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VC's Secret: 53 Emails Secured Benioff Interview
22 Nov, 2025
Summary
- Harry Stebbings sent 53 cold emails over a year to secure an interview.
- Effective cold emails require clarity, credibility, and personalization.
- Persistence and personalization are key to landing high-profile guests.
Harry Stebbings, founder of 20VC, shared his meticulous cold email strategy that led to an interview with Salesforce CEO Marc Benioff. This significant achievement required 53 emails sent over the course of a year, highlighting the power of persistent outreach. Stebbings stressed that effective cold emailing is a skill that can be learned by focusing on key components.
The core of Stebbings' strategy involves crafting a clear, non-needy subject line and stating the email's purpose early on. He advocates for providing credibility by mentioning metrics like subscriber counts and notable past guests. Furthermore, he suggests personalizing emails, even to the point of offering gifts or referencing specific details about the recipient, a tactic he utilized with Benioff and now recommends using AI to discover unique facts.
Stebbings also underscored the importance of timely follow-ups, especially after in-person encounters, to keep the interaction fresh in the recipient's mind. His philosophy encourages seizing opportunities that can open new doors, a principle echoed by Benioff's public acknowledgment of Stebbings' persistence. This approach has also secured interviews with other prominent figures like Bill Ackman and Sam Altman.
