Apple has a newish Switch to Safari website and a couple of YouTube videos. Something about the website especially feels off to me. I’m being picky here, but what’s the point of writing articles about Apple if you can’t be picky every once in a while?

“Safari is a more powerful and private browser than Chrome” is the tagline. I get what Apple is saying, but “more… private” sounds funny to my ear. I also don’t think “more powerful” means what Apple wants it to mean here, because the first big point Apple makes is that Safari uses less power when it comes to maintaining battery life.

I’m not sure what Apple should say instead, to be fair. “Safari is a better browser than Chrome” is blah. “Safari is a friendlier browser than Chrome” doesn’t mean anything. But “more powerful and private” is an odd phrase to me.

The next tagline on the page is “Safari succeeds where Chrome trails.” That’s another very odd sentence to me. To use a too-common insult these days, it sounds like an LLM wrote it.

The next graphic, though, works for me. “Safari sips; Chrome slurps.” When you’re on a laptop, battery-guzzling apps are a problem. I like calling out the disparity.

Apple then uses some iffy animations to promote its claims that “Safari cuts the clutter while Chrome piles it on”. (I don’t think this one’s fair. Chrome doesn’t add extra crap to websites, in my experience.)

I’m fine with Apple’s claim that “Safari shields you while Chrome reveals you,” though internal rhyme is never my favorite.

Then the next one says “Safari blazes; Chrome cruises.” I don’t think those are opposites, and the rabbit with a snail shell is a weird image to me. And even Apple’s explainer text — “Safari is up to 35% faster than Chrome when loading frequently visited sites on Mac” — feels heavily caveated.

Then comes the chart, which is fine. Though I’ll admit I first misread “Fights tracking with machine learning” as relating to tracking fights, which I’ve never needed to do. I’m not a boxing or MMA fan.

After a few more chunks of marketing copy that I think is pretty well done, there’s a list of questions. Where every other website would call this a FAQ, Apple headlines it: Questions? Answers. Okay.

The very first one is “Is Safari better than Chrome?”, which again, feels very off to me. We’re on apple.com, the whole page is promoting Safari over Chrome, and we know Apple’s stance here. It feels a little… desperate?

I’m a Safari user. I prefer it to Chrome. There’s some cute stuff on this page. But it definitely also feels odd.

After I posted X is bad, though, I got a metric ton of feedback. That’s a scientific measurement.

John Gruber, for his part, has pushed back to some on Mastodon with a fair question: If I’m judging platforms by their owners, the Ellisons aren’t much better than Musk. So should I stop watching Warner Bros. and Paramount movies? HBO? CBS? CNN?

Fair question.

First, I agree with John: The Ellisons are not the good guys. Larry is a major Trump backer. Paramount paid $16 million to settle a Trump lawsuit over a 60 Minutes edit that First Amendment lawyers considered laughable. A few days after Stephen Colbert called that settlement a “big fat bribe” on air, CBS canceled his show. And now the Warner Bros. deal is backed by sovereign wealth vehicles from Saudi Arabia, Qatar, and Abu Dhabi, which will put CBS News and CNN under the same family’s roof. If you worry about billionaires bending the news toward whoever’s in power, that’s plenty to worry about. I do.

But saying the Ellisons “aren’t much better” misses the point.

Go back to my list from my previous piece on this topic, which I look forward to talking about less starting soon. Every single receipt was something Musk personally said or did. He co-signed the Great Replacement. He made Nazi puns. He told a London crowd to fight back or die. He posted a slogan from The Turner Diaries. His words, from his account, on his platform.

The case against the Ellisons is that they’re craven. They kiss the ring to get their mergers approved. That’s bad! But it’s a different kind of bad. One is a cynical businessman protecting a deal. The other is a true believer with a megaphone. I don’t love either of them running a newsroom. But only one of them is the content.

Musk personally uses X as a vehicle for political messaging and amplifying hateful rhetoric. Watching HBO doesn’t inherently involve participating in Larry Ellison’s personal political communications.

