This week: some thoughts about the Apple Watch; and thoughts on iPadOS 26.
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Here’s the thing about reviewing the Alpha One Niner Whitley: I’m about to tell you it’s the best office backpack I’ve ever used, and you might wonder how I can be so sure when this isn’t like the typical bags I put through their paces. Fair question. But stick with me, because this is one hell of a backpack.
Alpha One Niner doesn’t just make good backpacks—they make backpacks that make you stop and think “holy shit, how did they nail this so perfectly?” Every single item I’ve tested from them triggers the same two-part reaction: first, pure appreciation for the craftsmanship, then genuine surprise at the low than expected price point.
The Whitley hits both notes flawlessly. This isn’t a backpack with asterisks or “but if you can overlook…” clauses. It’s simply exceptional, full stop. I’m testing the original version, and while the current generation has some tweaks, nothing that would change what I’m about to tell you.
So here’s my claim upfront: if you carry tech gear to an office or work remotely from coffee shops, airports, and client meetings, this is the backpack that’s going to make you wonder why you ever settled for anything else.

For the first time since the iPhone launch, Apple finds itself behind in a major technology shift — years after the shift was apparent. This is a major red flag for the company.
Leading up to WWDC 2025, most Apple pundits aligned around John Gruber’s article “Something Is Rotten in the State of Cupertino” where the defining concept being that the Apple Intelligence miss points to a more soured core at Apple, Gruber concluded:
When mediocrity, excuses, and bullshit take root, they take over. A culture of excellence, accountability, and integrity cannot abide the acceptance of any of those things, and will quickly collapse upon itself with the acceptance of all three.
Gruber was right with that, and he still is right. And nothing at all which happened at WWDC 2025 changed any of this. Pre-WWDC, there was not a notable Apple blogger-type disagreeing here, which is in itself rare, but points to how obviously bad things are.
WWDC was a shit show of half baked ideas, and mostly defensive bullshit, and a lot of time spent trying to make Craig look cool. Too much time.
Anyways, what we know post WWDC about Apple:
Jason Snell at Six Colors has a very weird article which is partly making clear that Apple is not good at AI, partly showing they are using AI, and partly saying maybe they shouldn’t bother thinking about AI, this line sticks out to me:
Apple’s AI stuff needs to get better, but what the company really needs to be is a builder of platforms that are good for users, including those who want to use AI to perform tasks.
Yes, but also, no. This has been bothering me all week. I was going to spend time talking about how shit Liquid Glass is as a UI (a UI that seemingly Snell and Gruber both like somehow?). Instead, I can’t get this AI bullshit out of my head when it comes to Apple.
And I only saw this post from Snell because Gruber linked to it, agreeing with Snell’s conclusion — wild times.
What I am saying is that Apple is acting like Blackberry and Nokia at the launch of the iPhone.
Apple is one of the largest and most profitable companies in the entire world.
So while OpenAI caught most of the huge tech companies flat footed, and really only Anthropic (and to a lesser extent Mistral) seemed prepared — it’s not to say Apple had not been aware of, or even working on, LLMs — but they didn’t have it. No big tech company did.
Let’s take a look at how big tech reacted to ChatGPT 3.5:
In billions of dollars, here’s the cumulative net income reported for those company from 2023-2024 to give you some perspective:
(Microsoft and Apple are estimated, waiting for reports, etc etc.) Those are all above the valuations of most of the prominent frontier LLM companies themselves.
This is also to say, that in no way, is Apple and underdog — they are the top dog. Does Apple primarily make platforms and devices? Kind of, yes, but Alphabet primarily does Search, and Meta is social media. That’s not really an excuse as to why Apple is behind, nor should it be a reason for them to “focus on the platforms” because those Platforms are not where AI is happening: web and NVIDIA are where it’s happening. And AI is already transcending platforms — this is Microsoft not shipping a web browser back in the mid-nineties.
It’s the first time since the iPhone, Apple’s not in the game in any major way. They may normally ship late, and ship great — but they are announcing early, and failing to ship. That’s not shade, that’s fact. It’s been years, still nothing.
They have the money. They have the talent, or at least the means (money) to get the talent.
It seems abundantly clear that Apple is lacking the vision. A dangerous spot for a company this large.
There are, as far as I can see, three paths to take (since 11/2022 at least): integrate AI tooling through partnerships, build your own LLMs, or do both. Microsoft did both. Everyone else went down building their own. Apple? They kind of are trying to do both, but they are failing horribly at both which is WILD.
Something I keep thinking about on this is Meta and Alphabet — two companies that I really dislike for privacy reasons — but two companies who were caught with nothing, then hit the accelerator so hard it’s been impressive to see.
I did some quick estimates, since ChatGPT hit mainstream in late 2022 here’s the (very rough, because I used AIs for this) model release estimates:
Depending on how you count, you’ll see that I left some out — there’s a lot of specialized models, I mostly focused on the larger releases. There are, some really interesting take aways from this:
Then there is Apple. I found three releases, and to be clear: none of these are releases people actually use outside of the Genmoji. In other words: Apple off loads to frontier models quickly (OpenAI). They have a few small models built, mostly exploring on-device quality of smaller models. And that is the correct term: exploration models. It is possible to be leading in this time: Meta, Alphabet, and xAI all pulled off huge feats in the same time.
Perhaps Apple is simply exploring, but even there they would be very behind. Microsoft is very much cranking the same type of exploration models out, and they have 15 out there. Could it be that Apple has more, and they are hidden from the public? It’s absolutely got to be the case. Yet, that would also stand to reason they are not great models.
And this is the worry: Apple, by every metric I can think of, is lagging further behind with each passing month in the generative AI space. It’s not a space where you can hide the models, you need people using them so you can make them better — which is another business area Apple is not good at — so even if they have some great stuff tucked away, it almost is a fallacy it could be that great since they don’t have any real practical experience.
Google didn’t take Gemini from being crap to being leading by toiling away hidden. Nope, they put it out there, and iterated. As has every company on the list, except Apple, who has largely stuck to keeping the models decently small and on device and releasing research papers.
It’s not a happy path for Apple long term.
Even if partnership is the right way forward for Apple, in that space they are not even remotely being active. Microsoft is taking that approach and they have partnered, and launched with partners, end user level features and products at breakneck speed. While Apple has touched on some of this, it’s mostly not good. So even if Apple has decided to focus on these partnerships, they are seemingly well behind the curve.
Apple is significantly behind no matter what their strategy is. Lagging partnerships with the integration Apple has done (Siri offloading to ChatGPT at different times) being pretty awful from a user experience standpoint.
On the LLM creation front, Apple is even further behind. The models they have released are very niche, and they’ve not really shown any reason to believe they’ll have competitive models soon.
Apple’s behind — and not by a little bit. I am not confident the current Apple leadership knows how to catch up, or are even willing to admit they are behind.

