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Lets be real.
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Nobody starts a business for the joy.
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Of calculating tax withholdings.
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That's where our partner Gusto comes in to take the stress out of payroll, benefits and HR so you can focus on why you started your business in the first place. Gusto is online payroll and benefits software built for small businesses. It's all in one remote, friendly and.
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Incredibly easy to use.
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So that means you can pay, hire onboard and support your team from anywhere. Talking about automatic payroll tax filing, simple direct deposits, health benefits, commuter benefits, workers comp 401k, you name it. Gusto makes it simple and all with.
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Plus, if you have any questions, their team of certified HR experts are standing by to help. It's no wonder why more than 400,000 small businesses already trust Gusto and why it's the number one rated payroll software for Fall 2025 according to the review site G2. So try Gusto today at gusto.comsidehustle and.
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Get three months free when you run your first payroll.
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That's three months of free payroll at gusto.comsidehUSTle one more time. Gusto G-U S T O.com Sidehustle this summer we went to part of the Rubik's Cube World Championships, which just happened to be in Seattle right around the the same time our kids had gotten very into cubing. The main event here is the traditional 3x3 Rubik's Cube and the fastest solvers in the world can do it in under 5 seconds.
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It's mind blowing to see because the fingers are moving so fast you can't.
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Even really tell what's happening.
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And then all of a sudden it drops and it's solved.
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But what was even more interesting, at.
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Least for me from a side hustle.
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Perspective, is that there was actual prize money involved. $5,000 for the first place competitor. It was yet another illustration that just.
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About any skill is monetizable if you're excited enough about it.
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And I tell you that story to tell you this one.
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Nothing gets me more excited than finding.
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Cool, creative ways to make extra money.
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And then sharing them with you.
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It is time for our annual Thanksgiving tradition on the show, a roundup of 10 of the most interesting and inspiring side hustles that have come across my desk this year. We've got product businesses, we've got service businesses, we've got content businesses. Something for everyone in what is always.
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One of my absolute favorite episodes to put together, and I want to start with one.
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I definitely had to do a double.
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Take when I saw it.
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This is Cutting Edge Firewood, the world's first luxury firewood company.
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I'm talking about $59 firewood boxes, $250.
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Firewood racks, cooking wood for high end grills, and wood fired pizza ovens. And people loved it. They grew to serve 30,000 plus customers, including some celebrity clients. They end up winning appearances on Netflix and the Today show and national media. But of course, success invites competition, and as many as 50 imitators pop up and try and play in the same space. But this is a story about taking the most boring, commoditized product imaginable and turning it into something that people brag about buying. Here, here's founder, Leroy Height.
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I founded Cutting edge firewood in 2013, but the idea started years earlier, where I went to school at Barry College, where I launched a few different businesses. And I realized something fairly simple. Firewood had never been disrupted. Everyone treated it like a commodity, really, even like lower than a commodity, because half of all firewood in the United States at the time that was sold was bug infested and the rest was rotten with mushrooms growing out of it. But I realized it's not a commodity, it's an experience. It's the aroma, the crackle, the warmth, the flicker of the flame. It brings people together and people will pay a premium for that experience.
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So Leroy's first firewood company actually started.
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While he was at Barry College.
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He joins a couple classmates.
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They start this firewood company called Premier Firewood. He's working as an operations manager. He's going through the entrepreneurship program there. He kind of catches the bug at that point.
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And after graduation, they keep it going but can't really make it work.
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The math isn't adding up. They're spending hours delivering wood for minimal profit at that point.
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So he moves on. He gets a job at Chick Fil A. He gets a job at Enterprise Rent a Car. He gets a corporate job in downtown Atlanta. He's doing his thing, but he can't stop thinking about firewood. It's this obsession. So he jokes with his wife, hey, when my 1993 Geo Prism breaks down with 266,000 miles on it, when the car breaks down, I'm going to buy a truck.
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I'm going to start this firewood business on the side. So two months into the corporate job, sure enough, the prism dies. It's going to cost $5,000 to repair. The car is only worth $300.
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So that weekend he tells a story about fasting and praying and trying to.
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Figure out the next step.
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But by the end of the day.
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He'S decided to go in on this firewood company.
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So Monday morning he goes to work and they fire him on the spot. Still doesn't know why, but he later.
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Says, that's the best thing that ever happened to me.
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Now I'm not starting the firewood thing as a side hustle.
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I'm going all in 2013, I went all in, maxed out every credit card I could get my hand on, worked 110 hour weeks doing hard manual labor. Everyone thought I was crazy except for my wife who stood by me.
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Now think about this, because it's does sound crazy.
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This is a product customers are literally going to light on fire. And maybe because of that, most firewood companies don't have any website, they don't have any branding. There's no such thing as customer service. You buy firewood from some guy on the side of the highway or some small moldy bundle from the grocery store. Now, Leroy grew up in northwest Georgia, maintaining the family wood pile. So he knows firewood, but as an adult, he's frustrated. Hey, I still love building fires, but I can't find good quality wood anywhere. The guy down the street dumps off, you know, dirty piles of wood into his backyard or into the driveway and he's got, Leroy's got to stack it and carry it himself. He's thinking there's got to be a better way. So cutting Edge starts in 2013 with this vision. We're going to be the world's first high end firewood and cooking wood company. The product is hand selected hardwoods, oak, hickory, cherry, pecan, apple, maplewood. Each of these pieces goes through this, this 48 hour kiln drying process. It's dry, it's mold free, it's pest free. And then trained specialists hand deliver every.
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Piece they toss out. Anything wet, rotten, ugly.
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Only the stuff that is photo shoot ready, that is Instagram worthy, is going.
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To make the cut.
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So the business is growing, it's getting.
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Some traction, but it's not quite enough.
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In 2017, Leroy realizes they're going to.
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Need some capital to reach the next level.
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2017, we were in a really tight spot when I went to my wife and I said, hey babe, I know we have a two year old and a three year old little girl's at home and you're eight months pregnant with our third. What now be a perfect time to sell our house and invest it in the business. And a couple weeks later, she had our third daughter at 11:30pm and then by 8am the next morning, I was with the lawyers selling the house. We took it, invested in the business, and reinvented how to do local deliveries.
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So that's what they do.
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They move into a rental. They use the funds to get a.
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Warehouse to refresh the brand, launch a new website, hire some employees, and that's when cutting edge really takes off.
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They are able to drop delivery time.
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From 2 hours to like 15 minutes. The product comes in these really cool, nice boxes with everything you need. Matches, fire starter, kindling. Along with the wood, it's like white glove. Delivered to the exact location the customers.
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Want inside or outside the house.
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The company grows to 25 employees each. Eventually, they've got eight trucks. They've got tens of thousands of customers nationwide. They get national media attention, the Today show, Fox and Friends, Hulu, Netflix, lots of newspapers and magazines. They get recognized as one of the.
