What's Killing Your Side Hustle Before It Starts | Ft. Ashley Negron

Welcome to the Optimizing Beyond podcast. I'm Josh Negron, and this show's all about sharing lessons, ideas, and strategies that sharpen your thinking, strengthen your habits, and push you to grow beyond comfort zones. Let's dive in. Welcome back to the show. I'm joined again by my co-host, wife, Ashley, and today we want to talk about Optimizing side hustles and finding your passions in order to execute those. We get those questions a lot. We have several businesses that we've had and grown over time. And so this is something that we love to talk about and that people ask us about. So we're going to cover what the main enemies of these kinds of things are, as well as some ideas of how to get to it, how to get into action and get those things started. And also that there's many ways to do these kinds of things, that there's not just one way to do it. And it kind of depends on your approach, your personality, And your risk aversion plays into that heavily. And then also whether you're going to go in it alone, or if partnerships are going to be a realistic part of what you're doing. Some of that depends on kind of what you want to tackle and what you're interested in. And so we'll go through those today. Welcome to the show, Ashley.

We're looking forward to this topic.

Yes, it's something that we are super passionate about and love doing. So just a little bit about what we do is back in 2020, I started my first business. And that was a sports car rental business back in April of 2020. And so my thought was it was something that I was—I had a lot of interest in. I love cars. Cars are notorious for being terrible investments and being a burden on a family if you're into cars a lot. And so I was like, man, how can I turn this into something that would be less of a burden and that I could turn into a business that it could pay for at least some of it or maybe all of it? And so in April of 2020, I decided, hey, what is the best. This was before AI, so I couldn't chat with AI about it. And I was like, what would be the best car to start out with? What's the biggest bang for buck? And if you're a car guy, a Corvette is typically high on that list. And so I was like, sweet, I'm going to get a C7 Corvette. Bought a 2014, 2015. I got an automatic because unfortunately most people don't know 3 pedals, especially if they're below a certain age. So I picked that up. I bought it in El Paso and I was driving back when the shutdown started happening in the middle of COVID Now, What a horrible time to start a business during the middle of this situation. And, uh, but due to the nature of it, you know, people were still allowed to drive and driving was some of the only ways you could get out and not really be around anyone else. So the car rented out all summer. It was crazy town. And there wasn't anything like that in our small town of Southwest Missouri. And so I realized, man, I might really have something here. And so I more than covered the expense of the car. Uh, insurance is an interesting, tricky little booger. And so it wasn't like super successful from the financial front. I've had a lot of people ask me over the years, so should I start a sports car rental business? I'm like, no, it's not for that purpose. But I started adding, added another car, a BMW convertible, and that did very well as well. And then brought on some partners that also had some good cars. And we grew the business to up to 5 cars. At one point, we had a high-end Mercedes. McLaren and some other cars. It was, it's been super fun. We've, and since 2024, we've scaled the business down a little bit because when interest rates went up and business went a little bit tighter. So it's just been that flux of that business over time. Still running, still renting. In fact, the last 2 weekends, the cars are fully rented out for prom and all those kinds of things. We're also heavily into real estate. We've started several other businesses and including a property management business as well. So these are things that we get asked about a lot. And so we wanted to cover some of these things. Now, the 3 enemies that I see pretty clearly that stop people from doing things like this, I'll list them into 3. So being overly conservative, fear, which can coincide with that obviously, and then perfectionism, this eternal preparation. So you're constantly like brainstorming and planning, but planning is not action. And so even before the AI age and now during it, you could have 1,000 chats with AI about all your ideas and gimme a business plan And show me the way to do it. But if you just get stuck in the planning, nothing's ever going to happen. So Ashley, let's run through how you view these, starting with the overly conservative. How does that stop somebody from starting a business?

