P006: Messaging, Evolved

This week, it was announced that Facebook had acquired WhatsApp for $16 billion in cash and stock and $3 billion in restricted stock units, setting into motion a commentary cycle that was instructive and insightful and occasionally ridiculously retrograde. Maybe the most useful piece was this week’s episode of The Talk Show which has Ben Thompson of Stratechery and John Gruber going deep on messaging for 2.5 hours. Through it all, it has become clear that messaging is the killer app on mobile and that American cultural attitudes have blinded some (myself included) to opportunities in that market.

Evolutionary Thinking

The easiest thing to understand about messaging is that the market for a good product is literally anyone with a mobile phone and the desire to connect with another human. Because of its enormous size, a company would only need to capture a small slice of the market to be profitable. Hence, most of the messaging products available today are forgoing the risk of innovation and instead are working on refining the experience that was defined by SMS and AOL IM back in the 90’s. The most obvious counter-example, Snapchat, is valued at about 1/5th of WhatsApp so it’s clear that the market is rewarding iterative evolution in messaging products.

With each iteration, a messaging product moves further and further from SMS, but at no point are its customers be confused about its utility. That steady reference point, however, is what drives a lot of the misplaced outrage when a $19B acquisition happens. I mean, it’s basically SMS, right? How hard could it be?

Which New Form of Journalism Are You?

There’s been a great deal of snark and even
a little bit of journalism lately about the latest scourge of your Facebook timeline, Buzzfeed Quizzes. I really like the Nieman article linked above, but I’m happy to play devil’s advocate with one of the best lines in it:

“A quiz is not, generally speaking, journalism, and it’s far from a new form.”

While this is a technically true statement, in my opinion, these quizzes are noteworthy evolution for BuzzFeed because it has the potential to link the two BuzzFeeds together in a new an interesting way. For the uninitiated, BuzzFeed is both a SEO’d-to-death viral timesuck that often reuses content without proper license and a legitimate news-gathering organization with a solid editorial component. Quizzes have the potential to combine these two halves with the slick interactive crack of the quiz yielding worthwhile editorial content. One example is Should You Learn To Code?, a one-question meta-quiz designed to illustrate the way that programming skills have somehow become the silver bullet that will save humanity.

The Shock of the New

So: Are quizzes a new form of journalism? It’s awfully difficult to watch the evolution of a medium as it is happening, but the biggest signifier to me is that the people who are happiest to dismiss quizzes as frivolity are the same people who would be way more interested if BuzzFeed Quizzes had evolved out of the journalism side of the enterprise and not the clickbait side. There’s no $19B shot fired that caused the industry to stop in their tracks, you just gradually started seeing more and more of them on Facebook until there were enough to warrant a think piece.

The Times They Are a-Changin’

If the WhatsApp acquisition is Dylan going electric at Newport, the difference between AOL IM and WhatsApp is the difference between Freewheelin’ Bob Dylan and Highway 61 Revisited: a 5-album stretch that saw Bob Dylan become Bob Dylan, America’s Greatest Songwriter. Now, nearly 50 years later, we can look back and see that plugging in an electric guitar was the logical next step for Dylan. In time, we will be able to see more clearly if $19B for WhatsApp was the right price at the right time, but if nothing else, it at least caused a ceaseless, scatter-shot industry to stop for a moment and consider a single topic.

Periodically Yours,

Bob Sherron


P005: The New Hotness vs The Hot Newness

While there’s probably more than two ways to advance your art/craft/business/industry, the most frequently discussed methods by far are innovation and iteration. Seduced by near-rhyme and the always-awesome affectation of alliteration, creative thinkers are typically content to describe progress in their field in terms of either:

  • radical leaps and bounds, or
  • constant, steady, predictable evolution.

Companies like Apple and Intel and Porsche have found great success by putting their products through alternating cycles of innovation and iteration, realizing that each breakthrough can be refined with time and dedication. This “tick/tock” development cycle is a pragmatic’s dream in that it gives an organization permission to manage costs and deliver a consistently high-quality product (tick) while periodically throwing caution to the wind with risky creative breakthroughs (tock). Of course, the success or failure of any product revision is affected greatly by the press that covers it, and the only thing that the press is interested in is disruption.

Hulk Disrupt

I’m not mad, I’m disappointed

Kevin Nguyen dropped an excellent review-slash-societal-critique over at the Bygone Bureau that was ostensibly about two new writing tools, Writer Pro and Hemingway, that have recently received a bit of backlash from the ol’ Internet. At the end of the day, these products are what they are, but surely the sheer volume of vitriol stems from the fact that they are not what they promised. Writer Pro announced itself with a truly beautiful video that completely oversold the innovation and utility of its tentpole feature, Syntax Control(TM), while Hemingway name-squats on America’s greatest author. These apps disappointed reviewers because they promised innovation – disruption, even – and that disappointment is going to make a meaningful iteration period much more difficult.

Under-promise, deliver

If the work you are doing is truly innovative, you don’t need to tell the world how good you are, the world will know and they will speak on your behalf. If the work you are doing is iterative, it is up to you to keep your audience from wanting The Next Big Thing when really what you are making is The Next Better Thing. Setting proper expectations is the only way you will have the room you need to do your best work.

