What can a private lender who's funded hundreds of real estate deals tell us about the future of housing in Canada? 

In this episode of the BLD Financial Podcast, we're joined by Matt Gonsalves, Vice President & Broker at Foremost Financial, one of Ontario's leading private construction lenders.

Drawing from more than a decade of experience financing construction, land development, bridge loans, and Missing Middle housing projects, Matt shares what he's seeing in today's market and where he believes the biggest opportunities exist moving forward.

From the collapse in new housing starts and the rise of small-scale multifamily development to the costly mistakes new developers make, this conversation provides a practical, lender's-eye view of where opportunities exist and what investors need to understand moving forward.

We break down:

✅ Why small multifamily projects are becoming the sweet spot in Canadian real estate
✅ Why large development projects are struggling while smaller projects continue to work
✅ The future of Missing Middle housing and urban infill development
✅ Why many new developers underestimate capital requirements
✅ The biggest mistakes Matt sees investors and developers make
✅ How CMHC financing has changed the development landscape
✅ Why some projects get funded while others don't
✅ The impact of development charges, approvals, and rising construction costs
✅ Why Matt believes today's housing slowdown could create tomorrow's opportunities

Whether you're a real estate investor, developer, mortgage professional, or someone interested in where housing is headed in Canada, this episode provides valuable insights from one of the industry's most active construction lenders.

If you enjoyed this episode, make sure to subscribe to the BLD Financial Podcast and share it with someone who would find it valuable.

About Matt Gonsalves:

Matt Gonsalves is Vice President, Broker, and loan originator at Foremost Financial, specializing in construction and land development financing across Ontario.

Since joining Foremost in 2013, Matt has become one of the industry's leading loan originators in the small-scale development and Missing Middle housing space. He has structured financing for land acquisitions, custom home construction, multiplex developments, walk-up apartments, bridge financing, condominium inventory financing, and commercial construction projects throughout Ontario.

Matt is particularly known for his expertise in financing multiplex construction and small infill housing developments in Toronto and the Greater Toronto Area.

Matt holds an Honours Bachelor of Business Administration from Wilfrid Laurier University.

Follow & Connect with Matt Gonsalves:
LinkedIn - https://www.linkedin.com/in/matthewgonsalves/
Instagram - https://www.instagram.com/mattgonsalvesto/

Learn more about Foremost Financial: 
Website - https://foremost-financial.com/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“The harder it is to build housing, the less housing gets built… and then we have an affordability crisis.”

Canada says it wants more housing…

So why does the system make it so difficult to actually build it?

In this episode of the BLD Financial Podcast, we sit down with developer, housing advocate, and Toronto Standard partner Chris Spoke to break down the real reasons Canada’s housing affordability crisis continues to get worse despite years of policy changes and government intervention.

From zoning restrictions and building code requirements to CMHC financing policies and development economics, this conversation explores how many of the systems designed to improve affordability may actually be making housing harder and more expensive to build.

Chris also shares his journey from software and housing policy advocacy into real estate development, and explains why he believes missing middle housing could play a major role in solving Canada’s supply crisis if governments stop getting in the way.

This conversation goes deep into what’s actually preventing housing from being built in Canada today, why developers are struggling to make projects viable, and what needs to change if the country wants to improve affordability for future generations.

We break down:

✅ Why Canada makes housing so difficult to build
✅ The real problems with CMHC financing programs
✅ Why overregulation is making affordability worse
✅ The challenges facing missing middle development in Toronto
✅ Why many small multifamily projects no longer work financially
✅ The hidden costs inside building code and zoning requirements
✅ Why developers are avoiding certain projects entirely
✅ The growing affordability crisis facing young Canadians
✅ How policy, financing, and construction costs are colliding
✅ What actually needs to change to increase housing supply

As Canada continues to face rising housing costs, affordability challenges, and slowing development activity, this episode provides a real, unfiltered look at the policies, incentives, and structural issues shaping the future of housing.

Whether you’re a real estate investor, developer, mortgage professional, policy enthusiast, or simply trying to understand why housing has become so expensive in Canada, this episode offers an insider perspective on the realities of building in today’s market.

If you enjoyed this episode, make sure to follow or subscribe to the BLD Financial Podcast and share it with someone who would find it valuable.

