the candler blog

Marco Arment and Context

Technology, Writing

Marco Arment is many things to many people. He’s a podcaster of great energy, one of the current best in the business. He’s an independent iOS developer who made Instapaper, an early hit on the iPhone and then the iPad, and currently develops the popular podcasting client, Overcast. He helped build Tumblr, which would ultimately be bought by Yahoo for over $1 billion.

Marco is a tech success story. He is a celebrity. When the media treats him like one, though, it catches him off guard. I don’t understand why.

On Sunday, Marco published “Don’t order the fish,” a piece that takes Apple to task for Apple Music. I’m going to quote Marco here directly. This bit comes after praising Apple’s rock-solid sync services, like push notifications and iCloud Photo Library. Then this:

But the iTunes Store back-end is a toxic hellstew of unreliability. Everything that touches the iTunes Store has a spotty record for me and almost every Mac owner I know.

And the iTunes app itself is the toxic hellstew. iTunes has an impossible combination of tasks on its plate that cannot be done well. iTunes is the definition of cruft and technical debt.

And later:

With the introduction of Apple Music, Apple confusingly introduced a confusing service backed by the iTunes Store that’s confusingly integrated into iTunes and the iOS Music app (don’t even get me started on that) and partially, maybe, mostly replaces the also very confusing and historically unreliable iTunes Match.

So iTunes is a toxic hellstew of technical cruft and a toxic hellstew of UI design, in the middle of a transition between two partly redundant cloud services, both of which are confusing and vague to most people about which songs of theirs are in the cloud, which are safe to delete, and which ones they actually have.

One could argue that the above takes Marco out of context; that the only way to get the full impact of Marco’s piece is to read it in full. That’s only sort of true, because context often runs deeper than a single article.

Today, CNBC’s Squawk Alley did a segment on Marco’s piece, attributing “toxic hellstew” to him. This seems to be bugging Marco.

Marco has updated his article to include a link to a catchy song by Jonathan Mann about the 2014 WWDC keynote. One line Mann picked up on was Tim Cook quoting the headline of a ZDNet article by Adrian Kingsley-Hughes: “Android fragmentation turning devices into a toxic hellstew of vulnerabilities.” Cook saying the line became something of a meme for a short while, most popularly in Mann’s song.

I follow Apple nerd stuff pretty closely, so I understood the reference. The thing is: it doesn’t much matter who invented the term, Marco absolutely just tied it to both Apple and himself. “iTunes is a toxic hellstew of technical cruft and a toxic hellstew of UI design” is absolutely something Marco Arment said. It sounds like he meant it and anyone, in any form of media, can pick up his words and run with them.

This isn’t the first time Marco’s words have taken on extra meaning. Back in January he published “Apple has lost the functional high ground,” a piece that blew up overnight and resulted in a mea culpa the following day. That piece, turns out, offers some great advice for Marco today:

I now need to write everything with the fear that any hastily written article might end up on TV, with the most extreme word in the article singled out with my name on it forever.


I understand Marco’s dilemma. He’s opinionated and loves blogging. But he sometimes acts oblivious to his standing in the tech community. His success has bred him an audience; his words hold more weight because of his status. I have trouble believing he didn’t know there would be an “Influential iOS developer Marco Arment says…” narrative thread others would pick up on from his post.

Back when the “functional high ground” thing flared up, I recall Marco discussing on his podcast, ATP, the idea that people who listen to the show and have been reading him for years have a better understanding of what that article was about. That’s true, but it’s irrelevant. The written word is amazing because it can be so easily quoted. Authors can be held accountable on a fairly even playing field. No inflection, no body language; just words.

It would be nice if everyone had the context they needed to understand the author’s intent, but that’s not reasonable. I know Marco’s work extremely well, but that’s years worth of material that I’ve slowly incorporated into my own knowledge. I’ve peppered this piece with a few tiny zingers that only those who follow Apple and/or Marco may understand, but that context doesn’t form the bedrock of this piece.

