What is the Ideal Advertising Platform?

I’m taking a short break from “How we solve problems” because I’ll be giving at talk at WordCamp NYC this month, so I thought I’d explore some of the ideas I’ll be touching on in blog form. I’d love your feedback below to further my research. This essay delves into an aspect of owning your own data vs. being someone else’s product.

Speaking personally, as a consumer, what sort of advertising would I actually like?

As a consumer, I like to find out about new things, or new products from companies whose products I like. Let’s get this out on the table, advertising isn’t necessarily bad.

As a product creator, I want to get it in front of people in case they need it.

On the other hand, waking up in the morning to 100+ emails in my inbox is ridiculous. And clicking a link to an article but not being able to find it on the page due to the 80/20 ratio of ads/content, is absurd.

What if there was a platform on which you could indicate somehow what things you were interested in, and based on that advertisers could target you (ahem, Facebook)?

Or what if when you were actually looking for something, creators of what you are looking for, or similar things, could let you know what they had to offer when you were looking for them (ahem, google)?

This weirdo loves ads. Probably not a weirdo. A well-written article, but it is hard to tell if the tone of the post is serious or not. She does make an important point about how ideally ads can work.

Some ads are outright adorable, hence, very effective.

So why do we hate ads?

With iOS9 one feature Apple added was the ability to create adblockers. Consequently the adblocking category exploded in the app store. Google it and it’s all people can talk about right now.

This demand for adblockers clearly indicates a market desire for blocking ads.

But why?

I have a few theories… and feel free to add your own below.

1) Freemium Media

Since the early days of the internet, the predominant model for supporting media has been advertising. As Jaron Lanier, the author of Who Owns the Future?, has argued, “The whole business of using advertising to fund communication on the Internet is inherently self-destructive.” We see that destruction inherent within this adblocker-driven backlash.

Can you really blame consumers of media? When you open most publications, even “respectable” ones have so many ads that it’s hard to find the content. Publications need their readers to see or click on a quota of ads in order to support themselves, but the readers have all become blind to the ads due to the overwhelming amount of them.

It has become a vicious cycle of more and more ads being added to the pages because obtuse or uncaring ad execs pile them on the page trying to trick visitors into clicking so they can meet their quota.

“It turned out not to be a sustainable business model. The number of websites, and thus the supply of slots for ads, went up exponentially every few months, but the total amount of advertising dollars remained relatively flat.”

– Walter Isaacson. “The Innovators”

This pattern also fuels the trend towards clickbait titles and articles pushing the majority of consumed ideas to the lowest common denominator, but that’s a different essay altogether.

2) The Creepy Factor

The major social and search engines have earned names for themselves as stalkers. You search for a product on Google and ads relating to the product follow you across every website you visit henceforth. You Like something on Facebook, post something to your status, or Retweet something and more ads follow you.


There is a battle being waged over your privacy among technologists. For every bill that comes out due to lobbying by media companies, and government agencies who want to open access to your online behavior, there are organizations like the EFF and Mozilla who fight against this legislature. For every “Evercookie” created to track you no matter what you do to get rid of them, there are adblockers that are developed against them.

I really do feel for product makers trying to sell their products, and services that rely on advertising to keep the doors open, but there is a line where following my tastes and behavior becomes invasive and abusive. The Evercookie, for instance, blatantly ignores a users intent to not be followed.

So what is the ideal advertising model?

Tracking users is an effective tool, because of relevance. If an ad is relevant to my needs I am more likely to follow that thread to see if it leads somewhere helpful. But on the other hand, THEY. ARE. CREEPY. Especially when I request not to be tracked.

What creeps me out most about tracking is that it is very hard to know whose hands my profile will fall into. Install Ghostery and see who is tracking you. Do you know who all those companies are? What do they intend to do with this data they track about you? Are their servers secure? Are they anonymizing your data? What happens if they’re hacked—could someone steal your identity, or build a profile about you to attack you or someone you know personally?

