Angel investing moves fast. Founders pitch with conviction, markets look massive, and it's easy to get swept up in momentum. But the investors who build consistent returns do one thing differently: they slow down and ask hard questions before writing a check.
Here are five questions I come back to on every deal.
1. Why is this team uniquely positioned to win?
The market might be real and the idea might be good — but ideas are plentiful. What matters is whether this specific team has an unfair advantage. Do they have domain expertise, a proprietary network, a technical edge, or lived experience of the problem? If you can't articulate why they have the right to win, that's a signal worth sitting with.
2. What would have to be true for this to be a fund-returner?
Most angel investors don't think about this explicitly. Work backwards from your ownership stake and what a realistic exit looks like. If you need the company to exit at $2B for you to get a meaningful return, and the most comparable acquisition in that space was $80M, the math doesn't work — regardless of how much you like the founders.
3. What's the biggest risk the founders aren't talking about?
Founders are salespeople. They'll cover market size, traction, and team all day. What they won't volunteer are the risks that keep them up at night. Ask directly: "What would most likely cause this to fail?" The quality of their answer tells you a lot about their self-awareness and honesty.
4. How does this market look in 5 years?
Timing matters enormously in early-stage investing. A great product in a shrinking market is a bad investment. A decent product in a structurally growing market can work out fine. Look at the macro tailwinds, the regulatory environment, and the competitive dynamics. Is the window opening or closing?
5. What am I getting for my check?
Understand the terms before you commit: valuation, pro-rata rights, information rights, any unusual protective provisions. A deal at the right price with fair terms is very different from the same deal with a 3x liquidation preference and no pro-rata. Read the documents.
These five questions won't catch every risk, but they'll force you to think clearly about the ones that matter most. The goal isn't to find reasons to say no — it's to make sure the reasons you say yes are the right ones.