Which brings me to what you’re actually feeding when you go back to X because it’s where the “fun” is. X’s product is attention. When you post there, you’re not the customer; you’re the inventory. Every interesting person who shows up makes the platform more valuable, and that’s the same platform Musk uses to boost the AfD and Tommy Robinson.

When I watch an HBO show, I’m paying for something made by hundreds of writers, actors, and crew, many of whom collect residuals. The Ellisons get a cut, sure. But I’m not lending my voice to make Larry’s timeline louder.

Elon actively uses X to bolster extremely aggressively right-wing propaganda. “Heated Rivalry” isn’t that.

Then there’s the bigger argument behind John’s question: You can’t avoid every bad billionaire, so why bother avoiding this one? Take that seriously and it’s an argument for never doing anything at all. Every line I draw is imperfect. I’m writing this on a Mac, made by a company whose then-CEO handed Trump a gold-plated plaque in the Oval Office. Imperfect lines are still lines.

As my friend James Thomson wrote on Mastodon, “if any of your friends say that they’ve had a shitty time in a particular bar, and you go ‘nah, it’s fine actually, I’ve had no problems there’, rather than ‘sorry, I didn’t know, let’s go somewhere else’, then you are a bad friend.”

I avoid X and encourage others to do the same because anything that helps Elon Musk amplify his hatred of minorities like trans people, Blacks, Jews, and more is bad. It hurts me, my trans kid, my family, and my friends.

John — like me — is white, male, cis, straight, and rich.

I don’t know how many of those labels apply to New York Times columnist Jamelle Bouie, but I know for sure that he’s Black. Bouie wrote on Bluesky:

I’m sure X is remarkably friendly if you aren’t the target of racial slurs and harassment campaigns.

Anyway, I wonder how many “n———” I’ll have to sift through if I start posting there again?

Enjoying HBO programming isn’t helping to spread hate speech. Musk uses X to do just that. And Musk plans to spend $100M promoting Trump acolytes in the November elections.

“The Ellisons are bad, too” is a great argument for paying attention to the Ellisons. It’s not an argument for X.

X is still bad, though.

There’s money to be made in podcasting. It’s getting harder, though — at least for some podcasters.

But while you may listen to podcasts, you might not be as familiar with the business side of podcasting. I am.

On the October 9 episode of Freakonomics Radio (episode #690), host Stephen Dubner welcomed Jenna Weiss-Berman — the executive producer of Good Hang with Amy Poehler, the CEO of Paper Kite Audio, and the cofounder of Pineapple Street Studios. He also had on Jeanine Wright, the cofounder of a company now called Liquid Studios AI (originally called Inception Point AI), which focuses on the business side of podcasting.

You’ve likely heard podcast ads, so you know that ad sales are a key part of the podcast industry. Not surprisingly, though, the largest shows get a disproportionately large amount of the ad dollars. The technology to serve the ads is limited. And scaling host-read ads is hard — there are many pain points between getting hosts to approve ads, getting product in their hands, getting them ad copy to read, getting them to record the ads properly, and then getting the ads in their episodes. Programmatic and pre-produced ads are a lot easier to scale, but a lot crappier to listen to, and thus a lot easier to ignore, and thus a lot less effective.

⤢

I sold podcast ads, and/or led teams that sold podcast ads, for about fifteen years. I started indie, then cofounded podcast ad sales company Midroll, which was eventually acquired by Scripps. (Scripps bought Stitcher a year later; Midroll renamed the whole business Stitcher, and eventually SiriusXM bought it, and later chopped it up for parts.) I left before the SiriusXM acquisition and went to ART19, a company focused on the technical side of podcasting (backend hosting infrastructure and dynamic ad insertion), which wanted to get into ad sales and originals. ART19 was the company Amazon acquired that led to my eventually working at Wondery for a year and a half.