To Facebook and Google I am an ID in an enormous database. It would cost too much for them to store irrelevant details about me. There is a profile for my tastes. That doesn’t bother me. I actually like that I can go into my preferences on Facebook and say exactly which things I’d like to see ads for. I’d love if this were universal across the web, this and only this.

Facebook ad preferences

Google has this too.

Control Your Google Ads

There is a huge difference between practices akin to Evercookies and this. Respect. Its also clear, when you visit a site and there are ads everywhere, that you are not respected. I believe that this is what the adblocker backlash is about.

Aside, Amazon has a similar tool, but the implementation is half-assed.

Another essential aspect of effective advertising is who says so besides you. It’s one reason why Facebook Likes are so powerful, why Hacker News is a boon for startups, and why Product Hunt launched so effectively. This topic, though, is a whole other essay.

Last Song Before Night By Ilana C. Myer

I’m a proud husband, what can I say.

I know on this blog I don’t normally stray from my usual topics about tech, and development. But I would be amiss if I did not mention this huge event in our life. So I hope you’ll forgive this digression.

I’m a not-so-closet geek complete with a love for fantasy. The first “grown-up” book I read myself was The Blue Sword, my oldest sister had started reading it to me, but I couldn’t wait for her to continue and I finished it myself. Some of my fondest early memories was of my mother reading me The Hobbit, and this one time I slept over my best friend’s house and his mother was reading the kids The Two Towers. I shared the Belgariad and Mallorean with my parents when I discovered David Eddings.

In short, fantasy was a big part of my identity growing up and has stayed with me. So when I met Ilana and she told me she was writing a fantasy novel, I thought that that was the coolest thing.

I’ve lost count how many times I’ve read various versions of Last Song Before Night. This past week I read the audiobook — as many of you I’m a little bit obsessed with audiobooks. I don’t know if it was the fifth or sixth time I’ve read it, but I was still swept away by its lyrical beauty, complex plot and characters. I laughed and cried, again.

am a bit biased, so I thought I’d share what others are saying. These are some of my favorite reviews of the book so far…

Jason Heller, Senior Writer for The A.V. Club, and writer for NPR,  described it as “A Beautifully Orchestrated Fantasy”.

“Myer’s depiction of Tamryllin and the land it inhabits is shadowy and lush, a tapestry of gossamer wonders as well as theocratic oppression and brutality. But the core of Last Song‘s strength is its characters. Bound by enmities, rivalries, lust, sacrifices and ancient tragedies, the novel’s sizable cast forms a dizzying chemistry.”

NPR’s review of Last Song Before Night by Ilana C. Myer

Seth Dickinson, Author of The Traitor Baru Cormorant, reveals some of the complexities of the book…

“The journey of this novel is their painful, bloody, heart-wrenching escape into a place of personal truth. One by one they begin to break away from their scripts. Even the world-threatening plot arc is predicated on a lie—not a lie of malice, but one of fragile, human self-deceit and shame.”

Seth Dickinson’s review of Last Song Before Night by Ilana C. Myer

And David Mack, New York Times bestselling author of more than twenty-five novels describes…

“One of the richest pleasures of Last Song is seeing how Myer subverts readers’ expectations of the epic fantasy genre. It evinces all the hallmarks of a typical quest tale—then it becomes something deeper, more intimate, and ultimately unflinching in its examination of its characters’ ugliest qualities and darkest secrets.”

David Mack’s review of Last Song Before Night by Ilana C. Myer

It’s been a journey, following the progression of this book, and it has been so rewarding to see the beautiful things people have been saying.

WordPress as a framework for a bank

I saw the following question on Quora: I am powering a bank’s website using WordPress. What security measures should I take?

Matt Mullenweg responded, awesomely as he does,  but in his answer he said the following.

“I agree there’s probably not a ton of benefit to having the online banking / billpay / etc portion of a bank’s website on WordPress.”

