When Bad Design Is Good & Why Snapchat Is Screwed

Sometime over the long holiday when Jess and I were back in Pittsburgh, our youngest cat Straka decided it would be a good idea to chew through the various cords running out the back of the TiVo. This prompted a quick trip to Best Buy – the putative choice for “I need something random in the tech universe at the last minute” now that Radio Shack has gone away – and for reasons that elude me in retrospect, a conversation about Snapchat on the cab ride back to DUMBO.

First, my personal feelings on Snapchat as an incredibly infrequent user: I think it’s fair to say that I get it and that I don’t get it at the same time. I can absolutely believe that it’s got a near hammerlock on the attention span on a very lucrative demographic; I saw that first hand the other day when three teenagers sitting in front of me at a Penguins game were glued to it for three straight hours. I can absolutely believe that it’s got decent potential as a distribution platform, if only for reasons that can generally be explained by this post.

That’s generally where the positives end for me; the second it goes public, I’m buying puts against it. The ability to be a sustainable platform for marketing requires you to present to the marketer as much demographic information as possible, since there is an obvious and direct correlation between targeting, conversion, and ROI. As far as I know, Snapchat offers very little of this, and certainly a laughable amount compared to it’s peers in Facebook and Twitter. Beyond that, there are obvious questions around the buying power of the userbase, the lack of brand safety given some of the more..salacious uses of Snapchat, the complete lack of switching cost that ephemerality destroys, and the unclear conversion funnels and units available on the buy side.

That’s not the biggest problem though. Their biggest problem is the UX, and it’s a problem that will kill them.

Let’s take a step back for a second: why do we think Snapchat (and to a lesser extent, Kik and the like) grew like it did, leaving Facebook and Instagram in the dust? The answer is simple: parents joined Facebook. What’s the point of being a teenager and doing morally and judgmentally dubious things if your Mom can find out about it and even worse, comment on it?

In that privacy vacuum, Snapchat emerged. Not only did it offer ephemerality, but a dense, complicated UX that was virtually guaranteed to be too confusing for anyone above a certain age to understand. This is the inflection point when bad design became good, designed intentionally to be confusing in order create enough of a learning curve to ensure that only the savviest and the familiar (ie: long-time users, which is to say, the teenagers trying to escape their parents’ watchful eye) would be able to use it.

(If you don’t believe me, go ask your Dad if he’s heard of Snapchat, and when he says no, show it to him and ask him what it’s for and how to use it.)

Of course, it’s also true on the other side that this intentionally difficult UX is what will ultimately kill them. Facebook is a fantastic business because it knows what just about every media company ever knows: revenue scales on audience. They became an exponentially more valuable company when they decided to open it beyond Harvard, just like they became an exponentially more valuable company when they opened it up beyond college students, and so on and so on. It’s simple math: the top of the funnel got almost infinitely bigger, and as it did, interest from advertisers got infinitely larger. And boom, it happened: Facebook took it’s largest asset – demographic and interest data that you willingly gave it – and packaged it for sale.

Snapchat won’t have any of that expansion without fundamentally changing the UI, but doing so will alienate their only core population and take away the only strong reason they have for being loyal to the app. They might resist that urge as a private company, but I’m certainly curious how and if they’ll be able to resist it as a public one. If they can’t and are forced to redesign, their complete lack of switching cost will do them in, as the teenagers they built their empire on will simply find another platform in which to document their dumb decisions.

It’s going to be an interesting ride, one that I will short all the way to the wastelands of Zynga, Groupon, and others.


The Final Post-Mortem

This is it, the last time I’m going to noodle over it. While it’s over and it ain’t going to change, don’t think I’ll be able to mentally turn the page unless I try a little harder to make sense of it. So here goes!

Ultimately, the one thing that I’ve failed to really recognize is the degree in which small town Americans are feeling upset and worried. Failures in education and the effects of globalization – although we’ll likely disagree on the effects of trade agreements – have dried up jobs and have made the pursuit of the American Dream very difficult for them. It has to be a very unsettling experience.

