"Harry Stebbings has a simple piece of advice for getting the attention of the world's top leaders: learn to be "a stalker" when it comes to cold emailing. He would know best. The 29-year-old VC founder emailed Salesforce CEO Marc Benioff 53 times to appear on his podcast, before accomplishing his goal in 2023. And since then, he's admitted he spends 30 minutes a week toward "hustle time" and has roped most of his guests in with cold emails."
""It is absolutely nuts to me that you can find anyone's email on the internet and just cold email them," Stebbings said on an episode of The Biography Podcast. "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 stalker.""
""Today, Stebbings says AI tools make that personalization even easier. "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 personalization that not many people engage with? And they will tell you," he added."
Cold emailing can reach top leaders when executed with persistence, concise messaging, and deep personalization. A founder secured a CEO's podcast appearance after sending 53 weekly emails and relentlessly testing personalization elements like favorite drink, holiday home, destination, and company results. Short, regular "hustle time" supports consistent outreach. AI tools can speed research and surface little-known details to add credibility. Common failures include messages that are too long, lack of personalization, and insufficient research. Focused follow-up, A/B testing of approaches, and brief tailored notes improve response rates.
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