First, some disclosures: I negotiated multiple deals with Stephen Dubner and Freakonomics when I signed him to Stitcher many years back, and he had the office next to mine. I negotiated multiple deals with Jenna Weiss-Berman when she was at Pineapple, including my favorite — a deal for the seminal podcast Missing Richard Simmons. And Jeanine Wright was eventually hired as my boss at Wondery after both Wondery and the company I was at, ART19, had been acquired by Amazon; I stayed at Amazon six months longer than I would have otherwise just because of how much I liked Jeanine. And I once ran an improv for enterprise workshop for her team, when the company she runs now was still called Inception Point AI.

So, yeah. I know many people in this story. Not Amy Poehler, though. I never met her.

The money in podcasting

Dubner also spoke to Ben Davis, his agent at WME (with whom I’ve done a slew of deals). As Ben references, an area that sets podcasting apart from, say, classic television deals, is this: On the ad-supported side, in both cases, the money comes from — surprise! — advertising. But in podcasting, from the very beginning, most deals were structured where the podcaster(s) got a cut of the ad revenue. So where a classic TV deal might be: We’ll pay you $250,000 an episode for this 22-episode season, podcasting deals usually take the form of we’ll pay you 70% of all the ad revenue this show generates. And very often, those deals get more nuanced: We’ll guarantee you the greater of this sum of money at a minimum or 70% of all the ad revenue — derisking the podcast host, and … *en*risking the company providing that minimum guarantee.

The episode covers the reality that the vast majority of podcasts make most of their money from ads. In the tech nerd podcast world, that’s still often true, but not always. Loyal fanbases often subscribe to “premium” versions of shows, which — at least for shows whose size means they can’t command as much ad revenue — can often mean memberships become the lion’s share of revenue.

So podcasters typically want as many ads as they can get in their show without alienating listeners. More ads is more money on which they can earn their revenue share. And sure, the common minimum guarantees that the biggest podcasters can command certainly help, but few creators are satisfied with just the minimum guarantee; they want to exceed it.

And it’s worth noting: The vast majority of podcasts that exist don’t get any ad sales at all. And of those that do get ads, most don’t have the power or leverage to score minimum guarantees. So the majority of money-earning podcasters are even more dependent on ads; if there are no ads in an episode, that episode isn’t directly generating revenue.

As Ben explains, most podcast ads are sold on a CPM basis, which means the advertiser spends some dollar figure per thousand downloads. (The “M” is for “mille” which means “thousand” and confuses people. Fun!) Industry standards in podcasting are around an $18 CPM for 30-second pre-rolls, and a $25 CPM for 60-second mid-rolls. So if a show can offer an advertiser 100,000 downloads, that spot might cost $2,500 (100,000 divided by 1000, multiplied by $25.) Over time, CPMs tend to trend lower — except for shows with incredibly lucrative audiences or incredibly famous hosts.

The ad technology

As someone with many years of podcast ad sales experience, it pained me when Dubner played a clip of Will Page, the former chief economist at Spotify, describing audience measurement in podcasts as “the wild west.” Podcasting, and podcast ad tech, has been described as “the wild west” for as long as there have been ads in podcasts.

“The wild west” label was the bane of my existence when I sold podcast ads full-time. Here’s why it gets thrown around:

Podcast listening essentially happens offline. Podcast hosting companies (Megaphone, ART19, etc) aren’t streaming; they’re serving up audio files for download. Your app (Apple Podcasts, Overcast, Castro) may well start playing the audio file before it’s fully downloaded, but you’re not streaming the episode: You’re downloading it.

And there’s the rub. We know you downloaded the episode. We have no idea if you listened to it.

So ad buyers get up in arms. There have been numerous revisions to the agreed-upon definition of what counts as a podcast download. It’s complicated, and you don’t want to dive deep into it. Apple caused industry-wide download reductions with iOS 17, which changed how automatic downloads worked in the Apple Podcasts app.

Translation: Apple stopped downloading new episodes when people weren’t listening to episodes, so total downloads decreased. Total listening, of course, didn’t.

