There is a restaurant owner I know who starts every day with the same question: Is he going to show up today?

Not “is the food going to be good today?” Not “are we going to hit our numbers today?” The first thought of the morning is whether one employee is going to show up — and if he does, what kind of mood he’s going to be in when he gets there.

That is not a staffing problem. That is a hostage situation.

How It Gets to This Point

It did not start this way. It never does.

You hire someone you trust. They show up, they learn the operation, they become reliable. You give them more responsibility because they’ve earned it. And somewhere in that process, the balance shifts — not all at once, but gradually — until you look up one day and realize you cannot function without them.

Not because they are exceptional. Because you never built the system that would let you operate without any single person.

In this case, the owner is driving this employee to work. Every day. Because without him, only one person remains on staff to run the floor. So the owner picks him up, absorbs whatever attitude comes with him that morning, and spends the rest of the day managing around him — his moods, his inconsistency, his effect on everyone else in the building.

The employee is not running the register. But he is running the owner.

The Cancer Nobody Talks About

There is a concept in small business called key person dependency — the idea that your operation is overly reliant on a single individual. Most people think about it in terms of talent: what happens if your best employee leaves?

But dependency does not only live in your best people. It lives in your most entrenched ones, too.

When someone becomes impossible to remove — not because of what they contribute, but because of the gap their absence would create — that is a different kind of problem. And when that person knows it, consciously or not, the dynamic in the building shifts. Their attitude reflects it. Their effort reflects it. And everyone else on staff feels it.

A bad attitude in a small operation is not just one person’s problem. It spreads. It sets the tone. It tells every other employee what is tolerated — and what is not.

What the E-Myth Actually Means

Michael Gerber’s E-Myth makes a simple argument: most small business owners build a job for themselves, not a business. They become the center of everything — the one who knows how it all works — and then wonder why they can never step away.

The same principle applies to the people you hire. When an employee steps into your operation without a clear process to follow, they fill the vacuum with their own way of doing things. Over time, their way becomes the way. And now you have a business that runs on a person instead of a system.

The fix is not firing people. The fix is building before you hire — so that anyone who walks through the door steps into your process, not creates their own.

The Real Cost Nobody Calculates

In this situation, the owner is not just losing money on a bad employee. He is losing something harder to quantify — mental energy, decision-making capacity, the headspace that should be going toward growing the business.

Every morning, he wonders if the employee is coming in; he is spending cognitive resources that a business owner cannot afford to waste. Every time he adjusts the schedule, the workflow, or his own day around one person’s unpredictability, the business pays a tax that never shows up on a profit-and-loss statement.

Bad employees are expensive. Trapped owners are more expensive.

The Way Out

The owner knows what needs to happen. He just cannot do it yet — because the gap it would leave is too big to absorb right now. So the immediate work is not firing. It is building. Recruit before you remove. Document the process so the knowledge lives in the system, not the person. Create a position that the next hire steps into — not a void they have to figure out on their own.

And while that is happening, stop driving him to work.

Small things matter. Every accommodation you make to keep a bad situation stable is energy you are not spending on making it better.

The Flipside

Strong businesses are modular. People come in, grow, move around, and sometimes leave — without the whole thing falling apart. That only happens when the process is documented, the roles are clear, and no single person — good or bad — is holding the operation hostage.

Build the system first. Then hire the people to run it.

If someone in your operation walked out today, would the business survive the week?

If this hit close to home, share it with a business owner who needs to hear it. And if you are not subscribed yet, this is what every issue looks like. financialflipside.com

The conversation about supporting Black businesses comes up every year. But we keep stopping at the same place.

The Number That Started the Conversation

During the Target fast of 2025, Pastor Jamal Bryant of a church in Atlanta estimated that spending among the Black community is $2 trillion per year — a sum that equals the GDP of some countries.

During this time, the call was to “support” Black-owned businesses, which is fine. Yet another way we need to support Black businesses is one that is rarely discussed.

What I’ve Seen From the Inside

As a DJ, I became an entrepreneur in 1992, while still in college, and became a licensed CPA in 2008. Since childhood, I shadowed my father, an accountant-entrepreneur, and recognized a common thread among Black businesses: undercapitalization.

Undercapitalization occurs when a business has enough money to get started, but not enough cushion to withstand the natural turbulence of business cycles — often leading to cash flow challenges that many of the community’s earliest businesses face.

These are the primary challenges of the businesses that “fail in the first five years.” Common knowledge holds that these businesses fail because the idea wasn’t good or for other reasons, but in many cases, cash flow problems are the culprit.

The Math Is Simple

What if we annually redeployed one-tenth of 1% (.001) of $2 trillion dollars or 2 billion dollars of the community’s estimated spending to business investment?

Resources we already spend could help reduce (not eliminate) business failures in the first five years, allowing them to survive and thrive. These thriving enterprises can increase hiring from the community and reduce the percentage — currently 96% — of Black businesses with no employees.

The deployment would assist the 50% of Black businesses that provide services, offering greater growth potential for those looking beyond tech and real estate. This capital would allow the development of factories, distribution companies, and medium to large-scale retailers.

