If you're overwhelmed by a chaotic business that's stealing time from your family, Streamlined Solopreneur is for you.
Hey, everybody, my name is Joe Casabona, and I've been there. And on this show, I will show you how to turn chaos into clarity so you can stop checking your email at the playground.
My dad was angry. I couldn't even tell you the company he was talking to or what exactly he was mad about. I just remember that there was this decisive feeling that the company that he was talking to on the phone did not care. And I remember him saying in his thick New York City accent, Never again. Never again will I buy anything from you.
And I thought, wow. I wonder if he's serious. And in this instance, he was. There were many times where you just can't follow through on that for whatever reason. I know because I have adopted this trait from my father whenever I experience poor customer service. And poor in the sense that there's just a complete apathy, right? Just not caring. I'll say in my best Pete Casabona impression, never again.
And for some things, it's true. I quit using Uber and DoorDash because of just the God awful service I got. But when I say it to an airline like American Airlines, I can't really follow through on that if they're the only reasonable flight flying to the destination I'm trying to get to.
I think about this a lot because it's really easy to say never again with tools. You can switch and try something new, but the cost of moving back and forth seems to be low. Is it though? That's what I want to talk about today because I chronically switch tools. I'm trying to be better, and there's a few reasons why. And that's what we're going to get into.
So, I'm going to talk about the real cost of switching tools. I'm going to talk about a few times. It's a rule of three story. A time where it was easy to switch, a time where it was hard to switch, and a time where I ended up switching back. And then I will get into a few questions you could ask yourself when you're considering switching tools.
So first, why do we switch? Well, it could be something like we're discovering a better tool. Right? I moved from Loom to Tela because Tela is generally a better tool than Loom is. It could be this new tool will solve all of my problems. Oh, if I just get the perfect CRM or the perfect second brain app. You know, maybe then there's a situation or an opportunity where you might consider switching.
And then there's the rage, Quit. This is a reason why I quit or threaten at least to switch tools a lot. I get frustrated with the company that makes the tool. I don't think they're doing right by their customer. And the best way for me to show my protest is to walk, which I'm considering switching banks as I record this, just because it's been so bad for so long. But in that case, the cost of me switching banks is great. It's a pain. Is the juice worth the squeeze? That's what we'll get to in a little bit. Aside from just whatever this one thing, right? It's cheaper or it's better, it'll solve all my problems, or the company sucks.
Now, there's still the bigger cost of switching tools, right? There's the time investment. You're going to have to spend time learning the new tool and migrating over to a new tool and setting it up the way that you like. This is part of the reason why I don't switch browsers super often. Like every year, around the time the new Apple operating systems come out, I think, oh, maybe I should move to Safari. But the reason isn't there, and the cost is too great for me to switch over full-time.
And like Arc just has my number. Like the way that things are set up in Arc are really good for me, and I wish that Apple would let other browsers steal that two-factor authentication text message thing. But sometimes the cost is too great there, right?
There's also the mental energy and the decision fatigue. There's so many of my brain cycles have gone to should I switch? Evaluating if I should switch, or in some cases not evaluating and just doing it and getting halfway through the switch and going, this is stupid. I've done that too many times, probably. This is things that you don't need to or shouldn't be spending your time on. There could be financial costs, right? New subscriptions or overlapping payments.
One reason that I don't really pay annually for a tool anymore is because I tend to move tools a lot for whatever reason or at the very least, I'd like the flexibility to not be locked in, right? And when I talk about Dropbox, we'll definitely see how that's biting me, right?
One of the few tools I do pay for on an annual basis is ConvertKit. Well, Kit, formerly ConvertKit. Because I'm very confident that the cost of switching would be too great for me at this point. AI tools definitely month to month on those because the cost for switching, it's getting a little harder, right? If you have custom projects and it learns stuff about you. But you know, moving from Gemini to Claude or Claude to Perplexity, that's not a huge cost month to month. It's almost like streaming services. You can stop paying and then pick it up, and you're right where you left off.
There's also the, you know, the potential downside, downtim,e and workflow disruption. Right. Again, I'll kind of talk about this in a little bit, but when you switch tools, especially tools that are core to your business, you are going to need to think through all of the ways that you use those tools and all of the people, if you have contractors, that could be affected by that.
And then finally, there's also like this sunk cost. I try to avoid the fallacy of the sunk cost. But like, you know, if you use Notion and you're like, oh, maybe I should switch to Obsidian, for example. You have so much stuff in Notion, you have it set up perfectly, and you have the knowledge of that system. Is there, is a sunk cost to jumping ship and moving platforms?
Those are some of like the hidden costs or the actual costs of switching tools. Right? There's the investment learning curve, time, mental energy, and decision fatigue, the potential downtime or workflow disruption, financial costs, and then the sunk cost of your knowledge and existing setup.
So, before we get to the things, like the things that you should ask yourself, I want to tell you three stories. The one that is freshest in my mind because I just did it over the weekend, as I'm recording this, is moving from Dropbox to Google Drive. This is completely unforeseen. So much so that Dropbox is one of the things I pay annually for because it's just such a crucial part of my workflow.
