From Military to Real Estate: A Journey of Growth

Brett McCollum (00:01.092)
All right, guys, welcome back to the show. I am your host, Brett McCollum, and I’m here today with Michael Greenwald. Today we’re going to be talking about personal growth and mindset. Before we do, guys, at Investor Fuel, we help real estate investors, service providers, and real estate entrepreneurs to 5x their businesses to allow them to build the businesses they’ve always wanted and live the lives they’ve always dreamed of. Without further ado, Michael, how are you,

Michael Greenwald (00:24.27)
I’m good, Brett. Thanks for having me. I really appreciate it.

Brett McCollum (00:26.654)
Dude, I’m honored to be here with you, man. I’m excited to have the conversation with you. We got to know each other a little bit pre-show, I’m genuinely excited to get into this. before we do, man, let’s do everybody little bit of favor. Let’s back up, rewind, give people some context, history. Who’s Michael Greenwald?

Michael Greenwald (00:43.15)
Yeah, absolutely. currently I’m living in San Diego, California. Originally I’m from Chicago, Illinois. Both my wife and I grew up in Chicago. know, kind of lower middle class family. My first, my first remembering of anything real estate related was my parents during the 08 housing crisis and

They had bought a condo and I don’t actually know what happened but they got burned pretty bad and I had just remembered this memory in my mind that, you know, they were… It was in the city of Chicago, yeah, downtown. No, you’re good. And so they bought it and something happened, it was awful, I don’t really…

Brett McCollum (01:22.036)
Where’s that at? That condo was in Chicago? Okay. Alright, sorry, continue, sorry.

Michael Greenwald (01:34.592)
understand the whole truth of what happened. yeah, just remember that they had this terrible memory in their mind of anything real estate investing, real estate related. So that was my first taste or introduction to real estate. after that, went through high school, was really looking for purpose or something to do what my career would have been. So.

Brett McCollum (01:55.528)
Yeah.

Michael Greenwald (01:59.734)
College was not the route for me. I chose to join the Marine Corps. So came out here to beautiful San Diego, California, served five years in the Marines. While I was enlisted, my wife and I bought our first Airbnb property, a single family home up in Big Bear, California.

Brett McCollum (02:08.115)
Wow.

Brett McCollum (02:18.718)
Uh-huh.

Michael Greenwald (02:23.64)
didn’t really understand everything that went into it when we first jumped in. Just kind of took action, jumped in, figured it out as we went along. But that kind of gave us the bug of real estate investing and understanding everything that comes along with it. So just had that first taste of it and couldn’t get enough. So used my VA loan down here in Oceanside and then went out, bought a few more single family homes. Been operating those for a few years.

Brett McCollum (02:27.058)
Yeah.

Michael Greenwald (02:51.736)
have my residence real estate license here in California now and we are also going into or switching out of single family home investing into multifamily apartments education.

Brett McCollum (03:02.792)
Wow, incredible. And how long have you been in the real estate, like, for how many years now have you been doing this?

Michael Greenwald (03:09.655)
just under four years total.

Brett McCollum (03:12.404)
Okay, so end of 21-ish? Yeah, yeah. Wow, man, like that’s incredible. So let’s back up a little bit. So you grew up, you’re in Chicago, you know, like that lower middle class, you know, fairly normal, most of us, right, kind of thing.

Michael Greenwald (03:15.692)
Yeah. Yeah.

Brett McCollum (03:34.004)
You say you don’t remember a lot, but did you have any idea what was going on during the 08, know, stuff with your parents? Or did they kind of keep it kind of separate from you?

Michael Greenwald (03:46.169)
They walled it off pretty well, you know, just the stress that I could tell they were going through and constantly worrying about, oh my gosh, are we going to lose this house? How are we going to make it through? Probably about 10 or 11. Yeah.

Brett McCollum (03:48.488)
Yeah.

Brett McCollum (03:53.844)
Sure.

Brett McCollum (04:03.198)
How old were you?

Brett McCollum (04:08.326)
Mm-hmm. Yeah, and I get it, you know, and that’s what’s interesting. My son’s 11, right? And kids, you don’t realize how much at that age, even, they really pick up on. You think that you’re wallowing them out, or you think as parents, and we do try to…

keep them insulated from things from struggle because I think every parent will identify with that. But it’s interesting that you’re saying even at that age, like they didn’t tell me but I knew something, you know? Yeah, interesting. So you get out of high school, you knew college isn’t for you, which that’s a lot of us, right? And what led you to the Marine Corps?

