inbox love 2012

Christina and I attended Inbox Love at Microsoft's Mountain View, CA campus on Oct 24, 2012. We were there to a) to demo Gander, and b) to get a better handle on some of the newer technologies and startups in the email ecosystem. On both accounts, I'd say we succeeded. Many thanks to Joshua Baer (OtherInbox), Jared Goralnick (AwayFind), and 500 Startups for putting together such a worthwhile conference.  

Before the session recaps, some notes:

The conference speakers furnished a lot of interesting stats; the following were particular thought-provoking to me.

  • 58% of workers do not go more than an hour without checking email. Some people check email up to 36 times per hour.
  • "You can build something for a million people and still not make an impact."
  • "The platform players (Gmail, Outlook, Yahoo) each have > 100M users. Don't try to compete with them."
  • Buzz word alert: monochronic, meaning single tasking. Sounds like a bad disease you get in your twenties.
  • Women are generally better than men at multitasking.
  • Email is like zombies: it keeps coming as we kill them!
  • From Baydin / Boomerang who have done both add-ins and rich clients: "Without autocomplete, attachments, good rendering, and 80,000 other things, your email client is dead."
  • Gmail users spread new tools virally. Corporate Outlook users don't, so more traditional marketing is needed.
  • Switching email clients causes friction because people stick with learned behaviors that may not be feasible in the new client.
  • From Rapportive: the five tenets of user credibility: trust, control, confidentiality, transparency and no spam.
  • OtherInbox went from storing all email headers to just two weeks and now down to three days. They learned the hard way that the less you store, the better.
  • An inbox from 1972 looks an awful lot like an inbox from 2012 - list of From, Subject, Date in chronological order. Sigh.
  • "Inbox workflows suck because engineers are the only people who can build them and they think that the rest of the world is like them." (Ed: and engineers don't get a large volume of time critical email.)

Onto the session recaps!

But first: Josh and Jared kicked off the conference by sharing what had happened in the world of email since the last Inbox Love, in February 2011.

Session 1: Email Devotion vs Addiction

Speaker: Kelly Gotogotomedia, LLC

  • Don't trust what people say--trust what they do. In one study, 60% of respondents reported attending church, but only 24% actually did.
  • 58% of people don't go more than an hour without checking email.
  • "Checking habit" is a habitual compulsive behavior.
  • We should strive to build products that enable human interaction rather than looking at our phones.
  • We need to create experiences that people love.
  • "I love it" lies in the middle of "it works," "meets my needs," "comfortable," and "personalized."
  • There are three states of being: Aware / conscious, Automatic / "inner conscious," and Meaningful / "I feel good, in control." It's the last state that we want our product to tap into. Doing so requires the presence of so-called "emotional connectors," which tie products to pleasurable rituals.
  • Steps to becoming a meaningful product: be easy to use, be trustworthy, meet needs, connect to habits, trigger aspirations. First it has to work, and eventually it needs to make you dream and help you build a better life.
  • Ringtones are an example of a a product with an emotional connector--they solve a purpose (alerting user to an incoming call)  while also creating identity, giving pleasure, and triggering nostalgia.
  • A new email platform should: Reimagine, Relief, Control. Those are the emotional connectors that Alto is using to engage people.

Session 2: Hotlook, G365, and Email's Merging Roles

Speakers: David Dennis (Microsoft), Roger Neel (Mavenlink), and Joshua Baer

David: Outlook 's new features include Quick Views of  documents, flagged items, photos, shipping updates, shopping, and new categories. You can also delete all and unsubscribe in one action and schedule cleanup for sets of messages. Outlook does auto identify/ classify, and provides social connections (Twitter and Facebook) for context. It has a better compose experience that completely changes screen. Documents can be sent via skydive attachment to recipients on any platform, in any browser. Recipients can edit or view with Skydrive without Office being installed. Note: As consumption experience moves away from web to devices, it's harder to make a good cross platform experience.

Josh: OtherInbox has 3 million users signed up within Yahoo Mail (Vast majority of users at the conference room use Gmail, though.) OtherInbox allows you to automatically sort email with the Automatic Organizer, and attach large files with UsendIt. Joshua thinks the Google Apps Marketplace isn't working well for consumer. Yahoo's add-in integration is more contextual, displayed right in the inbox. The big challenge is how to integrate add-ins not only with the platform, but with the experience of using the platform. Note: Gmail, Yahoo, and Outlook all support OAuth. This is the future platform.

 Roger: Mavenlink is a SaaS platform for consults and professional service orgs.It's the top-downloaded app in the Google Apps marketplace, and provides deep integration with all Google products (email, calendar, docs, contacts). Webmail is a big platform, like Outlook on desktop. Full PIM, not just email. It looks kinda like Facebook. It leverages Google task lists, Calendar to avoid duplication of functionality. MavenLink used the GMail platform to build their app, but they are now moving to support Microsoft webmail platform.  

