The Player, The Coach, The Owner

If you know me, you know I love sports.

I’ll find analogies and comparisons between sports and business with ease, and often overuse them when coaching/consulting (sorry, not sorry)

One of my favorites is the analogy of the player, the coach, and the GM.

I didn’t discover this framework in a book - I stumbled into it by running my own companies.

Let’s dive in.

At Pneuma, I started with no background in the marketing, web, and SEO space. However, someone had to be the product leader, the seller, the deliverer. My hands were in everything, and I was quite literally on the field, playing the game.

I was the player.

As soon as I could hire, I could. I poured into people, tightened culture, built systems, and kept alignment from slipping when the work got messy. I was still on the field, I just wasn’t always the one “doing”.

I became the coach.

Over time, I continued to build the business, which allowed me to take a larger step back. I could step away for a week at a time, but I never stayed there long. I’d get pulled back into the day to day with some inevitable issue. With more cash and scale, I could’ve gotten there, but never did.

I tried to become the Owner, but never fully did.

Why do I share the above? Because each of the “roles” I embodied helped me understand how to show up day to day in the business.

For me, it was helpful to understand what hat I was wearing, where my blind spots were, and how to manage that. And equally, where I was “the best”

Here’s how the three roles show up in the wild:

The Player

• Strengths: craft, credibility, elite delivery

• Weaknesses: business depends on them, scale capped by personal output, general “burnout” risk

• Pitfalls: builds a great job - struggles to build a great business

The Coach

• Strengths: develops people, builds culture, keeps the team aligned

• Weaknesses: becomes the bottleneck - everything routes through them

• Pitfall: drowns in middle management chaos - low leverage

The Owner

• Strengths: systems, capital allocation, long horizon bets

• Weaknesses: risks detachment from product and people

• Pitfall: spreadsheet mode - misses slow product or culture decay

In my opinion, none of these is morally better, which might be a surprise. Someone might take a quick pass at the above and say the “owner” is the best, but I would contend that each entrepreneur is built for one of these roles. Each can build a successful company. Each carries predictable blind spots. And to be blunt, I know plenty of people that fit each role that are financially “successful” as well.

The practical move is self awareness - know which seat you default to, what kind of business that implies, and which traps to design around.

This lens also maps cleanly across a team. Your best doers are usually Players. Your best managers are Coaches. Your VPs and execs should operate like Owners. Great - but how do you keep those layers aligned without becoming the bottleneck again?

That’s where the Waypoint comes from, and what I’m covering in today’s Working Theories.

Working Theories

The Waypoint was my operating ritual for staying close to the truth while (I tried) moving from Coach toward Owner.

Quarterly, I met with every teammate - at peak, 31 conversations per quarter. I sent the questions in advance so we could have a prepared, productive conversation, not a hallway chat.

Here’s how to apply it to your business

Resources

Doc Referenced In The Video

Full List Of Working Theories