Ad buyers want “real” numbers. Which is hilarious, because the numbers most ad buyers can see are all poppycock anyway; they’re just universally accepted bits of poppycock. Nielsen’s methods for measuring TV watching or radio listening are, in a word, hilarious. And even if I know for sure that your TV was on when a commercial was aired, I have no idea if you had left to use the toilet or grab a snack.

With podcast downloads as the key ad sales metric, we know one thing: You downloaded the podcast. That’s it. It’s a real number! But whether you listened to the episode at all, or skipped the ads if you did listen — that’s a black box.

There’s a more recent development on the business side of podcasting called The AMP Accords, spearheaded by Dan Granger, the CEO of Oxford Road, the largest ad agency spending money on podcast ads in the world. I’ve known Dan for as long as I’ve been in podcasting. I get this goal. I think the AMP effort is a futile one, because I can’t imagine a world where Apple or Spotify will start sharing data on ad consumption out from their apps, which The AMP Accords require as a baseline.

For now, podcast advertisers tend to rely on what they call pixels or prefixes. (Pixels is a silly name, dating back to display ads; they’re really just URLs.) A prefix is hit every time you download an episode of a podcast — it’s essentially a redirecting URL that sits in front of the actual audio file URL, so that someone, somewhere can count every download request.

“Pixels” are tracking URLs that are served up at the moment you download the byte range of a file containing the ad. That’s a mouthful. But essentially, your podcast app goes to download an episode — whether automatically, or because you pressed Play (triggering a progressive download) or just pressed Download — and the server starts sending you the file. With dynamic ad insertion, ads are stitched into the episode as you download it. And when an individual ad unit is stitched in, the “pixel” is fired, letting the ad delivery be measured by some third party.

It’s clunky.

Listeners worry that the point of such pixels is to track you, but tracking is somewhat limited. Advertisers want to use these pixels for attribution tracking (in other words, did you buy this product because you heard an ad on a podcast), but the attribution is, by necessity, fuzzy.

The server delivering the podcast download can see your IP address and your user agent, the latter of which may include the app you’re using, the OS you’re using, as self-identified by the app you’re using to download the episode. And that’s different for your podcast app than for your browser. So if your iPhone downloads a podcast using your home IP and the Spotify app, and then you check out a product you heard an ad for on your work computer — there’s no clean way for the pixel to attribute your purchase to your prior podcast download.

Also, if 20 folks on the same Wi-Fi in the same college dorm or office building all have the latest iPhone and all use Apple Podcasts and all download the same episode of SmartLess… It’s borderline impossible to measure that, or attribution from ads included in that podcast, with any accuracy. And the IAB v2 standards that the podcast ad sales industry relies upon treat those 20 people as a single download.

So everyone in the attribution space uses some measure of extrapolation and interpretation.

Like I said, it’s fuzzy.

The AI of it all

Jeanine Wright launched Inception Point AI (again, now Liquid Studios AI). When she was interviewed by Dubner for Freakonomics last May, Inception Point had 15,000 active shows, with 300,000 active episodes. The episodes were 100% AI-generated: the topics, scripts, hosts, and recordings were all AI.

The math was simple: If you could aggregate a slew of listens off content that was cheap to make with no human involvement, selling ads across those downloads (that could also be voiced by AI, or could simply be pre-produced programmatic spots) could be profitable.

I like Jeanine. I did not like this model. Neither did Jenna Weiss-Berman, who told Dubner, “I think they’re the devil, and I’m happy to say that.”

I do not hate LLMs; I’m amazed at what they can help me build, and all the projects they make possible. But I absolutely think creativity should be left to humans.

Liquid Studios AI is a pivot for Jeanine’s company. It turns written text into audio. It turns audio into video. It translates audio into other languages. It generates clips for social media sharing. These things I understand, and I think they make a lot more sense than creating AI-generated podcast content from scratch.

