Side Hustle Success Tips with Joan Posivy (EP 816)

Joan Posivy, Side Hustle Hero, reveals what it really takes to turn a side project into a thriving business. Her journey and the stories she shares prove that success is less about waiting for the perfect moment and more about starting, prioritizing, and sticking with it. If you’re looking for honest, actionable advice to move your business forward, this episode delivers.
Uncle Marv sits down with Joan Posivy—author, entrepreneur, and host of The Side Hustle Hero podcast—to unpack the real-world lessons behind building a successful side hustle. Joan’s story is anything but ordinary: from becoming Canada’s youngest bank manager to running a deli, self-storage business, and now a top-rated podcast, her journey is filled with pivots, persistence, and practical wisdom.
Joan shares why most people never start their dream business (hint: it’s all in your head), and why the best advice she’s heard from hundreds of guests is simply to “just start.” She breaks down the importance of understanding your market, managing your priorities, and building habits that actually move the needle. Listeners will hear about the power of accountability partners, the need for patience in the face of slow results, and the financial must-dos that keep your side hustle afloat.
The episode is packed with memorable stories—from a $500 cashew dip startup that grew to $6 million, to creative side hustles like party tent rentals and even luxury port-a-potties. Joan’s honest insights and practical tips will inspire you to take action, whether you’re just starting out or looking to level up your business.
Companies, Products, and Books Mentioned (with URLs):
- Side Hustle Hero Podcast: https://www.sidehustlehero.com
- The Way Success Works (Book by Joan Posivy): https://www.joanposivy.com/the-way-success-works-book.html
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[Uncle Marv]
Hello friends, Uncle Marv here with another episode of the IT Business Podcast, the show for IT professionals, managed service providers, and anyone that is supporting business. And we're here to help you run your business better, smarter, and faster. Today, I have a new guest to the show and I'm going to do a little bit of a preview to kind of give you the idea of why.
So, you know, in the past, I've talked about the fact that I like to have people outside of the channel on the show. Sometimes it's just for me. I may have seen something that I wanted to talk about or caught my interest.
And sometimes I think that the guest would be able to bring some insight into the channel that goes beyond the stuff that we talk about on a regular basis. Tonight, it's a little bit of both. So I have joining me is Joan Posivy.
And Joan, before you say hello to everybody, I want to explain, you have a podcast called The Side Hustle Hero. It caught my attention. And to be honest, I don't remember why.
I know that I was out searching the pod universe looking for something. You came up there and I think the first episode I listened to was one that was the AI-driven vending machine. So that's going to kind of give you the preview here.
So first of all, welcome to the show.
[Joan Posivy]
Thank you so much for having me, Marv.
[Uncle Marv]
All right. So as I described that intro and tell you how I came across you, what's the first thing that comes to mind?
[Joan Posivy]
That is actually one of our most popular episodes.
[Uncle Marv]
Really?
[Joan Posivy]
So I'm not surprised. Correct. Yeah.
Yeah. That one and the top 10 side hustles. Yeah.
Top 10 side hustles for the year. But definitely the AI one because of I think those two things, the AI component of it, as well as the vending machines are a popular side hustle.
[Uncle Marv]
OK, so now let's go back and do the proper runway into this. You have the Side Hustle podcast. Now, I know that you weren't always into side hustles, but it seems as though you were early on in your career.
So tell us how you got started.
[Joan Posivy]
In terms of the podcast, what happened was after a successful career in banking. Don't hold that against me. The allure of entrepreneurship and business was calling me.
And for several years already, I had been studying and applying what I was learning in the area of personal development, essentially understanding the connection between the way we think and then the results that that generates in our lives, because it's our thinking that drives our behavior, our choices. And those are creating results in our life, the opportunities that we take advantage of, the opportunities we let pass by. So that was a driving force.
However, and having said that, because I started teaching it because of results I was getting, I didn't want to be one of those platform speakers that just talked about stuff. And so along the sides, I always had businesses. So my career for the last few decades has really followed two parallel tracks.
One in the personal development space as a speaker and author and trainer, and then the other having businesses. Some of them side hustles, some of them more full time. And the last one that was more full time was in the self-storage industry.
And when I sold that, I thought, OK, there's a little opening in my calendar. And so the birth of the podcast came about because it's really a combination of those two things. Obviously, the business side of it, but then strong on the personal development piece, too, because typically the reason that a person does not start a side hustle, even though they say they want to, it's something in their head that's stopping them.
And so to me, it was the perfect marriage of those two things.
[Uncle Marv]
All right. So that didn't go where I thought it was going to go, because I got the impression that you were always a side hustler. The bio that I read, you know, usually starts out with you as the banker.
And then it talks about you love side hustles. And it goes into, you know, saying that you did side hustles from the storage center to the Christmas tree lot. That's all true.
What else? Delicatessen you've done.
[Joan Posivy]
Yep, that too.
[Uncle Marv]
So I just assume that you were always a side hustler. And that apparently isn't the case.
[Joan Posivy]
It went back and forth. So the delicatessen is a good example of that. So what happened was when I was at the age of 19, someone said to me, you know, Joan, there's a seminar occurring in town, you should go.
