The 3 Core Criteria I Use to Analyze Any Commercial Real Estate Deal

Commercial real estate isn’t about throwing darts and hoping one hits. It’s about strategic warfare. You don’t get into a deal because you have a gut feeling. You get into a deal because you have a proven set of criteria that stacks the odds in your favor. Let me be clear: commercial real estate can make you rich, or it can bury you. The difference? The due diligence and decision-making framework you use before you go to war.

Criterion #1: Cash Flow First, Everything Else Second

Every commercial real estate deal I analyze starts with one question: Does this asset cash flow from day one? If the answer is no, I’m out. I don’t buy based on potential, I buy based on proven performance. Millionaires buy on hope. Billionaires buy on math. Period.

If you have to raise rents, cut costs, or pray for the market to change just to break even, you’re already playing a dangerous game. Cash flow is your defense. It’s the shield that protects you from market shifts, interest rate hikes, and unexpected vacancies. If the asset doesn’t cash flow today, it’s a liability—not an opportunity.

Want to flip it? Great. Just make sure it cash flows while you wait. Hope is not a business model. You need to be able to service debt, pay your team, and hold through turbulence without bleeding out.

Example: I once walked away from a Class A office building in Miami. It was sexy, sleek, and priced below market—but the leases were short-term, tenants were startups, and current income didn’t cover expenses. The broker said, "The upside is insane." I said, "So is the risk." Next week, I bought a boring industrial park outside Atlanta with 12-year tenants and a 9% cap rate. Guess which one is still paying me like clockwork?

Criterion #2: Motivated Seller = Deal Control

In commercial real estate, the deal doesn’t start with the building—it starts with the seller. Motivation dictates negotiation. If a seller is emotionally or financially attached, you’re going to overpay. But when a seller is motivated—divorce, death, debt, or distress—you control the narrative. And in business, control equals power.

I don’t chase perfect properties. I chase imperfect sellers. The best deals I’ve ever done weren’t because the building was special—it was because the seller was desperate. You’re not buying walls and windows. You’re buying circumstances, leverage, and opportunity.

Pro tip: Always ask, "Why are they selling?" If you don’t know the seller’s pain point, you have zero leverage. Your job is not just to evaluate the property, but to psychoanalyze the seller. Remember: you make your money when you buy, not when you sell.

Example: A seller in Chicago once had a strip mall under contract that fell apart during due diligence. He was three months behind on taxes and panicking. I came in with a 14-day close, 40% under ask, and I got it. Why? Because I showed up when he was vulnerable. I didn’t pay less for the property—I paid less because I solved his problem.

Criterion #3: Asymmetric Strategy = Maximum ROI

This is what separates the amateurs from the empire builders. I don’t look for deals that make sense to everyone. I look for deals that shouldn’t work—and then I apply an asymmetric strategy to flip the script.

What does that mean?

• Can I repurpose a warehouse into flex space?
• Can I turn a retail strip into mixed-use with residential on top?
• Can I negotiate seller financing or a master lease option to reduce capital risk?

Asymmetric thinking is about doing what others don’t see—or don’t have the guts to try. It's where real money is made. I built my empire on asymmetric strategies. Anyone can buy a building. But only a few can reimagine it, reposition it, and maximize return with minimal risk. If you’re not thinking 10 steps ahead, you’re already losing.

Example: I once bought a run-down motel in a C-minus neighborhood. Everyone thought I was crazy. I rezoned it, converted half to short-term rentals and the other half to studio apartments for traveling nurses. Within six months, it was bringing in triple the original income. I paid $600K. Two years later, I exited at $2.4 million. That’s asymmetric execution.

Execution is King

Having criteria means nothing if you don't have the guts to execute. Don’t overanalyze yourself into paralysis. If it cash flows, the seller is motivated, and you have a strategy to force appreciation or value-add, pull the trigger. Speed beats size. Done beats perfect. Most people talk about deals. I do them.

Real estate is not about finding the perfect deal. It’s about making the deal perfect through execution. You can't win with a bulletproof plan if you never pull the trigger. Want to succeed? Commit first, figure it out second. Because overthinkers stay broke and action-takers build empires.

And remember this: The deal you pass on today could be the one someone else turns into a fortune tomorrow. That’s the cost of hesitation in this game. Don’t lose money because you hesitated one extra day to run numbers. If it checks your criteria, act. Business is war. The battlefield is the market. Now go dominate.