9 SIMPLEST Claude AI Side Hustles You Can Do Over The Age Of 50

Most people who go looking for the simplest cloud AAI side hustles that you can do over the age of 50, do the same thing. They either try a side hustle where they're making minimum wage, something like Uber or Uber Eats, or they go online. They try a Fiverr account or an Etsy shop or a faceless page about nothing where you're selling digital products that nobody cares about because that's what every video told them to do. The problem is that's the most crowded room on the internet. Fiverr alone has 4,000 poem listings and most of the sellers are 22 years old and charging $5. So, you're competing on price against kids with no rent, and a lot of them probably aren't even from the US. So, what actually happens is you put in three months, you make almost nothing, and you decide that AI isn't for people like you. And it's no knock on you, the advice was just wrong. Instead, you should either use the knowledge that you already have, or you should take a simple job on your own street that nobody in that room will do. Something like checking an empty house every two weeks or emailing 10 car dealers for a neighbor. And then you let Claude do the paperwork half, the tables, the letters, the checklists, etc. The result is you making your first dollar this weekend from somebody who already knows your name. For instance, a retired software tester in Vermont charges $65 a visit. A retired executive in Chicago charges $895 a report. And Ownwell keeps 25% of what it saves on your property taxes. And a guy with a laptop can do that on his own street. And once one neighbor pays you, the next three come from her. For instance, a stranger who found you by price doesn't send referrals. So this gets easier every single month instead of harder. Now, the reason I know so much about this subject is because I've made over $10 million from something that started off as a side hustle. And I was making videos about AI on YouTube three months before Chat GBT even came out. So, I've put thousands of hours into AI at this point. And every hustle in this video is a real person doing it right now with the name, the price, and page on the screen. And no part on this list came out of a machine cuz I checked every single one. So, if you appreciate me making this type of content and you want to see me make more of it in the future, then let me know by gently cheersing that like button. And let's jump into it right now. Okay, so the first one is going to be a YouTube channel about your old job. So, this is the one that I'd pick for myself. Obviously, I did a YouTube channel. I basically went $300,000 in student loan debt in order to get a doctorate so that I could become a pharmacist that kind of hated my job and was super burned out. And so, what I did is I created the YouTube career channel that I wish I had when I was trying to figure out what to do with my life. And since then, I've helped literally thousands of people land jobs, establish their personal brands, start side hustles, start full-time businesses, and scaled their YouTube channels as well. I started off just teaching other career coaches how to grow on YouTube, but then it expanded to a bunch of other things as well. And basically, I help anybody who has a problem to solve for other people, right? So, if you're interested in making educational content that actually helps to solve other people's problems, then I highly recommend you check out my live training. That'll be the first link in the description, the pin comment below, because that's who we help, right? We don't work with prank channels or gaming channels or entertainment YouTubers or anything like that. Now, a great example of somebody who was watching a video just like this a few months ago is Jyn. She was a nurse for 33 years. She's 60 years old, and she didn't start a business. She didn't learn to code. She just sat down in front of a camera and explained what she already knew with nursing, the stuff that she'd said out loud 10,000 times at work. And then she put it on YouTube. And today, she makes over $10,000 a month from AdSense alone, plus her first sponsorship and affiliate deals. And she got to quit her job as a nurse, and she's now traveling all over the United States in her camper van, which is epic. Craig is a realtor in Montana in his late 60s. and he'd been posting on YouTube for years, spinning his wheels, not getting any results. Then one of his first videos using our system got over 100,000 views immediately. And of course, he got tons of leads from that video. And of course, he talks about selling houses in Montana. That's the channel. So, here's how to do this. Every hustle in this video that I told you about, they all work, but the problem with all of them is they need traffic, right? You need people to actually know that you exist in order to pay you for a product or a service. And the best way to get traffic by far, in my opinion, is YouTube, specifically social media. So you start with YouTube, use it as the mother platform, and