Ask Paul: September 27 (Premium)

Happy Friday! It’s been a horribly busy week ahead of a trip to Dallas and then Mexico City, so I’m ready to kick off the weekend a bit early. This will be our last weekend in Pennsylvania until mid-November.

My preferences are now historical

MattHewitt asks:

Traveling to Boston for the first time ever for a weekend travel date with my brothers. Any tourist or restaurant recommendations? Wanted to hear from someone who lived in the area for a while rather than just punch it into ChatGPT.

We moved to Pennsylvania 7 years ago, and while we do get back to the Boston area as often as possible–my wife was just there a few weeks ago, visiting family and friends, though I skipped that trip to catch up on work–we haven’t actually gone into Boston proper that much. The last time I was in the city was June 2023. Worse, almost all our former favorite places are gone, many related to the pandemic. So everything here perhaps not as well informed as it could be.

As far as the tourist stuff, you can’t go wrong with the classics. We used to joke about the people who would visit us for a few days and see more of the city than we ever did, but a lot of that stuff is worthwhile. The Freedom Trail, the Boston Public Gardens, the U.S.S. Constitution are all worth experiencing. I would go to the top of the Prudential building for the views. Harvard Square (across the river in Cambridge), Faneuil Hall, and the green space along what used to be the overhead highway that was removed during Big Dig are both pretty and worth walking through. If you’re into art, the Museum of Fine Arts (MFA) and Isabella Gardener Stewart are excellent. The Red Sox will end another fruitless season on Monday, but go on a Fenway Park tour, that’s really nice. Do something on the water, like a Whale watch or harbor cruise. The Boston Public Library is gorgeous (and free); you could grab a to-go lunch nearby and eat in the courtyard there.

For food, you have to go to the North End for Italian. Most anything there will be pretty good, and it’s been a while, and while most of the well-known places are on Hanover Street, I’d look on the next block over (Salem Street) as well. Mike’s Pastry is famous there, but it’s always packed and Trattoria Il Pannino is next door, cheaper, and more easily accessible. For seafood, you can’t go wrong with Union Oyster House, Summer Shack, or Legal Sea Food (including Legal Kitchen in South Boston). I strongly recommend the pan-fried lobster at Summer Shack if you have to choose just one place/meal. (I went there and got that on my last trip into Boston.) Durgin-Park in Faneuil Hall is touristy and kitschy but they earned it.

Mostly obvious stuff I guess.

OpenAI is a train wreck that could take us all down with it

train_wreck asks:

What do you make of the high-level departures at OpenAI? Do you think they may be related to the for-profit changeover?

I am freaked out by everything that’s happened at OpenAI at a corporate level. As I’m sure Satya Nadella and Microsoft are, evidenced most obviously by its March creation of a Microsoft AI organization led and staffed largely by former Inflection executives and employees. This company is far too volatile, and while I get the whole “we’re different” thing, that was cute when Google did but terrifying now. OpenAI could disrupt the entire industry and probably the world, but it’s starting to look like its going to implode like a black hole eating itself instead. I don’t know what to make of this beyond what feels like a Sam Altman power play involving both the people running the company and the corporate structure he prefers.

This is a weird moment for Microsoft. It needs OpenAI desperately. But it also needs to dump OpenAI desperately. It’s going to end badly no matter what. I feel like that was always true, but with each passing month it just gets weirder and weirder.

TWiT, the next generation

helix2301 asks:

What do you think of Twit 4.0 as Leo calls it? It reminds me of the early Twit from the old days before Leo took over the entire cottage.

I was in New York the other day for a Google briefing and ended up hanging out with Lon Seidman of Lon.TV, who I had previously met at IFA. And it sort of clarified something I’d been thinking about lately, that there’s been a series of generational shifts in content creation, and that it’s easy to get left behind. When I started out, the world was all print–books, magazines, newspapers–and there was great expertise but limited means to communicate that. I started blogging before we called it that, and when I came to Windows NT Magazine (really, its publisher, Duke Publishing) in 1999, I was the new kid, the “web guy,” and I was greeted with suspicion by some of the old-school writers there at the time.

And then the world changed and my web-based approach became the norm and even a linchpin of the business. Podcasts–audio mostly, but also video–became a thing, a replacement for radio for many. And in more recent years, video, but really YouTube, became the go-to medium for content, and I often said that if I were starting out at the time, I’d probably just have a YouTube channel, though that’s a bit far-fetched because I do approach everything from a writing-first perspective. And now we have TikTok, which I have to think I’ll never be involved with. Change is hard, and on a surface level, democratizing content publishing is good. But one of the troubling things that accompanies the shifts I note above is the decline in expertise we see from content creators (generally). As you move from books to websites to blogs to YouTube and now to TikTok, the content is shorter, it’s less trustworthy, and the people creating it are no longer necessarily experts. And there are so many of them. Too many.

