Wassup y’all! Another week, another dollar.

This past week was one of those weeks where content reminded me why I care so much about it. I had a few client wins. A few moments that made me stop and say, “okay…this stuff actually works when you’re patient and intentional.” And a few conversations that reminded me how confusing content still is for most founders.

Not because they’re bad at it.

Not because they’re lazy.

But because they’re asking the wrong questions.

Let’s talk about that.

(And before we get into this - I have to say, to all the founders that are out there creating content no matter how awkward it may feel…shout out to YOU! As a creator myself, I will never forget the hump you have to get over to actually post content - creating it is the easy part, hitting post is the hard part. Just know I see you!)

The problem isn’t effort. It’s the questions.

Most founders don’t struggle with content because they aren’t doing enough.

They struggle because they’re optimizing for immediate sales instead of building a funnel of future customers.

That shows up very clearly in the questions they ask.

Here are some of the most common ones I hear and what’s actually going on underneath them.

❌ “Can’t we just repost the same content across all platforms?”

I see creators do it all the time.

Short answer: No.

Different platforms mean:

• different audiences

• different intent

• different behavior

• different algorithms

Creators can get away with this because they’re often shooting from the hip. Sometimes a hook pops on TikTok. Sometimes it pops on Instagram. Sometimes it doesn’t pop at all and that’s fine because their “brand” isn’t under the same pressure as a business.

Founders are playing a different game.

Platforms treat businesses and creators differently, and users behave differently on each platform too. You should think about each platform as either:

• reaching your same audience, but broader, or

• reaching a completely different audience altogether

Same message ≠ same execution.

❌ “Why isn’t this content converting? The CTR is high.”

This one gets founders in trouble.

High CTR means people are interested.

It does not mean something is broken.

Not all content is meant to convert and sometimes it’s better that it doesn’t.

If a piece of content has a strong click-through rate, the issue is more likely:

• the landing page

• the offer

• the timing

• or the fact that the content was mid-funnel, not bottom-funnel

The marketing “rule of 7” exists for a reason. People need to see your brand multiple times (AT LEAST 7 TIMES) before buying. Very rarely does someone see something once and convert.

Content touches every layer of the funnel, but only if you’re clear about its role upfront.

❌ “We need this to go viral.”

No, you don’t.

Unless the goal is humor or pure awareness, virality is often the wrong metric to chase.

I worked with a founder who became obsessed with going viral. So we did it. One clip hit ~700k views.

Results:

• ~15k new followers

• 1 conversion

• engagement on future posts fell off a cliff

Why? Because the audience that followed expected more of the same content.

If the goal was awareness, it worked.

But the founder was measuring success by conversions.

Virality without intent is just noise.

❌ “Why aren’t our followers seeing this?”

Because platforms don’t work like that anymore.

Instagram and TikTok no longer prioritize showing content to your followers first. They test your content with a small subset of people they believe will be interested based on signals like:

• transcription

• captions

• visuals

• early engagement

Reels and videos are tested across:

• feed

• explore / FYP

• search

Static posts are more likely to show up in the feed.

Your content isn’t being “hidden.”

It’s being tested.

The better questions founders should be asking

This is where things change.

Instead of:

“Why isn’t this content working?”

Ask:

“What is the goal of this content, where does it sit in the funnel, and what KPIs actually matter here?”

Instead of:

“Can’t we just say the same thing everywhere?”

Ask:

“How do we create variations of this idea that are native to each platform and audience?”

The real takeaway

Most content frustration comes from misaligned expectations.

When founders expect:

• mid-funnel content to convert

• awareness content to drive sales

• one post to do everything

They end up disappointed.

When they understand:

• the role of each piece

• the audience it’s for

• the metric that actually matters

Content stops feeling random and starts compounding.

That’s when it works.

If this hit home for you, next week I’ll go deeper into how founders should think about content roles and ownership so expectations don’t break teams before content ever has a chance to work.

Until then, ask better questions (for your own sake).

They change everything.

Thanks for reading! You got this far! Did someone come to mind when reading? Do them a favor and share this article with them.

Chase Coleman

Founder of Social Playbook

Notes on content, creators, performance and building Social Playbook.