SHARED BY MIKE OBORN · MORTGAGE · REAL ESTATE · INVESTING

Mike Oborn

Know your calls, your follow-ups and what's due before you open your email.

An AI Chief of Staff for busy business owners. It reads your email and calendar, gives you a brief every morning, and drafts your follow-ups for you to approve. Set it up yourself in about an hour. $397 one time.

Self-paced. About an hour to set up. Needs a paid Claude plan ($20 a month). Stuck? A 24/7 Classroom Helper walks you through it, and Molly helps you directly.

Does your morning start like this?

  • You open your inbox and the day decides for you.
  • A borrower, a buyer and a partner all need an answer before 9am.
  • You promised someone "I'll get that over to you," and it slipped.
  • A closing date or deadline sneaks up on you.
  • You tried ChatGPT, got something generic, and went back to doing it yourself.

That's not a discipline problem. Nobody built you a system for it.

A business owner buried in email before his day starts

Meet your Chief of Staff

Your first AI employee. It lives inside Claude, connected to your Gmail, Calendar and Drive.

Your AI Chief of Staff (illustration)

Runs your morning before you do

Chief of Staff

  • A morning brief every workday, at the time you choose
  • Your inbox triaged: what needs you, what can wait, replies drafted
  • Today's calls, with a prep note for each one
  • Follow-ups and deadlines caught before they slip
  • A Monday check on where you stand against your monthly goal
  • Drafts only. Nothing gets sent without your yes.

How I use my Chief of Staff

Mike Oborn

Mike Oborn

I run mortgage work in Florida, real estate projects in Utah and an IV clinic launch in California. Every morning my Chief of Staff gives me a two-minute brief before I open email.

  • Email triage: it sorts my inbox into what needs me today, what can wait, and what already has a reply drafted.
  • Follow-ups: it flags which borrowers owe me documents and which lenders and partners I owe an answer, with the follow-up drafted for my OK.
  • Goals: on Mondays it shows where each business stands against my goal for the month.
  • Staying on track: on Fridays I get what got done, what's stuck, and my top 3 for next week.
  • Investor updates: when I ask, it drafts them, so I start from a draft, not a blank page.

Nothing goes out without my yes.

“Before Chief of Staff, my life was scattered across my notes app, my calendar and the lists in my head, right down to prescription refills and registering my car. Now it all lives in one place, connected to my email, calendar and CRM, and I finally trust that nothing is slipping through the cracks. It's saving me 5 to 10 hours a week, and the bigger gift is the mental space. It even reminds me to take a break when I'm hyper-focused, and flags an idea when it doesn't fit my bigger goals.”
Brooke Bishop

Brooke Bishop, Realtor and Coach

Results vary. This is Brooke's own experience.

Here's what lands on your desk

An example morning brief.

Your AI Chief of Staff (illustration)

Morning brief from your Chief of Staff

Tuesday, October 27, 2026

Greeting
Good morning, Ryan.
Today
3 calls. Prep notes are ready: Martinez pre-approval at 9, listing walkthrough at 11, investor call at 2.
Inbox
6 emails need you. 4 replies are drafted for your OK. The rest can wait.
Waiting on you
Hendricks appraisal response, 2 days now.
Waiting on others
Bank statements from the Lees. Follow-up drafted.
Coming up
Closing Thursday on 214 Palm Ave. A rate lock expires Friday.
Goal check
3 of 5 closings toward this month's goal.
Top 3 today
Answer the appraisal, send the Lees' follow-up, prep the investor update.

Example only. Names and numbers are made up. Yours follows the order you choose.

Want this waiting for you tomorrow morning?

Set it up in about an hour. $397, one time.

Talk to it like a real assistant

Type it, or click the microphone and say it out loud. The guide gives you the exact words.

"Good morning, brief me."

Your day on one page: calls with prep notes, emails that need you, and what's due.

"Triage my inbox."

What needs you today, what can wait, and replies drafted for your OK.

"Check my follow-ups."

Who you promised something to and who's waiting on you, with drafts ready.

"How am I tracking this month?"

Where you stand against your goal, and what's still open.

"Plan my week."

Time blocks built around your calendar and your top three priorities.

"Talk this through with me."

Stuck on a deal or a decision? It asks good questions, then gives you 2 or 3 options and its pick.

Mortgage · Real estate · Investing

Three mornings it was built for

01 / Mortgage

The loan officer with 14 files in motion.

Before your first call, you know which borrowers owe you documents, which lenders you owe a reply, and which closings are this week. The follow-ups are drafted. You approve them.

02 / Real estate

The agent with showings back to back.

Your brief lists today's showings, the buyers waiting on comps, and the listing paperwork due. Every lead from the weekend has a drafted reply waiting.

03 / Investing

The investor juggling three projects.

One brief covers every deal: what closed, what's stuck, and which partner or contractor is waiting on you. Investor updates start as a draft, not a blank page.

Your morning, before and after

The same owner calm, reading his morning brief

Before

You open your inbox at 7am and the day decides for you.

With your Chief of Staff

Your brief is waiting. You know your top three before you open email.

Before

Deals, deadlines and promises live in your head, your phone and a legal pad.

With your Chief of Staff

One brain dump, and it's sorted for you.

Before

You remember the follow-up a week late.

With your Chief of Staff

It finds what you promised and has the follow-up drafted.

What you get

Your first win: a morning brief

Your calendar, the messages that matter, and what needs you today, waiting before you open your inbox.

Short how-to videos

Your welcome, how to talk to your Chief of Staff, your morning brief, and what to do when it gets something wrong.

Before you start

Which Claude plan you need, the desktop app, and connecting Gmail, Calendar and Drive. Every step links to Claude's own help pages.

The Start With You Interview

About 20 to 30 minutes, so your assistant learns you. It asks one question at a time, with options you can tap: what drains you, how many hours it takes, and what it can and can't touch. You get your How I Work Guide and Your Assistant's Rulebook, the rules it follows every day.

Your Chief of Staff, step by step

Create the Project, paste the instructions, add your files, connect your tools and run your first prompt.

Your starter Library

Your business, written down for your assistant. Five short docs in your own Google Drive: Brand & Voice, Business Overview, Frameworks & Offers, Clients & Projects, and Preferences. Your assistant reads them first, so it sounds like you and gets your offers right, and they refresh every week.

One week in: how much time did you get back?

Your morning brief runs on its own every workday. Then on day 7, see how much time you got back.

Questions

Hire your first AI employee