709: 10 Creative Side Hustles That Make Real Money – Part 9

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0:01:18 This summer, we went to part of the Rubik’s Cube World Championships, which just happened to be in
0:01:24 Seattle right around the same time our kids had gotten very into cubing. The main event here is
0:01:31 the traditional 3×3 Rubik’s Cube, and the fastest solvers in the world can do it in under five
0:01:36 seconds. It’s mind-blowing to see because the fingers are moving so fast, you can’t even really
0:01:42 tell what’s happening, and then all of a sudden it drops and it’s solved. But what was even more
0:01:46 interesting, at least for me from a side hustle perspective, is that there was actual prize money
0:01:54 involved. $5,000 for the first place competitor. It was yet another illustration that just about any
0:02:00 skill is monetizable if you’re excited enough about it. And I tell you that story to tell you this one.
0:02:06 Nothing gets me more excited than finding cool creative ways to make extra money and then sharing them
0:02:12 with you. It is time for our annual Thanksgiving tradition on the show, a roundup of 10 of the
0:02:17 most interesting and inspiring side hustles that have come across my desk this year. We’ve got product
0:02:22 businesses, we’ve got service businesses, we’ve got content businesses, something for everyone in what
0:02:28 is always one of my absolute favorite episodes to put together. And I want to start with one I definitely
0:02:36 had to do a double take when I saw it. This is Cutting Edge Firewood, the world’s first luxury
0:02:44 firewood company. I’m talking about $59 firewood boxes, $250 firewood racks, cooking wood for high-end
0:02:51 grills and wood-fired pizza ovens. And people loved it. They grew to serve 30,000 plus customers,
0:02:56 including some celebrity clients. They end up winning appearances on Netflix and the Today Show and national
0:03:02 media. But of course, success invites competition, and as many as 50 imitators pop up and try and play
0:03:08 in the same space. But this is a story about taking the most boring, commoditized product imaginable
0:03:13 and turning it into something that people brag about buying. Here’s founder Leroy Height.
0:03:21 I founded Cutting Edge Firewood in 2013, but the idea started years earlier where I went to school at
0:03:28 Berry College, where I launched a few different businesses. And I realized something fairly simple.
0:03:36 Firewood had never been disrupted. Everyone treated it like a commodity, really even like lower than a
0:03:43 commodity, because half of all firewood in the United States at the time that was sold was bug-infested,
0:03:50 and the rest was rotten with mushrooms growing out of it. But I realized it’s not a commodity. It’s an
0:03:57 experience. It’s the aroma, the crackle, the warmth, the flicker of the flame. It brings people together,
0:04:02 and people will pay a premium for that experience.
0:04:08 So Leroy’s first firewood company actually started while he was at Berry College. He joins a couple
0:04:13 classmates. They start this firewood company called Premier Firewood. He’s working as an operations
0:04:17 manager. He’s going through the entrepreneurship program there. He kind of catches the bug at that
0:04:23 point. And after graduation, they keep it going, but can’t really make it work. The math isn’t adding
0:04:29 up. They’re spending hours delivering wood for minimal profit at that point. So he moves on. He gets a
0:04:33 job at Chick-fil-A. He gets a job at Enterprise Rent-A-Car. He gets a corporate job in downtown
0:04:39 Atlanta. He’s doing his thing. But he can’t stop thinking about firewood. It’s this obsession. So he
0:04:47 jokes with his wife, hey, when my 1993 Geo Prism breaks down with 266,000 miles on it, when the car
0:04:51 breaks down, I’m going to buy a truck. I’m going to start this firewood business on the side. So two months
0:04:57 into the corporate job, sure enough, the Prism dies. It’s going to cost $5,000 to repair. The car’s only
0:05:04 worth $300. So that weekend, he tells the story about fasting and praying and trying to figure out
0:05:09 the next step. But by the end of the day, he’s decided to go in on this firewood company. So
0:05:15 Monday morning, he goes to work and they fire him on the spot. Still doesn’t know why, but he later
0:05:19 says, that’s the best thing that ever happened to me. Now, I’m not starting the firewood thing as a
0:05:25 side hustle. I’m going all in. 2013, I went all in, maxed out every credit card I could get my hand
0:05:31 on, worked 110 hour weeks doing hard manual labor. Everyone thought I was crazy, except for my wife
0:05:36 who stood by me. Now think about this, because it does sound crazy. This is a product customers are
0:05:43 literally going to light on fire. And maybe because of that, most firewood companies don’t have any
0:05:47 website. They don’t have any branding. There’s no such thing as customer service. You buy firewood from
0:05:52 some guy on the side of the highway or some small moldy bundle from the grocery store. Now, Leroy
0:05:59 grew up in Northwest Georgia, maintaining the family wood pile. So he knows firewood. But as an adult,
0:06:05 he’s frustrated. Hey, I still love building fires, but I can’t find good quality wood anywhere. The guy
0:06:10 down the street dumps off, you know, dirty piles of wood into his backyard or into the driveway. And he’s
0:06:15 got Leroy’s got to stack it and carry it himself. He’s thinking there’s got to be a better way. So
0:06:20 cutting edge starts in 2013. With this vision, we’re going to be the world’s first high end firewood and
0:06:28 cooking wood company. The product is hand selected hardwoods, oak, hickory, cherry, pecan, apple,
0:06:36 maple wood. Each of these pieces goes through this 48 hour kiln drying process. It’s dry, it’s mold free,
0:06:43 it’s pest free, and then trained specialists hand deliver every piece. They toss out anything wet,
0:06:48 rotten, ugly. Only the stuff that is photo shoot ready, that is Instagram worthy, is going to make
0:06:54 the cut. So the business is growing. It’s getting some traction, but it’s not quite enough. In 2017,
0:06:58 Leroy realizes they’re going to need some capital to reach the next level.
0:07:06 2017, we were in a really tight spot. And I went to my wife and I said, Hey babe, I know we have a
0:07:13 two-year-old and a three-year-old little girls at home and you’re eight months pregnant with our third.
0:07:19 What now be a perfect time to sell our house and invest it in the business? And a couple of weeks
0:07:26 later, she had our third daughter at 1130 PM. And then by 8 AM the next morning, I was with the lawyers
0:07:31 selling the house. We took it, invested in the business and reinvented how to do local deliveries.
