The AI
Executive
System
If this helps you reclaim even 10 hours a week while protecting the quality of your work, it pays for itself.
The bigger question:
What will you do with the extra time, energy, and opportunities — for yourself, your family, your team, and your community?
20+ Assistants. 3 Phases. 1 Ecosystem.
Use case:
Multiply your professional value and quality of life by building your own team of AI assistants & advisors.
Note:
You’ll build an ecosystem of AI “coworkers” — also called agents or assistants — and configure them to act as a coordinated high-performance team.
Hey 👋, Rob here.
You’ve been doing the work: Building your career, sharpening your craft, delivering real value in your field. That’s not small.
But here’s something a lot of our students run into around this stage:
The career grows… and so does the chaos.
More responsibility means more emails, more meetings, more deliverables, more decisions. And at some point the bottleneck isn’t your skills or your strategy — it’s you, personally, running out of hours in the day.
That’s exactly what The AI Executive System is built to solve.
AIEX helps you build the operating system behind you — your own team of AI coworkers: a frontline assistant handling emails, calendars, and research; a subject matter expert who multiplies the quality of your deliverables; and an Executive Advisory Council that helps you think through big decisions at the 1–3 year altitude.
Here’s what students are walking away with:
- 10–20 hours reclaimed per week. Not by doing less — by building systems that do more.
- A “Home Office” interface that acts as your AI command center, organized around your real work.
- An AI Chief of Staff that helps you run your career (and your personal life) with more clarity and less friction.
You’ve already proven you can do the work. AIEX is how you stop being the single point of failure in it.
What you’re looking at today isn’t a program we designed in a vacuum. Over the past 6+ months, I’ve worked daily with more than 100 students in our founding membership — helping them build real, working AI agents and assistants for their inboxes, their pipelines, their proposals, their homes, and their long-term decisions. Every lesson, every template, every tool inside the program has been shaped by what those students actually got stuck on and what actually worked.
You’re standing on the shoulders of all of that.
Here’s the biggest thing we learned along the way: the initial friction for a non-engineer trying to build AI agents is enormous. Lots of tools claim to be easy. In practice, most non-technical students who sat down with a so-called “agent builder” tool got stuck on obscure errors, buggy integrations, or confusing documentation. It wasn’t a failure of effort or intelligence. It was a failure of tooling.
That’s not what we wanted. So we did something about it.
We rebuilt the program from the ground up around the friction points we saw — and, because some of those friction points couldn’t be solved with better teaching alone, we built new software and tools exclusively for AIEX students. More on that a bit further down the page.
What you should know right now: we’ve brought the learning curve for building real, useful AI agents as close to zero as we could get it. You start building immediately.
Once you’re in, you’ll have immediate access to the curriculum, our continuously-updated template library, the private community, and our live AIEX Demo Days — plus, depending on the tier you choose, direct 1:1 coaching sessions with our team or a full done-for-you engagement where our team builds the system alongside you.
Everything is recorded, so if you’ve got time-zone or schedule concerns, rest assured, you won’t be left behind. Every session gets added to your private library, and you can work through the curriculum on your own schedule.
As for the nuts and bolts of what we’ll be doing over the next six months?
Well, read on, my friend. This is all about making the year ahead one where you actually feel the compounding benefit of AI in your work and your life.
-Rob
Quick Recap: How we got here…
Over the past couple of years, a lot of our students have used AI to grow their income, land better clients, and level up their careers.
That’s still important.
But as I’ve been watching the “AI productivity” space evolve, I’ve noticed something that doesn’t sit right with me:
Most people talk about using AI just to squeeze more output out of one person.
Very few talk about using AI to give people more presence, more stability, and more time with the people who rely on them.
I don’t believe the goal is to become a slightly more efficient cog.
I believe the goal is to become an AI Executive: someone who designs a small ecosystem of AI coworkers that makes their work and life better – and then uses that extra capacity to support their loved ones, their team, and their community.
That’s the core “why” that’s driven us here at IWAI to create The AI Executive System.
You’ve already heard quite a bit about this, so instead, let’s get to the fun stuff – how this all actually works.
The Goal: Where we’re going…
Picture this: You and I work closely to design your very own…
System of AI coworkers that multiply your professional value and quality of life.
- Objective:
- Build a tailored ecosystem of AI coworkers for your role, your work, and your life – so you’re no longer the bottleneck for everything that matters.
- Time:
- Over a focused 6-month cohort, with a clear plan, live support, and a group of peers. You keep lifetime access to all lessons, templates and downloads.
- Efficiency:
- Multiply yourself as a “solo” AI Executive of your career, consultancy, or team. Effectively multiply your individual work quality, capacity, and output (before you try to put the oxygen mask on anybody else).
- Lifestyle:
- Reclaim time and mental bandwidth, then reinvest it intentionally into deep work, your loved ones, and the projects that matter most.
Depending on your situation, this might look a bit different for you:
Executives & team leaders
Design a team of AI coworkers that take work off your plate, sharpen your decisions, and support your team – so you can lead at a higher level without burning out.
For senior professionals & high-performance ICs
Stop being your team’s bottleneck. Leverage your team of AI coworkers to protect the quality of your work, stay ahead of the curve, and create more space for strategic projects instead of constantly putting out fires.
For consultants (including AICP alumni)
Become the AI Executive of your own consultancy first – build the coworkers, systems, and capacity you need personally, before you ever decide to roll AI out as a new line of business for clients.
For founders
Scale your individual capacity, output, and life quality before you try to roll AI across an entire company – so if and when you do, you’ll lead from firsthand experience instead of (invisibly expensive) theory.
By the end of this program, my goal is that you’ll be among the most advanced people in your field at using AI responsibly: not just to move faster, but to build a healthier, more human future of work in your corner of the world.
If that’s the future you want to lead, The AI Executive System is how we get there – together.
Everything we build together is S.O.L.I.D.
We know the AI space can be full of hype, empty promises, and privacy nightmares — not to mention every company trying to lock you into their software.
We built AIEX around a different standard.
Every assistant, every workflow, every foundation you set up inside the program is designed to be S.O.L.I.D. — because we hold ourselves to five specific commitments across every lesson, every template, every tool decision.
Secure
Your data is safe, your work is yours. Prompts, knowledge, outputs — all owned by you. We teach privacy first.
Open
Portable by design, no lock-in. Use any LLM, current or future. Every build ships as a template for all tech tracks.
Lasting
Every assistant compounds with the ones you’ve built. An operating system that keeps improving, not a one-off tool.
Instant
Every assistant ships as a ready-to-use template. Plug in your accounts and you’re running — no build required.
Direct
We tell you the truth, tradeoffs included. AIEX is a no-hype zone — always our honest take on every tool.
The Plan: What you’ll build…
20+ Assistants. 3 Phases. 1 AIEX System.
