Upgrade

00:00:00 ◼   ► [Music]

00:00:10 ◼   ► From Relay FM, welcome to the first ever Upgradies Hall of Fame.

00:00:16 ◼   ► This very special episode is brought to you by our broadcast partners, FitBud, ExpressVPN and Squarespace.

00:00:23 ◼   ► Once again, Simon Cast from London, England and Mill Valley, California.

00:00:27 ◼   ► I'm one of your hosts for this evening's festivities and joining me is my co-host, Jason Snow.

00:00:33 ◼   ► Jason Snow, welcome back to the Upgradies yet again.

00:00:36 ◼   ► Thank you, Mike Hurley. Weren't we just here?

00:00:38 ◼   ► We just were. Well, as you would have heard on our last Upgradies just a couple of weeks ago,

00:00:44 ◼   ► it was Upgradies 10, Upgradies X, the 10th annual Upgradie.

00:00:49 ◼   ► So we thought to honor that we would create a Hall of Fame for the Upgradies.

00:00:57 ◼   ► Now this is separate to the lifetime achievement award, which is one if somebody wins three times in a singular category,

00:01:04 ◼   ► they are elevated into the rafters.

00:01:06 ◼   ► They have a little banner up in the rafters at the Upgradies offices where they're enshrined for all time.

00:01:13 ◼   ► So it stops the same things from winning over and over and over again.

00:01:17 ◼   ► But we thought to celebrate the 10 editions of the Upgradies,

00:01:22 ◼   ► that we would look back from the winners of all of our current categories and choose a Hall of Fame entrant from them.

00:01:29 ◼   ► So a lifetime achievement award winner could also be a Hall of Fame award winner.

00:01:34 ◼   ► We'll just have to see how it goes.

00:01:37 ◼   ► I have some credits again.

00:01:41 ◼   ► Sure.

00:01:41 ◼   ► I would like to thank the following people for helping make the Upgradies possible.

00:01:45 ◼   ► Zach Knox for web design, JD Davis for artwork, Chris Breen for music, Jim Metzendorf for audio editing, Chip Sudduth for video editing,

00:01:53 ◼   ► and Jamie Snell for social media management.

00:01:56 ◼   ► Once again, just noting that these people are involved in all the upgrades.

00:02:01 ◼   ► So we thank them, especially as we've entered into a new year again.

00:02:04 ◼   ► Thank you all for helping make the show possible.

00:02:07 ◼   ► Should we go right into it for the first award?

00:02:12 ◼   ► Do you have any opening statements you would like to make?

00:02:15 ◼   ► How does it work? Do I have any opening statements?

00:02:17 ◼   ► I'm proud of all of you.

00:02:20 ◼   ► It's an honor to be an Upgradies nominee and winner.

00:02:26 ◼   ► And this is only an exhibition and it's not a competition.

00:02:32 ◼   ► We're just choosing our favorites of our favorites.

00:02:36 ◼   ► Yes.

00:02:36 ◼   ► Because we thought it would be fun.

00:02:38 ◼   ► And somebody will be coveted, you know.

00:02:41 ◼   ► Something in this, which is nice, is that we will get the opportunity to mention all of the winners across each year,

00:02:49 ◼   ► which I think will be a nice thing for today to highlight the many illustrious winners over the first 10 Upgradies competitions.

00:02:57 ◼   ► So we will start with the first round today, which is best iOS app.

00:03:03 ◼   ► And we're going to go to the beginning.

00:03:05 ◼   ► In 2014, Overcast was the winner.

00:03:08 ◼   ► In 2015, Slack. Can you imagine a world in which the best iOS app was Slack?

00:03:15 ◼   ► Like if you think about it today.

00:03:16 ◼   ► We were all using Slack. We all started using Slack that year.

00:03:18 ◼   ► Incredible.

00:03:19 ◼   ► And relying on it.

00:03:19 ◼   ► Yep. 2016 was Workflow.

00:03:23 ◼   ► What happened to that app?

00:03:25 ◼   ► Nobody knows. Where are those people now?

00:03:28 ◼   ► Carrotweather in 2017. Overcast in 2018 and 2019, making it a Lifetime Achievement Award winner.

00:03:36 ◼   ► Drafts in 2020. Carrotweather again in 2021.

00:03:41 ◼   ► And then the last two years, 22 and 23, has been Flighty.

00:03:46 ◼   ► So Carrot and Flighty, right on the edge of Lifetime Achievement.

00:03:51 ◼   ► I have, I think for me, an early gut feeling here.

00:03:57 ◼   ► Slack, clearly.

00:03:59 ◼   ► Yeah, Slack.

00:04:01 ◼   ► No, I would be leaning towards Carrot. So by the way, we have not made nominations for this between the two of us like we usually would with the upgradeers.

00:04:09 ◼   ► The whole point of today's episode is we're just going to talk through all of them and come up with a winner ourselves.

00:04:15 ◼   ► And so like I would be leaning towards Carrotweather here.

00:04:21 ◼   ► Interesting.

00:04:22 ◼   ► It is also like a runner up so many years too. Which we're not going to go through the runners up, but it's in there.

00:04:28 ◼   ► Carrotweather is great. Overcast is also one that I am, I mean, is it the iOS app I use the most?

00:04:38 ◼   ► I mean, I don't know. Maybe. Maybe.

00:04:43 ◼   ► But Carrotweather is good. Flighty is good. These are our most commonly chosen things.

00:04:52 ◼   ► So I feel like for some categories we are judging the app, I think, over its entire time period.

00:04:59 ◼   ► And I think for some categories we are judging a winner or a nominee for its initial impact.

00:05:05 ◼   ► And I think we'll have some later on where that is.

00:05:07 ◼   ► And for me, I just feel like over the period of time, going all the way back to the beginning, Carrotweather has seen such advancement and has only gotten better and better and better over time.

00:05:20 ◼   ► I feel like its kind of share amongst the audience has grown and grown and grown.

00:05:26 ◼   ► Whenever Carrotweather is nominated for any award, it is nominated heavy amongst the upgradients too.

00:05:33 ◼   ► And I feel that way myself. It's an app that I feel like over time, it's done the things that are best for the users in a sense of like, now it is mostly interacted by many people with the watch app or the widgets rather than the actual app itself.

00:05:49 ◼   ► Like it's doing all of the things that a good iOS app should do.

00:05:54 ◼   ► But that's where I'm leaning. If you want to make a case for Overcast or somewhere else, then I'm very willing to hear it.

00:06:03 ◼   ► Well, I mean, the case for Overcast is that it is an independent podcast app that when it began, it was, you know, along with some of its competitors, it was offering a real solid alternative to what Apple offered.

00:06:15 ◼   ► And Apple has really upgraded the podcast app over the years. A lot of those independent podcast apps have sort of fallen by the wayside.

00:06:24 ◼   ► Overcast remains and is certainly, it still offers a bunch of things that Apple's podcast app doesn't.

00:06:33 ◼   ► And, you know, I still rely on it for things like using it on my watch as well as using it on my phone.

00:06:40 ◼   ► So I think that there's a strong case to be made for it.

00:06:45 ◼   ► So where I would say for Overcast, because I use Overcast every day too, it's my podcast app of choice, I think Marco would be the first person to tell you that the app is not where he wants it to be right now.

00:06:56 ◼   ► Well, he's rewriting it right now. We know that. And it hasn't had a lot of progress in the last few years.

00:07:01 ◼   ► And we know that he knows that and that he's working on it. But right now, I absolutely think that's true.

00:07:07 ◼   ► Also, I mean, you make a great point with Carrot Weather also, which is the support from Upgrading and the fact that it has evolved so much over time.

00:07:16 ◼   ► Like almost every year, there's other sets of huge Carrot Weather features that are coming in.

00:07:22 ◼   ► And it also has Apple App Competition. And I think that the Apple Weather app has a lot going for it and has improved as well.

00:07:29 ◼   ► But Carrot is also still great. And one of the things I like about Carrot is that it can be what you want it to be.

00:07:35 ◼   ► Like for me, some people love Carrot because it's got jokes and snark and stuff. I don't. I turn that off because I don't like it.

00:07:44 ◼   ► But it doesn't matter. You can literally lay out the app, in the app, to show whatever you want to show, which is really remarkable.

00:07:51 ◼   ► So I'm okay with Carrot Weather.

00:07:54 ◼   ► That is where I lean. And it is purely because, as you say, if there's a new system feature, Carrot adds it.

00:08:04 ◼   ► And does it well. With the, I would say, the caveat, which we spoke about in the upgrades, I don't think they did a good job with their interactive widgets.

00:08:14 ◼   ► But maybe it wasn't that needed for what their type of widgets are. I don't know.

00:08:20 ◼   ► Yeah, I say, I mean, clearly, the winner is Peacock.

00:08:26 ◼   ► Hang on a second.

00:08:29 ◼   ► What if we just picked something totally random? That isn't anything that's been in there.

00:08:33 ◼   ► No, I feel like that is the one thing that we set in the rules, is that we're picking from previous winners.

00:08:38 ◼   ► It really needs to be one of the previous winners. Okay, well then, in that case...

00:08:42 ◼   ► Before we do it, I will just make the case of we are a podcast, right? And so an overcast is the way that the majority of our listeners listen to this show.

00:08:52 ◼   ► And so there is also the point of, do we just go with it because that fits?

00:09:00 ◼   ► I don't think that's enough of a reason.

00:09:03 ◼   ► Okay.

00:09:04 ◼   ► I mean, it's a tough decision, but I like your suggestion and your argument.

00:09:09 ◼   ► Again, as I said in my opening statement that I made up very much on the spot, you're all doing great. We love all of you.

00:09:17 ◼   ► But we have to pick a Hall of Famer.

00:09:19 ◼   ► Just to be in the conversation, you know?

00:09:22 ◼   ► Yes.

00:09:23 ◼   ► That's the important thing. Carrot Weather.

00:09:24 ◼   ► Carrot Weather.

00:09:25 ◼   ► Alright, so that's the first Hall of Fame entrant for the best iOS app, is Carrot Weather.

00:09:31 ◼   ► Alright.

00:09:32 ◼   ► This is my favorite. Talking about best newcomer.

00:09:37 ◼   ► I love the idea. I've been very excited just about the idea of judging a Hall of Fame newcomer.

00:09:45 ◼   ► And I guess that this is like all-time rookie kind of thing that we're looking for here, right?

00:09:50 ◼   ► Yes, rookie. Also still a weird concept actually, but okay.

00:09:54 ◼   ► But like, so the way I was thinking of this is considering an app and the impact that it had at the time in which it was released.

00:10:04 ◼   ► And we can maybe consider how something has evolved, but personally I would like to consider initial impact.

00:10:15 ◼   ► You can see how we feel about that through conversation.

00:10:18 ◼   ► So our winners starting from 2014 go Workflow, Ferrite in 2015, Swift Playgrounds in 2016, Files in 2017.

00:10:27 ◼   ► We were just excited to have file management.

00:10:29 ◼   ► Apple, two in a row.

00:10:30 ◼   ► And then a three in a row, Shortcuts 2018.

00:10:32 ◼   ► Oh, three in a row.

00:10:33 ◼   ► 2019 was Timery. 2020 was Widgetsmith. 2021, Noir. Sticker Drop in 2022 and Coal Sheet in 2023.

