Aspiring to or navigating the hospital C-Suite? Transitioning to retirement? Maximize your wealth and embrace abundance.

If you’re a high-capacity man who’s done everything “right” and still feels that quiet ache for more alignment, you’re not imagining it.

Some friends and I used to call it Restless Soul Syndrome.  When life looks good, but something deeper keeps tugging at you.

Most financial planning doesn’t touch that.
It optimizes accounts, runs projections, and treats you like a spreadsheet.
It rarely asks who you’re becoming or how your wealth can support a life of presence, calling, and meaning.

My view is simple: wealth is a tool for becoming.
When your financial structure reflects your true priorities, you get both clarity and permission to act instead of drifting through the next decade.

In my work, men clarify what matters most and build a plan around it.
They leave with financial clarity and the confidence to move toward major life transitions with calm intention.

Here’s how I help:

Gather truth — your current reality, your resources, and the life you actually want to live.

Map priorities — turn future priorities (kids’ college, travel seasons, home plans, time away) into today’s dollar decisions.

Build the plan — a simple financial structure and portfolio that fund the identity you’re stepping into.

If you’re grateful but not fulfilled and ready to live more fully as who you are send me a message with the word “Identity.”

We can explore, without pressure, whether this kind of intentional stewardship is right for you.

All it takes is a first step.

John Montgomery

AI Cult Leader | AI-Augmented VAs, AI-First Training & Custom AI Solutions | Turning Teams into AI Superstars

AI-First puts humans second. That's backwards.

I believe in Human + AI. Together. Not versus. Not competing. Working alongside each other to create what neither could alone.

That's why I built AI Operator, created the ADOPT Method™, and started the Human + AI Manifesto movement at humanaimanifesto.org.

THE PROBLEM I SOLVE

Your team has AI tools. But adoption is scattered, results are inconsistent, and it's not hitting the P&L. 95% of AI initiatives fail to deliver business value (MIT 2025).

WHAT I DO DIFFERENTLY

The ADOPT Method™ transforms behavior, not just skills. Our Innovation Competition is where teams ship real production AI solutions (not demos) - this alone generates $250K+ in value per client.

Results:
- 1,000+ professionals trained (including Google)
- $21M+ client value created
- Up to 1,211% documented ROI
- 6-Week ROI Guarantee

THE JOURNEY HERE

I've been in AI for 10 years. But before that: door-to-door sales, printed magazine marketing, translator. Many failed entrepreneurial attempts.

Then I found my path:
- 3 years teaching at 2 universities (giving back)
- Growth consultant for 50+ companies and coach to CEOs
- CGO/Head of Growth at multiple Deep Tech startups
- COO scaling a B2B SaaS from $58K MRR to $300K MRR in 18 months
- CEO of a 110-person company

After all that, I finally found my passion. My obsession.

WHAT I'M BUILDING

AI for Better Lives is the vision. AI Operator is where it starts.

If your team has AI tools but isn't seeing real results, that's what we fix: aioperator.com

THE HUMAN SIDE

AI geek who builds systems in spare time—not just for fun, but to push boundaries and bring what I learn to businesses. Dad who partners with Claude on family adventures. Sailor dreaming of sailing the world. Multilingual (EN/FR/ES/TR). Bodrum beachside based, traveling to clients across the globe.

Let's talk: tim@aioperator.com

Tim Cakir

14 years, 3 C‑level roles, 1 promise for 2026.

I’m using AI on myself before I touch your team.

Right now Claude Code with Opus 4.5 runs my work.

Terminal. Chrome. MCPs into my Notion, Gmail, Zapier, SEMrush, Search Console.

Ridiculous.

It reads long docs, checks comments, replies with context.
It runs SEO analysis I used to pay experts 25K for.

Not theory.

I rebuilt complex workflows that made 250K in revenue.
I now run them from my own laptop, my own browser, my own IP.

No pilot purgatory.

Before AI Operator I spent 14 years in the arena:
CEO of a 110‑person company.
COO of a 65‑person B2B SaaS.
Chief Growth Officer at a 20M revenue cannabis company.

Plus professor, growth hacker, deep tech, computer vision.

Now I test everything on myself first.

If I cannot get clear ROI in my own workflows, I do not bring it to your team.
If AI does not remove repetitive work for me, I do not sell it as “transformation.”

Human + AI.

In 12 months we certified 1,000+ people.
Worked with 25+ companies.
Made close to 500K with a tiny team.

The best messages I get are simple:
“Less boring work.”
“More time for the best parts of my job.”

That is my promise for 2026.

I am here to help ambitious Founders work with AI, not fear it.

If you want to see how I run my own stack first, start with my LinkedIn, newsletter, or YouTube, or if you do take your AI transformation seriously, DM me.

Comment Happy New Year below to show each other some love. Why not right?

My 2026 tech stack runs like a small AI army.

Here’s what each tool does so I don’t have to.

Claude Code is my HQ.

I run Opus 4.5 on my computer with a full AI Operator folder.
Inside: sales, content, customers, each with Claude markdown files full of context, skills, agents, and workflows.

Result

Claude Code trains me to think in systems and code.
The terminal looks scary, but it makes me more technical every single day.

