How an investor prepped three founder meetings in 7 minutes
⏱ ~7 minutes · 35 turns · 33 tool calls · ~$3–8 in API cost · replaced ~30–45 minutes of manual digging
Anonymized — but every detail actually happened, in one live session.
An investor runs weekly office hours for the founders he backs: three back-to-back 20-minute slots where he reviews each company's profile and sharpens their elevator pitch. He had about thirty minutes before the first one — and wanted to walk in genuinely prepped on every founder, not just reading names off a calendar.
The information existed. It was just scattered across calendars, a document drive, and a startup-profile database, with nothing pulling it together. So he delegated the pulling-together.
The first prompt
No setup, no careful prompt engineering — just what he'd say to a chief of staff:
help me prep for my 3 office hours sessions this afternoon. I do this every week — I work with each founder on their profile page and their elevator pitch. this'll be the first time since the new profile tool launched. see if you can find transcripts from any of my previous office hours sessions.
What the agent did with it
Found the lineup. A direct search for "office hours" only turned up the parent calendar block — no founders. The three actual bookings lived on a separate booking calendar (number 41 of 41 on the account). The agent enumerated every calendar to find the one with the real attendees. Calendar archaeology, not a single search.
Learned the format from history. Instead of guessing how he runs these, the agent found a transcript of a past office-hours session and read it — extracting his exact flow: the two-minute check-in, the profile review, the elevator-pitch teardown, the closing "none of this is gospel, keep iterating." Nobody had to explain the format. It was already in his history.
Delivered a first brief — and missed something. The agent pulled each founder's public profile and drafted a per-founder brief. Good, but incomplete. He nudged:
did you look at each of their docs with their pitches in them?
It hadn't. The founders submit their own pitch docs before every session — a standard step the first pass skipped. A second nudge, fired off while the agent was already searching:
look at the prep on the todo calendar
Both corrections pointed at the same root cause: the pre-work was already collected in one place — a dedicated prep event holding every doc link, every assignment, even a rebrand confirmation — and the agent had started researching from scratch instead of finding it.
The real find
Once it read the founders' docs, the payoff surfaced: a colleague on the investment team had already rewritten all three pitches and left coaching notes — what he changed, why, and each founder's specific questions for the meeting. The agent's job flipped from "draft critiques from scratch" to "synthesize the work your team already did into one screen."
Final output: one screen per founder — the founder's pitch, the colleague's revision, the notes, the open questions, and the profile gaps to flag. Plus a cross-cutting catch that only shows up when you look at all three at once: the same field left blank on every profile, worth fixing upstream. He scanned all three in two minutes and walked into the room ready.
The whole session, in three prompts
That's it. Three casual, typo-tolerant messages — no special syntax, no prompt engineering:
1. help me prep for my 3 office hours sessions this afternoon… find transcripts from my previous sessions.
2. did you look at each of their docs with their pitches in them?
3. look at the prep on the todo calendar
What you can steal
- Search your own history before planning. For any recurring meeting, a transcript of a past one teaches the agent your format — no explaining required.
- Ask "where's the pre-work collected?" first. If you've already aggregated the materials somewhere, pointing the agent there beats re-gathering from scratch.
- Let batch analysis catch the cross-cutting thing. "What's true across all three?" surfaces patterns no single review will — trivial for an agent, tedious for you.
This is the kind of work delegation.school teaches — on your real tasks, live. Start the course →