June 2018: Apple's WWDC, A birthday & A New RoughlyDrafted

June 2018: Apple's WWDC, A birthday & A New RoughlyDrafted

June 2018 was a spectacular month for me. First off, it was (as usual) Apple’s WWDC. If you have a minute, I’d like to tell you some stories about it. The kind I can’t publish on AppleInsider.

WWDC is like a week-long Apple Event

Apple’s Worldwide Developer Conference is a week long series of labs and sessions that dive into the details of everything the company is doing. For a tech nerd, it’s both exciting and overwhelming, like getting thrown in the pool as your first swimming lesson, but on an annual basis.

It’s more than just a week of new information. There’s always major new software releases that are timed to give third party developers several months to work with them in beta before Apple is officially ready to deploy them to the masses, typically in the fall. There are also technological works in progress that indicate the strategic direction of where Apple’s headed (sometimes these are only apparent in hindsight). 

Sometimes (like last year) there is even new hardware introduced. This is almost too much. Trying to focus on a new macOS, iOS, watchOS and tvOS is a lot to think about even before Apple launched its iMac Pro, new MacBooks and the HomePod on top. Thankfully, this year WWDC was laser focused on new software.

WWDC 2018 was all about the software platforms.

WWDC 2018 was all about the software platforms.

Fiktionsbescheinigung und Komplikationen

WWDC happens to be scheduled typically in the first week of June, which makes it feel like my personal birthday present, because I was born June 10th. And in fact, I’m generally so focused on making plans for WWDC that I sort of forget to plan anything for my birthday.

And this year, there were further complications because I had rather spontaneously moved myself to Berlin, and was working through some visa issues.

In May, I had already blown through my 90 day Schengen Visa, which is what Americans get when they arrive as a tourist in the E.U. After 90 days, you have to leave the Schengen Zone for 90 days before you can return again (you can’t just step outside and come back).

But because I had applied for a freelance visa in Berlin, I was granted a Fiktionsbescheinigung, literally "fake documents" that allow you to legally stay in Germany (a "fiction" of legal residency) while your visa application continues. However, I was told I couldn’t travel with this.

So there was a bit of a panic because Apple had invited me to WWDC and I had paid for my plane ticket and a hotel, and now I was concerned that if I left Germany I couldn’t return without canceling my visa application. And I was told visas could take 6-8 months to finalize. 

This went back and forth for a bit in the typical nature of German bureaucracy, where everyone seems really strict about following rules but nobody really seems to know exactly what the rules are (and there seems to be many contradictions between the various stories about said rules), but in the end there always seems to be huge exceptions and the rules don’t really seem to matter at all in practice, as long as you pretend they do.

In my case, I was told that my Fiktionsbescheinigung was probably okay to travel to the US and return, and in the end I was actually granted a visa in record time (I believe the very helpful people at "Berlin Partner for Business and Technology" ( helped to make this happen, as part of their efforts to foster economic development and investment in Berlin).

But no matter, upon my return via a layover in Dublin, Ireland, my passport was stamped with another 90 day tourist stamp even though I didn’t technically need one and had a valid visa. It feels like all these fictional lines on a map are super critically important and also a total bullshit charade at the same time. 

Saw a bit of Ireland for my first time ever, a bit late given that my grandfather was born there. 

Saw a bit of Ireland for my first time ever, a bit late given that my grandfather was born there. 

It’s not lost upon me that if I were migrating in the opposite direction, into what is my own native country, that in today’s climate of populist, unthinking nationalism I could face unconscionable human rights abuses, including having my children stolen away from me to satisfy the perversions of Stephen Miller, a morally bankrupt bag of shit installed in the ear of the President of the United States, who diminishes the nation by shouting racist rhetoric into national policy that the Administration follows because it excites the deplorable base.

Smart Republicans I know who are farmers, manufacturers and innovators are all fully aware that migrant labor and immigration are essential to the economy of the United States, and that racist attacks on immigration is just what weak and awful people use to get uneducated people wound up and afraid.

How is it that despite having total control of all branches of government, Republicans in office can’t innovate or produce any viable solutions to the very real problems involved with immigration, and instead can only turn existing issues into a wildly expensive, inhumane shitshow of jaw dropping incompetence? 

