✊ What it takes to win


​

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.

📈 2025 Indie Podcaster Survey

Compared to the larger podcast industry, the goals, obstacles, and day-to-day, on the ground realities of indie podcasters are unique... and often under-represented.

That's why every year, my friends at The Podcast Host run the annual Indie Podcasters Survey to get a pulse on where the current challenges and opportunities lie for the indie podcaster community.

The survey is now open, takes about 5-minutes to complete, and everyone who completes it will be entered to win $500 in podcast equipment.

​

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,

If you're a founder that feels like you've got all the pieces in place (offer, podcast, email marketing)... but they aren't working together in a cohesive system, I've got 6 slots left for 2025 in my 1:1 Podcast Growth Engine Program.

In the program, we'll do a full assessment of your show, marketing, sales system, and offer, and then design a strategy and system to bring them into alignment, to help you sell more and grow faster with less effort.

It's not an overnight process, but if you've already got the pieces in place, it wouldn't be unreasonable to expect to add $100k in revenue over the next year.

Here's who nails the bull's eye:

  • You're a coach, consultant, service provider, or online educator with a high-ticket offer ($5k+) that already sells consistently.
  • You have a stable business that pays you a solid, predictable salary (ie. you're not in "need cash now mode") and are in mid-to-long-term planning mode, looking to build out the systems and strategy to take your business to the next level over the next 2-5 years.
  • You've got all of core business assets already established—offer, sales process, email marketing, podcast, operations—but while all of them are performing OK, none of them are really optimized... and you know you're leaving money on the table and working harder than you need to to generate revenue.
  • You can see all the pieces and know you've built something of real value... but don't know how to connect them all in a cohesive way.
  • You understand business and marketing, but could really use some outside perspective from someone who deeply understands their work (creatively, strategically, and tactically) and what they're trying to do to bounce ideas off of, challenge their assumptions, and guide them.

If that's you, reply with the words "Growth Engine" and I'll send over all the info on how the process works.

Thanks for being a PMA Member!

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!

Reply anytime, I love hearing from you!

​