Alex with Gingerbread Christmas Tree Cookie

If you kept a close eye on our Twitter accounts during the holidays, you may have wondered how we were managing to respond to customer emails while we should have been opening presents. Of course, we were using Boomerang to write the messages before, but have them go out later.

Since we know our users are a creative bunch, we wanted to know how they used Boomerang during the holidays to make their hectic lives easier. So we held a contest to give away some gorgeous Boomerang T-shirts.  We got many tweets with varying degrees of cleverness, usefulness and hilarity. Thank you to everyone who tweeted a suggestion, and here are the 5 winners, picked by our team.

Winners of The Boomerang for Holidays T-shirt Contest

@baydin I am setting reminders for next year’s holidays based on this year’s lessons! #boomerang4holidays

— mblogler (@mblogler) December 23, 2011

Boomerang helped me this holiday season by automagically emailing invoices while i was on vacation #boomerang4holidays boomeranggmail.com
— Brian Lyman (@valestudios) January 5, 2012

Watched all my important emails from the holidays greet me throughout first day at work #boomerang4holiday
— Raoul N. (@rananava) January 5, 2012

Wanna know how productive my holidays were? Sent emails early morning w/o waking up before noon! boomeranggmail.com #boomerang4holidays
— Arturo Cárdenas (@arturocm) January 5, 2012

I used Boomerang to email Santa @ midnight Xmas eve, telling him coordinates to my chimney w/ brownies waiting on roof! #boomerang4holiday
— HERBIVORE PUBLICITY (@Herbivorepr) January 5, 2012

Congratulations, winners! Please email us at boomerang+tshirt at baydin.com with your choice of T-shirt size and color, along with a mailing address. For colors, we have bright blue and dark grey. Sizes range from XS to XL (for size reference, these are American Apparel t-shirts).

Since there are more than 5 that we really liked, we decided to award 3 extra runner-up prizes as well. Each of them will be getting a spin of our Wheel o’ Prizes.

Boomerang for Holidays Runner-up prize winners

Boomerang sent my pre-written email to remind Santa about my Christmas presents at 3am on 25th! #boomerang4holidays boomeranggmail.com

— lcdvirgo (@lcdvirgo) January 5, 2012

Boomerang helped me really enjoy my vacay because I knew EXACTLY who I needed to contact once I was back at the office! #boomerang4holidays

— Stephania Andrade (@OstephaniaO) January 5, 2012

Hey @baydin check out my post about boomerang for SEO’s bit.ly/w8daX5 Please give me a t-shirt IM COLD! #boomerang4holidays

— Nico Miceli (@NicoMiceli) January 5, 2012

If you are a runner-up prize winner, please email us at boomerang at baydin.com  to claim your link to spin the Wheel o’ Prizes.

This was a lot of fun and we really appreciate everyone who participated!

We think that’s awesome and we made the following video in tribute to all of the Boomerang’ing lovebirds out there:

We hope that Joe and Sarah live happily ever after—and continue to use Boomerang, of course.  As for Roger Jones and the rest of you, we suggest clicking here and learning from Joe’s success.

When a TV show finds success; money, fame, and inertia make it so that as long as networks are willing to renew the contracts, producers are willing to go along. You can’t blame them for not saying no. They don’t want to disband the crew, they have sentimental attachments to the characters, and it’s really hard to say ‘No’ to a boatload of cash. So artistic legend be damned, they will keep making new shows well beyond the point when the story runs out of momentum.  While Happy Days is the iconic version of this, you can look at many of the currently running series to see this pattern – How I Met Your Mother, Desperate Housewives, The Office, and plenty more. And even HBO, where artistic license often trumps popular opinion, sometimes lets series go overboard with sequels. Sex and The City ended at the right place after 6 seasons. But now there are movies. The first movie wasn’t not that bad but please stop making them! When they got to the second movie, it was so bad that I fell asleep.

You must be wondering ‘what about the shows that ended too early instead of too late?’ The truth is there’s no such TV shows that ended too early if they are ‘successful’. They got canceled because the network didn’t consider them successful enough. Audiences’ preference or the fact that you or I think it’s a great show doesn’t translate to millions of eyeballs.

Does the same phenomenon happen with software?

The day after we talked about letting a TV show end, I was working on designing a few new features for Boomerang for Gmail. As the product designer and manager, I spend a lot of time prioritizing which feature requests we will build and which we won’t. Then I saw a tweet from someone evaluating the product. He drew the conclusion that we have added too many features so that we could justify the paid subscriptions. Of course, I got mad. How dare he call MY PRODUCT feature laden?!

