A new way of entering the job market
A Draft Advice Note
I’ve been thinking about the job market and the AI hysteria. I have never believed that the two things are related. I’ve been drafting a note to a young woman I’ve been advising. She’s sure (because she heard it on the internet) that entry level jobs have evaporated. This is me trying to explain what’s going on.
In a nutshell, the territory has changed but the map remains the same. A lot of what we hear is better explained by that than by doomer AI prophesies.
Please let me know if I have this right
Hey
I’ve been thinking about your job hunt and wanted to get this down before you fire off another round of applications to Google.
The market you’re walking into isn’t broken. It just got rewired, and nobody bothered to print a new map.
Quick history. When I came up, the big companies were the school. IBM, GE, Westinghouse, Accenture, the banks. They hired kids out of college and spent two or three years teaching them how a business actually works. The first job out of school was an apprenticeship that came with a salary. They expected to turn you into someone useful, and most of the time they did.
That’s over.
Public companies optimize quarter to quarter now. Training is expensive, slow, and doesn’t show up on an earnings call. Hiring someone already trained does. So the big outfits stopped growing their own people. They buy them. And when they need a whole team they buy the startup that already built it.
That’s why every “entry level” posting at a Fortune 500 asks for three to five years of experience. They aren’t confused. They’re just no longer in the business of teaching anyone anything.
Stop there and it looks like there’s nothing left for someone at your stage. There’s plenty. It just moved.
Here’s a number that doesn’t get nearly enough attention. Americans filed about 5.6 million new business applications in 2025 , and we’ve been running something close to that every year since the pandemic. Before COVID, applications averaged around 270,000 a month; we’re now well over 400,000 . The strongest years for new business formation on record have all happened in this decade . That isn’t a blip. That’s where the work is going.
Most of those new outfits will fail. Plenty will stay tiny on purpose. But a real chunk of them are exactly the places that hire somebody smart who’s willing to learn and put them straight to work on real problems. They can’t afford the polished thirty-five-year-old with the right resume, so they hire someone earlier in their career and bet on them.
You won’t get a careful onboarding. You’ll get handed a problem Tuesday morning and figure it out by Friday. That’s the good part.
In a small company you don’t get siloed. You see the money come in and go out. You watch customers complain to your face. You find out what ships and what doesn’t because you’re one of the people shipping it. When something breaks you’re three feet from it. When you make somebody’s life easier, the founder knows your name by the end of the week.
The trick is finding them. They don’t run ads on Indeed.
Look for places that are obviously moving fast and a little ragged. Outdated website. A job post written by an exhausted founder at one in the morning. Customer reviews asking for features that don’t exist yet. Anybody in town who just closed a Series A. Local news about a company suddenly hiring.
When you reach out, you aren’t applying. You’re showing up with your hand raised, offering to solve something. That’s more work than the Easy Apply button. That’s the point. The corporate doors are welded shut. The smaller doors open if you walk up and knock.
Quit wasting your good years on companies that want a finished product. Find one that needs you and will let you learn the job by doing it. That’s where people at your stage still build something.
Grab coffee this week if you want to talk it through. On me.
Best,
John
Great summary of what’s happening in the market.
I think you have it right John, and the solution is to teach young people a different operating model.
The broken move is telling them to keep firing resumes into Fortune 500 portals where the filters are built to reject ambiguity. Early-career people are, by definition, ambiguous. They have potential, but not much proof yet.
So the playbook has to change:
Pick a lane: sales support, customer success, operations, marketing ops, research, implementation, product support - something specific enough to be understood.
Find growing companies with visible pain.
Build a one-page proof note: “Here is what I noticed. Here is what I would improve. Here is why I think it matters.”
Send it directly to founders, operators, department heads, and investors connected to the company.
Ask for a 15-minute problem conversation, not a job.
That is how young people bypass the résumé pile. They stop asking, “Do you have a job for me?” and start asking, “Do you have a problem I can help solve?”
That is where the market still rewards initiative.