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WINSTON FOWLKES

Jacksonville, Florida.
Working wherever good projects happen.

winston@winstonf.com

AI assistants for executives and teams

Your own AI
chief of staff.

A personal assistant that lives on the phone you already use. Text it, send it a voice note, or call it. It works your inbox, your calendar and your task list, and Winston builds it, runs it and keeps it tuned.

Setup plus a monthly management plan, scoped after a short call.

Astra, Winston's own AI chief of staff, explains how it works. Tap for sound.

01What it handles

The work that fills your day, handled.

Your phone

  • Answers calls on its own number and takes messages
  • Places calls for you
  • Texts and voice notes on Telegram or WhatsApp, and it can reply by voice

Inbox and calendar

  • Summarizes what came in and what needs you
  • Drafts replies for you to send
  • Finds times and handles scheduling

Tasks and follow-ups

  • One task list, wherever you add to it
  • Reminders before things slip
  • Nudges on the follow-ups you would rather not chase

Team coordination

  • Lives in your group chats
  • Runs check-ins and keeps projects moving
  • Routes questions to the right person

Briefs and reporting

  • A morning brief and an order of operations for the day
  • Weekly summaries and scorecards
  • Research on a company, a person or a market

02Running in production today

Winston runs his own businesses on a team of these.

Not a demo. These assistants do real work every day, across phone calls, group chats, inboxes and task lists.

Chief of staff

Astra

  • Answers Winston's phone line by live voice and places outbound calls
  • Works over Telegram and WhatsApp
  • Keeps his task list, with proactive check-ins and morning briefs
  • Tracks retainers and invoices, and nudges on payments
  • Sends email, does research, and makes images and video

Project manager

Rex

  • Sits in client WhatsApp groups and runs the check-ins
  • Triages bug reports from a product's feedback form
  • Ships website changes for clients
  • Posts a weekly scorecard

Household assistant

Nyx

  • Runs the family side: bills, goals and home-fitness coaching

Marketing

Motive

  • Drafts posts and campaigns, and nothing goes out without approval

03How it works

From one call to an assistant you use daily.

  1. Discovery call

    We talk through what eats your time, whether you run on Google or Microsoft, and the systems your day depends on. You leave with a clear picture of what your assistant would handle first.

  2. Build

    Winston builds your assistant around that list: its phone number, its connections to your email, calendar and tools, and the rules for what it can do on its own.

  3. Launch

    You get your own onboarding page and a short video that walks through how to use it. Text it, call it, or send a voice note from day one.

  4. Ongoing management

    Winston runs it and keeps tuning it as your work changes. New skills get added when the need is real, not before.

04Guardrails

You stay in charge.

An assistant is only useful if you can trust what it does. These are part of every build.

  • It works only for the people you choose.
  • You decide what it does on its own and what needs your OK. For example, it drafts the email and you hit send.
  • Your data stays in your own Google or Microsoft accounts.
  • You can revoke its access at any time.

Have a few minutes?

LET'S TALK ABOUT
YOUR DAY.

Tell Winston what eats your time. He'll tell you plainly what an assistant could take off your plate, and what it shouldn't.

Book a call

239-271-8495winston@winstonf.com