The Truth About Real Estate Investing... for Canad

Milena Simsic made $300,000 in commissions in her first year as a realtor, without any prior real estate connections, using nothing but TikTok and Instagram. She had no social media presence before she got her license. She figured it out in public.    Milena is the founder of WindSocial Realty in Windsor, Ontario, and the publisher of the Windsor Real Estate Insider, a newsletter and magazine that grew to 9,000 subscribers in under a year. She also runs Windsor REI Social, a 3,000-member community that fills events with 100 to 200 investors. She is currently switching brokerages from EXP to Real and building a community for realtors who want to learn AI-powered marketing.    In this conversation, we cover:  Why Windsor's single-family homes have held value while student rentals and investment properties have softened  What the Gordy Howe Bridge delay and the EV plant mean for Windsor's growth trajectory  How Milena made $300K her first year as a realtor off TikTok and Instagram alone  Why she replaced her virtual assistant with Claude AI and built her CRM systems in an afternoon  How the top agents implementing AI are going to absorb market share from those who are not  Why she left EXP for Real, and what Real is getting right that most online brokerages are not  The health crisis that doubled her business once she fixed it  Why business owners are particularly vulnerable to loneliness and what she did about it  How Windsor REI Social went from monthly to biannual events and why that made it bigger    Milena's arc is the arc TAFI was rebranded to celebrate: a factory worker and ICU nurse who saw where the highest-leverage play was, went all in, and built a media brand and a business that works without grinding 60 hours a week.  CONNECT WITH MILENA SIMSIC Windsor Real Estate Insider: https://www.windsorrealestateinsider.comInstagram / LinkedIn / Facebook / YouTube: search 'Milena Simsic' Chapters 00:00: Introduction and Cold Open  01:20: Milena's background: factory worker, nursing, COVID, Windsor  03:00: Breaking news: brokerage switch from EXP to Real  04:00: Windsor Real Estate Insider magazine, 9,000 subscribers  05:30: Windsor market conditions: what is holding and what is not  07:00: The Gordy Howe Bridge delay  08:30: EV plant, population growth, downtown development  09:30: What investors are doing in Windsor right now  13:00: $300K first year off TikTok and Instagram  17:00: Building Windsor REI Social to 3,000 members  22:00: AI adoption gap: top agents vs. everyone else  28:00: Replacing a virtual assistant with Claude  31:00: How many hours per week to run the business  33:30: Teaching other realtors AI-powered marketing  38:00: The Windsor pageant: why she entered, first runner up  41:00: The autoimmune condition, the health pivot, business doubling  45:00: Salsa dancing as the one thing that started everything  48:00: Business owner loneliness and why dance helps  51:00: EXP vs. Real: why the switch and what Real is doing differently  58:00: AI tools, Fiverr comparison, what Claude does that nobody else can match  01:01:00: Advice for young people: build your skill set, buy a business, zero excuses  01:03:00: Wrap up and where to find Milena 