Next soldier

Aqua Voice is my brain-to-text pipe.
I talk, it writes. No keyboard. No fixing typos. No broken flow.
It already saved me over 20 hours by letting me think out loud while I work.

Inbox

I am moving from Superhuman to Jace AI after 5 years.
Jace now has multi-inbox, AI rules, and deep links into Notion, Drive, Slack.
It feels like a chief of staff that reads everything and replies for me.

Pipeline

I am also switching from Folk CRM to Lightfield.
Chat-first CRM that updates deals, creates emails, and catches every potential lead.
Less “did I forget something?” in my head, more clarity in my pipeline.

Nervous system

Notion + Notion AI + Notion agents hold the whole company.
Agents send Friday week reports, Monday plans, and my daily morning brief from all tools.
My founder time goes into the right problems, not hunting for context.

Support crew

Granola for meeting notes.
Stoic for daily journaling.
Raycast as my launcher.
NotebookLM for custom learning podcasts on systems, first principles, and behavior change during walks with my son.

My goal

Use AI to remove busywork, grow my skills, and keep my focus on people, product, and vision.

What part of this stack feels most useful for your own AI army this year?

We’re entering a split AI world.
Chat-first toys for consumers, deep integrations and agents for operators.

Today I canceled ChatGPT Pro and downgraded to Plus.

Key reason is very simple. Claude Code took over my life.

Everywhere.

Claude Code lives inside my Notion with the Notion MCP.
It talks to my Gmail and Google Calendar with Zapier MCP.

It runs 75+ agents with skills for client work and CEO work.

It writes to GitHub repos.

It runs my company systems from intake to delivery.

It runs my personal CEO systems from planning to reporting.

Non‑stop.

I paid $200 for ChatGPT Pro with love because it added value.
I would pay $400 or even more for Claude Max because it runs my whole stack.

ChatGPT moved to consumers: health, images, Sora, kitchen use cases.
Fun for my family. Not how I run an AI transformation practice.

Custom GPTs and Projects had huge promise.

Then progress slowed and focus spread thin.

Claude Code shipped deep agents, MCPs, real integrations instead.

For operators that need ROI, not toys, that split now matters.

I help founders build these AI systems inside their teams every week.

If you are an ambitious founder, think about where your AI time goes.

Chat toys or operating system.

DM me if you want a sherpa for the operator side of this split.

No alternative text description for this image

Claude Code was intimidating.

Claude Cowork makes it accessible for everyone.

What's even crazier is that Anthropic used Claude Code to build it 🤯

This week, I'm talking about Claude Cowork and why this is a huge shift in the right direction.

Introducing Cowork, an easy-to-use interface that makes Claude Code more accessible. Hi everyone, Something dropped yesterday that has me more energiz

Open article: Claude Code is now for everyone. It's called Cowork. by Tim Cakir • 5 min read

Claude Code is now for everyone. It's called Cowork.

In 2026, I’m not using AI to cut people.

I’m working with AI to cut the wrong versions of myself.

For years, my identity was “do everything, be everywhere, say yes to every project.”
Founder, operator, advisor, mentor, recruiter, builder of ten different things at once.

From the outside, it looked exciting.
Inside, it was noise.

I started asking myself in a quiet way:
Where do I create the most value?
Where do I feel alive, not drained?
Where does my weird brain plus AI create real change for people at work?

The answer was clear:
Helping leaders and teams with AI to gain more energy, more focus, and more meaning.

So in 2026, I am cutting:
→ The version of me who says yes out of fear
→ The version of me who hides behind “busy”
→ The version of me who builds things that do not fit my strengths

I am doubling down on:
→ AI as a partner to protect human focus, not destroy it
→ AI to remove the boring work, not the people
→ AI systems that give teams confidence, not fear

Human + AI for me means one thing:

More clarity for leaders and teams.

Clear vision.
Clear strengths.
Clear boundaries.
Clear systems that support humans, not replace them.

I want leaders to feel safe to do the same.
To let go of old versions that do not fit the AI era.
To build cultures where humans + AI win together.

What part of your old leadership self are you ready to cut this year?

Had a great conversation with Chris Daigle on his podcast about why so many companies feel overwhelmed by AI.

The short version: most aren't "bad at AI"—they're just chasing tools instead of outcomes.

We dug into what actually works: building habits over policies, role-specific training over generic prompts, and positioning AI as a collaborator rather than a replacement.

Link to the full episode is in the comments 👇

AI Transformation - I teach AI to Execs & their teams, develop & execute their AI strategy, implement AI across departments and make them AI Enabled businesses

Most companies aren’t “bad at AI.” They’re just drowning in tools and calling it strategy.

In the new podcast episode, I sat down with Tim Cakir, founder of AI Operator, to unpack why AI adoption feels overwhelming and how leaders can actually fix it.

→ AI fails when companies chase tools instead of outcomes
→ Training breaks when everyone gets the same prompts, regardless of role
→ Policies don’t change behavior—habits do
→ Fear drops when AI is positioned as a collaborator, not a replacement

This episode is for operators and executives who want results, not another dashboard.


🎙️ Full episode link in comments

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