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Fastest growing private companies in Atlanta.
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We were able to take over the Atlanta market, and in 2019, we started shipping nationwide because we had really taken over the Internet, all things firewood. And we started putting up yard signs in metro Atlanta and a few other cities in the southeast and really became like a household name in metro Atlanta and had explosive growth and continued to grow. And I exited the business about a year ago.
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Customers don't just leave reviews for cutting.
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Edge, they write love letters.
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Leroy pioneered this luxury firewood category, built.
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It into a national brand, proved you.
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Could take the most commoditized product again, stuff that people are literally lighting on fire and.
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And turn it into something premium.
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And then he eventually sold his stake.
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In the business for an undisclosed sum.
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So what's the takeaway? Is that every industry has low standards somewhere. So you find the one where people are really doing the bare minimum and then ask, what can you do to raise the bar? Obviously, Leroy didn't invent firewood. He just refused to accept the mediocrity that he saw in the industry. It was like an obsession. It annoyed him, and he turned it.
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Into an experience worth paying for.
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Creative side hustle number two is called.
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Boss as a service, which I think we've mentioned on the show before.
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But it's another story that I love because it's about solving your own problem.
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And turning it into a business, scratching your own itch.
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This comes from Manasvini Krishna, who was a lawyer, who then left the law.
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Job to start a tech law startup.
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Which sounded great, right? Except she quickly realized something was missing. When she was working the day job, she had deadlines. She had accountability. She had co workers depending on her when she started working for herself.
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None of that.
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If I missed a goal, she says.
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There was no consequence.
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She needed someone to help keep her.
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On track, but couldn't find a service that fit. So she ends up building Boss as.
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A service, really for her own use.
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Case how it works is you pay.
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As little as $25 a month to hire a quote, unquote boss who keeps you accountable. You send them your to dos for.
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The day or the week. They've got to be quantifiable because you'll need to prove that you did them. It could be a screenshot, it could be a photo, whatever.
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And if you don't follow through, they follow up and they don't stop bugging you until it's done.
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Now, admittedly, service isn't for everyone. If you're already really disciplined, you probably don't need it.
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But if you're someone who never misses a client deadline but sometimes misses on your own goals, that's the gap that this one fills. Manasvini started by personally keeping users accountable.
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She was the boss for hire. Her first customers came from the Beeminder productivity community. Then she got a little bit of.
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Traction on Product Hunt, but it was still just a side project. Then she created this quiz called why do I Procrastinate?
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And it was based on a productivity book.
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She puts it up on Hacker News. It goes viral. When people get their quiz results. There's a link to Boss as a service. Tons of people sign up. Now, three months later, someone else, maybe.
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A customer, posts Boss as a service to Hacker News again.
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And it goes viral again. Multiple people were signing up every minute, Montesvini says. And it was just me running the service. I couldn't handle anymore. So she had to shut down signups and start a wait list. Now, for most startups, virality is the dream, right? But there's still manual labor on the other side of this. So for her, it was overwhelming. She's working 14 hour days, she's like, I gotta hire a team. And that didn't come naturally. She said she struggled to delegate. She made some bad early hires, but.
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When she found the right operations lead, everything changed. That was when I realized this wasn't a side project anymore. She said it was a serious business. The other realization that she had was.
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That virality isn't a great long term growth strategy.
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She says.
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I was great at launching things. I was great at getting the first few customers. But taking a business from 100 users to a Thousand.
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I had no idea what I was doing.
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So she turned to mentorship. She started learning SEO systematically, you know, booking weekly calls with experts. She'd go back, apply what she learned. She'd get stuck at the next level and then book another call.
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Lather, rinse, and repeat that for months.
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And now SEO is one of the.
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Biggest traffic drivers for Boss as a service.
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Today, Boss as a Service has over.
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2,500 users at a minimum of $25 a month.
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That's over $60,000 in monthly recurring revenue. Solo founder profitable.
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They're also expanding beyond basic accountability.
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They're adding coaching, goal setting, support, building a mobile app too.
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They've even got interactive challenges like eat the frog for tackling your hardest task. First, a few takeaways for me here. One, virality is exciting, but maybe not sustainable.
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You gotta have a real growth plan for consistent lead flow. Two is you might need to sooner than you think, especially if you do have that viral moment.
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Because trying to do everything yourself, you're going to get burned out in those 14 hour days.
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Not sustainable. And three, the bigger lesson probably is.
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That there's money in accountability services. Boss as a service doing $60,000 a month. There's another one we've referenced before called MyBody Tutor.
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In the health and fitness space, they've got like 7,500 customers at almost 400 bucks a month. That's a $3 million monthly run rate on that one. So people are going to pay to.
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Help stay on track.
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And what I love about this one.
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Is Manasvini didn't complicate it.
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Look, she had this problem. She built a simple solution, tested it.
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With real users, and then scaled it when it worked. I think that's a great side Hustle playbook right there.
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Creative side Hustle number three is one.
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That is near and dear to my heart. And that's a ski tuning service.
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But of course, you could swap that.
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Out with a niche maintenance service in whatever hobby that you're into.
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Side Hustle show listener Ryan Goodwin does around $20,000 a year with his seasonal side hust Hustle and credited a simple.
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Google business profile with helping him get started.
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Hey there.
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My name's Ryan. I run a little ski tuning shop out of my garage here in Denver. It's called Peak Rover Tuning. This project started as an SEO experiment. Actually, I was messing around with the snowboarding blog. I figured it couldn't hurt to set up a Google my business profile and then link it to my site. So I put up a page advertising skeet tunes and pointed the GMB to that and it just sat there for a while. But then the snow came and the shops got backed up and I started getting phone calls. It didn't really matter that I had no reviews and I was working out of my garage in an alley and it turns out it's kind of a cool way to connect with the neighborhood and people who like the things that you like. So over the last couple years business has grown little by little. Working on my techniques picked up some new tools, expanded service. I offer local delivery so most of downtown Denver you don't even need to haul your stuff around. It's like pretty big advantage over the big shops. I was surprised, but I think a lot of people also are tired of walking into traditional shops and getting sold on new equipment and kind of feeling like not cool and your gear just gets passed down the chain or tossed in a machine for marketing. What's worked for me is just staying listed on Google, collecting reviews for something like this that's so super local might just be enough. It's kind of surprised how many people actually do this. I connected with a local tuner a while back does the same thing, but he also does bikes in the summer and we started kind of trying to build stuff to make it easier for others to do what we're doing. So we recently launched an iOS app. It's called Gear Fix on the App Store, but you can also find this at Gear Fix IO. The general idea is if you need your Gear Fix, there's probably someone in your neighborhood that has some knowledge and experience and likes tinkering. And it'd be cool if we could help build a network of little neighborhood gear shops.
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Peakrover.com if you're in the Denver area and need a little tune up before hitting the slopes in Gearfix IO. If you're thinking this is probably something.
