Patience & Discipline: Keys to Thriving in Real Estate

Stephen Schmidt (00:02.457)
Welcome back to the show where we interview the nation’s leading real estate entrepreneurs. We’ve got a special treat for you guys in the house today. We’ve got Jake Ostrich in the studio and we’re going to have a great conversation. Jake has been investing in real estate for 25 years. He’s done a little bit of everything in the single multifamily space from what it sounds like. Hasn’t had as many as 90 doors at one point. Still owns quite a few and does some flips and everything in between. And we’re going to talk about

how he’s navigated the landscape over the last 25 years with all of the lessons he’s learned and some of the things that you might want to avoid to do potentially even. So just remember at Investor Fuel, we help real estate investors, service providers, and real estate entrepreneurs, 2 to 5X their businesses, which allows them to build the businesses they’ve always wanted to allow them to live the lives they’ve always dreamed of. That being said, Jay, welcome to the show today.

Jake Ostrich (00:57.774)
Stephen, thank you. It’s privilege to be here. Thank you. Thank you.

Stephen Schmidt (00:59.363)
Super, super excited to have you on.

So tell us this, before we get started on some real estate, which we generally talk about, how did you get started in 2000 and what got you here?

Jake Ostrich (01:17.806)
So what got me started in 2000, I’ll kind of rewind back all the way to 1996. I was, me and my fiance, which is now my wife, we were living in an apartment right outside of Philly, kind of just making sure the relationship was gonna work right till you get to the next level.

Stephen Schmidt (01:45.005)
Mm-hmm.

Jake Ostrich (01:47.074)
you know, there was this infomercial that it kept playing. It felt as though it was on like an hour loop. it was an older gentleman, name’s Carlton Sheets. you know, some of the, don’t think he’s, unfortunately, I don’t think he’s with us anymore today, but some of the viewers might remember him. And you know, he was an investor, I think in Florida. And at the time, you know, like I didn’t, I,

do zero about real estate. I barely even knew what a mortgage was. you know, so these infomercials would play and you know, was was these common folks, they, you know, they’re buying a house, they’re putting a little money into it, and they’re selling it, and they’re making all this profit, or they’re renting it out, and they’re making all this cash flow a month. And what how I really related to it was I

grew up in a family general contracting business. So what was relatable at the time was, you know, could kind of see what renovations they were doing. And I’m like, well, you know, I could, you know, I can do that. Right. So I’m like, you know, I got to, I got to buy this. I got to buy this course. I think it was like $200 at the time. And cause I was just, I was just so fascinated by this. said something that’s not adding up here. Right. I just, this can’t be possible.

Stephen Schmidt (03:07.833)
you

Jake Ostrich (03:10.894)
I didn’t think it was possible. So I bought it, it came in like this big thick three ring binder, right? There was no, you know, back in 96, wasn’t, oh, you know, click on this link and we’ll send you the package. There wasn’t any thing like that. So, you know, it showed up, had like all kinds of CDs that you put in a CD player, right? And that’s how you listen to the audible part. And then, you know, all of the paper, you know, the paperwork and…

Stephen Schmidt (03:25.721)
you

Jake Ostrich (03:40.578)
the outline. I rifled through it and I put it on the shelf and it sat there for like a year. I did nothing with it. And it wasn’t until we eventually bought our house in 98 and the guy who we used to use to paint our renovation projects in my family business, he actually had like two or three rental properties and

Yeah, he also knew of Carlton Sheets and we got talking because like, hey, you know, if you’re interested in this thing, you should come to this group. It was like a local real estate investment group. And so I fast forward a little bit. I went and it was like, you know, really eye opening for me. There was all, you know, there’s all kinds of vendors there and hard money lenders, insurance brokers. I mean, you name it, it was there.

And I probably, I joined that in 98 and I just was like a sponge. I would go once a month and I would just keep absorbing, absorbing all this and thinking that I think I might wanna buy one of these places, but it took me like, it took me two years to gain enough confidence to actually.

take action and buy something so we bought our first one in January of 2000 and you know it’s like everything else even like you know once once you get over that hump it’s kind of like wow that wasn’t bad let me you know you know you have like this huge weight off your shoulders right and you’re like so I just I bought I bought another probably 12

in like a little over a year. just kept it cookie cutter. It was the same type of house, same price range, same construction, same area, same township. I didn’t kind of veer out of the sandbox. I just kept everything the same. I just kept repeating the process.

Jake Ostrich (06:05.582)
That lasted, let’s see, 2000. I still had my full-time job and I would go over after work and kind of do some of the things on the house. We would use our subcontractors. They would come over and like the HVAC guys and roofers, they would put that part of the house together. That lasted. We had, we got, you know.

