Macpreneur

Stop Typing: The AI Workflow That Writes Everything For You with Samantha Hartley

• Damien Schreurs • Season 7 • Episode 163

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In this episode, you'll learn how business consultant Samantha Hartley uses her Mac to streamline her business. 

Discover how tools like Wispr Flow for dictation, Apple Notes for organization, Time Machine for backups, Loom for client communication, and how AI assistants can help consultants break revenue ceilings while overcoming macOS limitations.

Connect with Samantha Hartley:

Highlights:

  • [00:00] Teaser  
  • [01:30] Samantha's Mac Setup  
  • [02:50] Essential Apps for Business  
  • [09:26] Exploring AI Tools: GPT and Claude  
  • [11:06] Backup Strategies and Time Machine  
  • [15:04] Advanced AI Usage and Customization  
  • [26:18] Synthesis of Information and Custom Instructions  
  • [29:05] Gemini's Integration with Google Workspace  
  • [32:05] Wispr Flow: The Ultimate Dictation Tool  
  • [37:58] Time Machine and Backup Solutions  
  • [43:04] Improving Finder Search on Mac  
  • [51:07] Applying to be a guest too  
  • [51:31] Outro  

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MP163 - Stop Typing: The AI Workflow That Writes Everything For You with Samantha Hartley


Teaser

Samantha Hartley: It's the fastest I've ever adopted anything, which is Wispr Flow. I can type, but I just don't like to type. I talk really fast and need to be able to dictate into something quickly. Wispr Flow has AI built into it. It works on the phone and also on the MacBook, and it's got a hot key on the MacBook. It's the most convenient, time-saving thing I've installed in the past six months. I use it constantly, and it just gets smarter and better.

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.


Introducing Samantha Hartley

Damien Schreurs: Hello. Today I have the pleasure to introduce Samantha Hartley. Samantha partners with well-established mid-six-figure consultancies that have hit a revenue ceiling or feel weighed down by delivery and people challenges. Her clients often double revenues in their first year and cross the million-dollar mark by increasing engagement size while reducing client load. She licenses her proven frameworks to firms ready to grow without costly trial and error. Previously in international marketing at the Coca-Cola Company, Samantha lives on Martha's Vineyard with her husband and their three spoiled fur kids. Samantha, welcome to the show!

Samantha Hartley: Thank you so much for having me, Damien.


Samantha's Mac Setup

Damien Schreurs: So let's jump directly into the first segment. What's your current Mac setup?

Samantha Hartley: My current Mac setup: I have a MacBook Air M2. It has 24 gigabytes of memory, 995 gigabytes of hard drive, and I'm running Sequoia 15.7.0.1.

Damien Schreurs: So it's good. I haven't jumped yet to the latest version, the 26. I'm reading horror stories from time to time.

Samantha Hartley: I looked into it before I did it. I just had this inkling: why don't I find out a little bit more? I know there's Tahoe, right? That's the big, big jump—a new version of Sequoia. So I saw the Tahoe and usually, I'm a beta on the iPhone. I'm always like, oh no, we'll just do it. Fine. But my MacBook is the heart and soul of my business, a very important piece of equipment. So I was like, let me just find out a little bit more, and then I was like, oh, we're not gonna do that just yet.

Damien Schreurs: I always wait one or two years before installing it on my main machines. I usually try them out on an external hard drive—it’s always safer, safer.

Samantha Hartley: Yeah, it's kind of a big deal.

Damien Schreurs: One of the reasons is that, even though Apple is developing everything for the new operating system, not every app developer has had time to make it work fully.


Essential Apps for Business

Damien Schreurs: So what are the apps that you rely upon to run your business?

Samantha Hartley: I have several that I'm very dedicated to. I run everything through Chrome right now, unless it fights me and I have to go somewhere else.


The Power of Notes and Superhuman

Samantha Hartley: On the MacBook, I am a notes person, and I'm in a subreddit about notes—about how dedicated I am to notes—and someone, you know, there's always the horror stories, like somebody's notes got purged and they lost everything. And I was like, everybody would be completely devastated. So it's where absolutely everything is kept: all of my session notes with clients, all of my personal notes. I do a data dump when I get up in the morning, which is a bullet point list of what's on my mind today, cute things that I find, links to social media, or things I get interrupted by while I'm in the middle of looking at something. I'll put those links in there. It's really the brain, heart, and soul of my business. A lot of people have tried to convince me to try Notion or something else instead, and I'm like, no, simple is best. The simplicity of Notes is amazing, and I have it on my phone so I can always be working, but I don't have to be working. I have developed, let's say over the past few years, much better work boundaries. And what I love is being available to my clients and team whenever I want to, even if during traditional work time I might not be working at my desk officially. I really love Notes—the portability and shareability of it—for that reason.

