The Truth About Real Estate Investing... for Canadians – Details, episodes & analysis

Are you a Canadian investor struggling with low cash flow, rent control, or expensive renovations? In this episode, we sit down with Ben Barry, a U.S. real estate expert who's deployed over $2 billion in capital and helped transform how investors like you succeed south of the border.
 What You’ll Learn:

• How Canadian investors can tap into high-yield U.S. rental markets

• Why technology and data are changing the game in real estate
  

• The real story behind turnkey rentals and institutional landlords
  

• Tips on navigating taxes, financing, and management across borders
  

Whether you're fed up with Ontario's eviction delays or you're just curious about basement conversions vs. single-family rentals, this is your roadmap to smarter investing.

Hey friends, this is Erwin Szeto, and welcome to The Truth About Real Estate Investing for Canadians, where it’s my job to interview the top minds in real estate and business to uncover the strategies, mindsets, and habits that actually work—especially in today’s market.

My guest today is Michael Ponte—a full-time real estate investor, educator, and co-founder of Savvy Investor. He’s been investing for more than 20 years and owns a multi-provincial portfolio that spans Alberta, BC, and Atlantic Canada. He’s raised capital, survived multiple recessions, and built a strategy around what he calls “lazy investing”—focused on cash flow, simplicity, and long-term success.

In this episode, we get into:

• Why he avoids over-leveraged strategies like promissory notes and MLI Select
• What it’s like to refinance and pull nearly $1 million out of a property
• And how he built a business around student rentals, multi-family units, and zero tolerance for rent control

Also—Michael is hosting a free virtual boot camp on May 3rd, and I’ll be one of the speakers. It’s called The Savvy Investor Boot Camp, and it covers everything from BRRRRs to private lending to U.S. investing. You can register at thesavvyinvestor.ca -- again, it’s completely free.

Now, please enjoy my conversation with Michael Ponte.

On to this week’s guest!

Again, Hart is a friend, I refer him clients all the time for tenant location services.  This may sound like a paid endorsement and full disclosure, Hart Pays me nothing. We receive zero compensation for me having Hart on this show and sending him referrals.  It’s too bad we’re selling the rest of our Ontario portfolio in the near future so I could have asked him for favours but no. Nothing LOL. Which I don’t mind so my judgement is not clouded.

We get a long because we’re both on a mission to help Canadians get a head in life without taking away too much time from their lives and families by streamlining their investments. Let them sleep at night and we both volunteer for non-profits that support landlords.

Hart’s company Rent Panda is an expert on rentals providing both property management and tenant location services while also using the same tools we recommend like SingleKey and Front Lobby.  Any Ontario landlord not using them is exposing themselves to unnecessary risk. Risks that honestly don’t exist in landlord friendly USA but I digress.

You can find Rent Panda along with a bunch of free online resources every Ontario landlord needs at www.rentpanda.ca

On to this week’s show!

We have something different in that our guest is a successful entrepreneur in the world of Business and not real estate investing, YET.

Nick Kindler is the Chapter President of Entrepreneur’s Organization, a private membership of seven figure entrepreneurs that Cherry and I also belong too.

As a member of the real estate community, I find learning from entrepreneurs just as helpful as learning from real estate investors to broaden my learning.  I also see all these memberships and masterminds costing $20,000-30,000 or more, I wanted you my 17 listeners to be aware of other masterminds, membership groups and Entrepreneurs Organization is less than $10,000 per year and I’m a big fan.

Who better to talk about Entrepreneurship than our very own Chapter President Nick Kindler who also happens to be my client who’s working with team member, Chris “the Captain” Hook to acquire quality investment properties.

Nick is here today to share his experience as an EO member, President, his entrepreneurial journey which includes a $4.5M business that went bankrupt but more importantly how he bounced back, the lessons learned so you may avoid the same mistakes.

FYI - failing businesses, losing money and letting staff is not a fun experience in my experience. Please take notes.

If you would like to learn more about Entrepreneurs Organisation please reach out to Nick on his company website www.kindlerandcompany.com/contact you can hit me up on email on DM or you look up your local chapter at https://hub.eonetwork.org/

I’ll be a the open house event on March 9th that Nick mentions so I hope to see you there! Link: https://www.eonetwork.org/toronto/Pages/upcoming-events.aspx?i=2&s=5

Nick’s consulting business helps innovative leaders communicate better, for example I attended Nick’s two day workshop on how to give a TED talk which was excellent where Nick deconstructed what goes into an excellent talk then walked us through to write our own and how to deliver with stage presence. 

Nick is also the author of Impact: Simplify, Transform, and Perform Pitches and Presentations available at https://www.impactbook.ca/

Without further ado, I give you Nick Kindler.