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I could start in my own garage. Thanks to Ryan for sharing that.
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I've got more creative side hustles coming.
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Up right after this.
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If you're still overpaying for wireless, it's.
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Time to say yes to saying no.
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At Mint Mobile, their favorite word is no. No contracts, no monthly bills, no overages.
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No hidden fees, no bs.
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Here's why I said yes to making the switch and started getting Premium Wireless.
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For 15 bucks a month way back in 2019.
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All Mint plans come with high speed.
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Data and unlimited talk and text delivered on nation's largest 5G network. That means I can stay connected wherever I go. Plus I was able to bring my.
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Own phone, keep my existing phone number.
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And all my existing contacts. It was an easy move that's added thousands of dollars back to our bottom line over the years compared to overpriced wireless plans.
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If you're ready to say yes to.
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Saying no, make the switch@mintmobile.com Sidehustle that's mintmobile.com Sidehustle upfront payment of $45 required, equivalent to $15 per month limited time.
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New customer offer for first 3 months only.
A
Speeds may slow above 35gb on unlimited.
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Plan taxes and fees extra.
A
See Mint Mobile for details.
B
Whether you're a seasoned business or you're.
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Experiencing your very first Black Friday Cyber Monday, you need a platform that can handle the rush.
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The last thing you want is inventory.
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Errors or your point of sale crashing.
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When new customers are trying to buy for the first time. So make sure your business is ready for the busiest time of the year.
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With help from our sponsor, Shopify.
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Shopify is the commerce platform behind millions.
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Of businesses around the world, including dozens of Side Hustle show guests and 10% of all e commerce in the US.
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Shopify has thousands of templates and tools to make sure your site looks great.
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And is functional at the same time.
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And if you ever have any issues or questions, Shopify's award winning customer support team is standing by 247 so you.
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Can get back to business as fast as possible.
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If you want to give your customers the best shopping experience this holiday season, you need Shopify this Black Friday. Join the thousands of new entrepreneurs hearing.
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For the first time with Shopify.
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Sign up for your free trial today@shopify.com.
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SideHustle that's shopify.com SideHustle go to shopify.com.
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SideHustLe and make this Black Friday one to remember. Creative Side Hustle number four is a.
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Baseball bat rental service that's doing over $50,000 a month.
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This one hits on a few of.
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My favorite themes, scratching your own itch, starting lean, and building recurring revenue.
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This one comes from a couple friends, Oscar Urana and Eric Rico, who grew up playing baseball together in Florida.
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Eric actually got drafted by the Toronto.
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Blue Jays and after his playing career he opened up this youth baseball academy and that's where he started noticing something. Kids would show up with talent, but they would be discouraged because they couldn't afford the equipment and they're competing against.
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Teams where every kid has brand new gear. And here they are with these beat up hand me down bats.
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And here's the thing, a quality baseball.
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Bat is pretty expensive. We're talking like 300 to $500 up front.
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And for a lot of families, especially.
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When their kids are constantly growing and growing out of equipment that's just not in the budget.
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So Oscar and Eric figure there's got.
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To be a better way.
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So they come up with Bat Club.
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USA batclubusa.com It's essentially a bat rental subscription. So Instead of dropping 500 all at once, families pay a monthly fee starting as low as 17amonth for younger players and going up to like $45 or more for older kids with higher end bats. And they run these on 12 month contracts.
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But here's the thing. This was really smart. Before they went all in. They tested it with 15 different families.
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At Eric's baseball academy and get overwhelmingly positive feedback. And so that gives them the confidence to really go out and invest.
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So there's a recurring revenue element to this business, but it's inventory.
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So they have to come up with $40,000 of their own money, in this case to go out and buy inventory.
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To serve 2000 members, they're buying a lot of bats.
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So Eric uses some of his baseball.
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Connections to source these bats. And they start by storing everything in his garage. And their marketing approach was really hands on at first. So they would start to show up at tournaments in Florida, in Texas. They would set up a booth, they would talk to the parents. And what made it work was that kids could walk away with a bat that same day.
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So they're bringing the inventory with them.
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Hey, subscribe right here. Instant value, you know, as low as $17 a month. No shipping, del plays, no nothing. And then those kids eventually become their sales force.
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Everybody else on the team is like, hey, dang, where did you get that?
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Oh, it's from these guys. So later they ended up scaling up with Facebook ads.
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They would target parents who were already following baseball related brands, baseball related content. And Facebook knows everything about you.
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If they're hanging out at baseball tournaments on the weekend, you're going to be.
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A prime candidate for this.
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And that combination took them to that.
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50 grand in monthly recurring revenue.
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Now, rapid growth brought its own challenges.
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They had issues with fraud. They had to stop taking prepaid cards.
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Inventory tracking, you know, shipping, you know.
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30 inch long metal things across the country.
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Inventory tracking becomes kind of this logistical challenge to solve.
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But they ended up building out a system with stripe and Shopify to help keep everything organized. And their biggest piece of advice was to test your idea first. You got to validate before you invest big.
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Those first 15 families at the academy proved that the concept could work and.
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It gave them the confidence to go out and scale the thing and put down that inventory investment.
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And now they're looking at expanding into other youth sports using the same rental.
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Model, making athletics more accessible across the board. I've got a couple questions around the.
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Depreciation of this equipment.
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Like how long before a bat wears out? I don't know if it's just superstition, but when I was playing some people.
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Were really protective of their bats. Like they believed it only had a certain number of hits in it. They didn't want anybody else to waste them.
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So there's something there. But really cool example Bat Club usa. Check it out. If you are in the market for some rental equipment, rental baseball equipment, or thinking, well what else could I pivot that same model to? And we've seen, you know, rental musical instruments.
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That's been a thing for a long time.
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But curious what other ideas you might have on a creative rental business.
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Creative side Hustle number five is a car seat cleaning service. And this one brought in $5,600 in first for months. And it started with this simple question.
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Why doesn't somebody do this?
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Shelby Merrill is a stay at home mom in Utah with two little kids.
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Under 3 years old.
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And she loved staying at home with them. But she wanted to find a way.
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To bring in an extra thousand dollars a month. Good to have that kind of concrete goal.
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She says. I came up with the idea to start cleaning car seats because cleaning car seats is the worst. My kids car seats are always dirty and every time I clean them I.
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Think there needs to be someone who does this.
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Her light bulb moment is when she realizes I could be the someone who does this. So she took the idea and ran with it, mostly working at night after the kids go to bed and made.
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That thousand dollars in profit in her first two weeks. So here's the timeline and this is pretty wild. Saturday is when she comes up with the idea. Also on Saturday, she registers the llc.
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She completes her legal paperwork. Sunday, her sister in law designs a logo. By Monday, Car Seat Scrub Club is officially in business. Her first client is her cousin.
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She did it for free and asked her to help spread the word to other moms and offered to waive the.
