Major Announcement. How We are Making Real Estate Great Again

Hello and welcome to the Truth About Real Estate Investing for Canadians, my name is Erwin Szeto, residential real estate investor since 2005, and in my experience, the investment that has gotten my over 350 clients ahead in life is direct ownership of real estate as they own the property, manage it themselves or hire a property manager, and grow their portfolios by borrowing cheap mortgage money. My team here at iWIN real estate has been coaching clients to do so since 2010 and it’s been a great run.

Yesterday, I was supporting one of my clients who I’ve helped acquire several properties whose tenant has not paid rent in 13 months even though they won at the Landlord Tenant Board five months ago.  He also shared with me how his rental portfolio was the highest source of stress in his life.

Another client, a real estate mortgage professional, he’s had minor basement leakage in one property in a brand new renovation and in his other brand new renovation, the tenant move out because the floors are out of whack having been installed onto of an uneven floor.  The tenant said the flooring edges are sharp and too dangerous for their baby to be crawling around on. My client is back and forth with the flooring manufacturer and the general contractor and it’s been months.

The truth about real estate investing is it can be stressful and there are challenges.  I have my own stories too for another day but this is not why I first got into real estate.  I started investing for an alternate source of income. I would side hustle as a real estate investor for a return of more freedom, more control over my finances and bring my clients along for the same journey.

It’s always my job as chief investment officer of my household and for my clients to find ways to optimize their portfolios including reducing risk.

In the current environment with inflation, rent control, dysfunctional Landlord Tenant Board, and elevated interest rates.  Add to that how anti landlord the politicians and media are, I don’t feel I’m in control anymore hence I see the writing on the wall.  Cherry and I are selling several if not all of our rental properties in Ontario to take profits, pay off debts, raise cash to take advantage of other opportunities mostly in landlord friendly locations in and around the top 10 cities for investment in the USA.

Both Americans from California and New York along with Canadians are making the move to red, sunbelt states.

The business environment in certain states where I will be targeting offers better numbers and less risk. No question.  At my stage of investing career, I’ve invested in over 40 houses, done many advanced BRRRRs but because I can cash flow better on single family houses in the US, 5-7 cap rates, the same cap rates past guest of this show do with apartment buildings after 5-10 years of renovating, turning over apartments.

I see no reason to take on so much risk when there’s an easier way.

I finally have easy financing, it’s actually easier to get a Mortgage in the US than in Canada. Scott Dillingham of LendCity, who I’ve been working for years to get me mortgage brokers on income properties shared with me in the summer he would soon be able to offer easy, commercial style mortgages for Canadians to invest in an unlimited number of American income properties.  No credit needed.

Investing in real estate without mortgages makes little sense hence I’d never taken US investing seriously but Scott opened the door, I walked through it and went all in on my due diligence.

I’ve never been so frustrated as an Ontario landlord.  For example, did you know tenanted properties for sale are getting next to no showings?  In my nearly two decades, I have never seen showings volume so bad for turnkey income properties at the same time the LTB is so broken, the allowable rent increase so far below inflation, the government anti landlord rhetoric so bad.  I just witnessed a turnkey duplex in Hamilton, ON sell for almost 30% off from peak this past weekend.

But that’s OK, I’m going to pivot to investing the the USA but big but, I’m risk adverse and I’ve seen so many deals go sideways when remote investing.  Plus I don’t like sharing my investments, I prefer to keep all of the equity and all of the upside returns to myself.

Then by fate, a past client of mine, Brent introduced me to his friend Andrew and it was as if the universe was telling me something.

Andrew Kim, I read about his start up, a tech, Ai, enabled asset management company in the Toronto Star and Brent out of the blue introduces me to Andrew. 

First off, what’s an asset manager? Let’s first start with explaining what a property manager is as we’re most familiar with that. Per ChatGPT a property manager handles daily operations, tenant relations, maintenance, and rent collection to ensure the property runs smoothly.

An asset manager manages the property manager, focuses on maximizing the property’s value and investment returns, dealing with acquisitions, dispositions, and strategic financial planning like when to refinance.  That’s what Andrew’s company SHARE does specializing in single family rentals.

I’ve invested the last three months conducting due diligence on investing in the US, on Andrew’s Share, Scott’s Lendcity (I’ve researched their competition, checked references), and we delivered our first ever US investing workshop to much success. Feedback rating was 9.5/10, we’ll announce our next one mid January and we raised $5,400 for charity.  Win-win-win-win, the way I like it. A win for Andrew, Scott; a win for my business iWIN, the attendees loved it, and $5,400 goes a long way at my charity the Hamilton Basket Brigade.