I also use my Photos that way as well. I'm looking forward to a time when we can categorize photos better. My photos are also used similarly for organizing videos, screenshots, and swipe files. I also use Superhuman for my email. That is a paid email app that sits on top of Gmail. I'm sure a lot of people would have trouble with the idea of paying for something when Gmail does everything you want it to do. Superhuman is very much about the efficiency of being able to get through your inbox without distractions. They talk about Inbox Zero; I don't care about Inbox Zero. What I care about is that when I come in, you can segment your inboxes so that when I'm looking at the main screen of my email in Superhuman, I see the actual important ones. If you have filters in Gmail, the scary thing for me is that if it's completely filtered—if it's not on page one of Gmail—I'll never see that email again. And that's too stressful. So Superhuman does a better job, and I have sophisticated filters on my Gmail because I’ve been using it for years, so almost nothing ever makes it through, but Superhuman makes it so that the things I really do need to see are prioritized. When I open my emails, I see the three important things without my squirrel brain going, "Oh, what's that? Here's some over there." That’s a really, really good thing about it. It also has a lot of AI features built into it, which honestly, everybody's got that, and Gmail's stuff is improving—it’s about equal in that way. The other thing it has is the ability to see when your email is delivered and when it was opened—a read receipt thing like we used to have back in the day with Outlook and some other systems. Well, Superhuman has very reliable read receipts, which is important for me because if you're in sales and you need to know whether somebody has opened your email—if you're my potential client, Damien, and I've sent you an email, and I don't hear back for two days—I might think, "Deliverability, right? Maybe it got caught up in spam filters if you're a large company." But I can see on there if you've opened it, and that's peace of mind. I can also see if you've opened it several times over the past three days; even if I haven't heard from you, I can assume there's a little bit of interest or purchase intent. A lot of times, when I'm thinking of following up with someone, I'll be able to check. Another interesting thing it shows is a running list in the sidebar of my main email indicating recent opens. So if somebody I was in touch with six months ago opens that email again, I'm like, "Well, look who's resurfacing." It is, in a way, nefarious spyware—or maybe just good data—to help me figure out intent. That is a very important feature: if you're in sales and you're not using something like that, then you're at a real disadvantage.

Damien Schreurs: Yeah, I remember I used a plugin for Gmail at one point that did that, but I stopped—I don't remember what it was called—but it was very handy to know whether or not your emails had been opened.

Samantha Hartley: And then, knowing the number of times they're opened and things like that—it's really good. I know the EU is much, much stricter about privacy than we are in the United States. I get why some people are opposed to it, and I'm using it while it's still working.

So that's Notes and Superhuman. There are a couple more apps I wanted to mention.


Loom and Basecamp: Tools for Efficiency

Samantha Hartley: One is Loom. I was an early user of Loom. This is a screen recording software, and you can also now record yourself. I'll make a Loom video that's 15 or 30 seconds long just for anybody—for instance, if you're a friend of mine and you couldn't figure something out, I might send you a link and if you're like, "I don't understand why it's doing that," I'll make you a Loom video. It's so easy and convenient. What people might not remember is there was a time when, to screen record something, you then had to upload it somewhere to be hosted, then figure out where that link was, and then pay—it was so onerous. The magic of Loom is that you have a link pasted instantly. It saved me, especially in the early days when working with an international team with people who don't necessarily have English as their first language. I'm in marketing, so so much is visual. I need to explain that this webpage needs to change, move, or what have you—it’s the whole "a picture is worth a thousand words" scenario. It saves so much time. Loom is something I urge everybody to get. Or, you know, things are evolving; somebody might acquire it and it’ll be part of G Suite soon, but for now, get Loom.

On another note, I'm doing Basecamp. We talked about Basecamp. Basecamp is online—it does have a desktop app, but I try to keep things off my desktop. So that probably is where we get into GPT.


Exploring AI Tools: ChatGPT and Claude

Samantha Hartley: So GPT—I do have the desktop version of that—and I'm a dedicated GPT/Claude user, going back and forth between the two for various reasons. We can come back and talk about those specifically, but those are my Mac apps. I also love this wonderfully simple tool called Freeform that you can use. It's kind of like a PowerPoint slide but much simpler. You can tell how I love to strip everything away and just have a basic board where I can put some photos and a little bit of text, or even make a mind map out of it. I use that a lot in my hobbies outside of work.

Damien Schreurs: Yeah, I would like to circle back to Notes and Loom a little bit. Have you heard about the application called Exporter? It's a free application available in the Mac App Store that allows you to manually create backups—so you can export your notes into either markdown or HTML format. I have a recurring reminder: every Saturday at 6:00 PM, I go on my computer, push a button on my Stream Deck, and it launches Exporter. I just have to click a button. I have more than 1,000 nodes—oh, I have 2,179 nodes!

Samantha Hartley: Goodness.

