732: 24 Years of Side Hustle Advice

0:00There's a side hustle that's exploding right now, and that's live selling on Whatnot. I've seen Whatnot climb to the top of the app store. I've seen the seller earnings, everything from small part-time projects to multi-million dollar businesses. Whatnot is the largest dedicated live shopping platform. Whether you're selling beauty products, collectibles, electronics, thrift store finds, luxury fashion, even food products like cookies, sellers are building real thriving businesses. So how about this? People selling on Whatnot sell 10 times more than on other major marketplaces. That's because you're not just listing products and hoping somebody finds them.

0:37You're building real connections with buyers. And those buyers, they're spending more than an hour a day in the app. They're not just browsing. They're bidding, they're buying, and they're coming back. You go live, show off your products in real time, and then turn what you love into real income. And for a limited time, Whatnot is matching your first$150 sold in the first month. Visit whatnot.com slash sell to start selling. That's W-H-A-T-N-O-T dot com slash sell. whatnot.com slash sell. 24 years of side hustle advice in 41-ish minutes, starting with your driving motivation. A lot of people approach side hustles from the standpoint of, well, I want to make extra money.

1:19But what you need to do is kind of put yourself in the shoes of that annoyingly curious five-year-old and ask why. And then ask why again. Well, why do you want to make extra money? Well, I need a little extra breathing room in my budget. You know, that would make life a little more comfortable. Well, why? What do you want to do? Well, I want to pay off some debt. I want to maybe go on this family trip. Well, why? You know, well, maybe eventually I want to be able to quit my job and be in more control of my calendar. Well, why? Well, I really value having autonomy over my time. And you start to drill down and you get more and more honest with yourself on why it's important to you.

1:56What do you really want and value? Because this is going to keep you going when times get tough in your side hustle. It's like, you see, it's hard. If it were easy, everybody would be doing it. And I think it's really important to know that driving motivation. Otherwise, it's too easy to throw in the towel. And when you find a side hustle idea that strikes your fancy that is really inspiring, you got to understand that inspiration is temporary. So do everything you can to build some positive momentum as quickly as you can before that inspiration expires. Maybe that's registering that domain name.

2:32Maybe that is making an offer. Maybe that is putting a product up for sale. Whatever it is, like taking important action, because I think you'll find momentum breeds momentum and momentum breeds results and results It's kind of a virtuous cycle in that way. And so just recognize inspiration has an expiration date. And if you can take action before then, I think you're going to be quite a bit better off. And if you don't take action in time, also recognize, look, business ideas are like buses. This is the Richard Branson line. There's always another one coming along. So don't stress if you missed the boat on one because there's always something else coming along.

3:08When it comes to coming up with business ideas in the first place, you got to ask yourself, well, what are you obsessed with? And the reason I bring this up is it's hard to compete with somebody who's obsessed. Now, give the example of, you know, credit card points and miles. Like, I like playing this game. I like signing up for new credit card bonuses. Traveling for free is a fun little life hack. But if I were to compete in this space as a content creator, I'm never going to compete with the points guy, with all the hacks, the people who really live and breathe this stuff day in and day out.

3:41Now, where I can compete, what I have been obsessed with for the last decade plus is side hustle ideas, right? This was the same, kind of the same questions that I asked early on. Well, what do you never get tired of talking about? Well, I really love deconstructing these business ideas and finding and sharing creative ways to make extra money. That really lights me up. I mean, it still does today the way it did 12, 13 years ago. There's a lot of advice around following your passion, but I would argue if you don't have something you're undyingly passionate about and going back to the obsession thing, maybe you can follow your curiosity because this is kind of what drives a lot of the content in my case as well.

4:18I'm curious, what would happen if we tested this? Or what would happen if we did this experiment? Like one example, just recently I published an episode that was generated by AI and it was universally panned. The audience didn't love it. I thought it was super cool. I was excited by it. I found these side hustle case studies and stories, fed it into Notebook LM. It came back with this cool 17-minute back and forth. It was an experiment. The crowd has spoken. It wasn't a winner. So back to the drawing board on that. But it was something I was curious to play around with. And so if you can follow your curiosity and kind of be testing different things.

