EP 490 - Discover how Tom "The Skyscraperguy" raised over $3B and revitalized $2B+ worth of historic skyscrapers and iconic city blocks.

Discover what it takes to raise over $3 billion in capital and revitalize more than $2 billion worth of historic skyscrapers and iconic city blocks.

In this episode, Tom “The Skyscraperguy” Liravongsa, managing partner of Landmark Collection, shares the remarkable journey that took him from starting a fund with negative $10,000 on a credit card to acquiring and restoring landmark skyscrapers across major U.S. cities. Tom reveals how mastering institutional underwriting, understanding the mechanics of syndication, and thinking beyond “the zeros” allowed him to transition from trading derivatives to orchestrating massive real estate projects. He also explains why skyscrapers—assets once reserved for institutional players—are becoming accessible to new investors, how large-scale developments create powerful economies of scale, and why cities and density provide a unique form of market insulation during economic disruptions. For investors and entrepreneurs who want to think bigger about capital raising, deal structuring, and transformative real estate opportunities, this conversation delivers insights you won’t hear anywhere else.

5 Key Takeaways from the Episode

1. Capital Raising Is the Core of Commercial Real Estate
   Tom explains that at its core, commercial real estate is about syndication—raising capital, finding deals investors believe in, and executing them together.
2. Institutional Knowledge Creates Massive Advantage
   By underwriting billions in real estate projects while working with European investors, Tom learned how institutional capital flows and used that knowledge to scale his own deals.
3. Large Deals Can Reduce Risk Through Scale
   While skyscraper projects involve large numbers, Tom argues that economies of scale, performance bonds, and professional teams can actually mitigate risk compared to smaller projects.
4. Skyscrapers Offer Unique Market Insulation
   Because they exist in dense urban centers where economic activity is concentrated, skyscraper assets can benefit from strong demand, higher rents, and greater government support during crises.
5. Retail Investors Can Participate in Institutional Deals
   Through modern fundraising methods, social media reach, and flexible deal structures, Tom is opening access to skyscraper investments that were historically limited to institutional capital.

About Tim Mai

Tim Mai is a real estate investor, fund manager, mentor, and founder of HERO Mastermind for REI coaches.

He has helped many real estate investors and coaches become millionaires. Tim continues to help busy professionals earn income and build wealth through passive investing.

He is also a creative marketer and promoter with incredible knowledge and experience, which he freely shares.

He has lifted himself from the aftermath of war, achieving technical expertise in computers, followed by investment success in real estate, management skills, and a lofty position among real estate educators and internet marketers.

Tim is an industry leader who has acquired and exited well over $50 million worth of real estate and is currently an investor in over 2700 units of multifamily apartments.

Connect with Tim
Website: Capital Raising Party
Facebook: Tim Mai | Capital Raising Nation
Instagram: @timmaicom
Twitter: @timmai
LinkedIn: Tim Mai
YouTube: Tim Mai