Damien Schreurs: All my standard operating procedures are in Apple Notes. And I would be furious if I lost those. So every Saturday, I make a backup of those nodes in a different format. So it is called Exporter.


Backup Strategies and Time Machine

Samantha Hartley: And why do you do that—in addition to iCloud? Because mine is backed up to iCloud and I do go into iCloud and double-check.

Damien Schreurs: iCloud is not a backup; iCloud is—

Samantha Hartley: Yeah,...

Damien Schreurs: iCloud is a synchronization service. You have a copy in the cloud—a copy on the iCloud server—and technically it would be the master copy. Whatever you do on any device, if there is an issue on the server itself, that issue will propagate everywhere.

Samantha Hartley: Uhhuh.

Damien Schreurs: And so there is still a "get out of jail" card, which is a 30-day bin. When you delete a note, it’s still available for 30 days. But if you delete part of a note and then realize, "Oh no, I should not have deleted that," how do you get it back? Unless you realize immediately and then command-Z for undo, a few hours later—it’s gone.

Samantha Hartley: And you're saying iCloud has synchronized that...

Damien Schreurs: Yes. If you are connected to the internet, that's the power of Apple Notes.

Samantha Hartley: I know.

Damien Schreurs: Sometimes I'm on the same note on my MacBook Pro and my iMac. I make a change on the MacBook Pro and I see it after a few seconds. Boom, it's there.

Samantha Hartley: Exactly. Me too, on the phone. And if I come in and it has really picked up—because for months it would not do that—and now it is instantaneous, that is very helpful for me. And I am not entirely surprised. I'll tell you why: I'm not surprised that iCloud is not a true backup. When I was thinking about installing Tahoe, I went to my friend GPT and I said, "Should I do this? And if so, what should I know before I do it?" And it said, "Well, first you're gonna want to make a backup." And I was like, "Why do I need a backup? Because I have a backup of my whole computer in iCloud?" And it said, "No, no, no, my dear, actually what you have is a synchronization, Damien. You do not have a backup." And I was like, "What? Tell me more." And it said, "Well, let's talk about this thing called Time Machine." So I know you're gonna ask me in a minute, "What's the new thing that you've learned about the Mac?" Guess what—I learned about Time Machine last week. On its way to me right now—and possibly on my doorstep—is an external hard drive, which I have just purchased and with which I will do a real backup. God forbid anything happens in the next 48 hours before I get that done. And I will also be backing up my...

Damien Schreurs: Very good.

Samantha Hartley: So thank you for the tip about Exporter. I will do that as...

Damien Schreurs: When I discovered that, I was like, "Wow. It was something I didn't know I needed." Well, actually, I knew I needed it, but I thought there was no solution until I discovered that.

Samantha Hartley: That's really good—when you think there's no solution, but there actually is.

Damien Schreurs: And then, it's a good link. I was talking about standard operating procedure. If we go back to Loom, I've heard that now it's possible to get Loom to create an SOP out of a recording. Have you played with that?

Samantha Hartley: I have not, because I don't really use the AI features of Loom as much—mostly because we do things manually—but I think it makes total sense that you could do that. It's really imitating a manual process we use: You, my new team member, sit beside me and I'll walk you through everything I do while recording it, and then you'll have this video to go back to if you need to remember anything. I would have you, as the person writing the SOP, write all the steps down, and then we'd confirm them with each other. That would output an SOP. This is basically doing the exact same thing, except the AI is able to pull it out of a video, which makes total sense.

Damien Schreurs: Yeah, and you're right. What I've seen, or heard, is it’s an AI feature that uses a large language model and the transcription to pull out the steps of the process.

Samantha Hartley: Some of the best of them are doing that right now. I think Fathom, to me, is the best I've seen in meetings for pulling out what happened in the meeting and the next steps.


Advanced AI Usage and Customization

Damien Schreurs: So it's a good way to enter the AI segment. You mentioned ChatGPT—do you have a paid account?

Samantha Hartley: Oh yeah, definitely. I have the $20 level paid account for ChatGPT, and I also have the paid version of Claude. I've been using ChatGPT since January, when everybody started using it, and I jumped in immediately.

Damien Schreurs: What do you like most about ChatGPT and Claude, and what makes you go to one versus the other?

Samantha Hartley: What I specifically love about ChatGPT is strategy. All of my items down the left-hand side are named categories. I don't have projects for everything—some are just really long chats because they're not that long—but I'll have, you know, cooking, recipes, pet stuff (dog and cat topics), gardening, themed topics that I can dip into and ask a question, house plants, dream interpretation, and then obviously all my work topics like search engine optimization and legal things. I have a long series of topics and then I can just dip back into them.

