How to Build a Real Estate Portfolio While Keeping Your Day Job

Dylan Silver (00:00.855)
Hey folks, welcome back to the show. I’m your host Dylan Silver and today on the show I have Jason Tindol who is a school superintendent and real estate enthusiast and investor out of the Vancouver, Washington area. I’ll have to travel out there sometime. Jason, welcome to the show.

Jason Tindol (00:20.108)
Yeah, thanks for having me.

Dylan Silver (00:21.953)
Before we hopped on here, was mentioning, you know, anytime someone gives a ringing endorsement for any area of the world that I haven’t been or that I didn’t know about, now I have the bug to go. And you were saying it’s 74 degrees on average out there. So I don’t know why I thought it would be freezing cold out

Jason Tindol (00:38.222)
No, it’s a beautiful, beautiful area. In the mountains, it’s a lot colder and in the mountains, it’s more snow and more severe weather, but we’re nestled in between the Columbia River, the Pacific Ocean and the Cascade Mountains. So we’re kind of in the heart of a beautiful country.

Dylan Silver (00:59.971)
I gotta say, what speaks very loudly in your bio was I don’t know how anyone could be busier than you. I imagine you gotta be so busy. I imagine between having a real estate portfolio and also being a school superintendent, that sounds like eight jobs. How does anyone manage that?

Jason Tindol (01:20.206)
Yeah, well, I think I love education. education is my passion. And when you do it, your love, it doesn’t feel as much like work. And then real estate is something I like. I like doing it. I started, you know, years ago, we just kept with it. And it’s allowed me to stay in education. So I’ve been in education for 28 years and start off as a history teacher.

You just heard our bells start off as a history teacher and then athletic director then principal and now superintendent of a private school district here in Vancouver, Washington. So I do stay busy, but it’s a good busy. And I think that’s part of real estate that I think people can get to. What I mean by can get to is if you manage it the right way, you really don’t have to do much.

That doesn’t mean it’s easy. It doesn’t mean that you don’t have problems, but you can manage it correctly and still do what you feel you’re called to do in life.

Dylan Silver (02:28.129)
Wow. I feel like every time I talk to someone in the education space, I feel like saying, you know, thank you, because I know it takes a specific type of person to carve out a career in that space to be effective, to not just, you know, collect the check, but to provide value in a difficult, difficult, difficult job. So truly, from from me to you, thank you so much for what you do for raising the next generation of

leaders really in our country. It’s incredible. And so when I’m pairing that with being a real estate entrepreneur, still is incredible to me because it’s in a lot of ways, there’s probably some similarities. There’s probably a lot of differences, but I can imagine one of the big similarities is being a problem solver. And so how has that panned out for you in your career?

Jason Tindol (03:23.598)
Yeah, I think anytime you’re in business, whether it’s real estate or education, if you know how to solve problems, then your organization or your portfolio is going to benefit from that. Because every day the problems are new. Every day there are operations that you do that you can’t get around. It’s just the same thing every day.

And those folks make really good managers. But, but people who are able to do the day to day and navigate around the different challenges, now you’re getting into leadership. so leaders are able to be great problem solvers and, you know, and honestly, it’s not just being able to be great problem solvers that, that you made the right decision. In fact, most of the time.

It’s you’ve made the wrong decision enough to where you can make the right decision in the future. And so you just develop that experience of solving problems.

Dylan Silver (04:25.954)
Yeah.

Dylan Silver (04:29.953)
Let’s pivot a bit here and talk about two tracks, but also how they’re running parallel. So you started off as a history teacher. At that point, did you know that one day I’m going to be a superintendent at that point? it on the was it in your mind somewhere or was it taken a day by day, year by year type of career approach?

Jason Tindol (04:50.712)
Yeah, no. So in seventh grade, I knew I wanted to get an education. And I’m kind of an achiever. So I had a suspicion that I probably would be a school principal at some point. But ironically, I was a terrible middle schooler. So I wasn’t well behaved and I didn’t make all my grades weren’t great. But I’ve always had that entrepreneurial mind and always

you know, had some of that vision. so you it takes vision to be an educator if you want to be a leader in education. And it takes vision in real estate if you want to be someone that has a portfolio that you can, you know, utilize and grow over time and manage over time and create niches and create vision and try to gain traction in that area as well.

Dylan Silver (05:46.571)
Yeah, mean, wow. So for folks who are listening to this and thinking, well, I have enough difficulty managing my part-time job in my real estate portfolio. And then they hear you talking about scaling in one career, which is certainly heavily, heavily time intensive. And then also doing real estate. How did this happen? What was the beginning phases like? Help us make sense of what sounds like a Herculean effort. Of course, you’re passionate about it, but

to get a deal in real estate to manage it while also having a career in real estate spanning decades is a lot of work. So what was the first real estate deal like and how did that deal happen?

