Behind the Content of Not Boring

Not Boring is your best alternative to Business School. We spoke with the voice behind the content, Packy McCormick to learn more about his motivations, process, and goals of creating Not Boring. Not Boring is a newsletter about what’s going on in business and technology via pop culture. The perfect balance between fun and educational to get you up to speed on business concepts and trends. 

We delved into his early career, the parallels between running track and running a newsletter, his unorganized organized process, and his favorite newsletters that everyone should subscribe to.

Who’s Packy?

Packy McCormick is what I like to call, a career nomad. Seeking new activities, people to meet, and new industries to explore. 

Packy’s first appearance in the finance industry was back in 2009 at Bank of America, after a couple of years, he worked for Breather— an international office real estate company that specializes in short and medium-term rentals. Packy didn’t go to business school, but has always had an inquisitive mind and  understood the concept of due diligence - he started with the title of General Manager of NYC making his way to VP of Experience. After making his mark at Breather, he decided to leave in 2019 and move on to his next adventure, The Not Boring Club.

The Not Boring Club is like the extra-curricular layer for grownup life. The idea was the perfect hybrid between online and offline social communities. The platform allowed for people to connect online with similar passions with the goal of contributing to an in-person social club. There was a level of nostalgia at the Not Boring Club, a place where people could gather and participate in all sorts of activities such as debate, chess--really anything along with the option to start your own club right there on the platform. “It was an incredible feeling creating something that I really wanted to do and just did it. I wanted to start a community.”

As a supplemental to the Not Boring Club, he also wrote a newsletter talking through what’s going on in the mind of Packy McCormick. It was all going great until COVID-19 blew in and destroyed the concept of, well, anything in-person. So, what now?

“Content is the beacon to start a community.” — Packy

So that’s what he did, he ran with content. In High School, his sport was running track. If you bring it, you win and if you don’t, you fall behind. It’s all about how much effort you want to put in --you're the sole-being that reaps that effort. So he decided to run and run fast.

The Not Boring Newsletter You Know Today

Motivations for Curating

I always loved writing. I had a Medium account with about ten different drafts that I was too scared to send out — I knew I wanted to be writing, share my thoughts, stretch my brain, and deep-dive into a topic I was interested in. Plus, my memory sucks, I would read a lot of things and wouldn’t retain anything -- so for me, the newsletter was the perfect selfish and selfless combination. I got started by taking David Perrell's Write of Passage course, I liked the regimented process and stuck with it and evolved with it.

Why did you choose this specific topic to cover? 

It’s been all over the place with plenty of trial and error. The newsletters that are the most successful stick to a niche topic. It's hit a few different audiences, but the people I love speaking to those in the tech space but want to understand the logistics of business. I didn't get my MBA, but I would love for readers to gain enough framework to grow their business.

Do you have a goal for your newsletter? 

My overall goal for my newsletter really changes all the time, at first it was to meet interesting people, then growing my audience, and the end goal is to generate enough revenue and have Not Boring pay the rent. 

What’s your process like when creating an issue? 

Research and Collection

It really starts off with a conversation with my friends. I find out what people are interested in, then I do some digging and check out the different articles, search Twitter Threads, and do your average Google Search to see if I could offer a unique point of view.
I definitely wish my process was more organized such as having a bank of all my research that influences my issues, but for right now, the tools I use are Twitter Bookmarks for saving, Roam Research for taking notes, and Google Docs for article dumping and drafting.

If I could offer one piece of advice to people seeking to start a newsletter it would be “just do it”, click send. Don’t worry about perfection. In the beginning, no one will care if you have a typo or two. Just run and when you run, run fast. It’s the only way.


When picking and choosing the articles I place in my issues, it’s super important to see who the author is and what publication it’s listed on. It’s also vital to cross-reference and explain why I decided to take that story, add context, and information about the author/source. 


I write everything in Google Docs. When I find a topic I want to write about, I just write, edit, and then build something from scratch. I will then pull statistics, graphics that I created on Figma, and fill in the blanks.

The Disney Education FlyWheel

Formatting is definitely tricky, I started posting on Monday or Tuesday and then decided to be more consistent with it so I landed on Mondays. I recently added a Thursday edition where I create a guest post or something that I’m building for Not Boring. I tend to write long form pieces anywhere from 3000 - 4000 words, to the point where Substack shows me a red bar warning me it’s too long. When I see that bar, I cut and cut and cut. At that point, I’ll send it to my brother who I like to call my de facto editor. He helps with the editing process plenty, this is one of the most important steps of the process. Whether it’s your mom, brother, partner, whoever, it’s super important to have someone else that you trust and love to look over your work. 


Publishing in the beginning was really hard. Before I created a Substack, I had a Medium account with 10 different drafts that I just didn’t publish. It will always be scary to publish but it’s important to keep in mind that no one cares if you have a typo here or a type there. You’re human and mistakes are part of it. Now, there’s definitely a sense of completion and excitement. The most important thing is that people are enjoying the content that I write and it’s even better when the readers let me know like replying to the email, tweeting the issue, or commenting on the page. The excitement that readers bring will always make me happy, that never diminishes or lessens.


Distribution and Marketing a newsletter is vital to the process. I start by adding a promo email along with a post on Twitter. Then, when the issue is published I post to:

  1. Twitter: This is the #1 spot. It's where the kind of people who read Not Boring hang out, and my favorite place to have a conversation about the things I'm writing about. I'm a little addicted. I typically send a tweet with a link to the day's newsletter once I write it, and then either later in the day or the following day, and tweet a thread with the highlights from the piece.
  2. LinkedIn: a great way to share with former co-workers, friends who aren't on Twitter, and friends of friends. I've been surprised at how much traction LinkedIn posts get.
  3. Reddit: I find the relevant subreddits for whatever I wrote about that day and post. I made the mistake of just posting a link, and the moderators don't love that, so now I copy and paste the full post into Reddit with a link at the bottom. Reddit's pretty hit-or-miss. My most popular one was posting this Kim and Kanye piece in the KUWTK subreddit.
Lastly, my one-piece of advice for a new newsletter would be just do it. Don’t worry about perfection at all and in the beginning no one will care but if you have a typo that's totally fine and as mentioned, have someone you trust to read and edit for you.