Five Open Questions in Email

The email space is heating up after a long cool-off: The modern email desktop application was invented 15 years ago, and webmail is now 12 years old. With few exceptions, little about how users interact with email has changed since then. Yet, email clients are under attack from all sides: People under 25 use Facebook, not email. Overloaded office workers hate the email flood so much that companies are introducing email-free Fridays.

Email is being pulled in all sorts of directions. Here are places in which there will be lots of movement in the next years. They're ranked them by how much they'll affect you as a user.

1. Email vs. Facebook: Until recently, all my electronic communication took place in email. Now it's moving away, being replaced by more casual media, like IM, your Facebook wall, Twitter, or SMS. In the future, email could be where snail mail is today: A medium to receive advertising and official stuff.
   
   But there's an alternate world in which your email client could once again becomes your hub, by pulling in data from all these sources and displaying it in a sensible fashion.



2. Folders vs. Tasks vs. People: 10 years from now, will you still be organizing your email in folders that you manually create? Or will your email be automatically organized around tasks, or even better, around people who are important to you and their profiles? It's clear that the "move to folders, sort by arrival time" system is broken - what will step into its place?



3. Is search good enough? With the arrival of fast full-text indexes, email search sucks a little bit less than it used to. But there's still no PageRank-type magic to help you find those emails you're looking for. Hopefully, there will be smarter email search that learns from my search patterns (e.g. you might search twice a week for the same email that contains a password you can't remember) or understands the meaning behind your queries.



4. Does email need Artificial Intelligence? In the AI / machine learning / natural language community, there's been tons of research on making email smarter. We've looked into automatically summarizing email, predicting whether it needs a reply, generating a reply automatically, and clustering or automatically foldering emails to your heart's desire. Most of this stuff already works reasonably well, but no one has bothered to implement it in a consumer product. AI-based spam filtering is the norm today. Five years from now, are we going to be using intelligent email agents? Or are consumers not going to trust these helpers?



5. Little guys vs. the big guys: Email is hot again. Companies like Xobni, Xoopit, Zenbe, or Orgoo are being started, some with serious funding. On the other hand, established players like Microsoft, Google, and Yahoo are launching new features and opening up access to their data. Big players have traditionally been making slow incremental progress. It will be interesting to see if they can evolve their products more quickly and bring them to users faster than the little guys ever could.

This entry was inspired by discussions at the AAAI Enhanced Messaging Workshop in Chicago.

A New Company

I am leaving Xobni in late August and starting a new company.

Xobni has been an amazing ride, and I'm proud how much we learned and achieved together. We took Xobni from humble beginnings in Adam's apartment to a wildly successful product that is used by hundreds of thousands for hours a day. I've learned tremendously, and went full-cycle from making the original mockups, managing the team, and writing a large part of the product's code.

Ever since reading a biography of Bill Gates when I was 14 years old, I've wanted to be a founder of a company that makes a difference. I've wanted to build a workplace where people can be creative, productive, and happy, and a product that delights users and improves their lives. I feel like the time is now.

There are lots of challenges left in the email and communication space. I have some exciting product ideas for my new company, and I feel like I understand the space like few others do.

After wrapping up at Xobni at the end of August, I'm going on a trip around the world, covering Switzerland, Germany, India, Thailand, Hong Kong, and Australia. This trip is mostly for pleasure: I figured this would be my last break for a while. However, I will also be raising a small angel round from investors around the world.

iPhone 2, Week 2

Last week on the way back from Chicago, my beloved iPhone 1.0 slipped out of my pocket in a taxi cab. Calling the cab company didn't help: Apparently, people don't return iPhones to their rightful owner.

I already had withdrawal symptoms after 2 minutes without my iPhone. Thus, I bought the iPhone 3G the next day. Some observations:

1. Oh, the wait! Yes, it took me 3 hours to get the phone. I was in this line. I thought it would take about an hour, but that's how they get you: You've already waited so long! Why not wait an another 15, and another 15, and so on.
   
2. Oh, the slowness!: Yes, typing is slower. Is that the end of the world? Not for me.
   
3. New Headphone jack: Love it.
   
4. Apps: I use Instapaper, and the Google Search App, and Yelp. It's easy to see how 2 years down the road, some immensely useful apps could be built.

So, is it worth the upgrade? Probably not.

Enhanced Messaging Workshop at AAAI

I'm in Chicago for the AAAI 2008 Conference's Enhanced Messaging Workshop. Greg and I will be talking about some of the driving ideas behind Xobni, the hardships of building commercial email software. We'll also demo some products from our skunkworks.

I'm hoping that this workshop will hopefully fill an important gap: There are some conferences about spam fighting on one end, and general machine learning / data mining / user interfaces on the other end, but no forum for academic discussions of fighting email overload. See you there!

Six Mobile Ideas

Here are 6 ideas for mobile applications I’d like to use. Two of them are about easier data access:

1. Access to desktop files: I’d like to list, search, and open files from my desktop on my phone. Dropbox lets you do this through an iGoogle gadget, but I’d like to go to a simple page on my iPhone.


2. Offline content: When it has WiFi reception, my phone preloads itself with all the content that’s on top of Hacker News, and lets me to quickly browse it when on the go. Similar to AvantGo from the old Palm days, but doesn’t need you to plug your phone into your computer.

The rest are location-based services which require either good position triangulation or built-in GPS on your phone:

3. Instant Meetup: An extension to my Academic Lunch Dating idea from years ago. I’d like to do things like: “I’m in Washington Square Park right now and would like to find someone with similar interests”. It’s GPS-powered instant friendship building or dating.
4. A Location-based Upcoming: “I’m at 3rd and Market and would like to do something exciting within walking distance.” This would give recommendations of what to do – it might give you your friends’ party 4 blocks down, or the latest SFMOMA special exhibit.
5. Yelp it now: Instead of tediously going through Yelp’s interface – which is super slow on my iPhone – I want a simple, fast-loading page that returns the top 3 rated restaurants on Yelp within walking distance.
6. NextBus plus GPS: Using built-in GPS, finds out which bus stop I’m at. List the next bus arrivals here, in any directions. Much like the existing NextBus, but no scrolling through pages of stops.

Has someone already done any of this? If so, please leave a comment and let me know.