While reaction to the recent #PepsiLivesMatter commercial set the internet ablaze, leave it to Damon Young to deliver a pitch-perfect response that stood out among others:

“I always wanted to know what would happen if I handed a cop a can of Pepsi instead of my license and registration the next time I’m pulled over,” writes the co-founder of VerySmartBrothas.com (VSB), “and now I know.”

In a time when we’re trained to take our wit by the Twitter-sized micro-dose, the essay-length blog post is becoming a lost art. But VSB is about as good as it gets if you want a take on the intersection of pop culture, politics and race that’s thoughtful, heartfelt, hilarious and near-bulletproof in its logic.

That name, though. It’s a little misleading, but it’s also a little late to change it.

“I’ve been trying to re-brand it as VSB like Kentucky Fried Chicken did with KFC,” says Young, laughing. There are at least a dozen women who are contributing writers now, and 63 percent of VSB’s readership is female, notes Young.

VerySmartBrothas got its start discussing relationships in 2008, but gradually other subjects took precedence. “We wanted to be the irreverent, down-to-earth form of that conversation—’10 Ways to Make a Sex Tape,’ or ‘5 Things To Ask Her Mom,’” says Young. “As the site grew, our content became more diverse, and we left the initial theme behind.”

VSB’s readership is national, and it gets about 1.5 to 2 million readers per month. Young thinks it can get to 5 million. There aren’t a lot of Pittsburgh-based sites that get that kind of traffic, and fewer still that do it without the aid of the Black and Gold. (Well, there was a post about Mike Tomlin.)

“When you want a certain take on race that involves humor and thoughtfulness, on VSB those ambitions overlap,” says Young, who runs the site from his home in Pittsburgh. It took him years to learn this delicate balance, he says. But now, “I’m so used to doing it. I have a collection of templates in my head. I’ll start here, and connect this to that.”

That said, there isn’t really a formula for VSB’s content. The draw is simply good writing and perhaps a certain fearlessness.

It’s deeply personal and confessional one moment and sharp elbows the next. Whether he’s talking about police brutality or Twitter feuds by third-tier rappers, there’s always a point to be made, and often not one you see coming. You don’t really know if you’re being set up for heartbreaking profundity or a punchline (or both).

Young’s business partner, Panama Jackson, contributes frequently from D.C. and a regular crew of writers keeps the site changing every day.

Panama Jackson and Damon Young of VSB (VerySmartBrothas.com). Photo courtesy of Damon Young.

Panama Jackson and Damon Young of VSB (VerySmartBrothas.com). Photo courtesy of Damon Young.

Another surprise is VSB’s dedicated community of commenters who are often as good as the regular writers and add something to the discussiona rarity on the internet.

Whenever, say, Trump’s HUD secretary—or as Young dubs him, “repurposed Barcalounger with two dozen 10-year-old copies of Jet Magazine stuffed into it” Ben Carson—says that slaves were immigrants too, ridicule seems to be the healthiest response for Young. In the comments, the pitfalls of the sharing economy get pulled in—they weren’t slaves, they were “freelance agriculturalists,” or “unpaid interns.”

Not everything VSB does is determined by the news cycle, though.

Some of the best posts are one-off tangents like “The Definitive List (and Explanation) of Letters That Work as Nicknames.” (“G” always, “Y” nope), or “White People Shit That Black People (Not So) Secretly Love.”

Serious topics get taken seriously, when necessary: “Yup, I Have My Own Kid Now. And Yup, I Still Believe Spanking is a Terrible and Cruel Form of Discipline,” and “Hi Everyone. I had an Aortic Aneurysm Last Weekend, Which is As Deadly and Fucking Scary As It Sounds” (he’s fine now), or “I Don’t Want the Obamas To Ever Come Back,” an appreciation of the former First Family that isn’t what it seems upon first glance.

Occasionally, there are helpful guides for what to bring to a Black person’s cookout or how to behave in a Black church. It’s certainly possible for these things to be both (A) meant as a joke and (B) a vehicle for the truth, which is often unpleasant.

For instance, there’s “Dear White People: Here’s 10 Ways To Tell If A Black Person Actually Likes You.” If you’re allowed to bring the potato salad, you’re okay. Or, if the comfort level is such that, “We accept your invitation to all-White spaces that might lead to our death,” which includes, “A dinner party. Or a camping trip. Or West Virginia.”

Young grew up in Penn Hills and played Division 1 college basketball at Canisius College in Buffalo. He credits his father’s detailed critiques of his high school papers with helping him understand “how limitless language could be.”

“In college, I realized that the NBA thing wasn’t going to happen,” says Young. “So I took [writing] more seriously.”

His cousin, designer and blogger Sarah Huny Young, helped design the website and lent her own considerable online experience to the enterprise.

“When I started, I already had a fanbase by being her cousin,” says Young.

He notes that VSB posts can be about almost anything: “Depression . . . spelunking . . . what it’s like to be Black in Anchorage, Alaska. To have a hand in the Diaspora experience.”

A smaller city like Pittsburgh isn’t the obvious place for an enterprise like this but it works.

“I have a deconstructive, observational view—being distant from things is what I prefer,” says Young. “My literary agent likes that I’m not in New York or D.C. Those places can be distracting. There’s always a party or a signing or something.”

“I’m not at ground zero for cultural movements. I did have a little bit of angst about living in Pittsburgh, but I’ve been able to take VSB to places that transcend place.”

The workload is considerable when you factor in all the non-writing aspects of running a website. In addition, Young writes columns for Ebony and GQ, and his writing can also be found in Slate and The Guardian (UK); he’s also been a guest on MSNBC.

“One obvious advantage is financial,” says Young. “Because Pittsburgh’s cost of living is what it is, I can make a living doing this. It’s a city where you can be a working artist or a freelancer. You just don’t go into it thinking you’re going to work eight-hour days.”

Donald Trump and his administration, who made racial resentment a key part of their electoral strategy, present a target-rich environment for VSB. They’re also a perpetual outrage-generating machine that never seems to stop.

“I don’t know how to capture all that’s going on,” says Young. “A lot of us are trying to find a balance, between resisting . . . and writing about pizza or basketball.”

Young is currently working on a book for Ecco (HarperCollins), tentatively titled N*gga Neurosis.

It’s “a collection of interconnected essays, with memoir-ish characteristics,” says Young.

“It’s about being Black and experiencing something, and not knowing if your race colored it in any way,” says Young. “Like going to a department store, and being followed around by security, and wondering—‘Is it because I’m black, or are they just trying to help?’”