Now, they told me, Marv, that it was on business matters, predominantly marketing. I think they said that so that I would go, which I did. But it turns out the speaker wasn't talking about marketing at all.
He was talking about your mind and your potential. And this was a first for me. I'd never heard anything like that before.
But essentially, his message was, regardless of what's happened to you in the past, despite what you think your limitations are, you can have, do or be anything you want with your life. Well, I was blown away, and that set me on a course of studying what I ended up studying for decades. But as I was applying what I was learning, I could see that this was working.
I was getting the results. And it wasn't just me. Anybody that applies these can literally live their best life.
And that's the subtitle of my book, actually, The Way Success Works, How to Decide, Believe, and Begin to Live Your Best Life. So at any rate, one of those goals for me that I set as I was studying all this and applying was to become a bank manager. And Marv, I thought that once I achieved that, my life would be made.
Like, what more could I possibly want? Well, it turns out that I did achieve that. I was 22 years old at the time.
Youngest in Canada, I'm told. But after I worked at it for a couple of years, I thought, you know what? This isn't it.
I thought that this was what I wanted. And so I started looking for these side gigs. And one of the first ones, now this actually, no, the Christmas tree lot was first.
The deli came after. But what happened was I saw this business that was for sale. And essentially, they were going out of business.
So I basically bought the equipment. And so it was a turnaround project. And so I worked on that as a side hustle for about a year.
To get it up to the point where I could quit the banking and do the deli full time until we sold that and then went on to other things.
[Uncle Marv]
OK, so I'll be honest. That story sounds like a lot of my listeners. And me, actually, I'll just come right out and say that, because most of us and I can't say all, but a lot of us in tech started as a side hustle.
We may have had a full time gig either at a tech company or at another company, which I did, but did tech on the side. And a lot of us got to the point where we finally made enough money to leave the day job. And that's what I did.
I mean, I worked until the boss at the computer store could afford to hire me. And that began my career in tech.
[Joan Posivy]
That's great. But that makes total sense, right? Because if you've got full time employment, sometimes if you're fortunate enough to have benefits as well, you know that eliminates the pressure of the side hustle having to perform right away.
It leaves the stress out of it so that you can. Take your time to build this side hustle and figure out if this is what you want and how to market yourself and all those good things that make a successful side hustle without that pressure that it has to produce that income right away. Yeah.
[Uncle Marv]
So let me try to weasel this transition because there's not a real smooth way to do it. So I guess that I've been listening to your podcast and I've probably been listening at least two years and could not figure out a way of, hmm, I think this would be a good person to interview. I just don't know how or why.
And so I came up with this idea and at least so far you've agreed that it's a good idea because you're here. But because a lot of us in tech start off as a side hustle, you talk to people. Either in their side hustle or that have, you know, turned their side hustle into a full time gig.
[Joan Posivy]
Yes.
[Uncle Marv]
A lot of what goes into a side hustle is the same regardless of whatever the hustle is.
[Joan Posivy]
Totally agree.
[Uncle Marv]
And so I thought, you know what? Here's somebody who has talked to hundreds of side hustlers. And I'm like, I wonder what would be the knowledge that you could share of the things that you've learned as part of this process.
So how do you want to start?
[Joan Posivy]
OK, well, yeah, let's go there, because I've often said that, you know, 90 percent of business is all the same. It comes down to having delivering stellar product and service. One that is in demand.
And most of our challenges tend to be person related, whether that's employees, subcontractors, issues with clients. And so all those skills that you develop in one industry you can apply to the next. And so there are, say, for example, overriding themes in the side hustle hero podcast.
First one that comes to mind towards the end of the episode. I always ask everybody, what's your best tip for side hustle success? And I would say, Marv, probably a good 70, 80 percent of them say, just start.
There's no magic to it. Just start. Stop your researching and procrastinating and just start.
So, again, that's universal, regardless of that's a new direction that you want to take your I.T. business into or whether that's starting a new side hustle.
[Uncle Marv]
Yeah, I've heard that many times, and it's funny because there are times where I'm in my head, I'm thinking, OK, they're going to give a great answer. But then a lot of times I'm like, then I'm like, you know what? This person is just going to say, just get started.
Because a lot of times that's it. You'll figure it out along the way.
[Joan Posivy]
Yeah, it's simple because it's excuse me. It's simple, but it's not easy. It's simple because you and I and everyone listening or watching understand that.
Yeah, we just got to get started. And we can all feel examples in our own life of when we've procrastinated. Oftentimes we are not doing that very thing that we should be doing.
However, the challenge is changing that habit. And you and me. Are driven by habit.
I mean, think of your morning routine. It's pretty darn consistent in terms of from the time you get out of bed. First thing in the morning.
And suddenly you're bringing in this new side hustler again, a new division of your I.T. You're going after a different market. Suddenly, number one, you've got to make time for it. So something else you're going to be trading off for.
