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

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 inves...