Best U.S. Real Estate Investment Structures For Canadians With Gillian Irving & Michael Matthew

Gillian Irving:

Welcome everybody to the Wisdom Lifestyle and Money Show. My name is Gillian Irving. I'm a mortgage agent with Lend City Mortgages. I specialize in helping, real estate investors scale their portfolio. I'm also a coach as well, so I can help you improve your portfolio in a myriad of ways.

Gillian Irving:

I love to come on this podcast and talk to other professionals in the field, people who can help us save taxes, which is who we're gonna speak to you today. Today, we're we have the great pleasure of having Michael Mathew with us. He has been a professional accountant for more than 30 years. He has a bachelor of arts bachelor of arts from chartered accountancy studies from the University of Waterloo. As a small business owner in the fields of computer and business consulting for more than 20 years, Michael has a real appreciation of the challenges and frustrations that are faced by his clients.

Gillian Irving:

He understands that clients want accountant who will do more than just fill out forms. They want a trusted adviser who will add value to their bottom line. Welcome today, Michael.

Michael Matthew:

Thanks so much for having me here, Gillian.

Gillian Irving:

Oh, it is it's my pleasure. So we obviously would like we're gonna have you on many times, Michael. I feel like there are so many things that you and I could discuss. But I think, primarily, today, the focus of our conversation is gonna be for our investors who have this new and deep interest in investing in the states. At Lendly, we have a whole new program where we can help foreign nationals purchase properties there.

Gillian Irving:

And, honestly, we have so many investors calling us to help prepare them for getting, you know, mortgages down in the states, but there's a whole lot that has to happen before you can actually get a mortgage. Isn't there?

Michael Matthew:

Yes. That's absolutely right. And it's actually a good fit for what I do because I help Canadians set up properly to do real estate investment in the US. And one of the questions they're always asking is, how do I get financing? So the new program that you just mentioned will be of great interest to my clients for sure.

Gillian Irving:

So I think, you know, when people come to me and say, I need a mortgage, I say, well, you gotta set up your corporate structure first. And they say, what is that, and what do I do? So can you help us understand, Michael, what let's just start with a a beginning investor, someone who is just getting started. So not a sophisticated investor, but just someone who might wanna go and buy 1 property or maybe 2 properties in the States. What kind of entity they need to set up with you to go and do that successfully?

Michael Matthew:

The first question I would ask is what is their goal? Like you mentioned, perhaps 1 or 2 properties. Is this something that they're gonna use primarily for their own personal use and perhaps rent out a bit to offset the cost. Mhmm. Because that tends to mean they don't need to set up a lot of these more detailed structures because they're actually not running a business.

Michael Matthew:

If however though, it's meant to be a money making venture, they want to build up some long term cash flow from rental income, they're probably gonna wanna set up a corporate structure. And typically, what I recommend for someone that especially if they plan on leaving some or all the income in the states that's generated to use what I call a triple c structure.

Gillian Irving:

Mhmm.

Michael Matthew:

There's no point in googling it because it's my term. You're not gonna find any information on it.

Gillian Irving:

Oh, I love it. A secret. An accountant strategy secret.

Michael Matthew:

That's it.

Gillian Irving:

So tell us more about this.

Michael Matthew:

Typically, it involves setting up a Canadian corporation. So a lot of my clients are Ontario. So as an example, you would set up a Ontario numbered corporation. You don't need a name for it because you're not gonna market under this company. It's not public facing.

Gillian Irving:

So So it's just an Ontario 1, 2, 3, 4, 5 company.

Michael Matthew:

Exactly. Exactly. And then you get what's called a c corporation. The US has several types of corporations. You know, here, the 3 main ones are c corporation, s corporation, we can dispense with quite quickly because that only applies if you're a US resident.

Michael Matthew:

So if you're doing business from Canada that one's off the table anyway. The next one, LLC, you can use but you have to be careful. You can't hold it directly as a Canadian and that's because the LLC is considered to be a flow through entity, or are sometimes called a disregarded entity. That works very well if you're an American resident because you get the protection of a corporation from the legal liability concerns, but you flow through the actual income expenses from your LLC to your personal US tax return. Works great if you're, as I said, a US resident.