So, less than a week after I renewed, I'm switching. But the thing that prompted it was that I got an email saying that I'd be subject to the Philippines VAT tax. What bothered me was that they, when I said, like, what is this? I'm based in the US. I don't understand. They came back with, well, it looks like you're using A plus account for business, and that's for personal use only, which I didn't know, but they didn't answer my question. And the only thing they said was you have to upgrade to Dropbox Business or Dropbox Professional to avoid the VAT Tax, and I'm like, and I'm just like why? And they just gave me the stock answer over and over again. And that just really rubbed me the wrong way.
I also find like that when I use Dropbox on my Mac and I search for files, they don't show up on my Mac. So if I want to search for something, I have to go to Dropbox. Like that's a bit of a headache. And to be honest, I upgraded to the, I think it's called Business Starter, in Google Workspace. So, you get like the advanced Google LM and Gemini features, but you also get signing like e-ignatures and two terabytes, which is what I was paying for with Dropbox. And so it's a considerable cost savings for me. And it's 120, I guess, with the 12% it's going to be like 130 bucks for Dropbox, or I upgrade and it's 200 bucks a year. Right?
And I'll probably still have the issue because my VA is probably going to log in with that account anyway. And I just like that, that was the problem for me. They didn't make it clear why I was getting emailed about the VAT tax. They didn't make it that if like I stopped logging in in the Philippines, I could avoid it. They just like this is unavoidable because you're using it for personal use. Which again doesn't make sense to me. So, you know like it was like sudden and insufficient and very clear that they don't care. They were just, it was a very frustrating experience for me.
And then I looked at Google Drive, and I'm like oh, the same space. I'm eliminating HelloSign and Dropbox, and it's cheaper. I'm getting all the things I'm already paying for with Google, and it's cheaper, and I can log in on multiple accounts on my computer. And when I search for a file in Google Drive on my computer, it actually shows up as a file. It's not doing whatever weirdness Dropbox is doing. So, I decided to do the switch.
Honestly, it was, that part was a lot easier. But here are the things I had to think through. What automations are currently using Dropbox? What team members, or what people or what freebies are currently accessing Dropbox? If I downgrade to free, which I did, how much space will I have? And it turns out it's like 14 gigs because I got a bunch of referrals and so like what is using all of my space?
So when I did the switch, I have the Dropbox app, and the Google Drive app on my computer. And so it really was as simple as dragging out of Dropbox and dropping into Google Drive. And it gave me the opportunity to clean out Dropbox, organize Google Drive, and everything worked pretty flawlessly.
Except, and this is a consideration I hadn't made. My editor for this show doesn't use or pay for Google Drive, and his workflow is to upload episodes to a production folder in Dropbox, and he said he would hit his limit pretty quickly, and the way he does things is through Dropbox. And so I thought, oh, this was a consideration I hadn't made.
Another thing I really need to test still is like, how is it going to impact my VA? She should be able to just access all of the files. She doesn't really need to put anything into Dropbox. So I don't think that will be an issue. But it's something I had to think through. What I'm doing with my editor now is because I have 14 gigs in Dropbox and on the Hazel app on my computer, when a file hits the production folder and Dropbox, it moves it to the production folder in Google Drive. So like that's easy peasy, right? So that. But that was, I kind of shotgunned it. I didn't talk to anybody, I just did it. And that's fine. I'm a solopreneur, and if that's the tool I want to use and that's the tool I'm going to use.
And then the automations were another thing. Turns out that was also really easy. It was like slightly different than Dropbox, but it was a very clear switch, and so I don't, I didn't have to worry about that. Everything appeared to be working properly, swapping one out for the other.
So the only real unexpected challenge was the team access. Right? File organization was fine. Sharing links. Anything that I was sharing in Dropbox is still there by virtue of the free account. And I'll probably keep doing it that way, though, who knows? Like I'm going to have to keep a job. I won't be able to completely quit Dropbox when I have to keep a Dropbox account. But using Google Drive is also fine for that.
So was it worth it? Yes, I think so, so far. It's still early days, but the savings and the just like customer service is a really important thing to me, and as long as you show me that you care, I won't get mad. But like when you just give me the same stock answer, over and over again, no matter how I ask the question, it shows that you don't care. And that's what bothered me about Dropbox.
Okay. So that was Google Drive to Dropbox.
Number two, moving from Castos to Transistor. This was another thing I shotgunned a little bit, because, again, for kind of the same reason, I didn't feel like Castos cared. So the thing that made me switch from Castos to Transistor was that they let go of my friend, and he was the only person who I felt there at least cared about the product.
And about podcasting, the product had a lot of issues that I overlooked because I had my friend's ear, and I said, hey, man, like, this stuff is going on. He's like, I'll check into it. And once they let him go, I was like, no one's gonna care now. So I moved to Transistor.
So, moving podcast hosts in general is fairly straightforward. There's a whole SOP that I have for it. What made it hard for me was I had this big Rube Goldberg machine of a website for my podcast with a bunch of custom code that relied on Castos, and I had to change that. And so ultimately, I had my VA, I'm sorry, Ana. That was probably a really annoying project, but she went through updated the embeds for every episode, which I think at the time is probably like 300 episodes. So she went through and updated the embeds everywhere. I had to update, I had to rewrite some of the code, and really make some decisions about how I was going to do things. And I just went through that again. I'm trying to simplify, but I'm not switching hosts anytime soon.