I love reading and listening to Marco. I hope he never slows down his creative output. I just think he shouldn’t be surprised when people take his words at face value, which is ultimately all they’re worth.

#buysmall Newsletter


#buysmall is a very cool new newsletter from the folks behind Cotton Bureau. The idea is to spotlight the wares of some pretty neat small businesses. Here’s how they describe it in the first edition:

#buysmall is our way of shining a light on the interesting, clever, and/or exceptional folks who are in this fight, too. Business isn’t a zero-sum game. It’s a great big world out there, room enough for all of us, and when we help each other, we help ourselves.

I love the pennants they showed off from Oxford Pennant, and I’m kind of lusting after this Grovemade Walnut Monitor Stand. This is a no-brainer instant subscribe for me.

Apple Music is My Dream Streaming Service

Music, Technology

Jim Dalrymple, yesterday, in a post titled “Apple Music is a nightmare and I’m done with it”:

I had high hopes for Apple Music. I really wanted it to work and become my default music streaming service, but after the problems I’ve experienced over the last couple of weeks, I’m disabling it altogether.

His piece is a scathing indictment of the service. Dalrymple says he is “missing about 4,700 songs from my library with little hope of getting them back.” That sucks big time. My heart goes out to him.

I have tried to replicate Jim’s problems, but I can’t. My guess is that the culprit is his transitioning from Beats Music to Apple Music, which I never did. So maybe I dodged a bullet there.

As to where his 4,700 songs went: that’s scary and I want to know more about it. I understand that Jim is a bit beleaguered at this point, but I really wish he would go into more detail about how he experienced his songs going missing. Here’s what he tells us:

Over the weekend, I turned off Apple Music and it took large chunks of my purchased music with it. Sadly, many of the songs were added from CDs years ago that I no longer have access to. Looking at my old iTunes Match library, before Apple Music, I’m missing about 4,700 songs.

It’s Apple’s fault that these services are so difficult to talk about, but I don’t get what Jim’s iTunes Match library is in this context. Is he looking at a smart playlist? Are they still in his library but showing up with dreaded exclamation points? What I think is important for Apple Music and iTunes users to learn from Jim’s troubles is how to know what you don’t have. Unless I knew which tracks to look for, I don’t know that I’d know what I was missing. Right now, though, I think this should give us all huge pause before turning off Apple Music. I hope Jim (or anyone) can shed some light on what went wrong and how to prevent it.1

Now, all that said, I do want to share my experience with Apple Music. I absolutely love it. If Apple Music is Jim’s nightmare, it’s my dream. For me it’s the perfect mix of my own musical tastes (my 98+ GB library that I’ve been building since at least 2002) and an infinite library of songs brought to my attention by others. That integration with my own library is crucial, and it’s really what I missed with Spotify and Rdio, the only other streaming services I ever really tried.

I’ll concede that there is a learning curve to using Apple Music in conjunction with your own library. The highest point of friction for me is search, which is basically the only tool I use to get to music I want. You can search either Apple Music or My Music. It takes some getting used to, but I think of it like this:

  • My Music is your iTunes library
  • Apple Music is all2 other music; it’s the streaming service

There are things in my library3 that I know will never be available in Apple Music, like my single track of the entirety of Radiohead’s OK Computer that I sometimes like to listen to even though I have the full album as tracks and it sounds just fine. I should mention that I’ve been an iTunes Match subscriber since February 2013, so my entire library was already in Apple’s cloud. Flipping on Apple Music created zero friction for me.

Since subscribing to the streaming service, I’ve been adding music to my library left and right, mostly while listening to Beats 1 (sometimes by way of Connect). I hear something I like and I either add it to “My Music” or put it into a playlist. That last part, adding songs from the Apple Music to my playlists, is pretty amazing. I have a playlist for running4 that went stagnant for months. Now I add music to it a few times a week. I love that I didn’t have to recreate that playlist in Apple Music with matched tracks or anything; I get to have the best of both worlds.