Michael Greenwald (04:36.76)
Yeah.

Michael Greenwald (04:50.988)
Yeah, so I had done a little bit of research because even since I was a younger child, like probably seven or eight, I had always been wanting to be a soldier of some kind. I remember logging onto goarmy.com and a bunch of the different armed service branches, websites to check it out. And the Marine Corps is the one I settled on finally because…

because it was the most difficult, because I wanted to challenge myself the most. And I just knew it was time for me to kind of go have other experiences outside of my hometown and expand my perspective.

Brett McCollum (05:22.494)
Wow.

Brett McCollum (05:34.516)
Yeah, you know what’s interesting is I mean, I talked to a lot of people obviously doing this and and I’ve known a lot of people over the years like a lot that many more over the years just I’m being in the industry. There’s three, like there’s three different people like groups of people that I find to have the most success in real estate. And one there is the ex athlete.

Okay? Two, this is gonna be a funny one. Most people are like, they think it’s funny when I say this, they’ve been to jail at some point or prison, right? I’m serious. And then three is ex-military. The most successful. know, and more often athletes in military that you see are the biggest, and my assumption is probably the discipline.

Michael Greenwald (06:07.01)
Yeah. Yeah.

Michael Greenwald (06:25.282)
Yeah.

Brett McCollum (06:26.142)
that’s taught from both things is why that carries over. Do you see any correlations in your business today that you have taken away from your service time? Like any disciplinary, like I do this every day, I do that every day. You know what mean? Is there any kind of disciplinary habits that maybe you’ve carried over?

Michael Greenwald (06:51.01)
I think more than any specific habit, maybe the character traits that I learned throughout my service are what serve me the most right now. being number one, think, accountability to…

Brett McCollum (07:05.287)
Yeah.

Michael Greenwald (07:06.478)
myself and my own actions and that I am am responsible for my reality and my success or my failure and second being consistency in some shape or form you know every day is not perfect life life throws its ups ups and downs bad days good days but the the consistency is is there even if it’s you know not not a steady linear path all the time

Brett McCollum (07:36.328)
Yeah, I like that, the accountability aspect of it. I know a lot of branches in military preach this a lot too, of like, you have to do your job because your neighbor beside you counts on you to do your job. Right? And I think that I see a lot of that from the folks that I know that like, I have to do my job well because people are counting on me to do my job well.

Michael Greenwald (07:51.32)
Mm-hmm.

Brett McCollum (08:02.062)
Do you see any, does that track at all from anything you’ve seen and what you do?

Michael Greenwald (08:09.58)
Definitely does. it goes back to the character traits and not just becoming this person who is not only accountable to myself but accountable to others and contributing to the success of others as well. I think that ties in with that.

Brett McCollum (08:25.417)
Yeah.

Yeah, very interesting. thank you for your service. I don’t think it’s said enough to our military vets. Thank you for your service, man. We love and appreciate all of you. We appreciate that. All right, so you’re in the service still. You’re married at this point, and you and your wife buy this Airbnb. What? And I don’t mean this in a bad way, in a funny way. What possesses you to buy an Airbnb while you’re in the service, man? Tell me about it.

Michael Greenwald (08:55.82)
Yeah, so the first one was up in Big Bear and being down in San Diego, we would go up there some weekends to go, you know, especially in the winter season, check out the snow, just to be around snow again, being from Chicago, not having to live in it, but just getting to enjoy it. And went up there a few times and seeing how just how expensive it was some nights when we would go up there, we were

something there’s something here like we should dig into this a little bit at least do some research and see you know if it would be possible to run our own Airbnb here and this was at the back end of COVID and everybody and their mother was kind of jumping into Airbnb or figuring out different streams of income so still got into the market at the right time got a killer rate on a second home loan 10 % down

Brett McCollum (09:34.6)
Right.

Brett McCollum (09:45.651)
Yep.

Michael Greenwald (09:48.866)
dumped our savings into it and kind of just figured it out.

