158: Rookie Reply: The Best Career Moves for an Aspiring Real Estate Investor
7 Dec 2025 · 17 min
Podcast episode 158 of Real Estate Rookie (hosts Ashley Kerr and Tony Robinson). The episode opens with host updates and a personal anecdote about helping a friend displaced when two people crashed into her rent-to-own house. The main segment is a listener Q from Ryan Costner (Chicago) asking what jobs best immerse someone in real estate without large pay cuts; Ryan currently works for a contractor doing maintenance for a property management company and has construction experience plus a business management degree. Hosts advise reflecting on learned maintenance skills, expanding current role (shadowing, taking initiative), working directly for an investor or as a project manager, partnering with property owners, doing time studies to find spare hours instead of taking lower-pay roles, and tactics to find owners/contacts. Sponsors and a call for guest applicants close the episode.
Chapters
This is Real estate rookie episode 158.
My name is Ashley Kerr and I am here with my co host, Tony Robinson.
And welcome to the Real Estate Rookie Podcast where we give you the inspiration, the motivation to get started or keep going in real estate investing. And actually every Saturday we pick a lucky, lucky listener and we answer their question live on the show. But before we do that, actually, what's going on with you? What's new in your neck of the woods?
Well, I went to this real estate event for my property management company recently. It was their 10 year anniversary since they've been open, so congratulations to them. But I met one of the Rookie listeners there and we were talking and I was telling him the story of what happened. He's like, you've got to tell that on the podcast. So if you don't mind, I'm going to go ahead and tell a story real quick.
Yeah, story time. Let's go.
So I think one of the great benefits of being a real estate investor and becoming financially free and becoming in a better financial position is that you can help other people. And my goal really is to be able to do things for my friends like buy a huge cabin somewhere and say like, hey, you guys, go stay there for free. You know, things like that I love to do. And so I have a friend that needed to move into an apartment just for a short amount of time and she was willing to pay whatever. It's just she couldn't find anything. And I had something available and that was like super nice that I had that available at that time. She needed it and it was just worked out really well. So she moved into that and it was a super tiny, tiny one bedroom apartment for her, her boyfriend and her dog. And they were doing rent to own on a single family residence and they were remodeling it before they moved in. So that's why they needed somewhere to stay for those couple months. So she was about a week before moving into that property and she let me know her move out date and said, you know, just thank you so much for letting us stay here for only a couple. And worked out really well. We're going to be leaving in the States. You can get it rented, we'll have it all cleaned, everything. Well, about five days before she's supposed to move out, I get a text from her at almost midnight saying somebody ran their car into our house. Can we stay longer? I am not kidding. This really just happened. So what happened was two meth heads were escaping the police and drove their car at 90 mph into the front of her house and shifted the house off of its foundation. Just did tons of damage to the house. The people ended up dying on the front lawn there. While she had never signed the rent to own contract yet. So all that money, all that work, all that time put into rehabbing that property for her to about to move into, she lost all of that. And basically the owner just said, I'll give you back the first payment you made. And I think she had maybe put a security deposit or something down. So that was really devastating for her. And I guess a lesson learned that you sign a contract before you go in and do work on a property. Well, it ended up I had another property that came up for rent and so I was able to give that to her to rent for a reduced rate. And now she's moving into that property and actually hopes to eventually buy that property from me. But just like a crazy story of like something that could happen to somebody and she is just like such a trooper. She just had surgery too and she's transitioning, trying to move in between these places when she thought she was moving somewhere else. And so yeah, just so wild, wild, crazy story I guess. I mean, who thinks that someone's going to drive into the front of their house?
I'm so glad you share that story actually, because I think a lot of what drives people who are entrepreneurial in spirit isn't just for their own financial well being or for their own success, but like you said, it's to be able to provide, I guess to let that success extend to the people that you care about and to allow your success to positively impact and benefit other people. And what a terrible experience for your friend. And I'm sure you know, so many emotions that she experienced, but where to live was one less thing she had to worry about because of the success that you've had. So man, for those of you that are listening, obviously we're all motivated for what real estate can give to us personally. But sometimes it's also helpful to think about how all the hard work you're doing can kind of impact people around you as well.
