Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free

I remember when Nextel first launched its "push-to-talk" walkie-talkie feature back in the late 90s. It mostly resulted in people yelling into their phones at the mall, and it honestly made me hate the idea of talking to my phone in public for decades. But things have changed.

Between the rise of asynchronous communication and the power of AI transcription, I’ve found that talking to my phone is actually one of the best ways to stay productive while I’m away from my desk.

In this episode, I’m breaking down why I’ve embraced talking to my phone. I’ll share the two specific apps that have simplified my workflow—Whisper Memos and Todoist’s Ramble feature—so I can capture context, brain dump my shutdown routines, and turn spoken ideas into actionable tasks without losing a single thought.

Is your tech stack helping you or just adding to the noise? Take my free tech stack assessment to see if your tools are actually worth it at streamlined.fm/tools.

Show Notes


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What is Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free?

You started your business for freedom, not to be chained to your desk. I help solopreneurs replace manual tasks with a reliable system so they can take time off worry-free.

On Streamlined Solopreneur you'll get real-world strategies, smarter workflows, and practical tools to help you reclaim your time and actually enjoy the freedom you set out to create.

Your host, Joe Casabona, is a seasoned technologist with over 25 years of experience. He's seen how the right systems can transform a business. But more than that, He's a teacher at heart.

His goal isn’t to overwhelm you with jargon, but to make complex ideas simple and give you an actionable plan you can actually use.

Because your business should support your life—not take it over.

Tune in every Monday, wherever you get your podcasts.

Intro: My coaching client, Laura, recently told me that she saved more money than she spent on my coaching because I helped her simplify and consolidate her tech stack. And now I want to do the same thing for you, too. I have put out a free tool called the Tools Audit. It will help you determine what tools you use, how much you're paying, and where you can consolidate and eliminate to simplify what your small business tech stack. You can go to streamlined.fm/tools to get your free tools audit today. That's streamlined.fm/tools.

I remember when Nextel came out with their walkie-talkie feature for their phones. You could push to talk over cellular. I won't deny that this served in some practical settings, like on a construction site or something, but it largely amounted to a bunch of ding-dongs yelling into their phones at the mall, having short, fragmented conversations for all to hear. This is probably what made me hate talking to my phone.

If I had the ability to type discreetly while I was in public, why would I opt to tell the whole world what I was typing or what I was trying to talk about? They don't need to know that I can't find the specific sauce my mom wants from the store. But a few things have changed since 1997, and I find myself talking to my phone a lot more. Today I'm going to tell you how and why I am using my phone in this way. \\

Hey everybody, welcome to another episode of The Streamlined Solopreneur. A show that helps you simplify your tech stack so you can confidently step away from your business without fear of it crumbling.

So, one of the big reasons that I have gotten over this, let's say, hesitancy to talk to my phone, is that lots of people are actively recording and broadcasting themselves on the internet. Earlier this yea,r I was in Disney World, and I am always just gobsmacked by how many people choose to livestream or record their entire experience at the park.

But I don't do that. I don't like doing that. I'm uncomfortable doing that. I had to record myself for, uh, a piece of user-generated content for a brand, and I didn't even like doing that out in front of my house. So, that's not really the reason I'm more comfortable talking to my phone in public. No, there's actually more utility— there's more practicality to talking to your phone now.

I have embraced audio notes in the Messages app. Uh, it is asynchronous, and so I can choose when to both send and listen to messages. This is again, 30 years on from when Nextel's walkie-talkie feature came out. Uh, it is more likely that I'm talking to people in other time zones and with different schedules. And so the async ability to still speak with a voice is very appealing to me. I can again choose to, uh, send and listen to messages on my own schedule.

Headphones are also a thing now, uh, so you can— at the very least, uh, you're not broadcasting both sides of a conversation. And so you're not, you know, putting somebody else's privacy at risk, but you can also find a quiet place and talk more quietly. But of course, the biggest change and the most practical change for me has been the ability to talk through my thoughts to a little robot on my phone that is transcribing and processing what I'm saying. This has made me far more productive because it means that I can process thoughts away from my desk. I don't lose ideas or forget tasks. When I get inspired or think of a solution, I can capture the entire context. Heck, when I need to change context, I can talk to my phone as I'm changing that context. And I'll get to that one in a minute, though. Longtime listeners will know exactly what I'm talking about here.

One of the most impactful things my Computer Science teachers did was to think out loud through problems in class. It's very, very likely that my teachers had solved those exact problems for many years. But whether they consciously knew it or not, they knew how important it was to talk through problems, even if it's just with yourself. And so as Dr. McCloskey stood up there talking through some classic Computer Science problem like the Dutch national flag problem, it was very instructive to us because we saw how he was solving the problem, and it helped him think more thoroughly through it.

This is where the whole notion of rubber ducking comes from, which if you're not familiar with the term rubber ducking, it's the idea that programmers specifically, which is weird, I really thought this was more of a universal term, but programmers specifically would get a rubber duck to sit on their desk and then they would just talk to the rubber duck. They would get to a problem that they were having trouble solving and they would crunch through it by thinking out loud. Talking to the rubber duck on their desk.