I know of others in the AI space who are quietly working on different ways to use synthetic voices for ads. Can we get a host-read ad in the host’s voice that doesn’t require the host’s time? Sure, in theory, if the host is willing to let you use their voice like that. I doubt the ad will sound as good or compelling as one actually voiced by said host. I know of sneakier tech that fixes mispronounced words or substitutes in new or custom per-show promo codes in the ad reader’s voice. Those are much harder to detect. That’s just the reality.

What did Freakonomics get wrong, exactly?

I stand by my distaste for that “Wild West” analogy.

I also think Dubner gets it wrong when he goes deep on the word “podcast” and how bad he thinks it is. I do appreciate the idea of just calling podcasts “shows,” but I don’t mind that there’s a word that refers specifically to a format we all immediately know without any context (which “show” doesn’t do). Yes, “podcast” is outdated since the “pod” came from “iPod.” But the iPhone’s still an iPhone even though we barely use it for phone calls. What matters is we have a term we all understand.

Also, in his section talking about those AMP Accords, Dubner says “the podcast industry is trying to mature.” I don’t think that’s exactly right. I think that podcast ad buyers are looking to get ever more hard data on who’s listening to ads. I get that. The folks spending hundreds of millions of dollars on ads want more intel. But podcast ads are mature; that’s how the industry has grown so much already. We already know the ads work from promo codes and vanity URLs alone. I understand that buyers want even more data, but I don’t think they’ll get it.

So what is the future of podcasting?

I’m sorry to disappoint you, but I don’t have any shocking prognostications to share.

Just as with blogs and video creators and everything else, there are tiers. There are enormously famous and successful podcasters — Poehler, Conan O’Brien, the SmartLess guys, Bill Simmons, etc. They’ll continue to do just fine. Advertisers can buy ads on those shows and have hugely famous people voice those ads — while talking directly to their fans.

Mid-size and smaller podcasters who at least sometimes run ads will continue to face increasing challenges. It’s easier and more scalable for an ad buyer to run fewer ads on bigger shows. Hosts who reach niche, or affluent, or otherwise desirable listeners will continue to get some ads, but if you’re not doing hundreds of thousands or more downloads per episode, getting custom ads for your show will only get harder.

That may well mean you end up running more radio-sounding programmatic ads. These ads, in turn, alienate listeners, who will increasingly train themselves to press the 30-second skip button a few times every time ads come up. That will make ads perform worse, which will make the rates for ads decrease, which may lead to some creators cramming even more ads into their shows to make up the shortfall, and everything will get worse.

Technology like Jeanine’s will help, in some ways: Every podcaster wants their show to be bigger. A bigger audience translates directly to more revenue, if you’re monetizing your listenership with ads, subscriptions, merch, or even live events. You need more fans to make more money. So if Liquid Studios can help you create more easily shareable social assets from your podcast, that may help grow your listener base. Automatic translations may help too, but if you’re looking for US ad dollars, a French localization that sounds like you but serves listeners overseas is a bit less monetizable.

In effect, I think the biggest podcasts will get bigger. I think more famous people will launch podcasts, and some of them will be successful. I think hobbyist and prosumer podcasts will increasingly rely on subscription revenue as ad revenue gets more challenging to earn.

But I think people who are passionate and have things to share will at least occasionally continue to find audiences, and find follow-on success from there.

PS: Oh yeah, video

Dubner didn’t go deep on video, so I didn’t either. They say comedians want to be rock stars and rock stars want to be comedians, and apparently now huge swaths of people in podcasting also want to be YouTube stars. Okay.

Audio podcast consumption is different from video podcast consumption, is my hot take. Audio listeners are completionists; video watchers have shorter attention spans and are more prone to multitasking. (There’s a reason YouTube changed its counting methodology.) There’s a place for video podcasts; meet your audience where they are. But television didn’t kill radio. There’s still plenty of room for audio-only success.

I admire John Gruber.

I think he’s a great writer. I think he’s smart as hell. He’s annoyingly funny, too. I am impressed and inspired by his success with both Daring Fireball and The Talk Show.