0:07:37 So that’s what they do. They move into a rental, they use the funds to get a warehouse, to refresh
0:07:42 the brand, launch a new website, hire some employees. And that’s when Cutting Edge really takes off.
0:07:48 They’re able to drop delivery time from two hours to like 15 minutes. And the product comes in these
0:07:53 really cool, nice boxes with everything you need, matches, fire starter, kindling, along with the wood.
0:07:59 It’s like white glove delivered to the exact location the customers want inside or outside
0:08:04 the house. The company grows to 25 employees. Eventually they’ve got eight trucks. They’ve got
0:08:10 tens of thousands of customers nationwide. They get national media attention. The Today Show,
0:08:16 Fox and Friends, Hulu, Netflix, lots of newspapers and magazines. They get recognized as one of the
0:08:23 fastest growing private companies in Atlanta. We were able to take over the Atlanta market. And in 2019,
0:08:29 we started shipping nationwide because we had really taken over the internet, all things firewood.
0:08:36 And we started putting up yard signs in Metro Atlanta and a few other cities in the Southeast and
0:08:43 really became like a household name in Metro Atlanta and had explosive growth and continue to grow.
0:08:46 And I exited the business about a year ago.
0:08:52 Customers don’t just leave reviews for cutting edge. They write love letters. Leroy pioneered this
0:08:57 luxury firewood category, built it into a national brand, proved you can take the most commoditized
0:09:02 product against stuff that people are literally lighting on fire and turn it into something premium.
0:09:06 And then he eventually sold his stake in the business for an undisclosed sum.
0:09:12 So what’s the takeaway is that every industry has low standards somewhere. So you find the ones where
0:09:17 people are really doing the bare minimum and then ask, what can you do to raise the bar? Obviously,
0:09:23 Leroy didn’t invent firewood. He just refused to accept the mediocrity that he saw in the industry.
0:09:28 It was like an obsession. It annoyed him. And he turned it into an experience worth paying for.
0:09:34 Creative side hustle number two is called Boss as a Service, which I think we’ve mentioned on the
0:09:39 show before. But it’s another story that I love because it’s about solving your own problem and
0:09:45 turning it into a business, scratching your own itch. This comes from Manasvini Krishna, who was
0:09:52 a lawyer who then left the law job to start a tech law startup, which sounded great, right? Except she
0:09:58 quickly realized something was missing. When she was working the day job, she had deadlines. She had
0:10:03 accountability. She had co-workers depending on her. When she started working for herself,
0:10:09 none of that. If I missed a goal, she says, there was no consequence. She needed someone to help keep
0:10:16 her on track, but couldn’t find a service that fit. So she ends up building Boss as a Service really for
0:10:23 her own use case. How it works is you pay as little as $25 a month to hire a quote unquote boss who keeps you
0:10:30 accountable. You send them your to-do’s for the day or the week. They’ve got to be quantifiable because
0:10:35 you’ll need to prove that you did them. It could be a screenshot. It could be a photo, whatever. And if you
0:10:40 don’t follow through, they follow up and they don’t stop bugging you until it’s done. Now, admittedly,
0:10:46 service isn’t for everyone. If you’re already really disciplined, you probably don’t need it. But if you’re
0:10:53 someone who never misses a client deadline, but sometimes misses on your own goals, that’s the gap that this
0:11:00 one fills. Manasvini started by personally keeping users accountable. She was the boss for hire. Now,
0:11:05 her first customers came from the Beeminder productivity community. Then she got a little
0:11:11 bit of traction on Product Hunt, but it was still just a side project. Then she created this quiz called
0:11:17 Why Do I Procrastinate? It was based on a productivity book. She puts it up on Hacker News. It goes viral.
0:11:24 When people get their quiz results, there’s a link to Boss as a Service. Tons of people sign up. Now,
0:11:31 three months later, someone else, maybe a customer, posts Boss as a Service to Hacker News again. And
0:11:37 it goes viral again. Multiple people were signing up every minute, Manasvini says. And it was just me
0:11:42 running the service. I couldn’t handle anymore. So she had to shut down signups and start a wait list.
0:11:47 Now, for most startups, virality is the dream, right? But there’s still manual labor on the other
0:11:53 side of this. So for her, it was overwhelming. She’s working 14-hour days. She’s like, I gotta hire
0:11:58 a team. And that didn’t come naturally. She said she struggled to delegate. She made some bad early
0:12:05 hires. But when she found the right operations lead, everything changed. That was when I realized
0:12:09 this wasn’t a side project anymore. She said it was a serious business. The other realization
0:12:15 that she had was that virality isn’t a great long-term growth strategy. She says, I was great
0:12:20 at launching things. I was great at getting the first few customers. But taking a business from 100
0:12:26 users to 1,000, I had no idea what I was doing. So she turned to mentorship. She started learning
0:12:33 SEO systematically, booking weekly calls with experts. She’d go back, apply what she learned. She’d get stuck
0:12:38 at the next level, and then book another call, lather, rinse, and repeat that for months. And now SEO is
0:12:45 one of the biggest traffic drivers for Boss as a Service. Today, Boss as a Service has over 2,500
0:12:53 users at a minimum of $25 a month. That’s over $60,000 in monthly recurring revenue. Solo founder,
0:12:59 profitable. They’re also expanding beyond basic accountability. They’re adding coaching, goal-setting
0:13:03 support, building a mobile app too. They’ve even got interactive challenges like,
0:13:08 eat the frog for tackling your hardest task first. A few takeaways for me here. One,
0:13:13 you know, virality is exciting, but maybe not sustainable. You got to have a real growth plan
0:13:18 for consistent lead flow. Two is you might need to hire sooner than you think, especially if you do
0:13:22 have that viral moment, because trying to do everything yourself, you’re going to get burned
0:13:27 out in those 14-hour days. Not sustainable. And three, the bigger lesson probably is that there’s money
0:13:33 in accountability services. Boss as a Service doing $60,000 a month. There’s another one we’ve
0:13:38 referenced before called My Body Tutor in the health and fitness space. They’ve got like 7,500 customers
0:13:43 at almost 400 bucks a month. That’s a $3 million monthly run rate on that one. So people are going
0:13:49 to pay to help stay on track. And what I love about this one is Montesvini didn’t complicate it. Look,
0:13:55 she had this problem. She built a simple solution, tested it with real users, and then scaled it when it
0:14:00 worked. I think that’s a great side hustle playbook right there. Creative side hustle number three is one that
0:14:06 is near and dear to my heart, and that’s a ski tuning service. But of course, you could swap that out with a
0:14:11 niche maintenance service in whatever hobby that you’re into. Side hustle show listener Ryan Goodwin does around
0:14:19 $20,000 a year with his seasonal side hustle and credited a simple Google business profile with helping him get
0:14:24 started. Hey there. My name is Ryan. I run a little ski tuning shop out of my garage here in
0:14:31 Denver. It’s called Peak Rover Tuning. This project started as an SEO experiment. Actually, I was messing
0:14:36 around with the snowboarding blog. I figured it couldn’t hurt to set up a Google My Business profile
0:14:43 and then link it to my site. So I put up a page advertising ski tunes and pointed the GMB to that.