For as strong of a candidate Hillary may have been on paper, I don’t think at this point you can really defend her inability to communicate to these voters. She may have had plans for clean energy jobs and for education and for everything and they have been rock-solid pieces of policy, but they weren’t communicated well and certainly not presented well in person – instead it was dispassionately placed on a website, without context or fiery, buzzword-y rheotoric to back it up. The sole job of her campaign wasn’t merely to convince people why they shouldn’t vote for Trump, but they should vote for her. Her messages weren’t received where it mattered the most, and I think it’s too much of a cop out just to say that the electorate wasn’t willing to listen.

However, and I should probably put that in capitals like HOWEVER, I don’t believe that endorsing a racist platform as a means of expressing your resentment is the answer. I don’t believe that voting for local and state representatives who make them false, impossible promises is the answer. I don’t believe that allowing yourself to be fooled by a charlatan who takes advantage of your fear and nostalgia is the answer. Many voted for Trump, but they did so at a significant hit to their credibility; they cannot say in their true hearts that they didn’t know what Trump was about. They unequivocally said that they are voting for themselves and their families, not to ensure the safety, prosperity, or even basic Constitutional rights of minorities that they’ve never met. They said that feeling that their personal shot at the American Dream, the one they’ve been promised, is worth more than social justice.

They simply cannot say they didn’t know. That’s as much of a cop out as saying people weren’t willing to listen to Hillary just because she’s a woman.

In thinking about what’s next though, I’m flummoxed by the sudden rush for people to try to find a middle ground, to find the unity to move forward. Why would the Democrats show unity when there wasn’t even a hearing for Merrick Garland? Why would there be unity when Republicans refused to work with the Obama administration, calling into question his authority as a President in the most hateful and bizarrely obstinate ways? The Republicans fought and stalled and stalled and fought, and now the overarching message is to listen to will of the people and work together? Screw that.

The next step for the Democratic party is to take a page out of the Red playbook. Tap into your most vocal fringes – tacitly supporting their views without outright endorsing them – and stop confusing “centrism” with “electability”. Fight like hell. Re-organize at the lowest levels and above all, listen. Go to places where you’re not welcome, and listen. Ultimately, people on either side of the spectrum want to know that they’re important, that their voices are being heard, and that someone is listening. Judging from afar and just saying “Hey, I know things are tough, but go check out my website!” is not the answer, and it’ll be even less the answer after four years of Trump.

My prediction, admittedly hopeful: four years from now, we’ll be celebrating our first female President as Michelle Obama absolutely wipes the floor with Trump.

(And now, back to sports and startups. Thank God.)


In Times Of Great Uncertainty

I know that I’ve been behind the schedule I set; no excuses, I’ll just to be more mindful of it. But I want to veer off schedule a bit and talk about the election, because frankly I’ve spent the last 18 hours or do in a weird state of disbelief and I worry that unless I try to put pen to paper and release my thoughts, I’ll be in that fog for a long, long time.

First things first, I’m not a doom-and-gloom guy. The sun came up, I went to work, our kittens needed fed – none of that changed, and it won’t tomorrow or the next day. Of course, it’s very easy for me to say that: as a white Christian male, I’m significantly less vulnerable to what could happen than others, including my fiancee, my black Muslim best friend, and my small, impressionable nieces.

Try as I might to assign blame, I also know it’s not that simple. For as many people who can point to latent racism and sexism as the cause, you can also point to a very lethargic Democratic voter turnout in states where they were counting on it the most. For as many people can point to Comey and the bizarre intervention of Russia, you can also point to the fact that the coastal elite class of the Democratic party often does very little to truly understand or empathize with the concerns of middle America. Assigning a singular point of failure trivializes the lessons that everyone needs to learn from this.

But don’t get it twisted, either; just because the issue is complex doesn’t mean I can’t ultimately feel that the conclusion was bafflingly wrong. America as a country voted for a completely unqualified person, just totally and utterly incompetent for the role in every single facet in which you can judge that sort of thing. I can’t say that clear enough. Resentment may explain a dumb, incomprehensible decision, but it doesn’t excuse it.

