Today Dannie and Caitlyn are talking with Jackie Minchillo of Pineapple Development.

We believe in accessible content and that anyone who wants to learn from this content should be able to. In order to support this, we’ve had every episode of Season 4 transcribed. The transcriptions are available at the bottom of every episode blog post.

SHOW HIGHLIGHTS:

• Taking advantage of hidden opportunities when they represent themselves.

• Working with your partner to create a thriving business.

• Not allowing where you are located to affect your side hustle negatively.

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Episode Transcript

Dannie Lynn Fountain: [00:00:21] Hello and welcome back to the side hustle gal podcast. Today we have Jackie Minchillo, and we were actually joking around before we started recording that this is our first legit stranger interview. So as you listeners know, we find guests. Um, who are either introduced to us who either Katelyn and I know, and this is our first straight up like meeting on the podcasts stranger interview.

And I'm really excited. So Jackie, I'm going to toss it over to you to talk about what you do, why you identify as a side hustler and all those good things. 

Jackie Minchillo: [00:01:00] Okay. It sounds good. Um, well, what I do is kind of a medley of a description these days. So I guess I'll start with our, our, my husband and I own a small boutique, a web development agency where we focus on eCommerce websites, and that company is called pineapple development.

Um, and so interestingly enough. Years ago, probably about 12 years ago now, web development was a side hustle for him. Um, and through the years he continued to freelance, picking up freelance projects, bigger projects where he needed to bring in additional developers to help with the workload and such. So he had kind of started building a little bit of a team, even as a

Freelancer. Um, and in, in my previous corporate life, I was a publicist, so I always worked in an agency setting. Um, and at the time that we really made a big shift in our lives. This was early 2015 we were living in Chicago, which I think you live in Chicago now, right? Yeah. So we were living in Chicago. We were both working full time.

He was freelancing on the side. Uh, we were kind of the classic story of hitting a wall, feeling burned out, feeling like we were having a really low quality of life outside of work. That whole. That whole feel that we've now heard over and over again on ex Pat shows and, and the stories from entrepreneurs.

So anyway, we decided to sell all of our stuff. Quit our jobs and move to Costa Rica in 2015 so at that time, that is when really his freelance side hustle became like, okay, this, this really needs to turn into a hustle and support us while we figure out what we're going to do. Now that we've. Taken the leap and left everything behind.

Um, so during that time period of us living in Costa Rica, we were down there for almost four years. Um, that is kind of when I would say, I started identifying as a side hustler because I was just trying to pool from. My previous experience and what can I do at a distance and what types of jobs can I get people to hire me for?

Um, I ended up getting hired by international living magazine to cover Costa Rica, but was doing some freelance writing on the side and helping him with the overflow of his business. And at that point, mainly just. Administrative type things in terms of invoicing and writing up client communication or writing proposals, that kind of thing.

Um, and we hit a point towards, towards the end of our time in Costa Rica where I was feeling very frustrated with, with trying to attach a, um, financial responsibility to writing, which has always been a passion of mine and has always been something that has been a part of everything that I do. Um, but I was struggling to turn that into a job.

Um, and enjoy it at the same time. So that really kind of was a little bit of an ego check for me in taking a step back and saying, why, why do I continue to spin my wheels and feel like I'm banging my head against the wall trying to make this work when, when my husband has this freelance business. Quote, unquote, that keeps growing and we keep needing to find other people to help with it.

And it is, it is financially supporting us. And so I, um. I, as I said, I had a background working in agencies and I just came up with the idea that why? Why is it that I necessarily need to have my own thing? Why don't we work on focusing on this business that is financially lucrative and turn it into something more formal and let's start an agency.

So at that point, uh, that's really when that turned into a full time gig for both of us, and we started building the company into what pineapple development is today. Um, so fast forward to, um, let's see, when, what was the timeline here? Fast forward to late 2018 I would say. Uh, we were growing. We had a small team of people working for us full time and hit that point where we're, we're enjoying a very relaxed lifestyle in Costa Rica, but if we want to continue to grow this business, it's probably time to go back to the United States, um, and be available to people in person.

Focus on some more networking type activities and be here where we continue to, where we have the, uh, additional resources to continue growing a team, um, and be able to connect with other companies to collaborate with as well. Because when you're trying to do something like that from abroad. Sometimes you feel like you're on a bit of an Island in terms of what you're trying to do and that there's a lot of people around you that are living a very relaxed lifestyle, so it can be tough too.

