You know what’s best for you—that’s the advice today’s guest offers, and it’s the exact mindset that took him from house hacking on a teacher’s salary in his mid-20s to quitting his job with a four-property portfolio at 30. If you’re still stuck answering to someone else, today’s guest will show you that you don’t have to!
Welcome back to the Real Estate Rookie podcast! Jake Handler took a bet on himself, from buying his first property on a teacher’s salary to building a four-property portfolio and walking away from the career he once expected to keep for life. Jake breaks down how he house hacked his way into real estate after a lender told him no, how he negotiated a seller-financed deal that soon housed his in-laws down the road, and how to score someone else’s 2.75% interest rate!
If you have a stable career and every reason to stay comfortable, Jake’s story is proof that the biggest risk might actually be staying where you are!
Ashley:
What happens when the safe career you worked hard to build starts feeling like a bigger risk? Jake had job security as a teacher, limited buying power in an expensive market, and plenty of people telling him why real estate would not work. But eventually staying comfortable felt more dangerous than betting on himself.
Tony:
And that bet took Jake from buying his first property on a teacher salary to building a for property portfolio and walking away from the career he once expected to keep for life. And today we’re breaking down the pivotal decisions, the doubts and the ordinary deals behind that transformation.
Ashley:
This is the Real Estate Rookie Podcast. I’m Ashley Kehr.
Tony:
And I’m Tony J. Robinson. And with that, let’s give a big warm welcome to Jake. Jake, thank you for joining us on the rookie podcast today, brother.
Jake:
Tony and Ashley, I have been a listener since day one.
Ashley:
What day was that? Let’s test your knowledge.
Jake:
I think March of 2020, right around COVID from memory, right? March 13th is my birthday. It’s easy to remember. Friday the 13th that year.
Ashley:
Yeah, it’s funny because we started the podcast and we had rerecorded ahead of time and we basically got, I think, three episodes out and then we had to scrap all the other ones we recorded because COVID hit and was like, we can’t just come on here and talk. Nothing happened. Oh yeah, real estate’s great, blah, blah, blah. And we had to rerecord a bunch of shows. But yeah, right from the beginning, March of 2020. So take us back to 2020. You must have been starting your real estate journey then if you were tuning into real estate rookies. So what did your life and career look like at that time?
Jake:
Sure. I was a teacher and a high school baseball coach back in 2020. I also had my real estate license, so I was a realtor on the side as well. And I really got a lot of validation from listening to this podcast, just knowing that there’s people in the world and you’re talking to other people that sounded like me and there were some all over the country that could do what I wanted to do. And that was really that boost in this knowledge kick for me to decide that I should be house hacking.
Ashley:
Now, something during that time period, you were a teacher, correct? During this time period? What made you think that that was something you didn’t want to do forever?
Jake:
So I was living at home at the time and I was in my mid-twenties. I had lived away from home and then back home. That’s a tough transition to do when you’re single in your mid-twenties. So I knew I wanted to go and live somewhere. And with the combination of educating myself through BiggerPockets and having that real estate license that I had just gotten, I said, “You know what? I could buy something.” And again, being a single teacher, I was on one salary in a really expensive market in Northern New Jersey. My options were limited, especially if I wanted to house hack. So I was trying to buy a two-family multifamily, of course, because I wanted to house hack and I just couldn’t do it. My pre-approval was up to 350,000, which is not even. I could barely smell a two-family in North Jersey for 350,000.
So I ended up, I’ll say settling, but it ends up not to be settling on a two bedroom condo. And I house hacked. I rented one bedroom to a friend and I lived there for a few years.
Tony:
Jake, I think just one follow-up question from you. A lot of people listening, the idea of house hacking seems appealing because you can get into an investment property for less down. But the other drawback, or maybe one of the things that deters people from wanting to do a house hack is sharing their living space with someone else. And to your point, you said, “Hey, it would’ve been great to get a two family, but I can’t do a two family. So instead I’m going to get a condo.” So you’re literally sharing within the same four walls. Was that at all, the idea of sharing the same living space, was that at all an obstacle for you or something that you were maybe uncomfortable with or maybe not excited about? And if so, how did you move past that, still pull the trigger?
