How a Nurse Became a Millionaire and Top 1% Realtor With Milena Simsic


I sure hope interest rates are cut on June 5th! I could use the bump to help sell my daughter’s house.  That is the Truth About Real Estate Investing for Canadians! My name is Erwin Szeto, host of this little podcast, 17 devout listeners, thank you to all 17 of you who said hello and some of you joined me for dinner at the Multifamily Conference! I always appreciate the kind words both in person and on iTunes’ 5 star reviews.

I do have to say I’m grateful for our listeners and past guests of this show who share with me both how they make money AND unfortunately lose money.  I had one listener share with me at the Multifamily Conference. She has five private mortgages that have gone bad. I already knew this is a main area of losses as my wife Cherry has an Accounting practice specializing in Real Estate and private lending is the current #1 loser for investment categories.

I know some out there don’t agree with my stance that I don’t lend privately and probably never will. The worse case scenario that many investors are facing today falls outside my investment criteria.  As my regular listeners know, I’m very diligent and risk averse and if I ever did lend, I would be registered on title.

As for a real estate market update, activity is definitely increasing compared to Victoria Day long weekend. Showing volume is up, I’m getting offers though it’s mostly from what I call vultures: investors throwing out low ball offers looking for motivated sellers.  I don’t blame them, I would be doing the same.

My student rentals had considerably more interest so I’m guessing I’m not the only one steering away from long term, residential tenants.  While tenants in Ontario and BC have all the rights, I don’t see how rents don’t keep climbing as housing is not built, immigration is high, mom and pop landlords are generally exiting.

If you’re a parent or renter, I’d recommend taking action asap.  As many of you know my story, I bought each of my kids a house as a RESP when they were born. I’ve sold one and am selling another now and will redeploy in the USA.  Housing inflation in the USA has been 5.5% each year over the last 53 years so I’m hedging my inflation risk and building wealth for the family.

Speaking of kids, how cute is it that my kids participated in a Dragon’s Den style public speaking competition.  They were taught how to structure a business business pitch then pitched their fictitious businesses in front of a live audience including judges.

My son pitched his flying magic carpet business as an alternative to driving a boring car to avoid traffic jams.  The price of a flying magic carpet? Only $50,000 each LOL. Never forget talk is cheap, in real estate execution is everything, those who don’t execute go bankrupt as we’re seeing in our community.

The cash flow and effort involved never worked for Cherry and I for a large scale portfolio with investment partners in Ontario when commercial interest rates were 4% (we now dream of those days…even at 4% we were conservatively forecasting negative cash flow).  Today we’re at historic highs and I feel sorry for all those losing their shirts and retirement funds.

Keep it boring investors, focus on cash flow, and be passive as possible.  Unless you’re prepared to invest more than 15 hours per week and like being an active investor, go for it. Otherwise, keep it boring and go back to work and your family.

If you want to know the truth about how Cherry and I will be investing boring and for cash flow in the USA then, Saturday June 8th for a hybrid workshop meaning both in person in our offices in Oakville and broadcast online via Zoom webinar.  This is for beginner to experienced investors who have little previous experience investing in the USA and we’re teaching everything you need to know for a whopping $30 plus tax and Eventbrite fees.  That’s tremendous value considering attendees will be learning about the future of Canadians investing in real estate.  The writing is on the wall and from my research, my conclusion is buy American. Pretty much everyone at the Multifamily Conference was saying the same, it’s only a matter of education on how to at this point. 

Link to register:

How a Nurse Became a Millionaire and Top 1% Realtor With Milena Simsic

On to this week’s show!

In the latest episode of our podcast, we had the pleasure of speaking with Milena Simsic, a remarkable individual who transitioned from being an ICU nurse to becoming a top 1% Realtors in Windsor, ON. Milena’s journey is a testament to the power of determination, strategic thinking, and adaptability.