Inside The AI Executive System, we’ll work together to:
1. Stabilize
Reclaim 10–20 hours of your time (and energy) per week. Set up your AI Executive Office, build your first assistants, put your frontline team to work, and get your connected agents acting on the accounts you already use — so the day-to-day work stops depending entirely on you.
2. Systemize
Multiply your work quality and personal capacity. Turn your expertise into a working library, layer on subject matter expert agents that draft in your voice, and build an Advisory Council with long-term memory across your professional life.
3. Scale
Scale long-term work and life quality. Design your Chief of Staff and Home Manager so your ecosystem of AI coworkers supports 1–3 year goals at work and at home.
Every build in the program ships as a downloadable template ready to plug into platforms along multiple tech tracks. The library grows continuously as the field evolves — so the version you download six months from now reflects what actually works six months from now, not what worked at your enrollment date.
That’s the high-level. And here are the targeted details.
Stabilize
Value: Reclaim 10–20 hours per week
Set up your AI Executive Office
Before you build a single agent, you set up the private space where all of them will live. This is the interface you’ll come back to every day — the boardroom where you brief the team and review their work.
First you’ll choose your tech track: Fast Start, Integrated Suite, or the Self-Hosted & Open-Source Stack. You can move between them as your system grows. Then you’ll get your accounts and API keys in order and learn the DROID framework — the four moves every agent makes — plus the four components every agent is built from.
S.O.L.I.D. Outcome: A private AI Executive Office on the track that fits you, and a mental model that makes every future build feel legible rather than magical.
Milestones
- Tech track chosen (Fast Start, Integrated Suite, or Self-Hosted Stack).
- Executive Office set up in your chosen environment and named.
- Accounts and API keys stored securely for the LLM providers you’ll use.
- DROID framework and four-component architecture internalized.
Tools
- AI Executive Office setup kits (one per tech track).
- Account and API key setup guides for OpenAI, Anthropic, Google, and other providers.
- DROID framework reference and comparison of the four components across tracks.
- Tech-track decision worksheet.
Your first two assistants
Two small, deliberate builds that teach you the shape.
- Your News Analyst — give it the topics you care about, and it pulls the current headlines, reads through them, and hands you back a tight briefing instead of a wall of links.
- Your Weather and Commute Planner — checks the day’s conditions and tells you what to actually do about them, from what to wear to when to leave.
Both are simple on purpose. Once you’ve seen these two work end to end, the more capable agents that follow feel like extensions rather than new territory.
S.O.L.I.D. Outcome: Two working assistants in your Executive Office, and the five-part build shape learned by doing rather than reading.
Milestones
- News Analyst deployed and returning daily briefings on the topics you chose.
- Weather and Commute Planner deployed and returning daily reports for your location.
- Both assistants accessible from your primary Communicator (chat surface).
- Optional: same builds ported to a second tech track.
Tools
- Complete News Analyst build, with downloadable workflow files.
- Complete Weather and Commute Planner build.
- Communicator setup guides (Slack, Zulip, in-track chat).
- “Inside three orchestrators” reference lesson so you understand what changes when you swap tracks.
Your frontline team
Assistants that pull real weight in a working day. Each adds one load-bearing piece to the shape you already know — persistent memory, live information, or a stack of API calls.
- Your Expenses and Mileage Tracker — logs business travel and expenses across data tables, and works out mileage with a mapping API.
- Your Grocery and Pantry Manager — runs your grocery list and pantry inventory from tables and reasoning alone. No external services required.
- Your Weekend Planner — searches the open web and pulls out what’s actually happening near you.
- Your Billing and Time-Tracking Assistant — handles billing and time-tracking through a stack of API calls. This is the build where wiring tools by hand starts to feel like work, which is exactly the problem the next chapter solves.
S.O.L.I.D. Outcome: Four assistants handling recurring tasks that used to eat your day, plus working knowledge of data tables, HTTP requests, and API stacks — so future builds go faster.
Milestones
- Expenses and Mileage Tracker live, with your business travel logging into it.
- Grocery and Pantry Manager live, with your household data.
- Weekend Planner returning suggestions based on your location.
- Billing and Time-Tracking Assistant integrated with your invoicing tool.
Tools
- Complete downloadable builds for all four assistants.
- Data-table templates for expenses, mileage, groceries, and pantry inventory.
- “Talking to tables” and “Everything is an HTTP request” reference lessons.
- API-stack wiring guide.
Your connected team
Now your team stops working in isolation and starts acting on the accounts you use every day — your inbox, your calendar, your CRM, your project workspace. You’ll learn OAuth, connectors, and the Model Context Protocol so your agents can reach into real systems and act cleanly inside them.
- Your Lead Prospector — surfaces new leads with live web search and saves the results straight into Google Docs and Sheets.
- Your Inbox Manager — triages your inbox, tags mail by a scheme you define, and never touches anything it shouldn’t.
- Your Scheduling Assistant — plans your days and finds meeting times across calendars.
- Your CRM Assistant — keeps your CRM current through a single clean connection.
- Your Project Planner — turns a vague project into a structured plan in Notion, whether it’s a marketing campaign or a home renovation.
Together these cover work that normally eats three or four hours a day. Mail, calendar, pipeline, projects, research — all with a specialist agent whose whole job is that one lane.
S.O.L.I.D. Outcome: Five specialists acting on your live accounts, and enough command of OAuth, connectors, and MCP that the next integration takes an afternoon.
Milestones
- Lead Prospector live and surfacing leads into your Docs and Sheets.
- Inbox Manager triaging mail with your labeling scheme.
- Scheduling Assistant coordinating meetings across your calendars.
- CRM Assistant updating records through your CRM connector.
- Project Planner turning a real project brief into a working Notion plan.
Tools
- Complete downloadable builds for all five assistants.
- OAuth and connector setup guide.
- Model Context Protocol (MCP) reference lesson.
- Connector safety and permissioning checklist.
“We’re the most high-performing team … and we’re also the smallest team in the company, managing the biggest footprint”
My weekly report as an executive used to take me hours every week. Now it takes about 30 minutes for the entire week … I can do eight hours of work in about three hours, and nobody believes me until they see my output.
Systemize
Value: Multiply your work quality and personal capacity
Your Unique Expertise Library
Every language model already knows the general 80% of any subject. What it doesn’t know — and can’t know — is your specific 20%: your methodology, your brand voice, the way your firm actually talks. Your Unique Expertise Library is where that lives.
This is the foundation for everything else in Phase 2. Get it right, and the assistants drawing on it produce work that sounds like you. Get it wrong — dump in every document you’ve ever touched — and retrieval goes noisy while the output goes generic.
You’ll learn what earns a place in a library and what doesn’t, and how to prepare documents so agents can actually use them. You’ll also see how vector stores and embeddings work, and how to wire the finished library into your Executive Office.
S.O.L.I.D. Outcome: A working Library built from your real documents, and the judgment to know what belongs in it — which matters more than the mechanics.
Milestones
- Source audit complete: you know which documents carry your unique 20%.
- Priority documents prepared and cleaned for ingestion.
