A 29-year-old VC founder cold-emailed Marc Benioff 53 times to get his attention. It worked.

• Investor Harry Stebbings secured Marc Benioff as a podcast guest after 53 cold emails.

• Cold emailing is a skill that’s “super learnable” and one he still uses, Stebbings said.

• Stebbings shared his cold email strategy, emphasizing clarity, credibility, and personalization.

Harry Stebbings isn’t shy about sliding into inboxes. And he’s persistent — just ask Marc Benioff.

Stebbings, the 29-year-old founder of venture capital firm 20VC, interviewed the Salesforce CEO in 2023 for his podcast. He wasn’t the easiest guest to score, but Stebbings was committed to getting him on the show.

Stebbings spoke about his strategy for getting Benioff to say yes — which involved sending 53 cold emails over a year — during a November 12 episode of the “Biography” podcast with Wouter Teunissen. It’s a skill that Stebbings has honed over the years of hitting up potential guests.

Stebbings shared his winning formula for landing Benioff.

“Do you know how few people cold email well?” Stebbing asked the host. “It’s super learnable.”

It starts with a clear subject line that doesn’t sound needy, he said, and an introduction that skips the filler phrases like, “‘I hope you’re well.'” You should state your objective almost right away after your salutations.

Then, he said, you’ll want to give your claim some validity and explain why the receiver should say yes, using some brief background information.

“‘We have X amount of subscribers, followers, you name it, and I have had guests like X, Y, and Z,'” Stebbings said.

After letting them know how much time is required of them, Stebbings wraps it up with a personal touch. For his emails to Benioff, he tested different options. For some, he’d offer to gift him his favorite whiskey. For others, he’d mention his holiday home, favorite vacation destination, or Salesforce’s quarterly results.

In the era of AI, Stebbings said you can use LLMs to quickly find out little-known facts about your intended recipient that could show you’ve done your homework.

If you’ve already met them at a dinner or a chance encounter, Stebbings said, don’t make the mistake of waiting to email them the next day.

“It’s so important because it just shows them that you’re on it, and it’s fresh in their mind,” he said.

Some of 20VC’s other notable guests include Scooter Braun, Bill Ackman, and Sam Altman. Ultimately, it’s about putting yourself out there for connections and new opportunities.

“I just always think, always take the option which has another door opening,” he said.

It’s also clear that Benioff was aware of the sheer number of attempts.

In a 2023 post on X after the release of their interview together, the Salesforce CEO highlighted the value of not giving up.

“Harry must have texted and emailed me 100 times before I agreed to be on his podcast,” Benioff said. “Persistence pays Harry.”

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