Come Watch a Company Build Itself and Bring the Popcorn

THE COUL & GOLD BRIEFING · ISSUE Nº 29 · SEPTEMBER 8, 2026

Labor Day is behind us, which means everyone came back from the long weekend with A Big Idea. My inbox knows. Yours does too. September is when the entire professional world decides, at the same moment and with no coordination, that this is the quarter things finally get serious — and nobody carries more September energy than a founder who spent three days in a hammock, thinking.

Which brings me, not remotely by accident, to founders.

There’s a job posting I see some version of about once a week. “Chief of Staff to a visionary founder. A once-in-a-career chance to see a company built from the ground up, to sit at the center of everything, to learn how a business is really made.” It reads like a scholarship. And every time, I want to write back one line: none of that is a chief of staff job, so could you consider calling it what it really is? It’s a front-row seat to someone likely failing at management in real time, sold to you as an apprenticeship.

Since saying the thing out loud is the entire job of this newsletter, allow me to do it. Most founders are hard to work for (to put it mildly) as a Chief of Staff. Not because they’re all universally villains (some are lovely, some belong in the abandoned corners of Hades, and most are just exhausted), but because the exact trait that makes someone a founder is the trait that makes them impossible to organize around.

They ideate. Constantly. It’s the engine, and the engine has no off switch. A founder walks into Monday with four new directions and no memory of having killed two of them on Friday. Ideas are their native language and their whole theory of leadership, and nothing is ever allowed to leave the building, because killing an idea feels to them like killing a piece of the company. So you inherit forty open loops and a boss who is wounded that you’d suggest closing any of them.

Volume, though, I could manage. What actually breaks the machine is that nothing is ranked. A founder will hand you ten priorities and mean all ten, at full heat, today, and when you ask which one comes first, the question doesn’t parse. Sequencing is a management act. It means deciding that this matters more than that right now, and then saying so to the people who love that. Founders are spectacular at generating the ten. They have given roughly no thought to the order. (I have watched more than one treat “prioritize” as a fancy word for “do everything, but faster.”)

And let’s just cut right to it and I’ll say the part nobody prints – most of them cannot manage people even if you handed them a step-by-step playbook with specific instructions tailored to each person. That’s not some personal failing. They’re remarkably gifted at one thing and not everything else – they can manage ideas brilliantly and obsessively. But you cannot run a human being the way you run an idea. People need to know what they own and whether the plan will still exist by Thursday. The founder who can hold an entire market in their head often can’t hold the emotional weather of the six people sitting three feet away. So the Chief of Staff gets hired to be the buffer, the translator who turns the geyser into something a team can actually stand under. Real work. Hard, dignified work. The posting just sold something else entirely. It said learn from a visionary. Read: absorb the chaos so the visionary never has to feel it.

We have collectively decided that founders are leaders. It’s in the decks and the reverent little origin myths. And it is a fiction. Founding a company and leading one are not the same job — they’re barely within the same family of skills. Founding is a thinking act: you see something that isn’t there and you will it into being. Leading is a people act: you take a room full of humans who never had the vision, and you get them to build it anyway – with enthusiasm and devotion – and do it without breaking them.

The chiefs of staff who are actually worth studying worked for operators who understood that the Presidency is fundamentally a different job from grinding the gears of the federal government. Panetta, Baker, Podesta. Those partnerships worked because the person in the chair understood the job was people and process, staffed it that way, and let the Chief of Staff own the sequence. That’s a boss who knows his own gaps and hires straight into them, and it’s rare then and much rarer now, inside a founder culture that has taught a whole generation to mistake the idea for the leadership.

To be fair, the good ones are out there. There is a Venn diagram of founders who are also remarkable leaders. I’ve worked with a few (and one who was my favorite). You clock them inside a single meeting, because they can end a sentence with “not yet, and here’s what has to be true first.” They kill their own ideas out loud. One in particular would aggressively invite criticism because he put the company before anything else. They can tell you flat out what they’re bad at without it damaging their ego or the aura of gravitas they aspire to, and then they hire directly into that weakness instead of repackaging it as a “growth opportunity” for a 26-year-old. Those founders make phenomenal partners. They’re also about one in ten. (Hyperbole? A little. Ask anyone who’s held the seat.)

So before you take one of those front-row seats, get three answers first:

Who owns prioritization here today, and can they say the name out loud?

What happened to the last person in this chair?

And when the founder is wrong, who tells them, and is that person still employed?

You already know which postings can’t answer number three.

None of this is thrown from the cheap seats. We’re founders too, and our version of the disease is real. Suzi and I care deeply about people, and we’ve spent decades thinking about how to lead and manage them, and we still walked straight into the founder trap of build, build, build with no clear focus. We caught it with the help of Jen Phillips, whose guidance changed how we work. I think we’ve recovered, and I hope you’ll feel the difference. It’s subtle but real. Over the next few weeks you’ll see us more focused, and more tailored to the actual challenges you’re carrying. Every word of this was written from inside the house, and the mistakes are ours too.

— Rachael

If this edition had you quietly sizing up a founder you’re about to go work for (or the one you already work for), that instinct is most of the reason we built the Chief of Staff Readiness Assessment. Know your own wiring before you agree to hold someone else’s.

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One voice from inside the role. One from the blueprints. Same mission.