Jason Tindol (06:30.446)
Well, I think it started with just, you know, you have to be a learner. You have to be someone that enjoys learning. And you have to, I think, first invest in yourself. Investing in yourself looks different to different people. But for me, investing in myself meant reading. And I’m an avid reader. And so I read a lot. Early on, I read

Dave Ramsey, cut from I was from from the Nashville area. So I was aware of Dave Ramsey When he was a little bit more local and just starting out And obviously since then I have left his thought process. I like I mean, he’s great But to me when it comes to real estate, I’m not going to be paying cash for everything And so I’ve kind of left that and then I you know, rich dad poor dad was a huge I call

Dylan Silver (07:05.891)
Mm-hmm.

Jason Tindol (07:24.236)
Robert Kiyosaki, my godfather, but he doesn’t know it yet. So he’s someone that really has revolutionized my family tree forever. And again, he doesn’t know that yet. I think one time he liked my post and so that made my day. It was probably some bot that liked it. But it’s something that, you know, through the reading, I just kind of was challenged with the thought process of, you know, I think

I think we might want to look at this, the idea of passive income and the idea of portfolio income and the idea of earned income and how every April 15th, which of course was yesterday, you know, if you’re an earned income earner, you felt the pain pretty bad yesterday. And so with my real job, I felt the pain yesterday. But with my passive income through real estate and my portfolio income through

Dylan Silver (08:09.324)
Go.

Jason Tindol (08:19.47)
you know, whatever assets, you know, I didn’t feel any pain. In fact, I received benefits yesterday because of it. the, the, all began with the idea of Robert Kiyosaki and starting businesses, you know, little side businesses, you know, one yard led to 76 yards and a landscaping business. And that was by accident. And it really was by accident.

Dylan Silver (08:25.229)
Right.

Jason Tindol (08:45.102)
And then one driveway led to, I don’t know, 50 plus driveways through redoing driveways. And again, it wasn’t me doing the work. It was just kind of that entrepreneurial background of, I bet we can figure out kids that want to make some money. And I just have to be smart and try to find business and market the right way. And so that turned into a little bit of cash reserves. And then that turned into, we should probably get some real estate.

You know, I was a private school teacher at the time. This is in 2007, 2008, and making pennies. But I had some funds to where it’s like, hey, we should probably, we should probably, you know, get into real estate with the income from the landscaping business. And it wasn’t a ton, but it was some. And, lo and behold, 2008 happened. I didn’t even know because I was broke anyway.

Dylan Silver (09:25.89)
Really?

Dylan Silver (09:34.883)
Mmm.

Jason Tindol (09:44.718)
So I didn’t know the country was in a near depression after 2008. And so I just started looking at properties and found a little duplex in Nashville and found a little triplex right next to it. Actually, we bought the duplex in 2009, June of 2009. And then right after that, three months later, the same lady who sold us a duplex wanted to sell her triplex.

And so we bought those things and that kind of started our journey. And I stayed in private education making pennies on the dollar and we had to scrape and grind and, but my wife and I both, had no kids at the time. My wife and I both said, we’re not selling these things. Our vacation were those rentals and our Starbucks were those rentals and our

You know, we really live disciplined because of those rental units, because we just didn’t have the extra money. And then one day, you know, once 2012, 13, 14 hit, it just blew up. Nashville just blew up. And then we just slowly began to, you know, make some decisions from there, which we’ll get to if I’m trying to answer your first question, how did it all begin? And that’s, that’s kind of how it all began.

Dylan Silver (11:07.177)
Yeah

So talk about bootstrapping this, right? So you’re a teacher, private school at this point in time. Maybe you have career aspirations, ambitious, you know, but at the same point in time, you’re finding the time to educate yourself about real estate. You happen to buy maybe at the best point in time in either of our lives to buy real estate, like divine intervention. Not everyone’s going to have that opportunity, but you have that opportunity. You were there.

I like to say that if you’re a gorilla networking, if you’re constantly shaking hands, you might meet the right person. But if you’re not doing that, you got no shot. So you were out there finding the time away from your busy career. And then also, this is actually something that I haven’t talked about in the podcast at all, but having a spouse who’s supportive of let’s like not go on the vacation.

eat out you know however many times a month or a week and live live kind of kind of like live like we’re we’re broke you know and so the the reality is is that I know personally right now I know some real estate investors with millions in assets plenty of homes who are still living like they’re broke because you know time markets can change you know people might have varying cash reserves and some people just put it all

into the game, into real estate. I can definitely relate to that sentiment. So at that point in time, you have your duplexes and you’re working and you’re seeing proof of concept. 2012 comes around, these properties probably double or triple in value. And you’re thinking, wow, I’m going to sell these things. I’m going to hold onto them. I’m going to buy some more. What’s going through your mind at that point in time?