With that said, I’m trying my hardest not to condescend to the half of the country who voted for Trump, as I want to be as reasonable as I expect others to be and not just be a paragon of the coastal elite that conservatives show up in great force to counteract. I want to be empathetic because you can’t just tell people that their feelings are wrong and they’re dumb for having them. Still, I find it next to impossible to find a legitimate reason for their choice. Simply choosing an extreme alternative because the status quo isn’t working isn’t what reasonable people do; only people who would rather watch it burn than fix it think that way.

For as much negativity surrounded both campaigns, I resist in the sense that, at the end of the day, I love America. America is badass. America is innovation, America is propersity, and America is a nebulous ideal in which I assign everyone a great benefit of the doubt, to assume that everyone who participates in the global experiment is a good actor that wants to see good things for everyone. I choose to refuse cynicism – as easy as it would be to adopt that mindset – because cynicism in this sense would imply indifference, a resignation that individual effort is useless. I choose to not label all opposition to my belief as racist, sexist, or poorly thought of, for the same reason I would reject anyone calling my beliefs the result of an educate elite bias.

The decision has been made, and it’s not changing. Moving on. I’m willing to try to find middle ground and assume the best of intentions for the time being. So here’s some rope; if you hang yourself, you’ve got no one else to blame and you’ll have to answer the bell for it in four very, very short years.


Multivariate Logistics

I think it’s fair to assume at this point that on-demand is generally here to stay. Now, it’s possible and more likely probable that you’ll see a few more companies die off due to unit economics and/or over-aggressive expansion (and definitely consolidation of similar companies), but the general pattern has now been established and certainly the demand for someone else doing something for you will always be there.

As it currently stands though, full value isn’t really being met. We’re still stuck in this unitary view, a one-to-one relationship where a single user is interacting with a single service and a single deliverer of labor. (I know that last part is awkward; I don’t know how to phrase it.) This doesn’t really impact the user all that much apart from surge pricing, but it absolutely impacts the worker, as they are very inefficient relative to opportunity. Let me give you an example.

It’s an average Saturday night, and my lovely fiancee is getting cocktails with her friends. I’m staying in because Alabama/LSU is on, and because the easiest thing in the world to do is nothing. Instead of making myself dinner like a normal adult, I decide to get some Thai food. I send the order out via Postmates, it gets accepted, and the wheels turn.

Now imagine concurrently, someone in the building across the street from me puts in an order from the same restaurant. Or imagine that a worker driving for Uber has a request to take someone two blocks down the road from the Thai place into DUMBO where I live. In a perfect world, whatever dispatch logistic system the driver is using should be able to determine that and allow him or her to double down, since it’s unlikely that the passenger would be all that upset to have the delicious smell of Thai food as their traveling companion.

I assume that all of the logistics of these companies are handled internally and thus, there’s no chance for them to speak to each other. I think that’s a missed opportunity. As these companies get larger and face more competition (and as more labor enters the market), the labor is going to get squeezed as the companies either up their revenue share or decrease the fixed payments. As such, you’ve got an increasing dissatisfaction amongst the labor, which causes them to churn as making a living becomes nearly impossible. Having this multi-variate logistics – potentially served by a third-party which not only means the on-demand service doesn’t have to build/maintain it, but theoretically would increase demand – would make everyone happy.


Going Where The People Are

Today HBO announced that they are canceling Bill Simmons’ “Any Given Wednesday”, his first attempt at establishing himself as a reliable draw outside of the ESPN universe. I can’t say I’m surprised.

No one can ever really doubt that Simmons brought a fresh, new voice to the fray when he started writing his sports columns back in the late 90s. He was on the first wave of writers who grew up not just loving sports but pop culture in general, mixing it all together to simultaneously be entertaining and relevant to a very wide audience. Gone were the old, crotchety writers in the press box; the Internet was a new medium and he accurately foreshadowed the abrupt tonal shift towards the snarky and the irreverent that was to come.