Which I don’t entirely agree with. So I commented my thoughts, but thought I should share them here too:

I’d be interesting in hearing why not…

One reason I use WordPress is its ubiquity, knowing that since so many people use it, the moment something is revealed to be insecure in the system, I know that some of the top security minds are working on it. Not to mention the other features that exist out of the box, that are constantly being developed and improved upon by a great community of great minds: user management, database structure and connections, data structures, a templating system.

Now one could argue that a bank of all places should have a dedicated team focused on all these features making sure that they are as secure and well-built as possible.

But you all see the results in you own bank’s web portals. I’m sure many of you have jumped into helping maintain a legacy system which constantly requires new features while many out-of-date systems are not updated.

This is why I have my team build many of our projects on top of WordPress, as a framework. We can focus on the specific features I need and leverage the WordPress community for the rest. I make sure that my team could build these features themselves, that they understand what they are building on, but why reinvent the wheel each time you need to drive to the store to get milk?

Are there other frameworks out there I can use? Of course, are they better? Now you’re splitting hairs, because for most of my projects I need a great deal of the functionality already baked in.

Because I rely so much on WordPress I try, when I can, to give back. Many people feel the way I do and that creates a positive reinforcing cycle.

So thank you Matt for what you’ve given us.

[UX] My Issue with Windows 10’s Multiple Desktop Feature

One of the more productive features I’ve embraced is the multiple desktops. I tend to compartmentalize tasks, and being able to actually do that visually, helps me focus on what I’m doing, and keep my process organized.

I use Windows at my day job and I was thrilled when I saw that Windows 10 was adding this feature. Unfortunately it comes up short due to one major flaw in the UX, the implementation.

OS X splits the various programs running in to the program and the windows (or instances) of that program. Windows does that too. OS X indicates which  programs are running in the dock with a little dot underneath the icon of that program. Windows does too.

But here’s where Windows, sadly, goes amiss. In OS X you can have different instances of a program running in multiple desktops. No matter which desktop you’re on, if the program is active on ANY desktop, it will show a dot under the icon. If you click that icon it will (should at least) take you to the most recent instance of that program regardless of the desktop that instance is in. Yes, it could work a little more smoothly as it doesn’t always work that way, but it DOES indicate that it’s running somewhere.

Windows 10 separates completely between desktops so that there is no connection between the programs running on the different desktops. This means that when I need a program, I can’t see that it’s running on a different desktop, because the dock only shows me what’s running on the current desktop I’m on. This leads to unnecessary instances of a program running leaving the benefits of the multiple desktops mute and void.

If I don’t know what’s running on my computer I’ll never find that instance, or I’ll waste time trying to find it. If I need my email and I don’t see it’s open, I’ll open it up again. If I waste time looking for it on the 5 different desktops I have open I lost the benefits of having multiple desktops.

True, multiple desktops came in on the Mac in 2009 with OS X 10.5 “Leopard”, and true, it wasn’t great with it came out either. But I had hoped that Microsoft would learn from Apple’s mistakes with this feature.

All in all, I must saw that upgrading from Windows 7 to Windows 10 has been painless, it’s a shame it wasn’t eventful.


[UX] The Chicken and the Egg Problem

I recently had the honor of advising a startup on their initial launch design. The biggest issue I encountered, and I’ve encountered this quite a bit with new companies, is the problem of the chicken and the egg.

Many products rely on two separate types of users in order to get off the ground. A marketplace needs sellers and buyers, a social network needs followers and people worth connecting with, big data needs sources as well as consumers.

The big issue is that you cannot cannot cannot gear a site to both effectively.

Imagine going into an electronics store with sections geared towards the supplier. Would you really want to buy there? The message it sends is that you can’t get suppliers. If you supplied to that store, would you feel confident that that store would be able to sell your wares?

This is a design problem as much as it’s a business problem.

One classic pattern that tries to straddle both is to have two big buttons: “I’m a buyer” / “I’m a seller”. In lieu of the above paragraph, does that still sound like a good idea to you?

