It Might Work

New York City, as you are very aware, is a challenging place. It's dirty, loud, crowded, expensive, and sometimes the MTA (the Metropolitan Transportation Authority) sucks. New Yorkers are therefore a frequently annoyed people, on the whole. This is off-putting to many. Not to me. Sometimes I think the truest frequency of the city is the harmonious humming energy when you and everyone around you are simultaneously annoyed at the exact same thing. In the moments when that particular vibration hits just right, I can't tell you how happy it makes me. It's one of the things that makes the city feel like home.

Before you pooh-pooh this, let me ask you a question: How does it feel when someone randomly shares an annoyance that also drives you crazy, but is a thing you rarely or maybe never share with anyone else because you worry it's just you? It feels pretty good, right? Ok, sure, no one likes a complainer, we should focus on the positive, we should connect over shared interests, blah blah blah. I too love learning that a stranger loves a band I haven't thought about in years, or that a friend also harbors a tennis obsession and wishes they had someone else to text during matches. But there is still so much room in my heart for petty hatreds and shared aggravations.

Speaking of tennis and shared aggravations (you knew this was coming), here's something fun: On Saturday night, in the middle of an exciting third round match between Tommy Paul and Alexander Bublik, ESPN absolutely shit the bed and stopped working. I don't know if "shit the bed" is the technical term for what happened, but I'm not sure how else to neatly sum up what happened, which was this: It was the middle of the third set. TP (yes) had won a set and Bublik had won a set (for non-tennis watchers: during a grand slam, the men play best-of-five matches, so a player has to win three sets). Neither player had broken the other's serve, as both sets had been won in tiebreaks. Suddenly, in this crucial third set, TP (I know) finally had an opening, a chance to break Bublik's serve. And then the image on my television sort of just... melted? Turned into a series of impressionist oil paintings? Became a lost LSD sequence from Pink Floyd's The Wall? I was too dumb to pull out my phone and take a photo, so here are some visuals I borrowed (stole) from Reddit users (thanks guys).

Then, after our journey through psychedelic AI art, the stream never recovered. Instead, this screen stayed up for basically the remainder of the match. Some ESPN/ESPN+ viewers managed to find functional alternate feeds, like the Spanish feed or a court-specific feed, but for many of us, that was it. We were mad. We had to, like, go to bed, or get stuff done. That's not what I pay $12.99 for!

After that, ESPN and ESPN+ mostly worked, except for some garbage scheduling today, as well as another fun moment on Monday when I was watching the Félix Auger-Aliassime v Andrey Rublev match. FAA was rushing the net to hit a volley and possibly win the set! It was so exciting! Then suddenly my feed cut out and there was a big black screen from ESPN that said NO INTERNET CONNECTION (which was not true, as I was using it on another device). When the stream came back, I missed whatever had happened with both the point and then the set. The screen said COMMERCIAL BREAK. This is also not what I pay $12.99 for.

Do you remember the early 2000s, when we were all a lot more innocent and trusting? So much was happening then. Consumers had embraced the big, colorful iMacs and iBooks! Then came the iPod! Then the iPhone! Social media unfortunately arrived. Netflix pivoted from DVDs to streaming, while other streaming services like Hulu launched! We were all gonna cancel cable and finally be free! The future looked bright! Everything just worked!

I've been thinking lately about this famous Steve Jobs-ism. "It just works." Because does it?

Let me get this out of the way first: I was never a Steve Jobs or Apple fangirl. We are not about to embark on some sort of weird hero worship. My take on Jobs, especially after many years working in tech companies, is that he was undoubtedly brilliant in some ways but also undoubtedly a huge asshole. Don't get me wrong, I like Apple products. I've liked and used them since the early '80s, when I wrote little BASIC programs about The Ramones on an Apple IIe. I also used PCs for many years (how else would I have played in Quake tournaments in the '90s?). My real move over to Apple products probably started in that pre-2010 time period with Mac laptops, and then whenever I finally gave up my beloved Samsung flip phone and got my first iPhone, around 2011ish. Apple products are good! Or they can be. They used to be? The AirTag is great.

