In a world of thousands of LinkedIn messages and random inbox pitches, sometimes annoying does win out. Harry Stebbings, a 29-year-old founder of the venture capital firm 20VC, sent Mr. Benioff’s assistant 53 cold emails over just over a year before finally securing an interview with the billionaire chief executive of Salesforce. What sounded like a fanatical obsession was, in fact, a repeatable outreach strategy—and it worked.
In Stebbings’ recent appearance on the “Biography” podcast, he describes it as methodical rather than desperate: begin by opening with a clear and non-needy subject line telling them precisely what you want so that they read below; jump immediately into why you have credibility — e.g., “podcast X subscribers, previous guests Y and Z”; continue with a personal hook, like “I noticed you collected Pappy Van Winkle” or “I actually lived in the Marina where you started Salesforce,” and finally always follow up. He said he used large language models to help fill gaps in public information and test subject lines.
What is notable in this is how Benioff himself called the campaign. In a subsequent post about the interview, he said, “Harry must have texted and emailed me 100 times before I agreed to be on his podcast. 53 cold emails later. Never ever give up. Persistence pays Harry.” That sort of public acknowledgment from a major tech titan adds both luster and legitimacy to the win.
And for other founders, creators, and aspirants, the lesson is clear: It’s about more than the message — it’s about consistency and shrewd positioning. Most people give up after one, two, or three outreaches; Stebbings sent 53 before receiving a yes. That gives you a sense of how much faith, planning, and time it took.
Sure, some elements made his success more probable than average: he already had a podcast as a known quantity, guests with star power, and a straightforward proposition. But the mechanics of his outreach — clarity, credibility, personalisation, cadence — have broader application.
It does not hurt that one way to unlock doors is to have a podcast with Marc Benioff. But there’s something bigger in Stebbings’ journey: how he created an opportunity out of a “cold inbox” by building a structure on top of repetition. For anyone trying to reach someone else who feels unreachable, the takeaway isn’t magic — it’s method.
53 emails, a campaign with a single focus, and a lesson in persistence. Harry Stebbings didn’t just “get lucky” — he ran a playbook when 95%+ of everyone else didn’t even move their pens.
