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Illustration: Lazaro Gamio/Axios

Shasta Ventures, a Silicon Valley-based VC firm whose investments have included Nest and Anaplan, is facing a major fundraising challenge after the unexpected departure of one of its top partners.

What's happening: Doug Pepper, who joined Shasta in 2016 after more than 15 years with InterWest Partners, quit several weeks ago for a job with Iconiq Capital, Axios has learned from multiple sources.

  • Pepper was one of three "key men" on Shasta's sixth fund, which had closed on around $175 million of its $325 million target. The loss of any key man would allow limited partners to cancel their commitments, if they so chose.
    • This is particularly problematic for Shasta, as this is its first fundraise without co-founder Rob Coneybeer as a full-timer.
  • Shasta now is in discussions with those existing investors and, if it can keep them on board, is expected to lower the overall fund size target.
    • There was talk that fundraising sluggishness might have played into Pepper's departure, but the real reason for why he bailed on his partners is unclear. LPs are annoyed at having to repeat some of their due diligence, although it may be tough for them to further punish the jilted.
    • Shasta's second fund is considered to be its blockbuster, while its past couple are weaker performers.
  • There also is talk of at least one more significant departure, albeit not of remaining key men Jason Pressman or Ravi Mohan.

Axios reached out to Pepper and several Shasta representatives, but did not receive a call back.

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