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Travel fee for in exchange for those referrals.
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Then she went hard on the marketing.
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She posted on Instagram stories, posts she.
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Shared in local Facebook mom groups.
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She even ran some paid Instagram ads. And by Tuesday, three days after the initial idea, she's got her first paying.
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Customer, and then two weeks later, she's already made a thousand dollars in profit.
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So after she puts her kid to bed, like logistically how this is happening?
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She's driving around picking up car seats anywhere from one to five in a night. And this got to be pretty localized service. And now she's expanding to doing strollers as well.
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$40 per car seat, plus a $15.
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To $25 travel fee depending on how far it is.
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She brings them home to the garage, takes them apart, cleans them according to the manufacturer's manual.
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Those different seats apparently have different guidelines. So when people book on her website, they're going to tell her the model.
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Of the car seat so she can look it up beforehand. They air dry overnight. In the morning, before the kids wake up, she ties a bow and a thank you note to each seat and then returns them.
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Guaranteed delivery before 9am how's that for turnaround service?
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Because the people are going to need the car seats to go about their day and then it's back to regular.
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Mom mode for the rest of the day. I don't know how sustainable that is.
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Just where you're supposed to sleep when.
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The kids are sleeping when you got young kids. But in any case, really cool example of taking action. And yes, since I know you're asking, part of that initial weekend setup was a legal consultation and getting insurance before getting started. Smart move when you're taking apart other people's car seats.
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But then what is really interesting, Shelby makes this Night in the Life of.
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A Car Seat Cleaner video for her business.
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Instagram cross posts it on TikTok because.
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Well, you know, whatever, I already made it, it's fine.
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Doesn't think much of it. Then her mom texts her at like 11 at night. Your video is doing so well, you got to go in and respond to these people's.
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So she opens up TikTok and finds.
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Thousands of new followers.
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The next day she posts another video. So in two days she goes to like 30,000 followers. And that first video, the Night in the Life of the Car Seat Cleaner.
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Has two and a half million views.
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That virality helped and it hurt at the same time. It brought awareness, it drummed up business. It helped her actually earn money from TikTok's creator fund. But it also meant competitors started to pop up in her area because people.
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Watched her videos and they started their.
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Own car seat cleaning business. Now here's where it gets even more interesting. She goes viral, right? Her DMs start to explode with people asking how to start their own car seat cleaning business. Now, the first day, she says. Shelby says, I was just responding to everyone and telling them how to do it.
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And I was probably on my phone.
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For like nine hours that day because I was just trying to help everyone out. Then she realized, wait, why am I giving this away for free?
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So she launched Scrub Club courses with.
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A couple different options. A $500 ultimate business plan and a $75 mini course. Through August, she had earned the $5,600 from cleaning the car seats. That was like 100 plus, you know, car seats that she'd done the overnight thing for.
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Plus she'd made an extra $6,000 from selling the courses to other people who.
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Wanted to start the business. So she's expanded now to a couple.
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Different counties in Utah.
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She's hired a couple other cleaners to.
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Kind of expand the geography there.
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And the money has helped her family pay off some debt and book a trip to Disneyland. The next goal is to upgrade her Honda Civic to a new car.
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Shelby says she's limiting the car seat.
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Cleaning business to four nights a week so she doesn't get burned out and to maintain some boundaries between work and rest and family time. And what I love about this is Shelby identified this pain point that every parent has. Look, the car seats are gross.
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And she went out and solved it, didn't overthink it, Registered the business on.
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Saturday, had a paying customer by Tuesday.
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And then when competition emerged from her own viral success. Look, I'm not going to panic. I'm going to find another revenue stream teaching other people how to do what I did.
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Super smart. So look around at the things you hate doing.
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Chances are other people hate doing them too.
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Maybe they're going to pay someone to handle it. Remember Erica Kruipen's pet waste removal business? Exact same thing. Oh, I got to go take out. They got to go pick up after the dog.
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Hey, look, if I hate doing it, it's going to be a pain point.
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For other people too. Maybe I could turn that into a business. Creative side hustle number six. This is probably the most interesting one that's come across my desk this year. It is the Swiftologist. This is Zachary Howahan, who is known online as the Swiftologist, who has become a full time Taylor Swift content creator. Could you turn your own fandom into a full time income like Zachary has today?
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He's got over a quarter million followers across YouTube, TikTok and Instagram. And he was even featured in HBO's.
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Documentary about the Swift Scooter Braun controversy. I don't know what that is, but he was on HBO video about it.
B
Zachary is a journalist by training and.
A
Before making videos he was writing full time. But he noticed something and then that was articles have limited reach these days. Your main goal as a writer is for your ideas to be heard, he says. But video first content reaches a much wider audience in a more engaging manner.
B
Zachary's been a Taylor fan since he was 13, but his content creation really.
A
Kicked off during the pandemic when Taylor surprise dropped her album Folklore Reaction. Videos were becoming a thing on YouTube, Zachary explained it was this seismic event in Taylor's career. I usually just wrote down my first.
B
Impressions, but this time I wanted to.
A
Record it for posterity. That video ended up gaining some traction.
B
Then came the Evermore album. And then Zachary's day job started laying off writers. I hated being in a position where.
A
Something could be taken away from me, he said. I decided I wanted to own what I did and I've highlighted that in my little working doc here because that's such a powerful line. I wanted to own what I did. I think that's something we can all relate to.
B
So in 2022, he starts treating it like a full time job, the Taylor.
A
Swift's content while he's still working the main job.
B
And two years later it actually becomes.
A
His full time focus.
B
Today he co hosts a podcast called.
A
Evolution of a Snake with Madeline Rubicam.
B
It goes year by year through Taylor's entire recording catalog. In her career.
A
It generates between 50 and 100,000 listeners every week. This is according to Pedestrian TV free version of the show. It's available just like this one wherever you get your podcast.
B
But the real money for Zachary and.
A
For Madeline in this case comes from Patreon, where they share exclusive episodes, they do deep dives, they have, you know.
B
Content that is apparently too spicy for the algorithm. According to Patreon Today, you've got 15,000.
A
Patreon subscribers paying between 3 and $25 a month. And let's assume that most go for like the $6 tier on average. There's a whole bunch of different options you can choose from on that page.
B
And now split between co hosts, you.
A
Know, there's some podcasting overhead, there's some.
B
Costs involved, but we're doing the math on that. 15,000 subscribers times a six dollar monthly average is $90,000 in top line subscription revenue just for the podcast alone. Now here's what makes Zachary different from.
A
Other fan creators is that he's not 100% fanboy.
B
He's critical, right? He'll analyze Taylor as a real person, including the stuff that might be uncomfortable.
A
For example, he did a video essay about her billionaire status and her private.
B
Jet usage, and the Swifty community didn't love it. He's actually gotten death threats before. People take this stuff really seriously, he told Pedestrian tv. People misconstrue me, wanting to critique her as me being a covert hater.
