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.”

How this millennial founder got the attention of Marc Benioff

Stebbings, who believes relationships are a key driver to success, says cold emailing is a “super learnable” skill people should learn to do well. 

When he gained Benioff’s attention, he emailed him weekly and A/B tested which emails would be the best form of personalization. For example, he’d email and reference his favorite drink, his holiday home, his favorite holiday destination, Salesforce’s quarterly results, and more.  

“I would absolutely just relentlessly never give up,” he said.

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. 

To be the most efficient cold emailer, Stebbings said people usually go wrong when the emails are “too long,” “not nearly personalized enough,” and they just don’t do the work. 

Cold emailing has been an effective tool for creating new relationships or expanding a network. The issue Stebbings has though, is that few people seem to be able to do it right. When emailing Benioff, here are four steps he took to win him over for his podcast. 

A clear subject line 

Stebbings said it’s best not to do a “needy” subject line with grabby words like “attention”. In his case, “20VC podcast appearance” was sufficient enough. 

Skip the “I hope you’re well” 

“Who’s like, ‘I hope you’re unwell'” Stebbings joked on the podcast. Instead, “Hi Marc, keeping things short out of respect for your time” was better in his case. In addition, state your objective for the email. “I would love to have you on 20VC” was how he went about it. 

Social validity

Stebbings says the key to a cold email is to clearly explain why the person should take you up on your offer, and make them feel like they are not the first. He suggests laying out social proof (“we have X amount of subscribers, followers… and have had guests like X, Y, and Z”)

“Super simple: we require 30 minutes of time and it’s done on Riverside,” he said.

Personalization 

In Stebbings case, the personalization was a P.S. bribe tailored to Benioff.

 “P.S. If you do it, I will send you a bottle of your favorite Macallan 75,” he said—knowing the whiskey was Benioff’s favorite.