0:14:48 And it just sat there for a while. But then the snow came and the shops got backed up and I started
0:14:53 getting phone calls. It didn’t really matter that I had no reviews and I was working out of my garage in an
0:14:59 alley. And it turns out it’s kind of a cool way to connect with the neighborhood and people who like
0:15:04 the things that you like. So over the last couple years, business has grown little by little. Working
0:15:10 on my techniques, picked up some new tools, expanded service. I’d offer local delivery. So most of downtown
0:15:15 Denver, you don’t even need to haul your stuff around. It’s like pretty big advantage over the big
0:15:21 shops. I was surprised, but I think a lot of people also are tired of walking into traditional shops and
0:15:26 getting sold on new equipment and kind of feeling like not cool and your gear just gets passed down
0:15:31 the chain or tossed in a machine. For marketing, what’s worked for me is just staying listed on Google,
0:15:37 collecting reviews. For something like this that’s so super local, it might just be enough. It’s kind of
0:15:44 surprised how many people actually do this. I connected with a local tuner a while back, does the same thing,
0:15:49 but he also does bikes in the summer. And we started kind of trying to build stuff to make it
0:15:54 easier for others to do what we’re doing. So we recently launched an iOS app. It’s called
0:16:01 Gear Fix on the App Store, but you can also find us at Gear Fix IO. The general idea is if you need
0:16:05 your gear fix, there’s probably someone in your neighborhood that has some knowledge and experience
0:16:09 and likes tinkering. And it’d be cool if we could help build a network of little neighborhood gear
0:16:15 shops. Peakrover.com if you’re in the Denver area and need a little tune up before hitting the slopes
0:16:22 and gearfix.io if you’re thinking, this is probably something I could start in my own garage. Thanks to
0:16:26 Ryan for sharing that. I’ve got more creative side hustles coming up right after this.
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0:18:48 number. Quo. No missed calls, no missed customers. Creative side hustle number four is a baseball bat
0:18:55 rental service that’s doing over $50,000 a month. This one hits on a few of my favorite themes,
0:19:00 scratching your own itch, starting lean, and building recurring revenue. This one comes from a couple
0:19:06 friends, Oscar Urana and Eric Rico, who grew up playing baseball together in Florida. Eric actually
0:19:11 got drafted by the Toronto Blue Jays. And after his playing career, he opened up this youth baseball
0:19:16 academy. And that’s where he started noticing something. Kids would show up with talent, but they
0:19:20 would be discouraged because they couldn’t afford the equipment. And they’re competing against teams
0:19:26 where every kid has brand new gear. And here they are with these beat up hand-me-down bats. And here’s
0:19:33 the thing. A quality baseball bat is pretty expensive. We’re talking like $300 to $500 up
0:19:38 front. And for a lot of families, especially when their kids are constantly growing and growing out of
0:19:44 equipment, that’s just not in the budget. So Oscar and Eric figure there’s got to be a better way.
0:19:51 So they come up with Bat Club USA, BatClubUSA.com. It’s essentially a bat rental subscription. So instead of
0:19:57 dropping $500 all at once, families pay a monthly fee starting as low as $17 a month for younger
0:20:04 players and going up to like $45 or more for older kids with higher end bats. And they run these on
0:20:09 12-month contracts. But here’s the thing. This was really smart. Before they went all in, they tested it
0:20:16 with 15 different families at Eric’s Baseball Academy and get overwhelmingly positive feedback. And so that
0:20:23 gives them the confidence to really go out and invest. So there’s a recurring revenue element to
0:20:28 this business, but it’s inventory. So they have to come up with $40,000 of their own money in this case
0:20:34 to go out and buy inventory to serve $2,000. They’re buying a lot of bats. So Eric uses some of his
0:20:40 baseball connections to source these bats. And they start by storing everything in his garage. And their
0:20:46 marketing approach was really hands-on at first. So they would start to show up at tournaments in
0:20:51 Florida, in Texas. They would set up a booth. They would talk to the parents. And what made it work
0:20:57 was that kids could walk away with a bat that same day. So they bring in the inventory with them. Hey,
0:21:02 subscribe right here, instant value, you know, as low as $17 a month, no shipping delays, no nothing.
0:21:07 And then those kids eventually become their sales force. Everybody else on the team is like,
0:21:11 hey, dang, where did you get that? Oh, it’s from these guys. So later, they ended up scaling up with
0:21:17 Facebook ads. They would target parents who were already following baseball-related brands, baseball-related
0:21:20 content. And Facebook knows everything about you. If they’re hanging out at baseball tournaments on the
0:21:26 weekend, you’re going to be a prime candidate for this. And that combination took them to that $50,000
0:21:32 in monthly recurring revenue. Now, rapid growth brought its own challenges. They had issues with
0:21:36 fraud. They had to stop taking prepaid cards, inventory tracking, you know, shipping
0:21:42 30-inch long metal things across the country. Inventory tracking becomes kind of this logistical
0:21:47 challenge to solve. But they ended up building out a system with Stripe and Shopify to help keep
0:21:53 everything organized. And their biggest piece of advice was to test your idea first. You got to
0:21:59 validate before you invest big. Those first 15 families at the academy proved that the concept could
0:22:04 work. And it gave them the confidence to go out and scale the thing and put down that inventory
0:22:09 investment. And now they’re looking at expanding into other youth sports using the same rental model,
0:22:15 making athletics more accessible across the board. I’ve got a couple questions around the depreciation
0:22:20 of this equipment, like how long before a bat wears out. I don’t know if it’s just superstition,
0:22:23 but when I was playing, some people were really protective of their bats. Like,
0:22:28 they believed it only had a certain number of hits in it, and they didn’t want anybody else to
0:22:34 waste them. So there’s something there. But really cool example, Bat Club USA. Check it out if you are
0:22:40 in the market for some rental equipment, a rental baseball equipment, or thinking, well, what else
0:22:46 could I pivot that same model to? And we’ve seen, you know, rental musical instruments. That’s been a
0:22:51 thing for a long time. But I’m curious what other ideas you might have on a creative rental business.
