Hey there, audience! This is the Investing to WIN podcast, the show dedicated to inspiring budding entrepreneurs and business owners to live balanced, fulfilled lives. Our guests share their personal journeys, struggles, adversity and success stories. If you're a person that is working too hard, thinking of change or looking towards a future goal, you've come to the right place!
This show is committed to offering honest conversations to discuss common sense strategies and professional guidance to achieving success and fulfillment.
Your host is Garret Wong; an Ex-Scientist turned Serial Entrepreneur who, while growing up saw his father and mother run 4 businesses simultaneously while still being able to travel. But when his father passed away at the early age of 59, just before he was ready to retire, Garret's path and perspective of "success" was changed forever. In addition to his other businesses he brings decades of experience in buying, renovating, and managing rental properties for investors across the world.
Thanks for being here and get ready to Invest to Win!
AVAILABLE ON THESE PLATFORMS:
EPISODES:
EP: 064
James Christie
Dean of the Faculty of Theology at The University of Winnipeg and Director of the Ridd Institute for Religion and Global Policy
How Religion Shapes Ethics, Global Politics, and Human Cooperation
Most people confuse personal morality with global ethics. James Christie explains why this mistake leads to flawed decisions—and how understanding the difference changes how you view religion, culture, and global conflict.
EP: 063
Grant Reaves
Co-Founder and Managing Director of Stoic Equity Partners
How Flex Industrial Real Estate Creates Scalable, High-Upside Investment Returns
Most investors chase saturated asset classes without questioning supply dynamics. Grant Reaves explains why flex industrial remains overlooked—and how that gap creates a clear path to stronger, scalable returns.
EP: 062
Gary Prenevost
Real Estate Investor
Franchise vs Startup: How to Choose the Right Business Path
Most entrepreneurs underestimate the cost of trial and error. Gary Prenevost explains how franchising accelerates early growth—and why the wrong business choice can quietly stall your progress for years.
EP: 061
August Biniaz
Co-founder and Chief Investment Officer of CPI Capital
How to Invest in U.S. Multifamily Syndications as a Canadian Investor
Most Canadian investors unknowingly get double taxed in U.S. real estate deals. August Biniaz explains the structural mistake behind it—and how the right setup completely changes your returns.
EP: 060
Alex Levin
Co-founder and CEO of Regal.io
How AI-Powered Contact Centers Turn Conversations Into Revenue Growth
Most companies treat customer conversations as a cost. Alex Levin explains why that mindset kills growth—and how real-time, personalized outreach turns contact centers into a powerful revenue driver.
EP: 059
Matt Raad
Business and Website Investor
How to Build Cash Flow by Buying and Scaling Websites
Most investors chase appreciation and ignore cash flow. This episode reveals how undervalued websites can generate income faster—and why this overlooked asset class is attracting serious capital.
EP: 058
Dean Court
Hockey Canada High Performance Certified Coach
From Underdog Player to Elite Coach: Building Winning Teams
Most people chase growth without mastering their role first. Dean Court explains why failing to earn your position quietly limits success—and what high performers do differently to move ahead.
EP: 057
Garret Wong
Real Estate Investor
How to Convert a Single-Family Home Into a Profitable Secondary Suite
Most investors underestimate permit complexity. Garret Wong reveals how one overlooked detail caused weeks of delays—and what to fix upfront to avoid costly setbacks in secondary suite conversions.
EP: 056
Darcy Marler
Real Estate Investor
How to Build Wealth Faster with Real Estate Development
Most investors chase value in buildings. Darcy Marler explains why the real opportunity is in the land—and how overlooking this shift could be costing you significant upside.
EP: 055
Dan Bush
Real Estate Investor
How to Build, Hold, and Scale Rental Properties Profitably
Most investors obsess over cash flow—but overlook their largest expense. This episode reveals why tax strategy, not rent, often determines whether your real estate portfolio actually performs.