About Chris Spoke

Chris Spoke is a Toronto-based real estate developer, housing advocate, and partner at Toronto Standard, a development firm focused on midrise rental housing and missing middle development in Toronto. Before entering real estate development, Chris spent years studying housing policy and advocating for zoning reform and increased housing supply in Canadian cities. He is widely known for his work and commentary around housing affordability, urban planning, development policy, and missing middle housing.

Chris is also a founder of the Missing Middle Summit, an annual conference focused on housing policy, urban development, and the future of housing in Canada. Through Toronto Standard and his public commentary, Chris has become one of the leading voices in Canada discussing the intersection of housing policy, development economics, financing, and affordability.

Follow & Connect with Chris Spoke:
Website - https://chrisspoke.com/
LinkedIn - https://www.linkedin.com/in/chris-spoke/
X - https://x.com/chrisspoke
Instagram - https://www.instagram.com/chrisspoke/

Toronto Standard - https://www.torontostandard.co/

Missing Middle Summit - https://missingmiddlesummit.com/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

"Does the BRRRR strategy still work in Canada… or is it over?”

In this episode of the BLD Financial Podcast, we’re joined by Jack Bernstein of Bernstone Capital to break down what’s actually happening in today’s Canadian real estate market and why many of the strategies that worked over the last cycle are no longer producing the same results and how investors are being forced to adapt in today’s market.

From rising interest rates and shifting cap rates to softening rents and tighter lending conditions, the environment that made BRRRR so effective has fundamentally changed.

This conversation goes deep into what investors are getting wrong right now, where deals are breaking down, and how experienced operators are adapting their strategies to survive and scale in this new market cycle.

We also explore the growing shift from small residential portfolios into mid-size multifamily (5–25 units), and why access to deals, proper underwriting, and long-term thinking matter more than ever.

We break down:

✅ Does the BRRRR strategy still work in Canada today
✅ Why high-leverage deals (90–95% LTV) are becoming increasingly risky
✅ The truth about cash flow and why it’s often an illusion early on
✅ Why many investors are struggling with refinancing and negative equity
✅ How cap rates, rent shifts, and market cycles are impacting deal viability
✅ The shift from “velocity investing” to long-term buy-and-hold strategies
✅ Why most multifamily deals aren’t as simple as they look on paper
✅ How serious investors are adapting their approach in 2026 and beyond

As the Canadian housing market continues to reset, this episode provides a real, unfiltered look at what’s working, what’s not, and what investors need to understand before making their next move.

Whether you’re a real estate investor, developer, mortgage professional, or simply trying to understand where the market is heading, this episode offers a grounded, insider perspective on navigating today’s investment landscape.

If you enjoyed this episode, make sure to follow or subscribe to the BLD Financial Podcast and share it with someone who would find it valuable.

About Jack Bernstein:

Jack Bernstein is the founder of Bernstone Capital, a real estate firm focused on mid market multifamily transactions across Ontario.

Specializing in the 5 to 50 unit space, Jack works directly with investors to source, structure, and execute deals that sit between traditional residential investing and institutional grade assets.

His approach is centered on guiding clients through the full transaction process, from acquisition strategy and underwriting to stabilization and long term portfolio growth, with a focus on navigating complex deals in today’s shifting market.

With a strong understanding of capital markets, deal structuring, and evolving investor behavior, Jack helps bridge the gap between opportunity and execution for investors looking to scale beyond small residential portfolios.

In a market where many traditional strategies are breaking down, his focus is on helping investors adapt to changing fundamentals and make more informed, long term decisions.

Follow & Connect with Jack Bernstein:
Instagram - https://www.instagram.com/bernstonecapital/
Facebook - https://www.facebook.com/jackdanielb
YouTube - https://www.youtube.com/@BernstoneCapital
Website - https://www.bernstonecapital.com/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“We believe the next 5 years will be the best 5 years the mortgage industry has ever seen.”

In this episode of the BLD Financial Podcast, we’re joined by Eddy Cocciollo, President of DLCG Mortgage Group, one of Canada’s largest mortgage brokerage groups, supporting over 9,000 agents Canada wide.

This episode breaks down where the Canadian mortgage and real estate market is actually headed, from someone who has worked inside banks, CMHC, and now leads one of the most influential mortgage organizations in the country.

