Kais Khimji has dedicated most of his career to venture investing, spending six years as a partner at the well-known VC firm Sequoia Capital. However, like several other former Sequoia partners—including David Vélez, who founded the Brazilian digital bank Nubank—Khimji has always aspired to be a startup founder. Recently, he announced he’s bringing back an idea he developed as a Harvard student nearly a decade ago, launching the AI calendar-scheduling company Blockit. In a significant show of support, his former employer Sequoia led Blockit’s $5 million seed funding round.
“Blockit has a chance to become a $1 billion+ revenue business, and Kais will make sure it gets there,” said Pat Grady, a general partner at Sequoia and the investment round’s leader, in a blog post.
While numerous startups have attempted to automate scheduling in the past, Khimji believes that with advancements in large language models (LLMs), Blockit’s AI agents can manage scheduling more smoothly and effectively than many previous efforts, such as the now-defunct Clara Labs and x.ai (the domain ultimately went to Elon Musk’s AI company).
In contrast to the leading scheduling service Calendly—valued at $3 billion, which relies on users sharing links to check availability—Blockit aims for its AI agents to master the nuances required to handle the entire scheduling process without human intervention.
Khimji, along with co-founder John Hahn—who has experience with calendar products such as Timeful, Google Calendar, and Clockwise—are creating what they describe as an AI social network for managing time.
“It always felt very odd. I have a time database—my calendar. You have a time database—your calendar, and ours just can’t communicate,” Khimji explained to TechCrunch.
Khimji believes Blockit can finally resolve this disconnect. When two users need to meet, their respective AI agents will communicate directly to negotiate a time, eliminating the usual back-and-forth emails.
Users can activate the Blockit agent by copying it on an email or messaging it in Slack regarding a meeting. The AI then handles the logistics, figuring out a time and location that works for all parties involved.
Khimji noted that Blockit can function as seamlessly as a human executive assistant. Users just need to give the system specific guidance about their preferences, like which meetings are essential and which can be flexible based on the day’s demands. “Sometimes my calendar is hectic, so I might need to skip lunch, and the agent needs to understand that it’s acceptable,” he said.
The system can also learn to prioritize meetings based on the tone of an email. For example, a user might instruct the agent that a request signed off with a formal “Best regards” should take precedence over something more casual that ends with “Cheers.”
By personalizing user experiences, Blockit taps into what Jaya Gupta and Ashu Garg of venture firm Foundation Capital refer to as “context graphs.” In a widely circulated essay, they outlined the multibillion-dollar potential for AI agents to uncover the rationale behind business decisions by leveraging hidden logic that previously resided only in a person’s mind.
Blockit is already serving over 200 companies, including AI startup Together.ai, recently acquired fintech firm Brex, and robotics company Rogo, along with venture firms like a16z, Accel, and Index. The app is available for free for the first 30 days, after which it costs $1,000 per year for individual users and $5,000 annually for a team license that accommodates multiple users, according to Khimji.
