Persistence Pays Off: The Case of 53 Cold Emails
Harry Stebbings’s approach to outreach has become the stuff of startup lore. The founder of 20VC didn’t rely on luck or casual connections to get the attention of Marc Benioff, the Salesforce CEO. Instead, he built a disciplined, data-driven campaign that culminated in a pivotal interview in 2023 for his podcast. This is a closer look at the tactics behind his success and what aspiring founders can learn about cold outreach to top-tier industry leaders.
Understanding the Why: What Made Benioff a Worthy Target
Marc Benioff is not only a billionaire entrepreneur; he’s also a powerful voice in technology, philanthropy, and business leadership. For a podcast focused on venture capital, founders, and the future of software, securing an interview with Benioff could unlock credibility, audience growth, and strategic insights. The decision to pursue him was guided by alignment with 20VC’s mission and the value his perspectives would bring to listeners.
Defining the Offer: A Clear Value Proposition
Stebbings didn’t send generic messages. He framed a compelling value proposition for Benioff’s team from the outset. The pitch emphasized how the interview would reach a specific audience—early-stage founders and tech leaders—and how it would reflect well on Benioff’s own visions and initiatives. A well-defined audience, a clear topic, and measurable benefits are pillars of successful cold outreach to high-profile figures.
The Cadence: 53 Touchpoints That Built Momentum
Persistence is a core element of Stebbings’s approach. The number 53 is more than a staggering tally; it reflects a deliberate cadence that blends persistence with respect for the recipient’s time. Each outreach attempt was designed to be different—refining subject lines, adjusting the value hook, and varying the channel. The goal wasn’t to overwhelm but to create a sequence that remained professional, personalized, and relevant over time.
Subject Lines and Personalization
Effective cold emails begin with a subject line that conveys relevance and curiosity. Stebbings reportedly experimented with multiple angles, from timely industry topics to personal reflections on Benioff’s leadership. Personalization didn’t require intimate knowledge of Benioff, but it did require acknowledging his work, linking it to a concrete episode or idea, and promising a crisp, value-forward conversation.
Multi-Channel Persistence
Beyond emails, successful outreach often spans multiple channels. While the core message remained consistent, Stebbings leveraged different platforms—email, social messages, and polite follow-ups—to increase visibility without crossing lines into spam. The key was to provide a reason to respond that felt mutually beneficial and time-conscious.
Delivering Value: What the Interview Offered Benioff
The interview served as a two-way exchange. For Benioff, appearing on a high-profile venture capital podcast offered a platform to discuss his strategic priorities and his broader perspective on technology trends and philanthropy. For listeners, the episode provided actionable insights from a figure at the intersection of software, enterprise sales, and global business leadership. The mutual benefit was clear, making the invitation more appealing once a relationship was established.
Takeaways for Founders: Building a Cold Email Playbook
From Stebbings’s experience, aspiring founders and operators can extract several practical principles:
- Start with a specific, measurable value proposition tailored to the recipient.
- Design a structured outreach cadence that evolves based on feedback and timing.
- Prioritize personalization over volume; quality beats quantity when dealing with busy leaders.
- Be respectful of schedules and preferences; offer flexible formats and concise conversations.
Long-Term Impact: Beyond One Interview
The payoff of a well-executed outreach campaign isn’t only the interview itself. It’s the broader credibility, content library, and access it unlocks for future opportunities. For Stebbings and 20VC, the Benioff interview could serve as a magnet for other industry leaders and a model for future outreach campaigns beyond the tech sector.
Conclusion: A Strategic Blueprint for Cold Outreach
Harry Stebbings’s experience with 53 cold emails to Marc Benioff demonstrates that perseverance paired with a clear value proposition can open doors often guarded by time-constrained executives. For founders building a brand and seeking authoritative voices, the lesson is simple: be purposeful, be patient, and deliver content that aligns with the recipient’s interests and your audience’s needs.
