Jason Scott Montoya is a lifelong entrepreneur, not surprising as he’s come from four previous generations of entrepreneurs. Jason grows their online influence & program sales for people development-oriented organizations. He is guided by his values of love, mindfulness, mastery, dependability, and openness.
Today, Jason joins the show to discuss his journey from entrepreneurship to freelancing, the importance of meeting people where they are, and the incredible value that entrepreneurship can bring to your life. Jason and Jonathan talk about cutting out the noise, what Jason misses the most about running a team, and what the transition was like going from running a business to becoming a full-time freelancer.
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00:51 – Jonathan introduces today’s guest, Jason Montoya, who joins the show to share his experience as a fifth generation entrepreneur and being open about discussing money
09:11 – Early financial lessons imparted on Jason
15:08 – Jason’s career arc
18:38 – The importance of fully committing
21:44 – Defining ‘freelancing’ and the transition from business owner to freelancing
31:20 – Considering entrepreneurship as a path
36:52 – The Jump: a letter to Jason’s younger self
40:07 – What Jason misses about running a team
43:04 – One piece of business advice to heed and one thing to completely ignore
46:20 – The last thing Jason changed his mind about and the one question Jason would like to know the answer to
49:52 – Jonathan thanks Jason for joining the show today and lets listeners know where to connect with him
“Entrepreneurialism was always something in me, and just my personality of being highly extroverted and ambitious, and just having a safe and loving home, community, family, and church life. It just gave me that safe space to dream big and go after it.” (04:38) (Jason)
“Money is a vehicle for some destination. And I think, for many people, they lose sight of that and make it about the money itself.” (12:48) (Jason)
“If I’m gonna do this – and I’m gonna do it right, and I’m gonna steward this business well – it’s gonna be really hard. And so, if I’m going to do something really hard like that, I gotta be fully committed to it.” (18:38) (Jason)
“One of the things I ask freelancers to try to figure out if they are fully committed – and it’s a key question that you need to ask yourself – ‘if your bank account was empty, and you didn’t have any work in front of you, is your first thought: ‘Where am I gonna get my next project?’ or is it, ‘I need to get a job?’ Because if you’re fully committed, you’re looking for next project.” (20:03) (Jason)
“As a freelancer, there’s benefits and downsides to being independent. We have the freedom to be independent, but the downside is we’re in the fire. We are the firefighter. And so, we have to be resilient to deal with the heat.” (28:19) (Jason)
“In a lot of ways the book is also a letter to the clients I work with. I work with clients to help them grow their sales and influence. I use different digital marketing strategies and tactics. But, my Trojan Horse is really how do I help them become the type of person that runs these types of systems to make their business better, and to be a better boss, and be a better leader and a better fulfiller.” (39:31) (Jason)
“We are distracted when we don’t know the finish line. But when we know the finish line, we know if something is or is not a distraction because it is either contributing to us moving towards the finish line or it is detracting from it.” (45:25) (Jason)
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Jonathan DeYoe: Hey there. Welcome back. On this episode of the Mindful Money podcast, I’m chatting with Jason Scott Montoya. Jason has the heart of an entrepreneur. He graduated from the Art Institute of Atlanta in 2008, attempted to make an animated feature film, launched a political news website, and owned a marketing agency for seven years before he started freelancing in 2014. Today, he remains a freelancer. He blogs, he hosts a podcast, hosts a couple podcasts. He sort of carved out his niche as a freelancer’s guide, and in 2017, he published the path of the Freelancer, an actionable guide to flourishing in Freelancing, and followed up in 2019 with the jump from chaos to clarity for your striving small business. Jason, welcome to the Mindful Money podcast.
Jason Scott Montoya: Thank you for having me. Jonathan. Looking forward to chatting with you.
Jonathan DeYoe: Yeah, uh, I’m excited for the conversation. Just to lay some groundwork. I know we said that you moved to Atlanta, but where do you call home now, and where are you connecting from?
Jason Scott Montoya: Yeah, so, originally from Arizona, me and my wife got married in 2005, and we jumped from the west coast to the east coast to Atlanta, Georgia. And we live in a county called Gwinnett county, and we lived in three different parts of it since 2005. And really, this county for Gwinnett, that’s the shirt I’m wearing. That’s what we call home. Like, we’ve been here so long. It’s been. What is that? It’ll be 18 years in June. Both how long I’ve been married and how long I’ve been here. And, yeah, so this is home. Gwinnett county is kind of the northeast side of Atlanta, metro Atlanta. And, uh, we’re kind of on the, uh, northeast side of Gwinnett county. So pretty far away from downtown Atlanta. But unless someone knows the area, pretty much just say, yeah, we’re from Atlanta. That’s where we’re at.
Jonathan DeYoe: So those 1st 18 years you said in Arizona, 18 years.
Jason Scott Montoya: So from 1984 to 2005. So almost 21 years. About 20 years there and then 18 years land. But, uh, yeah, it’s kind of funny just to think I’ve been here almost as long as I’ve been in Arizona. And I grew up in a little city called Blackstaff, which was kind of by the Grand Canyon north of Phoenix, a couple of hours, and grew up there. A population of 70,000 when the college was in class and probably 50,000 when it wasn’t. Atlanta is 8 million or something. So, uh, quite a bit.
Jonathan DeYoe: And sprawly Atlanta is pretty sprawling, spreads out pretty far.
Jason Scott Montoya: Yeah.
Jonathan DeYoe: So what did you. I’m just growing up Flagstaff, Arizona. Tell us about your parents. What kind of things did you learn about money and entrepreneurship when you were a kid?
