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732: 24 Years of Side Hustle Advice

39m 32s

732: 24 Years of Side Hustle Advice

The transcription highlights the explosive growth of live selling on Whatnot, a platform where sellers can earn significantly more by engaging buyers in real time compared to passive listings. It then shifts to broader side hustle advice, emphasizing the importance of understanding your core motivation to sustain effort during challenges. Success comes from acting quickly on inspiration, focusing on solving painful problems for customers, and leveraging curiosity. Entrepreneurs should test ideas with low-cost experiments before fully committing, adopt just-in-time learning, and view failure as a normal step toward improvement. Perfectionism should be avoided; launching an imperfect product and iterating is key. When evaluating opportunities, consider the potential upside and whether the outcome justifies the effort. Finally, effective marketing means meeting customers where they already spend, and competition can be addressed by being different or better, not necessarily first. Time management is reframed as a matter of priority, not availability.

Transcription

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English
There's a side hustle that's exploding right now and that's alive selling on what not. I've seen what not 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. But what not 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 what not sell 10 times more than on other major marketplaces. That's because you're not just listing products and hoping somebody finds them, you'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, what not is matching your first $150 sold in the first month? Visit whatnot.com/sell to start selling. That's WHATNOT.com/sell. Whatnot.com/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. But what you need to do is kind of put yourself in the issues 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? Well, I want to pay off some debt. I want to maybe go on this family trip. Well, why? 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. What do you really want in 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 people 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. Maybe 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 kind of is 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. These are always something else coming along. When 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 credit card points in 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 point sky, with all the hacks. The people who really live and breathe this stuff day in and day out. Now 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. Like 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 go 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. I'm curious. What would happen if we tested this or what would happen if we did this experiment? Like one example, just recently I had 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 like 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, I 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.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 done 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. And it's like, okay, hey, you gave it a non-istry, you gave it the experiment, it didn't work. It was following that curiosity. If I ever come around 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. 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 in 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. And I kind of stumbled into that with my first online side hustle. It was this comparison shopping site for shoes, where it started for the noble purpose of, how do I make money online? But the end result was it was a helpful tool, 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 et cetera, and 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. Like, what's that expensive problem? What's that driving pain that you can take away for customers? And it's all 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. 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 a fine audience that start making money that way. One 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 this. Somebody did it first. And so Jonathan Vintanza from Choose If I gave me this line on the show. He said, if you can't be first, be different. In his case, who's talking about the financial independence movement, but really retirement, they're like, look, there were already dozens of blogs talking about this. But there were very few podcasts. And so Choose If I 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. This 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. I'll shoot somebody already wrote this idea. Now, you know, back to the drawing board. It's like, oh, wait, I can still add my own unique approach to this. I can be different. I can hopefully be better. So if you can't be first, be different. There's this proverb that talks about when it comes to chasing business ideas about this lion on the African Savannah. It says, well, it could either spend its time chasing analogues or chasing mice. It's going to take the same amount of effort either way. One is going to feed them 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 analogue idea or you're going after the mouse idea? Like, 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 spent a lot of time talking about we had a minimized 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, you know, three or five years ahead of you and say, 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? Is there income where you would want it to be 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, you know, the side hustle mentality in general. There's this connotation of some entrepreneurial upside that separates it from, you know, taking a second job bartending on the weekends, delivering pizzas, you know, driving for a door dash, stuff like that, where there is a 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 just your week might look different from mine. But 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 doing 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. Maybe 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 one, 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, response, or jobs. 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Try Quote for free plus get 20% off your first six months when you go to Quote.com/scithustle. That's QuoteQ-U-O.com/scithustle. Quote, no missed calls, no missed customers. Okay, let's say you've got your side hustle idea now and it comes to kind of this validation stage or testing phase. I want to share this phrase, Bullets Before Cannonballs, which comes from the book Good to Great by Jim Collins. 