On YikYak, Anonymity, and Schadenfreude

Okay, well, I’ve been marinating these concepts in my head for awhile, so this is going to be a long one. Fair warning.

For those of you who don’t follow tech news all of those closely, YikYak shut down last week. At it’s peak, it was used by over one million users per day – mostly college students – and was valued privately at nearly $400 million after having raised $73.5 million in venture capital funding.

I’d like to say that I’m sad about it. I suppose I am in a virtual, detached sense, but I find myself feeling ambivalent at best and not happy but perhaps exasperated at worst, since their failure is just so symptomatic of so many inherent flaws in the way startups are invested in and operated. It’s a failure on multiple levels, levels in which lessons never seem to be learned.

First, it’s important to note whether you’re familiar with the app or not that it was, at least in the era of it’s peak popularity, completely anonymous. It was nicely geofenced into certain locations – such as a college campus – and as such, it spread like wildfire. Hyperlocal memes and gossip and discussion and conversation; all very sticky and moderately useful stuff. Of course, it wasn’t a new idea – gossip-y sites like Juicy Campus and College ACB had mined this area and failed due to bullying, harassment, and general shittiness. This was mobile though! And venture backed! And growing like crazy! Allons-y!

The problem with anonymity however is obvious: it enables people to be their worst. Without some sense of authentication tied to an actual profile of some social worth, there are no negative repercussions for abusive behavior. Go ask Twitter. Go ask 4chan. My reaction is not just pessimistic. The complexity of human behavior in an anonymous environment isn’t something to ignore.

Of course, anonymity also allows for products to grow like wildfire, perhaps because they enable people to be awful publicly, for the same reason a little kid grins whenever he gets away with swearing – it’s fun to be transgressive. After all, 4chan is huge, right? And for VCs, this is music to their ears; growth is valued above all things – at least at stages of earlier investment.

What ultimately happens however is the anonymity that powers the growth also makes it impossible to control abusive behavior and monetize effectively. Advertising is the only business model that works here – because no one in the right mind would ever pay for such an app – and the core hook for why the app is interesting makes that business model impossible. Think about it: what brand wants their product next to something where there is no editorial control of content? Do you think Snickers would be cool with their ad below a post calling someone else a racial slur? Or how about Coke right above an anonymous message saying that so-and-so is a slut?

Beyond the challenge of monetizing an app used for anonymous social commentary, there’s a host of other mountains to climb. Anonymity means no email addresses or any non-notification way of reaching a user, which makes it impossible to get them back if they’ve uninstalled the app. Having no access to any data tied to an actual human’s demographics further hinders marketing, since you have almost no vectors for segmentation beyond geography. I could go on and on.

Interestingly, unlike Secret and a few others, YikYak did try to address these challenges. About eight months ago, amid rapidly declining downloads and usage, they forced user handles on everyone. Users were betrayed that the app that they once loved was taking away the thing that made it interesting, and ultimately it was a nail in the coffin of the fading app.

I’m trying to be reasonable though, because it’s very easy for some to be critical of obvious problems in hindsight. After all, Facebook didn’t look like Facebook when early investors wrote their checks. Of course, to invest in YikYak at the time – assuming they had similar growth patterns, which I doubt – you’d have to simultaneously believe the their founders were product visionaries on the level of Zuckerberg, that the market was as big and that the product team was talented enough to capitalize on it, and that they’d somehow figure out a way to monetize anonymity that no one else ever could. It’s frankly an absurd set of conditions to believe were or ever had the potential to be all true.

YikYak did have pretty explosive growth though, and in case you’re curious and/or ignorant to why that is critical, it’s basically because the people who give the VCs money are doing so to diversify and add risk to their portfolios. I can’t speak for all VC funds, but a decent chunk of them are backed by huge pools of capital, like state pension funds and the like. The managers of those funds likely allocate 99% of their investment to very low-risk things like bonds and mutual funds, leaving a 1% allocation for something specifically high-risk like venture investing. Risk obviously is correlated with big outcomes, ergo a win and the ultimate goal for a VC isn’t a $3 million sale to Square, it’s a $2 billion IPO.

