Harry Stebbings, founder of venture capital firm 20VC, send Salesforce CEO Marc Benioff 53 emails before the business leader finally agreed to appear on his podcast, 20VC. Stebbings discussed his strategy November 12 on Wouter Teunissen’s The Biography Podcast, and shared some tips for making your communications stand out.
To Stebbings, nothing matters more than relationships. That’s why, in a world where you can find anyone’s email online, he thinks “everyone should learn to be a really efficient SDR, but essentially a stalker.”
The 29-year-old puts 30 minutes a week toward “hustle time,” when he thinks about who he wants on his podcast and how to make it happen. To this day, he said he’s roped most of his guests in with cold emails.
Stebbings told Teunissen that while cold emailing is “super learnable,” it’s ridiculous that “so few people can do that well.” So he offered some clear cut advice.
How to Write a Cold Email
The subject line should be “f—-ing clear” and to the point, as should the body of the email, Stebbings said. Skip the filler phrases.
“I hope you’re well? Never,” he said. “Who says I hope you’re unwell? No one.”
Instead, Stebbings advises to immediately state your objective. Tell the person what you’re asking and how much of their time you need.
Provide some background information to steer them towards agreeing to your ask. In Stebbings’ case, he lists the subscriber count and a few guests he’s had on the podcast to give his request some validity.
Next comes a “P.S.” followed by a personal touch. Stebbings tried a few different routes, like offering Marc Benioff his favorite whiskey, or mentioning his holiday home and favorite vacation spot.
“Wow,” Stebbings said, imitating a recipient of his emails. “Super clear, really well outlined, and holy s–t he’s done his work on my favorite whiskey. Well done.”
Don’t Delay the Follow Up
If you’re lucky enough to connect in person, don’t wait until the day after to reach out. Stebbings said he always emails in the Uber home from the event or dinner.
“It’s so important because it just shows them that you’re on it, and it’s fresh in their mind,” he said. “Not hard at all. Honestly, sometimes it can be a copy and paste and you just put the first line as personalized. Makes such a difference.”
His slew of emails paid off when Benioff came on the podcast in a September 2023 episode. Benioff shouted out his unrelenting efforts in a post on X.
“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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Ava Levinson
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