Former Sequoia partner’s new startup uses AI to negotiate your calendar for you

Qais Khimji has spent most of his career as a venture capitalist, including six years as a partner at prominent venture capital firm Sequoia Capital.

But just like many of Sequoia’s other former partners — including David Velez, who founded Brazilian digital bank Nubank — Khimji (pictured left) always wanted to be a startup founder. He announced Thursday that he has revived an idea he started working on when he was a student at Harvard about 10 years ago, turning it into AI-based calendar scheduling company Blockit. In a major vote of confidence, Khimji’s former employer, Sequoia, led the company’s $5 million seed round.

“Blockit has an opportunity to become a $1 billion-plus revenue company, and Kais will make sure it gets there,” Pat Grady, Sequoia’s general partner and co-supervisor who led the investment, wrote in a blog post.

While many startups have tried to automate scheduling in the past, Khimji believes that thanks to advances in LLMs, Blockit’s AI agents can handle scheduling more smoothly and efficiently than many of its predecessors, including now-defunct startups Clara Labs and x.ai. (Yes, that domain name ended up with Elon Musk’s AI company.)

Unlike current category leader Calendly, which was last valued at $3 billion and relies on users sharing links to find availability, Blockit is betting that its AI agents can master the nuances required to handle the entire scheduling process without human intervention.

With Blockit, Khimji and co-founder John Hahn — who previously worked on calendar products, including Timeful, Google Calendar, and Clockwise — are building what is essentially an AI-powered social network for people’s time.

“I’ve always felt weird. I have a database of time — my calendar. You have a database of time — your calendar, and our databases can’t talk to each other,” Khimji told TechCrunch.

Blockit can finally resolve this disconnect, Khimji says. When two users need to meet, their AI agents communicate directly to negotiate time, bypassing typical emails altogether.

Users can summon a Blockit agent by copying it onto an email or sending it in Slack about a meeting. The robot then takes care of the logistics, negotiating a mutually convenient time and location that suits the preferences of all participants.

Khimji said Blockit can seamlessly work as a human executive assistant. Users simply need to provide the system with specific instructions about their preferences, such as which meetings are non-negotiable and which are “changeable” based on daily needs. “Sometimes my calendar is crazy, so I need to skip lunch, and the agent needs to know it’s okay to skip lunch,” he said.

The system can also be trained to prioritize meetings based on the tone of the email. For example, a user might instruct an agent that a meeting request signed with a formal “Best regards” should take precedence over an informal interaction ending with “Cheers.”

By learning about its users’ preferences, Blockit appears to benefit from what Jaya Gupta and Ashu Garg, partners at investment firm Foundation Capital, call “contextual graphs.” In a widely shared article, investors describe a multi-billion-dollar opportunity for AI agents to learn the “why” behind every business decision by relying on hidden logic that previously existed only in a person’s head.

Blockit is already used by more than 200 companies, including AI startup Together.ai, newly acquired fintech Brex, robotics startup Rogo, as well as venture firms a16z, Accel, and Index. The app is available for free for 30 days. After that, the cost is $1,000 per year for individual users and $5,000 per year for a team license with support for multiple users, Khimji said.