What Most Operators Won’t Tell You (But You Should Ask Anyway)

The Polished Pitch Isn’t the Whole Story

Every operator has a deck. They have projections. They talk about track records and IRR. But what they don’t say—what they don’t want you to ask—is often more important than what’s in the slide deck.

At Infinity⁹, we believe in the opposite approach: full transparency. Why? Because private real estate investing isn’t about “hype”—it’s about aligned interests, capital stewardship, and strategy that works in good markets and bad.

There are no bad markets, just bad strategies.

Here’s what you should ask, even when it feels awkward—and what most sponsors won’t tell you unless you do.

1. “How Much of Your Own Money Is in This Deal?”

Most operators talk about "skin in the game," but very few actually invest meaningful personal capital alongside investors. Some might count fees they've earned or promote interest as “skin.” That’s not alignment—it’s accounting.

What to listen for: True co-investment, with real cash in the deal. Not just sweat equity. If they won't share the number, that's your answer.

2. “What Happens If This Doesn’t Go As Planned?”

Every deal looks great on a pro forma. But real estate is real. Tenants don’t pay. Interest rates change. Markets slow down.

Ask directly: What’s your downside plan? What’s your worst-case scenario underwriting? Who absorbs losses first?

At Infinity⁹, our Building Capital Framework is built to withstand volatility—not just ride momentum.

3. “How Do You Actually Make Money on This Deal?”

If an operator makes most of their profit on fees, not performance, your interests are misaligned. Be wary of stacked fees, one-sided promotes, or aggressive waterfall structures that prioritize the GP over the LP.

Ask for a simple breakdown of all fees and when they’re paid. If the explanation gets vague, complex, or defensive—that’s a red flag.

4. “Can I Talk to LPs From Your Last 3 Deals?”

Testimonials are curated. What you want is direct access to real investors—not just the ones who had great outcomes. Ask to speak with LPs in projects that faced delays, cost overruns, or tenant issues.

What you’ll learn: How the operator communicates when things don’t go well—and how they treat investor capital when times are tough.

5. “Why This Deal? Why Now?”

Most deals are pitched as "can’t-miss" opportunities. But the real question is: why this asset, in this market, with this capital stack, right now?

Smart investors dig deeper. What’s the thesis? Why is this operator uniquely qualified to execute it? How is this deal different from what they did in 2021—or from what every other firm is doing?

Private Investing Isn’t Passive. It’s Personal.

When you invest in a private real estate deal, you’re not just buying an asset—you’re backing a strategy, a team, and a philosophy. You deserve transparency, not marketing. And if you're not getting answers, you're already getting answers.

Your money doesn’t need a visa. But it does need a plan.

At Infinity⁹, we encourage tough questions. In fact, we ask them of ourselves before we ever bring a deal to investors. That’s what institutional-quality real estate should look like—and it’s what we’re building.

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