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The Newsletter System I Actually Use

How I Learned Not to be Consistently Boring

Author

Bryan Wish
January 07, 2026

In May 2025, after we launched the evolved Arcbound brand, I committed to publishing a newsletter every week.

My first thought was anxiety.

That’s a lot of content. People are going to unsubscribe.

The opposite happened.

The newsletter quietly became our most effective channel for moving people from top of the funnel into real consideration.

Here’s what surprised me: almost anyone can write a passable LinkedIn post. Some people can record a decent video with the right prompts. But a good newsletter, the kind people actually read, requires a different level of thought, intention, and discipline.

It’s slower. More deliberate. And because of that, it builds trust in a way most other formats don’t. For instance, this newsletter took me 2 hours to write beginning to end.

Doing an omni-channel approach (posts, video, newsletters), works because people consume differently. The medium dictates the message.

But today, I want to isolate the newsletter itself, because not all newsletters are created equal.

Most feel interchangeable. Same structure, tone, and outcome. I didn’t want ours to feel like that.

Ours also hasn’t been about growing a massive list. I’ve always cared more about who is on it than how many. What mattered was the thinking behind why the newsletter existed in the first place.

There’s a saying I’ve come to believe deeply: writing is thinking. When people understand how you think, clearly, consistently, and over time, they form a durable impression of you. Not just what you know, but how you arrive there.

This was the first time I slowed down enough to examine my own thinking around the newsletter itself. How I approached it, why I structured it the way I did, and what made it work.

So I want to break down the strategy, approach, and system I use.

Creating Novelty

When I first started the newsletter more than five years ago, every issue followed the same structure and format. I needed the guardrails. They gave my creativity somewhere to land.

Over time, as I became more comfortable in my voice and started having ideas show up at inconvenient hours, usually around 3 a.m., I began loosening those guardrails. Not abandoning structure, but expanding it. Letting the format breathe and letting the delivery change when the insight demanded it.

I wanted content that did three things at once.

1) Hit people in the heart.
2) Make them think.
3) Give them systems they could actually apply to their lives and work.

Purely regurgitating actionable takeaways and recommended reads, packaged the same way every time, rarely creates an emotional connection. It might be useful, but usefulness alone doesn’t build intimacy. And if you want an audience that actually follows your thinking over time, you can’t afford to get stale.

Here’s how I approached it.

Newsletter Content Themes 

Posts about systems to show subject matter expertise 🎤

If someone is going to buy from you, they need confidence that you actually know what you’re doing. Not just in theory, but in practice. They need to see that you’ve done the work, lived the mistakes, studied the edge cases, and built a repeatable way of operating.

That means more than opinions. It means case studies. It means tradeoffs. It means a clear process for how you approach your work.

For us, that clarity started to form last year through a series of system-based newsletters.

Unexpectedly, those pieces did two things at once. They helped move deals over the line, and they forced me to articulate what we’ve actually been building for the past seven years. Writing them required me to slow down, name the patterns, and turn intuition into something explainable.

That alone made the exercise worthwhile.

Here’s what the audience consistently responded to most.

The Thought Leader Operating System | The Brand System | The Relationship System

Highly relevant pieces that turn someone’s head up and to the Right 🧠

I never took a philosophy class. But I care about writing that interrupts autopilot.

These pieces weren’t meant to teach. They were meant to slow people down just enough to notice something they’d been skimming past, or finally put words to a thought they hadn’t named.

Most content optimizes for clarity or utility. These optimized for reflection.

They asked questions without rushing to answers. They challenged assumptions without tying things up neatly. The goal wasn’t to tell people what to do next, but to make it harder to keep thinking the same way.

If someone finished one of these and kept thinking about it in their next meeting, on their commute, or right before sleep, it did its job.

Response from the Newsletter: Who Holds You Up?

Here’s what consistently resonated most.

Data Driven Pieces 📈

Some pieces called for a different approach.

For these, I went deeper. I spent time researching, pulling data, and using charts to support the writing. Not to prove a point, but to remove guesswork.

What stood out wasn’t the engagement volume, but the people who responded.

The replies came from operators and builders. People who don’t comment often, but read closely when something is grounded in reality.

Data shifts the conversation. It moves readers from whether they agree to what this changes about how they operate.

Here’s what the audience consistently responded to most.

Vulnerable: personal pieces about my life ❤️

Over the years, I’ve tried to use vulnerability in a way that’s actually useful to other people. Not venting or oversharing. And definitely not writing something that makes readers feel like they need to send a tissue box.

When done well, vulnerability is a skill. A strategic one.

It makes you human without asking for sympathy. It makes you relatable without turning the focus inward. And in the right context, with the right audience, it gives people permission to reflect on their own lives without being told to.

That’s what these pieces aimed to do.

Vision pieces 🏰

Life gets more interesting when you can connect with people around where they’re headed, not just where they’ve been. I’ve always been drawn to those conversations. Talking about direction. Possibility. What someone is quietly working toward.