What I've really enjoyed is watching it evolve over time because it was so clunky in the beginning compared to how it is now. I think we were all using it and feeling like, "Oh, amazing. Not too bad." And then after a while it started to be like, "Holy cow, this is incredible." I'm on version 5.1 now, and I think it's really remarkable. But about three-fourths of the way through, it drove me to Claude. Somebody had said to me in the very beginning, "Claude is way better at writing—you should definitely use Claude." And I was dedicated to ChatGPT, but then it started to be terrible at writing, so I went to Claude. As Claude ramped up—that's when version 5 came out—that's when I started using that. What I mostly advise people to do is bounce back and forth between them. I think ChatGPT is stronger at strategy and structural thinking, but nobody will ever write like Claude. Claude can sound like me. I have an advantage working with these models because I've worked with ghostwriters; I have ghostwriters on my team who have written for my clients. When it's your own stuff, you feel more protective of your voice. I know the difference between my voice and that of the ghostwritten client stuff. Claude has been able to emulate my best ghostwriters to the point I can't remember who wrote what piece—whether I or the ghostwriter did it. Once you get that real blend, it's seamless. That's really how Claude has written for me on some things. We can get into all the mixed feelings about the ethics, environmental impact, and whether you should allow AI to write for you—and how your audience can tell. There's so much about that. I had ghostwriters who wrote for me, and now I have a machine that's a ghostwriter. Does that mean my ghostwriters are out of work? No, they’re using these tools to help them be more efficient, produce more work, and work fewer hours.

So those are the things I'm using them for. But what I really enjoy is being able to do my personal work—journaling, interactive journaling—with these models. And for work stuff, a lot of us want thought partners. As a consultant for my clients, I am a thought partner to my own clients. And what's funny is, it's easy to think, "Well, you'll end up out of a job too." But it’s like a third partner in my client relationships. It's not like I've been replaced by them. They'll say, "Well, ChatGPT said blah, blah, blah," and I'll say, "Well, here's my take." Or somebody will call me and ask, "What should I do about X?" And I'll give advice. Then they'll say, "That's what ChatGPT said." And I'm like, "Well, good." So I feel like it's just another smart person in the room—whether it's Claude or ChatGPT—and it's not something to be threatened by. It's just cool to have another smart participant in the experience.

Damien Schreurs: How much of the personalization and customization are you using? For Claude, I know they have Claude Projects where you can have custom instructions; for ChatGPT, you can do that with a project or with a custom GPT. How much have you experimented with that?

Samantha Hartley: I definitely use projects in both of them. As much as you can load into there, they get smarter with that. I’ve added a lot of custom instructions. I made a custom GPT way back in the very beginning because I was curious when I heard other people talking about it—they’d be like, "Oh, I have a custom GPT." And I'd be like, "Do people know something I don’t?" Because what I find is if you create it with this strong, specific personality, over time it just starts to sound like generic ChatGPT again. If I'm creating something where I want it to have my knowledge, something I did recently was start working with an online journal called Rosebud. I've talked to you about this one before. It's a journaling app, but it's also about mental health self-care—they have a gratitude journal and other features. But it's basically an interactive, facilitated journal. The reason I started using it was because it's exactly what I've been doing with both ChatGPT and Claude. The problem with those is that their memory would be crap. If you referenced something, it would forget. I have a specific protocol for doing dream interpretation. It could not remember the protocol; every five attempts it would just fail. I would be like, "Why are you not using the protocol?" (Imagine if an employee forgot five times—Damien, you can only forget once, twice, but three strikes you're out.) So that was my problem; I fled ChatGPT after that because I felt I couldn't trust the business information it gave me. If it can't remember a five-step process, that erodes credibility. So I would work with Claude, and Claude would be better about remembering things—even with projects and continuity it would still screw up sometimes. I'm like, "You can't be screwing up again if I'm going to create a GPT to sell to someone else or a custom chatbot." To me, these tools are not ready for primetime. They need guardrails; they need structures. So I'm using a lot of other people's tools because I want to see what they can make happen—or if I can also break their bots the way they programmed them. I know that Rosebud uses both ChatGPT and Claude—you can maybe select for both. In my experience, it has failed to remember the dream protocol at least once, but it has been the best at maintaining a specific personality that I think they programmed into it. I have also coded my preferences into it, and it's been the most consistent thing I've seen so far. And I'm only maybe a hundred days into using it, so I don't have the long history I have with ChatGPT and Claude. So far, I'm seeing that it's better at being consistent.

