The Newsletter You Haven’t Started

I am coming up on eight years since I launched BryanWish.com.

Most people launch a personal website and then get on with their lives. Mine sent me crawling into every crevasse of what it means to build a brand.

If you had told me where that decision would lead, I would have thought you were crazy. But it became one of the best educations of my life. I learned an entire set of interrelated, yet very different, industries from the inside out. We've worked with incredible people. I continue to learn how to build a business around scalable economics, repeatable systems, and an organizational structure that can support the work.

Most people build the business first. Then, once the business works, they think about their impact. Eventually, they have enough money to invest in the brand.

For some reason, I started from the other direction.

Learn how to build the brand. Then build the business around it.

When I launched my website, my thought process was fairly simple: define my identity, what I could offer, communicate what I was learning, show up consistently, earn people’s trust, and figure out the rest from there.

Truthfully, I did not have much of a plan. I just had a belief that it would all come together.

In retrospect, I wish I had possessed a more structured roadmap and a better understanding of business before I began. I would have made far fewer mistakes. The beauty is that we are still standing, hitting our stride, and I can now share the hard-earned lessons so you do not have to suffer quite as much in the process.

Today, I can see the system much more clearly:

1. Launch a website that explains who you are, what you know, and the work you want to do. I outlined that process in The Brand System.

2. Start sharing your ideas on LinkedIn so people can discover your thinking OR choose to work with you because you're not invisible.

3. Launch a newsletter so you control the distribution of that thinking (read below!)!

4. Launch a podcast that deepens your relationships and feeds both LinkedIn and the newsletter. I explained our approach in The Podcast Philosophy System.

5. Build a go-to-market motion that turns visibility into conversations and opportunity (newsletter coming soon).

6. Productize the work into something repeatable, valuable, and capable of generating recurring revenue (newsletter coming soon)!

The newsletter sits directly in the middle of that progression. It is the bridge between having something valuable to say and building an audience that remembers you.

And launching one involves far less friction than most people think.

Two Very Different Newsletter Paths

I see people taking one of two paths.

Path A is the creator path. You join Substack, Beehiiv, or Kit, start publishing, build a large audience, and eventually try to monetize it with ads, courses, or membership subscribtions. People occasionally act as though they can write a few pieces and money will begin falling from the sky.

For a certain kind of creator and audience, that path works well.

But it is not the only path.

Path B is for the 44-year-old who is operating a nice business or just exited a company after spending 20 years building a career with their head down. Or for the executive who isn't trying to be an influencer, but want an intentionally crafted presence. They have probably earned a strong reputation, developed meaningful relationships, and accumulated more knowledge than they realize. Now, they are beginning to ask, “What’s ahead?”

That newsletter does not need to reach 111,000 strangers. It needs to reach the right people.

The path is more intentional, more relational, and more focused on the quality of the audience than its size.

That is the path I took.

I have now written my newsletter for seven years and built it to nearly 6,000 subscribers. Here is what I have learned about starting and growing one.

1. Give the Newsletter an Identity

Your newsletter should feel like an extension of your larger brand.

A distinct name can give it a world of its own. The name does not have to explain everything, but it should carry some connection to who you are, what you explore, and what readers can expect from you.

I may sound hypocritical saying this because I never officially gave my own newsletter a distinct name. But we now do it for nearly all of our clients.

Take John Grover. John may have been born with one of the best personalities in the world. He is a leadership junkie, a student of high performance, an incredible storyteller, and someone who occasionally risks his life in the wild.

His newsletter is called Three Streams. The name reflects his outdoorsy nature, but it also carries symbolic meaning connected to the ideas and craft within his upcoming book.

A strong name gives people something memorable to return to. I wrote more about that process in The Naming System for Your Brand.

2. Start With the People Who Already Know You

This is where most people create unnecessary friction.

They think they need to build an audience from zero. In reality, their audience is usually sitting in several different places, waiting to be organized.

Your existing network is likely spread across:

• LinkedIn connections

• Google contacts

• Outlook contacts

• Email history

• Calendar history

• Former clients, colleagues, collaborators, investors, and friends

Your calendar may be the most revealing source because it shows the people with whom you have actually spent time.

Export those contacts and bring them into one place. Then resist the temptation to add every name you find.

Ask one simple question:

Would this person recognize me in their inbox?

If the answer is yes, they may belong in your starting audience. If they are a stranger, a purchased contact, or someone with whom you have never meaningfully interacted, leave them off.

The guiding principle should be simple: a recognizable relationship, a clear reason for reaching out, and an easy way to leave. . . And if people don't like they were added, they can unsubscribe.

A smaller, warmer list will almost always be more valuable than a massive list of people who barely know you. The quality of the relationship matters far more than the number attached to the list.

I recommend identifying at least 300 quality people as your initial universe. You do not need to wait until you have all 300 perfectly organized before publishing. Start with the strongest relationships and build from there. Obviously, the more the merrier, and the more people you can build trust with routinely. 

3. Give Every Relationship a Place to Live

Contacts are difficult to manage because they are scattered across platforms that were never designed to work together.