then you automatically syndicate that content to the other platforms. And so you don't have to chase clients and chase customers. They will start coming to you. This is what I've helped countless amounts of people do. And it actually works better if you're over 50 because anybody can look up general information on Google or CatchBT or Claude. But what you can't look up is wisdom, knowledge, and experience. That's the kind of thing that you can only have with age. And so you probably have been noticing older people blowing up left and right on YouTube. And there is a reason for that. There's a supply and demand imbalance. If you're on the older side, it is significantly easier for you to get success on YouTube. All right, YouTube just got 10 times easier and nobody is talking about it. You used to need an entire film crew and it used to be a full-time job for you to just do any work at all on YouTube. But now you can get work done in as little as 15 to 30 minutes a day and you can actually grow a fulltime YouTube channel. That's exactly what I'm going to be talking about at the live training that we're doing this week. Exactly how to start YouTube step by step for beginners. So, click the link in the description in the pin comment below to check that out. Guys, I will be answering questions before, during, and after the live training. It's completely free. Plus, I'll be giving away an AI that is designed to help you pick your niche if you don't have one in the first place. Or if you already have a niche, it's going to help you make it 10 times better. So, really looking forward to talking with you guys. This is stuff that we never talked about before. So, click that link in the description and comment below and I look forward to seeing you there. All right, so the next one is going to be Homew Watch. Now, Charlie Pausnik is 65. He was a software tester and he retired and in December of 2022, he started driving to empty houses in Vermont and that's the side hustle, right? That could be the business. People leave for the winter or the summer and somebody has to check the house. Charlie charges $65 a visit and he tells clients to book at least one visit every other week. So, here's the job. You walk through an empty house with a checklist. Is the heat on? Is there water on the floor? Is there mice? Is mail piling up? If a storm is coming, are the chairs off the deck? You take photos, you send a report, you lock up, and it takes 20 minutes, and you get paid $65. Now, do that for 25 houses twice a month. That's $3,250 a month. But a woman in Florida, Diane Pasani, says that she's got 150 clients and three employees doing exactly this. So, this is a real side hustle that you can actually do. Now, Claude builds the checklist for that house and that season, what to check, what bad looks like. Then it turns your phone photos into the report that the owner reads in Phoenix. Then it writes a one-page agreement. Now, you might be thinking, "Well, Shane, who hands a stranger the keys to their house?" That is the question because that's the job, not the walking, but the trust. And Charlie solved it the old way. A newspaper wrote a story about him. And the story in the paper vouches for you, and it says, "This is a real person. Here's his name. Here's his price." And the exact steps to start are going to be on the screen. Pause it if you want them. Now, by the way, I'll also have resources in the description in the pin comment below. It should be the third link down there. These are going to be AI resources as well as prompts that go along with this video and they can be really useful. Now, all of these side hustles on this list really do work. With that being said, they all have the same problem, which is you need customers, right? You need people that are actually willing to pay you money. And depending on your situation, that might end up being really difficult. So, the actual side hustle itself is pretty easy to do and it doesn't take that much time, but you might spend all of your time trying to get customers. And so that's why I made a free live training talking about exactly how I've been getting customers for the last 5 years on YouTube as well as social media just making simple videos. And now it's easier than ever using Claude AI. And if you want to attend that, go ahead and click the first link in the description and the pin comment below. All right, the next one is property tax protests. So there's a company called OwnWell and they protest your property taxes for you and take 25% of whatever they save you. And in their own numbers, they win 86% of the time and the average homeowner saves $774 a year. So, do the math. $774 in savings, 25% cut. That's about $190 a house. And Ownwell just raised venture money to do this at scale. But a guy in your county with a laptop can easily do it for the 30 houses on his street. So, here's the job. The county says your house is worth $400,000. So, you pay taxes on 400,000. But the house down the street, same size, same year, just sold for 350. So, you pull five of