Damien Schreurs: Yeah, so there's something many people don't realize: there is something called the context window. The context window is on a per-conversation basis, and depending on the model, certain models have smaller context windows while others have longer ones. ChatGPT is actually much worse than Claude in that respect. I think it was all one that started to increase the context window. But before that, it was a maximum of 24,000 words. So if you create a GPT, you start the conversation with the GPT's custom instructions at the top, and then as you keep interacting, once you hit the 24,000-word limit, it starts to forget because it can only refer back to those 24,000 words. The trick is, at one point, to create a new conversation. Claude has a higher context window—I don't remember exactly which one, but I think it's closer to a few hundred thousand tokens, which is much bigger than ChatGPT's. The best, though—I don't know if you've experimented with this because I think you have a Google Workspace for Business account—is Gemini. Gemini has a 1 million token context window, and I have very long conversations with Gemini. For my GPTs—sorry, with my Gems in Gemini—the equivalent of a custom GPT is a Gem. I have a co-CEO, a co-CMO, a co-CFO, because I'm providing corporate training, such as Microsoft Office training for corporations. I have a curriculum developer, instructions, and I have given it a few examples of how I structured my training courses. Now I'm able, in half a day, to create a brand-new module with the instructor loads. Half a day is more like submitting a training proposal to a client, and then it takes me another half day to prepare the slides and training material. This is much faster than what I did in the past. The reason why I'm using Gemini more and more for these kinds of tasks is that I still keep ChatGPT for research, which is very good. I also really enjoy the voice mode of ChatGPT—the way it interacts as a conversation. There is nothing better than ChatGPT for a voice conversation, but regarding context, Gemini is still the best, and I can have a very long conversation with Gemini without it losing the instructions at the very top of that conversation.

Samantha Hartley: Yeah, I remember the first time I ran out of conversation—it was one of those, you know, soul-touching moments. I had sculpted it, got feedback, and it was finally exactly how I wanted it. Then we ran out, and I was like, "Oh dear Lord, now—" I think my favorite thing to do is at that point: "Prepare your replacement. Tell your replacement everything it needs to know about how to work best with me." That is actually what I put into Rosebud. That's how I'll train the others. I also do something similar with each of my clients: I put a bunch of context in and then say, "Tell me everything you need about this client, their writing style, their preferences," and have the AI itself handle that context.


Synthesis of Information and Custom Instructions

Samantha Hartley: Because what it's remarkable at is synthesizing information and the ability to be concise and specific in communicating that. But that's great to know about Gemini. I've heard you talk about your coworkers...

Damien Schreurs: My C-Suite.

Samantha Hartley: C-Suite. Yeah, that's fabulous.

Damien Schreurs: I can spot immediately when it has lost track of instructions. For people who start, I heard a nice tip: at the end of the custom instruction, you tell it to write a specific word—say, "cauliflower"—to create a new paragraph. It will then output "cauliflower" as soon as it stops following that instruction. If you don’t see that word, it means it lost the thread.

Samantha Hartley: Interesting.


Exporting Chat Data and Browser Extensions

Samantha Hartley: Well, I think also, in the sense of decluttering and not hanging onto too much stuff, you could also tidy up all these old chats and start new ones on an ongoing basis because we don't need to hoard all the information in those. But it's kind of like, why—like your Exporter idea—aren't there good exporters for ChatGPT and Claude to output this information in a better, more usable format than these epic chats?

Damien Schreurs: I haven't found one yet. That's a good point. I'm going to write that down to look for, potentially, a Chrome extension or something like that—a browser add-on that would be able to export the chat. Thanks to Europe and GDPR, it's possible to ask those services to export all your chats, but it's one big file.

Samantha Hartley: Yeah. It's a beast.

Damien Schreurs: It's a good point.

Samantha Hartley: I found something—I was so upset about potentially losing data. I went in, got it, and it was, I don't know, 40 pages or something like that. I did have to use a browser extension to select all of it. Originally, it would only select one chat at a time. I mean, it's years of my life—I need to be able to get the whole thing. So that is an improvement. Everything is evolving, and our needs are evolving. Maybe someone has already invented this, but I have the same thing with the Roosevelt app—the journal—and I'd want to pull that stuff out someday. So far, as you're saying, it's like you can get a CSV file or some nonsense, but that's not going to...

Damien Schreurs: Yeah.


Gemini's Integration with Google Workspace

Damien Schreurs: One of the reasons I like Gemini is whenever you ask it to do some deep research and create a report or ask it to create a table, there is a neat button that says "copy to Google Sheets." It creates a table. You say, "copy to Google Sheets," and it's automatically in your Google Drive. If you have a big report after a deep research project, you have a "copy to Google Doc" button— it creates a Google Doc for you instantly. With ChatGPT, that's always the problem: when you have a big report, you have to drag and copy, and if you use the copy button, the formatting is often off. You really have to select with the mouse to maintain formatting. With Gemini, it's a simple button—they even added new features; I don't remember, I haven't played with that much, but I've noticed the "copy to Google Doc" button has a few more options now, like creating an app and stuff like that.

Samantha Hartley: That's great. I have not used Gemini at all except for what happens naturally with Google Workspace. But I will definitely take a look at that, because my business is built around Gmail, Google, all of Google Suite. For a long time, I was dedicated to Microsoft Office, which I know is a lot of your work when you come out of corporate—it's in your blood. Over time, I don't think I'll ever fully switch to Google Drive with all their presentation nonsense. I do use Google Sheets and Google Docs, and I think those are fantastic, especially since we're collaborative. We're a distributed, online team, collaborating. I just like the interactive nature of it. And that's really good to be able to use that way.