I’ll cope with the frustrations of dealing with moderately left-leaning bureaucrats any day compared to the outrageous, hateful evil of extremists on the far right. My family in part escaped Germany when fascist right wing nationalists began to take hold and turn Berlin—which had been the world’s bastion of liberal freedom—into a sloppy, destructive and purely wicked political experiment led by the worst people in the nation. How the fuck are we allowing this to happen again? 

Secrets and Spoilers

Just as all of my visa issues cleared up, I was contacted by Apple with a similar sort of panic-inducing notification that reduced the certainty about whether I would be invited to the entire WWDC event to a mere 95 percent.

I’ve attended WWDC many times in the past at my own expense across several years, running up to the point where tickets started to get hard to acquire as Steve Jobs turned Apple from a curiosity into a multiple industry game changer.

There was a time where the only way to get into WWDC was to create a sort of Fiktionsbescheinigung of your own, where one might photoshop a pass that looked legitimate enough to waltz past the security staff trying to eyeball crowds of badged developers marching into Moscone Center in huge waves. But that was before the modern era of NFC card readers verifying your work.

For as long as I can remember, Apple has rather non-selectively invited members of the global media to its WWDC Keynote, but then strictly chased them out afterward, erected its security barriers, and then insisted to all of the developers attending the rest of the week’s sessions that they were forbidden from blogging or even talking online with each other about any of the stuff Apple was working on. A severe loose lips sink ships sort of secrecy.

I tried to respect this policy even in years where I flew in under the radar and managed to see everything without signing any Non-Disclosure Agreement. I didn’t sneak into WWDC as a spy trying to steal secrets or spoil surprises. While I get the interest in covert pictures of new iPhone case designs and other rumors, I don’t really understand the focus of the clickbait tech media on delivering product spoilers as malicious, punitive strikes.

When an artist works on a new album, or a hotly anticipated new film is in production, why would anyone seek to destroy the value of that work by stealing and broadly distributing spoilers that erased surprises and deflated the excitement at their release? That’s the same way I feel about product events. When I watch a Keynote or an Apple Event launch, I love the craft involved in dramatic reveals and finding out what’s new in real-time. I don't want that spoiled, and I don't want to spoil that joy for everyone else.

What purpose is served when a rumor leaks some new announcement a few days (or hours) in advance, or when software under NDA is taken apart by a developer solely to spoil any surprise at its introduction? On the other hand, I love informed speculation looking at where companies are going. Can’t we have both the excitement and discussion without pure spoilers trying to ruin the experience of the reveal? 

The Background Invitation

Over the last several years, Apple has both clamped down on security and cautiously opened itself up to the kind of people who seem to share my thoughts on secrets and the aversion to pure spoilers. Starting in 2014, the company began inviting a few people to attend WWDC to better understand what the company and its developers were doing. I felt super privileged to be included in this trial run.

Over the years since, I’ve profiled student developers and sat through labs and sessions and participated in events as WWDC migrated from San Francisco to San Jose. And this year, with just days to spare, I was again set up to observe the week’s events.

It was a little sad to see that some of Apple’s news had been marginalized by spoilers. But there were also so many massive new developments that were either wholly unanticipated or much greater than expected. 

Apple delivered a lot to think about, from ARKit 2 (holy shit is Apple moving fast here—it’s like it’s a core strategic effort that it’s banking on heavily or something) to Siri Shortcuts (which I don’t think I "spoiled" when I speculated that of course that’s what Apple would be doing with Workflow: turning it in to a way to create automations that can not only be triggered with a tap, but also invoked by voice with Siri, creating a predictable, extendable way to address the problem inherent in promising that a computer in the cloud can understand and provide a useful response to whatever disjointed gibberish run-on you can come up with). 

Apple is moving fast in Augmented Realty.

Apple is moving fast in Augmented Realty.

At the same time, WWDC also revealed a lot about what drives Apple's work. Sure, the profit motive of earning tens of billions of dollars globally is very real, but at the same time, Apple is doing lots of things that have little or no short term profit associated with them.