EP: 054
Grant Shipman
Founder of Livingsmith
How Co-Living Real Estate Creates Higher Cash Flow With Less Work
Most investors treat co-living like rent-by-the-room—and miss the real opportunity. Grant Shipman reveals the one shift that turns a standard property into a significantly higher-performing asset.
EP: 053
Jonathan Faerman
Founder of Investium
How to Find Real Estate Investment Partners Using Data and Technology
Most investors struggle to find the right partners, relying on slow, outdated networking. This episode reveals a faster, data-driven approach to connecting with aligned investors and turning conversations into deals.
EP: 052
Denis Brunet
Mortgage Broker
Private Lending and Mortgage Strategy Every Real Estate Investor Should Understand
Most investors focus on interest rates and overlook deal structure. This conversation reveals why financing flexibility—and a clear exit strategy—often matter more than securing the lowest possible rate.
EP: 051
Adam Bighill
Canadian Football League linebacker, motivational speaker, and financial advisor
How Adam Bighill Built Elite Discipline On and Off the Field
Most people believe hard work guarantees success. Adam Bighill explains why preparation—not effort—is the real differentiator, and how failing to recognize this quietly limits performance in sports, business, and life.
EP: 050
Rachel Covert
Financial Coach
How to Achieve Financial Independence Without Sacrificing Your Lifestyle
Most people think financial independence requires extreme sacrifice. Rachel Covert reveals the real mistake keeping high earners stuck—and how a simple shift can change your entire financial trajectory.
EP: 049
Mike McLenehan
Founder and Owner of McLenehan and Associates CPAs
How to Build a Scalable CPA Firm with Systems and Strategy
Many accountants focus only on year-end taxes—missing opportunities to grow clients’ businesses. Mike McLenehan reveals how proactive advisory and systems can transform a firm’s impact and revenue.
EP: 048
Wyatt
Counter-Terrorism and Protective Security Specialist
How Modern Surveillance Technology Is Changing Personal Security and Privacy
A counter-terrorism security expert reveals how surveillance devices once used by intelligence agencies are now widely accessible — and why most homeowners and property managers underestimate the real privacy risks.
EP: 047
Sam Primm
Founder of FasterFreedom
How Sam Primm Built a $47M Real Estate Portfolio Using the BRRRR Method
Most investors believe they need large amounts of cash to start in real estate. Sam Primm explains why that assumption is wrong—and how private lending changes the entire path to scaling.
EP: 046
Brian Brown
One of the Founders of IIA Canada
Internal Audits Explained: Risk, Governance, and Board Oversight
Most leaders think audits are about compliance. They’re wrong. Brian Brown reveals how internal audits actually protect organizations, expose hidden risk, and give boards the clarity they’re missing.
EP: 045
Shawn Hart
Real Estate Investor
How to Build and Sell Profitable Mobile Homes in 4 Months
Many investors overlook manufactured homes, assuming low quality or slow returns. Shawn Hart reveals why modern mobile homes deliver fast builds, strong ROI, and a hidden path to affordable housing wealth.
EP: 044
Amanda Han and Matthew MacFarland
Real Estate Investors
Real Estate Tax Strategies Every Investor Must Know in 2026
Many real estate investors overlook how depreciation and 1031 exchanges can dramatically reduce taxes. Amanda Han and Matthew MacFarland explain why missing these strategies can cost you thousands.
EP: 043
Jesse Cramer
Founder, The Best Interest; Mechanical and Aerospace Engineer
How to Run a Year-End Financial Review That Works
Most people think they’re saving, but their cash flow tells a different story. Jesse Cramer explains the overlooked step that determines whether your money actually grows or disappears.
EP: 042
Tiffany Taylor
NLP, Mindset, and Business Coach
Rewire Your Subconscious to Unlock Business and Investment Growth
Most investors think strategy is the problem. Tiffany Taylor reveals why subconscious beliefs, not market conditions, quietly sabotage growth—and how rewiring them changes everything.
EP: 041
Justin Peters
Podcast Coach & Editor
How to Save for Your First Rental Property Down Payment Efficiently
Most investors underestimate how hard the first down payment really is. Justin Peters breaks down the income and mindset shifts that make buying your first rental property achievable.
