Job description says “We’ll train you,” then rejects you for not having experience. Gen-Z is struggling to find jobs in the current market.

Finance commentator Damon Cassidy says the modern entry-level job market has turned into something close to a bad joke. The jobs are called “entry level,” the postings say things like “we’ll train you,” and then the rejection comes because the applicant does not already have enough experience.

That contradiction sits at the center of Cassidy’s argument. In his recent video, he says Gen Z is walking into the worst possible version of a problem that has been building for decades, where the first rung of the career ladder is still advertised, but in many cases, it is no longer really there.

His framing is blunt. Cassidy says Gen Z is facing the worst entry-level market in nearly 40 years, in a system where young people are told to go to college, take on debt, build credentials, and then somehow compete for beginner jobs that increasingly demand years of prior work history.

That is the part that makes the whole thing feel absurd. A society cannot keep telling people to “start somewhere” while quietly redesigning every starting point for people who already started somewhere else.

Cassidy’s broader point is that this is not some sudden collapse that came out of nowhere. It is the result of a long shift in how companies think about labor, training, cost, and risk, and now Gen Z is paying for all of it.

The “Entry-Level” Label Barely Means Anything Anymore

Right at the start, Cassidy argues that what employers call entry-level work no longer matches what the phrase used to mean. He points to figures he says show that two-thirds of all entry-level roles are being filled by people with more than seven years of experience.

If that number sounds ridiculous, that is because it is. The whole point of an entry-level role is supposed to be entry.

Cassidy also says most employers are not even seriously considering recent graduates, which helps explain why so many young job seekers feel like they are trapped in a loop. They are told to apply broadly, build skills, and stay patient, yet the market keeps rewarding people who are already established.

He argues that the result is not just frustration, but a kind of career paralysis. A role that once would have been the starting point for long-term growth has become another gatekeeping device.

That is especially damaging for Gen Z because the generation is not only competing with itself. Cassidy says young workers are also competing with Millennials, Gen X, and even Baby Boomers in a market that is already short on true beginner opportunities.

Once that happens, the term “entry level” starts sounding less like a job category and more like marketing language.

The Problem Did Not Start With Gen Z

One of Cassidy’s strongest points is that this did not begin with Gen Z, even if Gen Z is taking the hit right now. He traces the problem back through earlier generations and argues that each group inherited a worse version of the same broken setup.

He says that in the 1980s, as the country pushed college harder, deindustrialized large parts of the economy, and prioritized shareholder returns, employers began abandoning the older idea that someone could build a stable life with a high school diploma and a decent first job. Instead, the bar for entry kept rising while the quality of available jobs sank.

Cassidy cites a Time magazine piece about blue-collar decline and mentions William West, a crane operator in Pennsylvania, who wondered what kind of future his son could have if even a high school education was no longer enough to get a decent job. That quote lands because it shows this anxiety is not new.

He also notes that only 28 percent of jobs created in the 1980s were in high-level occupations, while many of the openings left for high school graduates clustered in low-wage service work. At the same time, he says wages for young men and women fell sharply over time.

In Cassidy’s telling, this is where the modern mess began to take shape. A college degree slowly became the new baseline instead of the advantage, and once that happened, employers started asking for even more on top of it.

That is how a system ends up telling applicants they need experience to get the job that was supposed to give them experience in the first place.

Every Generation Got The Same Lecture, But The Ladder Kept Moving

Cassidy argues that Gen X and Millennials were fed the same basic script. Work hard, get educated, stay flexible, and eventually things will click. But the ladder kept moving upward while the floor kept dropping away.

He points to the dot-com era and says Gen X entered adulthood in an intensely competitive environment where college degrees were more common, student debt was growing, and employers could offer low pay because there was always another applicant waiting. In his telling, entry-level jobs began demanding expert-level ability for entry-level wages.

He quotes intellectual property lawyer John Conway reflecting in 2001 that his generation got stuck in entry-level jobs while the cost of living kept climbing. Conway’s line that “in the middle of the game, the rules changed” captures Cassidy’s argument well.

Then came Millennials, who Cassidy says became the most educated generation in history by 2008 just in time for youth unemployment to surge to 19.2 percent. At the same time, he argues, internships increasingly replaced real entry-level jobs.

That shift matters because internships were sold as stepping stones, but Cassidy suggests they often became detours, delays, or outright substitutes for paid career starts. He notes that internship participation rose dramatically and unpaid internships multiplied as the economy weakened.

So when people now act like Gen Z just does not understand hardship, Cassidy’s answer is that this same breakdown has been happening for decades. The difference is that each generation inherited a thinner version of the old promise.

Gen Z, in his view, simply got the most hollowed-out version yet.

