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LEARN TO HOW PROFESSIONALS RAISE $1M-$100M FOR FUNDS AND SYNDICATIONS: https://go.fundraisecapital.co/apply How do you turn a single student rental house into a $10 billion real estate empire? Most fund managers dream of the billion-dollar mark, but Jason Castellan actually lived the grind to get there—starting from a single basement rental in Guelph. In this episode of Making Billions, host Ryan Miller sits down with the CEO of Skyline Group of Companies to deconstruct the ruthless discipline required to scale to $10 billion AUM. Jason strips away the fluff to reveal how he transitioned from "big hat, no cattle" to a vertically integrated titan, dominating secondary markets where institutional competitors are too slow to play. From the early days of student rentals in Guelph to managing massive REITs across multifamily, industrial, and clean energy, Jason shares the exact inflection points that turned a local operation into a nationwide powerhouse. If you want to know how to "squeeze the lemon" of a portfolio, this is your blueprint. From multifamily REITs to pioneering clean energy infrastructure, learn why Jason believes the biggest risk isn't the deal itself, but losing the trust of your investors. Chapters: [0:00] Jason Castellan explains how over-communication and disciplined "no-go" rules protect LP capital. [1:12] Discover how Skyline scaled from a $123,000 student rental to a multi-billion dollar real estate firm. [4:42] Analyzing the shift from asset management to becoming an Exempt Market Dealer (EMD) [6:19] Why secondary and tertiary markets provide more reliable cap rate compression and alpha. [12:25] How altruistic value and seeing the impact on retired investors drives company culture. [13:59] The logic behind testing a new investment thesis through syndications before launching a fund. [16:29] Why you must crawl before you walk to protect your reputation and track record. [20:56] How Skyline successfully navigated the .com bubble, the 2008 crisis, and COVID-19. [23:30: Managing mark-to-market gains and inflationary pressures in a high-interest-rate environment. [25:56] Strategic insights into Clean Energy Funds. [31:04] The power of vertical integration in generating repeatable operational alpha. [34:20] Transitioning from subsidized energy to self-sustaining biogas and solar infrastructure. [39:28] Maintaining decision velocity and succession planning while growing to 10 billion AUM. [43:05] High-stakes risk management rules for institutional-level allocators and deal filters. [45:36] Building a multi-generational legacy for the next 25 years. [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 acquisition, management, development, and investment. PODCAST LINKS: Subscribe on Apple: https://podcasts.apple.com/ca/podcast... Subscribe on Spotify: https://open.spotify.com/show/1OvE6Ie... Connect with Ryan Miller: Linkedin: / rcmiller1 Instagram: / makingbillionspodcast X: https://x.com/_MakingBillions Website: https://www.Making-Billions.com The Private Equity Podcast for Fund Managers, Alternative Asset Managers, and Venture Capital Investors 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 to 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 based on 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. #RealEstateInvesting #PrivateEquity #EnergyTransition #FundManagement #RaisingCapital