Jake:
So did I want a 4,000 square foot mansion to myself? Of course I did. Being in your mid-twenties and single at the time, is there a better time to share space? I mean, I knew that that period of my life was not going to last forever and I wanted to optimize that. And again, not being pre-approved and not being able to afford a much bigger space combined with the fact that I can compromise some space at that point in my life, I was happy to do it.
Ashley:
I mean, roommates, you get to choose them. Kids, they are who they are. They come out and don’t get to choose. So you’re right as this is the perfect timing, not only because of most people will eventually go on to have kids and have them as roommates. So at least with having another adult as a roommate, you can evict them or kick them out. Yeah.
Jake:
And I mean, if I wanted to build a real estate portfolio and I didn’t start by house hacking or owner occupying a property, that would’ve been really difficult for me. I’m looking at 20 to 25% down, higher interest rates. Then I’m really crunching numbers and spreadsheets and thinking, okay, is my huge down payment better here or in another asset class? But when I was young and naive and okay with sharing walls and only had to come with a down payment of what I chose to do was 10% down, that was much more manageable for me to start my real estate investing career. And I love talking to younger people who have that dilemma. Whenever you can occupy a property, I think it’s the best way to get started.
Ashley:
And most people, when they go to college, they are sharing a room anyways. I mean, I’m assuming as a teacher, you had to go to college. Did you dorm at all?
Jake:
I did. And my college roommate ended up to be the roommate I’m talking about. So he knew my snore schedule already. He knew I sleepwalk every day at 2:00 AM. I didn’t have to tell him.
Tony:
Now, Jake, one of the things you mentioned that I thought was interesting, you said that you got pre-approved for 350,000, but I also know that that wasn’t your first experience. So I guess walk us through what happened when you first tried to get pre-approved.
Jake:
Yeah. So I had a phone conversation with a lender. And again, I was a new real estate agent at the time too, so I was connecting with mortgage lenders on that side of things as well. And I called someone and I knew him and I gave him my rundown. And he kind of just told me that, yeah, okay, that’s your salary. Okay, you don’t make any extra income. That’s your debts. Yeah, this isn’t going to work.You might want to save up and wait for. You know what’s funny? You might want to save up and wait for rates to go up because you guys remember back in 2020 when rates were down, that was an awesome thing. But everyone said once rates come back up, the prices are going to go down. So there’s always a challenge, right? That was a challenge at the time. And if I listened to this lender who kind of just didn’t want my time and didn’t want the whole time of day, I definitely wouldn’t be on this podcast, but also I’d probably still be teaching, which I did leave teaching a few years later.
Ashley:
It just shows how many deals that lender probably was having come across his desk that he got to pick and choose his clients. And I’m sure that’s very different right now. I have lenders texting me all the time as to like, “Hey, you want to refinance anything?”
Jake:
Yeah. It really taught me you don’t. Maybe it’s stubborn, but I don’t take no for an answer, especially just not only one time. My mom would tell you that’s true. It’s just like, no, no, but why? I need to understand why or how.
Tony:
But I think you bring up a really good point as well, Jaker. Your story illustrates an important point that two lenders can look at the same borrower, the same potential buyer, and come up with a totally different suite of options that that person can go follow. And I give the example oftentimes that the mortgage industry is kind of like the ice cream industry where I can go to these different stores. I can go to HaagenDaw’s, I can go to Baskin Robins, I can go here, Ben & Jerry’s, and I can get ice cream. They all sell ice cream, but they’re all slightly different flavors. And they all give you a slightly different experience. And it’s the same thing when you go talk to lenders. They’re all giving you a mortgage, but the flavor and the type of mortgage they can offer, completely different. So if you stop at the first one, who knows?
Maybe lender number two or lender number five is the right person to align with your situation. So I love that you didn’t stop. I guess one last question on that piece, Jick, before we move on. How did you find the lender that actually pre-approved you? Was it like a Bank of America type loan or how did you find this person that gave you the yes?
Jake:
So it’s weird because you didn’t know that, Tony, but it was Bank of America that I used. I think they still have this. It’s a really awesome first time home buyers program. And if your income and credit score is within a certain relation to the median in the county, then you can get some awesome benefits. And I qualified for all of those benefits. So I actually got a sweet down payment grant as well.