4:56I read at one point that Amazon is testing at any given point like a thousand different variables on their website trying to eke out another 0.01 % conversion rate or something. Because at their scale and volume, that would be a significant bump to the bottom line, every little micro percentage. I don't think you need to go to that extreme, but you can kind of run these little experiments, these tests in your day-to-day life. Well, what would happen if I did this? And it kind of gives yourself permission to take a swing and say like, oh, if it doesn't work, it was just an experiment. And similarly, I had to shut down my Facebook content monetization experiment last month, just because it was like, well, for the time that I'm putting into this, the results aren't what I would be hoping to get out.

5:41It's like, okay, hey, you gave it an honest try. You gave it the experiment. It didn't work. It was following that curiosity. If I ever come around with coming up with a kid's book, it would be, mommy, where do business ideas come from? And the truth is that business ideas or money comes from solving problems, right? A business is just a repeatable system for solving a problem. So if you can put yourself in that mindset, like early on, I probably Googled, like a lot of us have, you know, ways to make money online. And what a lot of these listicles that you'll find, and I've written some of them myself, they kind of dance around the issue of, well, the real money comes from solving problems.

6:20And I kind of stumbled into that with my first side hustle, or my first online side hustle was this comparison shopping site for shoes where it started for the noble purpose of, well, how do I make money online? But the end result was it was a helpful tool. It was a helpful website to help people find the best price on their next pair of shoes. And that's why it worked. So money comes from solving problems. Another thing we talk about quite a bit on the show is the idea of pain pills versus vitamins. And I think it is quite a bit easier to sell pain pills than it is to sell a vitamin. Because if you think you've got this splitting headache, you're going for the Excedrin, you're going for the Tylenol right away versus, hey, if I forget to take my vitamin today, it's probably not the end of the world.

7:03Like what's that expensive problem? What's that driving pain that you can take away from customers and solve that kind of problem? Early on, a friend of mine gave me this line. He called it the rule of the internet. He said people are only ever online for one of two reasons. Number one, to solve a problem. Boom. I think that's easier to play in. And number two, to be entertained. And if you are very entertaining, you can still play in that space. But you're competing against Mr. Beast and ESPN and HBO and like all of this stuff versus if you can solve a very specific problem for a very specific customer, I think it would be much easier to find an audience and start making money that way.

7:39One thing that comes up a lot is the idea of competition. Well, somebody else is already doing my idea. Somebody else already came up with it. Somebody did it first. And so Jonathan Ventanza from ChooseFI gave me this line on the show. He said, if you can't be first, be different. In his case, he was talking about the financial independence movement, early retirement. Like, look, there were already dozens of blogs talking about this, but there were very few podcasts. And so ChooseFI kind of filled that podcast void for that early retirement community. And I'll add the corollary to that. If you can't be different, be better, right?

8:12This is how the internet overall improves in quality, hopefully over time, because, well, Somebody else had the same idea, but I can do it better. I can kind of leapfrog what's already been created. And you see this in physical products all the time where it's like, oh, this already exists. Shoot. But here are some little tweaks, little improvements, little iterations that we can make to that to improve it over time. And I've done the same thing with website articles. Oh, shoot. Somebody already wrote this idea. You know, back to the drawing board. It's like, oh, wait, I can still add my own unique approach to this.

8:44I can be different. I can hopefully be better. So if you can't be first, be different. If you can't be different, be better. There's this proverb that talks about when it comes to chasing business ideas about this lion on the African savanna and says, well, it could either spend its time chasing antelopes or chasing mice. It's going to take the same amount of effort either way. One is going to feed him for a week. The other is going to still be hungry afterwards. And so I wanted you to think about this when you're evaluating different opportunities, different business ideas. like, are you going after the antelope idea or are you going after the mouse idea?

