Can Your Business Run Without You?

Can You Take a Real Vacation?

Announcer: You are listening to the Mastering Business Basics podcast, where we discuss how to build a solid foundation under your small business to improve your chances of success. And now, here is your host, Roger Pearson. 

Roger: I have a special guest today by the name of Joe Casabona. He helps solo businesses save 25 hours a month without over-reliance on AI, which is the big thing nowadays, or hiring a full team of people to take everything off of his hands. Now, that's the trick, if you've ever managed to run your own business. 

He's also been a TED speaker, which I find amazing. I'd probably be scared to death getting up in front of people doing that. And he has a master's degree in software engineering, so he knows how to build systems. So welcome to the show, Joe. 

Joe Casabona: Thanks so much for having me, Roger. I'm excited to be here.  

Roger: You know, one of the things that your main focal point is, your podcast, your books, and all the other activities that you do is teach people basically time management, as I understand it. Is that correct? 

Joe Casabona: Yeah, absolutely. It all starts there.  

Roger: So before we get to that though, I always like to ask people, what journey did you take in life to get you to the point that you're at now? 

Joe Casabona: Mm. Great question. I'll give the abridged version. But I was always trying to figure out how to make money just, like, outside of a job, where I would try to, like, turn profit at yard sales. I would... I made mix CDs, like, I had, like, the first CD burner in my high school and one day my church came to me and they said, "We need a website." And I said, "I don't know how to make websites." and they said, "We'll pay you." And I'm like, "Perfect." So I learned how to make websites, did that for a while, and I really enjoyed it. Um, So I went through college. I got my master's in software engineering, and I really wanted to keep working for myself. I did that until I needed health insurance, and then I got a job that provided health insurance, based in the United States for those listening. 

And I got married, and I was not enjoying my job anymore, we'll say. So I spoke to my wife and I said, "I think I wanna start my own business again." she fully supported me. We had a three-month-old at home. And, she still fully supported me. And so I was married, so I had health insurance, and I started my own business again. that was going really well for a while until our babysitter quit, and the pandemic happened, and we had another kid, and my wife is a nurse, and I couldn't handle it anymore. And so, like, I couldn't manage raising my kids and running a business and I ended up having a panic attack, and I knew that things had to change that day, and it really came down to, how am I spending my time? Am I spending my time on the things that are moving the needle in my business, or am I doing a bunch of nonsense that I could give to robots or other people? And a year later, I was able to take six weeks off. We had our third child, and I was able to take six weeks off to spend with my newly expanded family. 

So, it really has made a huge impact on me, I wanna help as many business owners as possible, so that they don't have a panic attack, 'cause that was a very unpleasant feeling. It was a very helpless feeling. 

Roger: Oh, I can imagine. I can imagine. I mean, we both are kind of on the same mission with different paths, you know, because my whole thing is for the last quarter century I've been doing business taxes for people. And every year I see how much money they lose and how messed up they are. 

And of course, so I've written books and the podcast and everything, but, about the legal part of it, the accounting part of it, the tax part of it, which people don't realize till they get into business, is one of your largest line item expenses, and you have to know how to manage it. And so you have to learn this stuff. 

I have so many people that say, "Well, I'll just hire somebody to take care of that for me." And, I ask them, "Do you interview them first?" "Okay. No. No, Uncle Joe recommended this person." I say, "Okay. Do they sit down with you at least once or twice a year and discuss how your business is doing?" "Well, no, I just hand my stuff over and they call me when it's done." 

I said, "Well, then go fire them, because they don't care about you and your business." And those are the type of things I get. The time management is the next level above that, of course. Once you get your structure built properly, then you gotta start doing things. Hiring people, if you've got that type of business, and all the other things that go into marketing and so forth and so on. 

And that's where the time management that you're talking about comes into play. And the thing about people, I think they have to understand that if you can't walk away from your business for a couple of weeks and have it still make money for you, you've got something wrong. 

Joe Casabona: Yeah, you've just got a worse boss, right? Like, I mean, that's, you left your full-time job to start a business, but now you have, you're an employee in a worse company where you have no other people to cover you while you're gone 

Roger: That, that's true, and I think a lot of people don't realize they have to view themselves as an employee of their business. 

Joe Casabona: Mm-hmm. 

Roger: Too many people just say, "Well, I'm the, I'm the owner, I'm the boss, I'm yada, yada." which sounds great, but you have to view yourself as the employee also. So if you were your own employee, what would you be telling yourself? 

