My favorite books of 2018

Over the past year I spent a lot of time on the subway reading books. Here’s my year-end list of favorites. If you want a look at what else I read in 2018, you can check out my reading log here.

Have any recommendations or books I missed on this list? Please give me a shout in the comments section or shoot me a note.

Enjoy the list and see you in 2019!

General non-fiction

  • The Literary Churchill. My first Churchill biography. The Literary Churchill takes an interesting approach to its subject, trying to explain his life not through his actions or his policies, but through his reading material. This book will teach you about Churchill and about how what we read defines us.  

  • Seven Brief Lessons on Physics. An enlightening little book on physics. Carlo Rovelli first published these seven essays as a Sunday series in his local newspaper. The result is an Italian stroll through the principles that govern our world. A great read over coffee on a weekend morning.

  • Bad Blood. You’ve already heard about this book and about how you have to read it. The movie should be fun.

  • Educated. A memoir about finding knowledge for yourself. “In retrospect, I see that this was my education, the one that would matter: the hours I spent sitting at a borrowed desk, struggling to parse narrow strands of Mormon doctrine in mimicry of a brother who’d deserted me. The skill I was learning was a crucial one, the patience to read things I could not yet understand.” This book will remind you what it is you love about learning and reading.

  • Red Notice. Probably the closest look you can get at the wave of capitalism that broke across Russia in the 1990s and the pool of corruption it left behind in its wake.

  • Barbarians at the Gate. This book details one of the all-time great bidding wars in the history of Wall Street. A fantastic piece of journalism that provides a detailed view of how deal-making actually happens in the upper echelon of buyouts.

  • How to Change Your Mind. A book about the emerging science of psychedelic-aided therapy. I didn’t love this book, but it did make me think about how our minds work and how we can strive to stay open-minded as we age. Once you start this book, you’ll find yourself bringing it up in conversation constantly.

Business non-fiction

  • 7 Powers. Operational excellence does not equal long-term sustainable value. Instead, it’s using that operational excellence to build an unassailable advantage that creates the long-term value that comes from high market share and high defensible margins. With 7 Powers, Hamilton Helmer takes the best insights from Porter’s theory of competitive strategy and turns it into a digestible reference to use during points of flux in a company’s trajectory. Highly recommended for product people.

  • The Score Takes Care of Itself. Do the little things right and the score will take care of itself. Bill Walsh’s treatise on leadership after a career in which he took the Niners to three super bowl championships.

  • The Phoenix Project. All of the groan-inducing, cringe-worthy business fiction of Eli Goldratt’s The Goal is back and better than ever in The Phoenix Project. A great, fun read for anyone working within a product organization.

  • Beyond Entrepreneurship. I watched a Reed Hastings lecture. He mentioned he tries to read the first 80 pages of this book once a year. So now I do, too. A good refresher on what great leadership looks like and the importance of setting a vision within a company.  

  • The Hard Thing About Hard Things. A book of “most important rules” and hip-hop epigraphs. Though tailored for the founder or CEO, The Hard Thing About Hard Things is a great read for anyone who knows how difficult startups can be (no matter the role) and wants well-worn advice on how to survive.


  • Stoner. “Sometimes, immersed in his books, there would come to him the awareness of all that he did not know, of all that he had not read; and the serenity for which he labored was shattered as he realized the little time he had in life to read so much, to learn what he had to know.” This novel is one of the better works of American literature I’ve read in a long time. The book’s protagonist, William Stoner, comes of age on the barren soil of a Missouri farm before attending the local university for agriculture school. There, amidst the trappings of chinch bugs and manganese, Stoner takes a required course in English literature. In the hazy afternoon of that classroom, the words of Shakespeare’s Sonnet #73—”this thou perceivest, which makes thy love more strong, To love that well which thou must leave ere long”—set him in reverie. When he awakens, his life has found a new path: teaching. A great campus read on finding your own purpose and happiness in life.

  • The Moon and Sixpence. I first read the name Somerset Maugham in the byline of an epigraph. It was a suitable introduction. Maugham’s writing—tight, dry, British—lends itself to quotation with ease. He’s also very funny. The Moon and Sixpence, Maugham’s novel based on the life of painter Paul Gauguin, lends itself both to its author’s quiet humor, and to his meditations on work and purpose. For Maugham’s painter protagonist, it isn’t fame or acclaim or success that he chases. It’s beauty. Beauty, and what it means to find it in life, emerges as the dominant theme of this book. It shows itself most in the protagonist’s monastic pursuit—his paintings, and the dark shroud of understanding contained within them, are its explicit manifestation. But beauty reveals itself in other, subtler ways throughout the novel. There are characters who find beauty in quiet, apartment-bound relationships, characters who find beauty in the families they build. It’s a nudge from Maugham. Create something. Make it beautiful. Be at peace. — Great book.

  • The Shining. A happy story for winter in the mountains. A fun way to dive deeper into the mythology of the movie while you test the heart rate monitor on your Apple watch.

Two quotes

“The fox knows many things, but the hedgehog knows one big thing.” — Archilochus

“The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” — F. Scott Fitzgerald

The life of a product manager is one of pattern recognition. You look at problems and try to remember whether you’ve seen them before.

I like quotes as a pattern recognition tool. They’re pithy and memorable, and yet, despite their simplicity, they can provide a lens into deeper, more complex ideas and problems.

Take the two quotes above. They stand strong enough on their own—the first a classifier for idealists and pragmatists, the second a reminder on the role of contradiction and self-doubt in great thinking—but when taken together, these two quotes provide an important lesson to the aspiring product manager, a pattern to recognize.

This lesson is simple. To be a great product manager, you must be both the hedgehog and the fox.

Foxes and hedgehogs

Let’s start with the first quote. “The fox knows many things, but the hedgehog knows one big thing.” I found this a few years ago in Isaiah Berlin’s essay The Hedgehog and the Fox.

In the essay, Berlin classifies the great writers of literature into two categories. On one hand are the hedgehogs, those minds who know one big thing, who forge their worldview with monastic belief into a single, fervent truth. Dante, Proust, Dostoyevsky: these are the cheery titans of camp hedgehog. In the other corner are the foxes. They fashion their pen not around a philosophy, but around the world itself. They write of the reality around them in all of its details and complexities, but without the unifying principle that embodies the work of a hedgehog. Shakespeare, Chekhov, Austen. All foxes.

In his book On Grand Strategy, John Lewis Gaddis’s takes Berlin’s idea out of the world of literature and into the world of war and diplomacy. Here, the hedgehogs represent those leaders with an ultimate purpose or mission, the foxes those leaders with a more tactical, pragmatic bent.

The book looks at these hedgehogs and foxes of history and asks, which is it better to be?

Gaddis starts with the hedgehogs. History is littered with stories of “too much hedgehog, not enough fox.” Napoleon is a good example. Hot off a winning streak through continental Europe, Napoleon set his sights on a trip into Russia. A true hedgehog, he was completely indebted to his vision. He dreamed of a French flag soaring over Moscow. He did not, regrettably, dream of Russian winters or of overextended supply chains. The result speaks for itself: one of the great military fiascos of history. Napoleon marched into Russia with 685,000 men. He marched out with 22,000.

