Ep. 60-Nick Loper: The Side Hustle Expert

Nick Loper, founder of Side Hustle Nation, explains how side hustles differ from second jobs through upside potential. He built a podcast empire from an affiliate site and emphasizes learning, taking the first step, and failing fast. The core move: validate ideas before spending money, work in public to turn what you're doing into content, and act instead of overthinking.
Chapters
This is the You Winning Life Podcast, your number one source for mastering a positive existence. Each episode, we'll be interviewing exceptional people, giving you empowering insights and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, winner and certified entrepreneur coach, Jason Wasser. All right guys, welcome back to the You Winning Life podcast. I have a really awesome guest today. His name is Nick Loper. He's a chief side hustler at Side Hustle Nation. He's an entrepreneur involved in a large variety of projects. You're really working on helping people figure out how life can get less stressful by creating something in addition to maybe your first income, second income, starting a business, and relying on your job as your only source of income. I'm really curious, this Side Hustle Nation. So what is a Side Hustle Nation? What is a side hustle? How did this start about? What are you doing? Let's start there.
Sure, sure. And on the surface, that probably sounds like more stressful. You make me do more work? Like, that doesn't sound great. Promise the, uh, the rewards on the other side, uh, make it worthwhile. Uh, so a side hustle, broadly speaking, is anything that you're doing to make money outside of your day job. Uh, generations ago might have called it moonlighting. There is a subtle difference though between a side hustle and a second job, or, you know, delivering pizzas on the weekends and stuff. Yeah, I would probably still call that a side hustle, but there is a more entrepreneurial connotation here where it's like this has some upside potential, this could go beyond hours for dollars, this could become a thing, right? So that's how I would kind of think of a side hustle. Side Hustle Nation is the blog and podcast I've been running since 2013 to kind of showcase these different random ideas, my own experiments in trying to make extra money, and almost 400 episodes of The Side Hustle Show. Featuring other, other people like us who are crazy and want to figure out how to make extra money too.
Incredible. How did this all start? Because I can— like, you need the distinction between a second job and a side hustle, and I think the psychology of that is incredibly important, the breakdown between those two things. It's not work harder versus working smarter. It sounds like something very, very different. So let's— can we break that down a little bit more on a psychological perspective?
Yeah. And there's maybe one difference too, is like, if you need to make money quickly, second job, freelancing, consulting, like totally viable option. Lyft, Uber, uh, DoorDash, awesome stuff. In fact, Instacart, I think, brought on a quarter million new drivers this spring, like surging in demand as nobody wants to go out of their house anymore. Um, plug and play, very simple, uh, to get started. That said, if you do have a longer time horizon, maybe you're not the person that needs to make rent this month. I never was the person who hated my job, I just didn't see myself climbing the ladder there. And so I was like, okay, could I build something here? Where in the early days, my hourly wage was so far below minimum wage, it should have been illegal. Toiling away, trying to get that flywheel spinning, trying to get something off the ground. In my case, it was a comparison shopping site for footwear, which total random niche, not a sneakerhead,— but here was a physical product. This is dating myself, like comparison shopping is not what it once was. If you remember, you know, in the early days of the internet, you would go to Bizrate or NexTag or Shopping.com and say, "Where can I find the best price on my next thing that I want to buy?" Whereas nowadays, most people just go straight to Amazon. In any case, comparison shopping for shoes, it works on an affiliate model, which is basically helping other companies sell their products and services online in exchange for a commission. So when anybody would buy shoes through the site, I would earn a commission, usually between 5% and 20% at the very high end. And that was the vehicle that let me quit my job. That was what I naively thought that I could probably grow old being, selling shoes on the internet. Didn't last forever. And so while I was running it, was really fortunate to have started a couple other side projects. Actually, more than a couple, most of them were abject failures, but a couple are still around today. And one of those was the blog and podcast. And so that was kind of where it got started for me. It was like, hey, this was my experience in being able to build an extra income, quit my job, and become in more control of my calendar. And like, how can I spread this gospel of a lower-risk brand of entrepreneurship?
Love it. And I'm wondering, like, is there a personality type that is more predisposed, right? 'Cause you have decided to take these risks. You have decided to leave the comfort of a job at whatever pay rate, go out on your own, learn a new trade, learn new skills, learn new technology. Like, what do you think, like, some of the barriers to entry are? What do you think some of, like, the personality predispositions are for people who are gonna maybe, A, decide to take this risk, but B, once they do decide to take this risk, to become successful? In doing this?
That's an interesting one. I mean, one of the primary personality traits is like a love of learning, which I was a good student in school and that was exciting to me. And there were some subjects that I kind of dreaded, like foreign language, like everybody speaks English, this is dumb. And then once I got into it, I was like, this is really cool. I get exercises, a different portion of my brain and you learn to love it. And it kind of was like, hey, learning new stuff is awesome. And it's the same thing as an entrepreneur every day. Trying to figure new stuff out and work through different logic problems. Like just this morning, I'm in ActiveCampaign, it's my email newsletter provider, and it's like, well, if I wanna tag someone who takes this action, and then logically what should happen after that? It's like, I don't know, it uses a lot of brain capacity, but it's not easy for me, but it is kind of fun to think through those types of problems. The other personality trait that really stands out through all the interviews is the willingness to take that first step, recognizing that it doesn't have to be forever. This doesn't have to be the thing that I do forever. Like, I started out, um, you know, trying to sell candy at summer camp, trying to paint houses during the summer. It's like, all of those were important, but none of them were like— I—
that wasn't gonna be— weren't your end-all be-all, this is what I'm gonna do for the rest of my life, right?
