SSS #51: 4 Tips on Writing a Newsletter


Livin’ La Vida Luna


Luna is proud of her mom for passing her citizenship test. We celebrated with this American Flag cake from Costco.

4 Tips on Writing a Newsletter

About this time last year, I was itching to flex my creative muscle in the form of a weekly newsletter.

Fast forward to today and we’re just one week away from issue #52 of SunShakSunday.

It’s been quite the journey.

Over the past year, there were a handful of times where I’d have the next 3-4 weeks of articles planned out.

However, more often than not, I started from scratch at 8pm Saturday night with less than 11 hours until my self-imposed deadline.

So why do it?

Two Reasons:

First, writing is the antidote to confusion.

When I write about a personal struggle, it’s a little bit like therapy.

When I write about an investment of time or money, it doubles as a reflection on how I could do better next time.

When I write about a book I read or a podcast I listened to, it’s an effort to imprint the newly acquired knowledge into my subconscious mind.

Second, the quick and shallow dopamine hits of posting on IG, FB, Snap, etc. don’t resonate with me. I’m trying to go deep. Long form written content is the best way I know how to do that. I just checked my IG feed and I only had one post in the past 52 weeks.

As I wrap up year one of the newsletter, I wanted to take some time and reflect on some of the things that made this process enjoyable.

Here are 4 tips on writing a weekly newsletter.

Document, Don’t Create

I write for 3 main reasons. In no particular order, they are:

  • Share my story in a way that’s helpful for the reader
  • Clarify my thoughts on a given subject
  • Leave tangible memories of me behind in case of an untimely death

Creating content from scratch is difficult. It’s much easier to simply document what I’m doing in the moment.

That’s why so many of my posts are book notes. It may seem like filler content, but I’m actually reading those books in real time and I take notes along the way. Why not share them?

I’d also rather write about actual real estate investments I’ve made than write a generic “How To Invest in Real Estate” post.

And although these are tough topics to talk about, it was somewhat easy for me to write about IVF, Placenta Accreta, and Subchorionic Hematomas because Dia and I went through all of those things in our journey to have Luna.

In short, when something interesting happens in my otherwise boring life, I take the time to write about it.

Short Sprints > Marathons

If you work, inspiration will come. If you wait, inspiration will wait too.

For this reason, I subscribe to the Seinfeld Strategy.

If you don’t know what that is, here’s the story told by Brad Isaac as a young comedian starting out on the circuit.

“He said the way to be a better comic was to create better jokes and the way to create better jokes was to write every day.

He told me to get a big wall calendar that has a whole year on one page and hang it on a prominent wall. The next step was to get a big red magic marker. He said for each day that I do my task of writing, I get to put a big red X over that day.

After a few days you'll have a chain. Just keep at it and the chain will grow longer every day. You'll like seeing that chain, especially when you get a few weeks under your belt. Your only job is to not break the chain.”


When I first started the newsletter, I was writing the bulk of my posts on two or three days: Tuesday, Thursday, and Saturday.

For about 8-10 weeks after Luna was born, I would stay up until 3am Saturday night / Sunday morning to squeeze out whatever I could just to stay on track. These nights were painful.

More recently, I’ve made an effort to write 250 words every single day. I skip a day here and there, but I never skip two days in a row.

I’m typically done with 90% of the text by Thursday. Fridays are for last minute touches. Saturdays are for editing, scheduling, and publishing.

I started tracking my daily effort in a Google Doc. My goal is to not break the chain.

When I do miss a day, I try to insert a note into the cell with my excuse. The excuse typically feels like bullshit and I hop back on the wagon the next day.


Details, Details, Details

Someone I look up to when it comes to writing told me the one thing that keeps him coming back to my newsletter every Sunday is the intricate detail I go into.

Compare this: “I bought a rental property. It will make some money. It’s an investment for my family’s future”.

To this: I bought a 3-family rental property for $215,000. The monthly rental income is expected to be $4,300 after accounting for vacancy. Our monthly expenses are $1,700, which leaves $2,500 in monthly net operating income… Here’s exactly how I did it…”

When I write about real estate, I use actual numbers and precise deal structure to make the content unique.

When I write about something personal, I try not to hold back potentially embarrassing details or sensitive information.

These details are the only thing separating my story from anyone else’s. Without the specifics, there’s no unique value proposition for the reader.

Write For an Audience of One

Every week I pick one person to write to. I will even start my Google Doc draft with, “Hey (Name)”.

I pretend I’m writing an email to a friend who just asked me for advice on that topic. If I’m really struggling to find my voice, I’ll actually open Gmail and start my first draft in the compose box.

There’s an upside and a downside to this.

The upside is I’m being hyper specific, which is typically more helpful than general advice.

The downside is I’m alienating anyone who doesn’t want or need help in that particular area.

The solution to this would be to niche down to one subject and beat it like a dead horse. But nah, I’m not about that life. I want to write about whatever I’m dealing with in the moment.

Today that happens to be Real Estate Investing, Personal Finance, Fatherhood, and Content Creation. Next year it could be completely different.

Full Circle

If the word behind the first 52 emails was Consistency, the word behind the next 52 emails will be Growth.

After next week’s email, I’m going to cull down my list to Active Readers only. I’m not interested in having a large number of subscribers if readership is low.

I’d rather continue writing for 100 people that actually read the content than have 10,000 subscribers that swipe right and click Mark as Read without actually opening the email.

Then I’m going to make an effort to distribute one post per week on a more public platform. I see Medium, Facebook, Reddit, and Biggerpockets as top contenders for distribution.

I may try some side projects in addition to the weekly newsletter as well. I’m thinking eBooks, another (monthly) newsletter that outlines the performance of my real estate investment portfolio, and some other cool stuff.

Hope to see you there.