He also fell to the same issues that a lot of guitarists and second fiddles on championship sports teams fall to, which is to say he began to see himself as something larger than the entity in which he was launched. He reasoned that on the basis of Grantland’s success, his fanbase would follow up onto whatever platform he chose. He was wrong.

That’s not to say that he’s suddenly become irrelevant or he won’t have a second act in his career. He’ll simply have to go to where the people are, and not expect the people to come to him. First, that’s just not the way it works anymore, which is why you’ll increasingly see celebrities and other large brands get involved with Facebook Live, Snapchat, and other areas where the community is congregating. Second, an individual creator like Bill Simmons is unlikely to ever create the same kind of brand strength that the platform itself can generate; ultimately they’re not loyal to you, they’re loyal to the platform that supported you and will be around before and after your popularity peaks.

As for ESPN? They may have a host of other issues to struggle with as people cut their cords (although their OTT offerings are exceptional) but they’ll rock solid in one regard: there are easily millions of people around the world who want to be and in fact think they’re the next Bill Simmons. One will emerge, and the cycle will happen all over again.


Aliases

So I know it’s Wednesday – the sports day – but unfortunately I’m behind with some things I have to do today and therefore I cannot post the long, thoughtful rumination of the sports world that I previous planned. Doh.

Instead, I’ll share with you a quick story that I was reminded of earlier today, when I was setting up alias emails for our customer support to use.

Back at Carnegie Mellon, all of our email addresses were tied to the Andrew file system, which was a super revolutionary enterprise-wide file management system that CMU built in the 1970s that even today I don’t really have my head fully wrapped around. As such, to email me in 1999, you’d have to email nmb2@andrew.cmu.edu and not simply nmb2@cmu.edu, which caused a lot of problems for parents, friends, and various well-wishers who may not have been as knowledgeable of CMU’s system.

To combat this, you were allowed to create aliases that forwarded the email on as a simple pass-through. The first one I created was simply nmb2@, to solve the obvious problem above. Once we learned however that CMU didn’t protect the namespace or set really any kind of rules on what (or how many!) aliases you could set up, my friends and I had a field day. It basically became a race with other parts of the University, most of which had no idea they could or even how to set up these aliases in the first place.

One of my friends reserved admissions@, which basically meant that he got a ton of overflow mail from prospective applicants, SAT results, and a host of other stuff. Another reserved dining@, and he got tons of requests for various catered lunches and presentations within the university.

Me? I went with housing@, which made me privy to an awful lot of hilarious emails about different mishaps that happened around various dorms as well as the occasional “My roommate used my toothbrush!” kind of stories. The only one we couldn’t get was police@, which in retrospect, was probably better that we didn’t.

(I will say that for anything really serious, involving abuse and the like, it was forwarded on correctly.)

Retrospectively and with the wisdom of age, it’s not quite as funny as it was to us back then because it’s very possible that had an actual email gotten to admissions or to housing to whomever correctly (or if it had just bounced and that person had realized their trivial error), lives could have been permanently changed. But it was for me an example of what happens when you give a lot of leeway to very bored 18 year olds, and it’s sort of the kind of random jackassery you can see all over the Internet today.


Fraternity

Yesterday was the first entry in my new commitment to writing; I hope you enjoyed it. I think I’m going to like the Monday entries the most, because they let me postulate a little bit about current opportunities available in the marketplace for entrepreneurs. The Tuesday one will also be fun, albeit in a different way; it will allow to really think outside of the box and dream up some crazy ass ideas that you would never attempt unless you had a few years and a large trove of someone else’s money.