Michael Matthew:

The issue is if you try to do that as a Canadian, CRA will said, oh, you're claiming these foreign tax credits or the credit the tax you paid, in this case in the US, where is that coming from? You say it's coming from this LLC, and they stop you right there. Mhmm. Because you thought you would take these tax credits from your US personal tax return that you flowed through to just like the US citizen or resident did, and then you claim that on your Canadian personal tax return, and you're both in the same level, both personal tax returns.

Gillian Irving:

Mhmm.

Michael Matthew:

The problem is, CRA won't allow that. They'll say, you're trying to claim corporate tax credits because they're coming from an LLC, and you're trying to claim them on your personal tax return in Canada, if it's matched, we won't allow that. And that's how you end up paying double tax or potentially more, but you'll pay extra tax. Mhmm. And if you're gonna have an LLC as a Canadian resident, you have to have an intervening corporation.

Michael Matthew:

Mhmm. And that's where the c corporation comes into play. In this case, you'd have your Ontario numbered corporation which would own the Wyoming, because that's where most of them go. C Corporation which owns the LLC. The LLC is the entity that actually takes title to the property.

Michael Matthew:

A lot of Ontario residents like to invest in the east coast, so places like Georgia, Florida.

Gillian Irving:

Those kind

Michael Matthew:

of cases. So you'd set up, say, a Florida LLC to buy your Orlando area property, and you would treat that as a disregarded entity just like most of the other LLC's, would flow the income and expenses in this case to your Wyoming c corporation. Mhmm. But you'd only file in the US for one corporation, the Wyoming one. So the first one drops out just like it does for the US residents.

Michael Matthew:

The difference is if you're a US resident, it goes to your personal tax return. As a Canadian resident in this scenario, it goes to your Wyoming c corporation that pays the taxes.

Gillian Irving:

Right. And so this LLC, you said, for the purposes of our illustration, you said this was a Florida LLC and that you can buy your property in Orlando. But what if you set up this structure and you're like, okay. I've got my Wyoming c corp ready to go. I've got my Florida LLC, and now all of a sudden I wanna buy in, you know, Ohio.

Michael Matthew:

That's a great question. With the c corporation, you can all you only have to ever set up 1. Mhmm. You can then run multiple LLCs underneath that. Mhmm.

Michael Matthew:

You could run there's no limit, actually. So you could run 2, 5, 10, 50 for that matter. The whole point is the Wyoming Corporation isn't doing business directly.

Gillian Irving:

Mhmm.

Michael Matthew:

It only doesn't have the legal exposure. And the reason why you'd have different LLCs is you wanna separate your investments such that a problem with say your Orlando property doesn't affect your Ohio property. You can abs absolutely use your Florida LLC to invest in another state like Ohio. You just have to one extra step, that's all. And you would have to register your Florida LLC in Ohio to do business there, is what they call a foreign corporation.

Gillian Irving:

Mhmm.

Michael Matthew:

I get a kick out of that because are you not all in the states? But that's not how they look at it. If you're not, your corporation isn't local to that specific state, it's considered a foreign corporate. But all that means it's a one time registration fee to do business, and then everything else is the same.

Gillian Irving:

And are those expensive fees? I mean, is that something, like, you really wish you had thought about that first before you registered your LLC, or is it minor and it's really not that big a deal?

Michael Matthew:

It's the latter. These fees are minor, and they vary from state to state, but you're looking in the range of a 100 to 200 to maybe $300. That's Mhmm. The state's registration fees just to start the corporation, they range from nothing up to about that. So it's 100 of dollars, it's not 1,000.

Michael Matthew:

Mhmm. One of the reasons I like Wyoming is their fees tend to be among the lowest in the country. Wyoming has no state income tax, All those reasons, and it everything's automated, so you can get companies registered in as little as 2 to 3 days if things go well. And

Gillian Irving:

So if you would so if you registered, the c corp in a state other than Wyoming, tell tell me what that might look like. I mean, it's so more more expensive, lengthier.

Michael Matthew:

The fees are gonna be more in almost every case. Mhmm. They're not gonna have as good privacy protection. And also, the way it assesses legal judgments, it's more beneficial in Wyoming such that, if you don't distribute from that company, your creditors can't get in to get the money. It's only if you pay money out from that company that they're able to to yourself, that they're able to swoop in and take it.