Menard’s map of the French invasion. The brown line marks Napoleon’s path to Moscow. The black line marks his retreat. The line’s width marks the army’s size.

Menard’s map of the French invasion. The brown line marks Napoleon’s path to Moscow. The black line marks his retreat. The line’s width marks the army’s size.

The foxes, too, have their faults. Where hedgehogs (such as Napoleon) err in overcommitting themselves, foxes err in not committing themselves enough. Take General George McClellan, the fastidious Union general who, after weeks of careful planning, preparation, and fortification, always found a reason to call off his latest impending engagement with the Confederate army. These delays, always carefully justified in tidy correspondence, enabled the escape of the Confederate army on multiple occasions, leading to the extension of the Civil War and a massive loss of American life.

It’s here, with the faults of hedgehogs and foxes strewn across history, that Gaddis asks, if a leader can’t find success as a hedgehog or a fox, where can good leadership be found?

His answer: in the middle. To be both hedgehog and fox. To lead others towards a vision with drive and purpose, while spotting the logistical potholes that pock the road leading towards it.

No leader better exemplifies this balance than Abraham Lincoln. Throughout the Civil War, he had but one goal: the preservation of the Union. Everything he did, he did with that goal in mind.  Despite his steadfast commitment to that end, Lincoln realized better than anyone the immediate concessions that were needed to ensure the Union’s survival. This meant stomaching his own support of the Fugitive Slave Act in his inaugural (a hugely unpopular decision in the North that allowed Lincoln to keep crucial border-state allies) so that two years later he could be in a position to announce the Emancipation Proclamation. He made short-term concessions in support of a long-term vision.

It’s in this contrast—the short-term and the long-term, the fox and the hedgehog—that we can see what made Lincoln such a great leader: his ability to hold two ideas in opposition.

Ideas in opposition

This brings us to the second quote at the top of this post, Fitzgerald’s famous aphorism: “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”

I love this quote. On the surface, it’s so academic, so perfunctory. If you only ever read the quote, it would stay that way forever. But when you read the larger piece it comes from—Fitzgerald’s 1936 essay The Crack-Up—you realize that those words, with their definition of a “first-rate intelligence”, are not coming from a man who has retained the ability to function. Fitzgerald is writing in the waning years of his life. In a few years he’ll be dead at the age of forty four. In this quote, he’s lamenting something he’s lost: the ability to hold two ideas in opposition. For Fitzgerald these ideas were (i) the supreme confidence that he could produce something great and (ii) the complete self-doubt that actually drove him to that greatness. It was faith in the long-term coupled with an almost maniacal attention to detail in the short-term. It was the hedgehog and the fox.

For Fitzgerald, it was a paradox he could only hold on to for so long. He wrote his great novel and then fell into relative obscurity.

I drift into the backstory of The Crack-Up not to mourn Fitzgerald, but to underline that being both fox and hedgehog is hard. To drive towards a vision while embracing the complexities that keep you from achieving it; it’s an ability beyond most of the great figures of history.

The paradox of product

What these quotes are really about is our ability to deal with paradox. To me, there’s no place where that’s more true than the seat of a product leader or founder. A product leader is responsible for contributing to the strategy and vision of the product they help to build. To make that vision a compelling one—not just as something users want to use, but as something that team members wants to build. The only way to do that is by believing, with every ounce of one’s being, that the vision they promote is the right one.

But if the lessons of history tell us anything, it’s that we can’t just set a blind course and expect to find success. Like Napoleon, we, too, might find ourselves walking back the way we came with half the team that started with us. Instead, we have to constantly test that vision and strategy. We have to constantly poke and prod to see whether it’s still relevant, to see whether the landscape has shifted around us. Even when we do arrive at a sound conclusion, we need to doubt whether we’re executing well enough against it, whether the team we’re a part of has the discipline to stay focused against that plan.

So where does that leave us? As product managers, we need to be both believer and doubter. To continue driving forward while always checking to make sure we’re moving in the right direction. This comes forward in a few ways when you’re in product.

The first is in vision and strategy. In tech, where “the platform [sic] for all of your x needs” value props abound, any vision needs to be looked at from an objective distance. Do we want to be the platform of x because we can offer differentiated, defensible value in all of the specific functions that roll up into x; or are we oversimplifying the complexity of our market in pursuit of the grandest vision imaginable? To choose the latter is to look back at three years of product decisions and see a litany of unfocused, unforced errors. It’s the path of too much hedgehog, not enough fox.

On the other end of that spectrum are the aptly named “feature factories” of the product world. The feature factory looks at the immediate short-term wins and tacks them into the product one after another, not stopping to think of the single cohesive vision that those features should work towards. These small fixes make pockets of customers happy, but they rarely build the sort of long-term sustainable value that comes from a continued focus on a single goal or strategy. Herein lies the path of too much fox, not enough hedgehog.

So how do we stay both fox and hedgehog when we work in product?

One way is to look to the other product leaders who have done it. I’ve pointed to Stewart Butterfield’s We Don’t Build Saddles Here on this blog before, but I’ll bring it up again as a careful balance between end vision and the short-term details that get you there. The essay is a bugle blast for Slack employees to rally behind the company’s mission, but its final call to action is actually one about doing all the little things right. That’s not the easiest message to communicate in an inspiring way, but whenever I come back to this essay, it still gets me just as excited to go out and build something great as the first time I read it.

The other way to maintain this balance between the short and long-term is to recognize when you’re drifting too far in either direction. It’s in those moments that you have to remember to constantly redirect yourself back towards the middle, back to an uncomfortable position of paradox. The two quotes above have helped me to strive towards that position, and I hope they can do the same for you.

Plus / minus

Last month I heard Slack’s Noah Weiss speak at a First Round Capital event here in NYC.

When I first started in product, Weiss’s reading list was my north star. I spent my first month as a PM pouring through its articles, writing down everything I learned along the way. It’s still the first resource I point people to when they tell me they’re interested in product management.

At the event, Weiss told his story and sprinkled in a few do’s and don’ts throughout. The advice that stuck with me most was a sports analogy: “+/-”.

+/-, or plus-minus, is a statistic that measures a player’s impact on a game. If your plus-minus rating is positive, your team scores more points than its opponent when you’re in the game. When your plus-minus rating is negative, bad things.

Why do sports statisticians track plus-minus? Because it helps show the intangibles, it shows which players make their teams better.

Basketball player Shane Battier, who earned his own write-up in the Times on account of his stellar plus-minus rating, is a good example. By any conventional measure—points, assists, steals—Battier lagged behind others in the league. He was regarded as a “marginal athlete at best.” But a trend emerged. In spite of Battier’s box score reputation, his team won more when he played.

“Here we have a basketball mystery: a player is widely regarded inside the N.B.A. as, at best, a replaceable cog in a machine driven by superstars. And yet every team he has ever played on has acquired some magical ability to win.”