9:17Like, even if you work, if you succeed, if you catch the thing, is that really going to be worth your time? So the question is, you know, what if this works? We spend a lot of time talking about how to minimize failure, you know, minimize risk. And I think all of that is important. But you also have to ask yourself, well, what if it works? And if it does, would that be a win for you? And the way to do that is to look at somebody who's done it before you, who's three or five years ahead of you and say, well, what does their life look like day to day? Are they still putting in 80 hour work weeks or do they have a little more freedom and flexibility?

9:56Is their income where you would want it to be? And kind of evaluate different side hustle options based on what if it works? What if the thing takes off? And is that going to be a win for me? The idea here is to make an asymmetric bet or several asymmetric bets because the first thing that you try may not work and that's okay. But if I minimize my downside risk and swing for the big enough antelope or the big enough upside, then that's going to erase all my losses and I'm still going to win. So look at those side hustles or those business ideas in terms of what has an asymmetric upside. And I think that's the side hustle mentality in general.

10:34There's this connotation of some entrepreneurial upside that separates it from taking a second job, bartending on the weekends, delivering pizzas, driving for DoorDash, stuff like that, where there's a path here where I can go beyond hours for dollars if I do this right. One phrase that I have tried to remove from my vocabulary is, I don't have time, or I didn't have time. And what I've been trying to replace that with is the more brutally honest, I prioritized something else. Because we vote our time with our priorities. And we're all dealt the same number of hours in the week. And your week might look different from mine.

11:12But there is some level of truth to that. We have to look in the mirror and say, well, what did I prioritize? Did I prioritize watching Netflix? Did I prioritize doom scrolling social media? Did I prioritize spending time with my kids? Like, nobody's going to fault you for that. But you need to be honest with you and stop saying, I don't have time. The time is there. But you got to figure out the priorities. And maybe the helpful framework that I've heard is kind of think of the bookends of your days, first thing in the morning, last thing before bed, and try and carve out some level of consistency.

11:43Maybe it's 15 minutes, maybe it's half an hour, but doing it and being dedicated and deliberate about it and try to move the ball forward on your own agenda, on your own proactive stuff before reacting to other people's problems and putting out fires and dealing with the rest of life's responsibilities. The time is there if you dedicate to it, if you really make it a priority. More hard-won side hustle advice coming up right after this. When you're a small business, the right hire can be make or break. Hoping the right people see your job posting isn't the best growth strategy. When the pressure's on and you need the right hire, this is a job for sponsored jobs.

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13:02Just go to Indeed.com slash podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com slash podcast. Terms and conditions apply. Need to hire. This is a job for Indeed sponsored jobs. So last month, it was time to replace the air filter in the car, which is about the level of vehicle maintenance I'm qualified to do. So I Google up the part number, I find this random store that is selling it. And then to my absolute delight, I see that they're running on Shopify. How could I tell? That little purple shop pay button at checkout. It meant not having to create yet another new account.

13:38It meant not having to find my wallet. I am paid and checked out in just a couple clicks. You already know that our sponsor Shopify is the commerce platform behind millions of businesses around the world, including that car parts website and dozens of side hustle show guests. And you probably already know about the built-in store templates and marketing tools that make it easy to get your store online and get found. But what you might not know is that Shopify can also help manage your inventory, ship products internationally, and even handle customer returns. On top of that, you've got access to their award-winning 24-7 customer support if you have any trouble.

14:10So let's see less carts go abandoned and more sales going with Shopify and their ShopPay button. Sign up for your$1 per month trial today at shopify.com slash side hustle. That's shopify.com slash side hustle. One more time, it's shopify.com slash side hustle. Okay, let's say you've got your side hustle idea now, and it comes to kind of this validation stage or testing phase. And I want to share this phrase, bullets before cannonballs, which comes from the book Good to Great by Jim Collins. And he talks about these companies, when they have a new initiative, they have a new idea, they want to test it on a really low risk calibration stage.