- Vector store live and searchable in your chosen tech track.
- First “ask the library” retrieval test returning accurate, grounded answers.
- Library connected to your Executive Office so every agent can reach it.
Tools
- Library design canvas and source-audit checklist — what to ingest, what to leave out.
- Document preparation guide.
- Vector stores and embeddings reference, with a stack comparison across all three tracks.
- Optional technical guide to Pinecone vector databases.
- Boardroom connection guide, with retrieval test prompts.
Your subject matter experts
This is where AI stops feeling like a chat window and starts feeling like a colleague who has read everything you’ve ever written. Subject Matter Expert Integrators don’t just answer questions in the moment — they produce deliverables grounded in your Library.
- Your Proposal Writer — drafts client proposals in your voice, grounded in your past work, your pricing approach, and your firm’s actual offerings.
The build teaches three patterns that transfer to every knowledge-powered assistant you’ll make:
- The three-phase workflow. Intake, brainstorm, produce. The assistant clarifies before it drafts, and shows you the outline before it writes six pages.
- Never-invent discipline. When something isn’t in the Library, the assistant asks instead of fabricating.
- Register separation. The conversation you have with the assistant is chat; the deliverable it hands back is a finished document, ready to send.
Once you’ve built one SME Integrator, you have the template for every knowledge-powered assistant that follows — in any domain, on any track.
S.O.L.I.D. Outcome: A working SME Integrator producing client-ready deliverables from your Library — and three patterns that make the next one an afternoon’s work.
Milestones
- Proposal Writer deployed and drafting in your voice from your Library.
- Three-phase workflow verified: the assistant clarifies, outlines, then produces.
- A real deliverable produced end to end and judged good enough to send.
- The pattern documented so you can point it at your next domain.
Tools
- Complete downloadable Proposal Writer build.
- SME Integrator architecture templates.
- Three-phase workflow system-prompt patterns.
- “Good enough to edit” draft review rubric.
- Improvement log template tied back to your Library.
Your quality-of-life assistants
The same Library pattern, pointed at the parts of life that have nothing to do with your job. The architecture is identical. The content is completely different — and so are the privacy rules.
- Your Family History Advisor — answers questions from a structured personal archive: names, dates, relationships, stories, and the details you’d otherwise have to keep asking your parents about.
- Your Recipe and Meal Planner — plans meals around your household’s real constraints: allergies, medical conditions, dietary needs, preferences, and what’s actually in the pantry tonight.
The Recipe and Meal Planner introduces one more pattern worth carrying forward: mode labeling. It tells you whether an answer came straight from your cookbook, was modified from a recipe you already have, or is brand new — so you always know how much to trust it. That idea generalizes well past cooking.
This is also where your personal-side library takes shape, with its own structure and its own boundaries. Household data is different from work data, and it gets treated that way.
S.O.L.I.D. Outcome: A personal-side assistant running against a Personal Life Library you built — with boundaries you set on what goes in.
Milestones
- Personal Life Library created for at least one domain (family history, food, health, learning, or household operations).
- Privacy rules written for what goes in and what stays out.
- One personal-side assistant deployed and used at least weekly.
- A specific quality-of-life improvement you can point to and name.
Tools
- Complete downloadable builds for Family History Advisor and Recipe & Meal Planner.
- Personal Life Library structure and privacy policy template.
- Household and life-operations mapping worksheet.
- Mode-labeling prompt patterns.
- Quality-of-life reflection worksheet (before and after).
Privacy, local models, and your own hardware
For some students this chapter is a curiosity. For others — therapists, attorneys, financial advisors, anyone whose work involves data that legally cannot pass through someone else’s servers — it’s the entire reason they’re here.
You’ll learn how to run your AI Executive System on infrastructure you control: language models on your own hardware, orchestration self-hosted on a machine you own, and a chat surface that never sends a message off your network.
- Running local models on your own hardware — what a Mac Mini can actually handle, where local models are strong, and where you’ll still want a frontier model.
- Self-hosting your orchestrator and communicator on infrastructure you control.
- A local document sanitizer that strips sensitive details before anything leaves your machine.
- Honest assessments of the tools that aren’t ready yet — including what we recommend against, and why.
The trade-offs get named throughout. Local models lag the frontier by six to twelve months, and self-hosting makes you the system administrator. For students in regulated work, that trade is usually worth making. For everyone else, this is a good chapter to know exists.
S.O.L.I.D. Outcome: A clear-eyed understanding of what running AI on your own infrastructure actually requires — and, if your work demands it, a working self-hosted stack where sensitive data never leaves your control.
Milestones
- Privacy requirements assessed honestly against the work you actually do.
- If applicable: a local model running on hardware you own.
- If applicable: orchestrator and communicator self-hosted on infrastructure you control.
- If applicable: document sanitization workflow in place for sensitive material.
Tools
- Local model setup guide (hardware recommendations, model selection, quantization basics).
- Self-hosting guides for your orchestrator and communicator.
- Complete downloadable Local Document Sanitizer build.
- Hybrid architecture patterns — local for sensitive work, cloud for everything else.
- Honest tool assessments, including the ones we steer students away from.
“Placeholder quote … the short, punchy line from the video”
Placeholder for the longer pull-quote — the two or three sentences from this student’s video that carry the most weight.
Scale
Value: Scale long-term work and life quality
Your Executive Advisory Council
Up to this point, your agents have been helping you with this-week work — drafting emails, scheduling meetings, writing proposals. The Council is where you build something different: a small group of AI advisors with long-term memory across your professional life that helps you think at 1–3 year altitude. The decisions that don’t show up in this week’s task list.
The Council isn’t one agent doing a task. It’s a group of advisors — Strategy, Finance, People, Innovation, plus an optional Ethics & Risk seat — each with their own lens, each remembering what you’ve discussed before, each ready to weigh in on your next major decision.
You’ll learn the Council pattern and the long-term memory architecture that spans years, not chats. You’ll also set up the review rhythms — weekly and quarterly — and a decision log that lets future-you audit past-you.
S.O.L.I.D. Outcome: A Council of 3–5 advisors with long-term memory, a quarterly cadence on your calendar, and one real decision documented in the “before → Council input → after” format that turns isolated calls into compounding judgment.
Milestones
- Council seats chosen and each seat charter drafted.
- Long-term memory pattern implemented in your tech track.
- Decision log format created and running.
- First quarterly Council review held with real inputs from your Library and specialist agents.
Tools
- Council seat charter templates.
- Long-term memory build guides.
- Decision log template.
- Weekly review and quarterly review agendas with prep prompts.
Release in progress. Phase 3 lessons and templates are publishing as they’re finished — complete by September 2026.
Your Chief of Staff
Your Chief of Staff is the agent you talk to first. Rather than remembering which specialist handles your mail and which handles your calendar, you bring your day to one place. The Chief routes the work to the right specialist, pulls the threads together, and hands you back something coherent.