The first big idea I have requires a bit of exposition. Like almost everyone in the tech world, I was what you could charitably call a nerd growing up and in high school. I’m not saying that from a point of regret or from self-deprecation or anything like that; it’s just the truth and there’s no longer any reason not to be open about it. It wasn’t until college at CMU that I really blossomed into the social and moderately extroverted person I am today. The root of that development is partly due to the demographics of the school and being surrounded by other people with similar interests, career goals, and experiences. Another, perhaps equally large part, is due to the structure in which social life at CMU is set up, with a surprisingly robust Greek life and a host of activities and traditions baked into that experience. It’s fair to say that at just about any other school, it’s unlikely I would have found myself in a fraternity. But I did, and inasmuch as those experiences were the most CMU could do to create a proxy of the prototypical college experience, it ended up a profound effect on my life then and my friendships to this very day.

Now, into the meat of the post: I think the current fraternity system, despite it being an overall net positive for me, is outdated and tangibly useless.

If we take the idea of college at it’s most utilitarian value, we conclude that it’s there to prepare the student for professional life. We can assert that the whole reason why people choose to attend and to pick a course of study is to set themselves up for a long-lasting career in the field that they choose. We all know however that the full potential of that career is not only shaped by domain knowledge, but the development of a professional network and the social skills necessary to succeed in the real world. Given that, we can generally conclude the traditional idea of college is well-suited for the former but very ill-suited to the latter.

The question then becomes, what’s the best way for students to gain those skills? For a minority of the population, they’re self-starters and can do it themselves, hustling their way into internships, conferences, networking events, and a host of other things that allow them to hit the ground running upon graduation day. Those students are few and far between, and if we’re being realistic about how we develop those skills in the majority, the scale of resources required to teach that on an individual level to a student is functionally impossible for a university to take on.

To solve this problem, I look at the opportunity for a third-party organization or club to take on this role, sort of like a finishing school. Play this out with me for a second:

Let’s say I wanted to create a non-profit company called Success, Incorporated. (Or whatever, I didn’t think about the name too much.) This company would be tasked with starting branches at college campuses, merging the social concept and exclusivity of fraternities (only accept the most promising of students, creating a cache of interest) with the utility of exposing those students to business executives, career advice, skill development, and the social intelligence that conventional education doesn’t teach. Keeping it in the tech world, I would start with a campus like CMU and reach out to established alumni executives in the Valley and elsewhere to join the cause for that specific branch of the company. The value prop for them would be the honest chance to help out students who are interested – thereby leveraging the natural altruism of people – and concurrently give them first crack of graduates coming out of CMU – thereby leveraging their pragmatic side. I’m also somewhat convinced that both sides of this would pay money for the opportunity, given the difficult competition for the best young talent (corporate) and the value of having this advantage as an emerging graduate (student).

The perfect implementation of this is figuring out a way to combine the positive things that people report about being in a fraternity – the shared experiences, the leadership development, the philanthropy, and yes, the social life – with all of the advantages that a strong professional network and a course of education in the more intangible aspects of career success can bring you. How it potentially could work out in the real world is beyond me, but it’s fun for this ex-frat boy to think about, and given how many people in the startup ecosystem were also in college fraternities during their undergraduate days, I wouldn’t be surprised at all if there were people who are already working on something similar.


Verification

I’ve know I’ve said this before but I’ve generally decided to take a more consistent approach to writing. I haven’t been particularly active on this front; not necessarily due to lack of time or content ideas, but rather I’m simply one of those people who finds it very difficult to do things that I consider to be routine. It’s just not who I am.

But like I said, I’m going to give it another honest shot and to achieve this goal, I’m going to take a page from Fred Wilson and try to form some habits around it. I almost always up eating lunch at my desk, so instead of randomly perusing ESPN, why not take some time and jot down some thoughts, as incomplete as they might be? I have to be fair with myself in this regard and recognize that to achieve the kind of volume I want, I’ll have to not be as perfectionist as I usually am and maybe even adhere to a consistent set of themes for the content. So with that in mind, here’s my first attempt at a consistent structure:

Monday: Realistic Things Someone Should Build
Tuesday: Crazy Ass Ideas
Wednesday: Sports
Thursday: Fly or Die
Friday: Fearless Prognostications

So without further adieu, here is my first shot at forging a routine and writing more, and it’s a semi-realistic thing that someone – not me – should build. (And forgive the choppiness of the segue; they were originally written as two separate posts.)