“A magical ability to win.” But why Battier? Because, despite his shortcomings, he brought an intelligence and a hustle to the game that showed up in his plus-minus rating, even if it didn’t show up in the stats we talk about most—shooting percentage, assists, steals. The example of Shane Battier isn’t meant to de-value these traditional statistics (the top of the all-time plus-minus leaderboard is full of players we’d normally associate with great box score stats) but instead to show that there are other, less visible elements of the game that contribute to winning.

Let’s tie it back to product management. When you first start out as a product manager, with that bountiful range of responsibilities in front of you, it’s natural to gravitate towards those that help you stand out, to the parts of the role you’ve spent months reading about. Market research, feature definition, prototyping. You want to pull up from beyond the arc and toss up a deep three, that game-changing silver bullet of a feature that’s going to define your legacy.

The more time you spend in product, the more you realize that as important as the big ideas are (and they are important, just like points and assists are important in basketball,) it’s the work you do to make the team better that matters most. What can you do as a PM to make design, engineering, marketing, services, and others, more successful? What can you do to give your company a “magical ability to win”?

This is the great insight of Andy Grove’s High Output Management, that a manager’s output is measured not by what they produce in a vacuum, but by what his or her entire team (and the teams within his or her sphere of influence) accomplishes.

Sometimes that’s the game winner from deep, other times it’s QA, documentation, removing blockers for engineering, thinking through the details of a piece of UX. In my own experience as a PM, it’s helped a lot to keep these other focuses in mind, the ones that only show up on plus-minus, even when I’m stewing on some larger product theme.

Enterprise complexity

A few weeks ago, Terry Crowley, former manager of Microsoft’s Office team, wrote a great post about essential complexity in systems.

In it Crowley discusses essential complexity, the cost of adding a new feature to a large system, and how the team at Microsoft embraced essential complexity to build a cloud Office suite that could compete with Google Apps on previously asymmetrical features (like concurrency,) while maintaining the robust feature set (and file format) that enabled Microsoft to keep business from Google Apps’s collaborative cloud in the first place.

Much of the response I read concerning the post treated it in a triumphant light (likely influenced by good news re: Office 360 v. Google Apps market share)---the words of a man who had wrested complexity to the ground.

But any who cite victory against complexity should be taken with a grain of salt. Complexity is the emergent behavior that arises from the interaction of lower-level primitives. It is, by many accounts, unpredictable. A complex system can’t be controlled or used to elicit a specific result, it can only be loosely guided towards an objective from the bottom-up. (If you’re looking for a good primer on the science of complexity, check out Mitchell Waldrop’s Complexity.)

When Crowley talks about taking on the “essential complexity” inherent in a large system, and reducing the “accidental complexity” or “unnecessary complexity” introduced to it via a new feature, it’s important to note that he isn’t conquering complexity so much as embracing it (and accepting that his users will, to a certain extent, have to embrace it as well. More on this later.)

In reading Crowley’s discussion of the essential complexity within a given system, I was reminded of two other complexity concepts I’ve been reading about lately. In this post, I’ll explore those different types of complexity, their relation to essential complexity, and how all of this introduces a host of questions that product management (and company leadership) need to consider.

I’ll start with essential complexity and then look at what happens when we abstract it to a higher order of behavior. The first abstraction lands us at what I call “stack complexity”, or the behavior that emerges when different systems interact. The second abstraction moves to “enterprise complexity”, or the behavior that emerges when that stack of systems and vendors interact with the scale and process of an enterprise organization.

Essential Complexity

First, let’s look at what Crowley means when he says “essential complexity.”

He starts with the function-cost curve, a way to ascribe the functionality a team develops within a system, and the marginal cost of adding each new feature to that system as more and more functionality gets built in. The general position is that in large systems, the cost of adding a new feature to the system is higher because it needs to consider its interaction with more total product.

In product strategy, you’re always thinking about essential complexity within the context of new features. Crowley explains how at Microsoft they often had to decide whether or not to take on essential complexity. Either make a new product completely compatible with the other feature sets in the suite, thereby increasing its essential complexity (as they attempted with the co-editing features in Office 360,) or cast aside that essential complexity and start the new feature in isolation (as they did with OneNote.)

In the case of Office 360’s Word app, Crowley+co decided to “embrace essential complexity” and build co-editing features on top of the existing Office feature set, rather than build a new, simpler version of Office designed for in-browser collaboration.

This decision gave Microsoft a cloud word processor app compatible with Word formats, “a critical competitive moat with immensely strong network effects.” This led to Microsoft stealing a lot of productivity software market share back from Google Apps.

But the decision also led to a lot of new complexity within Office360. For any user looking for an easy way to collaborate on a document online, the simplest solution still sits within Google Docs. And this is the grain of salt I mentioned earlier. Crowley’s post is fantastic, but we should be careful to read it not as a triumph over complexity, but as an acquiescence to it. The Office team decided to lump co-editing in with their existing feature set and the result is a more complex product than Google Apps---one that’s more difficult to use but offers the range of functionality certain enterprise users need.

So this is essential complexity. Weighing the decision to introduce a new feature into the existing context of the system. Considering that decision within the light of the features your competitors in that space offer. But, in most cases, the decisions around essential complexity are inward ones. Decisions about how things interact within your product suite.

When you move to a higher order of complexity and start thinking about how a system interacts with other systems, you get stack complexity.

Stack Complexity

Stack complexity is interesting in that it poses an entirely different set of questions to product management. A set of questions that exist on a different plane than those in essential complexity, and likely exist outside of the scope of what those essential complexity systems are able to do. (I.e. for a long time systems like Microsoft have natively integrated within their suite, and relied on SIs to integrate them within their larger stack.)

Ben Thompson addressed the idea of stack complexity on his blog a few weeks ago:

“When enterprise software first came to be it was primarily focused on automating routine business processes like accounting and enterprise resource planning. At first these solutions were self-contained, but over time, particularly as companies sought to gain usable insights from the data they were collecting, it became necessary for these monolithic software installations to talk to each other.

At the beginning nearly all of these integrations were custom-built and maintained by system integrators; this was manageable as long as the number of integrations were small, but as the number of applications increased the number of potential integrations increased exponentially (integrations = n(n-1)/2 in which n is the number of apps). This not only made it difficult to connect applications, it made even updating a single application a very dicey proposition — what if the custom integrations stopped working?”

With the cloud and its proliferation of services all touting integration-friendly, API-first applications, stack complexity abounds. There are a few different approaches vendors have taken to this problem. Like essential complexity, one approach is to embrace stack complexity, the other is to bow out if it.

Companies embrace stack complexity in different ways. On one hand you have vendors like Slack who want to be the interface on top of everything. Their message to IT buyers is “purchase whatever you want, you can rest assured it’s in the Slack app directory so you can tie it all together.” But being the interface to all systems doesn’t necessarily mean handling the regular and systematic flow of data between those systems. For that use case there are vendors like Mulesoft, seeking to be the common layer between everything. In either case, these vendors are similar in that they’re betting on customers embracing complexity, building a stack out of multiple point solutions and then trying to piece it all together into something that works.

