In a remarkable revelation that underscores the power of persistence, venture capital fund 20VC founder Harry Stebbings has disclosed that it took him 53 cold emails to secure an interview with Salesforce CEO Marc Benioff for his popular podcast. The 29-year-old entrepreneur's relentless approach finally paid off in 2023 when Benioff agreed to appear on "The Twenty Minute VC" podcast.
The Art of Strategic Stalking
Stebbings, who has built his podcast into one of the most respected in the venture capital space, doesn't shy away from describing his method as learning to be "a stalker" when it comes to cold emailing top executives. During an appearance on The Biography Podcast, he emphasized the accessibility of email communication in today's digital age.
"It is absolutely nuts to me that you can find anyone's email on the internet and just cold email them," Stebbings remarked. "I'm pretty sure if you're a good enough stalker, because you have to be a stalker, by the way—everyone should learn to be a really efficient SDR, but essentially a stalker."
The Hustle Time Strategy
What makes Stebbings' approach systematic rather than random is his dedicated "hustle time" - a weekly 30-minute block where he focuses entirely on crafting personalized cold emails to high-profile potential guests. This disciplined approach has helped him secure most of his prominent interviewees through cold outreach.
The young venture capitalist believes that cold emailing is a "super learnable" skill that anyone can master with the right approach. After initially capturing Benioff's attention, Stebbings maintained weekly communication, constantly testing different email versions to determine which messages felt most personal and compelling.
Mastering Personalization Techniques
Stebbings' personalization strategy went beyond surface-level details. He meticulously researched Benioff's preferences, mentioning everything from his favorite drink and holiday home to his preferred vacation spots and Salesforce's quarterly results. This deep level of personalization demonstrated genuine interest and effort.
"I would absolutely just relentlessly never give up," Stebbings noted about his approach. He also highlighted how modern AI tools can significantly enhance personalization efforts, making research more efficient and effective.
Stebbings explained how AI can be leveraged: "You can actually leverage them to say, 'Hey, I want to write an email to Marc Benioff, and I want to show that I've really done my work. What are five things that very few people know about Mark that would really impress him and add a layer of personalisation that not many people engage with? And they will tell you."
The Four-Step Cold Email Framework
When emailing Benioff, Stebbings followed a precise four-step framework that ultimately convinced the Salesforce CEO to appear on his show:
Subject Line Strategy: Avoid "needy" subject lines containing words like "attention." Instead, Stebbings used the straightforward "20VC podcast appearance" which proved effective.
Opening Approach: Rather than generic greetings, he used respectful openings like "Hi Marc, keeping things short out of respect for your time," followed by a clear statement of purpose: "I would love to have you on 20VC."
Social Proof Integration: Stebbings emphasizes the importance of explaining why the recipient should say yes and making them feel others have agreed before. He recommends including social proof such as subscriber counts, follower numbers, and previous high-profile guests.
Simple Ask with Personal Touch: He kept the request simple - "Super simple: we require 30 minutes of time and it's done on Riverside." The masterstroke came in the form of a personalized P.S.: "P.S. If you do it, I will send you a bottle of your favorite Macallan 75," knowing Benioff's preference for that particular whiskey.
Stebbings identifies common cold email mistakes as messages that are "too long" and "not nearly personalised enough," attributing these failures to insufficient effort rather than technique. His success with Benioff demonstrates that while cold emailing can help build valuable relationships and expand networks, most people fail to execute it effectively.
The story serves as both inspiration and practical guidance for entrepreneurs, podcasters, and professionals looking to connect with influential figures in their industries.