Tony:
And it’s funny because we typically times. Oftentimes we’ll say like, “Hey, Bank of America, Chase, the bigger banks are a little bit harder for investors.” And sometimes it’s the local and regional banks to give more flexibility. But man, you went to the big bank and you found the right loan product, so it worked out for you.
Jake:
I called a bunch and I found some smaller banks as well that were willing to, but then I saw after I got a few yeses, I was like, “You know what? Let me try to get the best yes that there is.” And that down payment program was the best yes for me.
Tony:
Now, when you began looking, you said that you were looking for a small multifamily, like a two unit hopefully, but you ended up transitioning into a condo. So just walk us through what that transition looked like from small multifamily, maybe single family option back to a condo.
Jake:
Desperation, right? I mean, I know I was dealt a hand and I played the hand I was dealt. I was not dealt pocket aces, so I couldn’t play pocket aces. And anything more than one bedroom, I was open to. And this condo is in a really awesome area. It’s where young people want to be. I still have it today as a rental property, and I rent it out really easily because it’s such a great location. Of course, everyone knows the most important three rules of real estate, location, location, location. So I had no problems holding that condo, buying that condo and still holding it now.
Ashley:
Let’s look at the numbers on this deal. So what was it listed at and what did you purchase it for?
Jake:
My favorite part about telling my story is that this property and the next one that I bought, I paid over asking price on the market. So this is not some secret deal I have because I’m a realtor. This is not some crazy algorithm I pulled. Anyone could have bought it for the same price I did. I probably overpaid for them too. So it was listed at 315,000 and I bought it for 320,000. And my down payment was 10%. I believe I wanted a lower down payment, but the lender required me to put down 10% because of the monthly payments.
Ashley:
It’s funny you say that about the over-asking. I know this was years ago that you bought that, but I’m seeing that in my market right now again, where agents are actually going and pricing the houses low to attract more buyers. And I just had a friend that put an offer in 50,000 over asking and it did not get accepted. So they’re marking the properties way lower. So I talked to my agent about it and she said she’s seeing that a lot happen as they’re doing that to get these over-askings. So my point of this is just because you pay over asking doesn’t mean you’re overpaying for a property. It could be that they didn’t price it correctly, that it actually is worth more than what you were asking for.
Jake:
Yeah. A lot of times it’s a marketing strategy. The seller wants, maybe they have a closing date that they need to have. So they want seven offers so they can choose one that matches their closing date or when they want to control the terms during the appraisal or inspection. It’s a strategy.
Tony:
And Ashley, I think the inverse of that is true as well. It’s like sometimes a rookie will look at a deal and see that it’s been on the market for 180 days and that there’s been like six price reductions and they’re like, “Oh, it must be a bad deal.” That isn’t necessarily true. It could just be that the agent was like, “Hey, Tony, you need to list this at 300.” And Tony’s like, “No, I’m going to list this at 400.” And the agent’s like, “I don’t think it’s going to sell at 400. We’re going to list it at 400.” And they list it at 400, it doesn’t sell. And they spend 180 days doing price reductions to finally get it down to the price where the market actually responds. And now it’s at a price that actually does make sense. So even if you’re a rookie investor, don’t necessarily let days on market or price reductions scare you away.
Just underwrite the deal and find out where it works for you. And it sounds like that’s what you did. Even though you were slightly over-asking, the deal still made a ton of sense.
Jake:
Well, so I bought it for 320,000 and it appraised for 330,000. So Ashley’s point right on the money there. And I was living in one bedroom renting out the other. So my monthly payment was 2,100 and my roommate was paying me 1,000. So I was living for half off, maybe a little even less than half off. And a lot of rookies that I speak with personally, they say they want a house hack to live for free. And I say, why not 48% off? Tony, we were talking about our shirts before we were recording. If my shirt was 48% off, I’d be buying it. Why not?
Tony:
And I guess you said that your roommate was the same roommate you had in college. Just walk us through how that came to be. Did you reach out to him and say, “Hey, I know we were roommates. It worked out well. Do you want to do this again?” Was this before or after you closed in the property? How did you actually fill that space?