14:52This is the firing bullets, like low cost. Okay. You can buy a box, but get them by the dozen, right? And you're going to kind of calibrate, calibrate. Okay. Boom. We hit now that we're lined up. That's when we're going all in. That's when we're going to fire the cannonball. In my case, this was, you know, direct link text ads on Google ads for a budget of a dollar a day starting out. Those were my bullets before I felt comfortable investing in having this whole shoe shopping website built out. That was the cannonball. So what is it in your side hustle, in your business idea where you can kind of find the low cost validation before going all in?

15:30For a lot of people, there's this hesitation to get going. Well, I don't know enough. They have this imposter syndrome and it never really goes away. The only cure for imposter syndrome is doing the work. So I want to propose this idea of just-in-time learning. This is not knowing everything that you could possibly ever need to know about the thing, but knowing just enough to take step one and figuring out step two through ten as you go. In fact, there's a whole book on the shelf behind me from Pat Flynn called Lean Learning, which talks about this exact idea. You almost don't want to know what you don't know, and you just want to know just enough to do the thing.

16:09And then when the next, you know, you're going to bump up against the ceiling of your ability or the bump up against the next problem and hurdle. Okay, I'll figure it out then. And have the confidence that you are able to figure it out. This is probably the most important skill for entrepreneurs is the skill of learning new skills. It never really goes away. So this idea of practicing just-in-time learning has been really helpful for me. The other important thing is that you've got to get started before you can get good. In Arnold Schwarzenegger's book, he talks about this idea of reps, reps, reps.

16:43And that one really hit home for me because I feel the same way with the Side Hustle show. Whereas, you know, 50 episodes before I've felt more comfortable behind the mic, it was reps, reps, reps, putting in the work, being maybe a little bit cringe and trying to improve your craft. The other thing that stood out to me in that book was, you know, for weightlifters, for bodybuilders, failure is 100 % normal. It is a daily occurrence. We have to train to the point of failure to build the muscle that we want. And that one hit home for me because it's like we kind of shy away from failure. But in certain fields, like, no, that's just a part of the game.

17:21It's like a ticket to entry in a way. And so looking at failure not as, you know, I'm an abject failure. It's just, well, that little thing failed. and I know I'm going to be stronger because of it, because I'm going to take the lessons into the next thing. When my brother and I were kids and we'd be helping dad out with projects around the house, he would give us permission to help out and hammer in nails here and there. And he had this line, it's not a piano. And what he meant by that was it doesn't have to be perfectly aligned. If you bend a nail, if you give him a little dent in the wood, it's not the end of the world.

17:54And that stood out to me. It's not to say he didn't care about quality, cared about doing a good job for sure. But it was the idea that perfection is the enemy of good enough. And I think back to that first shoe site and the idea of that first version of the site. I'll see if I can bring it up on the Wayback Machine. Not the greatest looking thing, right? It's kind of like, well, I'm a little bit embarrassed to show people when they ask about my side project. And it brings back this Reid Hoffman line of, well, if you're not embarrassed by the first version of your product, you launched too late.

18:21So keep that in mind. Perfection is the enemy of good enough. You can kind of improve as you go and you'll learn as you go. When it comes to marketing your product, one of the most common themes on the show is to go where the cash is already flowing. We've called this the buy buttons theory. Where are the platforms where you can put your buy button and make it easy for customers to do business with you? Comes for services, comes for products. And in terms of services, we've seen people kind of shortcut the marketing channels by going direct to these kind of strategic referral partners. So the marketing question you have to ask is, who are my target customers already doing business with?

19:01I think this was first introduced to me by Daniel DiPiazza years and years ago, where he had this tutoring business. And he was working for this tutoring company, making 18 bucks an hour. Meanwhile, they're charging the customers like 100 bucks an hour. So he's like, well, what if I put on this, group class about SAT prep or something. So he goes to these guidance counselors and hands out flyers and markets this class and fills up the seat, 30 seats or something at his same, I forget what his rate was, but it exploded his hourly rate from$18 an hour to$1 ,000 an hour for that three-hour session or whatever he was doing this test prep thing by kind of going direct to the source.

