How to Spot a Bad Deal Before It’s Too Late.

By Richard Maize

In business and in real estate, bad deals rarely show up wearing red flags. More often, they’re dressed up with pitch decks, urgency, and buzzwords. They look just good enough to pull you in—but if you’ve been around long enough, you start to see through the polish.

Over the years, I’ve walked away from more deals than I’ve said yes to. That’s not fear—it’s experience. Here are a few of the most common warning signs I’ve learned to trust, no matter how promising the opportunity seems on paper:

1. The Numbers Only Work in the Best-Case Scenario

If your margins disappear the second interest rates tick up or occupancy drops by 5%, it’s not a solid deal—it’s a gamble. A good investment can take a few hits and still stand. If the pro forma only works when everything goes right, walk away.

2. The Pitch Feels Rushed or Overhyped

Any time someone’s telling you to "act fast" or trying to hype urgency, it’s worth slowing down. Solid deals don’t need pressure tactics. When someone’s selling hard instead of showing substance, I take that as a sign they’re more interested in moving the deal than making it work.

3. The Team Has No Track Record

I’ll invest with someone new—but not someone unproven. If the person behind the project can’t show me previous deals they’ve executed successfully (especially under stress), I’m not handing over capital. I’m investing in people first, numbers second.

4. No Exit Strategy

If a deal doesn’t clearly spell out how and when I get my money back, it’s not a deal—it’s a black hole. I always want to know the exit plan up front, not just for me, but for every party involved. A fuzzy exit is a major red flag.

5. Too Much Emotion, Not Enough Logic

Sometimes the biggest red flag is gut-level. If I find myself being drawn in by emotion—excitement, FOMO, relationships—I stop and re-check the numbers. I’ve learned the hard way: the more emotionally charged a deal feels, the more likely it is to unravel.

Bottom Line
There’s no shortage of deals out there. The trick is learning which ones to walk away from before they drain your time, capital, or reputation. In the long run, saying no is what keeps you in the game.

I’ve built my career on discipline, not hype. And that’s a deal I never regret.

— Richard Maize