Jason Scott Montoya: Yeah. So it’s interesting, there’s a lot of different lessons I’ve learned along the way from my family. I’m a, uh, fifth generational entrepreneur. So my dad was an entrepreneur. He, uh, worked with a company called RPS. He bought a route, they call them routes. And RPS was bought by FedEx ground. And FedEx ground had a contract model. So you ran your own business within the FedEx delivery system. And over the years, he kind of built up these, uh, different routes, five or six of them. When he finally was finished, my grandfather, his dad was also an entrepreneur. He had a laundry business. And, uh, my dad actually worked for him, did the commercial laundry for the city, for different businesses within the city of Flagstaff. They ended up having a big fire. And when it burnt down, grandfather decided with my dad he didn’t want to continue that direction. So they ended up shutting it down. So my grandfather is an entrepreneur on my mom’s side. Grandfather was also an entrepreneur. He was a mason. He built fireplaces both commercially and residentially. He just did a lot of really interesting masonry work and also dabbling in video production and other types of buying and selling stuff. Uh, and anyway, the entrepreneurial spirit goes even beyond those generations, but those are the ones I’m most familiar with. So entrepreneurism was always something in me and just my personality. Being highly extroverted and being ambitious and just having a safe and loving home and community and family and church life. It gave me that safe place to sort of just dream big and go after it. And so I used to make movies through, uh, high school. My uncle on an animation, little animation studio. He did stuff for PBS and Discovery Channel. And I’d always go over to his house and see him in his little lab, because he worked at home, he had this computer lab. And I’d tell my cousin, hey, grab me a couple of books off the shelf so I can learn this stuff at home and flip through the books. So finally it’s kind of gone up the courage. And he set me up with the workstation and I’d go there after school and teach myself 3d animations. That was kind of how the entrepreneurial side of it went from a financial side, always kind of solid, but simple financial principles. Being not going into debt, saving before you buy, being generous and giving. And so those were things that were taught to me and also modeled well. An interesting thing I’ve kind of learned through growing up, but also after the fact was my grandfather’s. Both of them ended up passing away a little over a decade ago, probably like twelve or 13 years ago now. But anyways, when they both died, they both left completely different financial legacies. One of them, uh, my grandfather, who had the laundry, and after that he had these buildings and he ended up renting those out. And he operated in a way that was financially sustainable for him and his family, but also that allowed him to his wife, grandma, is still alive, and to have enough of a trust to continue to take care of her without ever her having to work. And then an inheritance that will eventually family when she passes. But anyways, the point being is he did things right in a lot of ways. He got the will figured out before he died. All those types of things that are important, but, uh, we don’t care about them until it’s either too late. He was pretty good about that. And I’m sure there were some things he could have done better. But on the other side, on my mom’s side, it was kind of the opposite. When he passed, there was tax liabilities that hadn’t been dealt with. There was debt, there was no savings, no retirement. So both of their passings, I got a really good picture of what not to do and what to do. And that’s something that other family members, little bits and pieces that I’ve witnessed from other family members on how they’ve handled money. And so I’ve definitely been someone who’s like, watched that and go, okay, I think it’s unfair or maybe just even wrong to sort of leave something behind your kid. You can either leave a mess or something.
Jonathan DeYoe: Blessing.
Jason Scott Montoya: Uh, and so those choices kind of start today. And where did those go? So those are kind of a couple of pieces I can kind of uh, talk more about how that parlays into when I moved to Atlanta, but that’s a good foundation to start.
Jonathan DeYoe: Yeah, I want to pick at that a little bit, because the thing that’s most interesting about that to me is how much detail you know about it. Most families keep those cards pretty close to the chest. They don’t really. Or, uh, cards close to the vest, I guess, is the saying. Right. They don’t really share that as much. And it sounds like you have a lot of detail. So is that something of value in your family, like an openness around discussions about money?
Jason Scott Montoya: So with my father, my parents, that definitely was the case, and it probably was more so than it was with his parents. So I think he kind of pushed the envelope in a bit. And part of it was probably to try and carry those lessons forward, I think, with, on my dad’s side, his great grandmother was also tied into the laundry business, and, uh, his great grandfather, who died, like, way before his grandmother died, I think they were involved in the business somehow. So anyway, there was certain things that were more open to discussing, and money seemed to be one of those, which is very different than my wife’s family. Right.
Jonathan DeYoe: Than anyone’s family. Yeah, that’s different than anyone’s family.
Jason Scott Montoya: No one amazing. But in her family, it was almost, like, offensive to bring it up.
Jonathan DeYoe: Yeah, that’s normal. That is normal.
Jason Scott Montoya: So I definitely am in the unusual there, and I’m very open as well for myself. So I’ve carried that legacy on in sense of not making it taboo. And I know there’s probably some appropriateness and discretion that we need to use, but as a general rule, I’m pretty open. And even when my kids ask me those kind of questions, I’m pretty open. Like, hey, there is how much money I make per hour, and here’s how much I earn. I don’t hold that back. I don’t know if that answers your question or not.
Jonathan DeYoe: It’s great. So just sort of adding onto it a little bit. So when you were younger and your dad or mom or dad were sharing some stories about money, were you interested at the time, say, when you’re 910, 1112 years old or at what age did you turn the corner? Like, you know, dad, I want to hear about this because I imagine an eight year old going, I want to go play with my, I don’t know what you gi joes or my matchbox cars or something, not wanting to hear about money. So what age were you when you said, I do want to hear about this dad. Thanks.
Jason Scott Montoya: Yeah, so that’s interesting. And there is a kind of a connection, probably, to the entrepreneurial side of it. I think part of it was a desire to kind of pursue the things I wanted to pursue and finding the problem solving of finding ways to get what I wanted. So I’ll give you an example. Uh, or I can give you several examples, but one of them, um, in junior high, my parents. So we did talk a lot about money and that kind of thing. And part of that may have also been like, my parents were, they were probably lower middle class, so we didn’t necessarily have. We had a home and we kind of had things we were lacking, but it wasn’t, like, abundant in the way that maybe my kids experience or even others have. Uh, so one of the examples of. So for lunches at junior high and school, I had to bring a lunch. I couldn’t buy a lunch, but I had other friends that their parents would give them money to buy lunch when they got to school. And so a domino’s pizza would come in and they would sell the per slice. But if you bought a box, you could get a better deal. So what I did is I, uh, wanted pizza, and I also wanted, like, soda and a candy. So I’d get all my friends who were going to already buy the pizza and stand in line, and I’d get them all to give me their money. I’d stand in line for all of them. I’d buy the full pizza. I’d give them their slices. So now they’re getting their slice and they don’t have to stay in line. So it’s a win win for them. Uh, there’s usually, like, a couple of extra slices, which I get. I now have a few dollars extra that I can go buy a drink and candy. So the money thing was more of a vehicle to get what I wanted. Does that make sense?
