Kais Khimji has spent most of his professional career as a venture investor, including six years as a partner at the renowned VC firm Sequoia Capital.
But like several other former Sequoia partners—including David Velez, who founded Brazilian digital bank Nubank—Khimji (pictured left) always wanted to be a startup founder. On Thursday, he announced that he has revived an idea he started 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 post a blog.
While many startups have tried to automate scheduling in the past, Khimji believes that thanks to the advances in LLM, Blockit’s AI agent can handle scheduling more smoothly and efficiently than many before it, including the now-defunct startup Clara Labs and x.ai. (Yes, that domain name ends up with Elon Musk’s AI company.)
Unlike the current category leader Calendly, which is the last valued at $3 billion and relying on users sharing links to find availability, Blockit is betting that AI agents can master the nuances needed 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 strange. I have my time-calendar database. You have your time-calendar database, and our databases just can’t talk to each other,” Khimji told TechCrunch.
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Khimji says that Blockit is finally able to bridge this disconnect. When two users need to meet, their respective AI agents communicate directly to negotiate a time, bypassing the typical email back and forth.
Users can request a Blockit agent by copying them in an email or messaging them in Slack about a meeting. The bot then takes over the logistics, negotiating a time and location that suits the preferences of all participants.
Khimji says Blockit can work seamlessly as a human executive assistant. Users only need to give specific instructions to the system about their preferences, such as non-negotiable and “movable” meetings based on their daily needs. “Sometimes my calendar is crazy, so I have to skip lunch, and the agent has to know that I can’t have lunch,” he said.
The system may be trained to prioritize meetings based on email tone. For example, users can instruct agents that meeting requests signed off with a formal “Greetings” should take precedence over casual interactions ending with “Cheers.”
By learning about user preferences, Blockit looks to capitalize on what Foundation Capital venture partners Jaya Gupta and Ashu Garg call “context graphs.” In a shared essayinvestors describe a multi-billion dollar opportunity for AI agents to capture the “why” behind every business decision by relying on hidden logic that previously only existed in people’s heads.
Blockit is already used by more than 200 companies, including AI startup Together.ai 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 per year for individual users and $5,000 per year for a team license with support for multiple users, Khimji said.