In January 2026, Ming Lim and Bryan Ma closed on AccounTrain, a 25-year-old bookkeeping firm based in Ottawa with clients across Canada. They beat out five other offers. They paid 1.3 times annual revenue. They spent almost two years searching for the right deal.  Ming is the managing partner of Volition Properties, where his team has helped Canadians transact on more than $300 million of Toronto investment real estate. Bryan spent 20 years in Canadian financial services. He's a CPA, a CFA, and holds an MBA. He worked at three of the biggest professional services firms in the country and most recently at Intact Insurance in mergers and acquisitions.  In this conversation, we cover:  Why these two real estate operators are buying a business instead of more rentals  How they sourced AccounTrain through Poe Group and a buy-side community called Village Wealth  The difference between bookkeeping and full accounting firms, and why the simpler business won  How multiples in this industry actually work (1.2 to 2.5 times revenue depending on quality)  Why vendor take-back mortgages are standard in business sales, even though they're rare in Canadian real estate  The seller's 25 years of institutional knowledge that was kept entirely in one person's head  How Bryan and Ming approached due diligence with Bryan's M&A background as the advantage  The lifestyle case for a business over a rental portfolio  What they're modernizing now that they own it (CRM, workflow management, AI tools)  Practical advice for small business owners with messy books  This episode is part of TAFI's coverage of the great wealth transfer from retiring boomers to the next generation of Canadian operators. If you're an active real estate investor looking at what's next, this is the playbook. 📩Connect with Ming and Bryan AccounTrain: https://accountrain.com/ (Their bookkeeping firm) Volition Properties: https://www.volitionprop.com/ (Ming's real estate brokerage) Reach them through LinkedIn or via the AccounTrain website 📌 Free training on the investment loan strategy: Saturday, June 27th (Oakville hybrid):https://wealthhacker.krtra.com/t/x5X1OCIDrAXc and Tuesday, July 7th (Zoom only): https://wealthhacker.krtra.com/t/n98gpqD3cVoQ Walking through the math, the loss scenarios, and how it fits alongside a real estate portfolio. 📌 Timestamps00:00 – Welcome & Tesla update01:30 – Investment club math ($35K → $140K)07:12 – Introducing Ming Lim & Bryan Ma09:30 – Why buy a business when you already own real estate 13:00 – How Ming and Bryan met and decided to partner up 17:00 – Two years of searching, joining Village Wealth 21:00 – Bookkeeping vs full accounting, why the simpler business won 26:00 – Deals closing in 24 to 48 hours, the competitive reality 31:00 – Multiples in the industry, 1.2 to 2.5 times revenue 41:00 – Vendor take-back mortgages, standard in business sales 46:00 – Maintaining the seller relationship after closing 52:00 – AI in the accounting industry, where it is and isn't useful 63:00 – Cash flow management as the real value of bookkeeping 67:00 – Toronto market check-in, May 2026 72:00 – Final thoughts on buying a business

Carlos Rodrigues spent 20 years in Canadian financial services. Mutual funds, life insurance both levels, and a full mortgage broker with five agents under him. He tried to start his own fund. Canadian compliance costs killed it.  Now he drives 4.5 hours each way from Hamilton to Cleveland, Ohio to buy duplexes for $70,000 that appraise at $170,000 after renovation.  In this episode, we get into:  The $70,000 duplex near the Cleveland Clinic with a toilet falling through the floor  How Section 8 rentals pay 20 to 30% above market, with one tenant paying $14 of her $1,400 rent  Why 100% loan-to-cost financing is back, and why this isn't 2008  The joint venture partner who added $30,000 to $40,000 in renovation scope while Carlos was at Home Depot  The contractor who ghosted him a week before closing  How ICE enforcement is hitting the US construction labor pool  Cleveland's side yard program: buy a vacant lot next to your house for $100  Why Carlos won't invest in Hamilton anymore, even though he lives there  Plus my own update: my Hamilton duplex tenant has been non-paying for 7 months, $12,000 deep, and we're still waiting on the LTB. This is the world we're operating in.  Want the investment loan strategy that produced a 40.6% return since September 2025?  I'm hosting a free training on Saturday May 30 (Oakville hybrid) and Tuesday June 2 (Zoom only). Walking through the complete strategy, the math, every loss scenario, and how it fits alongside a real estate portfolio.  Register at: ⁠https://wealthhacker.krtra.com/t/uqyHFbipnPrK⁠ Connect with Carlos:  Website: cashflowcarlos.com, Instagram & TikTok: @cashflowcarlos  Connect with Erwin:  Podcast: tafipod.ca Free Wealth Freedom Blueprint: infinitywealth.ca/freereport  Book a Wealth Planning Call: linked at ⁠www.infinitywealth.ca⁠ 

In this episode, Erwin sits down with Greg—an engineer turned real estate investor and e-commerce entrepreneur who scaled his business to $700K/month and is now leveraging AI to build apps, automate workflows, and save tens of thousands of dollars. From buying his first property with no experience to renovating duplexes across Ontario, Greg shares the real ups and downs of real estate investing—along with how he expanded into e-commerce and built multiple income streams. But the biggest shift? AI. Greg breaks down how he’s using tools like ChatGPT, Claude, and Gemini to: Build apps without coding Replace $50K–$70K development costs Create product images without expensive photoshoots Automate business processes and marketing To follow Greg: https://www.gregkowalczyk.com/ https://www.bronteharbourclassic.com/ (Discount code: Erwin) This episode is packed with insights for anyone looking to stay ahead in real estate, business, and the AI revolution.