To put it another way, let’s assume that at one point in time, YikYak did reasonable resemble Facebook. Hugely explosive growth, geofenced to a college, and so on. Absurd in hindsight obviously, but go with me. If the market cap of Facebook at their IPO was $104 billion and you thought there was a 0.5% chance that you’ve found the next Facebook, then the imputed value of YikYak even without any revenue, user data, or hard IP would be $520mm. All you would realistically have to do is say, “Alright, this has got a 1-in-200 chance of being the next Facebook, and the limited partners funding my VC firm have told them they want to find the next Facebook, so..”

Thinking like that is very flawed however, because it ignores that most market sectors in tech don’t have the capacity for multiple concurrent winners. We know for example that the era of consumer/social is basically over, and that it was won by Facebook and to a much lesser extent Twitter, Tumblr, and a few others. This is similar to the era immediately before social, search, which was won by Google and to a much lesser extent a few others. It’s a pattern that has existed throughout computing; mainframe was won by IBM, personal computing by Microsoft, web 1.0 by Amazon, search by Google, social by Facebook, mobile by Apple, and the next phases (VR/AR, blockchain) are yet to be decided.

If we agree that each epochal shift in computing has a winner-takes-most pattern and that pattern recognition is basically what VC is all about, how can you reconcile the logic of investing in YikYak based on one pattern (they looked like Facebook, sort of) while ignoring the other, which is that there is usually only one winner and that Facebook already dominated and won social? It’s not just that you’d have to think that there’s a 0.5% chance that you’ve found the next Facebook, you’d also have to factor in the unlikely probability that Facebook falls from it’s perch, since without it, you’d never be able to reach a big enough scale to be able to satisfy the home-run seeking thesis of the investment in the first place.

(As an aside: there are never VC post-mortems about failed investments and the logic behind them, which is a bummer, because that’d be an interesting read and frankly, that level of transparency would not only benefit the VC world and help them build trust among their partners, but could even drive increased deal flow as a function of uniqueness and provide a valuable resource for everyone to learn from. But I digress.)

All of that sort of brings me to my next point: why then did they raise $75 million in funding, given the incredible simplicity of the app from a technical perspective? It’s very unlikely they needed that money for advertising, as it’d be the ultimate fool’s errand to spend money advertising something that has no business model. It’s doubtful that it was for hosting or tech, since even at the speak of ~1m DAU, that’s a blip on any reasonable cloud computing platform.

I would then have to assume it was R&D, but even as an infrequent user of the app, I certainly didn’t notice any fruits of that labor. It seems doubtful they ever really needed it, for any purpose. Given that, $75m seems inordinately high to assign to R&D and/or to a rainy-day/what-if-the-bubble-pops fund – especially given the problems I elucidated above – and if the ultimate sale price was between $1 million and $3 million, I have to wonder where exactly that money went and why it wasn’t shut down well before it got to that point in order to at least return cash to the investors. After all, downloads and usage were plummeting, right? I find it hard to believe the writing wasn’t on the wall with failure inevitable, so why not cut bait and return capital in the same way that Secret did?

This is where it gets a bit sticky for me, because on one hand, as a founder I know how difficult the journey can be and I know that the difference between success and failure can be very slim. With that said, no one forced them to accept the money that was offered with all of it’s attendant expectations, and in general I find it difficult to drum up a lot of sympathy even for their employees as I’m sure they were handsomely compensated.

All of that for me basically adds up to my strong dislike when startups post their “it was an incredible journey!” self-congratulating post-mortem, as if it’s somehow notable or impressive to take in a ton of money and completely waste it. It ties into the weird and extremely troubling belief within the startup world that raising money is an accomplishment unto itself, as opposed to the ticking time bomb that it more accurately is. It’s exacerbated by the news cycle of TechCrunch and the like, with a bit of dick measuring/keeping up with the Jones built into it as well. But it’s still gross and a very misguided way of looking at it; had YikYak raised less and kept to a much lower valuation, their vectors for an exit would have been much broader and certainly less scrutinized by a board that was hungry for a return.

(I suspect this is a trap that first-time founders fall prey to a lot more often than experienced ones.)