A
But here's the thing.
B
Look, he's seen her in concert 20 plus times.
A
He's met her at secret sessions.
B
He calls her the world's great greatest songwriter. He just refuses to pretend that she's perfect. His advice for building an audience is to be consistent and to show up week after week, he told Authority Magazine. People will meet you where you are, but you have to show up for them frequently. The best audience isn't the biggest one, it's the most engaged one.
A
For that reason, you gotta live in the comment section. Zachary also gave the advice to balance.
B
What you love with what the audience loves, even when those conflict, and not.
A
To measure success by the numbers alone.
B
Sometimes the content you really put your heart into doesn't resonate as widely as something that didn't matter to you at all, he said.
A
But it's just as important to scratch that creative itch. What I find interesting here is Zachary is tapping into an existing passionate audience. He didn't create Taylor Swift fandom, but.
B
He did become a trusted voice within.
A
It by bringing his journalism skills to fan content.
B
And he treats it like a job. He posts consistently, he does quality analysis, he takes the time to engage with his community, and he's not afraid to be contrarian, even if it brings him some haters. The Patreon model works really well because superfans, they want more than just the free stuff. They want the unfiltered takes, the deeper analysis, the stuff that may be a little more nuanced than a TikTok video is going to allow. And they'll pay for it. The book 80:20 sales and marketing comes to mind here. If we start out with the huge, huge addressable market, the Taylor Swift fans, the Swifties, maybe 20% of those seek out additional information about her, the kind.
A
Of content that Zachary produces.
B
And maybe 20% of those are willing.
A
To pay for even more.
B
So the question is, could you do this in your niche?
A
It could be gaming, it could be.
B
Sports, it could be a TV show. Whatever it is that you're obsessed with.
A
Could you bring that same level of commitment and analysis to the game.
B
The playbook here is just what Zachary's done. Bring the real expertise, be consistent, build.
A
Community, and then figure out a way to monetize with subscriptions.
B
Zachary proved that you can turn fandom.
A
Into a career if you're willing to.
B
Do the work More Creative side hustles in just a moment, including getting paid.
A
To read Reddit posts and the Six Figure Wedding Proposal Planner coming up right after this.
B
As a business owner, you worked hard.
A
To make that phone ring.
B
But missing a business call?
A
It's like watching money fly right out the window.
B
That's why today's episode is brought to you by Quo, spelled Q U O.
A
It's the smarter way to run your.
B
Business communications Quo is the number one business phone system built for 2025, not 1995. In fact, it's rated the top choice for customer satisfaction with over 3000 reviews on G2.
A
Quo works right from an app on.
B
Your phone or computer, and it means.
A
Your team can share one number and collaborate on calls and texts, just like a shared inbox. And here is what is really cool because if you can't answer the phone, Quo's AI agent can. It can qualify leads, it can route calls to the right person, and it's going to make sure no customer is ever left hanging. Think of it like having 247 support without the 24. 7 payroll, more than 90,000 businesses are already running on Quo, from solo operators to growing teams. Try it free when you go to quo.comsidehustle that's Q-U-O.comsidehustle. you can even keep your existing number quo. No missed calls, no missed customers.
B
Creative side hustle number seven is getting.
A
Paid to read Reddit posts. Now here's a content model that's so absurdly simple. It's reading Reddit stories out loud that ask Am I the Jerk? This is a podcast called Am I the Jerk? They take stories from Reddit, usually from Am I the A hole Subreddit. They've got voice actors who perform them.
B
They might add some commentary and then.
A
They publish every day. There are over a million subscribers to the Am I the Jerk? YouTube channel. Their podcast, with more or less the same content, has over 12,000 reviews on Spotify, so lots of people tuning in over there. Some example episode titles include Vegan Friend Demands We Eat a Vegan Thanksgiving Dinner.
B
Entitled Mom Wants Me to Babysit Her.
A
Three Kids for Free.
B
Chinese Restaurant Reuses Customers Leftovers to Save Money on food. It is Reddit content arbitrage and is.
A
Working really well for this Business.
B
Pretty straightforward concept. People submit their real life drama to Reddit, asking if they're in the wrong.
A
Most of the time knowing that they're not.
B
Am I the Jerk takes those stories, dramatizes them with some voice acting in.
A
The packaging, pages them together as 20 minute episodes. Sometimes some of the YouTube videos are quite a bit longer than that, but.
B
The appeal is it can be background content. People can listen in while they're driving, while they're studying, while they're working out, doing chores. And the stories are relatable. It's entitled co workers, it's overbearing parents, it's frustrating partners, it's stuff that everybody.
A
Has dealt with or there's a voyeurism aspect to it. On both the podcast side and the YouTube side, they're publishing daily over 1500 episodes at press time and revenue, Estimator Tools put their potential earnings between $20,000.
B
And $100,000 per month just from YouTube.
A
And then you can tack on podcast sponsorship revenue.
B
On top of that, they've also got.
A
A spinoff show called Am I the Genius? Same model, slightly different angle.
B
And the real genius here is they're not creating the core content, it's user generated. The Reddit users are creating it and.
A
They create it every single day.
B
You don't have to worry about running out of material.
A
Am I the Jerk is just curating it and repackaging it it a lot of times you might not even need a script writer.
B
The stories are free.
A
The only real cost is voice actors and production time. And actually the recent ones sound like.
B
They'Re, in my opinion, fairly low grade.
A
AI voices, but people are still tuning in.
B
Plus the format is pretty evergreen.
A
A story about a bad boss or a nightmare mother in law from three years ago, still relevant, still relatable. And here's the thing.
B
Am I the Jerk isn't alone in this space either.
A
There's R Slash, there's one called Mark.
B
Narrations, there's a bunch of other channels doing basically the same thing, reading Reddit stories, monetizing with ads and sponsorships.
A
And Reddit keeps pumping out the drama every single day.
B
So the takeaway here is that curation and then repackaging to a different medium.
A
Is a business model in itself.
B
What's cool is that you don't always need to create original content from scratch. Sometimes the content content already exists.
A
And with Reddit's upvoting, you can see what resonated by what is risen to.
B
The top of those subreddits. You just need to make it more accessible, maybe more entertaining, presented in a different format. I think this one is ripe for.
A
Replication in another niche. Whatever it is that you're into, financial.
B
Advice, relationship questions, tech news, there is no shortage of user generated content in pretty much any niche out there. The question is whether you can package.
A
That in a way that adds value, that builds the audience, and that is going to be monetizable in some way through YouTube views or through podcast sponsorships.
B
The bar to create something like this.
A
Super low, you got to have some recording equipment.
B
Maybe not if you're going the AI route.
A
I don't know.
B
This is a crazy new world to me.
A
I was really excited when I came across am I the jerk? So check that one out. And big thanks to E Biz Facts for highlighting that one because I think it's a pretty cool example.
