
Loading summary
Ashley Kerr
I don't have the money to invest. It's the number one thing we hear from rookies. But here's the thing. Some of our most successful guests started with nothing. They side hustled their way to a down payment. One even flipped couches off of Facebook marketplace for $10,000 a month. Another sold exotic plants and netted $100,000 in two years. Somebody else made more money dog sitting than some of her rental properties were producing. And every single one of them use that cash to buy rental property.
Tony J. Robinson
Today, Ashley and I are breaking down eight real side hustles that real rookie guests use to fund their deals. This is in theory, this isn't hypothetical. These are people who sat in this chair and told us their stories. And for every single one, we're scoring it on the same five point scorecard so you can figure out which one fits your life. We're covering what it is, what it costs to start and what you can realistically earn. And most importantly, if you exactly how that guest turned that side Hustle dollar into their first rental property.
Ashley Kerr
This is the Real Estate Rookie podcast. I'm Ashley Kerr.
Tony J. Robinson
And I'm Tony J. Robinson. And with that, let's get into our first side hustle. So the first thing that we have is the gig delivery. You know, you can think doordash, Uber Eats, Instacart, all those options that are out there. So what is this? Right, so basically you're delivering food or groceries or whatever it may be using your car in an app. There's also maybe one to add on to. This is Amazon Flex. I don't know if they have that out by you, Ash, but like basically you can Uber.
Ashley Kerr
Never even heard of it.
Tony J. Robinson
Amazon. So I live in an area where there's just like a lot of Amazon warehouses. And because that there are a lot of people can, you know, you can basically just get your own car, drive to an Amazon warehouse, they'll load you up with a bunch of stuff and you go deliver it to places around the, around the community. So we, when we get Amazon delivery, sometimes it's the guys and girls in the Amazon truck, sometimes it's UPS or, you know, whoever it may be, but sometimes it's like, you know, Jimmy pulling up in a Civic and he's just pulling stuff out the back of his truck. Right.
Ashley Kerr
You know what, we do have that, we do get deliveries like that sometimes. And I didn't realize that was what it was called, but we actually had a friend that came to us and told us he was interested in buying An Amazon route. So that must be part of it is to, like, you buy the route and.
Tony J. Robinson
Yeah, yeah. And that's a whole nother thing. And I actually have a cousin who's going through that process right now to apply to own a route. So maybe once he's done with that, we'll pull them on. But, guys, there's so many different options now in the gig economy on different ways you can do it. But obviously, Uber Eats, Door dash, Ubering, Lyft, all those are things that you can do. But, you know, before you take it on, you see where the pickup is, where the drop off is, what the pay is, and you can accept or decline each one. And the cool thing here is that you get to set your own hours, right? And you can log on or log off whenever you want.
Ashley Kerr
So the guest that we actually had do this was Josh Janis. And you can go Back to episode 294. So he was door dashing while he was in college. So age 18, 19. And he didn't want to get a traditional job, which is actually pretty hard when you're in college, to accommodate when the party schedule is and when your classes are, to be able to get jobs that you can do in between your classes. I had met this sheriff before, and he was doing an eviction for me. And he had said when he was in college, he used to do maintenance requests. So he would get the maintenance request from the investor in the morning. And then in between his college classes, he would schedule the maintenance request and go do maintenance and then go back to college and go to another class and things like that. But we also had Jordan Scroggins from episode 608, and he actually worked at Geek Squad, and He was mounting TVs and making about 17 to $18 an hour and driving Instacart on the side. So between these deliveries, these people were also studying bigger pockets and learning about different strategies, things like that. So while you're driving, lots of opportunity to do your research. But those are two guests to check out that had made money doing these side hustles.
Tony J. Robinson
Yeah, and Josh Janis from 2 94. I remember him saying that he. He'd actually, like, taken it to the next level where he had, like, multiple cell phones and he was, like, stacking deliveries on top of each other to really maximize his income. So, yeah, really cool options out there to help you maximize the revenue here. Now, let's talk about startup costs next. The startup costs for the gig industry is basically zero, right? I mean, you need a car That I think is less than 10 years old. A valid driver's license, gas money registration office takes a couple of days, but they don't charge you to get on these platforms and some of these platforms or even rent a vehicle to you, you don't own one. Joss mentioned just keeping a phone, mount some good headphones, snacks and water in his car. And that was his full kit to get started here. So very minimal startup costs.
