Editorial Independence and Money

Like any normal reader, I have mixed and varied reactions to the things posted on Deadspin, a venerable and popular blog presumably about sports but more about… things. However, I do not have mixed feelings about whether Deadspin should exist, or whether it has written, reported, and uncovered some truly incredible things in addition to creating the Hater’s Guide to the Williams Sonoma Catalog. My feelings to both of those things are extremely affirmative.

So it’s too bad that in the weird, continuing jihad against everything ever associated with the defunct-for-a-while Gawker Media, a bunch of private equity -- look, let’s just say “people” instead of “morons” -- are effectively driving the site into the ground and out of existence with not just a bad plan for running a website/business, but a boring one. Does it get any more predictable than —

  1. stuffing the site with the loudest, most annoying (autoplay!) advertisements possible, and tons of third party tracking javascript
  2. driving out beloved staff members and clearly skilled, well-credentialed, leadership (not over money, but editorial practices)
  3. hiring a bunch of bros from Forbes and other worthless, despised internet organs
  4. … and finally putting the kibosh on what makes Deadspin, well, Deadspin but issuing an ESPN-style “stick to sports” mandate that couldn’t possibly, in a million years, work?

No, it does not. These goobers are wrong, they are murdering something that should probably exist, and they will walk away with nothing. This isn’t an investment in anything other than eliminating Deadspin, which was probably the idea.

Don’t get mad, get even.

But anyone can say that, and a lot of people will do exactly that, and do it better than I ever could. So instead, I’m going to ask this — how do people like the writers and minds behind Deadspin, Splinter, and other publications that disappear at the whims of a billionaire protect themselves from something like this?

I’ve seen lots of editorial unions pop up recently, and I think unions are cool and a good idea. But ultimately, I don’t think they’ll do anything to stop this kind of publication murder. The private equity guys are going to ruin Deadspin in ways that can’t be countered with collective bargaining, and in the end they’ll simply make it so no one wants to work there, so no one will, end of story. Unions work when there’s a threat of mutually assured destruction, but the problem is that the union can only destroy Deadspin; it can’t destroy Grey Hill Partners or whatever the hell they're called, so if those guys are fine with Deadspin being destroyed (and they clearly are), that’s what will happen. Checkmate.

Ultimately, Deadspin can’t be saved because Deadspin — like the editorial staffs at most publications — doesn’t control how they make money, and therefore are at the mercy of business people. Now again, if those business people need the publication to work, they have some skin in the game, and you can reason/bargain with them. I have worked at organizations with this shared fate; where business people want to make money off of great journalism (or at least good, useful journalism), and that dance is danced. It’s fine.

But a lot of situations are not like that at all, which too often leads to hastily formed, realtively weak unions making “HOW DARE YOU, SIR” statements on Twitter and not a lot else, other than a slow bleed of talent and the eventual defenestration and Sports Illustrated-fication of a publication. This is no way to grow a media ecosystem.

Great journalism needs business allies, with aligned interests. It just does. And I really do think that means some journalists need to go into business (and some do, but I want MORE), just as more technology companies need to form without raising huge amounts of venture capital that then necessitate huge returns that themselves necessitate deception and monopolies and anti-civic behavior. Can you imagine how great Facebook could be (as a product) if they only ever wanted/needed to make $100 million a year in revenue? Does being able to have 50,000 employees and buy Oculus Rift and all that make up for the cost of needing to ruin democracy to meet revenue targets? I would venture that it does not.

Similarly, journalism HAS to get into advertising, or whatever form of revenue it expects to generate in order to pay its bills. Outsourcing to third party ad networks, Facebook, Google, etc., is cutting a deal with the devil. Saying “you handle the money, and we’ll handle the journalism” is a fine way for two journalists to start a publication. It is not a fine way to work with a bunch of people who don’t actually care about journalism.

So that’s what I want. I don’t want Deadspin writers to go find a bunch of business people and try again with a bigger promise of editorial independence. I want someone who is mad, right now, about what’s happening to Deadspin to build a business — even a small one — that is focused on owning it’s own financial future, so it can determine its own management and policies, and make sure this kind of thing never, ever happens to it again.

Not sure I can help, but if I think of any ideas I’ll let you know.

The Clueless Majority

It's been an interesting couple of years for minority-majority relations. So many of the different have/have-not dividing factors in American society -- gender, race, wealth, geography, even technical knowledge -- seem to be chippier, more emotional, and increasingly called out by people on the less advantaged side. Sometimes it's because the situation for the people on one side is getting worse, and sometimes it's just because those people have a means of making the divisions visible, or easier to understand. But either way, there's huge, multi-factional backlash in almost every power dynamic today, and it has a lot to do with why every issue seems "more polarized".

It's always relatively easy to dismiss basically any dividing line you're on the "right" side, or "easier" side to be on as the result of victimhood culture, or if you're less inclined, to figure out a way to exclude yourself from the advantaged group. That doesn't mean there are literally no people who live in artificially generated oppression (there's basically someone doing this in every office/workplace/organization, right?). But it does mean that when you dismiss or rationalize away a dividing line, as people on the easier side naturally have a tendency to do, more often than not you are missing something.

I read a story about a basement comedy show in New York where a couple of performers felt obligated to call out the fact that Harvey Weinstein was in the audience. He -- unsurprisingly -- did not like being called out and mocked for the long list of unspeakably despicable acts he's accused of.

“This scene was uncalled for, downright rude and an example of how due process today is being squashed by the public, trying to take it away in the courtroom too,” the representative said in a statement to the Hollywood Reporter. “Accusations are, in fact, not convictions."

The Washington Post

To me, this is a great example of why so many of the traditional societal norms we rely on to interact, establish moral authority, and assess situations feel like they are falling apart, or just not working anymore -- and despite the histrionics from Weinstein's rep in that statement to the Hollywood Reporter, they're not falling apart because a bunch of young, semi-professional comics decided to call out Harvey Weinstein in a bar. To think that they are completely misses the point in a way only people on the right side of social divide can.

Family as micro-society

Humans, like all animals, inevitably deal with the concept of "power", including who has it and who does not. Some of us are bigger, stronger, smarter, faster, more charismatic, whatever, than others. In life, almost immediately, we create some kind of methodology for dealing with these discrepancies. My daughter is a year and a half older than my son, and (as I write this) they are young enough that it's a massive physical difference. A very physical three and a half year old has an immediate power advantage over a generally peaceful two year sibling that she has to decide what to do with.

Now, she also has parents, who are both way bigger and more powerful than either her or her brother, and that gives us the ability to build a little society, with rules in it. We inject concepts like fairness into their interactions, and we enforce those concepts with our own power, in an attempt to both (a) create a somewhat equitable little society in our home, and (b) model that kind of society for two little developing citizens.

