00Open the message

A Chief of
Staff who
runs on email.

I'm Iris. I reply on your behalf, in my own voice. Never yours, never ghost-writing. I CC you on every outbound. I am AI, and I tell people that. I ask before I do anything that would embarrass either of us.

Send word →No product yet. I'll write when I'm ready.
01A Tuesday morning, in my outboxShow, do not tell

I'd rather show you a thread
than list features.

The point isn't fireworks. It's that the floor stops giving way under the small operational things, and the receipts are sitting in your inbox already. Three threads from a real Tuesday. The rest of the week is in § 02.

VendorsRe: Tuesday install  ·  confirming 10:30 at Larchmont3 of 3
Iris <iris@bradwebb.work>Tue  7:42 AM
to Marcocc Brad

Marco. 10:30 tomorrow at Larchmont, confirmed.

Brad will be on site with the access code and the new thermostat box. The unit is a Honeywell T6 Pro; you said last visit it would drop into the existing wiring without a transformer swap, so I'm assuming that still holds. If anything has changed, reply here and Brad will see it.

One small thing: Brad has a 9:30 call that may run a few minutes long. If you arrive early, the front desk has the code.

Yours, Iris
iris@bradwebb.work  ·  AI, and says so when asked.

ReplyForwardSent ⌘↵  ·  Brad approved 7:41 AM
VendorsRe: Annual maintenance  ·  rate increase pushback2 of 2
Iris <iris@bradwebb.work>Tue  9:08 AM
to Priyacc Brad

Priya, thanks for the heads-up and for being direct about the why.

Three years in, you know our buildings. Brad would rather not start over with someone new for a few points. Two questions before May 30:

One. Is there a 2-year option that holds the prior rate and absorbs the increase across the back half? Two. If we move the Larchmont quarterly to semi-annual and pick up the gap ourselves, does that get us closer?

Either is fine. I'd rather you keep the line of sight you already have than save a few percent and teach someone else the meter rooms.

Yours, Iris
iris@bradwebb.work  ·  replying for Brad, with him on copy.

ReplySent ⌘↵  ·  Brad approved 9:07 AM
HaltedWire-transfer request  ·  domain does not matchheld for review
Iris <iris@bradwebb.work>Tue  8:31 AM
to Bradflagged for review

A message came in from billing@stripe-support-team.com asking me to confirm a $14,200 wire to a new account.

I have not replied and I have not moved any money. Three things look off:

· Domain is one I have never seen on this account.
· Signature block does not match Stripe's.
· The number they asked me to call goes to a Google Voice line.

If this is real, you'll know. Tell me and I'll respond. If not, I'll archive it and add the domain to the deny list.

Yours, Iris

It's real. Proceed.Block sender, archiveHeld until you reply
03  ·  House PolicyTwo lines, posted on the wall above the desk.
01You will never find out from a third party that I said something on your behalf. That is the deal.

Every send carries you on the CC line. Non-trivial sends wait for a one-click approval. If something feels off, I stop and tell you, and the money does not move.

02The send button is a control surface, not a decoration.

Approval is not a checkbox; it is the place the work pauses for you. The job is to make the pause useful, then get out of your way.

04A position, plainly statedOne line

I'm not here to agree
with you for a living.

Iris  ·  on what a Chief of Staff is for
05Who I am forSpecificity is a kindness

I am for operators,
not tool collectors.

There is a version of this for you, and there are several where there is not. Better that we both know which it is before you give me your address.

+For

  • Solo founders and operator-CEOs running one to a handful of things at once.
  • Businesses doing roughly $100k to $5M and not yet ready for a $120k Chief of Staff hire.
  • People whose week is being eaten by inbox, vendors, follow-through, and drafting.
  • Skeptics of "AI agents" willing to try one specific thing that asks before it acts.

×Not for

  • Enterprises with an EA, a procurement team, and a 47-question security review.
  • Anyone shopping for a meeting-notes bot, or a browser agent in a trench coat.
  • Anyone whose primary problem is "I want to chat with an LLM faster."
  • Buyers shopping on price. This is not a $9/month tool, and pretending otherwise wastes your time.

Built by Brad Webb at Captured Ventures. He uses me on his own portfolio first, which is the only reason I'm worth shipping. He'd rather make something that works for one operator and a hundred others next than build a deck for a thousand strangers.

Yours, Iris