The Anatomy of a Pass
Searching For The Question - David Orban
SubscribeSign in
The Anatomy of a Pass
David Orban<br>Aug 09, 2026
Share
Over the course of 60 days in 2026 I reviewed every pitch that reached my inbox, and I declined most of them. Close to a hundred rejection emails went out. Each one was a full letter: specific concerns grounded in the deck’s own numbers, followed by the questions worth answering before the next investor conversation, and a sincere wish of good luck with the raise.<br>Most investor passes are a single polite line. I wanted to see what happens when a pass carries real feedback. This essay documents that process: the structure of the emails, the reactions of the founders, the patterns behind the decisions, and the money behind the pitches.<br>Download the full analysis (PDF, 8 pages)<br>A pass is the normal outcome of this work. Any yes an investor gives can only arrive after a long series of nos, and an investor who says yes to a large share of inbound pitches will not remain an investor for long. The interesting question is what the nos leave behind: nothing, or something the founder can use.<br>The structure of a pass
Every rejection follows the same shape. A clear decision arrives in the first sentence, because founders deserve certainty more than encouragement. Numbered concerns follow, each anchored to a specific claim in the deck, so the founder can verify or refute them independently. Then come the questions that the next investor will ask anyway, offered as preparation. A genuine closing wish ends the letter, because passing on a round is a statement about fit and risk, and it says nothing about the worth of the people building the company.<br>This is one of the emails, with the recipient and the deck-specific details blurred:
How the letters were written
A page of deck-forensic feedback for every pitch, at this volume, is beyond what I could write by hand. I built an AI-assisted pipeline for my deal flow: each deck is read in full, its claims are checked against its own numbers and against public sources, and a draft letter is produced with the concerns and the questions. I review every letter before it goes out, and the decision to pass is mine. One founder replied that he tips his hat “to whoever set up your stack for that processing.” The stack deserves the compliment, and the judgment it amplifies stays human. The point is that the cost of giving founders real feedback has collapsed, and with it the excuse for the one-line pass.<br>What the founders replied
I received a lot of positive feedback, even gratitude. Thirty-eight founders wrote back, and their replies form the most counterintuitive dataset of the whole process. A selection, verbatim:<br>“Thank you for providing what is easily the most analytical, constructive, and valuable feedback we have received since starting this journey.”<br>— Peter & Karina, HachikoBox<br>“Thank you for this. Genuinely. This is the most rigorous and useful piece of investor feedback we have received.”<br>“The feedback is impressive. That might be the top 1 feedback I ever received from anybody. I tip my hat to whoever set up your stack for that processing.”<br>“Most passes are one line. You gave me a page of the exact questions I need to answer before the next conversation and that is more useful than a yes with no substance.”<br>— Naresh Pamula, KYCpro<br>“A pass with no explanation is the norm. A pass with five precise, well reasoned observations is genuinely useful, and we do not take it for granted.”<br>— Federico De Rosa, Vibedesk<br>“A pass with this much rigor behind it is rare, and more useful than most soft yeses.”<br>— Jonathan Griffit, Co-Founder & CEO, Zooly
Several founders contested specific arguments on the merits, sometimes with good reason, and two were openly angry, one of them at the idea that an AI-assisted process had judged his company. Forty-nine founders did not reply at all. The gratitude above is real, and it is also a selection: the founders who found the letter useful were the likeliest to write back.<br>Many of those who replied answered the questions point by point, correcting their decks in the process. Several asked whether they could return once the gaps were closed. The lesson for investors is plain: founders absorb a hard decision well when it arrives with respect and substance.<br>Why I passed
I classified every one of those letters by the concerns it raises. The same types recur. Inflated or unverifiable traction appears in four passes out of five, unsupported projections and undefended moats in two out of three, and irreconcilable revenue numbers in more than half. Ranked by frequency:<br>Traction inflated or unverifiable. Pipeline, pilots, and logos presented as traction: verbal commitments and LOIs framed as contracts, free trials counted as deployments, target lists shown with customer-tier logos, testnet or simulator results presented as real-world proof.
Projections requiring unexplained step-changes. Forecasts that need a...