Then there are those companies attempting to eliminate stack complexity for their customers. This is the path for Microsoft and the other full suite providers---in the process of taking on essential complexity, they bow out of stack complexity. For while Microsoft’s Office suite (and other suites like it) provide plenty of integration solutions, they’re not differentiating on them. What they’re differentiating on is the ease of the native integrations within their system; Outlook working with Word working with OneDrive and so on. It’s an interoperability that 1) with a strong enough network effect creates the aforementioned moat of file formats and 2) helps to win out against point solutions. In a late 2015 CIO article on Microsoft’s winning of market share against Google, Outlook was actually cited by IT consultants as the primary driver behind customers switching from Google Apps to Office365. I was stunned when I read that. Outlook over the ease and simplicity of Gmail? But that’s the power of a system that takes on its own essential complexity (and to Crowley’s point, I think Microsoft has done a better job of acquiescing to their own complexity than Google Apps has) so that its customers can opt out of some stack complexity.

On top of this, Microsoft makes it easy for an organization to opt into their entire suite. Not just through their software, or their product strategy, but through an enterprise culture that embraces the organizational complexity of the enterprise. This brings us to our last abstraction of complexity.  

Enterprise Complexity

If essential complexity is the complexity within a single system, and stack complexity is that within a collection of systems, then enterprise complexity is the loose term I use for what happens when you move to yet a higher order behavior and start to look at how the users (and buyers) within an organization interact with that collection of systems.

Like stack complexity, enterprise complexity asks a completely different set of questions than essential complexity, this time not just of product management, but of the entire vendor as a whole. How is implementation run? Are customers expected to learn how to use the product on their own, or are you putting people on the ground to help them? Do you offer dedicated support teams for your biggest customers? How does your product’s system administration scale to a true enterprise organization? These are the types of questions posed by enterprise complexity. And what’s more, since it’s a higher-level of complexity involving the lower-level elements already discussed---each feature, each system, the interaction of all of those systems and features, the people that use them, etc---it gets even harder to predict what emergent behavior will come out of it.

This means that when it comes to enterprise complexity, there is no single product management strategy that makes it all better. Instead, a vendor embraces enterprise complexity from the bottom-up by making sure every lower-level element within their own business (just one part of which is product) drives towards the emergent behavior of enterprise success. A lot of people call this bottom-up structuring “enterprise ready”. Whatever we call it, the takeaway is this: you only survive in the enterprise by embracing it everywhere in your business. Sales. Services. Marketing. It doesn’t just come from product.

A great example of this is Charles Fitzgerald’s recent post Google’s Scalability Day. In a fun twist, it starts with the example of Microsoft in the late 90s, a giant who, by many measures, hadn’t yet become “enterprise ready.”

“Microsoft at the time was an extremely engineering-centric company, so it processed all the criticisms through a technical lens. Soft, cultural, customer, and go-to-market issues were discarded as they did not readily compute and the broader case against Microsoft’s enterprise maturity was distilled down to the concrete and measurable issue of scalability. The company assumed some benchmarks plus updated product roadmaps would clear up any remaining “misunderstandings” about Microsoft and the enterprise.

The event was a disaster and served to underscore that all the criticism was true. It was a technical response to non-technical issues and showed that the company didn’t even know what it didn’t know about serving enterprise customers. Internally, the event served as a painful wake-up call that helped the company realize that going after the enterprise was going to be a long slog and would require lots of hard and not very exciting work.”

Fitzgerald then brings the thread back to where we started: Microsoft Office v. Google Apps, and the latter’s push into the enterprise through an asymmetrical product strategy focusing on collaboration and co-editing.

“I couldn’t help but think about Scalability Day while watching Google’s #GCPNext event today. After telling us for months that this event would demonstrate a step function in their ability to compete for the enterprise, it was a technology fest oblivious to the elephant in the room: does Google have any interest in or actual focus on addressing all the boring and non-product issues required to level up and serve enterprise customers?”

This is the importance of enterprise complexity. Even if you’re the vendor with the simpler, easier-to-use solution---in this case, Google---if you haven’t embraced the complexity of the enterprise and “all the boring...non-product issues” required to succeed within it, you might actually be the more difficult solution for enterprise buyers to purchase and scale across their organization.

For product and non-product managers alike, it’s important to consider the essential complexity within their own solution, as well as how it plays with their customers’ stacks and organizations. The simplest product isn’t always the one that wins in the enterprise.

Vestigial stories

Long time no post.

Last year I set out to write a post a week. It was hard and rewarding and made me a better writer. It also took a lot of time away from side projects queued on my weekend backlog.

This year I’ve set the considerably vaguer goal of writing when I can. As the date on this post indicates, that’s going to be a lot less than once a week. Still, a month-plus of lag between posts is too much time away---from here on out I’ll be pushing for every two weeks.

The end of this blog remains the same as last year: to explore new ideas and clarify my own thinking.

Thanks for reading.

Sometimes when asleep, I get the sudden sensation of being in free fall, only to wake with my head on my pillow, safe and sound.

If you, too, get sudden sensations of free fall whilst asleep, fear not. Its official name is the hypnic jerk, and it’s a type of vestigial response, believed a leftover instinct from when our primate ancestors slept in trees.

While reading Annie Dillard’s Pilgrim at Tinker Creek over the holidays, I came across another sort of vestigial response.

From Dillard:

"I wonder how long it would take you to notice the regular recurrence of the seasons if you were the first man on earth. What would it be like to live in open-ended time broken only by days and nights? You could say, “it’s cold again; it was cold before,” but you couldn’t make the key connection and say, “it was cold this time last year,” because the notion of “year” is precisely the one you lack. Assuming that you hadn’t yet noticed any orderly progression of heavenly bodies, how long would you have to live on earth before you could feel with any assurance that any one particular long period of cold would, in fact, end? “While the earth remaineth, seedtime and harvest, and cold and heat, and summer and winter, and day and night shall not cease”: God makes this guarantee very early in Genesis to a people whose fears on this point had perhaps not been completely allayed.

It must have been fantastically important, at the real beginnings of human culture, to conserve and relay this vital seasonal information, so that the people could anticipate dry or cold seasons, and not huddle on some November rock hoping pathetically that spring was just around the corner."

I like this passage because it hints at why we tell stories in the first place. As Dillard mentions above, and as Jonathan Gottschall argues in his book The Storytelling Animal, for early generations of homo sapien, stories were an effective way to pass important information from one generation to the next. For early humans, that meant ensuring that future generations understood seasons and how to prepare for them.

But this passage also presents seasons as a story we still tell today. Dillard continues:

"We still very much stress the simple fact of four seasons to schoolchildren, even the most modern of modern new teachers, who don’t seem to care if their charges can read or write or name two products of Peru, will still muster some seasonal chitchat and set the kids to making paper pumpkins, or tulips, for the walls."

And so the season stories told today (an example I remember from childhood is The Ant and the Grasshopper,) made irrelevant by Doppler radar forecasts and weather apps, have become, in a strange sort of way, a remnant of our distant past. An artifact with waning functional purpose but a lingering place in the human canon of fiction. A vestigial story.

