From 20 Subscribers to a $40 Million Venture Fund

Write of Passage is now open for enrollment. If you’ve been wanting to write online but haven't taken the leap, there’s never been a better time. 

Hey writers,

Imagine you’re a fan in the stands. Cheering, booing, or munching on popcorn. You’re entertained but powerless over the outcome. 

Now, imagine you’re a player in the game. As a player, you’re in total control. You’re making plays. You’re finding flow. You’re exercising your full potential, and having fun as you do it.

Fans vs. players. Consumers vs. creators. This is The Great Online Game. 

On the Internet, you can jump in and play whenever you want. There are no try-outs or gatekeepers. The game is free to play for everyone, and the upside of playing is infinite.

That’s how it was for Packy McCormick, a Write of Passage alum whose life transformed when he began to write online. For Packy, what started as a fun experiment turned into a $40 million venture fund. 

See? Infinite upside. As you learn about Packy’s story, imagine: What could The Great Online Game do for you?

2017: New York City

Packy worked at a fast-paced startup called Breather — so fast-paced that the company expanded too quickly and began to collapse. Packy fired up a Google doc and wrote a detailed memo on how to save the company. His ideas were spiky, and his writing was persuasive.

Packy’s plan worked. Breather went from -25% to +25% profit margins. 

Something clicked in his brain. Packy realized the power of communicating his ideas through writing. Inspired, he started binge-reading Ben Thompson’s memos and teaching himself about tech strategy.

Packy had all sorts of ideas but never shared them online. He was bursting with creativity, but had no outlet. He felt stuck and wanted to try something new.

That’s when Packy discovered Write of Passage and enrolled in Cohort 1. He thought, Why not jump in and play? In his own words, Packy wanted to see if he could “shake any magic out of the Internet.” 

The magic didn’t happen right away. But it did happen. 

2019: Write of Passage Cohort 1

Packy published his first article online in the cohort — a piece titled The Best of Ben, where he analyzed his favorite essays from Ben Thompson’s Stratechery newsletter. 

I remember reading this essay for the first time. Right away it stood out as a great piece of writing. I encouraged him to keep publishing. 

For the first few months, Packy imitated the style of his writing role-model. But Ben Thompson was already writing online. Packy knew he needed to find his own voice, and Write of Passage helped him do just that. 

Packly learned to play on the page. He started to write like himself. 

2020: The Not Boring Newsletter

Class clown meets tech strategy. Memes meet entrepreneurship. Packy’s interests didn’t exactly fit a niche, and that’s what made his voice and his message unique. He started to write what he wanted to write about. 

Within a year, he grew his newsletter to 25,000 subscribers.

2021: The Great Online Game

Packy now had a die-hard following, and he started to capitalize on the serendipity of the Internet. 

• He launched a venture capital firm through his newsletter, called Not Boring Capital.

When he announced his firm was raising funds, 900 subscribers showed $50 million in interest. Now, Not Boring Capital has invested $40 million across 200 companies. 

• He received job offers that, as he joked, he “would have murdered for” in the past. 

The thing is, he didn't need these opportunities anymore. He was already making more money than he ever had in a full-time job. When you have an audience, you don’t need to sacrifice your autonomy to another CEO. You are your own CEO. 

• Not Boring became the #1 business newsletter on Substack. 

In 2021, Packy 4x’d his audience — from 25,000 subscribers to over 100,000. And today, he has over 200,000 subscribers. His ideas were resonating with hundreds of thousands of people. 

• Most recently, Packy appeared on a podcast with Ben Thompson. 

Yes, that Ben Thompson — Packy’s favorite writer and creative role-model. Now, Packy and Ben are peers. That’s the power of the Internet's serendipity. 

From zero to 200,000+ subscribers. From anonymous to being cited by Stratechery and The New York Times. From writing about your professional idol to talking with him on air.

Packy’s most popular piece is titled — you guessed it — “The Great Online Game”: 

“Every tweet is a lottery ticket….Financial and social capital are no longer tied so tightly to where you went, who you know, or what your boss thinks of you….It’s exponential instead of linear.”

In Write of Passage, Packy started playing The Great Online Game. And now, it’s safe to say, he’s winning.

So, what about you? Are you satisfied being a fan in the stands? Or are you ready to jump in and play? 

Like Packy, you can find your voice and unlock the serendipity of the Internet. You can enroll in Write of Passage today. Cohort 11 will run from October 2 to November 8, and there are 7 days left to join. We make three commitments to our students. You will:

• Publish five quality articles
• Meet a lifelong friend
• And 2x your potential.

“Write of Passage changed the trajectory of my life and career.” – Packy McCormick 

What will it do for you?

Chat soon,

David 

P.S. The world is awash with opportunity — and online writing can open new doors in your life. But aspiring writers often smack into two mental blockers: 1) Is my writing too boring? 2) Who am I writing for? If you’ve faced these blockers, our next free workshop is built for you. Come experience Write of Passage firsthand.

Join us this Thursday, September 21, at 12 pm ET to Test Drive Write of Passage.