In every industry, there are moments when people stop and ask themselves:

What are we really doing here?

How do we build something that lasts?

What truly matters in the way we work and lead?

Today, many entrepreneurs and managers are wrestling with these questions.

The world is full of noise, technology hype cycles, shifting business models, changing expectations.

We’ve been told repeatedly that success comes from being “tech-enabled,” “AI-first,” or “infinitely scalable.”

But then someone steps forward with a completely different message, one grounded in lived experience, humility, discipline, and human relationships.

Someone who reminds us that business is, at its core, about people. That someone is Steve Schwab, CEO of Casago.

His story—from Ranger training, to accidental entrepreneur, to leading thousands of people, offers a powerful reminder of what actually works in business, especially when the world feels uncertain.

This is not a story about disruption. It’s a story about clarity.

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1. The Unexpected Beginning: Success That Starts With Kindness

Schwab didn’t begin with a master plan or a business school blueprint.

He began with a small, simple act of kindness in Mexico—helping a sick man repair a roof when he had nothing to gain.

That act led to another.

And another.

And eventually, a business.

What’s striking is not the scale Casago would later reach.

It’s the philosophy behind that beginning:

• Help without expecting anything back.
  
• Do the right thing even when no one is watching.
  
• Show up when others don’t.
  

These choices didn’t just shape a company—they shaped a reputation.

In Schwab’s words, those early actions “lifted me up” because doing good quietly created trust in ways he didn’t expect.

Many leaders today are searching for purpose, wondering if the work they do makes a difference.

Schwab’s origin story is a reminder:

doing what’s right is a business strategy, too.

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2. Ranger Discipline: The Foundation of Leadership

Before Mexico, Schwab’s world was the U.S. Army Rangers—a place defined by:

• discipline
  
• humility
  
• relentless practice
  
• team before self
  

In Ranger training, he lived by a creed repeated daily.

There, he learned something he would later recognize in business:

Success is not a moment. Success is a daily ritual.

This becomes important later—when his company grows faster than he feels ready for.

For many leaders, rapid growth creates pressure, insecurity, and self-doubt.

Schwab felt all of it. But Ranger training had taught him something essential:

When things grow beyond your comfort zone, you don’t shrink. You sharpen.

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3. Culture: From Compliance to Conviction

As Casago expanded, Schwab faced a crisis familiar to many entrepreneurs: The business was growing faster than the culture could hold it together.

People were making decisions he didn’t understand. New hires were joining without alignment.

Mistakes multiplied. Instead of blaming others, Schwab asked a harder question: Have I actually defined what we stand for?

So he did something bold—and vulnerable.

He wrote down a set of principles, inspired partly by the Ranger creed, and asked every employee to read and discuss them daily.

At first, people pushed back. Some mocked it. Some quit. But then something changed.

Teams began to use the principles to guide decisions. Housekeepers gathered in corners to teach new employees from the book.

Managers referenced it before calling homeowners.

Schwab describes this moment as the shift from compliance to conviction.

Culture wasn’t a poster. It was a practice. And this is the lesson: Strong culture is not about slogans.

It is about shared decisions when the leader is not in the room.

For leaders trying to figure out how to build alignment, this is a roadmap.

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4. The Franchise Strategy: Local Relationships Over Distant Control

As Casago grew across cities, Schwab confronted a truth that many companies eventually face: Being everywhere is not the same as being effective.

He realized that quality declined when leadership was too far from the ground.

Margins shrank. Local problems needed local ownership.

So he made a dramatic decision: decentralize.

Instead of one big centralized organization, he built a franchise model rooted in:

• local accountability
  
• local relationships
  
• local leadership
  

This wasn’t a rejection of technology. It was a refocusing:

Technology helps. But relationships build the business.

His message to investors captured this perfectly: “This is a relationship business.”

Not a slogan. A structure.

Casago’s tools support operators, but it’s the local trust that sustains growth. For leaders unsure whether to scale up, scale down, or scale differently, Schwab’s model offers clarity: Scale relationships, not distance.

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5. Leadership Beyond Growth: Humility, Gratitude, and Inner Work

One of the most unexpected parts of Schwab’s philosophy is how openly he speaks about fear, inadequacy, and self-development.

He talks about:

• feeling unqualified
• not knowing the right terminology
• failing publicly
• learning to delegate
• hiring people smarter than him
• lifting his own “leadership lid”

This honesty is rare—and valuable. He also speaks about something even more personal: the practice of gratitude.

He believes gratitude builds the “mental pathways” that allow a leader to stay calm under stress: “Every time you allow anger to be transmitted, you give away your power.”

In an industry full of pressure—owner demands, guest issues, staffing challenges—this message resonates deeply.

Leaders aren’t just managing companies. They’re managing themselves.

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6. Owner-Centricity: The Guiding Principle

If one idea sits at the center of Schwab’s entire philosophy, it is this:

Always act in the homeowner’s best interest.

Not sometimes. Not when it’s easy. Always.

He calls homeowners one of the three critical relationships in life—alongside spouses and pets—to emphasize how carefully they must be chosen and cared for.

This principle shapes everything:

• guest experience
• financial decisions
• property care
• communication
• business growth

It also explains why Casago retains owners—and why this philosophy appeals to operators questioning the right way forward.

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Conclusion: The Real Secret Isn’t a Secret at All

What makes Steve Schwab’s story meaningful is that it returns business to something human, grounded, and accessible.

Here is the throughline of his message:

• Do the right thing.
• Build trust through actions.
• Create culture through daily practice.
• Lead with humility.
• Stay grateful.
• Keep owners at the center.
• Use technology to empower people—not replace them.
• Grow only at the speed of relationships.

This is why his philosophy resonates with anyone trying to build a business today, especially those unsure of the “right way” or overwhelmed by the noise of the moment.

Because at the end of the day, business is not mystery.

It is not magic. And it is definitely not hype.

Business is relationships. Leadership is service. And growth is the natural outcome of both.

Thibault’s notes from listening to and meeting Steve in person this year:

What struck me most in Steve Schwab’s story is that his real advantage was never technology or investor decks. Yet behind the scenes, Schwab had something far more valuable: years of trusted relationships he could draw on when he needed real advice.

He simply had the right people — people who were willing to help because he had earned their trust long before he asked for it.

This is why his path stands in contrast to firms like Sonder and Vacasa. It’s easy to critique them now, but they were also entrepreneurial experiments shaped by the pressures of their time. To raise money, they had to present themselves as tech-first. That was the only language investors responded to. Once the capital came in, the logic took over: raise, scale, go public (through a SPAC, as you did at the time) and then face the correction when the story no longer matched the fundamentals.

It reminds me of the early 2000s, when every company suddenly had to be a “dot-com,” or today, when every firm claims to be “AI-first.” These narratives attract attention, but they can also trap companies inside expectations they cannot sustain.

Schwab avoided that path. His foundation wasn’t hype — it was people. And when the noise fades, that kind of foundation tends to hold.