B
That was number seven on the list. Getting paid to read Reddit post hosts. Number eight is the six figure proposal planner.
A
Now talk about a niche I never knew existed. Professional proposal planning. This comes from Lexi Tobin in New York. She helps people plan marriage proposals.
B
Talking lights, flowers, photography, filming the moment, coordinating vendors. You gotta have vendors at your marriage proposal these days. In any case, she's built this into a six figure side hustle while working a full time corporate job. In her best month, she made over $20,000. And it all started by helping her brother in law proposed to her sister.
A
In 2019, her brother in law asked.
B
For help planning his proposal to Lexi's sister. She told CNBC she'd always been known as the planner in the family.
A
So she goes all in for the brother in law.
B
She orders picture frames, string lights across this archway, she's putting candles in paper bags. She's setting everything up at this beach house in New York. Then to capture the moment, she films her sister running down this white runner into into her fiance's arms. And the whole time, Lexi's having a blast.
A
The whole process.
B
The planning, the coordination, the surprise, the celebration afterwards. So a few months after that, she.
A
Decides to post the proposal video that she made on TikTok.
B
Didn't expect much. It goes viral. 100 million views. Friends, family, strangers, everybody starts pouring in, asking for help with their proposal. She realized, oh my gosh, there's actually.
A
Demand for this service. So she did what any good entrepreneur would do.
B
She started charging for it.
A
So here's what proposal planning looks like.
B
Clients come to her wanting to pop the question. They've got no idea how to execute it.
A
And so Lexi helps them handle everything.
B
She typically hires One to three vendors per event.
A
It could be a photographer, it could be a florist, maybe it's a musician. And right now, a proposal with five vendors she says can cost upwards of $10,000.
B
And the number is climbing.
A
As the wedding industry gets more and expensive.
B
Lexi keeps about 15% of that as.
A
As her fee, as 15% of the event planning fee as her profit.
B
But where it gets interesting is that.
A
Isn'T her only revenue stream.
B
She also makes money from brand deals and affiliate marketing through TikTok, where she.
A
Now has over 300,000 followers and Instagram as well.
B
And she posts the proposal reactions.
A
People love watching them.
B
So that kind of content fuels her own social media, which then drives more.
A
Clients, more brand partnerships. Very self fulfilling or virtuous circle in that way. Over 12 months, she brought in six figures in revenue with a median monthly income of $9,000.
B
November 2023 was her best month ever.
A
According to CNBC at $20,000. And she's not just doing proposals anymore, she's doing bridesmaid proposals.
B
This is inviting friends to be in your wedding party.
A
She's doing engagement parties, she's planning birthday.
B
Parties, she's even doing full weddings now, now. And all of that is still a.
A
Side hustle because she's still got a full time job in ad tech where she earns quote unquote, substantially more than.
B
Her side hustle stuff to give up that gig. But she still spends up to 40.
A
Hours a week on her side business on top of 60 hours a week at her day job.
B
So that's pretty grueling.
A
That's 100 hours a week in total of work. So maybe not sustainable in the long run. But she says she's investing all of her side hustle earnings, earnings into the market while trying to live off just her corporate salary to really accelerate that path to financial independence. Now what's interesting about that CNBC article where Lexi's featured is According to the Knot 2023 Real Wedding Study, one in.
B
Four proposers now pay someone to help them pop the question. One in four, that's like a pretty sizable market, much more than I would have expected. So Lexi narrowed in on just that.
A
Specific part of the wedding industry, just.
B
The proposal, not the whole wedding starting out. And I think that specificity that niching down really good for business. Less competition, clear positioning, gets people talking.
A
Oh, I didn't know that was a thing. And oh shoot, I need some help with that.
B
So here's a high emotion moment in.
A
Somebody'S life where they would be willing.
B
To hire some help if they knew it exists.
A
She says, yes, it does exist.
B
You can hire me. Proposals are stressful. People want it to be perfect.
A
They're willing to pay for somebody to.
B
Handle the details so they can just enjoy the moment.
A
I think Lexi did a really nice.
B
Job of identifying that gap, filling it.
A
And then building this content engine around it that creates those multiple revenue streams.
B
And she did it all while keeping.
A
Her corporate job because she's playing that long game.
B
The question is, could you do something similar?
A
I mean, maybe she's got proposals on lock and maybe, I don't know if she does them remote or just it's got to be in New York, whatever it is.
B
But could you do something similar for another life moment?
A
A baby announcement, a gender reveal, a.
B
Retirement party, some milestone birthdays.
A
I don't know. I think there's something to this niche event planning type of thing here. So that's the formula. Find the event, offer the service, document it, build that virtuous cycle. As the audience grows, you can start to monetize it in a few different ways. So that was creative side hustle number eight.
B
The next story on our list of creative side hustles today is about a high school kid who turned a hobby.
A
Hobby into around $20,000 in profit.
B
Paul Castor started woodworking at around age 12 after watching some YouTube videos. He would make cutting boards, bottle stoppers. He would do bowls. He would sell them occasionally on Etsy, but mostly to family and friends. Of course. His first customer was his mom. Then somebody gives him a wooden bow.
A
Tie as a gift. He thought it was a cool idea.
B
But this particular one was was pretty chunky. He thought it was unattractive, it was poorly finished. He figured, look, I could do better. And it turns out he was right. And that turned into Crooked Branch Studios.
A
Wooden bow ties number nine on our list of creative side hustles today.
B
So Paul noticed something about the wooden.
A
Bow tie market on Etsy. Most of them were either too large.
B
Too chunky, or they were just flat, boring, lacking depth, not a lot of middle ground. So he wanted to create what he called called a Goldilocks version.
A
Something that looked and felt like a classic fabric bow tie, but made out of wood.
B
Smooth contours, three dimensional, not too thick, not too thin. And he starts experimenting.
A
And he actually started out using PowerPoint to design the profile before graduating to some CAD software. Once he had the shape and contours.
B
He liked, he added fabric in the center, which made it less cold, made it easier to customize and he was able to source some really cool reclaimed exotic woods like walnut, cherry maple, zebra wood, cocobolo. I don't know if I'm pronouncing that right. And then he priced each bow tie between 40 and $50 each, listed them on Etsy, and then the natural search and discovery features on Etsy are what drove those initial sales. And he quickly realized that Hades are.
A
Selling a lot better than than the bowls and cutting boards that I used to be making. Like here's something really unique.
B
So he started getting requests for customizations. So he would do laser engraving for initials on the back.
A
People wanted their names, they wanted dates if it was going to be like.
B
A groomsman gift kind of thing. So the wooden bow ties are selling well on Etsy.
A
And Paul sets up his own storefront.
B
Called Crooked Branch Studio, which would allow a little more flexibility in his marketing. He says that move directly led led.
A
To about $6,000 in increased sales and boosted his credibility. It actually got him featured on NPR's.