Jonathan DeYoe: Totally. Um, do you know the commercial? There’s a commercial that talks about little kids are being interviewed about what they want to be when they grow up. And it’s kind of a jest. I want to be a middleman when I grow up.
Jason Scott Montoya: Okay.
Jonathan DeYoe: Ah, you’re kind of a middleman right there. You sort of put yourself.
Jason Scott Montoya: I was a broker. A middleman broker. So there was lots of other examples. Shoveling snow, because we were in blackset, which is the mountain. So me and a friend would go shovel snow and get it. But we weren’t, like, super ambitious. We would just shovel as much as we needed to get the amount of money that we wanted. And then we were like, know. So a lot of the financial stuff was very real, like, how do I do something to earn something to get what I want? My mom used to do these talk about Middleland. I got my mom to sell stuff for me as a kid. So they had those catalogs where you sell candy and other things. And you’d get enough points? Yeah, you’d get enough points. And you could get, like, a basketball hoop or this or that. And so I’d go to some neighbors and sell stuff, and then my mom would take it to her painting class, church group, and things like that. But she always sold, like, way more than I ever sold. So, uh, she was kind of carrying most of the weight, but I definitely got the benefits of all the points for her efforts.
Jonathan DeYoe: That’s awesome. So you’re saying you’re trying to do it because there’s things you wanted, and this was the path for you to get the things you wanted, probably because you had sort of that lower middle class. You saw people that had things, so you wanted the things that they had, and you couldn’t get it unless you did something to raise the money to do it.
Jason Scott Montoya: Yeah, that’s a good point.
Jonathan DeYoe: How does that experience then translate into 29 years later today? What lessons do you pull from that?
Jason Scott Montoya: Yeah, so I think there’s some really profound lessons. I’ll say one thing that I think might be helpful, too, is, well, I think just maybe at the core of it is money is a vehicle for some, um, vision, for some destination. And I think for many people, they lose sight of that and make it about the money itself, accumulating it. Or it could even be the flip side, where you don’t accumulate any money, you kind of live in poverty more, not as a potential choice, but out of some sort of insecurity or something. So I think it’s important. And the reason I bring that up, because I came to Atlanta and I had the marketing business, and there’s some things there that I can definitely share. But now, where I am now as a freelancer, one of the things I decided early on and that I even have in path, freelancer is one of the key steps is to determine how much money I want to earn per year. And that is determined by what, if the money is a vehicle towards what’s the life I want to live now? And it’s also considering, uh, next year and the years that follow. So not just the immediate term, but also the long term. And so how much money does it take to do that, to take care of my responsibilities, to have fun, to give all of those things and to determine that right up front. And then I also kind of tie that into how many hours I want to work. And then you essentially could divide that and kind of get a practical hourly rate. Whether you charge hourly or not, you just get an idea of that’s how much you want to earn. M so I think money can control us or we can control it. And I think it partially is tethered to whether or not we see it as a vehicle towards something or whether it is the desired outcome or accumulation. Does that make sense?
Jonathan DeYoe: It does. What you’re describing is thinking about it today, what do we want to have for the rest of this year and the next year? You’re talking about the sort of interrelation between your cash flow statement and your balance sheet, and that’s a financial plan. Whether you’re a business and you have goals or you’re an individual who’s got personal financial goals. That’s a plan. You’re writing a plan.
Jason Scott Montoya: Yes.
Jonathan DeYoe: You can do it back in napkin, you can do it complex with an advisor, but it’s, what do I want to have in my life? How do I make it happen? Let’s have a plan for that. That’s genius.
Jason Scott Montoya: Yeah. And I think that kind of plays out at different levels. Like, even just thinking about, I guess it’s kind of asking ourselves, what’s the finish line before we start the race? And I think a lot of times we run that race and then we get halfway through the race and we’re like, what is the finish line? Where is it? And there never was one. We’re just running it in circles.
Jonathan DeYoe: Yeah. Could you do like a thumbnail sketch? Because we’ve talked about, you have this marketing agency, you talk about freelancing, but just give us the arc. How do all those years fit together?
Jason Scott Montoya: Yeah. So when I moved here, this is another interesting financial lesson for sure, is before I moved, uh, financially speaking, when it comes to college specifically, I was on the right path the first year. I went to a university in lifestyle called Northern Arizona University. I had a Pell grant. I didn’t have to go into debt. And so I kind of rode funds that were given to me and did that first year in college. And that was great. And sort of my mentality, know, I’m going to get through college. I didn’t really want to go to college, but just to kind of honor my father. That was one of the things that decided to do. I wanted to just skip college and go straight to entrepreneurship, which, ironically, was actually kind of what pulled all the story around. So you’ll understand that in a minute. But anyways, that second year, I didn’t get those same grant. So I decided I’ll go to a community college so that I can afford to do it and not get myself in trouble financially. And I’ve learned this, and this is one example, and I can give another one. I was someone who was very staunchly against going into debt. But what I didn’t realize is that we, me can get into debt indirectly without realizing, um, know or get tethered up into it in a way that’s more, uh, severe than we realize. So with school. So I went to the university, I went to the community college. And then me and my wife got married. We moved to Atlanta. So I now needed to transfer. I transferred to the Art Institute of Atlanta, which he mentioned that I graduated from in 2008. Well, all of my financial sense went out the window when I did that, because the art student is very expensive. But I had student loans. I wasn’t thinking about it. And so my wife also transferred, and she went to an online school, university. So between the two of us, we borrowed about $90,000 for college, which a few things, uh, we didn’t realize. But when we ended up paying all of that off in ten years, and it was about $160,000, $155,000 including interest. Yeah. So then that’s the thing is, they didn’t say this, but we paid 90,000 for the school, but then we paid almost 65,000 in interest, both in capitalized interest and then accruing interest as we did it. So we wanted to knock that out. Took us about ten years, and, uh, there’s a kind of a story there. So went to college, transferred to Atlanta. We’re in this college. I also started, and I started the news website, but it didn’t make any money. So putting in a lot of time into this thing. Then I started the marketing agency, finally started to kind of make some money. But with the marketing company, I always struggled because when you have a staff and you have payroll, you got to make a lot of money to cover that. And it just feels like a leaky bucket that never ends. You fill the bucket and you’re like, oh, I’m finally there. And then all of a sudden, it’s like you look in the bucket, it’s all gone.