And this, my friends, is why I've really come to love talking to my phone. It allows me to capture ideas in full when I think of them. It allows me to think through complex problems no matter where I am, so I don't lose my train of thought.

And then it allows me to send all of that information wherever I want. It could be Obsidian, it could be Todoist, it could be my email, all for me to review later when I'm actually at my desk. I can and have written tomes on how I think AI is making us lose our critical thinking skills. By letting it do stuff for us, we lose the skill to do that stuff.

Critical thinking is not like riding a bike, but talking to our phone in this way— well, that's one way where AI can help us preserve our critical thinking skills. This is the exact thing that we talked about a few weeks ago when I interviewed Christian Åhlström about feeding a bunch of data to your phone or to an AI and then having it come up with 3 deep, meaningful, unique questions for the new— to answer by talking into your phone.

So, let me tell you two apps I love that are perfect for this.

The first is Whisper Memos. It is an iOS app, and you can push a button on your phone or your watch, talk into it, and then it will give you the entire transcript. It'll email it to you. I also have an automation set up to send it to, uh, Obsidian, which is my kind of second brain personal knowledge management app. But it also has two really great features. One is it will create different summaries based on different prompts or templates. And so I have one for a journal entry. I have another one for Todoist. I have another one for a spoken article. And so I can apply any of these summaries to the same transcript and get different output.

The other feature that they have, but their different summary templates have kind of killed this for me, is Zapier integration. And their Zapier integration is especially good because you can set it up where if the note starts with different words, it will send the text to different Zaps. So for a long time, I had a custom Zap set up with Whisper Memos where I said, "Shut down routine for—" and then whatever day it was. And then I would just brain dump everything in there. It would send that text to Zapier, which would in turn send it to ChatGPT to create a list of to-do— items or task list. And then it sends that to Todoist, my task manager.

And again, I had this same one where it was like a spoken article where I would say an article idea, and then I would speak the article, and it would send it to ChatGPT and come up with an article using only my words. And that was okay, I never really used the output — from that, but at least I had the skeleton of an article ready to go.

I don't really use either of those anymore because of the custom summaries in Whisper Memos, and because of the other way I really use the ability to talk to my phone, and that is with the Ramble feature in Todoist. So I put out a video a while ago called, uh, Todoist killed my favorite automation and I'm happy about it. And I should say full disclosure here that Todoist saw that video, liked what they saw, and then, uh, partnered with me to create user-generated content around the Todoist Ramble feature. You can see some of that on my YouTube channel. I'll probably add the rest of it very soon. So, just full disclosure there, but they reached out to me because of the content I was already creating.

And so the great thing about the ramble feature in Todoist is that I push a button on my home screen. I have— they have like a lock screen widget that I can use with my iPhone, and I just start talking to i,t and I say what I need to do and what project it's for, and when it's due. And the priority and a whole bunch of other stuff. And it's so much better than my custom Zap because it integrates directly with Todoist, and it understands the context of what I'm saying.

And so in both of these cases, they adhere to my core philosophy of the fewest links in the chain, the better with Whisper Memos, it's summaries inside of Whisper Memos. And with Todoist, it's the ramble feature inside of Todoist to create a task list just from me rambling, me brain dumping. It does a really, really good job, which means that if I run out of, uh, OpenAI credits or Zapier goes down or, or something like that, I don't have to worry about losing very crucial text, right? Those things help me switch context, help me capture what I'm thinking about in the moment so that I can iterate on it later.

My goal is to make life as simple as possible for solopreneurs who want to use tech and leverage tech we all have to. And Talking to your phone in a reliable way that gives you a full transcript and the full context could not be a simpler way to do things.

So that's what really wanted to talk about. If you don't want to shell out for Whisper Memos, you could always use the Voice Notes app or the Voice Memos app, uh, the audio recorder if you use Android. Or one of the many other audio transcription apps that you can get now. There's like Super Whisper, uh, there's another one from the makers of MacWhisper, uh, which I'm escaping— the name is escaping me. But I love, love, love Whisper Memos. Of all the ones I've tried, it's best in class.

And again, with Todoist, I have been using Todoist for what feels like my entire adult life on and off. And I finally, just a few years ago, thought, why do I keep switching away from this app? I finally switched back to it. I'm going to stick with it. And ramble is definitely a feature that will keep me using it.

So that's it for this episode. Let me know what you think. Do you talk to your phone? How, why, and when? What tools or apps are you using? Let me know over at streamlinedfeedback.com. If you are wondering if your tools are worth it, or if you're using too many, if you feel like your tech stack is too complicated, you can do a free assessment that I built inside Notion over at streamlined.fm/tools. That's streamlined.fm/tools. I will have all of that, as well as the apps I mentioned in the show notes for this episode. You can find this in every episode over at streamlined.fm.

Thanks so much for listening. And until next time, I hope you find some space in your week.