Brad Feld

Tag: ios

For starters, let’s look at some Golden Retriever puppies instead.

I watched most of the Apple announcement last week (I was on vacation and hanging out waiting for Amy, so I just plopped down on the floor and watched Special Events on the Apple TV channel.) I fell asleep for a few minutes part way through it. I turned it off about halfway through the iPhone X announcement.

I’ve been an Apple user for many years now. Every few years, I switch to an Android phone for a month (whatever the newest model is) but always end up going back to my iPhone. Whenever each new iPhone model has come out (for at least the past five years) there’s been a mad rush among my partners to make sure all of us have a new phone the day they ship. I even sported a rose gold one during one upgrade cycle just because I could.

When Amy and I went to lunch after the iPhone 8 and X announcement, she asked me if I was going to get a new iPhone. I said no. I realized I was profoundly uninspired – both by the new phone and the way the Apple team presented it. I’d go so far as to say I was bored, which as a lifetime nerd, is unusual when Amy lets me hang out and do anything related to computers (including watching TV about computers.)

Amy then said, “I didn’t mean the 8, I meant the X.”

For some reason, I’m completely uninterested right now in the iPhone X. I don’t know why. It might be the presentation. It might be that’s it’s not available for another few months. It might be that I just spend too much money and time fixing my iPhone 7+ screen (twice) after dropping it. Why twice? Because the first time I stupidly sent it over to one of the non-Apple “we can fix your iPhone for you for less money” stores who replaced the glass but totally screwed up a bunch of other things (the home button, the touch dynamics, and the edge feel of things.) That resulted in me buying a new iPhone 7+. Dumb Brad – just to go the Apple store even if it’s five miles further away and you have to drive instead of walk.

On the other hand, iOS 11 just installed on my phone while I was writing this post. A cursory glance shows that it’s working fine but other than different fonts, new icon styling, shading on an iMessage reply, and a different control center, it looks the same so far. At least I can play with fun new apps like Occipital’s TapMeasure to see how ARKit works.

I’m perplexed by the current Apple release cycle dynamics. I know they’ll mint money with the new phones, but my feeling of disappointment lingers as a user. Suddenly, I’m more inspired by Amazon’s new hardware.


Before I get into my rant of the morning, if you have a gluten intolerance, or just want less gluten in your life, we just invested in a company called Nima that can help you.

Today, as I was going through my daily reading, I read Fred Wilson’s Feature Friday: GBoard about Google’s new third-party keyboard app for iOS. I clicked on the link to download and try it and, as it was doing its thing, though to myself “why does Apple iOS Mail suck?” And then I thought “why does Apple iOS Calendar suck?”

When I’m using my iPhone, I spend a lot of time in Mail and Calendar. I’ve always been unhappy with Apple’s Mail and Calendar. I’ve gone through using lots of other ones, but in most cases, once the Mail or Calendar app is acquired by another, bigger company, it eventually stales out and vanishes. About a year about I started using Outlook on My iPhone and used it for a long time. I can’t remember what happened, but at some point I abandoned it and switched back to Apple Mail and Calendar.

As Gboard was downloading, I decided to try Gmail and Google Calendar on iOS for a while. I used them when they first came out and they were inferior to Apple’s Mail and Calendar. I tried them again about a year ago and they were good, but for some reason I didn’t stay with them.

I know that if I don’t use something for at least some extended period of time it won’t stick. Some I’m going to try having Google World on my iPhone until at least June 1st. At that point I’ll re-evaluate.

If you have any hints or suggestions, I’m all ears.


Yesterday I wrote about getting stuck in an hour long reading loop on the Apple / FBI situation. As much as I didn’t want it to happen again today, it did. More on that in a minute.

But first, I want to encourage you to go watch the movie Race which is the story of Jesse Owens and the 1936 Berlin Olympics. It was superb and the double entendre of the title played out for a full two hours as the movie made us think hard about race in America in the 1930s and what was happening in Nazi Germany at the same time. I also thought the acting by the primary characters, including Stephan James (Jesse Owens), Jason Sudeikis (Larry Sanders – Owens coach), and Barnaby Metschurat (Joseph Goebbels – Nazi propaganda minister) was incredible.  Metschurat was a special bonus – he brought an extremely uncomfortable feeling of deep menace to every scene he is in.

At the end of the movie, the entire theater clapped (that doesn’t happen very often.) As Amy and I walked to our car, we commented that while we’ve made a lot of progress since 1936, we’ve got a very long way to go. On our way home, we talked about current events against a backdrop of 1936 racism in America and a systemic racism in preparation for a genocide in Nazi Germany. I read the NPR review of Race this morning after seeing the movie and agreed with everything in it.

This morning, as I was going through my morning reading stuff online, I fell down the FBI / Apple rabbit hole again. It’s interesting how the substantive analysis is improving every day, and I finally feel like I have my mind around the technical issue, the mistakes the government already made that prevented it from getting the data it wanted, Apple’s consistent and appropriate supportive behavior with law enforcement up to this point, the government overreach that is now happening, and the correctness of Apple’s position. In other words, nothing has changed in my opinion that Apple is in the right in this situation, but I can now explain it a lot more clearly.

