The Finance Gem 💎 #109: The 3 CEO Gaps and How to Trust the CFOs Numbers

Hi there, 

A CEO, a CFO, and a finance lead walk into a bar.

The CEO says, “I’ll order once I can trust that the forecast is right.”
The CFO says, “I’ll order after I see the cash impact.”
The finance lead says, “I’ll order once last month’s numbers reconcile.”

The bartender just shrugs:
“Sounds like nobody’s drinking tonight…”

That’s most companies. The forecast looks professional, the reports look polished—yet no one trusts them enough to make a real decision.

So here’s what I’m covering in today’s issue:

• How CEOs Lose Trust (and Enterprise Value ) Without Realizing It

• Enrollment for the final 2025 cohort of The CEO Financial Intelligence Program

• This Thursday’s free masterclass: The 10 CEO Mistakes

Enrollment is now open for the Fall 2025 Cohort of the CEO Financial Intelligence Program

After 15+ years working alongside CEOs and CFOs across industries and continents, I’ve noticed a pattern: the leaders who scale furthest aren’t always the loudest, flashiest, or most charismatic.

They’re the ones who source & allocate their capital with discipline.

They don’t just fund ideas. They fund priorities — at the right time, with a clear view of trade-offs, risk, and return.

Right now, I’m seeing CEOs from the U.S. to Saudi Arabia, From Trinidad to Singapore, and from Latin America to Asia, operating at an entirely different level because they’ve made this shift.

They’re asking sharper questions. They’re planning with greater confidence. They’re showing up in boardrooms with foresight and conviction — not reacting from confusion.

When you stop outsourcing financial clarity and start owning it, you gain three things every CEO needs:

• The right questions to push your finance team further

• The right answers to give your board and investors confidence

• The right metrics to keep strategy and execution aligned

If you’ve ever felt that:

• You’re making big investment calls without the visibility you want

• Your CFO delivers data but not real decisions

• Your board meetings feel more defensive than strategic...

Then this is the time to change that.

Enrollment is now open for the Fall 2025 Cohort of the CEO Financial Intelligence Program — the final cohort of this year.

This isn’t financial ABCs. This is strategic financial mastery for growth-minded CEOs and executives.

Over six weeks, you’ll learn how to:

• Make smarter, faster decisions even in volatile markets

• Spot risk before it surfaces and build resilient cash flow plans

• Tie strategy to real numbers that guide and align your leadership team

• Earn investor and board trust by showing up with credibility and foresight

• Grow and protect enterprise value without wasting a dollar or a quarter

🎯 Early Bird: Save $500 when you enroll by Friday, Sept 20
🎓 Program kicks off Nov 12.

Seats are limited to ensure the cohort experience. Secure yours today.

Free CEO Masterclass This Thursday

Topic: The 10 CEO Mistakes That Erode Control, Cash, and Valuation
📅 Sept 18 | 🕘 9 AM PT / 12 PM ET / 5 PM GMT

Most CEOs don’t fail because of market conditions. They fail because of the decisions they make — or don’t make — with capital.

This masterclass is a direct look at the hidden mistakes that quietly drain control, cash, and enterprise value, and the shifts you need to lead with foresight instead of hindsight.

We’ll cover

• Why your budgets quietly sabotage long-term growth

• The “EBITDA trap”

• How cash planning blindsides even profitable companies

• The board and investor conversations that erode trust

• Why your dashboards are keeping you stuck

And if you attend live, you’ll unlock a private bonus — something designed to help you lead differently starting the very next day.

Register here

How CEOs Lose Trust (and Enterprise Value ) Without Realizing It

Here’s the reality: if the CEO hesitates, the CFO is reacting after the fact, and the finance team is buried in reporting, it’s not just a finance problem.

It’s a leadership gap with three root causes: capability, expertise, and systems.

• Capability — Your team can report history, but can they connect numbers to capital decisions that drive the future?

• Expertise — If your CFO is stuck in “chief analyst” mode, you’re missing the architect who turns forecasts into strategy.

• Systems — A forecast that collapses when one assumption changes isn’t a system. It’s a spreadsheet.

When these gaps pile up, they don’t just slow you down — they destroy trust in the numbers and pull down valuation.

The three gaps every CEO must close:

1. Capability — Preparing for the future

Yes, the books close. Yes, the dashboards refresh. But none of that matters if you don’t know what to do next.

Great CEOs don’t need to know what happened — they need to know what’s about to happen and what should happen. And that requires finance capability that ties numbers directly to capital:

• What does this decision cost in cash, time, and trade-offs?

• What’s the return if we get it right — and the downside if we don’t?

• How will today’s choice shape enterprise value six months from now?

The strongest companies don’t stop at reporting. They build finance capability that delivers foresight — turning numbers into a forward-looking guide for execution and growth.

2. Expertise — A CFO who architects

If your CFO is still playing “chief analyst,” you’ve got a problem. Anyone can explain what the numbers say. Very few can architect decisions from them.

The best CFOs don’t just comment on results — they engineer the path forward:

• Tying forecasts directly to headcount, capital, and valuation

• Designing models that anticipate volatility instead of assuming stability

• Giving the CEO not just answers, but quantifiable options, outcomes, impact

That’s how finance earns its seat at the strategy table — not as a reporter of outcomes, but as a builder of them.

3. Systems: A forecast that tells you everything

Plenty of models look impressive in Excel. But the second you try to use them to actually plan better — test scenarios, guide trade-offs, make capital decisions — they offer no insight, no intelligent guidance, no warnings, no opportunity spotting.

Just pretty formatting and fragile formulas.

What' you’re missing is connected systems where every change — every headcount decision, pricing move, or capital spend— whether short or long term, instantly shows its impact on cash and valuation.

That’s the difference between a forecast that reports numbers, and a system that drives strategy.

Fail to close all three of these gaps and here’s what you get:

No trust, all chaos

If no one believes the forecast, you end up with three versions of the truth: the CEO’s model, the CFO’s model, and the board’s back-of-the-envelope model.

Decisions slow down, capital stalls, and every leadership meeting turns into a data debate instead of a strategy debate.

In strong companies, trust flips the script. No one argues over the numbers because everyone can see the impact—they argue over the assumptions and the strategy. And execution moves 20x faster because they have a common language.

Valuation rewards discipline—not vibes

Investors and lenders aren’t buying your spreadsheets. They’re buying your system.

If your forecast looks like guesswork, they mark down valuation and price in risk. If your model shows credibility—connected assumptions, disciplined capital sequencing, and clear visibility—they pay a premium.

Valuation isn’t just about what happened last quarter. It’s about proving you can see around corners.

Financiario - transform in just 7 days

By the way, if you want this level of visibility and control inside your business—capability, expertise, and systems working together in one connected infrastructure—Financiario will build it for you in just 7 days. And once you start to look forward you will never go back.

It’s the CFO-grade infrastructure that turns your finance from reporting into strategy. Dashboards, engineered forecasts, board-ready outputs—all in one. Never leaves, never takes vacation, always trustworthy.

Watch it in action here.

The companies that scale with confidence don’t wait until the board or the market forces their hand. They build capability, expertise, and systems before they need them. That’s what this fall’s cohort of the CEO Financial Intelligence Program is designed to give you.

If you want to lead with foresight—not reaction—this is your chance. Enrollment for The CEO Financial Intelligence Program closes soon, and once we begin, there won’t be another cohort this year.

Warm regards,
Oana

P.S. Don’t forget—the free masterclass is this Thursday, September 18. I’ll walk through the 10 CEO mistakes draining growth, cash, and valuation. Seats are limited. Grab your spot here.