exceeds exit value.

28:30–34:30 — Angel Investing → Tumblr & Etsy

Starts hanging around USV; angels into Tumblr and Etsy.
Etsy thesis: highly engaged sellers + low fees rejected by West Coast VCs.
USV style crystallizes: large networks of engaged users, differentiated by user experience.
Pattern recognition over fashionable narratives.

34:30–41:30 — New York vs Silicon Valley Narratives

Stereotype debate: “taste vs engineering.”
MongoDB as proof that deep infrastructure can emerge in NYC.
LP skepticism toward NYC as a tech hub in mid-2000s.
USV flies constantly to SF while nurturing NYC companies.

41:30–50:30 — Foursquare: When Too Much Money Breaks a Company

Andreessen Horowitz forces entry by dramatically increasing valuation.
Overcapitalization causes bloat, loss of product discipline, slow execution.
Facebook clones features; Instagram ultimately captures the category.
Lesson: capital velocity can destroy product velocity.

50:30–55:30 — Tumblr, Pinterest Miss, and Product Geometry

Pinterest originally incubated in NYC; misread as “too similar” to Tumblr.
Key insight missed: flow (Tumblr) vs stack/board (Pinterest).
Small UX topology differences create massive outcome divergence.

55:30–01:04:30 — E-commerce, Network Effects & What USV Avoided

Vertical e-commerce lacked strong network effects.
USV generally avoided pure “sell stuff online” models (Etsy exception).
Preference for compounding networks over margin arbitrage.

01:04:30–01:09:30 — Tech “Mafias,” Google’s Gift to NYC

NYC historically lost talent after acquisitions forced westward relocation.
Google’s NYC engineering presence reverses brain drain.
Alumni effects begin to seed local startups.
Bloomberg’s closed culture inhibited entrepreneurial spinouts.

01:09:30–01:12:30 — Crypto: Stablecoins as the Quiet Killer App

Stablecoins transforming cross-border trade, especially emerging markets.
New rails replacing old banking infrastructure.
NYC initially constrained by regulatory friction and legacy finance antibodies.

01:12:30–01:16:30 — AI: The Four Futures Framework

Two axes: speed of AI improvement × openness of models → four futures.
Possibility of massive closed-model monopolies vs open chaotic ecosystems.
Crypto potentially essential for machine-to-machine economies.
Existential risk acknowledged without theatrics.

01:16:30–01:19:30 — Physical AI & Deep Tech in NYC

Portfolio example: Veeam (robotics / physical AI) founded by MongoDB alumni.
NYC strength in biotech + robotics + applied AI despite weaker infra dominance.
Convergence of AI, physical systems, and biology as next frontier.

01:19:30–01:22:30 — Looking Forward: Bubbles, Cycles, Curiosity

Comparing AI hype curve vs dot-com timeline.
Reminder: dot-com valuations were far more extreme than today’s AI multiples.
Closing reflections on curiosity, long-term compounding, and ecosystem evolution.

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