In the Know with Amol Sarva

Albert Wenger, Union Square Ventures

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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.
                                  • ...more
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                                  In the Know with Amol SarvaBy Amol Sarva
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