21 Oct 2026
Real Estate Investing Is HARD! Why You Should Still Bet on Yourself
Real Estate Investing Is HARD! Why You Should Still Bet on Yourself
Real estate investing is not always easy.
There will be difficult days, difficult weeks, and sometimes even difficult years.
And even after more than 15 years of investing experience, Wayne and Gabby Hillier are not immune to those challenges.
In today's episode of the Canadian Real Estate Investing Morning Show, Wayne and Gabby have an unusually personal and unscripted conversation about resilience, entrepreneurship, financial freedom, and what happens when everything seems to go wrong at once.
After experiencing one of the most difficult business days they've had in years, Wayne shares how unexpected setbacks affected their investment portfolio, why even experienced investors can be overwhelmed, and what allows them to continue moving forward.
But this episode isn't about complaining or feeling sorry for yourself.
It's about understanding that difficult times are part of building something worthwhile.
And more importantly, it's about why Wayne believes you should always bet on yourself.
When Everything Goes Wrong at Once
Wayne opens the episode by explaining that he and Gabby recently experienced an unusually difficult day across their businesses.
Several unrelated problems appeared at nearly the same time.
Each issue was manageable on its own, but the combination created a level of pressure they hadn't experienced in quite some time.
Wayne admits that the day affected him emotionally.
He even missed his daughter's soccer practice, something that was particularly difficult because one of the reasons he became an entrepreneur was to have more flexibility and time with his family.
Gabby explains that 2026 has been a challenging year overall.
At times, the only way to move forward has been to focus on the immediate task rather than becoming overwhelmed by everything happening around them.
Their experience is a reminder that successful entrepreneurs and investors still have bad days.
Experience doesn't prevent problems.
It changes how you respond to them.
Resilience Is One of the Most Important Skills in Real Estate Investing
Wayne explains that resilience is not simply about being mentally tough.
It's about preparing your business so that unexpected problems don't destroy everything you've built.
Real estate investors cannot control every external factor.
They cannot control interest rates, market conditions, contractors, unexpected expenses, or every decision made by other people.
What they can control is how they structure their business.
That means developing systems, maintaining financial reserves, planning for unexpected situations, and creating backup options.
Wayne and Gabby have spent years developing their investment businesses to withstand difficult circumstances.
Those preparations are what allow them to experience setbacks without being forced to sell properties or abandon their long-term plans.
Why Cash Reserves Are So Important
One of the biggest lessons from today's episode is the importance of having money available when things go wrong.
Wayne explains that cash reserves provide investors with options.
Imagine owning a rental property where rents suddenly fall by 30%.
An investor without sufficient cash flow or savings may be forced to sell, potentially at a substantial loss.
An investor with adequate reserves may have the ability to continue operating the property until conditions improve.
That doesn't mean the setback disappears or that holding the property guarantees a recovery.
It means the investor has more flexibility and time to make decisions.
Wayne reinforces a principle he regularly teaches through the REI Masters Mentorship Program.
Cash flow protects your investments, and reserves help protect you from being forced to sell.
This is one of the reasons Wayne places so much importance on the 5% Rule™ Cash Flow Test.
Even the Worst Investment Can Still Be Profitable
Wayne also shares a difficult conversation he recently had with one of his joint venture partners.
An unexpected development had affected an investment property.
Although Wayne does not disclose the specific details publicly, he explains that the situation changed how the investment was expected to perform.
It was not a conversation he was looking forward to having.
However, his partner understood the circumstances and recognized that finding out about the issue early provided them with more options.
Wayne explains that the investment may now be one of the least successful deals he has ever completed.
Yet he still expects it to be profitable over the long term.
The lesson is not that every real estate investment will succeed.
It's that strong fundamentals, careful planning, appropriate reserves, and a long-term investment horizon can help investors withstand unexpected challenges.
Choosing the Right Joint Venture Partners
Another important lesson from the experience is the value of choosing compatible investment partners.
Wayne explains that the conversation could have gone very differently with someone who had unrealistic expectations or could not accept that unexpected problems are part of investing.
Instead, his partner understood the circumstances and focused on identifying solutions.
For anyone considering joint venture real estate investing, Wayne emphasizes the importance of working with people who understand the business, appreciate the risks, and share a long-term perspective.
The right partnership is not simply about finding someone with money.
It is about finding someone you can work with when things don't go according to plan.
Why Time Can Be an Investor's Greatest Advantage
Wayne discusses why he approaches real estate investing with a long-term perspective.
When a property has strong fundamentals and the financial ability to withstand difficult periods, time can provide opportunities for mortgage paydown, rental income, and potential appreciation.
Not every investment will perform according to its original projections.
Some properties will require more time, money, or effort than expected.
But a temporary setback does not necessarily mean the entire investment has failed.
Investors who understand their financial position and have the ability to hold an asset may have more choices than those who are forced to sell at the first sign of trouble.
This is why Wayne encourages investors to plan for difficult market conditions before they arrive.
What's the Alternative to Entrepreneurship?
One of the biggest questions Wayne raises during the episode is simple.
What's the alternative?
He acknowledges that entrepreneurship is difficult.
Business owners assume responsibility for their decisions, finances, employees, clients, and the problems that arise.
But traditional employment comes with its own compromises.
Employees may have greater income predictability, but they often have less control over their schedules, working conditions, and earning potential.
Wayne and Gabby discuss the trade-offs between employment and business ownership, including the flexibility they have created by becoming full-time entrepreneurs.
Even after a terrible business day, Wayne says he would still choose the life they have built over returning to a traditional job.
Why Wayne Left His Career to Become an Entrepreneur
Wayne shares a story about the day he decided to leave his previous career.
