“What got you here won’t get you there” applies not only to founders, but to the organizations they build. An underappreciated aspect of this is risk and chaos, and how it appeals to discrete personalities. I consider most of these archteype to respond mostly to certain levels of organizational chaos - and as such, there are areas where they thrive, and areas where they are out of their depth. I’ll hearken back partially to Wardley’s Pioneers, Settlers, Town Planners as part of this.

Cowboys (Initial Build) Link to heading

Maximum chaos. Processes and people pop in and out of existence from day to day. This is the Time of Legends, when the great elder gods of the organization will be formed.

Things matter, but at the same time, the business could be gone tomorrow, so nothing really matters all that much. You do what has to be done to survive another day, and hope that the compromises you make don’t kill you later.

This requires maximum appetite for chaos, and an ability to roll with the punches. Trying to bring order before a company is at 1 is foolishness - as the business may immediately pivot away, leaving only dead weight. Your employees job is to live in that frontier and make the best of it, until such time as order can be brought to bear.

Frontiersmen (MVP) Link to heading

These are the first ‘settlers’ in a land of chaos, and the first to start enforcing order. Everything is haphazard, but there are now permanent durable structures. Ad-hoc but shared processes begin. Efficiency gains can start taking hold. People start thinking about and planning for the future.

To be successful here, you first need to be comfortable with chaos. You then need to have a knack for paving over some of the chaos with order. The product now exists in some form and is seeking product market fit. You have users, and you probably don’t want to shed them if you can afford it. Striving forward is still important, but the cost of doing so vs breaking what you have is changing.

Settlers (Product Market Fit) Link to heading

This is the transition between chaos and order. With product market fit, the core of the product snaps into a static state, which can be sold and resold. This means more processes and personalities can coalesce around that.

To be successful here is to balance order and chaos. Frontiersmen have hacked away at the chaos to a point where it is yielding, and settlers literally build on top of that. Success is build on establishing repeatable processes and executing on them. Ad-hoc activities start falling away, and become more expensive.

Townspeople (Scaling) Link to heading

Scaling is the order of the day. The processes of the settlers are refined and turned to 11. Success is doing more, more more of everything. This means refinement and systems for efficiency. Chaos still exists, but is wrapped in process. As process is refined, things turn towards figuring out how to mechanize for efficiency.

Cityfolk (Exit/Large Business) Link to heading

We’re now in the ‘modern era’. Chaos is pushed below the fold and to the edges. Employees are expected to know and follow processes. Everything is mechanized for efficiency gains. Growth has topped out. There are frontiers still, but they exist on the edges. Everyone, even the CEO, is a small piece of a greater whole

It’s really important to know where you’re most comfortable in this scale. I’ve found that each group can get along well with the surrounding groups, but as groups become more distant, communication becomes more difficult. As an example, Cityfolk and Cowboys speak an entirely different language.

One principle failure I see is when an organization outgrows a given person. A cowboy can stick around through product market fit, but they’ll generally become less effective and less happy. That said, the opposite can be true. If a company slips out of product market fit, early scaling hires will rapidly slip out of effectiveness. Survival becomes the law of the land, and efficiency slips to a backburner, making them less effective.

This is especially important for executives. Many executives try to cling to a C title (or politic for one), when they’d be better served with a lower title but access to more effective help. An easy example is when your founding engineer becomes CTO rather than Principal Engineer - if you’re scaling, the people leadership is more important than the execution.

I should add that I don’t think these roles are necessarily durable over time. Rather, at a given time, someone’s risk appetite biases them towards one group. Extensive Enterprise experience makes for Cityfolk, but taking a early startup job and rolling with the punches can let someone shift to a Cowboy. Or, your startup gets acquired by IBM, and you (a Cowboy) have to learn how to work with Cityfolk, even if you’re at the frontier.