If you want to spend time in the rabbit hole with me (I’ve set up a couch, have poured some drinks, and have nice music playing down here), here are some things to read.

As humans, I think it’s important to remember that the TechnoCore is paying attention to this and watching everything we do. Even if they are looking back at us from the future, what we are doing now matters.


Super Cooper (our new dog – now one year old) woke me up at 4:45 this morning so I got up, let him out, got a cup of coffee, sat down in front of my computer, and spent the next hour going down the rabbit hole of the FBI / Apple phone unlock backdoor encryption security controversy.

After an hour of reading, I feel even more certain that Apple is totally in the right and the FBI’s request should be denied.

The easiest to understand argument is Bruce Schneier‘s in the Washington Post titled Why you should side with Apple, not the FBI, in the San Bernardino iPhone caseHis punch line is extremely clear.

“Either everyone gets security or no one does. Either everyone gets access or no one does. The current case is about a single iPhone 5c, but the precedent it sets will apply to all smartphones, computers, cars and everything the Internet of Things promises. The danger is that the court’s demands will pave the way to the FBI forcing Apple and others to reduce the security levels of their smart phones and computers, as well as the security of cars, medical devices, homes, and everything else that will soon be computerized. The FBI may be targeting the iPhone of the San Bernardino shooter, but its actions imperil us all.”

Given that the law being used to try to compel Apple to do this is based on the All Writs Act of 1789, precedent matters a lot here. And, if you thought the legal decisions from 1789 anticipated the digital age, please fasten your seat belts – or maybe even encase yourself in an impermeable bubble – for the next 50 years as it’s going to get really complicated.

Once I got past the advocacy articles like Why Apple Is Right to Challenge an Order to Help the F.B.I. in the NY Times, I read a few of the “what is really going on here” articles like Wired’s Apple’s FBI Battle Is Complicated. Here’s What’s Really Going On. The context was starting to repeat, so I got it at a high level but wanted to understand the technical underpinnings of what was happening.

Since it’s the Internet, it was pretty easy to find that. The Motherboard article Why the FBI’s Order to Apple Is So Technically Clever was a good start. Dan Guido’s Trail of Bits post Apple can comply with the FBI court order was super interesting since he only focused on the technical aspects rather – focusing on feasibility rather than getting tangled up in whether it’s a good idea or not. Ars Technica has an article that ads a little in Encryption isn’t at stake, the FBI knows Apple already has the desired key.

I think wandered around a few random articles. Troy Hunt’s Everything you need to know about the Apple versus FBI case has some great historical context and then unloads with current activity including Google’s CEO Sundar Pichai’s Twitter support of Apple / Tim Cook. I ended with Why Tim Cook is wrong: A privacy advocate’s view.

Interestingly (and not surprisingly), the titles don’t reflect the actual critical thinking you can derive from reading the article, so just scanning headlines creates huge bias, whether you realize it or not. When I started reading the various articles, I immediately forgot most of the headlines and was surprised by some of them when I put this post together since the headline didn’t correspond with the message of the post.

I expect there will be lots of additional commentary on this as it continues to unfold in court and in public view. What I read, and thought about this morning, reinforced my view that I’m very glad Tim Cook and Apple are taking a public – and loud – stand against this. We are going to have to deal with stuff like this with increasing frequency over the next 50 years and what happens in the next decade is going to matter a lot.


Here’s a perplexing thing to ponder.

After trying virtually every email configuration on iPhone and Android devices, the best experience that I have had so far is using Microsoft Outlook on my Apple iPhone to access Google Gmail.

I’ve been using Outlook on my iPhone for the past few months. I’ve tried several times to go back to Apple Mail, but it is impossibly bad when compared to Outlook. I’ve also tried using the Google iOS Gmail client, which – while better than Apple Mail – is still very klutzy at certain things.

I know that Microsoft Outlook is really Acompli rebranded at Outlook, but in the eight months since the acquisition the product has continued to get better and better.

Go figure.


I just spent around an hour shrinking my Facebook friends list from 1,500+ to 535. I ignored another 2,000 friend requests. I made my entire Facebook feed from the beginning of time private, which eliminated 33,000+ followers (dear Facebook followers – you really meant to follow me on Twitter, that’s where all the public fun is.) I turned off all my email notifications.

Hint – if you want to do stuff like this, use the iOS app instead of the web app – it’s so, so, so much faster. Last night I tried to do this on the Facebook web app in front of the TV. It was a total fail – every few unfriends caused the page to refresh and I had to start scrolling all over again. This morning I was pleasantly surprised with how much better / cleaner / faster it was with the iOS app.

I cleared out all my outstanding LinkedIn friend requests. I’m much more promiscuous there and will accept anyone who either I recognize, writes me a personal note, or seems interesting. I turned off all my email notifications and re-inserted LinkedIn in my Daily browser folder.