I’m sure I’m not alone in saying this, but I want this election to be over. I’ve wanted it to be over basically since it started, and I’m incredulous that there could possibly be any undecided voters at this point. Regardless of your politics, I think at this point you’ve generally chosen your side and likely dug your heels in super deep against the opposition. I can’t name really a single positive attribute about the candidate I’m not voting for, and sadly I’m sure there’s a reciprocal feeling among the other half of the population.

One of the more distasteful aspects of the election for me has been the rise of super partisan, extremely misleading echo chamber media. While I don’t doubt a big swath of it is simply opportunistic scumbags exploiting the worst in people, you shouldn’t minimize or ignore the impact it has. It’s simply a matter of fact that this election features two very, very polarizing candidates, and their faults are exacerbated by an ever-present constant news cycle and the rise of easily shareable memes as a means of disseminating political opinion. In this vacuum of nearly infinite content demand, it’s no surprise that this echo chamber has formed, dramatically wounding discourse and the general civility of the electoral process.

Whether you visit Breitbart and their ilk as a check-in to see what the other side says or as a trusted source of unbiased news, you’ll see a pattern form very quickly. “Confident Trump Sprints Into Blue States”. “Border Deluge The Worst We’ve Ever Seen”. “Early Numbers Show Trump On Warpath To Victory”. And on and on it goes.

It’s worth noting at this point that Breitbart, relatively speaking, is much more established and polished than many of the outlets on their ideological side. There’s nothing inherently wrong to speaking of a population you’re self-selecting for and presenting your opinion from that point of view. When it crosses over to something more vicious or blatantly untrue or abusive, that’s where the issues start to rise, and ironically it’s that type of content that are more likely to see on Facebook. The more incredible the headline, the more it gets shared, and you better believe these publishers know it: why else would a headline like “ALERT – WikiLeaks Exposes THIS Shocking Hillary Secret, ARREST HER!” even exist?

It’s a post-fact world, which is sad in and of itself, and the more I see friends and family of mine from back home in Pennsylvania pulled into it, the more I try to figure out what a solution might look like. It’s difficult because on one hand, I don’t want to censor anyone and I certainly don’t want to stop someone from publishing simply because I may ideologically disagree. However, I think it’s reasonable to provide some level of consumer protection against unverified sources, the more cynical operations that are exploiting the more base instincts of partisan voters, the ones who are simply stoking the flame in order to get cheap page views.

The more I think about this problem, the more I get hung up on the idea of “unverified”. It’s an analogous situation to Twitter; if I were to start posting as if I were Penguins goalie Marc-Andre Fleury (And I did as recently as 2009, but that’s a separate post), people might believe me solely on the basis of how I was presenting myself. After all, I *say* I’m Marc-Andre Fleury, why would I be making it up? The simple solution of the verified profile on Twitter mostly solved this problem; people should have no reason to believe that it’s actually Fleury unless the blue check mark appears next to his profile.

This situation also analogous to site verification through SSL/TLS, which provides consumers protection against fraud and ensuring trust in any transaction the user and a third-party involve themselves in. This SSL security is managed in the form of a digital certificate that is managed by a trusted authority, so given that, why isn’t it intrinsically possible to ask the same of publishers? If you are truly a publisher that is operating earnestly then getting verified should be something you’d welcome, for the same reason that public figure welcome the verification process on Twitter.

I’m fully cognizant of course that this concept ultimately is somewhat subjective, in the sense that at some point you’d have to have a human being determining whether or not someone is worthy of this level of verification. Embedded in that subjectivity is the potential for political bias, unwitting censorship, and a whole host of other issues that Twitter itself is trying to grapple with. Still, I think you’d be hard-pressed to say that the state of verification/authority/trust amongst notable voices on Twitter is somehow worse than it is on the open web, and given the ever increasing number of these super-partisan publishers, I think taking a firm approach is probably the right step.