0:22:59 Creative Side Hustle No. 5 is a car seat cleaning service. And this one brought in $5,600 in its first
0:23:04 four months. And it started with this simple question, why doesn’t somebody do this?
0:23:10 Shelby Merrill is a stay-at-home mom in Utah with two little kids under three years old. And she loved
0:23:15 staying at home with them, but she wanted to find a way to bring in an extra $1,000 a month. Good to have
0:23:20 that kind of concrete goal. She says, I came up with the idea to start cleaning car seats because
0:23:25 cleaning car seats is the worst. My kids’ car seats are always dirty. And every time I clean them,
0:23:32 I think there needs to be someone who does this. Her light bulb moment is when she realizes I could be
0:23:37 the someone who does this. So she took the idea and ran with it, mostly working at night after the kids
0:23:42 go to bed and made that $1,000 in profit in her first two weeks. So here’s the timeline. And this is
0:23:47 pretty wild. Saturday is when she comes up with the idea. Also on Saturday, she registers the LLC.
0:23:52 She completes her legal paperwork. Sunday, her sister-in-law designs a logo. By Monday,
0:23:57 Car Seat Scrub Club is officially in business. Her first client is her cousin. She did it for free
0:24:03 and asked her to help spread the word to other moms and offered to waive the travel fee in exchange for
0:24:09 those referrals. Then she went hard on the marketing. She posted on Instagram stories, posts. She shared in
0:24:15 local Facebook mom groups. She even ran some paid Instagram ads. And by Tuesday, three days after the
0:24:20 initial idea, she’s got her first paying customer. And then two weeks later, she’s already made $1,000
0:24:26 in profit. So after she puts her kid to bed, like just logistically, how this is happening, she’s
0:24:31 driving around, picking up car seats anywhere from one to five in a night. And this has got to be pretty
0:24:38 localized to service. And now she’s expanding to doing strollers as well. $40 per car seat plus a $15 to $25
0:24:43 travel fee, depending on how far it is. She brings them home to the garage, takes them apart, cleans them
0:24:48 according to the manufacturer’s manual. There’s different seats apparently have different guidelines.
0:24:52 So when people book on her website, they’re going to tell her the model of the car seat. So she can
0:24:58 look it up beforehand. They air dry overnight in the morning before the kids wake up. She ties a bow and
0:25:04 thank you note to each seat and then returns them guaranteed delivery before 9am. How’s that for
0:25:09 turnaround service? Because the people are going to need the car seats to go about their day. And then
0:25:13 it’s back to regular mom mode for the rest of the day. I don’t know how sustainable that is. Just
0:25:17 where you’re supposed to sleep when the kids are sleeping when you got young kids. But in any case,
0:25:22 really cool example of taking action. And yes, since I know you’re asking part of that initial weekend
0:25:28 setup was a legal consultation and getting insurance before getting started smart move when you’re taking
0:25:33 apart other people’s car seats. But then what is really interesting, Shelby makes this night in the
0:25:40 life of a car seat cleaner video for her business Instagram. Cross posts it on TikTok because, well,
0:25:46 you know, whatever. I already made it. It’s fine. Doesn’t think much of it. Then her mom texts her at
0:25:51 like 11 at night. Your video is doing so well. You got to go in and respond to these people’s comments.
0:25:57 So, she opens up TikTok and finds thousands of new followers. The next day, she posts another video.
0:26:02 So, in two days, she goes to like 30,000 followers. And that first video, the night in the life of the
0:26:09 car seat cleaner, has two and a half million views. And that virality helped and it hurt at the same
0:26:13 time. It brought awareness. It drummed up business. It helped her actually earn money from TikTok’s
0:26:19 creator fund. But it also meant competitors started to pop up in her area because people watched her
0:26:23 videos and they started their own car seat cleaning business. Now, here’s where it gets even more
0:26:28 interesting. She goes viral, right? Her DMs start to explode with people asking to how to start their
0:26:33 own car seat cleaning business. Now, the first day, she says, Shelby says, I was just responding to
0:26:37 everyone and telling them how to do it. And I was probably on my phone for like nine hours that day
0:26:42 because I was just trying to help everyone out. Then she realized, wait, why am I giving this away for
0:26:49 free? So, she launched Scrub Club Courses with a couple different options. A $500 ultimate business plan
0:26:56 course and a $75 mini course. Through August, she had earned the $5,600 from cleaning the car seats.
0:27:02 That was like 100 plus, you know, car seats that she had done the overnight thing for. Plus, she’d made
0:27:08 an extra $6,000 from selling the courses to other people who wanted to start the business. So, she’s
0:27:13 expanded now to a couple different counties in Utah. She’s hired a couple other cleaners to kind of expand
0:27:18 the geography there. And the money has helped her family pay off some debt and book a trip to
0:27:25 Disneyland. The next goal is to upgrade her Honda Civic to a new car. Shelby says she’s limiting the
0:27:29 car seat cleaning business to four nights a week so she doesn’t get burned out and to maintain some
0:27:35 boundaries between work and rest and family time. Now, what I love about this is Shelby identified this
0:27:40 pain point that every parent has. Look, the car seats are gross. And she went out and solved it.
0:27:45 Didn’t overthink it. Registered the business on Saturday. Had a paying customer by Tuesday. And then
0:27:50 when competition emerged from her own viral success, look, I’m not going to panic. I’m going to find
0:27:56 another revenue stream teaching other people how to do what I did. Super smart. So, look around at the
0:28:00 things you hate doing. Chances are other people hate doing them too. Maybe they’re going to pay someone
0:28:05 to handle it. Remember Erica Crouppen’s pet waste removal business? Exact same thing. Oh, I got to go
0:28:09 pick up after the dog. Hey, look, if I hate doing it, it’s going to be a pain point for other people
0:28:14 too. Maybe I could turn that into a business. Creative side hustle number six. This is probably
0:28:22 the most interesting one that’s come across my desk this year. It is the Swiftologist. This is
0:28:29 Zachary Hauerhan, who is known online as the Swiftologist, who has become a full-time Taylor Swift
0:28:36 content creator. Could you turn your own fandom into a full-time income like Zachary has? Today,
0:28:41 he’s got over a quarter million followers across YouTube, TikTok, and Instagram. And he was even
0:28:46 featured in HBO’s documentary about the Swift-Scooter Braun controversy. I don’t know what that is,
0:28:53 but he was on HBO about it. Zachary is a journalist by training. And before making videos, he was writing
0:28:57 full-time, but he noticed something. And then that was, articles have limited reach these days.