Jim Dalrymple is one of the most respected writers in the Apple and tech communities. A one-word blog post from him (usually “Nope.” or “Yep.”) holds more weight than the sum total of all Apple “analysis” out there, so a blistering takedown from him is not something to be dismissed. I hope Apple does right by him and other users affected by any bugginess.

I just want to put it out there that Apple Music is the best streaming service I have ever used. My guess is that there are a lot of people out there who have used it without any issues. But that’s not much of a story.

  1. Back up your libraries, folks. I use Backblaze. Use this link to sign up for it and I get a little kickback.

  2. I know it’s not all music ever. I’m being hyperbolic, but the massiveness of streaming libraries feels like every song ever to me. Pulling the hyperbole back and saying something like “most other music” feels inaccurate too.

  3. Ahem, My Music, see above where I said Apple doesn’t make it easy to talk about this stuff.

  4. I really don’t mean to talk about running this much. It just happens…

Day One as Running Diary

Fitness, Technology

When I wrote about running with my Apple Watch two weeks ago, I mentioned in a footnote that “entering run notes into Day One” was a key reason I preferred keeping my phone on me. I’d like to elaborate on that just a small bit.

In case you don’t know, Day One is a journaling app for iOS and Mac. You can file your writings by date, tag posts, add a photo and even add numerous bits of metadata to each piece. Your location, the weather, what music you’re listening to and whether or not you were walking, driving or sitting still can all be attached to each entry. It’s like your own private little blog (it can even become a public blog if you like).1

While I have done plenty of writing in Day One, lately I tend to do most of my writing either in a Field Notes memo book or in Ulysses on my Mac. But Day One is still one of my most used apps. I’ve been using it for over a year2 as a running diary. Every time I run I create an entry with a photo (usually a selfie) and a few words about how I felt during the run. I always add the tag “Running” to these so I can keep track.

Now, RunKeeper can hold all of this information pretty well too. Each run can have a photo and a note attached to it. I tend to upload photos to RunKeeper as well, and will sometimes add a short note. The truth is that, while RunKeeper does an incredible job displaying and tracking data related to exercise, it’s not great at displaying anything personal. It’s a colder app, which is fitting since it needs to be as reliable as a stopwatch. But for storing and retrieving how running makes me feel I need something more personal, more beautiful. Day One fits the bill.

Here are screen grabs of what my Day One “Timeline” (left) and “Photos” (right) views look like today.

Somewhere around the end of my run, I take a photo of myself. I may use filters in VSCO Cam, but more often I’ve been enjoying Apple’s built-in photo filters. As I cool down I create a new Day One photo entry and tap out a few notes.3 I may include my split times, or I may just talk about how I feel and what in my life may have caused the run to go the way it did (e.g. too little sleep, a heavy meal). Sometimes it has almost nothing to do with running, as when I spotted a dog that had ventured out of his owner’s yard and I helped him get back home.

This is where Day One really shines over something like RunKeeper. I run for many reasons; going faster and further are only a small part of that. Running is now part of my routine. It’s part of (most of) my days. There is a macro view of the thoughts I have while running and what the long-term effects it has on my health and demeanor that Day One allows me to track. No other tool comes close.

  1. When I get the urge to tweet something that I really shouldn’t, I type it into Day One and tag it as “Untweet.” I like to think this has kept me out of more than a few shouting matches.

  2. First running entry: November 15, 2013.

  3. Day One also offers an excellent Watch app that allows me to pre-populate a post with a “Running” tag and the most recent photo. I don’t really use this though as I’m so used to actually typing out the entry as I create it.

The Internet Sucks: A Reading List

Technology, Writing

In the past week (and then some) I’ve read so many stories that have done an excellent job articulating something I’ve been feeling for awhile now: the Internet sucks, and this is a new thing. I’ve tried to put this into words before, but the below articles do a better job.

