Venture capitalist and podcaster Harry Stebbings secured Salesforce Inc. (NYSE:CRM) CEO Marc Benioff as a 20VC podcast guest by sending him 53 weekly cold emails, turning relentless outreach into a case study in how persistence can open doors to the world’s most powerful executives.
Stebbings Turns Cold Emails Into Access
The 29-year-old founder of 20VC accomplished the goal in 2023. Since then, he has said he spends 30 minutes a week on "hustle time" and has booked many guests through 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" in November 2025. "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."
An SDR, or sales development representative, is someone who finds and qualifies potential customers. Stebbings used the term to argue that relationship-building is a learnable skill, not magic reserved for insiders.
Personalized Outreach Finally Wins Benioff Over
Stebbings, who says relationships drive success, called cold emailing "super learnable." To win over Benioff, he emailed weekly and tested different forms of personalization. He referenced Benioff’s favorite drink, holiday home, favorite vacation spot, Salesforce’s quarterly results and other details.
"I would absolutely just relentlessly never give up," Stebbings said.
He said artificial intelligence tools now make that research 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.
Stebbings said people fail because their emails are "too long," "not nearly personalized enough," and show they did not do the work.
Cold Email Formula Stays Surprisingly Simple
His Benioff playbook had four parts, which included a clear subject line, a direct opening, social proof, and personalization. He avoided needy subject lines and used "20VC podcast appearance." He skipped the standard "I hope you’re well," joking, "Who’s like, ‘I hope you’re unwell.’" Instead, he opened with, "Hi Marc, keeping things short out of respect for your time," then stated, "I would love to have you on 20VC."
He also used proof, citing audience size and past guests, and made the ask easy. "Super simple: we require 30 minutes of time and it’s done on Riverside," he said.
The final touch was a tailored P.S. bribe. "P.S. If you do it, I will send you a bottle of your favorite Macallan 75," he said, referring to Benioff’s favorite whiskey.
The episode also lands as Benioff remains central to the AI business conversation.
Stebbings is not alone. Sara Blakely cold-called department stores before Spanx broke through, while a founder recently landed Mark Cuban as an investor through email outreach. The lesson is old, boring, and still annoyingly effective, which is to do the homework, ask, and keep going.
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