DESKTHEORY
First Edition · 2026
AI for CEOs Starting from Scratch

You are using a tenth
of what you already pay for.

Every CEO has a paid ChatGPT or Claude account. Almost none of them get more than a tenth of the leverage, because they use it like a smarter search box. This book takes you from one question at a time to a daily AI practice that gives you back a day a week, against your own work, in your own voice. 170 pages, 19 chapters. No terminal, no setup, no technical background.

Get the book → Read 3 chapters free →
170 pages 6 parts 19 chapters 1 day a week back
AI for
CEOs
Starting from Scratch
Andrew Lissimore
DeskTheory · First Edition
The Problem

Three things a search box cannot do.

The model behind your chat window is one of the most capable tools ever built. The bottleneck is not the model; it is how you use it. A CEO needs three things that typing one question at a time will never give. A daily practice does.

01 · A method

A way of asking that actually works.

Most people type a question, get a generic answer, and give up. There is a small set of moves (give it context, iterate like an editor, ask for the format you want) that turns the same tool into a real thinking partner. That is most of the gap, and it is learnable in an afternoon.

02 · Reuse

Work that does not start from zero.

A one-off answer disappears the moment you close the tab. The CEOs getting leverage keep a small library of prompts that sound like them, pointed at the work they do every week. The weekly update, the board pre-read, the hiring screen. Built once, run every time.

03 · A practice

Habits that compound, not tricks.

A clever prompt you saw on the internet does nothing for you next Monday. A 20-minute morning routine run every day does. The book is built around the daily practice, because that is the thing that turns AI from a novelty into a day a week, back.

There is a widening gap between operators who master AI and operators who use ChatGPT to help them write emails. The first group compounds. The second treads water. Closing that gap is the highest-leverage thing a CEO can do right now.
From the Foreword · Andrew Lissimore
The Contents

Six parts. One hundred and seventy pages. Nineteen chapters that go somewhere.

Written for the CEO who pays for ChatGPT or Claude, uses it like a smarter search box, and suspects there is more. There is, and this is the path to it.

Part I

The mindset shift

  • The CEO's AI starting line: where you are, and the gap to leverage
  • Assistant, agent, tool: the three ways to use AI, in plain English
  • What "leverage" actually means for your week
Part II

Talking to AI well

  • The anatomy of a prompt that works
  • Context is everything, and what is safe to share
  • Iterate like an editor, not a vending machine
  • The prompts a CEO reuses: a starter library
Part III

Your first real outputs

  • Your first high-leverage output
  • Email and the writing you do every week
  • A thinking partner: memos and decisions
  • Reading faster: reports and data you do not have time for
Part IV

A daily practice

  • The 20-minute morning AI routine
  • Saving what works: your prompt library and your voice
  • Privacy, accuracy, and what to never hand AI
  • Bringing your team along
Part V

The Monday workflows

  • The weekly update
  • The board and investor pre-read
  • The hiring and 1:1 toolkit
Part VI + Reference

Where you go next

  • When chat is not enough: graduating to tools, and the 30-day path
  • Glossary of terms
  • The starter prompt library
The Destination

From a search box to a day a week back.

Three phases of the same book. By the end of the third, the recurring blocks that used to eat your week have moved from drafting time to review time.

This week · Parts I-III

The first win

The mindset shift, the way of asking that actually works, and your first high-leverage output. An afternoon win you can feel, the kind that pays for the book on its own, all in the chat window you already have.

Weeks 2-3 · Part IV

The daily practice

A 20-minute morning routine. A prompt library that sounds like you, not a robot. A clear line on privacy and what to never hand AI. The point where AI stops being a novelty and becomes a habit.

Ongoing · Part V

The Monday workflows

The weekly update, the board pre-read, and the hiring and 1:1 toolkit. Each replaces a recognizable block of executive work. Each moves from a blank page on Sunday night to a quick review on Monday morning.

By Chapter 19

"You have a daily AI practice and a prompt library that sounds like you. The recurring blocks that drained your week are down to a quick review with edits. The book ends with you running the workflows, not reading about them, and a day a week back to spend on the work only a CEO can do."

Fit Check

Who this book is for.

And, more importantly, who it is not for.

For the CEO who thinks "I am not a tech person."

  • Founders and owner-operators of 5-150 person companies who pay for AI and get a fraction of it
  • Operators who have been told just use ChatGPT one too many times, and bounced off it
  • Leaders who want a result this week, not a project
  • Anyone willing to give the chat window they already have one focused week of real attention

Not for

  • People who already run a daily AI practice and want advanced tooling (start with the Claude Code guide instead)
  • Anyone shopping for a magic system that will run the company for them
  • Readers who want vendor comparisons and model benchmarks
  • People who do not actually want to change how one part of their week works
The Author

Written by an operator, not a vendor.

Andrew Lissimore
Founder · DeskTheory

Andrew Lissimore

Andrew runs Headphones.com, the largest specialty headphone retailer in the world, and Lantern, a venture-backed software company. Both got outsized leverage when he started using AI seriously, as a beginner, in the same chat window you already have. He wrote this book because he kept having the same call with CEO friends, helping them filter signal from the noise. Everything in it is what he would tell a friend about what is working in his own companies today.

Get the book

One hundred and seventy pages.
One focused week.

The full PDF, every Monday workflow, the starter prompt library, and a twelve-month update window as new chapters and prompts drop.

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