Jonathan DeYoe: I was actually wondering, as I was reading your story, I was actually wondering if that played into the reasoning behind the shift. From marketing agency with lots of employees to freelancing with no employees. Is that really the fundamental reason why it happened?
Jason Scott Montoya: Well, uh, I think I would just lay the way, I would phrase it a little bit broader, but I think you’re hitting on it, which is, I knew when I shut down the company in 2013, and I, uh, spent, uh, about a year kind of going through that process, and it ended in 2014, one of the things I realized is I said, and this is something I hadn’t really fully grasped when I started the company. And even as I ran it was, if I’m going to do this and I’m going to do it right and I’m going to do it well, I’m going to steward this business well, it’s going to be really hard. And so if I’m going to do something really hard like that, I got to be fully committed to it, because if I’m not fully committed, I’m always going to be kind of not doing what I need to do to make it work. And that’s one of the specific examples is like, okay, I know what it would take to kind of have enough of a sales system to really drive enough revenue to make things work and not be kind of always having empty buckets. And I said, if that’s the mission, then I don’t want that mission. And it’s not that I don’t want to do a hard thing, but it’s just the outcome. The end goal of that mission was not what I wanted. So I don’t know if that answer.
Jonathan DeYoe: Your question or my, no, I think it was a lot of work, and it ended up in a place, and you didn’t want to be in the place. It ended up, and you saw that going at the outset. So you say, you know what? I got to change something.
Jason Scott Montoya: Yeah. So it’s like, hey, you want to climb Mount Everest? Oh, that sounds cool. Then I’m like, halfway up and I’m like, actually, do I really want to climb out Everest? Not really. Maybe I want to swim in a lake over in Arizona.
Jonathan DeYoe: And you write about this in your books. You write about the importance of one of the, I think that’s your first thing in the freelancer book, is if you’re going to know it freelance and commit, you have to commit to it. If you’re not going to commit to it, then that’s, uh, like the first step towards success.
Jason Scott Montoya: Yeah. And it’s a double edged sword. And one of the things when I talk to freelancers and they’re struggling and trying to figure out if they are fully committed. The key question is to ask yourself if your bank was empty, if your bank account was empty and you didn’t have any work in front of you, as your first thought, where am I going to get my next project? Or is it I need to get a job? That kind of tells you if you’re fully committed, because if you’re fully committed, you’re looking for the next gig, the next project. But if you’re not fully committed, you’re thinking of, uh, maybe I should do something else. Maybe I should go to the job.
Jonathan DeYoe: Yeah. Plan B. What’s my plan B here?
Jason Scott Montoya: So, being fully committed is kind of cutting out plan B, which there’s kind of a way to sort of reconcile that without it being too extreme, but where you drive yourself into the ground unnecessarily. But anyway, the idea is being fully committed. And the other interesting thing about this, the irony of being fully committed, is that it’s actually not as hard as it is if we’re not fully committed.
Jonathan DeYoe: Getting there. The steps aren’t as hard if you’re fully committed.
Jason Scott Montoya: Yeah. What I mean by that is if you know something, you know the risk is coming, then I can expect that risk, because I’m fully committed. So I can expect the risk, and then I can mitigate against that risk. And it, uh, may be a lot more work at the front end, at the very beginning, but to maintain that is fairly easy. So that’s, I think the irony, uh, with being fully committed is it actually is easier in the long run.
Jonathan DeYoe: Well, I look at it this way, like, if you’re fully committed, all your energies and whatever energies the universe can provide because of your commitment, are at your beck and call. If you’re 1ft in, 1ft out, then you don’t get your energies, you don’t get the universe energies, either one of them in your pocket. You’ve been a freelancer since 2014, so tell the audience what freelancing is, and then tell us about a little bit about the transition from business owner employees to freelancer. No employees. And I asked this question because I think most people go the other way. Like, um, I’m a freelancer for a bit, and then I hire an employee to help me out, and then I hire another employee, and then I hire another employee, and now we have a business.
Jason Scott Montoya: Yeah. And I would also add that the tension you’re describing, people go the other way. It’s very strong, even with people around me. So when I shut down the company, I had a very, like, I’m not going to create another marketing company. And so I had like this hard, fast rule, but it was like, because I was fully committed, all of a sudden it was like, hey, you should think about hiring people. Hey, you should leave hiring people, growing that other business. And it doesn’t mean that I couldn’t or I won’t, but I’m just going to do it for this. So, like you mentioned my books and my podcasting, that, uh, could turn into something that maybe that might be a business that I wouldn’t mind, would be okay hiring someone. So it’s not that I’m against hiring, it’s just that I don’t want to build that type of business again. That’s why I chose not to do it. I knew what it takes and I don’t want to do that. And the more I work, because I work with a lot of agencies where they’ll outsource stuff to me and I realize how much it just reminds me, oh, yeah, I don’t want to do that. But, uh, kind of what is a freelancer? At a basic level, a freelancer is if someone who has a job is balled into a single employer, their work week is committed to that, allocated to that business. A freelancer essentially has diversified bosses, right? So you have multiple clients, might work with six to twelve clients at a time, and probably three or four of those are going to be a bulk of my time each month. And so a, uh, freelancer is simply someone who has multiple clients now that can get more specific in different varieties, forms. But at the basic level, that’s what is a freelancer.