00:10:43 ◼   ► Hmm. Interesting. You know, well, okay. So among the ones that stick out here.

00:10:51 ◼   ► Yep.

00:10:52 ◼   ► Ferrite for me.

00:10:53 ◼   ► Yep.

00:10:54 ◼   ► Huge. Great, you know, iPad app, audio editor. I love it. It's my favorite way to edit podcasts. So good. So powerful.

00:11:06 ◼   ► I would imagine you feel the same way about Timery.

00:11:09 ◼   ► I do, but I wouldn't be holding Timery here.

00:11:13 ◼   ► I love Timery, but it's not one of the ones that I'm making the case for because I think we have three very strong contenders for impact, which are in my mind Workflow, Shortcuts and Widgetsmith.

00:11:29 ◼   ► Yeah. I agree. I agree. I think between Workflow and Shortcuts, I think it's Workflow because Workflow encompasses all of what happened with Shortcuts as well.

00:11:42 ◼   ► And it was such a revelation. And I'm glad we were there. We were on it in our very first upgrade-ies. I'm really happy we got it.

00:11:51 ◼   ► I maybe haven't paid much attention to going all the way back to the beginning, right, when I've been looking at these things.

00:11:56 ◼   ► But there is something so beautiful, I think, about us having Workflow and then four years later, Shortcuts.

00:12:02 ◼   ► There's just something really nice about that that I enjoy. That that was a thing.

00:12:06 ◼   ► And then also, Workflow was best newcomer in 2014. It won best app in 2016.

00:12:14 ◼   ► Yes.

00:12:15 ◼   ► So it improved. And then by 2018, it was the Apple version.

00:12:19 ◼   ► Mm-hmm.

00:12:21 ◼   ► But again, like, I don't know.

00:12:24 ◼   ► So what's the case for Widgetsmith?

00:12:26 ◼   ► Has any app made such an impact on the global stage?

00:12:31 ◼   ► On the world?

00:12:32 ◼   ► Like, I can't think of any other example of an app with virality like Widgetsmith.

00:12:40 ◼   ► Like, you get these AI services and this kind of stuff that go around a lot.

00:12:45 ◼   ► But the idea of just an indie app that is released and then goes viral?

00:12:51 ◼   ► It's the only time I can remember this happening.

00:12:54 ◼   ► And I think that even if you, again, if we're just looking at it within the year that it came out,

00:13:01 ◼   ► 2020, like the fall of 2020, that was the fall of Widgetsmith.

00:13:05 ◼   ► Like, that's what everything was about.

00:13:07 ◼   ► Widgets were about Widgetsmith.

00:13:09 ◼   ► And I just think as a, from an impact, that was a pretty big one to use as.

00:13:17 ◼   ► But then Workflow was a pretty big one for nerds.

00:13:23 ◼   ► Oh, this is, this is the, yes, this is the contrast.

00:13:25 ◼   ► And I would say Widgetsmith, what it has going for it is, it was, it went viral.

00:13:30 ◼   ► It's used by an enormous number of people.

00:13:33 ◼   ► It's an incredible success story.

00:13:34 ◼   ► And when you're representing the newcomer hall of fame, what better newcomer than an app that hits on a new feature and goes viral and is wild?

00:13:42 ◼   ► But I would also say best newcomer Workflow, that's an indie app that became part of the OS infrastructure.

00:13:49 ◼   ► An indie app became the future of automation on Apple's platforms, which is pretty wild.

00:13:58 ◼   ► But can we judge its newcomer-ness based on the fact that it became that later on?

00:14:04 ◼   ► I'm not saying one way or another.

00:14:06 ◼   ► I don't know.

00:14:07 ◼   ► Right? Like, would we say it was best newcomer because later on Apple acquired it?

00:14:12 ◼   ► I don't, I don't know.

00:14:13 ◼   ► I'm just making the argument for like the impact of, this is a new indie app that happened and it ended up changing the future of automation on the entire platform, is the argument for Workflow.

00:14:23 ◼   ► But I, I am also going to agree with you here.

00:14:25 ◼   ► I think that Widget Smith's debut and what happened is about as hall of fame newcomer as you can get.

00:14:34 ◼   ► Yeah.

00:14:35 ◼   ► That is a beautiful way of putting it.

00:14:37 ◼   ► Like we have another newcomer category later on and we have like movie, TV, all that kind of stuff.

00:14:41 ◼   ► I don't think that there is a bigger like this thing appeared and then everything changed in our categories as Widget Smith.

00:14:49 ◼   ► Yeah.

00:14:50 ◼   ► All right.

00:14:51 ◼   ► So I think we're going to do it.

00:14:52 ◼   ► The best newcomer iOS app and entrant into the hall of fame is Widget Smith.

00:14:59 ◼   ► Hall of Famer, first ballot.

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00:17:30 ◼   ► So we move on now to our next category which is Best Mac App.

00:17:37 ◼   ► So going through the list all the way back to 2014 was Fantastical.

00:17:44 ◼   ► 2015 was Logic Pro 10. Is it 10 or X?

00:17:50 ◼   ► It's 10.

00:17:51 ◼   ► Ok, I can never remember. Some things are 10, some things are X, right? Sometimes they're not the 10th version?

00:17:57 ◼   ► Most things are 10. Most things are 10.

00:17:59 ◼   ► Ok. We have 2016 Audio Hijack, 2017 Final Cut Pro 10.

00:18:07 ◼   ► The 10th.

00:18:08 ◼   ► 2018 was Audio Hijack, 2019 was Affinity Designer. I don't remember that at all.

00:18:14 ◼   ► 2020 was Fantastical, 2021 was Bartender, 2022 was Audio Hijack, picking up a Lifetime Achievement Award,

00:18:22 ◼   ► 2023 Whisper.

00:18:24 ◼   ► Interesting here. So we got some Apple apps, we got Audio Hijack, Fantastical twice, Bartender thrown in there.

00:18:35 ◼   ► I know, I mean, in any category where there's a Lifetime winner, the easy selection is to choose the Lifetime winner.

00:18:42 ◼   ► But I kind of want to choose Audio Hijack as the Lifetime winner, even though it's a, or as a Hall of Famer.

00:18:49 ◼   ► It's all, like, you talk to people who are on Windows and then know about Mac stuff, like, Anze Toma is just like this.

00:18:58 ◼   ► Like, Audio Hijack, like, it's so good. Like, it's so smart.

00:19:04 ◼   ► There's nothing like it.

00:19:05 ◼   ► That interface that they built, because for people who don't remember, the old Audio Hijack interface was terrible.

00:19:10 ◼   ► But the new Audio Hijack interface with the little blocks that are all connected and that you can like record from different things and process them and send them different places.

00:19:17 ◼   ► And for podcasts, it's invaluable.

00:19:20 ◼   ► But actually, it's one of those things that the Rogue Amoeba stuff in general, as a Mac user, it does make you wonder why that stuff is not in the operating system.

00:19:29 ◼   ► It's so powerful and so useful, and they keep getting better.

00:19:34 ◼   ► They added automation support. They added their new transcription block.

00:19:38 ◼   ► So I feel like I had just a huge amount of love for that app.

00:19:45 ◼   ► I can see the argument for Fantastical, which has stuck out of space trying to do something better than Apple.

00:19:54 ◼   ► Although I got to be honest, I have a little bit of a crisis of faith right now about Fantastical, where I feel like in order to try and justify itself and build its business around features that don't interest me.

00:20:07 ◼   ► And I'm starting to wonder if I might actually be better off just saving my money and going back to Calendar.

00:20:14 ◼   ► There are things in Fantastical that I really value, but I do agree that the app is maybe going to places that I'm not interested in.

00:20:24 ◼   ► And I know as well that a lot of people aren't super happy with the subscriptions.

00:20:28 ◼   ► And Fantastical subscription is one of the more expensive ones.

00:20:32 ◼   ► It is. And I think those go hand in hand.

00:20:36 ◼   ► Just spitballing here. And again, we love everybody.

00:20:39 ◼   ► And it's a great app and I do love it.

00:20:41 ◼   ► I still recommend it.

00:20:42 ◼   ► With the price, which is they set the price because they felt like that's what they needed to do to run their business.

00:20:47 ◼   ► I have no problem with that. You can buy it or you cannot buy it.

00:20:50 ◼   ► But I do feel like that at that price, they then feel pressure to drive the product into places that are going to justify the price to businesses and to people who, again, that's their choice.

00:21:01 ◼   ► And if you are somebody who's served by those features, that's great.

00:21:04 ◼   ► For me, I see these new features like, "Oh, we'll schedule you and you've got free and busy time and things like that for people to schedule meetings with you."

00:21:12 ◼   ► And I'm like, "Doesn't interest me."

00:21:14 ◼   ► None of these features actually serve me.

00:21:18 ◼   ► And so, yeah, I find myself wondering, is it a subscription I should really keep or not?

00:21:24 ◼   ► So here's what I'll say.

00:21:26 ◼   ► So going back to what I was talking about in the iOS app one, I just think Audio Hijack is an app that over its time period, since we first awarded it, and we first awarded it in 2016 because it got so good.

00:21:40 ◼   ► I think that was when the UI changed.

00:21:42 ◼   ► Because it was an app that I didn't use before 2016 because it just didn't make any sense to me.

00:21:49 ◼   ► And then since then, it's become probably the most important app on my Mac for me and what I do.

00:21:57 ◼   ► And it has consistently gotten better and better and better over time when they integrated live streaming into the app, which is super important for us.

00:22:06 ◼   ► And now, from where we are now looking into the future that they did, if you say the AI transcription block, that feels like that's going to be important for us going into the future.

00:22:17 ◼   ► Yeah, so the new version came out at the beginning of 2015.

00:22:21 ◼   ► Okay.

00:22:22 ◼   ► So right there, almost at the beginning of when we started doing upgrade is when Audio Hijack appeared.

00:22:30 ◼   ► Which is helpful for me.

00:22:31 ◼   ► It feels like a no-brainer to me.

00:22:35 ◼   ► Yeah, I agree.

00:22:37 ◼   ► All right, so that's that, right?

00:22:39 ◼   ► Audio Hijack is the Hall of Fame winner for Mac app.

00:22:44 ◼   ► Yeah.

00:22:45 ◼   ► We're happy about that one.

00:22:47 ◼   ► Hooray.

00:22:48 ◼   ► All right, so next up, our next category will be the best newcomer Mac app, which I think we can maybe give this entire category a note here to say it is the reason that we introduced upgrade in nominations.

00:23:08 ◼   ► Because we were really struggling to come up.

00:23:12 ◼   ► Ah, yes, yeah.

00:23:13 ◼   ► With new Mac apps.

00:23:14 ◼   ► With new Mac apps.

00:23:15 ◼   ► Especially in the darkest time.

00:23:16 ◼   ► Because there was a time period.

00:23:17 ◼   ► Oh, yeah, the darkest time.

00:23:18 ◼   ► Probably around 2017, where we only gave one runner up in the category.

00:23:23 ◼   ► There was a problem here.

00:23:26 ◼   ► And so that was kind of like a dip time, and we needed help.

00:23:30 ◼   ► And so we started asking the upgrade-ients to vote too, and that gave us much more to talk about.

00:23:36 ◼   ► So, going back to 2014, pull one out for one of my favorite apps of all time, Mailbox.

00:23:42 ◼   ► Oh, Mailbox.

