Single-Family Rentals Are RISKIER Than $100M Apartment Deals with John Casmon

Think buying one rental house is safer than investing in apartment buildings? John Casmon is about to flip everything you know about real estate investing upside down.

John has helped families invest in over $100 million of multifamily real estate and is about to go "full cycle" on deals that could change his family's life forever. But here's what shocked us most: he argues that owning ONE rental house is actually MORE dangerous than owning 100 apartment units.

In this eye-opening conversation, John breaks down why corporate professionals are perfectly positioned for multifamily investing, how apartment buildings operate like the businesses they already know, and why the "one house" strategy keeps most people stuck in landlord hell.

The Corporate Professional's Secret Weapon:

• Why your W-2 experience is actually perfect training for apartment investing
• How managing a $100M advertising budget translates to multifamily success
• The mindset shift from "side hustle" to "business operation"

The Single House Trap:

• Why 100% income dependency on ONE tenant is financial suicide
• The "3am furnace call" vs. professional property management
• How one vacancy can wipe out an entire year of profits

The "Leveling Up" Strategy:

• What "going full cycle" really means (and why it's the ultimate proof)
• How John's 4-5 year bets are about to pay off massively
• Why repositioning beats buying and holding

💡 Key Insights Revealed:

1. The Risk Reversal: More units = less risk (not more)
2. The Scale Economics: How 10+ units justify professional management
3. The Corporate Advantage: Your business skills are your secret weapon
4. The Passive Option: GP vs LP - operator vs investor paths
5. The Full Cycle Proof: Why projections don't matter until you sell

🎯 Perfect For:

• Corporate professionals feeling trapped in the W-2 game
• Single-house investors wondering why it's so stressful
• Anyone with capital who wants true passive income
• Ambitious beginners ready to think bigger
• Experienced investors looking to scale properly

📈 The Numbers That Matter:

• Over $100M in multifamily investments facilitated
• 7 years full-time in real estate
• Multiple properties going full cycle
• From small multifamily to major apartment deals
• Corporate background managing $100M advertising budgets

🌟 Why This Episode Hits Different:

John doesn't just talk theory - he's actively exiting deals and proving his strategies work. While other investors are struggling in today's market, he's exceeding projections and going full cycle. His corporate background gives him a unique perspective that most "gurus" lack.

🎧 What You'll Walk Away With:

✅ A complete reframe of what "safe" real estate investing looks like
✅ Understanding of GP vs LP investment options
✅ Corporate skills that translate to real estate success
✅ Why multifamily beats single-family for busy professionals

📞 Connect with John Casmon:

• Podcast: Multifamily Insights (#1 rated multifamily podcast)
• Free Guide: "7 Questions You Must Ask Before Investing in Apartments"
• Website: https://casmoncapital.com/7questions

🔮 Coming Up in Part 2:

We're splitting this into a two-part series! Part 2 will dive deep into:

• Specific multifamily investment strategies
• How to get started as an LP or GP

Transcript

Rob Pene (00:01.282)
All right, so we wanna thank John Casman here to the show because for people that know me, there's a little bit of background on the marketing side with multifamily and real estate. I've done the SEO stuff for the wholesaling, buy a house now, sell fast. I used to rank like crazy back in the day. And then I was able to do a little bit on the multifamily side, education side, and that's where John comes in. Cause he's helped families.

to invest in over $100 million of real estate and multifamily. And I'm testing out this idea where let's talk to John about his personal side, and then we'll release a second episode about specifically the multifamily investments and then how people can get involved because I know a lot of listeners understand real estate, are curious about real estate, but...

don't really take action or don't really know what to do. So that's why we've got people like John on the call. So appreciate you, ma'am.

John Casmon (01:03.008)
Hey Rob, thanks for having me man. Excited chat today and yeah, I mean I'd love to maybe we can focus today on why real estate and specifically multifamily so we can get to that with my story and then in kind of the the continued version we can get into more of the what to do and how.

Rob Pene (01:13.678)
Mm-hmm.

