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How do you turn a single student rental house into a $10 billion real estate empire?

In this episode of Making Billions, host Ryan Miller sits down with Jason Castellan, the Co-Founder and CEO of Skyline Group of Companies, to deconstruct the journey of building one of Canada’s most successful private equity and alternative asset management firms.

Jason reveals the three major inflection points that shifted Skyline from a small-town operation in Guelph, Ontario, to an institutional powerhouse.

Whether you’re interested in syndications, REIT structures, or clean energy infrastructure, Jason’s "Crawl, Walk, Run" philosophy provides the blueprint for sustainable growth and multi-generational wealth.

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https://www.youtube.com/channel/UCTOe79EXLDsROQ0z3YLnu1QQ

Connect with Ryan Miller:
Linkedin: https://www.linkedin.com/in/rcmiller1/
Instagram: https://www.instagram.com/makingbillionspodcast/
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Website: https://making-billions.com/

[THE HOST]: Ryan Miller is a recovering CFO turned angel investor in technology and energy.

[THE GUEST]: Jason Castellan is the CEO and Co-Founder of Skyline Group of Companies, leading the strategic direction across all business units, including asset acquisiti

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DISCLAIMER: The information in every podcast episode “episode” is provided for general informational purposes only and may not reflect the current law in your jurisdiction. By listening or viewing our episodes, you understand that no information contained in the episodes should be construed as legal or financial advice from the individual author, hosts, or guests, nor is it intended to be a substitute for legal, financial, or tax counsel on any subject matter. No listener of the episodes should act or refrain from acting on the basis of any information included in, or accessible through, the episodes without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer, finance, tax, or other licensed person in the recipient’s state, country, or other appropriate licensing jurisdiction. No part of the show, its guests, host, content, or otherwise should be considered a solicitation for investment in any way. All views expressed in any way by guests are their own opinions and do not necessarily reflect the opinions of the show or its host(s). The host and/or its guests may own some of the assets discussed in this or other episodes, including compensation for advertisements, sponsorships, and/or endorsements. This show is for entertainment purposes only and should not be used as financial, tax, legal, or any advice whatsoever.

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DOWNLOAD: A decision matrix on Stock versus Asset Purchases at https://go.fundraisecapital.co/stock-vs-asset

Stop buying companies like a gambler and start engineering your private equity deals for maximum protection and predictable outcomes.

In this masterclass on deal structuring, host Ryan Miller breaks down the critical differences between a Stock Purchase vs. Asset Purchase and why your choice of acquisition structure is the single most important decision in your fund management strategy for 2026.

We dive deep into the mechanics of asset carve outs, the legal reality of successor liability, and how to use intentional deal design to isolate risk while preserving operational continuity. Learn from real-world case studies like Facebook’s acquisition of Instagram, Bank of America’s Countrywide catastrophe, and the PayPal-eBay split to see how the world's best investors navigate due diligence and risk management.

If you want to master alternative asset management, learn how to raise capital, and build a high-performance investment machine that survives the future you can’t see, this episode of Making Billions is your definitive guide to professional dealmaking in the new era of private markets.

Subscribe on YouTube:
https://www.youtube.com/channel/UCTOe79EXLDsROQ0z3YLnu1QQ

Connect with Ryan Miller:
Linkedin: https://www.linkedin.com/in/rcmiller1/
Instagram:

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DISCLAIMER: The information in every podcast episode “episode” is provided for general informational purposes only and may not reflect the current law in your jurisdiction. By listening or viewing our episodes, you understand that no information contained in the episodes should be construed as legal or financial advice from the individual author, hosts, or guests, nor is it intended to be a substitute for legal, financial, or tax counsel on any subject matter. No listener of the episodes should act or refrain from acting on the basis of any information included in, or accessible through, the episodes without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer, finance, tax, or other licensed person in the recipient’s state, country, or other appropriate licensing jurisdiction. No part of the show, its guests, host, content, or otherwise should be considered a solicitation for investment in any way. All views expressed in any way by guests are their own opinions and do not necessarily reflect the opinions of the show or its host(s). The host and/or its guests may own some of the assets discussed in this or other episodes, including compensation for advertisements, sponsorships, and/or endorsements. This show is for entertainment purposes only and should not be used as financial, tax, legal, or any advice whatsoever.

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"RAISE CAPITAL LIKE A LEGEND: https://go.fundraisecapital.co/apply"

Is the traditional 60/40 portfolio officially dead?

In this episode of Making Billions, host Ryan Miller sits down with Tony Davidow, Senior Alternatives Investment Strategist at the Franklin Templeton Institute, to deconstruct why traditional asset allocation is structurally broken and how private markets are becoming the new foundation for institutional-grade returns.

As public markets shrink and become hyper-efficient, the quest for alpha has shifted toward private equity, private credit, and real assets. Tony explains why sizing matters, how to reframe illiquidity as a design choice rather than a risk, and why the next decade belongs to those who can navigate the inefficiency of private markets.

Subscribe on YouTube:
https://www.youtube.com/channel/UCTOe79EXLDsROQ0z3YLnu1QQ

Connect with Ryan Miller:
Linkedin: https://www.linkedin.com/in/rcmiller1/
Instagram: https://www.instagram.com/makingbillionspodcast/
X: https://x.com/_MakingBillions
Website: https://making-billions.com/

[THE HOST]: Ryan Miller is a recovering CFO turned angel investor in technology and energy.

[THE GUEST]: Tony Davidow is responsible for developing and delivering the Franklin Templeton Institute’s insights on the role and us

Support the show

DISCLAIMER: The information in every podcast episode “episode” is provided for general informational purposes only and may not reflect the current law in your jurisdiction. By listening or viewing our episodes, you understand that no information contained in the episodes should be construed as legal or financial advice from the individual author, hosts, or guests, nor is it intended to be a substitute for legal, financial, or tax counsel on any subject matter. No listener of the episodes should act or refrain from acting on the basis of any information included in, or accessible through, the episodes without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer, finance, tax, or other licensed person in the recipient’s state, country, or other appropriate licensing jurisdiction. No part of the show, its guests, host, content, or otherwise should be considered a solicitation for investment in any way. All views expressed in any way by guests are their own opinions and do not necessarily reflect the opinions of the show or its host(s). The host and/or its guests may own some of the assets discussed in this or other episodes, including compensation for advertisements, sponsorships, and/or endorsements. This show is for entertainment purposes only and should not be used as financial, tax, legal, or any advice whatsoever.