Brad Feld

Tag: apple

Someone mentioned that Apple stock is having a difficult time right now, along with their Q4 performance, China strategy, and “let’s just raise the price on iPhones to make up for lower demand” strategy.

I’m not really interested in Apple stock (I don’t own any.) I’m more concerned with the Apple Dock. My MacOS Dock to be more specific.

Here’s the one from my laptop.

Here’s the one from my desktop, which is in a room about 25 feet away.

Why in the world are they different? Many things sync via iCloud already and even though the UX is obtuse to get it set up correctly across machines, when it’s finally set it, it works pretty well.

But the Dock? Seriously?

In contrast, following are the two Chrome ribbons on my two machines.

Shockingly similar, like you’d expect.

It’s fascinating to me that even in this “all cloud, all the time” era, Apple still is struggling with the dichotomy between a “computer-centric” view of the world and a “user-centric” view of the world. Sync across machines is simply not a new idea. I get that there is endless complexity everywhere, but this is one of those examples that I think of every day.


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.


After all these years, I’m still a heavy RSS user. Every morning I click on my Daily folder in Chrome, open it up, and spend whatever time I feel like on it. The vast majority of what I read is in Feedly and includes my VC Collection as well as a bunch of other stuff. It’s almost entirely tech related, as I stay away from mainstream media during the week (e.g. no CNN, no CNBC, no NYT, no WSJ, no USA Today, no … well – you get the idea) since I view all this stuff as an intellectual distraction (and much of it is just entertainment anyway, and I’d rather read a book.)

This morning I came across a number of interesting things that created some intellectual dissonance in my brain since they came from different perspectives. I’d categorize it as the collision between optimist and pessimist, startup and already started up, and offense vs. defense. However, they all shared one thing in common – the message and thoughts were clear.

Let’s start with Tim Cook’s remarkable Message to Our Customers around the San Bernardino case and the need for encryption. My first reaction was wow, my second reaction was to read it again slowly, and my third reaction was to clap quietly in the darkness of my office. I then went on an exploration of the web to understand the All Writs Act of 1789 which is what the FBI is using to justify an expansion of its authority. I love the last two paragraphs as they reflect how I feel.

“We are challenging the FBI’s demands with the deepest respect for American democracy and a love of our country. We believe it would be in the best interest of everyone to step back and consider the implications.

While we believe the FBI’s intentions are good, it would be wrong for the government to force us to build a backdoor into our products. And ultimately, we fear that this demand would undermine the very freedoms and liberty our government is meant to protect.”

Thank you Tim Cook and Apple for starting my day out with something deeply relevant to our near term, and long term, future in a digital age.

Shortly after I came across Danielle Morrill’s post Surviving Whatever Comes Next and Heidi Roizen’s post Dear Startups: Here’s How to Stay AliveI’m an investor in Danielle’s company Mattermark and was partners with Heidi at Mobius Venture Capital. I have deep respect for each of them, think they are excellent writers, and thought there were plenty of actionable items in each of their posts, unlike many of the things people I’ve seen in the last few weeks about how the technology / startup world is ending.

Unlike the sentiment I’ve been hearing in the background about deal pace slowing down (not directly – no one is saying it – but lots of folks are signaling it through body language and clearly hedging about what they are actually thinking because they aren’t sure yet), our deal pace at Foundry Group is unchanged. Since we started in 2007, we’ve done around ten new investments per year. I expect in 2016 we’ll do about ten new investments, in 2017 we’ll do about ten new investments, in 2018 we’ll do about ten new investments – you get the picture. We have a deeply held belief that to maximize the value and opportunity in a VC fund, investment pace should be consistent over a very long period of time. We did about ten investments in 2007, 2008, and 2009 – which, if I remember correctly, is a period of time referred to as the Global Financial Crisis. Hmmm …

So it was fun to see my partner Seth’s post titled Welcome to Foundry on the same morning as Danielle and Heidi’s posts. That started the intellectual dissonance in my brain. If you want to see what Seth sends every company he joins the board of after we make an investment in, it’s a good read. It also clearly expresses how we approach working with companies the day after we become an investor.

I then read Ian Hathaway‘s great article for the Brookings Institute titled Accelerating growth: Startup accelerator programs in the United StatesThere are a few people doing real research of the impact of Accelerators and Ian’s work is outstanding. If you are interested in accelerators, how they work, how they impact company creation, and what trajectory they are on, read this article slowly. It’s got a bonus video interview with me embedded in it.

