The Missing Middle
32:14 Share

Hello and welcome to App Stories. Today's episode is brought to you by Incogni. I'm John Voorhees and with me is Federico Vittici. Hey Federico. Hello John, how are you? I'm having a great day. I'm having a great day. I wanted to talk to you about apps today. What do you think? Well, it's like a different way to go for this. Well, I mean the podcast is called App Stories after all, so it only seems fair that we talk about apps today.

Every once in a while. Every once in a while. You came up with this topic, which is something that I think we have discussed on and off on Mac Stories Weekly, on the monthly log, on the site, on App Stories. This idea of, you call it the missing middle. Can you explain what you mean by this? What sort of topic we're going to talk about? Yeah, we're going to talk about kind of the evolution of...

projects and businesses and their software needs. And we're specifically going to be talking about Mac Stories because, you know, I think when you and I first started working together, and for many years, we have used essentially consumer apps to run Mac Stories. Very, you know, we did have, we were using Slack for a while, but we're not anymore. We have had, you know, the one-off here and there, and we use Google Workspace. We've been using that for a very long time.

and its many iterations and names. But for the most part, you know, we kind of all, and this is one of the actually, one of the things that I love about what we do is that nobody's telling me what app to use, which was something that drove me bananas as somebody who really was into apps, drove me bananas when I was in the Windows world working as a lawyer because, you know, not only did I have to use

and PowerPoint and all those kind of apps. But I had a bunch of like enterprisey stuff I had to deal with. I didn't have any control over when things got updated. So even if I were excited about a new feature coming to Outlook 365 or something like that, I might have to wait months before I ever saw the light of day on my desktop. And that stuff drove me to run a parallel Mac

in my office and I would essentially do all my work on my Mac and then transfer over the written work product and stuff over to Windows when it had to go to somebody else. And what you and I do, and this is true with all the people we work with is that

You know, we're kind of doing our own thing with task managers and email. And you and I are probably more on the same page with apps than most of the rest of the team, just because you and I have a lot more crossover and things that we have to work on from like a business end of things. And that really is true with both.

both task managers and email in particular, but now we're using Discord. And we've always used, like I said, a lot of consumer-oriented software. What the problem with that is, though, is that it only takes you so far. One of the things about consumer software is it's generally not built for coordination, collaboration, communication, and that sort of thing.

Yeah. Yeah.

And it's $100 a month, not just for you, but it's $100 a month for everybody who uses the service of the software. And so it becomes exponentially expensive, which I think for a lot of small companies, and particularly I'm talking about really small companies like we are,

There's this uncomfortable middle where you could benefit from some of those features, but oftentimes they are cost prohibitive. Or even if they're not cost prohibitive, to get to that one feature that you kind of want or need for what you're doing is

you're adding a lot of complexity that you don't want. And we've got a pretty simple setup for the most part. And so you're introducing complexity and more kind of administrative overhead. Yeah, I think the main problem is that... So when I started Mac Stories, I was just by myself and I was mostly using like...

personal apps right i was right using the email clients that i wanted to use i didn't have to communicate with anybody else i would just get email into my email clients i didn't have any any requirements in terms of sharing those emails because it was just it was just me and over the course of multiple iterations of the mac stories team over the past 16 years um

You know, services have come and gone and apps have come and gone. And, you know, I've been through it all. Like I remember going from consolidating all of our chats in, oh gosh, what was the name?

GroupMe. No, before GroupMe. Oh, before GroupMe. Adium. Was that the IM? You used Adium? I did use Adium. For Mac Stories? Yes. I didn't know that. I didn't know that. The Mac app with the duck icon, I think. Adium was like this. Yeah, that's the one. You know, this idea of consolidating multiple cats into a single experience. You see it right now with like all these services that are all the rage like

beeper for example which is now owned by automatic recently came out with a new beta version actually but this idea of consolidating chats from multiple services goes way back like the days of aol days basically right yeah yeah and so back in the day like we're talking 2009 2010 i would use idiom and put like uh irc

AIM, like all of those services together into a single chat. And then eventually, you know, the Mac Stories team was like three people. And we moved to GroupMe. And then Slack came around and we started using Slack. And then you came around. And so we kept using Slack. And then for a while, we moved over to iMessage. And we had this giant group thread in iMessage and realized, oh, this is a bad idea. Yeah, very bad idea, yeah.

Before threads and replies on iMessage, it was just a long transcript. And so eventually, a few years ago, we settled. After Slack, we settled on Discord. But this is just one example. My...