After an unpleasant interaction with someone at a job site, he began questioning why he was continuing to work for someone else.
By that point, he had already developed a profitable business outside his employment.
He was staying in his job primarily for the security of a regular paycheque.
That experience helped him realize that he no longer needed to continue working in an environment where he felt he had little control over his time.
He had already proven to himself that he could create income independently.
So he made the decision to leave.
Wayne explains that becoming an entrepreneur meant taking responsibility for his own financial future.
His ideas, decisions, effort, and results would now directly affect his own businesses.
The Airport Story That Changed Wayne's Perspective
Wayne also revisits a story he shared years ago on the podcast.
While travelling through an airport, he witnessed a manager unexpectedly tell an employee that she would need to work additional hours.
The employee appeared visibly upset but seemed unable to challenge the decision.
Wayne remembers how strongly that interaction affected him.
It reinforced his belief that having control over your time is one of the most valuable forms of freedom.
He reflects on how many people remain in jobs or circumstances they dislike because they feel they have no alternative.
For Wayne, the experience strengthened his commitment to entrepreneurship and building a life where he could make more of his own decisions.
Your Story Doesn't End at 18
One of Wayne's most important messages is that the direction of your life is not permanently determined by your education, early career choices, or circumstances at 18 years old.
He reflects on his own struggles with school and how he initially entered the workforce without the direction or opportunities he would eventually create for himself.
At one point, he was working at a gas station.
He did not have the real estate portfolio, businesses, financial freedom, or lifestyle that he enjoys today.
Those things came later.
Through education, experience, hard work, and a willingness to take responsibility for his choices, Wayne was able to change the direction of his life.
His message is that people can continue learning, improving, and pursuing new opportunities at any age.
Whether you're 19, 35, 47, or 64, your past does not have to determine your future.
Sometimes You Have to Take a Step Back to Move Forward
Wayne discusses why making a meaningful change sometimes requires accepting temporary discomfort.
That might mean returning to school, learning a new skill, reducing expenses, changing careers, or beginning a business while still employed.
For some people, the transition may take years.
For others, it may require changing their financial priorities or making difficult decisions.
The important part is developing a realistic plan and taking action rather than assuming your current circumstances are permanent.
Wayne encourages listeners to believe they can improve their situations while accepting the responsibilities and consequences that come with their decisions.
Bet on Yourself
The central theme of today's episode is believing in your ability to create something better.
Wayne explains that every investment involves risk.
Starting a business involves risk.
Changing careers involves risk.
But remaining in a situation where you have little control over your future can also involve risk.
His message is not that everyone needs to quit their job immediately.
It's that people should invest in their own education, develop useful skills, build confidence, and create opportunities for themselves.
Real estate investing is one potential path toward that goal.
The most important thing is taking an active role in designing your future rather than simply accepting whatever circumstances happen to come your way.
Build a Business That Can Survive Difficult Times
Wayne brings the discussion back to the fundamentals of successful real estate investing.
Strong cash flow.
Adequate reserves.
Good business systems.
A long-term investment strategy.
The right partners.
And the ability to manage unexpected problems without abandoning your goals.
These principles are what allow Wayne and Gabby to continue operating their businesses even during difficult periods.
Real estate investing can be challenging, but it can also create opportunities for financial independence, flexibility, and long-term wealth.
Wayne and Gabby close the episode by reminding listeners that education is available to help them navigate these challenges.
Also Discussed in This Episode
Why 2026 has been a challenging year for Wayne and Gabby
How experienced investors respond when several problems occur at once
The importance of resilience in business and real estate investing
Why financial reserves help prevent forced property sales
The role of cash flow during difficult market conditions
What makes a good joint venture partner
Why difficult investment conversations require honesty and perspective
The importance of building systems and backup plans
Why long-term investing requires patience
The trade-offs between employment and entrepreneurship
The experience that encouraged Wayne to leave his career
Why having control over your time matters
How Wayne's early career differed from the life he eventually created
Why it's never too late to pursue a different future
Why personal responsibility matters in entrepreneurship
How the 5% Rule™ supports a more sustainable rental property business
About the Canadian Real Estate Investing Morning Show
Join real estate investing coaches Wayne and Gabby Hillier live every weekday morning at 7:00 AM Mountain Time.
With more than 1,300 episodes, the Canadian Real Estate Investing Morning Show provides free real estate investing education, practical strategies, and real-world insights from experienced Canadian investors.
Whether you're purchasing your first rental property, exploring creative financing, managing an existing portfolio, or considering entrepreneurship, Wayne and Gabby share lessons from their own experiences to help you make informed decisions.
REI Masters Mentorship Program
Want to be personally coached by Wayne and Gabby?
The REI Masters Mentorship Program helps Canadian real estate investors develop the knowledge, confidence, and strategies needed to build successful long-term investment portfolios.
Members receive:
Weekly live real estate investing coaching every Wednesday from 7:00 PM to 8:00 PM Mountain Time
Access to the Masters Vault, including educational courses, workshops, and resources
A private Facebook community of like-minded Canadian real estate investors
Education covering BRRRR, seller financing, Agreements for Sale, rent to own, fix and flips, joint ventures, property management, financing, and other investing strategies
Help analyzing properties, evaluating cash flow, and identifying investment opportunities
Guidance on building a personalized investment strategy and roadmap
Ongoing coaching, accountability, and support from Wayne and Gabby
Access to an experienced investor community for practical knowledge and encouragement
The goal is not simply to acquire more rental properties.
It's to build a portfolio that helps create financial independence and allows you to live the life you want.
Learn more about the program or book a discovery call:
https://www.reimasters.ca
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