From Printing Flyers to Fractional Head of Content

Waddup y'all!

I’m writing this week’s newsletter as I head back from Miami where I met with one of my clients and saw a Bare Knuckle Fight for the first time. I won’t lie, I was nervous af before the fights started because I saw it going one of two ways - either I enjoyed it and had a blast with my client OR they looked at me in shock with how I cringed at the blows.

Luckily, it was a blast, I built some great long lasting relationships and got to enjoy some entertaining fights while I was at it.

As I’m on this flight, I’ve been reflecting heavily on the last week.

Last week's newsletter was the most personal thing I've ever written. The layoff, Baldwin, walking into dental offices with flyers, all of it. I've never shared that story publicly before and honestly I was nervous to hit send.

The replies I got were incredible. Some of you shared your own stories. Some of you just said "I needed to hear this." That meant more to me than any open rate ever could.

So thank you. Seriously.

Now. Let me show you the other side of that story.

Last week I told you about the failures. The pivots. The 30 days of walking into dental offices with no credibility and no results.

This week I want to show you what it looks like when all of that stacks into something that actually works. Because it did. And it's working right now.

I'm currently the fractional head of content for a VC-backed DTC brand. I'm not going to name them, but I'll tell you exactly what I do and what it's produced.

And this is the part that separates what I do from what most "content strategists" or "consultants" do.

Most fractional content people will hand you a strategy deck, hop on a weekly call, give you some feedback, and send an invoice.

That's not what I do.

For this client, I'm in the trenches. I'm on camera. I'm the one creating the ads. I'm the one building the systems. I'm the one looking at the data every single day and making decisions based on what's actually working.

Here's a real example.

I had just started working with this client. Like, a little over a month working with them. And we shot a podcast-style ad. Just me and the founder having a real conversation about the product. No script. No teleprompter. Just two people talking authentically.

That ad became their top performer. And it's STILL running. Five months later. Still outperforming everything else in the account.

Here's the thing. I didn't need months of brand immersion to make that happen. I'm a storyteller. I know how to connect with audiences emotionally. That's the skill.

It actually reminds me of when I first started at Suckerpunch. Day TWO at the company, I got invited to go on the Tennis Channel to talk about the brand on live TV. 2 million people tuning in globally. I had been with the company for 48 hours. And I knocked it out of the park. Not because I had memorized the brand bible. Because I know how to tell a story and connect with people.

That's what most brands don't understand about content. It's not about how long you've been with the company. It's about whether you can walk into any room, any set, any camera and make people feel something real.

And here's the other piece of storytelling that most founders miss. The best content makes people see themselves in the problem. It puts things in simple enough terms that someone goes "ah yeah, that's me. I need that."

Most founders overcomplicate their messaging because they know TOO much. They know every feature, every technical detail, every edge case. And they dump all of that into their content. But your customer doesn't care about the specs. They care about the problem they're dealing with right now and whether you understand it.

That podcast ad worked because we didn't talk about product specifications. We told a story that made people feel seen. Simple. Human. Real.

Think about that podcast ad for a second. One piece of creator-led content, shot in a single session, has been carrying a significant chunk of their paid content performance for half a year.

A few weeks ago, I flew out to shoot fresh creative with the team. Same approach. Same format that's been winning. But with new angles, new hooks, new stories.

We now have enough footage to produce multiple new ads in the same style that's already proven. We're not guessing what might work. We're scaling what we already know works.

This is what most brands get wrong with content. They keep starting from scratch. New concept, new creator, new format, new everything. Every single time. And then they wonder why nothing builds momentum.

When you find something that works, you don't abandon it. You build variations. You test new hooks on the same foundation. You scale what's winning and cut what's not.

Here's where it gets deeper.

I didn't just show up and make some ads. I built the entire operational infrastructure around their content.

I created a custom performance dashboard that tracks every ad by audience segment. It ranks hooks by cost efficiency. It measures hold rates to see where people drop off. And it auto-generates strategic recommendations based on the data. Not "here's a spreadsheet, good luck." An actual system that tells you what to scale, what to optimize, what to cut, and what to test next.

I'm also automating their content workflows wherever possible. There's still a human element, always will be, but the repetitive stuff? The reporting? The data pulls? The performance tracking? That's all systemized now.

This is what I mean when I say AI is a tool for multiplying expertise. I didn't use AI to replace the creative thinking or the strategy. I used it to build systems that make the creative thinking and strategy go further, faster.

I'm not sharing this to flex. I'm sharing it because this is exactly the kind of thing I was trying to build when I was printing flyers and walking into dental offices.

Back then, I had the skills but no credibility. No proof. No one knew who I was.

Now I have the proof. A podcast-style ad that's been the top performer for 5+ months. A dashboard that gives the founder and their investors real visibility into what's working. An automated workflow that saves hours every week. Fresh creative shot on location that's already being cut into new winners.

That guy walking into dental offices? He wasn't failing. He was learning what it takes to actually deliver results worth paying for. And now he does.

Here's something I've learned that I think matters for anyone in this space.

The reason clients stick with me isn't because I hand them a pretty strategy deck. It's because I'm in it with them. I ask questions. I challenge their assumptions. I'm not intimidated by anyone, but I'm also 100% myself. Authentic. Open to new ideas. Fun to work with.

That last part sounds soft but it's everything. Founders are stressed. They're juggling a million things. The last thing they want is a contractor who makes their life harder or who they dread getting on a call with.

Be someone people want to work with. Be someone who dives in. That's worth more than any framework or certification.

Oh and any tennis fans out there? I got to kick it with the former World #1 Women’s Tennis Player, Tracy Austin on set that day. Still one of the coolest experiences of my career.

What I showed you today is one client. One example of what this looks like.

But the work I do spans a lot more than creator-led ads. For other clients I'm building out influencer marketing strategies, mapping creators to funnel stages, figuring out which partnerships are actually driving results and which are just burning budget. For others it's content workflow automation, reporting systems, or full creative strategy from the ground up.

The common thread is always the same. I get in the trenches. I build systems. I create the content. I don't hand you a deck and disappear.

Here's what I'm currently offering:

Fractional Head of Content for VC-backed DTC and CPG brands. Strategy, creative, influencer, systems. The whole thing. Not a consultant who advises from the sidelines. A person who's in it with you.

Custom Content & Performance Dashboards as a standalone offering. You can see exactly what these look like here:

These are demo versions with fictional brands, but the structure and functionality is identical to what I build for real clients.

If any of this sounds like what your brand needs, just reply to this email. No pitch deck. No sales call. Just a conversation about what you're working on and whether I can help.

Talk soon,

Chase