Hello and welcome to another episode of the Truth About Real Estate, my name is Erwin Szeto, the four time award winning Realtor to investors, host of this podcast, the #81 Business podcast per iTunes, where we focus on bringing you true experts, masters of their craft and we have a great guest for you today in real estate coach and educator Elizabeth Kelly.

The term coach has been used lightly these days. I see even folks with 1-2 properties as side hustles call themselves coaches. Elizabeth Kelly has a bit more to her resume than that. Her own property management company hundreds of doors, she was a full time real estate investing educator at Rich Dad Canada having personally taught a couple thousand investors including many of the infuencers and coaches you see today on social media.

Today we touch on a couple subjects such as the investment in real estate education and some of the different options out there as there are more than ever but some offer better value than others.

Elizabeth shares about her career and investor journey to arrive at where she is today.  Her strategies when starting out investing in 2008 is very different than how she invests today and my intention for you my 17 listeners is to see for yourself how a professional investors at different stages, lessons learn so you may avoid mistakes and make more money.

Then we will offend many when we discuss what’s working and what’s not working in 2023. This may shock you, many of the fad investments getting a lot of hype won’t work in 2023. Make sure to have a listen before investing in any coaching or courses or even property.

2023 is going to be a fascinating year and here at iWIN real estate, we will be arming our community with the best information possible. Staring with our free webinar on how to sell a tenanted property for maximum return on January 17th, followed by our iWIN, in personal networking meeting on Saturday morning Jan 28th when my team and I share our bold predictions for 2023 for our target investment markets and we have at REIT in the house, Lawrence Raponi of Equiton with a brand new presentation explain how professionals buy apartment buildings, from how they find deals, to the numbers they need before even looking further into.

Learn how the professionals invest or at least learn how investing in a REIT works including cash flowing from day 1.

If you’re on my email newsletter, then you know how to register. If you don’t? Well that’s just silly, go to www.truthaboutrealestateinvesting.ca enter your name and email and you will receive an email when we have events and when new episodes of this show is available.

New to 2023 is we will be producing a lot more free educational videos and podcasts. If you have suggestions for topics you would like covered please let us know.

It’s my pleasure to introduce to you, my friend who passed our strict screening, Elizabeth Kelly.

Please enjoy the show!

LinkedIn: https://www.linkedin.com/in/elizabeth-kelly-consulting

FB: https://m.facebook.com/EKConsulting.ca/

IG: https://instagram.com/elizabethkellyconsulting?igshid=MWI4MTIyMDE=

Real Estate Resilience Summit: https://realestateresilience.ca/sumreal-estate-resilience-summit-ek

We have Ken Bekendam who is up to many things to generate cash flow and build wealth in real estate.  The best part is Ken is available for hire! One can hire Ken’s company https://legalsecondsuites.com for major renos to your home or investment property including basement apartments and garden suites.

Ken and Legal Second Suites has even been in the news representing one of his clients, a mutual friend of ours Alex who happens to be Ukrainian who wants to convert his garage into a garden suite to rent to Ukrainian immigrants but the rich neighbours think the added density of tenants living in a garage will damage the neighbourhood and increase traffic.  

Thankfully, with municipalities trending in the right direction to allow for us private investors to create more housing… well I won’t spoil it and let Ken explain to you how the story ends. Rich homeowners vs. rental housing for Ukrainian immigrants….

In today’s show, Ken details what strategy makes up the majority of his portfolio and provides him with the massive cash flows. It’s not what you expect as none of the influencers out there are promoting, nor offering courses on this strategy.  

Ken shares how to invest in garden suites including build costs and rents plus some conversion projects both big and small.  This is really great episode for education purposes so do have those pens and pencils ready.

I give you my friend Ken Bekendam

Please enjoy the show!

Web: https://legalsecondsuites.com/

IG: https://www.instagram.com/legalsecondsuites/

FB: https://www.facebook.com/people/Legal-Second-Suites/100086295136299/

Victor shares a lot today about how to scale up a real estate portfolio, how novices can get started interning/volunteering on development projects to gain invaluable experience for a smoother transition from side hustle developer to full timer. 

There’s Victor’s strategy of “buy on the line, move the line” for investing in gentrifying locations.  We’ve been practising the same strategy in our local markets, I just didn’t know there was a name for it.  In Hamilton the old rules were to stay south of Main St. and West of James St., as a rule breaker we didn’t listen knowing affordability would cause the areas we targeted to appreciate and it worked out incredibly well. 