These funds could help prop up our businesses so they can contribute to the broader economy and bring profits back to the community, rather than constantly sending funds out. Black unemployment rates can be affected, even reduced by a couple of percentage points. Increased profits can help create more livable wages and environments for Black employees who are culturally aligned.

Where to Start

While I wholeheartedly believe in this concept, this is an aspirational outlook that will require a massive effort to implement. There are mental barriers to achieving this goal because people haven’t thought about money or investment in these terms.

Like any social change, starting and staying consistent are the movement’s engine. A good way to start the conversation is to ask a business owner whether they are taking on investors — or, if you’re not comfortable with investing, simply ask how you could help them grow.

The $2 trillion is already moving. The question is where it lands.

I

Americans have some of the most complicated relationships with money on the planet. Not because we have less of it — but because we’ve attached so much meaning to it.

In this country, money isn’t just a resource. It’s a report card. It tells you whether you worked hard enough, whether God favors you, whether you’re winning or losing at life. That idea didn’t come from nowhere — it traces back to what sociologist Max Weber called the Protestant work ethic: the belief that financial success signals moral virtue, and financial struggle signals the opposite.

The flipside of that belief? If you’re not “self-made,” you’re either lazy, unlucky, or lacking something fundamental. That’s a brutal framework to carry around — and most of us are carrying it, whether we know it or not.

The Fear Is Real — and It’s Everywhere

The Chapman University Survey of American Fears has consistently ranked “not having enough money for the future” among the top fears Americans report year after year. Not spiders. Not public speaking. Money.

We’re not afraid of money itself. We’re afraid of what it means if we don’t have enough — that we failed, that we’re falling behind, that we’re headed somewhere we can’t come back from.

Most people think of themselves as middle class: not rich, not poor, just trying to stay on the right side of an invisible line. That constant effort to hold position — to not slide backward — is exhausting. And it creates a quiet, grinding anxiety that most people never name out loud. Every unexpected expense feels like a threat. Every financial decision carries weight it shouldn’t have to carry. And over time, that pressure makes it easier to just… not look.

Do not open the statement. Not check the balance. Not to do the math.

Because as long as you don’t look, you don’t have to know for sure.

Avoidance Is the Enemy

Here’s what I’ve seen in 17 years of sitting across from business owners and individuals: the fear doesn’t come from knowing your numbers. It comes from not knowing them.

Think about the last time you avoided opening a bill or put off looking at your account after a rough month. It wasn’t because you knew it was bad. It was because you weren’t sure — and your brain decided that not knowing was safer than finding out. So the anxiety just sat there, unnamed and unresolved, taking up space and quietly influencing every financial decision you made.

The uncertainty is what feeds the fear. When you don’t know exactly where you stand, your brain fills in the blanks — and it almost always fills them in with the worst possible version of the story.

The antidote isn’t a budgeting app or a new savings account. It’s a confrontation — a direct, honest look at what’s actually there.

Start Here

This doesn’t have to be complicated. Five steps:

1. Write down what actually hits your account — not your salary, the actual deposit.

2. List your necessities: housing, utilities, transportation, food, communication, clothing.

3. Subtract your necessities from your deposits.

4. If there’s a surplus — that’s your working number for savings, extras, and building.

5. If there’s a deficit — that’s your starting point. Not a verdict. A starting point. It means you now know something you didn’t know before, and knowing is always better than guessing. You can’t fix what you won’t face — but you absolutely can fix what you can see.

That’s it. Do that exercise once, then do it again next month. The fear doesn’t disappear overnight — but it starts to lose its grip when you stop letting it live in the dark.

The system wasn’t built to make this easy for you. That’s exactly why we’re here.

The Financial Flipside publishes every two weeks. If someone forwarded this to you —

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After 30 years of building businesses and 15 years running a CPA firm, I can tell you that one of the hardest obstacles that I have faced is US!

I love black people! We are creative, smart, resilient, and innovative. But we have a hard time dealing with each other when it comes to money and business.

Black folks have historically been underserved and underrepresented in the US capitalist system, but we have managed to excel through education, hard work, and perseverance.

Unfortunately, the term “Black Business” is loaded with silent adjectives—unprofessional, unreliable, inferior—that sometimes create apprehension, mostly from our own people. This skepticism shrinks an already limited market. To be successful, Black businesses have to cater to everybody because we’re only 12% of the population, and that small market gets even smaller when our own people doubt us without ever becoming patrons.

There is an overwhelming lack of trust in one another when it comes to getting things done, along with disrespect for each other’s experience. Some of us are obsessed with our titles and the appearance of being “professional” without striving to be elite. These same “professionals” are afraid to look ignorant and feel like they need to challenge someone who is a Black expert.

Most of all, we extoll the need to be twice as good to make it, but don’t acknowledge that we force our own people to be twice, maybe thrice as good to serve us.

We have a sickness, passed down from slavery and Jim Crow, where we expect inferiority from our own people. In the 26th year of the 21st century, some of us still follow the adage that “white is right” and are willing to pay them more than our own people.

I ask: Why are we in this state, and how can this change?

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