Brett McCollum (09:52.178)
Rest is history. Yeah, I love that. Yeah, and that was that time too man when rates were incredibly low and You having the beautiful beautiful VA loan Exists, you know if the used right it’s one of the biggest

I’m a bully, by the way, and I’m not gonna make it. It’s not politically charged in any way. I don’t think we do enough for our veterans in general as a whole. just don’t think we do. However, one of the best things that that exists for veterans is the VA loan. If it’s used wisely and appropriately, it is the it is a hack to it’s a cheat code almost. And I’m like low key jealous of you that you have that you don’t even it’s like, dang it, that is so cool. And I’m, I’m excited that hear you like you said that a little bit earlier with the VA loan and doing this like

you being able to use that to your benefit for your future and man that’s so cool. So you’re in 2021, you start buying a couple more properties, you know get your license out you know and so are you practicing now with the license? Like what is what is the day to day with that look like?

Michael Greenwald (10:59.98)
Yeah, so right now my day to day is residential agent duties here in San Diego County and Riverside County. And like you said.

you know, VA loan, veteran affiliation, military affiliation, still being near Camp Pendleton and all the bases that are here in San Diego. My niche is helping veterans and service members. Because, like you said, I tell it to people all the time, it is such a cheat code that this benefit that we have and, you know, until you really understand the power that it holds to be able to use over your lifetime, like that understanding can be gained.

Brett McCollum (11:21.16)
Love that.

Brett McCollum (11:37.362)
Yep.

Michael Greenwald (11:38.948)
in a month or two of some good research, once you have that understanding, you can’t unsee it. And it’s just incredible. So that is my focus as well as helping veterans and service members use their VA loan and see the benefit that it has.

Brett McCollum (11:50.836)
I love that. Yeah, so let’s talk about this a little bit, because we kind let off the episode with talking about personal growth and mindset and that sort of thing. You grew up in lower middle class, probably using wealth.

Using real estate to grow wealth is probably not something you’re taught at much at a young age of that. I’m guessing, and if it was, I apologize. But learn the mindset shift that you have to go through to create a world where not only do you see it, but now you believe it’s possible. Because I think that’s a big deal. It’s one thing you’re like, yeah, that’s for these other people, it’s not for me. Especially because I grew up…

I grew up on the lower, lower level, not even middle class, like you probably looked rich to me growing up, right? But having that mindset of like, it was always when I was growing up, you see these people that are living in these nice homes, these big neighborhoods and da da da da, and you see this stuff, like, and I had these quote unquote friends from baseball or whatever, and I’m like, that’s for them, that’s not, we don’t get that. What’s the mindset shift that you had to go through in some of that to…

work I’m becoming. Like what does that look like?

Michael Greenwald (13:16.908)
I think it more than anything was a decision that just as I, you know, at some point took action to change the course of my life by joining the military, that in the same vein, I had to take that same action and make a decision that I would not let…

finances or my lack of education be something that held me back from the life that I wanted. So that decision that I would figure it out, yeah, it’s a struggle coming from the understanding and the conditioning that…

Brett McCollum (14:01.107)
Right.

Michael Greenwald (14:06.818)
we don’t have these things, I don’t deserve these things. So having to change that is really, really difficult and it’s always a process.

Brett McCollum (14:16.564)
Sure, yeah, and it’s, I mean, that’s the hardest thing is like, I think, I mean, you see a lot, and I could probably categorize a fourth person into that, like, successful personality profile is you grew up without much kind of thing, you know? And so some people just have that chip on their shoulder. For me, man, I don’t know if it was ever like this chip as much as it was something just inside of me said that, dude, I put my pants on just like you. You know, like.

Why are you more special than I am? But then when you, I don’t know, let me ask you this question. And if it doesn’t resonate, doesn’t resonate. For something I’ve walked through, the moment success starts to come, this doubt has creeped in my mind sometimes of like, I don’t deserve that. You didn’t grow up with this. You don’t deserve this. Has that ever been a thing that you’ve ever experienced? Or am I just the crazy person over here?

Michael Greenwald (15:11.074)
I think through each level of growth that I’ve gone through, it’s always a fight of this imposter syndrome of you don’t know what you’re doing, you shouldn’t be doing this, you’re not qualified to do this. So definitely, exact same feelings through each level that we’ve hit, and I’m sure every level going forward that I’ll feel that uncomfortability. it’s something that…

Brett McCollum (15:26.452)
Mm-hmm.

Brett McCollum (15:36.244)
Yeah. What do you do to fight it, man? Like, what are some of the things you do to fight that? Because we know it’s a lie, right? That’s at end of the day. You know it’s a lie intellectually. Let me rephrase that. Intellectually, I know this is a lie. But something’s still just that, you know, spiraling feeling sometimes that you have to… are some tools? What are something you use to help with that?

