100 Videos Later: The Untold Story of Gameday Grails

HOMEFIELD HEATER OF THE WEEK

Here’s why Homefield is great: I logged on looking for a fun hat for summer and ended up with a cool history lesson. The short version is that this menacing body of water was Pepperdine’s mascot from 1945 - 1951. Lore like that is why nobody’s touching Homefield when it comes to vintage-inspired sportswear.

Use code GRAILS15 for 15% off your first Homefield order.

GRAILS OF THE WEEK

Every week, we dive deep into eBay to bring you curated links to rare vintage sportswear at “cop this NOW!” prices.

100 VIDEOS LATER 

In the last year, I’ve made 100 videos about vintage sportswear.

That number is making me feel some type of way.

Especially because for years, I was that writer who rolled his eyes at the "pivot to video" conversation.

I built my whole career on words. Had my byline in Pitchfork, Complex, Gawker, columns for the Chicago Tribune, built newsletters that worked, won awards and made $.

Naively, I felt like videos were for “pictures” people. I was a “words” person.

But here's the secret I will now share: I was letting my ego get in the way of evolution.

Adding video to my toolkit didn't replace my writing - it amplified everything I was already doing while opening doors I didn't even know existed.

I turned my cool off and joined Cut30, a program where world-class marketing minds like Oren John demystify the process of making short-form social content and teach you how to make stuff people want to watch on the internet. If you’re looking to get started with video, I cannot recommend it enough, it's worth it.

This is the first Gameday Grails video from last March.

gamedaygrails

8,010 followers

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When I finally decided to press record, my hands were literally shaking. Here I was, a professional writer for over a decade, standing in my laundry room while my family slept upstairs, terrified of looking stupid on camera.

That first shaky video, filmed in my laundry room at 11pm, got 8K views and 11 shares. For context: Grails had about 3500 followers at the time, no paid promotion, and it was a 60-second ramble about how to spot fake vintage. The engagement wasn't from my existing writing audience - it came from vintage collectors and sports fans who'd never read a word I'd written. A year later, we’ve gained over 4,500 followers and a few of our videos have 200k - 500k views and thousands of shares.

Here's what actually worked for me:

• Finding images first before writing. What you show > what you say.

• Scripting my first 5-10 videos word-for-word to build confidence. I did this old copywriting practice called copy work where I downloaded tiktoks and IGs that went viral and literally rewrote out the scripts from each video so I could get a feel for what goes into a winning clip.

• Following female creators. Full stop: Women are better at the internet than men are. Don’t just follow people in your niche, either.

• Edit ruthlessly - my 1-minute videos start as 5 minutes of footage.

Look, I wasn't trying to build a media empire. I just knew there were stories in vintage sportswear that needed to be told. Stories about culture, history, design - the kind of stories that get overlooked because they don't fit into neat mainstream boxes. Turns out, some stories hit differently when you can show the pieces, demonstrate the details, share the excitement in real time. Weird, right?

So yeah, 100 videos later, I'm still learning. Still growing. Still occasionally cringing at my on-camera presence. But I'm showing up, telling these stories, and building something that feels true. That writer who was afraid of video? He's still here - just with more tools in his belt.

Because here's what I know after years in media: The world doesn't need more polished content. It needs more storytellers willing to push past their fears and share what they genuinely care about, in whatever medium serves the story best. The world is getting dumber because the people who can teach and share the why behind culture aren’t pivoting to video. We need all of you to make stuff suck less in the future.

In a very simplistic way, that's what we're doing here with Gameday Grails. Making stuff suck less. One story, one video, one newsletter at a time.

The best part? We're just getting started. There are thousands of untold stories in vintage sportswear from the local screen printers who created NHL jerseys in the 80s, to the forgotten designers behind your favorite team's colorways, to the cultural movements that turned specific jerseys into symbols of entire generations.

Keep an eye out. The stories we're working on for the next 100 videos are some of the best we've ever uncovered. Trust me - you won't want to miss what's coming.

-Ernest

P.S. For the record, my first videos are still up. Not because I'm proud of them, but because everyone needs proof that starting somewhere beats not starting at all.

OUR BEST STUFF 

CULT CLASSICS

100 videos in, it’s clear we stumbled upon a clear gem. Our Cult Classics series is a content franchise that encapsulates the history of vintage sportswear brands in under a minute. Catch up with past episodes:

Until next time,