Michael Matthew:

Mhmm. It's called a charging order. So the the other states, they're not as friendly and when it comes to all those factors.

Gillian Irving:

Mhmm. And from the tax perspective as well too for the state tax level. It sounds like it's the lowest.

Michael Matthew:

You know, the state tax level, as I said, there's no corporate income taxes. Mhmm. Actually, no personal income tax either in Wyoming.

Gillian Irving:

Why does everyone not live in Wyoming?

Michael Matthew:

Interesting enough, it's the least popular state in the country. What that means is you can buy a property there, you absolutely pay no income tax at the state level. The problem is, you're not likely gonna get much appreciation because you simply don't have the demand. Mhmm. If it's the least popular state, that means not a lot of people wanna live there in the first place.

Gillian Irving:

So you have to weigh your pros and cons from a business perspective. It's no use having a property that you can't sell to anyone.

Michael Matthew:

And I always tell people the first thing to look for, where to invest is simply, is this a landlord friendly state or is this a tenant friendly state?

Gillian Irving:

Mhmm.

Michael Matthew:

Because in states like California, New York, New Jersey, you can have a tenant being default for a year or more before you can kick them out.

Gillian Irving:

That sounds familiar with Ontario.

Michael Matthew:

It's like Ontario and Texas, it's about 3 weeks.

Gillian Irving:

They're not messing around there.

Michael Matthew:

No. You know, don't invest in practice. So that's the number one criteria. I always tell people, Yes. You can debate about which state has a slightly better tax rate.

Michael Matthew:

You have a federal tax rate for corporations, which is currently 21%, That's gonna apply in every state. Mhmm. So what you're talking about is a range of 0. I think the top state is around 11 a half or 12%. But those are the states that I don't suggest you invest in anyway.

Michael Matthew:

States like New Jersey, New York, California with the one exception of your flipping properties. That then you can do that anywhere because you're not actually taking title in most cases. You're not actually holding on to it for a long term. So those sorts of things don't really matter. But for any longer term play, you're gonna start with that evaluation.

Michael Matthew:

Does this state favor tenants or landlords?

Gillian Irving:

You know, it's funny you should bring that up because I would say the primary reason people have been approaching us at Lendly to help with their mortgages and the reason why we feel like there's this huge demand and surge for US lending is because of exactly that, that the Ontario landlord tenant board has just made it really difficult to do business here. Right? And people are finding it hard to be able to evict tenants in any sort of expeditious way, and so they're looking to move their money into areas where there is a more landlord friendly environment to to connect business, really.

Michael Matthew:

Yeah. I'm a landlord myself in Ontario, and I've experienced some frustrations around trying to get a tenant to move out because there was a pest problem, frankly, roaches. And I was so stubborn, I didn't want to pay them to leave. But that's actually encouraged in the Ontario market is to pay tenants to leave. Yep.

Michael Matthew:

And that just struck me as why would I wanna reward someone for, you know, damaging my property. Right. I assigned a property manager, a friend of mine, and she said, you have to remember, the landlord and tenant board is not there to kick tenants out of their homes. So if they can find any excuse possible to not do it Yeah. They will not do it.

Michael Matthew:

Write down including you make some simple clerical error on your paperwork. They don't allow you to just cross it out, initial it, and keep going. You have to start all over and get a brand new hearing. And it's just craziness. It's

Gillian Irving:

Yeah. It's very frustrating.

Michael Matthew:

Not to get too political, but the the politicians keep going on and on about housing crisis, and we've got to do something to improve it. And they keep trying to tinker with demand when they should really be concentrating on increasing supply. Mhmm. And one of the ways to increase supply is to have a fair landlord and tenant board that doesn't cater to the tenants so much that they can continue not paying rent for a year or more before they're kicked out. And the even when you get the order, it's not like they leave the next day.

Michael Matthew:

No. Weeks down the road, and then the police do not get involved. The sheriff is the only one who can legally kick your delinquent tenants out. And the sheriff posted notes, and again, it's not the next day. So even after you've quote, won at trial, it can be a couple of months before you even get into your property.

Michael Matthew:

So it's definitely stacked against you, and that and also the high prices of entering into the real estate market in the Greater Toronto area and the Vancouver area in particular is what is encouraging my clients to look to the US because you can get into properties for much less money.