Does he not realize this product started out as 2 buttons inside Gmail? It literally was 2 buttons integrated into Gmail, with nothing else – not even a way to see, cancel or manage the messages you scheduled. Every new feature you now see in the product, including the new features I was designing at that moment, have been requested by many, many users, over and over again. All of us are heavy users of our own product, but every step of the way we’ve made sure we’re building the product for our customers, not just for ourselves.

As I was fuming, I started to see how the same problem that bothered me about TV shows could manifest itself in software. The guy on Twitter wasn’t there when we coded up our management page the first weekend, when we realized it was a hole that we must fill or our customers would be mad. He didn’t see the hundreds of emails requesting response tracking. He’s the guy who’s starting to watch How I Met Your Mother or The Office for the first time this season. He doesn’t know how it got there, or  why each feature was added, but he doesn’t care. The product, like new seasons of a TV show, has to be able to stand up the way it is now. It doesn’t matter that each individual step made sense at the time. The product’s history is our problem, not his.

When Facebook came out in 2004, back when I was in college, all “The Facebook” included was a personal profile where you can upload a single photo and ability for users to add each other as Friends. That’s it. No Wall, no multiple photos, and not even private messaging. Aside from the ubiquitous shade of blue, it’s hard to even tell that the modern version of Facebook evolved from the original.

But it was successful. And as it continued to grow, the team decided to add more features, like the Wall and the News Feed. Likewise, people kept asking for new things: the ability to chat, ability to add videos to your Wall, and dozens of other requests.

These features have dramatically changed Facebook’s experience from what it was in 2004. But the numbers of their user growth (700 Million users as of 2011) show that the new changes have worked. Facebook, as it is today, adds value to new users who have no idea about its history and how it evolved. Maybe Facebook hasn’t reached the point where the product story has been fully told. But as they add more and more features, reacting to user requests, and more recently, responding to the competition from Google Plus and Twitter, that day may be quite near.

Microsoft Office spent the last two release cycles without adding very many new features at all. Instead, the development team’s focus was on exposing the features that were already there, since most of them were only being used by less than 5% of the total user base. They’re in a tough position – even a feature that’s used by only 1% of Office users is still used by millions and millions of people. The result is a product that does so many things that it took over five years of development for Microsoft to figure out a way to combine all of those features in a coherent way.

So how do you know when your product has told its whole story, and it’s time to work on something else?

If your product isn’t successful, it’s easy. Like a network show that nobody watches, the product is almost certain to get canceled early. You won’t have any users, and you won’t have anyone urgently demanding for features they must have. You won’t have any obligations to fulfill these demands either.

If your product is successful, it’s much harder. Feature requests will continue to roll in forever. If you implement them all, your product will jump the shark. I don’t believe we are there for Boomerang quite yet. I believe it will be important for us to know when the product will be complete in advance, and to have the strength to stick to the plan. After all, the most important part of a great story is a great ending.

Thanks to Alex Moore for his help with editing this post.

But earlier this month, Sam Grobart of The New York Times laid out a coping strategy that offers a fresh perspective on email management.  The best part: it’s easy to follow.

For those practicing David Allen‘s Getting Things Done (GTD), Grobart’s system might make you anxious just reading about it.  But for those with swollen inboxes and no system yet in place to deal with it, this just might be the answer you’ve been waiting for.

The LTG Method

Grobart calls his system Letting Things Go (LTG) and presents a more laid back approach to email management.  In his words:

…the problem with a lot of organizational systems is that they replace one anxiety (“My stuff’s not organized”) with another (“My stuff’s not organized according to this specific system”).

To avoid this secondary anxiety, Grobart suggests that we should actually avoid the organization step altogether—or at least automate it.  LTG instead relies on basic search techniques and a few new tools to automate the rest.  He breaks the system down into the following 5 steps:

Stop organizing, start searching – Today’s email clients, Gmail in particular, offer robust search capabilities that essentially eliminate the need for other organization.  That’s right—labeling or filing is largely a waste of time.  Next time you need a message, try searching for it organically rather than browsing within a folder.  If anything, searching is quicker.

Be ruthless about blocking – To reduce the amount of email you receive in the first place, consider blocking addresses that send inappropriate messages.  Don’t bother unsubscribing, that takes too long.  And don’t be hesitant, block ruthlessly.

Build a digital nag – There are also tools available to make sure that nothing falls through the cracks, even without folders.  For Gmail users, Boomerang for Gmail is the clear winner.  With Boomerang, you can select a message to be archived for now and automatically returned to the top of your inbox at the perfect time.  So instead of letting messages get buried in your inbox, use Boomerang to get them out of your inbox for now and bring them back at appropriate times.

