Persistence pays off: the 53 cold emails behind a landmark interview
Harry Stebbings, the 29-year-old founder of VC firm 20VC, is renowned for his relentless outreach. In 2023, his audacious strategy paid off when he secured an interview with Marc Benioff, the CEO of Salesforce. The story isn’t just about luck; it’s a case study in disciplined outreach, brand building, and the power of a well-timed pitch.
Stebbings didn’t land the interview with a single, perfectly crafted message. Instead, he deployed a patient, multi-step approach that began long before the first email landed in Benioff’s inbox. The objective: convert a busy tech titan into a compelling guest who could illuminate venture capital trends for Stebbings’ podcast audience and the broader startup community.
The strategy behind the 53 emails
Cold-email psychology often hinges on relevance, value, and credibility. For Stebbings, the framework included: a precise value proposition, clear social proof, and a multi-channel cadence that respected Benioff’s time. Each message built on the prior, refining the hook and the pitch based on responses (or the lack thereof). The goal wasn’t to pressure but to persist with purpose.
Key to the strategy was tailoring content to what Benioff cared about: leadership, social impact, and the future of technology. Stebbings leaned into data points, trend analyses, and potential episode formats that would translate into meaningful insights for listeners. He also leveraged his growing profile in the VC and podcast space, along with tangible examples of how previous guests had amplified their brands by appearing on his show.
Crafting the invitation that broke through
What distinguished Stebbings’ approach was not merely the volume of outreach, but the quality of the invitation. The messages typically featured: a succinct elevator pitch, a stated impact for Benioff’s brand, and a concrete plan for the interview structure. He proposed angles that aligned with Benioff’s expertise—innovation in enterprise software, leadership in a dynamic market, and the evolving responsibilities of tech founders in society.
Over time, the cadence toggled between persistence and respect. Some emails were brief, others offered data-backed insights or suggested rough timelines. The underlying theory was clear: even a busy executive sometimes responds to a well-timed, well-crafted request that promises value to their audience and their personal narrative.
The payoff: a candid, influential conversation
When Marc Benioff finally agreed to appear, the interview delivered more than just content. It provided legitimacy for Stebbings’ platform and broadened 20VC’s reach within the tech and startup communities. For listeners, the episode offered a rare glimpse into the leadership philosophy of one of the tech industry’s most influential figures. For Stebbings, the interview validated a long-term strategy rooted in consistent, targeted outreach and a willingness to stand out in a crowded media space.
The fallout extended beyond a single episode. The Benioff interview helped illuminate broader themes about the venture ecosystem: the importance of authentic storytelling, the role of personal branding in fundraising, and how thoughtful persistence can unlock opportunities that feel out of reach for many founders and operators.
Lessons for founders and communicators
Stebbings’ experience offers practical takeaways for anyone looking to reach top-tier guests, partners, or customers:
- Persistence matters, but it should be purposeful. A sequence of messages with clear value beats one-off, generic outreach.
- Lead with impact. Demonstrate how a collaboration benefits the guest’s own goals or public narrative.
- Build credibility before you ask. Social proof, early wins, and a compelling platform help recipients see the upside quickly.
- Respect the channel and the timeline. Busy leaders appreciate concise requests and flexible scheduling options.
Harry Stebbings’ 53-email odyssey to Marc Benioff isn’t a blueprint for spamming. It’s a blueprint for strategic perseverance—an example of how a relentless, well-crafted approach to outreach can turn an audacious idea into a watershed moment for a brand and its audience.
