The weird newsletter trick nobody's using

✨_{Day 50/100} ✨

Hey - It's Tim.

50 days. 50 newsletters. No breaks.

Started as an experiment. Turned into an obsession.

_{Estimated read time: 5 minutes 12 seconds.}

By The Numbers

• 50 consecutive daily emails

• 1,803 subscribers (up from 1,224)

• 38.7% average open rate

• 7.2% average click rate

• 143 personal replies

• 1 writer's block meltdown

• 0 complaints about frequency (seriously)

These numbers tell a story. But not the whole story.

Let me walk you through what really happens when you go all-in on email.

Three Things That Actually Matter

1/ Consistency trumps perfection

The newsletter I rushed in 20 minutes got more replies than the one I spent 3 hours crafting.

Your readers don't see your process. They see what lands in their inbox.

Ship it. Fix it tomorrow.

2/ The subject line is 80% of the battle

I tested 50 different approaches. The winners?

• Questions that trigger curiosity

• Ultra-specific promises

• Slightly odd statements

"7 ways to improve your content" got 18% opens. "The weird Google trick nobody's using" got 34%.

The best subject line makes it impossible not to click.

3/ Make one point. Make it well.

My worst newsletters tried to cover too much ground.

The ones people actually shared? Dead simple.

One idea. Explained clearly. With a concrete example.

That's it.

Two Big Mistakes I Made

1/ Overthinking the tech stack

Spent a week researching platforms, templates, and automations.

Know what actually moved the needle? The words I wrote.

Use simple tools. Focus on the message.

I send with Beehiiv. I plan all the newsletter in Coda. I did all the planning in 1 day pretty much.

Trying to think of what to write is harder than actually writing the thing. Getting that all done was easily 80% of writing every day.

2/ Writing for everyone

My first 10 emails tried to please everyone.

They landed with no one.

Then I started writing like I was emailing one specific person.

Open rates jumped 11%. Reply rates tripled.

Your Burning Questions (Answered)

First thing. I write the newsletter first thing every day. Most days I'll get the first draft done the night before. But not always.

The ROI is nuts. Sign ups to Penfriend have nearly doubled every day.

I'm currently working out how many emails it takes to go from new subscriber to a Penfriend free trial. I think it's about 5 so far. Depends on what I talk about. Be it new things we're working on. Or patch notes, product updates etc.

It's made it pretty high priority.

When something doubles your sign-ups, you protect it like gold. The newsletter isn't my side project anymore - it's the engine.

Five emails to convert a free trial? That's a bargain compared to paid ads.

Email is the rare marketing channel where effort correlates directly with results. No middleman. No algorithm changes. Just you, delivering value, consistently.

"How do you come up with ideas every day?" - Marcus T.

I don't. As above, I have everything planned out for the next 2 months. And a system to do it again and again. Also, we have an internal Penny Drop slack channel. Every time I or someone on the team read something interesting, it goes in the file.

The well never runs dry.

The newsletter is up +600 subs since I started this. Which, admittedly, isn't huge. Just over 12 a day.

But, I did the dumb dumb move of not promoting the newsletter at all for the first 40 days. I was locked in. Write every day. Build the habit.

I should have been promoting. That's the goal now.

And the audience? You guys are the best. I've literally had people tell me their goal is to read every single email I send.

That's when you know you're onto something. Not when the numbers explode, but when individual readers make a commitment to open everything you write.

One reader who opens every day > 100 who open sometimes.

"Doesn't sending daily annoy your subscribers?" - Sarah K.

The data says no. Unsubscribe rate: 0.18% weekly, 0.5% daily. Engagement: up 27%.

The product data says even more. We have nearly double the daily sign-ups to Penfriend.ai since the newsletter turned daily. It made me focus far more on that side of things too. From the free trial, to the sign up. There’s a whole mini course now for free signups to Penfriend.

People don't leave because of frequency. They leave because of irrelevance.

Here's where email sits: It's my sanctuary.

Social? Crowded. Ads? Expensive. Search? I love you, but it’s hard.

But the inbox? Just me and them. No algorithm. No noise.

I don't "sell" in my emails. I just talk about what we're doing at Penfriend. Show the work. Share the journey. Point people back to the app.

Email is the only touch point I'm virtually guaranteed every day. The only channel where I get unfettered access to someone's attention. So I treat it like gold.

The real magic isn't just getting subscribers. It's making them anticipate your emails. To actually look forward to them.

When someone adds you to their "mental inbox" — the five emails they actually open each day — you've won the game.

Social comes and goes. Email endures.

"Do you ever think about giving up?" — Jamie P.

Day 24. Laptop died. Lost the charger. Was in the mountains, in a storm, with patchy internet. Newsletter went out at 3:42 AM.

Yes, I thought about it. Then I remembered why I started.

Because I told myself I would do 100 days. Honestly, it’s as simple as that.

I just said I would.

Five Quick-Fire Lessons

1/ The first line must earn the second line

If your opener doesn't grab them, nothing else matters.

2/ Plain text > fancy design

The newsletters that felt like they came from a friend outperformed the "professional" ones every time.

3/ Ask questions to get replies

End with something specific they can respond to. Engagement compounds.

4/ Write drunk, edit sober

Not literally (though sometimes). But first drafts should flow without judgment. Cut the fluff later.

5/ The P.S. gets read more than the body

Put your most important CTA here. It works.

The Hard Truth About Daily Content

Most people quit because:

• It feels like shouting into the void (weeks 1-2)

• The dopamine hits plateau (weeks 3-4)

• Life gets in the way (always)

But something magical happens around day 30.

The habit solidifies. Ideas flow easier. Readers start replying with "I was just thinking about this yesterday!"

You're no longer creating content.

You're joining a conversation.

The Surprising ROI

Everyone asks if it's worth the time investment.

Let me flip the question: What's the ROI of not showing up when your competitors disappear?

When everyone else goes quiet, consistency becomes your competitive advantage.

The newsletter has become my most valuable marketing asset.

Not because it's perfect. Because it's there. Every. Single. Day.

What could you build in 50 days?

✌️ Tim "Marathon Not A Sprint But Definitely Sprinting" Hanson
CMO @Penfriend.ai

P.S. Oh, that weird trick? It’s sending them. It’s sending an email every day.
It’s been every day Ben. The grind is real.

P.P.S. Here’s to the second half. What do you want to see from me? Reply to this email. I read all them personally. I would love to hear your ideas.

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