The Finance Gem 💎 #102: The 5 Financial Skills Every CEO Needs to Master

Hi everyone,

There are two types of CEOs and founders. 

The first type doesn’t just know the numbers—they get what’s behind them. In boardrooms, investor meetings, or team discussions, they connect strategy to financials. They can explain how stock compensation shows up in the P&L, how capital decisions affect the balance sheet, and how it all ties back to cash and value.

The second type depends on their CFO for every financial conversation. They make major calls based on instinct, not insight—because they can’t grasp the impact or understand the outcomes themselves.

Which one are you?

If you're in the second group, you're not alone. But you're also not reaching your full potential as a leader.

So in today’s issue of the Finance Gem, I’m breaking down the 5 financial skills that matter most for every CEO.

But first, a quick reminder:

Free masterclass for CEOs & C-suite executives this Friday

Join me this Friday (August 1st) for a free masterclass about 6 budgeting mistakes that kill growth and valuation.

…and that often also get CEOs fired.

We'll cover:

• The 6 budget mistakes that get CEOs fired

• How to link your budget to strategy

• A framework for tracking performance before it's too late

• Why most budgets destroy board trust

This is for CEOs and C-suite executives who make capital decisions. Because when results miss expectations, the board looks at the CEO, not the CFO.

Plus, I have two surprises for everyone who attends live.

Now, let's get to those five essential skills...

Skill 1: Plan 3–5 Years Ahead by Reverse Engineering Your Outcomes

Most companies plan forward from last year. Smart ones work backward.

Start with your 3–5 year targets—revenue, margins, valuation—and reverse engineer the path to get there.

Then use:

✔️ Strategic Plan to allocate capital
✔️ Budget to resource Year 1
✔️ Forecasts to track and adjust

This forces focus. You’ll see what must change—pricing, headcount, product—so you can fund what actually moves the needle.

Stop asking, “What can we afford?”
Start asking, “What must we fund to win?”

Skill 2: Track Cash to Fund Strategy, Not Just Stay Afloat

Start with a 5-year capital allocation roadmap:
What will it take to grow, hire, expand, or raise?

Then manage cash flow weekly to stay aligned. Use a 16-week rolling cash view to track:
✔️ Cash on hand
✔️ Timing of inflows and outflows
✔️ Burn rate vs. plan

This lets you adjust in real time—so your long-term strategy never gets derailed by short-term surprises.

Skill 3: Know when to borrow money and when to sell equity

(This skill alone can double your company value in 3-5 years.)

Here is how to think about it in simple terms:

Debt is for funding initiatives with predictable cash flows and clear payback—without giving up control.

Equity is for big strategic moves you can’t fund internally or with debt—when the upside is worth the dilution.

But neither decision stands alone. Every capital decision should:

✔️ Support your long-term strategy
✔️ Fit within your 5-year capital allocation plan
✔️ Preserve flexibility and control

It’s not about cheap vs. expensive capital. It’s about deploying the right capital at the right time—to drive the outcomes that matter.

Skill 4: Know if each customer makes or loses money

You need to know if you're making or losing money on each customer.

Calculate these numbers for your business:

• Cost to get a customer: Marketing spend divided by new customers

• Customer lifetime value: Total revenue from one customer over time

• Profit per sale: Revenue minus all costs for that sale

• How long customers stay: Track this by groups who joined at the same time

The math is simple:

• If a customer costs $1,000 to acquire

• And they only bring in $500 over their lifetime

• You lose $500 on every new customer

If these numbers are negative, you will need to fix them before you can start scaling.

Skill 5: Plan for Multiple Futures—Not Just the One You Hope For

Markets shift. Capital dries up. Competitors move faster than expected.

The job of a CEO is not to predict—it’s to be ready.

Pressure-test your plan across real scenarios:

• Customers – What if demand drops 50%? What if it surges?
• Competitors – What if one raises $100M? Or exits the market?
• Suppliers – What if materials become scarce or spike in cost?
• Funding – What if your line of credit gets cut in half? Or investors pause?

For each, define two things:

✔️ Early signals – What will tip you off before it’s too late?
✔️ Response plan – What actions will you take to adapt fast?

When others freeze, you’ll already be executing.
That’s more than just resilience. It’s strategic foresight.

I know finance can feel intimidating, especially when you don’t have a finance background.

But mastering these skills only requires two things you can easily learn: 

1️⃣ Tracking the right numbers

2️⃣ Asking the right questions

When you do, board meetings become easier, and facts inform investment discussions. And most importantly, you start making decisions with confidence because you understand their financial impact.

Your CFO remains equally valuable. But now they become your partner, not your translator.

Which one of these will you start improving this week? I recommend picking the one that makes you most uncomfortable. That's probably the one your company needs most.

Ready to master these skills with my guidance?

If you want to go deeper on financial intelligence and learn alongside other CEOs, my CEO coaching program launches on August 27.

Here's what you get when you join:

• Live sessions where we work through the most essential skills you need  

• Templates and frameworks you can use immediately in your business

• A peer group of CEOs who understand the pressure you're under

• Direct access to ask questions when you're facing real decisions

• Community and accountability to implement what you learn

Past participants have used these skills to raise funding at better valuations, make smarter acquisition decisions, and finally feel confident in board meetings.

Best wishes, 

Oana

PS. Don’t forget to register for the Friday masterclass and secure your seat before registration closes.