Right. Um, but taking that first step, not knowing where the trail may lead. Super important in recognizing, okay, what's next doesn't mean what's forever. And then maybe number 3, kind of a caveat or an add-on to number 2, is a willingness to fail. And failure sucks. I'm super risk-averse. There are people who are like, "Fail fast, fail forward." It's like failure still stings. It still isn't any fun, but you almost have to be willing to accept that that comes with the territory. In fact, I found there's a video that Noah Kagan put out. Noah runs AppSumo and OKDork and the Noah Kagan Presents podcast. Awesome guy to pay attention to in the entrepreneurial world. And he's like, over the last 20 years, I've started, I think it was 20 or 25 different businesses. 6 of them were successful. It's like, it's not a bad batting average, you know? But I think it almost comes with the territory. It's like, you know, not everything that you try is going to stick., but you have to take a few swings to find something that does.
Right, and the one that he's known for right now, that AppSumo, is incredible because it's leveraging day-to-day resources that we all need in all of our technology. And if you're a small business owner, if you're a social media person, every week there's a new— just as a plug, because I've invested/bought in so many of the products over the last couple years— that it gives you such an incredible deal. For what you need, and you get to try it, and there's a 30-day refund policy if you don't like it, which is like, no one does that, especially when it comes to like, you buy a tech thing, you buy a program, you're like, ah, yeah, like if it's download, that's it, too bad. But I think you could have a model. He calls it Groupon for geeks. Hmm?
Sorry, I lost you. He calls it Groupon for geeks.
Hmm, so I never heard him say that, so that's really cool, but I know that their technology that they're offering and their programs they're offering, and I tell a lot of people, I'm like, hey, this is for you, here's this link, go follow up. So I send it out to a lot of my friends, But that's like not even realizing that he's creating a community of people that are advocates for his own brand, which I think is— how does that play into like what you're sharing when it comes to creating something? I know as a therapist and as a coach, I work with— until 2.5, 3 months ago, I was working in office. I had a very small amount of handful of clients that were coaching that were fully digital, but now my practice has entirely shifted to my home office where you see me in right now. There's constantly a pivot. Like you said, this may not be where you're doing for the rest of what you're going to do for the rest of your life. How does creating advocates and creating a community around what you're doing go hand in hand with what you've been trying to create with this whole side hustle project?
Yeah, this is really an interesting point. This is kind of an important thing. There's probably a couple signs of it. One is this idea of, quote, working in public, where you're documenting your journey along the way, you're blogging about it, your Instagram stories are filled with this, you're YouTubing about it, whatever it is. People like to follow along with that human journey. And that can turn into content and it can be actually profitable down the road too. I'll give an example of, well, Nathan Barry from ConvertKit is a good example of this, having run his personal blog alongside the business for years where he shares the ins and outs of kind of what's working, the mistakes we made along the way. That's kind of a prolific example. One guy who's a little less known, one of my favorite guests on the Side Hustle Show, was a guy, an engineer out of Chicago, where his side hustle was fixing motorcycles. Straight up service business, hours for dollars, ad on Craigslist, don't take your bike to the dealership, don't pay dealership, whatever, I know what I'm doing, I'll fix your bike. What was really cool was his working in public, like set up the camera, here's how I'm fixing this, problem on this model of bike. I gave him, you know, he wasn't getting paid to do that, but that guy gave him content for YouTube. Um, that eventually was able to package up some of these longer videos, sell those as digital download products. And over time, the time leveraged income streams from YouTube ads, from digital product sales, from sponsored content on the YouTube channel started to outclipse the hours for dollars service-based business. I was like, This is fascinating, as everybody kind of starts out with this, you know, income pie that's 100% hours for dollars, at least most of us do. But he found an interesting way to kind of like chip away and like start building this other little segment of the pie that was a little more passive, a little more time leveraged.
Incredible. Then I know like in the concept of The E-Myth, right, uh, Gerber's book, where you have the entrepreneur, the manager, and the technician. And the technician, really, whether it's us working on our project, and you can be a doctor or an attorney, you're only getting paid, right? You're getting paid per hour and you're getting paid at, let's say, at a higher rate is no different than a person who's a barista or a janitor or someone who's making minimum wage. You're still getting time for money, right? And as you try to evolve and move in and out of this space, it's kind of like you said, this passive income, creating content where you can actually monetize that while you're sleeping, which I think is like the biggest successes of what moves you into into a whole different place of operating as a business professional, right?
Yeah.
And you would agree with that?
One of the crazy ones that came across my desk just this week was an attorney, and I believe she quit her job in advance, so not necessarily a side hustle, but instead of doing, you know, hours for dollars as an attorney, which is a fantastic hourly rate, she started creating this YouTube channel and then quickly pivoted to talk about like what's going on with your stimulus check, what's going on with these small business loan programs, and it starts off with lawyer explains and then fill in the blank, you know, the name of the program. Like these videos have like tens of thousands of views in just a matter of a couple months. And she said like, honestly went from like $0 to $20 grand a month in YouTube ads. It was like, wow, you know, just it can blow up really quickly.
Well, so are you saying that when you claim expert status in something, that will help drive some type of, I don't want to use the word marketing, but some type of attraction to that which you can offer? Because, right, I can say like, okay, I'm Jason Wasser, LMFT 🎗️ versus therapist interviews, right, whatever it is. Are you, is there a, from your perspective of doing this, is there a perspective difference in identification of expertise versus a name with a title?
Um, especially in the case of an attorney, like a lawyer, like, okay, there's a certain perceived level of expertise there. The, the other interest— there's probably a couple ways to go about it. So it's really common, like, hey, I, I built this thing, I had some success doing this, um, you can pay me to do this for, you know, a pretty decent rate. Or, you know, I maybe now I've created my downmarket offer where it's like, here's the, um you know, over-the-shoulder video tutorial series of like, here's my process. If you wanna do it yourself, you can get this digital course or, you know, guidebook for a fraction of the cost. So some people do go that way where they're targeting the same customer base, but slightly different angle, or what's especially in the online world, like really common, like, hey, I started this successful freelance whatever business, or I had a successful podcast. Now let me turn around and teach you how to start a successful podcast. Working in public can kind of go both ways there. Does that make sense?