Apple makes virtually nothing from Apple Music (it keeps getting pitted against Spotify, which has never earned money streaming music, as if Apple desperately wants all those non-dollars in streaming others’ content) or Podcasts or News; from ResearchKit or CareKit; or from HomeKit Automation. 

Efforts in Privacy, Security and Accessibility are not direct profit drivers. Most of these things are simply what you do when you have the luxury of time and money, and you want to make the world better in the ways that you see fit and feel attainable. 

Note that while some other companies have recently worked to copy or catch up in some of these areas (out of pure "oh shit, look what Apple is doing we better do it too"), other companies that are also working hard to be profitable simply can’t manage to pull off music streaming, podcasting, news, health and home automation while also not obliterating privacy and security and without trampling all over accessibility.

Google News isn't there to inform you. It's there to find out what subjects you might be vulnerable to in advertising. The reason why Google killed Reader is because RSS as a technology doesn't support surveillance ad tracking. 

It’s as if it's a big secret that in reality, the ad business sucks and everyone who works in it knows it sucks and understands that they are part of a sucky industry, and that they aren’t really making the world better. They’re just amplifying the worst voices of people who offer money to be heard and placed prominently in your face when you're most susceptible.

As somebody who lived through the 90s, I feel like the technology world’s equivalent to the people who escaped repressive fascism or communism and are now super hell bent on making sure everyone remembers how bad it was and appreciates things being different now. 

My appreciation of how things are trending right now in a world largely charted by Apple is reflected in my preview of macOS Mojave, which a couple people on Reddit accurately described as having a few bits of gushing about how things are looking up in the world of technology, thanks to Apple’s combination of competency and, well, class. I wrote it that way on purpose, because it's true.

And I got older

The other side of the WWDC-is-my-birthday-present coin is that I officially incremented my age number in June. With all the visa shenanigans and travel issues (suffice it to say that my initial flight to San Francisco was canceled, my bag ended up lost in transit on the way the San Jose, and the fire alarm in my hotel room went off at 2AM, so on day one I had nothing and felt like I'd been hit by a truck), I finished the conference and headed up to San Francisco to see old friends and find out what would happen on my birthday. 

By Thursday my brain was already a bit melted.

By Thursday my brain was already a bit melted.

It was a big one. I turned thirty-fifteen, which is deep into severe mid-life crisis territory. I had planned no party, not even slightly. Fortunately, however, I know some really great people after living in the City since Apple bought NeXT.

Huntly Gordon (who took delivery of my lost bag and schlepped it all the way down to San Jose just for me, thank you very much) took me out and reminded me what it was like to party in San Francisco. I got to see Elliott C Nathan’s art show where Danny Snodgrass was spinning records. Keith Kraft and Jared Grestoni plugged me into the latest Bay Area zeitgeist: the electric scooter world, just before the City leaned in to regulate the things more harshly than heroin needles. 

Anthony Brichetto, who had visited me in Berlin on his own birthday trip, turned around and led me on a trip in the Haight Ashbury and then to an urban burner experience at City Hearts. Calvin Klein made me stare at the moon from my old panoramic vista in the Berkeley Hills and contemplate what kind of person I wanted to be; Douglass Chan took me out to an emperor’s feast; Raymond Houston Bridges discovered a vintage cosplay costume for me to wear to a thematic party I hadn't packed for; and Cegan Dodge gave me a really comfortable place to crash. I even met a new friend and we burned a camp flame at Black Sands, the best beach in SF for a number of reasons.

There were parties with tech people and parties with cool people. San Francisco was as beautiful as I'd left it, and the sun was shining in June.

I found some wild new apps

And then things got crazy. I discovered a new way to fly: you just order a seat on a small jet last minute and walk into a tiny airport and don’t deal with TSA frisking you down and making sure you don’t have a dime or a gum wrapper in your pocket while they bombard you with radiation and then annoyingly pick through your stuff because they thought they maybe missed a 4 oz bottle of shampoo. 

It’s an app called Blackbird Air. You can, for example, jump on a small plane from Oakland to Burbank for as little as $129. It feels like business class, and from the airport waiting area to the sky they hand out free snacks, drinks and even an inflight cocktail. Best thing about it is there's no SFO or LAX involved.