Jason Tindol (13:03.374)
Yeah, we definitely stayed broke on purpose. So our thought process, so a single income family, my wife was a stay at home mother and loved every bit of it. being a stay at home mother, was able to, she doesn’t really love real estate. She didn’t then, but she didn’t hate it either. She just supported it. And she didn’t really understand, okay, we’re not really making a lot of money from these things, so why do we have them?

She didn’t understand yet, did I frankly, the idea of appreciation. She didn’t understand yet the idea of, we’re not paying the mortgage, our renters are. And then the idea of the tax benefits. She really didn’t grasp that because again, we were just young at the time. We were babies. But we just kind of worked together and we kind of figured it out together.

through some of the challenges and one year we were audited and it cost us a fortune. We still remember the name of the auditor. That’s how fresh the memory that is. Because it was an eye-opening experience of, man, we actually have some businesses that we didn’t claim the right way. But we learned from that and now we have a lot more than what we had then.

we realize that, you’ve got to have CPAs and you’ve got to have a team of people that help you with this. So like you said, you you do have to network quite a bit, but you don’t have to really work hard on that. It’s just the people that you interact with. And I’ve just been blessed to interact with some pretty amazing people and none of our stuff. We do have some, some that we team up with, but for the most part, our stuff is our stuff. It’s not, it’s not in a, in a partnership in any, in any way.

And that kind of led to, like you said, in 2012 and 2013, so we bought these places, both of them, for $300,000 combined. A duplex and a triplex combined for $300,000. So five doors, basically. And then, and you know, in 2018, we sold them and we sold them for about $850,000.

Dylan Silver (15:08.546)
Mm.

Jason Tindol (15:27.054)
And when we sold them, yeah, when we were sold them, I mean, we had, we had a lot, we put a lot down for those places too. When I say a lot, mean, we put about $25,000 for each place. You know, today that doesn’t seem like a lot, but back then it was, I mean, again, that $25,000 was a car that we didn’t have. Uh, but we made the choice of, no, this is our, this is our legacy. This is what we’re going to do. Um, and then we took that, the funds from that in 2018 and we.

Dylan Silver (15:27.351)
Holy smokes.

Dylan Silver (15:42.339)
farm.

Jason Tindol (15:57.326)
1031 exchanged them into an apartment complex. And then the rest is history. Every year since then, we’re picking something up. And usually now, anyway, it’s a lot bigger than it was back in 2008 and 2009. So if I could give any thoughts, there is a lot of luck that’s out there. We feel that God’s blessing has been put on us. We really feel that way.

Um, we could not have done it without, you know, some of that, um, nine intervention that you talked about earlier. But with that being said, um, we also feel that we set ourselves up to be ready for when, when the time comes for a deal. And we’re always looking for a deal right now. In fact, right now are the best times to find really good deals. I don’t care what anybody says about the interest rates. You know, you can get good deals right now. Um, and.

Dylan Silver (16:31.223)
Yeah.

Preach.

Dylan Silver (16:43.075)
Yeah.

Dylan Silver (16:49.697)
They are.

Jason Tindol (16:55.278)
And that’s what we’re doing. We’re actively pursuing. have, I don’t know if your audience knows Michael Zuber, but you know, we have one rental at a time. I’m a big fan of Michael Zuber and we have our buy box. looking at our buy box. We’re, you know, we’re making offers all the time. Most of our offers are what he calls disrespectful. I call smart. He calls it disrespectful. So, um, yeah.

Dylan Silver (17:02.817)
the

Dylan Silver (17:18.765)
Well, you know what it is, Jason is I’m an agent myself in in Texas and Dallas newly licensed. I’m a wholesaler too. I was a wholesaler before I was an agent for two years and I I feel and I see and I sense when I’m talking with the realtors that they don’t like that I was a wholesaler and they they they might not say it to my face, but some of them do and When you’re making

like you said, disrespectfully low offers, which is what I did and what I still do if I’m representing certain buyers, especially in Texas, but I think anywhere agents are required to present these offers to their seller unless the seller has it in writing. Like we’re not looking at anything below X. And so as a seller, like if I’m getting the, used to, I used to almost feel badly like, we’re making these offers as a seller. I want to know that my agent’s working.

