Web 2.0: Making Email a Useful Web App

Making Email a Useful Web App
Web 2.0 Conference
April 23, 2008
San Francisco
Andy Denmark
TripIt, Co-Founder and VP Engineering

Email Bankruptcy “ I routinely declare email bankruptcy and simply delete my entire inbox.” - Michael Arrington, TechCrunch “ Wondering if I can get a Bear Sterns bailout for my email bankruptcy.” - willpate on Twitter “ (He) just declared email bankruptcy. I've read those declarations enough to know it means our email tools aren't usable.” - garrickvanburen on Twitter So, why is email still around despite all the challenges and criticism… ?

Email Is Still The “Killer App”
Email is a natural extension of a metaphor for communication that humans have used forever
Everyone has email and the overwhelming majority of all person to person Internet communication takes place there
No matter what else people use to communicate, they all use email too
Email contains an amazing amount of context and data about our lives
Our relationships
Our purchases
Our thoughts and the thoughts of people we know

What More Can We Do With Email?
Spam and mass email marketing may be contributing to the problems outlined earlier
But think of all the things we can do to make our applications better by making better use of email:
Broadcasting data
Query interfaces
Data transfer
Intelligent parsing of data
Mining of social connections (“Inbox 2.0”)

Does An Email App Make Sense?
PROS
Ubiquity – everyone has email
Exposure – email is on all day and captures a lot of attention
Simplicity – easy to send email, everyone knows how to do it
Embedded identity
CONS
May just not fit your service
May be too complex for your users to understand
It’s challenging to properly support all email clients, versions and formats
Building and supporting a system that sends, receives, and reads email is a pain

Prehistoric Email Apps

Domain Registration Email Sign-Up
Email to: [email_address]
From address authentication for new sign-ups
Choose to receive your bill via email or USPS
Authentication schemes for modify/delete were CRYPT-PW and PGP

Archie File Query Email Interface
Available Interfaces
Text-based client
Graphical client
Telnet client
Email

Browsing The Web Via Email “ For personal reasons, I do not browse the web from my computer. (I also have no net connection much of the time.) To look at page I send mail to a demon which runs wget and mails the page back to me. It is very efficient use of my time, but it is slow in real time.” -- Richard Stallman (2007-12-15)

About TripIt ?

***CONFIDENTIAL***

Forward Any Confirmation Email Automated Online Master Itinerary Automated Weather, Maps, Guides… Trip Sharing & Social Alerts iCal & Atom Support Email & Mobile Access Add Meetings, Activities, Restaurants, etc.

Why Email Made Sense For TripIt
The native format of travel data is varied and unfriendly
The travel industry isn’t moving to expose that data
Partnering with big travel companies and building APIs would take too long
Users already have all their travel data in email, but that data is “dead”
Auto-account creation using the embedded identity of an email message
It has become an “instant delight” factor for users

Types Of Email App Services Command Line Interface Data Transfer Semantic Parsing Broadcast ?

Types Of Email App Services Command Line Interface Data Transfer Semantic Parsing Broadcast
One Way
User requests email information to be sent to them
Typically triggered by an action or an alert
Examples
Mailing Lists
Google Alerts

Example: Mailing Lists Searchable knowledge base built as a by-product of natural human communication

Example: Google Alerts
“ Real time” alerts delivered right to my desktop
Useful way to asynchronously broadcast data I’ve requested as it’s available
With linkage to the web, alerts are actionable and controllable

CLI
Users emails a command and Email App replies with a response
Typically a standard list of commands and responses
Examples
I Want Sandy
TripIt
Twitter

Example: I Want Sandy http://iwantsandy.com/

Example: TripIt

Example: Twitter
Messaging platform with multiple UIs
Web (http://twitter.com/)
SMS (40404)
IM (Jabber: twitter@twitter.com)
Facebook (http://www.facebook.com/)
FriendFeed ( http://friendfeed.com/ )
Desktop (e.g. Twhirl)
Email
I can tweet by email?!?
Yes, it’s just another way to use the messaging platform’s CLI
Very natural, ubiquitous and free (no SMS charges)!
See: http://emailtwitter.com/ and http://twittermail.com/

Types Of Email App Services Command Line Interface Data Transfer Semantic Parsing
Email Forwarding
Users forward emails and Email App recognizes and parses them
Typically converts “unstructured” data into “structured” data making it more usable to the app and user
Examples
Flickr
Blogger
Broadcast