B
How I Built this Podcast. And while he was still in high school, Crooked Branch Studio hit $40,000 in.
A
Revenue, of which he said about $20,000 was profit in a single year.
B
But then college happens and Paul knows.
A
He can't keep up the same pace of production.
B
But instead of shutting down the business.
A
He hires three private contractors and partners and with a couple different manufacturing companies to help keep building the bow ties, which I thought was pretty smart move for a young kid.
B
This let him continue to sell over.
A
2,000 wooden bow ties a year, both retail and wholesale, while he's busy studying engineering, computer science and business at usc.
B
During this time, the business is still pulling in around $1,000 a month in.
A
Profit with less than one hour a week of his time time. Basically passive income as a college kid. Love it now.
B
From there, Paul moved to expand the product line.
A
Wood was, was really cool and all, that's what gave him his start. But what else can we make bow ties out of? So he launches a sub brand called Carbon Cravat bow ties made out of aerospace carbon fiber. That sounds pretty cool. Marketed them as the bow tie made from rockets. According to Startland News.
B
Different appeal. Car guys love it. Airplane enthusiasts love it. It's this high tech material of the future. Paul also gets into wholesale, meaning he.
A
Found four or five retail stores to carry his products, which he said amounted to around 10% of overall sales. And an interesting side benefit of that was that customers would see them in the stores and then they would come to his website for Custom orders or for wedding packages. And so the takeaway here for me at least is Paul sees this product.
B
Category that already exists but wasn't done.
A
Well, in his opinion. He didn't invent wooden bow ties.
B
He just set out to make better ones.
A
Literally building a better mousetrap kind of a thing.
B
Etsy is crowded, no doubt about that. But there's still opportunity if you offer something unique or higher quality than what's already out there. The other lesson is outsource when you need to scale. Like Paul built the business hands on.
A
Look, it's me making these things in high school. But then as his time diminishes, as.
B
He moves across the country, he systematically.
A
Replaced himself with other people who could do that work. Other contractors, other manufacturing partners. He turned this labor intensive operation into an essentially passive income stream. Really cool, really inspiring.
B
And he didn't let his age stop him. Some people didn't take him seriously because.
A
He was young, but he proves them wrong with results.
B
This business, it doesn't appear to be as active now, but looks like it.
A
Had a really solid run. Paul built something real while most kids in his age are just looking for summer jobs, minimum wage type of stuff.
B
So that's kind of entrepreneurial thinking I.
A
Think is going to set him up really well for the long term. You can check it out@crookedbranchstudio.com Creative side.
B
Hustle number 10 is a marketing agency.
A
Which by itself is not that exciting.
B
Except this is a marketing agency specifically for dog trainers. This business is called digi woof digiwoof.com and according to E Biz Facts, it's generating over $10,000 a month. But it's this kind of hyper focused niche agency that a lot of people probably going to dismiss as being too small.
A
But I think that's exactly why it works. Josh Boutel, who runs this business with.
B
His wife Mandy, isn't some random marketer who picked dog trainers out of a hat. Oh, the keyword research led me to this niche. No, he's got over 10 years of running own certified dog training business in San Francisco. It's called City Pups SF Helping dog owners deal with leash reactivity, separation anxiety, real problems that dog owners are dealing with. So he knows the industry, he knows the clients, he knows what dog trainers are struggling with because he was living this world. They're not outsiders. Parachuting into quote, unquote, disrupt an industry that they don't really understand. So digiwoof, the agency offers everything a.
A
Dog trainer needs to market Themselves, online.
B
Website design, graphic design, social media marketing, email and SMS marketing, process automation. And the website's only been around since 2021. So this is a relatively new operation. But when Josh is talking to dog trainers, he's one of them. He can speak their language. He's not some generic agency pitching marketing services. And having lived it, he understands the.
A
Specific pain points that dog trainers are dealing with.
B
They don't want to mess with tech, they want to want to train dogs. That's why they got into the business. So Josh builds systems that automates client onboarding, appointments, scheduling, follow ups, all the administrative stuff that keeps trainers from doing the stuff that they actually love. And even more interesting is that it's.
A
Actually even more niche than just targeting dog trainers. I debated about including this because, like, I don't know if people will know what this is.
B
Josh is creating content specifically for the R community within the dog training world. That is positive reinforcement training. He's got a podcast called the Digital Dog Trainer.
A
He's writing blog posts about how dog.
B
Trainers can use mini courses to market themselves, how to grow an email list, how to manage Google reviews.
A
It's not just generic marketing advice. It's really tailored to a niche within a niche. And that is a formula I think.
B
Could work across any different niche that.
A
You, you happen to have a foot in the door too.
B
Josh mentioned that he uses the software.
A
High Level to deliver the services at scale. That way he's not, you know, custom building everything from scratch. There's some built in templates, automations and systems that are working across all his different clients.
B
And so other people are using High Level to do pretty much this exact.
A
Same thing in other niches. Maybe it's music teachers, maybe it's dance studios, maybe it's tattoo parlors, maybe it's church searches, whatever that you might have that, that little in or that industry knowledge of.
B
And the services are basically the same.
A
You know, websites, social media, email, marketing, automation.
B
The difference is the positioning. We're really going to be the expert.
A
In this one industry and we're going to seek to understand that client better than anybody else.
B
And a lot of people will think.
A
That niching down is going to limit your business.
B
But I think Josh proves the opposite. If you're trying to grow your business, your r dog training business, he's the obvious choice.
A
He's not competing with every generic marketing agency out there. He's the dog training marketing guy. And when you own a niche like.
B
That, I think 10 grand a month is just the starting point.
A
Really cool example of coming to dominate a niche.
B
So I hope these businesses got some creative gears turning in your head. To recap, we had the Luxury Firewood service taking a commodity product and making it it an experience. We had Boss as a service selling some accountability. We had the ski tuning business in Denver. We had the Car Seat Scrub Club in Utah and the subsequent Side Hustle that spun off helping other people start.
A
A car seat cleaning business.
B
We had the Swiftologist, a full time Taylor Swift content creator. We had getting paid to read Reddit.
A
Posts with the example being am I the jerk? Check them out on YouTube and whatever podcast platform you are. See how they're doing that.
B
And could you spin off something similar in your own niche that you like? We had the six Figure Proposal Planner helping people plan epic wedding proposals. We had a teenager making wooden bow ties and selling those in retail stores and online.
A
And we had Digi Woof, the marketing agency specifically for dog trainers.
B
So I want to wish you a.
A
Really happy Thanksgiving to you and your family. Make sure to take a moment for.
B
Gratitude today and every day to appreciate.
A
What you have, how far you've come. I am grateful for you spending some time with me today and really every time you spend some time with the Side Hustle show in your earbuds.
B
I'm grateful for everyone who sends me these great side Hustle stories like the ones you heard today. And I'm grateful for our sponsors for.