19:41So we think of the lead fountains, who are the steady stream of people my customers are already doing business with, how can I get in front of them in a helpful or complimentary way where it's like, we're not competitors, but we could help each other out. Another example was Carter Osborne. He had a college essay admissions consulting business, and his strategic partner, the one that kind of took off the business was somebody who was a broader college admissions consultant person who just didn't like doing the essay work. So he became kind of almost a white label partner underneath her business.

20:18So that was really cool. My wife has done this in her photography business where it's just the wedding venues where their brides, the brides being their target customers, but the wedding venues are kind of the strategic referral partners here. Well, what does it take to get on your preferred vendors list? Well, we need to see your portfolio and proof of insurance. In some cases, it was really that simple. So again, think of those buy buttons where how can you get in front of your target customers. In the case of the Side Hustle show, it was guesting on a lot of personal finance related podcasts where the common themes were saving and budgeting and frugal living.

20:52And it was fun for me to come on and be like, well, let's talk about the revenue side of the equation. How can you increase the income? What are the creative ways you can do to make extra money? And that really resonated with that audience and helped me grow the show. Similarly, we talk a lot about filling demand versus creating demand. This is kind of the online business equivalent of skating where the puck is going versus trying to create demand from scratch. And so this is practicing good search engine optimization. This is kind of figuring out, well, what are people looking for that I can help out with versus trying to like, well, I came up with this cool idea for this brand new thing that nobody knows exists.

21:34And I don't know. I mean, it's really, it's cool if you can do that. That's kind of the Steve Jobs and the Henry Fords of the world, but for side hustles or side hustles in particular, probably easier to try and get in front of some demand that already exists. And that's why you hear so many guests reference, oh, I use this keyword research tool to find, oh, it had this search volume, it had this level of competitiveness. And that's what I was going to go create my product about, or that's what I was going to create my content about, my video, my article about to fill that existing demand versus, you know, what I did for years and years in the early days of the site was like, I'm going to write the article that I want to write, paying zero attention to SEO and getting close to zero traffic as a result.

22:16So don't do what I did and try and get in front of that demand in a more strategic way. As you're building your business, there's this tendency to all of a sudden see all the different potential directions you could go, the shiny objects that are out there. And from my seat as the host of the Side Hustle Show, it's especially dangerous because that to me is the mark of a good episode when I hang up the call being like, well, dang, how come I don't have a billboard on the side of the highway? Or why don't I have a vending machine route? Or I could probably start that business. If I'm saying that, I know it's going to be a hit, but it can be dangerous too.

22:49And so the advice for side hustlers is this idea of simplicity first, diversification second. Find one offer, one marketing channel, one target customer that's working before you go out and expand into channel number two, offer number two, et cetera. We had the advice from Brian Feraldi recently. It is better to be excellent at one platform, and in his case, he started with Twitter or X, than it is to be mediocre at 10 different platforms. There's a lot of pressure to, you know, quote unquote, be everywhere and cast a wide net. And with AI and content repurposing, like you can do it, but I don't know if you can do it well.

23:27And so his advice was like, look, master the first thing, get it working, get it spinning in your favor, and then go do that for a second platform, do that for a third platform. One thing that it took me a while to realize was, look, nobody else is going to do it for you. I would have items that would sit on my to-do list soon after quitting my job and becoming a full-time entrepreneur. It would sit on my to-do list and it would be there week after week after week. And eventually it kind of hit me like, dude, it's on you to move this thing forward. Nobody else is going to do it for you. And that is both the appeal of entrepreneurship.

24:04I want to call my own shots. I want to be my own boss, but also the realization of now I got to call my own shots. Nobody else is going to come up with my priority list and I got to do it. If I want to make progress, it's going to be on me. And for some people, that can be a real challenge. I was at this conference early on, and this was for the shoe business where the speaker gets up and he starts talking about outsourcing and delegation. And the punchline is really to work on your business instead of in it. So yes, nobody else is going to do it for you, but there's also probably stuff that you don't need to be doing yourself.