Life & Career
By WORKFLOX Team • June 2026

In a candid, emotional, and statistic-packed conversation with actor Ben Stiller, NYU professor and entrepreneur Scott Galloway breaks down why young men are struggling more than ever, what's gone wrong with modern role models of masculinity, and why the alliance between men and women is the greatest force in human history.
"The most dangerous person in the world is a lonely, broke, young man." > — Scott Galloway
If you've ever watched someone speak and thought, I understood maybe 30% of that but I believe every word of it — you've probably encountered Scott Galloway.
Galloway is a brand strategist, NYU professor, author, podcast host (the legendary Pivot with Kara Swisher), and entrepreneur who has built and sold multiple companies. He's a man who can say "Tesla is a drunken tourist with a Hublot watch" and somehow make it the clearest thing you've heard all week.
Much like the founders who build AI powered web and mobile products to solve real-world problems at scale, Galloway has built a media empire — newsletters, books, television, podcasts — all in service of one mission: helping people understand a fast-moving world before it leaves them behind.
Ben Stiller — yes, that Ben Stiller — sat down with Scott to discuss his latest book, and what unfolded was part intellectual fireside chat, part emotional confession, and part urgent call to action for a generation of struggling young men.
Scott Galloway doesn't just have opinions — he has receipts. And the data on young men in America is sobering.
Here are the hard numbers:
These aren't just statistics. They represent real human beings — sons, brothers, friends — falling off the map.

This is the question Ben Stiller asked, and Galloway's answer is one of the most thoughtful responses you'll find on the subject.
The gag reflex is understandable.
Men — particularly white men — have had a 30,000-year head start. Between 1945 and 2000, the United States registered a third of all global economic prosperity with just 5% of the world's population. That prosperity was largely concentrated among white, heterosexual males.
So when someone starts talking about "poor men," the immediate reaction is: Is this just a thinly veiled attempt to set back the rights of women and minorities?
But Galloway argues that empathy is not a zero-sum game. Lifting men up doesn't mean pushing women down.
"Civil rights didn't hurt white people. Gay marriage didn't hurt heteronormative marriage. We can walk and chew gum at the same time."
Two groups have failed young men simultaneously:
The Far Right recognized the problem but offered a toxic remedy — return to the 1950s, where women and minorities had fewer rights. They conflated masculinity with cruelty and coarseness.
The Left dismissed the problem entirely, telling struggling men they don't have problems — they are the problem. Their advice? "Act more like a woman." Not helpful.
The result? A generation of young men with no one speaking their language constructively.
One of Galloway's most important points goes largely undiscussed: the deepest-pocketed companies in the world have built a profit motive around keeping young men isolated, enraged, and online.
Young men, with their less-developed prefrontal cortexes, are particularly susceptible to algorithms designed to enrage and addict. The result is a generation of men who are:
When women lack romantic relationships, they tend to invest in their friendships and professional lives. When men lack romantic relationships, too many fall into rabbit holes of online radicalization.
This is not a moral failure of young men. It's the predictable outcome of a system designed to exploit their vulnerabilities for profit.
This is perhaps the most powerful framework in Galloway's worldview — and the antidote to the "toxic masculinity" conversation that tends to go nowhere.
Leg 1: Be a Provider
Get strong. Get skilled. Get economically viable. Not because money equals worth, but because building capability gives you the foundation to do something meaningful with your life. Think of it like building a product: you need a stable foundation before you can scale.
Leg 2: Protect
Once you're strong, use that strength to protect others — your family, your community. The most universally respected professions — military, firefighter, police officer — are all rooted in protection.
Leg 3: Plant Trees Whose Shade You'll Never Sit Under
This is the whole point. The ultimate expression of masculinity is protecting people you'll never meet. Contributing to something bigger than yourself.
"If you're the richest man in the world and you're cutting aid to HIV-positive mothers, that should be a reputational extinction event. The whole point of masculinity is: take care of yourself, then protect your family, then protect your community, then protect strangers."

