Packy McCormick


Case Study: Packy, the author of the wildly popular 'Not Boring' newsletter, started his journey in Write of Passage Cohort 1. Since then, he's built a business, found his voice, and amassed a die-hard fan base.

Leaning In To The Great Online Game

Packy McCormick has become a popular Internet writer over the last 3 years. His “Not Boring” newsletter about Tech Strategy is at 125,000 subscribers and growing. He stands out for fusing rigorous thinking on tech strategy with a class-clown styled writing voice. Packy started his newsletter in the 1st cohort of Write of Passage. By publishing an essay every week, he built an audience, left his job, and raised a $30 million venture fund. He coined the term, “the Great Online Game,” and is becoming the role model in how to play it.

It’s easy for a beginner to look at Packy and think, “this is some kind of irregular, highly exceptional moonshot. Surely, this couldn’t happen to me. Packy’s special.” This is exactly what he thought too when he entered Write of Passage.

By understanding Packy’s journey, frustrations, and perspective in the early days, it can help you make decisions as you start writing. You don’t have to force a path to grow. You can follow your obsessions, flow with the universe, and trust fall into the Internet. You’ll be met with opportunities you couldn’t have imagined.

Packy’s story shows us that the Internet rewards you for quality, for consistency, and for the courage to be yourself.

2017: The power of business writing

A Philly-native and Duke-graduate, Packy first saw the power of writing back in 2017. He was an early employee at Breather in New York City. The company started to collapse after it expanded too fast. He fired up a Google Doc and wrote a long memo on what Breather should do to save itself. It worked.

He suggested some controversial ideas, but he used writing to persuade the leaders of the company. They shifted from -25% to +25% profit margins. This let the power of clarifying and communicating ideas through writing click with Packy. He started binge-reading Ben Thompson’s memos to understand tech strategy. However, when a new CEO came in and suppressed their budding culture of writing, Packy was stuck. He had a newfound interest, but no professional outlet. 

In the search for new ways to stretch his brain and exercise his writing chops, he came across David Perell on Twitter. He wanted to give writing another shot, in public, and under his own name. The idea of diving into Write of Passage course was scary, foreign, and expensive, but it was worth a shot.

2019: Write of Passage Cohort 1. The early days.

Packy didn’t start off with any kind of master plan. There was no ambition to start a wildly successful newsletter. He wasn’t one of the “special” writers. He’d be happy with 100 followers. In the early days, his perspective was simple.

“It was never obvious that writing was going to be anything more for me than a way to exercise my brain, organize what I was reading, and keep in touch with friends.”

His first Write of Passage essay was titled, “The Best of Ben,” a curation piece on Ben Thompson. He thought it was garbage, but David called it out in a live session as a great piece of writing. It encouraged him to stick with it, and to think bigger.

At the end of Write of Passage, Packy launched his newsletter, “Per My Last Email.” He got 20 people to sign-up through a Twitter post (without realizing that his Twitter thumbnail accidentally said Ethel’s Newsletter– the hottest Blog You See). For the rest of 2019, Packy put in the reps, consistently curating links and sending them each week. He wasn’t terribly concerned with inventing original ideas– he just wanted to make his research public.

In the early days, Packy had the all-too-familiar fear of sending his writing out each week. He thought his friends would think he’s an idiot, with nothing to add, and talk shit about him in a group text. By the end of the year, he only had 300 followers on Twitter. He’d tweet about the Philadelphia Eagles and no one would like it.

At this point, Packy is 8 months into online writing, and there are no signs of a promising future. It goes to show that in the early days, you can’t trust the crickets of indifference. All it takes is a slight tweak for everything to suddenly explode.

2020: Not Boring, and the Packy voice.

By 2020, Packy left his job at Breather to start the “Not Boring Club.” Separate from his writing, he had a vision for an in-person community, inspired by the SOHO House, debate clubs, and college extracurriculars. The pandemic quickly made it impossible to launch. 

