What I Learned as a Founder, CFO, and Private Equity Investor — So You Don’t Have To

Bob Wang
Jun 30
3 min read

I'm a Private Equity CFO

If there’s one thing I’ve learned over the years - building my own businesses, stepping into CFO roles, and sitting on the investor side of the table - it’s that growth looks very different depending on where you’re sitting.

As a founder, you’re in the trenches.

As a CFO, you’re making sense of the chaos.

As an investor, you’re deciding which businesses are worth betting on.

And after experiencing all three, I’ve come to realize: most entrepreneurs only ever see one side. Which means they often miss the playbook that could save them years of frustration — or millions of dollars.

Today, I want to share a few hard-earned lessons from each seat. My hope? That you can avoid some of the headaches I’ve lived through — and grow your business with a little more clarity and a lot fewer surprises.

Lesson 1: Founders Often Wait Too Long to Get Financial Help

When I built my first business, I made the same mistake many founders do — waiting until things were “big enough” to bring in real financial leadership.

Seeing a business from multiple perspectives

The problem is, by the time you think you need a CFO, you’ve probably been operating with blind spots for months. Forecasts don’t align with reality. Margins quietly erode. Cash gets tight — and you’re not sure why.

The truth is, a good CFO isn’t a luxury for later. It’s how you build an enduringly profitable company from the ground up.

Lesson 2: As CFO, You See the Cracks Before They Become Craters

Once I transitioned into CFO roles, the patterns were hard to miss.

Revenue looked great - but the sales assumptions didn’t hold up under scrutiny.

Gross margins were strong - but operating costs were creeping up quietly.

Forecasts told a good story - but cash flow told the real one.

What I’ve learned is that most businesses don’t break overnight. They erode slowly, in the margins and missed details. A strategic CFO doesn’t just report numbers - they challenge assumptions, spot the leaks, and force uncomfortable (but necessary) conversations.

Lesson 3: Investors Aren’t Just Buying Your Business - They’re Buying the Story and the Systems

When I was on the investor side, reviewing hundreds of companies, I started to see what separates the “fundable” businesses from the rest.

It’s not always revenue. It’s not always growth rate.

It’s whether the numbers make sense — and whether the operator does too.

The businesses that command premium valuations have more than potential. They have:

✔ Reliable, clean financials

✔ Realistic, defensible forecasts

✔ Leadership teams that understand their numbers — not just their product

✔ Operational maturity that shows this isn’t their first rodeo

And the ones that struggle? Usually, they’re still winging it behind the scenes - even if the topline looks good.

The Advantage of Seeing All Three Angles

Sitting in each of these roles has shaped how I work with entrepreneurs today.

As a Fractional CFO, I’m not just thinking like an accountant. I’m thinking like an operator — and like an investor. I know what buyers look for. I know where the cracks hide. And I know how overwhelming it can feel when you’re still building the plane mid-flight.

That’s why I started Tee Up Advisors - to help founders avoid some of the expensive lessons I learned the hard way.