Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.
Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
How Solopreneurs Can Save Hours Every Week With a Mac
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Your Mac can either be a fancy typewriter or a serious business advantage, and the difference is usually a handful of habits you set up once. We sit down with Damian Schres, the explainer-in-chief at EasyTech and host of the Mac Preneur Podcast, to talk about the practical side of running a lean solopreneur business on Apple gear without chasing every shiny new tool.
We start with Damian’s story: a Fortune 500 engineer who took a slow, careful path into entrepreneurship. Instead of quitting overnight, he spent years running mini-experiments, building confidence, and reducing risk before going full-time. If you’re risk-averse, juggling family priorities, or just tired of “go all in” advice, this conversation offers a more realistic roadmap that still leads to freedom and control.
Then we get into the fun part: Mac productivity, automation, and AI for entrepreneurs. Damian shares why macOS longevity and security can be a win for small business owners, plus the specific workflows that save time daily, like iCloud-synced Text Replacement for instant emails and repeat replies. We also explore templates for Gmail and client docs, and Damian’s AI setup using API-driven tools like Writers Brew, alongside Mac utilities like PopClip, Apple Shortcuts, and Hazel, including an automation that renames screenshots based on the text inside them. The takeaway is simple: build systems that remove friction, and you buy back hours every week.
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Cold Open: Safer Leaps And Snippets
SPEAKER_03So I I really de-risked the transition because I was not even sure that I would be I would like entrepreneurship or I as as I it turned out to be solopreneurship and I don't think I'm gonna grow in terms of the of the business. I I think I like the solopreneur lifestyle. But really um I'm very risk-averse. Yeah, so if they don't use text replacement, that's that should be the first first thing, right? You find that in settings and it synchronizes over iCloud. So most Mac users they also have an iPhone and potentially an iPad. And so text replacement is you just configure a short snippet, ideally something that cannot be typed normally. So the trick is to use like semicolon or dash as a small character preceding the the shortcut, right? The the the snippet.
SPEAKER_00Hi
Meet Damian And His Mac Focus
SPEAKER_00and welcome back to Plan Like a Boss. I'm your host, Tanya Lawson, and today I am super excited to be here with Damian Schroes. He's the explainer-in-chief of EasyTech, a company providing IT training and coaching on topics such as Apple products, Microsoft Office, cybersecurity, and AI. In parallel, Domien hosts the Mac Preneur Podcast, featuring practical tips, effective strategies, and insightful interviews to help solopreneurs save time and money running their business on a Mac. Before that, he worked as a research and developer engineer for a Fortune 500 US company. In 2013, Dominion started Easy Tech as a side hustle to experience entrepreneurship while preserving a steady paycheck. In September 2016, he finally quit his nine to five job to offer Apple training and consultancy services in Luxembourg and regain control of when and how he can dedicate time to his family and work. Welcome, Damian, I'm so excited to have you on the show.
SPEAKER_03Yeah, thank you for having me, Tonya.
SPEAKER_00So I like to start these interviews by asking my guest to tell us your story. How did you get here? What led you to where you are today?
SPEAKER_03Yeah, so if you'd ask me how I see myself, I see myself as a continuous learner and passionate educator. And when I look back in my career and even university and so on, it has always been the through line. And basically, I'm trying to always optimize optimize the the way I my life, basically, right? I'm I'm I'm a continuous optimizer. And um it's a series of of iterations and pivots and and basically yeah, following. I've always tried to follow my gut or my heart, and when something fell off, try to uh yeah, found found a path to to someplace else. Right. That's um that's uh where I am today, actually.
SPEAKER_00Love that. And you're I like that you point out that you follow your gut. Your that intuition is so important in business, I think.
De-Risking The Move To Solo Work
SPEAKER_00Now you transitioned from full-time employment to entrepreneurship. And I know there are a lot of people out there listening right now who may be thinking, you know, I either did that or I'm trying desperately to do that. So what was the path you took? How did you do that?