00:23:43 ◼   ► Remember Mailbox?

00:23:44 ◼   ► Man, I tell you what, 2014, this is a mood, right?

00:23:48 ◼   ► Overcast, Workflow, Fantastical, Mailbox as iOS and Mac.

00:23:53 ◼   ► God, what a great time.

00:23:54 ◼   ► That's when we started.

00:23:55 ◼   ► That is the time.

00:23:56 ◼   ► That is the moment we started, was that time.

00:23:58 ◼   ► That's my nostalgia right there.

00:23:59 ◼   ► So, best newcomer Mac app.

00:24:01 ◼   ► We'll go back to that.

00:24:02 ◼   ► 2014 was Mailbox.

00:24:03 ◼   ► 2015 was Fantastical.

00:24:05 ◼   ► 2016 was Bear.

00:24:06 ◼   ► 2017 was Twitterrific.

00:24:09 ◼   ► 2018 was Drafts.

00:24:10 ◼   ► 2019 was NetNewswire.

00:24:12 ◼   ► 2020 was Nova.

00:24:14 ◼   ► 2021 was MimeStream.

00:24:16 ◼   ► 2022 was MimeStream.

00:24:18 ◼   ► MimeStream again.

00:24:19 ◼   ► And then '23, Ivory.

00:24:21 ◼   ► Yes.

00:24:22 ◼   ► I mean, look, I will just say for Mailbox, all right?

00:24:26 ◼   ► Mailbox is, in my opinion, the best email app ever made.

00:24:30 ◼   ► And it was the first app to do a bunch of things, like swiping on emails to perform actions on them.

00:24:37 ◼   ► Snoozing came from Mailbox.

00:24:39 ◼   ► And also one of the greatest features in an email app of all time that nobody has ever done, which I don't understand,

00:24:45 ◼   ► is allowing you to manually just drag and drop the order of your emails in your inbox around.

00:24:50 ◼   ► I don't know why nobody else has ever done that, but nobody else has ever done that.

00:24:54 ◼   ► But it just allowed you to kind of -- I mean, what Mailbox was doing was a thing that people don't like,

00:24:59 ◼   ► which was using your email inbox as a to-do list.

00:25:04 ◼   ► But for so many people in the world, that is just the function of an email app.

00:25:08 ◼   ► And so they just made the best possible version of that app.

00:25:12 ◼   ► I don't think Mailbox is going to win this category, but I just had to give it its time,

00:25:16 ◼   ► because I just think it was so innovative and so cool, and Dropbox bought it and killed it.

00:25:21 ◼   ► Yeah, Dropbox just bought it and killed it. That was what happened.

00:25:24 ◼   ► Why? Why?

00:25:26 ◼   ► This was at the time when Dropbox was trying to work out what on earth it could charge people for,

00:25:31 ◼   ► and it thought email was one of those things.

00:25:33 ◼   ► Then it thought document collaboration was another one with Dropbox Paper, and the list goes on and on.

00:25:38 ◼   ► I struggle with this one outside of Mailbox, honestly.

00:25:43 ◼   ► Honestly, I think the answer is MimeStream.

00:25:46 ◼   ► Not only is it a hall of famer because it was the newcomer two years in a row, how is that possible?

00:25:51 ◼   ► And a runner-up the following year. Just amazing.

00:25:55 ◼   ► Like, the long game played by MimeStream, well done.

00:25:58 ◼   ► But also, look, it's a developer inside Apple who works on the Mail app, and I don't like the Mail app.

00:26:05 ◼   ► I don't think it's very good. I'm frustrated by it. Constantly, I gave it up.

00:26:08 ◼   ► He goes out on his own, starts a business, says, "We're going to make a great Mail app for the Mac."

00:26:15 ◼   ► "Mac first" focuses on Gmail, which is great because I use Gmail, and says,

00:26:19 ◼   ► "We're going to build a great Mac-only, at least first, email app

00:26:26 ◼   ► and compete with the app that I used to work on inside Apple."

00:26:30 ◼   ► What a great story. And the net result is, it's a legitimately great app.

00:26:35 ◼   ► And I think when you're talking about building a legitimately great Mac first, Mac-only app,

00:26:41 ◼   ► that is part of the story of a really great Mac newcomer.

00:26:46 ◼   ► And there are a couple in that category, right? Like, Nova is Mac only.

00:26:51 ◼   ► But MimeStream, being great and being from somebody who was on the inside

00:26:57 ◼   ► and decided they could do better on the outside, and then they did it, right?

00:27:00 ◼   ► Then they did it, because MimeStream is legitimately a great app.

00:27:04 ◼   ► I feel like that, plus, again, managed to win twice, newcomer twice. What? So great.

00:27:12 ◼   ► I'm happy to go with MimeStream, because I don't really have particularly strong feelings for...

00:27:19 ◼   ► Okay. I mean, I think that's the best case I can make for any of them, is that one.

00:27:22 ◼   ► It's the most fun for me, because it won it twice. I just think that's so hilarious,

00:27:26 ◼   ► that we might as well give it a third award in this category.

00:27:29 ◼   ► So the best newcomer Mac app, Hall of Fame entrant, MimeStream.

00:27:35 ◼   ► The next category we're not going to award, which is, because we've just created the best feature category,

00:27:41 ◼   ► which WidgetSmith won, and we can't really give somebody a Hall of Fame for one time.

00:27:47 ◼   ► So we'll move on to the next category now, which is Game of the Year.

00:27:52 ◼   ► Game of many years, Game of the Decades.

00:27:56 ◼   ► The title of Game of the Year is funny.

00:27:58 ◼   ► So the Game of the Year award winners go as 2014 Mario Kart 8, 2015 Splatoon, 2016 Firewatch,

00:28:07 ◼   ► 2017 The Legend of Zelda Breath of the Wild, 2018 Pokemon Let's Go,

00:28:13 ◼   ► 2019 Pokemon Sword and Shield, 2020 Animal Crossing New Horizons, 2021 Forza Horizon 5,

00:28:23 ◼   ► or as I have written it in our document, Forizan Horizon.

00:28:27 ◼   ► Which, that's not correct.

00:28:29 ◼   ► Forza Horizon 5, 2022 Marvel Snap, and 2023 Zelda Tears of the Kingdom.

00:28:38 ◼   ► Alright, so, this is very difficult, okay? So I'm going to tell you where I'm leaning right now, Jason.

00:28:45 ◼   ► Looking at this list, I think this needs to be out of Mario Kart 8, Legend of Zelda Breath of the Wild, Pokemon Let's Go,

00:28:55 ◼   ► or Animal Crossing New Horizons.

00:28:57 ◼   ► While I think Tears of the Kingdom is a better game than Breath of the Wild,

00:29:01 ◼   ► and why I think it's what I believe right now is my favorite over that, I think it's too close in time to make that judgment,

00:29:10 ◼   ► and to call Tears of the Kingdom the Hall of Fame winner.

00:29:14 ◼   ► Animal Crossing New Horizons was just a time and place, you know?

00:29:19 ◼   ► It was a game that many people needed when we needed it.

00:29:23 ◼   ► Pandemic time and pandemic place, yeah.

00:29:25 ◼   ► Pokemon Let's Go was a game that just took over the world, right?

00:29:31 ◼   ► Everyone was playing Let's Go.

00:29:33 ◼   ► Oh no, that's Pokemon Go. Pokemon Let's Go is a different thing.

00:29:37 ◼   ► We can exclude Pokemon Let's Go from this conversation.

00:29:40 ◼   ► No, yeah, it's not what you think.

00:29:42 ◼   ► So Breath of the Wild, Mario Kart, I think it's between Breath of the Wild, Mario Kart 8, and Animal Crossing New Horizons.

00:29:50 ◼   ► I'm now going to knock out Animal Crossing from this list.

00:29:55 ◼   ► I love the game, but it's not like, compared to the other two, it's not as high a quality.

00:30:00 ◼   ► And so then I'm thinking, right, so we've got,

00:30:02 ◼   ► Zelda is the better game, but then I think if it's the two of us deciding, probably Mario Kart, right?

00:30:08 ◼   ► Well, I mean, I have both of them, but the one that I play all the time is Mario Kart,

00:30:12 ◼   ► although I played lots of versions of Mario Kart.

00:30:14 ◼   ► Mario Kart 8 is just the one that came out at that point on Switch and on Wii U, actually.

00:30:22 ◼   ► Yep.

00:30:23 ◼   ► Woo!

00:30:24 ◼   ► Technically the 2014 winner was Mario Kart 8 Deluxe.

00:30:28 ◼   ► The Wii U one was Mario Kart 8, and the Switch one is Mario Kart 8 Deluxe.

00:30:34 ◼   ► And that is actually what we're talking about here.

00:30:36 ◼   ► We were not talking about the Wii U game then.

00:30:38 ◼   ► Well, I love Mario Kart, but there are many of them.

00:30:40 ◼   ► I feel like Breath of the Wild was new and influential and then led on to the amazing follow-up as well.

00:30:47 ◼   ► And I'd say it gets the Julian endorsement as well.

00:30:50 ◼   ► Oh, I am wrong.

00:30:52 ◼   ► We are talking about Mario Kart 8, because that was in 2014.

00:30:56 ◼   ► Switch one didn't come out until 2017.

00:30:58 ◼   ► My opinion is, knock this out and it's Breath of the Wild.

00:31:01 ◼   ► That's where I'm living.

00:31:02 ◼   ► Okay, great.

00:31:03 ◼   ► Cool.

00:31:04 ◼   ► Legend of Zelda Breath of the Wild is the winner.

00:31:06 ◼   ► I love Mario Kart 8, but Mario Kart 8 Deluxe is the actual one that everyone knows and plays and is better.

00:31:12 ◼   ► Sure.

00:31:13 ◼   ► And if we're talking about that, then Zelda should take it, in my opinion.

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00:33:07 ◼   ► So now we move into favorite movie.

00:33:12 ◼   ► Oh yeah, nice.

00:33:14 ◼   ► We go back to 2014. Captain America Winter Soldier.

00:33:20 ◼   ► That's a good movie.

00:33:21 ◼   ► What a great movie.

00:33:22 ◼   ► 2015 Star Wars Episode VII The Force Awakens.

00:33:27 ◼   ► Force Awakens.

00:33:28 ◼   ► 2016 Star Wars Rogue One.

00:33:31 ◼   ► Yeah, big Star Wars boys.

00:33:33 ◼   ► Yep, well there we go into the next time.

00:33:35 ◼   ► We love our Pokemans. We love our Star Warses.

00:33:38 ◼   ► Yep, Star Wars.

00:33:40 ◼   ► In 2017, Spider-Man Homecoming.

00:33:43 ◼   ► In 2018, Spider-Man Into the Spider-Verse.

00:33:47 ◼   ► Oh, big Spider-Man boys.

00:33:49 ◼   ► 2019 Avengers Endgame.

00:33:52 ◼   ► 2020 Hamilton.

00:33:54 ◼   ► Hey, there were no other movies.

00:33:58 ◼   ► 2021 Spider-Man No Way Home. Back to Spider-Boys.

00:34:02 ◼   ► 2022 Turning Red.

00:34:04 ◼   ► 2023 Oppenheimer.

00:34:06 ◼   ► This one is easy for me.

00:34:09 ◼   ► Okay, what's your choice?

