One of the downsides of being an investor is that you spend a lot of time in meetings. What’s worse is that most of these meetings need to be scheduled. And yes, in 2012, we all still mostly schedule meetings via email. Consequently, a fair number of emails that I exchange with people are about scheduling.

Whenever I’ve mentioned this problem to others, their response is usually “Manu, you need an assistant.” Well, I’ve never had an assistant, and I manage my calendar pretty tightly. It’s possible that with time to reverse engineer the complicated heuristics I use to optimize my calendar, a human assistant may indeed be able to relieve me of this work. However, as a technologist, my preference is to find scalable solutions to problems. Having a human assistant may solve the problem for me, but does that mean the millions of people out there who have the same problem should all have human assistants?

Over the years I’ve developed a fairly streamlined way of managing my calendar. When I’m on my desktop, I usually have two browser windows open side by side — one with GMail and the other with Google Calendar. On my laptop, there are still two windows, but in different spaces (virtual desktops). When I’m processing scheduling-related emails, I bounce back and forth between these two windows. I need to check if I’m free on certain days and times, often propose multiple time slots for meetings, and once we agree on a date/time/location, add it to my calendar. I make it a point to add it to the calendar before I respond to the email as otherwise I run the risk of confirming a meeting but not having it on my calendar. All of this isn’t rocket science, but it takes up so much time to be switching between email and calendar over and over again.

Email, calendar, contacts, and todo lists are the picks and shovels of information workers. Think about it, so many of us spend more of our waking hours in our email than with our family and friends.  It’s a sobering thought.

It baffles me that companies like Microsoft, Google, Yahoo, and, Apple haven’t done a better job of building tools that address this space better. There is stagnation of innovation in productivity tools — because they all ended up in big companies – where things don’t get done unless it’s a billion dollar business (hat tip to @hunterwalk).

Outlook… uh, don’t even get me started on that. In all fairness the front-end that Outlook provides is actually better designed and better integrated than all the other offerings out there. The real problem with Outlook is the backend: Exchange.

When Google released GMail (2004) and Google Calendar (2006) there was hope for a better future. But GMail and Google Calendar have stagnated. In fact, GMail has regressed — it looks and performs worse than it did in the past, but that’s a whole other blog post. It’s shocking to me that with all the location data that Google has access to, Google Calendar has zero location integration. It doesn’t remember places I frequent. It doesn’t even look up places in a location database. And most of all GMail and Google Calendar don’t really know much about each other. I’m sure everyone in Google uses GMail and Google Calendar, so they’re eating their own dog food, but alas it’s still just that — dog food.

Fortunately, the kick-ass (and I don’t use that term lightly) team at Baydin decided to take a fresh look at the problem of productivity. They started with Boomerang for GMail which helps you to schedule when you send and receive emails. (Yes, you can schedule when you want to an email to come back to your inbox — it’s awesome. Try it!).

 Enter Boomerang Calendar. With Boomerang Calendar, GMail and Google Calendar users can streamline their workflow. Boomerang Calendar is kind of like the missing glue between GMail and Google Calendar.

Boomerang Calendar (BCal) detects potential meeting times in-line in your email. When you hover on the highlighted time, it shows you the agenda for that day. If you click, it  shows the calendar for the week. You can add the event to your calendar with a single click. It does a best effort attempt at guessing the right date and time of the event for you (BCal is currently in beta — its guesses will get a whole lot better yet!). If you’re offering times to someone you can do that on your calendar and it will create the email template for you. All right there in your inbox. Without ever having to switch windows over the the calendar. It’s all about intelligent use of contexts and defaults.

Scheduling a group event with Boomerang is somewhat mind-blowing. The email that is sent to the attendees updates as folks respond. Check out this video about Boomerang Calendar:So when you open the email, you can already see all the times proposed by others, right there in your email, without opening up yet another tab. And you get to respond to the suggested time in a form in your email. Yes, I have a biased view since it’s one of  my portfolio companies, but I was amazed at how well they thought through the information flow here.

Check out this video about Boomerang Calendar:

The value of Baydin’s tools is in the fewer clicks, the lower cognitive load from keeping things in short term memory, the reduced context switching and most of all in the minutes and hours of your life that you get back every day and every week by just being a tad more productive than you were before.

The beauty of what Baydin does comes from better observation and understanding of how people work. It’s not about building better email, or better calendaring. It’s about making people more productive. Helping them to get the mundane stuff that we all need to do out of the way faster so that we can work more (if we choose to!), or have more fun.

What hundreds of people working at the Internet giants have not been able to improve for years, is finally being improved by a small team of four in Mountain View. Congrats Team Baydin: Alex Moore (@awmoore), Aye Moah (@ayemoah), Mike Chin (@mikejchin),  and Jeremy Long (@jeremyaaronlong).

You can follow me on Twitter at @ManuKumar or @K9Ventures for just the K9 Ventures related tweets. K9 Ventures is also on Facebook and Google+.