I ended up getting married and we had kids. had twins in 2001, so I kind of put all the real estate stuff on hold. And in 2008, needless to say, when the housing market blew up, I had an intuition from God and he told me to leave my job and to go do that full time.

And that’s, that’s, you know, I just, from 2008, I don’t know, I probably bought my last one like 2018. And that, know, I just was able to buy 90 before, you know, when 2018 hit, like I kind of got a little stagnant. I didn’t, I kind of wasn’t, the market changed again and it was a little more difficult to find good deals.

and I kinda got a little complacent and just kinda rode things out a little bit with the acquisition part of the single family house. So that’s pretty much how I got started.

Stephen Schmidt (07:46.398)
Wow, that’s amazing. What now? One of the things that you mentioned in there is you had this intuition from the Lord and you quit your job during the market crashing. What was that like?

Jake Ostrich (08:03.234)
Well, so in 2008, you know, we had the general contracting business and we also had like another little division was like a cabinet shop and I kind of ran the cabinet shop. It was only like me and another guy, but and you know, could tell that business was like really slowing down and I knew in the back of my head that my dad didn’t really have enough

financial capabilities or probably interest into like moving the shop because at the same time in 2008, you know, we rented the shop and you know, the owner was, or the realtor for the owner was like, hey guys, you know, we’re not going to renew your lease. We sold the building. I don’t know. You have like maybe like 60 days or something to, you know, to move. So.

You know, between that, the cost of moving and the bad economy, I just knew that, I just knew it wasn’t going to be a good move for him to try to relocate this thing. And I always kind of wanted to do the real estate full time. Like I had a vision of doing it. And I remember this intuition hit me. It was, you know, I…

Stephen Schmidt (09:16.354)
Huh.

Jake Ostrich (09:32.31)
to get too spiritual on the show but yeah he spoke to me and I’ll never forget it and I just called my dad up and I said I’m gonna try to do this real estate thing full-time I know I had no idea if that was gonna be successful or not I didn’t I didn’t have any any plan I didn’t have a business plan I’m not I just

woke up and he spoke to me and he said to go jump and I jumped. It comes, it’s like anything in life. There’s ups and downs and there’s lessons and it’s 10 times harder than you think it’s gonna be and it takes 10 times longer, like Annie Frisilla always says.

Stephen Schmidt (10:01.897)
Wow.

Jake Ostrich (10:29.078)
Here we are. Here I am.

Stephen Schmidt (10:30.42)
Right, you got.

I love that you said that. That’s super cool. I know you’re my people now too. I know we just met, but you mentioned Andy Purcell. He’s been somebody I’ve been following since the MFCEO project. Even back actually like right around 2020 time is when I really started listening to him. And for context for people that don’t know who that is, he’s, you know, like essentially built a billion dollar supplement company, which I don’t know if it’s actually at that evaluation, but nine figure entrepreneur, a hundred percent who

Jake Ostrich (10:41.44)
wow, yeah.

Stephen Schmidt (11:01.017)
Basically in the first 10 years of his entrepreneurial journey, he made a collective total of, me if wrong here, but it’s something like 67,000 bucks. Like in the first 10 years of being an entrepreneur, almost shut everything down, but he stayed the course and now 25 years later, kind of funny that you guys almost started around the same time in your entrepreneurial journeys too.

Jake Ostrich (11:09.634)
Yeah. Yeah.

Jake Ostrich (11:23.406)
Yeah, a little different outcome between the two. anyways, yeah, the adversity and the struggles are, you know, they’re real. you if you would ask me or if someone would ask me if you could go back in time and change anything or, you know, and I would say no.

Stephen Schmidt (11:26.455)
Yeah. Well…

Jake Ostrich (11:50.368)
And that might sound odd. I appreciate the lessons and the failures and the sleepless nights more than what the 90 properties brought.

Unless you go through that, you aren’t the person that you are going to grow into the person that you want to become, right? You know what I mean? You can’t be who you want to be without those lessons. And those lessons, take time. for me, it was a 25-year span. You don’t get dropped off at the top of the mountain.

You started at the bottom and you had to take one step up and you can’t rush it. You can’t skip steps. Life doesn’t work that way. again, I’m extremely grateful for the hardships. Extremely grateful. I know that sounds like catter and toot of the say, but you just can’t get anywhere of,

Stephen Schmidt (12:58.681)
Right.

Jake Ostrich (13:10.016)
of value without tripping along the way and starting over. It just doesn’t work that way.