Before the Chief: finish a client call, then open your inbox manager for the follow-up, your scheduling assistant for next week’s time, your CRM assistant for the call notes, your project planner to check the timeline. Four chats, four context windows, four places to re-summarize what you just discussed.
After: you bring one message to the Chief. “Just got off with Henderson. Draft a follow-up, propose a time for next week, log the call in the CRM, check whether the project plan needs an update.” The Chief reads it, routes the four sub-tasks to the right specialists, and comes back with one consolidated reply. You confirm what you want to send, and you move on.
That’s not a small change. That’s the difference between operating a toolkit and directing a team.
S.O.L.I.D. Outcome: A Chief of Staff routing multi-step work across your specialist team and handing back one consolidated answer.
Milestones
- Chief of Staff deployed with routing instructions covering your full career team.
- First real multi-agent task run through the Chief (e.g., a full post-call follow-up sequence).
- Weekly review rhythm established through the Chief.
Tools
- Chief of Staff build guides (plus a Microsoft implementation covered in the appendix).
- Routing-instruction templates.
- Weekly review prompt patterns and prep checklists.
- Delegation tracker showing what the Chief handled versus what still needs you.
Release in progress. Phase 3 lessons and templates are publishing as they’re finished — complete by September 2026.
Your Home Manager
The Home Manager is the personal-side mirror. Same conductor role, different domain. Family logistics. The calendar that has soccer practice, the parent-teacher conference, and the recital on the same page. Meal planning. Travel and itineraries. The perennial “did anyone schedule the dentist.” The version of “having someone help” most of us have never been able to afford.
Together, the Chief and the Home Manager give you a single front door to your entire AI team, on both sides of your life. This is the moment your collection of individual builds stops being a toolkit and becomes a system you actually run your days through.
S.O.L.I.D. Outcome: A Home Manager coordinating the personal side — calendar, meals, travel, appointments — through the agents you’ve already built.
Milestones
- Home Manager deployed with your personal-side team attached.
- Family calendar integrated with clear privacy boundaries.
- First real household coordination task run through the Home Manager (trip planning, weekly meal plan, or equivalent).
Tools
- Home Manager build guides.
- Household ops mapping template.
- Family calendar integration recipes with privacy defaults.
- Personal-side privacy checklist for household and family data.
Release in progress. Phase 3 lessons and templates are publishing as they’re finished — complete by September 2026.
That’s the plan.
By the end of the program you’ll have 20+ working agents — covering your inbox, calendar, CRM, proposals, project workspace, briefings, family logistics, meals, long-term Council decisions, and more — all organized under a single Chief of Staff for your career and Home Manager for your life. All portable. All running on infrastructure you control, with data you own, using models you can swap when the next great release ships — and templates that keep updating as new orchestrators and platforms earn their place in AIEX.
“Work that before took weeks, months, maybe years … at record speed”
Having a full set of agents changed my work and my learning … they’re doing work that before took weeks, months, maybe years, at record speed. My focus doesn’t have to be on the work — my focus is on the outcome … Before, I’d do my learning in the middle of the night … now I’m patient, calm, and present … there for my family on an emotional level.
The Support: 5 Layers
Depending on the level of support you choose, you’ll have access to some or all of the following throughout the 6-month program. The goal is simple: you’re never left alone with a pile of prompts. You have humans, structure, and peers helping you actually build your ecosystem of AI coworkers.
Training
What it is
The full curriculum recorded and organized in the course platform — every lesson, every build, every reference — plus AIEX Demo Days: biweekly live sessions where a coach or a student walks through a full build they’ve shipped.
How it helps you
The recorded material gives you a clear path from your first assistant to your Chief of Staff, one lesson at a time, at your own pace. The Demo Days show you completed builds in the wild — what the assistant does, how it was configured, what the builder had to iterate on, and how it changed the way they work day to day. Less abstract pattern teaching, more “here’s the thing I built and here’s how you can build the same thing for yourself.”
Format & cadence
Recorded curriculum available in the member area and updated over the cohort. Live Demo Days every other Thursday, with recordings added to your private library.
Tools
What it is
A living template library of every assistant taught in The Plan, packaged as downloadable, ready-to-run builds for each of our supported tech tracks — IWAI Studio, Claude Cowork, n8n, and others as they earn a place in AIEX.
How it helps you
You don’t start from a blank page for any of it. Every assistant in the program lands in your library as a template that plugs directly into your track of choice — prompts, logic, tools, and integrations already wired. Adapt it to your context and it’s yours.
Format & cadence
Downloadable templates, prompts, checklists, and full workflow files inside the member area. Continuously updated as new orchestrators, platforms, and models earn a place in the AIEX focus — so what worked six months ago and what works today are both available, and the library grows with the field rather than freezing at your enrollment date.
Coaching
What it is
Direct 1:1 coaching from our team. It opens with a 30-minute kickoff session to map your build plan, then continues as AIEX Fast Passes — 30-minute, bookable sessions dedicated to your exact build — plus a private channel for questions in between.
How it helps you
Screenshare, and sit with the specific thing you’re stuck on. The OAuth flow that isn’t authorizing. The instruction that isn’t behaving. The Library that isn’t retrieving the way you expected. The Council configuration you can’t figure out how to hand off between advisors. Whatever it is — bring it to a Fast Pass and we’ll work through it in your actual environment until it’s working. A 30-minute session with a coach is almost always faster than another hour of you fighting it alone.
Format & cadence
Bookable directly from the course platform. Included with the Coaching tier (4 passes) and Executive Concierge (10 passes), available from Day One and good for a full year from your start date. The kickoff session is usually booked within about two weeks, depending on your availability.
Executive Concierge
What it is
Our done-for-you executive service. Our team works directly with you to select and build ten of the highest-impact assistants from The Plan — configured for your work, your accounts, your tools, and your life — over roughly 4–8 weeks.
How it helps you
You skip the learning curve. Instead of building assistants one at a time, you get a working team of AI coworkers installed by the people who wrote the curriculum. We handle the kickoff (which agents will move the needle most for you), the build, the connections, and the launch. Then we teach you how to run it and how to keep extending it yourself, using everything else already inside the program.
Format & cadence
Included in the top tier only. A single 4–8 week engagement — kickoff, build, launch, and handoff. This is a one-time buildout, not an ongoing service. Once your ten agents are live and you’re running them, the engagement completes. Ongoing advisory support is available as a separate add-on if you want it later.
Community
What it is
A private community space for AI executives and high-performance professionals in this cohort.
How it helps you
You’re surrounded by peers who are also building AI coworkers, not arguing about prompts. This is where you find collaborators, accountability, and long-term relationships.
Format & cadence
Private online space (Slack) with channels for wins, build logs, tech questions, and co-working. Optional pop-up events or peer circles during the cohort.
Exact cadence and access vary by tier. All tiers include Training, Tools, and Community. Coaching (delivered as Fast Passes) is included in the Coaching and Executive Concierge tiers, with more Fast Passes at the higher tier. Executive Concierge is a done-for-you engagement included only in the top tier. See The Investment for the specifics.