0:29:03 Your main goal as a writer is for your ideas to be heard, he says. But video-first content reaches
0:29:10 a much wider audience in a more engaging manner. Zachary’s been a Taylor fan since he was 13,
0:29:16 but his content creation really kicked off during the pandemic when Taylor’s surprise dropped her
0:29:22 album Folklore. Reaction videos were becoming a thing on YouTube, Zachary explained. It was this
0:29:27 seismic event in Taylor’s career. I usually just wrote down my first impressions, but this time I wanted
0:29:33 to record it for posterity. That video ended up gaining some traction, then came the Evermore album,
0:29:39 and then Zachary’s day job started laying off writers. I hated being in a position where something
0:29:45 could be taken away from me, he said. I decided I wanted to own what I did. And I’ve highlighted that
0:29:51 in my little working doc here because that’s such a powerful line. I wanted to own what I did. I think
0:29:56 that’s something we can all relate to. So in 2022, he starts treating it like a full-time job,
0:30:01 the Taylor Swift’s content, while he’s still working the main job. And two years later, it actually
0:30:07 becomes his full-time focus. Today, he co-hosts a podcast called Evolution of a Snake with Madeline
0:30:14 Rubicam. It goes year by year through Taylor’s entire recording catalog in her career. It generates
0:30:21 between 50 and 100,000 listeners every week. This is according to Pedestrian, that TV. The free version
0:30:25 of the show, it’s available just like this one, wherever you get your podcasts. But the real money
0:30:31 for Zachary and for Madeline, in this case, comes from Patreon, where they share exclusive episodes,
0:30:37 they do deep dives, they have content that is apparently too spicy for the algorithm, according
0:30:44 to Patreon. Today, they’ve got 15,000 Patreon subscribers paying between $3 and $25 a month.
0:30:50 And let’s assume that most go for like the $6 tier on average. There’s a whole bunch of different
0:30:55 options you can choose from on that page. And now, split between co-hosts, you know, there’s some
0:31:00 podcasting overhead, there’s some costs involved, but we’re doing the math on that. 15,000 subscribers
0:31:07 times a $6 monthly average is $90,000 in top-line subscription revenue, just for the podcast alone.
0:31:14 Now, here’s what makes Zachary different from other fan creators, is that he’s not 100% fanboy,
0:31:19 he’s critical, right? He’ll analyze Taylor as a real person, including the stuff that might be
0:31:25 uncomfortable. For example, he did a video essay about her billionaire status and her private jet
0:31:30 usage, and the Swifty community didn’t love it. He’s actually gotten death threats before,
0:31:34 people take this stuff really seriously. He told Pedestrian.tv,
0:31:40 people misconstrue me wanting to critique her as me being a covert hater. But here’s the thing,
0:31:45 look, he’s seen her in concert 20 plus times, he’s met her at secret sessions, he calls her the world’s
0:31:51 greatest songwriter, he just refuses to pretend that she’s perfect. His advice for building an audience
0:31:56 is to be consistent and to show up week after week. He told Authority Magazine, people will meet you
0:32:02 where you are, but you have to show up for them frequently. The best audience isn’t the biggest one,
0:32:07 it’s the most engaged one. For that reason, you got to live in the comment section. Zachary also gave
0:32:12 the advice to balance what you love with what the audience loves, even when those conflict,
0:32:17 and not to measure success by the numbers alone. Sometimes the content you really put your heart
0:32:22 into doesn’t resonate as widely as something that didn’t matter to you at all, he said. But it’s just
0:32:27 as important to scratch that creative itch. What I find interesting here is Zachary is tapping into
0:32:34 an existing passionate audience. He didn’t create Taylor Swift fandom, but he did become a trusted
0:32:40 voice within it by bringing his journalism skills to fan content. And he treats it like a job. He posts
0:32:45 consistently, he does quality analysis, he takes the time to engage with his community, and he’s not
0:32:50 afraid to be contrarian, even if it brings him some haters. The Patreon model works really well because
0:32:56 super fans, they want more than just the free stuff. They want the unfiltered takes, the deeper analysis,
0:33:02 the stuff that may be a little more nuanced than a TikTok video is going to allow. And they’ll pay for
0:33:08 it. The book 80-20 Sales and Marketing comes to mind here. If we start out with the huge addressable
0:33:14 market, the Taylor Swift fans, the Swifties, maybe 20% of those seek out additional information about her,
0:33:20 the kind of content that Zachary produces. And maybe 20% of those are willing to pay for even more.