Damien Schreurs: Yeah, you need at least the Google Workspace for Business Standard plan to have full access to the Gemini side panel in Sheets, Docs, Drive, and Mail. There's a Google Workspace for Business Starter plan where you can only use Gemini a little bit in Gmail and Notebook. But if you want the full power of Gemini inside Google Workspace, you need the Standard version. I've created my co-CEO, co-CMO, and co-CFO as Gems in Gemini. I can be in a Google Sheet, open the side panel, type "co-CEO," and then ask a question about the data. The co-CEO now sees not only the instructions and its knowledge but also the context of the Google Sheet I'm in.

Samantha Hartley: Oh my God!

Damien Schreurs: It's really magical to realize that you can pull the thing immediately—it’s really great.

Samantha Hartley: Ah, just like a real person. That's really good. I really like that.


Wispr Flow: The Ultimate Dictation Tool

Samantha Hartley: I remembered one tool that I didn't talk about much yet, Damien, and it's the fastest I've ever adopted anything: Wispr Flow. It's a dictation software. I think I was probably using something else before I got my Mac. I don't like to type—even though I've been typing since I was a child—and I talk really fast, so I need to be able to dictate really quickly. We've all had experiences talking into your phone and it wanting to punctuate with all the commas, then misunderstanding you with all kinds of silliness. 

So Wispr Flow has AI built into it. It works on the phone and on the MacBook, and it has a hot key on the MacBook. It's great on the phone because I don't want to type there either, but at my desk, you know, I have to use this little F5 key, and sometimes it wants to work and sometimes it conflicts with something else. With Wispr Flow, I just press and hold for two seconds, say two words, and then release it—it will punctuate and learn. It learns your specific words. For example, if I'm writing to you and it notices that you're "Damien EN" instead of just "Dan," it'll correct accordingly. And if it doesn't, it has a little AI mode: I can push the function key for dictation, or I can push the function and control keys at the same time (this is on the pro version—those two keys together), and then I can give it an AI command, like "Learn 'Damien' with an A, EN" or "Bold this sentence" or "Make this more concise," and it'll do that. It's intuitive. It’s AI and it learns quickly. I can make a bulleted list, and then the whole thing becomes a bulleted list. I can highlight everything with two fingers and remove all the bullets. It's the most convenient, time-saving thing I've installed in the past six months. I use it constantly, and it just gets smarter and better.

Damien Schreurs: I discovered that tool this week, and for the listener, it's spelled W-I-S-P-R and then Flow. I attended a webinar where they demonstrated another AI tool, and the guy was using W Flow to write the prompts because typing was so slow.

Samantha Hartley: Yeah.

Damien Schreurs: And so I discovered that; I looked at it this morning and realized that I already used a tool called MacWhisper. They've been using it for years now, and the primary use case for MacWhisper is not dictation—it's pure transcription. So I can give it the audio version of a webinar or podcast episode with multiple people speaking, and it'll recognize the speakers. I remember that there was a dictation button, and I was like, "Let's look at that." And now I'm able to reproduce Wispr Flow's features with MacWhisper. It's a game changer because the typical dictation—like the built-in Mac dictation—requires you to say "comma, space, new paragraph" and it's very slow. You don't see it working efficiently.

Samantha Hartley: Slow.

Damien Schreurs: And here, with Wispr Flow, what people need to realize is that it does the transcription, but on top of that, there is an LLM that reprocesses what has been transcribed. So if you say something like "Let's meet tomorrow at 5:00 PM, no, 5:30 PM, right?" Traditional transcription would just write "5:00 PM, no, no, no." You'll see that it writes everything correctly. Whereas with Wispr Flow or MacWhisper, it corrects the transcription. It's so great.

Samantha Hartley: It's fantastic. The only downside is that sometimes it makes editorial choices for me that I don't like, so I have to override it. My favorite example is when I was dictating a note and the dog barked in the background—it went "woof." One time the cat walked in while I was dictating, and it transcribed "meow, meow, meow," even typing "w wa." It is really clever and amusing. I'm just excited about the time when we won't have to be limited by typing everything out, because—as you said—it'll correct what you're saying. Then one time, it even put things in quotation marks unnecessarily, and it's tedious to fix that punctuation. It's just a huge time saver. What I'm doing a lot is taking text off large sheets of paper that I need to put into lists. It's part of my work, and you can't hold this thing and type; it would be a mess. So anyway, it's a huge time saver and a game changer. One last thing is that it also understands multiple languages. I can switch languages in the process, and it'll transcribe in the different language, which I also appreciate.