Reach for big goals and stay motivated and get inspiration from other people when you don't really have anyone around that's doing, doing what you're doing or anything similar. Really. Um, so we moved back to the United States. Uh, pineapple development is going well in April of 2019. Um, so last year, just this past spring, we decided to sign up for a, uh, business mentoring slash coaching program.

And through that program was born really. Two side hustles, one of which has become basically another main hustle. And then the other, what I would consider to be my side hustle today. So the whole focus was in, in focusing on scalability. If you really want to be an entrepreneur and you want to build a business.

W, how are you creating additional streams of revenue? How are you ensuring that you're going to have cashflow? What are you doing to, you know, not just focus on the business, the day to day operations of the business, but what, what, what is the future vision? And eventually also, what is the exit plan? So that was kind of the focus for this program.

Mmm. One of the coaches in the program made basically a light handed comment in one of the classes one day talking about the fact that people really overlook the opportunity of investing in a business that already exists instead of starting their own business. And lo and behold, about a month after that class.

Um, the, the company that we had used for, for cleaning our house. Mmm. The, the, the two people that had been cleaning our house for months are standing in our kitchen telling us that they are, um, going to be leaving. They're going to move to Seattle because they have another opportunity and they, they're not really sure what's going to happen to their company, but they're in the process of trying to find people to cover their clients essentially.

And my husband looks at them and says, well, have you thought about selling the company? And at that time they said, um, not really. I, we don't really know anyone that would want to buy it. And so lo and behold, that starts the conversation of looking at the numbers, looking at the books, talking about what they would, what they would value the company, and what really is, um, in, in its current state or current status.

Um, and so we, what we discovered is that it would basically be buying an existing book of business. Really without any sort of formal branding or anything like that. But there is definitely a foundation there for a company. Um, yeah, idea was we're going to hire a team and this business is going to be our side hustle and a way to create cashflow.

And now here we are six months later and. That that business has grown in a way that we. Really did not expect. Um, we've had an incredible amount of support from the community here in st Petersburg, Florida. That's where we're based. And so that's why I say that kind of has become more of a main hustle than, than we expected.

So simultaneously, we're, we're still running pineapple development. My husband has taken on the lion's share of managing daily operations for joy of cleaning. And here's where it comes. My side hustle, which is investing in real estate. Which probably is really the, really was the pinnacle of why we signed up for that particular program to begin with.

That was a huge sort of piece of the program. They were going to talk about using real estate in general as a way to. Create capital, create liquidity, create cashflow, just a Fort other ventures from a business perspective. Um, and we had talked, that's something that we had talked about for years, from a very simplistic point of view of saying, we should probably think about how maybe one day we could invest in some rental properties.

And then this course that we took kind of blew that wide open because there are so many other different avenues and ways to invest in real estate that we really didn't have any insight into previously. We really didn't. Uh. We don't know anyone really in the real estate investment world at that point.

Um, and so it's one of those things that just got our wheels turning. Um, and very shortly after we completed the course. We ended up falling into this discussion with another couple who are very, very good friends of ours. They're the first people, pretty much that we met when we moved here to st Petersburg.

Um, telling them about this course, telling them about what we wanna do, telling them about some systems that we had in mind in terms of softwares that can be used and ways to generate leads. And this kind of, cause we're always looking at something from the technology standpoint of what. What kind of tools can be used.

To, do more work than one person can do. Um, and so we got talking with them. One thing led to another. We were sitting at the table one day and they're saying, would you guys be interested in, in partnering up in real estate investment? And so I now am, am working with our partner, I would say anywhere between 15 and 25 hours a week at this point.

And we are, what we're doing is primarily looking for properties that are in need of renovation to flip. Mmm. And there are some other avenues as well. It just depends on the property and what the numbers look like. But that's primarily what we're doing. And there, again, it has evolved very quickly into something that I

Really enjoying learning about and can see so much potential for different ways that, that can evolve and develop. Um, so I think I'm like a, at this point, like a perpetual side hustler. That keeps, keeps picking up new jobs. 

Caitlyn Allen: [00:13:31] Yeah. I mean, it sounds like you're a serial entrepreneurs. What I'm hearing, like you just got to start businesses like,

Oh, that's so cool. I mean, that was a lot. That's, there's so much to take in, and I can't even imagine. Has this been in the span of a a year or two years, or how long has this timespan been ?

