The Persistence Playbook: 53 Cold Emails That Worked
In the high-stakes world of venture capital and media, a single email can be a turning point. Harry Stebbings, the founder of 20VC, is known for his relentless outreach and his knack for turning persistence into conversation. In 2023, Stebbings landed an interview with Marc Benioff, the Salesforce founder and tech industry icon, after a long sequence of targeted messages. The story isn’t just about luck; it’s a case study in how thoughtful, consistent outreach can pierce even the busiest inboxes.
Who Is Harry Stebbings and Why It Mattered
Harry Stebbings built 20VC into a prominent player in the venture capital scene by blending media with deal flow. His podcast became a launchpad for founders and investors alike, attracting high-profile guests and a growing audience. Securing an interview with Marc Benioff—an executive known for a demanding travel schedule and limited interview windows—was a signal achievement for 20VC. It also highlighted the strategic value of persistence when pursuing senior leaders who usually receive countless outreach attempts.
From Numbers to Nuance: The 53 Emails Strategy
The core idea behind Stebbings’ approach wasn’t simply to send more emails; it was to craft messages that resonated with Benioff’s priorities: leadership, social impact, and Salesforce’s long-term vision. The process likely involved:
- Research-driven messages: Each email was informed by an understanding of Benioff’s public statements, philanthropic interests, and business priorities.
- Incremental touchpoints: A sequence built to move from awareness to interest, avoiding volume-based spam tactics in favor of value-driven contact.
- Clear value proposition: The invitations emphasized how Benioff’s participation would benefit listeners, the broader community, and the storytelling goals of the podcast.
- Respect for boundaries: When possible, messages were tailored to fit Benioff’s schedule, signaling professionalism and consideration for his time.
While 53 messages might sound excessive, the underlying principle is common in successful cold outreach: blend persistence with relevance, and you increase the likelihood of a response that isn’t just polite but also actionable.
Turning Persistence into a Podcast Opportunity
Outreach to a marquee guest like Benioff often hinges on more than a clever subject line—it requires a compelling narrative about why the guest should engage at this moment. For Stebbings, the pitch wasn’t simply about selling a conversation; it was about creating a meaningful platform that could reach an audience hungry for expertise on leadership, technology, and entrepreneurship. The resulting interview became not only a personal milestone for Stebbings but a valuable asset for 20VC’s audience and credibility.
The Lessons for Aspiring Outreach Pros
Stebbings’ experience offers practical takeaways for anyone trying to reach influential figures:
- Lead with value: Communicate what the guest and their audience gain from participating.
- Be patient and disciplined: A multi-touch sequence, thoughtfully spaced, respects the recipient’s time while keeping the door open.
- Know your subject: Deep research pays off, turning generic emails into targeted, credible invitations.
- Measure and adapt: Treat outreach as a campaign—notice what works, refine, and persist with a respectful cadence.
Impact Beyond a Single Interview
The Benioff interview didn’t just satisfy a curiosity about a Salesforce leader; it amplified the reach of 20VC’s content strategy. Episodes featuring renowned guests can boost a firm’s profile, attract high-caliber founders, and unlock new investment conversations. More broadly, the tale underscores a core truth of modern media and investment: relationships built through consistent, value-driven outreach often translate into long-term opportunities.
Conclusion: Persistence with Purpose
Harry Stebbings’ 53 cold emails to Marc Benioff were more than a tedious tally. They encapsulated a disciplined approach to outreach—one that combines rigorous research, patient sequencing, and a clear value proposition. For anyone aiming to break through digital noise, the lesson is simple: be relentless, but be relevant. When a well-timed, well-crafted invitation aligns with a leader’s priorities, a single message can become a gateway to lasting impact.
