There's a moment early in the conversation between Andrew Pitcairn and Michael Dermer where the whole premise quietly flips. Pitcairn is a fourth-generation member of a 103-year-old family office — heir to a legacy that began with railroads, then oil and gas, and eventually his great-grandfather founding Pittsburgh Plate Glass. Dermer is a former acquisitions lawyer who walked away from a white-shoe firm for, in his words, "a basement and an idea for an industry that didn't exist." Two very different origins. And yet they arrive at the same conclusion about 2026 — and it isn't a comfortable one.

The conclusion is this: entrepreneurship used to be a choice. A brave, difficult, often lonely one, but a choice. Andrew's great-grandfather chose to build something. Michael chose to leave a safe career for a risky one. For most people, most of the time, the sensible alternative was simply to get a good job and climb. That alternative is disappearing. And when the safe path narrows to a thread, the risky path stops being optional.

It's almost like you have to be an entrepreneur, whether it's by choice or necessity. Not because it's aspirational — but because you have to create value for yourself.

To understand why that's so serious, look at what's actually happening to the "safe" path. By 2026, Bank of America received roughly 240,000 applications for fewer than 2,000 entry-level spots — an acceptance rate under 1%. Dermer raised almost exactly this in the video ("200,000 applications for 2,000 jobs"); the real number turned out even more brutal. The unemployment rate for recent college grads hit 5.6%, higher than the 4.2% overall rate — an inversion that used to run the other way. Young graduates once had lower unemployment than the general workforce. Now they have higher.

The great reversal: when choice became necessity

Dermer draws a sharp line between the great-grandfather's era and today, and it's worth sitting with. "Your great grandfather didn't have to — he chose to, and that created incredible wealth." Back then, building from nothing was the exception. "That was probably one in a million people who did that." The default was to find a place in the existing economy; the entrepreneur was the outlier.

In 2026 that ratio inverts. The default — the reliable corporate ladder, the pipeline into banking or consulting — is the thing becoming scarce and unreliable. So the skill that used to belong to the rare founder is becoming a baseline requirement for everyone. As Dermer puts it, "the new entrepreneurship" isn't about "an idiot like me leaving a white-shoe law firm and starting a business in a basement." It's narrower and more universal: how do I control my own destiny and create value that isn't controlled by someone else's hiring decision?

The second force is what Dermer described about new industries. Past technology waves destroyed some jobs but created many more — the internet erased travel agents but created podcasting, app development, social media as whole professions. This time is different: "When the new industry develops, instead of being ten jobs it's going to be two — because the other eight are going to be done by agents and AI." Roughly 50–55% of U.S. jobs are expected to be reshaped by AI within a few years. The escape hatch of "just get the equivalent job somewhere else" is closing at the exact moment the front door is overcrowded.

If you worked for Oracle and got let go, you're incredibly talented. But going to get the equivalent job somewhere else — that's going to be really hard.

The sketch artist and the graffiti kid

To anyone who says "creating value sounds nice, but I could never be an entrepreneur," Dermer tells two stories that dismantle the excuse. Years ago in Little Italy, he watched a street artist selling sketches to tourists for $20 apiece. The work was extraordinary. When he learned $20 was the going rate, he told her to take that exact talent to law firms instead — to sell art to firms that would pay real money. She now makes, by his account, around $400,000 a year. Same hand. Same talent. Different playground.

The second story is starker. A teenager in Memphis was doing graffiti and, by his own admission, was minutes from joining a gang because it looked like his most realistic route to economic survival. His graffiti art was remarkable. Today he holds contracts with roughly six agencies for that art and earns something like $250,000 a year. Dermer's framing is deliberate: these were "the two least-equipped people with means or opportunity." No capital. No network. No safety net.

These were the two least-equipped people with means or opportunity. All they needed was to shift their thinking into where can I create value a little bit differently.

The lesson isn't that everyone can make $400,000 sketching. It's that the barrier for these two people was never talent or resources — it was positioning. The willingness to ask where their existing value would be priced correctly, and to move it there. That's the muscle Dermer says now applies to ordinary career survival, not just visionary founders.

Passion and grit are not a plan

If there's a warning threaded through the whole conversation, it's this: telling people to "just become an entrepreneur" without teaching them how is reckless. Dermer is scathing about the old advice. "It would be the equivalent of saying, Andrew, I'm going to go perform heart surgery tomorrow" — no medical school, just passion and a willingness to "fail fast." We'd never accept that logic in any other high-stakes field, yet it's exactly what we've told aspiring founders for decades: have passion, grit, and a good idea, and go "play in traffic."

It's not OK, especially with AI, to just say "go play in traffic and hope you don't get hit by a bus."

That gap is what The Lonely Entrepreneur was built to close — a one-stop foundation of the things nobody teaches, whether you're trying to put food on the table or break out within a legacy family. Because the tools have never been more accessible. What used to take Andrew's family "75 years to learn," Dermer notes, "now takes 75 seconds to learn." The knowledge is available. The mindset — and the willingness to embrace the new reality rather than wait for the old one to return — is the part still up to you.

The skill that doesn't get automated

The comforting version of the AI story is that it just replaces tasks. The honest version — the one Pitcairn and Dermer keep circling back to — is that it replaces the safety of not having to think like an owner. The advice they land on isn't "quit and start a company." It's narrower and harder: develop the ability to create value that isn't controlled by someone else's hiring decision.

That's the difference between being one of a thousand résumés and being one of one. Small business was never fringe — roughly 98% of U.S. firms employ fewer than 100 people. What's changing is that a huge new wave is being pushed into building by necessity rather than pulled by ambition. Gen Z now shows the highest entrepreneurial intent of any generation, and for the first time is starting more businesses than Baby Boomers. The instinct Dermer describes isn't theoretical. It's already in the numbers.