Stephen Schmidt (13:20.619)
I had a former mentor and I’m sure he stole this from a book, but he said something one time that just has resonated with me. He said this to me probably six years ago now. And he said, Stephen’s struggles are the seasoning that make life so sweet.

Jake Ostrich (13:37.102)
I love it. That’s that’s great. Wow That’s that’s a good one Dirty throw. Yeah, that’s a really good

Stephen Schmidt (13:41.465)
What a profound statement, right? Telling you what, was like, never thought of it like that, but you got a point, Cody. 100%. So what are some of the things, because obviously you’re a veteran in this business, and you’ve pretty much seen it all. What are some of the common mistakes that you see?

Jake Ostrich (13:48.44)
Great! Very good. I love that. Wow. Nice.

Stephen Schmidt (14:08.341)
newer folks getting started or even people maybe when they’re right in that like five deal a year market wanting to scale, you know, kind like I said in the intro, like with investor flow, you know, we help people scale two to five X, right? And that’s one of the things we find that sweet spot between like five to 10 deals a year, people wanting to go to 50 deals a year, for example. And then obviously like the people that are just getting started, what are some of the pitfalls that you see people really making based on your own experience and what you’ve seen in last 25 years in the business?

Jake Ostrich (14:37.036)
I think if you’re, you know, if you’re at five deals a year, you know, whatever those deals are, and you want to, you know, scale to like what you’re saying. I think the biggest thing is. Well, one of the biggest things there’s there’s a lot, you know, there’s discipline, right? And there’s patience and like most entrepreneurs.

We’re not very patient people. just, you we have a thought and we have a vision and we just want to go make it happen. And that’s awesome. And but it’s just like I was saying with the mountain, just like life’s not going to just automatically pick you and jump you, you know, 10 times farther ahead of everybody else. So you have to have patience and you have to have the discipline.

to have those patients. And I think some folks, when they kind of lose sight of those two elements, they kind of get that shiny object syndrome where, well, this is taking too long and I don’t have the patience to go from five deals to 10 deals. And they kind of look for another kind of rich get quick. I hate that saying, but.

Stephen Schmidt (16:01.405)
you

Jake Ostrich (16:05.602)
you know, maybe, you know, they’ll look for something else that they think that they can, they can scale from zero to level 10 in two days, right? And where, where you’re like, you know, like, dude, now you’re starting from something that you, maybe you don’t even have any experience with. you know, reel everything back and stick with what you started because you already have momentum. You’re already doing five deals. You’re already doing five deals a year.

Stephen Schmidt (16:30.361)
Okay.

Jake Ostrich (16:34.902)
You know, to do 20 deals a year, you’re already halfway there, right? Like, we’re not quite halfway there, a third of the way there or whatever. And it’s basically, what got you there is not going to get you to where you want to be. So you have to have some mindset shifts. You have to associate yourself with different people. You have to have higher level conversations.

And you have to self audit who you’re hanging around with, what are you guys talking about? Is it something that’s gonna get you to that 15 deals a year or is it something, the conversation’s the same as you’re having with people that are still stuck at five deals a year? it’s a complex answer and that might have been a little long winded, but it’s without a doubt possible. It’s just, you know.

Who do you need to become to be able to get in that rhythm to get to the 15 deals a year? It’s all here. It’s all between our ears. It’s all mindset, all of it.

Stephen Schmidt (17:45.345)
Right. Yeah, I 100 % agree with you on all counts there. your point even with the patience aspect, sometimes

Jake Ostrich (17:50.414)
you

Stephen Schmidt (17:59.565)
I don’t know if you’ve ever heard of the kind of that journey where you start out in uninformed optimism and then it hits to informed pessimism and then you have the valley of despair. Have you ever heard of that chart? So the problem in what you’re what you’re saying there is exactly exactly the point of why that was created because most people they start something and they’re

Jake Ostrich (18:13.666)
Yes.

Stephen Schmidt (18:26.089)
They’re uninformed and they’re optimistic because it’s the best thing that’s ever happened and they’re going to crush it, right? And so they go there and then they realize, this is so much harder than I thought it was going to be. And then they get to a point where they’re in the valley of despair and most people quit between those two phases and go right back to some new shiny thing. That to your point, I think get rich quick is it’s just such a weird phrase that we use because I don’t think anybody’s, I don’t think anybody in our culture today thinks they’re just going to go from zero to a million bucks in a year.

But like for some people, an extra 10, 15 grand a month would be life changing. You know what I mean? Like in retrospect, not that much money, but at the same time, it’s like people even get stuck on, think, realizing how fast it actually takes to build the systems and the processes to actually create more income. And I think that’s what you were saying.

Jake Ostrich (19:00.462)
Yeah.