Gen Z Is Now Competing For Worse Jobs With Higher Demands

When Cassidy turns back to the present, he makes the situation sound especially grim. He says the United States has lost 43 percent of mid-wage occupations since the financial crisis and gained 58 percent more low-wage jobs.

That means many younger workers are not just fighting for fewer opportunities. They are fighting for lower-quality opportunities.

He says more than 70 percent of entry-level jobs now require a college degree, and nearly 40 percent ask for three to five years of experience. Median entry-level wages, he adds, sit only slightly above what a Ford factory worker earned in 1914.

That comparison is jarring, and it is supposed to be. Cassidy is trying to show how disconnected the modern labor market has become from the language companies still use to describe it.

He also points to a study from Business.com involving 300 job applications sent by departing interns. According to Cassidy, only 12 percent received any response, just 5 percent showed interest, and none resulted in a hire. He says candidates were actually more likely to be ghosted when they met over 90 percent of the listed requirements.

That part is especially bleak because it shows the problem is not simply underqualified applicants. Even people who closely match what a company says it wants are often getting nowhere.

And that is where a lot of Gen Z’s anger comes from. The rejection is one thing. The randomness is worse.

AI, Outsourcing, And Hiring Rules Are Making A Bad System Worse

Cassidy spends a large part of the video arguing that this broken market is now being pushed even harder by AI, outsourcing, and what he sees as distorted hiring incentives. He says tasks once assigned to junior workers are increasingly being automated, which is shrinking the number of beginner roles available.

He also disputes the comforting idea that entry-level jobs are too valuable for companies to cut. Some analysts, he notes, argue that entry-level hiring is necessary to build future leaders and create a healthy internal pipeline. Cassidy says that may sound nice, but it does not reflect the labor market companies have actually built.

His answer is simple: if entry-level roles mattered that much to employers, they would have protected them. Instead, he argues, those jobs have been neglected for more than 40 years.

Cassidy cites projections that by the end of 2026, more than a third of companies say they will have frozen entry-level hiring, and by 2027 nearly half expect to eliminate it entirely. He also references predictions that AI could wipe out 50 percent of entry-level jobs by 2030.

Even if those forecasts turn out too extreme, the direction is hard to miss. Companies are clearly looking for ways to cut training, reduce payroll, and automate basic functions.

Cassidy also ventures into another sensitive area: H-1B hiring in entry-level tech roles. He argues that growing “experience” demands in supposed beginner jobs may sometimes be less about skill and more about structuring hiring in a way that makes certain labor pipelines easier to justify.

Whether people agree with every part of that argument or not, the broader point is clear enough. Cassidy believes the system is increasingly being designed to avoid investing in young workers.

That is a dangerous habit for any economy.

His Most Personal Point May Be The Strongest One

Late in the video, Cassidy gets away from charts and studies and tells a story about his own first jobs. He says he worked at a garbage company, at a friend’s Chinese restaurant, and then at Torchy’s Tacos, where he was the first employee hired at one location.

He says that job taught him leadership, time management, and all sorts of foundational skills that still matter in his life now. But when he goes back to that same location today, the cashiers are gone. There are tablets.

That may sound like a small detail, but it is one of the most important moments in the whole video. Cassidy is not just mourning a nostalgic teenage job. He is pointing to the disappearance of low-stakes early work where people learned how to show up, deal with pressure, and become more employable.

When those jobs vanish, the loss does not just hit teenagers. It weakens the entire talent pipeline.

Cassidy also says he does not think it is healthy that older workers are being pushed into the kinds of positions that once would have served as stepping stones for younger people. That does not mean older people should not work. It means the entire market is becoming too crowded at the bottom because the middle has thinned out and the ladder above it is breaking.

That is what makes the situation feel so unstable. Too many people are standing on the same few lower rungs, and fewer are moving up.

The Market Still Has Opportunities, But The Trend Is Going The Wrong Way

Cassidy is not saying the world is over. He explicitly says there are still ways to build a career. He mentions the trades, networking, communication, entrepreneurship, and the more traditional paths that still work for some people.

But his warning is that things are getting worse, not better.

That distinction matters. It keeps the video from falling into empty doom. Cassidy is not claiming success is impossible. He is saying the path into adulthood has become far less stable, far less fair, and far less clear than it should be.

His closing argument is that none of this had to happen. In his view, decades of short-term thinking, weak leadership, and social indifference let the problem grow from one generation to the next. And now Gen Z is being told to fix itself inside a market that barely wants to train beginners anymore.

That is why the “we’ll train you” line stings so much when the rejection comes for lack of experience. It is not just hypocrisy. It is a small, polished version of the whole broken system.

And Cassidy’s message, underneath all the anger, is really pretty simple: if a country stops creating real places for young people to begin, it should not act confused when beginning gets harder every year.