Session 3 [Keynote]: Life without Email?

Speaker: Gloria Mark Our big problem is that we are caught between the pre-email and post-email eras. While there has been a widespread adoption of IT,  people cannot maintain a continuity of task and information flow, across contexts. This is because most people are monochronic (single taskers) in a polychronic world. Our average task length is 3mins before we move on or are interrupted. People work in 12 "working spheres," with an average or 10 min per sphere before switching. Every 12 minutes a person typically experiences an interruption lasting 2 min (broad average). 44% of these are self-interruptions, begging the question: Are we conditioned to self-interrupt? Maybe not, as it turns out high external interruptions create high internal interruptions. The worst thing about interruptions, from a company's standpoint: post-interruption, employees take an average of 23 minutes to resume working on the interrupted task--this even though they work significantly faster on the new task. The worst things about interruptions, from the interrupted employee's standpoint: significantly higher stress, mental workload, and frustration. Interruptions aren't always negative, but they are when they force people to switch topics. Gloria does a lot of research on multitasking. One of her findings: women are significantly better at multitasking. In her study, she found females worked in more spheres, experienced fewer interruptions (external and self), and were more likely to resume interrupted work. Moving from the general to the specific (email as interruption), Gloria says the line about email being like zombies. Great analogy. 70% of emails are attended to within 6 seconds, email can be checked up to 36 times an hour, and people spend 23% of their work day on email. Many audience members seemed to think 36 times an hour was low. Gloria's email cut-off study, "A Pace Not Dictated by Electrons," tracked the effects of an email-less life.  Participants went 6 days without email. They wore biometric sensors and their colleagues wore sociometric badges, in the first case to measure internal effects (heart rate, relaxation), and in the latter to see what the email-less peoples' colleagues did instead of emailing.

The results, in brief: Participants spent more time out of the office meeting people face-to-face, engaged in more metawork, and spent significantly longer amounts of time on their desktop (about double the amount of time). Participants' frequency of switching windows declined by half. Their heart rates were more varied, indicating higher relaxation. Communication-wise, the participants' colleagues said they could get the info they needed without email. However, while participants reported feeling much less stressed and more focused, they also felt cut off. Gloria says this illustrates the need for technology to rewrite social norms, eg make an email platform  that enables task continuity and somehow lets people off the hook for not constantly checking.  

Session 4: Platforms vs. Clients

Speakers:  David Claux (Microsoft), Alex Moore (Baydin), Sherman Dickman (Postbox)

David: Outlook Web App: OWA and Outlook converged. OWA has much better contextual support via Agaves, e.g. maps, meetings (pre-populated). Quick views in OWA include "all," "unread," "to me," and "flagged." Since users hate opening a new window with a new experience, there's also inline reply right in the reading pane.

Exchange APIs Gmail implemented Exchange Active Sync for existing devices. Outlook 2013 has native EAS connectivity (not MAPI). EAS is recommended for devices. Exchange Web Services is more server to server. Mac Outlook and Mac mail client use EWS only. Outlook uses EAS to connect to Gmail, which is real news. That connection includes offline, calendars, etc. The EWS managed API is written very well. THe EWS Java API is now available from MSFT, and will catch up with the EWS managed API 1.2. This will allow companies to recompile and change without submitting back to MSFT. They could be submitted back to MSFT in a legal way.

Alex: Boomerang now works on top of Outlook and Yahoo. Its bread and butter is message scheduling, but there's also a smart plugin for Google calendars, and a light, gamified email client, The Email Game. Since Baydin started in 2010, Boomerang for Gmail has been downloaded 1.5 MM times. The company is now profitable. Interestingly, Baydin started with Outlook first, then went to Gmail. Doing a client requires autocomplete, attachments, rendering and 80,000 other things, whereas a plugin allows you to just add the stuff you want to build on top of it, and users don't have to worry about switching. Because GMail doesn't have a supported API for front-end integration, Baydin ended up using Chrome and FF extensions by walking the DOM. Maintain or die. Things are shifting under your feet. Same for Chrome store. Shifting sands. #1 obstacle for them to overcome. Everything had to be written in Native JavaScript. Now the browser plugin environment is better. Two common complaints: speed, workflow / actionable email. People aren't going out and searching for Boomerang--it's spreading by word of mouth. Gmail has been biggest source of leads. Outlook supplies 10%, and needed paid marketing channels. Yahoo has been really hard.

Sherman: Clients are an all or nothing experience. Everyone has email. Switching is friction. Disruptive to workflow. Setup and config issues. They'd rather stick with what they know. For all that, Postbox still converts a high percentage of free to paid users. They're great for Gmail, but don't work with Exchange, because Microsoft can't bundle. Problems: Postbox can categorize using IMAP labels, but lots of servers do not use it consistently. Its conversation view was done using ReferenceHeader ID, which was stripped away by some servers, so they had to redo threading. IMAP partial word searches doesn't work on Gmail. Each new version of MacOS tightens up servers - iCal scripting no longer working.  