Ashley Kerr
And really with this is there's not really an income limit you can like, you're not limited to the income you can make. It's really just how often you want to drive. So like you could start off with $15 to $20 per an hour when you're starting out. But then as you learn, like we learned from Josh, is to like, you really kind of strategize which orders you pick up so that you're optimizing your time and you could be making 30 to $50 an hour. And that was kind of his secret with running the two phones and doing doordash, Uber eats and postmates all at the same time. So he could just line up deliveries that were all headed in the same direction. So I remember him talking about this one tip that he learned that was made his time way more valuable was like don't drive 10 miles across town for just a $2 tip. So but he said that another cool thing was he actually got free meals sometimes from the restaurants for orders that were unclaimed and things like that. So living expenses, he was cutting into those too.
Tony J. Robinson
Yeah, free food and he's getting paid. Right, so, so that, that was the income ceiling. Let's talk about how it actually funded real estate deal. So Josh used his door dash income to directly fund his first real estate deals, but he did it for two full years. So this wasn't something where it was like, hey, I'm going to jump in and do this for a month or two or you know, he, he was committed to this for 24 months, but it also gave him the added benefit of it actually showed up on two of his tax returns. Right. So he had documented two years of self employment income, which also helped him when it came time to apply for the loan. He also got things like mileage deductions and, you know, reducing his taxable income. But it did both. Right. It gave him the cash, but it also helped build his borrower profile. So it's something that isn't an overnight success like most side hustles and most ways of making money. But if you stick with it long enough, it will give you the cash that you need to get that first deal.
Ashley Kerr
One thing I like about this too, is that you're really getting to educate yourself while you're getting paid. I mean, what jobs can you, you know, start off at? You know, no experience necessary, and start the job and be able to spend most of your time during that job listening to biggerpockets, podcasts, or listening to the books while you drive around. I mean, I think of, you know, most teenage college kids in my area, they're getting jobs where maybe they're working retail or maybe they're working at the fast food place or things like that where you can' go ahead and listen to whatever you want while you're working too. So I think that's also a huge benefit. Plus the flexibility of being able to do it on your own schedule and your own time.
Tony J. Robinson
And last thing I'll say for Josh, he again started off DoorDash Uber eats college kid, and within the span of a couple years built a portfolio worth over a million bucks. Just put that in context. Someone who used DoorDash and UberEats to within a few years build a real estate portfolio worth over a million dollars. That's how straightforward and simple this process is if you just pick a lane and you really dedicate yourself toward it. And the last thing before we get off the DoorDash Uber Eats. I just did a quick search and I tried to find who are some of maybe the highlights of the gig economy in terms of how much money they made. I found three stories. One, a guy named Ronald Coleman, who actually showed his tax returns, showed that he made $114,000 in one year doing DoorDash. Now, he worked crazy hours. He said that he would work somewhere between 12 to 20 hours a day, but he had a strict goal of making at least $400 on, on every day. There was another guy in Oregon named Sam lyon who for 30 days straight worked 12 hours a day. Right? So again, crazy working hours, but he made $8,357, which puts him on pace to make 100k in that one year. So, guys, I mean, obviously long hours, but man, if you want to talk about just like grinding out and being able to do some real, real damage, there are some, some stories for you guys.
Ashley Kerr
Yeah, I mean, think about it. If you're working 40 hours a week now, making 4,000, 5,000, if you're able to double that amount of money and not even work at as many, like not even doubling your hours, just adding on some extra hours like that can be super beneficial side hustle for you. So the next one we want to go over is bartending. So this could be picking up shifts at a bar or restaurant, getting tips and nights, weekends benefit is this is cash in hand. When I was in high school and when I would be home the summers for college, I worked at a restaurant where I didn't bar ton, but I did hostess. And then I started waitressing. And I just remember those piles of cash and going home at night and putting them into my little safe under my bed. It stockpiled that cash. But yeah. So we had Alana Lipman. This was episode 674, if you want to go back. So she was living in a 4 Plex apartment, paying about $850 per month. And she just had this light bulb moment sitting in this apartment as to her landlord was collecting rent from four apartments, but he only had one mortgage to pay. And she just thought maybe I could do this too. So she had been newly separated, had moved to a new town, had almost no capital, so she actually took a bartending job. And her rule was she was very diligent. She set aside every single dollar of tip money and she used that to fund her down payment. So she had no exceptions. It was every single dollar of their tip money went to saving for that down payment. And she did it.
Tony J. Robinson
Now, the startup cost for this, essentially zero. Right. Like most restaurants that you work for are probably going to train you. There are some states that require certain certifications, but, you know, we're talking less than 100 bucks to get those. But there's no equipment, there's no vehicle, there's no inventory. You truly just show up and. And you work. Right. So one of the lower ways. Now, obviously it is maybe a little bit more difficult, depending on where you're at, to go get a job at a bar that's going to pay you well. But even if you start somewhere small and kind of work your way up, zero cost to get started here.