Jake Ostrich (19:11.107)
Yes.

Jake Ostrich (19:14.732)
Yes, exactly. Very good point. Very good point.

Stephen Schmidt (19:16.729)
100%.

So, and another thing that you mentioned there too, as far as like pitfalls, we’ve got a couple folks in our group who are just rock stars. I think you’d relate a lot to them. I won’t mention their names for anonymity sake, but I was just down in Dallas at one of our quarterly mastermind meetups and they were doing hot seats and they’ve got a thriving general contracting business, like killing it.

And they’re like, well, we’ve done some real estate and we do this and we’re like the go-to people in our market for real estate investors because they know we have all the price sheets, we do all the work, we’ve got all the subs, like this is what we’ve been doing for everybody else. So now we’re wanting to go and do this for ourselves and we want to go from X to X this fast. And we had another guy in the room as he was presenting going, by the way, this guy’s built $120 million portfolio in the last six years.

And he looked at them and he goes, guys, you guys have 10 kids between the two of you and you’re crushing it over here in this area, but you’re wanting to shut all this down to go and do real estate right now, just because you see what everybody else is doing, but you don’t have the systems that deal for the management to actually produce it. And you’re just going to let this thing potentially starve. And they’re like, well, that makes a lot of sense. We should probably focus and go a little bit slower.

have been built upon it because there’s acclamation to each level. Would you agree with that?

Jake Ostrich (20:49.72)
thousand percent totally agree with that that’s a really good point really good insight yes I yeah nothing saying the guys can’t do it no one who was saying they can’t but you know so this you know let’s let’s slow the horses down a little bit and and and approach it the right way like and and I mean it sounds like they have a ton of

People around them that that can you know that can guide them on the on the the on a way that’s sustainable Yeah, and and the eggs. man thousand percent. Yeah

Stephen Schmidt (21:23.07)
Power of a community.

How important on that note, important has community and mentors? How important has that been for you over the years? Or are you just one of those lucky people who just never had anybody speak life into them?

Jake Ostrich (21:39.182)
No, no, I’m not definitely not one of those folks. I’m a huge proponent of it. had my first coach, think it was 2021. you know, up to 2021, didn’t, I was like a lone ranger, right? didn’t, I did mostly everything myself. I didn’t like, I didn’t have an assistant. My wife would help me out a little bit here and there, but you know,

she was really raising the kids as well. So like, I, you know, couldn’t expect a lot. And yeah, 2021, I hired my first coach and he completely rearranged my life. I mean, I had him for six months. was a, you know, like a six month session. And you know, he basically, he basically stripped me down and rebuilt.

and like rebuilt me, know, I don’t want to say spiritually, but mentally, rearranging things of importance. And I was just blown away. I’ve never been, you know, witness to anything of what I went through with him. So I owe him a massive amount of gratitude and I still, you know, he’s local to my area, so.

Stephen Schmidt (22:38.441)
Boom.

Mm-hmm.

Jake Ostrich (23:06.838)
He’s in New Jersey, but it’s not far away. You know, we still connect and things like that. And yeah, I think I think the power of that is it’s it’s limitless. It’s you have to you have to be in those kind of rooms. You have to, you know, be be and be around people who who are positive people, you know, who are going to pull you along, right? Not push you down.

Stephen Schmidt (23:26.036)
Okay.

Jake Ostrich (23:37.006)
and be there when you have a question. When I first started, that painter, Steve, who did our painting, he was a mentor of mine in the beginning. I think I would call him, it felt like I’d call him every day, is this a good deal, is this a good deal, what do you think of this? And was, dude had a lot of patience.

Stephen Schmidt (23:56.445)
you

Jake Ostrich (24:06.19)
He kind of guided me along and to where I was kind of a little bit more comfortable, I didn’t have to call him that often. for people who are starting out, it’s extremely, extremely important to have people in your corner like that, extremely.

Stephen Schmidt (24:24.409)
Let me ask you this, if you were able to go back to the beginning and start all over in 2000, but you were able to take everything that you’ve brought with you in the last 25 years, all the wins, failures, lessons, et cetera, what would you do different and what would you do the same?

Jake Ostrich (24:49.838)
I would concentrate on doing more flips. So what I mean by that is, know, so I only bought rental properties. I did some flips here and there, but maybe, I don’t know, maybe like one or two a year. And, the rest of the time was spent just acquiring the rental portfolio. And,

The situation where I would run into is, the rental properties are great, but you’re kind of building a longer term asset. And it’s difficult to kind of live off of cash flow like I had to do because I left my W2 income job. So I just went on like a buying spree and

Stephen Schmidt (25:34.553)
Thank

Jake Ostrich (25:46.862)
you know, as I was buying them and renting them, renting the houses, I was kind of living off the cash flow. And I don’t think so I would supplement that with some more flips so you have, you know, more lump sum cash that you can draw from versus drawing from, you know, rental cash flow. It was massively stressful. And, you know, I what I was

kind of always behind the eight ball with, you know, like tax payments and things like that. Not income, like personal income tax, not that, but just, you know, municipality taxes, you know, cause like you’re just taking too much out of the business and.