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. This is the firing bullets. Low cost, okay, you can buy a box, you can get them by the dozen, right? I'm going to kind of calibrate calibrate. Okay, boom, we hit. Now that we're lined up, that's when we're going to fire the cannonball. In my case, this was 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? For 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. You just want to know just enough to do the thing. Then when the next, you're going to bump up against the ceiling of your ability or the bump up against the next problem in 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's Fortune Eggers book. He talks about this idea of reps, reps, reps. And 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. It's like a ticket to entry in a way. And so looking at failure, not as, you know, I'm an object failure is 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. Well, 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 get him a little dent in the wood, it's not the end of the world. And that stood out to me. It's not to say he didn't care about qualities 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 that that first version of the site, I'll see if I can bring it up on the way back machine. Not the greatest look at thing, right? It's kind of like, well, him a little bit embarrassed to show people when they ask about my side project and it brings back this read Hoffman line of, well, if you're not embarrassed by the first version of your product, you launched too late. So 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 button theory. What 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? I think this was first introduced to me by Daniel D. Piazza 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 a hundred bucks an hour. 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. So we think of the lead founds 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 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 was somebody who was a broader college admissions consultant person who just didn't like doing the essay work. So you became kind of almost a white label partner underneath underneath her business. So that was really cool. My wife has done this in her photography business where it's just the wedding venues where the brides are being their target customers, but the wedding venues are kind of the strategic referral partners here. 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 guessing on a lot of personal finance related podcasts where the common themes were saving and budgeting and frugal living. And 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? How can you-- 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-- well, I came up with this cool idea for this brand new thing and nobody knows exists. And I don't know. I mean, it's really cool if you can do that. That's kind of the Steve Jobs and the Henry Ford's 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, I had this search volume. I had this level of competitiveness. And that's what I was going to go create my product about. And that's what I was going to create my content about my video, my article about to fill that existing demand versus what I did for years and years in the early days of the site was, I want to write. 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. So 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, 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. And 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. For all the recently, it is better to be excellent at one platform. And in his case, you started with Twitter or X, then it is to be mediocre at 10 different platforms. There's a lot of pressure to, quote, unquote, beat 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. And 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, quoting 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 kind of hit me. Like, dude, no, 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. I 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. And so if you can build the recipe, if you can build the repeatable process, somebody else could take that off your plate. And I'm super grateful for the sign-assonation team members at this point. In fact, this spun off a whole separate business of mine is called Virtual Assistant Assistant that ran for nine years, like 2011 to 2020. And it was the idea, well, I need to help in the shoe business. And I had some curiosity and questions around, well, how do I hire somebody? I don't really want somebody coming over and working at my kitchen table. I've heard of these remote outsourced companies, but are they legit? Are they going to steal my ideas? I had every question in the book. How does it work in terms of taxes? So creative this directory that was kind of a fun ride to be on the growth curve of the outsourcing industry. But the main idea is if you find yourself working in the weeds day after day, kind of in maintenance mode in the business, is like trying to elevate yourself, trying to like take a moment to sharpen the saw and set the chopping down trees to work on the business rather than just in it to be the business owner and not just the business doer. And when it comes to selling your product or service, don't sell the product or service. You got to sell the transformation. That's what customers are really buying. How is it going to make them feel? How is it going to make them be a different person after the end of consuming your product or service? Like how is it going to remove their pain or improve their life in some way? This comes from my friend, Jack Hopkins, from Piano in 21 Days, where he's like, the product is this piano course, learn how to play piano. But the transformation is, oh, in three weeks, you're telling me I can learn how to play my favorite songs on the piano and impress my friends at parties. And that sounds really cool. And because of that, he's able to command like $500 to $1,000 for this piano course. It's a really, really cool idea of selling the transformation and not the product. Maybe you've seen the example of like the old school Mario video game where the product is the mushroom. But the transformation is, oh, now all of a sudden, I can jump higher. I'm twice as tall. I can break through bricks, right? It's like, what is the transformation of the Mario product is really offering? Another marketing lesson that I want to share is that businesses often live in this difference to the spread between lifetime value and the cost to acquire a customer, LTV versus CAC. And as you spend more and more time in your business, you're going to get a better sense of, well, what is the lifetime value of my customer? Is this a one-off purchase? Is this a recurring service that they're going to buy month after month after month? In which case, we had a pooper scooper business on the show recently. We said his lifetime value of a customer could be as high as $3,000, because it's a very sticky service, like as long as that dog is doing his business in the backyard, and they get used to paying for your service. They're going to keep coming back week after week after week. And so if you could acquire customers for way less than $3,000, kind of the spread is where your profit lies. And you can kind of, if I can acquire a $3,000 customer for $100, I'm going to make that trade all day along through meta ads, through Google ads, through referral relationships, whatever channel that you want to do, who's seen it in e-commerce as well, where it's like, OK, my product sells for $35, people