A page split down the middle doesn’t look all that good either. It gives the message that you don’t know what you’re doing, what your company’s focus is.

To solve this you need to focus on one. If you can do that effectively, you’ll never get both. Until you get the ball rolling you probably will have to do a lot of manual marketing to the other behind the scenes, to make the site work.

There are two ways to go about doing this:

The first is to put up a shell online for a very manual process that happens in the background. The shell is minimally automated, just enough to make it look like a fully functional site. What this does is it keeps the development costs down while you build a user base and test your assumptions.

Then focus on building it into the tool you would use, while you build up the user base. As you make successful deals through your site those deals make a great foundation for your next homepage that features your successes.

Airbnb did a version of this, I am not advocating for what they did as it might have been illegal, but when they were starting out and trying to grow aggressively, they pooled potential poster from Craigslist.

The second way is to provide a service for the first user-type regardless of whether the second user-type exists.

Kickstarter is a classic example of this. Kickstarter has two user types: project creators and project supporters. But Kickstarter became a platform for the creator to sell to the supporter. If you are a creator and you don’t have a community to begin with, you probably won’t find that community on Kickstarter. Kickstarter stays away from promising that. They created a platform that provides value for the user whether or not Kickstarter is huge.

If you can focus on one type of user you’ll be doing your website’s aesthetic and your company’s business plan a huge favor.

What do YOU thing? Please comment.

Why we need to avoid taboos

“At the great religious metropolis of Hierapolis on the Euphrates pigs were neither sacrificed nor eaten, and if a man touched a pig he was unclean for the rest of the day. Some people said this was because the pigs were unclean; others said it was because the pigs were sacred. This difference of opinion points to a hazy state of religious thought in which the ideas of sanctity and uncleanness are not yet sharply distinguished, both being blent in a sort of vaporous solution to which we give the name of taboo.”

– Sir James George Frazer, The Golden Bough

Frazer posits that the source of pig being forbidden in the Middle East in ancient times was due to its sanctity, via the worship of Attis and Adonis, rather than its uncleanliness. Throughout The Golden Bough Frazer brings numerous examples of how an animal, or object, or place went from being sacred to being profane due to its taboo status.

Whether you accept the thesis of the pig, this idea is found elsewhere. From one generation to the next, once something became forbidden, the reason for its being forbidden got lost.

I grew up with a story about a woman who wanted to get the recipe for her mother-in-law’s pot roast. One thing that puzzled her about the instructions was where that she was told that she needed to cut off the ends of the pot roast, or else it wouldn’t be kosher. When she found the source of this custom, she discovered that the pan, in which the originator of the recipe used to roast her pot-roast, was too small. But because her mother-in-law hadn’t asked why, she thought it was a necessity.

I was taught this story as an example of the importance of questioning things that don’t make sense to you. When people avoid something, and it becomes taboo, the reason they avoid it gets lost, because they don’t transfer that knowledge.

I’m concerned about how it’s no longer acceptable to discuss things that make people uncomfortable. I’m afraid that if we cannot talk about these things,  we are giving up our power to work through them and find real solutions. Whether it’s religion, race, or body image, it’s toxic to make discussion itself taboo. If we cannot talk about something, it means that we will lose the very reason why the issue is important.

Case in point, how many people who were so adamantly supporting the confederate flag knew that its popularity rose in the 50s and 60s in direct reaction to integration?

When we don’t talk about things, their knowledge gets lost.

How I Rea[r]d – Audible has changed everything

We all make resolutions as the new year comes around. Most don’t last a month, but half way through, mine seems to have stuck (tfoo tfoo) and I’ve been reading a book a week since January.

Over the past few years I’ve discovered that while I’m coding I am most productive when I listen to things. When I’m working on something that takes a lot of brain power that tends to be Bach or Mozart, a little less brain needed — Led Zeppelin or The Beatles. However, two thirds of the time I’m doing things I’ve done ten times before, it takes expertise, but not much brain power. That’s when I listened to podcasts.

