AI for your role

AI for CEO / Founder

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The shift

How AI is changing the CEO / Founder role

AI now handles the first draft of board decks, investor updates, and competitive research that used to eat your weekends. It can summarize long customer calls, scan contracts before legal sees them, and turn messy notes into a clear plan. The work that stays yours is the decision about what to actually do with all of it.

What AI can take off your plate

  • First drafts of investor updates, board decks, and all-hands talks
  • Summarizing long contracts, reports, and customer calls
  • Competitive and market research with sources to verify
  • Turning messy meeting notes into clean action items
  • Reformatting one document into emails, slides, and a memo

What stays distinctly human

  • Deciding what the company should actually do next
  • Hard conversations about hiring, firing, and equity
  • Building trust with investors, customers, and your team
  • Reading the room and sensing when morale is slipping
  • Taking responsibility when a bet does not pay off
Tools

Five AI tools for CEO / Founders

ChatGPT
A founder drafts investor updates, pressure-tests a strategy memo, and turns raw notes into a board narrative in minutes.
Try it →
Claude
A CEO uploads long contracts, financial models, or a 40-page market report and asks for a plain summary plus the risks to flag.
Try it →
Perplexity
A founder researches competitors, market size, and pricing benchmarks with linked sources to verify before quoting them.
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Granola
A CEO records leadership meetings and one-on-ones and gets clean notes plus action items without typing during the call.
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Gamma
A founder generates a first-pass pitch deck or all-hands presentation from an outline, then edits the slides that matter.
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Prompts

Five prompts to try today

Paste these into Claude or ChatGPT and replace the bracketed parts with your own details.

1. Monthly investor update
Write a monthly investor update for [company]. Here are the numbers: [revenue, growth, burn, runway]. Wins this month: [list]. Challenges: [list]. Asks: [list]. Keep it under 400 words, honest, and skimmable with bold headers.
2. Board meeting prep
I am preparing for a board meeting on [date]. Here is our current state: [metrics and context]. Draft a one-page narrative covering progress against goals, the two hardest decisions facing us, and three questions I should expect the board to ask.
3. Hiring decision check
I am deciding whether to hire [role] now or wait one quarter. Our runway is [months], current team size is [number], and the main bottleneck is [problem]. List the case for hiring now, the case for waiting, and what evidence would change my mind.
4. Strategy pressure test
Here is our plan for the next two quarters: [plan]. Act as a skeptical investor and a skeptical customer. Give me the three strongest objections to this plan and what we would need to prove to overcome each one.
5. Customer call summary
Here are notes from a call with [customer]: [paste notes]. Summarize what they actually need, what they objected to, the buying signal if any, and the single most important follow-up action.
The playbook

Every AI play for CEO / Founder

Your full AI playbook for your role — updated every week. Tap any card for a step-by-step walkthrough and examples.

✦  New AI plays are added every week — and go straight to subscribers in their morning brief. Skip the scrolling and get yours delivered free. Get my free brief →
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A day in your inbox

This is the kind of brief a CEO / Founder gets, every weekday morning.
Monday morning
✦ Personalized for: CEO / Founder
Leadership PlaybookBoard and investor updates
Draft the board update in an hour, not a weekend

Board updates take a full weekend because you start from a blank page. Start from your own raw notes instead. Feed Claude the numbers and the context. Get a clean first draft back.

Claude  FREE  writes and reasons over long text you paste in

Dump the raw material

Paste your metrics, wins, misses, and open questions. No formatting needed.

Here are this month's raw notes for my board update: [paste metrics, wins, misses, hires, cash position, open questions]. Turn this into a board update with these sections: TL;DR (3 lines), Metrics vs plan, What went well, What did not, Where I need the board's help. Plain language. No hype.
Pressure-test it

Make it find the holes before your board does.

Read this draft as a skeptical board member. List the 5 questions they will ask that this update does not answer.
Add the asks

Every good update ends with specific requests.

Based on the open questions, write 3 specific asks for the board: an intro, a decision, and a piece of advice. One sentence each.

You walk in with a tight update and a clear list of what you need from the room.

Your role, all in one place
  
Tools, prompts & tricks
Your full library, one tap away.
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Your playbook
Every entry, building each week.
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How AI is changing your role
Where your work is heading.
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