Periodically yours,

Bob Sherron


P004: This Ramen Metaphor Will Shock You

Step Into My DeLorean

2005 was a great year for making websites. The tech industry was starting to rebound from the bursting of the Dot Com Bubble and Web 2.0 was in full effect. Ruby on Rails, a platform that simplifies the early stages of web application development, was rapidly approaching version 1.0 with much fanfare. Optimism was running high, and with optimism came the NDAs.

A Non-Disclosure Agreement (NDA for short) is a contract that allows two or more parties to share information but prevents those parties from sharing said information with others. In 2005 it was pro forma to sign NDAs before job interviews or when meeting with investors or contractors but even a friendly lunch with a tech-oriented peer could produce a binding contract. Protecting your million-dollar idea was the order of the day, at least until Derek Sivers laid waste to the entire notion in just 130 words.

Ideas are just a multiplier of execution is a blog post by the founder and then-president of CD Baby Derek Siver that turned the NDA from a badge of honor into a bozo filter. It laid out a simple formula for the true worth of an idea: multiply the quality of the idea by the value of your execution. Like so:

The Value of an Idea

Having the dollar sign on the execution side of the equation makes all the sense in the world because you don’t get paid for thinking, you get paid for doing. Side note: you can definitely tell that this concept is nearly ten years old because the max value of any idea / execution combo is $200M (for my readers using the Metric system, that’s a deciSnapchat). Unfortunately, the mentality behind this has lead companies with solid execution to pursue mediocre ideas.

BREAKING: Huge Corporations Are Missing The Point

One of the big “success” stories of 2013 was Upworthy, a site that produces viral-but-meaningful content, for varying values of “meaningful.” Mostly notable for their click-bait headlines, Upworthy has spawned an infinite number of pageview chasing clones, but one in particular will shock you (trigger warning):

CNN Is Terrible

I Mean, Really.

CNN was rightfully castigated by people who care about journalism (cough) but their behavior, while vile, makes a certain kind of economic sense. Their news organization is consistently (regardless of content) a million-dollar execution machine. Tossing a one-dollar idea at it still makes a million dollars in pageviews. By following Upworthy’s click-bait recipe, CNN traded their own ideas for a shallow approximation of the original.

The Thing About Recipes

Momofuku Ramen

Two years ago, my buddy Yao and I (mostly Yao) collaborated to make David Chang’s Momofuku Ramen out of his completely awesome cookbook. It took us a day and a half and the result was awesome, but no one is mistaking either one of us for David Chang. On the flipside, I make a pretty decent pot of chili, but if David Chang were to follow my recipe, people would wonder why he was lowering himself to the status of an enthusiastic home cook from the midwest. CNN shouldn’t be following Upworthy’s recipe either.

The use of formulas are attractive because they allow for quick replication of winning ideas but when you’ve established yourself as a leader you have to keep delivering new, original ideas rather than cynically following the latest trends.

Periodically yours,

Bob Sherron


P003: Minimum Viable Process

Mind The Gap

Ira Glass is the host and producer of the hugely influential weekly radio show This American Life, but that wasn’t always the case. In 2008, he recorded a four part interview with Current TV detailing his growth in the arts that resonated so completely with creative people worldwide that it is being referenced and built upon to this day. In a section of the interview dubbed “Closing the Taste Gap,” Glass takes two minutes to expertly distill the doubt and exasperation that surely afflicts anyone who is just starting and prescribes a way forward. Last week, videographer Daniel Sax gave that quote a vibrant typographic treatment that elevated the entire concept. I beg you to take a moment and enjoy:

The Gap on Vimeo

While the idea that you can brute force your way to proficiency is not unique, a question that is left unanswered is what to do with the substandard work being produced before your reach proficiency? Is it possible to make an impact with your work before your skills are fully formed?


Perhaps the most confusingly-named concept in the world of lean startup tactics is the Minimum Viable Product, or MVP for short. In a nutshell, a MVP measures enthusiasm for a product while minimizing the up-front development time of said product, allowing for the message to be molded and refined in response to the market. Perhaps the canonical example would be the landing page announcing a new product or service that encourages you to “sign up for more information.” Of course at this point, the product doesn’t exist any more than the Photoshop comps required to build the landing page. Following a modest paid-media campaign, development will start on the product only if enough people express interest. If this all sounds horribly cynical to you, then congratulations: you are a human being. But maybe we can find a way to reconcile MVP and brute force creative iteration?

Try Minimum Viable Process

If we accept that there are no shortcuts to creative competency, then we must find efficiencies elsewhere at the start. By refining your process and stripping away the overhead, you get out of the gate quicker and simplify the revision and refinement cycles. Some target areas to consider:

  • Manage expectations. Don’t just stamp the word “beta” across your logo. Communicate directly with your audience and let them know that this is a work in progress. Create tight feedback loops that trades the polish of the finished product for a sense that the reader is being heard.
  • Skip the big launch. Do you have a website and a Twitter account? No? That’s cool I’ll wait here for the 5 minutes it takes to set that up. Once you do, put the absolute bare minimum on each. Launch with a default website template and an Egg Twitter icon and put the focus on your work.
  • Reserve the right to pivot. For example, if you realize you don’t really care about adding week-in-review-style links to your email newsletter, then stop doing it in the third issue.
  • Listen, listen, listen. Google Analytics isn’t enough. Create a dialog with your audience and value their response. By minimizing your overhead at the start, you can iterate against user feedback without backtracking over months worth of work.