The Internet is a vast landscape, yet all the same garbage bubbles up to the top these days. I don’t have any answers, but I do know it’s something we should be vigilant about. The web is too important to give up on. So here’s a reading list enumerating where we are today.

“Self Referential” by Gabe Weatherhead:

It’s obvious that publishing original content is a fading career opportunity and is being replaced by micro blogs such as Medium, Twitter and even Instagram. Not only do I think these are replacing individual blogs, such as this site, but I believe they are actively speeding the demise of original work.

“The Web We Have to Save” by Hossein Derakhshan:

There’s no question to me that the diversity of themes and opinions is less online today than it was in the past. New, different, and challenging ideas get suppressed by today’s social networks because their ranking strategies prioritize the popular and habitual.

“Escaping the new media cargo cult” by David Moldawer:

Whether you blame Facebook, Buzzfeed, HuffPo, or “algorithms,” the new media landscape has grown a big fat mainstream of its own. Not at one particular site, but in the sense of a particular mechanic of creative expression: tailored for clicks, pasteurized, grabby. The long tail of odd and authentic content is bigger than ever, but if you find your content the way most people do, through the algorithmically warped suggestions in your social media feeds, the stuff you stumble onto feels less like writing and more like wordage, a sort of tips-and-tragedies lorem ipsum.

“The trolls are winning the battle for the Internet” by Ellen Pao:

The Internet started as a bastion for free expression. It encouraged broad engagement and a diversity of ideas. Over time, however, that openness has enabled the harassment of people for their views, experiences, appearances or demographic backgrounds. Balancing free expression with privacy and the protection of participants has always been a challenge for open-content platforms on the Internet. But that balancing act is getting harder. The trolls are winning.

It’s Friday, so let’s end on a high note. Here’s a link to the instructions for the Penicillin, a cocktail my pal Noah turned me on to with a tweet. And here’s a video of its inventor, Sam Ross, demonstrating how to properly make it. The Internet doesn’t always suck, it seems.

Bottoms up.

My First Field Notes


Last night I decided to tidy up my collection of Field Notes memo books. For a few years now I’ve kept one in my back pocket everywhere I go. Even if most days I don’t grab for it, I’m happy to have it there just in case.

After organizing my unused and sealed books, I went to put my filled up books in order.1 With few exceptions, almost every memo book I’ve written in has functioned as a sort of ongoing journal. To-do lists, creative pieces and work-related notes are often mixed in with more diaristic writing, but there is certainly an order to the books.

While flipping through pages to find the dates they were started and finished2 last night, I came across my first Field Notes memo book. I actually remember picking up that first three-pack, a limited edition Raven’s Wing from 2010, at McNally-Jackson, one of the great NYC book stores, long before I knew that these little notebooks would become pined after by collectors.3

I was surprised to find a notebook that actually said flat out that it was the first of the collection. When I opened up this little black book, there it was staring me in the face. My first Field Notes. An occasion worth calling out back then, apparently.

The next thing that surprised me was how specific the entry was about my relationship to digital tools, and how excited I seemed to be to be putting pen to paper once again. I had no idea, back in 2011, that writing in Field Notes would become a habit. But it has.

So I thought it would be fun to post the first thing I ever wrote in a Field Notes here on the candler blog. This was never supposed to see the light of day, but I rather like reading it again four years down the line. I wonder what other little nuggets are hidden within my collection of little filled notebooks.4 So here it is: what a twenty-six year-old version of myself thought about writing his thoughts out by hand.


Picked up my first Field Notes pack today. I’m not positive, but I believe this is my first notebook purchase since the iPad. Most of my writing has moved to an all digital format, something I’ve dreamed of from a young age. I had a Palm, and always wanted to try an iPaq because it seemed like a palm sized computer. But nothing compares to the ubiquity of the iPad and the iPhone.

I now produce more content than ever before, and of a higher caliber than any other point in my writing life. My digital workflow is refined and something elegant. But not writing in notebooks has also taken its toll on me. I rarely write digital work that goes unpublished, whereas most of my notebook work has never been seen by anyone other than myself.

