I'm Addicted to Marketing and Here's How It Happened

I've been in marketing in one way or another since before I was in high school.

In 2002, while I was still in grade 8, I was designing banner ads for my brother’s pay-per-click campaigns and learning how people bought, sold and monetized internet traffic. He was getting $20 per lead every time someone filled out an application for the service we were promoting. After seeing that, I could never look at a computer the same again.

Then, during the Tumblr era, I started a clothing brand called Enrollment with a few friends. We launched a Facebook Page, started an Instagram account before I even had a personal one, organized photoshoots and hosted live events. It was grassroots.

Next came the blog era and my first foray into affiliate marketing.

CourtneyStephen.com actually started as a recruiting tool. I bought the domain so college coaches could find my football highlights and stats all in one place. The site went dormant through college, but while I was playing professional football, I resurrected it as the home base for my personal brand.

I started writing about the books I was reading. I shared the articles on social media, connected with other bloggers and got a surprising amount of organic traffic. It was the golden era of writing online, when people actually read blogs and interacted with each other thoughtfully.

I started earning affiliate commissions from some of the books I recommended. Looking back, it's hard to keep a straight face when I call that "making money" because almost all of those affiliate cheques were so small they started with a $0.

Whether it was AdSense, WordPress, Amazon, MailChimp or whatever platform came next, every new tool I could get my hands on was another opportunity to learn how to turn clicks into customers.

My blogging hobby led me to email marketing, and when I started Overtime Football in 2014, email was at the centre of how I built my first successful business.

I grew the in-person athletic training side of Overtime Football Club into a six-figure business over the next 6 years, with multiple months over $25,000 in revenue. The craziest part is - we were only ever seasonal. I was still playing in the CFL. Overtime was an offseason business.

Eventually, I started thinking about how to take Overtime beyond in-person training and build an online football academy.

I took what I already knew about branding, copywriting, graphic design, and email marketing and added landing pages, funnels, conversion rate optimization, and Facebook ads.

My life became all about learning. I bought courses from Billy Gene Is Marketing and consumed everything I could from people like Pat Flynn, Amy Porterfield, Derek Halpern, John Lee Dumas, Russell Brunson and Ryan Deiss.

Then I met Susan Garrett.

Susan is a world-renowned dog agility trainer who had built a global business teaching people through online courses and communities. Football and dog agility have almost nothing in common, but the business model made perfect sense to me.

She taught me about direct-response marketing, list building and digital products. More importantly, she showed me that expertise didn't have to be limited by geography.

If she could build a global training business around dog agility, why couldn't I do it with football?

My first online win came a few months later. I remember it vividly. I was working out with some other CFL guys in a big training group. We were between sets when I heard the unmistakable cash-register notification from the Shopify app on my phone.

I had just made my first sale from an ad.

The product was a special-teams playbook for high school football coaches. I was driving paid traffic to a practice planning template, collecting contact information in exchange for the PDF, and following up by email with an offer for the digital product.

It was internet magic.

Until it wasn't...

The online version of Overtime never became what I hoped that it would. I wanted to recreate my entire in-person training experience online with demonstration videos, walkthroughs and full training programs. Unfortunately, I'd bit off way more than I could (or needed to!) chew.

I was trying to build too much. I didn't own a facility, producing the content was difficult, and I never quite got the product right.

Then COVID hit.

I couldn't run live training sessions or record the online program the way I had envisioned, and eventually I made the call to shut down my training business.

While I was upset about the way OT ended, there was a silver lining. I had gain years of hands-on experience doing real, brand and performance marketing. Of course you can read books and watch videos, but there is no substitute for putting your own money on the line and learning things the hard way.

Not long after, I took a role with the Hamilton Tiger-Cats.

My job was basically event marketing. Create memorable experiences, bring in new fans, and turn attention into attendance. I became the ultimate lead generator. The work was some mix of experiential marketing, lead generation, email marketing, content creation, and sometimes sales.

As my responsibilities grew at Hamilton Sports Group, I realized I had done almost all of this before.

Only this time the scale was bigger. The budgets were bigger. The work was more public.

But I had already worked inside CRMs, built customer journeys, segmented audiences, built brands, positioned products, hired contractors, sourced vendors, created partnerships, designed, written and led big teams.

Now we were just doing it with more money and more people watching.

Fast forward a few years.

The allure of creative hobbies pulled me into starting a sports business podcast with one of my oldest friends, James.

James and I met in high school through football. He was there in 2014 when I was thinking about starting Overtime, and we'd worked on all kinds of projects together since.

We're a lot alike. We share similar values, similar motivations and the same obsession with marketing. But our strengths are different in useful ways.

I'm highly operational. I'm a builder. James is highly technical, with a depth of knowledge that complements what I bring to the table.

One day after recording the podcast, he said, "I'm thinking of starting a Google Ads agency and I want you to go in on it with me. Are you interested?"

It made too much sense.

Playbook Digital blends so much of what I've learned throughout my life. Starting an agency pulled from my experiences in entrepreneurship, sales, design, technology, leadership, communication and marketing.

Not to mention - I straight up love this stuff.

You never get tired of hearing that cash-register-ring moment.

There's power in creating something, finding someone who needs it and convincing them to exchange their money for it. I've experienced firsthand how life-changing it can be to learn how to make money on your own terms.

I want more people to experience that.

Maybe they're building their own business. Maybe they're working inside a company doing something they love. Either way, I want to help people get better at finding their next customer.

Because if you know how to find customers, you'll always have a way to make money.

James and I had the playbook.

It was time to share it.