"I Write What I Like" – Steve Biko

"Can I Keep It a Stack with You?"

As the young folks say, can I keep it a stack with you? I write this newsletter for selfish reasons. Sure, I hope you enjoy it—laugh, cry, maybe even spark a debate or two—but the real truth? I’m doing this for me. Call it what you want—therapy, self-expression, or just a man avoiding the traps of midlife boredom—but at its core, this newsletter is my playground. I’m here to unpack the stuff I love—business, music, film, books—and wrestle with big ideas while sprinkling in enough humor to keep us both entertained.

With that out of the way, this year I’m starting something new. I’m writing about whatever lessons or “messages” I can pull from the art pieces I love. And I’m kicking it off with music—specifically Jay-Z’s Reasonable Doubt.

What follows in the coming weeks is part memoir, part church, part therapy, and part exploration of why rap music deserves its rightful place in the pantheon of great art forms. Yeah, I said it. Rap music is art, and I’ve got receipts if you’re ready to argue.

Will I hit all my lofty goals? Who knows. But honestly, that’s not the point. Like the old folks say, “It’s about the journey, not the destination.” Or, to borrow from Kanye’s “Can’t Tell Me Nothing”: “I had a dream I could buy my way to heaven / When I awoke, I spent that on a necklace.” That line right there? It’s every hustler’s paradox—grinding for the dream while getting distracted by the shine along the way.

This project is also my healthier alternative to the dangerous trinity of black man stress relief: Ciroc (no Diddy), fried Chinese chicken wings, and Newports. (Is this list racist?! lol) I’m not saying I’m above any of these things—well, maybe Newports—but as a man over 40, I’ve seen too many brothers caught in that cycle to know I need a different outlet. And since black men and therapy are about as common as snowstorms in Miami, here we are. These newsletters? This is my couch. And I’m spilling my thoughts for the world to see.

Hopefully, as I wrestle with my demons and passions, you’ll find something to laugh about, cry about, think about, or vibe with. Let’s take this ride together—or, you know, you can choose to get off now.

Why Start with Reasonable Doubt?

If I were stranded on a deserted island for a year, here’s my “What I’m bringing” starter pack:

• 1 Movie: A four-way coin toss between The Usual Suspects, Goodfellas, The Devil’s Advocate, and Coming to America. (Yes, I know that’s too many choices, but I’d need a custom, multi-sided coin for this.)
• 1 Book (Fiction): The Great Gatsby.
• 1 Book (Nonfiction): The Judas Factor by Karl Evanzz.
• 1 Album: Jay-Z’s Reasonable Doubt, narrowly edging out American Gangster.

Now that I’m typing this, I realize there’s a common thread running through all these choices—an exploration of success, the blurry line between what’s real and fake, and a heavy dose of self-deception. (Look at me, accidentally psychoanalyzing myself. Y’all are getting your money’s worth today.)

None of these works are about happy endings. They’re about the hustle, the grind, the choices made along the way, and the inevitable consequences. We all know how these stories end—whether it’s Gatsby floating face-down in a pool or Keyser S?ze walking away like a ghost—but what fascinates me isn’t the ending. It’s how they got there.

So, what does my list say about me? Honestly, I don’t know yet. But hopefully, as I dig through these themes, we’ll figure it out together.

The Stockroom at The Wiz

Let’s talk about Reasonable Doubt. This album dropped in 1996. Back then, I was working in the stockroom at The Wiz. (If you’re too young to remember The Wiz, just know it was like Best Buy’s cooler cousin. Picture Circuit City with a touch more swag.)

In the stockroom, we had a rule: everyone got to pick an album to play in rotation while we worked. And you guessed it—Reasonable Doubt was one of my picks. Mind you, this wasn’t exactly a beloved or chart-topping album when it first came out. I could’ve easily swapped it out for All Eyez On Me or The Score without anyone complaining, but I kept returning to it.

Why? Because this wasn’t just music—it was a?blueprint?(pun intended)-although I did not necessarily know it in real-time. Jay wasn’t just talking about money and power; he was unpacking the chessboard of life—the calculated moves, the risks, the morality plays of the streets versus ambition.

Take “Can’t Knock the Hustle”, where Jay reminds us: “I’m makin’ short-term goals when the weather folds / Just put away the leathers and put ice on the gold.” That’s hustler logic in its purest form—plan for the now, but keep your eyes on the bigger picture.

Or look at “Politics as Usual”, where Jay hits us with: “My mind is infested, with sick thoughts that circle like a Lexus / If driven wrong, it’s sure to hurt you.” Your mind is your greatest asset—it can propel you to greatness or steer you straight into disaster, depending on how you use it. For me, this line is a reminder that ambition is a double-edged sword. The same drive that gets you to the top can destroy you if you lose focus or let greed take the wheel. It reflects the constant internal battle of the hustle—balancing hunger with control, ambition with discipline.

But the one that hits hardest as I’ve gotten older? “Regrets”. In it, Jay reflects: “This is the number one rule for your set / In order to survive, gotta learn to live with regrets.” That’s the truth no one wants to admit. We all carry regrets—choices we made, paths we didn’t take—but if you let them weigh you down, they’ll stop you from moving forward. You learn to live with them, or they’ll live with you.

Why This Album Matters

If I had to explain what this album means to me, I’d say this: Reasonable Doubt isn’t about the endgame—it’s about the grind, the moves, the strategy, and the question every man has to ask himself: “What’s your price?”

This was a hustler’s album. And in the broader sense, aren’t we all hustlers—or worse, being hustled? Whether you’re flipping bricks, stocks, or burgers, we’re all grinding for something.

So why start here? Because Reasonable Doubt mirrors what I’m trying to do with this series: unpack the journey. It’s about the choices we make, the illusions we cling to, and the truths we have to face along the way. And like Jay’s debut album, this series might not fly off the shelves at first, but give it time—it’ll grow on you.

Let’s see where this ride takes us. Check back next week for the first installment!