Top 5: 2016, a year in review

Twenty sixteen. Woof. A year of subtle ups and conspicuous downs. To live through this year was to hear the somber announcement that Prince had died, but then, in its wake, get to experience Purple Rain in theaters, where fans sashayed down the aisles and crooned into the high rafters in remembrance of the little purple one. A year of bad news that we got through.

In honor of the ups, I’m ending the year the same way I started it: top five lists.

For those who missed last year’s top five post, I got the idea from one of my favorite movies High Fidelity. You can top five list anything: 90s movies, Olympic sports, vegetables. This post will focus on my favorite reads and listens from the year.

This will be my last blog post of the year. Number fifty two. To all of those who followed along, provided feedback, and were part of the general conversations that turned into these posts, thank you! And, as always, thanks for reading.

Into the new year we go.

Top 5 Tech Reads

Top 5 Long Reads

Top 5 Non-Fiction Books I Read in 2016

Top 5 Fiction Books I Read in 2016

  • The Leopard, Giuseppe di Lampedusa. The Italian One Hundred Years of Solitude.

  • The Age of Innocence, Edith Wharton. Boy meets girl in old New York. Boy and girl find themselves suspended between two generations and are forced to compromise, accordingly. This book is one of the greats.

  • Still Life with Woodpecker, Tom Robbins. "Hostess Twinkies mate for life."

  • Plays, Anton Chekhov. Plays from the mid-19th century about unhappy people aspiring for something more: “In two or three hundred years life on this earth will be gorgeously beautiful and glorious. Mankind needs such a life, and if it is not ours to-day then we must look forward to it, wait, think, prepare for it. We must see and know more than our fathers and grandfathers saw and knew.”

  • Ready Player One, Ernest Cline. 80s and video games. A fun read for anyone else who used to be really into RPGs.

Top 5 Albums Released in 2016

Top 5 Old Albums I Re-discovered in 2016

  • To Bring You My Love, PJ Harvey. Worth a visit if you haven’t heard this before. Lots of range on this album.

  • Bee Thousand, Guided by Voices. The album the Beatles would have produced had they been a lo-fi basement band in the early 90s.

  • Special Beat Service, The English Beat. A fun cooking album. “Save It For Later” is my highlight.

  • Music for 18 Musicians, Steve Reich. Beautiful pulsing compositions that make for great work music.

  • J.S. Bach: Suites for Cello, Pablo Casals. Pablo Casal’s recording of Bach’s Cello Suites. The suites are one of the most popular pieces of classical music around today — the Yo Yo Ma version is all over the place. But I like Casal’s recording best. The suites were unknown and destined for oblivion until he stumbled across the sheet music in a thrift shop in the early 20th century. He recorded them in 1936 at Abbey Road and they’ve since become legend. A cool story and a beautiful piece of music.

Top 5 Blog Posts I Published in 2016

2016 predictions: a retrospective

I started the year with a list of predictions for 2016. In today’s post I’ll take a quick inventory of how I did on the year.

Predictions in bold. Outcomes follow.

1. Twitter will raise char limit to 10,000, but the average tweet length will stay below 200 chars.

It’s funny to look back on the year and think that, at it’s start, Twitter’s character limit decision carried the sort of weight that tops prediction lists (or, in any case, this one.) Given where the character limit policy landed, I’m counting this as a miss.

2. AWS will continue to dominate cloud computing services...

No change here. AWS continues to do very good things for Amazon.

That said, one of my favorite stories of the year (that I completely missed in my 2016 predictions) was the resurgence of Microsoft as a key player in cloud computing. Going into 2017, I’ll be keeping an eye out for how how Microsoft leverages its strong position in higher-level enterprise solutions (Office365, Active Directory) to drive adoption of its lower-level services, and vice versa.

3. ...but Amazon Prime will not unseat Netflix as a media streaming service.

At the start of the year, I wrote about how Netflix’s early jump on the global streaming market (and their CDN’s position with international network companies) was an advantage they’d hold over Amazon’s streaming offering. Now, in the light of Amazon’s own announcement to take their owned content global, I’m not so sure.

As both companies go global, the larger question I’ll look to in 2017 is how they’ll manage ballooning content costs. For Amazon, content costs can be justified as part of a larger strategy to bring consumers into their Prime model; for Netflix, not so much.

4. Oculus Rift will ship with early-platform games this year. VR won’t be a big deal for the general public until its use case expands to include GoPro360 home videos.

Though VR games shipped this year, the medium still seems more of a novelty for the majority of consumers. Moving into next year, I think the VR discussion will continue to revolve around gaming, with the main VR offerings (Oculus, Sony, Vive) duking it out in a VR platform war. (Here’s a great summary on the platform war from Lightspeed’s Alexander Taussig.)

5. Facebook (+Instagram) will continue to crush mobile ad sales.

Facebook had a big year. From the WSJ’s summary of their Q3 earnings report:

“The social media giant said Wednesday that third-quarter revenue soared 56% to $7 billion and its quarterly profit nearly tripled to $2.38 billion, as it reaps the spoils of its dominance in mobile advertising. Facebook’s top-line growth rate is double any other U.S. company with revenue of $20 billion or more, excluding those growing through acquisitions, according to data from Standard & Poor’s Capital IQ.”

For that, I’ll count this prediction as a win, but the interesting news from FB’s Q3 earnings report was what it held for 2017:

“Yet Facebook said that it can’t maintain its current pace. Starting in the middle of next year, Facebook will stop showing users more ads in their news feed, the tactic it has been using to juice revenue growth for the past two years, the company said Wednesday. As a result, advertising growth will “come down meaningfully,” Chief Financial Officer Dave Wehner said during a call with analysts.”

And so going into next year, as FB looks for new sources of growth, there are two main questions that I hope to see unfold:

  1. How much growth is left in the Instagram business. Given CFO Dave Wehrner’s comment from the Q3 call---“we’ve got 4 million advertisers on Facebook; 0.5 million advertisers on Instagram”--- I think the answer here is quite a bit. If that’s the case, perhaps we’ll get to see a breakout of the Instagram business in FB’s ‘17 reports.

  2. How Facebook will fare in mobile video. A few weeks ago I wrote about FB’s push to win mobile user-generated video share with FB Live, and how that live offering paled in comparison to Snapchat’s default ephemerality. Excited to see how this plays in ‘17, and whether FB Live or Instagram stories becomes the mobile video hit the company needs to compete with Snapchat on this front.  

6. The general public will continue to be underwhelmed by bitcoin’s impact, and overwhelmed by how it works.

In 2016 I heard little about bitcoin (outside of its recent rally) and lots about blockchain. I suspect this will be the lasting impact of bitcoin, that it introduced not a currency but a distributed canonical ledger for use in enterprise operations. IBM’s leveraging of blockchain in its supply chain management is one example of this from 2016. More to come in 2017.

7. ESPN will continue to lose subscription numbers; Disney will shrug off the ESPN decline because STAR WARS.

Cable subscriptions continue to decline at an increasing rate. The Force Awakens was a massive hit. We can expect to see Disney pump out a Star Wars movie annually, which is totally okay with me.