I get excited when John links to one of my apps or articles. When he linked to my story about relaunching Strategery, that led to a wave of extra exposure orders of magnitude over a typical story on this site.

With decreasing subtlety over the past few weeks, John keeps pointing out that there’s a lot of fun to be had over on X, culminating in his piece today that “X Once Again Marks The Spot.”

His point, as I see it, is that yes, Elon Musk is awful, but the X algorithm no longer shoves his posts into John’s feed, and new Apple CEO John Ternus is posting there (along with other Apple executives), and that there are interesting people who post on X and not elsewhere.

That all may be true. But it’s not the point.

It is true that X has, by some definition, “won.” Elon bought it, quickly ruined it, squandered its great Twitter branding, drove many users off the platform — but because it’s the most popular microblogging platform, it continues to succeed. And business leaders like Ternus, celebrities, and other smart and interesting people are posting there again, or they never left.

But it’s also true that Elon Musk absolutely sucks. Let’s use receipts.

1. He called an antisemitic conspiracy theory “the actual truth.” (Nov 2023) Someone on X claimed Jewish people want to replace white majorities with minorities, and Musk co-signed it. Apple and Lionsgate pulled their ads. He apologized, then told the advertisers who left to — quoting Elon here — “go fuck themselves” in the same interview. Of course, all the advertisers came back. It’s unclear to me whether they actually engaged in coitus with themselves, nor is it my business. CBS News

2. The salute, followed by the Nazi puns. (Jan 2025) He made a straight-arm gesture at an inauguration event. A few days later he posted wordplay on Goebbels, Hess, Göring, and Himmler. Even the ADL, which had defended Elon against claims he made the gesture — which, believe your eyeballs, he did — said the Holocaust isn’t a joke. Global News

3. He told Germany’s far right to get over “past guilt.” (Jan 2025) He appeared by video at an AfD rally, called the party Germany’s best hope, and said there’s too much focus on the past. The rally was in Halle, where a far-right gunman attacked a synagogue in 2019. JTA

4. He said his own trans daughter was “killed.” (July 2024) On Jordan Peterson’s show he deadnamed and misgendered Vivian over and over. He blamed the “woke mind virus” and said it’s what pushed him to the right. Rolling Stone

5. He quietly deleted X’s protections for trans users. (Apr 2023) Twitter dropped its 2018 rule against targeted misgendering and deadnaming. A weaker version came back later, but it only applies where local law requires it, and the person being targeted has to report it themselves. AP via Anchorage Daily News

6. His chatbot started calling itself MechaHitler. (July 2025) He announced he’d made Grok less “politically correct.” Within days it was praising Hitler and repeating antisemitic memes. xAI apologized and blamed a code update. TechCrunch

7. He told a London crowd “fight back or die.” (Sept 2025) He spoke by video at Tommy Robinson’s rally and told the crowd violence was coming for them either way. Police reported 26 officers injured and 25 arrests. Downing Street called his language dangerous and inflammatory. NBC News

8. He called a cave rescuer a “pedo guy.” (2018) The diver’s offense was saying Musk’s mini-sub wouldn’t work. A jury found it wasn’t legally defamation, and Musk admitted on the stand that he didn’t actually think the guy was a pedophile. CNBC

9. He boosted a conspiracy theory about the Paul Pelosi attack. (Oct 2022) Days after buying Twitter, he linked to a fringe site whose story on the hammer attack pushed an anti-LGBT conspiracy theory. It’s the same site that once reported Hillary Clinton was dead. He deleted the post later that day. CBS News

10. Everyone’s a traitor now. (July 2026) An Economist editor pushed back on him in an interview, and he called her a traitor to the West. He then declared that anyone who opposes “remigration” is a traitor too, and kept posting “first the traitors, then the invaders.” That slogan comes from The Turner Diaries. Il Foglio

11. He compared gender-care surgeons to Josef Mengele. (Feb 2026) That’s the Auschwitz doctor. Musk called the surgeons “modern day Mengeles” and predicted thousands of lawsuits. IOL

For the record, Musk says he’s not antisemitic, not a Nazi, and just protecting kids. I think his words tell a different story.

