Raise Less. Prove More.
I’ve put money into more than 20 startups. I’ve also been an LP in funds much bigger than anything I could do directly. I am now clearer about the difference between those two seats.
As an angel, I back one kind of company: the kind that proves something real, then raises once.
That is the whole strategy.
I did not always think this clearly. Like many angels, I’ve been impressed by big rounds, strong names on the cap table, and the feeling that “something is happening.” Sometimes that is progress. Sometimes it is just a company getting better at raising money.
There is a version of the startup game that sounds smart and is often dangerous. Raise. Grow. Raise. Hire ahead. Raise. Spend. Raise. Every round gets celebrated as progress. Often it is just dependency.
So the companies I back prove something first, by their own means. That people want it. That the team can build. That the founders can survive a while without someone wiring money into the account.
Then they raise once — not to buy status, but to reach a real destination. Profitability. Strategic value. An exit. A company that can stand on its own.
Because endless fundraising has a price. It dilutes you. It rewires your incentives. It pulls attention away from customers and toward investors. At some point, the next round becomes the product.
The next part is more personal.
Some companies genuinely need many rounds. Deep tech. Hard infrastructure. Winner-takes-most markets. Those are not bad companies — some are extraordinary, and the big funds are good at backing them.
I know this because I look at what has actually paid. The cash has come mostly from the bigger funds. My smaller funds have largely not returned, and my direct angel bets are still unproven. Not settled yet, but enough to show a pattern: money does best when it has power. Big funds have it — access, reserves, influence, the ability to hold their ownership through every round instead of being crushed by it.
A small angel check does not. You took the earliest risk, and each round dilutes you, grows the preference stack above you, and shrinks your say. And a small fund in the same company gets squeezed the same way. The trap is not the angel seat versus the fund seat — it is being the underpowered money in the room.
So the strategy is two seats, held honestly:
As an LP, I back funds when they have genuine access, reserves, and follow-on power.
As an angel, I back founders who prove something real with their own means, raise one meaningful round, and build toward a destination that does not depend on the next investor saying yes.
A multi-round company can be great and still not be mine to fund. That is not a verdict on the company. It is a verdict on the fit.
I am not trying to win every version of the startup game. I am trying to make sure that whatever seat I am in, my money still has power when it matters.