8. The Slack platform will be great, but not great enough to stave off a valuation markdown.

Big miss here. No valuation markdown and their platform strategy continues to grow, with a Google Apps integration announcement as the cherry on top. Still, Microsoft looms large in the enterprise collaboration space in 2017. And there will always be that open letter.

9. SpaceX Booster Landings. SpaceX will land two additional boosters in 2016, but the upcoming January landing at sea will miss.

Five booster landings on the year for the good people at SpaceX.  The January landing at sea missed. Counting this as a win.

10. Apple will be fine.

In 2016 Apple reported its first annual revenue decline in fifteen years. And yet, that news came in a quarter when Apple’s bottom line sat at $9B, when consumer demand for the 7-plus outpaced supply, and when their Q1’17 forecasts beat street estimates. No crisis here yet.

11. Hillary will win.

A miss.

12. “Facts” will not be on the new Kanye album.

Technically the “Charlie Heat Version” that made it onto TLOP, so counting this as a win.

13. You-know-who from Game of Thrones is still alive.

Got it.

14. The Warriors will set the record for most wins in a single NBA regular season.

Also got it.

Thus concludes my 2016 predictions wrap-up. With all matter of subjective generosity, I count four misses on the year. As always, thanks for reading.


Forever or not: what wins mobile video

A few weeks ago I wrote an anecdotal post about my early experiences with Facebook Live, and how what I perceived as its synchronous, ephemeral nature ran against the grain of the async viewing experiences users want.

Of course, as I learned from a few readers following that post, Facebook Live isn’t ephemeral by default -- it lets the user delete a live video or save it to their timeline following recording. This is part of the last post I just got plain wrong (and it’s what I get for trying to type out a quick post on a flight without wifi,) but in that subjective take, there’s an interesting read on consumers’ value perception of live and whether ephemerality-by-default is an inherent part of that value.

In this week’s post, I’ll revisit Facebook Live within the context of the mobile video ad market and the different content strategies companies are pursuing to win it. It’s my view that user-generated video (UGV) will differentiate mobile platforms in the coming years, and that despite Facebook’s early lead in the mobile advertising market, their hegemony is threatened not by content acquisitions from network operators, but by the best platform at supplying UGV: Snapchat.

Mobile video means money

To start any discussion of live video, it’s important to lay out the endgame, in this case, the mobile video brand advertising market. Here’s a good summary from Bloomberg of what’s at stake:

“Companies like AT&T are embracing mobile video for a simple reason: It’s the fastest-growing video type by consumption, according to the Interactive Advertising Bureau. Already, 14- to 25-year-olds watch more video on computers, tablets, and smartphones than on traditional TV, Deloitte says.

Advertising should bolster mobile-video revenue, which globally will reach $25 billion by 2021, up from $12 billion today, as the number of mobile-video users more than doubles to 2 billion by the end of 2022, says researcher Strategy Analytics.”

Or, without the numbers: mobile video attracts younger audiences which attract ad spend.

Facebook got the early jump on the mobile ad market, but it’s clear now that if they’re to maintain this position, they’ll need to supply the most engaging mobile video content available.

What we watch on our phones

If mobile video is the market, what are media companies doing to win it?

On one hand, you have the telecom operators who, faced with a maturing wireless business, are looking to buy their way into mobile video, Verizon with its go90 media properties (from AOL and Yahoo) and AT&T with its premium content (from Time Warner Cable and DirecTV.)

On the other hand, you have the social platforms -- Facebook, Twitter, YouTube, Snapchat -- pushing a hybrid publisher-user content model. The first side of this includes pursuing exclusive content deals: Twitter with its NFL rights, Facebook Live with its media and celebrity deals, et al. These deals are an important part of keeping users engaged, but their higher goal is to prop up the other side of these platforms’ content models: getting actual users to generate their own video content.

User-generated content is so valuable to internet companies because it’s content that’s proprietary-by-default to the platform on which it was created. When a user uploads a video to Snapchat or Facebook, that video is an exclusive differentiator for that platform unless the user manually shares it elsewhere. (This certainly happens but it’s an edge case.) Social platforms understand that as good as viral cat videos are at reach and engagement, they aren’t differentiators for their service.

In mobile, it’s user-generated video that’s king; everything else comes second. Social platforms have noticed this UGC dominance and responded. Snapchat featuring user stories above publisher content is one example. Facebook’s news feed change promoting content from friends and family is another. And so as platforms prioritize user-generated video within feeds, a new problem emerges: how to get users producing this content in the first place.

How platforms incentivize user-generated video

For the average user, sharing a video of oneself is a terrifying prospect. More than a status or a tweet or a photo, it’s video (especially live) that’s the hardest medium to curate, the hardest form to mold into the picture of self that we want to put on the internet. Zuckerburg acknowledged the pressures users face in creating video content in an interview earlier this year...

“People look at live video and they think [it] is a lot of pressure because it’s live; it takes a lot of courage to go live and put yourself out there.”

...he then goes on to address how he sees those pressures decreasing with app developments...

“But what we’re finding is the opposite, a lot of the biggest innovations have been things that take some of the pressure out of posting a photo or video.”

So what are these “innovations” that ease the pressure of posting video for end users?

For Facebook, they’re advancements like improved latency (to ensure video really is live for its audience) and live-streaming reactions floating across the screen like warbly sheet music (to validate users’ content.) Both are efforts to get the technology to a place where users can just have a live conversation with their followers sans curation.

While this has worked for a small subset of early adopters, the early stars of Facebook Live, for the larger majority of Facebook users, there’s an essential UGV incentive that, though present in the Facebook Live offering, isn’t salient enough to make users comfortable with the medium. Ephemerality.

All we are is pixels in the wind

Ephemerality is the third and, to date, best way to get users to share video. It’s a simple agreement with users. Want to share personal, uncurated content? Go ahead. It will be gone in twenty-four hours.

This is what Snap (nee Snapchat) has done so well. It’s not just that everything you publish within their application is ephemeral, it’s that from day one, everything associated with their brand has laddered up to this larger theme of ephemerality -- even with a hardware product launch like Spectacles. The result is users who default to Snapchat when they’re looking to share uncurated content of themselves, being themselves. When they’re looking to share video.

The numbers speak for themselves. As of earlier this year, a third of Snapchat’s daily users were publishing to their story once a day. It’s hard to know what percentage of that cohort includes users who uploaded video, but a safe bet it’s higher than the portion of Facebook users doing the same.

It’s in contrast to this Snapchat bugle call of “ephemerality is everything we do” that Facebook Live’s optional ephemerality wans. It’s a tough position for the company. Facebook’s traditional value prop has been permanent web identity, yet now they find themselves trying to win a UGV supply game in which the best thing you can give users is a twenty-four hour content lifetime.

It’s this dichotomy -- permanence vs. ephemerality -- that’s surfaced not only within Facebook’s go-to-market strategy, but within their Live app itself. As a user, you have to make a decision every time you use the app. Either make your content ephemeral (by not saving it to your timeline) in which case it’s truly live and synchronous, or make it permanent, thereby making it asynchronous (and increasing your audience size) but forgoing the ephemerality compact you likely associated with “live”in the first place.