In other words, on the computer, I rarely do any creative exploration anymore. My old notebooks are full of half-cocked stories.

But enough about that. I’m going to try to get back in the swing of putting pen to paper and see how I do. I have atrocious handwriting. Digital acquisition has always been something of a favor to myself. Let’s see if I can even read my own writing.

Two quick editorial notes:

  • I checked and I had been producing “more content than ever before” back in 2011; whether it was all that great (ugh, “high caliber,” Jon?) is something I’m scared to go back and adjudicate.
  • Remember iPAQs?
  1. For the curious here’s the breakdown:

    • 14 Sealed Packs (13 3-packs and 1 Arts and Sciences 2-pack)
    • 30 Singles
    • 30 Full Books

    101 books, plus the one I’m using right now. And honsetly I think a few more are hiding around the house…

  2. I haven’t filled out the inside covers on most of my books, which would have made this process easy. And no, I didn’t fill them out last night either.

  3. There’s a listing for a sealed Raven’s Wing 3-pack on eBay going for $150, which is high but actually not that much more than many would pay. There were only 15,000 of these books printed. For comparison, the latest “Colors” edition, Workshop Companion, was a run of 102,000 books. It’s not exactly apples-to-apples (there are six unique Workshop books in each box wheras all the Raven’s Wing were the same), but suffice it to say: older editions are scarecer, and collectors are always on the lookout.

    Speaking of which, if anyone has a Just Below Zero set they’d like to part with, be in touch.

  4. I don’t revisit them often, because, as the motto goes: “I’m not writing it down to remember it later. I’m writing it down to remember it now.”

Apple Music Connect is Too Good to Waste on Artists

Music, Technology

As soon as iOS 8.4 came out last week I downloaded it and signed up for my free trial of Apple Music. Yes, there are some problems, but overall Apple Music is everything I ever wanted in a streaming service. The near-perfect mix of streaming library mixed with music that clearly belongs to me.

I’d like to focus on one of the more maligned features of Apple Music: Connect. Here’s a small sampling of the reactions to Connect out there, starting with Dr. Drang:

This is, to me, the least interesting part of Apple Music because I’m far too jaded to believe that anything put here is straight from the artists themselves.

Walt Mossberg tried to explain it:

[Connect] is a sort of social network for artists to reach their fans; the artists post photos, videos and more, and can receive comments from fans.

Jim Dalrymple wasn’t sure about it, but invoked the name of one of Apple’s biggest black eyes, Ping:

I’m not really sure what to think about Connect, Apple’s service that allows us to follow bands and musicians. To me, it seems a lot like Ping, but we’ll have to see how it works.

And Brian X. Chen at the New York Times devoted an entire article to skewering it:

The weakness of Apple Music is Connect, the social network for musicians, which allows artists to upload media, like postings about their concert dates or album releases. Fans can follow artists and “love” or comment on these posts.

But the artists I followed, like Kings of Leon, Belle and Sebastian and Sonic Youth, used Connect as a portal to upload seemingly arbitrary photos and link to places where people could buy their iTunes albums. And they didn’t appear to be socializing with fans. That’s not a social network; it’s a broadcasting platform.

I actually agree with all of the above. Artists postings thus far have been less than stellar. I think Apple has made a massive mistake billing Connect as a place to follow musicians. Connect is actually a wonderful service being squandered by Apple. The things that Apple is expecting artists to post just aren’t that interesting. Links to their own music and original photos or videos are relatively weak sauce, and the posts have been few and far between for most artists.

However, Connect is great for sharing exactly what I came to the Music app for: music. The trouble is most artists aren’t posting music; they’re promoting themselves in a fairly bland manner. I’ve found the best people to follow are DJs and performers with shows on Beats 1, as well as Apple’s in-house “curators.”1

I follow not only Zane Lowe and Julie Adenuga, but the accounts for “The Pharmacy with Dr. Dre” and “St. Vincent’s Mixtape Delivery Service.” For good measure I started following Apple Music Jazz and Pitchfork.2 These and other accounts have made my Connect tab go from a wasteland to a vibrant, always updated landscape.