Jonathan DeYoe: Do you think there’s a benefit of a freelancer of, uh, focus, like a freelancer committed to a certain type of freelancing does this thing, whereas if you’re an employee of a company, they may ask you to do this thing and oh, by the way, could you do this other thing and this other thing? So does a freelancer have the ability to really focus on, say, their niche expertise, or are they also beholden to the client wanting other things?
Jason Scott Montoya: Yeah, I think you got both. You definitely have both. And this is one of the interesting dynamics that I think a lot of people that jump into freelancing with rose colored glasses fail to realize is it can actually be harder as a freelancer to set and enforce certain boundaries than when you are an employee or even when you’re an entrepreneur. And so everything is kind of dynamic, driven. So when you’re a freelancer, uh, like financially speaking, nobody’s going to say, here’s a 401K program and you need to be contributing and we’re going to match it. And da da da da da, uh, da luichi would get out of most companies that work with as an employee, unless it’s a startup person. But, um, as at a freelancer, nobody’s telling you that. So that’s kind of the idea with the path of freelancer. What are these systems that need to sort of we need to have because nobody else knows what to do. So I don’t know if that’s kind of what you’re hinting at, but that’s what came to mind.
Jonathan DeYoe: I’m actually wondering about, can you as a freelancer say, I’m a photographer and I just take pictures. They’re not going to ask me to write a blurb about the picture. They’ll have somebody else freelancer that will write the blurb about the picture, I just take the pictures. Whereas if I’m sitting in an office and my job is to take the pictures, my day might not be full. So they may say, you know what? You’ve got two more hours today. You’ve taken 6 hours of pictures.
Jason Scott Montoya: Why don’t you go take some pictures?
Jonathan DeYoe: Yeah, why don’t you wash the dishes or do something else? Right. There’s like more creep in a company than in a freelancing gig.
Jason Scott Montoya: So I think there’s definitely in terms of dynamics that can definitely be on the side of the freelancer to kind of avoid some of that. Uh, and there’s a few variables that can help shape that. But I think as a freelancer, the more specific you can get, the better, the more focused you can get with your industry, your audience, your target, and the problems you solve and how you solve them, then you create more value that you can deliver. And so I would definitely recommend that. And when I first started freelancing, you could say that it was sort of broader and then it kind of narrowed in as the longer I’ve done it, and I think that’ll continue as I continue. And now with me, I’m a little bit differently because I do pricing based on my time. So I mentioned hourly. I do batches of 10 hours at a time. So the creep is kind of interesting, the dynamic. One of the reasons some people charge per project, some people do other forms of pricing. But because I’m hourly, if you scope creep with me, you’re paying for it. So it creates a natural tension that the more you use me, the more you’re paying. So even if it does creep into something that, uh, I’ll give you example. There’s a lot of things, because I work with clients at both the project management strategic level and both tactical level. And sometimes the tactical level makes sense for me to do, to fill in the gap, but in the long term, because of the rates I charge, sometimes it doesn’t make sense for me to do those tactical things. You’re paying too much, essentially, if you’re having me to do that. So we’ll try and bring in another resource, but out of convenience, someone may have something urgent, and they just don’t want to kind of go through that, and they know that I’m reliable, and they just pay the premium, so to speak. But I’m happy to sort of accommodate because of that. Now, if I was charging a fixed fee, I would have to be very strict about my boundaries and not going outside of that scope creep, because that means I’m doing free work. Does that make sense? Right.
Jonathan DeYoe: Yes, totally. A lot of this comes out in their contractual arrangements. Like, what are we paying for? How is it written, uh, up? That becomes very important if you’re a freelancer, understanding how that works.
Jason Scott Montoya: Yeah.
Jonathan DeYoe: So question about, I want to go back to how you transitioned from, and what was that like, transitioning from running a business to being a freelancer?
Jason Scott Montoya: Yes. It’s definitely been, for me, like, all the benefits without the downsides. And there was actually one downside that I did struggle with at first. And this kind of has to do with maybe your earlier question, too, was, I had a company and I had a team. And when I shut down the company and I was on my own, I realized in retrospect that I had a wall or a shield with a team. I wasn’t on my own. So when things got hard or difficult or client challenges, I wasn’t feeling lonely or isolated. Right. And in some cases, I probably took that too far. I know that I did. I took it too far where I actually hid behind the team. Like, here’s a bad situation, uh, I’ll team deal with it. Uh, and so hiding from that. Well, as a freelancer, both the benefits and the downside of being independent is that we have freedom to be independent, but the downside is we’re in the fire. We are the firefighter, and so we have to be resilient to deal with the heat. Now, I think that creates some positive dynamics. One m. I want to make sure I do good work, so it kind of prevents me from getting too comfortable, because I got to stay focused and stay on target because I don’t want to deal with the heat. Right. So unnecessarily. And sometimes that still happens. There are things that are outside of my control that if I do everything right and things still go down in a dumpster fire. So, yeah, that’s part of that transition is going from being by myself to, uh, being with a team to being by myself. And this sometimes why people go from being by themselves to building a team is being in the fire as a firefighter is tough, or being in war is tough, being a soldier. Maybe I should be a general or, uh, I don’t have to be on the front lines because a rough place to be. So I think that’s a similar ship. Now, one of the other things, as far as the business goes, I learned a lot of things in the business, but it wasn’t until the business ended that some of those solidified inside of me. And so when I became a freelancer, and this is why a lot of freelancers struggle and why I wrote book and why I’ve been able to be successful as a freelancer, is I run my freelancing as if it is a business, even though it’s me. So I have systems and processes that I follow that I’m disciplined about following, and I follow them because I had the company, I learned those lessons, and I knew what happened when I didn’t. Well, I know what will happen as a freelancer if I don’t follow these systems. So I’ll give you an example. I have one of my systems called the water tower. Essentially, it’s an emergency savings. And as a freelancer, you’re going to have people that pay you on time, people that pay you late, some people that don’t pay you at all. So I wanted a financial buffer because I didn’t want to feel the stress of that reality. That is a reality. So I built financial buffer that essentially is a big old cushion that when those things happen, I don’t have to panic and freak out. I have time to figure it out.