SPEAKER_03Yeah, so I I really de-risked the um the transition because I was not even sure that I would be I would like entrepreneurship or I as as I it turned out to be solopreneurship, and I don't think I'm gonna grow in terms of the of the business. I think I like the solopreneur lifestyle, but really um I'm very risk-averse. I'm the kind of person who before buying a car, it takes three months and a huge Excel file and and research left and right. And so for these kinds of um yeah, f changes that that can have dramatic effect, right? Financially, emotionally, everything. It's a big change. Usually, yeah, take my time. I would say it was uh it was even 10 or 13 years in the making. Um before before 2013, when I actually incorporated EasyTech and got the approval from my employer to work 70% part-time and and launch a business on the site. Before that, there were there was already a lot of preparation, a lot of mini experiments, uh pro bono work and and stuff like that.
SPEAKER_00That's so smart. And the opposite of what you hear a lot of times. A lot of times you hear people, oh, I just quit and I went all in and it was feast or famine. I knew I had to make it work. But I like that you planned ahead. And and there are a lot of people out there who are risk averse, who are terrified of taking that leap. And to see your success story and how you did it in a way that was comfortable for you, I'm sure will help them as well. Now, you said that that you prefer solopreneurship. Um, do you do you have a team or are you still working as a one-man show?
SPEAKER_03No, no, I still I still work as a one-man show. I have um a contractor for the accounting side of things. So I have uh an accountant if you want, but he's not on payroll. Um and I have friends that from time to time help me with things like marketing stuff. Um, the logo, the new logo of EasyTech and the color palette was a friend of mine who is um uh a designer. And uh so yeah, from time to time I I hire subcontractors, or I have one on retainer for on a yearly retainer as well. Um, but for the day-to-day for how EasyTech operates, I'm alone. I'm alone, but I wouldn't say I would say less alone now with artificial intelligence, because I have built a team of AI assistants and AI agents that actually uh help me or support me when when I have questions or when I need uh yeah, when I need to save even more time.
SPEAKER_00Love that. And AI is definitely a bit of a controversial topic right now, but also one that I'm firmly believe it is here to stay. We need to adopt it, or we are gonna be left behind. So let's let's talk. I want to talk about AI, but I also want to talk about Mac because Mac is your thing, and you are I'm a Mac girl, and we're recording this on my Mac Mini right now. Um but we're gonna talk about Mac and AI and how they relate.
Why Mac Works Better For Business
SPEAKER_00But why do you believe a Mac is the best platform for entrepreneurs?
SPEAKER_03Yeah, first of all, from um longevity point of view, it's uh much better than than Windows machines, than than Windows computers, can be laptop. So the the build quality, right? So it's oftentimes I hear they are much more expensive. Actually, not the Mac is not that more exp much more expensive than a comparable Windows PC. So it's yes, you have cheap Windows PCs, but and actually it it's unfortunately even the the Windows PCs that are a bit more expensive, still the durability, the hardware durability is not that good. And on top of that, you have macOS versus Windows, which so I've been I I'm I'm still a Windows user because I I teach Windows user how to use Microsoft Office on Windows. So that means that on my iMac that I'm recording now, that iMac has a virtual machine that boots Windows, so I still boot Windows from time to time from my Mac.
SPEAKER_02Over the past five years, only one person, one trainee realized that there were these the three bubbles in the top left corner the yellow, red. Well, you are on a Mac. Yes, only one person noticed.
SPEAKER_00That's awesome.
SPEAKER_03But the the the thing is, um Microsoft is really, I don't know, I don't know what they are doing. First of all, from a security point of view, they don't have good security practices compared to Apple. Right? Mac OS and Mac OS now is taking more and more security features from the iPhone and the iPad, which is actually uh one of the strongest operating systems of uh that we have right now. And but on the flip side, it looks like for Microsoft, they're making so much money on the enterprise that they they don't really they don't really care. They don't care about security. Which is not the case for Apple, right? Apple is the privacy, they have a big privacy stand, but they have also a big security stance. And um it doesn't mean that the Mac is immune, is immune to viruses or no no it's at the end of the day, it's the user who configures the Mac versus Windows, and you can have Windows PCs that are more secure than Mac Macs because of the of the user, right? And also the user behavior and forgetting to install uh software security updates and things like that. But all in all, I believe that it's not only easier to use, but it's also easier to secure a Mac versus a Windows computer. And even though in the past you had to be a bit of a trailblazer to have a Mac because there were so many applications that were Windows only. Nowadays we with the cloud, most of the things that we do as entrepreneurs, it's web services, so it doesn't matter. We just need a web browser and and we're good to go.