And secondly, it's probably going to require skills and areas of expertise that you don't currently acquire or don't, excuse me, haven't acquired or things you just don't know how to do. And that stops a lot of people, Marv, to think, well, I don't know how to do this. And so.
I'll wait and they're waiting for that perfect time, which, of course, you and I both know, never come.
[Uncle Marv]
Yeah. Have you identified some common qualities that these people have, you know, we know that a lot of times.
The go getters are the ones that really make it happen, but is there anything beyond that that you've kind of been able to see as you're doing these interviews?
[Joan Posivy]
Sure. Yeah, a couple of things come to mind. The first one is what I would call perception, and that is understanding your market.
Is there a need for what it is that you want to do? Is the price point. In line with the service or product you're providing.
One person that just popped into mind, she did pottery and she was doing pottery that she really liked. Which is fine if that's the only reason you're doing it, but she wanted to turn it into a business and it's not what the market liked. And so she was she was having she there was a struggle there.
And so, number one, I would say market number two. Efficiency, and that's the time management piece. And it's really not time management.
That's not a good term. It's managing your priorities because we all get the same 24 hours in a day. It's what we do with that time.
And the people that are winning. Understand what their priorities are. And they get those things on their calendar.
So at the beginning of the week, you say, OK, and we'll just take the side hustle, for example, or your full time business. And you take a look at that and say, OK, what are the top three priorities that I want to get done this week that are really going to move the needle for me in the direction that I say that I want to go? Those get down on the calendar first, then the rest of the stuff gets filled in.
So that at least you've got those priorities down there, because if we don't do that, all of a sudden it's Friday and it's like, where the hell did the week go? I didn't even touch these things that I said. And again, oftentimes it's those priorities that are, oh, gosh, you know, there's things that we don't want to do or they're uncomfortable or it's like that deep work that we need some isolated time for.
But if we want to achieve the goals that we say we do, we've got to get them in there. And that sounds like it's one of those things, Marv, I bet you've heard before that, you know, what are your top three priorities and do those first thing? We've all heard it and I heard it for years.
But I got to tell you, the day that I actually started doing it because I forced myself to do it for I did it for a few weeks and then it became a habit. I couldn't believe the change in productivity. It was huge.
So I highly recommend it.
[Uncle Marv]
I remember because I did go to school for business, got my bachelor's in business administration. Remember going through all the all the tabletops of put down your all of your task list, put them in priority A1, A2, A3. And then it was just as, you know, it got to the point where, listen, just put your top three or five, just put them up there.
And those are the ones you get done. Everything else will figure itself out.
[Joan Posivy]
So and this is a tiny point, but it would made a huge difference for me is the day before the night before when I'm making that list for the next day, because now I'm breaking it down for the day is I number those priorities. So when I get into my office, I just take a look at number one. I don't even pay attention to number two until number one's done.
Because if you don't do that, you're looking at this list of maybe, you know, seven or eight things and you might pick out the easy one or I don't know, what do I feel like doing? No, no, no, no, no. You take a look at number one and stop the excuses.
Just get her done. See, there's a huge difference between knowing and doing. Are you and I paid, rewarded, compensated for what we do?
Excuse me, for what we know or for what we do with what we know, which is it the knowing or the doing?
[Uncle Marv]
So hopefully, hopefully it's both.
[Joan Posivy]
Yeah, well, but you can know a lot intellectually, right? But if you don't do anything with it, you're not going to get the results like you could be expert in your knowledge of I.T. But if you don't deliver for the client, if you're not doing it or getting somebody to do it, you're not going to get paid.
[Uncle Marv]
You're right. They want to see they want to see the result.
[Joan Posivy]
Yes. And so on an intellectual level, we can know a lot. But if we don't step out and act on those ideas, on that information, then we're not going to get the results that we're looking for.
And it's that behavior part. We're looping back now to those habits. So to break through that, you really got to want what's on the other side, particularly if those actions are the things that we don't want to do.
Like, for example, if some people in order to develop their business, they want to go out networking or doing presentations for the local chamber of commerce or border trade, and they really don't like doing that. They're going to have to they need a good reason to pull them through. So you're going to have to want what's on the other side of that.
[Uncle Marv]
Right.
[Joan Posivy]
OK, so you mentioned you were sorry you were asking me about top qualities that sort of make that that difference. And I wanted to add a third one, because it's really key. And that's persistence, giving yourself enough time to succeed, because too often we give up just before it could potentially turn into something.
Because when we start a side hustle or anything new business, it's exciting. There's so many things that are new. Finally, we're going to do this.
And we start out with these great and grand goals. And things might be playing out fine at first. But then there's going to be like a lull or a challenge that we have that we can't quite pull through and we give up.
We think, you know, we start to justify. Maybe this was a dumb idea anyway. You know, why am I even bothering with this?
You know, my life's OK. You know, I got food on the table. I don't really have to do this.
It was a dumb idea anyway. And then we go back to that comfort zone. So give yourself enough time.
And if I may want to add tip on how to do that, just from personal experience. Mentioned briefly, and you did as well about the book, The Way Success Works. I remember one particular February weekend when I was writing it.