And I think a lot of people miss that. 

Joe Casabona: Mm-hmm. Absolutely. Well, yeah, how would you feel if you denied, an employee vacation, right? Or how would your employee feel if you denied them vacation? But a lot of solopreneurs and small business owners deny themselves vacation, true vacations, right? Not working from a different place, actual close the laptop vacations all the time. 

Roger: That's true. It's absolutely true. So if somebody was gonna start out their own business and they came to you and sat down with you and say, what would you instruct them? How would you start teaching them what they need to know to manage their time to achieve that? 

Joe Casabona: Yeah. Well, you know, I went to the University of Scranton. It's a Jesuit university, and we were forced to learn about Socrates, which I didn't like as a 20 year old computer science major, but as a 41-year-old, uh, business owner and father, I really enjoy the philosophy side of things. And, something that routinely came up was you need to know what you don't know, right? 

Um, and so the first thing that I do with people is figure out what we don't know. How do you work? How do you decide what to work on every day? What are you doing? Are you doing planned work, or are you putting out fires all day? Because we need to understand if you're putting out fires all day, how do we prevent those fires from happening so you can sit down for a solid three or four hours and do the work that really matters? And how do we figure out the work that really matters? Those are all things that I think a lot of business owners, especially starting out, right? They're so busy trying to get things up and running and doing and reacting that they don't have time to step back and say, "Oh, I need to be doing more of this," or, " I need to stop doing this," or, you know, " I try to work from 6:00 AM to 8:00 PM and I just, like, I don't have, I don't have it in me," right? 

Uh, or, "I'm really unproductive from 2:00 to 4:00." And so I help people understand what they're doing and when they work best and the things that move the needle so that we can properly plan their week and lay out their tasks. And, and those are kind of all the parts that go into actually building a system, right? 

It's almost like Lego, right? You, need to know what parts you have so that you know what you're going to build. 

Roger: Right. And that takes, basically you have to sit down and analyze each person's business and what their aspirations are to be able to come up with their system. Because systems aren't one size fit all. I mean, over the last 50 years I've looked at so many systems and tried to fit myself into them, and they didn't work. 

Joe Casabona: I think, and, like, this is the problem, this is a problem I hear a lot, right? "Well, you know, I tried buying this Notion template," or, "I tried using this tool, and it just didn't work." And I'm like, sure. You know, like, you know, it's kind of like wearing someone else's shoes, right? If I... I'm five foot five. 

If I tried to wear Aaron Judge's shoes, it would not feel good, right? I went to the shoe store, and I got my feet measured, and I have great shoes that are perfect for me. And so is, this is the fir- And it doesn't have to be a long, arduous process, right? This whole thing can be iterative, right? And that's, like, kind of the goal of, I have this framework, uh, The Streamline Solopreneur System, where first we lay out your goals, right? 

'Cause this is the first thing we need to know to build your system. Do you wanna spend half of your days touching grass, or do you wanna volunteer more at your kids' school? Great. Do you wanna make as much money as possible? I'm probably not the right person for you, right? I'm here to help you build a lifestyle business where you can walk away from your business. If you wanna take, like, the Alex Hormozi approach, I can't help you with that 'cause I don't know anything about, I don't care anything about that, right? Um, once we know your goals, then we can say, "Okay. Well, what does your day look like? When do you have the most energy?" 'Cause we need to protect that time, and once we protect that time, we figure out what you need to work on.  

Roger: That's a good place to come from, I think. So, what do you think about all the automated systems out there? And in particular, what's coming up now, I keep getting tons of emails about AI. And I played with AI. I'm using AI to redo all of my websites. It's great for website design. . I can't imagine the amount of hours it has saved me. but I've looked at a couple of them that are supposed to help you organize, read your mail, and sort this and sort that and everything else, and I'm going, "This sounds more complicated than just doing it manually." What do you think about that? 

Joe Casabona: Yeah. You know, anybody who, anybody who tells me, "Oh, I've got 127 agents doing a bunch of things in the background," I'm like, "How long did it take you to set those things up, and what are they doing, and how are you measuring if what they're doing is actually helping you achieve your goals?" Like, I had a friend who's like, "Oh, man, Claude is so good at writing sales copy." And I was like, "Good at writing sales copy in the sense that it's something you didn't have to do, or in that it's actually converting people to buy from you?" 'Cause that's what sales copy is supposed to do, right? 

Roger: Right 

Joe Casabona: And like AI can take anything off of our plate, but that doesn't mean it's doing it well, right? 

