Insights on Portfolio Health, AI Integration, and U.S. Investment Opportunities

The Truth About Real Estate Investing... for Canadians

Greetings my fellow investors and truth seekers, this is the Truth About Real Estate Investing Show for Canadians and if you’re addicted to social media like I am, there’s not a lot of good news within our community. It’s not all bad, we just had Kelly Caldwell, Victoria Cluney, and Milena Simsic. Spencer and Ashley with their AirBnbs, Zac Killem whose company Front Lobby will thrive. In general those with healthier portfolios as in not over leveraged, focus on cash flow and operational execution are doing just fine like many past guests of this show. I was just speaking to one investor/Realtor while preparing this episode who did just that, he’s buying more multifamily buildings and completed two flips in the USA.

Off the top of my head, I can think of two past guests in significant financial trouble, one has already declared bankruptcy, the others owe a lot of people a lot of money to individual investors, not just banks. Individual investors post to social media and tell others to warn them. I know because I have friends everywhere in the community and the messages arrive in my DM’s.

Both were newer to real estate as they made the switch to full time within the last five years or so. I’ve left the episodes up because as far as I’ve know, there was no criminal intent nor are they being accused of any.

I run a real estate investment business called iWIN Real Estate where we are always looking to learn, evolve, and adopt best practices to help our clients optimize their investments and time, the only non-renewable resource. We started investing in single family, then multifamily, then student rentals, basement suite conversions, to garden/garage suites and it’s gotten unaffordable. We use Ai all through out our businesses.

I used Chatgpt to research case law when sellers accepted a higher competing offer when we had already accepted their counter offer. I’ve used Chatgpt to proof read my clauses for counter offers which saves everyone time: my clients, my lawyer, my broker.

I’m working on creating a digital duplicate of myself as I’m really busy booking calls to discuss USA investing. 80-90% of the questions are the same: what is the legal structure to own US properties, how do you get a mortgage, what are the fees like, etc… all repetitive I could have an Ai twin version of myself do.

If you think I’m crazy, check out the found of LinkedIn, Reid Hoffman’s two way interview of his own Ai twin: https://www.youtube.com/watch?v=rgD2gmwCS10

For anyone in sales or customer service, if you’re not afraid for your job, I don’t know what will. This is one reason I diversify my business, use Ai tools, own cash flowing real estate.

The owner of Property Guys was on BNN talking about how 25% of Realtors in the USA will leave the industry after those historic lawsuit settlements. This August, listings will no longer display co-operating commission for buyer agents hence buyer agents must negotiate commission from the buyer. Property Guy mentioned there are two lawsuits in the works in Canada which confirms the rumours I’ve heard. The implication is the public will be more aware that Realtor commissions are negotiable, they always have been and it my experience, sellers who want top dollar when selling will continue to offer co-operating commission. Most of the professional investors do it. I do it, I actually offer above market co-operating commission and use it as a marketing tool and negotiation piece. I mean it’s worked for me, the last four houses I sold, I did so, on average in 22 days on market.

Point is, I’m a Realtor, I’ve worried for my job since 2010 and never been more worried with Ai, class action lawsuits and competition among other Realtors at their highest levels ever. If only we had as many doctors and Realtors. Imagine how good our health care would be.

For complete business and investment sense, I of course partnered with SHARE, a tech enabled asset manager that allows Canadians to be US landlords without all the heavy lifting. My 17 listeners know I’ve conducted well over 300, hour long interviews with successful and some no longer successful real estate investors work, invest, blood, sweat and tears. In terms of cash flow and overall returns to effort, I haven’t seen anything before that beats SHARE’s offering.

In short, I’ve seen how the top investors implement their real estate investment business and can separate the hype from results. Those with results did not overleverage, were in control the whole time, delivered operationally to renovate and rent as fast as they could. Those who didn’t are the ones making all the headlines in the news for declaring bankruptcy protection or bankruptcy or have their names dragged through Facebook groups for owing money.

I had a call with a newer investor who’s got a great investment property in BC, she AirBnb’s the triplex in the summer months then rents to students during the school year. That’s investing on steroids and she’s rewarded with six figures of rental income.

The investor asked why I call in long-term single family rentals boring? To me it’s not exciting, there’s nothing innovative about it vs. what gets all the attention and likes on social media, note how many of those influencers have gone quiet or done major pivots. I know one big time condo agent appears to have pivoted to coaching Realtors which is going to be really tough in this market. My clients and I’s investing is as passive as possible and we’ve done quite well. Our biggest challenge is under rented properties due to rent control but over the long-term, we’ve all done amazing with market appreciation.

Compare that to Airbnb in the summer where this newer investor does all the client interaction and only outsources the maintenance and cleaning to a property manager for 10% PM fees. Student rentals in my experience are a niche investment that is much more challenging to insure, manage, and get cheap financing. My last student rental mortgage was with Home Trust at over 8% interest plus 1% lender fee.

