🔴 Building an audience for underdogs

And which social media platform is best for your newsletter, ft. Tyler O'Shea of Joker Mag

Today's guest is Tyler O’Shea, creator of Joker Mag, a website and newsletter about underdog stories in sports. He started the project in that “what am I gonna do with my life” period after graduating college. Nearly 7 years of posting later, he’s still doing it as a side project, but it’s also led him to a career in SEO (search engine optimization).

In this issue, we talk about:

  • ✍️ Learning how to write for the Internet

  • 🐶 The underdog story behind the underdog stories

  • 🔎 How posting led Tyler to discover and start working in SEO

  • 📱 How to figure out which social media platform is most useful for you

By the way, the podcast goes live 1 day before the newsletter ever week. Thursday mornings. Subscribe (Spotify, Apple Podcasts, YouTube) to get it earlier than the newsletter crowd.

— Francis Zierer, Editor

“To be totally honest, right after college, I was not a great writer. Like, I was used to essay-form writing and long-form and just kind of fluffing things up. It definitely took a lot of time to learn how to write for the Internet and for an audience in sports.”

After graduating college, unsure what to do with his life, Tyler O’Shea started writing for a small Philadelphia sports publication. He wasn’t being paid, but he’d always enjoyed writing in school and saw it as a way to try getting some articles published under his name.

It was addicting. Tyler soon decided to start his own website, but it was still just a hobby, a side project. At the time, he was working at a restaurant as a busboy. Soon, he left to work for a family member’s event planning firm. He spent time working as a stagehand, setting up and breaking down concerts, conventions, and trade shows around Philadelphia. All the while, he kept chipping away at Joker Mag, his passion project.

Eventually, 2.5 years after graduating college, Tyler’s work on his website taught him enough new skills to switch industries entirely. He landed a full-time job in SEO content strategy at a local advertising agency, all thanks to his persistent, experiment-happy work on the Joker Mag website:

“I would check my Google Analytics every day in the beginning, like the first year, year and a half. Like, man, I'll be lucky if I get 100 people on the website this month. And most of them were family members and friends.

Then, one day, we had an article that just took off, and I was like, what's organic traffic? I just kind of went down the rabbit hole, learned about SEO, and made a lot of mistakes.”

Tyler has now been running Joker Mag for about 6.5 years. Creator Spotlight subscribers often ask how to start creating content and build an audience from scratch. The answer is, just start. Do it in your spare time. Keep doing it. Try new things as you learn about them. That's all Tyler did.

It's simple, but it's hard work. It’s like starting to exercise — you know you should go for a run, that it’ll be good for your mind and body, but you just … don’t want to. You want to be fit, to run a flawless 7-minute mile, but you dread the months of repetition and failure it’ll take you to get there.

It’s the same with content: your posts might suck for years. But if you want to get good, you have to push through.

In seventh grade, Tyler got cut from the school baseball team. He was gutted — his dad, brother, and friends all played the sport. But he knew he deserved to be cut. He was smaller than the other kids and the bat was a little too heavy for him to swing properly.

Two days after being cut from the team, Tyler went to the family computer and started searching the web for other small guys who’d gone on to be successful baseball players. He read about people like David Eckstein, who at 5’6” was the shortest active player in Major League Baseball. Dustin Pedroia, the 5’9” Red Sox player.

Newly determined, Tyler tried again, and ended up playing baseball through college — where he became an all-conference player in his senior season. This, of course, is why he’s building a sports media brand around underdog stories. He’s carrying the torch.

When I contacted Tyler to schedule our interview, he said, "I feel like a total imposter." But he's been doing this for nearly 7 years, his newsletter has around 15k subscribers, and his website gets upwards of 50k pageviews every month. He regularly pays writers to contribute to the website. I certainly couldn't see myself playing imposter for that long and to that degree.

Joker Mag began mainly as a place for Tyler to try his hand writing about what he loved, but also with ambitions of building a profitable media company. Over the years, it’s been a platform where he can experiment, make mistakes, and work towards that ambition. He started a podcast “because it was the newest craze,” published 52 episodes over four years, then stopped because it took up more time than it was worth. He added his newsletter to the mix in 2020; it’s had more staying power than the podcast.

Tyler’s project generates enough ad revenue to sustain itself (though it doesn’t generate enough revenue for him to pay himself). He hit the 50k monthly pageviews milestone last November, the minimum requirement to work with ad management company Mediavine, which has increased his revenue. A Facebook ad campaign helped him drive enough traffic to get over the line; spend money to make money.

Next, Tyler plans to write a book, grow his newsletter list to 50k subscribers, and double his site’s monthly pageviews to 100k.