It’s a difficult decision to think through as a user. The easier option is just to record everything on Snapchat, where the decision is made for you. Put up whatever. It’s gone in a day. Simple.

Facebook has a great technical app with Live, but if they’re to get back into UGV in a meaningful way, they’ll need to make the hard commit to ephemerality. When users start to record everything, there’s only so much they’ll want to stay on the internet forever. For-eh-ver.

Clean bathrooms

I once heard someone say the key to great customer success is clean bathrooms.

It was a mantra at his previous startup that any employee of the company would always be on the lookout to make sure the bathrooms were spotless.

Customers often come to visit, and when they do, they may use the bathroom. When a customer has to use their vendor’s dirty bathroom -- crumpled paper towels near the waste basket, caked hand soap on the counter tops -- their reaction will be, “these guys can’t take care of themselves, how are they going to take care of my business?” No matter how great your meeting was. Keeping a clean bathroom ensures this doesn’t happen.

But there’s something else you instill in a company’s culture by making sure everyone looks out for clean bathrooms. It’s the Mr. Miyagi effect. In keeping the bathrooms clean, in picking up that stray paper towel that didn’t make it into the trash, people overcome their “someone else will do it” gene.

Once someone can overcome their “someone else will do it” gene in a bathroom, they can overcome it anywhere. Messy implementations. Hard customer calls. Doing the tough work that doesn’t scale.

It’s the kind of work that doesn’t slip through the cracks for a company with great customer success. A company with happy customers. And clean bathrooms.

Cellphone concertos

This week I came across a clip of pianist Christian Zacharias discussing cellphone interruptions during his performances. 

I’ve written before about finding little moments during the week to focus on one thing and one thing only. Zacharias’s take on that “rare moment when our minds can go and focus on one thing” (and what it’s like to be at the center of such a moment when a cellphone rings) is a good one.  

Surprisingly, by the end of his talk, Zacharias takes a near-optimistic spin on the ringtone interruption, saying that it can remind the audience that they’re part of a collective silence and focus, that there is “something happening.” 

Sure enough, at the end of the clip, we see such a moment. Zacharias waits at the piano in silence after the ringtone has been snuffed out, waits for a few beats, then plunges back into the piece with spirit anew. Even just watching the clip, you can tell there’s something special taking place in the concert hall. (The look on the face of the concertmaster at 2:29 is another giveaway.)

There’s a certain irony here in that the ringtone has, in a strange, roundabout sort of way, added to the performance. The phone rang out, the orchestra responded. A cellphone concerto.*

*This isn’t to say let’s all go to concerts with our ringers on blast. On the contrary, let’s not do that. Still, I thought Zacharias’s talk an interesting one, and the clip is worth your time.

A Grand Synthesis

This past weekend while reading Mitchell Waldrop’s Complexity, I came to a passage describing Charles Darwin’s theory of evolution as “a grand synthesis.”

“Darwin’s theory of biological evolution had been just such a grand synthesis in the 19th century. It combined evidence from biology, which revealed that different species of plants and animals were clearly related; from the emerging science of geology, which showed that the earth was incredibly ancient and that the past afforded immense vistas of time; and from paleontology, which proved that the plants and animals who dwelled in that immense past had been very different from those alive today.”

I’d primarily considered “On the Origin of Species” as belonging to the field of biology prior to the excerpt above, but I like Waldrop’s refresher* on Darwin’s theory as an interdisciplinary work that pulled from multiple fields to make its inferences about the natural world.

It loosely reminds me of “connecting the dots." The ideas worth pursuing are in between the dots; they emerge from the complexity between disciplines.

*via Murray Gell-Mann.

Product and the Narrative Gap

A few years ago I picked up Robert McKee’s Story, a book about the structure and stylings of plot and narrative. One of its concepts that’s since stuck with me is that of the narrative gap.

Here’s McKee on the gap:

“The moment [the protagonist] takes this action, the objective realm of his inner life, personal relationships, or extra-personal world, or a combination of these, react in a way that’s more powerful or different than he expected. This reaction from his world blocks his desire, thwarting him and bending him further from his desire than he was before he took this action. Rather than evoking cooperation from his world, his action provokes forces of antagonism that open up the gap between his subjective expectation and the objective result…”

The narrative gap is the result of a protagonist’s action, the difference between subjective expectations and objective result. As the audience, we recognize when a protagonist meets this gap; it creates tension, it makes us anxious, we want to see the protagonist’s worldview resolved and restored.

Gladiator is a good example.

Maximus is a good man. We know him to be a good man. Our collective expectation is that Maximus will win his battle against the barbarians and get to return home. The narrative gap emerges when Maximus’s subjective worldview meets objective reality; Commodus’s usurps the throne, Maximus’s family is killed, and Maximus is thrown into slavery. The rest of the movie is Maximus clawing his way back, struggling to make objective reality conform to his subjective view of what is right in the world.

It is the writer’s job to create this narrative tension. To surprise the audience with what is expected and what actually results.

Compare this to product, where it is the job of the product manager or designer to do the exact opposite, to eliminate all narrative tension a user encounters when using a product.

For every user interaction, the result must be exactly what was expected. If it isn’t, if objective reality doesn’t align with a user’s subjective expectations, if an interaction results in  an unexpected outcome, then the user encounters a “narrative gap” in the product, just as they would in a story.

But (unlike story) product has no promise of resolution. The only way a user can resolve narrative tension in a product is to either a) mold their subjective model of the world to the model presented in the product or b) find their subjective model somewhere else. Option A is unlikely. Option B is churn.  

I like the narrative gap as a lens for user experience. If the user meets unexpected results, if they are working against “forces of antagonism” to make the product do what it is supposed to do, then there is room to improve.

Thoughts on the election

It‘s been a difficult week. 

On Tuesday night, as the Florida panhandle vote arrived, as Ohio was called for Trump, as network touchscreen jockeys frantically tapped into counties, looking for votes that wouldn’t come, a special sense of dread flooded half the living rooms in this country. I won’t forget that feeling. 

When I first started to collect my thoughts on paper late Wednesday night, I tried to answer how and why this happened. I poured through articles and tweets from both sides. I wrote about how Trump had the better motto, how the democrats fell into the policy fallacy, how the media failed to empathize with rural america. I looked for a single reason for why we elected Trump. 

In the days following, I’ve stopped trying to rationalize every facet of Tuesday’s result. Instead, I find myself trying to answer a different question: what comes next?

The answer doesn’t come easy. Even within liberal circles, a divide has emerged.

On one side, there are those who, in the face of a president-elect Trump, mourn the end of this country, who proclaim, with certainty, that Trump’s election will lead to “all manner of national decline and suffering.” Despite the pessimism inherent in these statements, in response to Trump, and everything he’s represented for the past year, they are warranted.

But there’s part of me that still wants to believe in this country, that wants to believe Trump said what he needed to win, that wants to give him a chance. This is the message heard from the moderate side of the liberal base -- that it’s time to work with the right. It’s a positive message but one that’s difficult to accept. We consider Trump, and the misogyny, nationalism, and racism that he, still, has failed to speak against, and feel hopeless.