Well, anytime you start a business, there is definitely, um, this element of risk involved, right? Like you are pouring resources, time, money, effort, there's sacrifice involved. And so it can really, you can talk yourself out of it very quickly. Like, what if I do this? And then, well, Here's all the reasons that I shouldn't. And so learning to take a risk is just like any— anything else that you have to learn how to optimize. It's a muscle that you have to learn to exercise and you have to flex it in order to become more comfortable with it. You know, and depending on like the way in which that you grew up or, you know, the household that you came from, this area of risk is something that a lot of people just don't take, right? Like we have this aversion to failure. We actually opened a business a few years ago, and it wasn't overly successful. And so we ended up selling it, and we covered the expenses, like, but we didn't walk away with a lot from it, right? But the lessons that we learned through that were invaluable, and I'm not sure that we would have learned them any other way. And so it's, um, like I said, it's a muscle that you have to flex, and you have to get comfortable with not looking at failure as something that defines who you are as a person, or that the risk You know, it may not pay off huge dividends, but because of the mindset that you have and the way that you approach and look at things differently, what am I going to learn from this? What lessons and what strategies am I going to learn? What other things am I going to be able to pass on to other people? What, how can I help people learn from my own mistakes and my own failures? Right? Like every failure is an opportunity to learn a lesson if that's the way that you choose to look at it. And so that's kind of the way I see people being too conservative is, is that kind of also tied to fear. Just, yeah, the, the risk is hard to take and we so quickly talk ourselves out of it.

Yeah. And like you said, this, this dovetails a lot with fear, obviously, that you mentioned the fear of failure. And so the, this, this thought that you need to execute perfectly or that when you do a business, you, you're supposed to know everything upfront. The problem is, is things don't always go how you predict. So you put all this effort into executing this and anticipating for that. And what if something else that you totally didn't plan for or anticipate, then your whole plan is garbage anyway, was a complete waste of time to a certain degree. And then you have to pivot on the spot with the business already running. This happens countless times. You talk to any business owner and they're like, yeah, I mean, I totally didn't anticipate this. I actually didn't even plan on doing this and it ended up pivoting to this. And so some people get into business to think they're doing one thing and end up doing something completely different because through executing it this way, they realized there was actually a need that was maybe greater or slightly different or whatever it was. There's all of these pivots and we have, you know, our mentor, Danel Delgado says assets always adjust, you know? So Seth Godin in his books always talks about the concept of ship it. We've talked about that before, just do it. And so because of that, you are able to iterate on the spot. You can't always anticipate what's gonna happen. And so there is that element. And so fear really does keep you from almost any action. Because you're— that's often combined with running away or being paralyzed, and neither of those two exhibit any action that's useful in order to build a business. And so fear of failure is a huge one. The concept of failing forward and learning from your mistakes and executing and iterating on top of your failures is actually how you get better and how you get better ideas and implement and iterate more. And so I've seen people that have started multiple businesses. And when I mean multiple, I mean like a lot of businesses and it's almost second nature at that point. And they're able to just do it. There's minimal stress because they, they're like, yeah, I've done this before. This is easy, you know? And so fear is something huge that holds people back. And then the last one that I really, really fixated on, because this dovetails with my, I, you know, I call myself a recovering perfectionist, is that you are just stuck in this eternal preparation. Right. And so James Clear talks about this in Atomic Habits in the book, and that, you know, preparing is fine, but if you spend too much time preparing, there's a, there's a point where you just have to start. And so I like to really make sure I'm aiming that shot, but if you never take the shot, it doesn't matter. Um, and there's other people that like to shoot and then aim later. And so we always joke about that with, uh, with those personality types, but there is some value there in realizing, hey, When someone is sighting in a rifle, you have to shoot multiple times because you have to see if it's— if you're aiming dead on and it's off, then you have to adjust, right? You know, you just left, you're like, oh, well, I'm, you know, okay. So that insinuates that you have to iterate, you have to have execution, you have to have action in order to adjust that later shot to get that dialed in. And business works exactly the same way. And so perfectionism has a good heart behind it. However, again, I always say it's in the name, it's impossible. And in the same way you can't be perfect, your business can't either. And so you just need to get started and get going.