This episode of App Stories is brought to you by Incogni. Did you know that data brokers can collect, aggregate, and sell information, including names, social security numbers, login credentials, and more? That can lead to annoying spam and more serious issues like identity theft. Thankfully, you can solve those issues with Incogni. They reach out to data brokers on your behalf, request your personal data removal, and deal with any objections from their side.

- Privacy is really important. And you know what the thing is, is that you're exposed all over the place, from all the websites you visit, from all the services you sign up for, all that stuff. I'm constantly getting emails telling me that my privacy has been compromised in some way or another because I signed up for some service or with some business somewhere. And Incogni is there to try to help you avoid that stuff. Because with Incogni, you can protect your privacy in three easy steps.

Just create an account, grant them the right to contact data brokers on your behalf, and then kick back while they do all the work. And if you want to stay up to date with the progress, a user-friendly dashboard provides updates on the status of your removal requests. Just visit incogni.com slash appstories and secure your data today. Sign up and enjoy a 30-day money-back guarantee.

Protect your privacy with Incogni and experience peace of mind knowing that your personal information is safe. Take your personal data back with Incogni. Use the code appstories when you go to the link in the show notes and get 60% off an annual plan. That's incogni.com slash appstories. Our thanks to Incogni for their support of the show. The way when you propose this topic,

I immediately thought of this tension that I have between the apps that I want to use, but at the same time, the requirements and the needs that you have if you're running a small to medium company such as Mac Stories. We don't have corporate enterprise requirements in terms of security standards or controls for employees and certifications that we must use, but we do have...

pretty moderate needs in terms of like, we have to use something that allows us to easily share our email inboxes or something that allows us to have real-time conversations with a little bit more structure. And that's where I think you're driving at with the idea of the missing middle is that Apple products tend to be, and Apple services tend to be good to great for personal use. But the moment you enter like even a small team context,

that's when it sort of starts to fall apart. Yeah, no, I think that's absolutely right. And I think, and then from an economic standpoint, I think one of the things is, is that if you are a business that is making enterprise software,

Your target is somebody with a big, fat, juicy budget of tens of thousands of dollars with hundreds of employees, not a team of five or six people who are going to maybe be willing to pay you $20, $30, $40 a month, that kind of thing. So yeah, I think that's very true of Apple's apps. I think that that divide exists in more general third-party apps too. And I think that...

that one of the things that big companies want is something that you touched on is, first of all, they want some sort of guarantee certification for, you know, whether it's security, whether it's some sort of compliance with regulations in a particular country. But they also want a certain level of customer service and a lot of

A lot of what I consider consumer software doesn't offer that. Sure, you can email the developer and you might get a response, but a lot of this enterprise software comes along with a you'll make a phone call and someone will fix your problem immediately.

which is not something that you get with just kind of your off the app store app usually. Yeah, and this is a great point because it's very true, not because I want to criticize Apple's reminders or notes, but it is true for a whole bunch of third-party apps where,

I think you wrote about this, actually, maybe last year. Like this sort of, I don't want to say disappearance altogether, but the market for the so-called prosumer application has kind of dried up because you have the personal, you know, single player, to use a video game analogy, experience.

Or you have the Microsoft Teams and Slack and Salesforce, God forbid. Those enterprise-oriented tools. And so you have these two extremes, right? And somewhere in the middle, when there's maybe somebody like me, somebody like you, a company like Mac Stories, I'm not speaking on behalf of Relay, but I have to imagine that it has to be similar for Relay and other small to medium companies where you're like,

you're thinking and you're like, okay, I don't want to spend like $500 a month on a service, but this $5 a month app is not enough. And so that middle where you would be able to say allocate, I don't know, $50 a month budget to your email client or document collaboration service or, I don't know, a task manager with team functionalities, that middle is

is becoming more rare and rare to find. Yeah, no, that's absolutely true. I think there are some companies that do it better than others. There's more thin slicing of subscription models at times where you can get some of those team features without having to be

the large corporation with tens of thousands of dollars in your budget. And I'm thinking, for instance, I think Todoist does a good job of this. I think Todoist, like you and I are both using Todoist right now and you shared a project of yours with me so that I can see what you're planning to write about on Club Mac Stories for Mac Stories Weekly, which is helpful because then I don't go out and find the same link or the same app and write the same thing and waste my time. And

we're not really using it for true collaboration. It's more of like a reference source for me more than anything else. Cause I'm not like, you're not assigning me tasks. I'm not assigning you tasks, but it is nice to have that feature and be able to coordinate that way. And if we wanted to, we could go a step further and we could have joint projects that are assigned some to, you know, some tasks to you, some tasks to me. It's not kind of the style, the way we like to work really. But yeah,

But I think Todoist does a very nice job in that the way their pricing structure works, it's more doable to do that kind of thing than it is for a lot of other apps. Yeah. And a lot of the things that we do, they could be done with Apple software, right? We could share enlisting reminders. We could share... Well, we wouldn't be able to share...