All that’s standing in his way, Tyler says, is time. “I think it's just about executing day after day. And it might not be, like, the sexiest approach, but it's what's been working for me.”

You can connect with Tyler on Twitter or by emailing [email protected].

Listen to our full conversation in Tyler’s episode of The Creator Spotlight Podcast.

Editor’s note: Usually, I share a question and answer from our podcast here.

But, a few days after recording the podcast, Tyler sent a note that underlines what I like about his attitude and approach. We're sharing it in full here (we've bolded a few lines for emphasis).

“One idea I forgot to touch on in our interview:

The skills I have developed in growing this media company (my website, newsletter, and social channels) have proven to be invaluable. By having my own business to test new ideas and growth strategies, I’ve learned lessons that would’ve taken years to uncover in a corporate setting.

I can come up with a new idea and implement it on the same day, without having to get buy-in from anyone else. This allows me to fail fast and accelerate my learning.

On top of that, Joker Mag has led to more opportunities than I could’ve ever imagined. Not only the incredible people (subjects of my stories, podcasts, etc. and of course my amazing readers), but the career growth as well. It was the only thing on my resume that helped me land my first job in SEO, and it’s helped me generate a consistent stream of freelance consulting clients.

Basically, I want to emphasize to your audience that building your own thing has more benefits than the thing itself. Yes, making money from the business directly is and always will be the main goal. But the indirect benefits are pretty sweet, too.”

I spoke to Tyler for an hour, going in-depth about much more than we can cover in the space of a newsletter. Listen to our full conversation in his episode of The Creator Spotlight Podcast.

Three weeks ago, we featured internet illustrator PJ Milani. He joined a Ship 30 for 30 cohort and it helped him break into a rewarding creative habit and build a 200k+ online audience.

Today’s sponsorship comes from the same people who run Ship 30 for 30. Safe to say they know a thing or two about teaching writing.

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Run tests to figure out which social platforms work best for you; don’t just chase what’s popular

Facebook is dead. Right? Personally, I’ve probably logged on fewer than ten times since the start of this decade. But there are reportedly still around 3 billion monthly active users.

For Tyler and Joker Mag, Facebook has proven to be the best-fitting social media platform. (Maybe there are still billions of monthly active users.) “Facebook was something I ignored for a long time, and I would just post my links there directly to Stories,” Tyler said. He was trying harder on Twitter, writing threads and trying all the tactics he read about online.

But, over the past two years, Facebook has proven to be the best algorithm-driven distribution platform for Tyler’s content (besides Google search, of course). It took four years of low-effort posting to get there, but he did eventually get there. The Joker Mag page now has 15k followers.

“I had a handful of stories that I constantly recycle every six months and one of them got like five or six million impressions just out of nowhere. I posted it on a Friday, I checked on Saturday night, and it was like three or four million impressions, it was just going crazy.

I don't know how that happened, but it's happened multiple times now.”

Here’s how to figure out which social platform’s algorithm is best for you:

  1. Pick two or more social media platforms you want to experiment with.

  2. Look up best practices for posting on those platforms.

  3. Follow best practices. Post regularly for at least three months.

  4. Iterate and experiment. Tweak just one detail every time you post.

  5. Double down where you see success. Once performance improves on one platform, stop posting on the other one(s). Invest that time into the platform that’s working.

  6. Or go back to the drawing board. If none of the platforms you’re experimenting with are working, add another to the mix. Remove whichever one you’re getting the least out of (the least enjoyment and/or the least engagement).

Which algorithm-based platform works best for you?

(Or, which one *seems* to be working best)

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A few relevant highlights from the endless stream of content we consumed this week.

  • Someone shared an excellent piece of advice with me this week. It’s from MrBeast. He’s talking about how to start creating content on YouTube from scratch, but it applies to newsletters and, honestly, any creative work. Watch it here (63 seconds).

  • More advice, specifically for newsletter writers. From The Entertainment Strategy Guy newsletter. He’s been writing on Substack for six years and shared 17 pieces of advice from his experience.

  • Kyle Chayka wrote about curator-creators, a topic we touch on frequently in this newsletter.

Thank you for taking the time to read today's issue. If you liked this one, I highly recommend listening to the podcast version.

On to next week's issue, featuring a creator who’s built a 1.4 million-strong Instagram audience over the last 6 years (slowly, then all at once, adding most followers in just the past year). She’s also experimented with a podcast and, since the start of this year, a newsletter.

We talk about

Talk soon,
Francis Zierer, Editor

P.S. This issue was slightly shorter than usual. I dropped the “Zoom Out” section. Did you notice? Let me know when you click through the poll!

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