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Howdy there.

Last week you met you met Jake—my dearest pepper plant—whom I rescued from the clutches of death (aka aphids). Well... I have an update on Jake. But you'll have to scroll to the bottom.

In other (personal) news...

Y'all who follow me on LinkedIn might know I do triathlon.
You also might know I raced in September.
And finished 6th in my age group 🏅💪

Well, thanks to that result...

I qualified to represent Team Canada at the 2026 Triathlon Age Group World Championships—in Spain!

🤯

I am pumped. To say the least.

But I almost missed out on this opportunity entirely—

Here's why.

Just days before my race, I realized it was a "World Championship Qualifier" (WCQ) race.

World Championships?
I could qualify?
By placing top 8?
But how...

I dug deeper.

Turns out I needed to fill out an 'Expression of Interest' (EOI) for Triathlon Canada to even consider my result for qualification.

If I hadn't filled out that EOI, I could have finished 1st place—and it wouldn't have mattered one iota.
​
No Team Canada.
No Spain.
Nada.

Thankfully I did. And thankfully I had a good race that earned me the spot.

And now I have a big decision to make (should I go to Spain?)

I'll wrap up this story with two simple lessons for newsletter & content creators:

1) EXPRESS INTEREST.
​Be proactive and reach out.
Reach out to potential sponsors.
Reach out to collab partners.
Reach out to new social followers.
Your next big sponsor isn't going to magically appear in your inbox. And your next client could be a quick DM away. But if they don't know you're interested, you'll miss your chance.

2) HARD WORK GETS REWARDED. ​
Nothing is guaranteed. Obviously.
But putting in the extra effort stacks your odds of getting on the podium (whatever your podium is). And yes, AI can do a lot of "work" for us. But it can't replace the hard work—the grit—that's needed to succeed.

On to the newsletter...

FREE Resources (created & curated by GC⚡)

→ Increase opt-ins like a best-selling author (FREE templates)

→ 30 Days of Growth (via Chenell @ Growth In Reverse)

She sold her Substack
​for $150m — to CBS

Yes, that headline is dramatic. But it's not clickbait.

Bari Weiss sold her newsletter, The Free Press, to CBS News' parent company for $150m—and she's now the Editor-In-Chief at CBS News.

Awesome for her.
*golf clap*

But what does this mean for all of us newsletter folks?

Despite Weiss' absolute outlier of a deal, there are still some important lessons. Chenell and I break down the learnings we can all take away from this blockbuster media acqui-hire.

WATCH >>​
​LISTEN >>

We also discuss some other big news & happenings in the newsletter space, like:

→ How games are becoming a core offering for newsletters
→ How to build a referral program that *actually* works AND makes you money
→ Why newsletters need to focus on the Big 3 Media Strategy

What do you think?

Please share your thoughts on this episode.

Let me know on LinkedIn or just hit reply!

Newsletter Hits
Of The Week

​

⚡ The anti-growth strategy that built a $1M newsletter out of 900 subscribers.

​

⚡ Could your best newsletter revenue strategy be with... physical products?

​

⚡ More ways to get newsletter replies.

​

⚡ Everything is so expensive. But these guys* are offering to build you a website for FREE. (*affiliate)

Growing your newsletter feel like this?

Stop beating your head against a wall.

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30-minute Strategy Sesh →

Includes:
​→ Live 1:1 call with me
→ Recording of the call + transcript
​

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Includes:
​→ Live 1:1 call with me
→ Recording of the call + transcript
→ 1-month async support (via email)

Got more questions about these sessions? Just hit reply and ask me!

Improve your newsletter with these:

→ The 1KS Roadmap: A Free Course To Your First 1,000 Subscribers​
→ Increase opt-ins like a best-selling author (FREE templates)​
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→ Book a 1:1 newsletter strategy sesh w/me: 30 mins || 60 mins

OH YEAH!

Here's a quick update on Jake: He was quarantined for a week in my garage. I brought him back into the office yesterday (it's getting too cold in my garage).

No more aphids ��
For now...

PPS - I put together a Fall Mixtape. I made it for me, but thought I'd share. Check it out here. (Can you guess how many of these artists are Canadian?)

Peace and platonic love,

Dylan

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