Macpreneur

Unlock Amazing Mac Tricks and Protect Your Files with Shawn Lemon

• Damien Schreurs • Season 6 • Episode 134

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In this episode, Shawn Lemon, founder of The Digital Organizer, discusses his favorite apps and tools, and provides valuable insights into using web apps for efficiency. Tune in for practical tips to optimize your Mac setup and improve your tech workflow.

Links and video version at https://macpreneur.com/episode134

Connect with Shawn:

Highlights:

  • [00:00] Hook  
  • [00:35] Introduction to Shawn Lemon  
  • [01:24] Starting the Business Journey  
  • [01:40] Current Tech Setup  
  • [03:23] First Mac Experience  
  • [05:43] Working at Apple  
  • [06:33] Essential Business Applications  
  • [09:33] Google Chrome Profiles  
  • [15:17] Mac Tips and Tricks  
  • [18:24] Improving Mac Backup Solutions  
  • [26:23] Connecting with Shawn  
  • [27:10] Applying to be a guest too  
  • [27:33] Outro  


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Unlock Amazing Mac Tricks and Protect Your Files with Shawn Lemon


Hook

Shawn Lemon: I wish that we could turn that on and then click a button in Time Machine's preferences to say download and put all of this stuff onto my external drive automatically. Then, as it sees changes, it would just download the copy and put it on the hard drive. We don't need to put it actually on the Mac; we just want to make sure that it's backed up.

Nova AI: Welcome to Macpreneur, the show for seasoned solopreneurs looking to streamline their business on a Mac. Unlock the secrets to saving time and money with your host and technology mentor, Damien Schreurs. 


Introduction to Shawn Lemon

Damien Schreurs: Hello, hello! Today, I have the pleasure of introducing Shawn Lemon. Shawn is the founder of The Digital Organizer and has spent the last 17 years helping individuals and businesses get better at using their technology. A teacher at heart, Shawn believes that the biggest reason people struggle with their tech is because of a lack of understanding of the tools, which isn't surprising because they're constantly changing as technology advances.

Damien Schreurs: When not helping businesses operate more efficiently, Shawn loves making pottery, riding motorcycles, and spending time with his wife, Madeline, and their two-year-old son, Nico. 

Shawn, welcome to the show.

Shawn Lemon: Thanks so much for having me. I'm excited to talk to you.

Damien Schreurs: Yeah, thank you for coming on the show. 


Starting the Business Journey

Damien Schreurs: When we talked in the pre-show, I realized we started our businesses almost at the same time. You started in 2014, and I started in 2013. So let's jump right into the main topic. 


Current Tech Setup

Damien Schreurs: Which Mac are you using today to run your business?

Shawn Lemon: Yeah, I'm running the 2020 M1 MacBook Air, the total baseline 999 MacBook. I actually bought it as an experiment because everyone was talking about how incredible it was. I went from a very expensive iMac that was loaded up to this, just as an experiment. It did so well that I just kept it in production, gave the iMac to another employee, and got a monitor. 

I've been using it ever since, and it's about time for a new one.

Damien Schreurs: Yeah, I noticed as well. I still have my 2020 iMac, still an Intel Mac, but when I bought my MacBook Pro, I noticed immediately the difference. So you have a MacBook Air; do you have an external monitor as well?

Shawn Lemon: I do. It's a 34-inch ultra-wide Samsung. It's got charging capabilities, so it puts out like 80 watts to charge the bigger MacBook Pros and such. It's a nice one; I've enjoyed it.

Damien Schreurs: Is it a curved one or a flat one?

Shawn Lemon: It is slightly curved. Yeah. I actually kind of want to size down again and get 4K for just a little bit sharper, but every once in a while, it's nice to have it big. I go back and forth wanting to focus more and then wanting to have more on the screen at once.

Damien Schreurs: Do you still use your MacBook Air screen as a secondary screen, or is it just in clamshell mode?

Shawn Lemon: It's in clamshell mode, and it's in a vertical stand that I slipped behind the screen. So it's nice and clean when I'm looking at it.

Damien Schreurs: Very good. 


First Mac Experience

Damien Schreurs: So you mentioned an iMac before. What was your first Mac? When did you start?

