08/05/2026
People ask me all the time, how do you decide what's worth investing in?
They're usually expecting a financial formula. Cap rates. ROI projections. Cash-on-cash return.
Those things matter. I look at all of them.
But they're not where I start.
Here's where I actually start:
1. Does this solve a real problem or serve a real need? Not a trend. Not a feeling. A genuine, durable need. If I can't answer that clearly, I slow down.
2. Who are the people involved? I have walked away from deals with great numbers because I didn't trust the people. I have leaned into deals with more risk because the people were exceptional. Character matters more than most investors want to admit.
3. What does the worst case actually look like? Not the surface-level worst case. The real one. Can I live with it? Can I recover from it? If I can honestly answer yes, I can move forward with clarity.
4. Am I investing, or am I gambling? There's a difference. Investing means I understand the asset, the market, and my role. Gambling means I'm just hoping. I only do the first one.
5. Does this align with where I want to be in ten years? Not just financially. Strategically. Every investment is also a direction. I want to be intentional about where mine are pointing.
No formula replaces judgment. And judgment only develops through the deals you do and the ones you don't.
I've learned as much from passing on something as I have from pulling the trigger.
What's your most important criteria before you invest? I'm always interested in how other operators think about this.