“The biggest thing that surprised me … is just how involved the team is”
You can feel like you’re on an island when you’re exploring something emerging … Just knowing you have a community you can tap into, and seeing how helpful everyone is towards one another — if you ask something, people are quick to add on and really help out.
Learn from people on a mission to make AI work for everyone
Plus — an ever-growing cast of IWAI teammates and guest instructors.
Rob is a 20-year tech-industry veteran, software developer, and entrepreneur who started coding at age 12. He founded a million-user cloud-storage startup (acquired in 2009) and is CEO of HDC, a development firm whose software has powered more than 100,000 websites — including work for Harvard, MIT, The World Bank, Marriott, Intel, Facebook, and The Oscars. His work has appeared in Wired, Forbes, Fortune, and TechCrunch.
But Rob’s real mission is teaching. After a successful tech career, he found that helping tens of thousands of people gain comfort and confidence with technology was even more fulfilling than the work that came before it. He built Innovating with AI on a simple belief: that everyone — not just engineers and executives — deserves to thrive as AI reshapes work and life.
Nyasha is an educator and software developer on a mission to make AI and technology accessible for everyone — no gatekeeping, no jargon, no overwhelm. As a LinkedIn Learning instructor, she has created multiple courses and taught more than 50,000 students, and she shares practical, jargon-free guidance through her YouTube channel and “The Hopeful Workspace” podcast. Her creativity and insights have been featured in Time Magazine and The Guardian.
Nyasha believes tech education shouldn’t be reserved for computer-science graduates or gatekeepers — every person should have the tools to understand and use technology for their own goals. That mission is the very heart of what we do at IWAI.
IWAI Studio: The Fast Start
The fastest path from “I have an idea” to “I have a working assistant.” Model-agnostic, fully portable, free with enrollment.
Early on, students spent their first weekend fighting tooling instead of building. The workflow was about 20% of the work. Setup was the other 80%.
So we built IWAI Studio to flip that ratio. It isn’t a substitute for the curriculum — it’s the fastest path through it.
Use whichever model you want. Claude, GPT, or Gemini on your own API key. Or pick an open model — Qwen, Kimi, DeepSeek — and Studio runs it in a U.S. datacenter or sets it up on your own computer. Far cheaper, and nothing goes offshore either way.
In August, Studio arrives on Mac and Windows, free for AIEX students just like the web app. The desktop app is ideal for anyone who needs to handle sensitive documents that can’t go to the cloud — and for everyone who wants the most privacy-first approach without sacrificing functionality.
One app, everything in it
Chat, orchestrator, model, and tools in one workspace. First assistant inside 30 minutes.
Any model, your own API key
Claude, GPT, or Gemini — wired in once, swapped from a dropdown. No code, no rebuild.
Open models, no offshore risk
Qwen, Kimi, and DeepSeek run in U.S. datacenters — a fraction of frontier cost, and your data never leaves the country.
Local models on your machine
Starting in August, the Mac and Windows app sets up small models on your own computer. Nothing leaves it at all.
Export anywhere
Any assistant becomes a Cowork skill or n8n workflow in two clicks.
Share your workspace
Teammates and family use what you build. No extra accounts, no extra cost.
Free for AIEX members, web and desktop. Bring your own API keys — typical usage runs a few dollars a month. Very high-volume users may see paid capacity options later; for nearly everyone it stays free.
Meet Your Future AI Executive Team
Every one of these is a real, working build inside the program — a template you can install, adapt, and start using right away. The library is always growing, and students routinely create unique and novel assistants based on what they learn in the program.
Your News Analyst Daily briefings pulled from the topics you follow.
Your Weather and Commute Planner What to wear, when to leave, whether to reroute.
Your Expenses and Mileage Tracker Expenses and mileage, reconciled automatically.
Your Grocery and Pantry Manager Grocery list and pantry inventory, always current.
Your Weekend Planner Local plans tuned to what your household enjoys.
Your Billing and Time-Tracking Assistant Time entries and invoicing, handled for you.
Your Lead Prospector Fresh leads, saved straight into Docs and Sheets.
Your Inbox Manager Triages your inbox by the rules you set.
Your Scheduling Assistant Finds meeting times across everyone’s calendars.
Your CRM Assistant Keeps contacts and deals current, automatically.
Your Project Planner Turns a vague brief into a structured plan.
Your Proposal Writer Client proposals, drafted in your voice.
Your Family History Advisor Answers from your structured family archive.
Your Recipe and Meal Planner Meals planned around your household’s real needs.
Your Strategy Advisor* — release in progress Council seat on positioning, competition, and horizon.
Your Finance Advisor* — release in progress Council seat tracking cash, margins, and commitments.
Your People Advisor* — release in progress Council seat for team and hiring decisions.
Your Innovation Advisor* — release in progress Council seat asking if the plan is bold enough.
Your Ethics & Risk Advisor* — release in progress Pressure-tests decisions against your values.
Your Chief of Staff* — release in progress Routes requests, one coherent answer back.
Your Home Manager* — release in progress Family calendar, meals, trips — one place, not six apps.
Release in progress. The seven Phase 3 builds are publishing as they’re finished — complete by September 2026.
“I’m very attentive to detail … and they have that same lens of quality”
Rob’s attention to detail, his thoroughness in the curriculum, his empathy and understanding … proactively imagining what concerns a person would have, then solving them before they even realize that’s going to be a thing. It’s magical — you’re absolutely getting your money’s worth with this company.
Join The AI Executive System
3 Options for High-Performance Professionals…
I’ve priced this with the following intentions in mind:
- Make it a small fraction of the value of the time, energy, and opportunities we’re helping you unlock.
- Keep it accessible for the AI Executives joining our program.
- Limit the number of students so everyone gets the attention they need to be successful.
Training
Includes…
- The complete curriculum, from your first assistant through the Chief of Staff and Home Manager
- Downloadable workflow files and complete builds for 20+ assistants (prompts, checklists, systems, examples) in 3 tech tracks
- Live biweekly AIEX Demo Days — coaches and students walking through completed builds
- Private 24/7 Slack community access
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
12 payments of $297
(that’s only $9.76 a day)
(or pay in full and save $567)
Recommendation:
Select this if you’re disciplined enough to follow the recorded curriculum, use the tools, and implement on your own with community support. Good choice if cash flow is a factor and you want the freedom to move at your own pace.
(If cash flow is too limited to invest at this level, then I strongly recommend not investing in this program. Stay on our interest list to potentially join when you’re in a stable place that allows for making effective decisions without financial duress.)
Coaching
Includes everything in Training, plus…
- Your personalized build plan — a 30-minute kickoff session mapping which assistants will move the needle for your role. You start with a plan instead of a list.
- 4 Coaching Fast Passes — 30-minute bookable 1:1 sessions with our coaching team, dedicated to your exact build. Valid for one year.
