I have money coming in… but I have no idea if I’m actually making money

Why You Can Make Millions… and Still Feel Broke (Part 1)

May 07, 20266 min read

Why You Can Make Millions… and Still Feel Broke (Part 1)

Profit First Lessons from Mike Michalowicz

David Richter & Mike Michaelowicz

Have you ever had a big win in your business… but still felt broke?

Maybe you closed a huge deal. Maybe your revenue hit a record high. Maybe you looked at your pipeline and thought, “This is it. I’ve made it.”

But then… reality hit.

You checked your bank account.

You looked at your bills.

And suddenly, you felt stress instead of success.

If that sounds familiar, you’re not alone.

In this first part of a conversation between David Richter and Mike Michalowicz, they talk about a hard truth:

Making more money does NOT mean you’ll keep more money.

Let’s break down why that happens, and what you can do about it.

The $2 Million Problem

David shared a story about a real estate investor.

This guy had about 20 deals going at once. On paper, he was going to make over $2 million.

Sounds amazing, right?

But here’s what he said on the call:

> “I think I might need to declare bankruptcy.”

Wait… what?

How can someone go from millions in profit… to bankruptcy at the same time?

Here’s what was really happening:

  • His money was tied up in deals

  • Some projects were losing money

  • Costs kept piling up

  • Cash wasn’t available when he needed it

So even though he was “profitable,” he had no cash.

That’s a dangerous place to be.

And it happens more than you think.

The Truth Most Business Owners Won’t Say

Here’s something Mike pointed out that might surprise you:

Most business owners say they’re doing great… even when they’re struggling.

Why?

Because we feel like we have to.

When you talk to clients or partners, you don’t say:

“Hey, I’m struggling. I really need this deal.”

No, you say:

“We’re doing great. We’re successful. We’re the best choice.”

That’s normal. It’s part of business.

But here’s the problem:

If you pretend everything is fine… you never get the help you actually need.

And behind the scenes, many business owners feel:

  • Stressed

  • Alone

  • Confused about their numbers

In fact, most businesses are living check to check.

Yes, even the ones that look successful.

More Money = More Problems?

Here’s another truth that might feel backward:

The bigger your business gets… the more stress you can have.

Why?

Because:

  • More sales = more responsibility

  • More deals = more moving parts

  • More income = more spending

Mike said it simply:

> “Sales translates to stress.”

If your foundation isn’t strong, growth makes things worse.

It’s like building a bigger house on a cracked foundation.

Everything looks great… until it starts to break.

Why We Spend More When We Make More

Now let’s talk about something called Parkinson’s Law.

This idea is simple:

Whatever is available… we use.

  • If you have more time, you waste more time

  • If you have more money, you spend more money

So when your business makes more money…

You start to:

  • Spend more on marketing

  • Hire more people

  • Upgrade your lifestyle

And before you know it…

Your expenses grow just as fast as your income.

So even though you’re making more…

You’re still broke.

The “Big Bank Account” Trap

One of the biggest mistakes business owners make is this:

They keep all their money in one account.

David called it:

> “A big black hole bank account.”

Money goes in… and disappears.

When you have one big account:

  • You don’t know what’s for profit

  • You don’t know what’s for expenses

  • You don’t know what you can actually spend

So you make decisions based on what looks available.

And that leads to trouble.

The Caveman Money Problem

Mike shared a powerful idea that explains WHY we do this.

It goes all the way back to caveman days.

Stay with me here.

Long ago, humans were hunters.

When they caught a big animal—like a woolly mammoth—they had a problem:

The meat would rot.

So what did they do?

They ate as much as they could… as fast as they could.

This is called gorging.

And guess what?

That instinct is still in us today.

When you get a big check, your brain says:

> “Use it now before it’s gone!”

Even though money doesn’t rot…

Your brain still acts like it does.

So you:

  • Spend it

  • Reinvest it

  • Move it quickly

Without a plan.

The Real Solution: A System

So how do you fix this?

Not with willpower.

Not with guessing.

Not with hoping things work out.

You fix it with a system.

That’s where Profit First comes in.

Instead of one big account, you use multiple accounts to:

  • Separate your money

  • Control your spending

  • Protect your profit

Think of it like this:

Instead of eating the whole mammoth…

You cut it up and store it properly.

Now you have control.

Now you can plan.

Now you can actually keep what you earn.

Why This Matters Early (and Late)

Some people think:

“I’ll figure this out later when my business grows.”

That’s a mistake.

Because if you don’t fix your habits now…

You’ll just make bigger mistakes later.

As David said:

  • Small business → small problems

  • Big business → BIG problems

The best time to fix your money system is:

Before things get messy.

But if you’re already in a tough spot?

It’s not too late.

You just need to:

  • Step back

  • Get clarity

  • Put a system in place

Final Thought

If you feel like you’re making money… but not keeping it…

There’s nothing wrong with you.

You’re not bad with money.

You’re just missing a system.

Because without a system:

  • Success feels stressful

  • Growth feels scary

  • Money disappears

But with the right system?

You can finally:

  • Keep your profit

  • Pay yourself

  • Build a business that actually supports your life

Next up in Part 2:

We’ll dive deeper into behavior, habits, and how to break the cycle for good.


Ready to Take the Next Step?

At Simple CFO, we believe your financial strategy should be built by people who understand your vision — not just a computer program. Our team has helped hundreds of business owners implement smarter systems, keep more profit, and finally achieve peace of mind with their money.

👉 Book your free Financial Clarity Call today to see how we do things differently and how a CFO partner can transform your business.

And as a bonus, when you start your journey with us, you’ll also get a copy of David Richter’s book, Profit First for Real Estate Investors (REIs — completely free! It’s the perfect first step toward taking control of your cash flow and building a truly profitable business.

Click the button below to schedule your call and claim your free book from Simple CFO:

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David Richter is a former real estate investor who started Simple CFO Solutions after seeing the financial problems most REIs experienced. Using Profit First, Simple CFO Solutions helps business owners ensure they get paid, their expenses are controlled, and they make more profit.

David Richter

David Richter is a former real estate investor who started Simple CFO Solutions after seeing the financial problems most REIs experienced. Using Profit First, Simple CFO Solutions helps business owners ensure they get paid, their expenses are controlled, and they make more profit.

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