00:34:10 ◼   ► Avengers Endgame.

00:34:12 ◼   ► Wow, oh interesting, interesting.

00:34:15 ◼   ► Yeah.

00:34:16 ◼   ► Interesting.

00:34:17 ◼   ► That's not what I would pick.

00:34:19 ◼   ► You thought I would have gone with Spider-Man?

00:34:21 ◼   ► Yeah, Spider-Man Into the Spider-Verse, which would probably be my choice of these.

00:34:26 ◼   ► Avengers Endgame.

00:34:28 ◼   ► It's good. We saw Infinity War together.

00:34:31 ◼   ► We did.

00:34:32 ◼   ► And it's your bachelor party.

00:34:33 ◼   ► Yeah, I wish we'd seen Endgame together, but I liked Infinity War too.

00:34:37 ◼   ► It was a bit of a downer for the...

00:34:39 ◼   ► Well, I mean, yeah.

00:34:41 ◼   ► It's a downer ending.

00:34:42 ◼   ► Spoilers for Infinity War, there's a downer ending.

00:34:44 ◼   ► Thank you, seriously?

00:34:47 ◼   ► Good news is there's a whole other movie and that one doesn't have a downer ending, so just watch the next one.

00:34:53 ◼   ► It takes six hours out of your day.

00:34:55 ◼   ► My pitch for Endgame is it was just an incredible payoff for so much work, you know?

00:34:59 ◼   ► Yeah, I agree.

00:35:01 ◼   ► It's a really good movie, but Into the Spider-Verse is a technical marvel and fantastically fun.

00:35:06 ◼   ► Yeah, one of the best animated movies ever.

00:35:08 ◼   ► So I'm good with either.

00:35:10 ◼   ► Let's do Spider-Man Into the Spider-Verse.

00:35:12 ◼   ► Yeah, I think that's a good pick.

00:35:14 ◼   ► So much Spider-Man in this.

00:35:16 ◼   ► We are big Spider-Man boys.

00:35:18 ◼   ► Big Spider-Boys.

00:35:20 ◼   ► Yeah, now I'm feeling bad that I let Oppenheimer beat out Spider-Man Across the Spider-Verse.

00:35:25 ◼   ► Maybe I'm not. Maybe that's too much Spider-Man in this category.

00:35:29 ◼   ► Too many Spideys. Too many.

00:35:31 ◼   ► What that would have been like...

00:35:33 ◼   ► Was he in Winter Soldier?

00:35:35 ◼   ► No.

00:35:36 ◼   ► No, he was in Civil War, wasn't he?

00:35:38 ◼   ► Yeah, because that would have been incredible, because that would have been like half of the movies had Spider-Man.

00:35:42 ◼   ► Yeah, we have like four Spider-Men pointing at each other in the Upgrades.

00:35:46 ◼   ► That's a lot. We're really in the Spider-Verse.

00:35:49 ◼   ► The favorite movie category actually is the Spider-Verse, if you think about it.

00:35:53 ◼   ► It is, pretty much.

00:35:54 ◼   ► There's so much Spider-Man in there.

00:35:56 ◼   ► But we love Spider-Man at the Upgrades.

00:35:58 ◼   ► We do. That's right, we do.

00:36:00 ◼   ► I think similarly fun now is the favorite television show.

00:36:04 ◼   ► Oh, nice.

00:36:05 ◼   ► This one's going to be good, I think.

00:36:07 ◼   ► This started in 2018, so there are fewer here.

00:36:10 ◼   ► 2018's winner was Patriot.

00:36:12 ◼   ► 2019 was Watchmen.

00:36:14 ◼   ► 2020 was Ted Lasso.

00:36:17 ◼   ► 2021 was For All Mankind.

00:36:19 ◼   ► 2022 was Severance.

00:36:21 ◼   ► 2023 was The Bear.

00:36:23 ◼   ► Ooh.

00:36:27 ◼   ► Yeah.

00:36:28 ◼   ► Now, here's a question for you.

00:36:30 ◼   ► Do we just judge the season in which we're talking about?

00:36:35 ◼   ► I don't think we need to do that.

00:36:38 ◼   ► We could, but we don't have to.

00:36:40 ◼   ► I mean, Patriot only had two seasons, Watchmen only had the one.

00:36:44 ◼   ► Ted Lasso has three, For All Mankind has four.

00:36:47 ◼   ► Severance only has the one, Bear has two.

00:36:50 ◼   ► All right, so of this, right?

00:36:54 ◼   ► I'll try and stop breaking this down a little bit.

00:36:57 ◼   ► Pure television quality, Watchmen.

00:37:01 ◼   ► Yes, I agree.

00:37:03 ◼   ► Feeling, Ted Lasso.

00:37:07 ◼   ► Well, it depends on the feeling. It's a good feeling.

00:37:09 ◼   ► There's lots of other feelings in For All Mankind.

00:37:12 ◼   ► Right.

00:37:13 ◼   ► And I actually think, I loved Patriot,

00:37:16 ◼   ► but I think for me it's out of those three.

00:37:19 ◼   ► Watchmen, Ted Lasso, For All Mankind.

00:37:21 ◼   ► I feel like I would knock Ted Lasso out on that three.

00:37:27 ◼   ► Probably Watchmen.

00:37:30 ◼   ► I think it's Watchmen.

00:37:31 ◼   ► I've only seen it once.

00:37:32 ◼   ► I looked at this list, I just rewatched it.

00:37:35 ◼   ► Okay.

00:37:36 ◼   ► It is the best show of the last decade for me.

00:37:39 ◼   ► It's brilliant.

00:37:40 ◼   ► It's just brilliant.

00:37:41 ◼   ► It is truly.

00:37:42 ◼   ► I can't think of a show that has so much to say

00:37:50 ◼   ► and does it in such an elegant way as Watchmen does.

00:37:54 ◼   ► That makes it very special, I think.

00:37:59 ◼   ► Watchmen?

00:38:00 ◼   ► Watchmen.

00:38:02 ◼   ► Watchmen is the Hall of Fame winner

00:38:04 ◼   ► joining Spider-Man and The Spider-Verse for movies

00:38:06 ◼   ► and then Watchmen for TV.

00:38:08 ◼   ► I think there was a time when these were the same category

00:38:11 ◼   ► and we split it out over time.

00:38:13 ◼   ► Yeah, I think that was what we did.

00:38:16 ◼   ► So that's why it started in 2018.

00:38:18 ◼   ► I've got so much to say about the next one.

00:38:22 ◼   ► Favorite book?

00:38:24 ◼   ► Oh good.

00:38:25 ◼   ► Well, I mean, I had so much to say about Game.

00:38:27 ◼   ► Yeah, good point.

00:38:28 ◼   ► 2014.

00:38:29 ◼   ► Yeah.

00:38:30 ◼   ► The Golem and the Genie.

00:38:31 ◼   ► Yes.

00:38:32 ◼   ► 2015, The Goblin Emperor.

00:38:34 ◼   ► Oh, so good.

00:38:35 ◼   ► 2016, The Fifth Season.

00:38:37 ◼   ► 2017, The Caledonian Gambit.

00:38:40 ◼   ► Yay.

00:38:41 ◼   ► 2018, The Calculating Stars.

00:38:44 ◼   ► Good one.

00:38:45 ◼   ► 2019, Trail of Lightning.

00:38:47 ◼   ► Oh yeah, I did like that one.

00:38:49 ◼   ► You did like that one.

00:38:50 ◼   ► I don't know anything about that.

00:38:51 ◼   ► 2020, A Memory Called Empire.

00:38:53 ◼   ► Mm, so good.

00:38:54 ◼   ► 2021, Piranesi.

00:38:56 ◼   ► Piranesi.

00:38:57 ◼   ► 2022, Elder Race by Adrian Tchaikovsky.

00:39:01 ◼   ► Tchaikovsky.

00:39:02 ◼   ► I don't know why it's the only one I read the author name for, which is the hardest one.

00:39:05 ◼   ► I don't know why either.

00:39:06 ◼   ► And 2023, Mountain in the Sea.

00:39:09 ◼   ► Rainailer.

00:39:10 ◼   ► Yeah.

00:39:11 ◼   ► Okay, so if you want a little list of Jason's books that he recommends that you read, that's

00:39:16 ◼   ► a pretty good list.

00:39:17 ◼   ► That's a pretty good list.

00:39:19 ◼   ► The book that I keep coming, oh, there's so many really good books on here.

00:39:23 ◼   ► The book that I keep coming back to and recommending to people, that was such a find.

00:39:29 ◼   ► And now there are more books, it's not quite a series, there are more books in that world,

00:39:34 ◼   ► but that first book is, it stands alone and it's magical.

00:39:39 ◼   ► And so I think I'm just gonna say, again, what's my favorite book of the last decade?

00:39:46 ◼   ► 'Cause that's what we're doing here.

00:39:48 ◼   ► When you think of it that way, it's a little bit weird.

00:39:50 ◼   ► I mean, and it's not, it's the decade of 2014 to now, right?

00:39:55 ◼   ► So it's not a traditional kind of decade.

00:39:58 ◼   ► It's "The Goblin Emperor" by Katherine Addison from release 2014, the winner in 2015.

00:40:04 ◼   ► "The Goblin Emperor," it's just great.

00:40:09 ◼   ► It's a great book.

00:40:11 ◼   ► It's a coming of age story and it's about like machinations and all this stuff in this

00:40:16 ◼   ► fantasy, steampunk kind of world, but it's like way better than if you're turned off

00:40:21 ◼   ► by fantasy, steampunk.

00:40:23 ◼   ► It's so good.

00:40:24 ◼   ► It's just a great book.

00:40:25 ◼   ► It's like a big warm hug of a delight of a book.

00:40:27 ◼   ► I reread it when I was on vacation in Hawaii.

00:40:30 ◼   ► I was like, you know what?

00:40:31 ◼   ► I'm gonna reread "The Goblin Emperor" and I have no regrets.

00:40:33 ◼   ► It was great the second time too.

00:40:35 ◼   ► And I very rarely reread books, but I was happy to reread it.

00:40:39 ◼   ► So I'm gonna say "The Goblin Emperor."

00:40:40 ◼   ► There we go.

00:40:43 ◼   ► Oh, I've enjoyed in this one.

00:40:44 ◼   ► Our next category is favorite podcast.

00:40:47 ◼   ► And I feel like the only way to do this is to...

00:40:51 ◼   ► We have to roll in the other podcast categories, right?

00:40:53 ◼   ► Yeah.

00:40:54 ◼   ► So that includes...

00:40:57 ◼   ► This is gonna be really complicated.

00:40:58 ◼   ► This will include...

00:40:59 ◼   ► Let me take a crack at it.

00:41:01 ◼   ► Oh, here's the thing.

00:41:02 ◼   ► Here's the thing.

00:41:03 ◼   ► I wanna actually just discuss this with you before we decide.

00:41:06 ◼   ► Oh, okay.

00:41:07 ◼   ► All right.

00:41:08 ◼   ► Because we have multiple.

00:41:09 ◼   ► So we have favorite podcast now, but we used to have favorite tech podcast, favorite non-tech

00:41:13 ◼   ► podcast, and favorite podcast newcomer.

00:41:16 ◼   ► Now, do we include the podcast newcomers or do we just do...

00:41:19 ◼   ► Because that kind of is the award now.