Yeah, it's— I know one of the things that I struggled with until I actually heard someone else doing this was, as a therapist, obviously I have confidentiality and I can't go and throw a show, a therapy session, just like that online, like I'm doing this type of thing, even though now, right, every single one of my sessions are online. But I realized that if I'm doing a non-clinical strategy session, brainstorming session, a coaching session with someone that I can use. So I actually put out an offer to people in a certain community that I'm in. I don't know if you're familiar with Jesse Itzler and his Build Your Life Resume community. And so I put out an offer to people in that community. I'm like, "Hey, you know I'm a therapist, but I also do more coaching from this perspective. If there's something that you want to get handled that's not an emotional relationship dynamic thing," and you're willing to trade me helping you for using that on my podcast, reach out to me. And I did that and I created a few episodes of showing me how I would work from a coaching perspective into episodes of my podcast. So it's not—
Did that end up being an effective marketing strategy for you? Did you get other people who were curious, like, well, I'm not sure if I really want to sign up, but now that I hear how he works and how he's helping these other people, Okay, now I'm more comfortable doing that.
Well, it's interesting because the first time, even though I have people who are now, 'cause people are like, "Oh, are you making money on your podcast?" I'm like, "That wasn't my initiative." It'll be great if eventually I do, but I see it as a leverageable marketing tool that's a necessity at this point. And I know there's like, what, 1,000 new podcasts being created a month. And I know that Joe Rogan just got like a $100 million deal to become the Howard Stern of podcasts, right?
Right, right.
God bless him and mad props to him, like really, I think it's an amazing thing. I don't care about the timing that's in the middle of the pandemic and people are like, "Oh, this is ridiculous." Like, business is business and people need to get paid and people's talents are gonna get recognized. So, like, I have no negative qualms about that. I'm like, "Shh, this guy created and crafted it. Like, it's incredible." So, what I found is I recently started working with a teenage client who has a very similar background and experience to me. He's been through a few different therapists over the last couple years. So I had the mom have the kid listen to my first episode and then decide if he wants to get on a Zoom call with me, not as a session, but as a 20-minute get-to-know-Jason Wasser session, right? So that first episode had my background, why I'm doing all this, why I am where I am today, starting from high school, my family stuff and all that. And that allowed him to say, "Okay, I want to have a 20-minute call with him," versus his parents saying, "You're going to this therapist." "you're gonna work with him." Right, right. And it gave this teenage kid a buy-in, and we are having this incredible, incredible therapeutic relationship in the span of like 3 weeks, and like, stuff that he's never tackled in other therapy experiences has been tackled in 3 weeks. So there's, I feel like there's an additional buy-in to that, and I'm using that as a leverageable thing. But I'm also, I think the fact that I get to have certain people who are experts in the area, like you and other people that I've interviewed, If I'm able to get in front of them and no other— and other therapists aren't doing this, then that already makes me stand out.
Yeah, exactly. And you see that for service providers across the board. Like, we've got an upcoming episode from a ghostwriter, and what he started doing was creating video content around, like, super targeted keywords. Like, you know, he's got 250 subscribers on his YouTube channel. Like, he's not blowing up the YouTube algorithm in any sort of meaningful way from ad revenue or that sort of thing, but it's like really targeted stuff like, how much does a ghostwriter charge? Or how do I write a book proposal template or something? You were— it's like, hey, I can showcase my expertise, I can showcase my personality. By the way, I do this for a living. If you want to have an intro call, you know, click here to book your time. We've seen people do this, um, like in, in web content too, where it's like, here, if you want to do it yourself, here's how to— one of the ones was like And a super niche example was like commercial lease reviews. And it was like, guy had carved out an awesome little side business doing commercial lease reviews. And, you know, he would target keywords as specific clauses in these contracts, in these leases. And he would write, you know, the 3,000-word post, here's everything you need to know about this little addendum that they often throw in there. And he's like, at the bottom of the post, if you want somebody to look over your entire lease, Hey, this is what I do for a living. It's $500, call me.
So he leveraged himself as an expert that I'm gonna give you a ton of free information, but if you don't wanna have the effort, time, or energy spent into Googling and researching it, pay me for my time, right? And I think that's the most brilliant way of doing it. I really—
Yeah, and both of these guys position it against the amount that you're gonna spend or what the amount that a, in the ghostwriter case, like what this could be worth to you. He's got a cool calculator on his site. This is entrepreneurswordsmith.com if you wanna check it out, where it's like, okay, You have this many people in your audience, you expect to convert at this price point, this many people, and this is your high-end offer. And it's like, hey, this book project could be worth a quarter million dollars to you, right? So he's kind of anchoring it at the very high end. And on the lease review thing, it was like, you know, you're about to enter this 5-year legal agreement, it's probably going to cost you tens of thousands of dollars. Doesn't it make sense to have a pro take a look at it to get you the best terms first?
Man, people think they can get away with it just by Googling a few things. So it's really because I give a lot of— since this pandemic started, I've been teaching workshops for different young professional organizations, and I've been doing a lot of stuff around relationships and dating and single's life and mindset. And someone reached out to me afterwards on the class, and I'm like, listen, like, based on what you said in the class, this is what you need to get addressed. And like, well, everything is closed where I live in Canada. I'm like, that's not true. They're like, well, what advice would you give me? I'm like, sorry, like, ethically and legally, I don't give advice. And two, if you want to retain, like, hire me, you can hire me. But three, You have to do some due diligence on your side, but I can see how people would want to take advantage of that if a professional— At the beginning, we were like, we want to help. We want to get it from as many people as possible, and sometimes we'll diminish our value just to do that. But I find that as we evolve, we have to make sure that you're creating something that is monetizable. You do have good boundaries around it. You do say, listen, that's my product. You do have to pay me for that. And see how quickly they either jump on it or disappear because they're just trying to get something free out of it. So I'm wondering, like, for you, like, as you're— as you evolved, as you trading— because, right, we're still all trading some level of time for money, and, right, married, family, pandemic is going on right now. Like, what are some of the challenges and what are some of the positive things that have come out from the last 60 or so days for you in this experience?
