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Folks who have followed me for a while know that I have a proclivity to change things up and move forward (just like the tech sector, which I’ve covered for the past 30 years). I’m always on to the next thing that interests me. I’m now going to channel my tech self in the medium du jour: a newsletter.

Newsletters have taken off over the past year or so, as many journalists departed the safer harbors of more traditional news outlets to try their hand at this format. It’s an exciting development, but also sometimes leaves us thinking: Good God, not another one.

Everyone loves newsletters because they offer writers a fresh, intimate way to connect with readers. The goal is to ride the wave of this other clear trend sweeping media: fandom.

The fan economy is increasingly important, as players from a range of sectors — sports, Hollywood and, yes, journalism — try to remove every middleman possible and connect directly with their audiences. The boom in tech tools, from Twitter to Instagram to TikTok, has empowered creators to do this, and newsletters are a natural evolution of these creator-fan relationships, freeing the voice and personality of the writer (in my case) from the strictures of old media.

At least that’s the trope, since a newsletter is not exactly a new idea, despite a breathless series of articles about the unbundling of content and the dire implications for the news media.

Deconstruct newspapers! Pull apart magazines! The writer gets all the dough! To channel Herman Mankiewicz to Ben Hecht in 1925 about Tinseltown: “Millions are to be grabbed out here, and your only competition is idiots. Don’t let this get around.”

But like many such declarations about innovation, the truth is that some people will be good at it, and some will not. My goal, you might guess, is to be one of the former.

I have, in fact, been doing more or less this since 2007, when I founded, with the tech reviewer Walt Mossberg, All Things Digital, a skunk works blog inside The Wall Street Journal. We aimed to deliver analysis, scoops and a whole lot of voice to readers who wanted more than the anodyne omniscience that prevailed at the time.

So in a way, I am traveling back to the past to create something for the future. Which is an apt metaphor for tech: to reinvent and reinvent again. I hope to provide you with insight, news and perhaps even a few laughs.

Worms in the Apple

Within the next week, a U.S. District Court judge, Yvonne Gonzalez Rogers, is expected to rule on a case between Apple and Epic Games. For those unfamiliar with the story: Apple is asserting that its complete control of its App Store is critical for safety and quality, while Epic, the maker of Fortnite — as well as many other third-party app developers — wants more freedom from the tech giant’s hegemony, specifically when it comes to payments and customer contact.

Whatever the short-term result — and the over-under from legal sources I have talked with is that Apple is expected to garner a modified win, despite the somewhat testy exchange between Rogers and Apple’s chief executive, Tim Cook — it’s going to be appealed by whoever loses, and the case will move up the legal stack, perhaps even to the Supremes.

What’s clear is that Apple is making an unusual number of missteps (for it) as we move into tech’s postpandemic era. And while Apple has benefited from the pandemic (like other major tech companies), with its share price and revenue up, there many thorny challenges on the horizon for the company.

Apple faces regulatory tests all over the world, and it appears inevitable that the company (along with Google, which operates the Google Play store) will be forced to change its lucrative model of collecting 15 to 30 percent of app sales on its platform. South Korea, for example, is moving aggressively to force Apple and Google to allow app developers to choose their own payment systems. (As The Times recently reported, the Biden administration is not exactly bending over backward to help Apple’s lobbying efforts there.)

Apple came to a $100 million settlement in a class-action suit with developers that assuages some of the developers’ gripes. (Developers now get to have contact with customers, for example.) But most people I have spoken with think the settlement is weak sauce and definitely not enough to ease concerns over fairness in the App Store. Apple’s reputation is suffering a bit as a result.

That golden glow — and, let’s be clear, the company remains a consumer favorite — has always been part of its appeal, and it has largely avoided the evil empire image that has plagued Facebook and others. Apple will never sink that low, but the App Store issue (and others) is not a good look.

The company also faces questions about its recent rollout of safety measures to protect children and stamp out the pernicious and repulsive use of tech to perpetrate child sexual abuse material, called C.S.A.M. Apple’s method involves monitoring users’ personal devices, rather than information in the cloud, which has raised privacy concerns, a surprise from a company that has staked its rep on protecting consumer privacy.

