Inside the subtle art of succession

Over the past few years, I’ve come to see succession as more than a corporate formality — or a brilliant HBO series. It’s the essential tool to building anything that lasts. Put simply: if you care about compounding over time, you need systems that outlive you.

That’s why I’m excited to announce a new collaboration with VestGen Wealth Partners, where I’ll be writing a column on the art of succession — in business, investing, and life. The first installment is available here.

Earlier this year, I had the chance to meet the VestGen team and speak at their inaugural conference. I came away deeply impressed by their philosophy — and by founder Josh Gerry’s thoughtful approach to creating something that’s built to last. My first piece explores some of the world’s longest-lasting companies and how a culture of succession was embedded into their DNA — enabling them to endure for generations.

In fact, much of this research is now informing how I think about long-term investing. When analyzing a company, thinking about succession offers a powerful mental model to evaluate whether a business can continue to strengthen even after a key leader leaves. At a basic level, it’s about determining whether an organization is structurally designed to outlast any one individual.

Key quote: “It’s not just about continuity — it’s about the right continuity. A company doesn’t endure just because someone new steps in. The next leader must be more than a placeholder; they have to be deeply invested in the business — its craft, its people, its mission. And just as importantly, the current leader must be invested in preparing them. Any long-term investor, advisor, or business owner should always be focused on one thing: compounding. Sustaining and growing value over decades. But here’s the hard truth: without strong succession, compounding fails. A business without a clear plan for leadership transitions is a business on borrowed time.”

The link between quantum physics and business

My recent Long Game at Big Think column drifts into metaphysics — exploring the tension between coincidence, randomness, and the unseen connections at the heart of all systems.

Specifically, I write about quantum physics — not as a scientist, but as a long-term thinker. What can ideas like entanglement, wave collapse, and nonlocality teach us about building things that last? The column opens with a personal anecdote — how I met my wife — that I find too strange to chalk up to randomness. To me, this story raised deeper questions about time and connection.

Here’s my core idea: if we want to build things that endure — companies, art, relationships, investments — we need a different framework for time. Long-term success isn’t just about plans or goals, but about designing resilient systems and staying open to feedback. The long game is rarely about control. It’s about staying in motion: entangled, attentive, and willing to trust the deeper patterns we can’t always see.

Key quote: “And here’s where I’ve landed: If we want to build things that last — companies, books, relationships, ideas — we need a different framework for time. Not as a straight line, but as a wave. Not just cause and effect, but resonance and return. As the physicist David Bohm once wrote, ‘Everything is enfolded into everything.’ The world, and our experience of it, may not be a series of discrete events, but a flowing totality — a deeper order that connects us in ways we can sense, but rarely explain.”

OUTLAST field notes: A visit with Daniele Riva on Lake Como

Last week, I visited Daniele Riva, sixth-generation builder of the legendary Riva boats, at his family’s shipyard on Lake Como. We toured his company’s historic birthplace — founded in 1771 — just a few hundred feet from George Clooney’s villa.

One story in particular stayed with me. In the 1980s, customer preferences shifted dramatically: the market demanded fiberglass hulls. They were cheaper and easier to mass-produce. Most boatmakers made the switch. But Daniele’s father refused.

He believed in the integrity of wood — its beauty, its soul. For several lean years, demand cratered. To survive, the company leaned hard into maintenance and repair services, keeping the doors open while others chased the trend.

Then, the pendulum swung. A renewed appreciation for craftsmanship brought customers back, and Riva was ready. That bet — to stay true to quality even when it was out of fashion — now looks brilliantly prescient. It’s a reminder that outlasting isn’t about reacting to every shift in the market. It’s about knowing what matters most — and having the patience to let the world come back around.

A few more links I enjoyed:

The Surprisingly Sophisticated Mind Of An Insect – via Carrie Arnold

Key quote: “‍Nearly 400 years ago, the French philosopher and polymath René Descartes formulated a devastatingly simple answer to the question, ‘What is consciousness?’ Cogito, ergo sum — I think, therefore I am. Hidden in that three-word Latin phrase is the assumption that humans are the only thinking animals. No matter how emphatically you ask a monkey or a snail whether they are alive and conscious, they will never answer. As the only species endowed by God with a soul and rational mind, humans, Descartes believed, sat at the summit of all life on Earth. Cutting-edge research over the last few years has begun to shift this view.” 

Plants, Collective Metaphysics, and the Birthright of Kinship – Monica Gagliano

Key quote: “‍Over the past two decades, a remarkable body of scientific literature has emerged on the intelligence and sheer virtuosity of plants, and a maverick group of scientists and philosophers now talk about ‘vegetal consciousness.’ One of the leaders in this field is Monica Gagliano, an Italian evolutionary ecologist who is a senior research fellow at the University of Sydney in Australia.”