A short memo, four times a year, on the strategic patterns I'm seeing across the practice. Pricing, positioning, leadership-team design, the long-form questions that don't fit on a slide. Mailed to about three thousand readers. Free, no tracking.
After thirty-four engagements between Series A and B, three patterns are showing up reliably in the founders who raise the wrong round at the wrong time. None of them are about the deck.
The first is the founder who is raising because the runway is making them anxious, not because the company is ready. This is the most common pattern, by some distance — about one in three engagements I see is, on the surface, a fundraise question, but underneath it is a runway question that has become a fundraise question because the founder cannot tolerate the anxiety of the next four months. The honest answer in this case is almost never to raise faster. It is to extend the runway, and use the time to reach the milestone the round needs to be priced against.
The second is the founder who is raising the round shape they wish the company was at, rather than the round shape the company actually is at. This is the founder pitching a Series B story on Series A metrics — or a Series A story on Seed metrics — and getting back, accurately, that the deck is impressive but the data does not support it. The fix is rarely to revise the deck. It is to revise the round.
The third is harder to see, because it is structural. It is the founder who has been pre-anchored on a particular round size by a single investor who is, for their own reasons, keen to lead it at that price. The advice an outside advisor can give here is the most boring imaginable: take the next two weeks, send the same deck to nine other partners at adjacent funds, and price the round against what nine other people will offer. About half the time the original lead is right, and you just have a faster process now. The other half, you have a different round.
If any of these patterns sounds familiar, the fastest move is the same: separate the runway question from the fundraise question, separate the story question from the data question, and separate the price-discovery question from the lead-investor question. They are three different questions and they want three different conversations. The deck is a fourth conversation, and almost always the easiest one.
The Notes memo ships at the end of each quarter — a short, written-out long-form essay on a strategic pattern I'm seeing across the practice. Free to read here. Free to receive in your inbox. No tracking pixels. Cancel by writing back.