Hey there,

The wait is over: Enrollment is now open for The AI Executive System.

On Monday, I shared why The AI Executive System (AIEX) exists at all.

Yesterday, we walked through who this is for – what 200+ high-performance professionals from our IWAI community told us about AI at work (and in their personal lives), and the three things that most surprised us while we built it.

Today, I’d like to show you the system itself – and clarify exactly what to expect.

If that’s clear, let’s talk about what we’ll actually build together.

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1 | The Result:
​What AIEX is designed to change for you

At the highest level, The AI Executive System is a 6-month program for high-performance professionals to:

• Reclaim 10–20 hours of time (and energy) per week …without lowering the standard of your work.
• Multiply the quality of your decisions and deliverables …by pairing your unique expertise with a small team of specialized AI coworkers.
• Protect – and eventually improve – your personal quality of life …so your health, relationships, and sense of self stop getting the leftovers.

That said, if all it does is help you reclaim even 10 hours a week while protecting the quality of your work, it pays for itself.

The bigger question is: What will you do with the extra time, energy, and opportunities – for yourself, your family, your team, and your community?

Here’s how Jimmy, an executive who’s been with us for six months, put it:

2 | The Plan:
​3 phases → 20+ assistants → 1 AIEX System

On the enrollment page, you’ll see this laid out visually as 20+ assistants across 3 phases:

Here’s the email-friendly version (with a few nuances you won’t see on the page):

Phase 1 – STABILIZE

Reclaim 10–20 hours of your time & energy per week (Timeline: 1–2 months)

This phase is built for your 0–3 month horizon – the “keep the wheels from coming off” window we saw in the survey.

We’ll work together to:

1. Design your AI Executive Office Interface Create a futureproof “home base” where your AI coworkers and tools actually talk to each other – and to you – instead of living in 27 different tabs. Think: one “single source of truth” interface for briefs, summaries, decisions, and follow-through.
2. Design your Front-Line AI Coworkers Configure 1–3 front-line AI coworkers who help with things like meeting prep, inbox triage, research synthesis, and progress tracking – all tuned to deal with the “death by a thousand paper cuts” that eat up your time and energy every day and week. They won’t just “block and tackle” – you’ll design them to actually help with real work, and not with generic prompts either.
3. Design your Personal AI Assistants Build 1–2 AI assistants that help with all the personal life stuff we all have to stay on top of whether we’ve got kids or not. I’m talking about the planning, logistics, and everything that “makes life less chaotic”, so you can reclaim evenings, weekends, and mental bandwidth.

By the end of Phase 1, the goal is simple:

Your week feels less reactive, less leaky, and less noisy – without sacrificing the quality of your work.

The best part?

If you just get 8 hours back, then you’ve reclaimed a full work day that’s yours to keep, every week, for the entire year…and you keep that for life.

Phase 2 – SYSTEMIZE

Multiply your work quality & personal capacity (Timeline: 1–2 months)

This phase is mapped to your 3–12 month horizon – where you told us you want a more strategic, repeatable work rhythm.

We’ll:

1. Build Your Unique Expertise Library Turn your scattered notes, decks, SOPs, and experience into a coherent, AI-ready knowledge base that you and your AI coworkers can actually use. (This protects your craft from “prompt roulette” and keeps AI from dumbing your work down.)
2. Build Subject Matter Expert Integrators Configure AI coworkers who sit inside your real domain – strategy, ops, finance, product, marketing, etc. Their job: translate your expertise into reusable workflows and draft-quality outputs you can refine, not write from scratch.
3. Mostly, it’s the unique context of your life situation so any info, decisions, etc are then uniquely tailored to you (and doing it in a way that’s safe and sensitive to your privacy preferences).

By the end of Phase 2, your work and life start to feel more intentional and less brittle.

You’re not just coping week to week – you’re building a system that supports the way you actually want to live and work.

Phase 3 – SCALE

Scale long-term work & life quality (Timeline: 1–2 months)

This phase is aligned with your 1–3 year horizon – the “who I’m becoming” window where survey answers shifted toward stewardship, mastery, and being a better human.

Here, we’ll:

1. Install Your AI Leadership & Advisory Council Design a small “board” of AI advisors (strategy, finance, ops, health, etc.) that help you think in quarters and years – not just weeks. They stress-test ideas, reveal hidden trade-offs, and help you remember what you said long-term really matters.
2. Install Your AI Executive Chief of Staff Orchestrate your AI coworkers so they behave like a coordinated team, not a loose collection of tools. The Chief of Staff agent keeps projects moving, closes loops, and makes sure your best ideas don’t die in your notes app.
3. The goal isn’t “AI runs your life” – it’s that you have a trusted digital operations layer keeping the important-but-not-urgent parts of life from falling through the cracks.

One note on timing: Phase 3 is a release in progress. Those lessons and templates are publishing as they’re finished, and will be complete by September 2026. Phases 1 and 2 – the ones that reclaim your week – are available on Day One.

By the end of Phase 3, you’re not just “using AI better.” You’ll have a future-proof system of AI coworkers that supports your 1–3 year work and life goals.