EP: 040
Garret Wong
Real Estate Investor
Secondary Suite Conversion Update: Permits, Delays, and Costly Lessons
A simple drafting mistake delayed this secondary suite conversion by two months. Garret breaks down what went wrong—and the one decision that finally moved the permit forward.
EP: 039
Meredith Marsh
YouTube Strategist and Founder of Thriving Creators Society
How to Grow a YouTube Channel for Business and Investors
Most professionals misunderstand YouTube growth. Meredith Marsh reveals why subscriber counts don’t matter — and how watch time and audience clarity actually drive authority, leads, and long-term business results.
EP: 038
Chris Reavis
Technology and Cryptocurrency Expert
Bitcoin Explained: Mining, Risk, and Generational Wealth Strategy
Most investors misunderstand Bitcoin because they treat it like speculation instead of strategy. Chris Reavis explains the one mindset shift that separates short-term traders from long-term wealth builders.
EP: 037
Garret Wong
Real Estate Investor
AI Ethics in Real Estate: Power, Bias, and Responsibility
AI can build strategies in seconds—but are you outsourcing your judgment? Garret Wong explores the hidden risks of over-reliance, bias, and ethical blind spots in real estate.
EP: 036
Carrie Soave
AI Expert
How AI Is Transforming Real Estate Marketing and Lead Generation
Most agents treat AI like a writing tool. Carrie Soave explains why that mindset is dangerous—and how those who ignore real AI workflows risk becoming invisible in tomorrow’s search landscape.
EP: 035
Maya Corbic
Forensic Accountant & Founder of the Wealthy Kids Investment Club
How to Raise Financially Confident Kids Who Build Wealth Early
Most parents rely on schools to teach money, but investing and credit are rarely covered. Maya Corbic explains the one habit that can quietly build lifelong wealth for your children.
EP: 034
Garret Wong
Real Estate Investor
Why Finding Your Why Matters in Real Estate Investing
Most investors chase deals without defining their deeper purpose. Garret challenges you to clarify your “why” first—because without it, even success in real estate can feel misaligned and unfulfilling.
EP: 033
Jordan Muela
Owner of Multiple Businesses in Real Estate
How to Drive Employee Engagement and Leadership in Real Estate Businesses
Most leaders try to buy performance with pay and perks. Jordan Muela explains why engagement is driven by meaning, ownership, and culture—and how to build it intentionally.
EP: 032
Rene Rheault
Owner of A Buyer’s Choice Home Inspections
Home Inspections Explained: How to Avoid Costly Buying Mistakes
Many buyers skip inspections or trust new builds blindly. Rene Rheault explains why that assumption leads to costly mistakes—and how smart buyers protect themselves before committing.
EP: 031
Garret Wong
Real Estate Investor
Building a Legal Secondary Suite: Permits, Design, and Real-World Tradeoffs
Most investors treat secondary suites like simple renovations. This episode explains why permit strategy and design limits determine success long before construction starts—and how early missteps quietly kill returns.
EP: 030
Jeff Olafson
Founder and CEO of NeoADMC 3D
How 3D Concrete Printing Is Disrupting Construction and Real Estate Development
Traditional construction is still optimizing labor and materials—while additive manufacturing rewrites the process entirely. Discover why resisting this shift may be the most expensive mistake builders make next.
EP: 029
Tony LeBlanc
Property Management Expert
How to Scale Property Management with a Platform Business Model
Most property managers make one growth mistake that caps margins and burns them out. Tony LeBlanc explains why chasing doors isn’t leverage—and what actually creates scalable profit.
EP: 028
Matthew Tringali
CEO of BetterWho and Real Estate Investor
How Remote Team Members Scale Real Estate Businesses Without Burning Out
Most investors fail with virtual assistants because they treat them like tools, not teammates. This episode challenges that mindset—and explains why the shift determines productivity, loyalty, and long-term scale.