Milena’s story begins in the high-pressure environment of an ICU in Detroit, where she worked for four years, including during the COVID-19 pandemic. Despite her passion for nursing, she realized that her financial goals and long-term aspirations required a different path. Intrigued by the potential of real estate, she saved diligently and made her first property investment, a sixplex within eight months of starting her nursing career.

In February 2022, Milena made the full-time switch to real estate. Leveraging her skills, discipline, and having grown social media presence of 10,000, she quickly established herself as a formidable player in the Windsor market. By the end of her first year, she had achieved $300,000 in gross commission income, placing her in the top 1% of realtors in the area.

We talk about why and how Windsor’s market is booming unlike the rest of the province and how an investor can take advantage of it.

What I love about having this podcast is getting an hour of time from busy, successful talented people such as Milena so we can drill into what makes her tick, her secrets to success, how it didn’t come easy but rather with a lot of hard work.

I’ve been lucky to have many pasts guests of this show and I happen to hang out with 7 figure entrepreneurs all the time so I have experience hanging out with talented people and I’d count Milena among them. You don’t become a top 1% Realtor without talent and hard work. 

If you’re in the Windsor area, you definitely want to the check out the Windsor REI Social, the largest real estate networking event in Windsor, ON. Milena has honoured me with an invite to be the guest speaker Wednesday June 19th, 6pm at the Winelogy Restaurant and Bar.  I’ll be sharing my journey from 20 year landlord in Ontario to my recent pivot to the USA and I have to same kudos to Windsor REI Hosts Milena and Brandon Finn for hosting a speaker on the subject of USA Investing.  Not many local real estate professionals would.

To register for the meetup: Link:

To follow Milena:




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Before you go, if you’re interested in what kind of properties I am looking at in the landlord friendly states of the USA please go to for what I consider the best investment for most Canadians, most of the time.

I’ve been investing in Ontario since 2005 and while it’s been a great, great run. I started out buying properties in the 100,000s and now it’s $800,000 to $1,000,000.  How much higher can it go? I don’t know

To me, the remaining potential for appreciation does not match the risk hence I’m advising my clients to look to where one can find rental properties that are affordable range of $150,000 to $350,000 US$, with rents that range from $1,400 to 2,600/month plus utilities.   As many Canadians recognize, these numbers will be positive cash flow and are night and day compared to anything locally. Plus the landlord has all of the rights, no rent control, and income is US dollars which are better than Canadian dollars.

If you don’t believe me, US dollars are better than Canadian dollars, go ask 100 non-Canadians which currency they prefer to be paid in.

So to regain control of your retirement planning.  Go to and check out what great cash flow properties are available in the USA.  

The best part is, my US investments will be much more passive compared to by local investments as I’m hiring an asset manager called SHARE to hand hold me through the entire process.  As their client and shareholder, Share will source me quality income properties, help me with legal structure and taxes, they manage the property manager and insurance provider while passing down to me preferred rates so I save both time and money.  

Share will even tell me when to strategically refinance or sell.  SHARE can even support investors all over the country for proper diversification hence my plan is to own in Tennessee, Georgia, and Texas.  Share is like my joint venture partner but I only have to pay them fees while I keep 100% ownership and control.

If your goal in investing is to increase cash flow, I don’t know of a better strategy for most Canadians most of the time.  One last time that’s to see what boring, cash flowing real estate investing can look like on your path towards financial peace.

This is how I’m going to make real estate investing great again for my family and hope you choose the same.  Till next time!

Sponsored by:

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 event.

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



As a committed advocate for transparent and responsible real estate investment, I want to openly share my involvement with SHARE SFR (Single Family Rental) as an Advisor. I hold an equity position in this company and receive a referral commission for clients I introduce to their services. My endorsement of their business model – focusing on direct ownership of positive cash flow income properties – is consistent with my own personal investing since 2005, is based not only on a professional assessment but also on my personal experience and belief in their approach. Please note that while I stand behind my recommendations, it is crucial for each individual to conduct their own due diligence and consider their unique circumstances before making any investment decisions. As always, my priority is to provide you with honest, insightful, and practical real estate investment education.
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