Yeah, I think, you know, it's one of those things where so many people are so capable of more than they give themselves credit for, right? Like, people have got these crazy hidden talents or these crazy ideas. And we really are sometimes our own worst enemy and talking ourselves out of something that could bring so much good to the world, or you could solve a problem that people have. I think it's one of the reasons I love honestly like watching clips of Shark Tank. It's like these are people who have taken a risk and have found some niche, something that fills a void, that meets a need. One of my favorite kitchen products is straight off of Shark Tank. And so it's one of those things that, you know, then once you learn the backstory and you learn about people and you learn about what made them do— decide to create this crazy brand, right? So many of them saw a need, filled a niche, and probably have created this product multiple times over until the iteration that they pitched on Shark Tank, right? Like, they tried it and this part failed, and they kept trying and this part failed. Every good break starts as a series of failures. And you think about every big company, everybody that started in a garage or a basement Right? Took that risk and took their shot and decided to just somewhat jump in with 2 feet. Now, you don't always have to do that, but there's a reason that that works and that you have to learn to be comfortable with that failure. And I think that's a muscle that you and I really, over the last 6 or 7 years, have really worked on exercising and going, okay, like, it's gonna be okay and we're gonna choose to learn from it. And we're— now we're not gonna make stupid decisions that put us in, in our family in a risk, right? But We're going to maybe take more of a risk than our 20-year-old selves would've because we've learned to flex that muscle.

I totally agree. That is definitely true. We've made calculated decisions, but there have been times like in the, in the car rental business, there were cars that I thought would be amazing to have and would rent well, and they just didn't. And so I had to make, I like, hey, this car's not it, sell it, let's get something else. And so we did that multiple times. There were amazing cars that we had. We had an Audi R8 Spyder at one point. Amazing car, rented once, you know, maybe twice. Had a Toyota Supra, a brand new one, and it rented also like 2 or 3 times in a period of over a year. So amazing car, go-kart feel, great looks. Yeah, it's a BMW, I get it, but super quick and really fun to drive. Nobody ever rented it. And so it was one of those things, it was like, man, I could have sworn this would've been a good hit and it just wasn't. So you can do all those things, you can beat yourself up and maybe you lose some money, but you have to really recognize how you don't do that, not beating yourself up, Moving forward, learning the lesson, and maybe making an even better choice because of that other one in the future. So these are huge, huge things to, uh, to overcome. But if you can, that means you can get started and start to actually do some work. Now, people ask all the time, how do you do it? And some main questions that I would love for people to really exercise and think through that you can do a brainstorming session by yourself. You can have a conversation with AI about it, of course. And those are things like, what is your passion? What are you good at? And what do you love to do? Those things are important because sometimes they'll factor into an idea, to a business thought, some sort of service, and fit into some sort of passion that you would love to do, love to offer the world. And so, like you said, people on Shark Tank, there's other things like, you know, America's Got Talent and American Idol where people have actual talents that they've never shown anyone, and it's just super cool to see. So that's a good question for people to ask, like, what do you love to do? What's your passion? What are you good at? Those really get So that's getting to the heart of some of the things that you as an individual can offer that can be pretty massive in a business. And then there's common vehicles of business that, you know, whether that be, you know, maybe you're really savvy with, with numbers and investments. And that's something that you're like really interested in and really kind of nerdy about. And it wouldn't take a ton of effort for you to get like really good at executing those things for you and your family. There's obviously a massive vehicle of real estate, the barrier of entry is really high. And from the looks of it, not changing, likely getting worse. And so there's people who want to get into real estate but just don't feel like they can. There's some clever ways that you can do that. I mean, just one Google search will reveal multiple techniques that you can do to get into real estate. But that is a very common, very popular way, offering some sort of service to people. Like if there's a service that you think you can provide your town and there's not a lot of competition, that could be something very, very good. If you have an idea for a product, and in this day and age, this isn't just a physical product. There's tons of people building things with AI, you know, with Claude Code. You can do that in, in Lovable or any of those vibe coding apps. And, uh, you can build some really interesting things. A lot of my semi-tech friends have built things initially to solve annoyances and problems in their own life. So they're like, I'm only building this for me. And then people are like, hey, what, like, can I use that? And so, and some, some interesting apps have come out of people just building stuff. That, uh, that they wanted to fix some, some solution for their own life. And then other people ended up just wanting it. It's the same thing for a physical product. So if there's something that you think that you could do, that is a huge way to do it. And then just businesses with offerings that solve problems for people. If you follow entrepreneurs that are highly successful, they'll tell you that honestly, just solving a major problem for a large number of people is a huge way to have a successful business. And so That's a massive, massive thing that you can do. And then the last thing that I want you to weigh is asking yourself about you and your role. So for some people, they'll end up being the bottleneck to that business, either because they're the one with the skill and that skill doesn't scale unless they can multiply that skill to somebody else.