Shawn Lemon: My first Mac was a Power PC. What was it? The Mac Pro? No, what was it called? A Power Mac, Power PC, Power Mac. I got it in 2005. Actually, it was pretty well loaded. I got it for an internship doing video editing and learning Avid and everything like that. So I needed something powerful, and I got a nice Cinema Display. Between those two, I was set up and styling.

Damien Schreurs: Yeah, I remember the Cinema Display. I didn't have one, but I had a few clients who had it. Yes, it was a nice screen—one of the nicest screens at the time. 

Shawn Lemon: You know, it was actually how I got into this in the first place. That monitor had a few dead pixels, and it was a $1,200 monitor, whatever, even in 2005—very expensive. So I was moving from California to Tennessee, and I grew up in Las Vegas. I ended up stopping in Las Vegas because there was an Apple store there, and I was going to spend a few days with my family before moving to the other side of the country. While I was at the Apple store dropping off the monitor to get that pixel replaced, I overheard a conversation the technician was having with a customer who was asking the technician about something in iPhoto. 

He gave an answer that was completely wrong. I thought, "Wait a second. That's not how iPhoto works. You can do that, but if you continue down that path, you're going to be unhappy because that's not the way it was designed to work." I don't remember exactly what it was; it was something between events and albums. It just made me think that maybe I could do this job because I clearly know the software inside and out. I know the product line inside and out. I was just completely obsessed over it because I was young and had an internship, so I had time on my hands. 


Working at Apple

Shawn Lemon: A few months later, when I moved to Nashville, I ended up getting hired for the iPhone launch and I worked there for almost seven years.

Damien Schreurs: So did you also have the long queues every September?

Shawn Lemon: Yeah, oh yeah, every September. I mean, it would stretch outside. There were people camping—the whole thing. It was a lot of fun. Launch days were really fun, except for the 3G launch. Luckily, I had that day off, which is rare; you usually don't get a day off on a launch day. But I think I just worked 10 days in a row or something, just how it worked with weekends that they couldn't schedule me. It turned out to be a disaster, so I was happy not to be there for that one.

Damien Schreurs: Yeah. Now, let's switch gears a little bit in terms of applications. 


Essential Business Applications

Damien Schreurs: So which applications are you using now to run your business?

Shawn Lemon: Yeah. So the core of my business is all run off of Google Workspace. I use Spark for my email app, and that's how I like to communicate with my team. I'll share a message with them so we can have a conversation without actually emailing each other. I use templates and all kinds of stuff. I love that app. 

Then, I've created web apps using Chrome's shortcut feature to create a sort of app for Google Calendar, Contacts, Asana, Pipedrive, Freshdesk, ChatGPT, and then I actually have 1Password installed. I use Dialpad for my VOIP, Zoom for all of my calls, Spotify for music, and my webcam is an Opal C1. That's the core stack of apps that I use.

Damien Schreurs: Yeah, it took a while for Apple with Safari to bring the same capability to convert a website into a web app. But now that you talk about that, I don't think that in any of the episodes I've had so far, a guest has mentioned this capability in Chrome. We have talked a few times about Chrome profiles and the ability to have different Google accounts completely separated. So the idea of converting a website into an app—if I recall correctly, is it in the three dots in the top right corner? Then you go to—

Shawn Lemon: That's right.

Damien Schreurs: Save as app or something like that. There is a—

Shawn Lemon: They changed it now; it says, is it? Is it under more tools? Cast, save and share is the menu. Then you choose "Install page as app." So that's the new terminology for it, and it works really well. My calendar used to change so fast because I was very appointment-based, and we allowed people to reschedule on the same day and stuff as I traveled around the city working for people in their homes and businesses. 

I just had to switch to the web app and interface from there because Fantastical just didn't update fast enough. It's better than Apple Calendar, but Fantastical still wasn't accurate. So I need 100 percent accuracy. I switched to using the web apps, and then Google Contacts doesn't work with Apple Contacts properly. I've never gotten it to work right with my clients. It works at first, and then all of a sudden, a week later, you update a contact, and it just reverts right back to what it was before. So now I just use Contacts as a web app as well.

Damien Schreurs: Yeah. 