And so when I think about how to use... So first of all, I have been automating for a long time, right? I'm a software, I was a software engineer for a long time, and so I would write little apps to do certain things for me. And then, you know, Zapier and the no-code revolution happened, and I thought, "Oh man, I can do this at scale for more people," and it's so fun, and we can connect a bunch of things and make a real impact, right? And AI can be the next iteration of that. And something I say all the time is AI is for tasks and not craft. So you mentioned it makes your websites, it's really good at that. It's speaking its native language, right? It's writing computer code. It's a computer program that's writing computer code. It's super good at that. What it is not good at is judgment and taste and accountability. So it'll go off and do something, and I'll be like, "I didn't tell you to do that." And you're like, "Uh, you're absolut-..." It's, "You're absolutely right. I'm so sorry." but like, what am I gonna do? It doesn't care if I stop paying for the subscription. 

It doesn't care about anything 'cause it can't care. It's not a person. and so some of these things, you know, managing my email inbox, for example. At the end of the day, I have Claude run a skill that looks at all of the emails that came in that day that I have read and pull to-dos out of them. So like pull my tasks out of them and put them in to do list. This is something that I may have forgotten to do or you know, might have missed something. Sometimes it's a little overzealous. I would rather it be overzealous than not detailed enough. Um, but the key there is emails I've already read, right?  

I don't have an agent that's reading my emails and generating a report and telling me how to respond. That's still a me task 'cause, uh, like you said, setting that up is, the juice isn't worth the squeeze. And so when we think about how we use AI, we really need to think, "Does this task need to be done? Uh, what is the goal of the task? How will I measure if that goal is being accomplished?" And if you can't answer those three questions, AI probably is not the right tool for it because it means you need more information to determine if it should be automated or if it can be automated effectively. 

I think, and the last thing I'll say here, I was just talking for a while, but people talk about efficiency, right? "Oh, I’ll do this faster. Oh, this helps me do it faster." Faster is not better, right? I can jump out of a plane without a parachute. I'll hit the ground super fast, that would be very bad for me. We really need to think more about, especially as we let AI do more things for us, is efficacy. Is it effective? 'Cause that's the only way that AI is actually going to work for us. 

Roger: It really is. I found that you have to train them. You have to train them like you would train an employee. And so you really have to use them like if you hired an employee to do these tasks for you, how would you teach that employee, "This is the way I want it done”. And you kinda have to bring it from that, viewpoint, or it's just gonna throw garbage at you. 

Joe Casabona: Yeah. 

Roger: And the other problem was different ones work differently. You know, I tried one that it did the CSS and the JavaScript code for me fine, but it wanted me to go out and manually create all the directories and copy all of it in, blah, blah, blah, blah. 

Where I've got this one over here that just, okay, paste this into terminal, and it'll do all of it you know? That's a learning curve too. But so many... I get so many advertisements now and everything, of people coming up with, scripts, that they want you to buy their scripts, and, "Hey, this script will do this for you," or, "This script will do this for you," otherwise teaching the AI how to do it, basically. 

And I'm just wary of that too because, again, it's not necessarily the way you wanna work. And I wouldn't hire an employee like that, that the employee only does things this way. It doesn't make any sense. It doesn't make any sense at all.

Joe Casabona: Yeah. I mean, there's, you know, I've worked with countless people who would say things like, "Well, that's not the way we did it at my old job." Okay. Well, go back to your old job if that's the way you wanna do it. That's not the way we do it here, right? And that's kind of the same, right? Now, I am wary of comparing AI to employees, but, like, you do need to train it. 

But like you said, different models do things differently, and if the model changes overnight, right? If you go from Opus 5 to Opus 5.5, right? The model's gonna behave differently. I don't know of a healthy situation where an employee has walked into a job a completely different person the next day, right? 

So this is kind of why we wanna focus on the, the task of it, right? We want very predictable outcomes for our AI because the, quote-unquote, "judgment," right? The way it... Not judgment, that is the absolute wrong word. The way that it algorithmically decides to do something could change, and without warning. And then if you have something that you really relied on, how much time now are you... It's like firing an employee, right? Or, or an employee quitting with no warning. How much time, how many hours are you set back now trying to fix what suddenly broke? 

Roger: Exactly. And that's when we talk about employees, you know, one of the worst things you can have is a high turnover employees because a lot of business people don't realize the cost of retraining. 

Joe Casabona: Mm-hmm. 

Roger: in this case, the time, but time is money in a business. The cost of constant retraining is something you have to take into account also.