on average by a new thing every six months. And so the LTV is $100. So we go out and acquire customers for $20. We'll make that trade all day long. So this is kind of a call to get a better understanding of your unit economics and the numbers. Kind of that drive your business in terms of what is-- what's a customer really worth, not just in terms of revenue, but in terms of profit margin on that as well. The next idea that I want to present is if there is a shortcut, it's mentorship. This is tapping into the knowledge of somebody else who has walked the path ahead of you. Because you can absolutely learn everything that you need to do on your own, through trial and error, through consuming content, through figuring it out. I think that's a really important skill. But if there's a shortcut, it's mentorship. I've seen this from so many guests where OI invested in this person's course or I bought into their program. And I accelerated my learning curve. That's what it is. It's an accelerated way to figure something out and get it done. And I was hesitant to do this for a long time. Being a very frugal person, it's like, I don't know. I could probably figure it out. And it's like, OK, once I've realized, like, no, you could save months off of your timeline by just following somebody else's recipe and tapping into their expertise. It's a much faster way to go if you have the means to get that done that way. And sometimes mentorship can even come for free. You had a guest on recently who called LinkedIn message, the CEO, founder of Petsmart. He had a Pets product business. And a couple of weeks later, he gets this call out of the blue from a phone number. He doesn't recognize it's like, hey, this is Jim from Petsmart. I got your note. And it was like, wow, some people really are willing to give back in that way. So I thought that was really cool. More hard one side hustle advice coming up right after this. 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. 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? Well, that little purple shop pay button at checkout. It meant not having to create yet another new account. It 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. So let's see less carts go abandoned and more sales going with Shopify and their shop pay button. Sign up for your $1 per month trial today at shopify.com/side hustle. That's shopify.com/side hustle. One more time is shopify.com/side hustle. Running a business is hard. If it were easy, everybody would be doing it right. You've got a to-do list, am I along and you got a dozen different hats to wear. So here's a resource to help lighten your load. I'm excited to partner with Gusto for this episode because they've been one of the most recommended services by side hustle show guests. Gusto is the easy, affordable online payroll, HR and benefits tool for modern small businesses. In fact, they help over 400,000 businesses like yours take the pain out of tasks like payroll tax filing, direct deposit, health insurance administration, 401k benefits, onboarding tools and lots more. Of course, I encourage you to do your own due diligence, check out their reviews online and I think you'll find the common threads in the comments about how easy it is to use their great customer support and the great value. So here's the deal. To help you get started or to make the switch, side hustle show listeners can try Gusto today at gusto.com/side hustle and you'll get three months free when you run your first payroll. That's three months of free payroll at gusto.com/side hustle. One more time that's gusto. G-U-S-T-O.com/side hustle. One line that was given to me early on in the show, probably in its second year, was this idea that opportunities become visible once you're in motion. At the time, I dismissed it as a little hippie-woo-woo kind of stuff, but I've seen it come through over and over and over again. It's this idea that action breeds action and action breeds conversations you improve your network and that idea, that conversation with somebody else sparks this next idea. Going back to the virtual assistant business, I was working on a completely unrelated side project in the wine space, which I had no business being anything about wine, don't really drink wine, don't really care anything about wine, but it was, you know, for whatever reason, that's where I was trying to build this wine, or I came across this wine club review site. I looked up some of their affiliate programs and I was like, "Oh, this site is probably making pretty money. It was making good money. It ranked well for such and such wine club keyword plus review or plus reviews." I was like, "Oh, that's really interesting. Who could I pivot that to?" We talked about Rip Pivot and Jam. Rip taking somebody else's business idea, pivoting to your own niche, your own expertise, like whatever you're curious or obsessed about, and then Jam, go and do the work, do the hustle. In my case, it was like using the exact same WordPress theme as the wine club review site to build out the first version of the virtual assistant review site. It was a clear pivot that ended up working out really well. So that is something that I was excited about. It was an opportunity that became visible once I was in motion. Had I never built this silly-looking wine site, never would have come across that opportunity. It's true. It's come up over and over again from somebody guests. The business that they start with is often not the business that they end up doing, but it's what got the ball rolling. We have a line in our house, my wife and I, where we say the weather in Turkey, and where it came from was we had this upcoming trip to Istanbul, and I'm looking ahead at the 10-day forecast, and I'm like, "Oh, shoot, it looks like it's going to rain while we're there." She's like, "Whatever." We're not canceling the trip, right? It's the weather in Turkey. It's a call to control the controllables, right? I could bring a rain jacket, but I'm probably not going to cancel this trip, right? There's a line where you can't stop the waves, but you can learn how to surf. It is a call to control the elements of your business that you have control over and doing your best to weather the storms that come your way, but recognizing that sometimes stuff just happens, right? Now, I have told the story before of literally my first day of self-employment after I gave my notice at work and turned in the keys to my company car. That's the day that Google decides to shut down my advertising account that the shoe business relied on. It was like, "Okay, deep right, you go through the seven stages of anger and denial." Ultimately, acceptance and saying, "Well, what can I control here? I can control the landing pages. I can make some improvements based on what I think they might want to see." Ultimately, it was definitely a stressful summer and an expensive one in redeveloping a lot of this night. Ultimately, they came back and said, "Okay, we made an error. We're good to go. The ad account is back on." It was an example of, "Okay, their decision is somewhat outside of my control, but I can control the user experience on the site and hopefully get it back into their good graces and be able