Pillar 03

Expert Insights

Pros on law, tax, financing.

Lawyers, accountants, mortgage specialists sharing playbooks they normally reserve for their best clients.

34 episodes 18+ hours 28 guests
33 episodes
2026 11 episodes
How to Scale Your Real Estate Portfolio with Value-Add Strategies 1h 2m EP 122
EP 122 · 1h 2m · Sep 2026
How to Scale Your Real Estate Portfolio with Value-Add Strategies
with Alex Pal
Interview
How to Add a Legal Suite to Your Ontario Property: The Missing Middle Strategy 1h 0m EP 120
EP 120 · 1h 0m · Sep 2026
How to Add a Legal Suite to Your Ontario Property: The Missing Middle Strategy
with Andy Tran
Interview
How to Build a 2 to 6-Unit Rental Portfolio in Ontario: Expert Strategies 1h 32m EP 119
EP 119 · 1h 32m · Sep 2026
How to Build a 2 to 6-Unit Rental Portfolio in Ontario: Expert Strategies
with Ian Hawking
Panel
How to Structure Your Canadian Real Estate Portfolio with Cherry Chan 57 min EP 118
EP 118 · 57 min · Aug 2026
How to Structure Your Canadian Real Estate Portfolio with Cherry Chan
with Cherry Chan
Interview
How to Build a Profitable Rental Portfolio in Canada with Rich Spence 57 min EP 117
EP 117 · 57 min · Aug 2026
How to Build a Profitable Rental Portfolio in Canada with Rich Spence
with Rich Spence
Interview
Ontario Real Estate Closing Traps: Legal Essentials with Geoff Rabideau 52 min EP 115
EP 115 · 52 min · Aug 2026
Ontario Real Estate Closing Traps: Legal Essentials with Geoff Rabideau
with Geoff Rabideau
Interview
Self-Managing vs. Hiring a Property Manager in Ontario | Streetwise Wealth 37 min EP 114
EP 114 · 37 min · Jul 2026
Self-Managing vs. Hiring a Property Manager in Ontario | Streetwise Wealth
with Elizabeth Kelly
Interview
The Truth About Multifamily Investing: Why It's Not Just a Bigger Duplex 53 min EP 113
EP 113 · 53 min · Jul 2026
The Truth About Multifamily Investing: Why It's Not Just a Bigger Duplex
with Paul Hecht
Interview
How to Generate Passive Cash Flow with Rent-to-Own 2.0 49 min EP 112
EP 112 · 49 min · Jul 2026
How to Generate Passive Cash Flow with Rent-to-Own 2.0
with Rachel Oliver
Interview
How to Handle Non-Payment of Rent in Ontario: Expert Strategies 56 min EP 111
EP 111 · 56 min · Jul 2026
How to Handle Non-Payment of Rent in Ontario: Expert Strategies
with Kayla Andrade
Interview
Where to Find Cash-Flowing Properties in Ontario: 2026 Regional Roundtable 1h 33m EP 110
EP 110 · 1h 33m · Jun 2026
Where to Find Cash-Flowing Properties in Ontario: 2026 Regional Roundtable
with Alex Pal
Panel
2022 12 episodes
Alfonso Cuadra on Wealth Transfer Opportunities, Assumable Mortgages & Portfolio Optimization 25 min EP 044
EP 044 · 25 min · Nov 2022
Alfonso Cuadra on Wealth Transfer Opportunities, Assumable Mortgages & Portfolio Optimization
with Alfonso Cuadra
Interview
Adapt & Thrive: Protecting Cash Flow and Finding Opportunities in a Rising Rate Market with Michal Wach 16 min EP 040
EP 040 · 16 min · Sep 2022
Adapt & Thrive: Protecting Cash Flow and Finding Opportunities in a Rising Rate Market with Michal Wach
with Michal Wach
Interview
Adapt & Thrive: Real Estate Strategies for Rising Rates and Market Uncertainty with Danielle Chiasson 26 min EP 038
EP 038 · 26 min · Sep 2022
Adapt & Thrive: Real Estate Strategies for Rising Rates and Market Uncertainty with Danielle Chiasson
with Danielle Chiasson
Interview
Adapting to Rising Rates & Market Shifts with REIN's Patrick Francey & JG Francoeur 27 min EP 037
EP 037 · 27 min · Sep 2022
Adapting to Rising Rates & Market Shifts with REIN's Patrick Francey & JG Francoeur
with Patrick Francey
Interview
Adapt & Thrive: Real Estate Investing Through Market Cycles with Harry James 33 min EP 036
EP 036 · 33 min · Aug 2022
Adapt & Thrive: Real Estate Investing Through Market Cycles with Harry James
with Harry James
Interview
Adapt & Thrive: Managing Cash Flow and Finding Opportunities in a Shifting Market with Elizabeth Kelly 21 min EP 035
EP 035 · 21 min · Aug 2022
Adapt & Thrive: Managing Cash Flow and Finding Opportunities in a Shifting Market with Elizabeth Kelly
with Elizabeth Kelly
Interview
Adapt & Thrive: Mortgage Strategy in a Rising Rate Environment with Dustan Woodhouse 15 min EP 033
EP 033 · 15 min · Aug 2022
Adapt & Thrive: Mortgage Strategy in a Rising Rate Environment with Dustan Woodhouse
with Dustan Woodhouse
Interview
Adapt & Thrive: Cashflow Strategies and Market Opportunities with Kory Mackinnon 14 min EP 032
EP 032 · 14 min · Jul 2022
Adapt & Thrive: Cashflow Strategies and Market Opportunities with Kory Mackinnon
with Kory Mackinnon
Interview
Adapt & Thrive: Christian Szpilfogel on Cash Flow, Risk Management & Market Opportunities 21 min EP 031
EP 031 · 21 min · Jul 2022
Adapt & Thrive: Christian Szpilfogel on Cash Flow, Risk Management & Market Opportunities
with Christian Szpilfogel
Interview
Adapt & Thrive: Quentin D'Souza on Cash Flow, Opportunities and Rising Interest Rates 17 min EP 030
EP 030 · 17 min · Jul 2022
Adapt & Thrive: Quentin D'Souza on Cash Flow, Opportunities and Rising Interest Rates
with Quentin D'Souza
Interview
Adapt & Thrive: Investing Through Rising Rates with Chris Shebib 18 min EP 029
EP 029 · 18 min · Jul 2022
Adapt & Thrive: Investing Through Rising Rates with Chris Shebib
with Chris Shebib
Interview
Adapt & Thrive: Navigating Rising Rates & Finding Opportunities with Sarah Larbi 14 min EP 028
EP 028 · 14 min · Jul 2022
Adapt & Thrive: Navigating Rising Rates & Finding Opportunities with Sarah Larbi
with Sarah Larbi
Interview
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