those sales, they're public, and you put them in the table. You file a one-page protest, and you show up to a 10-minute hearing. That's it. The evidence is on the county's own website. And here's the part that makes me crazy. Only about 3 to 5% of homeowners ever file one. And this is basically free money. So 95% of people just pay it. And look, I get it. It feels like fighting city hall, but it isn't. It's a form. Now, you might be thinking, Shane, don't you need a license for this? Well, it depends on the state. And I'll be straight with you. Texas makes you register as a property tax consultant, which is 40 hours of classes and an exam. Georgia wants you to be an appraiser, but most states you need a homeowner signature on a one-year authorization, and that's all. So, check your state before you take a dollar. Again, resources in the description in the pin comment below if you're interested in that. That'll personalize the answer for you. Then there's the second half, which is even simpler, which is the exemptions. So, senior exemption, homestead, disabled veteran, surviving spouse, etc., etc. A huge number of older homeowners never filed them. And it's a form, right? You fill it out once and they save every year. And you can charge a flat $100 to do it at their kitchen table. And Chandler Crouch is a real estate broker in Fort Worth. He's also a registered senior property tax consultant and he protests taxes for free for over 40,000 people. Now, why free? because those 40,000 people list their houses with him. And last spring, he put out one video. Abbott's property tax freeze plan already backfired on 190,000 Texans and it got over 128,000 views on a channel with about 12,000 subscribers. And he found 190,000 overvalued homes in one county alone. So the protest is the hook. The house listing is the money. And you do not need a brokerage to copy the first half. So the exact steps to start on this are on the screen. Pause them if this sounds interesting to you. Okay, so the next one is house history reports. So there's a firm in Washington DC called Kelsey and Associates. You hire them and 6 to 8 weeks later you get a story of your house, the year it was built, every person who ever owned it, old photos, what the street looked like in 1920, and the price is $635 to $995. And in New York there's a company called Stoop Sleuths that turns it into a hardcover book. They sell it to realtors as a closing gift. Think about that. A realtor just made a $15,000 commission and a $700 gift that makes the buyer cry is nothing. So, here's the job. Deeds, old city directories, old newspapers, the census, it's all online now. You pull the chain of owners, you find the clippings, like 1931 fire on Maple Street. You find the old photo at the library. You write it up. Claude keeps the timeline straight and writes the story, and you're the detective. Now, you might be thinking, Shane, who in the heck is going to pay $700 for a story about a house? Well, nearly 4 million people watched a local news clip about a Kansas family finding the secrets in their old house. So, people love this stuff, and the number of Americans who do this for a living and have made a video about it is pretty much non-existent. That's why most people don't even know that this exists. Now, realistically, this one probably does have a bit of a low ceiling. This truly would be a side hustle, and it's likely not going to turn into a full-time gig. But when something has a low ceiling, that probably means that there's not a lot of competition, so it wouldn't be that hard to get into. All right, so the next one is a daily money manager. So CNBC did a story on this job and they talked about somebody who goes to an old person's house, pays the bills, balances the checkbooks, sorts the medical paperwork, etc., etc., and of course, watches for scams. And the going rate that they printed is $75 to $150 an hour. Now, a firm in California called Bedrock Fiduciaries charges $165 to $175 an hour to do this right now. And this is the part that got me. The professional association for this job has about 700 members in the entire country. So here's the job. Somebody's mom is 84. She's sharp, but the mail is a pile. The Medicare statements make no sense. And last month, she almost sent $3,000 to a grandson on the phone. Now, her daughter lives in Phoenix and the daughter is your customer. You show up twice a month. You open the mail, you pay what's due, you photograph the statements, and Claude builds the bill calendar, matches your statements against the checkbook, and flags anything that looks like a scam. Then, you send the daughter a one-page summary, and she sleeps easy that night. Now, you might be thinking, "Well, Shane, that's a lot of trust." It is. So, here's the honest part. Get a background check. Get bonded. Get the daughter's power of attorney paperwork right. That takes two to four weeks. And also just ask around in your community. Then it's eight families, six hours a month each at $125 an hour. And that's $6,000 a month. Now, Business Insider