00:41:22 ◼   ► It's taken place of all three of those categories.

00:41:25 ◼   ► So do we go through all of them and pick a winner?

00:41:30 ◼   ► I say yes.

00:41:33 ◼   ► All right.

00:41:34 ◼   ► I'm very happy to do this.

00:41:36 ◼   ► I have them in front of me.

00:41:37 ◼   ► So our favorite...

00:41:38 ◼   ► We'll just simplify the podcast category into one and then pick a winner.

00:41:46 ◼   ► Yep.

00:41:47 ◼   ► So favorite podcast newcomer, 2014 at isometric 2015, reconcilable differences.

00:41:53 ◼   ► 2016, Dubai Friday.

00:41:55 ◼   ► 2017, S-Town.

00:41:57 ◼   ► 2018, The Good Place, the podcast.

00:42:00 ◼   ► 2019, Two-Headed Girl.

00:42:02 ◼   ► 2020 was 20 max for 2020.

00:42:06 ◼   ► 2021 was downstream.

00:42:09 ◼   ► Then in 2014 for favorite non-tech podcast, we had The Flop House.

00:42:19 ◼   ► 2015, The Flop House.

00:42:21 ◼   ► 2016, The Flop House, Lifetime Achievement Award.

00:42:24 ◼   ► 2017, The Adventure Zone.

00:42:26 ◼   ► 2018, Dubai Friday.

00:42:28 ◼   ► 2019, Dubai Friday.

00:42:30 ◼   ► 2020, Reconcilable Differences.

00:42:32 ◼   ► 2021, Reconcilable Differences.

00:42:35 ◼   ► Then favorite tech podcast.

00:42:37 ◼   ► 2014, ATP.

00:42:39 ◼   ► 2015, ATP.

00:42:40 ◼   ► 2016, ATP.

00:42:42 ◼   ► 2017, Lifetime Achievement Award.

00:42:44 ◼   ► 2017, Welcome to Macintosh.

00:42:46 ◼   ► 2018, Connected.

00:42:48 ◼   ► 2019, Automators.

00:42:49 ◼   ► 2020, Dithering.

00:42:51 ◼   ► 2021, Mac Power Users.

00:42:53 ◼   ► Then favorite podcast from 2022, Connected.

00:42:58 ◼   ► 2023, The Town.

00:43:01 ◼   ► Yeah.

00:43:02 ◼   ► A lot of podcasts there.

00:43:04 ◼   ► This is hard.

00:43:05 ◼   ► This is very hard.

00:43:06 ◼   ► Podcast Hall of Fame.

00:43:08 ◼   ► I mean, it's the obvious places to start with the Lifetime Achievement Award winners, which

00:43:16 ◼   ► are The Flop House and ATP.

00:43:19 ◼   ► We created the Lifetime Achievement Award for these exact two shows because the first

00:43:23 ◼   ► three years they won in their respective categories.

00:43:26 ◼   ► And we were worried that it would end up just being ATP as the favorite tech podcast every

00:43:31 ◼   ► year because it is really good and it is loved by our audience.

00:43:36 ◼   ► And so we created the Lifetime Achievement Award.

00:43:38 ◼   ► And the same for The Flop House where we were both listening to the net.

00:43:41 ◼   ► I don't listen to The Flop House anymore.

00:43:43 ◼   ► Just rotate it out over time.

00:43:45 ◼   ► Sad.

00:43:46 ◼   ► I don't know.

00:43:49 ◼   ► I mean, I feel like it's probably going to be ATP.

00:43:53 ◼   ► I feel like.

00:43:54 ◼   ► Yeah, I think so.

00:43:55 ◼   ► That's where I'm leaning.

00:43:56 ◼   ► That's a good choice.

00:43:57 ◼   ► I think if we consider over the history of the show and think about ATP as a part of

00:44:05 ◼   ► our industry, the quality of the show over that time, it remains very consistent.

00:44:12 ◼   ► I mean, you were just talking with Jon about it.

00:44:14 ◼   ► Like the fact that they've won.

00:44:16 ◼   ► They're on every episode.

00:44:17 ◼   ► All three of them is actually.

00:44:19 ◼   ► Honestly, that is an achievement worth awarding on its own.

00:44:23 ◼   ► Honestly, like they have an episode where they have an achievement that they've won

00:44:26 ◼   ► honestly.

00:44:27 ◼   ► Like they have an episode every single week and it's all three of them.

00:44:29 ◼   ► Like that is so much harder than it sounds.

00:44:33 ◼   ► I tell you right now.

00:44:34 ◼   ► Like if you think of in your life, if you have a weekly meeting, how often someone's

00:44:38 ◼   ► missing from the weekly meeting.

00:44:40 ◼   ► Like they go on vacations, right?

00:44:43 ◼   ► Like they have emergencies in their lives, but the three of them do it.

00:44:46 ◼   ► So honestly, for just that reason, from my perspective, just that alone, they deserve

00:44:52 ◼   ► an award.

00:44:53 ◼   ► I think.

00:44:54 ◼   ► Yeah.

00:44:55 ◼   ► I think, I think making, given our awarding them and the fact that they are, and we still,

00:45:00 ◼   ► you know, we, we do a lot of follow-up and they're friends of the show, but they're also,

00:45:03 ◼   ► it's such an accomplishment for them to have done it for so long.

00:45:06 ◼   ► They started that before, before I left my job at IDG.

00:45:11 ◼   ► In fact, it's been going on a long time now.

00:45:13 ◼   ► Jason, this was, I mean, they did it before relay was a thing.

00:45:17 ◼   ► Yeah.

00:45:18 ◼   ► Yeah.

00:45:19 ◼   ► Well that's the, yeah.

00:45:20 ◼   ► The same timeframe, right?

00:45:21 ◼   ► Like we're talking about, about starting our 10th year and doing this after 10 upgrade-ies,

00:45:24 ◼   ► but they're, they're past their 10th anniversary now.

00:45:27 ◼   ► So incredible accomplishment.

00:45:28 ◼   ► So yeah, that, that, that alone, I would say.

00:45:31 ◼   ► And I feel like it will, I wanted to, there was so many people that I had to really think

00:45:35 ◼   ► about it, but realistically, this is probably the easiest win to give.

00:45:40 ◼   ► Yeah.

00:45:41 ◼   ► I mean, the flophouse is still my all time favorite podcast, but I think for this category,

00:45:45 ◼   ► this is the right choice.

00:45:47 ◼   ► Yep.

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00:48:11 ◼   ► Our next category is our favorite Apple product.

00:48:16 ◼   ► Ooh, this is a big one.

00:48:18 ◼   ► Yeah.

00:48:19 ◼   ► Oh boy, I need, there's some of these, they sneak up on you and you're like, uh oh.

00:48:23 ◼   ► Apple product of the decade.

00:48:24 ◼   ► Uh oh, this could be difficult.

00:48:26 ◼   ► All right, we're going to go back as we have been to 2014 with the 5K iMac.

00:48:32 ◼   ► Yeah, big deal.

00:48:34 ◼   ► That's not the iMac Pro, right?

00:48:36 ◼   ► No, that's the first Retina iMac, which I bought.

00:48:40 ◼   ► Yeah, first Retina iMac.

00:48:43 ◼   ► 2015 Apple Watch.

00:48:46 ◼   ► 2016 AirPods.

00:48:50 ◼   ► 2017 the iPhone 10.

00:48:54 ◼   ► Yeah.

00:48:55 ◼   ► 2018 the 12.9 inch iPad Pro.

00:48:59 ◼   ► 2019 AirPods Pro.

00:49:02 ◼   ► 2020 is the MacBook Air with M1.

00:49:06 ◼   ► 2021 is the 14 inch MacBook Pro.

00:49:10 ◼   ► 2022 is the M2 MacBook Air.

00:49:13 ◼   ► And 2023 is the iPhone 15 Pro Max.

00:49:16 ◼   ► The thing that is the most surprising to me, there is only two iPhones.

00:49:20 ◼   ► Yeah.

00:49:21 ◼   ► Way more Macs.

00:49:23 ◼   ► Big Mac boys.

00:49:24 ◼   ► That's us.

00:49:25 ◼   ► All right, so again, I'm going to mentally remove the iPhone 15 Pro Max for me in the liberation.

00:49:31 ◼   ► I just don't think it's worth including that.

00:49:33 ◼   ► The iPhone 10, I don't think I would put that there either.

00:49:37 ◼   ► I wouldn't.

00:49:38 ◼   ► I mean, that is a big step forward.

00:49:41 ◼   ► Essentially, the iPhone we have used since then is the iPhone 10, right?

00:49:46 ◼   ► Like essentially.

00:49:47 ◼   ► Yeah.

00:49:48 ◼   ► It's a little bigger and all that, but like that was the, you could really draw a line in the iPhone in before and after iPhone 10.

00:49:55 ◼   ► So big deal influentially, but I agree.

00:49:58 ◼   ► It would not be on my short list in this category.

00:50:00 ◼   ► I think AirPods would be.

00:50:04 ◼   ► Or AirPods Pro.

00:50:05 ◼   ► I don't.

00:50:06 ◼   ► Yeah, maybe.

00:50:07 ◼   ► I mean, the M2 MacBook Air, I think is the best Mac of all time.

00:50:11 ◼   ► So that's up there for me.

00:50:12 ◼   ► So I was going to say, how much do we want to short circuit this conversation?

00:50:16 ◼   ► Because I know what my vote is.

00:50:18 ◼   ► Your MacBook Air and M2?

00:50:20 ◼   ► It's the M2 MacBook Air.

00:50:21 ◼   ► I stopped at M1 MacBook Air and I was like, wow, okay.

00:50:24 ◼   ► Apple's most important and best selling product or laptop, Mac laptop.

00:50:29 ◼   ► Right?

00:50:30 ◼   ► Yeah.

00:50:31 ◼   ► MacBook Air.

00:50:32 ◼   ► M1.

00:50:33 ◼   ► They, super influential, still being sold, still good.

00:50:39 ◼   ► Excellent.

00:50:40 ◼   ► So good.

00:50:41 ◼   ► Adina has one and I've said to her multiple times, would you like to consider an M2 at some point?

00:50:45 ◼   ► And she's like, why would I do that?

00:50:46 ◼   ► I love this computer.

00:50:47 ◼   ► I much prefer, she much prefers the, like the wedge design to the like boxy design.

00:50:53 ◼   ► And she's like, and the battery's incredible.

00:50:55 ◼   ► The screen's great.

00:50:56 ◼   ► Like why would it?

00:50:57 ◼   ► I get it.

00:50:58 ◼   ► So that's the argument for the M1.

00:50:59 ◼   ► I look at the M1 and I think, well, yeah, but then the M2 is so much, it has all the attributes of the M1

00:51:05 ◼   ► and I think is so much better in terms of its design.

00:51:09 ◼   ► And I do think it's maybe the best Mac Apple has made in a very long time, if not ever.

00:51:16 ◼   ► And that, so it's got my vote, honestly.

00:51:20 ◼   ► MacBook Pro 14, like that screen is gorgeous and the power of those higher end chips.

00:51:24 ◼   ► Yes, absolutely, but like the MacBook Air, which is your number one Mac is the MacBook Air.

00:51:31 ◼   ► The story of the Mac over the last 15 years, basically 13 years is the MacBook Air.

