Pillar 03

Expert Insights

Pros on law, tax, financing.

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

28 episodes 12+ hours 24 guests
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Latest Episode
Ontario Real Estate Closing Traps: Legal Essentials with Geoff Rabideau 52 min
EP 115 · 52 min FEATURED
PILLAR 03 · EXPERT INSIGHTS

Ontario Real Estate Closing Traps: Legal Essentials with Geoff Rabideau

Geoff Rabideau

Interview Aug 2026
All Episodes 27 episodes
2026 5 episodes
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
2023 2 episodes
Investor Spotlight: Cory Froc on Surviving Over-Leverage and Rebuilding After the 2008 Crash 5 min EP 048
EP 048 · 5 min · Apr 2023
Investor Spotlight: Cory Froc on Surviving Over-Leverage and Rebuilding After the 2008 Crash
with Cory Froc
Interview
Multi-Family Investing with Brian Pulis: Building a $250M Portfolio in Any Market 19 min EP 046
EP 046 · 19 min · Jan 2023
Multi-Family Investing with Brian Pulis: Building a $250M Portfolio in Any Market
with Brian Pulis
Interview
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
2020 8 episodes
Property Development Strategy: Land Acquisition, Risk Mitigation & Construction Financing 8 min EP 020
EP 020 · 8 min · Dec 2020
Property Development Strategy: Land Acquisition, Risk Mitigation & Construction Financing
with Nick Stillo
Interview
Multi-Residential Investing: Apartment Building Strategies and Financing Tips 18 min EP 019
EP 019 · 18 min · Nov 2020
Multi-Residential Investing: Apartment Building Strategies and Financing Tips
with Matthew Frederick
Interview
Wholesaling Properties in Ontario: Strategies, Risks & Financing 12 min EP 018
EP 018 · 12 min · Sep 2020
Wholesaling Properties in Ontario: Strategies, Risks & Financing
with Luc Boiron
Interview
Buy & Hold Strategy: Market Outlook, Financing Tips & Expert Insights 8 min EP 016
EP 016 · 8 min · Aug 2020
Buy & Hold Strategy: Market Outlook, Financing Tips & Expert Insights
with Sarah Larbi
Interview
Student Rental Investing: Strategy, Risks & Financing Tips 7 min EP 015
EP 015 · 7 min · Aug 2020
Student Rental Investing: Strategy, Risks & Financing Tips
with Gillian Irving
Interview
Property Pulse: BRRR Strategy Financing & Refinancing Tips with Quentin D'Souza 19 min EP 014
EP 014 · 19 min · Jul 2020
Property Pulse: BRRR Strategy Financing & Refinancing Tips with Quentin D'Souza
with Quentin D'Souza
Interview
Rent-to-Own (RTO) Investment Strategy: Cash Flow Opportunities and Market Outlook 7 min EP 013
EP 013 · 7 min · Jul 2020
Rent-to-Own (RTO) Investment Strategy: Cash Flow Opportunities and Market Outlook
with Rachel Oliver
Interview
Property Pulse Report (EP2): COVID-19 Legal Guide for Real Estate Transactions & Tenancies 8 min EP 004
EP 004 · 8 min · May 2020
Property Pulse Report (EP2): COVID-19 Legal Guide for Real Estate Transactions & Tenancies
with Mark Weisleder
Interview
Explore Other Pillars View all pillars →
PILLAR 01 Wealth Foundations Timeless rules for wealth. PILLAR 02 Market Pulse What just changed, and what it means for you. PILLAR 04 Mindset & Operator Stories Think like a builder. PILLAR 05 Deal Dissections Real numbers, real decisions.
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