The Beats 1 show accounts are great because you can get playlists for a show you missed (or listened to and wanted to revisit). The other curator accounts surface other kinds of music and move that into my Connect feed, where I may end up finding my new favorite song.

Right now anyone can share playlists through Apple Music. However, not anyone can get an account that can be followed. When that happens, I think Connect will be, unabashedly, the best music social network on the planet. The trouble right now is that Apple wants it to be a “a place where musicians give their fans a closer look at their work, their inspirations, and their world.” That’s not an interesting enough proposition.

Connect is dying to be a killer destination on my phone. I hope Apple sets it free soon. When they do, you can bet it will for would-be DJs what Instagram has done for photographers. The next Zane Lowe will be found in Connect, not on the airwaves.

Where to Find Non-Artist Accounts in Apple Music

There are two main places to look.

To find Beats 1 show accounts, go to the Radio tab and tap Beats 1. Scroll down past the “Upcoming Shows” schedule until you hit “Featured Shows.” There you’ll see album art for the current main rotation on Beats 1. Tap on a show and then tap “Follow.”

To find Apple’s genre and curator accounts, go to the New Tab and scroll down just a bit. Apple Editors Playlists will show you the accounts for every genre. Curators Playlists will show you accounts for Apple’s launch partner playlist makers. These include Complex, The Fader and other magazines. I hope these accounts will open up to anyone soon. There is so much music within Apple Music to unearth.

  1. If ever there were an overused word…

  2. It’s eternally annoying that there are non-artist accounts in Connect but you have to have to be a big-name media launch partner to land one.

The Dissolve Shutters


Well this sucks. Keith Phipps, founder of The Dissolve, pens the movie site’s final post:

For the past two years—well, two years this Friday—it’s been our pleasure to put up this site, a site founded on and driven by a love for movies, alongside a company with passion and talent for creating thoughtful, important work. Sadly, because of the various challenges inherent in launching a freestanding website in a crowded publishing environment, financial and otherwise, today is the last day we will be doing that

The Dissolve was an ambitious effort. The pitch, from my outsider’s perspective, was a film site that could stay relevant while operating outside the daily grind of marketing nonsense (“leaked” set photos, regurgitated press releases, et al.). It kills me that they couldn’t make it.

They’ve got helluva stable of incredible film writers looking for work today. Best of luck to everyone.

Running With My Apple Watch

Fitness, Technology

From the moment I first strapped on my Apple Watch, I’ve been diligent to fill all three rings in the Activity app. Though it may seem silly, it felt great when I got the below badge for filling them all every day in the month of June.

I still use RunKeeper, which I’ve used to track my runs since October 2013. Rifling through my old running stats, I can see that I’ve gone through quite a few workout spurts over the years. The regimen I’ve kept up these last two months and change is by far my most consistent fitness effort to date.

And it’s working!

Since May I’ve shaved about 90 seconds off my first mile time and 6 pounds off my gut.1 This is after I spent a little over a year trying to lose all the weight I put on eating my way through Texas after I first moved here.

So, is this all because of Apple Watch? I don’t know. Will it last? Who knows. But I can tell you personally that I really, really like my Apple Watch, with this latest burst of fitness perseverance being my most illustrative reason.

I still always run with my iPhone. For one, Apple’s Workout app doesn’t let you retrieve split timings, so I need to rely on RunKeeper for that. Once they add splits I’ll most likely be done with RunKeeper. (Right now I use both apps to track my runs.)

The other, bigger reason I run with my phone is for safety’s sake. It allows me to call for help if I need it and provides emergency contacts for others to help me. While I appreciate the ability to run with only my Apple Watch, I don’t see myself heading out without my iPhone any time soon.2

Some Apple Watch Workout Tips & Tricks

Here are a few things I’ve learned from running with the Apple Watch. Some of these may be obvious or known, but they weren’t to me at first. So I thought I’d share them.