Michael Greenwald (15:58.924)
Yeah, so I think most importantly for myself when I’m feeling stuck in this cycle, these anxiety thoughts of, you know, I don’t belong here, I can’t do this, I take action on something to prove myself wrong. I’ll call a multifamily broker, I’ll start trying to figure out some lead sources, I’ll do something that…

two or three years ago, would have thought was impossible. Or even just taking some time to reflect. Think about a year and a half ago, two or three years ago, what I’m doing right now, what I’ve made my new normal, is something that I would not have thought possible, that I wouldn’t have thought I could do. So just that realization that I’ve already come so far, that I can do it. And the proof that I already have, that I have.

Brett McCollum (16:31.731)
Yeah.

Brett McCollum (16:55.06)
Yeah, I love that. Something I share a lot with different people inside my sphere of influence and community and stuff is you’ve probably heard of it. It’s a story. I’m pretty confident it’s a true story, actually. I gotta look it up. But it’s about being three feet short of gold. Have you heard about that?

Michael Greenwald (17:13.228)
Mm-hmm. Yeah. Yeah.

Brett McCollum (17:14.74)
I love it’s a great analogy. Um, you know, and I’ll do, I’ll tell the 10 second version of it really, but basically, you know, this guy leaves New York, goes out actually to California during the gold rush brings all of his mining equipment, starts digging, digging, and event never finds anything. Besides there’s a local that’s living there. He sells it to him for pennies on the dollar and the local, the guy goes back to New York, eventually becomes a millionaire of 35 some years later.

okay, in his late 60s and 70s and then but the he finds out that the guy that he sold it to the local straight school pretty quickly and he was three feet from where he stopped digging and so I always tell myself in those moments of like I can’t keep going like man I’ve already dug this far I what if I’m three feet short you know and that and and some people say that like well that’s not

Michael Greenwald (18:08.494)
Mm-hmm.

Brett McCollum (18:13.338)
It’s a motivating factor for me. You’ve come this far. You’ve built this long. You’ve worked this, like, the way you grew up, Michael, the way I grew up, maybe other people, you’ve made it every step of the way this far. know, adversity is gonna happen to all of us. You learned that in the military, right? Like, adversity is going to happen to you. How do you respond to it? You know?

Michael Greenwald (18:35.116)
Yeah, exactly. Exactly.

Brett McCollum (18:37.458)
Yeah, that’s something I carry. I was wondering, was like, man, I really enjoy mindset conversations with people and I genuinely love mindset conversations with military. Because you have a different perspective even that you, if there’s something that the military is trained well on, is how to look adversity in the eye and sorry for the language, tell it to go to hell. You know?

Michael Greenwald (19:00.236)
Yeah. Yeah.

Brett McCollum (19:03.388)
I think that’s really special, man. yeah, what else are you doing from the personal growth side that helps you? you read? What are you doing for personal growth?

Michael Greenwald (19:14.158)
So I do try to read, could probably be better about it. I have a book list that is just constantly being added to and can almost never catch up. But aside from that, I do some good…

mental health, know, kind of self-care things, meditation, visualization, kind of starting my day off on the right foot. And then aside from that, also, I think more importantly than those, or equally important, would be getting in contact with people who are a few steps ahead of me, who are willing to kind of share their journey and, you know, give me some guidance along the way and just learning from others.

Brett McCollum (19:52.756)
Sure.

Brett McCollum (20:00.67)
Very cool. Let me.

Brett McCollum (20:05.33)
I want to transition a little bit. don’t want to do it too quickly, but because this is such a powerful like topic of conversation, I think that people like you starting off your morning, right? Starting off with the visualization and things like that. I think that’s so powerful. And I think it’s that and this will be a good transition point. Probably it speaks to the way you’ve been able to. You’re still in the service and you’re buying it. You know your first property. Then you come out of the service and you’re actively pursuing and now you’ve got a handful of doors that you own and operate. And also now.

catch me up on this one, syndication departments, that sort of thing. What is that looking like? What’s going on there?

Michael Greenwald (20:41.666)
Yeah, so that was the shift from single-family short-term rentals to multi-family apartment syndication really, really came with time, I think, after operating these short-term rentals for so long. The initial goal jumping into them was passive income, super not passive income when you’re managing Airbnbs, especially across the country. So…

Brett McCollum (21:03.828)
Mm.