But, just like in life, our enforcement of these laws has normal biases that determine what the actual society of our home is like, versus the one we think we have. My daughter, for instance, like any smart three year old, has learned that by being older and thus more verbal, she is better at blaming her brother for things than he is at defending himself. She explains her side of the story, her brother can't, we start to believe her, he gets frustrated and reacts in the only way he can -- by hitting her -- and he gets dragged off into his room and punished. I know how this works, as I too was a little brother to a smart, verbal sister.

But I had good parents, who were aware of these sorts of in-home biases, and corrected for them pretty well. In the end, we actually had a fairly equitable in home society, and that's one of the reasons why I have good, open, baggage-free relationships with my parents and my sister. We can laugh about the inequities that existed because my parents did a generally good job at mitigating them (and not letting them create vicious cycles), and because as my sister grew up, she quickly internalized the value of that healthy in-home society and did less and less to sabotage it for personal gain, and more and more to protect it. As the youngest, I had the least amount of ability to do damage, but I too picked up these cues (including when my sister turned down chances to turn her inherent advantages into unfair outcomes that would benefit her) and basically grew up into a decent human being.

Society as a family without parents

When Harvey Weinstein's camp claims the moral high ground in an encounter like the one in the aforementioned comedy club, they're framing everything as if it's happening in an equitable society with consistent elements of individual rights and due process. That assumption is inherently part of the argument, just like it's part of the Trump administration's arguments against impeachment.

But the hypocrisy here is immediate. The very nature of what Harvey Weinstein is very, very, very credibly accused of is possible only due to the fact that the people he abused and assaulted did not have their individual rights and due process protected. Weinstein's message takes umbrage at a lack of societal decorum only when he needs societal decorum to protect him -- and for years and years, not only did he not need it, his lifestyle, outlook on life, and day to day routine actively required not respecting societal decorum in any way, at least when it came to limiting his actions or holding him responsible for them. He used his position, power, and wealth to completely circumvent the very idea of societal decorum so he could assault people.

Similarly, the Trump administration is operating in comedically bad faith. They control every lever of law enforcement except one, which is impeachment. And while they visibly enjoy flexing that power at every possible opportunity, with total impunity and 100% self-interest in mind, when it comes to that one other lever, they immediately demand that societal norms -- any norms you can think of -- limit the power, or even remove the existence, of that lever.

These bad-faith actors are like older siblings in a house with inattentive parents. They are happy to let the law of the jungle define how we interact with each other, until all of a sudden the jungle isn't favorable to them -- that's when you run to Dad and tell him to stop looking at his phone for a second.

Principles and academic arguments can matter, and we should build a society where they do matter. But that society is not one where those principles and academic arguments are applied only in defense of powerful people who have unexpectedly lost the ability to do whatever they feel like. Very few people are going to have sympathy for Harvey Weinstein receiving a relatively minor extrajudicial slap-on-the-wrist (being mocked at a comedy club) even if (and I know, roll your eyes, I'm rolling them too) he is potentially not guilty, when there are thousands and thousands of people abused, punished, exploited, and effectively tortured extra-judicially by Weinstein and people like him. In other words, you're not going to be able to successfully argue the relevance of due process to the masses when the masses frequently receive no due process rights from people like you, or the state, at all.

"It's a meritocracy!" claims are similar. They make sense in theory, and they definitely make sense in certain small social circles. But people aren't stupid -- they are constantly witnessing non-meritocratic outcomes, from family businesses, to legacy admissions at elite schools, to sons of senators becoming senators. They see and experience obviously different criminal justice outcomes, public service outcomes, political outcomes, and even consumer outcomes from various captured markets. They are pounded with more and more examples every day, in their own experiences and in the experiences of other people like them facing similar circumstances. You can make the argument that this is a system people should like -- that family businesses and inherited wealth have moral and social benefits that outweigh the benefits of a meritocracy, or that we are safer and happier by (extreme eye rolling) having different criminal justice policies for different kinds of people. But you can't deliver that second experience, and then retreat to the benefits of meritocracy and equity when people want a version of the world that's skewed a little bit more towards them instead of you and expect your argument to stick.

In business, this kind of self-serving hypocrisy is best represented by the idea of socialized losses, and privatized gains, and we do it all the time. It sucks, it's biased for people who have inherited, unearned advantages, and it pisses the average person off. In society, it's "let me use my power advantage uninhibited until I run out, at which point we should all have equal power". In meetings at tech companies, it's "let's use data until the data says my idea is bad, at which point let's use vision and experience" (and vice versa -- when someone else's experience trumps yours, all of a sudden this needs to be validated with data).

The view from the top

I am a mid-thirties, married, upper class white male with cute little kids who lives 30 minutes by accessible mass transit from New York City. I grew up in a nice, quiet suburb with two healthy, funny parents with post-graduate educations, and a big extended family that loved me and watched my back. I even work in technology! There are very, very few ways for me to feel like the odds are against me in any way, but even I can feel isolated and weird and unsupported and alone if I try hard enough. ("The business world is biased against introverts! I don't look good in suits!!! PEOPLE PREFER LIARS!!!!")

And that's the challenge, I guess; understanding that in the vast, vast amount of scenarios that exist, the checks and guardrails of society need to be put in place to protect people from me, not to protect me, and that I don't need to feel attacked or threatened by that. If you're a dude at a tech company in your 30s, and you have women in your 20s reporting to you, it's not that much of an imposition to take into account that you have certain levers available to you that others don't, and to go a little bit out of your way to make sure you don't push on them. It's also not that hard to resist taking massive umbrage when, despite your best efforts, you fail, and realize (or are told) that you've leaned on one of them. In fact, sometimes people will assume, or "accuse" you of doing that, and they will be wrong, or confused! OH MY GOD WHAT AN INJUSTICE. Just stay calm, be honest, and try to think about the scenario from other perspectives before you immediately declare your corner is under attack.

Ultimately, the problem is that we do live in an inequitable society, and it's difficult to maintain that unless you install some very real principles (ask the French), or are willing to go full-on, brutal caste system to protect your interests (ask... well, there are lots of places to ask).

I don't want to do the caste system thing, and "let them eat cake" is demonstrably unsustainable, so I'm voting for "ease off the personal gain throttle a hair" approach, and hoping we can soft-land this thing.

The Urban Millennial Lifestyle

There are -- and for some time, have been -- a lot of dumb, unprofitable business ideas designed to pique the interest of urban millennials (among others), and propped up by venture capital.

If you wake up on a Casper mattress, work out with a Peloton before breakfast, Uber to your desk at a WeWork, order DoorDash for lunch, take a Lyft home, and get dinner through Postmates, you’ve interacted with seven companies that will collectively lose nearly $14 billion this year. If you use Lime scooters to bop around the city, download Wag to walk your dog, and sign up for Blue Apron to make a meal, that’s three more brands that have never recorded a dime in earnings, or have seen their valuations fall by more than 50 percent.