My Blackbird ride and its cockpit

My Blackbird ride and its cockpit

You can also charter an entire plane for about $10 per mile. And after you pay for the flight, you can offer to sell the seats on the plane you charter and maybe even end up not paying anything. There’s also a new option where you can hitch a ride with a private pilot who is already going in your direction, and you pay "as little as $50" to tag along. I haven't tried that yet.

Just like Lyft, you can use my referral code 3W398 and save $300 off your first three Blackbird flights (when you sign up with it, I get the same deal). I highly recommend trying it out. It was a baller experience at plebe expense. 

There’s also a last minute "jet sharing" service called JetSmarter, which similarly seeks to set up new markets for empty seats on small planes that would otherwise go empty. It’s more subscription based, where you can buy in and get a substantial discount (or since recently, choose to fly as a non-member and just pay extra). It lists various city pairs for flights in Europe, the Middle East, and US. 

You can get a seat on a private or semi-private heavy jet (like a G6) with a flight attendant, amenities and WiFi, or jump on smaller mid-size or light jet, turboprop, even catch a helicopter when in the New York area. You can also charter an entire plane with it. I haven’t used the service yet, but if you sign up as a member and try it out, use my referral code 5QRW3W and we both get a free seat somewhere worth up to $1000. 

If you want to feel fancy without leaving the ground, you can try out Turo, a car sharing app oriented toward luxury and exotic cars. There are also "deal" cars that range from utilitarian to fun. It feels like less hassle than renting from a rental agency, and more like an AirBNB transaction where you’re getting use of a nicer place for the same or less than you’d pay for a hotel. 

I rented a Maserati to explore Mulholland Drive and throttle around West Hollywood just for fun, and even with premium insurance it wasn’t very expensive. But it felt really fancy. Unlike some basic rental cars, my ride included CarPlay. Again, try out Turo with my referral code and we both get a $25 credit. 

My Turo ride and its cockpit.

My Turo ride and its cockpit.

A Spontaneous Detour

I’m a pretty basic guy who lives pretty conservatively, so when I splurge a little it feels pretty exciting. As it turns out, I was introduced to these "splurge adventure" apps by The Technorati, a musician and producer who has a likeminded interest in Apple as a company. While I was in San Francisco for WWDC, he invited me to come to Los Angeles to see Horace Dediu speak.

The Technorati had me try out a Scoot-E-Bike up the California Coast.

The Technorati had me try out a Scoot-E-Bike up the California Coast.

I’ve been following Dediu and his writing (and charts) at for a long time, and while he seemed like a familiar friend from online chats, I realized that I was not sure if I’d ever actually met him in person. I sure wanted to.

After all of my bike, snowboarding and motorcycle wrecks, I have some problems remembering things unless they are about Apple or miscellany about the computer industry from the 90s. I’m also a font of useless knowledge in other areas. But when it comes to people, I sometimes block and occasionally can’t even immediately remember my best friend’s name or what I did (and with whom) yesterday afternoon, without a few hints. I'm the forgetful historian.

Horace Dediu of Asymco knows Apple frontwards and backwards.

Horace Dediu of Asymco knows Apple frontwards and backwards.

I wasn’t sure if I could swing Los Angeles, but my new friend insisted I come, and I’m glad I did. Everyone in SF is supposed to hate LA, but I love it in manageable doses. And I have friends there: Todd Markle showed me where to eat (and rescued the jacket I left behind at the Chateau). Ronen Bay took me out to party. And there was Kris and Will and an Elijah. 

But the main event was that I got to hear Dediu speak in person, and just as interesting, I got to discuss ideas with him and a circle of other attendees who stayed after the presentation and talked about their personal backgrounds, their industry connections, and projects they were working on. It was one of the most enjoyable experiences I’ve ever had at an industry-related event. 

Apple Summit LA attendees chat outside the bungalow John Belushi did his last speedball.

Apple Summit LA attendees chat outside the bungalow John Belushi did his last speedball.