A
Helping make this content free for everyone.
B
You can hit up Sidehustlenation.com deal for.
A
All the latest offers from our sponsors in one place.
B
Thank you for supporting the advertisers that support the show. That is it for me. Thank you so much for tuning in. If you're finding value in the show.
A
The greatest compliment is to share with a friend.
B
Until next time, let's go out there and make something happen and I'll catch.
A
You in the next edition of the Side Hustle Show. Hustle on the.
Title: 10 Creative Side Hustles That Make Real Money – Part 9
Host: Nick Loper (Side Hustle Nation)
Date: November 27, 2025
This special Thanksgiving edition of The Side Hustle Show features Nick Loper’s annual roundup of 10 of the most interesting, creative side hustle businesses discovered throughout the year. The episode showcases a mix of product, service, and content businesses—each demonstrating unique ways to turn ordinary (or even boring) ideas into profitable ventures.
(Start: 02:31)
Founder: Leroy Hite
Idea: Transforming ordinary firewood into a luxury product by focusing on quality, experience, and branding.
Details: Hand-selected, kiln-dried, pest-free hardwoods delivered “white glove” in premium packaging; $59 per box, $250 firewood racks; featured in national media.
Growth: Over 30,000 customers, national expansion, eventual successful exit.
Insight: Every industry has low standards—find where you can raise the bar and create an experience worth paying for.
“I realized it’s not a commodity, it’s an experience. It’s the aroma, the crackle, the warmth, the flicker of the flame…people will pay a premium for that experience.”
— Leroy Hite (03:33)
(09:31)
Founder: Manasvini Krishna
Idea: Users pay ($25/month+) for a “boss” to hold them accountable to personal or business goals.
Growth: From viral posts and quizzes, the business scaled to 2,500+ users and over $60,000/month in revenue.
Expansion: Added coaching, goal-setting, challenges, and is developing a mobile app.
Insights:
“I was great at launching things… But taking a business from 100 users to a thousand, I had no idea what I was doing.”
— Manasvini Krishna (12:21)
(14:00)
Founder: Ryan Goodwin
Idea: Seasonal ski-tuning business started as an SEO experiment, run out of a Denver garage.
Model: Google Business Profile brought in clients as local shops became backlogged; now offers delivery and is building a local network (Gear Fix app).
Diversification: Expanded into bikes and a platform for local gear repairs.
Insight: Super-local, niche services can succeed with minimal online presence and good community engagement.
“I was surprised, but I think a lot of people also are tired of walking into traditional shops…”
— Ryan Goodwin (15:01)
(18:39)
Founders: Oscar Urana & Eric Rico
Idea: Rent high-end baseball bats to kids via monthly subscription ($17–$45+), reducing upfront costs for families.
Results: $50,000/month in recurring revenue; started lean by testing with 15 families.
Scaling: Invested $40,000 in inventory, used in-person tournament booths and targeted Facebook ads to acquire customers.
Insights:
“Test your idea first...those first 15 families at the academy proved that the concept could work.”
— Nick Loper (21:47)
(22:44)
Founder: Shelby Merrill
Story: Stay-at-home mom in Utah rapidly built a profitable service cleaning car seats ($5,600 in first four months) and selling how-to courses after her TikTok videos went viral.
Business Model: $40 per car seat plus travel; upsells digital courses ($75–$500) to followers who wanted to start their own business.
Expansion: Hired staff, expanded geography, and limited cleaning to protect work-life balance.
“I could be the someone who does this.”
— Shelby Merrill (23:20)
“Shelby identified this pain point that every parent has. Look, the car seats are gross. And she went out and solved it, didn’t overthink it…”
— Nick Loper (27:30)
(28:01)
Founder: Zachary Howahan
Idea: Serving Taylor Swift fans with commentary, analysis, and podcasting (“Evolution of a Snake”); grew to 250k+ followers.
Monetization: Patreon has 15,000 members ($3–$25/mo), generating ~$90k/month; free podcast supports a larger audience.
Insights:
“I wanted to own what I did.”
— Zachary Howahan (29:31)
“The best audience isn’t the biggest one, it’s the most engaged one.”
— Zachary Howahan (31:53)
(35:05)
Idea: Voice actors read and dramatize user-generated Reddit stories (“Am I the A-hole?”/“Am I the Jerk?”) for YouTube and podcast release.
Scale: Over a million YouTube subs, 12,000+ Spotify reviews; daily publishing; estimated $20k–$100k/month.
Model: Curates and packages free, viral online content to new formats; voice acting is main expense.
Insight:
“What’s cool is that you don’t always need to create original content from scratch...sometimes the content already exists.”
— Nick Loper (38:05)
(39:15)
Founder: Lexi Tobin
Idea: Designs and manages custom marriage proposals, typically earning ~15% of proposal costs, with brand/affiliate income from TikTok (300k+ followers).
Revenue: Six figures per year; best month: $20,000.
Origin: Started as a passion project for family, went viral on TikTok, recognized market demand.
Insight:
“According to the Knot...one in four proposers now pay someone to help them pop the question. One in four, that’s like a pretty sizable market...”
— Nick Loper (42:43)
(44:13)
Founder: Paul Castor
Idea: Identified a gap in design/quality for wooden bow ties; created improved versions, scaled via Etsy and direct sales.
Results: ~$20,000 profit in a year as a high school senior, automated with contractors when at college.
Product Expansion: Added carbon fiber “Carbon Cravat” line and wholesale.
Insight:
“He didn’t invent wooden bow ties. He just set out to make better ones.”
— Nick Loper (48:26)
(49:34)
Founder: Josh Boutel & wife Mandy
Idea: Full stack marketing agency exclusively for dog trainers (especially positive reinforcement/R+ community).
Services: Web, automation, lead gen, tailored content.
Revenue: $10,000+/month via highly targeted, specialized offerings.
Insight:
“He’s not competing with every generic marketing agency out there. He’s the dog training marketing guy. And when you own a niche like that, I think $10k a month is just the starting point.”
— Nick Loper (53:01)
On why everything is monetizable:
“Just about any skill is monetizable if you’re excited enough about it.”
— Nick Loper (01:53)
On scaling solo businesses:
“Trying to do everything yourself, you’re going to get burned out in those 14 hour days.”
— Nick Loper (13:19)
On opportunity in overlooked industries:
“Every industry has low standards somewhere… what can you do to raise the bar?”
— Nick Loper (09:06)
On the content model for Reddit stories:
“The real genius here is they’re not creating the core content—it’s user-generated. The Reddit users are creating it and they create it every single day.”
— Nick Loper (37:01)
On age and entrepreneurship:
“He didn’t let his age stop him. Some people didn’t take him seriously because he was young, but he proves them wrong with results.”
— Nick Loper (49:05)
For inspiration, motivation, and lots of concrete, repeatable ideas—this is a must-listen episode for would-be side hustlers!