Session 5: Email & Data

Speakers: Joshua Baer, Eric Botto (Slice), Greg Gould (Return Path), Rahul Vohra (Rapportive / now part of LinkedIn)

Rahul: Rapportive brought in social data like FB, Twitter, LinkedIn to Gmail. Its goal: "make you brilliant with people," showing you everything you need to know about somebody within your inbox. Essentially, by providing you with a rich view of person within your mail service, Rapportive is the simplest relationship management tool. Rapportive has two audiences: 1) A smaller subset are people-centric professionals. Interactions are a key part of job. 2) Larger subject is consumer oriented. Want people's faces! Needs utility and emotional connection. Three big changes in email: 1) Rise of webmail, which is still easier to use than a rich client like Outlook 2) chrome and FF add-ins, with > 50% market share 3) lot more indexable information. Wasn't possible 5 years ago. 5 tenets of an email product:

  1. Trust - the most valuable thing
  2. Control
  3. Confidentiality
  4. Transparent
  5. Spam - we won't any won't let anyone else

Josh: OtherInbox is now trying to keep as little as possible from as much as possible. This gives them less liability and and makes data easier to keep track of. They went from storing all message headers to just three days of headers While Return Path owns OtherInbox, there is a wall between the two, but Return Path uses OtherInbox's data to certify/rate allowed emails. They have an Anonymous panel to help marketers understand emails. It's B2B inbox insight, kind of like ComScore. Answers questions like: "Are people reading your mail?," "Are they forwarding it?" Users vote with clicks, opens, in order to help mail marketers tune their message. Forwarded is even better than a FB like button. Note: OtherInbox let users keep their email addresses. Changing addresses is hard.

Eric: Slice is a spinout from Stanford. It tracks all your receipts, so you know what you are buying. Slice users can link their inboxes, track and get updates on purchases. Slice extracts item level info out of electronic receipts. opt in only. The "link inbox" option looks exactly like the iPhone signup by design. It works mostly via IMAP, Yahoo Cascade, and even POP3 for MSFT. Slice saves its users money through its price drop alert. It tracks the price of an item 30, 60, 90 days after purchase. The company started in 2010 and spent 18 mnths developing info-extraction procedure and machine learning algorithms. They now have 40M items in their database.  

Session 7:  Email Workflows, Today & Tomorrow

Speaker: Dave Troy (Mailstrom) Dave shows us an inbox from 1972. So much has changed! Just kidding. Breaking down the big guys:

  • Outlook: 800M users (kind of confusing, since Outlook is just a client)
  • Hotmail/ 360M
  • Yahoo: 300M
  • Gmail: 425M
  • iCloud: 150M
  • Other: 1.4B

Gmail's users are very diverse in their behaviorial/technological preferences. (web vs imap, inbox zero, public/private,…). There are 12 key traits, which works about to about 100,000 users per archetype. You could break these into maybe 64 personae, but 16 personae (27M users each) is more manageable. The personae identification is Myers-Briggs-inspired. Most email products don't appeal to more than 1-2 of 16 personae, because engineers make them, and engineers a) tend to fall into these personae, and b) few other people do. Likewise, inbox workflows suck because engineers are the only people who can build them and they think that the rest of the world is like them. "You are not f$cking normal," Dave tells the audience. Sorry, audience. Luckily, you can compensate for your abnormality through use intensive research and customer development. Which is what Dave did with Mailstrom. He surveyed 352 people and figured out that more than 100 emails received/day is a problem. Hence, Mailstrom lets you bang through a large number of emails at once. Mailstrom also sorts messages by sender, subject, lists, time, social, size. Geeks can sort by msgs at midnight, messages received today, messages removed today, messages news, 0 active tasks, and can color-code by volume.  It doesn't use algorithms--more like a machine gun that amplifies brain power. It will appeal to quantified selfies, for sure. Also, Esther Dyson is advisor. Tips: Beware "false consensus effect or bias." Otherwise known as leading the witness, lemming syndrome etc. Get live in-person testing. Most engineers are too obtuse to listen to users. Don't build on broken tools - make it better.  

Next up, the big announcement: ReturnPath Acquires is a REST email API. It grabs contacts, files, messages, threads, web hooks (post back). Return Path acquired them to advance their vision of email as a platform.  


  • Us!
  • nveloped : a way of sending secure email, layering authentication on top of email content
  • Notfymenot - sort who is allowed to send or not send
  • PowerInbox - makes email more active - ordering, play games, etc.
  • File Squirrel: Mobile app that lets you browse your email attachments (won hackathon of 50 users). Attachments do not need to downloaded to phone. It was built in less than 7 hours.

Aaaand that's all, folks. If you've made it this far in one go, you deserve a treat. Go buy yourself an icecream cone before the snow falls.