Jonathan DeYoe: The well is dry. Let’s go to the water tower.
Jason Scott Montoya: Yeah, exactly. And so that I have to expect the drought, and then when the drought comes, it’s not a big deal. And I built that into my hourly rate, too. I built, um, in every year, and probably there’s going to be like, I kind of just built in $2,000 a year where someone doesn’t pay me. Now, thankfully, it’s been much milder, but that just means I have a little bit more cash than I would have. But if someone doesn’t pay me, then I don’t lose anything out. Now, I do have other systems that help mitigate those type issues or risks that are flexible as well and does help me.
Jonathan DeYoe: Uh, there’s a lot of those written about in the book, so I’d just say we’re not going to cover all of them here. But if somebody picks up the book, then by all means. So you’ll see these all detailed. So we’re talking about mindful money is a podcast about money. We talk a lot about entrepreneurship. You coach entrepreneurs. So how important do you think it is for people to consider entrepreneurship as a path? I know that your life has been packed with it. My life has been packed with it. I think that most of my success derives from the business that I started, the less the fact that I’ve been successful in that business, but the fact that I have a business has built and grown, and the value of that thing becomes my net worth. The business is my net worth. How important do you think entrepreneurship is just for your clients, but us, for us generally?
Jason Scott Montoya: Yeah. So I think when we sort of open the entrepreneurial net, open it up into a variety of variations, I think it’s a big tent for a lot of people to get inside.
Jonathan DeYoe: Totally.
Jason Scott Montoya: Freelancing is a form of entrepreneurship or solopreneurship, and I think those historically have been diminished for the build a company, make it big, sell it for lots of money. If that’s the kind of person you are and the type of thing you want to do, then that’s fine, go after that. But I think for most people, the smaller approach is actually probably more common. And if you think about it, like I mentioned at the very beginning, about money being a vehicle, right? So if you want to build a business, grow it, scale it, and then sell it for a lot of money, well, you want to do that so that it gives you money for something. But you could also just create a business that generates enough income that does the same thing as well. So we can skin cats in a lot of different ways or a different animal, if you like cats. A. So, but the idea is that entrepreneurship is, there’s a lot of forms of it. And even like my father, even though he had the contractor business with the different routes, it was under FedEx, so he didn’t have to do the sales side of it. So people could do franchises, they can do all forms of entrepreneurship out there, and I think there’s a lot of them out there. I also think what people don’t realize until they’ve lost their job is how, as an entrepreneur, our risk can be diversified. Uh, this isn’t always the case. Sometimes you get freelancers where they only have one client, and they get all their income from this one client. And essentially, it is a job, so they’re not diversified. And then when that client stopped working with them, they’re like, in a big old mess. But for me, I’m intentional. Like, I have a rule. One of my systems is I won’t let any one client take more than, like, 30% of my income per month, except for a special project. I might go over it temporarily, but not in a long term sense. And part of that is to mitigate against that whale risk of, like, yeah, they bring in a lot of money and it’s great, but then when they leave, I’m starving to death.
Jonathan DeYoe: This hits home so beautifully, because this is probably seven or eight years ago, I took on a client. This one client was equal to maybe half of my assets under management. So this was an enormous client. Instantly became a third of my business. But she was a client for two, three years. And then when she wasn’t a client anymore, I had grown, still hurt, but the business had grown enough. So I flatlined for a couple of years. But it was so important to the business that she stay for as long as she stayed. Otherwise, I hired people. It would have been kind of a debacle if I’d lost that client early. So, yeah, it’s a really good idea to limit the power any one client has over your practice, your business.
Jason Scott Montoya: So that kind of them just having systems to diversify. And, uh, you probably know this as well. If you’re an employee, you can do the same thing, making sure you’re investing and maybe you’re buying real estate. You can diversify in other ways if you don’t are afraid of it. So I think the idea, though, is however you do it, do it. But wherever context you’re in, just figure out the best way to do it in that context versus feeling like you’re locked into one form or another of entrepreneurship.
Jonathan DeYoe: Do you think our culture pushes people away from entrepreneurship, or do you think it’s open? Anyone can do it.
Jason Scott Montoya: That’s an interesting question. So, I don’t know that I’ve felt that in any hobbyist way. In fact, I’ve probably felt it that it encourages, I mean, even just the idea of, like, shark tank as a show and how that kind of drives so much interesting and related type of activities online and even on social media, but I’m kind of in that type of entrepreneurial bubble that may not be representative of the normal employment experience. I’ll give you an example. If you’re an employee and you lose your job and you get fired, your income is all gone, right? So you have a high risk of, uh, loss of income. Whereas me, if, uh, I lose my biggest client or you lose your biggest client, 30%. It’s only 30%. I’m still making 70% on my paycheck. But if you’re an employee and you lose your paycheck, you lose 100%. So do you want to lose 30 or 100%? So I think that culturally, that is probably a narrative that’s out there, that it’s more secure to have a job when in fact, it’s actually more risky.
Jonathan DeYoe: I think you and I would agree on that because we’re entrepreneurs. But I think you’re right. I think culturally, the adopted sense is that having a job that you show up at 08:00 or 09:00 every day and clock out of 05:00 is definitely less risky. But hard to make the argument for it when you look at the way you’re looking at.
Jason Scott Montoya: I don’t know how to phrase it, but I would say we probably underestimate the risk of selling our soul to a job for money in terms of just depleting our passion and our motivation, where we’re simply just. We probably should do something else, but we’re just doing it because we need the paycheck. Because we need to pay for this or that.
Jonathan DeYoe: Yeah. That being said, I do know, and I’ve seen that in people, but I’ve also seen people that love their jobs. They’re working for a great company, treats really well, got a great benefits package. They love going to work every day. I’ve seen that as well. So you can find it. People can find that, and that’s equally good. So why the second book jumped off and you started freelancing. You write about freelancing, which makes perfect sense. You’re still freelancing. Where does the jump come from in this whole process?
