Gary Vaynerchuk has a message for suburb parents, and it’s not the one you’d expect from a guy who built his career on aggressive hustle culture.

Vaynerchuk, CEO of VaynerMedia and Chairman of VaynerX, sat down with Fatherly to talk about boys, screens, and where he thinks modern parenting went sideways. His self-assessment was surprisingly direct. “I know I was well parented,” he told Fatherly, “and I have all of my validation, and I mean all of it, wrapped up in being a nice guy.”

From someone famous for bluntness, that’s worth stopping on.

Here’s the problem Vaynerchuk is responding to. If you’ve got sons in middle school or high school right now, there’s a good chance they’ve encountered the manosphere, a sprawling online ecosystem built around resentment, rigid masculinity myths, and content engineered to make young men feel like the world owes them something it’s been withholding. The pipeline doesn’t announce itself. It starts with fitness advice or video game commentary and ends somewhere a lot darker. Suburban parents often don’t catch it until something the kid says at dinner stops the conversation cold.

Vaynerchuk doesn’t pretend the pressures on boys aren’t real. He’s talked openly about getting into roughly ten fights during his school years. His mother didn’t call a crisis line. She didn’t ground him into oblivion. The lesson he took wasn’t that fighting was fine, it’s that some friction in a kid’s life doesn’t require parental intervention at every turn.

That’s where his critique of contemporary parenting gets specific. “I do think, especially for boys, we got a little too into eighth-place trophies,” he said, adding that the cultural drift toward softening every hard edge left a generation of kids without the tools to handle disappointment. The American Psychological Association has documented at length how resilience develops through managed adversity, not its absence. Vaynerchuk wouldn’t cite APA research, but he’d recognize the point.

Still, he’s not making the case that parents should back off entirely. That’s where his argument gets interesting. He draws a clean line between two things that can look identical from the outside. “Supporting your child is everything,” Vaynerchuk said. “Enabling your child is a disaster.” Supporting means being present, engaged, willing to set limits. Enabling means absorbing every consequence on your kid’s behalf until they can’t absorb anything on their own.

Walking that line is the actual work. It doesn’t have a clean Tuesday night answer.

But Vaynerchuk doesn’t avoid the practical stuff. He tells parents to be willing to pull phones. Pull social media access. Not as performance discipline, but as a real intervention when something’s clearly wrong. That’s a parent doing their job, not overreacting.

The timing of this conversation isn’t accidental. Netflix dropped “Louis Theroux: Inside the Manosphere” this year, and it’s been circulating hard among parents trying to get a read on what their kids are actually watching. The documentary puts One British journalist, Louis Theroux himself, inside some of the most extreme corners of that world. What Theroux finds isn’t cartoon villainy. It’s a network of men who’ve turned their own Rage and Resentment into content, into income, into community. He gets trolled in real time. He asks questions that don’t get clean answers. The whole thing is uncomfortable in exactly the way it should be.

What the documentary makes clear, and what Vaynerchuk’s interview reinforces from a different angle, is that the manosphere fills a vacuum. Boys who feel unseen, underprepared, or stripped of any standard worth meeting don’t just shrug and move on. They find something that offers them a framework, even a bad one.

That’s what the eighth-place trophy argument is really about. Not that competition is sacred. That boys who never learn to lose, who never sit with disappointment without someone rushing in to fix it, become adults with no internal resources. And adults with no internal resources are exactly the audience those influencers are targeting.

“Supporting your child is everything,” he said. The word enabling is doing a lot of work in that sentence, and that’s the point.