A Game Worth Playing

I missed my newsletter this weekend.

I was at a men’s retreat.

And if you know me primarily as a CFO, Scaling strategist, or the guy constantly talking about cash flow and financial operating systems, you might reasonably wonder:

What does spending four days at a men’s retreat have to do with business?

Everything.

I spent four days at Camp Taconic with Man on Fire, surrounded by entrepreneurial men from different industries, backgrounds, and walks of life.

Men trying to become better husbands.

Better fathers.

Better business leaders.

Better friends.

Better citizens.

I’m not going to pretend it was four days of sitting around a campfire feeling inspired.

It was work.

The kind of work that asks you to look at yourself and ask harder questions:

How am I showing up?

Where am I holding back?

What am I actually building?

Who benefits if I become a better leader?

And perhaps most importantly:

What is all of this for?

The question behind the business

I’ve also been rereading Michael Gerber’s The E-Myth Revisited.

One passage has stayed with me:

“With no clear picture of how you wish your life to be, how on earth are you going to live it? What is your Primary Aim?”

Gerber isn’t really asking a business question.

He’s asking a life question.

Because before you decide what kind of company you want to build, you have to decide what kind of life you are trying to create.

Otherwise, the business becomes the master.

You become its employee.

Revenue becomes the score.

Growth becomes the objective.

And eventually you can find yourself running very fast without being entirely sure where you are going.

Gerber calls for something different:

A Game Worth Playing.

A life with purpose.

Values.

Worthwhile standards.

Community.

Discipline.

Meaning.

And this weekend, those ideas came together for me in a completely different way.

Your business is one of the places where your values become real

I believe business can be one of the greatest forces for good in the world.

But only when the people leading those businesses remember that there are human beings behind the numbers.

Employees have families.

Customers have problems they are trusting us to solve.

Vendors are building businesses of their own.

Communities are affected by the decisions we make.

And founders themselves are human beings — carrying enormous responsibility, uncertainty, fear, ambition, dreams, payrolls, families, and expectations.

We already have enough professionals who are technically excellent but disconnected from the human beings they serve.

People who can perform the technical function perfectly while completely forgetting the human being sitting across the table.

I don't want to build that kind of company.

And I don't want to become that kind of advisor.

I feel increasingly called to serve my clients at a different level.

To step further into leadership.

To lead from the heart without abandoning rigor.

To care deeply while still telling the truth.

To challenge someone while standing beside them.

And to build systems that give founders more confidence and freedom instead of simply producing another report they don't understand.

And strangely enough, this makes me a better CFO

Because a great CFO's job isn't simply to tell you what happened last month.

It is to help you build a company you can lead with confidence.

That requires numbers.

But it also requires understanding why the numbers matter.

Why do you want to grow?

What are you trying to build?

What kind of team do you want around you?

What do you want your life to look like?

How much is enough?

What are you unwilling to sacrifice to get there?

Only then do the systems make sense.

The forecast.

The cash plan.

The margins.

The KPIs.

The organizational structure.

The operating cadence.

The financial model.

Those aren't the destination.

They're infrastructure.

They give a founder visibility.

Visibility creates better decisions.

Better decisions create confidence.

And confidence gives a leader the capacity to stop constantly reacting and start actually leading.

That's the business I want to build.

And that's the work I want to do with my clients.

Systems and humanity are not opposites

This is one of the biggest lessons I keep taking from Gerber.

A business needs systems precisely because human beings matter.

Without systems, everything depends on heroic effort.

The founder becomes exhausted.

The team becomes confused.

Decisions become reactive.

Important things live inside someone's head.

And eventually the business begins consuming the very life it was supposed to create.

The right systems do the opposite.

They create space.

Space to think.

Space to lead.

Space to serve.

Space to spend time with the people we love.

Space to become the person capable of leading the next version of the company.

That is what financial infrastructure should ultimately do.

Not turn entrepreneurs into accountants.

Help entrepreneurs become better leaders.

Gerber writes that what many people are searching for is:

“…a place of community that has purpose, order, and meaning.”

And then he makes an extraordinary claim:

“That’s what a business can do; it can create a Game Worth Playing.”

I think he's right.

But that game doesn't happen accidentally.

We have to design it.

The company.

The systems.

The economics.

The culture.

And ourselves.

Four days with a group of men reminded me that leadership isn't something we exercise only in the boardroom.

It is who we become everywhere.

As husbands.

As fathers.

As friends.

As business owners.

As citizens.

As human beings.

And when we do that work, our businesses don't become weaker or softer.

They become stronger.

Because the leader becomes stronger.

That may be the most important scaling work of all.

And a special thank you to David Mehler and the entire Man on Fire team for creating the kind of space that helped me stand taller this weekend — as a man, as a leader, and as an entrepreneur. I came home with a deeper love for my business, a clearer connection to my purpose, and an even stronger conviction about the way I want to serve the people who trust me to help them grow.

And to the warriors I had the honor of spending 4 powerful days with, I see you!

— Cruz

P.S. This is increasingly how I think about the role of a fractional CFO. Not simply someone who manages the numbers, but someone who helps a founder create the financial clarity, systems, and confidence required to build a business — and a life — worth leading.