Use your inbox as an address book – There’s really no point in maintaining an external address book these days.  If you archive your messages, all of your contacts are accessible by search.  But if you insist on keeping an address book, use tools like Xobni to automatically update it.

Make your peace – No system is perfect, including this one.  The pure volume of email we receive on a daily basis makes a perfect system pretty much impossible—we simply don’t have the time that a perfect system requires.  There is too much email, and there always will be.

I personally have always followed the GTD method fairly closely, with a few caveats of my own.  Over the years the labeling and filing has become habitual, but it definitely takes up time and I rarely actually use them to locate a particular message.  I think LTG is definitely worth a shot.  I’m going to give it a try for a few weeks, but it will take some serious discipline to break the habit.

Well, readers, what do you think?  Is a loose system better than a strict organizational system?

GTD’ers, do you think you can break the habit?  Or are you even willing to try?

So this may not come as a surprise: one in five emails is now read on a phone.

The number of people accessing email on mobile platforms is on the rise.  This isn’t necessarily surprising—there are simply more capable devices, with more people paying for network access, and the email clients are easier than ever to set up.

But David Greiner, co-founder of CampaignMonitor, says it’s the magnitude of the rise in mobile email that is a bit surprising.

In June, Greiner tapped into CampaignMonitor’s client data to better understand the distribution of desktop, web, and mobile email clients (check out the full 2011 report).  The experiment collated data from over 3 billion email receipts and produced some interesting results:

The data suggests that desktop clients are still dominant, but their presence has declined about 12% over the past two years.  The web client usage also appears to have declined, but only by about 4%.  And clearly, mobile client usage is surging.  Over the past two years, people accessing email through mobile clients has increased from a mere 4% to nearly 20%–largely at the expense of the desktop clients.

While the trend is undeniable, it’s worth noting that the rise may not be quite as strong as the graph suggests.  CampaignMonitor can only detect the email client if images are displayed, so email clients that display images by default are inflated (i.e. Outlook 2000 and the iPhone) and those that block images by default are underrepresented (i.e. Gmail and Outlook 2007).  Even so, the rise of mobile is clear.

The Mobile Email Client Market

The explosion of mobile emailing in the past few years is largely attributed to the rapid adoption of smartphones and other network-enabled gadgets, like the iPad.  Two years ago, the iPhone 3G was only recently released, the iPad didn’t exist yet, and the Android platform was only beginning to take off.  But by Christmas, it’s estimated that 1 in every 2 Americans will have a smartphone.

Here’s the breakdown of the mobile email client market share based on CampaignMonitor’s data:

This does not include data from the Blackberry and Windows Phone mobile clients because they also block images by default.  But the chart nonetheless offers a decent diagnosis of the mobile market and clearly suggests that a lot of people use email on their iPhone—or at least about 1 in 5 people do.

Implications

The rise in mobile email has two major implications to consider.  First and foremost, standard email design must be reconfigured to ensure that people on mobile clients have a similar reading experience.  Fortunately, the mobile clients offer great CSS support, so modifying a template to adapt to a smaller screen isn’t too difficult.  In one Greiner’s other posts, he presents a walkthrough of how CampaignMonitor tweaked their template based on simple mobile design tenants.  He says that all you have to do is throw in an @media query, adjust the content width, and hide some of the less important stuff.  But for those less tech savvy, he also provides the new CampaignMonitor template to download and mess around with.

Secondly, the rise in mobile email presents the need for mobile email tools.  People have become accustomed to robust desktop and web email management applications—think Boomerang and Rapportive.  And now that mobile email clients are being used so heavily, the tools need to be available on the mobile platforms as well.  Here at Baydin we recognize the demand for mobile tools, so we launched Boomerang Mobile a few weeks ago to make the tools available on the go.  Check it out now and let us know what you think!

On September 1, 2010, we had 50,000 Boomerang downloads. I had $4000 in the bank, $3000 in credit card bills, and needed to loan the company another $2000. We’d tried and tried again to raise a seed round in Boston, to no avail. Every east coast angel and VC we could reach passed on the deal. We had a shelf life of about one more month, and then it was time to pull the plug and go get a job.

I was staying at the worst motel I’d ever been in, I had a mild cold, and the flight over had clogged up one of my ears so I could barely hear out of it. I was a wreck.

Then, miraculously, the most fortuitous Tweet in the history of Tweets appeared. Our startup was on the brink, and God intervened, in the form of a short bald dude who talks (and invests!) like a sailor in port.