Ashley Kerr
So she was able to, I think, save $10,000 over four months just from bartending. So like you said, depending where you are, this can drastically change what your income would be. But if you're like me and you have no idea how to make any kind of cocktail, you could start at, you know, your dive bar that only serves, you know, beer and wine or, you know, things like that where they don't make any kind of fancy drinks. So you might be able to survive to it or rubbing coke. But I'm Sure. On your high end. I mean, we've all. We went to BPCON Las Vegas last year and I mean, you're spending $30 on one drink, and if you know people tipping on $30, that amount of money can definitely add up.
Tony J. Robinson
So how did it actually fund a deal for Alana? Well, she bought her next property basically entirely from her bartending savings. Her first property was a house hack, and that was a home that was just listed as a single family that turned into a duplex. And she'd Airbnb one side and then immediately fill it the other side and covering her entire mortgage. So she never paid a mortgage on that property. Then she moved out after six months, bought another house a few doors down and repeated that process. And while doing this, she was still working her full time W2 job and she was bartending on the side. So she used the W2 income to qualify for the loans, and the bartending cash helped with the down payments in the furnishing. And today she's got, I think, almost 15 doors across. Short term rentals, long term rentals, and the mix. And she even bought a mixed use building. So again, we're talking about someone who, from very simple, humble beginnings, where probably a lot of our rookies are, since someone who started with a golden spoon in her mouth, was able to build a portfolio in a relatively short period of time by strategically using the side hustle of being a bartender. All right, so side hustle number three is TaskRabbit, right? Or any of those other apps that are similar to TaskRabbit. But basically what this is, it's a handyman style app where you set your own hours and your own rates to to do tasks that people don't want to do themselves. It could be assembling furniture, it could be moving someone, lawn mowing, cleaning, painting, organizing errands, even personal assistant work. You pick the categories you're comfortable with and you set your own price. So it's almost like an Uber, but for service work. Right, so that's the general idea of what this actually is.
Ashley Kerr
So our guest we had on was Dan McDonald. This is episode 341. So he was a marketing researcher in Boston and he was only making $38,000 a year. And his motivation was his girlfriend wanted a nicer apartment, so he ended up trying everything. DoorDash, UberEats, started working part time at Banana Republic, but he ended up doing TaskRabbit. And this is the one where he found that the hourly rates were actually higher and he could actually have Repeat clients through there. So he described himself as a serial side hustler. I remember. But this worked the best for him doing TaskRabbit and doing different things like building IKEA furniture, mowing lawns, moving furniture. Literally whatever came up, he would be open to doing for somebody.
Tony J. Robinson
And just for me, like, you know, volunteering yourself to build more IKEA furniture is a level of pain. I'm not open to experience it for myself. But the benefit for this side hustle is that the startup cost, again, we're seeing a trend here, is basically zero. You sign up, you list your skills, you set your rate, some tasks you benefit from. Basic tools that you hopefully already own. Dan said the only investment was his time and his willingness to do the job that no one else wanted.
Ashley Kerr
Yeah, so he actually ended up doing sixteen hundred dollars in his first month. He filled every available hour that he could. And then over three, three years, he made about $12,000 just doing it on nights and weekends. He actually built the small list of repeat clients. And so they just kept using him over and over again. And it ended up they would just start texting him directly instead of even going through the app, which I'm sure probably eliminates a commission or percentage that the app takes. But yeah, he then even started doing it for an investor, doing it tasks like that for rental properties, which is just getting him into the realm of real estate investing. Same way I got involved in real estate was I worked for an investor. So that's another great way that TaskRabbit can kind of get you in the door into real estate investing without actually having to invest to start.
Tony J. Robinson
Yeah. So how did Dan use it? So he combined his taskrapid income with his other forms of income to save up 3 1/2% down for an FHA loan on a $500,000 duplex outside of Boston. And he combined that with some money he got from a small inheritance. And that property that he bought for 500k is now worth $700,000. Right. Almost 200k in appreciation in about 3 years, at least at the time of the recording. And it all started again with him building IKEA furniture. So again, another very simple, low cost way to get started.
Ashley Kerr
So coming up, a 16 year old made $10,000 a month flipping couches off of Facebook Marketplace and actually used it to acquire 900,000 DOL in real estate. Before she even graduated high school, a corporate Banker accidentally ordered two exotic plans and turned that mistake into $100,000 profit. And one guest built a $15,000 per month digital product empire with zero startup capital. The Flip something for Profit round is next. We'll be right back after a word from our show sponsor.