But to be invited into other people’s visions, we had to be clear about our own.

These pieces were about naming the direction we were moving in and explaining why it mattered. Not to convince, but to orient. To help people decide whether they wanted to walk alongside it, contribute to it, or simply watch it unfold from a distance.

When vision is articulated well, it gives people something to align with, build upon, even if the timing isn’t immediate.

Here’s what the audience consistently responded to most.

Surprisingly effective newsletter frameworks and Communication Hacks:

The problem–solution framework

This one surprised me.

Last year, the team at 1to100.com subconsciously pushed me to communicate almost everything through a simple problem–solution lens. Vision decks. Live conversations. Writing. Newsletters.

It sounds basic. It isn’t.

Framing thinking this way forces clarity. It gives readers a place to locate themselves before you ask them to follow you somewhere else. Over time, it became one of the most reliable ways to make complex ideas feel obvious without oversimplifying them.

Some of our most effective newsletters followed this structure exactly.

Same backbone. Different insights.

Write to one person

Sometimes I wasn’t writing to an audience at all. I was writing to one specific person.

I’d picture a single reader. Someone I knew well. Someone stuck on a real decision. Someone I wanted to be honest with. And I’d write directly to them.

More often than not, those were the pieces that sparked the most replies.

Someone once told me: if you can write to one person, one hundred times over, it will resonate with far more people than trying to write to everyone once.

They were right.

Here was that moment in action:

Cadence and follow-up 🎯

A weekly newsletter builds trust

Consistency compounds.

When you show up regularly and the thought quality stays high, the return matches the effort. We saw this firsthand. New clients came in warmer. Engagement deepened. Speaking and event opportunities started to appear automatically.

The newsletter became proof that we could think clearly and show up reliably over time.

Follow up with people who are already paying attention

Reaching out to people who consistently open your newsletter works because the relationship isn’t cold. They’ve already been spending time with your thinking.

For example, we’ve set up close to 30 meetings just in January with amazing people off our newsletter list.

You don’t need to reference the newsletter or call out their engagement. The door is already cracked open. You’ve been showing up with value, and that changes the tone of the conversation before it even starts.

Most newsletter platforms (like Beehiiv) make this easy to see. The real work is deciding to act on it thoughtfully.

Features of Community at bottom:

Often, in the course of normal conversations throughout the week, it becomes clear what people are working on and what actually matters to them.

Last year, we started featuring some of those people and the work they were doing. Not as promotion, but as acknowledgment. A way to reflect their momentum back to them.

It turned out to be one of the simplest ways to create value. Low friction. High utility. No overcommitment required.

And it strengthened relationships in a way no forced outreach ever could.

Growing our Newsletter List Through Webinars 

Last year, we added a meaningful number of high-quality people to the newsletter by hosting webinars with clients and close collaborators. On average 40-60 people came to each one, sometimes more. Then, those people were added to our newsletter!

We hosted them with people we already respected, clients, or others we were in active conversation with. Tim Springer. Sean Magennis. Bob Arciniaga. Sheila Gujrathi. Case Kenny. And others.

Even doing a webinar with Case Kenny, made my co-host, Sarah Moody, vouch for him for a paid speaking engagement.

What I learned was inviting their communities into those conversations proved far more effective than chasing attention directly. Outreach felt natural because it was rooted in shared context and genuine interest, not cold promotion.

As a side note, we’ll break down our strategy and process around webinars in a future newsletter, but we did a lot of outreach over email and Linkedin to drive engagement and had 400+ attendees in the few that we did in the backhalf of the year . . .More to come.

Community Notes

  1. If this spoke to you, and you now want to think about a newsletter for yourself, please reach out if you have questions. Always down to bounce around fun ideas.

  2. We are doing a webinar with Amy Norman on February 12 at 10 AM.
    Amy is the CEO of Go Nellie, and former founder of Little Passports. She’s an incredible soul and you’re in for a treat with her amazing story.

    Sign up here!

  3. On January 14, at 5 PM PT, Immad Akhund and and Rajat Suri are doing their first podcast event for Founders in Arms at Mercury HQ. They’re picking 50 awesome founders to join. If you’d like to join, apply by clicking this link.

    125+ have applied.


  4. Alex Bratton is hosting a great AI workshop details below:

    Build an Agent in 90 Minutes - Hands on for Leaders on Jan 20 3-430pm ET:

    This session is for owners & entrepreneurs - feel free to invite any team members you'd like to expose too. Tech folks are welcome but this is about all of us building a practical comfort level with agents, not geeking out.

    -What the heck is an agent really and how is it different than ChatGPT?

    -What would I use them for?

    -Keys to succeeding with agents


    Let's build some agents on 2 different agent platforms to see strengths of each for n8n & RelevanceAI


    RSVP here for connect info