Here's a statistic that might surprise you: widows are happier after their husband dies. Widowers are less happy.
This isn't a knock on marriage — it's a testament to how differently men and women experience relationships.
The research is clear:
Galloway himself admits he never wanted to get married or have kids. He was perfectly content with what he describes as "an empty and meaningless life in New York — but as far as empty and meaningless experiences go, it was pretty damn good."
Then he had children. And everything changed.
"The only time I have ever felt sated is when I'm with my boys and my partner, and the kids throw their legs over ours on the couch, and I know they're safe. I know they're loved. I know they love me. It's the only time I've thought: I get it. This is enough."
One of the most striking reframes Galloway offers: marriage has become a luxury good.
Why does this matter? Because historically, when men lack both economic and romantic opportunity, societies become unstable and violent.
"The most dangerous person in the world is a lonely, broke, young man. If you look at the most unstable, violent societies in the world, they have a disproportionate number of young men without economic or romantic opportunity."
Who is actually driving the conversation about young men forward? Not politicians. Not young men themselves.
Mothers.
Galloway's fanbase skews young male. But his supporters — the people who share his work, show up to his talks, and push this conversation into the mainstream — are overwhelmingly mothers.
Their message is always some version of:
"I have three kids. My two daughters are thriving — one's in PR, one's in grad school. My son is in the basement vaping and playing video games. What do I do?"
For all his data and statistics, Galloway's real power comes from vulnerability. And nowhere is that more evident than when he talks about his father.
Raised by a single Scottish immigrant mother who worked as a secretary her entire life, Galloway grew up with an absent father — a charming, handsome man who married (and divorced) four times. He left when Scott was eight.
For years, Galloway held onto resentment — a mental scorecard of every perceived failure and absence.
The shift came in his 40s.
"I asked myself: what kind of son do I want to be? What kind of friend? What kind of partner? And I decided to hold myself to that standard and put away the scoreboard — because you always inflate your own contributions and diminish theirs, and you end up unhappy."
The lesson: the scorecard approach to relationships will always leave you miserable. Decide the kind of person you want to be — and be that person, regardless of what you receive in return.
One of the most memorable frameworks in the conversation is what Galloway calls surplus value — and he considers it the true litmus test of whether a boy has become a man.
The question is simple: Are you creating more than you're consuming?
When you reach the point where you are adding more than you're taking — more love, more concern, more economic value, more emotional support — that's the whole point. That's adulthood. That's purpose.
From age 29 to 44, Scott Galloway did not cry once. Not when his company went bankrupt. Not when his mother died. Not when he got divorced.
He literally forgot how.
Then, somewhere in his 40s, he started again. And he's been making up for lost time.
His advice to men:
"When something moves you — a piece of art, a piece of music, something you've read — stop and really bask in it. Try to understand why it moves you. Let yourself lean into it. Life goes fast. If you aren't regularly practicing feeling things, your life will go like that — and at the end, you'll regret not having slowed down and actually been human. Sentient means feeling."
Men have been conditioned not to show weakness — and for 99% of human history, that was rational survival behavior. But we're not in that world anymore. The men who allow themselves to feel, to process, to cry — they tend to be less prone to the anxiety and rage that plagues so many of us.

Galloway ends with a call to unity that cuts through all the noise.
Young men are being told their problems are caused by women. Young women are being told that men are dangerous predators to be avoided. Both narratives are wrong — and both are being actively amplified by algorithms that profit from division.
Here's what the data actually shows:
The solution isn't more division. It's more alliance.
"There is 7.5 billion points of evidence that the greatest alliance in history is the alliance between men and women. The happiest households bring a combination of masculine and feminine energy. Let's decide we're allies again instead of finding reasons why it's the other gender's fault."
Here's what Scott Galloway wants every young man — and the people who love them — to walk away knowing:
For Young Men: - Get strong — physically, emotionally, financially - Pursue real relationships over digital substitutes - Put away the scorecard in every relationship - Decide what kind of man you want to be — and hold yourself to that standard - The goal isn't just to provide for yourself — it's to eventually protect and serve others
For Society: - We need to invest in young people economically — they are 24% less wealthy than their equivalent age cohort 40 years ago - Marriage and family formation are now luxury goods — that's a policy failure, not a cultural choice - The far right and the far left have both failed young men. The answer lies in empathy, not ideology
For Everyone: - Empathy is not zero-sum. Lifting up men does not mean pushing down women - The alliance between men and women is the foundation of every thriving civilization - Surplus value — giving more than you take — is the whole point of a human life
Young men are falling further and faster than any group in America. And we've been too politically paralyzed — or too caught in our own gag reflexes — to have an honest conversation about it.
Scott Galloway isn't asking us to go back to the 1950s. He isn't making excuses for privilege. He's asking us to look at the data, feel the weight of it, and act accordingly — because the cost of inaction isn't just paid by young men. It's paid by all of us.
The most rewarding thing a human being can do is build something — a family, a career, a community — with other people. Not in spite of them. What matters is that you're building with someone. That you're creating more than you're consuming. That you're planting trees whose shade you'll never sit under.
That's the whole shooting match.
Scott Galloway argues that young men in America are experiencing a genuine crisis — not a perceived one — backed by hard statistics. He points to skyrocketing suicide rates (4 in 5 suicides are men), rising rates of homelessness, incarceration, and addiction, and a dramatic collapse in romantic relationships and family formation. His core argument is that both the political left and right have failed young men: the right offers a toxic return to 1950s masculinity, while the left dismisses male struggle entirely. What's needed is honest, data-driven empathy — the same kind we extend to every other group in crisis.
Galloway's framework breaks masculinity into three stages of development. The first leg is Provider — building physical strength, professional skills, and economic viability so you can sustain yourself. The second leg is Protector — once you're stable, using that strength to shield your family and community. The third and most important leg is Plant trees whose shade you'll never sit under — contributing to people and causes beyond your own immediate circle. He argues that a man who has accumulated great wealth and power but uses it to punch down has entirely missed the point. True masculinity, in his view, is always expansive and protective, never extractive.
Galloway cites research showing that men derive significantly greater longevity and wellbeing benefits from committed relationships than women do. Women in relationships live 2–4 years longer; men in relationships live 4–7 years longer — nearly double the benefit. He also highlights that widowers (men who lose their wives) typically become less happy and more isolated, whereas widows often maintain stronger social networks and recover better. For men who lack romantic relationships before age 30, the research shows a 1 in 3 chance of developing substance abuse issues. His point is not that men are weaker, but that they rely more heavily on their primary relationship as their core emotional infrastructure — and society needs to help men build that infrastructure earlier and more intentionally.