Generation 1099: The Side Hustle Generation Isn't Lazy... The System Is Broken
Why You Haven't Started a Business
55% of young people surveyed said they've seriously considered starting a business. Only 11% said they weren't interested at all. So why is the rate of new business creation in America falling off a cliff?
The easy story is the one where young people are soft. Afraid. Too comfortable scrolling to build something real.
That story is a lie.
Hank Green recently dug into this question with a combination of his own Twitter survey data and macroeconomic research from Gallup, The Wall Street Journal, and the Economic Policy Institute. What he found should make every mentor, educator, and policy maker sit up straight... the entrepreneurial spirit in young people is alive and burning. The infrastructure around them is what's crumbling.
Let that land for a second.
The Desire Is There. The Doors Are Not.
15% of respondents over 18 had already started a business. Over half had seriously considered it. The hunger is real. But hunger doesn't mean much when the kitchen is locked.
Student debt has skyrocketed as schools compete for enrollment. The average debt per borrower has climbed steadily since 1993, and that weight pushes young people toward "safer" decisions. You don't jump off a cliff when you're carrying a boulder. You don't risk failure when failure means drowning in debt you can't discharge through bankruptcy.
Then there's healthcare costs in America. When your health insurance is tied to your employer, leaving that employer to chase a dream isn't bold... it's terrifying. The system literally punishes you for trying.
Three months without food, three days without water, three minutes without hope. And the current system is an industrial-grade hope suppressor for aspiring entrepreneurs.
Follow the Money... It's Not Coming Your Way
Here's where it gets structural. Venture capital mostly chases high-growth tech companies... the kind that promise 10x returns. A neighborhood bakery? A community bookstore? A small manufacturing shop? Those "boring" businesses that build the backbone of actual communities get ignored.
Community banks now make up just 13% of the banking sector. But they still originate 43% of all small business loans. That's a critical infrastructure gap hiding in plain sight. The one type of institution most likely to fund a young person's dream is disappearing.
Meanwhile, wealth inequality has reshaped who even has capital to risk. Between 1983 and 2009, the top 1% captured a massive share of total wealth gains while the bottom 80% actually lost ground. Between 1998 and 2013, median net worth for the lower, working, and middle classes decreased. The people with money see small business ownership as "an inconsequential investment in exchange for a whole lot of work." The people with the fire and the grit? Their pockets are empty.
The money flows upward into the stock market, inflating gigantic entrenched companies. Those behemoths then expand into new markets... Amazon, Netflix... swallowing the very spaces where small businesses used to thrive.
Generation 1099: They ARE Starting Businesses
Here's the plot twist nobody talks about enough.
Young people are starting businesses. More than ever, actually. They're just not the kind that show up in traditional metrics.
This is Generation 1099... the side-hustling, multi-income, patchwork entrepreneurs. The person running a podcast AND an Etsy store AND doing Postmates AND working a day job. Every single one of those side hustles is technically a sole proprietorship.
BAM... that changes the whole narrative.
But the path from sole proprietorship to hiring your first employee? That path is buried under mountains of regulatory red tape, business taxes, and global competition that makes every supply chain a battlefield. The leap from "I'm making it work" to "I'm building something that employs others" has never been harder.
It's not that young people don't want to build. It's that the system has made scaling nearly impossible for anyone who isn't already wealthy.
What This Means for Those of Us Who Serve Young People
If you mentor younglings... if you teach, coach, or champion young adults... this data matters. Because the kid sitting across from you who seems "unmotivated" might actually be drowning in structural barriers you can't see.
Our primary job in this life is to effectively understand other humans. And understanding this generation means seeing past the easy narratives. They're not lazy. They're not entitled. They're navigating an economic landscape that their parents and grandparents would barely recognize.
The question isn't "why aren't young people starting businesses?"
The question is "what are we going to do about the barriers crushing their ability to try?"
Access to capital. Student debt reform. Healthcare decoupled from employment. Community banking infrastructure. Simplified business regulations for small operators. These aren't abstract policy debates. They're the difference between a generation of dreamers and a generation of builders.
Light doesn't fight darkness... it just shows up. And showing up here means advocating for systems that actually serve the people inside them.
Hank Green closed his video with something that hit me in the chest: he wants more people, not fewer, to know the joy of starting your own thing. Of giving somebody a job. Of putting a team together to create value where there was none before. That's not a political statement. That's a human one. So whether you're a young person sitting on a dream, or someone with the power to remove a barrier... show up. The entrepreneurial spirit in this generation isn't dying. It's being suffocated. And that's something we can actually fix. 💪
--- Source: https://www.youtube.com/watch?v=Q_NrLQnmCBw
From TIG's Notebook
Thoughts that surfaced while watching this.
What I put into my mouth affects mostly me,— TIG's Notebook — New Captures
We don't build trust by offering help. We build trust by asking for help. — *Simon Sinek*— TIG's Notebook — On Connection & Understanding
TIG izms... one day we started collecting them and over the decades they turned into this little book.— TIG's Notebook — About This Document
Echoes
Wisdom from across the constellation that resonates with this article.
There should never be a pause in a comedy unless you decide it's gonna be funny to pause.
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