And the rest is history. Dave committed to invest on the spot, and we moved to the Bay Area two months later. We had the rest of our target round committed within 30 days, and ended up adding a couple investors afterward. For the last nine months, we’ve been able to stop worrying about how to feed ourselves and focus on making our products and our business into what we dreamed they could be.

It’s been fun being known as the guys who Dave funded in a car – almost everyone in Silicon Valley has heard the story – but some have labeled us the poster child for a tech bubble and irresponsible investment.

I’m happy to say that a year later, all labels aside, our company is in a very strong place.

• We’ve crossed 400,000 Boomerang for Gmail downloads, and they’re still going strong.
• We’ve helped our customers with over 2.5 million messages, helping close tens of thousands of deals.
• We’ve helped our customers save over 62,000 hours through The Email Game
• Baydin has appeared in the print and online versions of the New York Times. Twice.
• In the last three months, we’ve brought in more revenue from customers than Dave’s initial investment. (We still ate Ramen for lunch today. True story)

Working with Dave has been amazing. Dave, in private, is contemplative, self-aware, and cognizant of the magnitude of what he’s trying to do. He’s helped us close investors, make connections with journalists, with intros and building our silicon valley network, and with benchmarking and advice on our products and metrics. The public lightning-rod version of Dave gets a lot more exposure than the version who’s always hustling on behalf of his portfolio.

If you’re an entrepreneur looking for a great investor, Dave should be circled right at the top. If you’re looking for somewhere to invest LP money, I believe there is still an opportunity to invest in the 500 Startups fund. We won’t know for 10 years whether or not making a bunch of small bets on scrappy first time entrepreneurs with a ton of users, or betting $41 million on Color pre-launch is a better investment philosophy, but it’s looking good for Dave.

We have a long way to go before we can prove that Dave’s investment in us was a good one. We’re working hard every day toward that goal. We’re incredibly grateful to all of our customers who are finding so much value in our products, helping us pay the bills, and helping us spread the word about how we’re making email better.

Dave, thank you for giving us that opportunity.

The best analogy I can think of is to put yourself back in time, to when you were between 8 – 12 years old.  Now, think carefully about the things that 8 – 12 year old boys like (at least, the geeky ones).  Video games.  Caffeine.  Scooters.  Toys.  Computers. Bean bag chairs.  Junk food.  This should help orient you, and brings you to the right frame of mind about t-shirts.

T-shirts are a part of that culture.  In part, t-shirts represent the ultimate middle finger to those unnamed sources of authority who wanted software engineers to dress like “Thomas Anderson” in the Matrix.  Software engineers want to be Neo, not John Anderson.

Check out some of these awesome Android shirts that I found:

You can find some of them in the Google Store if you’re interested.  But as Adam Nash would put it, some of them are more for tribal cohesion—so good luck finding them anywhere!

We took these inspirations and brainstormed up a few concepts for our own Baydin tshirts.  We’re hoping to get some printed in the next week—so Baydin’s first company t-shirt is on the way!  If you’re interested in getting ahold of one, check back soon to find out how.

Over the past decade, numerous companies have sprung up with the intent of developing a solution to make email more manageable.  As a result, we now have a solid set of tools and applications at our side that certainly alleviate the pain.  But even with all of the tools in the world, email can still be difficult to control and takes up a lot of our precious time.

Chris Anderson, TED’s curator, wrote a blog post in June that offers a different kind of solution to the email quandary.

According to his theory, the underlying issue feeding the email problem is that we take more time to respond to messages than the message took to write originally.  We are too often forced to answer open-ended questions, read large blocks of pasted text, and click through various links.  And that’s only after we spend the time to scan our inboxes and decide which messages to even open.  As a result, a message that only took a few minutes to write can easily suck up much more time for the chain of recipients.

It is in fact a potent ‘tragedy of the commons’.  The commons in question here is the world’s pool of attention.  Email makes it just a little too easy to grab a piece of that attention. The unintended consequence of all those little acts of grabbing is a giant rats nest of voracious demands on our time, energy and sanity.

The Email Charter

Chris and his colleagues at TED believe that the solution is actually quite simple: everyone must agree to a new set of rules.  Chris believes that if everyone could follow these simple email tenants, the problem would alleviate itself.  The full set of rules that they came up with can be found on the Email Charter website, but some of my favorites are:

Quash Open Ended Questions - It is asking a lot to send someone an email with four long paragraphs of turgid text followed by “Thoughts?”. Even well-intended-but-open questions like “How can I help?” may not be that helpful. Email generosity requires simplifying, easy-to-answer questions. “Can I help best by a) calling b) visiting or c) staying right out of it?!”

