Zack Tomlin: Why Generic Business Advice Fails Leaders

The Size 12 Problem in Business

What if the business advice you’ve been following was never really designed for you in the first place?

Zack Tomlin - entrepreneur, former business owner, business coach, and author of Craft the Expedition of Business — believes this is one of the biggest hidden problems in entrepreneurship today.

After spending 12 years founding, growing, and ultimately exiting his own business, plus advising organizations ranging from 10 to 200 employees, Tomlin noticed a recurring pattern: leaders were frustrated not because they lacked effort, intelligence, or ambition, but because they were applying business strategies built for someone else’s reality.

Tomlin uses a memorable analogy to explain this. Business advice, he says, is like a size 12 shoe. In the U.S., men’s size 12 is among the most common sizes. If you wear a size 12, great—it fits perfectly. If you’re an 11 or 13, you can probably make it work. But if you’re a 9 or a 14, you’ll spend your time squeezing into something that was never built for you.

That’s exactly how many founders experience popular business books, courses, and consulting frameworks. A startup founder in their twenties, a mid-career executive launching a consulting firm, and a first-generation entrepreneur building a family business may all read the same advice, yet they operate with entirely different skills, cultures, goals, constraints, and life experiences. And still, they’re expected to follow the same playbook.

Why One-Size-Fits-All Business Advice Breaks Down

The business world is filled with formulas that promise clarity and results. Follow this sales process. Use this hiring framework. Implement these KPIs. Adopt this leadership style. While these systems can work in certain contexts, Tomlin argues they often fail because they ignore the most important variable: the leader and their environment.

As he puts it, “Most businesses aren’t average businesses, because they aren’t run by average people.”

Every founder brings a unique combination of strengths and blind spots, beliefs about leadership, tolerance for risk, communication style, and personal values. At the same time, each organization operates within its own set of market realities, team dynamics, operational constraints, and customer expectations. A creative founder might build an innovative, flexible culture but struggle with consistency, while a highly structured operator might create efficient systems but limit adaptability.

Neither approach is wrong. The problem arises when leaders try to force-fit a model that wasn’t designed for their context.

Take a moment to reflect: when a piece of business advice didn’t work for you, was it truly flawed—or simply misaligned with your reality?

The Mountain of Why: How Great Leaders Think Differently

Tomlin introduces a powerful concept called the “Mountain of Why,” describing how leaders evolve in their decision-making. Most begin at the base, relying on mimicry. They copy what appears to be working for others—competitors, mentors, or popular voices in the business world. It’s a natural and often necessary starting point.

With experience, leaders move toward heuristics, leaning on patterns they’ve seen before. From there, they may adopt frameworks that allow them to evaluate multiple variables at once. These stages bring increasing sophistication, but Tomlin suggests that true leadership maturity lies higher up the mountain.

At the top is first-principles thinking. Here, leaders stop asking what worked for others and begin asking what they believe is fundamentally true. As Tomlin explains, “The best business advice is built on principles that are true for all business. Then the leader builds their decisions from there.”

What Are First Principles in Business?

In business, first principles are rarely universal laws. More often, they are deeply held beliefs that guide decision-making. These beliefs might relate to how you view employees, how you approach competition, or what kind of value you aim to create.

For example, a leader who believes employees thrive with autonomy will design a very different organization from one who believes tight structure and oversight are necessary. A founder focused on long-term trust will make different trade-offs than one optimizing for short-term gains.

Neither perspective is inherently right or wrong. What matters is awareness. Problems arise when leaders adopt systems based on assumptions they don’t actually share.

Why Growth Creates Chaos

As businesses grow, complexity increases in ways that many leaders underestimate. What worked with a small, close-knit team begins to break down as more people join, communication channels expand, and responsibilities become more distributed.

Tomlin captures this challenge clearly: “Clarity gets lost because you’re introducing more voices.”

In a small team, alignment happens almost automatically. Everyone hears the same conversations and understands the same priorities. But as the organization grows, information becomes filtered, messages get interpreted differently, and alignment begins to drift. Leaders may assume everyone is on the same page, while in reality each person is working from a slightly different version of the story.

Machine vs. Ecosystem Thinking

When faced with this complexity, leaders tend to adopt one of two approaches.

Some treat the business like a machine, focusing on optimizing parts, tightening controls, and standardizing outputs. While this can create short-term efficiency, it often leads to fragility. Machines require constant maintenance, and as complexity grows, the system becomes harder to manage.

Tomlin offers a different perspective: treat the business as an ecosystem. Instead of forcing outcomes, focus on creating the right conditions. In a healthy environment, the desired behaviors emerge naturally. Rather than asking how to control people more tightly, leaders begin asking how to design an environment where good decisions happen without constant oversight.

This shift changes everything. It moves leadership from control to design.

The Four Parts of Every Business Expedition

To explain his holistic view of business, Tomlin uses the metaphor of an expedition. Every organization, he suggests, consists of four interconnected elements.

1. Destination

Where are you going?

This includes:

• goals

• vision

• mission

• beliefs

  
  

Without clarity here, teams drift.

2. Crew

Who is going with you?

Hiring is not simply about talent.

It’s about fit:

• values

• adaptability

• communication style

• role alignment

  
  

3. Leader

Who is responsible for direction?

This is where founders often struggle most.

At some point, success requires transitioning from:

• expert

  to

• executive

  
  

4. Expedition

How does the business function daily?

This includes:

• systems

• cadence

• communication rhythms

• accountability structures

A healthy expedition keeps moving even when the leader steps away.

When one of these elements is weak or unclear, the entire organization feels the impact.

The Four Horsemen of the Business Apocalypse

Tomlin also highlights four forces that every business must contend with: competition, human nature, limited resources, and entropy. These are not temporary challenges but constant realities.

Competition applies pressure from the outside, forcing businesses to differentiate. Human nature introduces limits in energy, focus, and behavior. Limited resources constrain what is possible at any given time. And entropy ensures that without effort, systems will gradually fall into disorder.

While these forces can feel restrictive, Tomlin offers a different perspective. Constraints, he argues, are what make effective decision-making possible. Without them, leaders would face an overwhelming number of choices. With them, priorities become clearer and decisions more grounded in reality.

Better Businesses Create Better Lives

At its core, Tomlin’s philosophy extends beyond business performance. He believes that the quality of an organization directly shapes the quality of people’s lives.

“It’s hard to have a good life if you’re working for a bad boss,” he says.

Poorly designed businesses create stress, burnout, and lost potential. Well-designed ones create space for growth, fulfillment, and balance—not only for employees, but for leaders as well.

Tomlin experienced this transformation himself. Early in his journey, his business consumed his time and energy, leaving little room for anything else. Over time, as he refined his approach and built better systems, the business began to support his life rather than control it. Growth improved, but more importantly, so did his freedom and overall well-being.

Final Reflection: Craft Your Own Expedition

Generic business advice isn’t inherently wrong, but it is often incomplete. The real work of leadership lies in understanding which principles are universal and which strategies are contextual.

Zack Tomlin’s message is ultimately a call for ownership. Instead of blindly following someone else’s roadmap, leaders must define their own beliefs, design their own systems, and build businesses that reflect their unique reality.

Because in the end, success doesn’t come from wearing the right shoe.

It comes from building a path that fits.