I was so close to giving up. I just it was not coming together no matter what I did. And then when I was looking at, of course, at the topic, the content I was writing, it's like, Joan, seriously, give your head a shake.
You need to figure this out. And of course, it came together and went on to be an Amazon bestseller. But at any rate, when I started this podcast, even before I launched, I knew that that time and I didn't know what it was looked like.
But there's going to be some point where you're. Offered an escape hatch, a way to bail because you can't do it, you don't have the time, whatever. And I knew that would happen.
I didn't know what it was going to be. So I made a commitment at the beginning, and I would recommend this to any of your viewers and listeners when they embark on something new, make a commitment to yourself that you're going to give it X amount of time, whatever that is for you. For me with the podcast, it was one year.
I said for one year, come hell or high water, I'm going to figure this out. And then on the year anniversary, I'm going to take a look at it and then decide, you know, does this make sense? Do I want to continue or not?
And I'm really glad I did, because there were times there, Marvin, where it's like, I don't know how to do this. I almost burnt the place down once using a green screen that got too close to a light.
[Uncle Marv]
Oh, my.
[Joan Posivy]
And so, you know, make that commitment to yourself. You'll be glad you did.
[Uncle Marv]
All right. So I just want to say great tip. And the reason I'm going to say great tip is I was talking with somebody a couple of weeks ago who wants to start a podcast.
And wasn't sure we were talking about it, she came to me for advice. And after we went through and talked about the initial stuff, that was the advice I gave her, said, listen, you need to commit to this. So you need to figure out, you know, what your purpose is, what your goal is.
And I'm going to say you need to do it for a year. So it's kind of interesting that you also said that.
[Joan Posivy]
Yes, yes. And what she could do, too, if you're open to it. And I did this for the book and I did it to launch the podcast as well, is I get an accountability partner.
You want an accountability partner who you respect and admire and that you don't want to disappoint. And they're probably very busy, and this will still fit probably with their calendar, because if you were my accountability for my next project, Marvin, what I would say to you is that once every two weeks, usually it was every other Monday for me, I'm going to send you an email and the subject line is going to be successes and commitments. And what I'm going to tell you, Marv, is.
Here is what I've done the last couple of weeks. So those were my successes. And here are my commitments for the next two weeks.
Here is what I'm going to do. And then two weeks from now, I'm going to write you again. And I got to tell you that I've got those done, because if I don't, you're going to go, all right, Joe, what's up?
Yeah. And I might try to make an excuse. And you're going to know me and go, come on, really, is that it?
And I had a personal rule that I would give, like when I was the accountability partner for someone, I would give them like three strikes and you're out. It's like, fine. OK, you didn't get it done.
This, you know, life happens sort of thing. If you're so serious about this, keep it on. But if that happens three times, it's like, I don't want to hear about it again because this is starting to be a story for you now.
You're not going to really do it. Yeah.
[Uncle Marv]
OK. I want to go back to your third quality. You said persistence, and I wanted to add patience in there as well, because some people really want those results right away.
And sometimes there's got to be you raise your hand, raise your hands.
[Joan Posivy]
Yep. Yep. That's me.
[Uncle Marv]
It's persistence with patience. Sometimes things will take a while to work or for you to see the benefit. And again, that's something that I, I had to go through because when I rebranded this podcast, who?
It was it was it was easy to be persistent, but it was hard to be patient, if that makes sense.
[Joan Posivy]
Oh, oh, very well said. Absolutely. All right.
That's what that makes that even harder. Yeah, absolutely. I wrote that down.
What makes that even harder these days is what we're delivered in social media.
[Uncle Marv]
Hmm.
[Joan Posivy]
You know, especially in the side hustle space, they're like, oh, start this side hustle, you make five grand in a week and you'll be on your sailboat in three months. Yeah, it doesn't work that way. I pretty much I was going to say 100 percent of the guests that I have on their success isn't measured in days and weeks or even months.
It's years that they got to that point. And so, you know, don't believe all those tick tock ads.
[Uncle Marv]
Yeah, I remember. So you mentioned that the one show that stands out for me is the gentleman that you hand on had on about the land, the land deals. OK, where he would go out and buy land.
And he said, you know, sometimes you got to wait a year or two for it to actually flip. And of course, my first thought is, OK, it's easy if you have money to sit and wait for that. But he also talked about the fact that you can get in, you know, really inexpensively and do some stuff.
And I'm sure he's probably had a whole bunch of people email him about that because land deals are huge.
[Joan Posivy]
Yes. And he was buying them. Yes.
Relatively cheap because they had problems with the lot in some way, shape or form. There's no access or there's issues with the title. So he would buy them really cheap.
And then a lot of the work that he was putting into it, he could do himself. And so that's where the kind of like the sweat, sweat equity of the timepiece.
[Uncle Marv]
Yeah. And he had the patience of knowing that if it would take a while for a permit, he was willing to wait. Yeah, because the reward on the other end was huge.
[Joan Posivy]
Yes.
[Uncle Marv]
So good point. Very nice. I'm going to ask a question that I didn't prep you for.
[Joan Posivy]
OK, I'm ready.
