Track #Olympics Time with Calendar #Hashtags

At Esper, we’re planning to watch the Rio Olympics – everything from Michael Phelps swimming to Mallory Pugh playing soccer to Usain Bolt running (and subsequently gloating). How much of our time these next two weeks will be spent watching Olympians and what sports?


We found a calendar online that has all the Rio events on one calendar and we could use Esper to tag each of these events. In the past, you would log into Esper to tag events on your calendar. Now, simply put a hashtag anywhere in your calendar event using Google, Outlook, Office365, or whatever calendar app you normally use.

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Log into Esper, and you’ll see that these hashtags create graphs to see what exactly you’re spending time on.

These hashtags also populate Esper’s weekly and daily email reports.Your weekly report shows you how your week went and how your week will turn out. Your daily agenda shows today’s agenda and the high-level tags that dominate your day.Screen Shot 2016-08-03 at 5.43.00 PM.png

So, now you can #Sales all those sales calls, #1on1 all your one-on-one meetings, and track all the #Olympics events to your heart’s content. We’re excited to see how you use Esper, and enjoy the 2016 Summer Olympics in Rio!

Make Time Great Again

A couple months ago, CEO Andrew Lee met up with a successful entrepreneur friend for dinner. The friend had just wrapped up a successful PR tour and was trying to make sure that he was doing everything he could to guard his most precious resource, his time.

He pulled out his phone at the dinner table and showed Andrew a “calendar audit.” This calendar audit showed all of his calendar events matched against his company’s strategic goals. The friend had exported all the data from his calendar, created a spreadsheet to assign categories to all his events, and calculated the total time he spent on each category. His friend remarked how useful it was, but that he was told this secret by another entrepreneur. His friend remarked, “Turns out the top CEOs, politicians, and leaders all do this in some form – heck, even Steve Ballmer does this.” However, he also observed how difficult it was because there was no readily available tool.

Weekly Percent Table

Andrew soon found others with this same problem. Sam Shank, CEO of Hotel Tonight, spent four weeks conducting his own labor intensive calendar audit. Keith Rabois, partner at Khosla Ventures, conducts periodic “calendar audits” for CEOs of companies he has invested in to make sure that their schedule allocation matches their goals. No one had a dedicated tool to help them solve this problem.

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Since then, the Esper team has been working tirelessly to bring this concept to life, following its mission of solving the problem of time mismanagement. With that in mind, we are excited to announce Esper – a quick and easy way to track how you are spending your time. Just as you track your expenses and maintain a budget, you can now do the same with your time. Let’s “make time great again.”  😉

The Future Assistant

Artificial intelligence is the new bogeyman of the 21st century. AI used to be the old spectres of chess champion Deep Blue or Jeopardy whiz Watson. Nowadays, the media seems to randomly choose an industry and finds every way it could be replaced by robots. Even Hollywood, in the latest Avengers movie, found a way to replace both antagonist and protagonist with robots. This noise has been most apparent in the world of assistants.

Whether arising from Siri, Google Now, or any number of touted assistant phone apps, the next day, the AI from Her will collate all our scintillating e-mails, publish them on the Kindle, and make us all best-selling authors! Evidence seems to suggest this future. Executive secretary and administrative assistant jobs have been whittled away from 1.4 million jobs in 2002 to a little over 713 thousand jobs in 2014. The spectres of AI are coming!

Where did those jobs go?

Contrary to popular belief, those jobs were disappearing for different reasons. First, executive assistant jobs were lost in the Great Recession, but many were replaced by a corresponding increase in the general assistant role. That loss can be attributed to firms cutting staff, not replacing executive support staff, and in many cases, increasing the burden on the remaining assistants. Despite that, the total number of general admins grew from 1.8 million in 2002 to 2.2 million in 2014. To be fair, there is still an overall job loss since the recession, but the assistant will not be a bygone profession.

Second, executives for a long time started making the move toward virtual assistants. I’m not talking about off-shoring, but rather, finding staff in more inexpensive locations (e.g. McKinsey has support staff in Florida) and providing greater time flexibility for their staff. Many administrative assistants can make a decent wage in areas where the EA role is in demand – Nevada, Colorado, and Florida to name a few.

