✊ What it takes to win


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Hi friends,

Tonight, my hometown team, the Edmonton Oilers, kick off the final challenge in their quest to claim the Stanley Cup—the NHL championship trophy—for the first time since 1990.

The Stanley Cup is generally agreed to be the most difficult trophy to win in North American professional sports.

To get this far, the Oilers have slogged through an 82-game regular season, then ground their way through three bruising best-of-seven series against some of the best teams in the league.

Almost all of them are playing hurt at this point—through fractured bones, hernias, sprains, bruises—and the ones that aren't are flat out exhausted.

If they hadn't played so well this season, they could be on the beach right now, or the golf course.

Instead, they find themselves back where they were one year ago: Facing down the defending champion Florida Panthers in the Stanley Cup Final.

Last year, they came up one game short, losing in game 7 by a single goal.

After that series, I was talking with my co-host (and fellow former Edmontonian) Justin, and he made a comment that has stuck with me.

Because it has as much to do with podcasting, business, and life as it does with hockey:

“To make it [to the Stanley Cup Final], every one of these players realized that they had another layer they could dig into, another gear they could shift into that they didn't realize they had”.

But not only did they realize that there was another layer to dig into… they learned the hard, heartbreaking way that that additional layer was required of them.

At least if they wanted to achieve the dream every one of them has held since they were 5 years old.

They realized that what they previously imagined it took to win wasn't enough.

That if they couldn't find that next gear, they'd be forever left on the outside looking in.

Having spent a decade doing creative work full-time, I can relatel.

When I think back to what I initially thought it took to be successful as an entrepreneur and creator was woefully inadequate.

And my results reflected it.

Sure, I fairly quickly found a way to support myself with my own business.

But in hindsight, that was the easy part.

I was scraping by, making enough to cover my expenses and nothing more.

I worked 12 hours (or more) a day, 7 days a week.

I went through severe burnout, dealt with problematic clients, and problematic team members.

And I was always, always, stressed.

It felt like I was giving everything to my work and my business.

And in some sense, energetically, emotionally, temporally… I was.

But there was yet another gear.

In fact, several more that I've since shifted into, and almost certainly many more to come.

Unseen, unacknowledged gears that have less to do with raw effort and more to do with strategy, wisdom, insight, and true understanding—of myself, my business, my niche, and the world and the people who make it up.

Listening to the Oilers talk this year, on the cusp of finishing the business they started last year—or rather that each of them started decades ago when they first strapped on their first pair of skates—a funny thing jumps out at me.

That the next gear they talk about, the lesson they took from last year’s loss, has nothing to do with flashy tactics, strategies, or skills.

Instead, the final gear is all about a commitment to the fundamentals.

To the things every coach they’ve ever had has preached to them ad nauseum:

  • Hustling back on defense
  • Blocking shots
  • Putting the team above your personal stats
  • Trusting your teammates
  • Playing through the whistle
  • Forechecking hard
  • Making your opponents work for every inch of ice

Most of these players have spent their careers to this point thinking they were doing these things.

Only now—having made their way to the doorstep of their goal and come up short—do they finally understand what true commitment to these fundamentals actually looks like.

The same is true for podcasting, marketing, product development, and business as a whole.

📈 I Analyzed 233 Podcast Show Names & Cover Artwork. Here's What to Do to Grow.

A potential listener's decision to listen to your show (or not) is based on the limited information available to them when they discover it.

Namely: Your show name and cover art.

These two elements, then, act as the first and most powerful listener filter. Get them wrong, and you’ll miss out on a constant stream of your ideal listeners who are passing the show over because they don’t realize it’s relevant or aligned with their taste.

But what does the “wrong” title or cover art even look like? And more importantly, what does the “right” packaging for your show look like (if it even exists)?

To find out, I analyzed 233 shows that submitted their growth data in the 2024 Podcast Marketing Trends Report to find out the branding trends between both high—and low—growth shows.

Or add to your podcast queue​

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Tactics, hacks, and shiny new tools occasionally work in the short term.

But sooner or later, the Creators and Founders that win recognize and buy into a few basic fundamental truths:

  1. The best marketing strategy is making something that people already want (and are actively seeking out)…
  2. That has a unique and refreshing value proposition…
  3. That is so good, they can’t help but talk about it.