[Uncle Marv]
So a lot of the things that you talk about in terms of teaching and all of that, it feels like the side hustle podcast is a side hustle to what you're really doing. Am I am I right with that or. Is this pretty much it now?
[Joan Posivy]
I've got so many interests that I'm involved in. I'm heavily involved in Rotary, which is an international service organization. So I do teaching through that a lot of volunteer work.
My particular club is one hundred and twelve years old. I'm stepping into the presidency role next year on the board of directors. I've had board positions.
I'm dedicated to riding horses, equestrian. So, yeah, I've got a lot going on.
[Uncle Marv]
OK.
[Joan Posivy]
All right. But I love all of it.
[Uncle Marv]
Out of all your shows, do you have a favorite?
[Joan Posivy]
That one's really tough. That's a really hard question. Oh, gosh.
Especially if it's on what it's for.
[Uncle Marv]
OK.
[Joan Posivy]
Yes. One of. Yeah, OK.
So one that comes to mind is Melissa Mills. She started her side hustle with. A bicycle, a blender and five hundred dollars.
And she was making cashew based dips, the end product. It tastes like cream cheese. But instead of using dairy, they're cashews.
Right. And I stumbled upon on her at a farmer's market. That's where I try to do a lot of my shopping.
I love supporting local farmers and their produce. And her husband was running the booth. And I'm a huge fan of testing products at farmers markets.
If a person does have a product that they want to start, because it's so cheap, you're not signing leases. You just go in there and you've got all this good foot traffic and potential customers you can talk with. Anyway, she went from starting this thing with five hundred dollars, completely bootstrapped the thing.
And by the time I was talking to her, they were up to three million dollars in sales. And then about a year and a half later, I had the opportunity to interview her in person there. They went up to six million now and they've expanded internationally.
And again, it no outside investment, all bootstrapping. They're now I mean, she started in her kitchen. They're now in a twenty thousand square foot facility.
And it's this this idea of putting one foot in front of the other. She didn't know all those steps. Another lady I had on was running a cafeteria at a ski hill.
And a lot of the skiers were saying, oh, I want the recipe for this. I want the recipe for that. She finally creates this cookbook and it became.
Gosh, she's on cookbook number seven now. Multiple bestsellers cooking up bestsellers. I think I called it Shelly Adams is her name.
Whitewater cooks, it's called. And at one point there were some sauces that she was making and marinades. And people said, well, we just want to buy it.
So she's like, fine, I'll do a line of sauces. She Googled, how do I bottle sauces? Didn't have a clue.
And so just because the lesson there is just because you don't know something, it doesn't mean that you can't do it, especially with all the tools more of at our disposal these days.
[Uncle Marv]
Yeah.
[Joan Posivy]
In Google searches and YouTube and A.I. And it's incredible. It's incredible.
[Uncle Marv]
Do you have people that reach out to you asking you for. Help on how to make their side hustle better.
[Joan Posivy]
Yeah, I mean, we're very social, whether that's through email, through the podcast, through the website.
[Uncle Marv]
Yeah. OK. So I guess the other thing would be is.
I know that you do your shows every now and then, I think you've done two where you've done the top side hustles of the year. Yes. For the top 10 side hustles and stuff.
And every now and then you'll do a show where you'll just talk about. A strategy or tip that people need to do, and it's just on that and stuff. Have you come up with like a top 10 list of.
You know. Lessons that a person doing a side hustle should know about.
[Joan Posivy]
Well, I mentioned a few of them already in terms of you got to understand your market, right? Make sure that you are. Let me backtrack a little bit.
As far as the time management piece, that's going to be a person's consideration in terms of what side hustle they're going to choose. Like, take a look at realistically how much time per week do you want to allocate to this? Based on these other things in your life that you some things you'll want to trade and get rid of and other things you'll want to keep.
So depending on how demanding that side hustle is, that's going to be part of a consideration. We touched on giving yourself enough time to succeed at it. Set a big goal so that it helps pull you through those uncomfortable moments when you're going to have to do things that are outside of comfort zone.
Accountability partner, I think is huge. Some. Side hustles that I really appreciate fly under the radar.
And so be open to looking for things that are maybe not your typical selling on Amazon or drop shipping, and not that there's anything wrong with those. But one of my other favorites, and this is oh, gosh, this is going back to I think it was episode 21. This business is cleaning up with Brian Winch.
He started by cleaning up garbage.
[Uncle Marv]
Yes.
[Joan Posivy]
Around industrial areas early in the morning. I'm like, man, this guy's getting paid to go for a walk.
[Uncle Marv]
Yeah.
[Joan Posivy]
And the startup cost was like less than a hundred bucks. And so if I were starting over again today, I would seriously look at that business in terms of seeing what market was, because as I grew that, see, he's done that. He grew it himself up to about a hundred grand doing it himself.
And then brought it up to, I think it was around six hundred thousand, if I have memory serves right. And the way he did that is he started to hire people to do the cleanup in the morning. And when I thought about it, I thought that's brilliant, because there are a lot of people who are retired or retiring.