Stephen Schmidt (26:29.58)
Hmm.

Jake Ostrich (26:36.812)
But I just, it worked out. Somehow I was able to work it out to where you do eventually get a critical mass of rental properties and as long as your way of living doesn’t go crazy high, as long as you keep that moderate, you do reach a threshold to where you’re like, okay, things are a little bit better, a little bit easier.

Stephen Schmidt (26:40.803)
Mm.

Stephen Schmidt (27:04.624)
All right.

Jake Ostrich (27:07.096)
But still, I still absolutely would not recommend doing that, like the way I did it. And I would definitely build the rental business and also supplement it with either wholesaling or flips, another lump sum type of business. So that’s one thing.

Stephen Schmidt (27:29.837)
What would you do the same?

Jake Ostrich (27:34.862)
What would I do the same? would have the same urgency. I would have the same desire. In my case, I was called and I walked away from…

Stephen Schmidt (27:42.466)
Hmm.

Jake Ostrich (28:04.514)
you a family business that, you know, was, was that I was able to make enough to pay my bills and I walked away from that. And I think you have to have, you have to have massive belief and massive faith that when you’re called, you have to go and you can’t, you know, where people get

tied up with that is they don’t believe it’s possible. They might get this intuition, they’ll, like we all do, we’ll spend the next five minutes of self-sabotaging it. And it’s to the point where we don’t take action on it. And there’s a reason this came to you. There’s a reason this intuition came to you. It’s not a mistake. He doesn’t make mistakes. It was sent to you for a reason.

Stephen Schmidt (28:38.809)
Mm.

Jake Ostrich (29:04.742)
And you again, you just have to have massive, massive faith and in yourself that embed on yourself that that you’re gonna you’re gonna make it work. And you you you’re gonna get to this vision that you have this this crazy vision that you have in your head. And and you know, knowing that it’s

Stephen Schmidt (29:24.665)
Hmm.

Jake Ostrich (29:32.032)
It’s extremely difficult and stressful and all of that stuff, but it has to be that way. Like it can’t, it’s not going to be easy. You know, it has to be that way. And that’s, wouldn’t, I wouldn’t, I wouldn’t change the intuition. I wouldn’t change that message that I got. Cause if I didn’t get it, I, I don’t know what I, I don’t know where I would have been. You know, I got.

Stephen Schmidt (29:50.379)
Hmm.

Jake Ostrich (30:00.108)
I wouldn’t be here. know that. But you know, when it helps, I find it like some people work well when they’re kind of their backs are up against the wall. Like I’m one of those people like when you have to do something like you need air to breathe, like you it’s the same as you needing air to breathe, you needing to go make money like you need air to breathe, then you’ll go do it. You just find a way to make shit happen.

Stephen Schmidt (30:02.83)
there.

Jake Ostrich (30:28.942)
It’s, it’s, it’s, you don’t think of, you don’t think of anything else other than that because it’s like survival mode. Yeah. And that’s, that’s, I like that question. I’ve never been asked that question before. I appreciate that. Thank you.

Stephen Schmidt (30:47.433)
You bet. Well, Jake, thanks for joining us. If anyone wants to learn more about you, what you’re working on, where should they go for that?

Jake Ostrich (30:54.702)
So, you know, I’m just gonna I love to talk to people I’m just gonna give my cell phone. I mean I’m on I guess I’ll get text first then anywhere You know my number is 610-331-9173 I mean on Instagram is Jake underscore ostrich. I’m on Facebook is just Jake ostrich and You can find me on LinkedIn

Stephen Schmidt (31:00.089)
Well, seven million people that listen will call you. Just fair warning.

Jake Ostrich (31:23.426)
Jake Ostridge too, pretty easy.

Stephen Schmidt (31:26.585)
Awesome, well I’m dropping you a follower right now on the olig. I think, it’s loading. Well, I it. Go drive him a follower, y’all. Shoot him a text if you want to. And we’ll see you on the next episode. Hope everybody enjoyed the show. Thanks again, Jake, for being here.

Jake Ostrich (31:30.53)
Thank you.

Jake Ostrich (31:43.704)
Thank you, Stephen. Thank you, brother.