Salesforce’s Marc Benioff Reluctant to Reply at First, VC Founder Says, Turning Cold Emails Into a Podcast Lesson

Salesforce CEO Marc Benioff reportedly did not respond to a venture capitalist’s outreach for more than a year, until the founder of the 20VC podcast said he finally received a reply. The anecdote is being used as a public example of how long-running, structured cold email campaigns can eventually break through with high-profile executives.

Harry Stebbings, the 20VC host and podcast producer, said he secured Benioff as a guest by sending cold emails consistently over time, reaching 53 weekly messages before he heard back, according to reporting carried by Yahoo Finance. The story frames the process as deliberate persistence rather than a one-off pitch.

In additional coverage of the same episode, Benzinga reported that Stebbings described spending about 30 minutes per week on what he called “hustle time.” He tied that routine to his view that business relationships are not strictly reserved for insiders, but instead can be cultivated through repeatable effort and sales-development discipline.

Benzinga also quoted Stebbings describing the mechanics behind that approach. He argued it is “absolutely nuts” that someone can find another person’s email online and still not cold email them. He further said that relationship-building can be learned, and referenced the need to be an effective sales development representative, or SDR, a role focused on identifying and qualifying potential customers or business contacts before deeper conversations occur.

The reports position the Benioff outreach as more than a personal win. Stebbings characterized the overall strategy as “super learnable,” presenting it as a skill set that can be trained. That emphasis matters in a market where many founders rely on referrals or warm intros, while others try to use direct outreach as a scalable acquisition and networking channel.

For Salesforce, the episode is not tied to a specific product launch or financial update in the reporting. Salesforce’s broader business context is its role in enterprise customer relationship management, the software category often described as helping companies organize sales, service, and marketing workflows. While the outreach story does not explain Benioff’s reasons for initially not replying, it shows how top executives still participate in the kinds of leadership media cycles that can shape how customers and investors perceive cloud software companies.

Even so, the disclosures remain limited. Neither Yahoo Finance nor Benzinga’s account, as reflected in the available reporting, provides details about what Stebbings actually wrote in the emails, how the conversation progressed once a response arrived, or whether Benioff’s reply referenced a specific reason for the timing. The reports also do not disclose whether Salesforce has an internal process for inbound media requests that might explain the delay.