I want to know that I’m getting some offers in, right? And so if it’s crickets and the home has been on the market for a hundred days and I get an offer, if it’s a home, like this is an example of something that just went down in Austin from an investor that I work with. Home was listed for like $330,000. He got it under contract for 200, like 30, $100,000 less. And these things can happen if you’re making, you know, a hundred offers. So I’m all, I’m all on board for, uh,

making some low offers.

Jason Tindol (18:46.402)
Yeah, well.

Yeah, obviously, you know, the offers usually are best when you look at days on market. They’re usually best when you look at, you know, how much activity has been around the place, you know, how, how much TLC it’s gotten. And that’s usually how we, you know, we’re just constantly hunting. And so all the stuff we own is out of state. I don’t know any, I don’t, the only thing we don’t own any of our personal property.

inside of Washington. It’s all in other states. So we’re out of state investors and we see our stuff maybe once a year, if that. That’s worked for us and I’ve heard horror stories about that, but we have never had a single issue with anything. Obviously, we have to fix the toilet sometimes, do all that stuff, but for the most part, it’s been

We don’t look at it as you’ve got to find real estate. We look at it as you got to find cashflow. And if you find cashflow, it may not be in your backyard. It may be in another state. And so we’re always looking for cashflow and we’re always looking for what we call disposable income. So it’s not how much income you make. It’s how much disposable income you have. And so we don’t buy crap. We don’t buy cars. We don’t buy all that stuff. We put it all in a tank and

Dylan Silver (19:48.387)
Yeah.

Jason Tindol (20:12.722)
And we stay broke. We go out and we spend it on real estate. I don’t know if you know who Grant Cardone is, but Grant Cardone is someone who says, stay broke. And I know he’s got a lot of fans, and he’s got a lot of haters. I’m a fan. And we try to follow his advice of live off 20 % of your funds and stay broke and invest in assets. And that’s worked out well for us.

Dylan Silver (20:21.975)
Yeah.

Dylan Silver (20:31.341)
Me too.

Dylan Silver (20:40.481)
What really opened my eyes, Jason, was I got a passport two years ago and it completely blew my mind when I was going to the places that I was traveling to. And specifically when I traveled to Santo Domingo in the Dominican Republic, I went by myself. And at that point in time, I’m 31 now, I think I was 28 years old when I went. And in my mind, I was thinking,

as an American in order to be anybody I needed to have a luxury car and I needed to be having the nicest clothes and that if I didn’t have either of those literally if I showed up this is how small-minded I was Jason if I showed up to the gym and didn’t have in Dylan’s mind the freshest fit that how was I gonna make a friend so I go to Santo Domingo and I’m seeing people driving cars that look like they’ve literally been like exploded like

like a carcass of a car. I’m seeing no laws on the roads, like oncoming traffic, 50 miles an hour. I’m seeing people living in this island with no drinkable water, no AC, and Jason, they were happier than me and happy, happy. And so they had friends, they had food, you know, and I just fell in love.

with that culture and so I came back and my mind was like blown and so really I was in real estate at the time but then I had a shift and I realized all these things that I valued as who I was like you know I had the car but boom I have clothes I have this nice apartment I’m now realizing like that was just like foolish like what was I even thinking what was I doing so somehow through the the Grant Cardone’s through

through the Dave Ramsey’s, through your own personal experiences, you were able to come to that realization that took me leaving the country to figure out.

Jason Tindol (22:46.924)
Yeah, Yeah, there, you know, none of this is new. There’s nothing new under the sun. It’s it’s, you know, learning through people like Ramsey and Zuber and Cardone and Brandon Dawson and, know, and all the other authors that are out there. And then and then really helping with people you come in contact with that, you know, are smarter than you. And there are a lot of people smarter than me.

And just having those conversations and say, Hey, tell me a little bit about that. And, and even thinking about, okay, can I kind of delve in that particular direction? And in, you know, in adjusting and adapting to each of the markets, know, 2020 was different in making an offer than in 2025 with these higher interest rates. So when it comes down to it, think being able to pivot and adapt and

continue to reinvest in yourself is extremely important for real estate.

Dylan Silver (23:49.217)
Jason, I’d love to get your perspective, just high level broad strokes for someone who loves their W2 job, right? And you hear a lot of people talking about maybe not loving it. Well, someone like yourself has the blessing to love their job, right? But they want to invest in real estate. And frankly, there’s people like this out there, but on the social media and just people’s attention, it seems like that isn’t as glorified as the people who leave completely to go and do real estate.