Mm-hmm.

And so think of like things like trade, like repair or the tactile trades with where you do things with your hands. If you're the only one that's doing it and it's difficult to teach, this is gonna be a business that could be limiting as far as scale and growth. If growth and scale are not something you're, you're super passionate about, you're like, no, I just wanna do this. That's totally fine. But you need to have that on your radar to know ahead of time that I have some friends, even with flourishing businesses, they feel like they're stuck. And that's the other piece that business owners can get stuck in that role where they're still the pivotal person where the business can't run without them being there. So they're stuck working in the business, not on the business. And so even if you do get people that you can teach those skills to, or it's actually not dependent on a skill of yours, but it's still dependent to run with and around you, then that is another scale problem that you need to think through of how can you teach others to help you run it? How can you teach others to have the same, same skillset if that's necessary? And how do you get out from being stuck in your business? Those are huge things that business coaches and mentors teach about all the time, cuz this is a very, very common thing that people get stuck in. And so this leads me to the fact that there's so many different ways to do this and so many different people types to execute. And so what I mean by that is, is there's a spectrum of different people where you can still be an effective person in business and highly successful. And be very conservative, whereas on the other side of that spectrum, you can be extremely aggressive, leverage aggressively, and also scale quickly. And so there are countless examples on both sides. Probably the most famous on the conservative side is Dave Ramsey, and he is very, very conservative, and he's consistent with those with those techniques. And I have a personal friend who has been. Who has, who has used a lot of his principles to pay off his house. And he has a rental house that's been paid off for several years, and in so doing has been saving for his second rental house to either do very short-term financing or pay in cash. And then he's like, I just want to snowball. And then his goal is in 5 years, I want to, I want to have 5 rental houses all paid off. And so, and then just snowball that into getting a 6th. And so obviously, at some point, that momentum is going to propel him into being able to have a sizable portfolio with all the equity out there and, and the ability to use that rent to do whatever, retire or keep buying. And so that's, that's crazy. But it is, it is the slow play for sure, right? So it takes multiple years, decades to do things that, you know, people are, people are impatient, they want— that's why get-rich-quit schemes are so schemey, right? Because they're like, well, what if I just win the lottery? That'd be so much easier. So by that, there goes the ability to get more aggressive and to use leverage to because there are some people that I know that would be like if I had a asset that was completely paid off, I would immediately leverage it and use that as a down payment for three more properties, right? And there's people already that are listening to this and like yeah dude, that's like that's exactly what I would do absolutely. And there's nothing wrong with that as long as you don't over leverage yourself and you stay responsible. And there's financial advisors and And mentors and even bankers that can help you do that in a way that where you're not putting yourself in compromised positions. And then you can grow that equity and grow your portfolio or your business that way. Obviously, the more aggressive you are, the more risky it is. You know, if things go sideways, then you, you're gonna, you might have to be stuck in a situation where you have to liquidate quickly. That's never good for getting a great price. And so you need to make sure that you have good connections and good partners. That, that has mattered for us. It's easy to look at a bank and be immediately negative and like, but there's a huge difference between a good bank partnership and one that is just a stiff-necked bank where you don't have any people that you know and trust in that organization to help you. And so that's super important to know where your comfort level is with those kinds of things. If you are going outside your comfort zone in that area, then you can really sacrifice a tremendous amount of peace. Which in my opinion, isn't, isn't worth it. If you're going against that, people say, well, you only grow when you're uncomfortable. I get that, that, that kind of philosophy of like getting out of your comfort zone. Sure. In this specific regard, talking about debt and leveraging and being aggressive in that route, I think it's important to do some internal review and understand like what you're comfortable with. And the friend that I mentioned earlier that was doing it in this snowball method, he's about to buy a second one and he's got a good goal. That 5 goal, and the math makes sense. Like, he's gonna, he's gonna achieve it, and he's gonna be 100% at peace with it and never stress about it. And he's gonna retain ultimate flexibility. If, if the worst happens in every horrible scenario, uh, it doesn't matter. He's good to go. He owned that first rental house during COVID and, uh, and it didn't matter because it was paid off. So even if the renter stopped paying rent, because there's a lot of people that couldn't afford rent, During the shutdowns. He's like, it wasn't a big deal because I didn't owe the bank anything. So we're just chilling, waiting, you know. And so that's just something that is very personal to you. A lot of people have strong opinions about it and can, can really sour your pudding if, if they're giving unsolicited advice. But just keep in mind, like, this is something that you need to explore for yourself. It can change too. I'm wired way more conservatively than, than a lot of people. And so initially, I had to work through some of that. In that, and that leads me to the last piece that dovetails with this as far as doing it alone or having a partner. And so my business partner is much more aggressive than I am as far as risk aversion, does not have much risk aversion. And so for me, actually, that's, that's a really good yin and yang scenario because we can really work through opportunities in a very holistic way, I believe, and seeing multiple dimensions of any particular opportunity. And that's been a really, really good—