Again, a wonderful business for the active investor. Just be prepared for plans B and C and D should the municipality turn against student rentals or AirBnb. Just last week, 10,000 protesters in Barcelona took to the streets, some even using water guns to shoot at tourists. The Mayor of Barcelona is banning 10,000 Airbnbs in the city… this makes me thing I need to buy some shares of hotels… source: https://www.ft.com/content/287c1d53-7dd0-410c-88bb-f43277c851b6

In my city, the City of Hamilton implemented rental licensing in the student neighbourhoods with plans to expand across the entire city and the mayor is former NDP leader Andrea Horwath. To conform to licensing could costing landlords from a couple to several thousands of dollars in order to comply along with ongoing fees. Thankfully I’ve sold my student rentals and I’m grateful for having done so as I look out the window of my office and know there are basements being flooded all over the province. There’s plenty of investors struggling out there already who don’t need this. This widespread flooding event will push up insurance rates yet again, more housing cost inflation we can NOT pass onto the tenant in a rent controlled environment.

As someone who despises risk, I’m removing basement flood risk by divesting local houses and investing in houses in the USA that don’t have basements. I’m advising friends, family and clients to not invest in suiting their basements as it makes more sense to allocate those funds to buying a house in the USA. To close on my house in San Antonio I need $97,000 US$ including a $10k reserve fund. A typical basement apartment conversion is $160,000 in my experience and you’re vacant six months. How long depends on the municipality and the quality of your contractor.

My San Antonio tenants are renting the house back from me so I have zero vacancy and can defer my renovations till after they move out which I hope is never since this is Texas and there is no rent control

Only in colder climates do we need basements that go below the frost line to prevent heaving. The same problem doesn’t happen in the southern USA making housing a lot less expensive to build, no need to ever have waterproof let alone flooding if you avoid coastal areas and Florida.

Even if you wanted to buy a turnkey duplex in Hamilton, Barrie, Oshawa, Ottawa etc… I’ve chosen those cities as prices and rents are similar there, I’ve calculated the capitalization rate = $ Net Operating Income / $ price at 4.1%.

Compare that to what my clients are getting, low five to mid 7 cap rates in the USA. The numbers don’t lie, the laws are landlord friendly, no rent control, and commercial style mortgages for us Canadian investors. I make way more commission selling a Canadian property than an American one but I want happy clients hence I recommend US investments over Canadian ones. Diversification and cash flow reasons alone make plain sense. The truth is also it’s way easier selling US income properties. I’ve sold way more US income properties than Canadian ones this year, never in my career since 2010 as a Realtor have I seen so little interest by investors to buy local income properties when the timing is ideal to pick up deals.

I do truly worry for my fellow real estate professionals in Realtors and mortgage agents/brokers. There’s a lot of them already and if they make a living focusing on selling local real estate investments and they not able to sell US products, I won’t be surprised to see many of them leave the industry.

To me, it’s all a matter of education before investing in the USA via SHARE by Canadians is the norm, I honestly love my work, SHARE is the partner every lazy investor like me is looking for except they don’t take any equity share of the investment. Control and ownership remind 100% mine and Cherry’s.

I’m going to record a video comparing a new condo investment vs. a duplex vs. my client’s property. He's from Montreal, has never seen the house that is a 7.6% cap rate that only cost him about $160,000 Canadian.

Link is in the show notes.

There is no guest this week. I literally had invited a former coach of a defunct real estate “university” as they invest big, nice people but their name is being blasted on social media for not making payments on their private mortgages. The coach didn’t respond which never happens as gurus generally love coming on my show. This isn’t an indictment on the coach/investor. If they can survive they’ll come out a winner. Even if they don’t, I believe them to be talented and will come back.

Personally I don’t like my investments to be a roller coaster hence I choose boring as I don’t have thick enough skin to tell people I’ve lost their money or I can’t pay them back. That’s just me. The world needs the self declared crazies like Steve Jobs and Elon Musk. I just know I’m not that and stay in my boring lane.

But I do have equity in SHARE, I have some say in the company’s direction as Head of Business Development in Canada and I don’t see a more efficient path to my company’s 10 year gold: help 200 Canadians become real estate millionaires. I’m at 45 or so now and I can see it in my mind’s eye, 10 years from now enjoying golf and dinner with 200 Canadian real estate millionaires who’ve gained a lot of financial peace via their boring real estate investments.

I can’t wait but I’m totally enjoying the journey. iwin.sharesfr.com if you’d like to learn about the deals my clients and I are doing, from there you can book a Zoom call with me. Past clients, I’m always down for coffee, dessert, breakfast, lunch, dinner, or golf. You know where to find me.