P114: On Auto-Antonyms

The funny thing about language is that sometimes a single word can have two opposite meanings. Smarter people than me call these words “auto-antonyms.” For example, the adverb “periodically” can mean:

  • Recurring at regular intervals of time, but also
  • Repeating at irregular intervals

When I launched this newsletter, the central gimmick was that it would be published every week, aligning with the first definition above. Effective immediately, the publication schedule will reflect the second definition: irregular, sporadic, from time to time. And I don’t even have to change the name!

I’m going to continue to write, I hope you continue to subscribe. Talk to you soon.

Periodically yours,

Bob Sherron


P113: All Bots Everything

Smart folks like Chris Messina have been talking a lot lately about “Conversational Commerce,” the ability to deliver information and brand experiences through natural language, meeting their customers where they live — their messaging apps. Industry observers like Casey Newton have been tracking these trends closely and went deep earlier this year on The Search for the Killer Bot. Even Adweek have is getting into it, so it was no surprise that Facebook’s F8 conference was all about the bot.

“We think that you should just be able to message a business in the same way that you message a friend,” Zuckerberg said. And it was so. And the bots were bad, but the tech journalists were cautiously non-committal as to whether this was A Good Thing because, really, what tech journalist can afford to write off and/or anger Facebook?

All the geeks go on about how hard it is to make a decent chatbot and all the marketing folks are worried about getting the brand voice just so and of course the Simpsons did it first.

It’s a bot, bot, bot, bot world.

Periodically yours,

Bob Sherron


P112: Periodically Recommends: Techies by Helena Price

Short and sweet this week: you owe it to yourself to check out Techies, a series of portraits and interviews from Helena Price that tell the stories of those underrepresented in the tech industry. In Price’s own words:

”I started this project with two main goals: I wanted to show the outside world a more comprehensive picture of people who work in tech. I also wanted to bring a bit of attention to folks in the industry whose stories have never been heard, considered or celebrated.”

The photography is stunning and the interviewees are generous to share their lived experiences in the frequently homogenous world of technology. Give it a try: you can view the project in full or follow along one story per day on Medium.

And if you, like me, frequently find a trip to the office to be similar to gazing into a mirror, maybe Techies will be a starting point for imaging what a more inclusive future would be like.

Periodically yours,

Bob Sherron


P111: The Genius and The Damage Done

Genius, the occasionally noxious, always useful, frequently brilliant platform for annotations might be wishing for a couple more highlights this week, after an article by Chelsea Hassler called out the company’s News Genius product as being a potential tool for abuse and bullying. Recently reinvigorated by the hiring of Leah Finnegan, News Genius builds on the power of the Genius Web Annotator to aggregate annotated articles from across the web. By simply prepending “genius.it/” to a valid URL (like this one), a Genius user can annotate the content without the publisher’s permission or even knowledge of the annotation. Hassler believes this becomes especially problematic when paired with the frequently misogynistic nature of so many online interactions:

“There’s a lot of truth to that. Female bloggers have a long, sordid history of harassment on the Web — Gamergate is just the tip of the iceberg — and while Genius-enabled annotations could theoretically bring a larger audience to unknown writers, some denizens of the Internet are not seeking to broaden their page views; they actively wish to stay in their own circles, avoiding potential readers who are likely to be unfriendly.”

Hassler’s article and the (annotated) discussion around it eventually made it to Congresswoman Katherine Clark who reached out to Genius for comment via her social channels. Genius responded and they have added a “report abuse” button to each annotation – a good and necessary move but one that has been known to telegraph a lack of thoughtfulness about issues of abuse. And since that last link brought Anil Dash into this, I’m obligated to link to his seminal article about building online communities titled “If your website’s full of a-holes, it’s your fault.

If you read Dash’s recommendations, it seems like Genius is following that playbook fairly closely: paid moderators, posted policies, accountable identity. Unfortunately, it doesn’t seem as if these authors are asking Genius to annotate their content. The good and honorable thing to do here is for Genius to provide an opt-out so those who don’t want to participate aren’t compelled to. That said, it’s more than a little bit interesting that after extensive annotation, Slate published three corrections to the original piece.

Periodically yours,

Bob Sherron


P110: On Hulk Hogan, Gawker, and the First Amendment

Hulk Hogan was awarded $140 million dollars in compensatory and punitive damages this week when a Florida jury sided with the professional wrestler and amateur racist in his lawsuit against the internet tabloid Gawker over the publishing of a video showing Hogan having sex with his friend’s wife. Gawker publisher Nick Denton was not amused, but supremely confident about their chances at appeal. Characteristically, Denton did not hold back in his response:

“Hogan did not sue us, as he has claimed, to recover damages from the emotional distress he purportedly experienced upon our revelation in 2012 of a sexual encounter with his best friend’s wife, Heather Cole (then Heather Clem). It turns out this case was never about the sex on the tape Gawker received, but about racist language on another, unpublished tape that threatened Hogan’s reputation and career.”