Sponsor/Advertiser
Billion dollar investors don't typically park their cash in high yield savings accounts. Instead, they often use one of the premier your passive income strategies for institutional investors. Private Credit. Now the same passive income strategy is available to investors of all sizes thanks to the Fundrise Income fund, which is more than $600 million invested and a 7.97% distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com Private pockets to invest in the Fundrise Income Fund in just minutes. The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results. Current distribution rate as of 12312025 carefully consider the investment material before investing, including objectives, risks, charges and expenses. This and other information can be found in the Income Funds prospectus@fundrise.com Income this is a paid advertisement. Most investors spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning to steadily. They focus exclusively on landlords. Whether it's a single family rental, a spur builders risk policy or midterm holiday guests, you get fast quotes, flexible coverage and protection for property damage, liability and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in minutes@biggerpockets.com landlordinsurance steadily landlord insurance Designed for the Modern Investor
the rise of the tech savvy investor is here. You don't need a huge team or tons of overhead to manage rental properties, just the right tools. So I want to tell you about how I use RentReady to get ahead for landlords who treat their time like capital and recognize the cost of sweat equity. This tool gives you everything you need to rent collection, tenant screening, maintenance, accounting so that you're organized come tax season and you can run numbers in preparation for future deals and more all in one platform via a mobile app or desktop. Modern landlords don't just own property, they optimize it Rent Ready will keep you organized, running leaner, and ready to grow. Start with rent ready. Visit rentready.com biggerpockets that's rent R E D I.com biggerpockets and use code BP2025 to get rent ready's six month plan for a dollar.
Ashley Kerr
All right, we just covered three ways to trade your time for immediate cash gig Delivery, Bartending, and TaskRabbit. Every one of those guests use that income to get a down payment. But what if you could use the same buy low, sell high, sell skill you'll need as an investor to fund your first deal? So that's what's up next. And those numbers are going to blow your mind. And the first one we're going to talk about is couch flipping. So this is where you go on Facebook, Marketplace, offerup, maybe even Craigslist or Driving for Couches and see one sitting out on someone's stoop. But you buy underpriced couches and clean them up. So steam clean them, take high quality photos and make a really great listing with measurements, type of fabric, whatever you can to really sell this thing. And you can sell them for two to ten times what you actually paid. So the I guess we'll go into the details of what this actually takes, but our guest that did this was Ava Jurgens. Episode 294.
Tony J. Robinson
Yeah, and Ava had a crazy backstory. She was, you know, 16 at the time when she started doing this, but she found this idea on YouTube. But basically the first couch that she flipped was free. They literally picked it up, cleaned it, and sold it the same day for $200 for a 200, 200 profit. And over time, they improved their processes and tried to figure out what's the best way to do this. And at some point they were able to buy things for 200 bucks and sell it for 1200. And they eventually even scaled this business up to the point where they had to buy storage to start storing all these couches they were flipping. So it was a very small, systematic approach. And who knew that there were that many couches being sold and bought and sold on a daily basis? But she's proof that it works.
Ashley Kerr
And for your startup cost, you need some way to move this couch. So whether it's a truck, a trailer, or access to one, or renting a U haul, so you will need to have that. You're not strapping this onto the top of your Tesla and hauling couches around. So then they eventually got a storage unit. So depending on how you scale, you May need a storage unit or maybe your mom's garage, you can shove these couches in. And then also if you are going to clean them, cleaning supplies, maybe a steamer, things like that. But yeah, I mean, not a ton of startup costs, obviously more than the other ones we talked about, because you're basically using your time for the other ones. And this one, there are still very minimal startup costs for the potential of what you could be making flipping these couches.
Tony J. Robinson
Let's talk about the income ceiling at, at her peak, ava was making 10,000 bucks a month. 10,000 bucks a month flipping couches. Right. They were flipping between 10 to 20 couches per month. Profit was between 200 to 700, and each one took about an hour to two hours of work. But on the high end, she was making almost a thousand bucks per couch, which is insane. So you think about the time that goes into this. Although the startup costs are a little bit higher than the first two that we talked about, the first few that we talked about, the income potential relative to the amount of time that goes in is probably higher on this one as well.
Ashley Kerr
Yeah. And so this couch flipping directly funded Ava's first rental property. She had done a 5050 partnership with her parents on the first deal. And so she was able to take her money from couch flipping to fund the down payment, closing costs and repair costs. And then from there she got her second property, which she actually turned into a short term rental. But she needed about $10,000 in furnishing. So she saved up $10,000 from couch flipping too, to be able to make that second deal work.