So the question becomes this: Can you disagree with Elon Musk, or consider him an anti-trans, racist Nazi, and still use X?

Sure, you can.

Full disclosure: I still own two Teslas. They’re old. One’s from 2017; one’s from 2019. We bought them, as our bumper stickers say, before we knew Elon was crazy. They have unlimited supercharging, so I feel like I’m costing Elon money every time I use them. I’m selling one of the two as soon as our new car arrives, which should be any day now. Tesla replaced the full battery on it recently under warranty, again, at their $20,000 expense, which brought me great joy — since they had to pay it and I didn’t.

I don’t visit X because I think X profits benefit Elon Musk, and I think Elon Musk is a bad person. My kids loved Harry Potter, but we don’t give any more money to trans-hater JK Rowling, either.

It’s hard to miss out on fun things. I miss what Twitter was. I wish I were still enjoying the party. But I sleep way better at night knowing I’m taking the steps I can to not make that smug, rich, hateful asshole any richer.

I want to love the new Siri in iOS 27. Apple calls it Siri AI, and it’s supposed to be smarter, more powerful, and faster. Sometimes, I’m impressed by the things it can do.

When I linked to David Pogue’s piece about all the ways he was using Siri AI, I was excited by that list. David wrote about the powerful things he got Siri to do, and about the hardest part of using the new Siri: remembering to use it after years of being underwhelmed by how Siri operates.

I am remembering to use it more. But it’s also pissing me off a lot again.

There’s one new feature of Siri that seems like a positive in theory, but in practice I find rather infuriating: When Siri isn’t quite sure it heard you properly, it seeks clarification.

⤢

Here’s one example. I needed to remember to send Donna photos of my kitchen. I asked Siri to remind me to send Donna photos on a specific day, at a specific time. Siri wasn’t sure what name I’d said, so it asked which of four names I’d been trying to say. Then I had to speak to Siri again to clarify. Then it set the reminder.

I get this kind of interaction all the time. Something about my diction doesn’t work for Siri, I guess.

The first problem is that sometimes providing the requested clarification is extremely annoying. The second problem is that it slows the whole process down.

I would much prefer that Siri set the reminder to send Donna photos—using the first name it thought I’d said, which was exactly correct—and then say: “I set a reminder to send Donna photos. If you said one of these other three names, let me know.”

Then I could move on with my day. Siri could make the most likely guess, and I could correct it if necessary.

I have another annoyance with the new Siri when I’m setting appointments, which used to work just fine under the old Siri. I have all kinds of annoying interactions when it comes to setting appointments, but here’s one from just this morning.

⤢

I was setting an appointment to go to the gym tomorrow. After I provided the event’s date and time, Siri asked me to provide both again. Then, before I could respond, it set the appointment anyway.

Except it assumed I meant I wanted to go to a human being named Jim, as opposed to the workout place. Contextually, I think that’s a bad guess.

It also appears that Apple is rolling out iOS 27 more slowly than in previous years. David Smith’s adoption data from Widgetsmith and Pedometer++ shows a slower rollout, which he suspects is deliberate, to help manage the Siri AI waiting list.

John Gruber wrote about this yesterday at Daring Fireball, and he thinks that explanation makes sense, too. In that same piece, Gruber wrote that Siri AI feels slower and sometimes gives worse answers than it did over the summer. He was careful to describe that as his personal experience, rather than a definitive finding. But it matches my experience, too.

All of this is to say: I’m trying to train myself to use Siri more. And I am more impressed by some of the powerful things it can do.

But in general, I’m just as annoyed by it as I’ve been for years when it makes common, frustrating mistakes that the other assistants and AI tools in my life don’t struggle with nearly as much.

Sindre Sorhus makes a slew of apps. His site puts the count at 63. Most are simple, which I mean as a legitimate compliment: They’re singularly focused, do what you expect, and are straightforward to use.