Gillian Irving:

Yeah. 100%. That's what I'm seeing across the board. You know, people Ontarians who look at homes for sale really anywhere in the states, and they come back to me excitedly and said, the number starts with a 2. And they can't really believe it that there's actually a house that might cash flow, that you can buy that's not a shack that is in the $200,000.

Gillian Irving:

You know? It feels exciting to be able to help people, really to scale businesses in the States and for us to be able to help them more readily now from Canada with tons of financing options. So let's jump back into these these LLCs again because you made a comment that was interesting to me. You said if you had 2 LLCs, you might wanna protect what's happening in one state from properties, like, from what was happening with properties in another state. Do you try to stack your LLCs up to a certain value, Michael?

Gillian Irving:

Is that what you try to do? You say, once we get to $500,000 with properties in Florida or wherever it is, then we're gonna make another LLC just to keep the value of them kind of distributed just so that there doesn't does that make sense? Just so that you don't have too much exposure in one company?

Michael Matthew:

Yeah. That that's a great question. And, yes, generally speaking, people have a rule of thumb and it's somewhere for most people between 500,000 and $1,000,000 worth of properties. Once they cross that threshold, they will then look to have another LLC opened up to purchase the next property.

Gillian Irving:

Mhmm.

Michael Matthew:

It comes down to peace of mind, which only the client can value versus cost to maintain and set up. I can certainly tell the client what it's gonna cost to set up another LLC, what the anticipated cost is to maintain it year to year. But what I can put a price on is their peace of mind such that some people may say, you know what? I don't think I'm gonna get sued. I've got good insurance in place.

Michael Matthew:

I don't mind having 4, 5, 6 properties in the same entity. Mhmm. Other people may say, you know what? I ran into a problem where there's one problem tenant at one property, and then all my real estate holdings were all of a sudden at risk because this guy decided that'd be a good place to break an arm and sue me because I didn't maintain a a safe home for him. And I'd rather have everything carved off into a separate entity.

Michael Matthew:

Yes. I know it's gonna cost me more, but then I don't have to worry that a problem with one property is gonna take down everything else I own. Mhmm. And I get to have more assets accumulated, it's gonna be more of an issue. Let's say that $200,000 property and you buy another $200,000 property, most people will be comfortable just leaving those 2 in the same structure.

Michael Matthew:

But it's, at the end of the day, the client's option because they're the one who has to sleep at night, not me.

Gillian Irving:

Right. And do you feel like the litigious nature of the states? I mean, people do suit there more than they do here. I mean, it really does sound like a consideration. I mean, I'd never thought about that as a property owner here in Ontario with several rental properties.

Gillian Irving:

I do have different holding companies for my properties just because they've been around for so long, but I've never really thought about people suing me for breaking their arm, but maybe I should even for my Ontario properties.

Michael Matthew:

The way the way I look at it is you have to assess the risk. And to me, having 10 individual homes is less risky than have 1 10 unit apartment building. Mhmm. It seems like everyone has at least 1 idiot friend. And if you're concentrating those 10 idiot friends in one building, the chance of having a problem goes up exponentially Mhmm.

Michael Matthew:

Versus 10 single family homes. You have to evaluate the risk and while you need insurance, especially if you have a catastrophic loss such as a fire or flood damage, insurance companies are pretty good at figuring out ways to not pay you.

Gillian Irving:

That's true.

Michael Matthew:

As an example, most people would be surprised to learn that if their rental unit lies vacant for more than 30 consecutive days, they have no insurance coverage whatsoever. This standard in the industry is, and I'm talking in Ontario, that the policies lapse or avoid after 30 days of not being occupied.

Gillian Irving:

Mhmm.

Michael Matthew:

And, personally, it's taken me 2 to 3 months, maybe even 4 months to rent my place out on several occasions. And had there been a problem during that time frame, I would have been on the hook potentially myself. Although, at least for some of that time, my policy explicitly had, I think it was a 120 days of coverage. So you can get these extra coverages, but you have to be aware of the need in the first place.

Gillian Irving:

Right. Now back to sort of setting up these corporations. Again, so many of the people who I'm talking to about who are really just starting their, you know, their research into the states and purchasing their, you know, they're being told that what they should do first is to shop and find the property and then open up their entity. And I'm not sure that is the correct order. What would you recommend for people who know they wanna get started soon?