Jake:
Yeah. So I just put it on my Instagram story and I said, “Does anyone. I’m looking for a roommate in this town.” So I had a few inquiries of all friends of mine or someone who knew a friend of mine. And I just showed them all the place and went with him.
Ashley:
Now, after this deal is done, what is next for you? Did you have a plan as you’re going to live there for one year? What did this kind of project you into next?
Jake:
So that was in 2020 when I bought my first deal. And then in 2022, I had a few years of being a real estate agent under my belt. So in addition to teaching, which I was still doing, I was also having this side hustle. So I was building up some money. I bought another property on the market, over asking, needed work, same kind of deal, and moved into it and brought my friend with me to house hack the second property while keeping the first as a rental.
Ashley:
Coming up, Jake explains how he repeated that same simple strategy, live for free, and use that lower cost of living to make a career decision his rental cashflow alone could not support. That’s right after this. Okay. Welcome back. So Jake, you gave us a little insight into your first deal, but what about your next deal? Let’s build the next rungs on this ladder here. So what was the second purchase and how did that actually impact your current career?
Jake:
So I just did what I did the first time, just at a bigger scale on the second property. Again, it was on the market. I paid over-asking. This time, ready for this, Ash? $25,000 over-asking. It was listed for 400,000 and I bought it for 425,000. It’s pretty cool when you’re also your own realtor though, because you make a commission on it. And this time I purchased at 5% down. And this was intentional. One, because the lender approved me for that. And two, because I want to come with less money down as I house hack and look to leverage my portfolio for a long period of time as a young person.
Tony:
Jake, just out of curiosity, because you were doing the real estate agent work on the side. Over those two years, if you could ballpark it, do you know how much you made in commissions during that timeframe that allowed you to get the better loan approval?
Jake:
I would say that year one was probably like 10 grand and year two might’ve been like 30 or 40 grand. But as we know, lenders average those two. So it boosted me, let’s say maybe 20 grand per year for income.
Tony:
Now let me ask this question because I think there are a lot of rookies who go back and forth on, do I need to get my license to become a real estate investor? And Ash and I typically say, no, it’s not a requirement to do that, but it seems like it did benefit you to an extent. So what was your motivating factor for getting the license? Was it, “Hey, eventually I want to be an agent kind of full-time and this is my path to get there?” Or was it more so I just want to learn the ropes or just the additional income? What was the motivating factor for you? And I guess knowing what you now know, would you have done it again that way?
Jake:
I would do it again the exact same way I’ve done it because my motivation was to continue to build a real estate portfolio. And honestly, just the way it played out and be in my 30s, which I now am, and be able to educate younger people on how I did it and be their realtor while doing that. I write this down. I’m crazy like that. I write goals down. I write how things look three years, five years from now. And I wrote that down back when I started this real estate career of mine. And now I’m doing what I wrote down six years ago.
Ashley:
How much does it cost you each year to have your real estate license? I hear people say it’s not worth it unless you’re actually going to sell houses. If you’re just doing it for yourself, you’re buying one house a year, not worth it. What does it actually cost a year to have your license?
Jake:
I’d say roughly about a thousand dollars between the MLSs and all the subscriptions that are mandatory. At this point, I’m essentially a full-time real estate agent. I also do some property management. So I sort of agree with the people who say, if you’re just doing it to buy your own deals and you’re only buying one a year, it might not be worth it to have your real estate license. For someone who makes a business out of it, of course that’s different. And
Ashley:
You have to take your CE credits every year too, right?
Jake:
Yeah. Online.
Ashley:
Yeah, those cost money and cost time of having to sit there. So I think just if anybody is interested in getting the real estate license, maybe talk to an agent and see what’s actually involved in not only the process to become an agent, but throughout the year, what are the requirements and things like that. I probably will never ever get my license because I don’t want to have to do the paperwork. I have a property where my tenant is buying it and I’m still having my real estate agent handle the deal to just, first of all, negotiate back and forth, handle the inspection, handle everything so I don’t have to do anything. To me, it’s worth it to pay the commission, even though I already had a buyer and she didn’t need to go out and find one. So just make sure you know everything that’s involved and maybe it’s something that actually would be super beneficial for you and can be like Jake and actually build a career out of it.
