Despite having helped build a startup 12 (!) years ago focused on keeping your address book up to date, despite the massive intervening adoption of smart phones and social networks, and despite being connected to an unusually tech-savvy cohort of friends and relatives, my address book is still a disastrous mess. Sound familiar? This thought always lingered in my head, but it confronted me full-force this weekend while my wife and I struggled in vain to produce an updated mailing list to announce the birth of our new son. We’d done this for our last child (sadly using a shared Google spreadsheet in absence of any more purpose-built tool), so we were only 2-3 years out-of-date, yet an astonishing 45% of the addresses of our friends and family needed updating, and the task was not easily achieved.

This led me to ponder why this seemingly tractable problem remains so stubbornly unsolved, and what, if any, hope lies ahead.

The false saviors

It’s hard to remember that when we started Plaxo in 2002, there was no iPhone, no Facebook, not even Friendster or Flickr. Our biggest opportunity was writing a Microsoft Outlook plugin. Since then, many people have said that the problem of out-of-date contact info would soon be a relic of the past. Smartphones would keep us seamlessly connected. Social network profiles would always contain our latest info. Number portability, Gmail, and mainstream messaging services would create long-lasting identifiers. The death of snail mail would obviate the need for physical addresses. And so on. We often worried about these trends, and in some sense they have each helped us get more connected, yet they clearly haven’t solved the core problem. Why not? A few reasons”¦

Contact info still changes frequently (esp. in aggregate). As mentioned above, nearly half of the people we sent birth announcements to last time physically moved in the past 2-3 years. Now in our age range that’s probably more than usual (buying a first house, getting a new job, etc.), but it’s still staggeringly high. And it’s not just physical addresses. I’m constantly wondering “is this the right email address or cell phone number to use for so-and-so, or is it dead / rarely checked these days?” Ditto for “who do I know who still works at [insert company here]?” Even using circles in Google+, I’m often wondering “gee, is my Googlers circle still a safe place for Google-only discussions?” Even when the info hasn’t changed, I’m often unsure if it’s still current. And of course I keep meeting new people, many of whom I haven’t ever collected the relevant info for (even if they wouldn’t mind me having it).

Social networks suck at contact info. As surprising as the staleness of our address list was, I was even more surprised how few of my contacts had their latest address in Google+, Facebook, or elsewhere online. Many of these people used to work at Plaxo, and all are online using social networks daily. Yet the info is either missing, stale, or not shared with me. Why? In theory, social networks subsumed Plaxo-like functionality, but in practice there are deep reasons why they fall short.

  • Contact info is buried. I have to click to someone’s profile, click to their about/contact tab, scroll down, and then hope their info is shared with me. When’s the last time you viewed your own “about” tab (let alone someone else’s contact info section)? It’s out of sight, out of mind. In fact, even my own home address was out of date on Google+ and Facebook until long after I moved. It’s just not something you naturally think about while checking your news feed.
  • You don’t want everyone to have your info. Even though most social networks provide a way for you to share personal contact info, most users don’t want all of their “friends” to have all of their personal details. I recall hearing back in the day as Facebook grew that more people were actually deleting their contact info because they were making more and more loose-tie friends who they didn’t feel comfortable sharing that info with. On Google+ you can (of course) use circles to finely control who sees your home info, and Facebook has since followed suit, but as my wife put it when I asked her today, “eew, I don’t want to put my home address on Facebook”. You have to trust the site itself, your ability to navigate their privacy controls (and keep them up-to-date as your life changes), and the site’s ability to honor your choices before you’ll use social networks to share sensitive info. For most people, that bar has not yet been met.
  • Oh, and that whole “data portability” thing. When I want to see if I have someone’s latest home address, where should I look? My address book? Only if I can pull in the info shared with me from social networks. Not surprisingly, Google+ syncs to Google Contacts, but everything else is still a walled garden. You have to go knock on all the doors. For every person you care about. Every time. Even though they chose to share it with you. Sound broken? I agree. But I guess we weren’t loud enough.