Gillian Irving:

Is it best to wait, or is it best to just get started with the setup of this entity now?

Michael Matthew:

If you're committed to proceeding, then it makes more sense probably to start setting up your entities. And the reason is, in order to open up a bank account, you're gonna need what's called an employer's identification number. Even if you don't have any employees, that's what the US calls their tax ID number for corporations. If you have a business in Canada, you know that CRA issues you a business number, this 9 digit number. The equivalent in the states is this EIN, and the IRS is the only entity that can issue these EINs and they sometimes are quite busy.

Michael Matthew:

So we're okay now, but starting sort of March to May because they're dealing with so much personal taxes, what should take perhaps 2 to 3 weeks can take 2 to 3 to 4 months to get that EIN issued. And while you needed to file your taxes, the more pressing concern is you're gonna need it to open up a bank account for your US entity. You cannot open up a bank account without it. Right. So

Gillian Irving:

So you can have the best property in the world, and you can't get it because you're waiting for the IRS to give you this EIN, and that might be weeks or even possibly months for that to happen.

Michael Matthew:

Possibly months. And, yeah, obviously, there are ways around it, but but in an ideal world, you don't wanna have to ship properties around from one entity to another at the last minute if you can avoid it. So, yes, if you're committed, by all means, get it things set up. To set up a numbered Ontario corporation, I mean, I say a week, just between us though, it can be happening that much faster, especially if there's just an if there's no name, it's and it is truly a numbered company. And setting up the c corp and the LC takes usually about 2 weeks.

Michael Matthew:

The fly in the ointment, so to speak, is that EIN number because they're very you think CRA's procedural, IRS is so much more procedural that there's no possibility of hurrying them along. As an example, I received some correspondence for from the IRS and I had to forward a response, which I did. And rather than read my response, which I thought they would do, they just sent a letter saying, yeah. We know you sent us something, but we need 45 days to read it. I'm thinking, just read it.

Michael Matthew:

Why are you sending me this letter?

Gillian Irving:

Yeah. Like, you could have read it in the time it took you to respond to the letter saying you're not gonna read it for 45 days.

Michael Matthew:

Exactly. So there's just no hurrying on them along. People get the EIN, documentation. If they somehow misplace it, the IRS refuses to reissue a copy. Again, I don't know why.

Michael Matthew:

It's So

Gillian Irving:

you'd have to apply again?

Michael Matthew:

You have to apply for this, not the EIN number. You have to apply for a confirmation. It's a different process and it's a whole thing. And the only reason I know is because I've had clients that did that. They lost the paperwork.

Michael Matthew:

Right.

Gillian Irving:

So public service announcement. If you get an EIN, take a picture of it. Do this.

Michael Matthew:

Yes. Great. Take a picture of it so that you can reproduce it for the bank because the banks wanna see the original letter from the I IRS. They won't just say what's the number. They wanna see the actual document.

Gillian Irving:

Fascinating. And what are there sort of classic mistakes that you see? Do you have people who come to you where they're like, oops, I set that up. That was not correct. And do you try to tidy up the messes for people, or do people come to you with preconceived ideas and you are mostly in the education game saying that's not the way I would set it up.

Gillian Irving:

I'm just wondering if there's, like, mistakes that people make that you're like, wow, I wish I had known or I would have done better had they

Michael Matthew:

come to me first. I I think of it as a mistake if they're buying a property that they're gonna be renting out over the long term. Even if it's a short term rental, but they're doing it year after year. And they did it in their personal name. Mhmm.

Michael Matthew:

Problem That's

Gillian Irving:

a mistake with that.

Michael Matthew:

The problem we had is I want that to be in the LLC, and to move it, that would trigger in Canada capital gain if the property is appreciated. And in this case, it was in Florida in a growth area. So even though they just bought it, I think the year before, the price had gone up more than 6 figures, which means half of that gain is taxable in Canada because when you move it from one entity to another, that's considered a taxable transaction. Right. And there's no rollovers that apply to foreign corporations.

Michael Matthew:

We just said, ugh.

Gillian Irving:

Let's not do that again.