I combination.

And also, we can talk about this more when I have him on the show, but there's this dynamic between us that, that he's a visionary and I'm an integrator, which is to borrow some of Gino Wickman's verbiage out of Traction in how we both look at business differently. And again, that also helps us execute on another level where it has a multiplicative effect, where 1 1 is not equal to 2, it's actually much, much more. And this is something that, again, is also a very personal decision. to bring in a partner because I, when I went into my first business and brought on a partner, this was something I sought advice from several people. And one businessman that I greatly respect told me he's not a fan of partnerships. And he said, partnerships work until they don't. Investors are one thing, but I don't think I'll ever do it. And I went against his advice, obviously, spoiler. And the way I viewed it, this was personal. I viewed it like, In the same way that you can look at marriage metrics and say, well, half of people get divorced, so why get married? I think you can look at it that way. I don't think that's— I mean, I'm married and I think it's worth it. And I think other people, if you find people with healthy marriages, they'll be like, yeah, no, I don't regret it one bit. Well, if you go into it looking at the statistics, you might think, uh, you know, I mean, it's a 50/50 shot. It'll be awesome or horrible. I think your role has something to do with that as well as your partner's. And so we always talk about you can only control yourself. You can't control other people. And same applies for a marriage. And I think also the same thing applies for a partnership. And so anytime that you go into a partnership, there are things that are going to be more difficult. There's another person or persons there that you have to— it can be clunky, you have to communicate, like all the very simple, very similar concepts to a marriage, that you have to be intentional. And those kinds of things we talk about often. And so for me, it was worth it not going in it alone, like working alongside others that are locked arm in arm with you is something that has been really fulfilling for me. And so that for me has been the answer. But for other people, they're like, no, I like being a sole proprietor. I like being the single person to make decisions and head it forward. But the more you scale and grow, sometimes you realize, man, I need, I need variety. I need a different spread of people around me. Sometimes that can be employees and it can be good. But other times, partners and people that are level with you can really offer something completely different because you don't sign their paychecks. It's a little bit different. Yeah.

