From 18 Income Streams to Zero: The Brutal Truth About “Passive” Real Estate Investing
Recorded: January 2026
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast
Guest: Serena Holmes, Award-winning Marketing and Business Professional, Podcaster and Author
Folks, welcome back to the show.
If you’ve been listening to me for a while, you know I am obsessed with control. I like to own the title. I like to control the bank account. I like to know that if everything hits the fan, I can drive to the property and change the locks.
Today’s guest, Serena Holmes, is here to share a cautionary tale that proves exactly why control is everything.
Serena is a powerhouse. She built and exited a multi-award-winning marketing agency, she’s a Realtor, an author, and the host of the Inspired to Invest podcast. But a few years ago, she did what many busy entrepreneurs do: she tried to move from “active” income to “passive” investments.
She invested in syndicated mortgages. She did private lending. She diversified into 18 different income streams.
And then? They all went to zero.
We’re talking about the collapse of major operators (like the Windrose Group) where hundreds of investors lost millions. Serena is open, vulnerable, and incredibly smart about what went wrong and, more importantly, how she is rebuilding.
If you are thinking about handing your money over to a “hands-off” operator, or if you are raising capital yourself and want to do it without ending up in court, you need to read this.
🎧 Listen to the full episode here
10 Capital Raising & Risk Questions Answered in This Episode
1. What happens when “Passive” Investing goes wrong?
Serena shares the reality of investing in syndicated mortgages and unsecured promissory notes. She thought she was diversified with 18 streams of income, but when the operators failed (due to fraud, mismanagement, or market shifts), every single stream dried up. The lesson: Diversification doesn’t help if the underlying asset structure is flawed.
2. What does “If you’re not first, you’re last” mean in lending?
This is the golden rule of private lending. Serena explains that if you are not in the first mortgage position, you are likely in trouble when a deal goes south. Unsecured notes or second/third positions often get wiped out completely during a power of sale or bankruptcy.
3. Can you trust a “Guaranteed” return?
No. We discuss how operators who scaled too fast (buying 600+ homes in 6 years) couldn’t refinance quickly enough when rates spiked. If an operator promises high returns without explaining the risks or having the liquidity to back it up, run the other way.
4. Why is “Control” the most important word in investing?
Serena admits she “shot herself in the foot” by giving away control. When you own the property on title, you have options. When you are a passive investor in a limited partnership or a promissory note holder, you are at the mercy of the operator’s competence and ethics.
5. What is the reality of the GTA Listing Market right now?
Serena is an active Realtor in the Durham/Toronto area. She notes that sellers are still stuck in 2022 pricing. She has listings where sellers turn down offers, only to receive lower offers months later as the market continues to soften. The “hold and hope” strategy is hurting sellers right now.
6. Is it worth suing to get your money back?
Serena has spent between $40,000 and $50,000 in legal fees trying to recover funds, with little to show for it yet. She highlights the harsh reality of the Canadian legal system: it is expensive, slow, and often, the money is simply gone.
7. Why are Canadian investors moving capital to the USA?
We discuss the “capital flight” to the US. Serena notes that the US GDP is expected to grow twice as fast as Canada’s . Between landlord-friendly laws, the 1031 exchange (tax-deferred selling), and better cash flow, many of her clients are pivoting south .
8. What is the “Wild West” of Capital Raising?
There was a time (and still is) where people raised millions on Facebook with zero compliance. Serena now works with M1 Real Capital, coaching investors on how to raise capital legally, ethically, and responsibly. You can’t just take money from people without the right paperwork and disclosure.
9. How do you spot a “Con Artist”?
I shared a quote from the book The Confidence Game: “Con artist” is short for “Confidence Artist.” Serena shares a story about seeing a prominent operator who looked the part—tall, commanding presence, confident on stage—who eventually went bankrupt owing investors millions. Confidence does not equal competence.
10. What is the best way to rebuild after a loss?
Serena’s advice is to get back to basics. She is focusing on her active income, helping others avoid her mistakes through coaching, and planning to return to purchasing multifamily properties where she controls the asset and the operations .
🎧 Listen to the full episode here
My Final Thoughts
Folks, I have seen too many people lose their life savings because they chased a high interest rate on a piece of paper.
Real estate is a fantastic asset class, but it is not magic. It requires due diligence. If you don’t understand where the yield is coming from, or if you don’t have your name on the title, you are taking a massive risk.
Serena’s story is a powerful reminder that return of capital is far more important than return on capital.
If you want to connect with Serena to learn about compliant capital raising or just to follow her journey, you can find her on Instagram at @serenaholmesofficial or listen to her podcast, Inspired to Invest .
As always, thanks for listening (all 17 of you!), and keep hustling.
To Listen:
YouTube: https://youtu.be/5t4Ht_vwq4o
You’ve Built Wealth. Now It’s Time to Understand It.
You’ve Built Wealth. Now It’s Time to Understand It.
After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.”
Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live.
Download your free Wealth Freedom Blueprint
Final Thoughts
Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life.
That’s what iWIN Wealth Planning is here for.
This is how we’re creating predictable, stress-free wealth for Canadian families…
so you can enjoy the life you’re building.
Book your Wealth Planning Call
Sponsored by… Me!
This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.
Till next time—just do it. I believe in you.
Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto
Disclaimer
As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.
My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.
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