to run that business for several more years." The next idea I want to present is this one called Sharp in Your Pencil. This comes from my dad when he would be helping me with homework as a kid. He would come over to the kitchen table and be like, "Look at this thing. Go sharpen your pencil. You can't do good work with a dull pencil." It's like, "Come on, just help me out with this math problem." It doesn't matter. He's like, "No, no, no. The tools you work with matter." This is the call to get a little bit better every day. It is looking for that 1% improvement, that slight optimization, that better, smarter, faster way to get things done. My virtual assistant back in the day, we were writing out hundreds of text ads for these specific models of shoes. She's like, "Whoa, have you heard of this little text-expander app?" I was like, "No, what's that?" She's like, "Oh, let me show you. It accelerates things." "Oh, and by the way, these campaigns are kind of slow to load because there's so many products in there. What if you kept four different tabs open?" Now we can do this. Four times is just to leave little micro improvements to the equivalent of sharpening the pencil in my case and trying to think of other examples when it comes to the podcast. Little workflow improvements and right now building out many AI agents to do certain parts of the process for me. It's like even after 13 years of doing it, there's still little performance improvements. There's still little ways to sharpen the pencil every day. I think you'll find the same in your business. A lot of entrepreneurs have the tendency to reinvest almost everything back into their business. You see this a lot in e-commerce. We have something that hits. I need more inventory. I've got all my capital tied up in inventory and growth sometimes for years. The idea that I want to present is it's okay. Take some chips off the table. Nobody ever went broke, taken a profit. In my case, trying to reinvest some of the earnings back into the business, of course, because it's probably the best ROI that you're ever going to see. You can get something that's compounding 20, 30, 50 percent a year. You'd be crazy not to feed that machine a little bit. At the same time, try to take some chips off the table and invest that into dividend-paying stocks, into real estate, into something where if I can get paid once, I want to make that dollar work for me over and over again. Sometimes it's going to be a very small percentage, but like, stocking a little bit of that away and trying to stack up some truly passive cash flow in that way. That's my call to take some chips off the table when it makes sense. For me, maybe the example of selling the virtual assistant site in 2020. There's like my time to work on it, had diminished, and it's like, "Okay, I don't want to see it, start to decline." So maybe it would be a good time to hand off the reins to the next stoner, to the next buyer. One question that comes up quite a bit is, "How do you know when it's time to throw in the towel on a side hustle?" The answer for me has historically been, "When you come to dread the work." The last thing that you need is a second job that you hate that you really don't look forward to doing, and there's a fine line between kind of like pushing through the tough parts, and okay, not every day is going to be rainbows and unicorns, but if you start to see a pattern where you're like, "This is not enjoyable. I'm not seeing the results that I want." You don't need this in your life, right? Business ideas are like buses. There's always another one coming. So I think it's totally fine. There's the, "Well, well, quitters never win and winters never quit." It's like, "Winter's quit all the time, right? If something is not serving you, it's totally okay to quit that." Or even put it on pause, put it on the back burner, and try and figure out the next stage. So I just want to put that out there as permission to not kind of work yourself, paint yourself into a corner where, you know, I'm now trapped doing this thing where it's like, "No, you're still in the driver's seat, and if it's not serving you, it's okay." Put a pause to throw in the towel or to say, "Okay, I'm going to pivot and I'm going to try something else." One of my most important side hustle habits is this practice, kind of a nightly, I done this exercise. What did I get done today? Did I do work that matter? Give yourself permission to celebrate some wins and some progress along the way because entrepreneurship can be a lonely road, right? And nobody else knows what you're going through. And so you kind of want to take stock of, you know, the way you're doing it. Okay, I checked this off my list. I got this off my list. This was important to me. I got this done and being really intentional both on that progress side What did I do and also for me really important is to say what am I going to do tomorrow that way? I know exactly what to do because yesterday Nick told me so in what order even before I start reacting to somebody else's agenda like what am I gonna do proactively for me in my business before kind of going into a reactive mode so tracking your progress and then taking a moment for gratitude This is all stuff that I have baked into my three question journal. It's what I get done today What am I grateful for and what am I what am I what am I top priorities for tomorrow? What am I gonna do tomorrow to win the next day and John Lee Doomsky the line you win tomorrow today And it's kind of the same idea of doing a little bit of advanced planning because the to-do list is never done right and that's kind of One of my struggles as an entrepreneur there's always more ideas than there are hours in the day But trying to be intentional. Okay. This is what I think I get done These are the my most important things to to go ahead so be intentional about Celebrating your wins and making some progress and finally I think the goal is to find a side hustle where you can I have a goal in mind of course. I think it's important to you know set the GPS where you want to go But then also appreciate the day-to-day journey the journey really is the destination you know finding work that you enjoy We've heard that the secret to happiness is meaningful work plus meaningful relationships plus a sense of progress a journey toward Mastery like getting better at your craft like Joe Salcihi from stacking Benjamin's he always gives me this line of you know I'm embarrassed by the work. I did a year ago and a year from now I hope to be embarrassed by the work that I did today, but he's on that journey that Every day I get to do work that I love and yes, there's a destination in mind. This is what I Want in terms of financial goals for my family or you know an end goal for my customers But along the way I'm gonna enjoy the moment. I'm gonna take a moment to look around and appreciate that This is pretty cool that we get to do this kind of work So really appreciate you tuning in if you find and value in the show the greatest compliment is to share with a friend So fire off that text message. We'll let them know about it Thanks so much for watching and make sure to subscribe for more money making ideas. Cheers