Um, well, positive side has made us rethink our whole relationship with preschool. So we had two boys, they're 2 and 4. Um, we've always just kind of assumed they would go to school. And so we've been sending them 4 days a week. That was my compromise. Like, I'll take days off, you know, I have this awesome business. Like, you know, I have some time flexibility. So we've had Fridays off for since they were born, but now it's questioning like, what was I doing the rest of the time that was more important than hanging out with these kids? And so it's like, a little bit of an existential thing over here. And that's not to say there's still, because they're together all day, every day, like there's more conflict than there's ever been, but they're also playing better together than they ever have. And like, we have more time, we feel less rushed in the mornings. Like, I feel like that's probably the biggest kind of shadow benefits. Like we're not, well, you gotta get to school or, you know, mom's gotta get to work. It's like, we got all day, let's figure this out. So that's been, kind of the positive side. The challenging piece has been trying to squeeze in the responsibilities. And I'm really, really fortunate that like all my deadlines are self-imposed. You know, outside of getting the podcast out every week, like nothing else, just because I have commitments to sponsors at this point, nothing else really needs to happen. And it's frustrating. It gives me anxiety to no end to see like the list of projects that I want to do that kind of pile up. Would it be helpful to talk about one way that I'm kind of like, I've been dealing with that? I don't know if it's effective, but I find that anytime there's a period of time where I'm not working or not working the full amount, like that actually sparks a lot of creative energy where like a couple years ago we took, you know, 5 or 6 weeks off and it was like, when I came back, it was like this catharsis of productivity. And I was like, ah, you know, got all these projects done. Cause it was like this pent up, energy for it. And I feel like the same thing is kind of happening now. We're like, okay, that would be cool. That sounds like a fun project. And I would put them on my paper to-do list, which I keep on my desk. It's down there. And I found that was giving me a lot of anxiety because it was like a daily in-your-face reminder of all the stuff that was not getting done because I'm like, oh, the family responsibilities. So I ended up booting those off into Asana. Like, I still think this is a good idea. I want to capture it. I just don't need to look at it right now. And so that's been my game plan. And granted, not a lot of those are moving forward right now, but they're there, they're captured. And I feel like if I now could go in and do like, okay, here's the 10 or 15 steps that need to happen to, you know, move this project from idea to execution, like then I can kind of move those onto the daily task list, if that makes sense.
It's interesting because what I do with my clients is similar but different with that, where I create this lifestyle by design. Where we do map out, we do plan out with intentionality, not 30 days, 60 days, 90 days, but even I'll go out 1, 2, 3, 4, 5 years out of where they want to be and reverse engineer it. Because, right, you can aimlessly wander. It's kind of like if you know, like, if you're going in a certain direction, but like you move yourself over a foot, but keep going in that direction, you're going to end up miles and miles away from where you were trying to get, right? But if you reverse engineer it and you know exactly what steps you need to take and when, right, then there's going to be a lot more success and you know you're not going to wander aimlessly. Consciously with tasks because there are key predictive indicators along the way. And I find that it alleviates a lot of the stress. It makes things a lot more simple. It gives you a lot more of a strategy. And you know, in a pretty binary way, whether you're on purpose or you're not on purpose.
Yeah, it is. It kind of forces you to, one, be grateful for what you have. And granted, we are not one of the 40 million people who are unemployed. So if you're in that situation, that's a different— conversation. And I understand that's like a brutal place to be. So, you know, we're incredibly fortunate. Like, that is not lost on us. But it makes you question, like, what, you know, where were you going before? Like, you know, this, this could be, this could be your life. And like, that would be totally fine. And how can you come to grips with being happy with that destination versus like always trying to chase the next thing? Like, we had a guest on the show Paul Jarvis wrote a book called The Company of One. He's like, why do all these companies— if you're not growing, you're dying. Like chasing growth for the sake of growth. Like, oh, you know, he's like, when I was younger, I wanted to have a million-dollar business. And then after 2 months, I was like, I don't need a million-dollar business. Like, why am I burning myself out working for this?
Right. But it becomes— I mean, at that— but if you think about it, like the business of one or that solopreneur mindset, at a certain point, you're still doing everything, and you've just created not just a job for yourself, but multiple jobs for yourself, but you're only getting paid at the level of one job, right? So that's where the challenge and difficulty thing is, unless it's something that's scalable and you yourself are not the product. But you still only have a certain amount of time in the day, and I, and I see that, right, especially as a small business owner where I know right now— and it's a big debate because my lease is up in, um, the end of June and And I'm like, do I keep my office? I'm fully online. I have another associate that's a therapist. She can be fully online, but I also have a chiropractor, right? In my office, 'cause we're a mind-body wellness practice. And my question is, is the headache of navigating that and worrying about that equivalent to the income that I'm making in, right? And bringing in. Versus having this identity now, right? Maybe it's time to pivot the brand of my practice. Maybe it's time to pivot, like, yes, I'm still working time for money on myself, but am I leveraging the amount of time that my associates are using the office in exchange for what the rent's gonna be if no one's going into the office in the first place, right? So, we're still always doing that, but I really also like the idea of what you're talking about, this passive idea of like making courses, making some type of training, doing something that you're able to be, you know, I have this belief that everybody needs a DRock that GaryVee has following him around, right? Everybody needs to have a documentary person following them around at some level, and if it's a college kid that you're doing, that you're paying, or whatever it is, you should be able to document some of your day if you're working in a specific niche. The challenge that I hear the most, and I would love to have your input on this as this brings me into this mindset, is how do you get out of the, "Well, I can pay myself or I can pay someone else, and I'm not making enough money right now to pay someone else, but I do really need that person to do it because if I do it by myself, it's not going to look so great." Yeah, this is definitely an existential entrepreneur question.