I spent some time fixing up all the friend requests in Goodreads. I don’t care who follows me, but I got rid of the folks I follow who I don’t know and focused that list a lot better to see if the feed would be useful going forward.

I just deleted everything off my iPhone that I never use and put the infrequently used stuff in various folders. That took things from eight screens to two. Charm King – how the fuck did you end up on my iPhone?

It will continue. Feedly – clean up feeds and add ones from companies in our portfolio that I haven’t been following. Consolidate all photos and music in one place and make sure they are accessible from all computers. And whatever else I run into.

There’s something very satisfying about the winter cleaning that I seem to do every year.


A month ago, I decided to switch from my iOS devices to Android devices for a month and see how it went. I turned off my iPhone and iPad and turned on a Nexus 5 and Nexus 7.

I enjoyed the Nexus / Android a lot.

But I couldn’t decide if I liked it better than the iOS experience. It was different in some ways and the same in others.

So yesterday after my digital sabbath was over I turned off my Nexus devices and turned on my iOS devices. I figured the only way I’d be able to really decided which I liked better was to switch back and decide how I felt after a few days.

The meta of the experience is that they are both great devices. Every app I used regularly on my iPhone existed for the Nexus. I found a few new things on the Nexus that I wasn’t using on my iPhone. And I started using my Nexus differently in a few ways, although I expect that behavior will carry back to my iPhone.

So – the experiment was completely and totally inconclusive for me.


I’m going to spend January using an Android phone and tablet instead of my iPhone and iPad. My Nexus 5 and Nexus 7 are charged up and ready to go – all I need is a SIM card.

I’ve been an iPhone user since I ditched my HTC Dash running some version of Windows Mobile 6 oh so many years ago. I’ve struggled with battery life, broken screens, water damage, and this insatiable urge to upgrade to the latest iPhone the day it comes out. When I travel overseas, I’ve gone completely off the rails trying to figure out how to get a SIM that works even in an unlocked iPhone 4. But, overall the iPhone has been good to me and the companies I invest in.

But recently I’ve been sad. I didn’t like iOS 7 when it came out and I’m still not loving it. I felt bummed out by the latest iPhone release which seems to have – well – nothing really new except some fingerprint thing and different colors. And as more and more of my world is Google-related, I find the iOS apps fine, but lacking.

I asked Fred Wilson which Android phone I should get. Fred’s been an unapologetic Android fan from the beginning because he hates the closedness of Apple. He told me “Nexus 7” so I bought it without looking. When it arrived, I realized I now had a really big phone since the Nexus 7 is actually a tablet. I just assumed it was better than the Nexus 5 (how’s that for not paying attention.) So I went online and got a Nexus 5 also.

That inspired me to run the January Android experiment. I use an iPad Mini for some stuff at home, although my favorite device to read on lately has been the Kindle Fire HD. But I’m going to see if I can consolidate all my activity to the Nexus 5 and Nexus 7 for January.

The one big miss was a SIM card. I ordered one with the Nexus 7 and then didn’t get one for the Nexus 5, as I assumed I’d just use the one that came with the Nexus 7 for the Nexus 5 (since the Nexus 7 would always be on WiFi). When the Nexus 7 arrived, the SIM and the wireless charging pad weren’t in the box. I’ve tried to figure out how to tell Google they blew the shipping on this (since I ordered it directly from Google Play) but there doesn’t seem to be any way to do that. So I ordered another wireless charging pad and I’ll swing by one of those old fashioned phone stores tomorrow and pick up a SIM.

In the mean time, if you are an Android fan, I’m all ears for any suggestions, tips, and tricks that you have for my month of Android.


This is a note from your Gmail tech support person (my life in a parallel universe) just trying to help with whatever frustration you are having today.

Over the weekend I noticed that my iPhone (which had recently upgraded to the latest iOS (5.0.1) was now regularly giving me an error from within the native email app. A little box would pop up and tell me that my Exchange Password was incorrect. I use Gmail, but use the Exchange connector on the iPhone (as recommended by Google). Until recently, this was working just fine.

I entered my password 100 times or so in a fit of stubbornness. It worked every now and then. However, when my iPad started borking with the same error message, I decided to figure out the problem.

My search “gmail iphone exchange password incorrect” turned up some interesting stuff. I quickly figured out the problem what the Google Captcha. Apparently the Microsoft connector logs in but then borks on the Captcha which is never surfaced in the connector. Fortunately, there’s an easy way to unlock (or disable) the Captcha in Google Apps.

It seems like Google could fix this on their end without waiting for Apple. Just don’t toss up the Captcha whenever an iOS device hits Gmail. My guess is a recent push on Google’s side broke this as I didn’t notice a real iOS upgrade correlation. While at first I thought it might be iOS 5.0.1, I realized there was a few day delay, pinning the issue most likely back on Google.

Either way, my near term frustration has once again vaporized and I can resume ferociously emailing on my iOS devices.