While there’s plenty of reasons to dislike Gawker — not the least of which is their gleeful publishing of celebrity sex tapes — this is an open and shut first amendment case and the fact that it even got to a jury is a travesty. And now that the decision was put to a bunch of average Floridians, Gawker Media is required to issue a bond, the cost of which could cripple or destroy the company. Yes, Gawker did this to themselves. Yes, the post in question was tacky and culturally unnecessary. That doesn’t mean it isn’t protected speech.

There’s lots of people running around out there saying that this decision doesn’t change the freedom of the press. That as long as you’re not publishing sex tapes, you have nothing to worry about. These people are wrong and they are letting their old-fashioned yearning for a more civilized age color their analysis. The fact of the matter is that every publication with less money than Gawker now has to reckon that reporting the news can get them shut down and held personally liable. The constitution won’t even get the chance to protect the hundreds of thousands of publishers writing, blogging, tweeting every day in this country. Lawyer and blogger Scott Greenfield puts it better than I ever could:

“Faced with the potential of there being someplace in America that a jury could be empaneled that would take offense to the editorial determination that something is newsworthy, decisions will be influenced. News will go unreported. Pictures will get buried. Information will never be revealed. You (and I) won’t know. And we won’t know what we won’t know.”

That’s what is at stake here, and just because you’ve never published someone’s sex tape doesn’t mean you won’t feel the chilling effects.

Periodically yours,

Bob Sherron


P109: Media Geeks Rejoice: Bill Simmons is Back

Mid-last month, we learned that Bill Simmons’s next venture, The Ringer, would be unveiled first as a newsletter. A week later, we learned that the site would live on Medium. This week, the first newsletter reached inboxes and it was all very Bill Simmons-y. It might sound like I’m damning with faint praise, but I mean that in all the possible ways you can mean it.

I’m a fan of Bill Simmons, a frequent listener to his podcast, and an eager observer of his burgeoning media company. I consider the 4 days I spent devouring The Book of Basketball on the beach in Punta Cana to be one of my most enjoyable reading experiences ever. I clearly enjoy tons of wordy prose with lots of pop culture references and running gags. So I know the voice, I know what to expect, and in the first issue of the newsletter:

  • Simmons delivered an enjoyable riff on how they settled on the name “The Ringer,”
  • Jonathan Tjarks had an interesting meditation on the makeup of Kentucky basketball teams from the past few years that didn’t really deliver on the awkward headline, and
  • Jason Concepcion revived the beloved Game of Thrones Q&A column, “Ask the Maester,” previously on Grantland (RIP).

As far as debut newsletters go, it’s a strong showing. Just as with the recent X-Files reboot, the first objective is surely was to give the fans a taste of what they’ve been missing. To me, though, the most interesting part is the fact that this newsletter exists at all. Here’s Simmons explaining the role of the newsletter in a recent episode of his podcast (quote starts at 12:16):

”We’re going to release this newsletter, I think, up to three times a week starting in mid-March. It’s not going to be a website jammed into a newsletter – we don’t want to flood your email box with 7000 words of text. We have writers we’ve already hired, we have people who are creative, and we’re not going to have a site for a few months so we wanted to have a place that people could go and read quicker takes and lists and fun stuff. And if something crazy happens in the NBA lottery, I’m going to need a place to write. So I think it’ll be a fun short term alternative until we actually have a site.”

My one beef would be the idea that this newsletter is a temporary bandaid. Yes, it’s important to have something out there while they build the site, but Simmons doesn’t have to look any further than his frequent podcast guest Lena Dunham to see the impact of a well-made newsletter. Smart money is that Simmons is playing these cards close to the vest. Keep an eye on this space.

Periodically yours,

Bob Sherron


P108: Set Adrift on Memory Bliss

It’s like when an episode of Serial starts off with an update to the real-time story.

It’s been a strange news cycle this week. I don’t really want to talk about Donald Trump and I don’t really feel like I have anything more to add to Hamza Shaban’s reporting on #AppleVsFBI so I thought I’d use this space to play a little “where are they now” with some of my favorite subjects from the last half-year or so.

I. Awl Y’all

Last week I fretted about some changes at The Awl but today they announced that they hired Silvia Killingsworth, managing editor of the New Yorker and a truly inspired choice to lead what I’m sure will continue to be my favorite Web Site.

II. Your Boy

The Ethan Crouch “Affluenza” case has had nothing of consequence happen since it came into my life in the waning hours of 2015, save the occasional blurry iPhone picture in the UK tabloids. This validates my prior ignorance of this story and makes me wish I could return to the old days.

III. These Are My Readers

The writers of Grantland have spread to the four corners of the web but none of their Nexts were as eagerly anticipated as the Next of founder Bill Simmons, who has announced that The Ringer will live on Medium. Something something Peter North reference.

