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

I’m a technology and transformation executive who helps complex organizations translate strategy into measurable operational outcomes.

Over the past 15+ years, I’ve partnered directly with Presidents and executive leadership teams across healthcare, manufacturing, financial services, and retail, including multiple Fortune 50–500 enterprises. My work has focused on enterprise transformation, operating model change, and disciplined execution—from CRM and ERP modernization to analytics- and AI-enabled decisioning.

Across roles, I’ve delivered outcomes such as:

→ Supporting $1B–$2B business units as an embedded technology and transformation leader
→  Leading $20M+ enterprise portfolios aligned to growth, margin, and operational resilience
→  Unlocking $4M+ annual cost savings, improving manufacturing throughput and execution efficiency
→  Scaling customer experience and commercial platforms while maintaining regulatory rigor

What differentiates me is not strategy alone, but building the operating reality that makes it stick—aligning leaders, teams, and investment decisions to deliver results in complex, regulated environments.

Since mid-2025, I’ve also taken on select advisory engagements, supporting leadership teams with operating model design, CRM optimization, and execution discipline while exploring senior executive and consulting leadership opportunities.

I’m currently engaging with organizations seeking senior leaders who can bridge strategy, technology, and execution. I welcome conversations where I can add significant value with a focus on transformation, operational excellence, and scalable growth.

Book time with me:
https://cal.com/nicksimsco

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The Battle

John Montgomery

Nick Sims

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