The chicken versus egg kind of a thing, right? Right. My, just speaking personally, my strategy has usually been to bootstrap as long as possible. And, you know, when is it time to hire? My historical answer has been when the pain of inaction is too great. Like, I just, I can't do this anymore. Like, it doesn't make sense. And that's kind of like, hopefully, hopefully by that point, the revenue justifies bringing somebody else on. Like, I'll give the example of the podcast, like, so 3 years into the show, um, my first son was about to be born, and, and an editor sent me, I think, a cold email pitch. It was like, hey, have you ever considered outsourcing the editing of your show? It's like, I haven't, but I am now, because now all of a sudden, like, these extra hours a week are going to be harder to come by. And thankfully, by that point, like, the show had gotten enough traction where it made a little bit more sense. Whereas I see other people take the opposite approach, like everything out of the gate, you know, they, and they tack on like some pretty significant overhead, like right out of the beginning. And it's okay if you're comfortable with that. But I mean, it was $15 a month to host the podcast. Had it been, I didn't know this was an expense that existed. Had it been $25 or $30, like the show might not exist. I was like, well, what am I signing myself up for? What if I don't like it? And you know, So I've tried to keep overhead intentionally really low. Other people are like, all right, I need a team for this. I need a professional web design. I need like, you know, I don't know. So I run pretty lean. When the pain of inaction becomes too great is when I tend to make a hiring decision. Lots of people have told me I need to level up and improve my, you know, add to my team. And then something like this happens and it's like, well, I don't have to lay anybody off. I don't have to It's just me. So there's definitely two sides. When I was running the shoe business, that's probably one of the mistakes I made was not scaling faster, recognizing in hindsight that the business kind of had a finite lifespan, whereas I was like, "Hey, I got time. I can do this stuff." So it kind of depends maybe what business you're in, what your comfort level is with spending.
Well, it's interesting. Until the pandemic started, for the last year, I committed to no longer doing my laundry by myself. And I realized—
You're just going to wear dirty clothes?
Yeah, that's it, right? I'm just going to wear it by myself. No, I was waiting for that nice little pause there. I'm no longer going to do my laundry by myself. And it's like that old joke, that old, like, let's eat, comma, grandma, right? The grammar is very important versus let's eat grandma, right? And I did the math on this. So if I do my laundry twice a month and it costs me average $17 to $20 whatever, to drop it off, have it washed, folded, and delivered back to me. I realized that it takes me two— it takes two client therapy hours to cover my entire year of laundry. So I have to work two hours, yeah, to do all the hours of laundry that I would be doing myself. Now think about it, if my laundry at home— because I'm in a, you know, building and have to go down the hallway, whatever— so let's say it cost me like 5 to $7 plus my time.
Yeah.
But if I can go see one client extra, right, that automatically covers 6 months of doing my laundry by myself, right? That was like when I broke it down to that, I'm like, okay, what other tasks can I now start seeing based on what I have to work for, what new client I have to get in order to now pay that? It's like Grant Cardone has that phrase of like, who's got my money? I'm not gonna buy my new shoes until I get the new client to pay for it. It's not coming out of my existing. Okay, come out of my new, right? I like that.
That's a really powerful way to frame it. And it's like, how can I, um, afford these luxuries? Or how do I kind of step up? How do I raise my expenses, right? You know, whatever expense is annoying you on your line item budget— your cell phone bill, your gym membership, probably not anymore, your whatever, Netflix, life insurance, whatever it is— like What would it take, extra income-wise, flip a product off of—
It's arbitrage, right? You're really arbitraging that. Yeah, and Gary Vee talks a lot about that. And it's so interesting right now, I have stuff on OfferUp that just like, as I'm cleaning out, and 4 months ago someone reached out to me on something, it's like a wah-wah pedal for my guitar that I haven't used in years. And I'm like, I'll sell it. It's brand new, I've used it 5 times. It's like, whatever, even though it's old, it's years old, but it's the same technology. They haven't changed the technology. There's no newer version of this pedal. And I'm like, ah, I'll put it up for like $10 cheaper than it's brand new, whatever it is. Someone reached out to me. I'm like, oh well, I might as well get it new for $10. Okay. This week they reached back out to me again, 5 months later.
I'm like, what happened to your $10?
For $10 you weren't willing to go and order it on that freaking Guitar Center, so you're now reaching out to me and you wanna drive down? But people— There are people out there, and this is what I don't get, 'cause at first I'm like, wow, I feel bad selling it at a marked-up price when they can go get it brand new for not much more. But people out there are willing to save $10 and drive 30 minutes each way to save $10.
Yeah.
And so sell your stuff. And I'm willing to do that for the, like, it's not my guilt anymore, right? It's not, I have to let that go. But I realized this when I created my podcast. The person who inspired me to create my podcast had an in-house social media expert, and that person was handling everything, including all the podcast editing and the video stuff. So when that person went solo from my friend's podcast and he started his own company, I was one of his first people that he reached out to. He's like, "Listen, low level, I'm gonna get you in, your ads can be this price," right? And I'm like, "Dang, that's really good." And I went to Podcast Movement this past summer. I think I had 2 or 3 episodes of my podcast released.
The Orlando one?
Yeah, the Orlando one.
Were you there? I missed it. I missed the last couple years. I went to like the first 4, but I missed the last couple.