Scheduling Requires Agency – Full AI Takes Away Agency

What’s more? Most of an assistant’s work consists of email and calendar scheduling. There hasn’t been a revolution in scheduling and time management since Microsoft Outlook. That revolution has not and probably will not be completely automated away.

I’m sure Larry Page would love to get artificial intelligence to manage your calendar, but from what we’ve seen at Esper, you still want a human being to be partially in control. We’ve all been in situations where a printer prints uncontrollably or been helpless when the doors to public transportation slam in your face. Much the same way, we get angry at technology when rules (even though we may have set those rules) take away our agency. No one gets angry at technology because of its function, except for when we don’t have any control over it.

“Trust, But Verify” Technology

One egg, please.

When human beings lose control, they choose not to use the technology. A good example of this was when they came out with bake mixes for housewives in the early 1950s. Just add water and heat, but those bake mixes NEVER sold. One enterprising designer changed it so that all you needed was to crack an egg, add water, and heat. Now the world of quick bake mixes have been ingrained in memory ever since. Human beings want control (or semblance of it) in order to truly trust technology.

We’ve had assistants for awhile and any executive/EA pair will tell you that the foundation is trust. Like the old adage – “trust but verify,” the key to future technology is to give AI trust, but to always have a human verifying the technology. In much the same way, the future of assistant technology will not be capital-letter AI, but what I’d say is lower-case AI. What the technology Linus Torvalds refers to as “targeted AI, rather than anything human-like at all. Language recognition, pattern recognition…” Combined with human verification/control, it’s unlikely going to ever truly replace the human touch of an assistant, just enhance it.

The Future Assistant is a Cyborg

The future assistant will be a combination of a human assistant and technology – think a cyborg suit, a piece of technology that automates the future of administrative tasks. Instead of talking head, think suggestion machine – giving you choices for your next calendar event, the next course of action based on an e-mail, or the next step it figures out based on your data. Luckily, you’ll have a trusty assistant (who may be supporting more people or providing deeper support) keeping a watchful eye.

Far from the doom and gloom of job loss, the role of the assistant will evolve becoming a time manager or a project manager that supervises AI and other human beings. We may even see a reversal of the current trend and see growth in human beings working in administrative services, creating more jobs than we’ve ever seen.
But hey, what do I know? Lots of smart people see Rosie the Robot to be the end of mankind. I just hope I become an AI-enabled best-selling author before that time rolls around.

1 – “Executive Secretaries and Administrative Assistants,” Occupational Employment and Wages, 2002;

2 – “Executive Secretaries and Administrative Assistants,” Occupational Employment and Wages, 2014,

3 – “43-6014 Secretaries and Administrative Assistants, Except Legal, Medical, and Executive,” Occupational Employment and Wages, May 2014

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Esper New Office Painting Party

What do Pac-man, a stick figure desperately needing the bathroom, a camel with a bow tie and top hat, and the San Francisco Giants all have in common? To the outside observer, this question might have no answer but for those who attended Esper’s new office painting party the answer is painted all over the walls. Thank you to all our lovely guests who helped make our office a beautiful work space, especially Julie Zhu. It was great seeing many familiar and new faces.

To watch the whole thing pan out please watch our time-lapse video.

We began painting at 4pm slowly making progress on the empty white walls. As our reinforcements arrived in the form of different guests (we even had some local high school students WHS) we were ready in full force to unleash our artsy side. Whatever came to mind found itself on the wall.

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The night drew to a close as many thanks and hugs were exchanged, we waited anxiously for the morning to begin phase 2: Operation Tape and Paint White. With our master of the beautiful arts aka you know who aka Julie Zhu in command, we overlaid different shapes and designs over the painted wall with painters tape. We then painted everything not covered in tape in white, waited for everything to dry then took of the protective painters tape.

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And of course, thank you to all the amazing guests! I hope everyone had fun. Stay posted for more events soon to happen at our new office.

Big thanks to Julie Zhu for arranging all this. The office would still be with white walls without your help.