When the discussion came around to me, other attendees’ glowing comments enlightened me in an epiphany of the obvious that there are a lot of people all over the world who have read my writing, from the original RoughlyDrafted back as far as 15 years ago to the last decade of my writing at AppleInsider. I have never received so many complements in one rapid-fire session before in my life. I felt flattered into the wallpaper.

It was like being in a live action version of my comments section, without any of the embittered anonymous people who hated me for being right about Microsoft’s inability to replicate the 90s, or the limited value of Android’s marketshare, or because I don’t agree that Apple’s primary directive should be producing a mini-ITX clone with a detachable touchscreen that turns into display for a refrigerator-toaster. Just people giving me a high five and a hand shake. 


Technology can be isolating. On the Internet, you can communicate in text and graphics and videos without ever feeling the real connection of speaking to people in person, or witnessing a group dynamic.

I'm already a bit socially oblivious, so I love making friends with people who are social catalysts who drag me into unfamiliar new worlds. I have learned that—for my own social health—I have to resist my repressive inclination and actively seek out FFAA: Friends, Fun, Action, Adventure. 

That’s what originally took me to San Francisco, the FFAA capital of the United States. It's what prompted me to jump across the Atlantic to Berlin, which has always been the most FFAA place in all of my travels around the world. I am ecstatically happy to be here. 

So when The Technorati suggested that I participate in more events just like the one he invited me to in LA, I was more than a little curious. Apple has attracted one of the largest groups of individual retail investors, and thanks to the company’s incredible performance over the last several years, those investors have done quite well. Many of them would clearly enjoy converging and discussing the future of this company they know so well.

Why not host a series of events where people can listen to incredibly erudite speakers like Dediu, and then afterward digest and discuss the world of consumer technology (and micromobility, one Dediu’s favorite topics—he apparently even originated the term) with a cocktail or whatever else one uses to lubricate the brain, among a group of other people who chose to be there and support the event? 

Under the name Apple Summit, the two hosts have already scheduled a second event in Manhattan, on August 16. And for this one, they’ve invited me to tag along and contribute as sort of a Kara Swisher—a role I feel privileged to even attempt. So if you can swing taking a day off for some intellectual fireworks and social interaction with a smart group of people, I more than just recommend it. 

And if New York is too far away, there is a schedule of Apple Summit 2018 events in the planning stages for Boston, Chicago, Las Vegas, and—coordinated with Apple’s February-ish 2019 Shareholder Meeting—one in Silicon Valley. They are also plans to do an international tour as well, likely reaching London, Paris, Rome, and Hong Kong. 

The New  RoughlyDrafted

The rest of my June involved shaking off the jet lag with CrossFit and working with a brilliant designer to refashion my old website as a portfolio of past work and a place for me to write about new things that don’t even try to entangle with the web’s soul-destroying monetization model of clickbait and surveillance advertising. 

I don’t have any advertising on my site. If I ever do any "native" or affiliation-based stuff, I’ll be really upfront about it (like the apps I recommended above; I discovered them without any promotion from their developers, and the referral codes I presented are simply that, not a special promotion). I’m not really paid to say things, even though that appears to be my job. I have no input or feedback from advertising on AppleInsider, for example. 

You’ll notice that my "New" RoughlyDrafted is fast and slim on mobile devices, because it doesn’t employ ad tracking. You can choose to Like my RD page on Facebook, but there’s no Facebook trackers on my pages. The comments are Discus, which has an ad model that’s entirely separate from my site, but appears to be pretty slim. And I have common web analytics for Google and Squarespace, which I use to see where my audience is visiting from and what they find interesting to read about. I am not doing any Google advertising with it. 

You can also follow RoughlyDrafted on Apple News on iPhones and iPad or—in the new macOS Mojave—on your Mac in the freshly minted News app. I may someday try a subscription model, or print t-shirts or shot-glasses or pocket mirrors with a stylus straw with my name on them. But for now, I’m just writing stuff for you to read.

If you enjoy it you can follow me on social media or leave incisive comments and maybe someday get a beer with me, or show me around your city, or give me a spare bed to sleep on when I’m in town—all of which, incidentally and sort of incredibly, a variety of readers have managed to do over the last 15 years!

So June was really excellent and I can’t wait to see what happens this month.