Breaking
Tech Strategy / Venture / Media

Packy
McCormick

The class clown who convinced 250,000 people that the future is not boring. Then charged startups to help him do it.

Not Boring Solo GP Tech Optimist Writer / Investor
250K+ Subscribers
$38M Deployed
79+ Investments
Packy McCormick
Not Boring
Since 2020
5K+ Words per essay
2020 Not Boring launched
19 Verticals invested
38 BTC sold for beer
The $2 Million Mistake

He Sold 38 Bitcoin. For Oktoberfest.

In 2013, Fred Wilson wrote a blog post about Coinbase. McCormick read it, bought 38 Bitcoin, and became an early crypto believer. Then he sold them to pay for an Oktoberfest trip in Germany. By the time the world caught up to crypto, that stack was worth somewhere in the neighborhood of $2 million. He tells the story openly. It's funnier that way.

The Bitcoin story is not a tragedy. It's a character note. McCormick is the kind of person who values a good experience enough to pay for it in retrospect, laughs at the cost, and then writes about it so other people can learn something from his mistake. That instinct - to find the human angle in every financial and technological shift - is what makes Not Boring different from every other tech publication.

The other origin story is quieter. After six years at Breather, managing teams of 150 people as VP of Experience for a venture-backed real estate startup, McCormick needed a change. He enrolled in Perell's writing course. The homework assignment was simple: start a newsletter. What he built out of that assignment has now become his entire career, his investment vehicle, and, it seems, his calling.

He tried a pivot first. "Not Boring Club" was supposed to be a real-world events business. Then COVID arrived and the real world went away. McCormick leaned into the newsletter. By March 2020, he had 400 readers. By June 2022, he had 125,000. A newsletter that started as homework was now one of the most-read tech publications in the world.

The Media Flywheel Nobody Else Has Built

The Not Boring Flywheel
Long Essays
5,000+ words on tech, startups, strategy, and the future
👥
250K Readers
Engaged, intelligent, invested in the ideas
💰
VC Fund
$38M deployed, deals sourced via newsletter reach
💡
Deep Dives
Portfolio companies amplified to 250K readers

Every venture fund promises to add value beyond capital. Most mean introductions and advice. McCormick means something different. When he writes a "Sponsored Deep Dive" on a portfolio company, he is putting out a 5,000-word analysis to 250,000 subscribers who trust his judgment. That is a media event, a customer acquisition exercise, and a talent recruitment tool packaged into a single newsletter issue.

The fund sourcing works in reverse too. Companies reach out because they want the coverage. The coverage creates the relationship. The relationship leads to the investment. In the traditional VC playbook, brand is a means to deal flow. For McCormick, the brand IS the product, and the fund is how he monetizes the credibility the brand generates.

Two Funds, One Operator, No Partners

Fund I - 2021 ~$8-10M
Fund II - 2022 $30M
Companies Invested 79+
Verticals Covered 19
2
Unicorn exits
WRITER, NexHealth
0
Analysts hired
Still just Packy
0
Board seats taken
Media instead
$2M
Bitcoin "mistake"
Best story ever

5,000 Words. Every Week. And People Read Them.

There is a simple question at the center of everything McCormick does: why would anyone read this when they could read something shorter? His answer is that shorter isn't always better - depth is better, if the depth earns its length.

His high school English teacher gave him A+ grades on essays with titles like "Jane Eyre is a dominatrix." The class clown energy was always there; it just needed a distribution channel. The newsletter became that channel. The writing blends rigorous business analysis with the kind of voice that makes you feel like you're receiving a very well-researched text message from someone who just spent a week going deep on one idea.

Each essay is a distinct structure: history, strategy memo, and prediction about impact over the next 10 years. McCormick pulls from a library of pop culture references, memes, and anecdotes that would be jarring in any traditional financial publication but feel essential in his. The technical detail is real. The jokes are actually funny. Both things at once - that's the trick.

His optimism is not naive. McCormick makes the case that the next 20 years will produce more value than the last 100, and he backs it with data, company case studies, and the kind of synthesizing-across-domains thinking that requires reading broadly and writing often. He reads history, science, and pop culture with equal intensity. The essays show it.