Mass. I had no clue what I was getting myself into. It was like 3,000 people there. It was like crazy. I've never been to anything like this before in my life. And I met some really good friends subsequently from there. And everybody's talking about how they're spending 6, 7, 8, 9, 10 hours audio on one episode by themselves. And I'm like, you're crazy. I'm like, how much time, effort, and money are you losing by doing it yourself? But then I'm wondering like, are they not making money to the level of where it might cost— they're making, let's say, $15 an hour, but it costs someone $20 an hour to edit their podcast. So then they're losing money on the deal.
That was me for the first 2 or 3 years. Right?
So I wonder, like, at what— like, there is a price point. Like, if it's the same amount of money or less than what you can charge an hour, then it might be worthwhile that someone else get it out. But can you also scale by, like, you know, taking a dip? For a year in your income. Now I'm not talking about going broke, but can you give up $15,000, $10,000, $8,000, $5,000, not be freaking out, but to use that to scale faster and quicker, which is what you said, like, a lot of people I hear is like, wow, had I known how to do this, you know, therapists, I hear this all the time for billing, and I do my billing paperwork myself, and I'm having issues with getting insurance money back. For $2 a submission, have some billing program do it for you. Oh, I don't wanna pay $300 a month. But if you charge $150 an hour, how many hours— you just need 2 clients more a month versus the 8 hours a week you're spending on your billing, right? So I really help— I want people to get that number down in their mind of what that costs for them for whatever.
Yeah, and you brought up the, the E-Myth, but it's similar. Like, think of, think of the dentist. The dentist is like the world's greatest outsourcer, right? He's not answering his phones, he's not welcoming you when you walk in, he's not billing insurance, he's not even doing the cleaning. He's like they'll call him in to like do the final check and he's in the back like doing high-dollar root canals and like crazy stuff with like only he can do. And I'm— this is something that I've admittedly struggled with because it's like, it has to— it's faster, I'll just do it myself. But like to really kind of put on that owner's mindset rather than the operator's mindset, say like, okay, who is, who is best to perform this task? Is it going to be me? And early on, it's probably going to be you, right? Until revenue justifies hiring somebody. But as soon as it does, it's like, okay, I can farm this out. I can hire an expert for this. They're going to be able to do it better, faster, cheaper than me anyways. And they do this for 10 other clients, like they've got a system down versus me like trying to figure it out on my own.
You have to putz your way through it, which is like the biggest thing. And I think that really ties into like know what you're an expert at, right? If you're going to create a side hustle, one thing is like, what are you already— and I find this with my clients right now, especially during the pandemic, where they're talking about, "Well, I was laid off," or "I have this and that." What are you already passionate about that you can share with other people? You just have to put it out there. Like you said, just put it out there, document it, social media, go Facebook Live. We have a captive audience right now. People are literally 24/7 in front of their digital media because this is just what the world is. And I really do believe that as much as I have my boundaries around the time of day where I shut off and I do whatever I do. I'm still a therapist at 11 o'clock at night. So if I want to do a Facebook Live at 11 o'clock at night, it's not 11 o'clock at night everywhere in the world. Someone is going to catch— someone's going to jump on. It's lunch right now, and the people that have been jumping on and off the Facebook Live that we're doing while we're recording this is still— this is not the final edit of everything, but it is creating interest in both people to look up you and to see more of what's going on in my world. So there's ways of leveraging, and I want people to to hear that. Can we just go a little bit more into, just for the sake of what we're working on, of how do people start thinking about where they can go to create this side hustle? I know you have this amazing list on your website of all the things that you can do. What would be a natural question or questions that people can start asking themself in order to know where they should start ending up?
Sure. So one place to start is that expertise question. Like, what am I good at? What have I been paid to do in the past? By definition, like any job you've ever had was a skill somebody thought was worth paying for. So, you know, start there. Any skills you've learned outside of work, which, you know, hobbies, stuff like that. I'll put that down in column number 1. Column number 2 is, you know, what are you interested in? What do you like to do? What do you, you know, how do you like to spend your time? What do you get excited about talking about. Like in my case, you know, this part-time business ideas, like kind of reverse engineering, deconstructing business models was super interesting to me. Never got, you know, first 4 years of blogging, never got paid to do it, but it was like, wait, how does that— you know, it was just a nerdy thing that I did in my spare time. Like that was, that was a sign. It took me a long time to realize it, but that was a sign. Um, column 3 is kind of the optional column, and this is your network. This is who do you know, who do they know, and maybe more broadly speaking, not like listing out 500 names, but what types of people do you know? Like, and this is purely for a foot in the door, you know, conversation starters. Um, if you can find an intersection between skills, interests, and network, like I provide web design for chiropractors, or, you know, whatever it is, like if I can marry some level of these three different columns That would be one place to start. An interesting counterpoint to this expert model is, you know, one, you could document the journey on becoming an expert, which is like, I don't— I wouldn't say I was like the world's foremost side hustle expert 7 years ago, but through the practice of doing and interviewing and learning, like I've become, you know, maybe one of the few people who would be an expert in this field. But that's one where you don't have to start out as an expert. The other interesting one is I'm just reading this book called Start from Zero by Dane Maxwell. Dane runs the foundation. He teaches people how to basically build software companies from nothing. It doesn't rely on your expertise. It doesn't rely on you even knowing how to build software. It relies on listening. It relies on asking questions and figuring out What hurts? What is the pain point for not even customers, like just humans, right?
What's the problem that really needs to be solved in that segment?
Yes, like, what are you currently doing today? Like, well, you know, he's got a whole series of exact questions and like scripts and language to use, but it's like calling up business owners and saying, well, you know, what's the biggest challenge facing your industry? In the next 5 years? Or, you know, if you, if you could wave a magic wand, how would business look differently today? What's the biggest headache that you face when you come into the office every day? And it's stuff like that. You're just trying to get people talking, and you start listening. So, well, so, so how, how are you currently doing that? Like, you know, what's the current solution for that? What, what would make that better? What would make that different, faster, cheaper? And it's like Just try to listen. So if I'm hearing you correctly, it sounds like billing clients is a major pain in the neck for you. Like, how do you handle that today? Okay. And then you can just kind of, you kind of start to piece together a bunch of these different conversations and come up with a solution. It could be a product, it could be a service, but it's just, you know, it's based from listening, not your specific expertise.