Google Chrome Profiles

Damien Schreurs: So I'm not using that with Google Chrome. I'm using the same capability with Edge for some reason because Microsoft Edge now is based on Chromium. So they have implemented the same technology. For my company, EasyTECH, I have Voice over IP, so my landline. I don't have any physical phone, and it's a web app.

Shawn Lemon: Same.

Damien Schreurs: Yeah, I think it's for that. I went to Microsoft Edge, logged in, created it as a web app, and now I just launch the web app. But to come back to what you said, the reason why you use it—and it's for the listeners—when you access the web app, there is no synchronization. You are on the server, on Google's server. Whatever change you make, you make it to the source, right? Afterward, it gets synchronized to your iPhone, iPad, the Mac, and so on. This is the reason why using the web app is better in your case.

Shawn Lemon: Yeah. And I just don’t like troubleshooting. Apps have bugs and things go wrong, and the most reliable thing is usually the website. Asana's app kind of sucks. ChatGPT—you don't get all of the features in the app as you do in the web browser. Now, they've got these new groups that you can create, and there's the opportunity to actually edit and refine a prompt without having to regenerate the whole thing in a new response. That's still in beta; in some conversations, it works, and in some, it doesn't, but you only get that in the web app. So if you want it ultra-reliable and you don’t like troubleshooting, going straight to the web is nice. 

But when I have four different email accounts I'm monitoring, I don't want to do that in four separate Chrome tabs. So that's why I use an app for it.

Damien Schreurs: And to come back to the compatibility or the lack of compatibility between Google Workspace and the built-in or native Mac apps, I've been burned by that. I don't remember a few years ago; I was using Mail. For a while, I used the native Mail app on the Mac. Then something happened, and either email wouldn't synchronize or it would take too much time, and I was fed up. I realized, okay, they don't play well together. That's when I decided, okay, when I do Gmail—because I also have a Google Workspace account for the company—I have my Google profile, and that's it. 

I have my EasyTech profile, and I have a Mac profile. When I want to do Gmail, Google Calendar, whatever for EasyTech, I fire up that profile in Google Chrome. Even though it works with any other Chromium, I think it's still best to use Google Chrome because at the same time when you're logged in with your Google account or Google Workspace account, you have bookmark synchronization and stuff like that. 

So there are some advantages, and it is nice to have a profile with a Google Workspace account because when I get a new Mac and I just install it, I sign in with my Google Workspace account, and everything comes back—all the history and your cookies, extensions; it all just pops right in. I'm a huge user of profiles; I have 12 profiles right now because I've got different client projects going on. 

We often do data migration; our thing is organizing people's email files, passwords, and project management. Sometimes organization means big data transfers. We need to use other tools, which means it's not just practical to download the content to their machine and then upload it somewhere else. So we'll do a migration. I have to gather logins for that, and so I use a totally different profile. It keeps things so clean. When I'm done with the project, I trash the profile, and all their stuff is off my machine. It's just so nice.

Damien Schreurs: Yeah, I think it's one of the underutilized features of Google Chrome, but the same thing with Edge. It's for Microsoft, for people who are in the Microsoft 365 ecosystem. Whatever we just talked about with Shawn, you do the same but with Microsoft Edge on the Mac.

Shawn Lemon: Yeah, and if anyone wants to learn more about those profiles, I did a Q&A for my clients a few months ago and recorded all of that. It's basically five things for efficiently using your web browser—from how I do bookmarks, use Chrome profiles, the extensions, using notes apps, and screen captures. 

There’s some really good stuff. You can just email me if you're interested in that, and I can send it your way.

Damien Schreurs: Or I could even put it in the show notes, right? If you send me the link after the episode, I can put it in the show notes. 

Shawn Lemon: Yeah, that’ll be perfect. We'll put that in there.

Damien Schreurs: Very good. 


Mac Tips and Tricks

Damien Schreurs: What tip or trick did you discover on your Mac recently that you wished you knew before? I know it's going to be a hard one for you, but let's try.

Shawn Lemon: Yes, I, oh! It's using the Option key. So using the Option key to skip between words and also to delete one word at a time instead of having to delete character by character or using an entire line. I was so often using the up and down arrow keys to move my cursor, and then I would use Shift + Command + left, right, up, down to highlight all from that point of the cursor. 

