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What an AI chief of staff actually does all day

A personal AI assistant for founders: the morning brief, inbox triage, drafts in your voice, and the approval rules that keep it safe.

Pratyush Agarwal · 3 min read

Most founders start the day reacting. Forty unread emails, a calendar that changed overnight, three things you promised someone last week. By the time you've sorted it out, the morning is gone.

A personal AI assistant won't run your company. But it can make sure you start each day knowing exactly what matters, with the boring parts already drafted.

The morning brief

At 8am, in WhatsApp, Slack or email, wherever you already look:

You reply "do 1 and 3", and it does.

During the day

  1. 1Email arrives
  2. 2Sorted: needs you, can wait, or routine
  3. 3Routine replies drafted in your voice
  4. 4You approve with one tap
  5. 5Follow-up reminder set

What it's good at

What it's not good at

Judgement calls, sensitive conversations and anything where the relationship matters more than speed. It should flag those, not handle them.

Questions people ask me

Does it need access to my email?

Yes, read access at minimum. Access is limited to what it actually needs, and you can see a log of everything it did.

How long does setup take?

Usually a few days. Most of the time goes into tuning the brief and your voice in the first week.

See our AI assistants service.

Pratyush Agarwal
Pratyush Agarwal

Founder of Overtake. I was a founding engineer at four startups, two of them in Y Combinator. I write about the AI systems I build for small businesses: what works, what doesn't, and how to start.

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