With decades of experience across Canada Trust, CIBC, CMHC, and executive leadership roles, Eddy shares a rare, full-spectrum perspective on lending, risk, and how the system has evolved through major economic cycles, including the 2008 financial crisis.

While uncertainty around rates, affordability, and AI continues to grow, Eddy explains why he believes the next 5 years could be the strongest the mortgage industry has ever seen, and what that means for brokers, investors, and everyday Canadians.

We break down:

✅ Why Canada’s mortgage system is more resilient than most countries
✅ Why mortgage brokers are gaining market share (and will continue to)
✅ The real impact AI will have on brokers, lenders, and deal flow
✅ Why complexity in lending is increasing demand for expert advice
✅ Where growth is coming from in the next phase of the market

As lending becomes more complex and technology continues to evolve, the role of the mortgage professional is changing, not disappearing.

Whether you’re a real estate investor, mortgage broker, or someone trying to understand where the housing market is going next, this episode provides a high-level, insider perspective on the future of lending in Canada.

If you enjoyed this episode, make sure to follow or subscribe to the BLD Financial Podcast and share it with someone who would find it valuable.

About Eddy Cocciollo:

Eddy Cocciollo is the President of DLCG Mortgage Group, the parent company to Dominion Lending Centres and its network of mortgage brands. With a career spanning banking, government (CMHC), and executive leadership, Eddy has played a pivotal role in shaping mortgage distribution and broker growth across the country. He oversees a national network of over 9,000 agents and supports one of the largest volumes of mortgage originations in Canada.

Follow & Connect with Eddy:
Instagram - https://www.instagram.com/eddycocciollo/
Facebook - https://www.facebook.com/eddy.cocciollo
E-mail - [email protected] 

Follow & Connect with DLC Group Of Companies:
Website - www.dlcg.ca
YouTube - https://www.youtube.com/@dlcgmortgagegroup637
LinkedIn - https://www.linkedin.com/company/dlcg-mortgage-group/
Instagram - https://www.instagram.com/dlcgmortgage/
Facebook - https://www.facebook.com/dlcgmortgage/

Follow & Connect with DLC:
Website - https://dominionlending.ca/?
YouTube - https://www.youtube.com/user/DLCcanada
LinkedIn - https://www.linkedin.com/company/dominion-lending-centres/
Instagram - https://www.instagram.com/dlccanada/
Facebook - https://www.facebook.com/DominionLendingCentresCanada 

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

 “You think you're walking into a project… and then you find out after you've acquired it, you can’t even do it.” 

In this episode of the BLD Financial Podcast, we’re joined by Zachary Jancsar, a mid-market real estate developer, brokerage owner, and investor who has scaled from small residential deals to over 70 multifamily units across Southwestern Ontario. 

This episode breaks down the real, behind-the-scenes truth of real estate development, from first deals to mid-size multifamily projects, and what actually happens when you try to scale in today’s market.

With over 20 years of experience in real estate, land, and multifamily development, Zack shares how he transitioned from student rentals and small BRRRR deals into larger infill developments, construction projects, and vertically integrated operations including property management and construction.

While many new investors are rushing into development chasing bigger deals, Zack explains why most first-time developers underestimate timelines, capital requirements, and risk, and how that leads to costly mistakes early in the process.

We break down:

✅ Why most developers fail before they even finish their first project
✅ The “experience tax” and mistakes that can cost you hundreds of thousands
✅ Why timelines, not costs, are the biggest risk in development
✅ How market shifts and financing changes can kill deals mid-project
✅ Why scaling multifamily requires more than just building bigger

As construction costs remain volatile and financing conditions continue to evolve, the path to becoming a successful developer is far more complex than it appears online.

Whether you’re looking to build your first multiplex, scale into mid-size multifamily, or better understand the risks behind development in Canada, this episode offers a grounded, experience-driven perspective on what it actually takes to succeed.

Who is Zachary Jancsar?

Zachary Jancsar is a real estate developer, Broker of Record, and investor based in Southwestern Ontario. With over 20 years of experience, he has built and scaled a portfolio of residential and multifamily properties while also operating across brokerage, construction, and property management. His approach focuses on long-term investing, strategic development, and helping others navigate real estate with a full-picture perspective.