  1. 6 Second Start
    • It takes 6 seconds from the moment you tap “Start” on a workout to the time your Watch actually starts tracking the workout
    • If you tap the screen after you hit “Start” it will end the countdown and go right into tracking
    • I have a 10 second countdown on RunKeeper runs, which gives me a little leeway to sync RunKeeper and Workout
  2. Elapsed Time, Distance and Heart Rate on One Screen
    • Here’s what I like to see on my watch during a run:
    • Set a distance goal so the middle numbers on the Watch screen will be your mileage
    • Swipe the bottom metric all the way to the right to get your live heart rate during your run
    • Tap the clock in the top of the workout screen to get your elapsed time to display there
    • If you need to know the time, I find it’s easier to just switch back to the watch face (double tap the crown) than cycle through your options on the line
    • For reference, here are the options for each row on the workout screen in the order you can cycle through them
      • Top row: Current Time, Pace or Elapsed Time
      • Middle row displays your goal, either: Calories, Time or Distance. An Open workout will display the elapsed time
      • Bottom row: Elapsed Time, Pace, Distance, Calories, Heart Rate
  3. Taking the Watch Off Mid-Workout Isn’t All That Bad
    • If you want to wipe some sweat out from under the heart rate sensor, just take the watch off to wipe it
    • You can pause your run if you want, but it will work and continue timing even if you don’t
  4. You Can’t Come Back From Accidentally Ending a Workout
    • If you accidentally end your workout instead of pausing it, there’s nothing you can do
    • Just save the workout and start another one where you left off
    • I learned this the hard way when I tried pausing a run to clean the heart rate sensor, which is also how I learned how to do that without pausing (see above)

That’s all I can think of for now. Apple’s Workout app is pretty rudimentary for now. I really hope it gets better because it’s the best Watch running app available today. I haven’t mentioned RunKeeper’s Watch app because it’s not so great yet. The text is hard to read while you’re running, and it’s missing some key metrics, namely heart rate. When watchOS 2 debuts later this year I’m sure RunKeeper will have a chance to give Apple a run for its money…or maybe the other way around.

  1. Give or take on both counts. It was just a holiday weekend, you know…

  2. Other reasons include: camera, streaming music (hello, Apple Music and Beats 1), listening to podcasts, entering run notes into Day One and probably a dozen others I can’t think of right now.

Review: Deep Web Tries to Unravel the Mystery of Silk Road

Movies, Reviews

The title of actor and director Alex Winter’s engrossing new documentary, Deep Web, contains multitudes. It primarily refers to a place, that obscure no-man’s-land on the Internet that goes unseen by the majority of users. It also alludes to another, more literary meaning. In traditional true crime reportage, if you pull the thread, the truth will unravel. Not so in this tale, though. When you pull the thread you just find more thread; a deep web that goes on forever.

The film, which I saw at this year’s SXSW, follows the story of Silk Road, a notorious underground marketplace for drugs and illicit goods that was shut down in 2013 after raids by multiple federal agencies. The site existed in the “dark net,” part of the “deep web” that goes unseen by the vast majority of connected users. Think of the Internet as an iceberg. Part of it sits just above water, visible to all. This is where we shop and download music, chat with friends, and read blogs. Below the surface, though, is an expanse exponentially greater in size and almost unfathomably, well, deep. It’s a place where everything from Oxycodon to rocket launchers can be purchased anonymously. When you connect to the dark net, there is nothing that ties you to an IP address; you have no identity, no nation. It is in this notorious pocket of the unseen Internet that the film takes place.

The Silk Road was something of an online Souk, a cacophonous nook of the world where nothing was above haggling, and where almost every drug imaginable could be purchased as easily as ordering paper towels off Amazon. Marijuana, cocaine, heroine; all could be ordered anonymously from the comforts of home, with a package arriving inconspicuously a few days later. The site relied on Bitcoin, the popular cryptocurrency that allows for anonymized transactions (if you’re careful). Since Bitcoin, like Silk Road, is nationless, it acts like an invisible dollar, keeping every aspect of the sales on the site undetected.