SPEAKER_00Awesome. Yeah, no, I agree with you totally on that. And you talked earlier about your your your AI stack. So your AI stack, do you
An AI Stack That Stays Stable
SPEAKER_00can we talk about it for a minute? And do you have anything that is specific to Mac or will it benefit both Mac and PC users?
SPEAKER_03Yeah, no, and actually because I'm I'm the kind of person who doesn't like uh instabilities. I'm I'm not on the bleeding edge on the Mac side, right? So I still have a 2020 iMac, that iMac is still running macOS Umte Sonoma, and because it is still supported by Apple, Apple, uh that's also something that very few people understand. That Apple supports the last three versions of the operating systems, and that means nine, sometimes ten years of security update versus Windows, where it's it's fewer than uh fewer years than that. But so I'm always behind. And because I'm behind and I'm still also on an Intel computer, there are many Apple intelligence features that are completely out of uh out of range for me. And on top of that, I'm in Europe, so that's that's even worse because Apple uh and because of the DMA, the Digital Market Act, uh, and the AI Act, Apple decided, okay, let's let's not uh take any chance with the European regulator. So, what I'm doing on my old iMac with an old operating system is actually uh almost cross-platform. First of all, I'm using more and more the cloud desktop application, and that's yeah, Windows and Mac. But more importantly, Cloud Desktop is the only one that still runs on an Intel computer. You you can't install Chat GPT on uh on an Intel Mac and even and and it's even um limited to macOS 15 minimum, and the same goes with um with what? I don't remember, there was another application that was yeah. So from that's the reason why in the end I switched to to the cloud, to cloud and uh to the cloud desktop app. Um, and also uh I'm still doing some AI stuff that is Mac specific because I uh I combined using OpenAI or the uh ChatGPT via the API, so via talking directly to ChatGPT's or OpenAI's servers, and that allowed me to integrate um uh ChatGPT inside shortcuts, which is an automation application that works on Mac, iPhone, and iPad. And so I can do uh like I I can automatically rename images, screenshots based on text that is inside the image. So I take a screenshot, it lands where it used to land in uh on my desktop, now it lands in the downloads folder, and I have another tool called Hazel, which is an uh uh an automation software that's also Mac only. And it sees it's an image, and then it kicks in, it's automatically launching a shortcut that um looks at the text inside the image, then queries chat GPT, it says this is the text in the image. Can you suggest a nice short name with the date at the beginning? I really like to have the year dash the month dash the day, and then the suggestion from ChatGPT, which is usually pretty good.
SPEAKER_00That is fascinating. And setting that up at this moment would be completely over my head. Now, I did some I did some research on you before the um interview, and you often mention that most people only
Text Replacement For Instant Replies
SPEAKER_00use maybe 20% of their max capabilities. So for a for small business owner or solopreneur who's really pressed for time because let's face it, you're wearing so many different hats. What are one or two built-in tools that they should start utilizing immediately?
SPEAKER_03Yeah, so if they don't use text replacement, that's that should be the first first thing, right? You find that in settings and it synchronizes over iCloud. So most Mac users they also have an iPhone and potentially an iPad. And so text replacement is you just configure a short snippet, ideally, something that cannot be typed normally. So the trick is to use like semicolon or dash as a small character preceding the the shortcut, right? The the the snippet. And and then it will automatically pre-write, could be like your email address. So in my case, um I think for sure for the built-in it is um comma, so comma em enters automatically my email address. And so you can do comma ph for phone and it it can enter your phone number. You can have your website, right? And it will pre pre fill the thing. And um, so that's and and also you can easily if you prepare the snippet at uh in advance, you can copy paste multiple paragraphs. So and and the the time you save is is the per snippet is not a lot, but you can't beat even if you took typing classes and you were a super fast typist, you can't beat text replacements. It's like I don't know how many hundreds of words per minute or thousands of words per minute that you get when you do that.