Follow & Connect with Zachary Jancsar:
Linked-In - https://www.linkedin.com/in/zachary-s-jancsar-6b221830/
Instagram - https://www.instagram.com/zacharyjancsar/
Building Group Website - https://www.jhbuildinggroup.ca/
Property Management Website - https://www.jhpm.ca/
Family Advantage Website - thefamilyadvantage.ca
Email - [email protected]
Phone - (226) 799-1963

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“A major mistake right now is that a lot of money gets left on the table when developers don’t think about rebates and incentives early enough.”

In this episode of the BLD Financial Podcast, we’re joined again by Jayden Haywood, founder of PL Energy, an engineering firm specializing in energy modeling, CMHC MLI Select compliance, and helping developers unlock energy rebates and incentives across Canada.

 This episode covers CMHC MLI Select, energy efficiency incentives, real estate development strategy, and how Canadian developers can leverage government rebates to improve project economics.

With nearly two decades in the energy and building science space and experience working with everyone from small multiplex developers to Canada’s largest high-rise builders Jayden explains how energy efficiency, CMHC financing, and government incentive programs are increasingly shaping the economics of real estate development.

While many developers assume that “building green” automatically means higher costs, Jayden explains why that isn’t always true and how rebates, automation, and smarter building systems can dramatically offset construction costs. 

We break down:

✅ How developers are securing 30–40% rebates on major mechanical systems
✅ Why millions in energy incentives are being left on the table by developers
✅ Ontario’s aggressive push toward energy efficiency and $11B in incentive programs
✅ Why energy modeling and rebate planning must start before architectural drawings are finalized
✅ The upcoming CMHC changes requiring buildings to reach 60–70% above national building code
✅ How smart automation, building controls, and AI-driven systems are becoming the “silver bullet” for energy performance
✅ Why building green may actually reduce costs when incentives are properly structured

As construction costs rise and policy changes continue to reshape the development landscape, understanding how to integrate energy efficiency, incentives, and smarter building design is quickly becoming a competitive advantage.

Whether you’re developing missing middle multiplex projects, scaling multifamily developments, or trying to understand how CMHC programs influence project economics, this conversation provides practical insight into where real estate development is heading in Canada.

Follow & Connect with Jayden Haywood:
Pacific Light & Energy - https://www.pacific-le.com/
YouTube - https://www.youtube.com/@PLEnergyRiverConsulting
Instagram - https://www.instagram.com/pl_energy/
Instagram - https://www.instagram.com/river.developments/
LinkedIn - https://www.linkedin.com/in/jayden-haywood-80b96762
River Developments - https://www.riverdevelopments.com/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

"We’re building a house behind a house.... we have a neighbor to the left, neighbor to the right, neighbor to the rear... very niche space in that aspect."

In this episode of the BLD Financial Podcast, we’re joined by Yasser Majd, owner/operator of 555 Construction Management Inc and the Original ADU Home Service Provider for Home Depot Canada. With over 15 years of experience as both a real estate investor and construction operator, Yasser brings a rare, ground-level perspective on how Ontario’s housing market is evolving through Accessory Dwelling Units (ADUs), infill development, and small-scale densification. 

Yasser shares how he transitioned from house hacking and basement conversions into large multifamily and infill development projects — and why today’s biggest opportunities in Ontario real estate are no longer driven by speculation or finishes, but by zoning knowledge, density strategy, execution, and capital structure.

We discuss:
✅ The real cost of building Accessory Dwelling Units (ADUs) in Ontario
✅ Basement suite conversions vs. garage retrofits vs. detached backyard homes
✅ How infill developments and small-scale densification are reshaping neighborhoods
✅ Why banks still classify ADUs as “outbuildings” — and how that affects financing
✅ The role of small commercial lending and CMHC in ADU and multiplex financing
✅ Municipal zoning changes, bylaw evolution, and Ontario’s push toward density
✅ Why infill development requires a different operational mindset than subdivision building

Whether you’re an investor looking to unlock hidden value in existing properties, a homeowner considering an ADU for family or income, or a professional trying to understand where construction and financing are actually headed, this conversation delivers clear, experience-backed insight into the future of density in Ontario real estate.