Many of us, searching for the answer somewhere in between these two sides, find ourselves caught in a paradox between our own values and the values of democracy. A democracy demands that its citizens accept the outcome of its process, and yet, here we are, barred from accepting that outcome by our own morals.

Caught within the seeming impossibility of this paradox, a single, absolute truth emerges: that our great nation must, above all else, persist. That it must endure.

In 1861, faced with an equally divided nation (and a real threat of secession,) a newly inaugurated President Lincoln made the same appeal, that “perpetuity is implied, if not expressed, in the fundamental law of all national governments,” that “descending from these general principles, we find the proposition that in legal contemplation the Union is perpetual confirmed by the history of the Union itself.”

In that history of the Union, in those “general principles,” is the foundation of this country, the belief that there are truths self-evident, “that all men and women* are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness.” 

I still have faith that the vast majority of this country, independent of party affiliation, believes in the promise inherent in those words. As long as that continues, I keep faith in “the ultimate justice of the people,” in the belief that there is “no better or equal hope in the world” than the fundamental law of humanity inherent in the declaration of independence and in our country. 

If we take this natural law to its furthest logical point, we find a future where anyone can be President, no matter their gender, ethnicity, or sexual orientation. Perhaps this is why Tuesday’s result is so difficult to accept, because we felt so close to that future, because we felt we were already living in it. To have it taken away in a night is to know that we’ve taken a step back.

For now, we hold tight to virtue, we become active members of our local communities, we remain vigilant for those who, in positions of neglect or targeted hate, do not have the privilege to wait until the next election. 

We keep an open dialogue between sides.

We keep the faith that “no administration by any extreme of wickedness or folly can very seriously injure the Government in the short space of four years.”

We keep the faith that the watchful eye of the people will win against the racism seen in the days since Tuesday, that this country, as haven for immigrants, for innovation, and for free will, will remain. 


*include women in the sequel.

Slack's Open Letter

Slack published an open letter to Microsoft in the New York Times this week. Like a valedictorian’s speech, which, at the outset, promises the deliverance of sage advice, only to then slip into the rote listing of its scribe’s accomplishments, the letter was received by many as smarmy* condescension.

I, too, found the open letter a little cringe-inducing, not just because of its tone, but because of its contrast with another piece of Slack’s open writing, CEO Stewart Butterfield’s excellent memo “We Don’t Sell Saddles Here”.

WDSSH was a bugle blast. A rousing call-to-action for a team about to put something new into the world. The essay’s focus was the customer and how Slack could bring them into the new market they were defining. It mentioned the word “competitor” once. I didn’t work at Slack and I still felt inspired when I read its closing line: “The answer to Why? is because why the fuck else would you even want to be alive but to do things as well as you can?”

Maybe that’s why last week’s open letter was a disappointment. Because it signaled that Slack had moved on to worrying about competitors, not customers.

For that’s what the letter said more than anything else, that in spite of its explicit appeal to customers, it was implicitly still a letter to a competitor.

The irony is, as a user of Slack, I didn’t consider Microsoft in the same ballpark when it came to team messaging. Even with the announcement of Teams, I’d been through too much with Lync to assume they’d ever be a part of the enterprise collaboration conversation.

Well, they certainly are now.

*all credit due to the Verge’s Casey Newton for finding the perfect word for the tone of Slack’s open letter.

Data Gravity

On Microsoft’s earnings call last week, an analyst asked why the company saw a 7% increase in the gross margin of their commercial cloud offering.

Nadella’s answer (emphasis my own):

When we do CAPEX we're buying the equipment for everything that Microsoft does, which is everything from Azure to Office 365 to Dynamics 365 as well as our consumer services like Xbox Live. And you see the growth that we talked about across all of this. we drive efficiency in our cloud infrastructure... that's an efficiency that we gain across the marginal cost and gross margin that spans everything that we do.

Then also what we think about as the mix, our goal is not to just sell a commodity services, but to actually use commodity services in some cases as a bootstrap for higher level services, because of things like data gravity.

…but I would ask our investor base to think more about the architecture as well as the financial outlays of what we are building. We're not just building Azure. We're building Azure, Office 365, Dynamics 365, as well as our consumer services which are all cloud oriented. And it's the combination of that that's driving margin.

I liked this response and the model of “data gravity” that Nadella put forward.

Nadella stresses that the architectural and financial benefits of the cloud are not just restricted to Azure. That as Microsoft onboards more customers for storage, compute, and other commodity services, they’ll expect them to subscribe to higher level services as well, thereby furthering the efficiency benefits that Microsoft saw in this quarter’s earnings.

This is data gravity, a customer’s predilection to use a single provider for a collection of services, and to select that provider based on the amount of data they already store with them.

This isn’t exactly news. When your service houses data valuable to a customer, it’s difficult for that customer to leave your service. Hence, why everyone continues to put up with the Salesforce UI -- if they left it, they’d lose a lot of historical sales data (or have to orchestrate a complex migration of said data to their new vendor of choice, a fate worse than trying to complete a Salesforce form with required fields.)

Though SaaS pundits and management have long written about the benefits of serving as a store of record, the term “data gravity” really strikes home the model.

Imagine Einstein’s fabric of spacetime, where instead of a planet and its mass, pulling rogue objects into orbit, you have a service provider and its data, pulling in additional services, thereby increasing the “mass” of that provider and the “pull” it has on other service offerings.

This is why Nadella asks investors to consider Microsoft’s commercial cloud as “not just Azure”, but as a larger offering of services that enterprises can adopt in full. It’s his belief that by offering all of these services to the enterprise, he can bring customers (and their data) into the entirety of Microsoft’s commercial cloud offering, thereby driving even more efficiency on their capex.

In practice, I’m not sure that storage and compute customers are going to rush to sign up for Office 365. But Active Directory customers probably will, and if there’s a segment ripe for the low-barrier decision of selecting the vendor you already use for identity management and commodity cloud services, it’s the enterprise.

Five Tool Player

My sophomore year of college, Jeff Weiner came to speak to my BUSN 174 class. It was 2009 and LinkedIn was a long way from becoming the company they are today. Jeff was still interim President -- a few months after speaking to our class he’d be named CEO.

During Q&A, a student asked him for the one piece of career advice he’d give to fresh grads.

Jeff’s answer: become a five tool player.

In baseball, a scout’s dream prospect is the the five tool player, the ballplayer who can hit for average, hit for power, run, throw, and field. My go-to example is Griffey: either because he’s the best ever, or because I watched more baseball as a seven-year-old in 1996 than I have in the cumulative years since.   

In business (and, specifically, in tech,) the five tool player is the candidate who has:

  • Technology vision. Sees the future and what needed to get there.
  • Product sensibility. Meets the needs of users with great product.  
  • Business acumen. Knows not to sell a dollar for a quarter.
  • Leadership. Inspires others to meet a shared vision.
  • Resourcefulness. Asks for forgiveness, not for permission.

This advice has always stuck with me. Since hearing it, I’ve kept it in the back of my mind, a sort of North Star for what to frame in the long-term.

If you want to read more about Jeff’s five tool player, he’s blogged about it on LinkedIn here.