Apple Mail, but, you know, Apple Notes. And we've done it. Yeah, we do. Notes, I think, is probably the Apple app where we have shared the most over time. I think now we're not doing that as much. But, yeah, Apple Notes is a good way to do that with some stuff. And passwords, I guess, we're using. Passwords, yeah. But I keep coming back to this idea of

The problem with Apple software in this regard, in this sort of middle scenario, is that the moment you want to go even slightly beyond and have some kind of web-based control, right? Maybe because you want to have a web page where you can go in and check in, okay, has Devon joined? Is, you know, Alex part of this project? Like,

Apple tends to fail when it comes to having a centralized web-based sort of dashboard for your team. Because Apple doesn't really, and I'm not saying that they should, because maybe they don't want to, but Apple doesn't really go after the team market. They're much more into the, it's either personal use or family use, right? True, although they do have a growing enterprise.

you know, team at Apple. And there are companies that are deploying Macs and iPads and iPhones all the time. Right, but we are not deploying a fleet of iPads. No, that's true. And that's the difference between hardware and software, I suppose, too. I mean, obviously there are third-party solutions. There are a lot of them you see advertised all the time where people are managing

managing groups of Apple hardware and the apps that are on them. But I get your point. I mean, I think the focus of the company and the focus of the software is first and foremost about consumer and personal technology, not about business software. Yeah. And I think another company that does a good job here, even though we don't use it, is Notion.

- Yeah, that's true. - A service that can be used for yourself for free, even if you want to. And they have their version for small teams, but they also have an enterprise version. And so you see Notion be used by individuals as well as small teams, as well as bigger companies that have built entire projects and databases and reference files on top of Notion. So that idea of being able to scale from personal use to small team use to enterprise use,

I think that's exactly the sort of flow that I've been missing in a whole bunch of products lately. And I don't know why. Here's the thing. I don't know why there's this almost like rejection of the prosumer small team as an entity that may be willing to give you money. It seems like it's either like these two extremes of like it's either personal or it's enterprise. And...

Yeah, I have a theory, Federico. My theory is that that prosumer small business is just as needy in terms of hands-on attention as the enterprise customer, but they don't have the budget and maybe aren't going to stick around as long. So the cost of...

maintaining that relationship is too high for some of these companies. Interesting. That's interesting. That's my theory. That's my theory. Another trend that we've seen obviously lately is the slow but steady rise of team-based AI products. Yeah.

And this is a whole other conversation. We are using some of them. We are sharing a cloud space together. We're also using, Sylvia is also using it. We're using Shortwave, which is the email client that we talked about. We're sharing, you know, you have a bunch of, like, we can share messages, we can comment on messages. And obviously that also gives you access to a whole bunch of AI features. But

We're seeing, I think, in this space, a repeat of the same idea. Like this AI features that you have to pay for, you go from personal usage and maybe a pro version like ChugGPT as ChugGPT free or ChugGPT plus, which is 20 bucks a month. Cloud as cloud free and cloud pro, which is also 20 bucks a month. But then immediately after that step, there's the

enterprise adjacent version where Claude, you must have five seats in your account if you want to use the team stuff. And ChatDVD, it goes from $20 to $200 a month. Like there's that middle where you could say, well, I guess I can give you, you know, instead of 20, I can give you 50 or 75. No, there's that big jump from 20 to 200. And you're like, oh God, okay.

Right, right. Let me give you another example of a company that I think does do it right. And I think your example of Notion is a good one. They're a past sponsor and you and I have used it before, along with Alex and others to plan out various projects. And I think it is particularly good for project oriented type things. Yeah.

But the other company that I'm thinking of is actually Memberful, another sponsor of Mac Stories in the past. Because they really, I mean, we've been using Memberful, as I've mentioned in the ads that I've read, for like 10 years now. And that really has spanned maybe not so much time.

a huge growth in number of people working at Mac Stories. Although, you know, back when that started, it was maybe three or four people for the most part, and we are bigger now. But it really has grown with us in terms of our needs and what we needed for the club, you know, going from just a simple newsletter to a bunch of other things. Yeah, I think that's a good example. And, you know, there are...