Tony:
Well, Jake, continue walking us through the second deal. So it sounds like this one was actually a single family home. You said you bought it for 425, 5% down. Once you’re actually inside of it, what was the strategy? How many rooms did you have to rent out? And were you still covering maybe 50% of your living expenses? Was it more or was it less on the second deal?
Jake:
Sure. So at this point, property number one, which is the condo, that’s rented out. I’m cash flowing about $500 a month for property number one. And I will say obviously 2020 interest rates have a lot to do with that cashflow.
Tony:
And Jake, sorry, one question on that. Were you renting out the entire condo or were you renting out the rooms individually?
Jake:
Yes, the entire condo. I don’t want to be the landlord that doesn’t live there and have rent by the room. I’m not into that. But then in property number two, I moved in. I brought that same friend with me and another friend. So yes, it’s a single family home, three bedrooms, and I was renting out two of them. And on that property, my monthly mortgage is $3,000 a month, including taxes and insurance. And I was renting each bedroom out for $1,000, which is a great deal for my friends. And so at that point, I’m almost living for free if you include property number one’s cashflow as well.
Tony:
You just told your friend like, “Hey dude, we’re moving. I upgraded us to a new place.”
Jake:
Yeah, upgraded is a good way to put it. Yes.
Ashley:
Now with these two properties, how did you handle the property management? And you had mentioned a little bit that you’re actually managing properties for other people, but for yourself at this point, were you using any tools, software? Did you have a handyman? What did your team and kind of software belt look like?
Jake:
Really not sexy. I just had that one condo, really solid couple living there, paying me monthly, Zelling me monthly for that first condo. And then two of my best friends living with me, Zelling me monthly. And that’s that.
Ashley:
So maintenance requests, they would text you. And were you handling any of the maintenance yourself?
Jake:
I could barely tie my shoes, so I definitely was not the person to do that. I do have local handymen. Again, being in real estate, I know people who are more talented than me to fix some things. So yes, I had some go-to calls.
Ashley:
As much as there are amazing tools for property management, when you do only have one or two properties, it is usually, depending on the tenant, very easy to manage yourself and not have a property manager in place.
Jake:
I agree. So I said I’m in property management. I have a HOA property management company, so I don’t manage rental properties. And part of the reason. I mean, I’ve thought about that, but I honestly don’t think it’s necessary for most landlords to have a property management company. Of course, unless you’re doing management landlording at scale.
Tony:
But Jake, talk to me.You said your HOA management company. Walk us through, break that down for us.
Jake:
Sure. So there are condo complexes out there that are managed by a property management company because no one owns the entire condo complex. Each condo owner owns their own unit. So someone has to be in charge of managing the common areas, paying insurance monthly, paying the lobby utility bills and maintaining cleanliness, all those things. So in 2022, I started a management company with a couple friends of mine that manages HOAs and we’re at about podcasts or evergreen. Right in 2026 today, we’re at about 30 associations managing. And I hope one day I listen back and laugh at that number.
Ashley:
Okay. So real quick, what would be some of the differences that stand out between managing an apartment complex for a landlord with property management compared to managing an HOA?
Jake:
Because if someone calls the HOA manager and says their toilet is leaking, I say, call your landlord. We don’t go into the units. We are just maintaining the roof and all common areas and budgeting. If you pay an HOA fee, so we come up with that fee with the board and a proper budget for each association. There’s a lot of flood zones as well where we have our buildings and that needs to be budgeted for. Flood policies need to be budgeted for as well.
Ashley:
So you’re not getting calls necessarily from the actual homeowners of the condos. It’s more the board comes to you and you kind of work directly with them?
Jake:
Unless there’s an emergency where the roof is leaking through the unit and they don’t know who to call, they’ll call us and we’ll say, “Hey, we can send a roofer out and here’s a handyman to call for your unit.” But yes.
Tony:
Yeah. We haven’t really talked to anyone that’s had this model, but I’m just curious, for the rookies that are listening, if they want to replicate that, because it feels like property management, but it’s almost like B2B property management as opposed to B2C. How are you sourcing these HOAs? Are you just walking in to the board of whoever the board is for this HOA and saying, “Hey, my name’s Jake and we do HOA management?” How do you find the first client?