I find it interesting that like there's so many things that people are already doing, but they're they're leaving crumbs on the table in a segment of what they're already doing that they don't even realize?
Could be possible.
And have you found that, like, as you're journeying through all this, that they're, like, if you're collaborating with a business owner and you throw a question at them and they're already thinking about creating something new, creating on the side, and you're like, but what about this in already what you're doing? How often do you find that? And they're like, oh crap, I never thought about that. Like, I didn't even think that would be like, because we're so stuck in this myopic view that, right? We're not— you know, it's the idea of like we need to bring someone else into our life to help us see the picture outside the frame, right?
And that's kind of where, you know, peer groups, accountability groups, mastermind groups can be tremendously valuable. It's like for me, I was like heads down, kind of in my cave, right over there, like on the treadmill desk, you know, just pounding out shoe ads all day long. And it was You know, not until getting some outside perspective of like, well, why are you doing it that way? And some of it came from people that I hired. They're like, well, did you know if you did it, you know, with 4 different tabs and these little text expander things, you could really accept— I was like, hmm, you know, I never, never thought of it that way. So of course, yes, that's a much better way to do it. Um, so I think you're right, there is the tremendous value in getting some outside perspective. And even more so is like you find like opportunities and conversations start to come up once you're in motion, if that makes sense. Whereas like if you're sitting on the sidelines waiting for this lightning bolt of inspiration to strike, you know, I need the perfect business idea, never been done before. It probably doesn't exist. And if it does exist, it might be too heavy for liftoff. And I've had, you know, a couple of those too where it's like, this is gonna be so awesome. Nobody's ever done it before. It's gonna be like, and then I don't know the next step.
And then 5 months later, someone else does the exact same thing. I remember when I was young, that was my idea, right?
Ideas, ideas, pretty worthless, right? Without an action, those ideas, execution. Yeah.
One of my mentors, Dr. Scott Walker, who had one of his favorite quotes is, um, the universe rewards the action step.
Yes.
Right. And I can tell you how many, especially when I was younger, like I would have like either a dream or like as if I'm so old, right? But when I was younger, when I was like, I don't know, high school or early 20s, I would have a dream about an idea in the middle of the night. I wouldn't write it down. I would forget about it. And a year or two later, I would see it show up in the marketplace somewhere. And I'm like, okay, that's really weird. How did someone else have this dream? And I'm wondering, on a spiritual level, is this idea being dropped into the world and who's going to pick it up first, right? Because nothing is new under the sun, right? And is there a universal energy energy of like, you know, the universe is ready, we're ready to receive this and it's ready to be brought into the world. Um, or is there just so many like-minded thinkers in the world that someone's going to come up with some type of right little thing? But I do want people to walk away knowing that like the more niche you can get to who is your ideal— one, who's your ideal person, but two, what is the reverse? Like why does that problem need to be solved? And how are you the best person to solve it?
Right.
Or how can you be the best person to hire the best people to solve it, which is really the better question to ask.
Right, if you don't want to get yourself caught in the, in the trap of doing all the labor yourself.
Yeah. So what's one thing that like you think people should absolutely completely stay away from, that they should absolutely not do? What's the no-go, like when they're thinking about all these different things? Like what's your like, okay, Do not pass go, do not collect $500.
Do not, uh, do not print business cards, do not invest in a logo, do not build a website. Like, seek validation first, like validation in the form of a paying customer, to whatever degree you're comfortable with. Like, you know, some, like, if you're building a physical product, like, it's going to be hard to pre-sell that, although people do it on Kickstarter all the time, right? There's There's something, and I'll get emails like, "Oh, I'm $30,000 into my website, it's almost live." I'm like, "Jesus, you don't have to do that." You don't have to be in debt. Yeah, do you have any customers? What are you doing? And I'll give you the example with the shoe business. The very first version of the shoe business, there was no website, which is weird for an affiliate marketing business. It was direct link text ads on Google AdWords. I don't even know if this is still a thing, uh, using my affiliate link, right? Would people click on my ad? Would they convert at a high enough rate such that it would be profitable? Okay, yes. Budget was $1 a day at the beginning. It cost $5 back in the day to set up your account. That was my, like, you know, as low of a startup cost as you're probably ever going to find. And then only once I had that validation, I was like, okay, now I think it makes sense, uh, having proven this out, to invest in having the website built. You can do it with products, you can do it with services, you can do it with digital products like, hey, sign up here for the presale, it's a special one-time thing. Because you don't want to spend 8 months building a thing that nobody wants. So I think that's probably one of the biggest mistakes to avoid that I see.
Yeah, I heard someone that they went— every time they have an idea, they buy the web domain name for it. But every year they have a renewal now for like, I don't know, $1,500, right? That they're like, Well, I'll use it one day. I'm like, that's a big expense. I'm like, what would it look like if you're gonna just arbitrage that and just sell one of those or two of those things that you know are way down on the trend, right? On that list of all those business ideas, rank them. And the bottom 5, just sell those web domains and maybe you'll make— Yeah. Right?