Note: this item was provided for review.
Desert boots have always been that perfect middle ground – more substantial than a shoe, but lighter than a proper boot. After going years without a pair, I’d forgotten just how effortlessly they fill that gap in your footwear rotation.
When Crown North Hampton offered to send me their Snuff Janus Suede desert boots, I figured it was time to reacquaint myself with this classic style. The wait for these hand-crafted English boots was worth every day – I’ve been wearing them so constantly that I have to consciously remind myself to reach for something else in my closet.
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These are a classic desert boot style, two eyelets and unlined. This pair is suede, which Crown Northampton has some thoughts about:
Thought to be one of the best if not the best quality suedes available. This is mainly due to Janus calf suede originating from some of the very best raw material in the world. The hides benefit from a secret combination of ingredients used in the subsequent tanning processes – all carried out by C F Stead in Leeds, England. The end product has a soft, luxurious look and feel, whilst offering reassuring strength and durability. Janus suede may feel delicate to the touch but it contains strong fibres that make it tough, flexible and resilient.

I do not normally like to quote that much, but that statement perfectly encapsulates my thoughts on this suede. It’s very soft and delicate feeling to the touch and when wearing them. At the same time they are holding up exceedingly well — I have no doubts about the durability overtime.

These boots have a stitch down construction on a natural crepe sole. They have a half-lined leather foot bed, keeping things rather simple. They are handmade, to order (they have a long lead time, FYI), in England — by the fifth generation of owners.
The overall fit and finish is fantastic as are the materials used.
As you might imagine, I receive items to test fairly often, and typically I show them to my wife first. Her responses are really all over, but before I could ask her about these boots, she was already telling me how much she liked the look. Each time I’ve put them on after a few days, she remarks on how much she likes these boots. We could end the review there, doesn’t get much better for me.

Desert boots are really a sleeper hit with boots, as they pair well with denim, with chinos, or even a pair of linen pants. You can wear them casually with ease. At the same time, a well crafted pair (like these), will add a little pep to an outfit to make the entire fit look a little more polished. They hit that perfect spot for someone who wants to be put together without looking over dressed.
What I cannot get over is the comfort these boots provide. I’ve had desert boots before, and I knew that the crepe sole would be nice to walk around in — that was expected. What wasn’t expected was how soft that suede upper is, such that it makes these boots feel like you are wearing a soft slipper. This feels like you are cheating: looking great, while feeling like you could kick your feet up next to a fire in slippers, but they are your boots.

They are boots I have walked a few miles in at a time, and not felt any slight discomfort. Boots I have stood around for hours in, and felt comfortable. And they’ve looked good doing it, and continue to look good.
The only downside I’ve found with these is that the upper is so soft, it requires me to use two hands to put the boots on, as I can’t slip my foot in without holding a side and the tongue as those areas will otherwise fall under my foot easily. This is the only downside.
The coloring on the tobacco snuff is spot on. Comfort is there. They are unlined so they wear quite comfortable in warmer weather — something I am looking forward to this summer. In the mean time they’ve been great riding a bike around the city, walking around in mild rain and wet, and on the odd summer hot days we’ve had my feet have kept their cool.

