The Relentless Pursuit: 29-Year-Old VC Founder Emails Marc Benioff Over 50 Times

Harry Stebbings, well-known for his audacious approach, isn't one to shy away from persistent email campaigns. Just ask Marc Benioff. As the head of the venture capital entity, 20VC, Stebbings was determined to have the Salesforce CEO join him on his podcast in 2023.

Stebbings detailed this journey on the November 12 episode of the "Biography" podcast with Wouter Teunissen. To have Benioff agree, he sent an impressive 53 unsolicited email invitations across a timespan of a year.

A Masterclass in Effective Cold Emails

Sharing his blueprint for success in email communication, Stebbings articulated the skill involved in crafting effective cold emails. He described it as a skill that anyone can learn with the right approach.

He emphasized starting with a straightforward subject line, avoiding any semblance of desperation, followed by a brief introduction devoid of clichéd pleasantries like 'I hope you're well.' Instead, he suggested getting straight to the point post-greeting.

Next, the email should establish credibility with pertinent background information. For example, Stebbings suggests mentioning media reach and previous guest appearances to reinforce the podcast's standing.

Adding a Personal Touch

The final touch involves personalization. Stebbings tailored some emails with promises of sharing a preferred whiskey or included specific mentions of Benioff's interests like a favorite vacation spot or recent Salesforce milestones.

In this modern age, he advocated using AI tools like Large Language Models to uncover unique insights into potential guests, demonstrating genuine interest.

Time is of the Essence

For those who have had chance interactions with potential contacts, Stebbings advised against delaying the follow-up email. Immediate outreach underscores attentiveness and captures the moment's immediacy.

The Power of Persistence

Among the noteworthy personalities who have featured on 20VC, icons like Scooter Braun, Bill Ackman, and Sam Altman stand out, echoing Stebbings' openness to forging connections.

Reflecting on his approach, Stebbings highlighted the importance of seizing opportunities that open more doors, underscoring the essence of never giving up.

Complementing this persistence, Benioff acknowledged the barrage of attempts in a 2023 social media post, lauding Stebbings' determination.

Benioff's words resonated with the mantra of resilience: "Persistence is everything." He remarked on the sheer volume of messages he received from Stebbings before finally agreeing to participate in the podcast.