She asked me one question: what does it cost you personally if this goes sideways. Not the IRR, not the equity multiple. What does it cost you. I said I had 60k of my own money in it, which is real money for me, and she wired 150k four days later. First outside capital I'd raised. I keep thinking about how nothing in my pitch deck answered that question, and the deck was 22 slides.
The deck thing is real. I spent probably three months building out a 28-slide deck for my first raise, waterfall models, sensitivity tables, the works, and the LP who actually came in never asked to see it. She wanted to know what I was doing with my W-2 while the project was running, whether I had reserves outside the deal, and what I'd already passed on before bringing her this one. That last question caught me off guard because I hadn't thought about it as a signal, but she had. She was looking for whether I had a filter or whether I was just pitching the first thing I found.
The 60k number you mentioned, I'd push on that framing a little. Not the amount itself, but how you said it. "Real money for me" is actually doing more work than people realize. An LP with 150k to place has probably seen operators come in with 200k in the deal that was, genuinely, throwaway money for them, and they can smell it. The alignment question isn't just the dollar figure, it's what that dollar figure means to you specifically. My first outside LP told me later she'd passed on a deal where the operator had more skin in the game numerically but it was clearly a rounding error in his net worth. She said she'd rather be in with someone whose stomach drops when they think about losing it. That's the actual underwrite she was doing.
Skin in the game matters, but watch the follow-up question she didn't ask yet.