"Optimism actually shapes reality. If you have to choose optimism or pessimism, you're more right if you're optimistic about how things are going to go."
- Packy McCormick
Weekly
Long-form tech/business strategy essays - history, mechanics, predictions
Friday
Weekly Dose of Optimism - five promising stories from the frontier
Daily
Boring News - three Polymarket-sourced stories, weekdays
Paid
Not Boring World - community contributions from founders, researchers, creatives

From Banker to Builder to Publisher

2009
Graduates Duke University with BA in Economics. Goes where economics graduates go: investment banking.
2009 - 2013
Investment Banking Associate at Bank of America Merrill Lynch, New York. Learns finance. Reads Fred Wilson's blog. Buys 38 Bitcoin.
2013 - 2019
Joins Breather, a venture-backed real estate startup. Rises from GM of NYC Operations to VP of Experience. Manages teams of 150. Sells his Bitcoin for Oktoberfest.
2019
Enrolls in Write of Passage. Launches "Per My Last Email" newsletter with 20 subscribers. Tries "Not Boring Club" events business - COVID ends that quickly.
April 2, 2020
Not Boring launches. Grows from 400 to 125,000+ subscribers in under 2 years. The homework assignment becomes a business.
2021
Launches Not Boring Capital Fund I (~$8-10M). Invests in companies. Writes about them. The flywheel turns.
2022
Not Boring Capital Fund II closes at $30M. Newsletter tops 200,000 subscribers. Two portfolio companies reach unicorn status.
2024 - 2025
Continues weekly publishing. Portfolio grows to 79+ companies. Publishes landmark analysis of a16z fund performance. Portfolio exit: LiquiFi (July 2025).

The Traits Behind the Byline

Core Trait

Militant Optimist

Not the "things will be fine" kind. The kind who believes optimism about technology and human ingenuity is empirically defensible - and acts on it with capital.

Personality

Class Clown, Professionally

Self-described. His English teacher gave him A+ grades for creative takes on canonical texts. The same instinct now earns him 250,000 weekly readers.

Method

Cross-Domain Synthesizer

History. Science. Pop culture. Business strategy. McCormick reads everything and makes connections that specialists miss because specialists only read their own field.

Approach

Rigorous and Irreverent

The analysis is real. The jokes are real. Both appear in the same paragraph. This combination is rare and deliberately difficult to replicate.

In His Own Words

"Not boring is a philosophy. It's about finding the things that are going to be important, and writing about them before they're obvious."
Packy McCormick
"The best way to understand a company is to write about it."
Packy McCormick
"Tech is going to get much bigger. We're still in the early innings."
Packy McCormick

The Details That Define the Man

📹

First Newsletter

Called "Per My Last Email" - the passive-aggressive phrase in every corporate email. His 20 subscribers found via Twitter DMs. All homework.

🍺

The Beer Decision

Sold 38 Bitcoin for an Oktoberfest trip in Germany. By the time he was explaining this publicly, the Bitcoin was worth $2 million. He still tells the story.

📖

The Essay That Started It

His breakthrough essay "Jane Eyre is a dominatrix" got an A+ in high school. The same creative instinct, applied to tech strategy, became a $38M venture fund.

🏠

Mother-in-Law's Basement

Where the early Not Boring essays were written. The newsletter that now reaches 250,000+ people started in a basement during COVID lockdowns.

Solo Operation

No analysts. No co-GPs. No editorial team. McCormick writes every essay, manages the entire fund, and handles portfolio relationships. Alone. Every week.

📈

Growth Rate

From 400 subscribers in March 2020 to 125,000 by June 2022. The kind of growth trajectory that makes VC investors jealous of a newsletter.

What's Happening Now

July 2025

Portfolio Exit: LiquiFi

Not Boring Capital's portfolio company LiquiFi was acquired, marking a successful exit for the fund.

May 2025

a16z: The Power Brokers

Published a landmark deep-dive on Andreessen Horowitz's fund performance, noting Fund III delivered 11.3x Net TVPI. The kind of analysis that makes VC firms uncomfortable.

March 2025

Venture Capital Landscape Analysis

Published analysis on $1B+ exits and $5B+ raises in 2025, arguing that venture capital's addressable value will reach into the trillions over the next 20 years.

October 2024

Investment: Merit Systems

Latest Not Boring Capital investment continues the fund's focus on ambitious, technology-driven companies.

McCormick keeps publishing at the same cadence he set in 2020. One major essay per week. The Weekly Dose of Optimism on Fridays. Daily Boring News on weekdays. The operation has scaled in readership and in capital but not in headcount.

His 2025 analysis of a16z - one of the most powerful and private firms in venture capital - was the kind of piece that only someone with his combination of credibility and independence could write. The essay analyzed fund performance using available data, called out the gap between narrative and numbers, and published it to an audience large enough that the firm had to acknowledge it.

The venture portfolio continues to grow. The newsletter continues to be the distribution engine. The model he built, which seemed experimental in 2021, now looks like something other people are trying to copy.

Aspiration, stated plainly: to make the world more optimistic by writing clearly about technology and business - and to back the founders who are actually building what he's writing about.

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