Tony J. Robinson
Also, crazy story. By the time she graduated from high school, she had two properties worth a combined 900k in. In value. Talking about someone who is 17 years old being able to do this. So I'm sure all of our, all of our Ricky's listening can do the same as well. All right, on to our side. Hustle number five. This was one I'd never heard of before, and I was super shocked when we actually had this guest on, but it was exotic plant flipping. Okay, exotic plant flipping or really any type of like niche product arbitrage. But what this is, basically you buy rare or trending products at wholesale prices from a supplier, add value by improving or rehabbing them, and then you resell them to retail buyers at two to three times a markup. So Paul, one of our guests, did this with rare houseplants. I kid you not, but the same principle applies here to sneakers, to vintage electronics, sports cars, thrifted designer Clothes, any product where there's a gap between wholesale supply and retail demand. Funny enough, my, my son actually did this for a little while. He would go to different, you know, we're like in Southern California, not too far from like Los Angeles and Orange County. He goes to all these, like, really cool, like, Goodwill stores in these different cities. And sometimes he'd pick up things that he could then resell on the site called Depop. I'm sounding like a boomer right now not knowing what the site's called. It's called Depop. And basically he would find cool things in the thrift store and be able to resell them. You're buying stuff at the thrift store for like a dollar or $2. He could resell it for 30 or 40 bucks on this Depop website. So it doesn't have to be exotic plants. That's just what our guest did, and that's how we're bringing this one to you.
Ashley Kerr
So our guest was Paul Lee. It was episode 295, and he was actually a corporate banker and he proves or rejects the loans for a living. But during COVID when everyone was stuck at home, a lot of people were buying house plants to kind of make their spaces look better. So Paul actually ordered a rare plant from South America from a wholesaler, and he accidentally put in an order for two. So he had to get rid of the other one. And when he listed it online to sell it was somebody paid him two to three times what he had actually paid. So that was kind of his light bulb moment that he could arbitrage plants. And so he reached out to the wholesaler and actually scaled it into a real operation.
Tony J. Robinson
Again, crazy. One of the craziest stories I think that we've had in terms of how to fund your deal, but the startup costs weren't too insane here, you know, a few hundred bucks for your initial wholesale inventory. Paul's average purchase price was about 140 bucks per plant, and he was selling them on average for about 400 right now. You do need a way to care for the plants. You know, in Paul's case, it was a space with good light and, you know, he just needed the patient to like, actually take care of these plants.
Ashley Kerr
A green thumb?
Tony J. Robinson
A green thumb. Me neither. Whatever the opposite of green thumb is is what I got. But the, the real insight here is that the value add was time and not necessarily capital.
Ashley Kerr
So with this, his income ceiling, he actually hit $100,000 in net profit over two years. So he ended up selling 381 plants with an average selling price of 400. And that gave him an average profit of $262 per plant. So that's like 4 to 5k a month. Just as a side hustle. While he still had his full time job too. So not a bad income limit there.
Tony J. Robinson
So Paul's plants funded directly his 3.5% down payment on an FHA $650,000 fourplex in Colorado Springs. Now, great timing. He got a 2.75% interest rate. But Paul knew that the exotic plant market was trendy and temporary. He said no one's going to pay 2,000 for three leaves forever. So he explicitly chose to convert every dollar of plant profit into real estate. That's an asset that stood the test of time. So again, we've got someone who purchased a $650,000 fourplex that cash flows about two grand per month using exotic plants. Like, like, tell me a better backstory than that. So the, the story's there, the proof is there if you want to go after it.
Ashley Kerr
Okay, so our next one, number six, is digital products. And if you've been on Instagram, you've probably seen somebody pushing you how to teach you how to sell digital products. But this is actually a really great side hustle. So you can create digital templates, printables, planners, checklists, worksheets, tons of them. And also if you're a BiggerPockets Pro member, you can go to BiggerPockets.com resource and you'll find all of our free downloads for pro members. Tons of these. So you guys don't have to pay for them. Just go to biggerpockets.com resource okay, but anyways, there's no inventory, there's no shipping, there's no physical product to manage. If you guys don't already know. I spent one time, one year turning my basement into a sweatshop. And I would sew baby clothes and sell them on Instagram and Etsy. I made like $16,000 in the year that I did this as a side hustle. But the worst part was the shipping. I would have to package everything. I'd have to label it, I'd have to print out the labels, all of this, and I'd have to go and physically drop them off at the post office. That was awful. With digital products, this cuts out a lot of that.
Tony J. Robinson
Now, in terms of guest proof, we interviewed Cody berman on episode 654 and he built a digital product business that makes over 15k per month. He had no graphic Design skills, no social media following, no startup capital when he got started. And he positioned himself on the show not as a real estate expert, but as the person who just teaches rookies how to make the money they need to invest. And to prove his model works. Still today he ran a public challenge and he started a brand new anonymous Etsy shop from scratch. Didn't tell anybody about it, and he was hitting 1k per month in revenue within about 100 days.