- Priority feedback in the coaching-tier-exclusive community channel — for the decisions and blockers between passes.
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
12 payments of $497
(that’s only $16.43 a day)
(or pay in full and save $967)
Recommendation:
Select this if you want more direct 1:1 access to our team when you hit a snag. The kickoff build plan, four Fast Passes, and a private channel to the team give you more room to ask questions and validate decisions as you build — while you still do the building yourself.
Executive Concierge
Includes everything in Training and Coaching, plus…
- Done-for-you build of 10 assistants — the highest-impact agents from The Plan, configured for your work, accounts, tools, and life.
- A structured 4–8 week engagement — kickoff, build, launch, and handoff, where we teach you to run and extend the system yourself.
- Priority access to our team during your engagement.
- 10 Coaching Fast Passes — six more than Coaching, for expansion and new builds after handoff.
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
$10,000
one-time payment
(or 12 payments of $997)
Note: This is a one-time buildout, not an ongoing service. Once your 10 agents are live, the done-for-you engagement completes. Ongoing support is available separately.
Recommendation:
Select this if you want the fastest possible path to a fully built AI Executive System, have limited time to design and build it yourself, and want a working team of AI coworkers installed by the people who wrote the curriculum. Ideal for busy executives, founders, and consultants who’d rather have the system built for them than build it themselves — and who then want the tools and knowledge to keep extending it on their own.
Important: All payment plans have a 12-month commitment. If you anticipate unpredictable finances or don’t feel confident you can complete the payment cycle, I’d advise against joining at this time.
If you have any questions or concerns about IWAI’s AI Executive System program, please send us a text message, WhatsApp message or email. We’re happy to help:
Text or WhatsApp: +1 (888) 210-2282support@innovatingwithai.com
Our 60-Day Guarantee
(TL;DR for existing students: This matches our standard for our other programs.)
More than 1,000 students have already started building successful consulting businesses with the AI Consultancy Project. We have similar goals for The AI Executive System — which is why I’m also making it completely risk-free.
Refund in the first 3 days for any reason—no questions asked.
Refund in the first 60 days if you try it and it doesn’t work.
From the moment you enroll, you have a 3-day grace period to cancel for any reason and receive a full refund.
After that, you can still try the program and request a refund within your first 60 days. Here’s what I ask:
- Watch at least 4 live or recorded trainings.
- Show your work in attempting to build at least 3 of the assistants in the early chapters of the program.
Once you’ve taken these steps, if you still feel the program isn’t right for you, I’ll refund 100% of your investment.
Why these steps? Because success comes from putting in the work. Whether it’s starting a new fitness routine or a new business, measurable progress requires consistent effort. This guarantee ensures you give yourself the best chance to succeed while keeping your investment safe.
Family & Medical Sabbatical Guarantee – so you can always put your loved ones first.
If you choose one of our 12-month payment plans, life’s unexpected challenges won’t stand in your way.
If an immediate family member experiences a major medical or financial problem, you can pause your payments for up to 3 months.
This applies to you, your spouse, children, parents, or anyone who shares your household. The most important thing to me is taking care of your loved ones – and I know that sometimes means diverting attention temporarily from work. Life happens! That’s why all my employees have plenty of paid family and medical leave, and why I extend the same courtesy to my students too.
If you need a break from payments for any reason described above, just email us and we’ll pause your payments for 3 months – and when you return from your sabbatical, my team and I will help you get back on track to accomplish all your goals.
Life happens, and supporting you through it is part of our commitment to your success.
Answers to Your Most Frequently Asked Questions
(TL;DR for existing students: This matches our standard for our other programs.)
No. You do not need to be a developer or ML engineer to benefit from this program.
AIEX is designed primarily for non-technical executives and professionals who want to design an ecosystem of AI coworkers around their existing expertise. We focus on practical, mostly no-code tools and workflows that you can use yourself and, later, delegate to technical partners if needed. That said, we have some advanced material too, so for our techie folks, don’t worry — we’ve got your back. Just don’t expect rocket-engineering-grade builds.
That’s totally fine.
We assume:
- You’re comfortable using modern software.
- You’re willing to experiment and learn.
We do not assume you’ve already built agents, RPA workflows, or AI products. The curriculum will guide you from “basic familiarity” to “I can design and run AI coworkers that actually do work for me.”
Yes. We’ve had students from around the world in our other programs.
Most live calls — including AIEX Demo Days — are scheduled in US daytime hours (Eastern Time), which may be early morning or evening for some regions. All sessions are recorded, and the community space is active across many time zones, so you can still get support even if you can’t attend everything live.
Think of it this way:
- AICP helps you build an AI consulting business.
- AIEX helps you become the AI Executive of your own work and life, whether you’re an executive, senior IC, consultant, or founder.
You do not need AICP first to join AIEX.
If you have taken AICP, AIEX is where you:
- Treat yourself as the FTE owner-operator,
- Build the ecosystem of AI coworkers around your own work first,
- And only then decide if/how you want to roll that into new services for clients.
AIEX is focused on you and your immediate sphere of control: your role, your responsibilities, your home, and the people who rely on you.
In many ways, it’s the pre-requisite to any full-company or enterprise rollout. Once you’ve proven what works for you (and possibly your team), you’ll be in a much stronger position to lead a broader transformation.
If your main goal is to re-engineer an entire organization right away, this isn’t that program. If your goal is to put the oxygen mask on yourself first, AIEX is the right place.
No.
AIEX is designed for high-performance executives, professionals, consultants, and founders who already have meaningful experience in their field. The program will absolutely make you more valuable and future-proof, but it’s not a formal job-training or placement program, and we don’t issue accredited certifications.
The AI Executive System is designed to be primarily self-paced, with a live component you can dip into as your schedule allows:
- Recorded curriculum. The full program — every lesson, every build — is recorded and available in the course platform on Day One. Go through it at your own pace, in any order that fits your work.
- Live AIEX Demo Days. Every other Thursday, a coach or a student walks through a full build they’ve shipped. Attend live if you can; recordings go into your private library if you can’t.
- Coaching Fast Passes (Coaching and Executive Concierge tiers). Bookable 1:1 sessions with our team when you get stuck on your specific build.
You can absolutely follow along on your own schedule. If life or work gets intense, you can step back, then use recordings and toolkits to catch up.
AIEX Demo Days are our biweekly live sessions, every other Thursday. Instead of abstract pattern teaching, a coach or a student walks through a full build they’ve shipped — what the assistant does, how they configured it, what they had to iterate on, and how it’s changed the way they work day to day.
Less “here’s how to think about the pattern,” more “here’s the thing I built and here’s how you can build the same thing for yourself.” Recordings go into your private library, so if you can’t attend live, you don’t miss anything.
It’s flexible, but we recommend being able to commit at least 5 hours a week. Some weeks you’ll lean in more, some weeks less — the curriculum is recorded and yours to work through on your own schedule.