SPEAKER_00That is fascinating. I did not know you could do that. I'm gonna go start playing with my computer after this call. And I can see that as really saving time if you're a small business owner and maybe you get the same question often through email. You could type out the reply and and make a short text replacement for it and just type that in and hit send.
SPEAKER_03Yeah. And and something I I use, and it's actually I don't replace a lot. It's actually the the snippet is bigger than what is replaced, what is uh after it's replaced, and it's emojis. And so I have pre I have the comma done and it's the green check mark emoji. I have the comma nope and op and the cross, the red cross emoji, and I have a bunch of emojis like that, yes.
SPEAKER_02So I call it nope.
SPEAKER_03And um, yeah, and and so you prepare a bunch of those in advance, and when you need to, you get them very quickly. And on an iPhone and an iPad, it's synchronized with iCloud. And as soon as you start typing it, you will have also uh prediction, right? Predictive typing at the top of the keyboard on the iPhone and the iPad, and you tap on it and immediately you have your your emoji. And you don't need to go tap on the emoji. And and on the on the on the Mac, it's it's a pain. It's a pain to open the emoji picker and find the right one.
SPEAKER_00Oh yeah, for sure. You gotta hit command shift spacebar, then you gotta start scrolling. Yes, yes, no, I could see how that could save so much time, especially as business owners. We tend to use a lot of emojis in emails because emails and messages they can be read in so many different ways. So adding that emoji in can can let people know, oh hey, you know, I'm not angry about this. I love that. What else should we do? I'm I'm all ears. I'm excited.
SPEAKER_03So yeah, templates, right? That's the for me the basic building block
Templates That Stop Rewriting Everything
SPEAKER_03of of a good business. You have templated uh contracts or even uh email emails. Um it's a little bit more complicated to if you use Apple Mail, but um if you use Gmail, the web version of Gmail, they have built-in templates there. You just need to you write once your response, including the subject line. And uh I don't remember now it's if it's on by default or if you need to go to Gmail settings and advanced and turn on the templates, but then you can have a bunch of of templated responses. And I have for so when when when the clients reach out to me, I have a uh default response. When I try when I contact somebody for the first time, I have also a template. When I have some um support questions, I have also a template. So yeah, templates, templates for contracts. So I have I have uh a few Google Docs. So for contracts, for um reports for for customers when I finish something. Now, because I give a lot of training and I prepare training sessions, I have templates for the training, uh, the summary of the training, right? The thing that I give to a prospective uh client if they want to know, okay, what's what's in the Excel advanced training? I have a one-pager or a two-pager.
SPEAKER_00That's super smart. And yeah, templates are a game changer. They save so much time. You don't need to reinvent the wheel every single time. Now, do you have any favorite AI integrated Mac tools that you like to use on a daily basis?
SPEAKER_03Yeah, it's a it's a combo of two things, actually. Well, it's a it's a non-AI tool and it's an AI tool.
Writers Brew And PopClip In Action
SPEAKER_03So the AI tool is called Writers Brew. And I've been using that for three years now. I think it was uh very quickly after Chat GPT got out. The the guy developed writers brew and it's uh it's a one-time fee, actually. It's not even a um it's not a subscription. So writers brew is it's an AI tool where you bring your API key. So that's why you don't have to pay a subscription. So you have to create an account with uh at platform.openai.com or platform.cloud.com, and you need to generate an API, create an API key to run directly or to query directly the model on the server. And once you do that, the uh writers brew has a bunch of predefined uh prompts, it's like a prompt library, but you can create your own prompts and to invoke them, I'm using a tool called Popclip. And um I could use so I could use writers brew directly and invoke it with a keyboard shortcut, but that means usually uh copy pasting things into that box. Right, it's it's like a like a chat GPT prompt box that appears in the middle of the screen. But PopClip that's not an AI specific tool, but Popclip is a tool on the Mac that makes you makes a menu pop up when you select text anywhere on your Mac. Could you be Apple notes, mail inside a browser, when you reply to some it's it anywhere. And among the options, so you have for instance if you want to capitalize words, if you want to count the number of words on the number of characters, with those little plugins, writer's brew has a plugin for popclip. And so I have a summarize and bullet. So I can select a bunch of text in Apple Notes. Automatically I have the popclip menu that appears, and one of the things is summarize. And I have another one that is translate. So I'm a French speaker, and from time to time I need to translate from English to French, even though it's my my native my mother tongue. I still it's it's good. Uh ChatGPT is good. Uh even if it makes a few mistakes, I can easily correct them. But yeah, I can do translation directly. Uh what else? Because I'm I'm in Apple Note here. Um yeah, fix grammar and punctuation. I'm using that all the time.