What would be your general advice to someone who maybe doesn’t have it in their blood, it’s not in their family, they don’t know if they can be successful at it? What’s life look like as you’re starting out and then also connecting the dots to today as someone who’s maintained a career while also being active in real estate?

Jason Tindol (24:38.67)
Yeah. First, daily discipline to invest in yourself, but then getting more practical. Let’s just use you, for example, at your age and let’s rewind it five years and let’s just say you have a young wife as well. In my mind, if you were able to house hack or you were able to buy a duplex and live there, so you can only put 5 % down or

around that. And then every two or three years, do it again. And then every two or three years, do it again. That is the fastest way I think it’s not, you know, the best way to get rich quick is to get rich slow. We know that. So it’s not fast, but it’s faster than, you know, than saving up and paying cash for a particular home.

The reason I like that is because once you have a family, it’s very difficult to do that unless you just buy a duplex and school is on the other side. But house hacking for someone like your age or someone younger is, is really something to look into, you know, getting into renting out a bedroom or two. You can get in there, put 5 % down, have someone else float the mortgage and just keep doing that. And it takes, in my opinion, it takes about 10 years. That’s again, I’m copycatting someone else. Zuber, think says that.

After about 10 years, you’ve got all this appreciation working for you. You’ve got all these tax benefits working for you and you starting to receive some real income from your doors. So if you’re making $150, $200 per door, well now all of a sudden things are looking up for you. And so that would be my biggest advice. The second piece of advice is from your daytime job, look to

increase your disposable income. You get a raise every year most of the time and it may be small, but if you live on where you are right now and then every year you get a raise, that’s your disposable income. You just stock it. Just stack it up and when you stack that up eventually you’ll be able to live on your income which is down here.

Jason Tindol (26:55.938)
But over time, the raises have gotten you to here or the promotions have gotten you to here. Well, now you’ve got this gap that you could use as disposable income. So my wife and I, we don’t look at ourselves as, man, we make a lot of income. We look at ourselves as, okay, we’ve created a lot of income from our disposable income based on how we live. And we don’t drive junk, not anymore. We drive nice, you know, but we’re not going to go out and get the Tesla truck and we’re not.

Dylan Silver (27:15.489)
Yeah.

Jason Tindol (27:25.314)
We’re not going to do that stuff. And the reason is because disposable income allows us to do more assets, things that create income. think sometimes a lot of people buy assets, but they don’t realize that if that asset is not putting money in your pocket, it’s not an asset until you sell it. Then you might make it. It makes some money then. But to me, we’re always looking to buy and create cashflow immediately with our and we’re going to buy with that.

Dylan Silver (27:51.959)
Yeah.

Jason Tindol (27:55.106)
with that disposable income. So young couples, tell them that all the time, or younger people, or even our age where kids are gone and it’s just you and your wife or you and your spouse and you can house hack and create that income pretty fast. That would be my biggest piece of advice.

Dylan Silver (28:19.284)
Amen. That is,

That is a strong testimony, honestly, going from starting out buying a home in the crash, quite literally, to then seeing it double, almost triple in value in a handful of years, scale to today, talking about doing it remotely without physically being there in person. You mentioned most of these, or if all of them are outside of the area. While having a career, scaling to the height of that career, incredible.

incredible. I my hat goes off to you Jason. We are coming up on time here. Where can where can folks go to get a hold of you?

Jason Tindol (29:00.718)
Do I want people to get a hold of me? Well, mean, you know, they certainly can email me. My email is Jason Tindol, spelled like it is on the screen there, at K, as in kite, W, C, S, dot org. I’m on Facebook, Jason Tindol, on LinkedIn.

Dylan Silver (29:03.427)
I

Jason Tindol (29:27.7)
on Instagram, all the different social media outlets. I don’t have a business website. I have a school website, but you know, it’s not mine, it’s the schools. But they can certainly look me up through our school, Kingsway, Kingsway Christian Schools. so I’m always interested in talking real estate and, you know, helping as much as I can. I’m not like you, Dylan, where you can spend more time with some folks. And so I can’t really commit to that as much.

But I’m happy to answer any questions or help anyone that I can, especially if they’re in a similar situation as I am. If they’re in Christian education, I’m all about that. So if you have someone that you know in Christian education, I can really help those folks for sure. I can make time for that. But otherwise, happy to answer emails and things like that.

Dylan Silver (30:20.503)
Jason, thank you so much for coming on the show. Thank you for time. Thank you for giving us your story and for providing some great value today. Thanks for coming on.

Jason Tindol (30:29.794)
Yeah, thanks Dylan. Take care, man.