Podcast Summary

Key Points:

  1. Whatnot is a leading live shopping platform where sellers can significantly increase sales by building real-time connections with buyers, far outperforming traditional marketplaces.
  2. Successful side hustles require deep self-reflection on personal motivations, taking action before inspiration fades, and focusing on solving specific problems or following genuine curiosity rather than just passion.
  3. Entrepreneurs should validate ideas with low-risk experiments ("bullets before cannonballs"), embrace just-in-time learning, accept failure as part of growth, and avoid perfectionism to launch and iterate quickly.
  4. Evaluate business ideas by their potential asymmetric upside—where the reward outweighs the risk—and prioritize time deliberately rather than claiming a lack of it.
  5. Effective marketing involves placing your "buy button" where customers are already spending money and differentiating or improving upon existing solutions rather than fearing competition.

Summary:

The transcription highlights the explosive growth of live selling on Whatnot, a platform where sellers can earn significantly more by engaging buyers in real time compared to passive listings. It then shifts to broader side hustle advice, emphasizing the importance of understanding your core motivation to sustain effort during challenges. Success comes from acting quickly on inspiration, focusing on solving painful problems for customers, and leveraging curiosity.

Entrepreneurs should test ideas with low-cost experiments before fully committing, adopt just-in-time learning, and view failure as a normal step toward improvement. Perfectionism should be avoided; launching an imperfect product and iterating is key. When evaluating opportunities, consider the potential upside and whether the outcome justifies the effort.

Finally, effective marketing means meeting customers where they already spend, and competition can be addressed by being different or better, not necessarily first. Time management is reframed as a matter of priority, not availability.

FAQs

Whatnot is the largest dedicated live shopping platform where sellers can go live to showcase products in real-time, building connections with buyers who spend over an hour daily in the app. Sellers often sell 10 times more than on other marketplaces because it fosters engagement through live interactions and bidding.

Drill down to your core motivation by repeatedly asking 'why' you want extra money, such as paying off debt or gaining autonomy over your time. This deeper purpose will keep you going when challenges arise in your side hustle.

Inspiration is temporary, so build positive momentum by taking immediate action, like registering a domain or listing a product, before it fades. Momentum breeds results and creates a virtuous cycle of progress.

Focus on solving problems or following your curiosity, as businesses thrive by addressing customer pains. Alternatively, if you're entertaining, you can compete in that space, but solving specific problems often makes it easier to find an audience and make money.

If you can't be first, aim to be different or better by adding unique improvements or approaches. Competition can drive quality, so look for ways to iterate and leapfrog existing solutions in your niche.

Ask 'what if it works?' and consider the potential upside by looking at someone who is already successful in that area. Focus on asymmetric bets where the potential reward outweighs the risk, minimizing downside while aiming for significant upside.

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