Uploaded July 2026 | Updated September 2026, 3 weeks ago
When a company is about to spend $100 million, Shawn Chan is the person in the room deciding whether it happens, and after fifteen years and roughly 200 investment committees he can spot the flaw fast. Now some of the decks in front of him are AI generated: cleaner formatting, never defensive, and confidently wrong. His frame is the difference between a demo and a memo. A demo is a beautiful confident slice built to impress; a memo is what survives a room whose entire job is to find what breaks. One marketing demo with a single wrong sentence, he reminds you, once erased enormous value the moment the market noticed.
So he lays out what an AI product needs to pass the memo test. Not every source deserves equal trust, since an audited filing is not a number from a group chat. Figures have to reconcile, and a contradiction between two numbers is not a bug but the most important signal in the room. Facts and guesses must stay labeled, because across three drafts an estimate quietly hardens into a fact nobody remembers assuming. Attach provenance rather than a citation tab, lock who claimed what, and the product that wins is the one that lets someone approve a deal without opening seven tabs at midnight.
Speaker info:
- linkedin.com/in/shawn-chan-2b58a9129
Timestamps:
0:00 - A fifteen year confession
3:27 - Two hundred investment committees
4:22 - Money follows trust
5:46 - Two machines: the demo and the memo
7:31 - When one wrong sentence costs billions
9:45 - Not every source deserves equal trust
11:22 - The numbers have to agree
14:59 - Facts and guesses stay separate
17:06 - When fake citations reach a court
19:21 - The airline chatbot that made a promise
21:30 - Attach provenance, not a citation tab
22:52 - The products that will win
When a company is about to spend $100 million, Shawn Chan is the person in the room deciding whether it happens, and after fifteen years and roughly 200 investment committees he can spot the flaw fast. Now some of the decks in front of him are AI generated: cleaner formatting, never defensive, and confidently wrong. His frame is the difference between a demo and a memo. A demo is a beautiful confident slice built to impress; a memo is what survives a room whose entire job is to find what breaks. One marketing demo with a single wrong sentence, he reminds you, once erased enormous value the moment the market noticed.
So he lays out what an AI product needs to pass the memo test. Not every source deserves equal trust, since an audited filing is not a number from a group chat. Figures have to reconcile, and a contradiction between two numbers is not a bug but the most important signal in the room. Facts and guesses must stay labeled, because across three drafts an estimate quietly hardens into a fact nobody remembers assuming. Attach provenance rather than a citation tab, lock who claimed what, and the product that wins is the one that lets someone approve a deal without opening seven tabs at midnight.
Speaker info:
- linkedin.com/in/shawn-chan-2b58a9129
Timestamps:
0:00 - A fifteen year confession
3:27 - Two hundred investment committees
4:22 - Money follows trust
5:46 - Two machines: the demo and the memo
7:31 - When one wrong sentence costs billions
9:45 - Not every source deserves equal trust
11:22 - The numbers have to agree
14:59 - Facts and guesses stay separate
17:06 - When fake citations reach a court
19:21 - The airline chatbot that made a promise
21:30 - Attach provenance, not a citation tab
22:52 - The products that will win