00:51:36 ◼   ► And that M2 is such a wonderful redesign of a design that it's sort of been the same for a very long time.

00:51:46 ◼   ► Basically always.

00:51:48 ◼   ► Always, like the original and the second edition was slightly different, but it was the same realistically.

00:51:56 ◼   ► And then it stayed that way.

00:51:58 ◼   ► It didn't change.

00:52:00 ◼   ► It really didn't.

00:52:01 ◼   ► It went retina, it didn't really change.

00:52:03 ◼   ► They wanted it to be as reminiscent of the old one as possible.

00:52:05 ◼   ► The M1 is based on that design and then they did the M2 and it's so good.

00:52:11 ◼   ► So yeah, I think that, I agree, AirPods Pro is a great, and AirPods, great product, some of my favorite Apple products.

00:52:20 ◼   ► Apple coming out with a brand new product in a brand new category, the Apple Watch, and they've been successful with that.

00:52:26 ◼   ► But I feel like it's the MacBook Air M2.

00:52:28 ◼   ► I just, the moment I saw these 10 products, I was, I literally was like, "Oh, M1 Air, such a landmark."

00:52:35 ◼   ► And then I thought, "Oh, but M2 Air."

00:52:39 ◼   ► But M2 Air has got all the goodness of the M1 Air and is a brand new design that I love.

00:52:44 ◼   ► So yeah, M2 Air.

00:52:47 ◼   ► Hall of Fame winner for the best, for our favorite Apple product is the MacBook Air with M2.

00:52:54 ◼   ► Yeah, love it.

00:52:56 ◼   ► Favorite non-Apple product?

00:52:58 ◼   ► This is going to be hilarious.

00:53:00 ◼   ► 2014 PlayStation 4.

00:53:02 ◼   ► 2015, the Sphero BB8.

00:53:06 ◼   ► Yep, I've used that for about one, about two months, and then never again.

00:53:10 ◼   ► Really impressive, though.

00:53:12 ◼   ► It was very impressive.

00:53:14 ◼   ► I do love the 2015 Star Wars influence.

00:53:18 ◼   ► Star Wars V.

00:53:19 ◼   ► On the upgrade, everyone was very excited.

00:53:22 ◼   ► We were really into it.

00:53:23 ◼   ► 2016, the Logitech Create 9.7.

00:53:26 ◼   ► I don't know what that is. I assume it's a keyboard.

00:53:29 ◼   ► It's a keyboard for the iPad.

00:53:31 ◼   ► We can probably shut it down with 2017, the Nintendo Switch.

00:53:36 ◼   ► 2018, the Bridge keyboard.

00:53:39 ◼   ► Another iPad keyboard.

00:53:41 ◼   ► Roomba.

00:53:43 ◼   ► Roomba!

00:53:44 ◼   ► 2020.

00:53:45 ◼   ► Who doesn't love a sweeper robot?

00:53:46 ◼   ► PlayStation 5.

00:53:48 ◼   ► 2021, the Nintendo Switch OLED.

00:53:51 ◼   ► Then 2022, Steam Deck.

00:53:53 ◼   ► And 2023, Steam Deck OLED.

00:53:55 ◼   ► Big OLED boys.

00:53:57 ◼   ► It's got to be Nintendo Switch.

00:53:59 ◼   ► It's got to be the Nintendo Switch.

00:54:01 ◼   ► And I would put Nintendo Switch over Switch OLED just because most people have just the Switch.

00:54:06 ◼   ► The whole platform just starts right there.

00:54:09 ◼   ► I was talking to Julian about this the other day.

00:54:12 ◼   ► We got him that for his birthday on Nintendo Switch while we were on a road trip.

00:54:16 ◼   ► Because he had to spend his birthday basically in a car because we were on a road trip.

00:54:21 ◼   ► And he still plays on the Nintendo Switch all the time.

00:54:26 ◼   ► The longevity, I mean yeah, he's got a PS5 that he loves so much that he brought it home for Christmas.

00:54:32 ◼   ► Like for the Christmas break.

00:54:34 ◼   ► Because he didn't want to not play it for a month.

00:54:37 ◼   ► But the Switch just...

00:54:39 ◼   ► Remember what position Nintendo was in right then?

00:54:43 ◼   ► The Wii had been a real success and then they did the Wii U and everybody kind of went "ugh".

00:54:47 ◼   ► And then it was like "Oh boy Nintendo, you're in trouble. What are you doing?"

00:54:50 ◼   ► And they did their thing where they released a product that was underpowered.

00:54:53 ◼   ► And a handheld that could be docked to a TV and had those detachable controllers.

00:54:59 ◼   ► And it was like "Well this is interesting Nintendo but it's also very weird."

00:55:02 ◼   ► And in hindsight it was like "They killed it. They nailed it."

00:55:04 ◼   ► What a great platform they absolutely did.

00:55:08 ◼   ► It's like exceeded all expectations for that product. Such a great product.

00:55:12 ◼   ► Ok Nintendo, we have now awarded you with the Hall of Fame winner.

00:55:16 ◼   ► Can you please make a new one? Please make a new one. Please?

00:55:20 ◼   ► Yeah it's time for Switch 2. It's time for Switch 2.

00:55:24 ◼   ► I've heard someone in a podcast that I listen to, they're pitching Super Nintendo Switch.

00:55:28 ◼   ► Which I just think is an incredibly good name.

00:55:31 ◼   ► And I beg them to do it but they won't. It'll be Switch 2 which is fine.

00:55:35 ◼   ► But Super Nintendo Switch is the way to go.

00:55:37 ◼   ► Just follow me here, Mike. Switch U.

00:55:40 ◼   ► You're fired.

00:55:43 ◼   ► Don't bring that to my door, Jason.

00:55:46 ◼   ► Switch U.

00:55:47 ◼   ► Why would you do that to me? Don't do that to me. I'm gonna be worried about this now.

00:55:51 ◼   ► I'm the one who has a Wii U in his house now. Still.

00:55:54 ◼   ► Oh god.

00:55:55 ◼   ► Yeah. Yeah.

00:55:57 ◼   ► A category full of I think some personal vendettas.

00:56:04 ◼   ► Grievances. Grievances. Grievances. Yeah yeah yeah yeah.

00:56:08 ◼   ► The worst gadget/most disappointing technology.

00:56:12 ◼   ► We go back to 2014 with the LG G Watch.

00:56:16 ◼   ► I don't know what that is.

00:56:18 ◼   ► I googled it just before I said it and it is a horrifically ugly looking Android Watch.

00:56:25 ◼   ► Oh it's like they're...

00:56:27 ◼   ► We have beaten the Apple Watch to market with this wonderful thing that is...

00:56:35 ◼   ► I think I may have used this.

00:56:38 ◼   ► I think is why I'm... but anyway.

00:56:41 ◼   ► 2015, the MacBook keyboard.

00:56:43 ◼   ► This was the butterfly keyboard.

00:56:45 ◼   ► That's the butterfly keyboard, baby. Yeah.

00:56:47 ◼   ► 2016, the Galaxy Note 7, which would catch fire.

00:56:50 ◼   ► Catch fire, yeah. Oh oh oh.

00:56:54 ◼   ► 2017.

00:56:55 ◼   ► That's good stuff.

00:56:56 ◼   ► There's good stuff in this category. I just took a little look ahead.

00:56:59 ◼   ► 2017, the iPad Pro smart connector.

00:57:03 ◼   ► Now why did we hate this so much?

00:57:07 ◼   ► Because it was a letdown. We wanted so much more.

00:57:09 ◼   ► It was just a letdown.

00:57:10 ◼   ► All it was was Apple's keyboard and then that weird charger that Belkin made.

00:57:15 ◼   ► Right. You're right. It disappointed us that there weren't more things and it didn't...

00:57:18 ◼   ► Yeah, that's right. Okay.

00:57:19 ◼   ► 2018, AirPower.

00:57:22 ◼   ► The charging product that they never got.

00:57:24 ◼   ► Wow. I mean the disappointment is that Apple announced a product that it never shipped, which never happened.

00:57:28 ◼   ► Incredible.

00:57:29 ◼   ► It's amazing. What a moment.

00:57:30 ◼   ► The AirPower is such a fantastic blip in history for them. So good.

00:57:36 ◼   ► 2019, Mac Catalyst.

00:57:40 ◼   ► 2020, iOS apps on M1 Macs. We were upset that no one was allowing it.

00:57:46 ◼   ► Yeah, yeah, absolutely. It was super disappointing.

00:57:49 ◼   ► 2021, the Breville Jewel Sous Vide.

00:57:52 ◼   ► Oh man, I saw this and I immediately became enraged.

00:57:55 ◼   ► This is a Sous Vide thing that requires you to use an app to use it.

00:57:59 ◼   ► It doesn't have any physical controls. It only has app controls.

00:58:02 ◼   ► It's like you should never make a product that has no physical controls. Never, ever, ever, ever.

00:58:07 ◼   ► We were angry because in 2021, I also said AppleCare Plus. This is when my iPhone was all scratched and they wouldn't replace the screen.

00:58:13 ◼   ► That was... 2021 was a bad year for us.

00:58:15 ◼   ► Yeah, NFTs was the other runner up too. Called it. Nailed it.

00:58:18 ◼   ► What a great time. What a great time.

00:58:20 ◼   ► Oh, to be alive in 2021. Yeah.

00:58:22 ◼   ► 2022 was the iPad Pro.

00:58:25 ◼   ► Yes, because remember, they didn't really do anything except update the chips and they didn't upgrade the screen in the lower end model.

00:58:32 ◼   ► We all felt like it was time for a new iPad Pro and they said, "How about 2024 for that?" So we were disappointed.

00:58:39 ◼   ► Hopefully. Hopefully 2024. We actually don't know, but it's hopeful.

00:58:44 ◼   ► And 2023 was the humane AI pin.

00:58:48 ◼   ► Ha.

00:58:49 ◼   ► I think we go back, I would say maybe MacBook keyboard, maybe AirPower.

00:58:56 ◼   ► I feel like the story of the worst gadget/most disappointing tech of the last decade in our space is the butterfly keyboard.

00:59:04 ◼   ► Yeah.

00:59:05 ◼   ► I feel like that's the answer.

00:59:07 ◼   ► I mean, the silver lining was the episode, the Christmas episode that we just spoke about.

00:59:11 ◼   ► That was the silver lining.

00:59:13 ◼   ► Yeah.

00:59:14 ◼   ► That whole...

00:59:15 ◼   ► Who killed the butterfly keyboard?

00:59:16 ◼   ► Mm-hmm.

00:59:17 ◼   ► And it did die eventually.

00:59:18 ◼   ► It did.

00:59:19 ◼   ► It did.

00:59:20 ◼   ► It took some time, but it did die.

00:59:22 ◼   ► But I think that's the way.

00:59:24 ◼   ► I mean, Galaxy Note 7, that's a good one.

00:59:27 ◼   ► AirPower, that's a great one.

00:59:30 ◼   ► But I feel like it's got to be the butterfly keyboard.

00:59:33 ◼   ► Yeah, I agree.

00:59:34 ◼   ► All right.

00:59:35 ◼   ► So the Hall of Fame most disappointing technology is the MacBook Pro keyboard, the butterfly version.

00:59:43 ◼   ► Yeah.