Jake:
It’s a great question because there’s a lot of decision makers in something like this. So if I was just managing rental properties, I would try to sell one landlord. This is multiple decision makers. So it does take a lot longer to get business. Hopefully also takes a lot longer to lose business should we ever lose any clients. But there’s a specific area in New Jersey. It’s Hoboken, New Jersey. It’s a nice little quiet one square mile town right outside of New York City. And there’s a lot of buildings that look like one another, like eight, 10 unit buildings. And we really just put flyers out. That’s how we got started. We put flyers out about how we’re going to change things. I have a condo, so I had that experience with my management company and my partners also had more negative experiences with their management companies.
So we’re trying to solve the problem that’s out there in HOA management. And I can’t believe way more than real estate investing. I can’t believe how many calls we received from flyers. You don’t get calls back when you’re mailing an owner trying to buy their house. One out of a thousand maybe. But yeah, you get calls back when you are a young, youthful HOA, relatable company that is trying to change the game in town.
Tony:
Yeah. Jake, what did you say in the flyer? I’m just curious.
Jake:
So it’s a little aggressive. You ready? It’s your HOA management company robbing you? Because they robbed us too. Call us, blah, blah, blah, blah, blah. My partner is in marketing and was really adamant that we should be that aggressive.
Ashley:
Yeah, that’s how it seems to be working for you. What is the typical fee that you charge? Property management, 10% on average or whatever. How does it work as far as fees for HOA for management?
Jake:
Depending on the services, anywhere from 50 to $100 per unit per month. So it’s really fixed. It’s recession proof. And it’s a fixed number. Our expenses, of course, we have overhead, they go up. We have a team of eight employees, but the income is really predictable, which is nice.
Ashley:
So that’s on top of whatever they need to cover their budget for the year.
Jake:
Exactly. Exactly. It’s
Tony:
An incredible business model. I don’t think we’ve ever interviewed someone that does HOA management. So I live in an HOA like my primary residence, and there is a management company that runs our HOA as well, but I never though about the business model behind that. But I love the marketing angle too. And I think about, obviously, I work in the short-term rental space mostly, and there’s a lot of people who co-host, and there’s a lot of legacy short-term rental property management companies who just aren’t doing a good job. And I think about that hook of like, “Hey, is your short-term rental property manager robbing you?” And we send that out on mailers to the homeowners.
Jake:
There was a picture of a robber too, and we used AI. It was a whole. It’s really cool. But I agree, complacency for legacy companies is exactly who we were targeting of those buildings that were being managed. It’s exactly right.
Ashley:
So I’m assuming this has played a role in you changing your career path. So what has happened since you started this management company since you’ve acquired your rentals with your career?
Jake:
Yeah, so I was able to leave teaching in 2023. And at this point, again, I’m a real estate agent and I have this property management company, and that’s where the bulk of my income is coming from. Right now, I’m at four rental, sorry, three rental properties plus my primary home. So four properties in total. And to be honest, I’m not making a ton of cash flow. I mean, I’m making some, but I didn’t quit my job, my teaching job because of these rental properties I had in terms of cash flow. But what it did allow me to do is create that foundation, almost like a retirement account, because I had such quality, I have high equity, I have really great areas of where my properties are. And I was then comfortable enough to take a bet on myself and take that leap.
Ashley:
I know a couple teachers, including family members, and one of their biggest concerns of ever leaving teaching is losing their retirement benefits that they have the potential to get after working X amount of years as a teacher. And then also health insurance, things like that. So how did you get comfortable with that idea of not getting that security blanket in retirement and also not having benefits anymore, becoming self-employed?
Jake:
So I was never comfortable and I’m still not. I thought to myself, I was 30 at the time when I made that decision. And I just though to myself, just like when I first house hacked that condo, if now’s not the right time, when is? That’s what I though to myself about leaving my career. I said, “I could keep telling myself that I want these retirement benefits, but I’m already flirting with the idea of quitting at 30. I can’t quit. I can’t retire as a teacher in New Jersey until I’m 65. It’s 35 more years. So even though I’m not economically there, honestly, financially, I probably should have waited a couple more years. My accountant told me the primaries are coming up, the tariffs, all these reasons I shouldn’t do it, but it’s only going to get harder.” So I did it.
