iOS 7 Tried to Kill My Company

How a series of unfortunate events conspired to destroy the momentum of my team, and what we learned. 

Fate is like a strange, unpopular restaurant filled with odd little waiters who bring you things you never asked for and don’t always like.

— Lemony Snicket

This is the story of how we launched our app, Canary, to the App Store. Hopefully you find excitement and humor in our anxiety, foolishness, and missteps (complete with a TL;DR story at the end).

Prologue—End of April, 2013

“I’m proud of what we’ve been through, and where we’re headed. I feel good about this one, guys.”

My team of four had just morphed ourselves from web developers to competent iOS developers in the last month, and we were starting with a clean slate. We wanted to build a calendar that helped entrepreneurs and people on-the-go actively manage and edit their calendars and efficiently schedule meetings from anywhere. We wanted to create a mobile calendar that was designed from the start to be more than a read-only tool. And so we set out, bright-eyed and bushy-tailed.

May 17, 2013—“A rose by any other name”

“If we can’t come up with a name, www.fuggit.com is available. We could tell people it’s like ‘Tempus Fugit’, but really it’s because ‘F*ck It’”

We have completed a few hundred interviews and surveys, done our market research, and have mockups and design documents in our hand. We don’t yet know what to call our iOS calendar — but we do have an internal code-name: Canary. At Google, we got used to the term to refer to experimental builds and this was our first app for the App Store. We loved Sparrow, and wanted to be the ‘Sparrow for GCal’ (and ‘Swan Song’ is too morbid), and I had just seen a cute canary at Petco when I was picking up dogfood, so Canary remained the top contender for a while. The stories we could tell people about naming the app Canary was enough to make it stick.

June 10, 2013—“iOS 6, I hardly knew thee”

“There’s a new iOS launching. iOS 7. It’s a complete UI overhaul. Are we in trouble? Let’s discuss EOD.”

We’ve just now hit the groove with iOS 6, and are churning out features. We let out a collective, “crap”. What does this mean for us? Should we stop? No. Course correct? Never! I urge everyone on. We should be fine. Canary was designed with a flat look from the start, and speculation put the iOS 7 launch in mid-September—we’d have weeks of lead time to migrate our app if we needed to. Better the devil you know than the devil you don’t — we should soldier on and tackle the challenges already on our plate.

July 12, 2013—“Canary prepares for a TestFlight”

“Everyone make sure to invite your peeps by the end of today.”

Surprisingly, things have come together really quickly, and we have a functional and well built beta. It’s time to set up TestFlight and start provisioning beta users. The team is pumped. Users are the lifeblood of any startup, and we’re feeling rejuvenated. Lists of beta users are being compiled, emails are flying out left and right, and confirmations are pouring in. Everything is going according to plan. We’ll wait until a week to give everyone a chance to respond, and then provision them all at once.

July 19, 2013—“Close, but no cigar”

“I’ve been trying to access developer center well over 24 hours but it’s not working. Of course this HAD to happen on the day that we start provisioning”

We’ve spent the last day trying to get access to Apple’s Developer Center, frantically Google for others who are stuck in the same predicament, but to no avail. Are we on some kind of Apple blacklist? Our prior collective “crap” is now a more emphatic, “Crap!” News breaks that Apple’s Developer Center is officially down. It’s good to know that we’re not the only one’s facing this problem. Apple should have it fixed in a day, and we’ll be ready to get our beta testers on board.

July 26, 2013—“A Canary in the hand, is worth two in the bush”

“Apple’s back up. I’ve added everyone to the beta. Email them and tell them to re-open TestFlight and begin the installation process”

We’ve been keeping people constantly updated on our status over the last week so as to hold their attention. It didn’t work well. People who had already begrudgingly waited a week from when we invited them on July 12, are tuning out. We should have put the app in their hand the day they agreed. We had committed a cardinal mistake — getting to “yes” and not closing. Always close. We agree to reach out again, 1:1, to each person, and try and re-close. Most quickly accept. People are nice. It’s important to remember that. A surprising positive is that a lot of latecomers to the party didn’t experience delays, so we end up with more beta testers than we had hoped for.

August 2013—“Do what we can, summer will have its flies”

“So there’s a bug that disables the keyboard so you can’t type anything anywhere in the app. I think we should prioritize finding a fix”

Summer is light on vacations and heavy on bugs. Our dedicated beta users continue to use Canary, and the bugs and feature requests pour in. The one week of Developer Center outage had pushed us back 2 weeks or more on the timeline, and bug fixes will push us even further. We’ve just wrapped up shooting a product video that we were proud of, but every single shot is of an iOS 6 phone — a platform suddenly approaching retirement. Now the specter of iOS 7 looms over us. While internet pundits continue fuming over the flaws in iOS 7’s design, almost everyone has come to terms with its inevitability. We’re still hoping to beat iOS 7, to be absolutely cutting edge from the moment we launch, if for a few moments. But that doesn’t stop gallows humor from entering team meetings.

September 25, 2013—“Close only counts in horseshoes and hand grenades”

“WE’RE LIVE!”

Canary has now officially launched to the App Store, a proud iOS 6 app. We submitted Canary on September 16, two days before the launch of iOS 7, guaranteeing that we wouldn’t be out before everyone started switching to a new iOS. But our victory is far from assured, and with iOS 7 adoption at “historic” rates, we’ve already begun the process of migrating Canary.

Lessons learned and a story

For those of you who have continued reading this far, I’ll leave you with a story that my father told me as a young child:

A little bird, flying south for the winter, got cold and landed in a field. While lying there, a cow came over and did a #2 on it. As the cold bird lay there in steaming cow excrement, it started to realize how warm it was getting, and was ecstatic! Laying there, warm and content, he started singing.

Just then, a passing cat heard the bird’s song, dug him out from the dung, and ate him.

Not everything that gets you in shit is bad and being neck deep is shit isn’t always bad either; but when you’re neck deep in shit, don’t sing. I don’t intend to sing about Canary just yet!