Follow & Connect with Yasser at 555 Construction Management Inc:
Website - https://555construction.ca/
Instagram - https://www.instagram.com/555construction_management_inc/
Facebook - https://www.facebook.com/profile.php?id=100090797359690
YouTube - https://www.youtube.com/channel/UCKvdW1KBTUJTDSJAEaMofPA

Want to see more of Yasser at 555 Construction Management Inc? 
Check out these videos on the Canadian Real Estate Channel: 

Accessory Dwelling Units in Canada | 300 sq/ft Detached Garage ADU Conversion Walkthrough - youtube.com/watch?v=LBf_J6s1O8U&list=PLVKh4BMVJHMP0bM3psIoFWVEz-mzbCcbl&index=10&pp=iAQB

Building an Accessory Dwelling Unit | How This 600 sq/ft ADU Earns $2,300/month - https://www.youtube.com/watch?v=78RZNX17gWE&list=PLVKh4BMVJHMP0bM3psIoFWVEz-mzbCcbl&index=10

Turn Your Backyard into Cash: 700 sq.ft Accessory Dwelling Unit Tour + Cost Breakdown - https://www.youtube.com/watch?v=iNPKTneyv0w&list=PLVKh4BMVJHMP0bM3psIoFWVEz-mzbCcbl&index=6

12 Bedroom Multi-Unit New Build in Hamilton, Ontario | Full Tour + Construction Breakdown - https://youtu.be/t3T5emzLW_E

Check Out Some of 555 Construction's Projects: 
 https://555construction.ca/home/projects/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“Once you control the land, everything becomes a business decision — not an emotional one.”

In this episode of the BLD Financial Podcast, we’re joined by Dane Buttenaar, a real estate developer who scaled from small multifamily properties into controlling 60 acres of development land in Ontario.

Dane walks through what scaling actually looks like — from early triplex and fourplex deals, to missing-middle projects, to large-scale land development. We unpack the realities behind construction costs, financing, partnerships, and why development forces investors to think like operators, not speculators.

This conversation goes beyond theory. Dane shares real war stories from the field, including near-miss deals, capital challenges, and the lessons that only come from building projects out of the ground.

In this episode, we explore:

✅ The transition from small multifamily to large-scale development
✅ Why scaling in real estate is not linear
✅ The real role of capital, experience, and partnerships in development
✅ Renovations vs. new builds — and why many developers are switching
✅ How credit unions, construction loans, and CMHC fit together
✅ Why controlling land changes the entire investment equation
✅ The biggest risks developers face before a shovel ever hits the ground
✅ What investors misunderstand about “scaling” in real estate

Whether you’re an investor looking to move beyond small multifamily, or someone trying to understand what real estate development actually entails, this episode delivers a grounded, experience-driven look at what it takes to scale responsibly.

Who is Dane Buttenaar?

Dane Buttenaar began his career in hands-on construction and site work, starting in landscape and project construction, where he developed a practical understanding of costs, timelines, and managing trades. That foundation led him into real estate investing, where he began acquiring and operating small multifamily properties, using triplexes and value-add rentals to build stable, active income.

Over time, Dane transitioned from renovations into ground-up development, scaling from small multifamily projects into missing-middle builds and ultimately large-scale land development, including controlling 60+ acres of development land in Ontario. Through DASA Properties, he focuses on purpose-built rental housing and infill development, applying a disciplined, numbers-first approach to construction, financing, and partnerships. His journey reflects the realities of scaling in real estate - where execution, experience, and capital matter more than speculation.

Follow & Connect with Dane Buttenaar:
Website - https://www.dasaproperties.ca/
Instagram - https://www.instagram.com/dbutts8/
The Beach Motel - https://thebeachmotel.ca/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“People were drunk off of the appreciation of the assets over two decades... It's almost like a bad hangover”

In this episode of the BLD Financial Podcast, we’re joined by Vince Gaetano, a veteran mortgage professional with over 35 years of experience who has lived through every major real estate cycle — from working with bailiffs in the early 1990s to advising homeowners and investors in today’s high-pressure market.

Vince brings a rare, data-first perspective shaped by decades in the industry. Together, we unpack the hard truths behind today’s housing market, the growing pressure on the middle class, and the consequences of relying on short-term fixes instead of fundamentals. Vince breaks down why financial literacy matters more than ever, how rising rates have exposed behavioral risks, and what Canadians need to understand before making their next financial move.

