As if my own personal iMessage problems weren’t enough, take a look at my wife’s iPhone storage. Her phone is close to unusable because her text messages are taking up TEN GIGABYTES of storage! WTF? Corrupt database? Unclearable cache? No clue how this is happening, nor how to clear out the space, etc.
I can’t wait until everyone is off the iMessages.

As if my own personal iMessage problems weren’t enough, take a look at my wife’s iPhone storage. Her phone is close to unusable because her text messages are taking up TEN GIGABYTES of storage! WTF? Corrupt database? Unclearable cache? No clue how this is happening, nor how to clear out the space, etc.


I can’t wait until everyone is off the iMessages.


iOS holding my phone number hostage = the worst bug I’ve ever experienced

Two months ago I switched from iPhone to Android. I’ve been a huge iOS fan since the first day, but just couldn’t deal with iOS7 (although that’s topic for another post).

I got a Verizon MotoX and couldn’t be happier. I could switch pretty much every app I used and was up and running w/ Android as my primary phone, fully loaded, within 24 hours.

But something really strange happened. I noticed I wasn’t getting text messages from lots of people. I was getting annoyed at them for not responding and they were getting annoyed that I wasn’t responding.

What happened? My work laptop was still configured with Messages.app so all their messages were still sending as iMessage. They were showing up on my work laptop, but not my phone.

This was pretty annoying, but understandable. Monday I went to the office, turned off iMessage, and thought everything would be fine.

Everything is very far from fine.

Here we are 8 weeks later and this is my current situation:

  1. If a friend on iOS (which is 99% of my friends) sends me a message, it first tries to send as iMessage and fails. The more tech savvy folks then get the option to “Resend as Text Message” and it will get through. This is pretty annoying for them, but not catastrophic.
  2. If a friend sends a group message and includes me, it will send as Group iMessage, not Group MMS, and I don’t receive it. And here’s the icing on the cake: it fails silently! They don’t get a “failed” notification. The message is just dropped in the ether. I never get it, and they don’t know that it failed.

Apple has tried very hard to help with this problem. Unfortunately their solution is TELL EVERY SINGLE ONE OF YOUR FRIENDS TO DELETE EVERY SINGLE MESSAGE THREAD THAT YOU HAVE EVER BEEN ON.

Let me recap: I no longer have iPhone. My phone number isn’t associated with Apple, iCloud, iMessage, or FaceTime any more. But every single iOS device I have ever messaged in the past 5 years has my phone number cached! Every single phone will only try to message me via iMessage, not SMS. And to make matters worse, it fails SILENTLY!

To add insult to injury, the vast majority of messaging I’ve done in the past 3 years are group messages with pictures of our children. It would be bad enough if *I* had to delete 5 years of messaging history. But to ask my wife, my sister, my best friends, and literally every person I know to delete THEIR message histories? You’ve got to be kidding me!

I feel completely hostage. They have no solution and it’s insane that Apple has my phone number held hostage with no way to get it back.


  • Apple Customer Support has tried very hard to help me, and everyone I’ve interacted with has been fantastic. Super friendly, and for a user who just left iOS for Android at that! 
  • Gotta love the irony that the founder and CTO of a hugely successful text messaging company can’t get text messages ;)

Updates/Responses to Hacker News

  • Yes, I’ve reset/deactivated/cancelled everything possible. iCloud, iMessage, FaceTime, etc. on every device and on Apple’s web sites
  • I’ve even had Apple support revoke my certificates so I couldn’t authenticate if I tried!
  • Apple engineers confirmed there is no record of my number server-side. It’s a client side cache issue on every other person’s handset
  • And no, changing my phone number of 15 years is not a very good solution.
  • When I say “I’ve ever experienced”, I mean it. The experience of messages failing silently is awful. For example, my sister messaged me to tell me she was having a baby girl. I had no idea for days, and didn’t even know to congratulate her!

I fell deeply in love with a computer that broke my heart by evolving in a future direction I can never hope to understand.

Plot of ‘Her’ or upgrade to iOS7?


Thank you Mike Bloomberg for a phenomenal 12 years.