Damien Schreurs: It's very quick. I saw someone using it on his MacBook, and it wasn’t instant—but just a few seconds. It's the same with MacWhisper, though it's better on an Apple Silicon Mac. On my iMac, which is still Intel-based, it's too slow. It takes too much time for the transcription to appear on the screen and then do the post-processing. Whereas on my MacBook Pro, which is Apple Silicon, it's much, much faster. Yeah. Very...

Samantha Hartley: Great tools.

Damien Schreurs: Very good. So let's go to the next segment of the show. I think you alluded to that tip or trick or something that you discovered on your Mac.


Time Machine and Backup Solutions

Samantha Hartley: Yeah, just in time before imminent disaster. I discovered that I was supposed to have been backing up all this time onto Time Machine. I had heard of Time Machine, but I thought it was probably automatic. I had no idea that I was supposed to have an external hard drive. So that was my discovery from last week, and it is a really good thing. One of the things I use ChatGPT for is to help me be diligent. I don't use it for generating silly pictures or doing research that I could have done with Google. I try to use it for sensible uses. I got an external hard drive recently—not a hard drive monitor, but something that would not connect easily. I have it on voice command when I'm, you know, in the middle of something. I don't usually talk to it—though it sounds like you talk a lot more than I do—but I'm talking while typing. I mean, I'm using Wispr Flow to talk to it. In this case, I had it talk me through how to hook these things up, and it also talked me through Time Machine. When that part comes, I'm sure it'll be quite intuitive, but either way I'm going to have it talk me through how to set that up. It's a pretty good combination.

It's an important feature on the Mac that I did not know about. I've been a Mac owner since 2016; this is my second one. And I've just been skating by with no real insurance policy.

Damien Schreurs: Time Machine is—I've used Windows machines in the past, and nothing is as easy as Time Machine on a PC even today. It's unbelievable. The beauty of Time Machine is twofold: Yes, it's a backup, and if you have an issue, you can restore files. It's a little bit like when you buy a new iPhone and you restore from iCloud, getting a clone of your iPhone. You can do the same thing with your Time Machine backup. You plug it into the new Mac, and it takes everything. But a feature I use much more than that is recovering or restoring files or applications.

Samantha Hartley: Yeah.

Damien Schreurs: And that's really great with Time Machine because it does a backup every—you can configure it to run every hour, once a day, or once a week if you use your Mac. If you have lots of calls or online meetings during the day, I recommend setting it to maybe once a day or once a week.

Samantha Hartley: Mm-hmm.

Damien Schreurs: There is an application called Time Machine Editor. With Time Machine Editor, you can configure when Time Machine backups take place. I've configured mine to run very early in the morning—like 4:00 AM or 5:00 AM—before I wake up. That way, it prevents Time Machine from running during the day, because if you're on a call and Time Machine starts a backup, in some cases it can slow the computer down. Very recently, an application auto-updated and suddenly it was not working anymore; so I just opened the Applications folder, fired up Time Machine, went back two or three days, selected the old version of the app, restored it, and I was good to go.

Samantha Hartley: Interesting. Do you think that the issue was that it hadn't, what was it—a problem with the update?

Damien Schreurs: Yes, there was a bug with the latest version of the app.

Samantha Hartley: You could go back to the previous version and then it would come back.

Damien Schreurs: Exactly. And if you delete files by mistake and empty the trash, you can go back in time. I had one client who had a lot of precious videos on his desktop. He deleted them by mistake and then emptied the trash, went on vacation, and when he came back, he realized, "Oh, where are those videos?" Luckily, he had a Time Machine backup, so we could go back one month and get those files back.

Samantha Hartley: Wow. Well, that's super important. And you mentioned the thing about the phone—because the phone backs up to the cloud—I thought that the Mac was also backing up to the cloud and that was the same thing. I've learned that it is something different now. I should set it not to back up during work hours because it will interfere with my many Zoom calls.

Damien Schreurs: It could. It can mess up with Zoom, exactly.

Samantha Hartley: Got it. These are great tips. Thank you.

Damien Schreurs: Very good. If you were in charge of the Mac division at Apple, what would be your first priority—whether it's hardware or software, or both?


Improving Finder Search on Mac

Samantha Hartley: My first priority would be to figure out how to help people find things in Finder. If you go to Search in Finder and type, "I was just working on a file called Tuesday this week," you might get some random file—like a JS file, or some sort of temporary file. You can literally put the name in, and it will not show the file you're looking for as the first result, unlike on a PC. When you search, a PC immediately shows you the most recent matching file. With Finder, when you search for a word inside a document—just like you can in Google Drive or Gmail—it doesn't work properly. What do I love about Gmail? I never delete anything; I have stuff in there from probably 15 years now. I can search for a word, and it will say, "Hey, you have an attachment with this word in it," and first surface probably six relevant items. The MacBook never does that. That would be my first improvement: some tool already exists, Damien, that could do that.

