In a Snap: Why Snapchat Isn’t Built to Last

Last weekend Snapchat ran its first ad. And while the trailer for the movie Ouija is being heralded as a success, I think it reveals much about the shortcomings of the social network.

Maybe I’m old (not in Snapchat’s core demographic), maybe I’m slow (didn’t have much use for Twitter originally either), and maybe I just feel excluded because of my unshakeable Windows Phone addiction. But I’ve always been skeptical of Snapchat’s long term prospects, and here’s why:

I won’t try to convince you that your naughty pix aren’t as secure as you think, or that the founder is a terrible human being, or that sending disappearing messages is as gimmicky as collecting Beanie Babies. There’s clearly something there; millions and millions of users can’t be completely wrong. Snapchat has tapped into some need for ephemeral self-expression, some way of escaping the prying eyes of parents that hits a chord with adults too. Personally, I don’t get it – I don’t want to waste my creative efforts, no matter how trivial, on something that’ll disappear. I like that we can relive our memories through social media. And it forces me to ask today’s version of the reputational gut-check question: “how would I feel if this were tomorrow’s New York Times front page?”

But Snapchat’s big problem isn’t that users are going to get bored with it. It’s that the network’s novelty is also its Achilles heel – it has virtually no data to sell.

Snapchat accounts aren’t connected with any other social media profiles and they don’t ask users for any additional info when they sign up. I’m guessing with the $3b Zuckerberg snub that Facebook profile data won’t be coming to Snapchat anytime soon. But not only are advertisers unable to target users based on their profiles, the Snaps themselves are devoid of any searchable data on the contents of the message. So the only thing advertisers can do is blanket the entire Snapchat network with the same message. That’s halfway useful if you’re going after the demographic that Snapchat primarily serves (which, on average, isn’t a particularly valuable one from a purchasing power perspective). But it completely misses out on all the benefits of the digital marketing revolution that allows marketers to target specific users with specific messages based on interest and intent.

Furthermore, they’re going to struggle with integrating Snap Ads into the app in a compelling way. The first ad just showed up as an incoming message, which users were free to ignore. Millions clicked on it anyway, but the success of that approach will be short-lived; when the novelty wears off then Snapchat will need to find a way to make users watch ads in between Snaps. Think about the difference between viewing a Snap and viewing content on Facebook, Twitter, Pinterest, Instagram or even Vine – there’s no newsfeed of Snaps you can scroll through, no natural way to embed marketing messages into your normal media consumption. Snapchat has commercialized the area next to the content you care about, and is hoping you click on it.

Snapchat may have built a compelling user experience, but they’ve failed to build a data-driven economic platform. And that’s what really drives the success of the Amazons, Ubers, Googles and Facebooks of the world.

Over dinner recently, I had one Snapchat fan in his early 20s describe why Snapchat is different, why it was destined for longevity in the way other fads like Farmville and Foursquare were not. “It’s mobile,” he said. “It’s always with you; it’s transformed the way people communicate. I use it a hundred times a day.”

I know the feeling he’s talking about. There was a company that was pretty transformative in the mobile technology space back when I was in my early 20s too. A technology, or at least a brand, that put millions of people in constant contact. Never again would you miss an email. Never again would you be stumped on an archaic piece of trivia. The company had tens of thousands of employees, a $150b market cap, and for a period of time it was synonymous with the smartphone – I’m, of course, talking about BlackBerry. That company is worth $5b today, having lost 97% of its value. Before Snapchat gets too cocky, they should take note that picture messages aren’t the only thing that fast-moving technology can make disappear.



One small boo boo for baby, one giant leap for mankind

Yesterday Lu turned two months old. Do know what present healthy babies get on such a day? They get their first big dose of vaccinations. Not exactly a pizza party, but beats the heck out of polio.

The shots made her scream like crazy. We held her as she shook and wailed, and she eventually reduced herself to whimpering as she lost her energy for crying. It’s hard to watch, as they’re so scared and confused and don’t know that the pain is behind them, nor how much pain they’ve avoided in the future. But in the time it took to print our vaccination certificate and take the elevator down to our car, she was fast asleep and protected from the eradicated scourges of generations past.

And the more I think about it, that’s the part that really gets me about the anti-vaccination movement. It’s not just that we disagree on the facts (vaccinations don’t cause autism), it’s that we fundamentally disagree about what it means to be human. Because what is the human condition if not striving for a better world for our children in the face of our own mortality?

For me, nothing represents this better than the vaccine, which I’d argue is mankind’s greatest accomplishment. Consider that over the course of 10,000 years, smallpox killed more people than anything else in history. And while it killed between 300-500 million in the 20th Century, the disease has been eradicated and relegated to a freezer thanks to the magic of vaccination. Science FTW.