 WiIth time on his hands, and 400 subscribers, Packy decided to re-purpose the name “Not Boring,” and focus all his energy into his newsletter.

This next chapter signaled a shift for Packy. Instead of curating links, he’d focus on writing original Ben-Thompson-style essays. He was faced with a dilemma though. He had no focus, no angle, no niche. Packy wrote about community, sleep, scientific papers, investing, tech strategy, and whatever came into the crosshairs of his obsession. His interests were all over the place.

The traditional Personal Monopoly concept didn’t jive with Packy (he admits he thought it was bullshit at first). The goal of a Personal Monopoly is to be the only one doing the thing you’re doing. It’s about having a distinct voice as a writer. While most people find this identity through writing about the same intersection of topics, consistently, Packy found a different approach. 

Packy’s approach was to become known for the *tone* of his writing voice. When you read Packy, you feel his personality on the page– his humor, jokes, sarcasm, memes, and pop culture references. He admits he was a class-clown in high school, and would submit air-tight essays like “Jane Eyre is a dominatrix” to his English teacher and get an A+. Not Boring is the fusion of tech strategy with an edgy voice. It’s an unusual combination, and the Internet loved it.

Over the next few months, Packy published weekly long-form essays. They were rigorous ideas on tech strategy, but with the Cleveland Indians, nerdy math rants, and memes thrown in. The quality and personality of his work accelerated the growth of his newsletter. From 400, he grew to 1,000. He posted his newsletter on Product Hunt, and then it grew to 3,000. His consistency, his re-brand, his intellectual rigor, and his unique voice, all led him to go viral. Now he has 125,000 followers.

2021 and beyond. The serendipity engine.

When you share your ideas with a large audience, all sorts of opportunities rush into your life. Since Write of Passage, Packy has been able to leave his old career, and build a new one around his obsessions. We’ll look into how Packy’s writing habits left him to a life of influence, freedom, and meaning.

Packy wrote a piece on Slack just before it got acquired by Salesforce. Slack was getting beat up by the market, and Packy said everyone was wrong about the company. He was right. Ben and David invited him on the Acquired podcast to talk about Slack’s acquisition. He had already written a long-form article on it, so he became the de-facto expert in the space. When you publish quality thinking online, others in the space will want to pick your brain. Write to become the authority on topics no one else is claiming.

During Packys’ rise, he was getting all sorts of job offers. On a Write of Passage workshop, he jokingly said, these were the kinds of jobs he would “murder multiple people for” back in 2019. But Packy didn’t even need these opportunities anymore. He outgrew them. When you have an audience, you don’t need to sacrifice your autonomy to another company. If you know how to use the Internet, it lets you live life on your own terms.

In the early days, Packy would be researching young tech companies, just because he was obsessed with the space. Now, through his newsletter, he has both tech companies and investors coming directly to him. In 2021, Packy launched a $30 million venture fund through his newsletter. Through writing about his obsessions, they literally bursted into his life. He’s doing the work he’s always dreamed of, and he’s raising capital to make an impact in the space.

Jump in and Play

Packy’s most famous article is The Great Online Game. It highlights the opportunity of the Internet. If you jump in and play, really wild stuff happens. There are 3 billion people online, and niches can be absolutely massive. If you can put out well-reasoned thoughts in an entertaining way, it attracts people and opportunities into your life. Packy coined the phrase, and he’s paving the way for how to do it.

The most inspiring thing about Packy’s story is how he doubled-down on himself and his  interests, even if they don’t fit neatly in one box. It’s not about defining the total addressable market at the intersection of X, Y, and Z. It’s about writing about something you actually care about and want to spend a lot of time talking and writing about. It’s organic and emergent. There’s a direct correlation between how organic your writing journey is, and how differentiated and sustainable it is. Packy didn’t need a consistent topic, instead, he brought sizzle to business writing. It was a long and winding road, but in time, it paid off.