Michael Matthew:

Let's get a good insurance policy and hope you don't have a problem with this property, but future properties should be set up in a corporation from day 1. Other mistakes are just not following up with the various bits of paperwork that has to be submitted on a timely basis, not understanding that while we have a similar tax system, it's not identical and so they have different requirements in the US and you basically need to be on top of things. And what I do is I work with American CPAs who handle all the entity creation in the US, and they also file all the tax returns and also the information returns. Those don't involve taxes directly, but that love letter I referred to earlier for I received from the IRS was because they said you paid money to related foreign entity, I e yourself, and you didn't file this information return, please send us $10,000. And that got my attention.

Gillian Irving:

So would.

Michael Matthew:

And they don't file my own US tax return. So I contacted the same CPAs that I just mentioned and say, I know we have filed an extension to file the corporate tax, and I know we filed it well with an extension. Time frame. Yes. That's correct.

Michael Matthew:

Now just curious, no real reason. Did you happen to file this information return related to related party payments? Oh, absolutely. That's a very important form to file. So now, good.

Michael Matthew:

Why? Because the IRS says, I didn't file it and they want $10,000 Oh no. We filed it. And why did they send this? Oh, they don't they have it.

Michael Matthew:

What happens? A lot of companies just pay it. So here's a left hand, right hand thing where one department, the IRS, received the document. The other one just sent out this notice because there was a related party

Gillian Irving:

payment. Hoping you might just pay.

Michael Matthew:

You're hoping I would pay. It's

Gillian Irving:

a pretty good strategy. Okay. But I could see how that would be incredibly stressful for a new investor who is starting out there who didn't know all of these things. Right? That kinda make you wanna be sick if you got the you owe me $10,000.

Gillian Irving:

So I am assuming then, like you were saying, that if someone were to set up their corporation with you, that all of those reporting and information requirements would be something that you would take care of on everyone's behalf.

Michael Matthew:

That's right. In coordination with my American CPA colleague, all that is dealt with. Right? It's just up to the client to get their details in terms of the transactions took place during the year Mhmm. On a timely basis and provided that's done, then everything falls into place after that.

Gillian Irving:

And then do do you also do just regular bookkeeping as well? Is that a service you would offer for someone who is setting up their properties that you do the the monthly expenses and all that kind of stuff as well, or is that something that they would have to take care of?

Michael Matthew:

I I I can handle that. I don't directly do it myself because I'm frankly too expensive. Mhmm. But I do work with a bookkeeper that can handle various type of assignments and that's something that he could do. And it's a good idea, at least starting out, for the clients to do it maybe for a year or 2, just to get some familiar familiarity with the file.

Michael Matthew:

Mhmm. But it's not something they have to do on an ongoing basis, and especially if they're investing in a big way, they have multiple properties.

Gillian Irving:

It's too much.

Michael Matthew:

It's too much work for them and it's gonna bog them down. And for sure they would need to work with a bookkeeper, you know, more or less from the start because what they do well is find and fund properties. They're not bookkeepers because if they were, they'd already be doing it as a business.

Gillian Irving:

So any last tips for new investors as they start on their journey to investing in the US?

Michael Matthew:

Get some education Mhmm. And take action. You need both because there's some people that get no education just take action and and that's made a lot of money digging themselves out of the hole they've created. And other people who are reluctant to take any action until they know everything. You're never gonna know everything.

Michael Matthew:

The deal's a good deal because it's generating the return that you're looking for. Just understand you will have some extra cost, no question about it. There is some extra complication, but that that's it's factored in to whether it's a good deal or not. Mhmm. So as long as you understand those factors, then you'll be fine.

Gillian Irving:

That sounds like fantastic advice. And if, our listeners wanna reach out to you to get your help in setting up this mythic mythical 3 stage corp that only you do. Where can I find you, Michael?

Michael Matthew:

The easiest way to get ahold of me is through email atmichael, that's michael@askmichael.ca. So michael@askmichael.ca.

Gillian Irving:

That sounds great. And, of course, if anyone needs assistance with the US Mortgages, you can reach out to me directly as well at gillian@lendcity.ca. And Michael and I are looking forward to helping you with your next US purchase. Thank you very much, everyone, and I hope to see you back here soon.

Michael Matthew:

Thanks, everyone. Bye now.

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