Ashley Kerr
So with this, the startup costs are effectively zero. So you can use different websites like Canva. Canva has a free subscription. You don't have to pay on Etsy if you're listing on there. They do charge like, I think it's like 20 cents per listing just to have it posted up there. But really your only investment is your time doing research what products you should sell, actually creating the products, which actually has gotten way easier with AI. You could have Claude go ahead and create a product for you and probably just clean it up in Canva, writing the listing descriptions and optimizing search results, things like that to really get started. But effectively very low startup costs.
Tony J. Robinson
And I think one of the things that makes the digital product so appealing is that unlike bartending or doordashing and Uber Eats or even tabs like all the other ones basically we talked about, require a heavy time investment to actually get paid. Like if you stop doordashing, then you don't get paid. There are no residuals on that. But in the digital product space, you can create something once and then reap those benefits for days and weeks and months and sometimes even years afterward right when you create it one time. So I think that's a big benefit here. All right, guys, after the break, we're going to go over two more side hustles you might not expect. One guest made more money dog sitting than some of her rental properties were producing. Another learned renovation skills on her first flip. Plus, we're giving you the five step playbook to go from side hustle income to closing on your first deal.
Sponsor/Advertiser
There's a point where basically every investor realizes traditional financing stops scaling with you. At first it works. You qualify with your income, your job, your tax returns. But as you grow, that model starts to break. Now it's not really about your personal income. It's about the income from your properties. That's where DSCR lending comes in. And it's why a lot of investors end up working with lenders like Host Financial. Host Financial qualifies deals based on property income, not personal income. So you're not dealing with W2s or tax returns or DTI constraints. And with 80 to 85% LTV, you can stay more flexible as you scale. It's just a different framework, one that tends to align better with how investing actually works. If you're buying rentals, refinancing, or growing your portfolio, go to host financial.com that's h o s t financial.com and see what you qualify for.
Ashley Kerr
When you first start something, whether it's a business, a side hustle, or even investing, it feels like you're doing 10 jobs at once. You're figuring out branding, setting things up, trying to get customers, and somehow keep keeping everything organized behind the scenes. That's where having the right platform actually changes the game for millions of businesses. That platform is Shopify. Shopify powers millions of businesses worldwide and handles about 10% of all E commerce in the U.S. it's built to help you manage everything in one place, from inventory and payments to analytics and growth. You can launch a store that actually looks professional using their ready to go templates, and even use built in AI tools to write product descriptions or improve your listings. And when it comes to growth, Shopify helps you market like you've got a full team behind you with easy email and social campaigns to reach your customers wherever they are. Plus, if you ever get stuck, they've got 24. 7 support to help you figure it out. So instead of juggling a bunch of disconnected tools, you can run your entire business from one platform and actually focus on growing it. It's time to turn those what ifs into with Shopify today. Sign up for your $1 per month trial today at shopify.com Rookie go to shopify.com Rookie that's shopify.com Rookie people love
Sponsor/Advertiser
to call real estate passive income, which is interesting because most of the investors I know are very busy. Busy finding deals, busy managing teams, busy worrying they picked the wrong market. Rent to Retirement flips that model. They help investors buy turnkey new construction homes, often 10% below market value, in top rental markets across the country. Their local teams handle the build, the property management and the details so you don't have to. In some cases, Investors even receive 50 to 75% of their down payment back at closing, and there are interest rates as low as 3.75%. They've been trusted partners with biggerpockets for over a decade, and if you want to learn more, visit biggerpockets.com retirement we
all joke that rentals are passive, but if you're spending nights Matching receipts or guessing what a property earned last month. That's not passive at all. Baselane fixes that part of landlording the financial chaos. Their banking and AI bookkeeping system automatically tags every transaction, updates cash flow insights in real time and builds the reports you need for tax season. You can even automate transfers and move money around without paying wire fees. It's just cleaner. Sign up@baselane.com BP and get $100 bonus. Baselane is a financial technology company and not a bank. Banking services provided by Threadbank member FDIC
Tax season reminder for all the real estate investors listening. If you own rental properties, short term rentals, commercial buildings, basically anything that's not your primary residence, you need to know about cost segregation. It's an IRS compliance strategy that lets you accelerate depreciation on your properties, which means you're paying less in taxes this year and keeping more cash in your pocket for your next deal. Cost segregation guys is the go to firm having done over 12,000 of these studies with 500 million in total depreciation identified. Head to cost segregation guys.combp to get a free proposal and see your potential tax savings.
Tony J. Robinson
All right guys, we talked about trading your time and flipping products for profit. Now let's close this out with two side hustles that require almost nothing to start. Just skills or space that you already have. Plus we're giving you the 5 sec playbook to go from side hustle income to closing day. So side hustle number seven dog sitting. So there's sites out there like Rover and Wagner where basically what this is is you host dogs in your home or sometimes you visit clients home using platforms like Rover or Wag. You get to set your own rates, your own availability, your own house rules. Owners search by location, they read your reviews and book you directly.