SPEAKER_00Wow, that's awesome. Yeah, because if I want to summarize something, I tend to pop it into notebook LM. But to have that right there on the Mac without having to go in some to without having to go somewhere else, that's brilliant.
SPEAKER_03Yeah, so there's so I select text, I say um, so I select some text, and then I say fix fix grammar and punctuation, then it obviously it sends the request to OpenAI servers, then it comes back in a second or two, and then at the in the middle of the screen I see the original text, the corrected text, and then I can do copy or I can do insert command i and it automatically replaces the selected text with the corrected text.
SPEAKER_00Oh wow, I love that. So it's it's all about using those tools you have on your Mac and AI to work smarter, not harder.
SPEAKER_01Exactly.
SPEAKER_00I love that. Now, if yeah, this is this is totally the geek out episode for all the Mac users out there. And um, some of this stuff is also applic applicable to PC users as well. But I want to ask you this. Um, I always like to kind of end the wrap these interviews up by asking the person I'm talking to
Simple Advice: Learn Key Shortcuts
SPEAKER_00to give a piece of advice or a tangible action for my listeners. So, as someone who, you know, you're a Mac specialist, you also worked that nine to five and transitioned into full-time solopreneurship. What is one piece of advice that you think will best help my audience today, based off of all of your history? It can be about business, it can be about the computer, it can be about anything. What is one piece of advice that you would give yourself back when you were first starting out? Yeah.
SPEAKER_03So for the tech side of things, it's very difficult because I realize that some people are uh tech native or they understand tech, and then people there are people who are tech challenged. And maybe for those tech challenged, uh, I would say it's less complicated than you think. Right? It's it's really the there are solutions that are not that complicated to put in place. And the example is uh we we didn't talk about keyboard shortcuts, but that's also something I think quite simple to put in place. It's just a matter of remembering. It's a little bit like um remembering phone numbers, right? Yeah, we have we have smartphones today, we can put stuff in the and I don't know half of a percent of what is in my con in my address book, but my wife's phone number, my mother's phone number, my father's phone number, my those phone. There are a few phone numbers that I remember by heart. And it doesn't matter that it's a one-touch speed dial, right? I still want to remember those those phone numbers just in case. And yeah, so yeah, a few keyboard shortcuts can can make your life much, much, much easier.
SPEAKER_00No, I agree, I agree 100%. And they're kind of ingrained in my brain because they've not changed. They've been the same. So the same keyboard shortcuts, shortcuts that I learned back in the 80s are still the same on my my little chunky Apple computer in school. They're they're still the same. So that's great. Now, where can listeners find you if they want to reach out?
SPEAKER_03Yeah, so if they if they run a business
Where To Find Damian Online
SPEAKER_03on a Mac, the best place to find me is MacPreneur.com where they'll find uh yeah, the the all the last episodes of the podcast. I release those episodes in both video and audio. And every episode has a blog post that has a summary, and also directly the the YouTube video is embedded there and the the video the audio player is there as well. But then if they want, they can easily go into their pod uh catcher of choice to follow the podcast. And if they are not on the Mac but they want to connect with me, uh I'm on LinkedIn and uh I'm the only uh Damiashger, so pretty once once you know how to spell it, you can find it.
SPEAKER_02Oh, that's but by the way, it's dash LKDN. That's my my my key my my uh shortcut for the my LinkedIn profile.
SPEAKER_00I love that. That's awesome. Well, thank you so much for coming on the show. I've had so much fun talking tech with you and geeking out in this episode. And I hope everybody else enjoyed it. And and take take Damian's advice. You know, remember those shortcuts, set up everything to make your life easier and keep planning like a boss.