So Nick's family went to NYC last week, and this week it was our family's turn.
That's a picture from this past Tuesday in Central Park.
We hit the skating rink and couldn't have asked for a better day.
Manhattan can be pretty intense during the Christmas season, and what always shocks me is how quickly a walk through Central Park rejuvenates you.
You can be just a few hundred feet into the park, and it will feel like you're out in the wilderness and not in the middle of a big city at all.
Amazing.
If you haven't checked out Manhattan during the holidays, it's a must-see in our opinion.
Three days ... that's all you need.
See a show, grab some great food, do some shopping, take a walking tour or two, visit the park, check out one of the museums and then get out of there!! LOL.
Let's dive into much serious business...
There's a piece of advice we've followed over the years, and it's served us very well.
"Watch what everyone else does - do the opposite. The majority is always wrong." - Earl Nightingale
This advice has served us so well.
When we got into real estate investing we were told by so many people to "do flips, do renos, buy condos, do vacation properties, go out East, go out West", etc.
And what we've found over the years is that the majority cannot focus.
We observed during the 1990s that single-family-starter-homes always seemed to have the most demand in any market.
Our family was flipping large luxury properties back in the 90s and when the real estate downturn hit... those properties got hit hard.
Demand evaporated overnight.
We had family friends buying condos in Mississauga, right by Square One, and in the 90s the prices of those condos collapsed and took years to recover.
And during that time we noticed that nice, smaller, starter homes, in good areas, always seemed to have the most demand.
In good times, people moved from renting into them.
And in bad times, people sold larger houses and moved back into starter homes.
So in any market, starter homes always had the most demand, they were the most liquid and had the most financing options.
This observation made us focus solely on single-family-starter-homes for years and years.
And the most beautiful part about single-family homes is, as an investor, you can run multiple strategies on them.
We have one property that we have run as a rent-to-own, then as a student rental and now as a single-family-rental.
The accountant who moved into it as a rent-to-own got a new girlfriend who convinced him to get a bigger house.
So he didn't end up buying it and moved out.
With that strategy, we got $15K upfront (non-refundable option fee) and monthly positive cash flow for 3 years.
When they moved out we rented it out to a group of students. We then had even higher positive cash flow for the next 7-8 years.
And for the last few years we have been renting it to a single family again, with positive cash flow.
Single-family homes offer a LOT of flexibility.
Especially when you buy them in the right areas.
We have another property next to McMaster University that we have rented out to students for almost 25 years now.
7-bedrooms, positive cash flow.
I think when we first bought it, we had a total rent on the house of about $2,500.
Not only did we have positive cash flow, but we refinanced that property twice over the next few years.
The first time, to raise money to renovate and update the basement.
The second time, to use the equity in that property to help buy another property.
Each time, it never fell into negative cash flow territory.
And now we're planning something a bit wild.
Zoning laws have gotten a lot more flexible over the last few years.
Ontario is realizing that there is a huge lack of housing.
And it's no surprise; look at this chart courtesy of our friend Ben Rabidoux...
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Single-family housing starts haven't increased in decades.
DECADES!
Because of this, cities have softened their zoning bylaws to encourage new housing starts.
And now, with these new bylaws, we're thinking of taking that 7-bedroom student rental and turning it into a beautiful new triplex.
It's right next to the Hospital at McMaster.
We can refinance the property, yet again, and have it pay for its own conversion into a triplex.
And after the reno the expected cash flow on that property will be...
Are you ready for this?
About $6,000 - $7,000 per month.
This is a single-family house that produced cash flow for over twenty years and now is capable of increasing that cash flow even more.
Patience, focus and not getting distracted has put us into this position.
Nothing magical has happened.
One property. Same address. More Cash Flow. Much more.
Wild.
So while everyone was running around buying condos, racing into vacation property rentals, flipping luxury homes... we have found that just staying the course, with a single thing that you believe in, can be very profitable.
Boring? Yes.
Profitable? Very.
And we're excited to announce something that we haven't done in a very long time.
We're going to share the latest strategies we're using and show examples of single-family home investing at our first LIVE and IN-PERSON training class in our Oakville offices in over 5 years!
LIVE & IN-PERSON
How To Invest in Cash-Flowing Properties
Right Here in the Toronto & Hamilton Area
"90-Minutes That Can Change Your Life"
Wednesday January 14, 2026
7:00 pm Sharp
Register: https://get.rockstarinnercircle.com/free-training-class_in-person/
We haven't presented live, in our Oakville offices, in so long that it's going to be a nice change.
The time has come to get together, in-person, with you and share what we're seeing right now.
There are opportunities everywhere if you know where to look
No hype. No "get rich quick" nonsense.
Just how to invest in good homes, in good areas, profitably.
We'll stick around to answer your questions too.
There's just too much confusion going on right now, we need to bring this back.
Look, over the next few years, it's going to be critical that you own good hard assets.
It's become necessary.
We like gold, we love Bitcoin and we know single-family-home investing like the back of our hands!
Visit this page to register for this class right now.
And bring anything that is on your mind.
Our training room has limited seats, so once they're gone, they're gone!
In the class, we'll share:
And more!!
Remember this...
"Watch what everyone else does - do the opposite. The majority is always wrong." - Earl Nightingale
Don't be the majority.
Register for this class right here...
https://get.rockstarinnercircle.com/free-training-class_in-person/
Here's to an amazing 2026 everyone!
Merry Christmas, Happy Holidays & Happy Freaking New Year!!
Tom & Nick
p.s. Life is short, embrace all of it, move fast, make mistakes, have fun, hug your loved ones, create memorable moments, live life on your terms!!