Mike Bloomberg has directly and indirectly influenced my life and career in so many ways, and more than any other single person. I am completely indebted to this total stranger.

My first real job after college was as a programmer at Bloomberg LP. It was 2002, the tech bubble burst, and no one would hire a programmer with little-to-no experience. But Bloomberg LP had plenty of cash and a fantastic new hire training program for junior programmers. It was my first job as a programmer and set me on my career track as a technologist.

And ironically, it was Bloomberg by Bloomberg, Mike’s autobiography about being entrepreneur, that inspired me to quit my job at Bloomberg to start my own company.

Fast forward to today. At Mobile Commons, we work with almost a dozen NYC agencies, enabling innovative agencies to engage with NYC residents in unprecedented ways. And it was the night before Election Day 2012, in the wake of Hurricane Sandy, that Mayor Bloomberg got on television and told everyone to text Mobile Commons to find out where to vote amid the chaos. And even further, it’s his generous philanthropy that funds so many of our nonprofit customers’ amazing campaigns, ranging from environmental protection to the prevention of gun violence.

Thank you Mike, for 12 years of hard work making NYC the best city on the planet and being a personal inspiration to me. I owe you a beer (with ice).


Question about syncing Android photos

I can sync pictures I take with my Android photos to my Mac easily enough.

But the Photos app has a bunch of pictures in folders, such as:

  • Auto Awesome (from Google+)
  • Downloads (email & MMS attachments)
  • Eye Fi (From my SLR)
  • Screen shots

These pictures don’t transfer when I sync to my Mac. I can see them in Android File Transfer but they don’t automatically sync like the regular photo album when I connect in USB Camera mode (PTP).

I’d really like a local copy of all of my photos in iPhoto, Aperature, Picasa, or similar. A single copy of pictures in Google+ cloud, which is the current behavior*, is not an option. (not totally true. Google+ Auto Backup doesn’t seem to have any of my Eye Fi pictures)

What is the best way to do this? Trawling through 4 subfolders with AFT every time I plug in my phone is not an option. 



Comparing iPhone & MotoX cameras is apples and oranges

It’s not fair to compare the iPhone camera to MotoX camera. iPhone cameras are phenomenal. The MotoX camera is so bad it shouldn’t even come with one.

They say that the best camera is the one you have with you. Well, I’d rather be forced to carry a separate camera at all times than to be stuck with hundreds of awful awful pictures of my kids.

Out of my first 400 pictures, I only got 2 or 3 that aren’t horrible. 

I’m a little stumped with what to do at the moment. Not being able to take great photos of my kids on the go for the next 2 years is unacceptable. 

I’m actually considering carrying my old iPhone5 with me, just for the convenience of the camera.


A Bit Like Windows XP

There’s still quite a bit of clunky, geeky, Windows-like experiences on Android.

For example, I wanted to import my podcast subscriptions. It should be easy: point the new plays to your OPML file and your done.

The instructions for one of the most popular podcast apps were “put your OPML files in /PocketCasts/opml_import folder”. This led to learning about Android file system and the lack of built in file manager. Fine. Download an OS X file manager, mount my phone. No /PocketCasts folder. Why? Android file system index doesn’t update immediately. Solutions: reboot or install an app that flushes the file system index.

Really? A 3rd party app to flush my cached file system index so I can mount a phone to copy a .opml file into a directory?

This is the tradeoff. And it’s really what Apple has going for it. It’s experiences exactly like this that made me switch 10 years ago away from Windows. I want my shit to work — I don’t have time to defrag and install drivers and google search every single thing i want to do. I just want it to work.



iOS notifications were never great, but they became intolerable with iOS7.

Every day after work I pick up my phone and wait 20-30 seconds while my entire day of mail, hangouts, imessage, words, zendesk, etc replayed in banners at the top of the screen. 

Android’s notifications, and specifically the notifications in MotoX’s Active Display are fantastic. From the persistent icons at the top, to the inline controls for pausing music & replying to emails, it’s a really pleasant experience. I’ve turned on way MORE notifications than I ever had before w/ iOS because they are so unobtrusive.