Example: Flickr

Example: Blogger

Intelligent Agent
Structured data from email is enriched by the Email App by retrieving related information from other sites
Typically leverages “keys” such as geo-coding to capture relevant data
Examples
TrackMyShipments
TripIt

Example: TrackMyShipments

Example: TripIt Timezone Online Checkin Flight Status Seat Advice Flight Details Weather

Types Of Email App Services Command Line Interface Data Transfer Semantic Parsing
Email Forwarding
Users forward emails and Email App recognizes and parses them
Typically converts “unstructured” data into “structured” data making it more usable to the app and user
Examples
Flickr
Blogger
Broadcast
CLI
Users emails a command and Email App replies with a response
Typically a standard list of commands and responses
Examples
I Want Sandy
TripIt
Twitter
One Way
User requests email information to be sent to them
Typically triggered by an action or an alert
Examples
Listserv
Google Alerts
Intelligent Agent
Structured data from email is enriched by the Email App by retrieving related information from other sites
Typically leverages “keys” such as geo-coding to capture relevant data
Examples
TrackMyShipments
TripIt

Caution: Email Is Full Of Problems CAUTION STANDARDS CAUTION CAUTION SPAM CAUTION CAUTION PRIVACY CAUTION CAUTION DELIVERABILITY CAUTION

Deliverability Issues
Your reputation is attached to your IPs
Monitor your logs, it’s a dynamic system
Work with the ESPs, they are as much invested in this as you are
Even if you're a good citizen, there are no guarantees email will get through
Tips for getting email delivered…
No Open Relays
Proper DNS Configuration (forward + reverse resolution)
SPF/DKIM
Privacy Policy
RFC Compliance
ESP “Whitelists”
Bounce Handling
CAUTION DELIVERABILITY CAUTION

Spam Issues
No silver bullet solutions, but a suite of counter-measures…
Spam assessment tools
Spam Firewalls (Hardware/Software) ‏
Improper/forged headers are key factor
Non-RFC Compliant Mailers (don't retry, don't try all your MXs, etc.) ‏
DHCP/home IPs w/ no reverse DNS
Blacklists (be very careful) ‏
But all of these cause you to run the risk of catching legitimate email in the net
Spammers like to go fast, so slowing things down in an RFC compliant way can help
CAUTION SPAM CAUTION

Privacy Issues
People are very protective of their Inbox, it’s their private space
Laws vary wildly but there’s a baseline in common sense
Make sure people can opt-out/in easily
Build mechanisms that prevent you from contacting people who don’t wish to be contacted
Listen to your communities, you’ll get some of this wrong, but you can fix it
Be transparent and responsive
CAUTION PRIVACY CAUTION

Standards Issues
There are no standards that are strictly followed across mail clients
Pretty much every mail-related RFC has been outright violated or creatively interpreted by at least one major mail client
White space, HTML markup, attachments are all mangled and re-interpreted depending on which mail client is working on the message
If you build a mail application that reads email you will have to deal with this, it’s expensive and painful
CAUTION STANDARDS CAUTION

Key Take-aways
Email is not dead!
Treasure-trove of data waiting to be mined
At least four different types of apps
Broadcast, CLI, Data transfer, Semantic parsing
Remember the gotchas:
Deliverability, Spam, Privacy, Standards
If you get it right, huge payoff for you and your users

Questions
Andy Denmark
TripIt, Co-Founder and VP Engineering

Appendix
ESP Whitelists/Resources
Microsoft Hotmail/MSN:
http://postmaster.msn.com/Services.aspx
https://postmaster.live.com/snds/
http://postmaster.live.com/Troubleshooting.aspx
http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-78f80be272fb/enhance_deliver.pdf
http://www.senderscorecertified.com/ by ReturnPath
Yahoo
http://help.yahoo.com/l/us/yahoo/mail/postmaster/
Google
http://www.google.com/mail/help/bulk_mail.html
AOL
http://postmaster.aol.com/

Appendix cont’d
Mail Server Setup
http://domainkeys.sourceforge.net/
http://www.openspf.org/
http://www.maawg.org/about/MAAWG_Sender_BCP/MAAWG_Senders_BCP_Combine.pdf
CLI Examples
http://microformats.org/wiki/picoformats
Relevant RFCs
http://rfc.net/rfc2821.html (SMTP)
http://rfc.net/rfc2822.html (Mail Headers)
http://rfc.net/rfc2045.html (MIME part 1)
http://rfc.net/rfc2046.html (MIME part 2)

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Web 2.0: Making Email a Useful Web App

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Web 2.0: Making Email a Useful Web App — Presentation Transcript