Ashley Kerr
On episode 668 we had Casey Wen and her husband and they were making $1 million a year in the Bay Area. So they actually were kind of burnt out with what they were doing and she just wanted to find another way out to change their life. And so they actually started hosting dogs in their homes and doing dog sitting.
Tony J. Robinson
So the startup costs on this are near zero. You need a home, a willingness to host other people's animals, a profile on Rover wag. But there's no equipment, there's no vehicles. I guess maybe some inventory, like some dog toys. I don't know. I don't know. I don't have, I don't have any pets. I'm not sure what they need to be happy. These Days. But Casey framed it as the ultimate zero barrier side hustle. You already have the space, you just need to open it up.
Ashley Kerr
The only thing that I would think about this is maybe like some kind of insurance. Like if the pet were to die under your care, you might want to have some kind of insurance, maybe that
Tony J. Robinson
or attack someone else, you know.
Ashley Kerr
Yeah, or attack someone else on your property or something. So like, that would be the only thing that my mind just always goes to liability. And anyone that knows me thinks it's the most annoying thing because they just want to like brainstorm these fun ideas. And I immediately think of the insurance costs and the liability behind this. But yeah, as far as like the income ceiling, it's really market dependent. And we, we learned that from Casey is to, you know, she also did this in different areas. And so the boarding rates really can change. One was like 30 to $80 in some of the metro areas. But then if you have two or three dogs at a time, that could be 60 to 240 a night. I mean, that 2:40 a night, that's like more than my Airbnb gets for a night, you know, and that's not even outing any properties. So there definitely is market dependent on this.
Tony J. Robinson
So Casey used this to fund her real estate deal. Right. So her, her dog sitting kept her family financially afloat during really one of the most uncertain seasons of their lives. That stability gave them the breathing room to make a strategic move. They sold their home in the Bay area, they made 460k tax free on the sale, and they relocated to a different city that actually went to Kentucky. And they specifically moved to the Red River Gorge area because Casey had identified that as a great market to continue to build her short term rental portfolio. And now she's building a short term rental portfolio from scratch using the equity from that Bay Area sell. But without that dog sitting income working as the bridge, they might have panicked into a different financial decision and wouldn't have the freedom, freedom to chase this dream of building this portfolio elsewhere. So not only is it helping her fund the deal, but it literally allowed her to pick up her whole family and move clear across the country and build a new life for themselves that aligned with what they actually wanted.
Ashley Kerr
So the next one is number eight and it's handyman services. So offering basic home repair or renovation services, painting, drywall, plumbing fixes, deck repair, appliances, installing them, just general maintenance, you know, depending on what your skill set is. Or you have YouTube university where you could kind of set your limit as to what you want to do and spend your time watching YouTube videos on how to install ring cameras, you know, things like that. But our guest proof is Elizabeth Esplin. So episode 590. She's a mom of three and her husband actually had a chronic illness and they lost their income. So what they ended up doing is they ended up doing handyman services and that ended up them doing their own flip house. They bought a house next door to them and it was a probate house. And so they worked on it and did all of the work themselves instead of hiring it out. So they actually saved themselves a lot of money doing it that way. But to start up handyman services, you're going to need some basic tools. You can't show up to someone's house and without a hammer and a drill and things like that. So this can vary, you know, depending on what quality you're getting. But you know, you're starting out with all those basic startup, you're probably 200 to $500 basic tools, or you go to your dad's house, borrow his tools anytime you get a job until you save up enough to go and buy your own tools. But yeah, that's really your startup cost or the tools. And again, I would have insurance.
Tony J. Robinson
Yeah. And in terms of the income ceiling, again, highly market dependent and depending on what skills you actually have. But somewhere between 50, 200 bucks per hour is pretty reasonable for handyman. Like, I know for me, if I call a plumber to go check something on the property, they're going to charge me, you know, x amount just to even step foot inside my house, regardless of what it is. Right. So there's a decent hourly rate attached to handyman services. But for Elizabeth and her husband, their handyman business actually became a business. Right. It evolved from a side hustle into a standalone income stream for her and her family. Not just a side hustle. So lots of upward potential there as well. But in terms of how it funded real estate, Elizabeth's first flip was a probate house that she bought for 200k, all in using a combination of HELOC and hard money. Her and her husband renovated it themselves and they sold it for $393,000. Right. Almost 200k that they made in profit on that deal. And they use those proceeds to pay off debt and launch the handyman business, which then gave them the cash flow to feed into their next deal and their next deal and their next deal. So they learned the skill, applied that skill to their first flip, and then they commercialized that skill. In a way that allowed them to get more real estate and produce more income and build more assets. So really was this kind of evolving loop.