Yeah, I think, you know, that's, that's such a personal decision. The cool thing is that we all bring so many different unique skills and abilities to the table. So, you know, if you're, if you're like, man, I don't know, like maybe like being the hype person, being the marketing person, like that's not my skill set, find someone to do it with you. You know, there's, there is so many ways to structure a partnership or a business. Get creative with it, have fun with it, you know, use it as a way to invest in other people, to bring them alongside You, you never know where the reward for that may end up being someday. You know, just like any other relationship in life, it's it's not guaranteed. But learning to work through, like you said, the communication and having trust in each other that you know you want to make this work is I think worth the risk. You know, money does do weird things to people, and so you know if if it gets super successful, you may you may see a different side of people. But like you said, you have to control you and how you approach it, and to be to be someone to. to be in that partnership with. And so it's definitely not for everybody, and it's not for every business that you may even own. You know, you, you never know what that's going to look like. Both of those 2 things that you were just talking about definitely are something that has to do with personal comfort level, um, and something for you to think through, to research, um, to look at different ways. The, the cool thing about the capitalist society that we live in is there's so many different ways in which to accomplish a goal. And so sometimes half of the fun is the creativity and the journey to get to that goal. And so use it as an opportunity to learn, research, learn things online, start watching YouTubes of people who are kind of doing a similar thing to what you're doing. Start researching and learning. Even if for some reason you decide that that's not the business, you've spent your time learning something. You're flexing a muscle.

Yeah.

You're farther down the road than maybe what you were before. And so use it Don't, don't see it as a waste of time. See it as like, oh cool, I learned something new, right? Like, it's all about the way in which that you look at it and the mindset that you view it through. And so I think this just really fits into, you know, so much of the things that we've been talking about, about optimizing our lives. You know, this topic actually came up because I had one of the young ladies that works with us just ask like, hey, what else do you do and how do I get into that? And she's super interested in that. And so she's just like starting to think and figure it out and ask questions. And so I think that's the best way for that to start. You know, some people do a side hustle or do whatever because it's a way to have fun and a passion and eventually take over their W-2 job. Some people, it's a way to save on their taxes. Sometimes it's, um, that they have this thing happen in their lives and they have to figure out how to meet this void. Or maybe there's something that happens and you have to create this product to fill and meet a need in your own life, and you're like, oh man, what if other people also wanted to think that this was really cool? And we live in a day and age where you can do your own marketing. It's so free and it's so easy. And there's so many resources, more resources available to you to start a business than any other time in history. And so if that's something that you're interested in, take the leap, do some research, put together a business plan, ask other people who are business owners, and then just see what happens. You genuinely never know where it may take you. And honestly, like, that's half the fun is the journey of figuring out and heading down that path.

Yeah. And I mean, I I know, uh, sometimes people get a little AI fatigued, but I mean, this is something that when I, like I said, when I started my first business, AI wasn't a thing. And, uh, it would've been super helpful to have something like AI. I think information aggregation is something it really does help with where you're like, hey, I'm thinking of like, these are my passions, this is what I'm good at. What do you think I could do? Or like, this is like a business I'm interested in. Can you show me other examples of how people have done it? You can ask it all sorts of interesting things to get forward movement to the things that you're stuck in. You know, like, I don't know how I would do that, or I don't even know who I would talk to, or, you know, whatever. And it could be like, no, just do this and do that. And I mean, I had to figure out all that stuff from the get-go, just one at a time. Like, you know, how does a brand new business that's never done any business get a loan for a car? That's a weird question. And so it was one I had to humbly walk into my bank and be like, hey, this is what I'm looking to do. What do you guys think? They were willing to gimme a chance. They're like, I mean, it, and it was pretty low risk for them. They're like, oh, this is a, I mean, we would loan you the individual. It's a car loan. They weren't, it wasn't that scary to them. So there's other things that you could ask AI and get answers to your questions to, again, to get forward movement to your thoughts, to the things that are swimming up in your head that never quite make it to action. So I hope some of that information was helpful. If there's some things swimming around in your head that you're thinking of doing, like what is holding you back? What is stopping you from taking action? And start asking yourself, what are the things that you're passionate about that you think that you can offer the world? Are there any ideas or products that you think that you could be a facilitator for to help? These things are really awesome questions to ask. And, you know, what approaches could you take? What is going to be your technique? These are good things to know in order to kind of assess kind of the paths that you could potentially take on some ideas that you might have in order to execute an awesome business potentially. Thanks for listening to the Optimizing Beyond podcast. Remember, growth happens when you take action. So subscribe, share this with a friend, and most importantly, put what you learned into practice because we know that daily anything changes everything.