If they've aged now, you're—
Right, right, right. Is that still a good, is that still an industry that exists or is it like, you know, I had a buddy of mine who was selling fidget spinners a few years after they were already out but he sold it to a startup such a niche population for a very specific holiday. And they sold out. And I was like shocked, but I'm like, okay, can you do this every year? Like, is this something that was like a one-time thing? It's kind of like selling Crocs now. Ain't nobody gonna buy a pair of Crocs today. I don't know why, again, like I'm trying to figure out how they're still in business. But there is obviously a brand of people who are buying that thing. But can you go now and make your own version of Crocs and try to sell it? Is there a big enough industry? For that. So like, that's another thing to look at. Like, what's like, what's out there? What's your— who's the person doing that in some way, shape, or form remotely close to what you're doing? That would be either the example or the industry standard for it. And if there's not, the first question I would then ask after that is, well, why isn't there, right? Do you think it's really an issue or a thing that needs to be solved? And no one's like, okay, that's just what we do. Or you said like proof of concept, go test society, go ask a bunch of people, you know.
Yeah, it's almost like you got a question. Well, if it's such a great idea, how come nobody else out of 7 billion people hasn't thought of it yet, right?
Why isn't it been on Shark Tank, right?
Whatever. And another Noah Kagan soundbite when he was on the show was like, dude, how many sushi restaurants in your town? How many dry cleaners are in your town? It's not necessarily a super innovative business model. It's like, just, hey, we serve a different customer base, we do things a little bit differently, whatever it is. And like, the pie is big enough for more than one service provider to compete.
Right. And there's only so much innovation in that community, so it really does become what are the services. It's either service and value are really the only two things in that type of place you can compete in at this point, right, in that type of service industry or that type of, like, especially dry cleaning. What's the next technological advance that you can— how many people are going to want only want organic? How many people are going to want wash and fold? How many people are going to want delivery? But what's the next— the next thing would be maybe creating an app for your company so they don't even have to call you or pick you up. They have the app or there's some easier leverageable way to make it more simple for your clients to access. But there's only— but also know how much growth can there be? How much evolution is that in your industry? We're seeing it right now in the therapy world, right? We moved from in-house to to online and how years ago people would like, not even, I would say a year ago, people would shame therapists. How could you? You lose the face-to-face interaction, you lose the in-person thing. And like, we've clearly been doing it for the last 90 days. And now they're giving shame people going back into private practice. How can you put yourself at risk? How can you put your clients at risk? Like how quickly, just like that, right? For an industry that is, there isn't so much advance in my There's theory advance, but the business side hasn't advanced. And now, and so people are jumping on that entrepreneur lens. So there's so much that someone out there can say like, hey guys, I can help you reinvent this. I'm not a therapist, but I can help you do this if you get unstuck from the— and there's that in any industry is my guess.
Yeah, I think you're right.
So cool. So if there was— and we'll wrap it up with this— if there was one thing, and this is my On One Foot question, that when you meet someone and you know you only have 2 minutes with them and you can kind of want to like distill, here's my experiences, here's what I know, here's what I want to leave you with, and I know I'm never going to talk to you again, like what would you want to share with that person?
That's interesting. I don't think anybody's ever asked me that before. I think I'd probably want to share that you can figure this out. I remember when I was in college and my wife, my girlfriend at the time, I was thinking of taking this college painting internship and mine was with College Works Painting. There's a handful of competitors. And I was like, it's one of these things where they don't tell you it's painting, right? They get you excited. Do you want a paid summer internship where you learn entrepreneurship and sales and marketing and customers? This sounds fantastic. And then like you're 3 steps down the process and they're like, by the way, it's painting houses. Um, it was like, well, is this a pyramid scheme? Is this a scam? Like, and she's like, you know what, it's 3 months of your life. If it sucks, it sucks. You can figure it out. It's not life-threatening. You know, you move on, move on with your thing. Um, but that's been really helpful to me, like that constant, you know, you're gonna have challenges, but you can figure it out, right? The vast majority of the things that you are going to face challenge-wise are not life-threatening, thankfully. Like, gone are the days of saber-toothed tigers and stuff. So it's like, okay, we can figure this out. You've got the entire library of human knowledge at your fingertips at all times. It's there, the resources are out there. It's not a lack of information, it's kind of a lack of action and, you know, putting the steps in order, if that makes sense.
Absolutely. So yeah, so I'm hearing you say like, if you have the idea brainstorm it, but then put it into motion. Otherwise, it's the idea without any action. It's just a thought. And I really do believe in that. So for people out there who are listening, The Side Hustle Show podcast, where like you said, you've had all these really awesome entrepreneurs coming in. And as I'm looking through the list of people, like, it's just, they're so cool, right? How to become a bookkeeper, make $70 an hour from home. How can you trade stocks and make $1,000 a day as a day trader? These are just some of my LinkedIn lead generation— like there's pretty much every single thing and you break it down by category which is really awesome and brilliant so you can dive right into wherever someone is looking for based on a vertical on that. So it's amazing that you laid it out that way and then your website is sidehustlenation.com? Is there any other ways they can track you down and follow you or those— That's the main one?
Those are good spots. Of course, we'd love to have you tune into The Side Hustle Show. If you are in the position of looking for a side hustle idea, sidehustlenation.com/ideas is my constantly updated laundry list of those. My hope is you get down to the bottom of the page, you got 8 or 10 different browser tabs open like, "That sounds interesting. I could do that. I gotta learn more about that." Definitely a good place to start just to get the creative juices flowing.
Awesome, awesome. Nick, thank you so much for hanging out with us today. And really guys, everybody out there, like if you have a spare right now, this is the perfect time to start thinking, what can I have as a fun side hustle that's exciting, that's uplifting, that brings you more income, that can maybe even do something you can do with a friend and a loved one and all those different things. Again, Nick, thank you so much for hanging out today.
You bet. Thanks for having me.
Of course.
Thanks for listening to the You Winning Life podcast.
If you If you are ready to minimize your personal and professional struggles and maximize your potential, we would love it if you subscribed so you don't miss an episode. You can follow us on Instagram and Facebook @JasonWasserLMFT 🎗️
More from Jason

Howard Behar Starbucks Former International President Heartwarming Story #kindness #shorts