Rob Pene (01:19.18)
Yeah, yeah, yeah. So this question usually starts the conversation and then it kind of takes off from there. So if you were to reflect back on the last six to 12 months of your life and you were to turn that into a Netflix special.

what would that movie look like and what would it be called?

John Casmon (01:42.828)
Man, what would that look like? So right now we're really repositioning our portfolio and we are in some ways mining some of the fruit and the labor that we've put out there. So we're getting ready to sell a couple of properties and go full cycle and it should be really good for us and our business. So I would say a lot of work to turn things around to get ready for an exit. A lot of

growth from a family standpoint, meaning like as a dad and you know what we're going through as a family, a family unit, a lot of transition. So I would call it maybe leveling up, know, leveling up is what that series would be about. And it's really talking about how we made our investments in multifamily. We played some big bets four or five years ago on some of these deals and these investments. And now we're going full cycle on a few of them. And that is going to be a great

a great ability for us to make some transitions to transition my home life looks like I've been full time real estate for about seven years now. But, you know, having the entire family now be focused on this business and really creating the lifestyle that we always envisioned. And, now, you know, as you know, that that's the next step. But, you know, we really have a lot more work to do. And our mission is to help other people change their life and level up. And that's really what we would focus on.

Rob Pene (03:07.33)
I like it. Level up and reposition me. That's a good movie. Nice.

John Casmon (03:10.924)
Yeah,

Rob Pene (03:12.76)
So for people that are listening, he mentioned very industry specific terms like full cycle and then multifamily, basically apartments, right? So traditionally regular people, normal people, normal W-2 think, okay, investing in real estate is go buy a house, right? And then they also equate real estate to financial freedom. Problem is if you want financial freedom and buying one house at a time, you'll be free in 50 years or something like that.

John Casmon (03:18.42)
Hehehe

Rob Pene (03:40.514)
takes forever for a house. But what John does is apartments. So the difference between one door in a house and apartment is multiple doors. You benefit from all these doors. Can you explain full cycle just so people know? Because that's significant. You put in money, four years later, you get a lot of back from the... Can you dive a little bit deeper into that and then why you started it?

John Casmon (03:55.285)
Yeah.

John Casmon (04:04.438)
Yeah, absolutely. So when it comes to apartment investing, like you said, right? First of all, we're obviously buying this apartment building. We have a plan to improve that property. It's called value add investing, right? Or having a value add strategy. And all that really means is we're buying the property for what it's doing today, what the rents are today, what it's operating at today. But we see a plan where we can make it make more money. So just like any other business investor, we're going to come in, buy that existing business.

implement our business plan to drive revenues, to drive the net operating income. And then over the course of that execution, the property or the business is going to be worth more in the future. So that's exactly what we do. So we talk about going full cycle. If you think about it, we buy the property, we start to do the renovations and rehab, we stabilize the asset and then eventually we will sell. And then we know we bought it. We exit the property that's going full cycle. I we've.

implemented our entire business plan and then sold that asset. And when we talk about exiting or going full cycle, that's what we want to do in a deal because that's when you get to actually actualize the returns. Right. I can tell you on paper, hey, it's going to be a 15 percent IRR or we projected to be this or we projected double your money over time. But as you know, those are all projections. And even when look at these big companies that are on the stock exchange.

They always have projections. Sometimes they make them, sometimes they miss them. So going full cycle is the proof. That means you actually delivered on what you said you were going to do. And we can see what the actual results were and compare them to what you initially thought you were going to do. In this current environment, what we're seeing is a lot of people are not being able to go full cycle and they're not able to sell because the properties are not worth as much as they thought they were going to be.

Rob Pene (05:54.723)
Yeah.

John Casmon (05:57.366)
that is mainly driven by the higher interest rates, its higher taxes and insurance costs and other factors where rent growth isn't as strong because there's been so much new supply that's come online. And let me say that when I say new supply, all I'm really saying is there have been a lot of developers, right? A lot of apartments have come online. So in fact, some of these projections that people had have not played out since the economy has softened up. And in our case, coming out here and being able to execute actually speaks more volume because

Rob Pene (05:57.37)
might be.