put out a video about Americans handling their aging parents money. Has over 285,000 views, and one section of it is just scams. So, the demand is there, but there's not a lot of competition. All right. So, the next one is a social security claiming consultant. So Ray Harris spent more than 30 years as an executive. Then he retired and now he sits down with couples in Chicago and answers one question. When should each of you take Social Security? The spousal benefits, the survivor benefits, etc. The timing between the two of you and he charges $895 for a couple. Other consultants charge $295 for a single and $495 for a couple. And the trade group says that people pay anywhere from $300 to $2,500 for one of these reports. So here's the job. A couple social security decision can be the difference of tens of thousands of dollars over a lifetime, maybe even hundreds of thousands. And most people decide it in the parking lot of a social security office. They don't really put a lot of thought into it. So, the software does the math and there's a program called Maximize My Social Security. It's $49 a year. And Claude turns the printout into a report that a normal person can read, plus the questions they should ask before they file. So, you're the person at the kitchen table who's been through it. Your age is the credential. And you might be thinking, "Well, Shane, isn't that giving financial advice?" No. And this line matters. It's education, not advice. You explain the options and the math. You never touch their investments. You never say, "Buy this." The moment you do, you need a license. And there's a credential for this, which is RSSA. And here's the strange part. An $18.75 IRS number, the PTIN, is enough to qualify you for the program. Now, the program itself is about $3,400 plus a $350 exam. Or skip it, just use the software and stay on the education side. Now, a guy named Trevor Fibs put one video out, which is Social Security at 62 versus 70. The math will surprise you. on a channel with under 10,000 subscribers and it got 1.6 million views. So demand is not the question. The question is whether you'll be the person in your town who does it face to face. We also have a community member R.J. who made a YouTube channel called R.J. the Unretired and he talks about the same stuff and he has videos on social security that have done very well. And he actually got that channel to $28,000 in a single month just a few months after starting the channel. So you can even make content on this and get paid again. Or again, you can get clients and customers by just simply making content on social media, which is what I'll show you how to do with Claude doing 90% of the heavy lifting in the live training that I'm doing this week. So, click that first link in the description, the pin comment below. All right, so the next one is freelancing your old job. So, this is basically you selling the skills that you acquired in the thousands of hours that you spent at your old job, maybe tens of thousands of hours, but instead of getting a job, you just become a freelancer. So, Chrysum, for instance, is an architect at the Port Authority in New York. She's got a full-time job and on the side, 5 to 10 hours a week, she makes 3D pictures of buildings for developers. The same thing that she does at work. And her side business did $414,000 in 2023. And it's not a new skill. It's her old skill that she already knew, just sold to someone else. And I know, Shane, she's 35 and she's an architect. Fine. Scott Tarsy does CAD drawings, the boring technical kind for small companies that can't afford a full-time drafter. He makes about $9,000 a month doing this. So, here's the pattern. What did your company pay you to do? Somebody smaller can't afford a full-time person, so they'll pay you for 10 hours of you on the side. And here's the job. Take the thing that you did for 25 years, like bookkeeping, nursing, HR, project management, drafting, purchasing, and sell it in pieces. The HR person becomes the I'll write your employee handbook for $1,500 person. The nurse becomes the I'll read your mom's discharge papers and tell you what to ask the doctor person. The purchasing manager becomes the I'll get you three supplier quotes person. And Claude does the part that you're bad at, which is turning 25 years into a menu with prices and a pitch. No, most people starting over at 50 have no idea what their skills are called on the outside. And that's not a knock. Nobody ever told you. Now, you might be thinking, "Shane, I'm not going to be competing with 22-year-olds on Fiverr for $5." Then don't. Chrysom's biggest client is a property developer. She started on the freelance sites, but the money came from the one big buyer who needed what she does. So, your buyer is the small company in your town that can't hire you full-time. Email them, not Fiverr. Now, Carlos Singen, for instance, did recruiting for years, and then she started recruiting for other people in other companies, and then she started making videos explaining it. And at about 14-500 