I think there are other services that do a pretty good job in terms of covering the full spectrum because it is a spectrum of different users and different small or medium businesses that you can cater to. For example, GitHub. I think GitHub, especially after the Microsoft acquisition, they have a lot. You can get plenty of...

of work done on GitHub without paying a single dime. And that was not the case years ago. Now it is the case. You can set up something like... I recently set up a GitHub code space, which basically gives you a terminal in the cloud where you actually have a virtual...

but a virtualized terminal in the cloud and you can set up a repo and you can just, you know, actually write files and edit files in there. It's a completely virtualized environment and you can just use it for free. Like it doesn't matter. And so, and obviously they have, they have pricing tiers and, you know, and also that service is changing now with GitHub Copilot, obviously, which is their AI product. Like, but mostly,

I feel like I'm concerned that the prosumer ship has sailed...

and it's not coming back. That is my concern. - Yeah, I think you're right about that. And I think it's an interesting, the dynamic reminds me a little bit of when apps go from paid upfront to subscription, at least in terms of the fallout for some of these companies, because I'm thinking of two examples in particular, two prosumer apps. One is PDF Pen. Remember PDF Pen for the Mac? - Oh yeah, oh yeah. - They went, that company got sold

And it went very much to the enterprise side of things. I think there's still some prosumer users using it on the Mac, but it's not like it was before where it was owned by Smile. And it was very much, you know, it was like the PDF app that everybody used if they had a Mac. And now it's more of an enterprise thing. And another one really is Fantastical because as much as I like Fantastical, I think...

For a lot of individuals, it has outgrown in terms of what it does. It's offering a lot of features that someone like you and me don't need. And you're paying for those if you're subscribing to Fantastical. And I've just seen a lot of people abandon it as a result from personal use.

And that's too bad, but I totally get it. I mean, an app like Fantastical and a calendaring app that handles things like Zoom calls is very much in the sweet spot for enterprises, and I'm sure they can make a lot more money that way. I just feel like they have kind of left behind some of their audience in terms of individual users.

Yeah. It'd be interesting, though, to see at some point Apple maybe tackle this space, right? And to see, you know, I could see a world in which Apple is, for example, selling new iCloud plans, right? Because that's their primary sort of subscription that they're selling and sort of have iCloud for personal usage or iCloud for family usage or iCloud for small and medium teams, right?

I think what 1Password is doing is interesting. You can use 1Password by yourself or they have separate products for families and teams. Because you have very different needs, whether you're setting up a shared space for a family or for a team. And I think it'd be interesting to see an iCloud for teams. That would be something that I'd be intrigued to check it out, but obviously it doesn't exist.

And same with iWork. I mean, I know Apple doesn't call it iWork anymore, but I feel like... They don't really, right? They don't really. No, they don't. And I feel like they've sort of tried with Pages and Keynote and Numbers to address that market. But I feel like the development of those apps is on kind of a slower back burner pace where it just doesn't quite...

I just don't feel like it meets enough of the needs of small and medium businesses to really become the default, I guess, the way that a lot of Microsoft products are or Google products for that matter. Can I tell you my dream? What's your dream? Shortcuts for Teams. How many times...

do I have to send you individual shortcuts with an iCloud link? And then a few days later, I'm like, John, here's an updated version of the shortcut and it's a new link. And then you're like, oh, I forgot. I was using an older version.

My dream, because like, and I think this will be part of, I have two, three articles that I'm planning for this spring before WWDC. And one of them is this idea of revisiting the concept that we hear so often in the Apple community of the locking effect. And because I think there are new types of locking on Apple platforms these days. And I'm not joking when I say that

Amongst others, shortcuts plays a big role in locking you into Apple platforms. Oh, I agree. It's going to play a much bigger role, I think, with Apple intelligence. I hope. Well, I hope. But I think the moment you get used, like I have, to get work done using shortcuts and to sort of design your workflow around the automations that shortcuts can let you build, it becomes really hard to use something else. Parentheses.

I know that I'm going to get comments from people saying, have you tried Microsoft Power Automate? Or have you tried Tasker on Android? Let me tell you, dear listener, I have. And...