By setting limitations on the secondary BS, you can force yourself to focus on producing the work. If the work turns out to be great, no one is going to remember that you launched without a proper logo.

Periodically yours,

Bob Sherron


P002: A Really Big Shoe

Objects in Motion

The practice of free writing is one where the author sits and writes continuously, heedless of spelling and grammar, on the subject at front of mind. By focusing on the quantity of words rather than the quality of the prose, the author can break free from stasis and build momentum.

If the stated goal of a publication is to examine the value of repetition and schedule, inertia must be given due consideration. Its two components, starting and sustaining, should be familiar to anyone who has read a self-help manual. But while seemingly the entire tech industry worships at the alter of the start, precious little is made of the maintenance. Turns out there are few page views to be had extolling the virtues of dogged enthusiasm for repetitive tasks.

But in 2014 you still have major publications writing about the Beatles on Ed Sullivan. Few would disagree that Beatles are icons, but why is this performance so fondly remembered? My theory: by 1964, the Ed Sullivan Show had been on the air every Sunday night for sixteen years. He had a devoted audience that trusted his enthusiasm for this band. And when seventy three million Americans laid eyes on the four lads from Liverpool that night in February, what was already a pop phenomenon became a full-scale invasion. The Beatles didn’t need anyone’s help by 1964, but Ed Sullivan didn’t become a cultural institution just by getting his show on the air. He got it by grinding it out every Sunday for more than two decades.

Fresh Starts and Modest Changes

The Back to Work podcast will be recording its 156th episode today (3 years!), but the one you need to know is #47: Utter Failure and Hotel Steak. Unless of course you have stuck with your New Years resolutions? For the rest of us, this gem of an episode can help you set reasonable goals and realistic expectations.

Just Ignore the Paragraph About How David Carr Was Ahead of His Time in 2001

Ezra Klein has left The Washington Post and will be running a new site at Vox Media. Carr eulogizes Old Media while writing for the New York Times and I kept waiting for him to break into Dogespeak to establish cred. Very Masthead. Such CMS. Wow. Anyway: I liked this move better the first time, when it was done by Nate Silver.

Two In The Can

Thanks for your time as I figure out this thing, and thanks to everyone who filled out the survey. If you didn’t get a chance, you can always reply to his email if you have feedback. Make sure to stay tuned as I incorporate (co-opt) some of your great ideas.

Periodically yours,
Bob Sherron



P001: This is Periodically

Forward-Looking Statements

Today I’m going to write several hundred words about email newsletters. Next week, I’m going to do the same thing, and the weeks to follow as well. As the weeks go by, I intend to forge a mutually beneficial relationship with you, Dear Reader. What has begun as a buffalo-sauced beta test will (hopefully) bloom into a long-running, bi-directional exchange of opinion and information about how people communicate today.

It’s my belief that publishing on a regular schedule to an audience that has proactively subscribed to your work yields a deeper connection than other methods. Together, we’re going to see if that’s true.

While in beta, I’ll be twerking the form and tone, but you can expect one brief “think piece” (can we get a better name for that?) and a few news items. Thanks, in advance, for your time and attention.

Changing Horses Mid-Stream

Last month, Alexis Madrigal wrote a fantastic piece for The Atlantic titled 2013: The Year ‘the Stream’ Crested. In it, Madrigal makes the compelling argument that the real-time, never-ending nature of the web has exhausted it’s most enthusiastic participants. Instead, we are seeing a shift towards content with natural boundaries that allows for completion and, ideally, reflection. While I, for one, welcome our new #longform overlords, the real appeal is in a hybrid approach: get the broad strokes of the latest issues from the stream, then let someone like Dave Pell sift through the noise to find the definitive take in his always excellent NextDraft.

The Magazine: The Book, The Kickstarter

Glenn Fleishman is no stranger to regularly scheduled content. The publisher of the biweekly iOS newsstand app The Magazine, freelance journalist for The Economist and prolific podcaster (among many other things) recently completed a successful Kickstarter campaign to collect the best works from the first year of The Magazine into a hard bound volume. Hear that story on the latest episode of his show, The New Disruptors. Oh, did I mention he recently started an email newsletter?

Steamy Newsletter Gossip

Today in Tabs, a snarky, link-heavy list of hatereads that got swallowed up by Newsweek (of all places) recently got dragged into the middle of some sort of drama scene. Turns out calling “dibs” doesn’t actually do anything in the internet? As with everything best suited for the E! Network, the Gawker recap is the only link you need.

Bye For Now

Thanks again, Dear Reader. Look for Periodically on Tuesday mornings. If you have any feedback or suggestions of newsletters for me to follow, just reply to this email.

Periodically yours,
Bob Sherron