Should You Be a Real Estate Wholesaler?
- Wayne Hillier
- Jul 17
- 3 min read
Updated: Aug 7
By Wayne Hillier, Real Estate Investing Masters
July 17, 2025 | Edmonton, Alberta
Wholesaling has become one of the most talked about strategies for getting started in real estate investing. But should you actually pursue it?
Today, I’m breaking down what wholesaling really looks like in Canada, who it’s best suited for, and why most people end up quitting long before they ever cash their first assignment cheque.
Let’s separate hype from reality.
What Is Wholesaling?
Wholesaling is the process of finding deeply discounted real estate deals, getting them under contract, and then assigning that contract to another investor for a fee. You’re not buying the property yourself. You’re selling the opportunity.
It sounds simple and in theory, it is. You get paid for finding great deals. But in practice, wholesaling is one of the most challenging and misunderstood strategies out there.
5 Reasons NOT to Be a Wholesaler
1. It’s a Full-Time Sales Job
Wholesaling requires constant outreach, follow-ups, lead generation, and negotiation. You’re in sales. And sales is exhausting if you're not built for it.
2. It’s Not Family-Friendly
If you’ve got young kids, this lifestyle is tough. Expect missed dinners, bedtime stories skipped, and lots of evening and weekend work.
3. You Only Get Paid When You Close
No base salary. No stability. If a deal falls through, or no one buys your deal, you don’t get paid. You can go months without income.
4. It Can Be Legally Risky If Done Wrong
Acting like a real estate broker without a license can get you in serious trouble. You need to understand provincial real estate laws and avoid crossing the line into practicing real estate without a license.
5. Burnout Is Common
Most wholesalers give up because the rejection is relentless. Door slams, angry sellers, ignored messages. It takes thick skin and serious grit to survive the grind.
Who Is Wholesaling Perfect For?
Wholesaling isn’t for everyone but it is perfect for the right type of person.
You’re in your 20s, full of energy, no kids, no distractions
You’re living at home, expenses are low, and you have time to hustle
You’re hungry to learn and ready to fail forward
You don’t have money for a down payment or formal education (yet)
You’re looking for a way to earn fast capital to fund future investments
If that’s you, wholesaling might be a great fit. Just know what you’re walking into.
The Right Way to Approach Wholesaling
Most people treat wholesaling like a side hustle. That’s why they fail.
Instead, build it like a business.
Create systems
Build a buyer’s list
Develop repeatable processes
Learn sales and negotiation
Understand your local real estate laws
Reinvent yourself as a solution provider
Success in wholesaling comes from treating it like a business, not a side gig.
A Better Path Forward?
For many, wholesaling is just the beginning. It’s a skill you can develop while earning capital. Then you take that capital and reinvest it into your education, your brand, and your long-term real estate goals.
Many of our most successful students started out wholesaling, then moved on to BRRRRs, flips, rentals, and creative strategies. The goal isn’t to stay a wholesaler forever. The goal is to build wealth and freedom through real estate.
And that takes time, effort, and the right mentorship.
Ready to build your wholesaling business the right way?
Reach out and book a free discovery call to see if the REI Masters Mentorship Program is right for you: Book a free discovery call
Listen to Today’s Episode:
Real Estate Investing Morning Show – Hosted by Wayne & Gabby Hillier
About the Author
Wayne Hillier is one of Canada’s trusted experts in real estate investing education, specializing in Alberta’s thriving markets. Based in Edmonton, Wayne has over a decade of experience building a high-performing rental portfolio and coaching investors to achieve strong cash flow, sustainable wealth, and creative financing success. As co-founder of Real Estate Investing Masters, Wayne is a respected real estate investing coach and mentor, dedicated to helping Canadian investors confidently scale their portfolios. He is also the host of The Real Estate Investing Morning Show, Canada’s #1 daily podcast.
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