Two prominent computer scientists outlined their worries, especially misuse by governments, in a recent op-ed in The Washington Post:

A foreign government could, for example, compel a service to out people sharing disfavored political speech. That’s no hypothetical: WeChat, the popular Chinese messaging app, already uses content matching to identify dissident material. India enacted rules this year that could require pre-screening content critical of government policy. Russia recently fined Google, Facebook and Twitter for not removing pro-democracy protest materials.

I did a “Sway” podcast last week with Thorn’s co-founder Ashton Kutcher and chief executive, Julie Cordua, about this and related issues. The nonprofit is focused on eradicating child sexual exploitation using tech.

As we noted in the opening of the episode, Apple’s “software reduces images to a kind of digital fingerprint called a hash and only flags things to review if there are numerous concerning images. Nonetheless, Apple’s move has sparked a debate between ending child exploitation, which I think we can all agree is worth doing, and protecting privacy, which is the trade-off here.”

Kutcher and Cordua defended Apple’s plans as important to stop the endless flow of this illegal and toxic content. “Is this the gold standard solution?” Kutcher said. “I don’t know. What I do know is that I’ve never been involved with a tech company that its first product was its final product.”

It’s a fair point, but even Apple knows it has a problem. It’s no surprise that the company has delayed the rollout from later this year to an unspecified time. In a statement the company said, “Based on feedback from customers, advocacy groups, researchers and others, we have decided to take additional time over the coming months to collect input and make improvements before releasing these critically important child safety features.”

A breather here is the right move, but it’s an unforced error from a company that seldom makes them, especially when it comes to communicating.

And that’s not all. Problems between the United States and China are sure to get worse, which will affect Apple, given its exposure there. And oh, yeah, employee unrest, which Apple had long managed to keep a lid on. Blabby workers are nothing new to tech, but blabby Apple ones? A new twist, for sure.

Which is to say, while most of the anger toward Silicon Valley is typically aimed at Facebook’s Mark Zuckerberg — deservedly so — it might be the perceived white hats of Apple whose future looks a little grayer. As it probably should be.

Still, the Apple jam goes on. The company announced a new product event for next week. More on that to come.

4 Questions

I talked to Jon Kelly, a founder of Puck News, which describes itself as “a new media company covering power, money and ego.” That is just my cup of kombucha.

1. Another newsletter company? Are you kidding me? Give me the pitch on why you’ll be different.

Kara, so glad you asked. Puck is not a newsletter company. We’re actually an omni-channel media brand built on the shoulders of elite journalists who cover the nexus of the power corridors of our culture — the intersection of Hollywood, Wall Street, Silicon Valley, Washington and the media.

To answer your question slightly more cogently and eloquently, however, we believe that journalists are the ultimate creators, and what makes our company different is that we want to arm them with every type of modern storytelling platform possible. And in 2021, that means allowing them to communicate beyond the page, so to speak, and to break down the fourth wall between themselves and their audiences.

2. How did you pick your writers, and what was the most attractive aspect of the platform to them? Did you give them equity?

I wanted to hire the best journalists, people’s whose work I admired and whose articles I salivated about reading when I saw them fresh off the presses on Twitter. And in certain cases, like Matt Belloni and Baratunde Thurston, who had spent years editing The Hollywood Reporter and working as a podcaster and public speaker, respectively, I had a deep suspicion their own singular voices would be both iconic and remarkably insightful. I also wanted to work with people like Julia Ioffe and Tina Nguyen, who wanted to make I.P. for new platforms. That was valuable to us creatively and financially.

What persuaded them to join us? I suppose you’d have to ask them, but I would surmise the answer is twofold. We raised our series A capital and began recruiting during Covid, a time when I think many of us wanted to break out of the collective ennui and try something new. We offered that option. It also helped that many elite journalists, encouraged by the fuel of the creator economy, were becoming more aware that they could start something from scratch and that their audiences would follow them. Furthermore, I believe that we offered top-notch journalists a happy medium: a lot of creative freedom but also a lot of editorial chops and business discipline that they wanted at this stage of their careers.