Smartphones aren’t smart about contact info. Your smartphone address book does a good job of following you around from device to device and desktop to mobile. The only problem is that it is syncing garbage data. You’d think that using it to send and receive phone calls, text messages, emails, and looking up driving directions would make your address book fresher and more complete. But you’d be wrong. Chalk it up to app fragmentation and no one really trying hard to solve the problem in the first place, esp. at the OS level. Even at Google, the Gmail Contacts team is separate from the android “People app” team, and most OEMs bundle their own separate address book. Good luck.

No one’s helping you scrounge. Another fascinating if infuriating aspect of my recent Labor Day labor to update our mailing list was how often I could find the addresses by scrounging through my email archives, text messages, and manually entered address book info. I’d even been to many of the homes I lacked addresses for! In the absence of a good contact info syncing solution, most people still solve the problem “out of band” via existing communication channels (“leaving now, btw what’s your address in SF?” “it’s 123 Fake St., see you soon!”). Yet nothing is helping you extract, save, and aggregate that info for the next time you need it. It’s still a painful, manual process that you need to “get good at”. And this is for close ties–not random acquaintances–so it’s surely just an “entropy” problem, not a “stalking” problem.

The wisdom of crowds? Another trend I was sure would take off in the age of the cloud was some kind of solution for pooling contact info between families, friends, and organizations. At Plaxo we used to always have the problem, “Who’s got the cell phone for that new guy we just hired?” and the answer was always “someone in the room” (you just don’t know who in advance, and you have to ask them first). Many families still have a designated aunt who dutifully maintains the conglomerated birthday and holiday card list. And “hey Garret, remind me what Pete’s new address is?” still gets the job done in a pinch without offending. So why does each address book still start from scratch as if it were the only record of knowledge in the universe?

A new hope?

In the years since leaving Plaxo to help start Google+, I’ve talked to nearly every “address book 2.0” startup that’s reared its head. Apparently I’ve got a reputation in the Valley for not being “over” this contact info problem. Many have offered clever twists, but none have fundamentally addressed the challenges above. And perhaps unsurprisingly, as a result, none have saved the world from its frustrating fragmentation. So why am I still eternally optimistic? Because it’s a real, mainstream problem, there’s no good reason people want fragmentation to persist, and increasingly smartphones do participate in the events that collect or verify contact info. Plus there’s still the cloud opportunity for making each other smarter. So how might such a solution emerge?

When trying to solve any complex social problem, one good question to ask is, “What does the ideal solution state look like?” In the case of up-to-date contact info, I’d argue we still don’t know. You could say it’s everyone being on a single social network and using it perfectly, but is that ever going to be realistic? I’d say it’s more likely a mix of assisted sync and scrounge. In other words: help me collect whatever’s been shared with me via social networks or communication tools. And the place to do that is logically a smartphone (backed by a cloud-hosted account). Google or Apple are, in theory, in a great position to make progress on this, but I suspect it will be a startup that gets the job done, since it can be their sole focus and brand identity.

Such a startup would have to embrace the messy reality I’ve outlined above and turn it into a strength. Use all the available APIs and other tricks to help me find the contact info that has been shared with me. Keep track of when it was last updated (don’t make me guess). Parse through all my emails and texts for stuff that looks like contact info. Use my phone’s location history to ask me whose house I just visited when it doesn’t look like a business. Remind me what email or phone number each contact last used, and let me easily ping them back if I need some updated info. Help me build custom lists for things like holiday or birth announcements, and use that as an opportunity to ask for updated info. And partner with sites like TinyPrints not only to send those cards but also to send change-of-address cards when I myself move (something you should also be able to detect using my phone). Once you start gaining traction helping individuals keep their address books up-to-date, add a layer to pool it with family, friends, and colleagues in a privacy-preserving way (e.g. an easy way to see who knows someone’s phone number, but you still have to ask them to share it with you).

Is there enough here to build a successful business around? You be the judge. But is this still a real problem that real people still wish someone would solve? Abso-f*cking-lutely.