The Commercial Real Estate Investor Podcast

Most investors overlook one of the simplest and most profitable business models in commercial real estate: monetizing land. In 2008, Chicago sold the rights to 36,000 parking meters for $1.15 billion. By 2025, the buyers had already collected every dollar back, plus roughly $500 million in profit, with decades of revenue still ahead. The city did not realize it was sitting on a land based cash flow machine. That deal is a clear reminder of a bigger truth in CRE. Some of the most boring properties quietly outperform the flashy ones. In this video, we break down how simple asphalt lots, parking meters, and industrial outdoor storage evolved into billion dollar assets, and why these land only plays keep winning. Low maintenance. Captive demand. Strong margins. Steady cash flow today, plus long term appreciation in the dirt underneath. If you are chasing stability, simplicity, and upside tied to scarcity and inflation, land monetization deserves a serious look. The opportunity is not in reinventing real estate. It is in charging for land everyone else ignores. Sponsored by www.CRECentral.com

Starting a family office sounds like something reserved for billionaires, but the truth is the “family office mindset” kicks in way earlier than most people realize. If you are sitting on a meaningful liquidity event, a paid off asset, or even a few million in deployable cash, you are already in the zone where strategy matters more than hustle. The problem is most investors hit that point and keep buying deals the same way they always have, reactive, scattered, and without a real portfolio blueprint. That is how wealth gets built, and quietly leaks. What separates families who compound for generations from those who stall out is not access to deals. It is structure. How you hold assets, how you protect them, how you finance them, and how you balance stability with upside. The goal is not just to grow your net worth. It is to build a machine that preserves it, produces cash flow, and stays aligned with what your family actually wants long term. In today’s breakdown, we cover: • How family offices really structure ownership and liability • The portfolio mix that keeps cash flow steady while still creating growth • Why single tenant net lease can act like “bonds” inside your CRE strategy • How to think about debt relationships, 1031 timing, and long term holds If you are serious about turning a strong balance sheet into lasting generational wealth, this is where the game changes. Let’s dive in. Sponsored by www.CRECentral.com

Heading into 2026, a lot of investors are still playing the same game they played in 2021: chasing whatever looks hot, reacting to headlines, and hoping the next deal fixes the last one. But markets don’t reward hustle forever. They reward positioning. If you’ve got real exposure in CRE—whether that’s a solid portfolio, meaningful liquidity, or even just a few good assets—you’re already at the point where strategy matters more than speed. The problem is most people hit that level and keep operating without a blueprint. That’s how returns get built… and quietly leak. What separates investors who compound cycles from the ones who stall out isn’t access. It’s structure. Knowing which sectors actually have tailwinds, which markets are earning real demand, how the capital stack is shifting, and what policy or rate moves will change your underwriting before your broker calls you. If you want 2026 to be an advantage—not a surprise—you need to stop reading news like entertainment and start reading it like allocation. In today’s Deal Desk breakdown, we cover: • What the ULI Emerging Trends report is really saying about 2026 winners and losers • Why niche sectors like data centers, self-storage, and senior housing are pulling ahead • The Trump White House ballroom story—and what it reveals about regulation and development power • The 50-year mortgage push and why “affordability fixes” can destroy long-term wealth • The NYC-to-Florida migration narrative—what’s real, what’s hype, and how to underwrite it • And whether a Fed cut is back on the table, plus what that means for cap rates and deal flow If you’re serious about making smart moves heading into next year, this is the kind of context that keeps you ahead of the market instead of chasing it. Sponsored by www.CRECentral.com

Flex space is heating up while most investors are still looking the other way. Headlines talk about industrial slowing, but small bay units between 2,000 and 6,000 square feet are leasing faster than they hit the market. Even older buildings in average locations are getting multiple offers. Years of underbuilding and redevelopment wiped out supply, yet the businesses that rely on these spaces never disappeared. Demand stayed strong. Inventory didn’t. Developers chased massive distribution centers all through the 2010s, leaving a gap that electricians, e-commerce shops, fabricators and startups are now fighting to fill. That shift turned flex space into one of the tightest and most approachable asset classes in CRE. In today’s breakdown, we cover: • Why small bay supply collapsed and demand surged • How logistics trends reshaped industrial development • What makes flex space ideal for new CRE investors • How to assess demand and structure projects the right way If you want to understand where the next real opportunity is in commercial real estate, flex space deserves your attention. Let’s dive in. Sponsored by www.CRECentral.com

What if I told you one of my friends raised $1,000,000 in just 24 hours—for his first solo real estate deal? No private equity. No institutional backing. No track record raising capital alone.Just one email… backed by years of invisible work. This is the story of Evan Holladay, a mission-driven developer who went from working at LDG Development to launching his own company, Holiday Ventures—and how his brand, his relationships, and his consistency led to a million-dollar raise overnight. If you’re trying to raise capital for your first commercial real estate deal—especially if you don’t have a ton of cash or experience—Evan’s story will show you exactly what actually moves the needle. Sponsored by www.CRECentral.com