It’s about time: Portland startup ReclaimAI helps users prioritize their work and personal calendars

The ReclaimAI team, from left to right: Ian White, principal software engineer, co-founder Henry Shapiro, and co-founder and CEO Patrick Lightbody. (ReclaimAI Photo)

Chances are you’ve asked yourself, likely more than once, the largely rhetorical question: “Where does the time go?”

Portland-based startup ReclaimAI wants to give you an answer.

Reclaim is building a product that helps people better manage their digital calendars by allowing them to rate their scheduled meetings and events by importance and by applying AI to figure out how their time is spent and if it’s being devoted to the things that matter most, professionally and personally.

“You have more demand for your time than you have ability to fill it,” said co-founder and CEO Patrick Lightbody.

The Reclaim tool helps individuals prioritize their schedles, identifying, for example, if someone is spending too little time on a high-importance issue and blocking out time to dedicate to it. It can also provide analysis to help managers understand how their employees’ time is being allocated, calculating how many hours are spent on tasks such as sales, in one-one-one meetings, meeting with certain people or interacting with customers.

“Computers are better at doing the complex math of finding the right times to work on the important stuff than people are,” Lightbody said.

When users create their ReclaimAI profile, they will be able to prioritize their activities. (ReclaimAI Image)

Reclaim launched in June 2019 and has already raised $1.5 million in angel and venture capital. The three-person team, which includes Lightbody, Henry Shapiro and Ian White, worked together as product leaders and engineers at Portland’s New Relic.

Lightbody has created and sold two companies in the software testing space, and was one of the original contributors to Selenium, a framework for testing web apps. Shapiro, Reclaim’s co-founder, has worked as a founding product manager at multiple startups in the Portland area. White is principal software engineer at the company and has been a developer for well over a decade. The trio’s university degrees span computer science, history and philosophy.

The Reclaim calendar tool is being tested in private beta mode, but the startup already released LifeWork Calendar, a free tool that lets people connect work and private calendars, without having to share personal information about appointments and other obligations outside of work. Their plan is to keep offering LifeWork for free, while eventually offering Reclaim’s main product on a subscription basis.

The team supports privacy and giving users control of their data, Lightbody said, and has made it easy for users to delete their information.

Competition in the calendar time-management realm include Clockwise, a San Francisco startup, and Calendly, which provides a scheduling tool. Lightbody predicts more businesses will be jumping into the area.

“This is going to be a growing space,” Lightbody said. “We’re in the world of intense distraction.”

We caught up with Lightbody for this Startup Spotlight, a regular GeekWire feature. Continue reading for his answers to our questionnaire.

What does your company do? Reclaim is an executive assistant for everyone. It automatically rebalances your schedule, blocks time for the things that matter most, and keeps you and your team on track with analytics and recommendations. It’s like inbox zero, but for your calendar.

Inspiration hit us when: We originally were very focused on the concept of “team health,” which had been a big focus for us at New Relic. We were fascinated with the idea of measuring and optimizing the inputs that led to highly productive and happy product teams. As we pulled on the thread, we spoke to hundreds of product people and started to notice a consistent pain point: the calendar.

People simply weren’t finding the time to do the important stuff during the week, weren’t good at defending their time, and lacked the tools and discipline to keep their workweeks in check. This seemed to be the ultimate arbiter in a team’s likelihood to succeed, and even in an organization’s ability to stay scrappy and agile. Instead of building more dev tools or monitoring platforms, we realized the best way to help make this problem go away was to attack the calendar directly.

VC, Angel or Bootstrap: We’re fortunate to have received $500,000 in angel funding from a variety of founders, product leaders and independent investors from across the globe, and an additional $1 million led by Geoff Harris at Flying Fish in Seattle.

We partnered with these folks because we realized throughout the fundraising process that raising capital isn’t just about getting “dumb money.” Founding a company is an extremely lonely experience at times, and your investors are the people who cheer you on, challenge you, and keep you going.

We wanted partners who truly believed in our vision, who believed in us as a founding team, and who wouldn’t mince words when the occasion called for it — and we were lucky to find it.

Our ‘secret sauce’ is: Calendars are deceptively complex. We’ve had to build a lot of logic into Reclaim to ensure we’re really providing a magical experience for users, for whom the calendar is a really sensitive space. We’ve built intelligence around detecting what kinds of meetings are on your calendar automatically, heuristics for automatically rebalancing and defending your calendar as your week fills up, and for generating recommendations based on your behavior.

ReclaimAI released LifeWork Calendar, a free tool for coordinating calendars while keeping personal information private. (ReclaimAI Image)

The smartest move we’ve made so far: Launching LifeWork Calendar, a simple utility for automatically defending time on your work calendar for personal events. We spent two months getting it built and getting it out on Product Hunt, and it’s led to a huge pile of signups and given us a massive user base to upsell to Reclaim as we move into public beta.

The biggest mistake we’ve made so far: Trying to raise too much capital before we built a product. Building is the best way to truly understand what you’re actually doing, and to create confidence in your vision. We decided to shift and raise less and instead focus on product, which has been really great for honing our pitch and our strategy for what comes next.

Which leading entrepreneur or executive would you most want working in your corner? Probably Scott Farquhar of Atlassian, an Australia-based company that makes tools for software development and project management. Patrick actually worked with him many years ago, building the original JIRA workflow engine before Atlassian was a big deal. Scott is a brilliant entrepreneur who has bucked a ton of the conventional wisdom around building companies, stays humble and healthily paranoid, and who valued product-led growth before it was cool to do so.

ReclaimAI’s analytical tool calculates the time spent on different tasks. (ReclaimAI Image)

Our favorite team-building activity is: Eating Twinkies

The biggest thing we look for when hiring is: Scrappiness, humor, flexibility and common sense. We think the resumé doesn’t really tell the story of how someone approaches tough problems, and we value growth mindsets above all else.

What’s the one piece of advice you’d give to other entrepreneurs just starting out: When you’ve got a big vision, break it down and launch one small part of it first. You’ll learn a lot, build strong foundations, and start to understand your users more than if you go dark for months and then launch the big thing all at once. It’s also a great way to get your confidence up.

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