Jason Scott Montoya: Yeah. So path of freelancer is very practical. You don’t even have to read the whole book. It’s very organized. You figure out what your problem is, and you go to that part of the book, and there’s the solution. Right. So the jump is a very different type of book, and in some ways, it’s a letter to my former self before I started the company. Like, what would I tell myself? Which maybe I wouldn’t have listened to anything I said. But part of it is I wrote the second book to entrepreneurs, and particularly entrepreneurs that are in a particular stage, which is the stage, uh, of they have been doing this a while, and like we’re talking about with the job, that soldier that was sort of draining their soul. They have a business that’s draining their soul. Right. I had a business that felt like a prison, probably like in 2000 and 910, and I kind of realized, okay, this isn’t working. So I shifted and I transformed the business into something much better. And then that gave me the visibility to go, actually, is this what I want to do? So the last question they asked is, if I could do anything vocationally, what would I do? And marketing agency wasn’t one of them. So I decided to move. But before I got to there, the question I asked before that was, if I were to reboot this company and do it differently than I had the first three or four years, how would I do it differently? So I restructured the business. And so the book talks about kind of the before and after and that transition and what that print is for that second half, and it’s really processing those things that I went through. And it was very therapeutic to write the book. And interestingly enough, and this kind of, it’s for entrepreneurs that feel stuck. Maybe they have three years where their revenues have plateaued and they can’t seem to get over that hump. And really, the essence of the book is to say that you can’t grow your company until you grow yourself. And so the book is geared towards, how do I help you one see that and also help you change, which is a difficult thing to do in a book, but I certainly tried.
Jonathan DeYoe: I want to give you this phrasing. I have a coach, one of my business coaches. So you get nuggets from business coaches, and this is one of the nuggets that has stuck with me for probably a decade. He said, jonathan, it is what it is. It is what you made it. It changes when you change.
Jason Scott Montoya: So that’s another system I have. It’s called wind it down, 530. So I want to end my day at six, and I have an alarm that says, hey, it’s time to start winding it down.
Jonathan DeYoe: Oh, that’s your wind down alarm. Are we getting close to end here? Anyways, that’s good.
Jason Scott Montoya: Yeah. Now, one of the interesting things that I’ve experienced as a freelancer is working with entrepreneurs in a lot of ways. The book is also a letter to my clients that I work with in some ways I work with clients to help them grow their sales and influence. I use different digital marketing strategies and tactics. But, uh, my Trojan horse is really how do I help them become the type of person that runs these types of systems to make their business better and to be a better boss and be a better leader and be a better fulfiller. So that kind of another layer is just kind of the deeper how do we help people become better versions themselves so that they can be better leaders for the people around them and their families and communities?
Jonathan DeYoe: Yeah, it does sort of spread out that way. So you’ve been a business owner running business with a team for seven years. You’ve freelanced for roughly eight years. I know that you prefer freelancing. Obviously you’ve said as much here, but are there some good things about having a team that you miss?
Jason Scott Montoya: Yeah. So, like I said, having the team and the community and camaraderie and have versions of that now. Right. And I have clients that I work with and their teams, but it shifts a little bit more. It’s not as permanent or it’s not as the volume in terms of how much time you spend with the team is different. So that camaraderie is definitely something that’s lost and kind of have to replicate in other aspects of life. There definitely is a diversification of, uh, skill sets and talents and roles and responsibility, as well as a healthy dependency of like, hey, I’m sick this week, I need help. That’s not necessarily I have to create systems to help kind of manage that, but to some degree, a lot of my income is labor dependent. So that’s where I’m certainly exploring other revenue source, like writing books and doing podcasts and things that can kind of play that role in a way. But yeah, those are definitely pieces of the puzzle. I think one of the things that an agency definitely has an advantage to providing is that scale. If you have a team and you need to do something big and fast, uh, sometimes they’re going to be certain types of projects that they’re just going to be better suited for, and I’m a better player of a role in that, probably not going to do all the pieces.
Jonathan DeYoe: So you sort of said something that I want to tease out because I’m wondering if the third book is in the works and if the third book is going to sort of compare and contrast your experiences as a business owner versus freelancing.
Jason Scott Montoya: Yeah. So actually my third book is very different than the first two. If the first one is practical, the second one is personal, the third one is religious, so it’s called from the garden to the cross. And it’s about Jesus’story. Now, there is a connection to the business, but it’s about when he was in the garden of Gethsemane all the way to when he was crucified. And what do we learn about ourselves and him through that process? But one of the triggering points as it relates to the business is when I was ending my company from 2013, I took a year to kind of figure out what I was going to do and to shut it down. And about probably halfway through that, or maybe two thirds or three quarters of the way through that, I really wanted to finish well. So the last three months up the business, I wanted to make sure that everyone was taken care of, clients were taken care of, and I made some mistakes, I did some things well. But ultimately, I had that kind of idea of what does it mean to finish well? And I thought of what Jesus said on the cross, it is finished. I thought, what could I learn about finishing well from him in that moment in the passion story? And so that kind of has some connections to the business, but it kind of also starts to go outside of the business to a higher level. Does that make sense?
Jonathan DeYoe: It, uh, makes perfect sense, and because I know you, it makes perfect sense. So there’s a ton of noise out there, and I want to ask you to simplify it for people. Let’s pretend you’re on a plane. You sit down next to somebody, they figure out what it is you do, and they say, I’m struggling with this business that I have. And what would you give them? Just one thing that they could do today that would lead to more personal and business success.