Sorhus is a full-time open-source developer. He quit his office job in 2014 to backpack around Southeast Asia while writing open-source code. He maintains more than 1,000 npm packages, which is the kind of number that sounds made up until you look at his GitHub. These days, much of his energy goes into Mac apps, written in Swift. His site also keeps a running tally of six million users and 10,000 answered support emails. I’m guessing he’s at least a little tired.

Most of Sorhus’s apps are free. The ones that cost money are one-time purchases, and affordable.

I’m not going to break down all 63 apps. But here are a few worth highlighting:

Mailway

Mailway ($4) fixes a tiny annoyance: You click an email address on a web page, and your Mac “helpfully” launches Apple Mail, even though you handle your email needs in a Gmail browser tab. Mailway makes itself your default email app and then routes every mailto link wherever you actually want it to go — Gmail, Fastmail, Outlook, a third-party app, whatever. You can add rules, too: Addresses at your work domain open in one place, everything else in another. The app doesn’t even stay running. It launches when you click a link, hands it off, and quits.

Menu Drop

Menu Drop (free) puts an AirDrop target in your menu bar. Drag a file, a folder, a link, or some selected text onto the icon, and the AirDrop picker appears. That’s it. It’s faster than digging through the Share menu, and it works. (It requires macOS 26.)

Simple Color Palette

Simple Color Palette (free, for Mac, iPhone, iPad, and Vision Pro) lets you create, view, and edit color palettes in an open file format Sorhus designed himself. It imports Adobe Swatch Exchange files, copies colors as hex, RGB, or OKLCH, and adds Quick Look previews for palette files. He’s explicit that it’s not a palette organizer or a palette generator; it’s a palette editor, period.

Googly Eyes

⤢

Googly Eyes (free) puts a pair of googly eyes in your menu bar. They follow your cursor around the screen. They blink when you click. There’s no point. It reminds me of similar utilities from the System 7 days. Sometimes, it’s fun to have an app whose only aim is silliness and joy. The App Store reviews are a treat, too. My favorite, in its entirety: “why are they all watching me. i did nothing wrong. it was an accident.”

Supercharge

⤢

Supercharge is in the category of Swiss Army knife Mac tools, and it does a lovely job with a few nitpicky features you just might want to enable. Every feature is opt-in, so you flip on only the stuff you care about. Option-N to create a new blank text file in the Finder, for one. You can make the red window button quit the app instead of merely closing the window, or require Shift-Command-Q to quit so a stray Command-Q doesn’t wreck your progress. You can clear every notification with a keyboard shortcut, and stop the Music app from launching every time you tap Play on your keyboard. There’s a tool that tells you which app has claimed a global keyboard shortcut. There’s screen OCR. There’s a QR code scanner. There’s a lot.

Supercharge is $20, one time, with a free trial, and it’s on Setapp as well. It requires macOS 26 or later.

Scratchpad

Scratchpad is another entry in quick note taking. I take a lot of quick notes. It’s a single, always-available, plain-text note that lives in your menu bar (or the Dock; your call), with a hotkey to summon it. On the iPhone, it can live on your Lock Screen or in Control Center, and iCloud sync is there if you want it. It keeps local backups, too. It’s $12, one time, and the purchase covers Mac, iPhone, iPad, Apple Watch, and Vision Pro.

Second Clock

Second Clock (free) is very clever when you want just one other time zone always visible. It puts a second clock in your menu bar, and you can stick a flag emoji in front of it so you remember whose clock it is. That’s it. Want more than one? Sorhus offers extra builds with different identifiers so you can run several at once, which is a delightfully brute-force solution. Or you could use a certain other menu bar app that shows what time it is around the world. I mean Time To Go. I made it.

And dozens more…

You’ll get it when you browse his site: These are tools to make you speedier, more productive, and to help you bend your Mac (or other Apple device) to your will.

Check out Sindre’s apps.