The real reason early-stage founders struggle with content

Over the years, we’ve been brought into many seed-stage companies. There’s a pattern I know so well now I can almost predict it. Those engagements always start with a lot of energy. Founders come in with a long list of blog ideas, a manifesto they’ve been working on in Notion, and a sense that content should start compounding immediately because everyone knows SEO takes time and serious companies publish consistently.

Then momentum tends to fizzle. Drafts written to the brief are somehow not quite right, though no one can fully articulate why. Or they get rubber-stamp approved but never published. Over time, the relationship stalls out. The whiplash reminds me of a song my toddler likes to sing: “This is fast, fast, fast — this is sloww, slowww, slowwww.”

In the past, I blamed the obvious startup challenges. Early-stage teams are stretched thin. Marketing priorities change quickly. Founders don’t have time to review drafts. The company is pivoting.

In fact, I’ve been on the verge of saying no to more early-stage engagements, mostly to protect my team. Maybe it just wasn’t structurally the right fit for us.

But the truth is, working with seed-stage companies is often the most fun work we do. You get to interface directly with really smart, inspiring founders. The ideas are new and raw. The stakes of each piece feel thrillingly high.

And that, right there, is the heart of the issue.

When the stakes are high

Content is always doing identity work, but nowhere is that more acutely felt than at seed stage. There’s no backlog of posts, no archive that gives people a sense of your range. Whatever you publish becomes the reference point.

That’s a very different emotional posture than scaling content at a Series B company with a well-defined ICP and a sales motion that already works. In later-stage companies, a single piece might perform well or poorly, but it doesn’t define the company. At seed, you’re aware that investors, early hires, and customers may all overfit to this one blog post or whitepaper.

Hesitation creeps in because you worry, often subconsciously, about being locked into a version of the company you’re not entirely sure you want to commit to.

Writing freezes what is still moving

When you’re building something that’s still taking shape, your narrative might change a bit every day. You’re constantly updating your understanding of the problem, testing language in investor meetings and customer calls. Writing, and especially publishing, freezes all that thinking in place.

When something still feels fluid internally, seeing it frozen can be unsettling. So even though you can’t find anything obviously wrong with a draft, it might still just feel like it’s not something you’re ready to own publicly. I’d experienced this from the writer’s side, but it took sitting in the founder seat myself to fully understand it.

Becoming the founder who hesitates

When we started building the Copytree blog, I had our team drafting pieces from outlines we’d discussed. I would approve the structure, give early feedback, and feel aligned.

Then I’d read a near-final draft and feel resistance — not because the writing was bad (usually it was excellent), but because of my own lack of clarity around what I believed and wanted for the company. Claims that sounded clean on the page still felt in-progress in my head. I could sense, even if I couldn’t clearly express, the gap between what I was exploring and what I was willing to publish.

And I could also appreciate how maddening that must feel for the writer. We agreed on the outline, and they’d followed it, so what changed? Nothing changed. Whatever issues I had were always there, only now I was confronting them, too late.

What we do differently now

The experience of rejecting pieces I’d commissioned and approved gave me much more empathy for what’s actually happening inside a seed-stage company, and it’s shifted how we work.

Today, we sometimes function less like a production engine and more like an editorial partner. The founder does most of the writing, and we’re there to push back, workshop live over a call, and help them get to the bottom of what they actually believe.

With another early team, we recently spent far more time on the outline of a major guide than we would have a year ago. Multiple calls just to work through sequencing, emphasis, and underlying assumptions before drafting anything substantial. In the past, I would have optimized for speed: outline approved, draft moving. Now, I’m more comfortable letting that stage stretch.

This hasn’t been an easy change, nor is it fully implemented or perfect. I’m wired to think in deliverables; like the founders we work with, I thrive on momentum. Feedback we’ve gotten in the past that work felt slow or required too much executive effort can be hard to shake. We’re always trying to hit the right balance.

But ultimately, more output doesn’t fix an unstable narrative. It just gives the founder more to react to: more language to hesitate over, more drafts that feel almost right, more time spent circling the real question of what they actually believe.

Surfacing instability earlier can feel slow, slow, slow, but it may be fast, fast, fast in the long run.