In this episode, we explore:
✅ The downside of the current real estate cycle and why so many Canadians are feeling financial pressure
✅ How cash-flow crunches are forcing difficult decisions for both new and experienced investors
✅ Why data, discipline, and behavior matter more than market predictions
✅ What the short-term outlook for Canadian real estate actually looks like 
✅ How CMHC policy decisions and ultra-low rates reshaped borrower behavior
✅ Why declining financial literacy is hurting Canadians more than market volatility
✅ What today’s buyers and homeowners need to understand before making their next move
✅ Vince’s mission to educate Canadians and cut through misinformation online

Whether you’re a first-time buyer, an investor navigating a tougher market, or someone trying to make sense of Canada’s shifting economy, this conversation delivers practical, experience-driven insights to help you make smarter financial decisions.

Who is Vince Gaetano?
From a young age, Vince Gaetano knew he wanted to run his own business. Starting with a newspaper route, grass cutting, and snow shovelling, he eventually made the decision to go into the lending branch of banking. During his university days, Vince was first exposed to the mortgage world through TD, and he would go on to spend his first decade in the mortgage business with TD Bank's national mortgage broker unit and with BMO as a national sales manager.

Vince has always enjoyed helping people buy homes and educating people on mortgages, as demonstrated by almost two decades worth of giving advice on CP24’s weekly Hot Property program. Born of this passion to educate, OwlMortgage.ca was created to provide an education-first and empathetic approach to mortgages.

Follow & Connect with Vince Gaetano:
YouTube - https://www.youtube.com/@wiseoldowlshow
Instagram - https://www.instagram.com/vincegmortgage/?hl=en
LinkedIn - https://www.linkedin.com/in/vince-gaetano-58a1106/
Facebook - https://www.facebook.com/OwlMortgage.ca
Twitter/X - http://x.com/VinceGaetano
Podcast - https://open.spotify.com/show/3928IWHSwO3avGMcaNJo27
Website - https://www.owlmortgage.ca/

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360

“People envy where you are now — they don’t envy how you got there.”

In this episode of the BLD Financial Podcast, we sit down with Jason Castellan, CEO and Co-Founder of Skyline Group of Companies, one of Canada’s largest private real estate operators with $10.5B+ investment in assets under management.

Jason breaks down how Skyline grew from student rentals in the early 1990s into a multi-fund platform spanning multifamily, retail, industrial, and clean energy — and why today’s market feels eerily similar to past downturns that created massive opportunity.

We dive deep into how institutional capital actually thinks, where money is flowing right now, and why secondary and tertiary markets are winning while some major cities fall behind.

This episode covers:
✅ How real estate cycles repeat and why today feels familiar
✅ Institutional capital vs small investor decision-making
✅ Why capital flows to the path of least resistance
✅ Government policy, housing supply & development charges
✅ CMHC financing and why scale matters
✅ Cap rate decompression, debt strategy & valuation shifts

Jason also shares why real estate is never truly passive, how Skyline manages debt through volatile cycles, and why balance-sheet strength matters more than ever in today’s environment.

If you want a real, unfiltered look at how serious real estate operators deploy capital through uncertainty, this is a must-watch.

Who is Jason Castellan?
Jason Castellan is the CEO & Co-Founder of Skyline Group of Companies. He has been purchasing, owning, managing, and financing income-producing real assets since 1991 and leads Skyline’s national strategy across asset acquisition, management, development, and investment.

His leadership philosophy is rooted in long-term thinking, disciplined capital allocation, and building trust with investors — a core reason Skyline has grown into one of Canada’s most respected private real estate platforms.

Follow & Connect with Jason Castellan & Skyline Group of Companies:
Instagram - https://www.instagram.com/skylinegroupofcompanies/?hl=en
LinkedIn - https://www.linkedin.com/in/jason-castellan-498a6810/?originalSubdomain=ca
Website - https://www.skylinegroupofcompanies.ca/
YouTube - https://www.youtube.com/@skylineGOC

Follow & Connect with Josh & Ehren:
Instagram - https://www.instagram.com/bldfinancial
Facebook - https://www.facebook.com/BLDfinancial
YouTube -  https://www.youtube.com/@bldfinancial

DLC National License: 12360