Derek Thompson, The Atlantic

Are the people who use these services in for a shock if the seemingly bottomless private funding for these services collapses, as it has for WeWork? It's hard to say, as (1) that's a pretty big if given how much potential investment capital just sits around waiting to be suckered by the next WeWork guy or Theranos lady, and (2) part of the reasons people used these services is that they were there. If you couldn't use DoorDash or Postmates (true story, I've never used either), I don't think a bunch of twenty somethings in Brooklyn would just collapse in a corner. They'd probably just get up and pick up food.

What I do find interesting is whether companies/capital look at these high-demand/low-profit businesses and think "forget it", or do they come back and try to meet these needs with real business models?

In a lot of cases, I think there is real opportunity for right-sized companies to provide similar services with much lower revenue and growth expectations, and as a result, with less capital. Wag doesn't need $300 million dollars in capital in order to figure out how to get people's dogs walked, and it really doesn't need growth targets on its back commeasurate with a company that's raised $300 million. This is a dumb way to solve relatively simple problems, but it doesn't mean it's the only way.

In other cases, all that capital is needed to subsidize a service that isn't actually better or more efficient than the alternative. This is Uber (and probably Lyft), so it's hard to predict what, if anything, pops up in the place of those two companies should they disappear. Do people want private car rides from independent drivers if they cost the same as a taxi? What if they cost more?

The elephant in the room, though, is that all of these companies are looking to provide services for what seems like a great demographic -- young educated people with in-demand skills in areas that are often thriving economically. But even these people don't actually have any money, as Derek Thompson (who I'm now citing twice) has also noted. So a (the?) common thread among all of the companies mentioned above is that they're trying to provide expensive, personalized services cheaply to a bunch of people who love services but don't have any money. In a few cases, those services can be provided more inexpensively through technology, but in most cases, technology is really just a device for laundering costs and passing them on to someone else, like a network of contractors. Alternatively, technology is used to make an expensive service easy to access on demand, and then the actual expense is covered by venture capital.

Seems like we can do better, here.

Little Data

I never really had to think about actual business data until about five years ago. Before that, like a lot of professionals, I dealt with lots of numbers, but none of them actually mattered because they were all basically vanity metrics that never got to the root of anything. I tracked things like open rates and leads created via campaign X and all of that, but as someone in a low level support role, or product marketing & copywriting at a small company, I never had to connect the elements of my work to -- literally -- how we made money.

When I joined Contactually in 2014, it was the first time a majority of a company's revenue went through something I was so directly involved in -- in that case, content and eventually product marketing, which by the time I left involved getting people through the trial phase of things and into a monthly subscription. Sure, there were sales people moving things along for certain clients, and eventually working on enterprise deals, but during my relatively short time there (about a year and a half), we made most of our money through self-service, and I was supposed to make or work on a lot of the things that made self-service work, from a business perspective.

Working with a cheaper, self-service business model also significantly expanded the scale of the numbers I did have to think about. We needed thousands of leads to get to our goals, and they came in (and left) very quickly. I spent a lot of time looking at spreadsheets, and "the leads" were sort of an amorphous concept of success to me, versus an amalgamation of actual people. While I didn't like, freak out and run out of the building screaming, I never felt like I had a real grip of what was going on, and instead sort of poked at various marketing tactics that were supposed to work while watching large numbers move up or down in ways that mostly seemed disconnected. I did not really know what I was doing, but I learned a lot, even if it was mostly just learning what I needed to get better at.

I joined FiscalNote in 2015 to go into a very different form of product marketing that was closer to what I knew -- basically glorified sales enablement for fairly large ($10k+) annual contracts. My work teed up a large sales team; it wasn't itself a revenue funnel. I knew how to do this sort of marketing-as-a-service (and how to think about it), so it was immediately less stressful. However, at the time, FiscalNote was still a very young company, and I was sitting in the room and providing supporting material for lead generation and sales processes that -- the more I looked -- were clearly leaning on absolutely atrocious data practices. Eventually, through what I can only assume was some sort of clerical error, I ended up being responsible for large parts of our marketing department, and eventually the entire thing (probably another clerical error). There was no looking the other way at that point.

When I talk about "atrocious data practices", I'm not talking about any one person's individual incompetence, and I don't mean that we were any worse with data than anyone else. What was horrifying is that we were actually pretty normal, and the people working with awful data were all pretty smart. But that doesn't mean we weren't often doing incredibly stupid things. Because while almost everyone was smart, almost no one was cynical about data, technology, or how the two were related.

The number one culprit for us -- and I think for many people -- was that we constantly looked at data exclusively from the top down. What I mean is that at some point, someone set up a giant Salesforce instance, or a Marketo instance, or whatever, and created some basic, automatic process for names, or companies, or something to get sucked into one or more of these systems. The automation works, the names go in there, there's a ton of metadata (probably TONS), and it all looks very robust and thorough. Welcome to BIG DATA.

If you're like everywhere I worked, the initial purpose of this system is to organize Sales, because if salespeople aren't organized and busy, they will kill you and eat you, and whether it's two or two hundred, you probably hired too many of them because someone built a capacity model that said "sales head = $X". Everyone does this, because to some degree it's true, but companies with big growth targets and some amount of traction tend to overstate it. So the salespeople create tons of "opportunities", or "deals", or whatever the basic unit of potential revenue is at your office, and includes exactly the bare minimum of information and updates required for them to be paid out by whatever the specifics of their compensation plan requires. So almost immediately, you end up with tons of zombie data, old opportunities, incorrect information, and outright lies from people who usually get fired after a while. Again, unless you're entirely self-service, this is your basic unit of business data.

Ghost in the Machine

At this point, something weird happens. Maybe it's because leaders come and go, and institutional knowledge disappears, or maybe it's that there's some amount of success, and it becomes taboo to really think about whether any of these systems were set up appropriately. But before you know it, the key decision makers -- and maybe everyone -- has becomes completely disconnected from what this data actually is. Don't get me wrong, people will acknowledge "data problems" in general, and create projects like "clean up Salesforce", and even spend money and time on it. But for some reason, at a certain stage it becomes incredibly rare and crazy-sounding for anyone with any seniority to want to get in and try to basically model out the business manually, without BI tools or whatever. But that means no one actually understands the data -- engineering, or accounting, or an SF admin know the computations that happen (but not why, or what it's supposed to represent in the real world), and business people look at overall performance and look for ones that make it look like whatever has been bothering them is, in fact, a problem.