subscribers, one video that only got 100 to 200 views got her a contract worth over $100,000. So, like I said before, making videos, making content on social media is basically a cheat code when it comes to actually getting clients or actually making money from your side hustle because it works literally with any side hustle. And the alternatives are going on some website where you're competing against a bunch of 20-year-olds from India or running paid ads or cold outreaching to people which you're probably going to get rejected a lot and it's also just very uncomfortable and timeconuming. So if you want people to actually come to you then making content specifically video content is the way to go. You treat YouTube as your mother platform and then you can syndicate that content with Claude doing 90% of the heavy lifting as well to all the other platforms. So this is the exact thing that Andrea who's a CMO who joined our community did. She obviously had lots of marketing skills as a CMO and she was making 300,000 a year. So, she was already making really good money. But what she wanted was freedom. And so, she started making content on YouTube and then syndicating that content to other platforms. And she ended up getting 37 clients and quitting her CMO career. That's all because of the systems that we taught her, which we'll be going over in the live training we're doing this week. So, click that first link in the description in the pin comment below. And by the way, this is a one-time training. We do have limited seats. Zoom actually caps it at a certain amount. And so, make sure to secure your seat right now. Click that first link. and I look forward to seeing you there. I'll also be answering questions before, during, and after. I'll be giving away an AI that specializes in helping you pick your niche, or if you already have a niche, it'll help you make it 10 times better. And I'll be teaching you exactly how to start this step by step, even if you're a beginner. And this works especially good for people that are over the age of 50. Okay, so the next one is going to be a coach or tutor for your old job. So Mary Lee Ganon is 64. She was a CEO and now she coaches people in their 50s and 60s on how to run things. She charges $100 to $200 an hour and she calls it a side gig. Tara Lzinski is a math teacher. She started teaching math online through a site called Outschool. And her best month was $22,735. So, same job, different customer. And instead of doing the thing, you teach the person who has to do the thing. So, here's the job. The nurse about to take her boards, the new manager who just got promoted and is terrified, the 24-year-old bookkeeper who has never closed a month by herself, the guy studying for the electrician exam, etc., etc. They will pay you $60 to $150 an hour for one hour with someone who has done it a thousand times because their boss won't teach them. And the textbook doesn't know what actually happens on a Tuesday. So Claude can build the curriculum, six sessions, what's in each one, the homework, it writes your why me paragraph, it writes the five questions that you ask on the first call to see if they're a fit and you show up and just be the person who has done the thing. Now you might be thinking, well Shane, I'm not a teacher. Mary Lee wasn't either. She was a CEO. The person paying you isn't buying teaching. They're buying the 25 years. Nicole, one of our community members, did this for GRC, which is governance, risk, and compliance, which is about as boring as a job title as it gets. And she did it for years. And she started making videos explaining it. And now she teaches it. And she had under 60,000 subscribers, but she made it to over $80,000 in a single month. Josh did the same exact thing with it and cyber security. He made it to over $185,000 a month with under 200,000 subscribers. And that money isn't ads. It's people who watched them explain the job and then paid them to teach it. So the exact steps to start this are on the screen. You can pause it if you want to. And also in the live training this week, I'll be going over exactly how we helped all these people get results. So click that first link in the description, the pin comment below. And that brings me to the very last one, which is home inventory documentation. So a guy named Fred Knap has been teaching retirees this side hustle/ business for years. You walk through somebody's house with your phone. You write down everything they own, the TV, the couch, the tools in the garage, grandma's ring, etc., and you hand them a list with a price on every line. Now, he says the going rate is $300 to $550 per house. And a company in North Carolina called Reclaim starts at $500 a house. So here's the side hustle. When a house burns or floods, the insurance company asks one question. What did you lose? And the homeowner has to remember every single thing standing in the parking lot. If you can't prove it, you don't get paid for it. So people pay to have the list made before anything happens. And almost nobody has one. Only 