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Chronicles

The story behind the story

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Profile of Bill Gurley, whose VC firm Benchmark scored huge wins in 2017 from Snap and Stitch Fix IPOs amid scandals at Uber, where Benchmark holds ~$8B stock

Ari Levy / CNBC : Tweets: @levynews Tweets: Ari Levy / @levynews : He “knew a storm was going to take place” and the rest of the world had no idea what was coming. http://www.cnbc.com/...

CNBC Ari Levy

Context & Ripple Effects

The profile lands at the end of a year when Benchmark's two IPO wins — Snap and Stitch Fix — papered over the firm's messiest chapter: the Uber culture scandals, with roughly $8 billion of stock riding on the company. Gurley had handed his Uber board seat to Matt Cohler back in June, stepping out of the line of fire as the fallout peaked.

What came after reinforces the profile's thesis: Benchmark kept its next fund at the size of its previous ones rather than joining the mega-fund wave, while Gurley redirected his public energy toward persuading startups to choose direct listings over bank-led IPOs.

First-order effects

  • Gurley and Benchmark enter 2018 with fresh evidence that their concentrated, small-fund model still produces outsized returns, even as the roughly $8 billion Uber position remains the firm's largest single exposure.
  • Matt Cohler inherits the Uber board seat, taking over Benchmark's oversight of its biggest holding amid continuing governance turmoil.

Second-order effects

  • Late-stage Uber investors such as SoftBank and Saudi Arabia's PIF face open questions about whether they will see serious profit on positions Benchmark bought into years earlier at a fraction of the cost.
  • As rivals raise ever-larger funds, Benchmark's decision to hold fund size flat becomes a visible counter-position that LPs must weigh against the mega-fund consensus.

Third-order effects

  • If Gurley's direct-listing advocacy gains traction, the bank-led IPO loses its default status for late-stage startups — restructuring how venture firms realize returns.
  • The pattern points toward a durable split in venture structure: small, concentrated funds competing with mega-funds on returns per dollar rather than assets under management.

The trend: Venture capital is splitting between mega-funds chasing scale and small firms like Benchmark betting that concentration plus exit-mechanism reform through direct listings beats sheer fund size.