What matters is that the time is real. This isn’t a “press play while you sleep” program: you’re building working assistants, and each one needs you to set it up, point it at your own accounts, and iterate until it behaves. If you can’t protect roughly that much time, you’ll get more out of joining a later cohort.
Continuously. New templates land in the library when:
- New orchestrators, platforms, or models earn a place in AIEX (we evaluate each carefully — not everything makes the cut).
- Students in the program share patterns that generalize well.
- Our team ships new builds worth adding.
You get access to every update at no additional cost, for as long as you’re enrolled. The library grows with the field rather than freezing at your enrollment date.
You’ll be able to build it. Once you’ve worked through one or two assistants in the program, you’ll have the pattern — the shape of every future build — and can apply it to whatever your work or life demands.
Students routinely build assistants we never taught: reading list curators, personal trainers, procurement analysts, editorial calendars, translators, symptom trackers, book club coordinators, homework tutors, household maintenance planners. The 20+ assistants in our curriculum are examples of the pattern in action, not the limit of what’s possible.
If you get stuck on a specific build that isn’t in the curriculum, that’s exactly what Fast Passes are for — included with the Coaching and Executive Concierge tiers.
AIEX Fast Passes are 30-minute, bookable 1:1 sessions with our coaching team, dedicated to your exact build.
Screenshare, sit with the specific thing you’re stuck on — an OAuth flow that isn’t authorizing, an instruction that isn’t behaving the way you expected, a Library that isn’t retrieving the right chunks — and we’ll work through it together until it’s working in your actual environment.
Fast Passes are included with the Coaching tier (4 passes, plus a 30-minute kickoff session) and Executive Concierge tier (10 passes). Book them directly from the course platform. They’re valid for a full year from your enrollment date.
In scope: Our team works directly with you across a structured 4–8 week engagement to select and build ten of the highest-impact assistants from The Plan — configured for your specific work, accounts, tools, and life. The engagement has four beats: kickoff (where we help you choose the ten agents that will make the biggest difference for you), build (where our team executes), launch (where they go live in your environment), and handoff (where we teach you how to run and extend the system yourself).
Not in scope: Ongoing maintenance. Ongoing advisory. Unlimited assistants beyond the ten you select. This is a one-time buildout, not an ongoing service.
After the engagement completes, you keep everything: the ten agents running, ongoing access to the continuously-updated template library, and 10 Coaching Fast Passes for post-handoff expansion, iteration, or new builds you want to try on your own. If you want ongoing advisory support after your engagement, that’s available as a separate add-on.
Yes. Email our team any time and we’ll send you a custom upgrade link — you’ll pay the difference between tiers, not the full higher-tier price.
Each tier has a hard cap (100 for Training, 50 for Coaching, 20 for Executive Concierge), so upgrades are first-come, first-served. The Executive Concierge tier in particular tends to fill quickly because of the team time involved in each build engagement.
IWAI Studio is our own platform — on the web today, and on Mac and Windows from August. It bundles the four components every assistant is made of into one clean app, so you can be talking to your first AI coworker inside 30 minutes. The desktop app keeps everything local by default and adds U.S.-hosted open-source models; both versions are free with enrollment.
Access to Studio is included free with your enrollment.
You don’t have to use it. The program teaches three tech tracks — Fast Start (IWAI Studio), Integrated Suite (Claude Cowork, or Microsoft Copilot Studio if required by your employer), and Self-Hosted Stack (n8n + Zulip). Every assistant we teach ships as a downloadable template for all supported tracks, so you can build on whichever one fits your situation.
That said, nearly every student starts in Studio, because it’s the fastest path through the curriculum. Many students stay in Studio permanently — not because they can’t move, but because the combination of ease of use, cross-vendor model access, and cost control matches how they actually want to build.
Short answer: most students should start with the Fast Start track (IWAI Studio). It’s the shortest path to a working assistant, the most flexible in terms of swapping models, and free with your enrollment.
Longer answer, in order of what should influence your choice:
- If you handle sensitive data that legally can’t touch a cloud SaaS — regulated healthcare, legal work, government contracts, financial services with strict data rules — the Self-Hosted Stack (n8n + Zulip) is your track. Your infrastructure, your rules.
- If your employer or client requires Microsoft, the Integrated Suite track via Microsoft Copilot Studio is available. See the Microsoft question below for our honest take.
- If you already live inside the Claude ecosystem and love it, the Integrated Suite track via Claude Cowork is a polished experience.
- For everyone else, Fast Start.
Switching tracks is always possible. Every assistant we teach ships as a downloadable template in every supported track’s format, and IWAI Studio has a built-in export tool that turns any assistant into a Cowork skill or n8n workflow. The concepts transfer across all tracks — only the wiring changes.
We support it. The program includes a dedicated Microsoft Ecosystem chapter covering how to build the whole AIEX system inside M365 — Copilot Studio, Dataverse, SharePoint, Entra ID — plus implementation recipes for the highest-impact assistants (Inbox Manager, Scheduling Assistant, CRM Assistant, Proposal Writer, and Chief of Staff).
Here’s our honest take: we generally don’t recommend the Microsoft track unless you have to use it.
- Microsoft is typically 3–6 months behind the leading-edge AI labs on new capabilities. The versions of Claude, GPT, and other models that ship in Copilot Studio arrive later than the versions that ship elsewhere.
- The tooling is more diffuse — you’re stacking seven Microsoft products (Copilot Chat, Copilot Studio, Dataverse, SharePoint, Teams, Entra ID, Microsoft Graph) instead of learning one platform. That’s real surface area.
- The cost picture is opaque and skews expensive for self-funded learners: M365 base + Copilot license + Copilot Studio credits stack up quickly.
If Microsoft is required for you — IT policy, enterprise governance, Microsoft Partner obligations, the simple gravity of “we’re an M365 shop and we’re not going anywhere” — the AIEX Microsoft chapter gives you a real path, and roughly 10% of our students land here for exactly those reasons. If you have the choice, one of the other tracks will serve you better.
It’s available as an appendix rather than one of the three primary tracks: sixteen lessons walking through Make.com as a middle-tier orchestration option that sits between IWAI Studio and a full self-hosted n8n stack — useful if you want more flexibility than a purpose-built platform without the setup overhead of a complete self-hosted stack.
Yes, in most cases. The program teaches you to work with your own API keys directly from OpenAI, Anthropic, and/or Google — so you own the accounts, control the spend, and can swap models as new ones ship.
Cheaper options exist, too. IWAI Studio can run open models like Qwen, Kimi, and DeepSeek in U.S. datacenters for a fraction of frontier pricing, and from August the desktop app can run small models directly on your own computer at no per-token cost at all.
Typical cost: a few dollars per month per provider for normal use — most students run their whole cabinet on $5–20 total across all providers. Heavy retrievers (writing lots of proposals against a big library, deep-research sessions) can push higher, but that’s usage-driven, not baseline.
