An Anecdote About Persistent Cold Email

A speaker describes repeated outreach and suggests researching personalization with a language model.

Channel
20VC with Harry Stebbings
Published
Nov 18, 2025
Video
0:48
Read
1 min
Original
English
Open on YouTube
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SUMMARY

In 30 seconds

In this short 20VC clip, a speaker recounts repeated emails to Marc Benioff and discusses using language models to research personalization. The clip does not establish the full outcome, and generated claims require verification.

  1. 1Repeated outreachThe speaker describes a long series of personalized cold emails.
  2. 2Limited contextThe short clip does not establish the result of the full exchange.
  3. 3Research and verificationVerify AI-generated details and respect recipients’ preferences.

Takeaways

  1. The speaker describes a long series of personalized cold emails.
  2. The short clip does not establish the result of the full exchange.
  3. Verify AI-generated details and respect recipients’ preferences.
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01

Personalization and persistence

The speaker recounts outreach and discusses AI-assisted research.

A speaker says they emailed Salesforce CEO Marc Benioff once a week for 53 weeks, testing different personalized approaches. The anecdote describes their experience, not evidence that persistent unsolicited emails generally work.

The speaker mentions experimenting with references to the recipient’s interests and company results. The clip emphasizes persistence, although it does not show the full exchange or explain the eventual outcome.

The speaker suggests asking a language model for less-obvious information to personalize an email. Model-generated claims should be checked against reliable public sources, and outreach should respect the recipient’s privacy and wishes.

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