Right now, these boots sit at the top of my daily rotation for good reason. They’ve nailed that sweet spot most of us chase – looking intentional without trying too hard, comfortable enough for all-day wear, yet polished enough to elevate whatever you throw on.
The craftsmanship speaks for itself, and I’m struggling to find anything not to love about them. If you’ve been on the fence about desert boots or looking to upgrade from a cheaper pair, these are worth the investment.

The first time I saw the Singi 28 backpack in person, it was hanging on the wall in a Fjallraven store. I was immediately drawn to it. The proportions are very nice, as are the aesthetics. Hitting a mark somewhere between traditional outdoor packs, and a more modern pack.
I made a mental note to check it out sometime. Then, months later, Fjallraven put the grey color on sale, and I snatched it up for a killer price.
Since then, I’ve taken it on one trip, and many hikes. I’ve found that it is quite good, and that’s before I consider the value proposition it offers.

I’ve had this jacket for some time now, and I’ve bought many less expensive clones of this jacket before getting this. So when I tell you that this is end-game for a waxed work-wear jacket, know that I say that as someone who has tried hard to avoid paying the premium and dealing with the sizing, but also as someone who now owns two of these iconic jackets.
No matter how you look at it, Filson’s Short Lined Tin Cloth Cruiser is amazing.

Note: this item was provided for review.
For those not aware, most of the major sunglasses brands are owned by two companies. Recently (in the last 5-10 years) there’s been more and more brands popping up which are smaller, independent companies — these brands typically make really exceptional products. Shinzo Tamura is one such brand, based out of Osaka in Japan. They sent over their Namba Slate Sunglasses for me to review.
I wasn’t sure what to expect with these. But what I got is easily the best pair of sunglasses I own, and have ever owned. From the optics, the materials, and the comfort — all outstanding.

Whenever I talk to people in person, that’s the question I get the most: why are you carrying all this gear and what the heck do you need it for? This is a fair question, and depending on how much I want to engage with the person, I have two answers:
It’s genuinely very easy to be incredulous when you start looking at everyday carry (EDC) posts and blogs. People are carrying a full pharmacy, or they have an auto-deploying mini-gun strapped their inner thigh and spend a lot of time talking about reducing chaffing from the belt fed rounds. Some people very seriously carry two to three knives. The community loves to quip and quote military sayings that they often don’t understand and only heard in a movie.
It’s a big joke, or so it feels like even to me most of the time.
Every year or so I tend to revisit this topic, to defend why you should carry things, and talk about why I carry these things. I go into specifics about why I carry a bag; a knife; a flashlight; a first aid kit; or whatever else the taste of the moment is.

Note: this item was provided for review.
A good standard, works for everything, pair of slacks has been hard to come by for me. Often I find the cuts to be too narrow, too low rise, or if they are a higher rise, they have a comically wide leg. I wanted something traditional, well made, and easy to wear.
I found exactly that with the Patrick James Garbadine Flat-Front Slacks — so much so that I really enjoy wearing these out and about.

At the start of 2021, Marathon released an ‘Arctic’ variant of their iconic GSAR. A welcomed release from a brand with a lot of history both with the Canadian military and the US Military among many others. The watch community loves to talk about tool watches, which just so happen to be luxury watches — to me they are talking about a Mercedes G-Wagen (the Orange County variants that is). Sure, that can go off road and do cool shit, but that’s certainly not why you buy it.
The GSAR, and Marathon watches generally, are the Jeep Wranglers of the lot — all utility, all tools. I picked this Arctic GSAR up second hand, and have been wearing it a ton.
Bottom line: this is a better watch than I expected, and better than I wanted it to be, but the current pricing makes it a tough sell near MSRP pricing.

I should start this by mentioning that I am not the biggest fan of a tote bag. I get their value, have loads of them, and I do use them often. However, it’s almost always for carrying food stuffs — either home from a grocery store, or to the next Airbnb adventure. Outside of that, I’ve always felt a little awkward with a long handled tote bag.
But, when DSPTCH dropped the Corpsware line, and I saw the Market Tote — I was intrigued enough to pick one up. One of the biggest selling points was the shoulder strap, making this a tote-messenger — it looks sharp too with a cotton fabric.
Unfortunately, in practice, this isn’t a very good bag for many reasons.

Note: this item was provided for review.
Dressing for summer weather always presents the same problem: there’s not a lot of cool-wearing, but casual pants for men. There’s effectively linen pants and a plethora of “lightweight” variants of standard pants, most of which are hardly lightweight enough. (Which I assume is also why so many men turn to synthetic pants better suited for hiking.) The problem with linen is that it is hard for most men to wear it in an easy going fashion as it can read formal, or quickly be engulfed in creasing — which bothers most people.
Enter these Linen Drawstring Pants from Patrick James, a linen blend ‘easy’ style pant with the perfect toss on to stay cool style, all while keeping the ease of wear like denim is.