So you get business assessments of things like "marketing-influenced pipeline" being exceptional, or exceptionally poor, or important, or unimportant, and some hoodie-wearing goober like me is tasked with responding right in the middle of a really good daydream/reminiscence about the 2008 Eastern Conference Semifinals.

And when I do get asked that -- again, because I am a hoodie-wearing goober -- I usually ask a simple question.

"Do we actually know what marketing-influenced pipeline is?"

Incredulous faces. MBA syllabi flicker to life in the minds of people desperate to reference them. "You see, what we're talking about is the amount of opportunity value that was specifically driven by a marketing activit---"

"No, I know that. I mean, how is that calculated at this company, and..."

(this one always ends badly)

"... can I see an example?"

I want to be really clear. I do not think I am smarter than the fictional co-worker archetype I'm lampooning here. I may think I like better music, I may think my jokes are better, and I may even think I have better taste in typography than these people (I do think this), but I do not actually think I'm smarter, because I am a moron about all kinds of things.

But what I'm really good at is detecting well-intentioned self-delusion. I don't know why this is. Maybe I should write about that someday. But detecting well-intentioned self-delusion is both an incredibly useful AND incredibly difficult skill in corporate America, because corporate America -- and I include any startups beyond "garage level", and certainly any startups with serious venture backing here -- often gets through tough days entirely with caffeine and well-intentioned self-delusion.

The business analytics industry, and the B2B software industry in general, knows this. Hell, I know this, because -- very meta -- I work in marketing spinning up elaborate, plausible scenarios for how we can make your self-delusion slightly more well-intentioned and slightly less (more?) deluded.

And all of this is possible because people, especially decision makers, simply cannot resist looking at data exclusively from the top down.

No, You May Not See an Example

Every executive loves a good dashboard. Why is that? In theory, it's because it gives you the executive holy grail of buzzwords... the "30,000 foot view" of a business, a function, or whatever. But what's really interesting, and maybe even more important, is what it doesn't tell you, which is specific instances of any of the trends, rates, or totals its reporting. Oh sure, it'll show you "top five sources of whatever", or "biggest deals of the quarter", but we're talking about a really small, featured subset of data, and often things that you already know intimately. Who sees something call out their third biggest source of revenue and goes "huh, never heard of that one"?

Instead, in a surprising amount of scenarios, you get things like total numbers -- or even better, month over month changes -- with no way to drill down into them directly from what you're looking at (which means you won't go look). Salesforce is notorious for this, or at least it should be, because it's one of the worst offenders while still allegedly being some kind of machine learning powered business wizard. But more times than I wish to remember, I literally could not drill down into the individual data that added up to some key business metric we expected to base a decision on, unless I exported it to an Excel file and worked on it myself. And when I find something weird, you know what I hear?

"Can you put that in a Salesforce report and send me the link?"

And the thing is, I don't blame anybody for asking that, because something like Salesforce, or your CRM or ERP or whatever is supposed to be your system of record. People should be skeptical of off-the-reservation analysis in a spreadsheet by anyone with an agenda, which is everyone, including me. But when your system of record makes it really difficult, or sometimes actually impossible, to audit your data piece by piece, you quickly end up with an analysis and decision making culture that's a messy combination of a few sales anecdotes from the loudest people in the company, and a top-down view of metrics full of unvetted, invisible assumptions.

I don't really know how to solve this institutional problem, but I did find a way to get my arms wrapped around what the hell was going on -- I used this crazy Google Sheets plugin to manually suck in every single lead, and tons of metadata, from Salesforce into a tab called "TEH DATAZ", and then I built a bunch of elaborate queries in with Google's kind of amazing query language to pull in things from different tabs and do a bunch of math for me. I'm not really a spreadsheet person, but I am a reality person, and the thing about having all my math in that stupid, bloated spreadsheet was that when some total seemed odd, or important, I could go check every individual record that comprised that total. And I did, all the time! It was incredibly informative, and literally every week I found everything from bullshit duplicates that were inflating marketing numbers (whoops, my bad guys) to piles of qualified leads that never got sent to anyone, or were marked as "unqualified" by a 23 year old, probably by accident because they had to get through thirty required drop-down fields in Salesforce.

Typical confusing, noisy startup data from more of a self-service scenario.

I've fixed a lot of stuff with this irritating, stubborn insistence on working with both big and "little" data, but I always get the feeling -- wherever I go -- that people resent it. And the thing is, I know it's not just my annoying face they resent (again, different blog post for that topic), because as soon as I go up to the 30,000 foot view again, people are so happy to hear what I have to say.

The difference is that when I say those things, I'm happy too, because I actually believe it, because I insisted on understanding the individual pieces behind the trend before I started thinking about the trend itself. I think we could all be a little happier, a little less defensive, and work for significantly more productive organizations if we stopped trying to avoid that part of the process.

What are we even DOING here?

For those of you keeping score, this here marks at least the fifth time I've re-assembled and (for lack of a less dramatic word) "relaunched" this site. That includes:

  • several WordPress installations
  • a few years on Tumblr
  • two SquareSpace iterations

... and probably some things I'm forgetting. Every time I do this, I try to think about what I really want out of having a website. That is an increasingly complicated, vague answer, but as I get older I'm kind of surprised to realize what it's not.

More than a few years ago, my friend and former Elementary bandmate Steve retired his amazingly-early 2000s, home-built site. He very reasonably stated that, like me, he was getting older, busier, and had less time to putz around with CSS classes and properly attribute block quotes in blog posts. He also mentioned that if he needed to share thoughts we people, he had Twitter and Facebook, and that seemed good enough.

Something really bothers me about that. Maybe it's as simple as just disliking the idea of my own effort being some company's monetizable "user-generated content". Maybe it's that I want to get my hands dirty with some kind of publishing system, even if it's pointless and duplicative, and in the end actually worse for me and anyone reading this than if I posted on something like Medium. Maybe it's a latent DIY-ethos from listening to and playing in punk rock bands for more than half my life.

Whatever the case, Twitter and Facebook don't cut it for me. Twitter is funny, lightweight, and kind of stupid, and I work in marketing so in a weird way it's a sort of cleverness resume that's actually kind of good to have. But it's like writing in sonnets; for whatever reason I feel way less self-important (and dumb) writing 3,000 words on a website I built than numbering out a threaded tweet. I feel like kind of a jackass just writing that.