While I swell with pride when I think of the American flag planted on the moon, it’s not as much as when I see the world’s tiniest Band-Aid.


Dear Lucia

I had been meaning to write to you while you were in your mom’s belly, but you surprised us by coming a little early! Maybe that’s the first lesson – you can’t plan everything, which knowing your genes you’re likely to think you can. But I’m glad you’re here now; I couldn’t wait to meet you either.

I wanted to impart upon you some fatherly advice for making your way in the world. Granted, it’ll be a few years until you can read this, and many more until you’ll understand it. But as much as a letter to you, it’s just as much a reminder to myself about what’s really important, what values I really care about sharing with you. Without further ado, a few things I’ve learned:

  • Surround yourself with the best people you can find. Under no circumstance compromise on this issue.
  • You can have anything you want if you work hard enough for it and get lucky. But you can’t have everything you want; choose wisely.
  • Stick up for the little guy. Better yet, help them no longer be the little guy.
  • The only opinions that matter are those of the people who matter. We’ll revisit this issue in greater detail before high school. In fact, I’m sending you an Outlook invite now for Saturday, August 26th, 2028 for us to watch Mean Girls together.
  • Find a problem that’s so important to you that you’ll spend your life working on it.
  • Resist the temptation to tell someone how much you despise them – you’ll almost certainly feel worse afterwards. The opposite is true of telling someone how much you love them.
  • Try every kind of food and art you can find; someone somewhere thought it was good, and maybe you will too.
  • Time is the only truly scarce resource you have; spend it doing what you really care about.
  • Love, really is, all you need.

Part of me wishes you could stay this small, but I’m looking forward to watching you grow up. And I’m looking forward to you teaching me new things about the world.

Low Information Density: Why You Should Never Attend a Tufte “Course”

Let me save you $400, 6 hours of your life, and considerable frustration by imparting upon you the key takeaways from the Tufte course I attended here in Seattle last week.

I may have gone in with hopes too high. I expected him to discuss the general principles of visualizing data, to work through some examples of information displayed poorly, and most importantly how it could be improved using said principles. But we didn’t get that. Instead, we got a rambling collection of the fetishes and grievances Tufte has built up over the past few decades, including:

  • An obsession with maps. He thinks maps are the purist example of good data visualization. Sure, they’ve stood the test of time; yes, Google Maps is one of the most widely used websites. But are maps really such a great metaphor for summarizing data? It’s much easier to visualize objects in the physical world than it is to communicate abstract notions such as volumes, times, averages, etc. A mouse can find its way around a maze, but good luck getting it to understand your multivariate regression.


  • Blaming the tools, not training the workman. I knew we were bound to get some PowerPoint bashing, but I didn’t quite appreciate what an existential issue he has with the product, its creators, or the entire software industry. He talks about the “software industry” the same way you might talk about “the military industrial complex.” He actually has halfway decent joke about how there are only two industries that refer to their customers as “users” (software and illegal drugs, har har.) But his vitriol goes so far that you’d think his father died at the hands of a PowerPoint animation.

    Farther down the rabbit hole, he recommends using Latex over Word and R/SAS/JMP over Excel. Because what people really need is a new, more complicated tool instead of learning how to use their current tools better.


  • Magical Screens. He has some bizarre theory about how new 4k screens are going to change the way people interact with data, as if pixel density was the limiting factor we were coming up against. This wasn’t a passing observation – he had about 20 minutes dedicated to how much better screen resolutions are getting and I still have no idea why it matters.


  • Life is $GOOG. While he used “marketing” as a pejorative term about 20 times during the day, Tufte has no problem extoling the virtues of the biggest advertising company in the world. From Google Maps to Google News, he’s tickled by everything coming out of Mountain View. He even spent about 15 minutes on this project of his where you can create a collage of Google Image results. While I don’t know what the point of it was, I did enjoy making my own collage with it.


    The only thing in the known universe potentially more awe-inspiring than search advertising is an $800 device that lets you check Facebook and watch cat videos. I’m of course referring to the iPad, which along with everything else made by Apple is created only with organic materials in fair trade factories and is filled with pixie dust and hugs.

Toward the end of the day, he started getting even weirder. He had this soliloquy on presentation tips that morphed into a philosophical piece on how to treat your fellow man. Some of his insights included “show up on time” and “write down questions people ask you.” I half expected him to say, “and wear a tie – you see these kids these days in their jeans and their hoodies and their messenger bags and it just doesn’t look professional.” And the whole thing was him reading several paragraphs of text from a couple of slides; here he was giving a presentation on how to give a good presentation while committing one of the cardinal presentation sins – meta.

And just when I thought we were done, he left us with this parting gem: “never hire an MBA.”

Well, Ed, the feeling’s mutual. I’d never hire you again either.