What would you do if you had to sell your entire real estate portfolio… and start over? In this episode, we sit down with investor Sarah Copeland, who went from managing over 60 doors to liquidating everything—and now rebuilding from scratch in today’s market. She shares the real, behind-the-scenes story of navigating divorce, selling cash-flowing properties, and resetting her entire strategy. We break down how she transformed a distressed 12-plex into a high-performing asset, the lessons from a $1M+ renovation, and why she’s shifting back to joint ventures and simpler deals. This is a raw and honest conversation about what actually happens in real estate investing—when things don’t go as planned. If you're an investor trying to make sense of today’s market or wondering how to move forward in uncertain times, this episode will give you clarity, perspective, and practical takeaways. 📩 Want to connect with Sarah? website: SarahCopeland.ca / tagproperties.caor, email: sarah@sarahcoupland.ca

Passive real estate investing in Canada has changed — and for many investors, the math no longer works. In this episode, Erwin Szeto explains why he’s been telling investors to diversify out of Ontario real estate since 2023 and what he’s personally doing instead to build wealth without turning investing into a second job. You’ll learn: Why passive real estate in Ontario is effectively gone How rent control, LTB delays, and rising costs changed the landscape Why U.S. real estate, business ownership, and leveraged investing matter The real‑estate‑style leverage strategy applied to the stock market This episode marks the evolution of the show into The Truth About Financial Independence for Canadians (TAFI) — focused on multiple paths to wealth, time freedom, and peace of mind. Also, don't miss the 🔥 Free Live Training: The $100,000 Zero‑Down StrategyI’m walking through the full math, risks, and real use cases live.📍 Saturday, May 30 (Hybrid – Oakville + Zoom)📍 Tuesday, June 3 (Zoom Only – 8pm ET)👉 Register here: https://www.infinitywealth.ca🎧 Subscribe to The Truth About Financial Independence for Canadians (TAFI)🌐 https://tafipod.ca

Real estate investors are feeling the squeeze—rising inflation, capital trapped in property, and nonstop landlord headaches. In this episode, Erwin breaks down the Zero-Down Wealth Strategy, a leveraged investing approach designed to help high‑income Canadians build long‑term wealth without buying more real estate. You’ll learn why investing $433/month can be equivalent to deploying $100,000, how leverage works outside of property, and who this strategy is (and isn’t) for. 🎓 Free Training (Limited Seats): • Saturday, May 30 (Hybrid – In Person + Online)• Tuesday, June 3 (Webinar Only)👉 Link to register: https://wealthhacker.krtra.com/t/uqyHFbipnPrK

In this episode of The Truth About Real Estate Investing, we unpack three stories that look disconnected in the headlines — but together reveal where Canadian real estate is really headed in 2026. Ontario’s HST rebate triggered a surge in new‑build sales, but the benefit for investors is far narrower than most realize — and the investor cutoff has already passed. In Alberta, especially Calgary, inventory is rising, rents are softening, and out‑of‑town investors are starting to walk away, despite the province’s long‑term fundamentals remaining intact. We also dig into a recent FSRA enforcement ruling that exposed major failures in private and syndicated mortgage lending — and share hard lessons about why due diligence on people matters just as much as due diligence on properties. This episode is about cutting through hype, spreadsheets, and sales pitches — and focusing on cash flow, landlord‑friendly rules, and real risk. If you’re investing (or thinking about investing) in Canada or looking beyond it, this conversation will challenge popular narratives and sharpen your decision‑making. Facts over headlines. Data over hype.

Why do Ontario landlords wait 7+ months for an eviction while Alberta wraps it up in 30 days? Erwin sits down with Mackenzie Wilson of SingleKey — Canada's largest tenant screening service — to expose the massive risk gap between provinces. Inside: a live AI reference-check demo, the $60K rent guarantee product, why 76% of landlords never get reference calls, Calgary's rezoning reversal, and why turnkey beats development in 2026. A must-listen for every Canadian real estate investor.

In this episode, we break down Canada’s rare population decline, rising unemployment, weakening income growth, and what these trends mean for housing prices, rents, and investment strategy. We also explore how inflation, interest rates, global conflicts, and political shifts are shaping capital flows—and why many investors are starting to look beyond Canada to places with stronger population and income growth. If you’re a Canadian real estate investor wondering where the market is heading next, this episode helps you skate to where the puck is going—not where it’s been.