Attack Attachments - Don’t use graphics files as logos or signatures that appear as attachments. Time is wasted trying to see if there’s something to open. Even worse is sending text as an attachment when it could have been included in the body of the email.

Celebrate Clarity - Start with a subject line that clearly labels the topic, and maybe includes a status category [Info], [Action], [Time Sens] [Low Priority]. Use crisp, muddle-free sentences. If the email has to be longer than five sentences, make sure the first provides the basic reason for writing. Avoid strange fonts and colors.

As an email software company, we aren’t convinced that adopting the Charter is an end all answer—but definitely a good start.  I think that a mix of improved email habits and smarter email applications can bring about the peace of mind that Chris and the rest of us are looking for.

But the full list is definitely worth a read.  Join the rest of the 15,000+ supporters by signing it, and be sure to spread the word on Facebook and Twitter so we can really put the TED idea to the test.

As much as I love Twitter, I have always hated the 140 character limit. Yes, I know. The limit encourages real time spontaneous sharing, light banter, and fluid commentary. I acknowledge Twitter’s role in breaking news of revolutions and natural disasters. I didn’t imagine where Twitter would be today when I started out with it but it’s a big part of my online identity now.

But aside from link sharing and instant access to the real time world events, it fails as a tool to communicate your thoughts. But then I was starting to get worried that people are losing their ability to coherently convey their thoughts. And I really like reading, reading a lot of words.

Yes, you can argue that when people don’t have the character limits, people write their inane thoughts even longer and you don’t have the patience to read through them. But think about it for a second. Anything that actually is worth reading is usually more than 140 characters. You can do a good witticism, one-liner joke in 140 characters. But are you aspiring to be a stand up comedian, sharing only witty comebacks and punch lines that will keep your audience entertained? Then yes, continue on with Twitter. I am not saying stand up comedians are not worthy of my attention. I love Twitter for other reasons besides satisfying my need for longer conversations and arguments with people I know.

Enter Google+. Looking at my stream on G+ this morning, I started to smile.

I shouldn’t have this problem. After all, I check my email every minute of the day. In fact, I’m surprised that my Gmail screen hasn’t been burned into my retinas yet.

I guess I’m a procrastinator. Therefore, my New Year’s Resolution is simple: get to an empty inbox every day in 2011.

Think I can do it? Here’s my plan. I’m going to tackle my email overload problem from three angles.

1. Stop Emails from Hitting My Inbox in the First Place

Half of my emails aren’t for me at all. They’re newsletters, notifications, and mailing-lists. I’ve set up a couple Gmail filters, but by creating more, I can do a more aggressive job of hiding the messages that don’t need my immediate attention.

For websites that require one-time registration, I’ll protect myself with Mailinator. Mailinator lets me create a temporary email account for services that ask for my email address. By offering me a temporary address, Mailinator not only protects my privacy but also prevents future spam.

If I still receive unwanted email from companies, I’ll use Unsubscribe.com. It seems silly, but sometimes I really am too lazy to scan for the unsubscribe link and click through multiple logins and checkboxes. With Unsubscribe, I only need to click a button.

2. Choose a Time and Place to Handle Emails

I’m a compulsive email-checker. Except when I’m sleeping, my unread email count rarely goes past “1″. These constant interruptions are unproductive.  It would be better to check my email five times a day instead of five hundred.

I’ve heard good things about Klok and RescueTime, which are two time-tracking applications. With either one of them, I can monitor how often I open my email client. I can also use Google Calendar to schedule daily times to check my email (although I don’t think its email reminders would work well in my case).

But the best tool might be AwayFind. With AwayFind, urgent emails will reach me by phone or IM, even when I’m away from the computer. I’ll be able to walk away from my inbox without feeling anxious.

3. Get Faster at Responding

Email takes a long time to process. I’d tell you how long it would take me to get through my remaining emails, but that’s time that I could use for getting through my remaining emails.

I’m very familiar with Gmail’s Canned Responses, which lets me use message templates for common responses. Outlook doesn’t have canned responses, but I’ve accomplished the same effect by creating email signatures corresponding with my usual replies.

To improve my email response time, I’ll use the three.sentenc.es approach when it is appropriate. According to this philosophy, I must keep my emails short and simple. This way, they’re faster to write and more likely to be read. It makes approaching an email less intimidating, and my short responses will help others reach an empty inbox, too.

Of course, the ultimate tool to fight procrastination is the Email Game. It lets me interact with my email in a totally different way, encouraging me to stay focused and make rapid decisions on emails. I get through my emails faster than before, and I feel good about doing it.

Is Inbox Zero something I can achieve this year?  I don’t know. But I encourage you to try reaching it, too.