0:33:26 So the question is, could you do this in your niche? It could be gaming, it could be sports, it could be a
0:33:32 TV show, whatever it is that you’re obsessed with. Could you bring that same level of commitment and
0:33:37 analysis to the game? The playbook here is just what Zachary’s done. Bring the real expertise, be
0:33:43 consistent, build community, and then figure out a way to monetize with subscriptions. Zachary proved that
0:33:49 you can turn fandom into a career if you’re willing to do the work. More creative side hustles in just
0:33:55 a moment, including getting paid to read Reddit posts and the six-figure wedding proposal planner
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0:35:06 this Black Friday want to remember. Creative side hustle number seven is getting paid to read
0:35:14 Reddit posts. Now here’s a content model that’s so absurdly simple. It’s reading Reddit stories out
0:35:20 loud that ask, am I the jerk? This is a podcast called Am I the Jerk? They take stories from Reddit,
0:35:26 usually from am I the a-hole subreddit. They’ve got voice actors who perform them. They might add some
0:35:32 commentary and then they publish every day. There are over a million subscribers to the Am I the
0:35:37 Jerk? YouTube channel. Their podcast with more or less the same content has over 12,000 reviews on
0:35:44 Spotify. So lots of people tuning in over there. Some example episode titles include Vegan Friend
0:35:49 Demands We Eat a Vegan Thanksgiving Dinner. Entitled Mom Wants Me to Babysit Her Three Kids
0:35:55 for Free. Chinese Restaurant Reuses Customers’ Leftovers to Save Money on Food. It is Reddit
0:36:01 content arbitrage and is working really well for this business. Pretty straightforward concept. People
0:36:08 submit their real-life drama to Reddit asking if they’re in the wrong, most of the time knowing that
0:36:13 they’re not. Am I the Jerk takes those stories, dramatizes them with some voice acting, and then
0:36:18 packages them together as 20-minute episodes. Some of the YouTube videos are quite a bit longer than
0:36:23 that. But the appeal is it can be background content. People can listen in while they’re driving, while
0:36:29 they’re studying, while they’re working out, doing chores, and the stories are relatable. It’s entitled
0:36:35 co-workers. It’s overbearing parents. It’s frustrating partners. It’s stuff that everybody has dealt with,
0:36:40 or there’s a voyeurism aspect to it. On both the podcast side and the YouTube side, they’re publishing
0:36:48 daily over 1,500 episodes at press time. And revenue estimator tools put their potential earnings between
0:36:55 $20,000 and $100,000 per month just from YouTube. And then you can tack on podcast sponsorship revenue
0:37:01 on top of that. They’ve also got a spinoff show called Am I the Genius? Same model, slightly different
0:37:06 angle. And the real genius here is they’re not creating the core content. It’s user-generated.
0:37:11 The Reddit users are creating it, and they create it every single day. You don’t have to worry about
0:37:16 running out of material. Am I the jerk is just curating it and repackaging it. A lot of times,
0:37:22 you might not even need a script writer. The stories are free. The only real cost is voice actors and
0:37:28 production time. And actually, the recent ones sound like they’re, in my opinion, fairly low-grade AI
0:37:35 voices. But people are still tuning in. Plus, the format is pretty evergreen. A story about a bad boss
0:37:41 or a nightmare mother-in-law from three years ago, still relevant, still relatable. And here’s the
0:37:47 thing. Am I the Jerk isn’t alone in this space either. There’s rslash. There’s one called Mark
0:37:52 Narrations. There’s a bunch of other channels doing basically the same thing. Reading Reddit stories,
0:37:59 monetizing with ads and sponsorships. And Reddit keeps pumping out the drama every single day. So
0:38:04 the takeaway here is that curation and then repackaging to a different medium is a business
0:38:09 model in itself. What’s cool is that you don’t always need to create original content from scratch.
0:38:15 Sometimes the content already exists. And with Reddit’s upvoting, you can see what resonated by
0:38:22 what is risen to the top of those subreddits. You just need to make it more accessible, maybe more
0:38:28 entertaining, presented in a different format. I think this one is ripe for replication in another
0:38:35 niche. Whatever it is that you’re into, financial advice, relationship questions, tech news. There
0:38:41 is no shortage of user-generated content in pretty much any niche out there. The question is whether
0:38:46 you can package that in a way that adds value, that builds the audience, and that is going to be
0:38:50 monetizable in some way through YouTube views or through podcast sponsorships. The bar to create
0:38:55 something like this, super low. You got to have some recording equipment. Maybe not. If you’re
0:38:59 going the AI route, I don’t know. This is a crazy new world to me. I was really excited when I came
0:39:05 across Am I the Jerk? So check that one out. And big thanks to eBizFacts for highlighting that one,
0:39:10 because I think it’s a pretty cool example. That was number seven on the list, getting paid to read
0:39:17 Reddit posts. Number eight is the six-figure proposal planner. Now talk about a niche I never knew
0:39:23 existed. Professional proposal planning. This comes from Alexi Tobin in New York. She helps people
0:39:29 plan marriage proposals. Talking lights, flowers, photography, filming the moment, coordinating
0:39:33 vendors. You got to have vendors at your marriage proposal these days. In any case, she’s built this
0:39:39 into a six-figure side hustle while working a full-time corporate job. In her best month,
0:39:45 she made over $20,000. And it all started by helping her brother-in-law propose to her sister.
0:39:53 In 2019, her brother-in-law asked for help planning his proposal to Alexi’s sister. She told CNBC she’d
0:39:59 always been known as the planner in the family. So she goes all in for the brother-in-law. She orders
0:40:04 picture frames, string lights across this archway. She’s putting candles in paper bags. She’s setting
0:40:09 everything up at this beach house in New York. Then to capture the moment, she films her sister
0:40:16 running down this white runner into her fiancé’s arms. And the whole time, Alexi’s having a blast.
0:40:22 The whole process. The planning, the coordination, the surprise, the celebration afterwards. So a few
0:40:28 months after that, she decides to post the proposal video that she made on TikTok. Didn’t expect much.
0:40:33 It goes viral. A hundred million views. Friends, family, strangers, everybody starts pouring in,
0:40:39 asking for help with their proposals. She realized, oh my gosh, there’s actually demand for this service.
0:40:44 So she did what any good entrepreneur would do. She started charging for it. So here’s what proposal
0:40:49 planning looks like. Clients come to her wanting to pop the question. They’ve got no idea how to execute
0:40:55 it. And so Alexi helps them handle everything. She typically hires one to three vendors per event.
0:41:00 It could be a photographer. It could be a florist. Maybe it’s a musician. And right now, a proposal
0:41:06 with five vendors, she says, can cost upwards of $10,000. And the number is climbing as the wedding
0:41:13 industry gets more and more expensive. Lexi keeps about 15% of that as her fee, as 15% of the event
0:41:18 planning fee as her profit. But where it gets interesting is that isn’t her only revenue stream.
