What if the most distressed buildings in your market don’t look distressed at all?

Some of the best off-market deals never hit LoopNet. They don’t show up in broker chatter. And on paper, they look “occupied.”

But the lights tell a different story.

In this breakdown, I dive into a fascinating strategy investors are using to uncover hidden vacancy by analyzing something most people ignore: energy usage. By comparing reported occupancy to actual electricity and utility consumption, you can spot buildings that are quietly bleeding—long before the market catches on.

Why did Starbucks ignore the billion-dollar real estate playbook that made McDonald’s rich?

Ray Kroc built McDonald’s into a $40+ billion property empire by owning the land under his restaurants. Howard Schultz knew that strategy… and deliberately did the opposite.

Heading into 2026, a lot of investors are still operating like it’s 2019—assuming industrial will bail them out, multifamily will never crack, and Silicon Valley will somehow innovate its way past fundamentals. But markets don’t reward nostalgia. They reward awareness. If you’re holding real exposure in today’s CRE landscape—whether that’s flex, medical, industrial, or even legacy office—your edge won’t come from speed. It’ll come from knowing which signals actually matter before the institutional money prices it in.

Most investors hit this point and keep moving as if every cycle works the same. That’s how portfolios grow… and quietly destabilize. Because what separates those who compound through volatility from those who stall isn’t hustle. It’s structure—understanding where demand is forming, which sectors are insulated, how freight and logistics are shifting, and what rising delinquencies are really telling you about capital risk in 2026. If you want next year to work for you instead of happening to you, you need to stop treating headlines like entertainment and start treating them like strategy.

Making real money in commercial real estate isn’t about finding ten different deals. It’s about learning how to get paid ten different ways on one deal. Most investors get stuck in the same cycle: grind to close, park the asset, and wait years for a payday that may or may not show up. Meanwhile, overhead keeps coming, momentum fades, and the business feels way harder than it needs to be. The truth is, if you structure your deals correctly, you can create income at closing, during the hold, and again on the exit—without needing a massive portfolio to survive.

The investors who last in this game aren’t just deal hunters. They’re deal architects. They understand that every transaction has multiple levers: brokerage, fees, operational cash flow, backend upside, and even debt positioning. You won’t stack all of them on every deal, but once you know the menu, you stop being reactive and start building predictable income around your acquisitions. That’s how you keep the lights on while your equity compounds in the background.

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.

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’re sitting on a meaningful liquidity event, a paid-off asset, or even a few million in deployable cash, you’re 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’s how wealth gets built… and quietly leaks.

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.

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.

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.

The headlines say “commercial real estate is cooling”—but the data tells a different story. According to Deloitte’s 2026 Outlook, most investors still expect to increase their CRE exposure over the next 12–18 months. Why? Because in uncertain times, hard assets win.

In this episode, Tyler interviews Nathan Weinberg, a Nashville-based real estate developer who got his start during the 2008–2009 recession - broke, unknown, and armed only with hustle and conviction. While others fled the industry, Nathan leaned in, picking up the phone faster than seasoned agents and betting on East Nashville before anyone else saw the opportunity.

This week, we tackled one of the toughest questions in commercial real estate — what do you do when a property just refuses to move? From a restaurant listing in Miami that’s been stuck on the market for nearly a decade to strategies for repositioning, remarketing, and even rethinking your buyer pool, we covered it all.

Commercial real estate isn’t just for millionaires — it’s for anyone who learns how to structure a deal the right way. In this video, I’ll show you proof. You’ll see how my business partner Jacob and I bought a failing self-storage facility in Nashville without millions in the bank — and turned it around in just 90 days. This wasn’t some big private-equity play or luxury development. It was a small, broken deal that became a massive opportunity because we knew how to stack capital, build partnerships, and fix operations instead of overbuilding. If you’ve ever thought you need to be rich to get into commercial real estate, this video will change your mind.

Partnerships can be the fastest way to scale your commercial real estate portfolio — or the fastest way to blow it up.

In this episode, we dive deep into how to structure real estate partnerships the right way so you protect your capital, avoid deadlocks, and set yourself up for long-term success. I’ll share real-world examples from my own deals, lessons learned from past mistakes, and how to keep your business relationships from turning into lawsuits.

Value-add commercial real estate is where true wealth is built — but only if you know how to underwrite it correctly.

In this episode, I review real-world commercial deals sent in by investors and break down how to evaluate them, uncover hidden upside, and avoid expensive mistakes. From outdated retail centers to underperforming office buildings, we’ll walk through how to identify opportunities, analyze risk, and structure deals that actually cash flow.

Most beginners lose thousands on their first commercial real estate deal — and it happens faster than you think. But here’s the truth: it’s not because they’re inexperienced or reckless. It’s because there are hidden traps in commercial real estate that no one talks about… until it’s too late.

After taking the summer to recharge, Office Hours is back—and we’re diving straight into one of the biggest opportunities in commercial real estate: vacant big box suites.

If you’ve ever driven past a shuttered anchor tenant and wondered what’s next for that space, this episode breaks it down. Tyler walks through the anatomy of a 30,000-square-foot former Big Lots—what to look for, how to evaluate build-out costs, and the smartest ways to reimagine these oversized vacancies.

Most people think real estate is all about luxury condos and chasing the biggest margins. But what if you could build a portfolio that actually makes a difference—while still making a solid return?

In this episode, I sit down with Evan Holladay, founder of Holladay Ventures, who has already developed over $500 million in affordable and workforce housing across the Southeast. His mission? To create 100,000+ units of housing that teachers, nurses, and service workers can actually afford.

Not all commercial properties are created equal — especially for beginners. Your first deal doesn’t have to be flashy to be profitable. What it does need is simplicity, stability, and a path to scale.

Most people think you need hundreds of thousands of dollars to get into commercial real estate.

The truth? You don’t.

In this video, I break down exactly how I got into one of my first commercial buildings in East Nashville with zero cash out of pocket. The property was 40% vacant, losing money, and overlooked by most investors. I stepped in with no capital—just leasing expertise, property management systems, and a plan to add value. Within two years, we stabilized the property to nearly 100% occupancy, more than doubled the building’s value, and I walked away with equity… without writing a single check.