My general knowledge of Jobs and Apple is such that I don't even know exactly when he started saying "It just works." A quick search tells me it was probably in the '80s or '90s, after he got kicked out of Apple and started NeXT. Even so, in my mind, and maybe in yours too, it's most associated with Apple products, particularly in the post-'90s era, from 2000 to just before Jobs died. I bring it up because lately it feels like abso-fucking-lutely nothing works, to paraphrase another late '90s/early '00s asshole. But what actually changed?

While I was cruising around the internet doing random Steve Jobs-related searches – what can I say? I'm a trained researcher with a PhD and everything – I came across a link to this video on Facebook. What I'm about to say next will be shocking, so get ready: In the comments, there was a calm and insightful debate about what actually happens in this video. I know! Miracles happen every day.

Here it is, from the 1997 WWDC. I know it's a few minutes long, but if you will indulge me, give it a watch before you read on.

Now, contrary to the title on this video, Steve Jobs is not "perfectly responding to an insult" or "shutting down a heckler." Thanks to my crack research (reading some YouTube comments and a bit of a Reddit thread), I've learned there's more going on here than that – apparently the guy who asks the very blunt and very spicy questions was an engineer who had worked at Apple and, rather than insulting Jobs, was responding to the insulting way Jobs had talked about the OpenDoc engineers earlier in the talk. This is the WWDC at which Jobs announced Apple was killing OpenDoc in favor of Java, and apparently he put the failures of OpenDoc on the engineers, essentially saying they'd done nothing for seven years.

Jobs' answer is fascinating to me, particularly given this context. On first blush, it's the kind of answer I should obviously love: Don't start with the technology, start with the customer experience. Customer's don't care so much about what's in the thing, they just want the thing to work. Isn't this what I keep saying?

But what's interesting is the sleight of hand, and the levels to what Jobs says. How much do customers care about how the thing works or what's inside? Not just the Apple products, but Apple itself? He's combining truths, some good and some distasteful, like baking icky vegetables into a cookie for a child: Put the customer first. Think about what the customer actually needs and wants. Make something that just works, that delights, that customers don't have to worry about, that is so good they don't question what's inside – inside the product or inside the company.

This is, as the kids say, is diabolical. In some ways, I think this is the true genius of Steve Jobs: When it just works, who the fuck cares how it comes to be?

I think this is what every tech company, every streaming service, every CEO has aspired to. They try to wield the same absolute control that Jobs had over Apple when he returned and resurrected it. They try to emulate his magical design, and his ethos of "it just works." But nothing fucking works anymore. Because as sociopathic and mercenary as all of them are, none of them hold a candle to him. None of them are truly willing to do the work of making the customer so happy and loyal that nearly 30 years later, Steve Jobs dick riders will still excuse him disparaging engineers that he likely drove into the ground in order to convince everyone else that his likely failure as a leader and subsequent decision was worth whatever human suffering was the cost of doing business. Because who cares? As long as it still works well enough to get people to fork over the money?

Every single day, there is something about the technology I use that doesn't work. ESPN shits the bed. My iPhone overheats. My laptop locks me out. I can't for the life of me figure out how to sync my Mac calendar with my Google calendar. I skim countless forums and Q&A sites to find answers, only to find more people desperately wishing something would just fucking work. And now we've got companies trying to convince us AI is great and the wave of the future, all while the existing technology we use barely functions.

My goal this week was to try and dig into some of the actual details of how all this happens, at companies with similarly megalomaniacal leaders who, smart as they are, lack the absolute sociopathy that allowed Jobs to get up and respond to an engineer with a grievance by making himself look like the hero who did the right thing. I want more than anything to build products that really are customer first, engineering second. But as much as I want things to just work – that's what I pay $12.99 for! – I don't want these walled gardens that allow companies to hide whatever they want inside. I'll keep noodling on this next week.

Until next Wednesday.

Lx