IV. Dat Taupe Blazer Life

My biggest geekout of 2015, “What is Code?,” won an Ellie for best Single-Topic Issue. Author Paul Ford went on to launch an agency, podcast, and blog/newsletter in the last 7 months, not that I’m measuring myself against Paul Ford in a totally healthy way, nope not me.

In short: #turnturnturn. Maybe next week I won’t be overwhelmed with American Politics.

Periodically yours,

Bob Sherron


P107: Sometimes We Get Mad When Good Things Happen to People We Like

Big changes at The Awl today, as it was announced that the Last Independent Media Company was seeking new leadership following the appointments of current co-editor John Herrman, Slate’s Amanda Hess, and Greg Howard of Deadspin to the prestigious David Carr Fellowship at the New York Times. Admittedly, my initial reaction was less than enthusiastic – The Awl’s peculiar brand of sarcastic literary dystopia checks all my boxes – but with time I’ve come to find a couple silver linings.

The Times Just Got a Lot Better

Any publication would be thrilled to add Herrman, Hess, or Howard to their staff, much less all three. They write the kind of journalism that gets noticed, at least by one-man late-night newsletter operations:

This is a huge win for the Times and surely what they must have dreamt of when they created the David Carr fellowship. Seeing these writers on an even bigger stage will be exciting.

Seasons Change at The Awl

If I force myself to tamp down the signature Awl emotion of existential dread, I can envision a world where new leadership at the site brings a new vitality, much in the way that Herrman and Matt Buchanan did when they took the reins two years ago. If you weren’t around or interested during that transition, I’d recommend this great interview of Awl founder Choire Sicha on Glenn Fleishman’s dearly departed New Disruptors podcast. It is some super inside baseball publishing stuff but I figure if you’ve read this far why not. And if it doesn’t work out and The Awl goes away, I guess we’ll finally know the true cost of ad blockers.

Periodically yours,

Bob Sherron


P106: The Three Best Things So Far About Quartz for iPhone

Last week, Atlantic Media’s business-focused website and all-around intriguing modern news source Quartz released an iPhone app and boy howdy was it enthusiastically received by Media Twitter. Unlike basically every other stream- or list-based news app that I know of, Quartz for iPhone uses a messaging interface to convey the day’s news. It’s super precious and highly engaging and 100% in my wheelhouse. Honestly, I could probably write 4000 words about this (give it time) but let’s start out with just three moments that truly tickled my fancy.

I. That icon. Oh my god the icon is pure gold.

QZ Icon

The way the Q fits inside the chat bubble. The way the bubble is oriented so “you” are the one speaking Quartz, as opposed to them broadcasting from on high. The way the Q is rendered so it evokes the power icon. So good!

II. The onboarding experience. I can’t compete with Samuel Hulick’s epic teardown of the app’s onboarding experience but I will direct you to go, immediately, and luxuriate in the way that Quartz welcomes you to the first-run experience. Key quote: “It’s like a UI turducken of onboarding goodness.”

III. Emoji as user interface. I don’t need to link to some clickbait trend piece to backup the idea that emoji is A Thing, right? So what better place to employ these expressive doodles than in situations that reward high information density and personality? Like in the user prompts…

…or the settings screen…

…or in notifications…

…or even in the notification action button!

Even the Apple Watch complication uses emoji to indicate market performance. 👏👏👏

I’m in love with the idea that there are those who spend each day stretching the definition of what it means to be a news / media organization. It’s even better when they aren’t stretching those definitions to include shady/lame/problematic behavior. Quartz, a site that spent the first two years of its existence without a homepage, that once described itself in an internal memo as “an API”, that does basic old email newsletters better than anyone, stretches those definitions further–and to more interesting places–than all others. For this reason, the new, charming, quirky, innovative experience that is Quartz for iPhone almost seems… expected? Hats off to Quartz. I’m excited to see how this app evolves.

Periodically yours,

Bob Sherron


P105: The Super Bowl of Super Bowl Ad Recaps

Hey did you know that last Sunday was The Super Bowl, or as people in the advertising industry call it, The Super Bowl of Advertising? It’s true! Americans have been groomed to believe that enthusiastically consuming and then discussing TV commercials is a totally normal thing for a person to do. It’s completely absurd and as an advertising professional, I bask in the evil genius of it all. My contribution to this ouroboros of “content” is this perfectly manageable list of links to articles and blog posts, helpfully grouped into sections appropriate for each type of commercial enthusiast.

Are you the type of person who only wants the very best?

Are you are really into schadenfreude?

Maybe you contain multitudes?

Could it be that you only read Adweek?

Were you operating under the delusion that Peyton Manning is anything other than a Company Man?

Are you still mad about the Rams?

What if you’re only here to talk about Beyoncé?


Is it? Is it really? Is it ever enough for you? No? Well you’ll just have to wait, breathlessly, until next year.

Periodically yours,

Bob Sherron