0:41:23 She also makes money from brand deals and affiliate marketing through TikTok, where she now has over
0:41:28 300,000 followers on Instagram as well. And she posts the proposal reactions. People love
0:41:34 watching them. So that kind of content fuels her own social media, which then drives more clients,
0:41:39 more brand partnerships, very self-fulfilling or virtuous circle in that way. Now, over 12 months,
0:41:46 she brought in six figures in revenue with a median monthly income of $9,000. November 2023 was her best
0:41:51 month ever, according to CNBC at $20,000. And she’s not just doing proposals anymore. She’s doing
0:41:58 bridesmaid proposals. This is inviting friends to be in your wedding party. She’s doing engagement
0:42:03 parties. She’s planning birthday parties. She’s even doing full weddings now. And all of that is still
0:42:08 a side hustle because she’s still got a full-time job in ad tech where she earns, quote unquote,
0:42:14 substantially more than her side hustle. So it’s tough to give up that gig. But she still spends up to 40
0:42:19 hours a week on her side business on top of 60 hours a week at her day job. So that’s pretty
0:42:24 grueling. That’s 100 hours a week in total of work. So maybe not sustainable in the long run. But she
0:42:29 says she’s investing all of her side hustle earnings into the market while trying to live off just her
0:42:34 corporate salary to really accelerate that path to financial independence. Now, what’s interesting
0:42:43 about that CNBC article where Lexi’s featured is, according to the NOT 2023 real wedding study, one in
0:42:49 four proposers now pay someone to help them pop the question. One in four, that’s like a pretty sizable
0:42:54 market, much more than I would have expected. So Lexi narrowed in on just that specific part of the
0:43:00 wedding industry, just the proposal, not the whole wedding starting out. And I think that specificity, that
0:43:05 niching down really good for business, less competition, clear positioning gets people talking. Oh, I didn’t know
0:43:12 that was a thing. And oh, shoot, I need some help with that. So here’s a high emotion moment in somebody’s life
0:43:19 where they would be willing to hire some help. If they knew it exists, she says, yes, it does exist, you can hire me
0:43:24 proposals are stressful, people want it to be perfect, they’re willing to pay for somebody to handle the detail so they can
0:43:30 just enjoy the moment. I think Lexi did a really nice job of identifying that gap, filling it and then
0:43:35 building this content engine around it that creates those multiple revenue streams. And she did it all
0:43:40 while keeping her corporate job because she’s playing that long game. The question is, could you do something
0:43:44 similar? I mean, maybe she’s got proposals on lock. I mean, I don’t know if she does them remote or just
0:43:48 it’s got to be in New York, whatever it is. But could you do something similar for another life moment,
0:43:56 a baby announcement, a gender reveal, a retirement party, some milestone birthdays? I don’t know. I
0:44:02 think there’s something to this niche event planning type of thing here. So that’s the formula, find the
0:44:07 event, offer the service, document it, build that virtuous cycle. As the audience grows, you can start
0:44:14 to monetize it in a few different ways. So that was creative side hustle number eight. The next story on
0:44:22 our list of creative side hustles today is about a high school kid who turned a hobby into around $20,000 in
0:44:29 profit. Paul Castor started woodworking at around age 12. After watching some YouTube videos, he would make
0:44:36 cutting boards, bottle stoppers, he would do bowls, he would sell them occasionally on Etsy, but mostly to
0:44:43 family and friends. Of course, his first customer was his mom. Then somebody gives him a wooden bow tie as a gift.
0:44:50 He thought it was a cool idea, but this particular one was pretty chunky. He thought it was unattractive. It
0:44:55 was poorly finished. He figured, look, I could do better. And it turns out he was right. And that turned
0:45:02 into Crooked Branch Studios wooden bow ties number nine on our list of creative side hustles today. So Paul
0:45:09 noticed something about the wooden bow tie market on Etsy. Most of them were either too large, too chunky, or
0:45:14 they were just flat, boring, lacking depth. Not a lot of middle ground. So he wanted to create what he
0:45:21 called a Goldilocks version. Something that looked and felt like a classic fabric bow tie, but made out of
0:45:28 wood. Smooth contours, three-dimensional, not too thick, not too thin. And he starts experimenting. And he
0:45:34 actually started out using PowerPoint to design the profile before graduating to some CAD software. Once he had
0:45:40 the shape and contours he liked, he added fabric in the center, which made it less cold, made it easier
0:45:47 to customize. And he was able to source some really cool reclaimed exotic woods, like walnut, cherry, maple,
0:45:52 zebra wood, coco bolo. I don’t know if I’m pronouncing that right. And then he priced each bow tie
0:46:00 between $40 and $50 each. Listed them on Etsy. And then the natural search and discovery features
0:46:06 on Etsy are what drove those initial sales. And he quickly realized that, hey, these are selling a lot
0:46:11 better than the bowls and cutting boards that I used to be making. Like, here’s something really unique.
0:46:18 So he started getting requests for customizations. So he would do laser engraving for initials on the back.
0:46:22 People wanted their names. They wanted dates. If it was going to be like a groomsman gift kind of thing.
0:46:27 So the wooden bow ties are selling well on Etsy. And Paul sets up his own shorefront called Crooked
0:46:32 Branch Studio, which would allow a little more flexibility in his marketing. He says that move
0:46:38 directly led to about $6,000 in increased sales and boosted his credibility. It actually got him
0:46:44 featured on NPR’s How I Built This podcast. And while he was still in high school, Crooked Branch Studio
0:46:51 hit $40,000 in revenue, of which he said about $20,000 was profit in a single year.
0:46:57 But then college happens. And Paul knows he can’t keep up the same pace of production. But instead of shutting
0:47:02 down the business, he hires three private contractors and partners with a couple different manufacturing
0:47:07 companies to help keep building the bow ties, which I thought was a pretty smart move for a young kid.
0:47:15 This let him continue to sell over 2,000 wooden bow ties a year, both retail and wholesale, while he’s busy
0:47:21 studying engineering, computer science, and business at USC. During this time, the business is still pulling in
0:47:26 around $1,000 a month in profit with less than one hour a week of his time.
0:47:32 Basically, passive income as a college kid. Love it. Now from there, Paul moved to expand the product
0:47:37 line. Wood was really cool and all. That’s what gave him his start. But what else can we make bow ties
0:47:43 out of? So he launches a sub-brand called Carbon Cravat, bow ties made out of aerospace carbon fiber.
0:47:49 That sounds pretty cool. Marketed them as the bow tie made from rockets, according to Startland News.
0:47:54 Different appeal. Car guys love it. Airplane enthusiasts love it. It’s this high-tech material
0:48:01 of the future. Paul also gets into wholesale, meaning he found four or five retail stores to
0:48:07 carry his products, which he said amounted to around 10% of overall sales. And an interesting side benefit
0:48:13 of that was that customers would see them in the stores, and then they would come to his website for
0:48:18 custom orders or for wedding packages. So the takeaway here, for me at least, is Paul sees
0:48:25 this product category that already existed but wasn’t done well, in his opinion. He didn’t invent
0:48:30 wooden bow ties. He just set out to make better ones, literally building a better mousetrap kind of a
0:48:36 thing. Etsy is crowded, no doubt about that, but there’s still opportunity if you offer something
0:48:42 unique or higher quality than what’s already out there. The other lesson is outsource when you need
0:48:47 to scale. Like Paul built the business hands-on, look, it’s me making these things in high school,
0:48:54 but then as his time diminishes, as he moves across the country, he systematically replaced himself with
0:48:59 other people who could do that work, other contractors, other manufacturing partners. He turned this
0:49:05 labor-intensive operation into an essentially passive income stream. Really cool, really inspiring.