Yeah, like around here it's very hard to find an apartment right now. And if you are looking for apartment, you have to go through background check, credit check, you know, get approved, fill out an application, pay an application fee, things like that. It was so cool for me to just be like, hey, here's the lockbox code, start moving your stuff in.
It was awesome for me to be able to do that for my friend and just say like, don't worry about it. Stay here as long as you need to. And so I think that's definitely a really awesome part of real estate investing, is being able to do those things for your friends and family.
Yeah. Well, thank you for sharing that story, Ashley. I'm sure it inspired a lot of folks.
Just a crazy story in general. Just that too is like the person that something like that would happen to. Just these crazy, crazy things. But okay, so let's get to today's question for the Rookie reply.
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So today's question is sent by Ryan Costner. Send this to my DMs. You can send me a DM elcomerentals or one for Tony onyjrobinson. And basically whoever jumps into our recording platform first gets to upload their dm. So who knows who it's gonna be.
So Ryan message says this hey Ashley, I'm Ryan from Chicago. Got a question for the rookie reply. I'm looking to get into rental properties starting with single family household or a duplex and doing the stack method. I'M not happy at my current job and I'm looking to make a change into the real estate world. What would y' all recommend for a job? To immerse myself in real estate without making crap for money. Not a part of this question because I think keeping it broad would help the question for the podcast, but talk about it where you want. I currently work work for a contractor who does the maintenance for a property management company. I thought I would learn more in the position, but after a year with minimal takeaway, I think it's time to move on. I would also like to go back to a W2. I'm very handy. Just got done with a full gut rehab on my personal residence. I also have a bachelor's degree in business for management. Based on that, what would be your recommendations to change my future by helping me along my journey for financial freedom.
So do you want to go first? How do you want to take it? I got some ideas.
I guess I kind of break it down real quick. Is that is in a job right now where he thought that he would learn more about real estate investing by working for a contractor who works for a property management company. So the property management company probably uses his employer as a contractor. We're saying, hey, I need this job done here, go to this unit and take care of it, things like that. And then he's asking what are some other positions or other jobs he could do to help him learn more about real estate investing. So go ahead, Tony, what do you have on that?
Yeah, I guess just like a couple things come to mind, Ryan. So I think my first question to you would be what were your expectations walking into that position? Right. Like what were you hoping to gain by taking this maintenance position with the contractor? And just kind of ask yourself if those expectations were, I guess, realistic to begin with. Right. Like, were you hoping that you would get this crash course on how to become a world star investor? If so, then maybe your expectations stepping into it are what's giving you this kind of jaded feeling about the position. But if your goal stepping into it was, hey, here's how you efficiently and effectively manage maintenance requests within a property, then I mean, I would hope that you've gained some experience with that. So I guess that leads me to my next question is can you reflect, Brian, within your current role on what are some of the things that you've learned that have benefited you as a potential real estate investor? The property management side of things and specifically managing the maintenance requests, I think is one of the biggest headaches for a lot of new investors, right. A lot of people shy away from managing their own properties because they don't want to deal with broken toilets. Right. And if you have worked for a company that's given you a playbook on how to effectively do that, then you're 10, 20, 30 steps ahead of other new investors that haven't learned that skill set yet. So that would be my first question is reflect on what you've learned that has already made you a great investor and can you lean into that even more? Then my last question, you know, I'm asking you questions, but you can't answer me back. So I guess take it for what it is. But my last question is, is there an opportunity for you, Ryan, to take some initiative outside of your general job description? Like can you go to your this contractor that you work with and offer to help him with some other parts of the business? Can you even maybe go to the property manager that you guys are contracting for and offer him maybe some additional work in exchange for whatever, allowing you to shadow him when he's doing all these other things? Like can you create more opportunity with the seat that you're in? Because you're already very much surrounded by real estate professionals. You're surrounded by a contractor, you've got a property manager. Those are two key pieces for everybody's team when it comes to real estate investing. And you've already got a line to those people. So is there a way for you to expand your job description within the current role that you have? Ryan, I know I didn't quite answer your question, but more so just kind of pointing questions back at you, but hopefully that kind of gets the wheels turning a little bit.