I’ll end with Joanne Wilson’s post #DianeProject. Joanne shared a bunch of info about the #DianeProject with me when we were together in LA two weeks ago. While I don’t know Kathyrn Finney, I now know of her and her platform Digital Undivided. I strongly recommend that you pay $0.99 (like I just did) to get a copy of the report The Real Unicorns of Tech: Black Women Founders, #ProjectDiane. The data is shocking, and there is an incredible paragraph buried deep within it.

“A small pool of angel and venture investors fund a majority of Black women Founders. For those in the $100,000-$1 million funding range, a majority of their funders were local accelerator programs and small venture firms (under $10 million in management). One angel investor, Joanne Wilson and Gotham Gal Ventures, has invested in three of the 11 companies that raised over $1 million. On the traditional venture rm side, Kapor Capital and Comcast’s Catalyst Fund have invested in at least two of the Black woman-led startups in the $1 million club. Wilson, Kapor, and Comcast often invest together, aka “co-invest”, in companies, thus increasing the amount of funding a company receives.”

So – was that more interesting than CNN or CNBC?


I’m three days into trying to figure out the best way to deal with our large collection of digital photos that have accumulated since 2000.

When I started (on Christmas Day – I figured it was a one day project) Picasa said we had around 35,000 photos. After several different clean up approaches, we now have about 15,000. That’s the power of Duplicate Photos Fixer Pro which has been probably the cleanest and most straightforward part of this whole exercise.

But – let’s start from the beginning. Several years ago I created a shared Dropbox folder for me and Amy and moved all of our many folders of photos into one folder in Dropbox. I didn’t try to organize anything then – just get them all in one place. I then installed Picasa on each computer, spent a little while with Amy figuring it out, and let time pass from there.

Amy spent a lot of time over the past few years cleaning up photos, arranging them in folders, and copying things from place to place from within Picasa. We had various applications, like Dropbox and iTunes, set up iPhone sync directories. We avoided iPhoto, but every now and then it opened up somewhere and did something. Amy would sync her digital SLR photos with Picasa and then move them around. A bunch of other stuff probably happened in the background as we connected Picasa to the web, installed various Google apps on our machines, and I had a brief foray into using an Android phone.

However, I mostly ignored the problem. Every few months Amy would get frustrated looking for a photo and ask if I was ever going to clean everything up. We constantly talked about getting our iPhones set up to share stuff in a useful way. I bought Amy a new camera (the Sony A7) and decided as part of it I was going to clean up the mess that I’d help create over the years.

I vaguely remembered installing a Google Photo uploader thing on my desktop at work several months ago and letting it run for a few days while it uploaded the mess of photos we had. I looked at https://photos.google.com/ and scrolled through a huge photo collection. Yup – it uploaded them, although preserved none of the folder hierarchy Amy had painstakingly created. And then I started noticing lots and lots of duplicates. That’s weird – I wonder how that happened. After poking around for a way to have Google just automatically eliminate them, I discovered no such feature existed. Ok – I can delete a bunch of duplicates – let’s just share all with Amy. Oops – no way to do that.

Well, that would have been too easy. So, I spent most of Christmas Day afternoon using Picasa to clean up all the folder hierarchies, move photos from the hundreds of randomly named (usually with a date) folders, or the folders named “Move These Later 7.” I started as a Picasa novice and now have mastered it, with all of its quirks.

And then I realized there we had nested folders of duplicates spread out all over the place. Aha – now I knew why Google had duplicates everywhere. After a few searches, I found Duplicate Photos Fixer Pro and, after making a backup of the gigantic photo folder (via the web – so there was no web to desktop to web traffic), I quickly reduced our photo collection by over 50%.

I went to bed and let Dropbox and Picasa do their thing as everything synchronized on my painfully slow home Internet connection (there’s nothing like seeing a “10 hours left” message to decide to call it quits for the night.)