What's under the hood

So, as a fairly occupied 37-year old Dad who wants a low-maintenance internet playground, here's what we're looking at for the 2020 and beyond world of nate sullivan dot com:

  1. Hosting. I moved hosting to WPEngine. They are great -- I've used them for work, and while they are expensive when compared to the bare bones, "good luck!" hosting I've used for almost fifteen years now, I am significantly less poor than I was in 2006. I can mess with everything and make bad decisions, but they have backup tools and really good support to help me fix things without having to spend an entire Sunday afternoon at Panera clicking on tiny CPanel admin buttons, which is something I don't really have time for anymore.
  2. Domain. This domain is now on https, which is probably pointless, but will -- if nothing else -- reduce the number of warnings you (and I) see when you visit.
  3. Store. This also allows me to safely sell stuff on the site, which is something I want to mess with not because I'm interested in selling things, but because I work for an online fulfillment technology company, and want to play with our product. So that's coming.
  4. Archives. Because I am terrible with domains (and impatient), I screwed up a number of things and have lots of old posts locked away in SQL databases I don't really know how to work with cleanly. A bunch of things made it over, but rather than sort it all out, I'm going to unpublish basically everything. Someday, when my kids grow up, I'll root through those old WordPress databases (there are so many, now) and dig out the best pieces. I really and truly feel bad that my technical incompetence has broken links and taken things that some people have liked offline -- but this is an extremely part-time gig and I'm bad at this. It's actually kind of funny, because unlike most people frantically deleting things, I've actually used this site to teach myself to be held accountable for what I write & say, so I didn't purge things out of embarrassment. My writing is often poor and my arguments inane, but it's not like I was posting "hot chick of the week" or whatever in 2008 and now I'm panicking. I'm just really undisciplined with permalinks and I don't know how to get things out of giant SQL files.
  5. For now, I mostly want to keep writing a little simply because I like to write and it's therapeutic, and also maintain a little bit of a museum on my weird, kind of interesting life. That includes work stuff, music, videos, and other projects I've worked on.

In other words, same old, same old. The site is dead, long live the site.

Why OKRs Kind Of Suck

The last two companies I’ve worked for have used OKRs, a system for company, team, and employee goal setting popularized (and possibly invented, for all I know) by Google. Personally, I’ve been very frustrated by OKRs, and if anything, they’ve made me less productive. I don’t think I was alone, and that’s one of several reasons Contactually scrapped them last spring.

It’s not a bad system, but like a lot of a business theories coming out of the startup world these days, it suffers from a desire to constantly evaluate everything quantitatively that isn’t matched by an ability to effectively measure things that way. In fact, OKRs are kind of the embodiment of this philosiphy, where for some reason startups still attempting to do basic things like define what their product is for and how it works decide that they’re going to operate like a Google, a billion dollar public company with one of the most (if not the most) advanced data infrastructures in the world.

The motivation behind being data-driven is fantastic, because it’s a motivation to not be driven by bullshit or blind ideology. This is a truly wonderful characteristic of the stereotypical venture-backed startup, and probably the main reason why I enjoy being a part of them so much. These companies want to do things that make a difference, not just things that make them feel like important companies, and that’s a big part of why startups have successfully shaken up or even dismantled long-established markets.

But that’s the emotional drive behind OKRs; the practical application is another matter altogether, and one that I think a lot of organizations have really struggled with. Recently, I’ve heard marketing people start referring to being “data-informed”, instead of “data-driven”, which I think attempts to fix the wrong part of the term. What you really want is to be reality-driven, where data is often an idealistic proxy for reality. If I’ve learned anything from the last ten years of work, it’s that getting reliable data and making sense of it is actually very difficult, and very expensive in both time and dollars. It’s easy to say “let the data decide”, until two people are waving contradictory Salesforce reports at each other that they both spent hours on — hours that could have been spent doing unquestionably useful things like talking to customers or fixing obvious problems in your product.

Basically, despite all of our wishful thinking, even rudimentary data science is still really hard for most businesses. But we’ve allowed the still-young analytics industry to convince us that it doesn’t have to be, as long as we buy the right tools. Well, by now I’ve used many of the best analytics tools, and while lots of them are really cool, none of them make the full business data experience — gathering, analyzing, interpreting, and auditing — easy, or even predictable, for a company without significant dedicated resources. Not one.

Back To OKRs

That brings us back to the OKR, an acronym that stands for “objectives and key results”. The “objective” part is fine — OKRs are designed to nest goals so that everything everyone is trying to do ultimately bubbles up to a company goal. If you do OKRs right, they ensure that everyone’s individualized little tasks are all generally pointing in the same direction, which is important if you want to make any significant progress as an organization. Strategically, it’s a really, really good way to operate, even if it’s essentially just a framework for continually using common sense and proper priorities in the workplace.

The problem is the second part — “key results”. See, with OKRs, your objectives aren’t really objectives unless they cause measureable change, which can be a problem for several reasons. If you’re trying to measure something qualitative, for instance, the reflexive OKR-style approach is to bolt some kind of metric to it. Unfortunately, this has a tendency to cause people to radically oversimplify extremely complex, qualitative parts of their business with iron-clad sounding, but actually very dubious logic.

“If our messaging is bad, and we improve it, our conversion rate should go up. Ergo, if our conversion rate doesn’t go up, the messaging isn’t any better, or messaging doesn’t matter. We will let the data decide.”

But wait — why are we assuming that effective communication is directly related to people doing what we want transactionally, like clicking a button? Where’s the statistically significant data that demonstrates how people interact with our messaging, evaluate our product, and eventually make purchasing decisions? In other words, where’s the data that validates our approach to data?

The fact is, for growth-based companies doing anything remotely new, that data is often completely non-existent. So ironically, many companies using OKRs end up building up highly quantified evaluation methods that our powered almost entirely by subjective, qualitative assessments of data. You’re not eliminating subjective decision making — you’re just obsfucating it behind a layer of numbers that make everything feel less random.

Worse Than Nothing

People who desperately want to be data-driven (for good reasons) often respond to these observations with the argument that some data is better than no data at all. I have always vehemently disagreed with this, probably based on the fact that I’ve justified a lot of really dumb things in both my personal and professional life with an incomplete, or logically flawed subset of technically accurate data. A simple example — I make pretty good judgments about personal spending. I’m inherently pretty conservative about cash flow and what I “need” versus what I want, and that’s served me well through a series of wildly different personal finance scenarios, from having literally no money and no job, to buying a house a start a family.

But you know what I do when I want to justify a bad financial decision of mine, or push back against something my wife wants to spend money on? I go online, and I start pulling data. How much cash we have. What we’ve spent recently. What we can cut back on. Anticipated future costs. Because we’ve never successfully built a strong enough financial model to respond to various purchase ideas with a simple, 100% metric-based “good idea/bad idea”, instead it’s up to me to equip myself with whatever amount of data I find useful, and make a decision from there. And unsurprisingly, whatever I thought before I had any data turns out to always be the conclusion “the numbers” indicate as well. What an amazing coincidence! To cite one of my favorite quotes, “If we have data, let’s look at data. If all we have are opinions, let’s go with mine.”