EP: 027
Garret Wong
Real Estate Investor
How to Raise Real Estate Capital Without Selling or Pitching
Most investors stall because they think raising capital means selling. This episode reframes capital raising as relationship-building—and explains why that mindset shift is the real accelerator.
EP: 026
Brad Blazar
Founder, Capital Connections
How to Raise Capital Without a Track Record or Big Network
Most investors fail because they pitch too early. Brad Blazar explains why slowing down, building trust first, and structuring conversations correctly changes who commits capital—and who never does.
EP: 025
Sandy Elders
Insurance Expert
How Insurance Really Works and What Most Policies Don’t Explain
Most people assume they’re covered until a claim proves otherwise. Sandy Elders explains the hidden insurance mistake that leaves investors exposed and how to rethink protection before it’s too late.
EP: 024
Doug Blaylock
Financial Planner and Senior Financial Consultant at IG Wealth Management
Real Estate vs Traditional Investments: How to Choose the Right Mix
Many investors chase high returns without understanding risk, cash flow, or taxes. Doug Blaylock reveals why a property’s true value isn’t what it’s worth—but what it pays.
EP: 023
Fercy Perez
Business Development Coordinator at Upper Edge Property Management
Why Cash Flow Alone Can Hurt Long-Term Real Estate Returns
Most investors chase cash flow. Few account for how tenant quality, vacancy, and ignored repairs quietly erase it. A property manager’s perspective on why “good numbers” still fail.
EP: 022
John Tsai
President of eXp Realty Canada
Collaboration Over Competition in Real Estate with eXp Canada’s President
Most agents sell ownership to clients while renting their own brokerage. John Tsai explains why collaboration and equity—not competition—are the real path to long-term leverage in real estate.
EP: 021
Stewart Heath
CEO, Harvard Grace Capital
Commercial Real Estate Investing: Managing Risk, Leverage, and Long-Term Returns
He survived 2008, but admits one simple mistake nearly wiped out a $25M portfolio. A candid lesson on leverage, reserves, and why smart investors walk away from “good” deals.
EP: 020
Garret Wong
Real Estate Investor
Commercial Lending Explained: The 5 C’s of Credit and Cap Rates
Most investors focus on numbers, but lenders are scoring something else entirely. This episode reveals the overlooked factor that quietly influences commercial loan approvals before the deal math is even reviewed.
EP: 019
Daryl Colin
Seasoned Mortgage Agent
Out-of-Province Real Estate Investing with a Seasoned Mortgage Agent
Many investors chase hot markets close to home. This episode explains why boring, out-of-province markets can deliver stronger cash flow, better margins of error, and long-term predictability.
EP: 018
Garret Wong
Real Estate Investor
How to Structure Real Estate Joint Ventures Without Costly Mistakes
Most investors focus on the deal and ignore the exit. Garret Wong explains why failing to plan exits upfront is the fastest way partnerships, profits, and trust quietly break down.
EP: 017
Cal Reich
Real Estate Investor
How Cal Reich Built Scalable Wealth Through Strategic Real Estate Investing
Many investors misunderstand co-ownership deals. Cal Reich explains the one structural mistake that quietly destroys returns—and how disciplined partners avoid conflicts before they ever buy a property.
EP: 016
Ataf Khokhar
Real Estate and Business Lawyer
Real Estate Joint Ventures: Legal Structures, Risks, and Exit Strategies Explained
Most joint venture failures aren’t legal—they’re personal. A real estate lawyer explains the overlooked trust mistake investors make before contracts, capital, and exit strategies ever come into play.
EP: 015
Donna Cook
Real Estate Investor
Building Wealth Through Real Estate Without Overcomplicating the Process
Most investors delay action waiting for the “perfect” deal. Donna Cook explains why simplicity and consistency outperform overanalysis—and how getting started sooner changes everything.
EP: 014
Matt Landsborough
Founder of Dwell Logic Investing
How to Build a Profitable Interprovincial Real Estate Portfolio in Canada
Most investors get stuck chasing the “right” market. This episode challenges that thinking—and explains why deals live or die on numbers, not location, when scaling across provinces.
