All I Knew Was Winning. Then I Didn't.

Waddup y'all! This one's different.

No frameworks today. No content strategy breakdowns. No dashboards.

Today I want to tell you a story I've never told publicly. My wife and I were talking about it the other night and she said "you should share this." The only people who know this story are her, a few close friends, and the people in our small group.

So you're getting something real today.

For most of my life, all I knew was winning.

I'm not saying that to brag. I'm saying it because it's important context for what happened next.

Growing up, I won every championship there was to win in youth sports. I played in four straight state championships in high school and won two of them. I played Division 1 football.

I graduated college with a job already in hand. Moved to Seattle to work at Starbucks. Then Nestle. Then Nordstrom. Then Amazon.

On paper, my career was a straight line up. Every door I knocked on opened. Every bet I made hit.

And then it didn't.

End of January 2025. I got laid off from Suckerpunch.

Here's the thing though. I had actually started Social Playbook a few weeks earlier in January as a safety net. I had a feeling things weren't stable and I wanted to have something going just in case. I set it up as head of marketing consulting and had one lead in the pipeline.

The day after I got laid off, that lead converted. My first client. The timing was almost too perfect.

Then I lost that client after one month. Budget constraints.

With three months of severance in my pocket, I poured myself into the thing I'd been dreaming about for years.

A few years before all of this, my roommate asked me a simple question: "What do you use on your head in the shower?"

I didn't have an answer. And after doing a ton of research, I realized nobody did. There was no scalp care for bald men. No education. No products designed for us. Everyone was focused on hair restoration, but nobody was talking to the guys who already shaved their heads.

Baldwin was my baby.

I teamed up with beauty industry vets to create a full suite of products. A super comfortable razor. A slow growth serum so you don't have to shave as often. A mattifying sunscreen moisturizer that takes away the shine and protects from the sun. A stop stick that instantly stops nicks and cuts. The whole thing.

We got all the way through formulation on the liquid products. We had a final mold of our razor.

Then I pitched 50+ VCs and angel investors.

And here's the thing. Unlike most founders who get a quick no, I kept making it to the final round. I'd get deep into the process. Feel the momentum building. And then fall flat on my face because we didn't have enough sales. We had very few pre-sale conversions and raising for a CPG brand is just difficult.

I still love Baldwin. I have a pipe dream that one day it'll come true. The timing just wasn't there. Too many guys are focused on hair restoration right now and one day the tides will turn. It just isn't going to be today.

But I couldn't just focus on Baldwin because I still needed to bring in income. So Social Playbook pivoted to personal branding for founders and former executives.

My first real client was Christine McHugh. We became close when she was a VP at Starbucks and I was working entry level there. We both had similar stories, both former baristas who made it into corporate. She gave me my first real chance with Social Playbook and it was wildly successful for both of us.

Then Christine had a family reason to stop working together. Completely fair. But as a new entrepreneur, it hit hard because I realized how fragile this world is. Working with founders and former executives isn't like working with a funded business that sees you as a line item on their P&L. It's personal budgets. Family decisions. Things that can change overnight.

This is the part of the story I've never really told.

After Christine, after Baldwin stalling, after losing my first client in month one, I was scrambling.

I did research and found that local dental practices focused almost entirely on SEO. There were studies showing that dental offices wanted social media help but didn't know where to start. I saw an opportunity.

I created a workshop for local businesses. Three hours. We'd work together building content for their specific office. Each practice would leave with 5 fully edited videos ready to post, a 30 day content plan, and content ideas that were easy to execute with front office staff or just the dentist. Less than 2 hours a week to maintain.

I couldn't get a single response via email. So I started calling. Nothing.

So I printed out flyers. And every single day, I walked into 15 to 20 dental offices trying to sell my workshop.

Day after day after day.

A friend in the dental industry told me to focus on cosmetic dentists because they have bigger margins. I pivoted. I tried med spas too. Same result.

I had friends who supported me, who knew I was a winner, who helped me refine my pitch and find the right offices. I took all their advice and put it into practice.

And it still didn't work.

Here's what I eventually realized. These offices likely looked at me and thought, this guy is hustling, but who is he? How can I trust him? I've never heard of him or his content.

I had no credibility in that industry. Zero.

After 30 days, I made the decision to stop. Not because I felt bad for myself. Not because I thought I failed. But because I needed to figure out what was actually going to work. And maybe relatively high ticket workshops for an industry where nobody knew me wasn't the way in.

Around this time, I got introduced to someone and we started a business together doing personal branding for founders. He was supposed to lead sales. I was supposed to lead operations and pump out content for clients.

Sounded promising. Turned out to be a shit show.

I brought in 2 clients. He brought in zero. And then he wanted a 50/50 revenue split.

What??

Once I realized what was happening, I made a decision that changed everything.

I reached out to both clients I had brought in personally. I told them I could do more than just pump out content. I could become their fractional head of content. I crafted a plan for each of them, presented it, negotiated a price, and boom.

My first real VC-backed DTC brand became my client.

Holy shit. THIS is exactly what I should be doing.

Looking back, every single experience stacked into the next.

I lost my first Social Playbook client because they were bootstrapped and couldn't afford it. I lost my personal branding clients because same thing, plus families and expenses. I walked into dental offices for 30 days and learned that credibility matters more than hustle. I entered a bad business deal and refused to let it break me.

Each one taught me something. Each one pushed me closer to the thing I was actually supposed to build.

Social Playbook isn't a content agency because I thought it sounded cool. It's a content agency because every failure, every pivot, every humbling moment pointed me here.

I can't tell this story without talking about my wife.

She's the one who pushed me to start Baldwin in the first place. When I'd come home and say "OH! I think this is going to work," she never argued with me. She never said "Chase, be realistic." She supported me. She stepped up and took care of our son so I could work on my crazy ideas. She celebrated me when one thing would go right.

When I was walking into dental offices with flyers and coming home with nothing, she didn't make me feel like I was failing. She kept me on track. She kept checking in. She kept me grounded.

And she kept me grounded in my faith. Something I believe deeply but don't push on anyone. These are just my beliefs, but I think they're relevant here.

My wife always kept God at the forefront. And here's what I've learned about faith through all of this.

You can't just sit on your ass waiting for God to do things for you. That's not how it works.

Faith is getting up every morning and trying again. It's moving forward even when you can't see where you're going. It's praying that you're headed in the right direction and trusting that God is leading you. He has your back. He's by your side the entire way. But you have to keep moving. Even if it's at a snail's pace and not the pace you'd like.

That's where faith truly lives. Not in the waiting. In the walking.

I share a lot of tactical stuff in this newsletter. How to structure content teams. How to use AI the right way. How to build dashboards that give you real visibility into performance.

But I've never shared the why.

Now you know. Every framework I teach, every client I work with, every newsletter I write comes from a guy who printed flyers and walked into dental offices because he had a 6 month old at home and a wife who believed in him and he refused to let either of them down.

That's Social Playbook. That's me.

Thank you for reading. And if you're in the middle of your own version of this story right now, just keep moving. Even if it's slow. Even if you can't see where it's going. You'll get there.

One more thing. I got through this because I had people I could lean on. My wife. My best friends who I would call in between dental office visits because I needed a little inspiration or motivation. Without them, I wouldn't have kept going.

If you're going through something right now, whether it's a layoff, a failed business, a pivot that isn't working, whatever it is, don't hesitate to reply to this email. I'm always happy to lend an ear or just be someone in your corner. Seriously. I've been there.

Talk soon,

Chase