Jason Scott Montoya: I think articulating what it is we want and kind of tying into the commitment and then getting committed to going after that. I think a lot of us don’t actually know what we want, and our desires drive us, or maybe we kind of do know what we want, but we don’t want to, um, put it out there. And this kind of does tie into the new book. There’s something about putting ourselves out there that makes us vulnerable to criticism or critique or challenge. And there’s very few things that make us feel as vulnerable as putting out what it is that we desire and want, our dreams and aspirations. And so I think if they don’t have clarity on what that is or they have some sort of tension around that, that would be one of the steps. And that’s one of the things I do talk about in the second book is like, your business is a vehicle to drive you towards somewhere that has to do with personal vision, your personal aspirations. And so it needs to be a vehicle that’s driving you there. And for me, my marketing company was actually driving me the wrong way. It took me east when I was going west or wanting to go west. And so I thought it was a vehicle that was going to take me where I wanted to go, but it was actually taking me further and further away. And I had to get out of the car, and then I had to walk back to where I started. And then from that starting point, it’s kind of that phrase you probably heard. Did you climb the ladder? The ladder was on the wrong building. You need to figure out, make sure the ladder is on the right building before you start climbing the ladder to get on that kind of idea.
Jonathan DeYoe: We’ve used that analogy on this podcast before. I love it. Before you start climbing, make sure your ladder is on the right wall. What is it? So the flip side of the same question is, you’re sitting down there with she’s lamenting about the business that she’s in. What’s one thing that she’s probably doing or people have told her she should be doing that she should ignore and stop doing? What’s one thing that’s sort of common parlance that hurts business owners.
Jason Scott Montoya: When I was talking earlier about the idea of, like, it’s the entrepreneurial tent, that there’s different types of entrepreneurship. And this kind of gets to getting clear on our vision and what we want, both for ourselves and for our business. We are distracted when we don’t know the finish line, but when we know the finish line, then we know if something is or is not, uh, a distraction, because it’s either contributing to us moving towards the finish line or it’s detracting from it. And so by having that clarity, it helps us to then go, okay, your advice. Someone may be giving you advice for their vision, for what they want. And when you apply that advice to yourself, that’s not what you want. So it takes you in the wrong direction. So you need to ignore the distractions or at least contextualize them. Take the piece that could help you, and then apply it to your vision. And so ultimately, the question would be, is you need to cut out the noise. And the way to do is to get clear on the finish line.
Jonathan DeYoe: Well said. Before we wrap, there’s a couple of questions I have to come back to the personal. I warned you about this. So what was the last thing you changed your mind about the last thing.
Jason Scott Montoya: I changed my mind about. Well, there’s a lot of things I’ve been changing my mind about. Just writing this. Yeah. Like, writing this book is like opening my mind up in a lot of ways. And even today, I was watching this video just about how people change. And I tend to be intellectual and knowledge oriented and so shifting my mindset to realize that has a place, but people, they don’t necessarily process that way. We’re more intuitive and kind of impulsive and less systematic and formal in what we think and how we think, and we’re organic, and so kind of learning how to speak to the heart of people and kind of get set their desires and figure out what is this that they want. So even though if someone is not investing in their long term in retirement, that may be simply an unawareness issue, or they just don’t know that they should be doing it, but they also might not be the type of person that wants that does that because it’s the appropriate thing to do. So those are two different dynamics. Becoming the type of person that would sort of do that. And I think as kind of being a, uh, fully committed freelancer, you, uh, kind of identify okay to do this. Well, I’ve got to figure these problems out, and someone might be able to help me, give me sort of fast forward that process, but I’m going to figure those things out. That’s different than someone who isn’t fully committed and isn’t going to try and solve those who doesn’t want to solve those problems. So kind of changing my mind about how to meet people where they are, that really connects with them, where they are in the way that they need it and not the way that I want to deliver it. I don’t know. That’s kind of a long answer, but.
Jonathan DeYoe: I don’t know if you know this word, upaya. I know that we had a conversation earlier about Buddhism and Christianity, but upaya is skillful means it’s, uh, offering people the piece of information or advice that they need in the way they need it at the time they need it. It’s just skillful means doing it in a skillful way, right? That’s kind of what you’re talking about.
Jason Scott Montoya: Yeah. I think stories and narratives, that’s one of those ways that we connect music, art, community, and it is different for different people in different ways and different times and different seasons.
Jonathan DeYoe: Yeah. I mean, tomorrow may be a totally today I wake up with back pain. And so I have one sort of set of philosophies about the world tomorrow. I don’t. I have a different set of philosophies about the world. Day to day, a person could change. So a second question. If you could get the truth about any single question about your life or your future, what would the question be?
Jason Scott Montoya: Well, interestingly enough, that question or that kind of thing, I’m changing my mind is kind of tied to it. How do I meet people where they are in the best way possible? But that’s right now I face really difficult challenges and then I sort of follow the breadcrumbs for answers. And I find really wonderful, interesting, neat things elite, this talk or this podcast or whatever. And it’s really kind of cool how that unfolds. I don’t know that I have anything more specific than that to say, but that’s a couple of things that come to mind.
Jonathan DeYoe: The idea that, uh, I need to meet them where they are. How do I meet them where they are? Tell the audience how they can connect with you. Where do they find you?
Jason Scott Montoya: So my website is Jason scottmantoya.com. That’s jasonscottmantoya.com. If you put a slash blog, you can see kind of the library podcast. You can see the podcast, the podcast much everywhere you find it, Stitcher, Spotify, so on and so forth. The podcast is called the share life systems and stories to live better and work smarter. And the books are on Amazon. You can check those out. I’m also on social media, Twitter, Facebook, LinkedIn and Instagram a little bit as well. Pinterest, all of those. YouTube. I’ve got a YouTube channel, the podcast on there as well. My podcast with Jonathan is on there as well. So you can check that out where we flip the there. But yeah, pretty active on the website, on social media. And you want to connect, feel free to connect in those. I do have a contact page on my site if you want to reach out, share your story, ask question and uh, great way to.
Jonathan DeYoe: I spent some time on your website for this interview today, and you’ve got a lot of content, a lot of stuff, and there’s a lot of little rabbit holes. You go down this rabbit hole. So go down some rabbit holes. Visit Jason’s site, go down some rabbit holes. The links will know in the show notes for everybody. Jason, thanks very much for coming on. I’ve enjoyed another conversation with you and I look forward to the next one.
Jason Scott Montoya: Cool, thank you, Jonathan. I appreciate it.
Jonathan DeYoe: Thanks, man.