Anyway, Lon and I both agreed on the basic premise that, were we starting out today, we’d pretty much have to go with TikTok. And God knows what comes next. Then, in a weird coincidence, I listened to a Verge Decoder audio interview with Arc cofounder and CEO Josh Miller on the way home from that briefing because I had an hour or more to kill in the car, and he touched on this same topic, which was interesting. And depressing. But whatever, the world is changing, and has been changing for a long time now.

I mention all that as framing for the TWiT thing: When Leo started TWiT in 2004/2005, he used technology to recreate the TV/radio studio experience of the day but in a much more streamlined and cost-effective way. But when you fast-forward today, suddenly what TWiT is competing with isn’t traditional studios but rather individuals walking around with an iPhone on a selfie stick. And so it’s become this thing it previously replaced.

TWiT could have just disappeared after existing off inertia for a while, I guess, but they’ve opted to go with the disruption instead of being subsumed by it. And I really respect that. I hope–and expect–that this business can be wildly successful and profitable using this stripped-down model, and I think it makes tons of sense. I guess it is a sort of “returning to its roots” thing in a way. But that’s sort of beside the point to me. I see this more as, the world has changed, and we can embrace it, ignore it, or fight it. And they made the right choice. I’m not surprised, as there are so many smart people there. But I’m also glad, because the world needs the expertise they bring too.

What do you think of Richard on Windows Weekly? I think Richard is great but I liked it when it was just you and Leo like back in the old days. Even Mary Jo gave the show a different feel is there any reason why the show has to be three people?

There’s a lot to that dynamic. I enjoyed doing it with just Leo before Mary Jo joined and then for a few months after she left. But this can be grueling for Leo, I think. And you need two people who are fully invested in the topic and can just sit there and yap about it off the top of their heads for 2-3 hours each week.

Richard and I have been friends for many years, and it never even occurred to me that he’d want to be on the show, let alone as the full-time co-host. And so that’s worked out wonderfully: We talk all the time anyway, and so this show has become a conduit for that, and it’s worked out well. The whole experience has been a highlight of my professional life. I would never have started a podcast on my own, certainly not back in 2006. And getting to do that with Leo, who I felt like I knew from afar from seeing him on The Site and then Tech TV, was incredible.

Becoming friends with Mary Jo and then having her partner with me for so many years was likewise excellent. And now Richard, an expert I’ve respected for years and years. And with him, as with Mary Jo, there’s a sort of comradery and natural chemistry thing that you can’t fake. We were also complementary in that we didn’t cover the industry in the same way, and that was nice, too. I was worried that I’d have to find someone, or some cast of someones, to fill in after Mary Jo left, so when getting Richard involved went from an unthinkable impossibility to happening, it was a huge weight off my mind. Richard is one of the smartest people I’ve ever met, he’s very well-spoken, and he hits our industry from an enterprise and developer focus, so that’s likewise complementary. It’s just worked out wonderfully.

I guess I could just drone on for a few hours by myself. But I’m more tired of the sound of my own voice than anyone else. It’s nice having others there with their own viewpoints and ideas.

Arc

Craig-Atkins asks:

How has the discovery of Arc Browser’s first major security vulnerability affected your view and usage of Arc? I’ve been using Arc for the last few months and have really come to enjoy it, but I am slightly concerned about how significant this vulnerability seemed to be. Curious what your take is on this.

Arc is small enough that it could use “security by obscurity” as a strategy, and while I had never really thought about this explicitly, I guess if I had been asked about this previously, I would have simply assumed that it benefits from whatever security work goes into Chromium and everything is probably fine. But this event happened, and, as I’ve often noted, you can really learn a lot about people–and in this case, a company, which is of course run by people–in seeing how they respond to tragedy. And this could not have gone better: The security researchers that found the vulnerability responsibly alerted The Browser Company privately. The Browser Company worked with those researchers to fix the underlying problem. The security researchers published their findings after the vulnerability was fixed. No bad actors had exploited the vulnerability and no customers were harmed. It came and went without impacting anyone.