When I woke up yesterday, Dropbox looked fine but Picasa wasn’t synchronized. After messing around with Picasa for a while, I decided to just unlink the scanned folder (which was just the high level photos folder) and let it reindex. That worked. I messed around with the Dropbox hierarchy some more to try to clean things up. I noticed that Picasa again got out of sync. After doing this a few times, I started reading about Picasa on the web and my soul was crushed. I had a fantasy that the long term solution for everything could be something that lived on top of Dropbox, but as I realized that Picasa was getting old and stale (it shows in the UI) and there was a pretty clear path for Google toward everything being entirely web, Android, and Google+ (or – well – Google Photos) based. In other words, Picasa isn’t likely a long term solution.

Deep breath. At this point I checked with my partner Ryan who has 10 zillion photos and he quickly responded Apple Photo plus iCloud Photo Library (iPL) with a backup on Google Photos.

So I spent the rest of yesterday getting my mind around Apple Photos including a multi-machine and user struggle to understand the implications of what Apple thinks a family is and what can be shared between family members. Of course, the relic of the Apple iPhoto library didn’t help, as it introduced a new wave of duplicates which Duplicate Photos Fixer Pro figured out. Eventually I realized I had about 20 remnant Picasa temp files, each which were getting indexed in Apple Photos, so I hunted down and expunged them all. I started a bunch of folders uploading (I was trying to create some semblance of an Album structure). I was getting the hang out it, but it was dinner time so I was done until the morning.

When I woke up this morning, iPL told me that it has 11,781 files left to upload. Amy and I went out to breakfast. When I got back 90 minutes later, iPL now only had 11,721 files left to upload. Well – that’s not going to work.

I gave up, deleted all the photos from my instance of Apple Photos that was uploading, and read a draft of Eliot Peper‘s newest book Cumulus, which was awesome. I did a few other things, had dinner, and am still waiting for Photos/iCloud to figure out what it’s doing several hours later.

For now, I’m taking a break as I ponder my next move. Suggestions welcome.


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.


A year ago if you had suggested that I’d be using Microsoft Outlook on my iPhone instead of the Apple Mail app, I would have said, simply, “No Fucking Way.” And I would have been wrong.

It’s kind of like chocolate in my peanut butter.

When I try something new, I use it for two weeks to see if it sticks. A month ago, my partner Jason told me he was loving Outlook on the iPhone. I figured it wouldn’t last but I was wrong. So two weeks ago I moved my Apple Mail icon to the last page on the iPhone and moved the Outlook app down into the special reserved place for email.

Outlook on the iPhone is better than Apple Mail on the iPhone. It’s one of those perplexing things – I’ve tried many of the other iOS email clients and none of them were ever more than incrementally better. I go back and forth with the Google Gmail iOS client but it never sticks for some reason, probably the UX. I tried Google Inbox for a few days and my brain simply doesn’t process email the way it presents it. So I kept ending up back at the Apple Mail iOS app.

While the Apple Mail iOS app is fine, it doesn’t delight, especially when using Gmail. Mail is often slow to download. Push has gotten better in a recent release, but I still find myself waiting for emails to download. Search is lousy. Calendar integration is non-existent.

Outlook is better at all of these things. It’s not that it adds any dramatic new features, but it does the stuff I’ve expected Apple Mail to do for many years. And, when I actually think about what is going on, I’m using Microsoft Outlook on my Apple iPhone to read my Google Gmail.

What iOS email client do you use and why?


There was plenty of Apple news yesterday, but the one that lit me up was the announcement that Apple is partnering with the National Center for Women and Information Technology  to help create a broader pipeline of female technology workers.

I’ve been chair of NCWIT since 2006 and have worked closely with Lucy Sanders, the founder and CEO. I’ve learned an amazing amount from her, and NCWIT, about the dynamics around women in information, the challenges we collectively face as an industry, and how to impact it.

While we’ve raised money from lots of different organizations, Apple’s give of about $10 million over four years is the largest corporate gift we’ve received to date. The relationship that Apple and NCWIT have developed over the years is a wonderful example of a large technology organization getting the issue, engaging with it, learning how to impact it, and putting its money where its mouth is.

NCWIT’s goal with this specific funding from Apple is to double the number of four-year-degree recipients supported by NCWIT’s internships, scholarships and other resources, and to reach 10,000 middle school girls over the next few years.

Apple – thank you for your leadership in this area.

Oh – and one more thing. Here’s a photo of this year’s NCWIT Aspirations in Computing award winners. These young women are the future.

NCWIT Aspirations Award


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.