00:59:44 ◼   ► It's a MacBook keyboard. Was it the MacBook Pro at that point? Was it just in the MacBook Pro?

00:59:47 ◼   ► It was the Pro then, I think.

00:59:48 ◼   ► I think it was...

00:59:49 ◼   ► Okay.

00:59:50 ◼   ► I don't know.

00:59:51 ◼   ► It started in the MacBook.

00:59:52 ◼   ► It doesn't matter.

00:59:53 ◼   ► But you know what it is.

00:59:54 ◼   ► It's the butterfly keyboard.

00:59:55 ◼   ► We're just going to call it the butterfly keyboard.

00:59:57 ◼   ► Everybody knows what we mean.

00:59:59 ◼   ► Yep.

01:00:00 ◼   ► Most life-changing hardware.

01:00:04 ◼   ► Which is a fun category name.

01:00:07 ◼   ► Fun category.

01:00:08 ◼   ► Interesting concept.

01:00:09 ◼   ► 2014, Jason's daughter's iPhone.

01:00:13 ◼   ► Yeah.

01:00:14 ◼   ► We'll get back to that.

01:00:16 ◼   ► 2015, iPad Pro.

01:00:19 ◼   ► 2016, Amazon Echo.

01:00:22 ◼   ► 2017, AirPods.

01:00:24 ◼   ► 2018, Apple Pencil 2.

01:00:27 ◼   ► 2019, it seems like there wasn't a winner according to my document, but I might be wrong.

01:00:33 ◼   ► I'll check the official upgrade.com.

01:00:35 ◼   ► Winner.

01:00:36 ◼   ► Okay.

01:00:37 ◼   ► 2020 was the magic keyboard for iPad Pro.

01:00:40 ◼   ► It's funny, keyboards.

01:00:41 ◼   ► We'll go back again.

01:00:43 ◼   ► We have 2021 was the Apple TV remote.

01:00:46 ◼   ► 2022 is our friend, the M2 MacBook Air.

01:00:50 ◼   ► 2023 was the Apple Watch Ultra 2.

01:00:54 ◼   ► Right.

01:00:55 ◼   ► So let me check the 2019.

01:00:57 ◼   ► 2019 was AirPods Pro.

01:00:59 ◼   ► I didn't put it in my spreadsheet.

01:01:02 ◼   ► So AirPods Pro was the 2019 winner.

01:01:05 ◼   ► Great.

01:01:06 ◼   ► Amazon Echo.

01:01:10 ◼   ► Nah, I don't think so.

01:01:12 ◼   ► No.

01:01:13 ◼   ► No.

01:01:14 ◼   ► No, Jamie's iPhone.

01:01:16 ◼   ► That's a real...

01:01:17 ◼   ► That was good for you, I suppose.

01:01:19 ◼   ► She's 13 and she got an iPhone.

01:01:22 ◼   ► I mean, it was a big deal and I was taking it literally, right?

01:01:25 ◼   ► Like life-changing hardware.

01:01:27 ◼   ► I think it's Apple's Pro.

01:01:29 ◼   ► I think it's AirPods Pro too.

01:01:30 ◼   ► Wow, we were just in sync.

01:01:32 ◼   ► I want to take you back.

01:01:34 ◼   ► Remember the AirPods came out at that time where it was like,

01:01:37 ◼   ► "Oh, Apple's going to remove the headphone jack."

01:01:40 ◼   ► And I was certainly upset about it because

01:01:43 ◼   ► I felt like wired headphones were so much better

01:01:46 ◼   ► and I used headphones with custom silicone

01:01:49 ◼   ► that fits my ears perfectly and in-ear monitors

01:01:52 ◼   ► and the quality is so great.

01:01:54 ◼   ► And Apple's headphones traditionally were terrible as well.

01:02:00 ◼   ► Let's not forget that.

01:02:01 ◼   ► Apple's headphones weren't good.

01:02:04 ◼   ► And then the AirPods came out

01:02:06 ◼   ► and it was a revelation like,

01:02:10 ◼   ► "Oh, wow, these are good."

01:02:13 ◼   ► I actually can most of the time just use AirPods.

01:02:18 ◼   ► They were kind of...

01:02:19 ◼   ► Whenever there was noise around and stuff, I couldn't.

01:02:21 ◼   ► But for general use, they were actually pretty good

01:02:24 ◼   ► and the wireless thing was great.

01:02:26 ◼   ► But then AirPods Pro came out

01:02:28 ◼   ► and all of those other use cases where it's like,

01:02:31 ◼   ► "Oh, when you're mowing the lawn, when you're on an airplane,

01:02:33 ◼   ► it's not as good as having the in-ear monitors,"

01:02:36 ◼   ► all went away because of the noise canceling.

01:02:39 ◼   ► And I think about how bad

01:02:42 ◼   ► I thought Apple's headphones were pre-AirPods.

01:02:46 ◼   ► And now, unless I'm doing a podcast like I am right now,

01:02:51 ◼   ► I just use AirPods Pro.

01:02:53 ◼   ► The only time I use wired headphones anymore is for podcasting.

01:02:56 ◼   ► That's it. That's literally it.

01:02:59 ◼   ► What a life-changing bit of hardware.

01:03:02 ◼   ► While the AirPods introduced it, the AirPods perfected it.

01:03:05 ◼   ► Perfected it.

01:03:06 ◼   ► It's the everything that it does.

01:03:09 ◼   ► The way in which you have the controls to pause

01:03:11 ◼   ► rather than smack in the side of your head,

01:03:13 ◼   ► which I hated with the AirPods.

01:03:16 ◼   ► You have volume control

01:03:17 ◼   ► and you also have transparency and active noise cancellation.

01:03:20 ◼   ► I feel like it's easy to forget

01:03:22 ◼   ► just how good Apple's noise cancellation was and is

01:03:26 ◼   ► and how I think it kind of pushed everybody to do more

01:03:29 ◼   ► in the earbud space.

01:03:33 ◼   ► Sure.

01:03:34 ◼   ► And they've only made it better and better

01:03:36 ◼   ► with the newer features that we've been talking about.

01:03:39 ◼   ► So, AirPods Pro.

01:03:40 ◼   ► And there's hearing aid functionality and stuff

01:03:42 ◼   ► is coming next year if reports are to be believed.

01:03:46 ◼   ► So, it's such a surprise in such a good way.

01:03:51 ◼   ► And again, life-changing.

01:03:53 ◼   ► And it has literally changed my behavior

01:03:55 ◼   ► in a bunch of different ways.

01:03:57 ◼   ► And now, when I go walk the dog or I go for a run,

01:04:00 ◼   ► it's Apple Watch and AirPods Pro and that's it.

01:04:03 ◼   ► That's all I take with me.

01:04:05 ◼   ► And I can still listen to podcasts and do what I want.

01:04:10 ◼   ► Just, yeah, great.

01:04:11 ◼   ► Great product.

01:04:13 ◼   ► Favorite tech story.

01:04:16 ◼   ► Wow.

01:04:17 ◼   ► Of the decade.

01:04:18 ◼   ► Yep.

01:04:19 ◼   ► Wow.

01:04:20 ◼   ► 2014, Tim Cook comes out as gay.

01:04:23 ◼   ► Oh, yeah.

01:04:24 ◼   ► 2015, Federico Viticci's iPad Pro review.

01:04:28 ◼   ► Sure.

01:04:29 ◼   ► 2016, Apple versus the FBI.

01:04:33 ◼   ► Ah, yes.

01:04:34 ◼   ► 2017, overreaching smartphone.

01:04:37 ◼   ► Don't know what that means.

01:04:39 ◼   ► What is that?

01:04:40 ◼   ► That might have been a specific story.

01:04:42 ◼   ► Zach probably has links.

01:04:44 ◼   ► So, Zach who put the Upgrades.com together.

01:04:47 ◼   ► I know it does a better job of...

01:04:49 ◼   ► So, maybe you want to check the Upgrades.com.

01:04:51 ◼   ► Yeah, I'll look there right now.

01:04:53 ◼   ► 2018.

01:04:54 ◼   ► Overreaching smartphones.

01:04:55 ◼   ► Oh, it's the...

01:04:56 ◼   ► Here it is.

01:04:57 ◼   ► I can provide some more color here.

01:04:59 ◼   ► Please.

01:05:00 ◼   ► Overreaching smartphones was our winner because that was the year that the Essential phone

01:05:04 ◼   ► and the red hydrogen one came out.

01:05:06 ◼   ► So, it was smartphones trying to out phone the iPhone by doing stupid things.

01:05:13 ◼   ► Yeah.

01:05:14 ◼   ► 2018, Apple spoils September event with bad URLs.

01:05:17 ◼   ► So, 9to5Mac found the site map and found everything.

01:05:21 ◼   ► Yeah.

01:05:22 ◼   ► 2019, understanding of technology privacy.

01:05:26 ◼   ► Don't know what that means.

01:05:29 ◼   ► 2020, the Apple Silicon transition.

01:05:32 ◼   ► 2021, App Store regulation.

01:05:35 ◼   ► 2022, FTX.

01:05:38 ◼   ► And 2023, the Apple Vision Pro.

01:05:43 ◼   ► All right.

01:05:45 ◼   ► Some standouts.

01:05:47 ◼   ► I mean, it just happened, but the Vision Pro was a really good story.

01:05:51 ◼   ► But maybe not.

01:05:53 ◼   ► 2020, the Apple Silicon transition.

01:05:55 ◼   ► Yeah.

01:05:57 ◼   ► Apple and the FBI was just like a fascinating thing that occurred and like, obviously, under

01:06:03 ◼   ► sad circumstances, but how that all...

01:06:05 ◼   ► That was just like an interesting thing to talk about.

01:06:07 ◼   ► Obviously, a monumental moment of Tim Cook coming out.

01:06:11 ◼   ► I think if I think back about the things that we've spoken about, the San Bernardino case

01:06:18 ◼   ► and the way all of that stuff around the FBI, like, it was really interesting to talk about.

01:06:25 ◼   ► And I actually feel like was maybe a bit of a turning point for our show about the way

01:06:31 ◼   ► in which the show would be, like the fact that we were having very big conversations

01:06:35 ◼   ► then about that stuff.

01:06:37 ◼   ► So that is up there for me.

01:06:40 ◼   ► It was one of the most interesting tech stories of the last decade.

01:06:43 ◼   ► It depends on how we want to do this.

01:06:44 ◼   ► I know.

01:06:45 ◼   ► I feel like the biggest story in our sphere of the last decade is probably the Apple Silicon

01:06:52 ◼   ► transition.

01:06:53 ◼   ► And think about how long we talked about Arm Max, right?

01:06:56 ◼   ► Like how many years beforehand we're like, are they going to do it?

01:06:59 ◼   ► When are they going to do it?

01:07:00 ◼   ► How can they do it?

01:07:01 ◼   ► Is it possible?

01:07:02 ◼   ► Will they be any good?

01:07:03 ◼   ► And then the story when it happened was also great.

01:07:06 ◼   ► Like it was a meaty, interesting, detailed story as the products came out.

01:07:11 ◼   ► And we had nothing but time to talk about it because of the pandemic as well.

01:07:15 ◼   ► So I think that that's a really strong contender.

01:07:17 ◼   ► And I'd say we have spent a lot of time talking about App Store regulation and the story continues.

01:07:23 ◼   ► And that has been a huge topic for this podcast.

