There's a question at the center of the conversation between Andrew Pitcairn and Michael Dermer that every wealthy family is now quietly asking: what role can entrepreneurship play in preparing the rising generation for the future? Pitcairn is a fourth-generation member of a 103-year-old family office — a lineage running from railroads to oil and gas to his great-grandfather founding Pittsburgh Plate Glass. Dermer built a company from "a basement and an idea," survived the 2008 crisis, sold it, and now runs The Lonely Entrepreneur. Their answer converges on one uncomfortable idea: inheritance is not preparation.

The funnel above is why that matters. Only about 12% of family businesses reach the third generation, and just 3% survive to the fourth. Pitcairn's family sits in that tiny sliver — and it got there by producing builders in every generation, not just custodians. As the great-grandfather's Pittsburgh Plate Glass shows, the wealth was created, not merely handed down. The families that fall off the cliff are the ones who forget that distinction.

Entrepreneurship shouldn't end with just the first-generation wealth creators. It's how do we instill that mindset that we all should be not just stewards — but wealth creators.

The timing makes it urgent. And it's arriving at the exact moment AI is dismantling the career tracks those heirs were groomed for. As a Wall Street Journal headline that framed this very event put it: "Forget Wall Street. Elite Students Are Spending Their Summers on Startup Dreams." Top students are skipping the prestige internships — banking, consulting, big tech — to launch AI startups instead. They can already see what's coming for the "safe" paths.

Why "maintaining" the asset is no longer enough

Dermer's most pointed argument is about entitlement — and it isn't a moral lecture, it's a survival argument. "Being a steward of wealth is a huge responsibility," he grants. "With great wealth comes great responsibility." But stewardship, done passively, has a failure mode: it teaches the next generation to protect what exists rather than build what's next. In an AI economy, protecting what exists is a losing strategy, because what exists is being disrupted whether the family participates or not.

He draws the sharpest line around risk itself. "When you have means behind you, it's easy to fail and then just say, well, that's OK, because I'm not worried about putting food on the table tomorrow." That safety net, so valuable in most respects, quietly removes the very pressure that builds capability. Entrepreneurship reintroduces it on purpose — it's what forces you to "sit up at night and worry about the people you're responsible for, or the investors whose money you took, or how you'll stay relevant when competition is coming up behind you."

It's very humbling. And it's not something that can be given to you. It's something you have to earn. Boots on the ground. It's scraping.

This reframes the family's central task. The old operating companies still have to cope and evolve — "maintaining" an asset in an AI world may not be enough to keep it alive. And the next generation has to arrive with genuinely new skills, not just a family name and a seat. The good news, both men agree: next-gen members bring something their predecessors couldn't — fluency in tools that didn't exist a few years ago. Integrated well, that's exactly what keeps a legacy business relevant instead of becoming a statistic on the funnel above.

The 75 years that now take 75 seconds

The most quietly radical moment in the conversation is a comparison of clocks. When Andrew's family opened its office to serve other families, it was itself an act of entrepreneurship — "we found ourselves with infrastructure we'd built, and said, how can we open our doors and work with other families?" They repurposed what they had. But that repositioning drew on knowledge accumulated over decades. As Dermer puts it, the kind of hard-won insight that used to take a family "75 years to learn" is now, in many domains, something the tools can help you learn in "75 seconds."

That collapse in the cost of capability cuts both ways for wealthy families. It means the moat around an old operating company can evaporate faster than anyone expects — the eight-person team becomes two, the specialist advantage becomes a prompt. But it also means a motivated next-gen member, armed with AI and an ownership mindset, can build or reinvent something at a speed that was previously impossible. The families who win won't be the ones who guard the old knowledge most carefully. They'll be the ones who teach the next generation to build with the new tools fastest.

Everybody has a little bit of foundation. In times like this, it's how can I repurpose, repivot, and reposition — with an entrepreneurial hat on.

Passion and grit are not a plan

Both men are blunt about a failure that runs deep in how we prepare people — the wealthy included — to build. We tell them all they need is passion, grit, and a good idea. Dermer's analogy is savage: "That would be the equivalent of saying, Andrew, I'm going to go perform heart surgery tomorrow" — with no medical school, just the willingness to "fail fast." We'd never accept that in medicine. Yet for aspiring builders we've long said, in effect, "go play in traffic and hope you don't get hit by a bus."

We didn't teach the foundational things. You need these five things to start — and you might need ten others. It's not OK, especially with AI, to just say go play in traffic.

This gap matters more, not less, for families with means — because the safety net masks the lack of foundation until it's expensive. That's what The Lonely Entrepreneur was built to close: the first one-stop foundation of what it actually takes to build, so the rising generation gets guidance instead of a shove. Academia teaches skills on a fixed timeline and then ends; ownership requires an ongoing community, because the questions never stop coming.

Builders, not beneficiaries

Andrew's own summary is the phrase that names the whole shift: entrepreneurship is "a way to cultivate builders, not just beneficiaries." The point isn't to reject stewardship — it's to recognize that stewardship without creation eventually decays. Purpose, both men insist, doesn't come from the wealth you steward. It comes from the value you create. "Most people — maybe all people — need to find a sense of purpose," Pitcairn says, "and it's easy for a wealth inheritor to become lost in 'well, I'm a wealth inheritor' and stop there."

Entrepreneurship is the antidote precisely because it can't be inherited. You can be handed capital, a company, a network, a name. You cannot be handed the humbling, character-building experience of worrying about people who depend on you and figuring out how to stay relevant. That has to be earned. And in an AI world where inherited advantages erode faster than ever, the families who deliberately cultivate that experience in their rising generation are the ones who will still be relevant in a hundred years.