Minima and Maxima

Computing, in the beginning, was all about less. It had to be – the computers were extremely limited, therefore almost all procedures were suited for a singular task with little room for error. Up until the introduction of the GUI, there wasn’t even the idea of multiple processes; you had to finish what you were doing, and therefore for everyone’s sanity, everything was designed with the speed and efficiency of process completion in mind.

In the desktop era, it eventually became all about more. Bigger monitors, more resolution, faster processors; more, more, more. As a result, designers and engineers began to create products that were packed dense with features, stretched to the edge of the screen with functionality for every use case. Sure, there was still a need for hierarchy and an architecture to the options, but they were a secondary concern to the density – why not have it all, if the form factor allowed for it? The Microsoft Office suite is a vestige of this, while more straight killed AOL’s Instant Messenger.

Then the mobile revolution happened, and it kicked off an inexorable revolution. Just as Moore’s law dictates a reduction in size while maintaining power, the reduction of form factor dictates that products eventually get distilled back down to the basics. An great example here is Tinder, which reduces the process of finding a mate to the most basic form imaginable. Or Twitter – 140 characters, bite sized, on the go for the mobile user.

This all leads me to what my subject is, which is chat bots. While the rise of the bots isn’t anywhere close to the revolution that the desktop, Internet, social, mobile epochs have proven to be, it’s certainly something that has caught the imagination of the technology world. And before I get too long-winded, I’m going to tip my hand on them: they’ve got it all wrong.

Let’s say you want to order lunch, and like me, a decent chunk of your time is spent in Slack collaborating with your team and getting into arguments about the proper ranking of Starburst flavors. Lucky for you, Postmates has a command line integration into Slack, and it wants to remedy that ache in your belly.

@postmates tacos near 37 east 28th street, 10036

So let’s stop it there, after the very first command. If you don’t know this already, please understand that handling even that initial request requires an ENORMOUS amount of intelligent, difficult code. First, you have to build the basic language processing to even parse the request. Second, you have to have a repository of locations, in order to determine the vicinity of the request.

Third, now, you have to start making some assumptions. For example, since there’s no scalable way to query in real-time to see if a restaurant is open, Postmates would have to pull that potentially outdated information from somewhere, and then assume that if the request falls within that window, the place is open…assuming of course that since you didn’t specify a delivery window, that you want it immediately, and also assuming the request itself is formatted in a way that parser can understand. Further down the chain, it has to assume that the menu it has saved is correct. And so on, and so on.

But let’s get back to the chat interface of this. Since the interface is reduced down to a very minimal form – unlike a desktop version! – it’s naturally not going to allow for much path deviation or special requests. (Much like the software built before the desktop revolution, of course. But I’m beating it into the ground at this point.) Ask yourself: is it going to be easy to request no beans on your taco? What if you want a hard shell instead of soft? What if you want to tell them to make the steak well-done, to call when they’re downstairs, or that you don’t need a plastic knife because there’s fifteen million at your office already? It’s really no different than wanting to know if the person on Tinder profile has a college degree; the form factor in which it is presented simply doesn’t allow for an effective way to branch out to that level of detail.

To do all of that effectively, you have to overlay so many steps that it kills the very utility it had in the first place. Eventually the user is going to wonder if it’s really worth all of the effort, especially when there are other interfaces for the same task that are likely quicker and easier to use. At a certain point, it’s like tweeting from your Wii. Yeah, you can, but why? Where’s the utility relative to other options?

That’s not to say that I don’t think that chat bots will be useful for certain tasks. Far from it, actually. You just can’t however go into it trying to replicate the functionality that a more robust form factor will allow, which is why I think none have yet made a significant impact. Early mobile development suffered from this problem – trying to mobilize all of their desktop functionality – until people realized that it required a completely different level of thinking. Unfortunately for bot programmers though, a lot of the hardware that phone manufacturers eventually put into their phones to facilitate that creativity (cameras, GPS, accelerometers, etc.) are going to be impossible to integrate into a chat bot.