They get up early. They want some exercise. I mean, it's perfect to pay them to do it.
And meanwhile, he was able to scale it that way. Another tip would be very aware of the cost to produce your product or service. I had one guest on who was in the retail space and her gross sales were pushing over a million bucks.
And it wouldn't surprise me if she was actually losing money, because I don't think she had a really solid handle on her costs. And that's something that we have to be really aware of. And as you are getting paid and the money's coming in, the money that's not yours, i.e. your state tax, your sales tax. Set that aside. Because you need to be remitting that on time. And in one business I was in, I had two partners and they were like, oh, we want to use this money for like these certain things.
And I'm like, no, we can't, because I don't want us to take a chance on something, lose it. And then I've got this tax bill that we have to pay. And so what I always did for my businesses was set up a separate account or like a sub account somewhere to kind of squirrel that away so that it's separate.
[Uncle Marv]
Absolutely.
[Joan Posivy]
Part of the banking and the financial side coming through. Yeah. Yeah.
[Uncle Marv]
So it is interesting. So I do remember some of those early episodes and some of those stories. The stories you've had on recently, a lot of them seem to be more prepared with coming with answers to those questions.
You know, whether it's the let's see, the mattress flipper gentleman that was on and some of these, even the even the vending machine guy. Yeah. These folks were pretty detailed in knowing what they needed to spend and what they needed to make.
And they had done a really good job of that. So have you seen an evolution of the people that have come onto the show that, you know, maybe started out in twenty, twenty two or whenever you started the podcast? So now is there a difference in the side hustler?
[Joan Posivy]
I think they're more aware of the length of time it actually takes to get those results that they're looking for, which circles back to your point about the patients, which is really key. And not be swayed by, like I was saying, those social media influencers that seem to convey the message that it's easy, it's going to be quick. That's not been my experience, nor that of.
My side hustle guests, right?
[Uncle Marv]
OK, any of these shows ever pull your strings to say, oh, I think I need to. Dip into this or do a new side hustle.
[Joan Posivy]
It has been tempting. Yes.
[Uncle Marv]
Yeah.
[Joan Posivy]
And I've got to be like, oh, look, squirrel. Try that over there. Yeah, no, probably one of the latest because I mentioned to you my love of all things equestrian and horses.
When I was doing a show recently on high ticket drop shipping, I thought, oh, that would be interesting. So the key there is that in how I was thinking is that if there was a product within that space, that number one, I would never sell something that I wasn't a big fan of. I've had people come to me in the in the past about selling their product or service, and I'm like, no, no, not going to do it.
So anything that I talk about on the on the show, I either use or love for some reason. So at any rate, so let's just use an example of like if there was a particular saddle manufacturer or something like that. That's a high ticket item.
You're talking a couple grand and the drop shipper. My role would be to set up the website and basically sell it and provide the education and the information. But then when the sales made off my site, it's the actual manufacturer distributor that ships the product out.
So I'm not paying for carrying any inventory. I like that aspect of it because I like to travel and any side hustles or yeah, any side hustle I take on would need to have that flexibility. So that's sort of one of my personal preferences.
[Uncle Marv]
OK.
[Joan Posivy]
And so. Yeah.
[Uncle Marv]
All right.
[Joan Posivy]
So that's one of the things that caught my eye.
[Uncle Marv]
All right.
[Joan Posivy]
But right. But quite recently, and this isn't out on the market yet, but it's going to be a free giveaway, actually. I've created what's called this smart start from idea to it's live and seven steps to help people through how to set up an actual side hustle.
And one of those steps is basically deciding what is the right fit for you. And I go through a bunch of questions like that. Is it something that you want to be doing like physically with your hands or do you want it more like e-commerce type style?
Do you want to be traveling? Do you want to be in one place? All that sort of thing to try to narrow it down for you.
[Uncle Marv]
All right. Interesting. You got me thinking about your little side hustle and see if it.
I thought for some reason there was going to be the luxury port-a-potty was going to be in there.
[Joan Posivy]
So I'm thinking, actually, you know what? That's not a bad one. I actually like that one, too.
That's another one that kind of like flies under the radar that that people don't think about. And I'm glad you mentioned that one, because that is an offshoot of that. That I would seriously look into is the party tent rentals.
Yes, I wish I had thought of that sometime during the 18 years that I had my self-storage facility because I had the storage space. So to be able to keep the tents and chairs and tables and all that, that would have been a real competitive advantage for me because I wouldn't have been paying for storage. And that's another thing about a person choosing their side hustle or expansion into a certain area of IT.
What have you already got going that's an advantage for you? I did a kayak side hustle for a while for a number of years based out of the storage facility, again, because I didn't have to pay for storage and my self-storage facility was called 12 Mile Storage. And so what I did was I called it 12 Mile Kayak so I could use all my existing staff.
So when the phone rang, they just said, Good afternoon, 12 Mile. How can I help you? And then based on the person's question, we knew whether to direct it to the storage side of the kayak.
[Uncle Marv]
Oh my, how? I don't think you've mentioned that one on the air.
[Joan Posivy]
Possibly not.