John Casmon (06:27.306)
Not only were we able to exceed our projections, but we were able to do it in a tougher economic environment. And I think that goes to show that we were really conservative, but also did a really good job implementing and executing on our business plan.

Rob Pene (06:41.89)
Now, did you always want to do multifamily or did you also start like, let's get a house and rent that out or fix and flip?

John Casmon (06:50.454)
Yeah, so I think, you know, real estate was always interesting to me, but I don't know anyone who really wants to be a landlord. Right. Like, I don't know of anyone I've ever met, like in high school and they're like, yeah, man, I'll be a landlord. So, you know, I know people know you can make money in real estate. But again, the landlording is not something that Americans, you know, get excited about, not a really a prestigious title to have. So, you know, like many of your listeners, I was in corporate America. I worked in advertising and marketing. I enjoyed what I was doing.

Uh, but I was at, you know, it was in Detroit. I was working there during the last recession and I watched what happened, you know, firsthand with people who only had their W-2 jobs. And I think some people look down upon that. Listen, there's nothing wrong with having a W-2, especially when you like, especially when that pays well, you like it. But the truth of the matter is you don't have full control over your career. You know, you can make some decisions, you can plan it out, you can plot it out. But if you're working for a corporation.

Rob Pene (07:39.293)
Mm-hmm.

John Casmon (07:50.102)
You're always going to have leaders, even if you're the CEO. You know, you've got a board of directors who is going to, you know, be influencing what you can and can't do. So for me, I just started to see the game being played at that level and watching the senior level folks at my company, right? The directors, the folks who had moved their families multiple times, changing schools, changing states. And I watched how they were really, you know, pawns in a larger game. And I don't mean that in a negative or derogatory way.

what I'm saying when you talk about multi-billion dollar corporation, listen, you're filling a seat. And I was fortunate enough to be exposed to that early in my career where some people, have a title and you got a big budget and you got some power and organization and it kind of goes through their head a little bit, right? They start to develop a little bit of an ego. And I was on the other side of that. So I was a person who that person was talking to earlier on in my career and then I flipped and I went on the other side of the table.

And I just always remember that something that I was told as an intern and I was an intern that this guy told me, you he had just one of this big TV shoot. So he came back from California and he was out Hollywood parties and you know, it's a bunch of interns, right? We're excited. is the stuff we're dreaming about. Like, you know, when you're an intern, you just got, you know, wide eyes on what you're going to do in your career. And I remember sitting there and he's talking about his travel. Oh, they pay for your hotel and you got to per diem. What does that mean? Like.

We're getting into it and he could just see how like we were eating it up and he stopped and he said, listen, I want y'all to understand something. And he grabbed his business card and he put it on the table in front of us. He said, the reason all of that happened is because of this name and it was the title. Okay. It was a creative director. He's like, you don't want to get these things because you sit in a chair at a specific moment in time.

You want to get it because it's yours and it's yours for life. You want to be able to travel. You want to be able to have the things you want because of your name, not because you work at this company and hold this title. Cause that could be taken away from you at any moment. And if you think about it, so many people tie up their self-worth into a title, into working for a company, into holding a degree. And if that gets taken away from them, they lose all sense of self-worth and

Rob Pene (10:14.349)
Mm-hmm.

John Casmon (10:15.264)
That moment, him telling me that, it kind of always pushed me to never get too comfortable, no matter what, you know, the perks were, the benefits were, not to read my own headlines, and to really focus on building for my name and my last name, which is for the family. So, you know, your initial question was what got me, you know, into multifamily. I started researching, man. I was watching these people lose their jobs. And I said, you know what? I need to take more control of my life.

Rob Pene (10:32.046)
you

John Casmon (10:43.17)
I started looking into real estate and rentals as I got into rentals. Most of the people I was reading about, they said how they wish they got into multifamily sooner. So I kind of always had my eye on multifamily, but I didn't know exactly how to get into it. But that's kind of after doing my initial research, most of the people who are successful that I was reading about or listening to talked about multifamily investing and it made sense to me. So that's where I focused.

