104. Real Estate Portfolio Strategy: Buying Commercial Property

Real Estate Portfolio Strategy: Buying Commercial Property

Are you diversifying your portfolio? Today, we’re talking about building your commercial real estate investment portfolio - why you should be investing in commercial real estate, strategies for approaching the investments, and how to properly scale your business. Commercial real estate is an incredible wealth-builder. These properties can provide you with cash flow, appreciation, tax advantages, and other benefits unlike any other investment vehicle. If you’re looking for the ultimate retirement plan, commercial real estate investments might just be the path for you and are a terrific way to diversify, if nothing else. Here’s how to add commercial property to your portfolio and why you should.

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355. Waterfront Flex, Medical Office Boom, Multifamily Delinquencies, and More | The Deal Desk
355. Waterfront Flex, Medical Office Boom, Multifamily Delinquencies, and More | The Deal Desk

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.

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354. 10 Ways to Make Money from ONE Deal | Office Hours
354. 10 Ways to Make Money from ONE Deal | Office Hours

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.

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353. The Hidden Economics Behind Parking Lots
353. The Hidden Economics Behind Parking Lots

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.

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351. Starting a Family Office | Office Hours
351. Starting a Family Office | Office Hours

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.

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352. 2026 Trends, Trump's Ballroom, 50-Year Mortgage, and More | The Deal Desk
352. 2026 Trends, Trump's Ballroom, 50-Year Mortgage, and More | The Deal Desk

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.

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350. Let's Talk Flex Space | Office Hours
350. Let's Talk Flex Space | Office Hours

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.

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349. How this Real Estate Developer Raised $1M from ONE Email
349. How this Real Estate Developer Raised $1M from ONE Email

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.

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348. Commercial Real Estate Outlook 2026 | Office Hours
348. Commercial Real Estate Outlook 2026 | Office Hours

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.

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347. How to Build Wealth Without Leaving Your Neighborhood
347. How to Build Wealth Without Leaving Your Neighborhood

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.

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346. What Do You Do When A Property Just Won't Sell? | Office Hours
346. What Do You Do When A Property Just Won't Sell? | Office Hours

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.

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About Your Host:

Tyler Cauble, Founder & President of The Cauble Group, is a commercial real estate broker and investor based in East Nashville. He’s the best selling author of Open for Business: The Insider’s Guide to Leasing Commercial Real Estate and has focused his career on serving commercial real estate investors as a board member for the Real Estate Investors of Nashville.