And that’s the Achilles heel of the OKR system, as well — tying qualitative objectives to quantitative key results outside of anything other than the most transactional jobs and tasks requires huge logical leaps of faith, and radical oversimplifications that in the end, rarely help you build a stronger business. “Building a product people love” becomes “increasing logins per month”, which probably makes sense in a thousand ways, and makes no sense at all in a thousand other ways. “Increasing brand awareness” becomes “unique blog visitors per week”, because hey, we need a key result, and that seems like something we can measure that would be good. But when the end of the quarter comes, you’re no longer thinking about brand awareness. You’re thinking about unique blog visitors, and in that way, OKRs are often responsible for shackling your team’s very powerful, entrepreneurial brains and turning them into stressed-out, metrics-hunting robots.

Accept That You Can’t Know Why Everything Happens, All The Time.

The bottom line is that everyone is at work for a reason, which means they already have a goal. And what’s ultimately important is that they get as close to reaching that goal as possible, and don’t do things that make reaching that goal more difficult. Marketing teams are probably going to be responsible for generating leads. Product teams are usually supposed to build products that work well and provide value. Sales teams have to close. None of this is rocket science — the real numbers that matter to those teams are obvious, and should be religiously tracked (although it helps to have the patience and perspective to not fool yourself into thinking you can immediately, effectively respond to daily, weekly, or even monthly tracking).

But micro-tracking at more granular layers is often little more than a vanity exercise, and the kind of pointless, administrative navel gazing that startups should be avoiding, not installing. What’s more important is for team leads to look at that one number that really does matter — be it sales, close rate, inbound leads, or whatever — and use their powerful little human brains to assess if the things their team is doing are aligned towards that goal. “Why am I doing this?” is a great question to ask yourself at work every day, and at home, too. When I talk to frustrated co-workers (especially younger ones), and I ask them why they’re doing something they think is a distraction or a waste of time, the answer is still too frequently “because (senior person X) wants this by the end of the week”, or even worse, “because it’s one of my OKRs”. To me, for all of it’s theoretical, well-intentioned benefits, that’s the sign of a system that’s not working. 

Thanks, John

John Anderson, my friend and co-worker at Bamboo, passed away from ALS this week. I’ve thought about it a lot — hell, I’ve thought about it a lot since I found out he even had ALS — and while I struggled even talking to him about it, or talking about it with anyone at all, I know he’d want me to write something. I know that, because John always wanted me, and seemingly everyone he worked with, to write something. Something funny, something helpful… just something. He always told us he’d take care of the rest, and I hope he does that here for me now.

As anyone who knew him could tell you, someone in my position obviously can’t write the definitive tribute to John. He did too much, and lived too much, and since he was a half a generation or so ahead of me, it often seemed like he had done a lot of it while I was probably still doing earth science homework, or trying to make my high school basketball team.

All I can do is tell you is what made him special to me, as a random, fairly introverted twenty-something he worked with for a couple of years, and who he made a permanent impression on.

The Pro

John was the first real editor I’d ever worked with, and he was really f——ing good at it. Like, almost intimidatingly good at it. He was a fantastic writer, even-keeled, patient, motivated, and incredibly supportive of writers and contributors in an almost unbelievably genuine way; he sucked the cynicism out of the room like some kind of Bruce Springsteen-loving human air filter. Writing for John as he and Dooley and Gaitten improbably built a successful online community out of essentially nothing was incredibly rewarding for me, mostly because it made him so damn happy.

He was also very likely the classiest guy I’ve ever worked with; the equivalent of your one friend you grow up with who never says anything bad about your other friends because he’s just a better person than you are. I loved having that friend, and I loved having John as a co-worker for the same reason. I’ve always tried to rise above bickering, sniping, and the other stuff that tears apart teams from the inside, but I don’t always succeed. Having John sitting across the hall, quietly, cheerfully busting his ass to make everyone that much more successful gave me something to shoot for, and still does. To me, he’s the gold standard for teammates.

When I joined him on Bamboo’s Marketing team sometime in ’09 or ’10 (I forget), he quickly became our group’s moral compass. I’m not kidding — we were in marketing, after all, and always under pressure to generate results through potentially dubious means. Eventually, we started just looking at John after every idea; if he frowned, we’d bag it. If he laughed… well, game on.

The Guy

The toughest price I pay for being a fairly introverted, borderline anti-social person is that I miss out on truly getting to know certain people in my life who would have been well worth the effort. John was one of those people. I knew him, but I didn't know him, and he wasn't the kind of guy to force you to do it.

Not once, literally, did John ever “bother” me. He never stopped by to yammer about his pet issue, or bitch about something going on at work, or at home. When I saw him (and I saw him a lot) it was almost always for one of three reasons :

  1. he really and truly needed help getting something important done, or he wanted to do something nice for someone
  2. he was excited — legitimately excited, almost like a little kid — about something I just wrote
  3. he had something to tell me about a band he thought I might like, or knew that I loved
I will, like many people who knew him, probably always associate John with great music. At some point, I wore a Bouncing Souls shirt to work, which was practically a secret handshake to someone like him. Once he found out that I was a Gaslight Anthem fan, it was all over — I was in the punk-rock singer-songwriter secret society, of which John was apparently the president. He burned me a copy of Gaslight’s new record once, months before it was even released. I don’t know how he had it, or where he got it, but I didn’t even have to ask him for it. He just brought it to my desk, and said “you’re really going to like this.” In fact, the strongest reaction I think I ever saw from him was when he found out I was in a band, and I sent him our demo.

“Why didn’t you tell me about this before???”, he asked, completely wide-eyed. “This is awesome!!! I can help you!!!”

Turns out, my random new friend from work ran an amazingly detailed, meticulously researched mailing list about the local music & club scene, that tons of cool people actually read. He wrote unspeakably kind things about us in it, which I can only assume he believed, because he was so freaking honest about everything else we talked about.

No lie, I think that of all the concerts I attended from 2009 to 2013, about 75% were recommendations from John, including the incredible Revival Tour, which he practically begged me to experience in person. (He was right.) Great shows were the only thing I ever saw crack his professionalism -- the most distracted I ever saw him at work was when we once had a serious meeting with our new-ish CEO scheduled at the same time he knew he'd need to be slamming "refresh" over and over on the Ticketmaster site. We inexplicably managed to arrange having the meeting in the room where John sat, and I'll never forget him looking across the room at me, smiling and nodding as he got the tickets in the middle of the meeting, like a teenager who snuck a 12-pack past his Dad. Best conference call ever.

Some of the gigs he told me about weren’t even listed. I have no idea how he knew about that Gaslight/Dave Hause show at the U Street Music Club, or how he got us tickets; but there I was, with the happiest wife in the world, singing along as John ran, friends-in-tow, into the borderline pit forming at the front of the stage.