[Uncle Marv]
How many side hustles have you done?
[Joan Posivy]
I haven't counted. But that the way that started is my business partner and I, we were definitely into water sports, and it was a time that kayaks were really gaining in popularity. And we thought, geez, we'd love to have a couple.
How many would we have to sell to get two for free? That's how it started. And we calculated that it was going to be I think it was around six or seven that we would have to sell.
And so we just started phoning and talking to friends and family and said, you know, is anybody interested? And we got enough orders and that we put that first order through, got our two for free and thought, well, this demand is there. Let's just keep going.
[Uncle Marv]
Interesting. OK. Which is another great reason to start a side hustle.
If you want to get something for free, calculate, you know, it's something you love. So calculate how much work it would take to reap a benefit from it. Cool.
[Joan Posivy]
Yes. I'm glad you mentioned that, because oftentimes to a personal say, I would love to do this thing, whatever it is. But I can't because I don't have the money.
Well, having the money in the bank account is only one way to get there from here. There could be others like the scenario I just described.
[Uncle Marv]
OK. So let me circle back to something you said in the beginning, which when we talked about the one year commitment. So obviously you got to one year and you said things are going well and you've continued on now.
So this is year three or four.
[Joan Posivy]
In one month, it will be three years.
[Uncle Marv]
OK. All right. How do you feel about it now?
Because now you have a three year thing to look at.
[Joan Posivy]
I pretty much can guarantee that there's going to be a year for.
[Uncle Marv]
There will. OK.
[Joan Posivy]
Yeah.
[Uncle Marv]
Any difference in future plans for the for the show?
[Joan Posivy]
I would describe it more as a natural progression. We're currently working on a more in-depth side hustle course. That will take help people take that deep dive into it to help ensure their success.
Yeah.
[Uncle Marv]
All right. And. I think when we talked before, you don't actually have to go looking for guests very often.
[Joan Posivy]
In the beginning, when I started it, it was 100 percent me going out and looking and to your friend who approached you about doing the podcast. I mean, that's one of the things that she's going to come up against, presumably depending on what her current network and expertise looks like. But yeah, when I started, it was 100 percent me going out doing Google searches.
I would be hearing something on the news and then try to find that person and have them on the show, that kind of thing. And that's where you you've got to stick with something long enough to start gaining that traction. So then people started hearing about the podcast and it getting referred.
And then, yeah. So now I've got the majority of people coming to me and pitching. But I'm also keeping my ears open and reaching out to people as well.
[Uncle Marv]
All right. I would love to ask you this on air, but I have a feeling it's probably not good protocol because I would love to hear what's the worst idea you've been pitched that you had to say no to.
[Joan Posivy]
So, OK, one came to mind right away, actually.
[Uncle Marv]
OK.
[Joan Posivy]
Her pitch was that she had. It was some crazy number. It was like 300 or 500 books on Amazon that she was selling that she personally authored.
And I and I went and took a look on Amazon and I'm like, oh, these are crap. These are like three, four or five pages. They're like, no, no, no, no, no.
I'm not recommending this to anyone. But, you know, she claimed there was some revenue sources from them.
[Uncle Marv]
And I'm like, that doesn't sound like a side hustle at all.
[Joan Posivy]
Well, her pitch was you there. They're revenue generators. So just producing them and they're so easy to be able to create and upload and do.
And but I would not feel comfortable promoting that or sounds like one of those YouTube pitches. Right. Yeah, yeah, yeah, yeah.
[Uncle Marv]
By this book that teaches you how to build a book to resell something like that.
[Joan Posivy]
Right. Exactly. Yeah, yeah, yeah, yeah.
[Uncle Marv]
Multi-level marketing is what it felt like there. All right. So I feel like, you know, I've asked you a ton of questions and it's all been about your show and all of that.
Let me ask you, have you, you know, during the course of sitting here or even before, is there questions that you have of me that you'd like to ask?
[Joan Posivy]
What have you found to be the thread that. Runs through the success of your guests that you've had on.
[Uncle Marv]
Oh, oh. So that's a multifaceted answer, because the guests that I have on that are actually, you know, technicians, business owners, managed service providers, it's basically the community aspect of learning from each other, helping each other out, tips, tricks, things of that nature. And then, of course, I have the vendors in the channel that are really, you know.
Some of them are here just to simply pitch their product, which we get. Some of them are actually trying to help build community as well. The for the last couple of years, you know.
Rising tides rise, all ships and, you know, the concept of vendors reaching out to us as partners and saying, look, how can we help? How can we educate? We have.
So in the space. A lot of times it's a struggle to get customers if they're not ready to buy. Because we're in this age where a lot of people think that, well, I don't need a computer technician, I can just Google.
And find my answer. OK, or we've gotten to the point where we've told people technology is getting cheaper and cheaper by the day. So why should I pay you thousands of dollars each month to help me keep my computers running?
So there is that thing where we have to go out and help each other educate.
[Joan Posivy]
Yes.
