Peter Thiel is one of the most successful founders and VCs of all time, and he has an unusual way of sending emails.
The insight comes from Keith Rabois, a veteran Silicon Valley executive who worked alongside Thiel at PayPal during its formative years. Rabois, who has gone on to become a prominent investor at Khosla Ventures and previously at Founders Fund, recently shared a compelling anecdote about one of Thiel’s most distinctive management practices—a seemingly simple email rule that revealed deeper principles about accountability and organizational efficiency.
According to Rabois, the lesson dates back to PayPal’s early days: “Peter taught me at PayPal a long time ago—maybe it was 2001. Peter was adamant that every email could only have one ‘to.’ You could have CCs. But every single email could be addressed to only one person.”
The reasoning behind this unconventional approach was elegantly simple. “Because then it’s very clear who is supposed to act on it. And there’s no confusion whatsoever,” Rabois explained. While he admits he doesn’t always follow this practice himself—”I would admit I don’t often do that, but it’s a really good discipline”—he recognizes its underlying brilliance.
The true genius of Thiel’s email philosophy lies in its implicit organizational design. As Rabois notes, “It effectively creates a DRI (Directly Responsible Individual) without the infrastructure of creating a DRI.” This approach cuts through one of the most persistent problems in corporate communication: the diffusion of responsibility that occurs when messages are sent to multiple recipients simultaneously.
This email discipline reflects broader management principles that have become increasingly relevant in today’s remote-first work environment. The concept of a Directly Responsible Individual—popularized by Apple and now widely adopted across Silicon Valley—ensures that every project or decision has a single point of accountability. Thiel’s email rule achieves the same outcome through a much simpler mechanism: the basic structure of digital communication itself.
The practice also anticipates problems that have become more acute with the rise of tools like Slack, Microsoft Teams, and asynchronous work cultures, where messages can easily get lost in channels with dozens of participants. Companies like GitLab and Buffer have implemented similar clarity-focused communication protocols, emphasizing explicit ownership and reducing the “someone else will handle it” mentality that can paralyze decision-making in distributed teams.