My trip to Atlanta, Georgia was hosted by Share, I invited along another real estate investor friend of mine, we got to hang out with both Andrew and Chief Investment Officer Dmitri who is a real estate investing wizard having experienced acquiring and managing 20,000 apartment units or $7 billion as an Executive Director of Investments at Starlight. Dmitri easily has the most institutional experience of anyone I know personally and for someone who has a million questions like I do, I was super excited. 

Our tour of investment properties in the suburbs of Atlanta was led by a nationwide, institutional, top tier property management company who manages 2,800 single family houses in America with 800 alone in the Atlanta area.  I was thoroughly impressed by what I saw: well oiled systems, reasonable renovation budgets and turnaround times, no rent control.

I had a deadline to complete my due diligence by the end of the Atlanta trip, to understand the asset I was investing in plus the operations and just as importantly the leadership.

As we were exiting the baggage area of Pearson Airport, we’re walking out together and we see a family with small kids.  Mom and dad are pushing three, fully loaded luggage carts, mom is trying to push two carts while herding her four year old.  I take a step in their direction to help out, Andrew, CEO of Share who’s been struggling with pain the whole trip due to a partially herniated disk in his back beats me to it and pushes one of the mom’s carts.

What a Boy Scout like I was growing up.

As my due diligence is complete, I have some exciting news to share effective immediately:

iWIN Real Estate is proud to announce its strategic partnership with SHARE, a Canadian real estate asset management company specializing in streamlining the end-to-end process of vetting, buying, and managing high-return single-family rental homes in the USA for investors. Using IWIN’s influence in the Canadian real estate investor community, more frustrated, everyday investors will have the opportunity to improve cash flow, diversify, and make real estate investing great again!

By combining SHARE’s U.S. investment expertise and IWIN’s commitment to delivering exceptional results and pioneering investment solutions, investors of all levels can access a wealth of benefits, from streamlined investment process, quality education, and coaching.

“Frustrated Canadian investors, especially in Ontario and BC are looking for diversification in a more landlord-friendly environment and modern solutions, including supercharged systems where everything an investor needs exists under one roof,” said Erwin Szeto, Founder of IWIN. “Together with SHARE, we aim to make direct ownership of income properties more affordable, profitable, less risk, and rewarding for the everyday mom and pop investors.”

SHARE offers investors a comprehensive suite of services for Canadians, including sourcing and acquiring high-quality single-family rental homes in prime locations, professional property management, financing options, legal structuring, and investment portfolio diversification.

“With SHARE’s diversified inventory and proven track record of generating high returns, investors can access even more lucrative opportunities with reduced risk,” said Andrew Kim, CEO and Co-Founder of SHARE. “Partnering with IWIN allows SHARE investors to tap into that passive income element and portfolio expansion all while knowing their assets are protected.” 

Partner With SHARE

SHARE offers real estate service providers with existing customer bases or audiences like iWIN Real Estate the opportunity to expand their investment offerings for a mutually beneficial relationship and provide clients with a comprehensive and seamless real estate investment experience in the USA.  Book a call with Erwin  to learn how partnering with SHARE can add value to your investment offerings.

End of press release.

My plan is to continue operating iWIN Real Estate as we are carrying more properties for sale than we ever had in my 13 year career as we continue to help our clients with their real estate needs.  Our offerings of real estate investments have simply expanded and when new investors come to me and ask what they should invest in, I simply present, side by side an $800,000 duplex or $1.2 million triplex here in Ontario vs. a single family for $100,000-300,000 in the US that cash flows better along with all the reasons a US investment is easier and they can decide for themselves.  

Officially, I’ve joined Share’s advisory board to guide the growth of the Canadian market as a part time role as part of my full time role as chief investment advisor for my family, to our hundreds of mom and pop investor clients, and my favourite people, our 17 listeners of the podcast.

The truth about real estate is, I haven’t been this excited about real estate investing since legal duplexes in 2015 and now with US investment properties on the table, I see the path to no longer have to subsidize the out of control housing inflation for my current tenants and make real estate investing great again.


This episode is brought to you by me! We don’t have sponsors for this show. I only share with you services owned by my wife Cherry and me.  Real estate investing is a staple in my life and allowed me to build wealth and, more importantly, achieve financial peace about the future, knowing our retirement is taken care of and my kids will be able to afford a home when they grow up.  If you, too, are interested in my systematic strategy to implement the #1 investment strategy, the same one pretty much all my guests are doing themselves, then go visit and register for our next FREE Online Training Class.  We will be back in person once legally allowed to do so, but for now, we are 100% virtual.

No need for you to reinvent the wheel; we have our system down pat. Again that’s and register for the FREE Online Training Class.

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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 on 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

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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