Yeah, I really like that last point you made there, Tony. Expanding on your current role or even if staying in your current position and taking on a side hustle or something different added on, so maybe working weekends or nights or something for that property management company, even if it's just doing little handyman things for them. But I think as far as like the big things I think of to get started in real estate is so you already have the construction knowledge, the construction skills. And it says that you do have a bachelor's degree in management. So maybe is there some kind of project management role you could take on also working for other investors? So instead of working for the property management company or a contractor, maybe you could work for an investor directly and get that side of you? Because sometimes property managers and also contractors, they're not investors themselves. And I think that there's a big difference as to how they look at a project, as to how an investor looks at a project and it looks at a property and analyzes a property. So I think going and seeing that if you could be of use to an actual investor and work with them directly would be a really big benefit for you. Or even staying in your current role and taking on business partner who is an investor and maybe he's going to supply the money. He'll help you analyze the deal and then you actually go and do the rehab, since you have that knowledge and you did your whole personal residents too. And you can show that as a sample as like, hey, look, this is my work. Take them through your house and prove that you can add value to a partnership that way too. So I think there's a bunch of different options for you. Yeah.
I just want to add on to that last point, Ashley, what a great idea. Right. And maybe even take it one step further. You know, like you're working on different properties for this property management company all day, every day. Can you reach out to some of those property owners and say, hey, I've actually worked on your property. I know it inside and out. Here's my skill set. And then maybe that's the person that you end up partnering with. Right. Because they've already seen your work. They didn't know it was you maybe. Right. But they are. They've already seen your work. You've already somewhat established a relationship there. So you can say, hey, I'm looking to get started. I have this skill set. You have the experience, you have the funds. Can we come together to take a deal down together?
Yeah. And to be clear, Tony's not saying to go and poach, you know.
Right.
Things from the property management company or the guy that you're doing. No. But to actually partner on a deal and become a part owner on a different deal and then, you know, hand it off to the property management company when you're done with the deal. Yeah, I think that's a great idea, Tony, too, because you can find out who those owners are pretty easily. You can go on to propstream, you can go on to your county's GIS mapping system and just type in the address to get the owner's name and to get their address, and then Google white pages, type in their name and find their phone number.
So. Okay, well, should we wrap this one up, Tony? Yeah.
I don't think I got anything else for you, man. Hopefully this. I know I didn't give you as much advice. I Just asked you a bunch of questions, but hopefully that at least points you in the right direction. But just, I guess the last thing I'll say, Ryan, is that sometimes we don't see the opportunities that are right in front of us. Right. Like when you're in the grind every day, you sometimes become blind to what's right in front of you. And I've shared the story before, but I have a friend who lives here in SoCal and she's telling me that I really want to get started in real estate investing, but I don't have the team, I don't really have the resources. She was like, I don't know if I should do this, I don't know if I should do that. And over the course of that conversation, she ends up mentioning to me that her dad is a general contractor for a big commercial real estate company. And I said, you were just telling me that you don't have the team or that you don't have the resources, but your dad is a general contractor. I was like, you have all the resources that everyone would die for. Right. So it's just sometimes when you're so close to it, you don't see the opportunities that are in front of you. So hopefully this conversation, Ryan, helps you see some of those.
Yeah. And one final thing from me too is that Ryan had mentioned that he didn't want to take a pay cut either. So I think a lot of times that there's two opportunities that are presented to someone and the first one is you take a pay cut and you work for an investor, you work for somebody where you're going to be getting that experience and knowledge and that's what the reasoning is behind taking that pay cut. The second thing is that you make more time with the job that you have. So we just had, you know, Anthony Michael on and he works full time for the military, he works part time as a hard money lender and he's still flipping houses. So do a time study if you need to and see where your time is going and see if there's still time to become an investor or to wholesale deals or work for another investor as an intern for free and finding that time in your schedule to actually do that and instead of taking a low paying job to learn more. Well, that's another rookie reply. My name is Ashley at Wealth from Rentals and he's Tony @tonyjrobinson on Instagram and we will be back on Wednesday. But first let's check out something you can get value from at biggerpockets 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.
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.
So head over to biggerpockets.com guest if you want to be a part of our show again. That's biggerpockets.com guest and we'd love to have you on.
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