A 29-year-old VC founder proved that persistence in cold emailing can open doors most people assume are locked. Harry Stebbings, the energetic founder behind 20VC, wanted Salesforce CEO Marc Benioff on his show so badly that he emailed him 53 times over the span of a year. The surprising part is that it worked.
Stebbings shared the story on the “Biography” podcast with Wouter Teunissen, and the way he told it makes the whole thing feel less like luck and more like a skill. He said most people cold-email poorly, but doing it well can get the attention of almost anyone if you’re willing to put in the work.
He explained that he always starts with a clear, direct subject line, without trying too hard or sounding desperate. Once the email opens, he gets straight to the point. He avoids the empty small talk most people add out of habit. Instead of “I hope you’re well,” he leads with why he’s reaching out. That clarity, he said, is what keeps busy people reading instead of deleting.
Then he establishes credibility. He keeps it short but sharp. He lists the size of his audience or the big names he has already interviewed. The idea is simple: show the recipient that saying yes will be worth their time. For Stebbings, mentioning previous guests like Sam Altman, Bill Ackman, or Scooter Braun adds weight without sounding like self-promotion.
Once the value is clear, he makes the ask feel manageable. He tells them exactly how much time he needs, so it doesn’t feel like a draining commitment. And then he closes with a personal touch, something tailored, not generic. With Benioff, he tested everything from whiskey gifts to references to his holiday home or Salesforce’s quarterly results. He wanted each email to feel like it actually had him in mind.
Today, finding these personal nuggets is easier than ever. Stebbings said AI has made research faster and richer. A quick scan with an LLM can surface interesting details or lesser-known facts that help you write an email that feels thoughtful instead of automated.
He also believes timing matters as much as tone. If you meet someone briefly at a dinner, he said you should email them immediately, not the next day. He thinks that delay gives the impression that the interaction wasn’t meaningful enough to act on. Moving fast keeps you memorable.
For Stebbings, all these habits come back to one principle: doors only open when you keep knocking. His podcast has hosted some of the biggest names in tech and investing, and he credits much of that to choosing the path that leads to more opportunities rather than fewer. He frames it simply: always take the option that opens another door.
Benioff eventually noticed the effort. In fact, he seemed amused by it. When the episode finally went live in 2023, Benioff posted about it on X, pointing out the number of attempts and celebrating the persistence behind them. He joked that Stebbings must have emailed or texted him a hundred times before he agreed to show up. But he also reinforced the message: persistence pays.
And Stebbings’ story proves that stubborn consistency, paired with a smart cold-email strategy, can turn “impossible” guests into real conversations.
Stebbings also made it clear that persistence only works when it is paired with respect. He said there is a fine line between being memorable and being annoying. Each follow-up has to add something new, whether that is a fresh angle, an updated milestone, or a relevant moment tied to the recipient’s world. Repeating the same message, he warned, is the fastest way to get ignored.
Another point he stressed was emotional control. Cold emailing can feel personal when it fails, especially after dozens of attempts. Stebbings said learning not to take silence as rejection was essential. Most inboxes are chaotic, not hostile. A missed reply often means bad timing, not a hard no. That mindset made it easier for him to keep going without burning out or sounding frustrated.
He also argued that persistence compounds over time. Early in his career, very few people responded. But each “yes” made the next ask easier. As the guest list grew, credibility stacked. What began as relentless outreach slowly turned into inbound interest. The strategy did not change, but the leverage did.
The lesson extends beyond podcasting. Founders raising capital, operators hiring talent, or anyone trying to break into closed networks face the same challenge. Stebbings’ approach shows that access is rarely about permission. It is about preparation, patience, and the willingness to follow up long after most people quit.
In the end, the Benioff story is less about one successful email and more about building a repeatable system. Persistence was the engine, but clarity, relevance, and respect were the fuel. Together, they turned a cold inbox into one of the most talked-about episodes in tech media.