“How old is Anderson?”, asked my wife, clearly impressed.

I scrunched up my face and thought for a second.

“I honestly have no idea.”

The End

Unsurprisingly, John dealt with ALS the way he did everything else in life, at least when I knew him — with humor, class, determination, and incredible perspective and love. I’ve never been so glad to have Facebook than when I would open it and see what book he was plowing through now, what badass lifelong dream he was accomplishing, which indescribably enormous hero he was meeting, or inspiring, today.

But that wasn’t the way John was just because he got sick, or at least that’s not what it ever felt like to me. He had already been traveling the world for Bamboo when I got asked to go to Vietnam (and to leave North America for the first time in my life) in 2011. I was pretty terrified, but I chose to do it in no small part because John told me — as bright-eyed and excited as he was when he learned I had a band, or that the Loved Ones might be getting back together — that “you just have to do it”. It wasn’t so much that he told me to do it. It was that he told me to do it like it really mattered, and when you’re 28 and working with a guy like Anderson, you listen when something matters to him.

John probably had a thousand better friends than me, maybe just in the span of my lifetime. People who really did know him, people who are posting amazing pictures online of him from house parties in the 90s with no shirt on, goofing around and being someone I’ll never really get to know, no matter how awesome it would have been.

But life is made up of a lot of different relationships; some big, some small. We know what John meant to the big relationships in his life. All I can tell you – and I think it’s worth saying – is that he aced the small ones, too.

Thanks for everything, John. I won't forget it.

Persecution

I was reading a bunch of posts about how Christian conservatives can/should/will gracefully adapt to a world where their strict definition of behavioral “rightness” isn’t shared by a majority of their fellow citizens.

More interesting, accomplished people have fully-baked thoughts about such a complex topic, but instead of talking about those, let’s talk about a completely different, only tangentially related observation of mine. When I was a kid – maybe 8 or 9 years old – I learned what “persecution” meant from a computer game called Revolution ‘76 that I played obsessively for several years.

I LOVED this game, even though there wasn’t a whole lot of military strategy or anything obviously cool like that. It was basically a policy game – you’d pick recruiting policies, and diplomatic policies, and economic policies, and then a bunch of stuff would happen and you’d react to it by changing (or keeping) those policies. Plus, you’d move troops around and invade Canada, and beg the French to get involved and all that.

Anyways, one of the policy questions each year was about how you’d choose to deal with British loyalists. There were four options, which I think I can still name off the top of my head – conciliation, tolerance, prosecution, and persecution. If you chose a policy that didn’t match the mood of the new country, or the situation on the ground, or your nascent government’s strength, the loyalists would get aggressive, organize, and you’d end up with a counter revolution in New Jersey or wherever.

I didn’t really connect the dots back then – to me, “persecution” was the option you chose when you were doing pretty well, and wanted to make sure you didn’t end up getting distracted from burning down Quebec by an unexpected uprising in Charleston. Now that I’m older, I realize what I was calling for. In short, lynch mobs, kangaroo courts, and political vigilanteism. Errr… oops. The picture above is from the DOS version, but I swear, in on the Apple IIGS it wasn’t just a little frowny face icon; there was a like, a guy hanging or something. Maybe I’m just making that up in my head out of guilt for all the digital Tories I condemned to death as a kid.

My point, I suppose, it that even though it amazes me, there was in fact a time in my life where I endorsed brutal, repressive measures against an unpopular minority group. Fortunately, that group did not consist of real world human beings, and my power did not extend beyond our 12 inch Apple RGB monitor. But still, it makes you think about what persecution really is, and gives you a tiny little sliver of insight into what may motivate some of it.

(short answer : social power, and the fear of losing it)

Mailing It In

I’m not very good at pretending to like things. I don’t like manually doing repetitive work that feels like it could be automated, or eliminated by a better process. I don’t like adhering to bad procedures simply because “that’s how things are done”. I don’t like avoiding a problem because acknowledging the existence of a problem makes someone important uncomfortable.

I don’t like any of these things. But… of course, I will do them if doing them makes sense in the grand scheme of things, no matter how dysfunctional and inefficient that grand scheme may appear to be. I grudgingly do all sorts of things for work, not because I think they are great ideas, but because I think they are the best decisions to make for my organization at the time

At first, this sounds incredibly high-maintenance, and to normal people, probably pretty annoying. I completely understand that, and trust me, I work very hard to make my philosophy as tolerable and non-instrusive as possible. And in my defense, there’s a good reason I fight against doing work just for the sake of work – I don’t believe in half-assing things

This is something I’ve found makes me a bit of an outlier. Half-assing is a huge part of American culture, business, politics, and just about everything else. Token efforts, olive branches, and “good faith” (even if it’s really the opposite) are key steps in the horrifying sausage-making that is getting something done in most organizations, not because they have to be, but just because a lot of our office and business habits grew out of historically low-information environments where asking questions was (and still is) often associated with rocking the boat or being difficult. Questions are percieved as inherently combative, even if they’re tactfully constructed and designed to reduce confusion, while mailing in a dumb task is somehow weirdly acceptable, or even seen as an example of good judgment. 

I’ve always had a bit of a problem with this, but people – smart people, mentors – have been trying to explain the importance of half-assing unimportant things to me for years. Once, when I was home from college, I was helping my Dad build some steps in our yard. Being unskilled (especially compared to Dad) my job was to drill holes in the steps, and then put in the screws. I wasn’t very good at it, and eventually, I stripped the head of one of the screws as it sat halfway in the hole. 

At first, I was frustrated, and a little embarassed. After all, to me, Dad always took his time, and always did things the right way. He built things with stone foundations, always pre-drilled holes, measured everything, and used lots of graph paper. If we were going to build stairs, we were going to build stairs the right way, dammit. They’d probably last two hundred years. 

Reluctantly, I showed him the screwhead I had shredded, and asked him what to do next.

“Oh yeah, this happens all the time,” he said. “Let me show you what I do.” He took the drill from me, flipped it over, and slammed the base onto the screw.

WHAM! WHAM! WHAM!

“Sometimes it can be a little stubborn.”

WHAM! WHAM WHAM WHAM!

“There you go.”

He laughed, and handed the drill back to me. I was flabbergasted, and I think he could tell. 

“I mean, I have more screws,” he said. “But… they’re all the way up in the garage.” This time, I laughed, even if it was partially in disbelief. Even my father, the engineer, who once designed and built me a beautiful, amazingly playable outdoor basketball court out of bricks that still stands today, knew when to hold them, and when to fold them. The stairs just weren’t that important. If they were, he probably would have made them out of stone. 