But I didn't realize before that I could just use Shift + Option and then use the arrow keys to highlight a few words, or Option + Delete was the big one—oh, I could just delete one word at a time. So it's been nice as I am a real stickler on naming conventions for my files. Being able to edit a name that someone else gave me or if I'm renaming a file that's very similar to something else with the same naming convention, except I'm changing one piece, it's just quicker to get there like that.

Damien Schreurs: Yeah. It's quicker than going character by character. With the Option key, you do it word by word, basically. Good. Talking about the Option key, that's something I need to remind myself to check more often—oh, the Option key before on all the keyboards was called the Alt, and Alt means alternate. Something I try to do now, and I try to remind myself, is whatever keyboard shortcut or action I can do somewhere—

Shawn Lemon: Mm hmm.

Damien Schreurs:—the Option key, and you will see some additional options, right? One that is nice in Preview, right? You can rotate a picture. I don't remember now, but if it's rotate 90 degrees left or 90 degrees right, basically the button is just one direction. If you want to go the other way, you would have to press three times normally or four times, or three times to get it what you want.

Shawn Lemon: Yeah, three.

Damien Schreurs: But if you press Option and you click, Option means rotate in the other direction.

Shawn Lemon: Oh, interesting. On the U.S. Keyboard, you have to do Command. It's usually Command that will switch it around. For me, I feel like what they really should have done is made the Alt key Control. Control should have been Alt because Apple calls a right click a secondary click or alternate options. 

Instead of holding Control to see the secondary options, it should have just been ALT for, yeah, alternative. But what do you do?

Damien Schreurs: Very good. We're almost at the end of the show. 


Improving Mac Backup Solutions

Damien Schreurs: If you were in charge of the Mac division at Apple, what would be your first priority?

Shawn Lemon: The Mac division? It's not software.

Damien Schreurs: Yeah, you could oversee hardware and software, yes.

Shawn Lemon: Okay. One of my biggest gripes is the ability to back up cloud accounts. When we use Time Machine to back up our Macs, if you're using iCloud, Dropbox, Google Drive—anything—and you're not physically downloading the file or making it available offline, then it won't back up to your Time Machine drive. Many people think they're backing up their computers, but really, it's like an iPhone backup—or not quite an iPhone; the opposite of an iPhone backup. 

It's backing up your applications and your settings, but not actually the majority of the data because it's so often offloading data and just streaming by default. My Google Drive, because I use almost exclusively shared drives, even for my personal stuff, I use a shared drive to share with my wife. None of that stuff gets backed up, and none of it gets downloaded. 

I wish that we could turn that on and then click a button in Time Machine's preferences to say download and put all of this stuff onto my external drive automatically. Then, as it sees changes, just download the copy and put it on the hard drive. We don't need to put it actually on the Mac; we just want to make sure that it's backed up. So that would be kind of the biggest thing that I would want to change. 

Then, make that cloud sync a little bit more reliable and faster because what is it? File Provider is the new protocol that they switched for Dropbox, OneDrive, Google Drive to all sync to our Macs and even iCloud. It's all the same protocol, which is nice for consistency, but we're three years into it, and it still has some issues here and there.

Damien Schreurs: Yeah. I'm still behind operating system wise; I'm still on Sonoma on my MacBook Pro and Ventura on the iMac. But I've heard that Sequoia now is implementing a new iCloud sync protocol that should be faster in the sense that now iCloud should only upload the delta version of files rather than re-uploading the full files, which is the reason why it's so slow on older operating system versions, macOS versions.

Shawn Lemon: Interesting. Yeah, I've really been unhappy with how iCloud's file sync works between devices and sharing and everything. It's just not quite as good as it needs to be. Especially if we're trying to consolidate someone's files into Google Drive and they've been using iCloud storage the entire time, it can be really difficult. 

There's no option to use something like CloudHQ to sync contents of iCloud Drive anywhere else. It has to download physically onto the Mac to then move. But once you initiate that download, it's like you can't stop it. Once it gets going, you have to—anyway, it's a real mess. Ha, ha.