And so with that, I hadn't thought through all of the ramifications, really. I just kind of switched and then put out fires. And I'm ultimately glad I switched, though. If I had waited a little longer and I got hired, you know, because I got hired at rss.com a few months after that, I probably wouldn't be using the dynamic content, and so those wouldn't be features I would have needed. I would have found other ways around it or just not used them.
So, like, while I'm happy, I think I would have benefited from waiting a little longer and thinking it through, but ultimately, Castos was just so bad that I don't think I would have been able to wait. You know, they're routinely, their updates, like, broke my stats because they didn't properly test things. And that was really frustrating.
Okay. And the third case study, this is gonna be a quick one. I was going to switch from Riverside to SquadCast because Descript acquired SquadCast, and I was using Descript already. And I figured why am I gonna pay for two services that basically do the same thing? But, nnd the switch was super easy, right? I didn't need any of the historical stuff from Riverside. I was paying month to month with Riverside. I would just switch where I recorded my podcast, and the automations more or less remained the same.
Riverside doesn't really have any automations, but you get like a set link or your studio. You could kind of do the same thing with SquadCast. But SquadCast also does have some automations in place. I used it for a bit and I ran into some trouble. I'm not going to say that there was like a quality issue. Recording over the Internet, especially when you're doing like 4K video, is just really hard. So I'm not going to blame that.
But the thing that really bothered me was the way projects were organized. Like it just, I didn't feel like it worked very well. And where Riverside is a fully web-based tool, the handoff from SquadCast to description when I was doing it was not smooth.
And then I stopped editing my own videos, or I stopped using Descript for other stuff. And I thought, well, I like Riverside better. And so I ended up switching back. So I don't know, there was like a switch trap to avoid there, you know. Except that I didn't have any good reason to move away from Riverside. I just thought I could save some money and like ultimately, again, the switch was a low lift. It's again, it's a lot like canceling Netflix to get Hulu. As long as you don't delete your account, you can go right back to Netflix and cancel Hulu the next month.
So that one was pretty easy. I don't have any regrets there, but those were kind of three stories, right? The easier than I expected. But some things I didn't think about. The big pain in the neck and the switchback.
So, as we're coming to the end here, before you decide to switch tools, before you say never again, what are the questions that you should ask yourself?
1. What specific problem am I solving? I think that's the number one thing. Why am I using this tool? What problem does it solve for me? Will this new tool solve that problem for me?
2. My friend Kronda, she was on the show a while ago; she recommended this. Write a job description for the tool, what everything it's going to have to do for you, and then evaluate if there's parity between the current tool you have and the new tool, or if the new tool does this thing that you now need that the old tool doesn't. That's like a really good reason to switch. All of a sudden, you've outgrown the current tool.
But if you're just switching for funsies, you need to make sure that there's parity. Have I exhausted solutions with my current tool? Right? Is there something that I haven't tried with my current tool? Is this a nice-to-have or a must-have? And can I test the tool without fully committing?
I think cost only is not a good reason to switch unless the cost is great. Like switching from a $20 a month tool to an $18 a month tool is not a good reason. But if the tool is 20 now and will be 60 next month, that's a considerable change, right? And it's probably worth the switch. So this is the thing that you should, it shouldn't just be about cost saving. It should be about cost saving and time saving, and solving a problem that you currently don't have solved.
So when switching, think about if it actually makes sense, if you actually need it, or if it's just shiny object syndrome. I should also say like, if there's like some moral reason, that's fine too. Like that's totally on you. Customer service is really important to me. If a company doesn't reflect my values, I'm less inclined to use them. If it's not a kind of moral or values-based question, then it's like does it make sense, or am I just having shiny object syndrome? Has the tool I'm using have I given it time to prove itself? I think another thing, like have I given it enough time? On the other hand, if you're learning a new tool, think about how much time you really want to sink into switching.
And I think the thing that you really want to consider is, is this going to make my life easier? Is the short-term cost worth the long-term investment? For Castos to Transistor, It probably was, though maybe not. I'm not 100% on that one. Dropbox to Google Drive, I'm confident it will be. I have removed a number of tools I've consolidated, and I've lowered my cost. And Riverside to SquadCast obviously wasn't.
This is what you should think about. Are you thinking about switching tools? Have you switched tools? You know, one I didn't talk about was moving from Airtable to Notion. That has been worth it for me in the long run because it has saved me like 2 to 300 bucks a year. And it's easier for my VA, and it's easier for me to share with other people, and it's just kind of nicer looking. And the feature gap that existed between Airtable and Notion when I switched is pretty much gone. So really happy with that switch too.
What's a tool that you use? Let me know. streamlinedfeedback.com. Tell me your switch story. Do you regret it? Are you happy? I'd love to hear it. Maybe I'll read it out on the show.
Thanks so much for listening. And until next time. I hope you find some space in your week.