[Uncle Marv]
Especially businesses, you know, where, you know, if you want your business to run, you've got to spend money on your infrastructure, the same as you would on your marketing, the same as you would on your employees. You know, you know, we talk about keeping your employees happy and healthy. Got to do the same with the computers.
[Joan Posivy]
Yes. Yes. Especially when you get into data security these days.
[Uncle Marv]
Yeah. So it's an interesting question. All right.
Well, I've run out of I mean, I have other questions, but they're not tied to this. But I do want to thank you for. I was going to say being brave enough to come on my show, but that's not true.
That's not the right way. But it was a stretch. I'll say that.
But thank you for doing that. Like I said, I've listened to your show a lot, and I think there is a lot of parallels in the side hustle mentality that a lot of us started out that way. And I wanted to introduce you to my listeners.
And I think some of them might want to, you know, also listen to your show because like me, I think that they would get little tidbits. Out of some of these stories that, yeah, they're not technical, but the things that they go through are the same things that we go through.
[Joan Posivy]
So I appreciate being. And yeah, yeah. The gentleman I had on actually the episode just dropped today, he created something called.
Bad cards for good golfers. And it's basically a card game that you play as you're golfing. It's pretty hilarious.
And normally I would have on a guest that's like teaching a side hustle. Right. But there's so many stories for all of us.
Excuse me. Lessons wrapped up in his story for all of us. Going back to a number of the things that you and I have already talked about.
But he had no experience in this space. But it's that lesson of I want to do this. What's my first step?
Oh, OK, here's a problem. Let's solve it. OK, that one's done.
We go a little bit further. Oh, new problem I need to figure out now. And on and on it goes.
But he had thought about the idea for well over four years. And one day he realized, I keep telling people I'm going to be doing this. And it's become a story.
And I realized that I've got to dump the story and just get started on this thing. And he's had a lot of fun with it. A lot of success, too.
[Uncle Marv]
All right. And of course, I did not do the proper prep here because I'm scrolling through my phone. Do you remember the episode of the person that built the app from scratch?
[Joan Posivy]
The person who was in college?
[Uncle Marv]
I think so.
[Joan Posivy]
Yes, that would have been we did it. That ended up I split it into two parts. So episode one thirty eight was the sort of time management piece because he had so much going on.
He was a football player going to college full time and then developing this app and then the one on the actual app. It was the meditation app. Is that the one?
[Uncle Marv]
Yes.
[Joan Posivy]
That would have been episode one thirty nine. OK, no idea where to start, how he built an app from scratch.
[Uncle Marv]
Yeah, right. I wanted to specifically mention that just because of the tech audience. I would say that's probably a good place to start hearing.
You know, of a tech related show, you've actually got a few tech shows in there, so we'll put the links to those episodes in there. So that would give people a great place to start.
[Joan Posivy]
But of course, everything, everything lives at SideHustleHero.com.
[Uncle Marv]
Yep. So there's your podcast. And interesting.
Be brave, be a hero, be a side hustle hero. So there you have it, folks. I hope you appreciate that.
And if you've made it this far, fantastic. And we'll have all the links in the show notes. I'll have a link to the website, the podcast, even her book, The Way Success Works, How to Decide, Believe and Begin to Live Your Best Life.
And it's in Audible, too. So techies love Audible books. I don't know why.
[Joan Posivy]
Awesome. All formats. Yeah.
[Uncle Marv]
All right, Joma. Thank you very much. And that's going to do it for this episode, folks.
We'll be back with a lot more. Go ahead.
[Joan Posivy]
I was just going to say thank you so much, Marv, for the opportunity. It's been lovely speaking with you.
[Uncle Marv]
Thank you. Folks, we'll see you out there. Remember, head over to the website, ITBusinessPodcast.com, hit follow. And if you like this episode, share it with somebody. That's going to do it. We'll see you out there.
And until next time, holla.

Joan Posivy
Side Hustle Expert
My first full-time job and career was as a banker. Please don’t hold that against me! My favourite (and very lucrative) hustle during that time was an annual Christmas Tree lot. It was the perfect! Tremendous traffic, high-income neighbourhood, and big volume in a very short period of time. Okay, maybe the below zero temperatures weren’t so perfect…but the profit margin made up for it.
I became the youngest bank manager of a Canadian financial institution.
Having an aptitude for number-crunching made it enjoyable, but I realized that it wasn’t the dream job I thought it’d be.
Towards the end of my banking journey, my business partner and I bought a delicatessen that was going out of business. I worked on it as a side hustle for a full year before quitting my day job…and I’ve never looked back.
Many of my adventures are outlined in the book, The Way Success Works. Suffice it to say, I’m a happy, healthy, and wealthy serial entrepreneur.
While I always have an eye on the “numbers” of a side hustle business, I’m thrilled to be introducing you to Side Hustle Heroes from around the world who share the story of their journeys, to educate and inspire us to take action and live our best life.
If you'd like to take a deeper dive into what's been holding you back from taking the action you know you need to take to improve your results, then I invite you to check out a program I wrote and produced that I cheekily call Turn Your Thoughts Into "Wanted" Things. The reality is, we're constantly turning our though… Read More