Entering & Breaking (+Insuring)

I had a great July 4th weekend here in Seattle, spending most of it grilling meat on various roof decks and patios. During one such session, I had a friend pitch me their idea for a new business venture.

On Monday, July 7th, I wrote back on my walk to work:

Been thinking more about your idea, and I think it’s bigger than <redacted>. An area that hasn’t been much impacted by the sharing economy yet is minor housework. Imagine a service where you can schedule (or book ad-hoc) various household services/chores like doing your laundry, dishes, cleaning, walking your dog, maybe even do some grocery shopping while you’re at it and put the food in the fridge…

As long as you had some kind of keyless entry, could be a pretty slick way to improve household work. Taskrabbit wasn’t able to tap this market because (1) remote home entry and (2) too much friction for small tasks. If a service provider has a large number of positive ratings, odds are pretty good they won’t steal your TV while you’re out.

A mere three days later I see the following headline:

Farther down they comment, “The biggest change is getting rid of the auction format. Instead of posting tasks and waiting for people to bid on them, clients will now post a task and let the algorithms match them up with people willing to carry it out.”

A very smart way to deal with the second problem I mentioned, which is reducing the friction in the matching process for small tasks. But if I were Task Rabbit I would look to partner with a keyless entry system to reduce the coordination headache further. If I’m already home then I don’t need to worry quite as much about the insurance; it makes a bigger difference when I’ve granted someone access to the property without my presence.

Are you going to keep your windows phone?

There’s no question I get asked more often about leaving Microsoft. Sure, people want to know what start-up culture is like (Ping pong table? Check. Kegerator? Check.) And folks who have never worked at a start-up want to know about how risky an endeavor it is. I would have expected that. But I never would have expected the fascination with my choice of phone OS.

Maybe it’s because there’s something about your phone in this day-and-age that’s so personal. It’s your constant companion, your gateway to the world; is there a product with which you have more interaction?

So you might imagine I feel really strongly one way or another, but I’m torn. Here’s what I’m thinking:

Keep Windows Phone

First and foremost, I love this phone. My current one is a Nokia Lumia 928 and it’s the best phone I’ve had. It takes amazing photos, can transfer data with NFC (which almost never gets used), and can charge wirelessly (which gets used all the time.) And I’m a big fan of the Live Tile / Metro interface and operating system.

Then why get rid of it? Apps. The app situation is every bit as bad as it’s made out to be. When I was at Microsoft I used to roll my eyes every time I would hear “we have 48 of the top 50 apps!” Because, while technically true, a more accurate stat would have been “we have 3 of the top 5 apps” (missing Instagram and Pinterest.)

Sure, we finally got Instagram, but we still have a deprecated experience on it. There’s still no Pinterest or Snapchat, which means it’s virtually impossible to plan my wedding or send pictures of my genitals to my wife. And if the big blockbuster apps are only 95% there, you better believe the long tail of up-and-coming apps are less than 5% there. It’s enough to make you feel as if there’s an entire economy you’re not participating in.

And I don’t see that changing in the foreseeable future. At Microsoft people touted the 50 million unit mark as a big one; once you start selling 50 million phones a year then the audience starts getting big enough for app developers to dedicate resources to the platform. But the reality is that app developers have limited resources, and you’re always going to get served third no matter how big in absolute terms your third slice of pie is.


I’ve been hating on the iPhone since ’07. I bring that up not necessarily as a point of pride, but to note that getting an iPhone now would be tantamount to admitting I was wrong for the last 7 years; cognitive dissonance is a powerful force.

I remember once in our apartment in DC having a race with Alex Field to see whether he could really type faster on his iPhone than I could on my state-of-the-art BlackBerry, which had a real keyboard like all real smartphones did. I don’t remember exactly what the paragraph was that we raced to complete (I think it might have been something from the Federalist Papers), but I remember that I lost.

On a more practical level, my iPhone would constantly be out of batteries. Aside from the aforementioned wireless charger I have, there are also a zillion USB chargers near every outlet and hidden away in every travel bag I own; replacing them all with iPhone 5 chargers would cost hundreds of dollars, which I’d need to do again if Apple decides it would be 2% faster or more stylish if they completely change the format on the iPhone 6 or some other hair-brained idea that puts aesthetics above practicality. As you can see, I have some issues with Apple as a brand. But seriously, does no one ever question why they’re using a non-standard charging format?


I think a big part of the Android pitch is that it’s married to all the other Google services you use and love; the problem for me is that I don’t use any of them anymore. I’d be fine switching over for maps and search, but I wonder what the Android experience is like using for email and OneDrive for storage. And I’m skeptical about using an OS from a company that’s fighting so hard to promote their inferior social network against Twitter and Facebook/Instagram. But if I can get my hands on one, I’ll give it a whirl.