Joe Casabona: And switching large language models is one thing, but the models update really frequently. It seems like monthly now. It seems like every few weeks Claude changes in some way that I hate, right? And so I'm really grateful that the things I have it do are things that are helpful to me, but are not things that if Claude disappeared tomorrow, my entire business would crumble 

Roger: I think it's an excellent way to look at it. Yeah. And the same way as if an employee left you tomorrow that was doing this, the business is still gonna go on. 

Joe Casabona: Mm-hmm. 

Roger: Just find somebody else to do it. 

Joe Casabona: Yeah. 

Roger: That's great. So what do you think, when you're working with people, is the number one thing or number two thing that they do that are detrimental to running their business properly? 

Joe Casabona: Well, so I think number one is they tell themselves that if they want it done right, they have to do it themselves, right? Like, that is a recipe for burnout and disaster, and it's just not true, right? I learned that the hard way, but, like, now I know that there are people who do things that I would do myself way better than I would do it. Um, but the number two thing is I think switching tools in the name of productivity. I think a lot of people think that some tool is going to be this magic elixir that fixes all of their problems. and they haven't done the pre-work that we talked about, where they look at, what am I doing and how am I doing it? Because once you know those things, then you can find a tool that actually helps you and stick with that tool, right? Oh, well, Notion didn't work for me, so I'm switching to ClickUp. So now you spend a whole day moving over to ClickUp only to realize in a few weeks that you don't use ClickUp either. so now you keep burning time 'cause you're like, "Oh, but ClickUp has this one feature that's gonna save my life." it's really the habits and understanding the way you work 

Roger: Yeah, I've done that. I tried ClickUp. I said , "This doesn't work the way I wanna work. It doesn't make any sense to me." So that was out, and I've done a lot of those, and I think probably a lot of people have. They're just so much just thrown at us as the solution to every problem in the world. 

So that's true also. So on the other hand, in a generic sense, what are the best, overall on businesses, what do you feel are is the best type of tools people should be using? 

Joe Casabona: Um, this is a really good question, and I kind of have this, uh, this idea that there are four frameworks or four systems that every solopreneur, every small business owner should have. the first is around admin. So, like, you need that you're going to actually use for note-taking and tasks, task management especially. and this goes to the point of a lot of people say like, "Oh, if it's important enough, I'll remember it." That is just demonstrably not true, right? Especially as you have more and more going on in your life. Uh, people praise me for my good memory, and I do have a good memory. I'm like pretty good. 

Uh, if you like give me a year, like post-1984 of who won the World Series, I will probably be able to tell you. I can tell you when a lot of movies, what year they came out. But like, I also have systems to put things places so I don't remember them, and then they surface when I need them or when I need to remember them.  So for admin work, I think that's really important.

Some sort of CRM is the second system. So I'm not saying you need a massive CRM, uh, but like just something to keep track of who you're reaching out to, potential clients, people who've expressed interest, and where they are kind of in your funnel or your pipeline because, again we're gonna forget, right? We're gonna send off the proposal and be like, "Oh, well, you know, when they're ready, they'll reach out," but they won't. You need to follow up with them. Last year, I found quote-unquote, $20,000 in extra revenue because of my follow-up system. at the beginning of quarter four, I followed up with a bunch of people who went cold over the summer, and a bunch of them were like, "Oh, yeah, I'm ready to pick up, you know, I'm ready to pick that up now." And so a CRM is really important.

Some sort of content creation system, right? I think we all need to create content in some way to-- not for the algorithm, not to go viral, but because in an environment where we only really can believe part of what we see or hear, showing up and showing people that you are an authority in the way you claim you are is really important. And so creating content is the way-- creating authentic content is the way to do that.

And the last system is idea capture, and this is like the wild card. People are like, "Why is this a separate one?" Uh, and it's because, like, you might get ideas anywhere, you wanna be able to capture them and organize them anywhere. Uh, and so I, you know, I can like shout at my watch. I like to leave my phone at home and go for a walk without my headphones, but if an idea strikes while I'm in nature, I wanna be able to capture that. And so I push a button on my watch, and I yell at it, and then it makes its way into my note-taking app. So those are the four kinda like general systems I think every business owner should have. 

Roger: So these are the type of things you help people develop depending on their situation and what their goals are. 