Rob Pene (10:46.188)
Okay.

Rob Pene (10:53.175)
Yeah, it is.

Rob Pene (11:07.51)
Yeah, yeah, yeah. So everybody that's listening, the message is think multifamily first. If you're interested in real estate, think multifamily first. Now, with your first investment, did you go in as like, so there's a GP general partner and then the limited partner, right? So for the listeners, the general partners are the operators and then the limited partners are the essentially the investors, right? The people, so I have a lot of family that have a lot of money that

think a lot about real estate, but traditional route is okay, buy one house. If you're listening, cousin and auntie, find a GP or be an LP in a multifamily because it's better, right? Did you start as an operator or did you start at like investing your money into somebody else's deal?

John Casmon (11:46.21)
Yeah.

John Casmon (12:01.974)
That's a great question, but I want to challenge what you said, Rob. You know, one of the beautiful things about investing in real estate is there's a strategy for every person. You know, if you're risk averse, if you love numbers, if you like more, you know, marketing stuff, whatever it is you like or your risk profile is or how much capital you have to invest. promise you there is a strategy for you, but you've got to understand and do the research on that. I agree and you agree, obviously, that multifamily is a great strategy.

But for some people, it's not the right fit. And it's OK for you to recognize that. If you want to be hands-on but don't want to be a landlord, listen, you're probably not going like multifamily, right? Because someone's got to be hands-on. Someone has to be working with the residents on a daily basis. Someone's got to be working with the maintenance guy and making sure that the right renovations are being made on time, on budget. And if that's not you, but you're also not constantly relinquishing that responsibility to someone else,

Rob Pene (12:32.675)
Mm-hmm.

John Casmon (12:57.078)
you may not enjoy investing in this way. With that said, I believe as a former corporate professional that it is a great strategy and probably the ideal way for corporate professionals to invest, not just corporate professionals, but specifically corporate professionals because it mimics what they're already used to. Right. So to give you a little side story, I started off with my small multifamily portfolio, right? A two unit building, a three unit building, about an eight unit building. And then I tried to flip a house.

Rob Pene (13:04.046)
.

John Casmon (13:26.262)
And I had a partner who was going to be the developer. had all this experience flipping. So he was going to be the one doing it. I was really more of the investor. Well, guess what? We ran into some challenges. This guy was co-mingling funds, which I didn't realize. And he ran out of my money and the draws that we had for the flip project. And I ended up having to take over this entire project with no flipping experience. And we ended up losing money and I lost money on that flip. Part of the reason was flipping is so much different.

than larger multifamily, even smaller multifamily. Because with smaller multifamily, know, once you have a unit available, you rent it out. Maybe there's a problem every six months, every three months, if you really have some issues, but you're not dealing with something every day there. When you're flipping a property, you've got work going on every day. And guess what? You got no income coming in, right? You're making no money, but you're spending money nonstop. You have crews there every day, the paint crew, the carpentry guys, like.

You have someone there all day and someone's got to oversee these people to make sure they're doing work on time and on budget and also helping them problem solve when there's an issue. And if you're not, you know, that's where deals can fall apart. Again, with multifamily, you really have to make sure you understand the property as a whole. You have to make sure you understand the property management of it. So when there's an issue, when there's a challenge, when there's a move out, the turns, all of that, there's certainly a process involved, but it's not as laborious as a flip.

So when it comes to having a rental, I know for a lot of people, it just feels safer. I want to have one house. I always want one rental, right? I can show that one time. I can get one renter. I can do that. That feels very feasible for a lot of people. But I would argue that it's actually less safe as an investment. Here's why. When you have one house, when you have one rental, you have 100 % of your income tied up into one individual. Now, if they're there and they're paying rental time, awesome.

But at some point, that person is going to move out or something's going to break or you have a leak in your roof. The HVAC goes out. You're going to have a big ticket cost or a big ticket item come up. And that's going to wipe out a lot of your profits for the year. When you have more units, let's just say even a 10 unit building. Well, now you have 10 people that are paying rent. Right. You may have 10 HVACs, it's unlikely that all 10 are going to go out at the same time. Right. Or every year. So.