Ashley Kerr
Well, thank you guys so much for listening to this episode of Real Estate Rookie. If you are interested in learning more about being a Bigger Pockets Pro member, go head over to biggerpockets.com because we actually added some new perks to being a Pro member including discounts on lending and a really nice discount on insurance for your rental properties with steadily. So go to biggerpockets.com I'm Ashley and he's Tony and this has been an episode of Real Estate Rookie. Thanks so much for listening and we'll see you guys next time.
Tony J. Robinson
Hey rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie Podcast. Now look, you don't need to be an expert. You don't need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener
Ashley Kerr
as a rookie investor. Especially if you just got your first deal. It is all fresh in your minds and you are the best person to tell your story. Give your experience on how you got it done to help someone else get their first deal.
Tony J. Robinson
So head over to biggerpockets.com guest if you want to be a part of our show again, that's biggerpockets.com, and we'd love to have you on the right Window treatments change everything. Your sleep, your privacy, the way every room looks and feels. @blinds.com We've spent 30 years making it surprisingly simple to get exactly what your home needs. We've covered over 25 million windows and have 50,000 five star reviews to prove we deliver. Whether you DIY it or want a pro to handle everything from measure to install, we have you covered. Real design professionals, free samples, zero real pressure. Right now. Get up to 45% off site wide plus get a free professional measure at blinds. Com. Rules and restrictions apply.
Hosts: Ashley Kerr & Tony J. Robinson | Date: April 22, 2026
Ashley Kerr and Tony J. Robinson break down eight real-life, rookie-proven side hustles that have directly funded guests’ first rental property deals. With stories of flipping couches, bartending, digital products, and even exotic plant arbitrage, this episode is a highly practical, inspirational playbook for anyone starting out in real estate without a big pile of cash. Each side hustle is evaluated for start-up costs, income potential, and step-by-step impact—plus advice on how guests converted hustle dollars into actual investment properties.
Ashley Kerr (00:00): “Some of our most successful guests started with nothing. They side hustled their way to a down payment… Every single one of them, use that cash to buy rental property.”
Tony J. Robinson (07:37): “Within the span of a couple years [Josh] built a portfolio worth over a million bucks… Someone who used DoorDash and UberEats...”
Ashley Kerr (11:07): “She was able to save $10,000 over four months just from bartending.”
Tony J. Robinson (13:25): “It’s almost like an Uber, but for service work.”
Ashley Kerr (21:01): “You’re not strapping this [couch] onto the top of your Tesla and hauling couches around.”
Tony J. Robinson (22:55): “By the time she graduated from high school, she had two properties worth a combined $900k…”
Ashley Kerr (25:48): “He actually hit $100,000 net profit over two years. So he ended up selling 381 plants…”
Ashley Kerr (29:29): “Unlike bartending or doordashing… all the other ones require a heavy time investment… in the digital product space, you can create something once and then reap those benefits for days and weeks and months…”
Ashley Kerr (35:34): “That would be the only thing that my mind just always goes to liability… But yeah, as far as the income ceiling, it’s really market dependent.”
Tony J. Robinson (39:09): “Their handyman business actually became a business. Right. It evolved from a side hustle into a standalone income stream for her and her family. Not just a side hustle.”
| Segment | Description | Timestamp | |-------------------------------|-----------------------------------------------------------|------------| | Why Side Hustles for Investing| Why rookies need to side hustle for down payments | 00:00–01:04| | Gig Delivery | How to maximize earnings delivering for apps | 01:07–07:37| | Bartending | How tips can stockpile for real estate fast | 08:59–11:54| | TaskRabbit | Handyman jobs for quick cash and networking | 13:25–16:07| | Couch Flipping | How a 16-year-old funded $900k in property | 19:16–22:55| | Exotic Plant Flipping | From plant mix-up to six-figure real estate seed money | 22:55–26:58| | Digital Products | Passive, scalable side hustle examples and setup tips | 26:58–29:29| | Dog Sitting | Zero cost, home-based bridge for a real estate leap | 34:14–37:31| | Handyman Services | DIY rehab, skill growth, and moving from hustle to biz | 37:31–40:24|
The hosts tease an actionable five-step playbook for taking side hustle cash and translating it into your first deal, emphasizing the importance of intentionality, documentation, and reinvestment.
Final Thought (Ashley, 40:24):
“Well, thank you guys so much for listening… Go to biggerpockets.com... and we’ll see you guys next time.”
This episode is a must-listen for aspiring property owners seeking realistic, tested pathways to their first deal—no rich relatives or perfect credit required.