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

Kais Khimji has spent most of his professional career as a venture investor, including six years as a partner at the prominent VC firm Sequoia Capital.

But just like several other former Sequoia partners — including David Vélez, who founded the Brazilian digital bank Nubank — Khimji (pictured left) has always wanted to be a startup founder. On Thursday, he announced that he has revived an idea he began working on as a student at Harvard about 10 years ago, turning it into the AI 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 a chance to become a $1Bn+ revenue business, and Kais will make sure it gets there,” Pat Grady, Sequoia’s general partner and co-steward 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 seamlessly 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 the 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 nuance required to handle the entire scheduling process without human involvement.

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 social network for people’s time.

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

Khimji says that Blockit can finally solve this disconnection. When two users need to meet, their respective AI agents communicate directly to negotiate a time, bypassing the typical back-and-forth emails entirely.

Users can invoke the Blockit agent by copying it on an email or messaging it in Slack about a meeting. The bot then takes over the logistics, negotiating a mutually convenient time and location that fits the preferences of all participants.

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

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

By learning the preferences of its users, Blockit appears to be capitalizing on what venture firm Foundation Capital’s partners Jaya Gupta and Ashu Garg call “context graphs.” In a widely shared essay, the investors describe a multibillion-dollar opportunity for AI agents to capture the “why” behind every business decision by relying on the hidden logic that previously only existed in a person’s head.

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