According to the Silk Road sellers interviewed anonymously for Deep Web, the site was also a community built around libertarian ideals. The idea was to make the sale and purchase of illicit items so dead simple, there would be no need for turf wars. Some on the site believed they could end the drug war by taking violence out of the equation completely. Perhaps the most illuminating point on the topic, featured in the film, comes from a 2012 episode of the Julian Assange Show, a roundtable discussion web series on RT that ran throughout that year. The episode featured noted “cypherpunks,” or cryptographic activists, including Tor developer Jacob Appelbaum, who says this:

Force of authority is derived from violence. One must acknowledge with cryptography, no amount of violence will ever solve a math problem.

In other words, since you can’t break down the door of an algorithm, violence is suddenly removed from the equation. The users of Silk Road were looking to do an end run around the drug war. In hindsight they proved unable to avoid that “force of authority” Appelbaum refers to. The government caught up with them.

Which brings us to Ross Ulbricht, the 30 year old whose current legal predicament lies at the heart of Deep Web. Earlier this year, Ulbricht was convicted of being a “digital kingpin” for running Silk Road under the pseudonym Dread Pirate Roberts, or “DPR,” the protagonist from William Goldman’s The Princess Bride. Just as in the book and popular film, “Dread Pirate Roberts,” is a title, not a name, belonging to whoever holds the position at present. Even though Ulbricht has been convicted, questions still loom over his exact role in Silk Road, and whether or not he was, in fact, the DPR. According to one Silk Road seller interviewed in the film, the DPR account, like the literary anti-hero, did not represent a single person. It was passed down from user to user, and was maintained by multiple people as well. So was Ulbricht the kingpin, or merely the fall guy?

The film offers no real answers because there are still so many murky details about Silk Road. To cite just one glaring example, there’s the issue of a federal agent who infiltrated the site using the name “nob.” Nob not only communicated with whoever was running the DPR account, he was supposedly contracted by DPR to commit murder for hire. Whenever DPR asked an enemy to be rubbed out, the federal agent would send photos of a staged murder. Ulbricht was pilloried in the press when his arrest was made public for this. Not only was he accused of being the head of a massive, international drug enterprise, but he was supposedly behind brutal, mob-like murders, even though the murders never actually occurred. In fact, when federal prosecutors brought their case against Ulbricht, no murder-for-hire charges were brought against him. Ulbricht’s defenders believe this was a calculated ploy to allow him to be found guilty in the eyes of the public before bringing charges against him.

In late March, an even stranger twist in the tale of Silk Road was revealed. Nob, the federal agent who staged the murders, was actually a DEA agent named Carl Mark Force IV. Force, who, along with Secret Service agent Shaun W. Bridges, deposited bitcoins extracted from Silk Road in the course of the investigation into his own personal account. The agents used the anonymized nature of their investigation to their advantage, keeping encrypted conversations and transactions from their superiors.

The version of Deep Web that EPIX will air this weekend will have an end title briefly explaining the stunning turn of events regarding Force and the federal corruption that came to light only after Ulbricht’s convition. The card will likely change further as Ulbricht recieved his sentence today: life in prison.

Deep Web raises more questions than answers, not just about Silk Road and Ulbricht, but about what is fast becoming one of the defining struggles of our times. Are we prepared for the crypto-revolution? When everything is encrypted and anonymous, what rule of law is there? As more and more of our lives become digital, what scrutiny, government or otherwise, are we opening ourselves up to?

The technology that allowed Silk Road to operate so successfully also enabled corrupt government agents to extort money for personal gain. In our digital future, who are the good guys? Winter’s film exposes us to the idea that it’s getting increasingly hard to tell.

Deep Web premieres on EPIX this Sunday, May 31st, at 8:00pm EDT.