Jackie Minchillo: [00:13:52] This time This time span of the of the of the outline that I just gave is about three a little over three years total Three businesses in three years That's insane Very fast Yeah 

Caitlyn Allen: [00:14:06] Oh my gosh I'm ready to hear this because if you've made or you've had these three businesses what are some mistakes that you've made that you're like why did I do that And you know somebody else may be able to learn from 

Jackie Minchillo: [00:14:21] Yeah Um well I mean a big one is is just I think sometimes when an opportunity is in front of you and you can see the upside of it it's really easy to get overly enthusiastic um and jump into something without really fully considering what some of the downsides might be Um and so I I definitely wouldn't be shy in saying that we probably have taken a bit more risks From a financial perspective then than would be recommended Mmm In such a short time So that is definitely something to think about And I I mean I think for us We're we're risk takers And that that is something that is really prevalent in in both of our personalities But I think a big thing is in terms of anything any kind of venture that you're looking at getting into is really trying to get clear with yourself in terms of how risk averse are you and and what type of what level of Mmm What level of pressure are you Truly able to take on um because there has been a lot of pressure in the last three years So it's it's in some of our friends and family kind of poke fun at us a little bit because it's like the complete opposite times 10 of the reason that we left in 2015 and went to Costa Rica and now we're back and like double full force into the grind of You know the day starts at 6:00 AM and it ends at nine or 10 or whatever time and then you get up and do it again But for me the biggest difference is that now we're doing it for for ourselves So we're not building someone else's future We're building our own future And in the process We've been able to employ other people and provide a livelihood for other people Um that is something that I never really actually had thought I had any interest in That was always very scary to me Um and it is scary on a day to day basis cause that's a lot of responsibility to take on from a from a mental mental emotional state Is that when you're when you're in the Weeds on a day to day basis You're not only now thinking about yourself but you're knowing you you know that you have other people that um are depending on this job to pay their rent or put food on the table or whatever whatever the case may be Um so I think that really analyzing things from a financial perspective is important And Trying to get really realistic about if you're going to take this risk what it what is it going to look like for the next three or five years and I think a big thing in terms of business ownership and starting to starting to go out on your own or do a venture of your own And a lot of entrepreneurs are people that have that entrepreneurial spirit um have this inside of them I think But The idea that you need to be willing to do things that most people are not willing to do And sometimes that looks like working your tail off for 16 hours a day And I I think that's the biggest thing is not getting jaded on on how fantastic and opportunity looks and going into it thinking that you're not going to have to hustle big time 

Caitlyn Allen: [00:18:12] What is something that's surprised you about yourself as you became an entrepreneur? 

Jackie Minchillo: [00:18:17] Um I think that the level probably the most surprising thing is the level of energy that the level of energy and the capacity I have to make things happen when I'm doing when I'm doing something that I'm actually excited about Yeah And it's a so I think back to the days of of being in a more traditional office job for lack of a better term and that feeling of like I don't want to get out of bed I don't want to get up I don't want to go out in the cold and go catch the train And that feeling of like every every next step you have to like coax yourself Did do it and get the Starbucks or do whatever the incentive is to get to the next step Um and I think that I sort of felt for a while they're very discouraged by that feeling of of lack of motivation and lack of like I'm really not excited about the day that I have tomorrow or the next day That's the biggest shift I think When you find something that you're truly excited about that you're truly interested in that truly plays to your strengths and what you have to offer I think everyone would be very surprised by the level of energy and capacity that they actually have Uh because I like now I I get up every day at six o'clock and I I I take some measures to make sure that happens I keep my phone in the kitchen so I have to get up and walk there to turn off the alarm but I like put my feet on the ground and jump out of bed and it's it It doesn't feel like a drag It feels like all right I have like I have my list I'm ready ready to go I know what I have to accomplish today And it's almost like a it's kind of like a game was like Whoa that seems like a  Like let's see how far we can get today But I think that's probably been the biggest surprise is just what I'm what I actually am capable of when the pressure is on 

Dannie Lynn Fountain: [00:20:31] So I'm curious because I've been there and because yeah I mean I I work at Google I have a side hustle I run this podcast and I'm getting a doctorate 

Jackie Minchillo: [00:20:42] Um yeah You got it going on.