And, for our super-detailed oriented readers, yes, you get to configure every part to leverage the parts you built before it. 20+ Assistants. 3 Phases. 1 Ecosystem. Multiplied quality of work and life.

Yes, it’s nuanced, and that’s why we won’t drop you off on an island for “Survivor: AI edition” to fend for yourself.

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3 | Where you’ll actually build all this

A fair question at this point: what am I building this in?

The answer, six months ago, was “a lot of off-the-shelf software that wasn’t very good.” So we did two things about it.

We built our own app to give you the fastest possible start.

IWAI Studio puts the chat, the orchestrator, the model, and the tools in one workspace – so you can be talking to your first AI coworker inside 30 minutes instead of losing a weekend to setup. It’s free with your enrollment. It’s on the web today and downloadable on Mac and Windows (for extra privacy) in August. It’s model-agnostic (Claude, GPT, Gemini with your own keys, plus open models like Qwen, Kimi and DeepSeek), and everything you build exports out in a couple of clicks. No lock-in, by design.

And we teach three tech tracks, not one:

• Fast Start – IWAI Studio. The quickest path through the curriculum, and where nearly everyone begins.
• Integrated Suite – Claude Cowork, or Microsoft Copilot Studio if your employer requires it. (There’s a full Microsoft/M365 chapter for exactly that situation.)
• Self-Hosted & Open-Source Stack – for people with privacy or compliance constraints, allowing you to run software that you fully own and control, and even to do it entirely on a Mac Mini if you want to.

You don’t have to pick now – the first module walks you through choosing. And you’re never locked in: every assistant we teach ships as a downloadable template in all three track formats, and we have designed the whole program with the knowledge that new technology will be released in the future. Change is built in rather than being a surprise or speed bump.

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4 | How we’ll support you

You won’t be left to do this alone with a PDF and vibes.

Inside the AI Executive System, you’ll have:

• A structured 6-month roadmap that walks you through the 3 phases & 20+ assistants – with lessons recorded and available from Day One, and lifetime access to all of it.
• AIEX Demo Days, our live sessions every other Thursday, where a coach or a fellow student walks through a full build they’ve actually shipped – what it does, how they configured it, what they had to iterate on. Recorded and added to your library if you can’t join live.
• A private Slack community of other high-performance professionals building their own AI Executive Systems – wins, build logs, “how do I actually wire this up?” questions, co-working, and an AI news channel.
• A template library of 20+ ready-to-run assistant builds, downloadable in every supported track format, and updated continuously as new models and platforms earn a place in the program. You get every update at no extra cost.
• Ready-to-use templates, prompts, and workflows designed from our real client work and, at times, from actual flows we’re using inside IWAI right now – these aren’t random “cool demo” experiments.

The exact cadence and access varies by level of support, but the core idea is unchanged:

Choosing your level

There are three ways to join:

Training is the full curriculum, the template library, Demo Days, the community, and lifetime access. Everything above.

Coaching adds one-to-one time: a 30-minute kickoff session to plan your build, plus AIEX Fast Passes – bookable 30-minute 1:1 sessions with our coaching team (actual software developers) where you screenshare and work through your specific build until it runs. Not “here’s how to think about it.” Here’s your bug, fixed, in your environment. Fast Passes are only available on Coaching and Executive Concierge – they’re not part of the Training level.

Executive Concierge is brand new this enrollment. Instead of building your first agents yourself, our team builds ten of them with you across a structured engagement – kickoff, build, launch, and a proper handoff where we teach you to run and extend the whole system. Then you get a set of Fast Passes for whatever you want to build next. It’s the most hands-on service we’ve ever offered.

Each level has a hard cap on spots, because there’s only so much of our team to go around – and Executive Concierge is the smallest group of the three. Full details, inclusions, and pricing are all on the enrollment page.

And three guarantees, so the decision is risk-free

• 3-Day Grace Period. Something urgent comes up in your first three days? Email us and we’ll refund you in full, no questions.
• 60-Day Guarantee. Do the work – watch the trainings, attempt the early builds – and if it still isn’t working for you inside 60 days, choose a full refund or hands-on help from our team reworking your plan until it fits.
• Family & Medical Sabbatical Guarantee. On a payment plan, if you or your household hit a major medical or financial hardship, you can pause payments for up to 3 months. Life happens; we support you through it.

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5 | About this cohort (and what happens next)

For the past six months, I’ve worked daily with more than 100 students in our founding membership. I wrote about that yesterday, including the parts that didn’t go to plan.

That group is the entire reason this version exists:

• We scrapped some tech tracks we were originally optimistic about, because we couldn’t get students to a place where the thing actually worked.
• We built our own free-for-students software to dramatically speed up the learning curve and early agent builds, and made it totally flexible and exportable so you can switch to other tools whenever you want.
• We rebuilt coaching around one-to-one sessions after learning that group calls – great as they are for community – were not the way to debug a specific build.

You’re not joining a beta. You’re joining the version those 100+ students built.

If you’ve been reading along this week thinking:

…then I’d love for you to read the full invite and decide, with a clear head, if you’d like to join us.