John Casmon (15:53.076)
You may have things that come up, but because you have more money coming in, you can predict some of these cash flow situations better. So I go back to my time in corporate. I oversaw a hundred million dollar advertising budget. I was not the person sitting there saying, hey, I want the seven 30 time slot on ESPN. No, there was a company that did that. There was a media buying company that did that. I set the strategy with my team. We figured out what we want to do, what the creative was going to be. We said, hey, we want to reach this demographic.

We have X amount of dollars to spend on media. Go find us and the most efficient business plan, the media buying plan that we can execute. It's the same thing we get to larger multifamily. You're not going to be the person sitting there saying, OK, hey, let's place an ad on Zillow and let's write this here and let's do that here. And why don't we go ahead and make the units all this color? No, there's a team of people that you work with.

And they handle a lot of that. So the more money you have flowing, the more you can operate it as a business. So you have one house, you're running a side hustle, right? It's just a hustle and you have no idea when that house is going to need your attention. Right. That furnace goes out at 2 a.m. Guess what? Time for you to come check in. But when you have a 10 unit or even let's go larger, say 100 unit building, there's enough money there to hire somebody full time, full time on site, private manager.

full-time onsite maintenance technician. They handle those things when they come up. So the more money that's flowing, the more you can run it like a business, the more you can anticipate the ebbs and flows of what happens. Sure, you're have some slow days, but sure you're gonna have some heavy days. But it all pans out and you know, it's more this, it's like little ripples versus huge waves where you go three months without doing anything with your house and it feels so easy to be a landlord because you haven't had to do anything in three months. The rent checks just, you know, clump through on your bank account and it's awesome.

But then, you know, one day you get that phone call and it now takes three days of your life, right? Or again, someone moves out, you got to turn a unit, you got to do all of this, you got to do all that, you got to show the unit. And now you've got, you you spent three weeks working on this vacant unit and you're mad that you can't get it rented when you weren't anticipating this at all, right? So it's just, I think it's the expectation, but also just understanding if you want to run it more professionally, definitely it goes bigger. And we didn't get into the passive side of it, right? Like.

Rob Pene (18:13.646)
Just like...

John Casmon (18:14.05)
You know, there's a GP and an LP side where, you know, that GP is the one that's active doing the day to day. That LP, once they invest, they're done. They don't have to do any of stuff. They get the check, they get the mailbox money. They're, you know, relaxing. Their only job is to make sure they pick the right operator and the right deal. And you want to learn how to do that. And there's some ways you can do that.

Rob Pene (18:24.492)
Yeah. Yeah.

Rob Pene (18:37.068)
Yeah, yeah. as I mentioned earlier, we're going to split this up into a two-part series because, I already have a ton of questions on the education and the other side. But I think the golden nugget here is that one house versus many doors, one door versus many doors. I think John's been able to argue the benefit of the many doors side. So for you listeners, I need you to go and do your research.

John Casmon (18:45.132)
Yeah.

Rob Pene (19:05.634)
dig a little bit deeper about what you really wanna do on real estate because the challenge between one door versus what you can do with multiple doors, it's pretty clear. So if you have any questions or if you want to find a little bit more about John, where can they find you online?

John Casmon (19:25.602)
Well, I've got a podcast called Multifamily Insights. It's a number one rated multifamily podcast. You can check me out there. We also have a free download. If you are interested in investing in apartments, I have a free guide. It's called Seven Questions You Must Ask Before Investing in Apartments. So you can check that out at casmancapital.com slash seven questions.

Rob Pene (19:47.118)
Great, I'll put that in the description so you guys can go and check it out. But be on the lookout, download these things. And then when we come back for part two, we'll get even more deeper and your excitement is gonna heighten because of how John's gonna go into the specifics on what you benefit from, right, long-term and even short-term as a multifamily real estate owner and investor. Right on, man. God bless you, John. Appreciate you, brother.

John Casmon (20:13.365)
Absolutely.