TWO Free Books on Audible

About a year and a half ago I decided to try Audible instead of podcasts, I had just finished the back log of This Week in Startups and my day was feeling empty.

I rarely listen to podcasts now, I still have my few favorites, but I’ve been eating up all the books I’ve been missing, and discovering so many more I never knew I’d been missing. During my commute, during workouts and at work. I am a fanboy and am grateful.

Check out my reading list, I’ll keep adding to it as the year goes on.

I’ve decided to share my list now, because I’ve been feeling more and more a need to discuss what I’ve read. So if something jumps out at you on the list, leave a comment, or email me directly. I’d love to discuss.

Note: since I am reading with my ears (rea[r]ding) I’m also considering literary audio performances and courses as a complete book. You may disagree that listening isn’t really reading, it’s not quite as it is passive. But the outcome is the same, I’ve consumed the literary work in it’s entirety.

Don’t be TOO clever with your UX designs – Why I cancelled my Coin

Edit: After reviewing Plastic, I decided to go with them. First and foremost, their security isn’t over-thinking things. Second, their card actually recharges, so you won’t have to buy a new one after a year+.

* * *

I was excited when Coin announced their campaign. I love technology, and this is a great example of innovation being used to make life easier. I have several credit cards, it’s good for your credit score, and keeping track of them is a pain and risky. I’d rather keep them safely at home and use secure device out in the wild.

When I first received the notification to download the app I set it up. I had a little trouble setting up the Tap Code. I had a little musical training growing up, but that was a long time ago, and I never got around to learning Morse Code. I finally entered a code that was acceptable, but how do you write that down?

Months later I saw that Coin was starting to ship so I tried to sign into my app to see when mine would come. I’d been waiting for it for a while and was excited.

Tap Code: Damn. What was it again?


I went to reset it, had trouble getting something complicated enough that was acceptable. Again. This time I tried noting it down in 1Password with dashes and dots.

Later that day I decided to try signing in again. Even with the dashes and dots I couldn’t sign into the app.

I applaud them for trying something new, but at that point I was starting to get concerned about ever being able to use my Coin. So I looked through the app, no there is no alternative to using the Tap Code.

At that point I wrote to them asking them if there are plans for an alternative for people like me who can’t seem to get their innovative password alternative working. The email I received in response, I felt, was patronizing. It explained how to set up the Tap Code, and made me feel like an idiot. I’ll give them the benefit of the doubt, maybe they’ve had a bunch of people who couldn’t set it up, maybe due to my frustration I was reading into the tone of the email. The person clearly didn’t read my complaint and sent me an answer explaining what they thought I was asking about.

Maybe I should learn Morse Code, but that wasn’t even the issue, I couldn’t get it working even after I had written down my code. I responded asking if they have plans integrating an alternative for people like me, and no they didn’t . So I requested a refund.

With innovations, it’s important to make sure they work well, if you want people to use them. If your innovation is truly unique and different, It’s also important to make sure there are alternatives, if you want your users to be comfortable enough to try your innovation out.

Even Apple had a password fallback when they first implemented the fingerprint reader. Now the password fallback is gone, but that was there for the first year+, until they ironed out all the details.

In addition to being concerned about being able to use my coin at all, I was just as concerned about their approach to UX. I’m not an average user, and I couldn’t use their technology effectively. If they’re not responsive nor thoughtful about THIS innovation, what other aspects of their system and security are they NOT thinking through?

At least I got my money back, but I’m disappointed. I wanted to use their tech.

I don’t know how many people they testing this concept with. I couldn’t find many articles about the security benefits of tap codes over pins. Historically Tap Codes are interesting, but they’re for communicating, not for identity. I think it’s a real shame that their approach is bullheaded and unthoughtful.