EP: 013
Garret Wong
Real Estate Investor
What a Near-Death Wake-Up Call Taught Me About Work and Life
He ignored a near-death warning and went straight back to 80-hour weeks. This episode confronts the dangerous belief that you can fix balance later—and what it really costs.
EP: 012
Rolf Hitzer
Real Estate Agent, Royal LePage (Winnipeg)
What Buyers and Sellers Misunderstand About Winnipeg Real Estate Today
Many investors misunderstand where wholesaling crosses into regulated real estate activity. Rolf Hitzer explains the gray areas, real risks, and why changes may be coming sooner than expected.
EP: 011
Kyle Kostenuk
President of Kenmare Developments
How to Build Profitable Real Estate Developments Without Overleveraging
Many developers underestimate how leverage and construction strategy quietly erode returns. Kyle Kostenuk explains the overlooked decisions that separate profitable projects from costly, drawn-out developments.
EP: 010
Derek Rolstone
Principal at Stone HR Strategies
How Smart HR Practices Help Small Businesses Hire & Retain Better People
Most businesses lose people before week one. Derek Rolstone explains why poor first-day onboarding creates immediate buyer’s remorse—and how small changes dramatically improve retention and performance.
EP: 009
Royce Finley
Licensed Realtor at Royal LePage
How to Build a Referral-Driven Real Estate Business That Scales
Most agents mistake silence for patience. Royce Finley explains why consistent follow-up and systems—not hope or hustle—are discovered to protect trust and deals when markets slow.
EP: 008
Marc Ting
Real Estate Entrepreneur
How Marc Ting Builds Profitable Real Estate Flips Without Cutting Corners
Many first-time flippers lose money by renovating beyond their market. This conversation reveals why knowing the neighborhood—not the house—often determines whether a flip succeeds or quietly fails.
EP: 007
Garret Wong
Real Estate Investor
Underused Housing Tax Explained for Canadian Rental Property Owners
Many Canadian investors assume the Underused Housing Tax doesn’t apply to them. This episode exposes the filing mistake that can trigger $5,000 to $10,000 penalties per property.
EP: 006
Rafiq Punjani
International award-winning serial entrep
Building Scalable Businesses & Real Estate Wealth Without Burning Out
Most entrepreneurs unknowingly build themselves a job. This episode explores the costly mistake of choosing non-scalable businesses—and how collapsing time with proven systems can change your investment trajectory.
EP: 005
Dakotah Charron
Real Estate Investor
How Networking Actually Grows a Real Estate Investing Business
Most investors miss opportunities by entering networking with the wrong mindset. Dakota Sharon explains why one conversation—not more content—often determines who actually moves ahead.
EP: 004
Melanie Mitchell
Real Estate Investor
Short-Term Rentals in Winnipeg: What New Hosts Must Know Now
Short-term rentals aren’t passive income—and Winnipeg’s proposed bylaw proves it. Melanie Mitchell explains the hidden workload, review-pressure reality, and why “grandfathering” could quietly eliminate most STR supply within a decade.
EP: 003
Garret Wong
Real Estate Investor
Rent Regulation Mistakes That Can Destroy a Real Estate Portfolio
One overlooked rent regulation rule turned renovations into a $260,000 liability. This episode breaks down the compliance mistake investors make after upgrades—and why “tenant approval” doesn’t protect you.
EP: 002
Mike Schroeder
Accredited Mortgage Professional (Canada)
Fixed vs Variable Mortgages: What Real Estate Investors Get Wrong
Most investors choose mortgage products based on rates - not risk. In this episode, mortgage broker Mike Schroeder explains why that mistake quietly costs investors tens of thousands of dollars.
EP: 001
Merouane Abed
Real Estate Investor & Sales and Marketing Manager
Exploring Secondary Suites: Insights from Merouane Abed
Most investors obsess over permits and layout, but the real profit killer is simpler: overestimating basement rents and underbudgeting renovations. Merouane Abed shares the pricing mistake that forced a $400 rent drop, and how he now stress-tests every secondary suite deal.