It's not that I'm biased because I like shortcuts. I've tried. I actually have some tasker automation set up on Android right now. I know what I'm talking about. It's like a thousand years behind just how intuitive and powerful shortcuts can be. And so the idea of the shortcuts for Teams or even Apple Mail for Teams, like

That would be a dream for me to be able to just onboard, you know, team members and just say, here's a folder of shortcuts that you can use. Or here's a bunch of like notes in Apple Notes that act as reference for Mac stories. Like this idea of like, I don't need to set up an enterprise. I'm not an enterprise. I am not deploying a fleet of iPads. I am not deploying a whole bunch of iPhones. I just run a small business and I want to have a shared space for my work.

Yeah, shortcuts for Teams would be crazy. Shared space is really what it comes down to, right? There is no such thing as a shared space for Apple software. The best you can come up with is iCloud.com, which is for personal use only. So yeah, I mean, a shared space would be great. Obviously, I mean, I guess maybe the elephant in the room with a lot of this stuff is Google Workspaces. And I think that Google does a pretty good job here. I mean, I don't think it's a great job. I think one of the things they're

I don't know. I think some of the recent pricing changes left me feeling kind of bad about what they're trying to do with how they're incorporating Gemini and where they're, you know, where they're raising prices and what the options are and the fact that, like, you know, if you want to add Gemini to your Google Workspace account, you have to add it for across the board. There's no way to kind of do that, like, for who needs it versus who doesn't need it. It's just kind of a problem, I think.

Yeah, yeah, yeah. I agree. So, I don't know. I think this was a

I think this was a good conversation, if only to crystallize the fact that obviously we get the majority of our work done on Apple devices, right? Even though we are and we will continue to be tech curious about other platforms and products. But I mean, I cannot work on anything else that is not my iPad Pro. But in an ideal scenario, I would very much just use Apple services because at the end of the day, like,

you know, all functionalities being equal, that goes back to the idea of like an ideal world, but all functionalities being equal, I prefer Apple design. I prefer shortcuts to something else. I prefer the look of Apple Mail, but I cannot use Apple Mail. So, and that, maybe, here's the final thing I will say.

I could see a scenario in which Apple may come up with an idea to sell Apple Intelligence for businesses as a product.

And I think that could be an interesting conversation, like to have sort of like Google, what Google is doing with Gemini for businesses, but done the Apple way with Apple intelligence. We're obviously talking way down the road because, you know, Apple intelligence right now can barely make an emoji for you. But like two, three years from now,

You know, imagine setting up, you know, an iCloud for Teams and you have Apple Intelligence for Teams and you have a shared space where you can analyze your Apple Notes and analyze your Apple Mail, share your Apple Mail with your teammates. This is all hypothetical, but I could see, and obviously because Apple likes to make money, there could be the potential there to say, well, Apple Intelligence for Teams, you know, it costs a little more, but you can share all this work and all these apps with your teammates. That'd be interesting, I think.

Yeah, I agree. I agree. I mean, I think, you know, the benefit of being on one platform and not spreading yourself across a lot of different services is the consistency and the integration. And Apple's always been good with that, with its software. It's just that, as we've been talking about, it just doesn't work so great for teams. And I do feel like Apple intelligence, it has the potential. It's a long way from this now, but to effectively be

new operating system that's kind of spans all of Apple's devices. And by that, I mean, is it, you know, Apple intelligence could become the glue that fits all these products together. And especially when it comes to a business type of scenario, having Apple intelligence at the center and be the thing that you pay for and then have the apps

the apps come with the service. The service will be Apple intelligence and the fact that you can have the AI do various things for you to short circuit your workflows and make things easier and more compatible. And then the apps are just the tools that access the Apple intelligence, whether that's for automation or for communication between team members. So I think that that's an exciting future to me. But I think, as you said, we're a long way off from that.

All right, Federico. Well, that's a good conversation. It's a lot to think about. If anybody out there in the audience has any suggestions where they think that services or apps are doing a particularly good job for smaller and medium-sized businesses, let us know. We'd like to think about them and maybe write about them at some point.

I want to thank our sponsor again for this episode. That is Incogni, Federico and I over at MacStories.net. We're going to go into the post show now. We've got some things lined up. I want to follow up a little bit on the 16E Federico. And I also have a thought about task managers that I want to bounce off you. So we're going to talk about that today. You can get that post show online.

by subscribing to AppStories Plus. That's appstories.plus, or you can become a Club Premier member. Just go to plus.club, and you'll learn all about all the benefits of being a Club Mac Stories Premier member, which includes AppStories Plus, but a whole bunch of other things as well.

All right, everybody, you can find Federico on social media. He's at Vitici. That's V-I-T-I-C-I. And I'm at John Voorhees. J-O-H-N-V-O-O-R-H-E-S. Talk to you next week, Federico. Ciao, John.