“The Crystal Goblet or Printing Should be Invisible”

This metaphor is truly stunning and puts into words the careful balance between that must be maintained between content and container. This is as true for a site’s design and the content it contains as it is for typography and the text it contains.

“Imagine that you have before you a flagon of wine. You may choose your own favorite vintage for this imaginary demonstration, so that it be a deep shimmering crimson in colour. You have two goblets before you. One is of solid gold, wrought in the most exquisite patterns. The other is of crystal-clear glass, thin as a bubble, and as transparent. Pour and drink; and according to your choice of goblet, I shall know whether or not you are a connoisseur of wine. For if you have no feelings about wine one way or the other, you will want the sensation of drinking the stuff out of a vessel that may have cost thousands of pounds; but if you are a member of that vanishing tribe, the amateurs of fine vintages, you will choose the crystal, because everything about it is calculated to reveal rather than to hide the beautiful thing which it was meant to contain.

“Bear with me in this long-winded and fragrant metaphor; for you will find that almost all the virtues of the perfect wine-glass have a parallel in typography. There is the long, thin stem that obviates fingerprints on the bowl. Why? Because no cloud must come between your eyes and the fiery heart of the liquid. Are not the margins on book pages similarly meant to obviate the necessity of fingering the type-page? Again: the glass is colourless or at the most only faintly tinged in the bowl, because the connoisseur judges wine partly by its colour and is impatient of anything that alters it. There are a thousand mannerisms in typography that are as impudent and arbitrary as putting port in tumblers of red or green glass! When a goblet has a base that looks too small for security, it does not matter how cleverly it is weighted; you feel nervous lest it should tip over. There are ways of setting lines of type which may work well enough, and yet keep the reader subconsciously worried by the fear of ‘doubling’ lines, reading three words as one, and so forth.”

“The Crystal Goblet or Printing Should be Invisible”
from Beatrice Warde, The Crystal Goblet, Sixteen Essays on Typography, Cleveland, 1956

Learning to Walk in Space

When a child learns to walk, they take leaps beyond what their skill and strength should allow. They look out at all the people walking around them, and see what is possible. Their muscles may not be strong enough to fully support them, to balance and stand, but they see what is possible. They pull themselves up by a table leg and stand. They may bounce on their feet a few times in anticipation of walking, and then they leap over, stumble a few steps, and fall onto a couch, or into a parent’s arms.

These are a child’s first steps.

When we, humanity, started our space journey our technological muscles were only beginning to be formed. Germanium was still being used in transistors, and Apollo’s computers had approximately 64Kbyte of memory and operated at 0.043MHz.

Landing on the moon was that stumbling first step that a baby takes from the table, lunging towards a couch.

Since then we’ve been strengthening our muscles. We now have cars that can drive themselves and more computing power than we know what to do with in our own pockets.

We have more than reached the time when we need to let go from holding on to the safety of the coffee table. We need to let go, and take steps out into the universe.

We dreamt of hotels on the moon and we think that we failed because they don’t exist yet.

But those dreams were the dreams of a baby believing they’re walking because a parent is holding their hands up. Our technological muscles weren’t strong enough to support hotels on the moon.

Our technology has matured and now is the time to build those hotels. Solving the problems that we will need to solve, to have a manned base on the moon, will reverberate through our economy. Such a project will reap dividends beyond our imagination.

There are a lot of technological problems that will need to be solved for man to safely set up camp off our planet. How will we cheaply and efficiently get past lower orbit? What sort of life sustaining systems will we need to build to survive there? Are there building materials there? How much water can be found there?

Cellphone cameras, solar cells, and artificial limbs each were developed by NASA to solve a problem, and each became an industry in itself, generating jobs, creating wealth, and improving our overall quality of life. The solutions we create to set up camp on the moon will do the same.

We should do this in parallel to the missions planned to Mars. The moon is close and shouldn’t wait. What we learn there will apply further out and it should pay for itself in dividends.

We should send man back to the moon. We should build science stations on the moon.

We should build hotels on the moon.