Oh, and the fact that no matter how great your product—whether a podcast or a paid offer—you’re always going to have to market it—and in the early days, fight tooth and nail to build your initial seed audience.

In podcasting, this commitment to fundamentals is often apparent in creators who’ve spent years grinding away on shows that never found traction…

And then launch a new show—with an ultra-sharp show concept, air-tight Episode Engineering, and a commitment to doing the legwork of getting the show in front of the target audience—that takes off immediately.

The difference?

A commitment not to the growth hacks and marketing tactics but to the fundamentals.

An aversion to cutting corners.

An allergy to anything presented as a “shortcut”.

Because they’ve already chased every shortcut to its inevitable dead end.

• â€˘ â€˘ 

Of the millions of kids who play competitive hockey, only 0.1% ever play a single NHL game.

Of the thousands of players that do, only 14% have ever won the Stanley Cup.

Which means only 0.014% of anyone who plays the game ever finds the gear needed to win the ultimate prize.

The exact stats don’t matter, but thinking of all the millions of people who create content online, the percentages of how many actually build sustainable businesses around their work can’t be far off.

Most of them give up within a few weeks or months of starting.

Most of the ones that stick with it spend their careers cutting corners, chasing shortcuts, and wondering why they’re perpetually scrambling, struggling to find an audience, find customers, find clients, find traction.

Wondering why it’s all so hard.

The reality is that marketing is hard when you’re chasing easy.

And easy when you commit to hard.

Commit to the fundamentals.

Commit to doing proper competitor and market research.

Commit to audience, client, and customer interviews.

Commit to developing, testing, and iterating on a show concept rather than taking the first, low-hanging fruit idea you have.

Commit to understanding the medium.

Commit to the craft.

None of these require a budget.

Or a team.

Or any particular skill set.

They’re there for the taking.

For any and all of us.

No one’s going to hand the Oilers (or anyone else) the Stanley Cup.

And no one’s going to hand you (or anyone else) their attention, much less their hard-earned cash.

These things must be earned.

And if you haven’t earned them yet, there’s a good chance it’s because you haven’t yet found that next gear, that deeper layer of resolve.

That gear is within you.

In fact, you have several—perhaps infinite, even.

Whether you find and commit to them, however…

That’s something only you can answer.

Stay Scrappy,

In 2026, I’m reducing the number of X-Ray Audit clients I’m working with down to 15.

These audits are the most powerful and comprehensive tool I offer, and I’ve designed them specifically to spot and solve the following problems for expertise-based business owners:

  • An audience that loves the show but refuses to buy from you (but will from your guests)
  • A proven offer that gets your clients results… but struggle to sell consistently, with leads regularly ghosting you after a sales call or email exchange.
  • Spiky, unpredictable revenue cycles that leave you constantly stressed about your next month’s income
  • You regularly get passed over for speaking, partnership, and summit opportunities in your space… even though you’re more qualified than the people who get them
  • Pouring countless hours into social media with barely any discernible impact on either your growth or your sales
  • The sneaking feeling that things should be easier, given everything you’ve built (podcast, product, lead magnets, newsletter, just to name a few), and the feedback you regularly get on the quality of your work.

Unlike other specialized programs that tend to optimize for narrow siloed aspects of a business…

My job with the audits is to give you the full, comprehensive picture of how the various pieces of your business and marketing strategy fit together (or as is probably the case right now, don’t).

The end result?

Full clarity into exactly why your show hasn’t been driving the sales and growth you thought it would…

And a step-by-step roadmap on what to do—in precisely what order—to fix it.

Here’s how it works:

First, we start with an intensive assessment of your business, offers, brand, and marketing assets to spot brand and strategy-level issues and opportunities.

Second, I spend 10–15 hours with your show and related material before delivering a feature-film-length video report talking through my findings, recommendations, and suggested sequencing (don’t worry, it’s timestamped and bullet-pointed).

Third, we systematically work through the roadmap, with me guiding you on exactly what to do, how to do it, and providing insight, feedback, ideation support at every step to cut down the time to results (and revenue).

There are currently 4 audits available for pre-booking before the price goes up in 2026.

If you're interested in learning more, hit reply with "Early bird audit info" and I'll shoot over the details.

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Jump into the community and let us know what you need help with... or if this issue sparked a question you'd love to discuss further!

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🤘 This email was crafted by a human (that’s me), for a human (that’s you) 🤘

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