Getting good at AI is the one thing you can’t delegate.
Your team can learn the tools. Someone else can build the systems. But knowing what AI can be trusted to do — and how to use it on the work only you can do — is becoming part of leading.
Over two private 90-minute sessions, we build your personal AI practice around your actual work: the documents, recurring responsibilities, strategy, analysis, and decisions that are yours alone.
No group. No generic examples. No lecture series.
John Frydman · Founder, Digismart · Miami
This is for you if…
- You have tried ChatGPT, received something generic, and quietly returned to doing the work the old way — while suspecting there is much more there.
- You are the person everyone expects to have the AI answer, which makes it difficult to ask the basic questions anywhere else.
- You do not want a course, a certification, or a playlist of demonstrations. You want to understand AI by using it on work that already matters to you.
- Your material is sensitive — strategy, financials, client matters, personnel — and a group setting was never going to work.
- You want to know what is genuinely useful, what is unreliable, and what is simply not worth your time.
What changes after two sessions.
You get hours back every week
Board preparation, competitive analysis, investor updates, research, and the first draft of almost anything can move much faster. The work is still done by you, with your judgment. It is not handed off. It remains yours.
You make better decisions — not merely faster ones
AI becomes a thinking partner on the difficult calls: pressure-testing a strategy, arguing the other side, identifying missing assumptions, and surfacing risks you may be too close to see.
You stop guessing
You understand what AI does reliably, where it tends to fail, and what requires verification. You begin using it with judgment instead of hope.
You leave with a practice of your own
Everything is built around your accounts, your context, your priorities, and your work. You are not trying to remember what happened in a demonstration. You leave able to do it again.
Understand AI. Build it around you.
We begin with the mental model: how today’s AI actually works, what it is reliably good and bad at, and where it belongs in an executive’s week. Then we map your work:
- What repeatedly consumes your time
- What requires more analysis than you can usually give it
- What you postpone because getting started is difficult
- What depends on your voice, knowledge, or judgment
- What should never be delegated to AI
From there, we build your personal AI operating system. We connect the relevant context — your priorities, documents, preferences, and ways of working — so AI stops responding like a generic assistant and begins working on your world. Before the session ends, we use the setup on a real piece of work already on your desk.
You leave session one with: a clear mental model, your personal setup running on your own accounts, and the first executive routine built and working.
The sessions take place approximately one week apart. During that week, you use what we built on your actual work. You notice where it saves time, where it disappoints, what questions arise, and what you still hesitate to trust it with. Session two begins there — not with another lesson.
Turn AI into a thinking partner.
The second session moves from productivity to judgment. You bring a live decision, strategy, negotiation, difficult document, or unresolved question. Together, we use AI to examine it from several directions:
- Pressure-test the reasoning
- Argue the strongest opposing case
- Identify assumptions and missing information
- Compare the conclusions reached by different AI models
- Separate useful analysis from confident nonsense
Then we build your standing council of advisors: the perspectives you most want in the room when a problem is ambiguous and no single answer is sufficient. You learn how to assemble the right voices for a particular question, make them challenge one another, and turn the discussion into a decision you can defend.
A council session with sample numbers. Yours argues about your business, in your language.
You leave session two with: a repeatable method for judgment work, your advisory council built and answering, and a clear playbook for using both again.
What you leave with.
- A practical understanding of how AI works and where it fails
- A personal AI operating system built around your context
- Working routines for recurring executive work
- A method for pressure-testing strategies and decisions
- A standing council of AI advisors you know how to rebuild for different challenges
- Clear boundaries for sensitive information
- A one-page playbook covering what to use, what to avoid, and what to explore next
No slides were harmed in the making of these sessions — because there are none.
Ask anything. Nobody is watching.
A private setting changes the questions an executive can ask. There is no team member interpreting every uncertainty. No group pace to keep up with. No need to perform expertise you are still developing. We can work with the strategy, financial model, board document, personnel question, or half-formed decision that would never belong in a workshop.
Privacy is not an added luxury. It is what allows the work to become specific enough to matter.
The two sessions stand on their own.
You do not need to join a longer program or commit to an implementation. If the sessions reveal a larger opportunity, there are two ways to bring the work into the company:
The honest answers.
What does it cost?
The two-session private program is $3,000. If you continue into a qualifying team engagement or SmartBoard build, the full fee is credited toward that work.
Do I need to prepare anything?
A list of what annoyed you this week is plenty. The best sessions begin with real irritations, delayed decisions, and work already sitting on your desk — not hypothetical use cases.
Is my information safe?
You remain logged into and in control of your own accounts. Before sensitive material enters any AI tool, we decide what can be used, what should be anonymized, and what should stay out entirely. We will also sign your NDA. Learning those boundaries is part of becoming capable with AI.
What if I am a complete beginner?
That is entirely fine. The sessions begin with the mental model and move at your pace. Nothing is assumed, and there is no group to keep up with.
What if I already use AI regularly?
Then we spend less time on fundamentals and more on reliability, context, judgment, model comparison, and the work you still do not trust AI to touch. Private means the sessions begin where you are.
Do I need to install anything?
No. We work with tools you already have access to and decide together whether anything else is worth adding.
Remote or in person?
Either. Sessions are available in person around Miami or privately by video call anywhere else. The work is identical.
Two sessions. Your real work. AI you know how to use.
Start with a 20-minute conversation. Tell me what is on your desk, how you are currently using AI, and where you suspect you are leaving value behind. If the sessions can materially help, we schedule them. If they cannot, I will say so.
Book a 20-minute fit call