Dannie Lynn Fountain: [00:20:46] Yeah

Caitlyn Allen: [00:20:47] She can add like three more businesses too I'm sure 

Dannie Lynn Fountain: [00:20:51] Um what does burnout look like Because like in a lot of ways Costa Rica was a refresh and like this Then did burnout recovery in a way um and now you've been back doing this Do you first see a big overwhelming burnout coming or are you protecting yourself in little ways every day to keep from that happening 

Jackie Minchillo: [00:21:15] Yeah that's a really great question I Yeah I definitely have that fear and I could see it happening and so but I have put some things into place that I never really prioritized before And there are things that are that are non negotiable for me now And that's my sanity So I'll just give an example or a couple of examples I guess but when we lived in Chicago I was not a big cook Never really went to the gym I would work out maybe once a week Um and we had like we had things in our like pots and pans and things in our kitchen that had literally never been opened Cause I'm pretty sure we ate out for every single meal now fast forward to today These these are habits that I was able to develop during that time living in Costa Rica when it was like okay we're we're we are kicking work out the door for a minute and we're going to refocus on ourselves and what do we need to create a happy healthy existence Um and so those habits that we were able to form by carving out the time to focus on them have now carried over So I Mmm love CrossFit I'm very into CrossFit these days and I go to the gym five days a week Usually And that number one is a non negotiable on my calendar as important as any meeting that I have or any call that I have or anything that I have to do So I go to the gym no matter what is going on Um and focusing on eating food at home too eating real food and making our own food and knowing what's going into it I cannot stress The difference in how we feel from a from both a physical and an emotional sense in in in making a shift in the way that we eat and the way that we're fueling our bodies Um And that is just so hugely important So for us now we we we've gone kind of to an extreme some people would say but we we transitioned over the past three years to up to a plant based diet So for me from a cooking perspective I find that a lot easier from a meal prep and plan I can make big batches of grains and lentils and beans and that kind of stuff and just keep it in the fridge and then mix it in with bowls of fresh ingredients And those things are a lot easier to make than if you're worried about cooking cooking meat or cooking a main dish for example So but regardless of what your diet is I think carving out time to meal prep and plan and make sure that Being yourself is a part of your schedule and not just like okay well it's three 30 I haven't eaten lunch I'm starving So now I'm going to go through the drive through and eat something out of a wrapper while I'm driving to wherever I have to be next Um so that goes back to the schedule too I think and just putting it on your calendar as this is this is crucial To me being able to function in all of the other elements of my life as well And then the other thing that has been so transformative for me is incorporating a morning routine Um and I know a lot of people talk about this and I had read about it in plenty of books and articles and whatever and you kind of read about it and you're like well who has time to do that Well once I made once I made the commitment to say okay I'm going to get up at six o'clock every day and before I do anything else I'm going to have my cup of tea I'm going to read a chapter of whatever book I'm reading and I'm going to do a 15 minute meditation before I do anything else That sets the tone for my day in such a positive way And it is the first time that I have ever felt like well I have a guarantee of having some me time every day regardless of what happens And I think that's probably the biggest problem when we're talking about burnout is that you you go into the day feeling frazzled already cause you have a million things to do And you're trying to grind through it to get everything done and hoping for the chance to relax at the end of the day which sometimes doesn't happen So for me making a priority to make that happen at the beginning of the day so that it that that I don't miss out on it has been A game changer. 

Caitlyn Allen: [00:26:12] wow those are so good because I feel like a lot of different episodes that we're doing throughout the season really relates to a lot of the things that you just mentioned So we have somebody who's talking about mindful eating and I just went okay Keto at the beginning of this year and I'm also allergic to gluten so I have like the food thing I can totally relate to And then the morning routine thing I think all of that is so important as an entrepreneur but specifically a side hustler who is not only working a regular job but then also maintaining Their own sidebar or their own business on the side So Oh that was all like such great information but we'd have to I wrap this up. So I was wondering where can we find you on the interwebs 

Jackie Minchillo: [00:27:03] Well I am on Instagram and Facebook as Jackie Minchillo So I'm pretty easy to find I use Instagram a lot more heavily these days and so and I try to really I'm trying to get better about posting content um that just about the different things that we're doing and and things that maybe other people could take away from it Um that's for both of us I think that we I've learned so much and we really would love to share it with other people so I think Instagram would be a good place to follow me and anything else that happens I'll definitely post there 

Caitlyn Allen: [00:27:42] Awesome Thank you so much Yeah we'll put all of the um tags and all of that information in the show notes So thank you so much for being here It was such a great time talking with you 

Jackie Minchillo: [00:27:53] Thank you guys, this was awesome!