So going back to my initial example, what can Postmates do in this arena? Through the bot itself, probably not all that much, which is it’s a bit perplexing to see so many companies try. What it could do however, is try to figure out a way to accept a parameter-rich link that is generated from the bot. Maybe something like this:

@postmates tacos near 37 east 28th street, 10036
>Sup Nik, hungry, eh? No worries. There’s six Mexican restaurants within 0.5 miles of your address. The highest reviewed one is Dos Toros.

Now imagine that entire string is a link, that sends a string of parameters into the Postmates app or website. Voila – the discovery aspect is knocked out, and you’re already on step three or four of the process. Dos Toros is preloaded, as is your receiving address, as is the request for tacos, and now you’re on an interface more ideally suited for handling all of the branching that might occur.

But getting back to my point, right now, the people building the bots are getting it all wrong, in the same way that early mobile development was all wrong in trying to “mobilize” desktop functionality. The Apple Watch, for example, doesn’t have the form factor to do much by itself, but it certainly is an effective and streamlined interface for your phone; this is a good start. The sooner chat bot developers turn the corner and start thinking of their tools as interfaces and/or completely new paradigms, the better.


The High Dive

I love the Olympics. Part of it is because of the spectacle and part of it is because I’m an acute track and field nerd, but I have to say that another significant part of it is that reinforces a lot of things that I’ve come to learn about life. I know it’s trite – and certainly heavily represented in the soft-focus human interest stories conventional TV coverage is throwing at me – but I find that sports can teach a lot of lessons, particularly about understanding other people.

Here’s an example. (And before you ask, this example has nothing to do with me. It’s just an example.)

Let’s all agree that startups are incredibly difficult. They’re mostly long, lonely strokes through the pool, punctuated by periodic gasps of air. You launched your first product? Awesome! Enjoy the traffic that the buzz of newness creates, because in two weeks you’re going to feel even further behind than when you started.

So what do you do? You grind and you grind and you grind and you grind. In a way, you’re declaring war: war against free time, war against other priorities, war against personal relationships, and war against your own emotions. Take it away, Thomas Powers:

The logic of war seems to be if the belligerent can fight, he will fight. That leaders will not surrender until surrender is academic. How is a national leader to explain the sacrifice of so much for nothing?

Next time you’re watching the Olympics – or any sport, really – watch very closely when the goals are scored, when the time is up. The events are almost always zero-sum, but I tend to almost always focus on the team on the wrong end of the match. They’re disconsolate, but I think most people misunderstand the nature of that: they’re not upset about what might have been, they’re upset because they let somebody down.

(And before someone asks about individual sports, let me stop you there. No man is an island; there are coaches, parents, and fans.)

This was in full-force the other day in the Olympics, when I was – of all the things I could have been doing for that hour – watching synchronized diving. One of the divers for Brazil had badly mangled his dive; he knew it the second he hit the water. When he got out of the pool, he was on the verge of tears; not for himself, but rather for letting his teammate down. You could see it so plainly on his face, even more so when his teammate tried in vain to console him. It was compelling to watch in the most heartbreaking of ways.

Looping this back to startups, this fear of letting your team down is one of the strongest and most pure virtues of early-stage startups. When the going is tough, more often than not what keeps the team coming back is the unspoken contract they have each other. The founders and the executives that do the best job of fostering that spirit are the ones who are truly worth backing, and it’s not an accident – it’s a gift, and that’s why certain founders get backed again and again.

This connection also illustrates a critical difference between a large company and a startup. Larger companies are simply unable to foster that spirit, essentially making every team member a mercenary unit, unwilling to fight through the muck. Lots of employee loyalty these days at Groupon, right? Timely to recent news, it also illustrates one of the problems that hit Yahoo! hard, particularly in their acqui-hire phase; when you bring teams on for their talent, it is next to impossible to keep that team together if their putative leader – the dreamer who is most likely to leave and try to start something new – leaves. The connection is no longer there.

Interestingly enough, the founders who are most successful fostering that spirit – at least from my anecdotal experience – seem to all have significant experience in some high-level team sport. But that is another topic for another day.