Clockwise Co-Founders Gary Lerhaupt, Matt Martin, and Mike Grinolds

Time for Clockwise

John Lilly
Greylock Perspectives
3 min readJun 17, 2019

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I never seem to have enough time. Nobody I know does, really.

We’re are living in a golden age of productivity tools: Slack and Zoom and Figma and Dropbox and Quip and Crew and many more. The combined macro trends of mobile, cloud, modern design, and machine learning have paid huge dividends in our ability to create, collaborate, and build things quickly.

But one of the ironies of the age is that as amazing as these tools are, it’s gotten increasingly tough to find the time to sit down and use them productively. Between meetings, notifications, alerts and on and on, we’ve lost the ability to control our calendars, to have time to think and to work in focused ways.

Which is why I’m really happy to be able (finally!) to talk about our investment in Clockwise! I met the Clockwise founders Matt Martin, Mike Grinolds, and Gary Lerhaupt early in 2018 and was immediately taken with them, their passion for helping us get control of our time, and their new approach to doing it — not by creating a new calendar app, but by using machine learning to make the calendars we already have work better. The approach would take a deep mix of product, UX, machine learning and systems thinking to make work, and that’s precisely what Matt, Mike & Gary demonstrated. This was a team I wanted to be in business with, building a technology that needed to exist in the world.

Clockwise makes a product and supporting technology that actually gives us time back. They’ve been heads down over the past couple of years building their first product — connect it to your own calendar and it figures out how to optimize your days to give you back meaningful chunks of time in whole blocks. For old school nerds (🙋‍♂️) , it will remind you of a disk defragmenter:

You can see from the animation above that Clockwise can figure out which meetings are movable (like weekly 1–1s) and which aren’t (like staff meetings), and can rework your weekly calendar to give you back time to think & time to work. The yellow time is fragmented time; the turquoise is time you can really use to do productive, concentrated work. The before & after difference is huge.

But the real magic happens when you connect it up as an organization. Clockwise can optimize across the whole organization to maximize what they call Focus Time — uninterrupted blocks of time. It’s amazing to see the results — even in the early beta it’s given literally thousands of hours of Focus Time back to folks at some of the world’s most productive companies like Lyft, Asana, Intercom and others.

And maybe it goes without saying, but this is a very tricky problem. It’s one thing to optimize a single individual’s calendar, but when you start to look at options, constraints and optimizations across multiple calendars and organizations, it gets hard fast. NP-hard, in fact, to use a computer science term. Happily, it happens to be the kind of problem that’s well suited for machines and machine learning to tackle, which is part of the secret sauce the team has been building for a couple of years now.

This Clockwise team is a team that nerds out on the details of productivity and Deep Work (to use Cal Newport’s framing). They’re obsessed with thinking about how to get all of us back the time we need to do real work. And they’ve already tackled a similar challenge at RelateIQ (focused on contacts rather than calendar), where they were before starting Clockwise. The team is full of passion, and with backgrounds in UX, machine learning and more — it’s an incredible team that’s laser focused on getting this right.

Getting time back to think and to create — that’s a job worth doing, and I’m really excited to be on the journey with Matt, Mike & Gary, as well as Steve Loughlin from Accel, their former leader at RelateIQ.

Go take a look and see if you can get a little more control over your own time.

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