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What Are The Rules of Engagement

Oct 20, 2026

I was reading Think and Grow Rich many years ago, and Napoleon Hill said something that took me by surprise.

He talked about how, when men turn 50, that’s when everything changes in their lives when it comes to finances.

The first time I heard that, I actually thought it was ignorant. My first thought was that a lot of Black men don’t live to see 50. Of course, I was basing that on my own bias from growing up where I did. I saw so many people die young.

But now that I’m older and over 50, I get it.

I made some good money when I became an entrepreneur, but I knew how to make money and not how to keep it.

Why? Because I didn’t understand the rules of engagement.

I didn’t know much about investing. I didn’t understand how to let my money make money and then let that money make more money.

For the last four years, I’ve been studying finance, and I’ve learned that money is meant to be in motion. It needs to be put to work instead of just sitting somewhere doing nothing.

I didn’t understand that I could open a brokerage account through Charles Schwab or a Roth IRA through Fidelity.

I didn’t understand that I could’ve opened a custodial account for Arie and started building wealth for her while she was still young.

I didn’t understand REITs and how they can pay dividends. I didn’t understand index funds or ETFs.

There was so much I didn’t know about putting my money to work.

I knew how to make money. I just didn’t know how to make my money make money.

If you want to build wealth, you have to start asking better questions.

Why should I have a business even if I still work a full-time job?

Why should I consider investing in real estate?

Most people buy houses just to live in them. There’s nothing wrong with that. It’s honorable to own your home.

But if your business is making real money, owning real estate may offer opportunities to build your portfolio and potentially benefit from certain tax advantages. I’m not against investment properties. I think they can be a good addition to a portfolio.

I’m an intellectual property guy. I create online businesses.

One of the reasons I got caught up with the IRS was that I didn’t understand how to offset my income properly.

I just didn’t know what questions to ask. I didn’t understand the rules of engagement.

My job had me making $50,000–$60,000 a year, but when I started making money as an entrepreneur, I didn’t have the financial knowledge to manage it the way I should have.

And I can’t blame anybody else for that.

I didn’t have anyone in my life to show me, but there are too many books out here. There are too many mentors available. We are way too grown to keep blaming everybody but ourselves.

We have to take responsibility for what we don’t know and make the effort to learn.

ASK BETTER QUESTIONS. LEARN THE RULES OF ENGAGEMENT.

Especially when it comes to starting a business.

Because knowing how to make money and knowing how to build wealth are two different things.