Why Great Investors Are Rarely Surprised

$100M+ in AUM—And the Lessons That Got Me Here

What I Don’t Do

You don’t get to $100M by winging it.
Here’s what I don’t do:

• I don’t invest in what I don’t understand.
• I don’t assume anything will go exactly as planned.
• I don’t guess where my returns are coming from.

Because here’s the truth:
The best investors are rarely surprised.

How I Actually Think About Deals

→ I know the market inside and out before I step in.
→ I understand my asset class better than anyone in the room.
→ I plan for both the upside and the risk—down to the dollar.

If closing costs are $60K, I already accounted for that.
If a timeline slips, I built in the cushion.
If a worst-case scenario hits, I’m not scrambling—I’m executing Plan B.

Playing to Win, Not Just Playing It Safe

Assumptions kill returns.

• Run the real numbers.
• Ask sharper questions.
• Prepare for the punch before it lands.

That’s not fear-based investing. That’s how you win in the long run.