Ashley:
Well, congratulations.
Tony:
Yeah, it’s an incredible story. And I just want to share because not everyone thinks that same way, but I found in my own personal experience that betting on yourself can oftentimes be the best choice. And there was a few moments in my life where I feel like I bet on myself and ended up working out in my favor. The first time I was in college and I was studying to be an engineer, and I’d interned at Chevron. They have a refinery here in Southern California. I got a job offer. I think I was going into my junior year. They’re like, “Hey, once you graduate, you have a job offer.” And I ended up saying, “I actually hate engineering. I don’t want to be an engineer.” And I walked away from that job offer. That decision led to me eventually working for Tesla. I ended up losing the job at Tesla.
And I had this decision of like, “Okay, do I go back into the workforce or do I double down on our real estate business?” And I double down on our real estate business. And that, to your point, Jake, led me to this conversation we’re having here today. So it’s like when you find yourself at these crossroads, the thing that I always ask myself is, okay, Okay, what is the worst case scenario? And if I can live with the worst case scenario, then my preference is always to bet on myself because I’ve proven that betting on myself has led to pretty good results. So for the rookies that are listening, I think Jake, your story’s an incredible example of that as well. But if the worst case scenario is that you end up living the life that everyone else is already living, it’s not a bad worst case scenario.
And if the best case is that you get to look back and realize that you’re now living the life of your dreams, the life that you journal about, that’s a pretty good best case scenario as well. So Jake, I love your story for that reason, brother.
Jake:
Thank you. And I love yours too, and I already knew it because I’m a listener.
Ashley:
Okay. Well, Jake, so far it seems like your story has been all sunshine and rainbows, but there was actually a challenge that came with one of your properties after closing. How did you handle it and what did this experience teach you?
Jake:
Sure. So for my third property I purchased, I actually bought it seller finance. So I actually mailed the seller. It’s on my street too. So I looked up his address. It was tenant occupied, so I couldn’t ring the doorbell. And I mailed him. He lived in Florida and he actually called me back and we ended up negotiating a deal that worked for both of us for nine months. It was a long time to the finish line. But yeah, essentially I inherited his problem, which was his tenants at the time. They weren’t paying him rent and they were living there for a long time. So I knew what I was taking on. So I bought his situation at the terms that made sense for me. And eventually those tenants did vacate. And now my in-laws live there actually down the street from us.
Ashley:
So with this property, so the seller actually told you that they were not paying rent?
Jake:
Seller told me they were not paying rent. Yes. Yes. Everything was straight up. He wanted to get this house sold and I said, “I really want to get this house bought, but for my terms.” So I explained seller financing and ended up putting 10% down with no PMI, no extra fees, no lender fees, of course, because there aren’t lenders. And it just totally made sense for us.
Ashley:
And what was the amortization and interest rate on that seller financing?
Jake:
Yeah, thank you. 30 years. 5% interest rate fixed for 30 years. No prepayment penalties. It was anything to get that property sold for him.
Tony:
So Jake, I’m assuming it must have been a pretty sticky situation then with these tenants if he was willing to give you such a sweetheart deal. So how did you actually, once you took ownership, what steps did you take to actually get these problem tenants to vacate?
Jake:
I live on the street, so I am not someone just eight states away who’s probably calling them and leaving them, saying bad words to them and things like that. So I was just face-to-face with them. It was pretty simple. I was more human than the previous owner was. And essentially we had an agreement on when they would move out. It was longer than I wanted, but we ended up being okay with that. And they eventually did vacate like they said they would.
Tony:
Did you give them cash for keys or just out of the goodness of their heart, they left?
Jake:
We had an agreement. So they paid me rent too. I forgot to add that part. I know they weren’t paying the previous owner rent, but they paid me the rent, although very under market value. So it was part of the agreement. Okay, you’ll pay me this for that long, and then you’ll vacate, and everything was smooth.
Tony:
And they actually did it. They held up their end of the bargain.
Jake:
Yes.
Tony:
Wow, that’s incredible.