In truth though, Dad wasn’t really half-assing the stairs project per se – he was just preventing the perfect from being the enemy of the good, which is actually really important. Good projects, systems, and even products are increasingly built iteratively (with good reason), and the last thing you want to do is build big, expensive, labor intensive stone steps when you’re not even sure how long you’ll want steps at all, and you need to finish that retaining wall on the other side of the property before winter. 

(As my Dad said at the time, half-jokingly, “in a couple of years, your mother will probably have me tear these out and put in a ramp, anyways.”)

No, the kind of thing I can’t stand is work that is designed to fail, which is what a lot of people spend way, way too much time doing. Dealing with potential investors at EEx (especially big, institutional investors and funds) became incredibly frustrating for me, because after a while I felt like the goalposts were CONSTANTLY moving, and eventually, that they were simply designed to move forever. They might tell you that your pitch deck was too long, but after somehow getting it down to six slides, they’d demand that you include more financial information. Then, when you did, they’d tell you that weren’t thinking big enough, and to include more long-term vision. So you’d do that, and they’d laugh and say “you have to explain how you’re going to do this”, so you’d do that and all of a sudden you’d be at twenty-five slides again, and the whole cycle would repeat, except you’d be out three weeks and a bunch of money, and you’d have flown to San Francisco twice. At some point, you just have to admit to yourself that all the great work you’re doing is pointless and isn’t helping your business, but in a lot of jobs, that’s not encouraged. You’d just keep making that deck again, and again, and again until someone told you to do something else, and then you’d do that. 

Back at Bamboo, like any ambitious, growing company, we had a few bad ideas that we really wanted to work, but never made a lot of sense. I remember working really, really hard on landing pages, email campaigns, and messaging for ideas with huge, obvious strategic holes in them that we either wished away, or refused to engage with altogether, because the project was exciting to someone with influence in the company. Then, after the project failed (of course it did), we’d sweep it under the rug and never speak of it again, until the next bad idea started to gain momentum. Those failures were exhausting and demoralizing for me primarily because I didn’t half-ass them (some of my best work isn’t available online because it was for these doomed projects, and has been taken down), even though – looking back – I probably should have done exactly that, and saved my ammunition for better thought out initiatives with real potential, which we also had a few of.

Part of me has always wanted to get better at making this kind of distinction, but another, louder part of me thinks my stubborn insistence on quality whenever possible is exactly what makes me valuable in the first place. Like most things, the answer is probably somewhere in the middle, and I’m just going to have to keep working on finding that happy medium. But the next time you find yourself wondering why we’re still debating the merits of something, remember – when I eventually do it, I’ll do it well

Things We Don't Understand

You can divide all the people who might care, or might find it interesting that a company like Facebook spent nineteen billion dollars on a company like Whatsapp, into what are essentially three groups. 

1) People who get the purchase, and the reasons behind it

2) People who don't get the purchase, but never claimed to understand why Facebook does what it does

3) People who don't get the purchase, and are horrified and annoyed that they don't get it

First of all, LOTS of people who claim to be in Group 1 are really in Group 3. Let's just get that out of the way, because this isn't a post about false expertise or imagined credentials or anything like that. Analysts and pundits feigning understanding is standard operating procedure, not something interesting.

What IS interesting is how big Group 3 really is — how many confused tech industry people there are struggling to process the implications of this kind of deal. "Nineteen billion dollars for an SMS app? Doesn't Facebook have a perfectly good messaging application, and doesn't practically everyone have Facebook? Even if this is something worth purchasing, how could it possibly be worth SO much money?"

i don't get it either, but that's okay

I'm not going to try to answer those questions, because there are smarter people out there  with a better understanding of things like international social networking business models who can do that for you, and because that's not really the kind of thing this site is about. What I am going to do is write about the feeling of suddenly not understanding something you thought you understood, and how to deal with it.

Everybody has blind spots, and in my experience, they're not necessarily intrinsic; they're usually formed — somewhat ironically — from experience and expertise. Anytime you learn how to do something in the real world, you find efficiencies to exploit and irrelevancies to ignore as you learn how to do the job. That's why you get better at your job, of course. Before you know it, you're confident, effective, and comfortable blasting through the questions and obstacles that might paralyze a less experienced professional than yourself.

That's when you get your blind spot. Marketers and media people assume everyone is on Twitter, designers assume that everyone has good taste (and cares about it), VCs assume that all good ideas get funded, developers assume everyone smart can code well, companies with sales lock-in assume their products are competitive, and the Knicks assume great players will demand to play in New York

(Okay, I can't explain that last one — some people are just delusional.)

This process happens to everybody. You can bring in consultants, and sometimes that helps (hi!), but what's more important than a voice coming from outside your organization is a voice coming from outside your discipline or culture. Facebook doesn't need a consultant from some Bay Area design firm; they already have a very good version of that perspective in-house. What they need is to figure how to deal with people outside that universe who post ugly memes and political rants, and also happen to comprise a majority of their user base. 

One of my old co-workers joined a company that made some kind of automation software for the government, and wanted to expand sales to the private sector. Great — except they used their government product/sales/marketing approach to do it, and refused to deviate because it had worked so well in the past, even when it didn't work. They couldn't see past the similarities of the two markets ("the purchasing guy at this telecom company used to work for the FCC!"), and as a result missed the differences. Success had made their world so small and focused that they lost the ability to live outside of it, or even to recognize that this had happened in the first place. 

MY blind spot

I brought up the Facebook/Whatsapp deal because it's a great example of this happening to lots of people who consider themselves more resistant to blind spots — people like me. But in my case, I've already been disabused of the notion that I understand international social networking — when I started working for EEx, I was introduced to WeChat, China's enormously popular (and profitable) messaging/social app. Internally, I dismissed it immediately. It was ugly, weird, and full of gimmicks like voice messages and the ability to send a message in a virtual bottle. Everything I knew about software, applications, and human beings said this app was a joke. 

As it turns out, WeChat is the opposite of a joke. It has 600 million users, including 70 million outside of China, and more importantly, is an active, immediately-understood method of communication in a huge market, and a vibrant ecosystem for things like Paypal-style payments and additional apps. My blind spot — a combination of my inability to see the potential of a platform based on messaging, along with my own personal preferences for design and usability — kept me from seeing WeChat for what it is. Fortunately, EEx has a great team of people from different disciplines and cultures, and we listen to each other. WeChat seemed insane to me, but the people telling me how important it was did not, so I got over it. 

I wouldn't say that's the IDEAL way to handle blind spots; if you're doing strategy or planning, you probably want to focus on not developing them in the first place. But you're only human, and ten or twenty years in an industry is likely to cause them no matter how open-minded you are. In that case, your best defense really is your ability to find and hear those outside voices — the ones that can tell you your technology is weak, your product is lame, or your sales channel is closing.

Hey, nobody said being in charge would be easy.