01:07:26 ◼   ► Just the idea of like, what are Apple's policies and how are regulators going to try to break

01:07:33 ◼   ► Apple's policies and will it be possible?

01:07:35 ◼   ► And then it's like, realistically, so I think those are two really good picks to choose from.

01:07:40 ◼   ► I enjoyed talking about the Apple Silicon transition because it was fun.

01:07:43 ◼   ► I enjoyed talking about App Store regulation because it's not fun.

01:07:46 ◼   ► Like I get pretty fired up about it and I like to talk about it.

01:07:50 ◼   ► Yeah.

01:07:52 ◼   ► But I feel like awarding something good feels better.

01:07:58 ◼   ► I agree. I agree.

01:07:59 ◼   ► Apple Silicon transition.

01:08:00 ◼   ► Apple Silicon transition.

01:08:02 ◼   ► Great story.

01:08:03 ◼   ► Story of the decade.

01:08:04 ◼   ► Yep.

01:08:05 ◼   ► The final category is our favorite tech screw up.

01:08:13 ◼   ► Oh, man.

01:08:14 ◼   ► Going back to 2014 with the Amazon Fire Phone.

01:08:19 ◼   ► 2015.

01:08:22 ◼   ► Aaron Rodgers throws a surface.

01:08:25 ◼   ► I do love that.

01:08:26 ◼   ► That moment is iconic to this day.

01:08:28 ◼   ► Although the other quarterbacks have emulated it.

01:08:33 ◼   ► It's just, I'm disgusted by your Microsoft service and I'm going to toss it away.

01:08:37 ◼   ► 2016, the Samsung Note 7 explodes.

01:08:41 ◼   ► 2017, the HomePod leak.

01:08:45 ◼   ► Oh yeah.

01:08:47 ◼   ► We learned all sorts of things about everything.

01:08:50 ◼   ► About future features and face ID and all sorts of things from a HomePod firmware update.

01:09:00 ◼   ► What?

01:09:01 ◼   ► Oh yeah.

01:09:02 ◼   ► It was more than just the HomePod.

01:09:04 ◼   ► It was like all over.

01:09:06 ◼   ► 2018.

01:09:07 ◼   ► Oh no.

01:09:08 ◼   ► Steve Trout and Smith took it apart and found like face ID, details, and iPhone 10 bezel with the notch.

01:09:21 ◼   ► It was all in there.

01:09:24 ◼   ► 2018 was the Facebook privacy scandals.

01:09:29 ◼   ► 2019 was the Samsung Galaxy Fold because it was breaking.

01:09:37 ◼   ► 2020 was Quibi.

01:09:39 ◼   ► Quibi.

01:09:41 ◼   ► 2021, Apple sees Sam announcement.

01:09:44 ◼   ► 2022, Elon Musk buys Twitter.

01:09:48 ◼   ► 2023, OpenAI fires Sam Altman.

01:09:53 ◼   ► I think early contenders for me.

01:09:56 ◼   ► Elon Musk buying Twitter, Apple sees Sam announcement.

01:10:00 ◼   ► So many good ones here.

01:10:03 ◼   ► I think they're my two big ones.

01:10:05 ◼   ► I got to put the Fire Phone on the list too.

01:10:09 ◼   ► I don't care about the Fire Phone.

01:10:11 ◼   ► Hey, remember when Amazon was going to redo, they made their own phone and nobody wanted it.

01:10:17 ◼   ► Just like rejected, talked in a hand.

01:10:20 ◼   ► Was that something we said 2014?

01:10:22 ◼   ► It was like 3D.

01:10:23 ◼   ► It was.

01:10:24 ◼   ► Yeah, you could like tilt it.

01:10:26 ◼   ► Boy, everybody keeps trying to make 3D screens happen.

01:10:28 ◼   ► It's not going to happen.

01:10:29 ◼   ► Yeah, because the red hydrogen tried to do that as well.

01:10:33 ◼   ► Clearly that's not good to do on a phone.

01:10:36 ◼   ► Galaxy Note exploding.

01:10:38 ◼   ► I mean, not only is there the point in laugh of Samsung, but also remember where like every, maybe you don't,

01:10:44 ◼   ► but in the US, I will tell you every flight you got on for like a year said,

01:10:47 ◼   ► "If you have a Samsung Galaxy Note 7, we must take it from you.

01:10:51 ◼   ► You must power it down or whatever it was."

01:10:53 ◼   ► It just kept on going of just like name blocking that phone.

01:10:59 ◼   ► I thought they would never do another Note.

01:11:01 ◼   ► Yeah, right.

01:11:03 ◼   ► And honestly, I will also speak for Quibi.

01:11:06 ◼   ► What a disaster.

01:11:08 ◼   ► Like people put money into this thing and there were executives and like it was very clear from the outside.

01:11:16 ◼   ► It was a terrible idea.

01:11:18 ◼   ► From the conception and yet they're like, "Nope, we're going to do it.

01:11:23 ◼   ► We got a Super Bowl ad. We're going."

01:11:26 ◼   ► And it was exactly as big a flop as everybody expected.

01:11:29 ◼   ► Apple CCM announcement is interesting because they were like, "Aha, this is going to solve it."

01:11:33 ◼   ► And it was broken in so many different ways.

01:11:37 ◼   ► Like some of their methodology was immediately called into question by experts who were like,

01:11:41 ◼   ► "It doesn't work like that."

01:11:43 ◼   ► And people got up in arms about the idea that your phone was going to scan your stuff and prevent it from being uploaded.

01:11:49 ◼   ► And like now there's on-device scanning and they thought they were working around like,

01:11:52 ◼   ► "Oh, but it's actually a security issue because we're not scanning it in the cloud."

01:11:55 ◼   ► And it became this whole thing that ended up being like they had kind of retracted and changed their whole approach.

01:12:01 ◼   ► So there was some special stuff there.

01:12:04 ◼   ► Yeah, this is a great category to revisit just for fun.

01:12:10 ◼   ► Yeah. I don't know. Elon Musk buying Twitter is one of the colossal screw-ups of all time.

01:12:16 ◼   ► It really is.

01:12:18 ◼   ► It is. I don't think we've ever had something that could have won it two years in a row.

01:12:25 ◼   ► And it could have.

01:12:26 ◼   ► It totally could have.

01:12:28 ◼   ► Without one thing happening, it would have.

01:12:30 ◼   ► And even then it was still on the bubble, right?

01:12:32 ◼   ► Yeah. In fact, I would say not only could it have won for 2023, but it also seems fairly likely that it could win it for 2024.

01:12:41 ◼   ► Yes.

01:12:42 ◼   ► Which would be like the idea that you could be in the, not the Hall of Fame, but in the, whatever we call it.

01:12:48 ◼   ► The Lifetime Achievement Award for tech screw-up.

01:12:53 ◼   ► That could be a thing that you could get.

01:12:55 ◼   ► But you could totally get it for that.

01:12:58 ◼   ► I feel like Elon Musk buys Twitter should be.

01:13:00 ◼   ► Let's do it.

01:13:01 ◼   ► We've got to put it in the Hall of Fame.

01:13:02 ◼   ► Hall of Fame screw-up.

01:13:03 ◼   ► So that's it. We've done it.

01:13:07 ◼   ► That's it.

01:13:08 ◼   ► I'm going to run through these again just as a, for completion's sake.

01:13:11 ◼   ► Okay. Yeah. Let's do it.

01:13:13 ◼   ► The best iOS app, Carrot Weather. Best newcomer iOS app, Widgetsmith. Best Mac app, Audio Hijack. Best newcomer Mac app, MimeStream.

01:13:24 ◼   ► Game of the Year, The Legend of Zelda, Breath of the Wild. Favorite movie, Spider-Man, Into the Spider-Verse.

01:13:32 ◼   ► Favorite TV show, Watchmen.

01:13:35 ◼   ► Favorite book, The Goblin Emperor.

01:13:37 ◼   ► Favorite podcast, ATP.

01:13:40 ◼   ► Favorite Apple product, the MacBook Air with M2.

01:13:44 ◼   ► Favorite non-Apple product is the Nintendo Switch.

01:13:47 ◼   ► The worst gadget or most disappointing technology is the butterfly keyboard.

01:13:52 ◼   ► The most life-changing hardware is the AirPods Pro.

01:13:55 ◼   ► Our favorite tech story is the Apple Silicon transition.

01:13:59 ◼   ► And our favorite tech screw-up, Elon Musk buys Twitter.

01:14:03 ◼   ► So that is it.

01:14:06 ◼   ► There you go.

01:14:07 ◼   ► For the very first, and I hope just first, Hall of Fame entry.

01:14:12 ◼   ► To be another one, I guess we have to do this for another 10 years?

01:14:18 ◼   ► I mean, not necessarily.

01:14:19 ◼   ► We could do it in five?

01:14:20 ◼   ► In five years if we wanted to.

01:14:22 ◼   ► We might want to.

01:14:23 ◼   ► It depends.

01:14:24 ◼   ► I feel like it depends on when the calendar falls and we need multiple special episodes.

01:14:28 ◼   ► To be fair, I had this thought before we needed this.

01:14:33 ◼   ► I had this thought in September, so like I wasn't really thinking that far ahead.

01:14:37 ◼   ► So like this is just something that I thought would be nice to do because we finally made it to the 10th annual, which was pretty cool.

01:14:45 ◼   ► If you'd like to send us your feedback, your follow up and your questions, please go to upgradefeedback.com.

01:14:50 ◼   ► You can check out Jason's work at sixcolors.com, the incomparable dot com and here on Relay FM where you'll find me too.

01:14:56 ◼   ► And you can find my work at cortexbrand.com.

01:14:59 ◼   ► We are on Mastodon.

01:15:00 ◼   ► Jason is at Jason now on zeppelin.flights.

01:15:03 ◼   ► I am at iMike, i-m-y-k-e on mike.social.

01:15:06 ◼   ► The show is Upgrade at relayfm.social.

01:15:09 ◼   ► You can watch video clips of the show there.

01:15:12 ◼   ► We pick out some of the best things that happen in an episode.

01:15:15 ◼   ► We have our wonderful team that help us out.

01:15:17 ◼   ► These are also on TikTok, Instagram and YouTube where we are at Upgrade Relay and all of them.

01:15:22 ◼   ► If you want to watch the full video episodes of the show, they are also on our YouTube channel.

01:15:27 ◼   ► I am on threads as @imike, i-m-y-k-e.

01:15:30 ◼   ► Jason is @jsnell, j-s-n-e-double-l.

01:15:33 ◼   ► Thank you to our members who support us with Upgrade Plus.

01:15:36 ◼   ► They get longer ad free versions of every single episode of Upgrade.

01:15:40 ◼   ► You can go to getupgradeplus.com to find out more.

01:15:43 ◼   ► Thank you to our sponsors of this episode, Squarespace, ExpressVPN and Fitbud.

01:15:48 ◼   ► But most of all, thank you for listening.

01:15:50 ◼   ► Happy New Year. We'll be back next week.

01:15:53 ◼   ► Until then, say goodbye, Jason Snell.

01:15:56 ◼   ► Happy New Year, Mike. Happy New Year, everybody.

01:15:59 ◼   ► Thanks for listening. See you next week.

01:16:01 ◼   ► [Music]

01:16:15 ◼   ► such as happiness or happiness for people's lives.