Michael Greenwald (21:10.446)
for the long term vision for my wife and I is to operate these multifamily apartment buildings and assets to eventually operate them from a truly passive position. So not as a general partner, but as a limited partner where we’re putting money into them, getting good returns from them and kind of diversifying from there. And aside from that.

You know, it just made sense in our brains as that’s the next, you know, most logical step in our investment journey. But also jumped into that because it scared us. Because it felt impossible and, you know, like it was so far beyond my level of understanding or realm of, you know, grasp like I can own an apartment building.

Brett McCollum (21:47.796)
Sure.

Michael Greenwald (22:02.326)
So having to tackle that one has been very difficult at times as well, but just love the challenge.

Brett McCollum (22:10.278)
I love that. Yeah, I mean that’s, and maybe it’s really good we just had the mindset conversation, right? Talking about that leading into the, because it’s a different animal going from a single family home to an apartment building. But I will say this, there are principles in real estate that exist across, whether it be a single family home, an apartment, a hotel, or, you know.

Name it development opportunity like name it right there are principles that exist no matter what and Something I I’ve learned is I’m learning only rephrase this because growing up without Financial acumen the way I I did and I don’t know sounds like maybe some learn to how you grew up to in some ways Having to learn financial acumen has been a challenge, you know, but the principles that the wealthy use are the same that we can use and

in everything, right? You don’t have to be, well, you know, this person was a billionaire and of course they can buy this, da da da da. No, like the same principles apply to you and I too. You know? So what’s the goal with the syndication department? What’s the, like, you obviously, you’re tackling that for the first time. What’s the long-term goal on that? Maybe let’s fast-forward this out, you know, another two years.

Michael Greenwald (23:18.51)
Yeah.

Michael Greenwald (23:35.544)
So two years from now, our main goal is to, obviously we’ll keep our single family portfolio as long as it’s cash flowing and kind of just have those as little pieces of equity to pull from eventually. on the syndication side, the main goal is.

get the experience that is required to actually succeed in the industry over the long term. getting in our first deal as a co-GP, whatever way we can, whatever way we can come to a team and help them and make it work and get our first deal. And then from there, continuing that same process and just learning throughout. So two years from now, I still expect to be.

Brett McCollum (24:19.956)
Yeah.

Michael Greenwald (24:23.47)
CoGP on a few deals, but also having a few deals of our own that we’re sourcing and markets we’re looking at and learning how to become a lead operator of assets like this.

Brett McCollum (24:35.924)
incredible. Yeah. Dude, I love that you had the foresight on that to look at that and look man, you’ve done it like at this point, like there’s nothing to believe that you can’t accomplish that. You’ve done it like you’ve taken each step thus far, you know.

And I think that’s incredible. on the risk of this sounding a little bit weird, okay, and uncomfortable maybe for some people, I don’t think men tell each other enough this. So I’m gonna tell you, man, I’m proud of you for what you’ve done, for where you’re going, and what you’re gonna be doing, man. So good on you for it.

Michael Greenwald (25:09.304)
Thank you. I appreciate the sentiment and I would agree that it’s not shared enough. yeah, thank you. Just put my best foot forward and make it happen one way or another.

Brett McCollum (25:18.952)
That’s it, man. I love that. So if people want to reach out to Michael connect with you and follow along the journey as you’re growing and going, what does that look like?

Michael Greenwald (25:28.866)
Yeah, so you can find me on Instagram as mastermindmichael, underscore, and then across, you know, Facebook, LinkedIn, Michael Greenwald, and aside from there, you can find all my other contacts, you know, on each of those pages.

Brett McCollum (25:30.79)
Good.

Brett McCollum (25:46.098)
Yeah, incredible guys. We’ll make sure we get the end of the show notes Dude, man, this has been great. I appreciate you sharing your story I love the conversation on mindset and growth because it’s I don’t think we can hear it enough especially with some of the challenges we’re facing out there today and You know and with where you’re going man, like, you know in constantly fighting that that inner Battle that we all fight, right? I don’t think it gets discussed enough. So thanks for taking the time and doing that with me

Michael Greenwald (26:14.222)
Thanks for having me on, I appreciate it.

Brett McCollum (26:16.53)
Yeah, perfect. Well, guys, our time is wrapping up here, but I appreciate you also hanging out with us, spending your time and energy with us listening, and I encourage you to, like I said, follow along with Michael. But we will see each of you guys on the next episode. Take care, everybody.