0:49:09 And he didn’t let his age stop him. Some people didn’t take him seriously because he was young,
0:49:15 but he proves them wrong with results. This business doesn’t appear to be as active now,
0:49:20 but looks like it had a really solid run. Paul built something real while most kids in his age are just
0:49:25 looking for summer jobs, minimum wage type of stuff. So that’s kind of entrepreneurial thinking,
0:49:30 I think is going to set him up really well for the long term. You can check it out at
0:49:38 crookedbranchstudio.com. Creative Side Hustle No. 10 is a marketing agency, which by itself is not
0:49:44 that exciting, except this is a marketing agency specifically for dog trainers. This business is
0:49:52 called DigiWoof, digiwoof.com, and according to eBizFacts, it’s generating over $10,000 a month. But it’s
0:49:57 this kind of hyper-focused niche agency that a lot of people probably going to dismiss as being too
0:50:03 small. But I think that’s exactly why it works. Josh Boutel, who runs this business with his wife,
0:50:09 Mandy, isn’t some random marketer who picked dog trainers out of a hat. Oh, the keyword research led
0:50:13 me to this niche. No, he’s got over 10 years of running his own certified dog training business
0:50:20 in San Francisco. It’s called City Pups SF, helping dog owners deal with leash reactivity,
0:50:25 separation anxiety, real problems that dog owners are dealing with. So he knows the industry. He knows
0:50:29 the clients. He knows what dog trainers are struggling with because he was living in this world. They’re
0:50:34 not outsiders parachuting in to, quote unquote, disrupt an industry that they don’t really understand.
0:50:40 So DigiWoof, the agency, offers everything a dog trainer needs to market themselves online.
0:50:46 Website design, graphic design, social media marketing, email and SMS marketing, process automation.
0:50:54 And the website’s only been around since 2021. So this is a relatively new operation. But when Josh
0:50:59 is talking to dog trainers, he’s one of them. He can speak their language. It’s not some generic agency
0:51:05 pitching marketing services. And having lived it, he understands the specific pain points that dog
0:51:10 trainers are dealing with. They don’t want to mess with tech. They want to train dogs. That’s why they got
0:51:15 into the business. So Josh builds the systems that automates a client onboarding, appointments,
0:51:21 scheduling, follow-ups, all the administrative stuff that keeps trainers from doing the stuff that they
0:51:27 actually love. And even more interesting is that it’s actually even more niche than just targeting dog
0:51:30 trainers. I debated about including this because like, I don’t know if people will know what this is.
0:51:37 Josh is creating content specifically for the R plus community within the dog training world.
0:51:42 that is positive reinforcement training. He’s got a podcast called the digital dog trainer.
0:51:49 He’s writing blog posts about how dog trainers can use mini courses to market themselves, how to grow an email
0:51:56 list, how to manage Google reviews. It’s not just generic marketing advice. It’s really tailored to a niche
0:52:03 within a niche. And that is a formula I think can work across any different niche that you happen to have a foot in
0:52:09 the door to. Josh mentioned that he uses the software high level to deliver the services
0:52:14 at scale. That way he’s not, you know, custom building everything from scratch. There’s some
0:52:20 built-in templates, automations, and systems that are working across all his different clients. And so other
0:52:26 people are using high level to do pretty much this exact same thing in other niches. Maybe it’s music
0:52:32 teachers, maybe it’s dance studios, maybe it’s tattoo parlors, maybe it’s churches, whatever that you
0:52:37 might have that, that little in or that industry knowledge of. And the services are basically the
0:52:42 same, you know, websites, social media, email marketing, automation. The difference is the
0:52:47 positioning. We’re really going to be the expert in this one industry. And we’re going to seek to
0:52:52 understand that client better than anybody else. And a lot of people will think that niching down is going
0:52:58 to limit your business. But I think Josh proves the opposite. If you’re trying to grow your R plus
0:53:03 dog training business, he’s the obvious choice. He’s not competing with every generic marketing agency
0:53:09 out there. He’s the dog training marketing guy. And when you own a niche like that, I think 10 grand a
0:53:14 month is just the starting point. Really cool example of coming to dominate a niche. So I hope these
0:53:20 businesses got some creative gears turning in your head. To recap, we had the luxury firewood service
0:53:26 taking a commodity product and making it an experience. We had boss as a service selling
0:53:33 some accountability. We had the ski tuning business in Denver. We had the car seat scrub club in Utah
0:53:39 and the subsequent side hustle that spun off helping other people start a car seat cleaning business.
0:53:46 We had the Swiftologist, a full-time Taylor Swift content creator. We had getting paid to read
0:53:52 reddit posts with the example being, am I the jerk? Check them out on YouTube and whatever podcast
0:53:56 platform you are. See how they’re doing that. And could you spin off something similar in your own
0:54:02 niche that you like? We had the six figure proposal planner helping people plan epic wedding proposals.
0:54:09 We had a teenager making wooden bow ties and selling those in retail stores and online. And we had
0:54:16 digi woof the marketing agency specifically for dog trainers. So I want to wish you a really happy
0:54:22 Thanksgiving to you and your family. Make sure to take a moment for gratitude today and every day to appreciate
0:54:29 what you have, how far you’ve come. I am grateful for you spending some time with me today and really every time
0:54:34 you spend some time with the side hustle show in your earbuds. I’m grateful for everyone who sends me these great
0:54:39 side hustle stories like the ones you heard today. And I’m grateful for our sponsors for helping make this
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0:54:51 our sponsors in one place. Thank you for supporting the advertisers that support the show. That is it for
0:54:56 me. Thank you so much for tuning in. If you’re finding value in the show, the greatest compliment is to
0:55:01 share with a friend. Until next time, let’s go out there and make something happen. And I’ll catch you in
0:55:05 the next edition of the Side Hustle Show. Hustle on.