47% of homeowners have home inventory. And that's the insurance industry's own survey. So more than half of the houses on your street are a potential customer. And chances are if you just mention that you do it to one of your neighbors, there's a good chance they're going to hire you because it could potentially save them hundreds of thousands of dollars. Now, you might be thinking, "Shane, I'm not an insurance person." You don't have to be. You're not negotiating a claim. That takes a license and you're not doing that. You're the person with the phone and the clipboard. That's it. So, here's the part that used to take a weekend and now takes 20 minutes. Let me show you. I made up this house for the demo. So, the prices are real for 2026, but the house isn't. And I walk the living room and talk into my phone. Samsung 65-in TV bought in 2023. good condition, gray sectional, 3 years old, Bose soundbar, etc., etc. And I paste those notes into Claude with this prompt and watch. Boom. Room, item, brand, what it costs to replace today, what proof they need, like a receipt, a photo, a serial number, etc. A flag on anything over $1,000 that should get a real appraisal. Then it adds up every room, and it writes the cover note for the insurance agent. And it gives me 10 things that people always forget, like the attic, the Christmas decorations, the tools, etc. Now, that's a $500 deliverable from a walk and a prompt. And they might even pay you to take pictures and document everything as well. Now, who pays first? Well, the insurance agent in your town. Ask them when a client asks how to do a home inventory. Who do you send to them? The answer is probably nobody. Now, it's you. So, six houses a month would be about $2,700. And of course, this is my estimate. It may vary depending on where you live. And one more thing, Clark Howard, the consumer money guy, did an entire episode called Essential Home Inventory before it's too late. And over 16,000 people watched that one episode. and over 200,000 people follow his advice. And the number of people who do home inventories for a living who have ever made a video about it, zero. Zero that I could find. So remember that. We're coming back to that right now. The exact steps to start this one are on the screen. If you want to get started with this, you can just go ahead and pause the video and follow those steps. So I know that 99% of you are just going to watch this video. You're going to get a ton of value out of it. You're going to download my free resources in the description, the pin comment below. Get a ton of value out of those. And you're definitely going to attend my live training because that is something you absolutely do not want to miss out on. So again, click that first link in the description, the pin comment below, and you're going to get a ton of value out of that. And we are not going to end up working together, and that is completely fine. I always want to give 10 or even 100 times more value than what I receive. With that being said, there's going to be 1% of you, maybe 0.1% of you out there that want a one-on-one mentorship or a one-on-one handholding experience, or you want us to literally just do the work for you. If that sounds like you, go ahead and click the second link in the description in the pin comment below to book a call directly with us. But only book a call if you're very serious about growing and making money on YouTube. One-on-one coaching or done for you work is very timeconuming. We can only work with a few people at a time and it is very expensive. So the types of people we typically work with are going to be professionals with at least 10 years of experience or people that are younger but they're overachievers. And basically these are people who have problems that they've solved in their life. They have wisdom and they want to educate or help other people overcome those problems. We also work with business owners who want to get more views, grow their brand, get more leads and make more sales and make more revenue from YouTube. We also work with YouTubers who are getting a ton of views, but they're struggling with monetization or they have a dead channel and they want to revive the channel or pivot niches. And we also work with YouTubers that are crushing it, but they want to crush it even harder. And we also work with people that have large audiences on other social media platforms and they want to bring that audience over to YouTube because they know it's the best. So, if that sounds like you, go ahead and book that call by clicking the second link in the description, the pin comment below. And we look forward to speaking with you. But again, only do it if you're very serious about growing and making money on YouTube and really treating it like a business. And also check out this video right here to see exactly how we helped nurse Jen go from zero to a full-time income in about 6 weeks with YouTube. And also just talking about what she already knew in her nursing career. And you can check that out by clicking right here.