Jake:
I know. I was ready for anything, but it worked.
Tony:
Another business, Jake, that you can go start is negotiating non-paying tenants on behalf of other landlords.
Jake:
Yeah. I mean, I would go with my wife. It was very human to human, and that was the goal there. So no, I don’t think it’s scalable for a business, but on my street, I could do it anytime.
Ashley:
Okay. Don’t go anywhere. Jake is closing out with the mindset shift that changed his life, the advice he’s going to give rookies that are stuck in analysis paralysis, and why his next move may be no move at all until the right opportunity calls. We’ll be right back after a word from our show sponsors. Okay. Welcome back. So Jake, you are now the owner of four properties, but you are not chasing doors just to grow and scale and have that unit count. So let’s bring this back to the life you are actually trying to build. How has real estate changed your life both financially and personally? And what does financial freedom mean to you today?
Jake:
So it’s given me the opportunity to create businesses, to create relationships that I typically wouldn’t. And to not. I don’t really answer to anyone, which has Tony, right? I mean, you were telling me you’re saying your story and it’s just, you can’t even quantify something like that. And I’m very lifestyle first and let your business or your real estate portfolio in this case fall into your life and not revolve your life around your business. And my properties are slow and steady. Like I said, they don’t really cashflow. They cash flow just a little bit, but they are retirement accounts for me. And I’m in no rush to be the biggest real estate investor in the country. I will slowly take on great debt and be happy with that.
Tony:
When a rookie who’s looking at you, Jake, and they’re like, “Hey, I want to do what you did. I want to get started the way that you got started.” What advice do you give them on getting started today as a real estate investor?
Jake:
I would like to give them the advice that only you know what’s best for you. If I took that lender’s advice when I first was looking for a house hack and didn’t buy that first property, I mean, that lender is not thinking about the consequences of me not buying that house hack and how that would affect my life. Only I’m thinking about that. I’ll make a quick analogy. I got a puppy a couple of weeks ago. His name is Arnold. So shout out Arnold. Love you if you’re listening. And I took him to a vet. I took him to two vets actually. And one vet told us that he should be eating dog food, puppy chow, and he should be neutered at six months old. And vet number two told us he shouldn’t be eating puppy chow, he should be eating raw meat only, and he should get neutered at two and a half years old.
So those are two just very conflicting opinions. So just like real estate investing, that’s the analogy I’m making. Only you know what’s best for you. So I’m sorry, but posting into the BiggerPockets forums and asking what I should do or asking AI what I should do, don’t do that. Ask yourself how you want real estate to fit into your life.
Ashley:
Was one of those a holistic vet?
Jake:
Yes.
Ashley:
Okay. So the last thing here before we wrap up is what are you building towards now? Are you actively looking for another deal? And what does the future kind of look like for you?
Jake:
I like to say that I have point guard vision and that’s the goal. So I don’t want my goal to be a result. I want my goal for me to stay opportunistic. So actually a few weeks ago, I also bought another property for an assumption loan where I’m a non-occupying co-borrower with someone who’s occupying the property. We took over a 2.75% interest rate and 25 years left on a loan, multifamily. It probably can have its own podcast, this story. But the point is there’s no way I was looking for that. I had point guard vision and opportunistic, and that’s my goal for forever.
Ashley:
We’ve talked quite a bit recently, I feel like about assumable loans where basically somebody wants to get out of the property they have. You are taking over the loan with the bank’s approval they’re going through. They’re vetting you. They’re adding you onto the loan product, but you’re keeping the exact same loan that they had, which turns can be the low interest rate that some people have secured. So yeah, that’s awesome. We are going to have to have you back to go into that deal just for a whole episode. But Jake, thank you so much for joining us on this episode of Real Estate Rookie. Where can people reach out to you and find out more information about you?
Jake:
Yes. So you can find me Jake Handler, NJ, Jake, J-A-K-E, Handler, H-A-N-D-L-E-R, and then NJ for New Jersey. That’s my handle on Instagram and really all platforms.
Ashley:
Well, thank you guys so much for listening to this episode of Real Estate Rookie. I’m Ashley. He’s Tony, and we’ll see you guys on the next episode.
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