But the best thing about this episode, to me, was how The Browser Company responded to this event. I found it to be not just credible, but perhaps above and beyond what one should expect of such a small company. I find these guys to be quirky and odd in some ways, but they have a “think differently” vibe I like, too, and their approach to the web as a platform and their rethinking of how we use it are compelling. Had The Browser Company responded differently, we might be having a different conversation. But this has elevated my respect of them and made me trust them explicitly in a way I didn’t before (because I didn’t really think about it all that much, not because I just didn’t trust them).

Long story short, I think Arc comes out looking better as a result of this incident.

The Eternal debate

markiehill asks:

If you could have only one would you choose Pixel 9 Pro or Iphone 16 Pro Max ? Based on your experiences so far.

If all goes according to schedule, and it rarely does, I’ll publish my Pixel 9 Pro XL review this weekend, switch to the iPhone, and then publish that review by the end of October. So I don’t want to undermine that work, in a way, but this is of course something I think about all the time. Not just in terms of these specific two smartphones, but in general. It’s a classic debate for the ages, really.

This seems like a cop-out, even to me as I write it, but they’re both fantastic, best-in-class phones. They’re incredibly similar: I had called out Google for copying the iPhone look and feel with the first Pixels, and then they went off on their own various style changes over the years, but Pixel and iPhone have never looked more similar than they do right now. When I’m at home, which is usually the case, I have both next to me most of the time, and I have picked up the wrong phone–the iPhone, for now–when we had to head out for whatever reason. I’ve never made it as far as the car, but I’ve gotten close. They’re very similar.

I discuss this notion of a “matrix of choices” when it comes to making big decisions. And smartphones are a great example of this: You could list out the various attributes that are important to you, “weight” them by awarding more points to those attributes that are most important, and then see where it lands. This will be different by the individual, of course, but as the platforms improve and new models come out, some things shift. There are vague ideas–the openness of Android, etc.–and specific, objective criteria, like the quality of the cameras or the battery life. Ecosystems matter, not just accessories and hardware, but also services. It goes on and on.

The iPhone is a high bar, but it’s a high bar that’s been undercut in some ways but some limitations and Apple strategies one might disagree with. And those are starting to fall away, so the decision matrix is shifting. On Google’s side, they’ve suffered from many quality and reliability issues, but those seem to be fading, and where the 8 series was terrific, the new Pixels are even better. So they’re reaching that high bar, complicating matters.

And there are so many little things. So many. These need to be factored in because they matter in a real-world day-to-day experience way. I like that I can basically toggle Do Not Disturb on the Pixel by just putting it face-down on a surface. I like that I can play to any speaker in my house using AirPlay on the iPhone and it just works. I prefer Android notifications over those on iPhone. But Apple did this oddly terrific thing with dynamic theming in iOS 18 that’s better than the similar feature on Pixel. I use a lot of Google services, so that integration is good on Pixel. But Dynamic Island is oddly amazing, and I miss it when it’s gone. Back and forth, back and forth.

So I don’t know. Right now, I’ve spent more time with the Pixel so it’s tilted in that direction. But my experience with the iPhone earlier this year was positive enough that I’ve since expanded my use of Apple hardware and services. So it’s kind of hanging in the balance.

There’s no real answer. I would be very happy to use either of these phones. And while I will use one or the other in a sort-of daily use way, I will also likely just shift back and forth as the need arises. This isn’t what any typical consumer would do, of course. But I’m not sure if there’s a huge market of people who would switch between these platforms at this point anyway. Most seem pretty certain about one or the other.

Dialing in on nice Surface futures

madthinus asks:

Random question but is the surface dial still supported and sold? The surface hub is surely discontinued by now?

Both are still sold and supported, but they’re also niche products and I can’t imagine either is top of mind for Microsoft or its customers.

I had this vague memory that Microsoft had mentioned Surface Dial during the Copilot+ PC launch this past May, but scanning through the video and the transcript, I don’t see that. Dial isn’t listed among the Surface Pro 11 accessories, and its product page doesn’t specifically mention Surface Pro 11, but I assume they do work together. (That said, the capacitive on-screen detection feature is apparently Surface Studio only, which doesn’t suggest good news. This feature worked on Pro, too, for a time, so it’s unclear if that continues through the newer models.)

Surface Dial is several years old, and it hasn’t been updated in a long time. But Surface Hub 3 is less than a year old. Looked at in the context of Microsoft honing down the Surface product lines to just those that makes sense, you could make a case that neither makes much sense. But Surface Hub is part of a broader Teams portfolio, too, and I think that may be important enough to Microsoft that it continues forward as a product. Surface Dial not so much.