Philosophic Lessons from Leadership with William Crossan

William Crossan sat at the top of the mountain—literally. His team had just built the number one organization for a Fortune 100 company nationally. They'd won. And that's when he realized the corporate culture around him had shifted so drastically that he could no longer stay. The values that got him there were no longer the values of the organization he was serving. So he left to build something different: a company focused on the one thing most businesses get backwards.

Culture isn't a poster on the wall or a Friday beer cart. It's not ping pong tables or unlimited PTO. Culture, as Crossan defines it, is "the art and tradition of a people group"—how they are with each other, and why that matters. After a journey from Air Force service to financial services leadership to founding Campfire Culture, he's landed on a philosophy that challenges the typical business playbook: culture drives structure, which drives results. Not the other way around.

On this episode of The Digital Transformist, Crossan breaks down the philosophic lessons that shaped his leadership approach—and why starting with the heart, not the head, creates businesses with actual meaning.

Work Is the New Church

Crossan doesn't mince words: "I believe work is the new church. We worship in the realm of work." Most people spend more waking hours with colleagues than with family. We exchange our lives for money in these spaces. And yet, businesses consistently treat culture as an afterthought—something to address after the strategy is set, after the org chart is drawn, after the problems emerge.

His insight cuts deeper: "Money is an illusion. Money is just a symbol for exchange of value." If that's true, then what are we actually exchanging when we go to work? Crossan's answer: our lives, our relationships, our sense of meaning. The companies that understand this don't just perform better—they create environments where people actually want to contribute their best work.

This isn't soft thinking. Crossan and his business partner Matthew Vahue took over a nonprofitable financial services company after the CEO's behavior created a toxic culture that tanked results. They had four years to turn it around. They did it in two and a half—by starting with culture, not spreadsheets.

Culture Drives Structure, Structure Drives Results

The typical business approach is backwards. Companies set financial targets, build organizational structures to hit those targets, then wonder why people are disengaged and results plateau. Crossan flips the script: "Culture drives structure which drives results. It's not just about outcomes. It's about meaningful outcomes."

What does that look like in practice? It means asking different questions at the beginning. Not "How do we hit this revenue target?" but "What kind of organization do we want to be? How do we want to treat each other? What values will we refuse to compromise?" Once you answer those questions, the structure becomes obvious. And when structure aligns with culture, results follow.

Crossan uses the Entrepreneurial Operating System (EOS) framework, sitting in the chief visionary officer seat while his partner serves as integrator—what EOS calls "rocket fuel." But the system only works when there's cultural alignment first. Tools and frameworks can't fix a culture problem. They can only amplify what's already there.

Breaking Out of Tribal Thinking

Born in El Paso to an Army aviator, Crossan moved to Germany, then Virginia, then Texas, then Delaware—all by age six. That early exposure to radically different environments gave him something rare: perspective on how much our surroundings shape our reality. "Oftentimes we don't recognize how much our environment shapes our experience and the lens of which we view reality," he explains. "I was early on exposed to many different ways of being which I believe broke me out of the box of tribal thinking."

This matters for leaders. Most of us grow up in one cultural context and assume it's universal. We build companies based on unexamined assumptions about how things "should" work. Crossan's background—military service, philosophy degree from University of Texas, entrepreneurship, Fortune 100 leadership—gave him multiple lenses. He's a self-described "deep thinker" with "anti-authority" and "visionary tendencies." That combination doesn't always fit neatly into corporate boxes.

But it's exactly what's needed to question the assumptions that keep most companies stuck. When everyone around you accepts that "this is just how business works," having someone who can see alternatives becomes a strategic advantage. Crossan's path taught him that there are always other ways of being—in life and in business.

Everything Is Spiritual

Ask Crossan when culture became his focus, and he'll tell you there's no single light bulb moment—there's a daily light bulb. "The underlying theme of all those light bulbs is everything is spiritual. We are born. We live. We die." At the end of life, people ask the same questions and have the same regrets: they wish they'd spent more time with people they love, doing things they love.

This isn't abstract philosophy. It's a business lens. "When we move into business and we disconnect the head in the heart, oftentimes we're serving the head. And at some point we recognize, man, my heart's not in this anymore." Crossan's approach: start with the heart, then engage the head. Build businesses that create purpose and meaning, not just profit.

That's why he hates when people say "we've got a great culture" without being able to define what that means. Culture isn't a feeling. It's observable behavior—how people treat each other, what they prioritize, what they refuse to tolerate. And in a "relational cosmos," as Crossan puts it, who you are being in relationship with others drives everything. Results included.

Listen to the full conversation with William Crossan on The Digital Transformist wherever you get your podcasts. Subscribe for more conversations on strategy, leadership, and the hard lessons that actually matter.