Joe Casabona: Yeah, that's exactly right. If they're like, "Hey, I know I need to create content, but I just don't know where to start.”  Let's talk about how you do it and put a system in place." Or if you're like, " I have a bunch of leads coming in, but then they fall through the cracks and none of them ever convert," I'm like, "Cool, let's put a CRM in place that you'll actually use that will remind you to follow up, and let's see if we can or let's put a system in place so that when you're done work, you collect the testimonial that you can use that in future proposals 

Roger: The key statement there is that you'll actually use. 

Joe Casabona: Yes. Yes. I, you know, people wanna know what tools I use, and I'm happy to always talk about it. Some people just wanna be told what to use. But I am very careful to not be fully prescriptive fully understanding a person's situation, especially with their relationship to technology, right? Like, they don't wanna use AI, I'm not gonna say, "Here's a bunch of agents. Install them," or whatever. but if people are like, "I've tried Notion and I hate it," I'm like, "All right. Let's, let's take a step back. Let's just try Google Sheets and see how that works for you." Just as long as we're logging the information somewhere where you know to look every day. 

Roger: And that's it. Look every day. I mean, for years I've used spreadsheets for everything. And sometimes you get so much data in them. The success is in the follow-up. It really is when you're in business. It's all in the follow-up. And that's where I learned the hard way that I got lost. 

I had all this spreadsheet worth of information, but I wasn't using it to do the follow-ups. And it's amazing once you start doing that how far your business will progress, you know. And the better you get at follow-ups, the more success you're gonna have. But you can't do that unless you have a system, because it gets lost, as you were saying. 

And that's what happened to me. 

Joe Casabona: Yeah. I've been in situations where, like, I've sent proposals and then a couple weeks go by and I'm like, oh my gosh, did I send the proposal? Oh, did I..." And then I look again and I'm like, "Oh, right. they said that, you know, they're gonna review the proposal, but they're going to Italy for a month or whatever, and so they're not..." 

And I already have the reminder to follow up five weeks later, right? Like, when the, you know, when they get back and settled in or whatever. Um, 'cause, like, once you do something, it's, it leaves your brain. Your brain's really good at optimizing for the information it needs to survive. And so, like, it'll kick things out with reckless abandon. So you wanna write things down as much as possible 

Roger: That's absolutely true. Because especially being, I find that being 76, I don't remember things as well as I used to. And, so I really depend a lot now on writing everything down, but that's... I probably should have always done that, so. Well, Joe, is there anything that we haven't talked about, today that you think you need to tell our audience about? 

Joe Casabona: Uh, you know, I think we, we've talked about kind of understanding how we work. I think a really underrated thing, and like I'm a techie, I love technology. I've got the latest. I try the apps so you don't have to and I love automating stuff, right? And if you want me to build automated systems for you, I'm great at that. But I think a super underrated thing for a lot of people is sitting down before Monday morning and planning out your week. this is something that I do. I have a weekly planner. Uh, I write down all of my appointments for the week. I write down all the stuff I need to get done, and then I say, "Okay, on Monday I'm gonna do X, Y, and Z. On Tuesday I'm gonna do A, B, and C." because that takes away some of the friction of starting when you sit down. Knowing what you're going to be working on takes away a lot of mental energy, uh, and it really helps you. It's, it's a really, I think, an underrated way to really optimize your time. Uh, and, and there was a week where I didn't plan my week 'cause I was just like traveling on a Monday, and I was like, "Ah, YOLO, I'll figure it out." It was one of my least productive weeks of the year 

Roger: It's true. It's so easy to procrastinate when you don't have it hard coded,  

Joe Casabona: Mm-hmm  

Roger: Which is one of my biggest problems. So I'm dealing with that also where I've now got my weekly planner and, I recently did a new one and I'm using it. And do I get everything done every week? No, because sometimes some things takes longer than I thought it was going to.  

Joe Casabona: Mm-hmm.  

Roger: But that's all right. It's there on that planner to transfer to the next one. And you do have to have systems like that. So if, people wanna get ahold of you, or see any of your work, where would they go? 

Joe Casabona: Uh, they can head over to streamlined, with a D, streamlined.fm/roger, there will be an opt-in, with a cheat sheet, and then my social media links over there. So, streamlined.fm/roger for listeners of this show.  

Roger: Thank you very much. I enjoyed the conversation, and good luck with all your future endeavors.  

Joe Casabona: Thanks so much for having me, Roger. I had a good time 

Announcer: You have been listening to the Mastering Business Basics Podcast with your host, Roger Pearson. For more information about all of the business education options that are available, we invite you to visit seagulltechnologies.com and continue your journey.