Damien Schreurs: Yeah. For the other, yeah, I think for the other, it works as well. But for Google Workspace, the way I do a local backup, a physical backup of all my data is through my Synology NAS.

Shawn Lemon: Yep. I do too. I've got a Synology NAS, and I'm probably going to go back and set up Spanning Sync again anyway, just for email synchronization between downloading everyone's emails, contacts, calendars. We'll see if I end up doing their individual My Drives because it can get a little more expensive when you add up more data, but I do like the Synology. It's local; I own it, and it's just nice peace of mind.

Damien Schreurs: Otherwise, Carbon Copy Cloner is an app that I'm using to do a backup of my Synology onto another external hard drive connected to my Mac. With Carbon Copy Cloner, I have to double-check starting from which version, but you can tell it to do some backup of cloud storage systems, and it will force the download.

Shawn Lemon: Oh, very nice. I'll have to look into that because I haven't used Carbon Copy Cloner in a long time. Since we've been doing so much more cloud-based stuff, I'll have to look into that. I used to use it all the time.

Damien Schreurs: I ended up purchasing a—how is it called? How do they call that? Company license or—

Shawn Lemon: Site license usually.

Damien Schreurs: Life license or something like that.

Shawn Lemon: Huh.

Damien Schreurs: When I was doing some Apple consulting, I've stopped doing that now, but when I was doing that, it was super handy. I could install it legally on any of my clients' machines—a quick clone backup, reinstall, or stuff like that—and then uninstall the app from the computer. I could then install it on any number of computers because, yeah, you're right; there are site licenses for within a company, and then there's a license for people like us—consultants who go and help clients.

Shawn Lemon: Yeah. I used it a good bit, and one of my favorite things about it—they stopped the ability to do this, but back in the day when I was doing a lot of SSD upgrades, some would come to me with an iMac or MacBook Pro with a standard hard drive. I'd pop an SSD in there, and I never liked to just clone somebody's data from one drive to another. Usually, by the time they got to me, their operating system was kind of messed up, and everything was slow. 

I wanted a fresh operating system, and I wanted to reinstall everything fresh, pulling the files over and organizing the files while we were doing it. I called it "reboot." In the day, I could install macOS on a partition on another SSD, so then I would plug both SSDs—the new one in a cradle, and then my other one into the Mac—and I could just clone one to the other. 

It would take three minutes to install an operating system on an SSD. Then I just popped it into the computer, and it was so fast. It saved me a bunch of time rather than sitting there for an hour waiting for it to download and then another hour to an hour and a half to actually install the operating system. The whole thing was just three minutes. I don't remember what operating system it all stopped with, and you had to install it fresh. 

At that point, I just downloaded the installers, so at least I didn't have to wait, but it still took a while—about 30 minutes—onto an SSD to install the operating system for that particular Mac.

Damien Schreurs: Very good. Thank you very much, Shawn. 


Connecting with Shawn

Damien Schreurs: Where can people find you online?

Shawn Lemon: Yeah, we are at thedigitalorganizer.com. If you go to thedigitalorganizer.com/macpreneur, I have a file organization guide. If you are interested in cleaning up your stuff, you have things all over the place and want to consolidate them with a really good folder structure, great archiving convention or strategy, and naming convention and everything, I’ve got all of it laid out. That’s what we normally take our clients through. 

If you want to go and self-implement and learn that, just go to that link, and then we'll give you another one for what is it? The browser tips and everything, but yeah, pretty easy.

Damien Schreurs: All of that in the show notes.


Applying to be a guest too

Damien Schreurs: If, like Shawn, you would like to share how you are using your Mac to run your solopreneur business, it's simple. Just visit macpreneur.com/apply. If you are already on Podmatch, just click on the button, and you will land on the show profile. Otherwise, fill out the application form, and I will get back to you within a few days. 

Once again, it's macpreneur.com/apply. 


Outro

Damien Schreurs: If you found this episode helpful, please share it with a fellow solopreneur and tag both Shawn and myself on LinkedIn. 

And until next time, I'm Damien Schreurs, wishing you a great day.

Nova AI: Thank you for listening to the Macpreneur Podcast. If you've enjoyed the show, please leave a review and share it with a friend right now.