Second, I believe that our founding team — myself, Joe Purzycki, Max Tcheyan and Liz Gough — approached the writers with an innovative business model that included equity and bonus compensation based on the number of subscribers they could drive. I very much believe that business-model innovation really does lead to creative innovation. I think the upside has been enormously motivating.

3. You’ve worked at a lot of places, starting as an assistant at Vanity Fair. What did you learn there that stays with you?

I’m very proud of how I started my career. I was hired as an assistant to two different assistants at Vanity Fair, smack dab in the heyday of the magazine business. And then I worked for years under Graydon Carter, its legendary editor in chief. This was back before the iPhone and in the early days of Facebook, when 22-year-olds had to behave and dress like mini adults. I ironed the same pair of khakis every morning for years.

The discipline of the job was significant. I may have made editorial assistant money, but I worked long hours. Nowadays, they call these jobs chief of staff or other more highfalutin titles, but the reality was that I was the kid who did everything, and all the time — I slept with my phone, fielded calls from writers and staff members around the clock and made sure Graydon had everything he needed at his fingertips to run the joint. That level of accountability grew me up fast.

Here’s the biggest takeaway, and I think it’s the key to being successful in every creative enterprise: mastering the simultaneous ability to keep your eye on the big-picture vision while ensuring that you are responsive to everyone on the team, even when they disagree. Graydon was a masterful communicator. He knew when to change his mind, was usually the first to realize if he was wrong and was open to being overruled at times. But he also never lost sight of the culture product that he was making. He had the courage to go with his gut when it mattered. Back then, that was the winning algorithm.

4. Who is the best newsletter writer not on your platform?

There’s so much talent out there, and I love the masters of the art like Mike Allen. I also love the narrative newsletter talents like your homie Casey Newton. But right before Covid, I got addicted to this business news newsletter called Snacks, which has since been bought by Robinhood. It’s a little shlocky, maybe a lot shlocky, but it breaks down three major investing and markets stories in totally unique and digestible ways. And the authors, both former Wall Street analysts, actually understand business. They’re not just aggregating Barron’s or the Journal. First thing I read every morning.

If You Missed It, Don’t

This Jessica Bennett story on Monica Lewinsky is terrific. I will be having Lewinsky on my “Sway” podcast soon to talk about the new show she is a producer on, “Impeachment: American Crime Story,” but this is a really good profile of her, and the photos are striking. Key quote: “Spend more than a few minutes with Lewinsky and you quickly realize she is far smarter, and funnier — often at her own expense — than she often got credit for.”

And … Scene

What happens in Vegas stays in Vegas. Really: It stays.

Tech continues leading the way with vaccine passport rules, despite a slap-back on them by pols. According to the Consumer Electronics Association, its annual huge show in Nevada in January “will require all in-person attendees to provide proof of Covid-19 vaccination.” C.E.S. 2022, it added, “will follow state and local guidelines and recommendations by the C.D.C. for masking and other protocols. Masks are currently required in all public indoor spaces in Las Vegas.”

I’m still not heading out to Vegas for the annual slog — after 15 years of the morass of noise and crowds and pointless product demos — but I applaud C.E.A. for its Covid policies.


When you invent the ship, you also invent the shipwreck; when you invent the plane, you also invent the plane crash; and when you invent electricity, you invent electrocution … Every technology carries its own negativity, which is invented at the same time as technical progress.

Paul Virilio

Lastly …

I’m hosting a virtual event on Tues., Sept. 14, for Times subscribers. I’m planning to chat with The Times reporter Maggie Haberman and Representative Cori Bush of Missouri. You can sign up here.

Have feedback? Send a note to [email protected]

Kara Swisher writes a newsletter for Opinion and is the host of “Sway,” an Opinion podcast. She has reported on technology and technology companies since the early days of the internet.

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