Age 26, Making $300,000 in 20 Months On Cash Flowing Duplexes and 70 Hour Weeks With Joe Costanza

What was I thinking not hiring a coach sooner?

For regular listeners, you know I’m a big fan of self development, learning, reading, and one of my favourite hacks is having coaches.

I have Crossfit coaches, a Realtor coach, two Stock Hacking coaches, a new real estate investing coach and a pretty new golf coach.

My golf coach’s name is Chris and he’s a lot better than I at golf.  He’s an associate golf pro at a pretty nice public golf course in Oakville, Ontario. He’s a tall, thin, 150 pound scratch golfer and drives the ball 300 yards.  Scratch golf means he’s in the top 1.6% of golfers who report their scores.

As with anything in life, business, health, investing, I view it all as an experiment. 

When the pandemic hit, the first thing we were allowed to do was golf so I took up the sport.  2020 is the first year I’ve played more than twice in a season so I think that qualifies me as a beginner.

This past Friday I had just my fourth golf lesson with Chris and finally made some massive improvements, the most improvement I’ve made all season.

Right after my lesson, we played nine holes and I proceeded to have my best 9 holes of the season highlighted by landing my ball 12 feet from the hole on a 193 par 3 with my 5 iron. That’s about 30 yards farther than I normally hit my 5 iron and I made the putt for my first birdie of the season. 

The next day, I was golfing with Cherry and ten other friends and I had one of my better rounds of the season include 3 pars and a birdie on the front 9.

What is the point of all this?

After the round was over I couldn’t help but kick myself how if I could do it all again, I would have invested more heavily into coaching near the beginning of the season as much of the practice I did this season was kinda wasted.

This was yet another experiment that proved to me the value of coaching. 

Practice and youtube and reading articles online as much as I did… those tens of hours did not compare to the 4 hours of coaching I’ve received. 

Going forward I will be taking weekly lessons as it is one of my Stock Hacking goals to afford me a nice golf membership.

In my experience, I pay tens of thousands each year for coaching and the investment has returned. 

My question to the listener is where can you fast track your success by hiring a coach? I’ve wasted a lot of time in all areas by not having a coach.

Please don’t make the same mistakes I did.

This week’s guest, 26-year-old Joe Costanza was smart and worked with Coach Tammy Ditomaso from my IWIN Real Estate team to begin his real estate journey. 

If you’re interested in learning for free the same strategy implemented by young Joe who’s increased his net worth by over $300,000 in just 20 months then go to and enter your contact information to be notified of our next free training class on the #1 investment strategy in real estate.

On to this week’s show!

Age 26, Making $300,000 in 20 Months On Cash Flowing Duplexes and 70 Hour Weeks With Joe Costanza

I first met Joe Costanza 20 months ago when he was a starry-eyed 24-year-old who had been hustling since a teenager, working several jobs, living at home to save up down payments for real estate. 

An architect by trade and having tried several side hustles less than successfully, Joe settled on real estate without much support from his parents.

Fast forward to today, Joe owns three properties, two he’s already duplexed and the third to be duplexed house with a joint venture partner. 

This is Joe’s story.  For those who like numbers, we’re pretty heavy with the numbers in this episode so have your pens ready.

I give you Joe Costanza.

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Before you go, if you’re interested in being a successful real estate investor like those who have been featured on this podcast and our hundreds of successful clients please let us know.

It is our honour to give back and educate others on how we build cash flowing real estate portfolios using all the best practices shared on this podcast, from the lessons of our hundreds of clients and of course our own experience in owning investment real estate.

If you didn’t know already, we pride ourselves at being the best of the best real estate coaches, having the best property managers, contractors, handy people, cleaners, lawyers, accountants, everyone you need on your power team and we’re happy to share them with our clients to ensure your success. 

New investor or seasoned veteran investor, we can help anyone by providing our award winning coaching services and this isn’t all talk.

We have been awarded Realtor of the Year to Investors in 2015 by the Real Estate Investment Network, 2016 by the Canadian Real Estate Wealth Magazine and again in 2017 because no one told the judges no one is supposed to win the award twice but on merit, our peers deemed us as the best.  In 2018, we again won the same award by the Real Estate Investment Network.

Hopefully being the most decorated team of Realtors in Ontario will make you consider us for your first or next real estate investment.  Even if you don’t invest in our areas, there’s a good chance I know who would be ideal for you. 

I’ve been around for a while, some Realtors are talented at servicing investors there are many with great ethics.  The intersection of the two, talent and ethics is limited to a handful in each city or town.

Only work with the best is what my father always taught me.  If you’re interested, drop us an email at

I hope to meet you at one of our meetups soon.

Again that’s

Looking to add another stream of income?

We just completed the long anticipated Stock Hacker Academy Live Introductory Course and it was awesome!

Stock Hacker Academy is the foundation that has helped Erwin, Cherry and many other Stock Hackers make thousands of $$ weekly and now they never have to worry about money again!

If you desire the same for yourself, click here to register now

NO MORE Confusion

After all the Youtube videos, books, and forum posts, you’re probably still left with questions. Starting in real estate is a tricky thing.

Frustrated beginners often ask how a legal basement suite conversion actually works. Most of the time we can only give general answers. But now, we get to dive in.

At this in-depth, free class you’ll learn how to take your first steps as a real estate investor.

Nothing is held back. Everything from analyzing basement suite conversion deals, to renting out your first property at a profit, and even how to refinance and do it all again!

More secrets you’ll uncover are:

Profiting in a HOT market…

Municipal bylaws to watch out for…

Mortgage terms that favour refinancing…

AND one barely used tactic for higher appraisals…

If you’re frustrated, unsure of how to get started, this is for you.

 Sign up now for the Invitation List and be one of the first to get an invite to the next class.

Sponsored by:

Infinity Wealth Investment Network – would you like to know how our investors returned 341.8% on positive cash flowing real estate over the last five years? On average, that was 68.4% per year.

Just imagine what winning in real estate could do for you.

If you would like to know how we did it, ask us how by calling 289-288-5019 or email us at

Don’t delay, the top markets we focus in are trending upward in price, so you can pay today’s price or tomorrow’s price.

Till next time, just do it because I believe in you.


Hamilton, St. Catharines and Toronto Land Development, Real Estate Investor, and soon to be builder.


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