If you too are looking to build out a team in the areas east and west of the GTA where properties actually cash flow then don’t miss out on our street smart tours! New to 2023 we’ll be operating tours of income properties in Oshawa followed by a mastermind lunch for which I’ll be in attendance as well. This a wonderful opportunity for investors of any level, especially novices to see how the FOUR time Realtors of the Year to investors service their clients enabling them to build intergenerational wealth.

Make sure you’re on our email newsletter along with 10,000+ other hard working Canadian investors available at www.truthaboutrealestateinvesting.ca. I hope to see you in 2023 at one of our iWIN Real Estate meetups and/or street smart tours.  Like Victor says, there are going to be some great deals available in the near future.  Learn what a deal looks like and work with an award winning team that produces successful, multi-millionaire investor clients.

BTW, Victor is also the President of OREIO and if you’re in Ottawa, you want to check them out. In my experience, the value and quality of group can’t be beat hence I’m a paying member as well.

LinkedIn: https://www.linkedin.com/in/vmenasce/?originalSubdomain=ca

Personal Website: http://www.victorjm.com/

Work Website: www.Ystreetcapital.com

OREIO: https://www.oreio.org/

This week is a lovely story about a young Millennial who started his journey in his passion: health and fitness, if you’ve seen Vince Lee in person, he’s jacked and looks like a personal fitness trainer.  Unfortunately for personal trainers living in Toronto, it’s hard to get by.

Thanks to his supportive partner, shout out Chewy and the Trust Your Talent community, shout out Tim Tsai, Vince has been able to create a side hustle in real estate investing, specifically rent-to-owns, scaling to larger and more projects, and moved the family from expensive Toronto to more affordable Edmonton, Alberta.

Vince’s story is a good one and reminds me of why I invest so hard, so I can afford to keep my kids close and living in Ontario.

Congrats to Vince’s success, please enjoy the show!

To follow Vince:

Web: Trustyourtalent.ca

Instagram: theonlyvincelee

Facebook: https://www.facebook.com/theonlyvince

How refreshing is our guest Diana today! It goes to show one can’t judge from an Instagram handle. Eg Diana’s is @investorgirldiana when really it should be @sophisticatedinvestordiana but I get it. We are supposed to be humble and modest in our marketing.

But screw it. Diana is legit. She shares her experience and numbers flipping from a $2.3M luxury house in Toronto and to a century home in Hamilton to Windsor private lending as well.  There are lots of numbers in this episode including mortgage rates as some of the capital was private money AND Diana shares how she personally lends her own money. 

Diana’s taken expensive courses and masterminds.  The quality of some is questionable as there were folks in the same masterminds as her years ago who are now bankrupt financially.  That’s right, some courses, memberships, and coaching have negative return on investment.  You as an investor have to conduct proper due diligence on anything you invest in including education.

Diana however with her conservative projections and husband as a skilled general contractor have navigated this declining market and exited flips profitably. Some are more profitable than others and not without challenges which Diana shares.

Sidenote: I’ve noticed a trend where an investor’s ability to execute on construction or renovations can be make or break for investors. Especially the full timers. In my experience, constantly working with the best of the best contractors has been instrumental to my clients and our own success in our portfolios. Those unable to execute 

Not that any contractor is perfect unless maybe you marry them like Diana but much risk can be mitigated with the right one and proper oversight.  That’s something we do for our clients, connect them with the same contractors we use and we are in regular weekly contact with them for our own projects and for our clients.  As we here at iWIN Real Estate, we do volume hence we are usually our contractors top referral source and we’re all looking for win-win-win results. Win for the contractor, win for the client, win for us in that we have a happy client who buys more houses and sends us referrals. 

We are in this for not just long-term but rather intergenerational relationships to create intergenerational wealth as we literally have three generation clients: grandparents, parents and the kids.

To follow Diana:

Linktree: https://linktr.ee/InvestorGirlDiana

Instagram: https://www.instagram.com/investorgirldiana/

Facebook: https://www.facebook.com/diana.lizarazorocha

We have old friend of the show Russell Westcott who was in town all the way from Vancouver to Toronto for the Wealth Hacker Conference.

Russell has owned 100+ properties and has the battle scars and lessons on how to invest better in Edmonton Alberta.  Russell is a smart guy and here to share about how his coaching clients are navigating this high interest rate environment with creative, above board financing and a couple different investment strategies for highest and best use to create more housing units and of course generate higher rents on properties that other investors simply don’t see.

As always it’s a treat to have the JV Jedi on the show, someone who’s always thinking outside the box on how to maximise returns for his coaching clients and on their properties.

I give you best-selling co-author Russell Westcott!

Website: www.russellwestcott.com

Instagram: @russellwestcott

Facebook: russellwestcott10