In this episode, rent‑to‑own expert Rachel Oliver shares how real estate investing has changed — and why the traditional rent‑to‑own model no longer works in today’s market. With over 16 years of experience and nearly 1,000 deals completed, Rachel explains Rent‑to‑Own 2.0, a strategy focused on cash flow, mortgage pay‑down, and stability in flat or uncertain markets. A must‑listen for investors, first‑time buyers, and anyone navigating modern real estate.

In this episode of The Truth About Real Estate Investing, Erwin Szeto sits down with best‑selling author and veteran investor Russell Westcott for an honest conversation about market cycles, hard lessons, and survival in Canadian real estate. Russell shares his personal journey through near‑bankruptcy, health scares, and tough portfolio decisions, along with why cash flow, fundamentals, and long‑term thinking matter more than hype. They discuss Alberta vs Ontario, development realities, policy challenges, and what investors should really focus on in today’s market. 🔗Connect with Russell: Website: https://www.russellwestcott.com/

In this episode, Andy Tran breaks down what’s really happening in the Canadian real estate market in 2026 and explains why 4+1 and 6+1 properties have become the new investment sweet spot in Toronto. We discuss housing supply shortages, CMHC financing, missing‑middle housing, garden suites, and why smaller, repeatable projects are outperforming large‑scale developments. A must‑listen for investors looking to adapt and find opportunity in today’s market. 🔗Connect with AndyWebsite: suiteadditions.com YouTube: suiteadditions

In this episode, Erwin sits down with Anderson, a professional trader who went from driving DoorDash and trading on his phone to getting paid to trade stocks, options, and futures. Anderson shares his real journey—immigrating to Canada, funding his trading account through side hustles, and learning disciplined risk management over years of hard work. They also discuss buy‑and‑hold investing, options trading for everyday people, real estate investing in Barbados, and why buying back your time matters more than chasing hype returns. 🔗Connect with Anderson Email: thetraderdesk@outlook.com Include your name and phone number -- one-on-one coaching through The Trader Desk.

In this episode, Erwin talks with Glen Sutherland, a full-time Canadian investor actively scaling US real estate from Canada. They break down what’s working in 2026, why relying on appreciation is risky, and how experienced investors use systems, creative financing, and organization to scale remotely. A practical conversation for Canadians investing in US real estate who want real-world insight—not hype.

Rasna Arora built a $50 million real estate portfolio across 70 properties using private money, refinancing, and aggressive scaling. Then the market shifted — and everything unraveled. In this raw and honest conversation, we unpack the realities of leverage, hard money loans, refinancing risk, and what happens when trusted advisors collapse. This episode goes beyond strategy and numbers — it dives into integrity, mental health, and the true cost of scaling too fast. There’s no Lamborghini story here. Just the real truth about real estate investing in Canada — the wins, the warnings, and the lessons every investor needs to hear.

Adam Kitchener built a $14 million real estate portfolio — and then lost it after a CRA audit. In this episode, he shares the hard lessons from scaling fast, navigating tax mistakes, surviving an audit battle, and rebuilding from scratch. If you're a real estate investor, landlord, or entrepreneur in Canada, this is a cautionary story you can’t afford to miss. Connect with Adam: https://renovationsolutions.ca/

Serena Holmes shares a powerful perspective on money, mindset, and real estate investing. In this episode, she breaks down why money isn’t evil, how scarcity thinking holds investors back, and the mindset shift required to build wealth with intention and impact. A must-listen for anyone serious about financial freedom

In this episode, Erwin Szeto sits down with former corporate CFO turned personal wealth strategist, Winnie Tsang, to unpack why so many Canadian real estate investors feel stuck—and what smarter, more resilient wealth planning actually looks like today. They dive into landlord challenges, diversification beyond property, leveraging the stock market, corporate‑owned life insurance, and how families can build long‑term financial security without sacrificing time, health, or peace of mind.

Thinking about investing in U.S. real estate as a Canadian? In this episode, Scott Dillingham shares the real truth about cross-border real estate investing — from mortgages and financing challenges to tariffs, hidden costs, and lifestyle impacts. A must-listen for Canadian investors exploring the U.S. market.