Exception: if you use the Integrated Suite track via Claude Cowork, your Claude subscription (starting around $20/month) covers your Claude work — you don’t need a separate API key for Cowork-only builds.
We walk through account setup, safe key storage, and cost-tracking tools in the first module — no surprises.
We offer 12-month payment plans for the Training and Coaching tiers, so you can spread your payments over time instead of paying all at once.
That said, we’re serious about financial health:
- If making the monthly payment would put you in chronic financial stress, we recommend waiting for a future cohort instead of stretching beyond what’s realistic.
- If your finances are stable but you’d simply like to smooth cash flow, the payment plan is there to support that.
Your enrollment comes with:
- A 3-day cancel-for-any-reason grace period. If you enroll and something urgent comes up in the first three days, email us and we’ll refund you in full, no questions asked.
- Our Family & Medical Sabbatical Guarantee for payment plans: if you experience a major medical or financial hardship for yourself or your immediate family/household, you can pause payments for up to 3 months — any time across your 12-month plan — so you can focus on what matters most.
We know life happens. The program is here to support your long-term success, not punish you for emergencies.
Yes — 100% of it. Your ideas, systems, assistants, data, client materials, and intellectual property stay entirely yours. We don’t claim your IP, and we’re not here to claim a percentage of your future value. Our job is to be your launchpad and advisor.
Anything sensitive stays that way: we never share your work or your story without your explicit consent, and we follow standard SaaS security practices.
Given the nature of our industry, we take data and privacy very seriously. And, even beyond our industry, we believe it’s just the moral and ethical thing to do in a decent society.
Your enrollment is protected by our 60-day performance guarantee.
Within the first 60 days of enrollment, if you’ve:
- Watched at least four live or recorded trainings, and
- Shown your work in attempting to build at least three of the assistants in the early chapters of the program…
…and you still feel the program isn’t working for you, you can choose between:
- A full refund, or
- Getting hands-on help from our team to rework your ecosystem plan until it fits your situation.
The same terms apply to Executive Concierge students — even though your engagement is done-for-you, the 60-day guarantee protects you exactly the same way as every other tier. We stand by all our work with our unparalleled guarantee.
We guarantee results to everyone who takes the program seriously and puts it into action — because we know, from experience, that this system works when you do.
Realistic Expectations…
and our shared responsibility
I’ve designed The AI Executive System for you to be successful with an average time investment of about 5 hours per week over 6 months.
Some weeks you’ll lean in more, some weeks less – but this isn’t a “press play while you sleep” kind of program. You’re building a real ecosystem of AI coworkers that will touch your work, your home, and the people you care about.
That also means I can’t guarantee a specific raise, promotion, revenue number, or hours reclaimed.
Not only would that be misleading and illegal – it also misses the point of what we’re building. The only guaranteed outcome in life is mortality; everything else is probability. There is risk, and there is work.
What I can guarantee is this:
- I’ll bring the same level of care and rigor I use with Fortune 500 clients and the 1,000+ students in our other programs.
- My team and I will treat this as a program for a better future of work – one where AI gives you more time, more capacity, and more presence with the people who matter, not less.
- We’ll keep improving the curriculum, tools, and support based on what’s actually working for you and your peers in the room.
- We’ll keep the AIEX template library current — as new orchestrators, platforms, and models earn a place in the program, the library grows with the field rather than freezing at your enrollment date.
On your side, here’s what I ask:
- You show up for the trainings (live or recorded) and use the tools.
- You give your AI coworkers real work to do – not just “play around with prompts” – and are willing to iterate when things are imperfect at first.
- You use the time and energy you free up on purpose: for deeper work, better leadership, time with family, community projects, or simply being more human with the people around you.
Because here’s my philosophy:
A small number of us are incredibly lucky.
We have careers, devices, and opportunities that AI can meaningfully improve.
When you’re one of those people, you have a responsibility to kick ass with it – and then use the gains to lift others, not just yourself.
That’s what this program is really about.
Yes, I selfishly want to brag about you later.
I want your story as an AI Executive to be one that inspires other people to build a more generous, human future of work.
Just imagine a future you, 6 months from now, looking back at this moment with a thought bubble above your head…
“At the time, I didn’t know exactly how it would play out… but I did it anyway, because I don’t want AI to happen to my work and family. I want to lead how it happens for us.”
If everything on this page makes sense, and you’re ready to build your own ecosystem of AI coworkers – for your work and your life – then there’s only one thing left to say:
I’m looking forward to seeing what you create.
To your innovation, and to the people who benefit from it,
Rob Howard
Innovating with AI
Join The AI Executive System
3 Options for High-Performance Professionals…
Training
Includes…
- The complete curriculum, from your first assistant through the Chief of Staff and Home Manager
- Downloadable workflow files and complete builds for 20+ assistants (prompts, checklists, systems, examples) in 3 tech tracks
- Live biweekly AIEX Demo Days — coaches and students walking through completed builds
- Private 24/7 Slack community access
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
12 payments of $297
(that’s only $9.76 a day)
Coaching
Includes everything in Training, plus…
- Your personalized build plan — a 30-minute kickoff session mapping which assistants will move the needle for your role. You start with a plan instead of a list.
- 4 Coaching Fast Passes — 30-minute bookable 1:1 sessions with our coaching team, dedicated to your exact build. Valid for one year.
- Priority feedback in the coaching-tier-exclusive community channel — for the decisions and blockers between passes.
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
12 payments of $497
(that’s only $16.43 a day)
Executive Concierge
Includes everything in Training and Coaching, plus…
- Done-for-you build of 10 assistants — the highest-impact agents from The Plan, configured for your work, accounts, tools, and life.
- A structured 4–8 week engagement — kickoff, build, launch, and handoff, where we teach you to run and extend the system yourself.
- Priority access to our team during your engagement.
- 10 Coaching Fast Passes — six more than Coaching, for expansion and new builds after handoff.
Plus…
- Lifetime Access to Recorded Materials: Take it at your own pace, start and stop as needed.
- 3-Day Grace Period: Cancel for any reason within your first 3 days.
- 60-Day Guarantee: Refund in the first 60 days if you try it and it doesn’t work.
Investment:
$10,000
one-time payment
(or 12 payments of $997)
Note: This is a one-time buildout, not an ongoing service. Once your 10 agents are live, the done-for-you engagement completes. Ongoing support is available separately.
Important: All payment plans have a 12-month commitment. If you anticipate unpredictable finances or don’t feel confident you can complete the payment cycle, I’d advise against joining at this time.
If you have any questions or concerns about IWAI’s AI Executive System program, please send us a text message, WhatsApp message or email. We’re happy to help:
Text or WhatsApp: +1 (888) 210-2282support@innovatingwithai.com
“Four weeks of my time … done in a few minutes”
I built 28 agents, and I’m saving 72 to 100 hours [a month]. I’m promising 30-day delivery and delivering in four days … It’s life-changing — not only for myself, but for my household, for my extended family, and for my community. I feel like I’m making an impact.