Chapter 1: Why Be a Monster, and Not a Hero

I did not come to the idea of being a monster from literary theory. I came to it from failure.

I came out of venture-backed startups. Across multiple tech companies, I helped return nearly $500 million to investors on about $65 million in fundraising. From the outside, that sounds like the kind of track record that should make the next chapter easier. It did not. After my last company, I decided to build something smaller, more meaningful, and more my own. I raised a little money from mentors I respected. I thought that would make things cleaner, more disciplined, more intentional.

Instead, I was a mess.

I offshored. I hired cheap. I hired expensive. I chased leverage in the wrong places. I thought I was being strategic when I was often trying to force progress. I had read the books. I knew the language. Marketing. Sales. Go to market. Positioning. Funnels. Story. Demand. I had already started building my own frame around demand-side growth, the idea that demand, not internal preference, has to drive the business. I had also absorbed the StoryBrand model, the idea that your customer is the hero and you are the guide. And I had spent a lot of time with jobs to be done, especially through Clayton Christensen and Anthony Ulwick, whose work helped clarify that the job already exists before you arrive.

There is value in all of those ideas. But I still felt like I was missing something.

Then, a few years ago, around Halloween, I took my daughter to a lecture on monsters. In that lecture, they discussed Jeffrey Jerome Cohen and his essay Monster Culture. He argues that the monster is not just a creature. It is a cultural signal. It reveals fear, desire, anxiety, contradiction, and the limits of the current order. It stands at the edge of what a culture can explain, tolerate, or absorb.

And when I heard that, it clicked.

It clicked because I realized high-growth builders are not heroes in the usual sense. They are much closer to monsters.

And I do not mean that narrowly. This is not only about a founder starting from scratch in a basement. It is about a mindset toward change. It applies to startups, yes, but it also applies to people inside existing organizations who are trying to create real movement, challenge stale assumptions, and build something with breakout potential instead of settling for safe, incremental progress.

Jobs to be done helped me see part of this. Christensen and Ulwick made the point in different ways, but the core insight is the same. The job already exists. You cannot sell people on imaginary jobs. The customer already has a way of getting the job done, even if that way is clumsy, expensive, slow, or frustrating. That means the real thing you are competing against is not some abstract market category. It is the status quo. It is the current habit. It is the current workflow. It is the current vendor. It is the current compromise. The customer is not wandering around waiting for a brave builder to rescue them. In many cases, the customer is defending the current order because it is familiar.

That changes the whole story.

If the customer is holding onto the status quo, then the builder is not the hero arriving to restore order. The builder is the force trying to disrupt the order that already exists. It is the thing that looks risky, unfamiliar, hard to classify, and possibly dangerous. It threatens habits. It threatens budgets. It threatens internal politics. It threatens the comfort of doing things the old way.

That is a monster.

Once I saw that, a lot of things about my own failures made more sense.

I had been too willing to use borrowed language. I had been too willing to sound acceptable. I had been too willing to pretend the market would reward effort. I had not fully respected how much I was competing against inertia. I had not fully understood that if you want to grow, you are not asking the world to applaud you. You are asking the world to change.

That is why Cohen mattered so much to me. He gave me a frame that explained something I had felt but had not fully named.

As I sat with Cohen's ideas, I realized I was looking at a description of the kind of company I was trying, badly at times, to build.

The monster is a cultural body. That felt true to me because a startup is never just a bundle of features. It belongs to a moment. It rises out of a specific pressure in the market, a specific frustration, a specific shift in technology, behavior, economics, or trust. If your company is not in the moment of what is happening, it may survive, and it may even grow, but it is far less likely to become explosive. Most of us do not choose entrepreneurship to create a harder version of a nine-to-five job. We take the risk because we want to build something that matters at scale. The companies that break out usually do so because they are not only selling a product. They are embodying a change whose time has come.

The monster creates category crisis. That felt true too. The companies I admired most were never easy to classify at first. They made the old labels feel weak. They made the existing category feel too small for what was coming. That is part of why they looked dangerous. They did not fit the old map.

The monster dwells at the gates of difference. I realized this was not only about serving people incumbents overlook, though that is often part of it. It is also about what happens whenever you propose a different way of doing things. The status quo has gravity. It has habit, trust, language, process, budget, politics, and cultural legitimacy. What you are proposing is not simply a product. It is a difference. It is a claim that something else should replace what people already accept. That is why the startup naturally lives at the gate between what is normal now and what might become normal next.

The monster polices the borders of the possible. That hit me hard too. A lot of what looks like loyalty to the status quo is really uncertainty about whether change will be worth the headache. Buyers ask themselves: if I go through all of this hassle, all of this switching cost, all of this disruption, will my life actually improve? Will this change anything meaningful? The border of the possible lives right there. It is the edge between the world the buyer knows and the world they are not yet sure is reachable. A great company has to do more than promise novelty. It has to make a better future feel possible, credible, and worth the risk.

And then there is one of Cohen's sharpest ideas, that fear of the monster is really a kind of desire. That maps cleanly to markets. Buyers fear change because change is disruptive. It requires risk, effort, budget, internal alignment, or public commitment. But that fear often points to desire. If there were no meaningful gain on the other side, there would be no real tension.

That is why I stopped thinking of the startup as the hero of the story.

The hero restores order. The monster threatens it. The hero protects the kingdom. The monster reveals that the kingdom is brittle, outdated, or incomplete. The hero helps the current world survive. The monster forces the world to change.

That does not make the builder evil. It makes the builder disruptive in the literal sense. They are trying to displace a way of doing things that already exists.

That is also why this book is not a celebration of chaos or ego. I am not interested in founder-warrior posturing. I am interested in what actually happens when you try to change something that does not want to change.

And once I looked at it that way, the role was hard to deny. If you are building something meaningful, you are competing against the status quo. If you are competing against the status quo, you will look dangerous to it. That is the role whether you name it or not.

MonsterBrand is my attempt to do that.

It is an attempt to build a business and a body of work around a harder truth. Markets do not move because founders want them to. They move when pressure builds against an old way of doing things and a new way becomes more compelling.

The monster frame helped me because it stopped me from flattering myself. I was not a guide leading a hero to safety. I was the disruptive force that most of the market would prefer to ignore. Seeing that clearly changed how I thought about selling, positioning, building, and hiring. It made me more honest about what I was actually asking the market to do.

There is one more thing I want to be honest about.

The monster does not have to win completely to matter. I have watched companies fail that still left a mark. They exposed a weakness in the current order. They forced incumbents to respond. They made customers question what they used to accept. They cracked the armor of the status quo even though they did not survive long enough to benefit from it.

That is part of why I kept building after my own failures. Not because I had a motivational story about perseverance. Because I could see that even the attempts that did not work had moved something. The old order was a little less secure. The next attempt, by me or by someone else, would find slightly softer ground.

That is the founding of the monster.

And if that is the role, then the next question is obvious. What kind of discipline does a builder need if they are going to play it well.

It is not ego. It is not hype. It is not more activity.

It is truth.

Chapter Takeaways

• The builder is not the hero restoring order. The builder is the force challenging the status quo. That is the monster's role.
• The monster metaphor is not a brand exercise. It is a way of seeing the real dynamics of what happens when you try to change something that does not want to change.
• The best breakout companies embody a market moment, not just a product idea.
• The status quo has gravity — habit, trust, budget, politics. Difference creates tension because it threatens all of those.
• Even failed monsters can crack the armor of the old order. The ground gets softer for the next attempt.