Damien Schreurs: First of all, you are not the only one. It's a known issue. Spotlight indexes everything on the Mac, and when you search in Finder, it looks only for files in the order of the Spotlight index. Historically, it has had issues. There are workarounds—for example, you can go to Settings, go to Spotlight, remove the locations that it indexes, then re-add those locations to refresh the index. That's one thing you can do. But honestly, like you, I've been frustrated. So I switched to...

Samantha Hartley: Is this a thing?

Damien Schreurs: I installed Raycast, which is basically a competitor to Spotlight—but on steroids. The reason it works better is that Raycast builds different indexes: one for files and folders, one for Apple Notes, another for things like that. For instance, if I'm searching for an Apple Note with Raycast, it's super quick. I invoke Raycast, type "SN" for search notes, and then a few words; usually, the note I'm looking for is at the top.

Samantha Hartley: But you don't do that from within Notes?

Damien Schreurs: I actually find my notes faster with Raycast than within the Notes app—and much faster than using Spotlight. And for files, same thing: I fire up Raycast, type "SF" for search files, type a few letters or a word, and usually the file I'm looking for is among the top results. Maybe not the first one, but, as you said, it doesn't show me crap like temporary files or irrelevant files. I was like, "Why do you show me those? I don't want to see temporary files," like some sort of digested files from deep within the computer. I don't think I'm supposed to be seeing that kind of thing. I've heard there was something—I've never used Spotlight much. I was on a Zoom call with a client, and she used it, and I thought, "Oh, I forgot about that Spotlight thing." I would prefer something that actually works properly. So I'll try Raycast. I had heard about something that sits on top of it to do an even better job, so I'll definitely look into that because it's ridiculous to have to come up with workarounds. It’s embarrassing for the company that this is an issue. I heard you say recently on an episode that you can go into your Photos and say, "Show me all the pictures of Satchel, my dog," and it will show them to you—even if it sometimes mistakes my other blue cat, Arin, and shows me some pictures of her. I'm like, "That's pretty good. It knows my friends by their faces but not my files by their literal names." So it's silly.

Damien Schreurs: Yeah, it's frustrating. I know that with Tahoe, with the latest version of macOS, they have improved Spotlight and incorporated functionalities that are now standard with Raycast. 

Samantha Hartley: Mm-hmm.

Damien Schreurs: Like you, I don't want to touch Tahoe for the moment, so I'm not trying out that new Spotlight. If you install Spotlight, it'll ask you what the trigger keys should be. Spotlight is usually Command-Space. Since I'm still using Spotlight for a few things like calculations or currency conversion, I've configured Raycast to use Option-Space. But nothing prevents you, if you don't use Spotlight at all, from configuring it to use Command-Space as well.

Samantha Hartley: Yeah, yeah, yeah.

Damien Schreurs: Exactly.

Samantha Hartley: I don't understand using Spotlight for file searches. For example, if I want to see all of my agreements, I go to Finder and type "agreement." I don't want to go somewhere on my desktop and see everything called "agreement." I should be able to stay within the ecosystem and not be thrown all over.

Damien Schreurs: Yeah. When you are in Finder, I think it's Command-F—the keyboard shortcut that immediately jumps to the search field in the top right corner of Finder. You can then start typing “name:” and it forces Finder to look for files whose name contains that word rather than the content inside the file.

Samantha Hartley: I shouldn't have to do that with a computer.

Damien Schreurs: You're totally right. It should show us the files with that name first and then search inside. But yeah, that's an issue.

Samantha Hartley: Mm-hmm.

Damien Schreurs: Very good.


Connecting with Samantha

Damien Schreurs: Where can people find you?

Samantha Hartley: You can find me at my website, which is samanthahartley.com. On social, I'm most active for my work on LinkedIn—I'm also on LinkedIn at linkedin.com/in/samanthahartley.

Damien Schreurs: Very good. I will put links in the show notes. Thank you very much for sharing with me and the audience all the tools you use. For me, Superhuman is something that I am looking at being on Google Workspace.

Samantha Hartley: It just merged with...

Damien Schreurs: They’re part of Grammarly now.

Samantha Hartley: I think it's more... Yeah, I'm not sure who merged with whom, but there was an acquisition or merger, and now they're together, which I think is a nice little marriage. Wispr Flow just raised 25 billion—I think that's a total of an $81 billion raise for them. So, you know, these companies are up-and-coming. We can also invest in them as well as use them.

Damien Schreurs: Thank you for being on the show and sharing all those tools with us.

Samantha Hartley: Thank you. I always love hearing your tips and tools, and I'd love to hear from anybody who has any ideas about how to make search on the Mac better.


Applying to be a Guest Too

Damien Schreurs: If you, like Samantha, 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, 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 your friends and tag both Samantha and me on LinkedIn. Until next time, I wish you a great day.

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