A simple personal CRM gives every new relationship a place to live. It helps you remember whom you met, what you discussed, and who might genuinely benefit from hearing from you again.

I use Relatable. It connects to my email accounts and automatically pulls in the people I meet. It was created by Zvi Band, a person who genuinely lives for thoughtful curated experiences and relationships, and is also a very good human.

The specific tool matters less than the habit. You need one reliable place where your relationships can accumulate instead of disappearing into the black holes of your inbox and calendar.

4. Keep the List Alive

You are most likely receiving this newsletter because I added you myself.

At least once a month, I review the people I recently met (in my CRM) and ask, “Did we have a meaningful conversation?”

If the answer is yes, I consider whether they would find the newsletter useful and add or invite them accordingly.

I take a fairly liberal approach because I am confident that I am not going to spam people or send them content that wastes their time. That confidence creates a useful standard: if I am going to enter someone’s inbox, I need to earn the right to remain there.

Updating the list is still a pain in the butt.

It is like going to the gym when you feel sluggish. You rarely want to begin, but you always feel better once you have done it.

The benefit of a consistent workout is that you look and feel better. The benefit of consistently maintaining your relationships is that valuable content reaches more of the right people. Over time, that attention compounds into trust, opportunity, and, yes, more money in your pocket.

5. Start Monthly, Then Earn the Right to Publish More

If you are beginning, send one thoughtful newsletter each month.

Long-form writing requires more intention than posting a quick observation online. You need enough substance and differentiation to avoid sounding like everyone else. That takes time.

My newsletter started monthly and eventually became weekly.

I was hesitant to publish every week. But the frequency forced me to think more carefully about my own thoughts. It sharpened my thinking around our own delivery, how I explain the work, and how I connect what I am observing to something useful for other people.

To my surprise, showing up consistently with valuable ideas has also generated a steady stream of new clients.

I spend my time speaking with people who fit a particular profile. I build real relationships with them. The right people join the newsletter. I continue showing up with something useful.

Eventually, the phone rings.

I do not think that is a miracle. I think it is what happens when relevance, quality, and consistency have enough time to work together.

6. Find the Time When Your Mind Opens Up

My best newsletters are usually written on Saturday nights.

There is something about Saturday when no one is bothering me. No wife. No screaming babies. Just me, four walls, and my fingers hammering away at a keyboard. 

It feels like catharsis, pulling internal energy outward. Then I take a long walk at night, decompress, and get a good night’s rest.

Your time may be 4:00 a.m. before the rest of the day starts. It may be Sunday afternoon or a quiet hour after your children go to sleep.

The exact time does not matter. What matters is protecting a window in which your mind can open up.

I am a big proponent of self-expression. When it compounds in a focused way, you feel better. I have also noticed how much long-form writing supports my own mental health. I do not have quantitative data to prove it. I can simply tell you that I almost always feel better after a good writing session.

7. Use Structure Until You Develop Range

I have used many different newsletter formats over the years.

These days, I rarely write two newsletters in exactly the same way. I am too ADHD for that. I like the novelty of the blank page and the freedom to follow an idea wherever it leads.

But I did not begin there.

When I first started, I relied on a clear structure. The constraints helped me organize my thinking and made the writing stronger.

There is no single right way to write a newsletter. The goal is to develop several right ways and learn when to use each one.

I broke down the formats I have used in The Newsletter System I Actually Use.

You Are Probably Closer Than You Think

You do not need a massive audience, a perfect brand strategy, or an elaborate content machine to launch a newsletter.

You need a point of view. You need a group of people who would benefit from hearing it. Then you need the discipline to continue showing up.

Begin with the people who already know you. Organize the relationships you have already earned. Share something genuinely useful once a month.

Then keep going.

The list grows. Your thinking sharpens. People begin to understand what you know and what you care about. Familiarity becomes trust. Trust creates conversations. Conversations create opportunities.

That is how a newsletter becomes part of a brand. And, eventually, how a brand becomes part of a business.

In the coming months and years, my promise is that we will continue making this process easier with user friendly technology, more personalized, and more cost-effective for the people who have something meaningful to say.

Your voice should not have to cost a fortune.

A place to start: Block 30 minutes this week. Export one contact list and identify the first 50 people who would recognize your name in their inbox. You may already have the beginning of your newsletter sitting in front of you.

Community Notes:

1. Take Your Story From the Page to the Room

A newsletter gives you space to find your voice. Bo Eason helps you carry that voice into a room.

After five years in the NFL, performing his own play on Broadway, and spending more than 20,000 hours onstage, Bo now helps leaders uncover their personal stories, shape them, and learn how to tell them live so people can actually feel what they are saying.

If you are preparing for a keynote, leadership summit, executive offsite, or another room that matters, explore Bo’s personal story training or keynotes and corporate workshops.

2. We’ve been on a roll with our podcast The One Away Show 

Some recent episodes include Marc Shaw’s journey automating the title industry, and Tyler and Stephanie’s Leshney’s journey building Dabble and Dallop.