Waiting Game

For now I’m waiting to see how the Windows Phone ecosystem evolves. I really want to be able to use this phone, but hate feeling like I’m stuck with the apps from 3 years ago.

Is there anything else I should be considering? Fangirls and fanboys of all platforms, sell me on yours.

Prosocial Networking

The Haverford Center for Careers and Professional Advancement asked me to write a post about the importance of using LinkedIn for college students to connect with alumni. Here’s what I said…



I used to think “networking” was a pejorative term, one that described the unsavory, backroom schmoozing that gave the unqualified-but-well-connected an express lane to the corner office. The scene I imagined was set at a country club, where the children of senators and industrialists would advance their careers at a white collar version of the NFL combine, putting on display critical life skills such as being able to have a functional conversation after three scotches and handling the embarrassment of your short game with grace.

The path to employment, at least in the meritocracy I wanted to believe in, was by doing well in school, writing a great cover letter describing your talents and passions, and applying to jobs through a company’s careers website. The universe, in its relentlessly rational way, would ensure that the most qualified applicants were whisked to the roles to maximize their marginal product of labor; think Milton Friedman wearing Hogwarts’ sorting hat. “Networking” was akin to cheating, giving a leg up to applicants with a coincidental personal connection to a hiring manager.

Nine years, four jobs, and an MBA later I’ve developed a more nuanced view of networking. I’d like to share with you some thoughts on the topic that I wish had been shared with me back when I was looking for my first job.

I have good news and bad news. The bad news is that networking is every bit as necessary as it’s made out to be, and might even be undersold. Personally, I’d be very hesitant to hire someone without having had someone I trust vouch for them; interviews and resumes are poor substitutes for a personal recommendation. For personality fit, only the most socially inept are unable to pull themselves together to seem employable during an hour-long interview. And for subject matter expertise, interview questions tend to be very predictable. Forward me any job description and I’ll give you ten questions you’re likely to be asked. As Sun Tzu said, “Know your resume, know the position, and you will get 100 jobs.” Or something like that.

Your resume isn’t helping you stand out either. For me the resume occupies a place right next to the fax machine in the category of business practices that need to die. No useful information other than proper nouns are ever conveyed, and they’re famously filled with exaggerations at best, and outright lies at worst. Plus, let’s be honest, when you’re 22 all your resumes pretty much look the same. Nota bene: you unfortunately still need to have a resume and make it conform to certain guidelines your career counsellor can help you with. But I’m hoping future generations will be as familiar with resumes as they will be with phones that require chargers or cars that require drivers.

A much better medium for networking purposes is your LinkedIn Profile. I’ll admit that I have a particular affinity for social networking given my company, Simply Measured, provides social media analytics for marketers. But I’ve long maintained that LinkedIn is a much better way for you to display your passions, your creativity, and your personality than a resume ever will be. It’s a place to have a multimedia expression of your career ambitions; talk about what you’re most proud of, what you’d like to accomplish, link to your work around the web (tip: start a blog, if you don’t already have one.)

And now the good news: networking is not nearly as reprehensible as you think. In fact, it can be enlightening and even fulfilling. But you need to change your approach 180 degrees from where it likely is. Don’t think of networking as a means-to-an-end, where the “end” is about calling in enough favors for you to land a job. Think of it as an opportunity to learn from people about their jobs (what do you do?), their passions (why do you do this?), and their backstory (how did you get here?). If you’re anything like me, you’ll be amazed by the diverse ways people can make a living in this world; I continue to be. Another pitch for LinkedIn: you’re just a few clicks away from finding alums who are happy to share their experience and perspective with you.

But as great as the accumulation of knowledge is, there’s yet another reason why you should embrace networking: it’s an opportunity for you to help someone else. Yes, you.

If I could send one book back in time to my 22-year-old self, it would be Adam Grant’s Give and Take. I want you to read it, because I think it’ll change your outlook on networking as it did mine. In short, when you think of networking you need to harness your inner JFK: ask not what your network can do for you, ask what you can do for your network. Networking isn’t about asking for favors, and it’s not even about tit-for-tat; it’s about creating more value for others than you appropriate for yourself. And there are some ways to get started, like the 5-minute favor, for example:

  1. “Use a product and offer concise, vivid and helpful feedback.
  2. Introduce two people with a well-written email, citing a mutual interest.
  3. Read a summary and offer crisp and concrete feedback.
  4. Serve as a relevant reference for a person, product, or service.
  5. Share, comment or retweet something on Facebook, Twitter, LinkedIn, Tumblr, Google+ or other social places.
  6. Write a short, specific and laudatory note to recognize or recommend someone on LinkedIn, Yelp, or other social place.”

So get out there. Make your LinkedIn profile a place for ambition and expression, and use the service to find people you can learn from and add value to. Need more specific suggestions? Well, you know where to find me: