The story of one of startup investing’s rising stars
Packy writes my current favorite source of info, Not Boring. Twice weekly, his newsletter deep dives into timely items in technology, from a strategic lens. His work is the antidote to algorithmic madness. In a world of shallow click-bait, Not Boring is in-depth storytelling.
👉 When Solana took off a few months ago, who was there to write about it? Packy.
👉 When Slack was acquired by Salesforce, who did the Acquired podcast turn to as an expert? Packy.
👉 When Primary Venture Partners spotlighted NYC FinTech VC leaders, who did they include? Packy.
To my amazement, Packy started two years ago. His work reads like that of a career journalist and tech equity analyst.
This is because he:
1. Constantly produces, twice a week
2. Writes on timely tech trends
3. Has built a unique monetization model, with sponsored deep-dives
It is a fascinating story.
Step 1: Start Writing
2019
After a successful career in investment banking and technology, in October of 2019 Packy had risen to VP of a venture backed startup. But, as new leadership was brought in, Packy did not believe in the new direction. His favorite mentor left the company. Soon thereafter, despite living in expensive NYC, Packy left as well.
Like many in tech, one of his ideas was to start his own thing. He had in mind a social club, like a debate club. He called it Not Boring. It would be a replacement for extra-curriculars in real life. The idea would be a slog to get off the ground, but he had the type of skillset to do it. At the same time, he was also continuing a hobby he had formed in David Perell’s course Write of Passage: an email newsletter. It was called ‘per my last email.’
2020
Packy pursued both activities. In January, he launched the not boring social club, via blog post. There was just one problem. Shortly into 2020, cities like New York City more or less shutdown, as the Covid-19 pandemic hit.
The not boring club was running social dinners and trivia nights. They were crushed. Plus, after working on the club for a year, Packy did not enjoy the one-to-one sales it required. He, however, had tons of fun writing 44 editions of his ‘Per my last email’ newsletter.
Meanwhile, without a paying job, Packy had a baby on the way.
So, on April 2nd, Packy decided to merge the newsletter he had created for David’s class with his club, renaming the newsletter Not Boring.
|| Not Boring, as we know it today, was born.
Packy doubled down his focus on the newsletter. He developed regular content, publishing twice a week without fail. By May, his subscriber count was 1,500. Things were starting to click.
Packy started to develop his signature style. In May, he published the piece Startup Economic Lessons from Shen Yun’s Empire. It includes many of the key elements that now describe Packy’s work: detailed analysis, tweet evidence, and memes & funny pictures. The piece runs 2,420 words and takes up 16 pages in Google Docs. But you would not notice the length as you breeze through it. If we compress it to look at it:
We can see that Packy keeps the detail and the memes balanced. He does not overwhelm the reader, but instead keeps them engaged. With all the funny pictures, the work is also highly shareable. As a result, Packy saw continued success with the newsletter.
There was just one problem. Packy was doing this all for free. He had no job. Writing a free newsletter does not magically bring in money. Packy was making no money.
Packy set out to make money. He publicly goes through his reasoning in Looking Back, Forward, and Up. The original idea was to launch a paid newsletter. In his signature style, he manages to brand the goal in a funny way. To cover rent:
[Goal] #2: Make Enough Money From the Newsletter to Cover Rent
At about that time came the turning point. In June, Packy worked with a growth friend. He decided to create a new domain for the site and launch on Product Hunt:
Packy brought the power of his existing loyal email subscriber base to bear. Asking his list to seed success on Product Hunt, the site launch ended up the #2 product of the day on the influential site for early adopters.
From there, the newsletter subscriber growth has been on a new curve. It went from a flat-ish trajectory to a rocket-like one:
Step 2: From Writer to Investor
By April, Packy was starting to become a known tech internet personality. The team at Apt reached out. Would he want to write about them? Packy did, but he also wanted to invest.
In July, Packy went from newsletter writer to angel investor. When he wrote his piece on the startup Apt, Apt: The Natively Integrated Developer, he included the news. He had made his first angel investment, in Apt. His writing on companies had snagged enough attention to get him connected with Apt before writing about them.
Following in the footsteps of many of the other great internet writers, he became an investor in the companies he was writing about. He followed the trend of writers like Lenny Rachitsky and Tim Ferriss to investing.
Step 3: Invest Other’s Money
It is one thing to invest your own money and another thing entirely to invest the money of others.
Packy went on to manage other people’s money rather quickly. In a mere few months, in fact. Thanks to the inherent network of interested parties provided by his newsletter, by late July, Packy created the Not Boring Syndicate. Packy went from the Apt discussion in April to starting an angel fund managing other people’s money in three months.
In the first year, the group invested $2 million dollars in 14 companies. Now, it has invested in over 20 companies:
Step 4: Grow the Flywheel
Meanwhile, Packy continued his consistency and momentum as a writer. He also continued to improve. I agree with how The Flywheel puts it in their analysis:
Towards late summer 2020, Not Boring’s essays got a little bit more serious, a little bit longer, and a little bit weedsier
His pieces become more serious, longer, and in the weeds. This approach pays off. It plays well in distribution channels – on twitter, for instance. In August, Packy’s twitter thread on Tencent blew up. It is a relatively simple tweet of the logo, but it packs many elements into the teaser. Then the thread delivers on the essay summary:
There’s no company like Tencent.
— Packy McC◎rmick 👾 (@packyM) August 23, 2020
It’s elements of Facebook, PayPal, Nintendo, Spotify, Netflix, and Shopify all rolled into one PLUS a 21st century Berkshire Hathaway.
But Americans know little about it. In prep for Part II tmrw, let’s break down Tencent’s history & portfolio👇🏻 pic.twitter.com/Odk7eUXgMi
The wild success of the tweet drove the success of the post. His two-part blog piece on Tencent accumulated over 100,000 views. Packy showcased his signature style: insightful analysis on the latest tech trends in a humble, fun, and detailed way.
Unlike the rest of the web, which tends to get overly serious in analysis, Packy’s writing truly began to leap off the page at this point. It flows, and is compulsively readable. I love this excerpt from the middle of the article. You want to keep going at each point:
If you add that number to the $538 billion operating businesses value from the last section, you get $640 billion, almost exactly in line with Tencent’s current market cap of $628 billion.
So far, so good.
But that $102.6 billion is just part of the portfolio – the publicly listed non-subsidiaries. When you include investments in private companies, based on most recently announced valuations and some rough estimates, I get a current portfolio value nearly twice as big, at $187 billion.
You even want to pick up the article now, don’t you? I could have picked almost any part of it for that excerpt. He uses a structure that is heavy on transitions. Plus, the writing is almost conversational.
The short sentence as a paragraph – “So far, so good,” acts like breath in speech. It gives a different feel, almost a pause, to the long paragraphs of detailed analysis and info images. This style makes the work seem shorter than it is.
It is quite long. The two parts of the Tencent article total over 10,000 words. In Google Docs, they are over 77 pages. That is a small book. Condensed, here are the stylistic techniques overlaid to visualize the piece:
All of Packy’s stylistic tools are on display. He uses 28 fun graphics, in blue. He starts and ends strongly. That is red. He has 16 lists. That is orange. He also does great detailed analysis, in grey 6 times. Finally, he makes use of quotes in 3 places throughout the piece. Packy’s writing is quintessential long-form internet writing in 2021.
Back to our story. In September, Packy decided on an alternate route for monetization of the newsletter. Instead of going paid, like Pomp or Lenny, he decided to go the sponsorship route. He explained the reasoning in a tweet thread. His models showed at Not Boring’s growth rate, sponsorship would be more lucrative. The transparency helped his readership come along for the ride and feel like they are supporting thim.
This also opened up an interesting article type for Packy that others do not have: the sponsored deep-dive. On Thursdays, he writes in-depth about a company that is a paid post. He often invests. As a result, his readers get an inside look at companies that are A) not written about a lot and B) have very little publicly available information about them. Packy also has skin in the game with the investment.
2021
As time has continued, Packy has continued in his signature fashion: consistently publishing. This cycle is creating momentum. As Packy’s readership grows rocket-like, his deal flow becomes riper, and his investor base larger. He is creating his own unique corner in the Startup Investing landscape. The cycle looks hard to disrupt.
Meanwhile, the thought pieces continue at a furious pace. In particular, Packy has dialed up the shareability recently. Dreams all the Way Up from February, for instance, tackles FAAMG valuations. I love his signature combination of imagery, details, and timely analysis. This hook infographic should get you to click the link as well:
The pieces have become increasingly timely. In his interview with David Perell, Packy mentioned that ideas he puts on his list are often stale by the time he goes back to them. This illustrates how Packy is writing about what is, at the height of the moment, an important tech topic. By putting what people are thinking into words, doing work for people in the form of research, and applying his rich lens in the form of having been a tech operator, Packy provides pieces that are instant classics and widely shared.
As mentioned at the top of the article, that was certainly the case with his piece Solana Summer, for instance. He caught the crypto in the middle of its bull run.
In April, Packy shared his story in his own words, in A Not Boring Adventure, One Year In. As he highlights in the piece, Not Boring is an unabashedly optimistic place. There is never going to be a company take-down. As an investor, Packy is also a supporter. Overall, the piece is a fun read that provides a different, more personal and humble take on the history I have chronicled. The fact that he shares all his obstacles and rough patches in his process is humble, but his style is as well:
I still view this newsletter today as just a bigger version of the little thing it was a year ago with a few friends and random internet people, but I also realize that with more readers comes more responsibility.
That said: I am not a journalist.
Packy had just one step left in his tremendous journey – from angel syndicate lead to venture capitalist. At this time, Packy also started worked on going from angel syndicate lead to full-blown Venture Capitalist. Behind the scenes, he started to leverage the power of his readership to raise from Limited Partners (LPs).
By July, he was ready to announce. He had taken the final step. He put together a $8M venture capital fund to make more, and bigger, investments. In traditional Packy fashion, he takes his readers behind the scenes of the fundraising process in his piece, Introducing Not Boring Capital.
Packy went from newsletter writer to full-blown VC. The last step is greater success at scale, which bring us to today.
Step 5: Success
Present
Now, even if he is not a journalist, Packy has one of the top business newsletters in the world. Not Boring is one of the most powerful brands in technology.
This has paid off, monetization wise. Packy shared in a recent tweet thread that his goal is to make $1M in one year. That means he went from $0 to $1Million a year in revenue in 2 years. That is a remarkable rate for any business.
The success has led Packy to become an internet celebrity. Being an internet celebrity is not unlike being a real-life celebrity. Packy has experienced tremendous success with his writing and this has resulted in celebrity-like interactions. For instance:
- Newspapers: Being cited in newspapers like the Financial and New York Times 📰
- Idols: Being cited by your idol, in Packy’s case, Ben Thompson, who created still the culturally most important paid tech newsletter, Stratechery 🗽
- Podcasts: Asked to be on the Acquired podcast for the slack acquisition 💬
- Sports: Tweeted about by Ndamukong Suh 🏈
- Newsletters: Being written up in other newsletters 📧
He is also achieving success in investing. As he himself describes it, has access to deals he has no business being in. He is able to outperform his stature as a relatively new angel syndicate lead. Instead of being in the deals at the bottom of the barrel, or elbowing his way into deals, because of his platform, he is invited into great deals.
It helps that the accolades from founders are over the top. Packy is kind of like interviewing someone and giving them an offer. Then, when you go to check the references, they are over the moon. Here is just one of many founders publicly vouching for Packy’s impact:
— Benjamin P Rollert (@benrollert) February 10, 2021
This overall combination of factors has resulted in various accolades for Packy’s investing. As mentioned at the beginning of the essay, he was cited in a recent piece on NYC fintech VCs. He was also featured by Business Insider in a piece on solo capitalists. Those two were just in the last week. He has been mentioned widely elsewhere, prior to this week, as well.
Packy has gone from 0 subscribers to buzzy VC in less than 2 years.
Next Time
While Packy is certainly towards the height of creator economy success, I think his example has lessons for everyone working in tech. We have two more parts in the series to get there. Subscribe to get them delivered to your inbox.
Huge thank you to Chris Wong, Chase Ruzek, and Fei-Lin Tseng for their feedback on this piece. Also thank you to Packy for helping me with my substack button!