As I mentioned in a tweet a few days ago, it’s been a red letter week for fans of schadenfreude. Between the absurdity of Juicero’s DRM for juice packets and the utter uselessness of their beautiful machine, the complete melt down of the Fyre Festival at the hands of the team behind the truly useless Magnises card, and YikYak, it’s very ripe for someone to come in and dive headfirst into the river of smug, hindsight-driven fingerpointing. I find myself very ambivalent on this topic, because on one hand, the problems for all of them were laughably obvious. On the other hand, being negative and cynical is one of my least favorite human qualities – particularly in regards how it fits on me – and too much of it ensures the inability to ever see the positive aspects of something unproven or new ever again.

Because of that ambivalence, I’m having a hard time figuring out how to conclude this post. Is it possible to wonder how in the world YikYak got the funding it did given the obvious problems and still believe in the transformative power of tech entrepreneurship? Is it possible to abhor the startup culture of celebrating fundraising as an accomplishment and celebrating failure as some kind of secret success and still be sympathetic to the amount of work and stress involved in the journey?

As of now, I don’t really know. And I’m not confident at all that I’ll ever know.

The Illusion Of Choice

One of the weirder aspects about getting older – and to be clear, I’m not that old – is stepping back and reflecting on how my political views have changed. It’s fair to say that I was indifferent to politics for a long time and as a byproduct of working in technology, tended to typically side with innovation over incumbents. I believed (and still do, really) in technology as the biggest agent for change.

Which is all a prelude to say that I find it very odd that recently I’ve been feeling myself swinging the other way. The first is about AirBnB, which I’ll have to post about it some other time, and the second is about Uber, which I’ve been pretty notably bearish on for awhile.

But now this whole mess with United Airlines and the involuntary removal of the passenger turned my focus a bit to airlines, and while it’s not surprising I find myself condemning what United did and their tone-deaf response, I’m finding it very difficult to separate their actions from the economic realities of the industry, which is turn causing me to almost give them a pass. Ugh. It’s a horrible feeling.

Look at it this way: airlines are, in my opinion, the biggest industry of colluding agents in the world. When you consider how many cities are basically locked up by certain airlines (Delta/ATL, America/DFW) and how the merge-down of the industry has basically eliminated any competition, marketplace economics simply don’t have any impact. What little competition that does exist on the routes is tempered by collusion; after all, why would the airplanes fight against each other when they control the frequency and thus can guarantee nearly full planes at mutually agreed and non-competitive prices? The cost of the airlines actually competing each other is too expensive, and the gains to be had are too little to justify the cost of the expenditure. It is profit-optimal for them to simply do nothing and collude; competing is literally the only conceivable way any of them could go bankrupt.

Extending this argument out further, you can basically point to the de-regulation of the industry in the 1970s as the root cause of this. I think generally you’d be hard-pressed to say that the experience of flying is notably better since then – certainly not to the degree that nearly 40 years of innovation should conceivably bear – and now you’re left with this oligarchic setup where prices are arbitrarily high and airlines like United recognize that they can act terribly because there really isn’t a ton of consumer choice.

And I get it, believe me – I can already hear the libertarian free-market arguments here that there are other options to flying, the market will vote with their wallets, and that generally speaking corporations owe no loyalty to anyone other than their shareholders and employees. Taking that argument implies such a simplistic, short-term view of the situation, that policy remains static over time and that there are no potential future repercussions for corporate irresponsbility now. United only acts the way they do because there are no short-term impacts, a function of the stacked industry they lobbied to create. Apologize? Why? It’s a blip on their radar, and apologizing only makes them a target for lawsuits. Not to mention the fact that the barrier to entry in the airline industry is absurdly high; it takes billions of dollars and landing slots that don’t exist!

(Of course, explaining this behavior is different than excusing it; it’s reprehensible but wholly understandable and predictable given the environment they’re operating in. That’s why its such a horrible feeling, because you just know that what they’re doing is completely expected, and that they’re crunched the numbers and concluded that acting terribly is more economically correct than acting responsibly. As an aside, this is also the reason why your ISP, mobile provider, health insurance, and a host of other large, faceless corporations are universally hated.)

To stop this, consumers either need to vastly expand their price elasticity – which I’m doubtful of, considering that Spirit exists and is thriving – or the government needs to intervene to establish more sensible regulation. Which is, to package up my entire post into a shiny bow, the exact same thing that I think the government should do in regards to both AirBnB and Uber, and also the exact same thing I would have been miles and miles away from considering as a solution even a few years ago. Isn’t it amazing what a few gray hairs will do?

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.


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.


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.


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.