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Hi friends 👋,

Last week, I binged all of the Packy McCormick content the internet has to offer in preparation for a fireside chat I’m hosting this Thursday:

As a result, I may now be the world’s leading Packy McCormick historian — and I’d love to share with you a little bit of what I’ve learned. The dude’s story is inspirational, as you’ll soon see.

💫 Packy McCormick is a masterful player of The Great Online Game — as well he should be, because he named it.

Over the past two years, Packy went from a part-time, low-stakes writer to the central actor in a new media and investing universe. In March 2020, Per My Last Email was a 500-subscriber outlet where Packy shared his favorite links of the week. Today, exactly 19 months and one day after its debut, Not Boring is a community of 80,000 crypto nerds, investors, startup operators, and other Very Online People that acts as the gravitational center of a robust advertising business, a startup hype machine, an Angel investor syndicate, a job board, and a venture fund.

It’s obvious that Packy has struck gold. His audience is growing fast, he’s harnessed that momentum into earning a living, and his recent foray into crypto has him re-energized in his writing. (If you like this newsletter, you’ll love his.)

For the purposes of Silicon Valley Outsider, however, we’ll focus not on Packy’s present-day successes but on how he got started. It’s important for anyone who wants to break into startups — or writing, or any self-determined career path — to have examples of successful people that they can follow. As you’ll see, Packy’s example is a great one: it’s relatable and inspiring both. I think you’ll learn a lot from seeing how he navigated his transition away from a career he didn’t love and towards his dreams.

Heading into 2019, Packy felt bored and unmotivated in his job. He had spent six years at Breather, a flexible workspace startup (think short-term WeWork rental) — but after their Series D closed, Packy saw the writing on the wall:

In early 2019, the board at Breather… had just brought in a new CEO, who himself was in the middle of bringing in a new, experienced executive team. 

A couple weeks into the new regime, Ben Rollert (then VP, Product at Breather, now CEO at Composer) and I presented at an exec team offsite about the need to differentiate and dig moats in an increasingly crowded and bubbly flex office market. We got cut off halfway through with something to the effect of: “Moats? This is a big market, we don’t need to worry about moats. We have a brand. That’s what Apple has.” 

I realized that my brain was going to shrivel up and rot if I didn’t do something.

His solution:

If work wasn’t going to give him the intellectual stimulation he needed, Packy would have to find it elsewhere. And, to his immense credit, he acted decisively. Packy joined the OnDeck Fellowship (which was then only for startup founders), “joined a book club, traveled more often, and generally started saying ‘yes’ more often.” Packy also began to incubate a startup idea: an in-person social club that, in his words, would offer the equivalent of college extracurriculars for working adults. And, unbeknownst to him, he also took the first steps toward what would actually become the next phase of this career: he took David Perell’s Write of Passage, a online writing course beloved by Very Online People and Silicon Valley folks alike.

💡 Packy didn’t go all-in on any one idea too early: rather, he increased his serendipity surface area.

Packy gave himself lots of ways to get lucky, get inspired, and meet people who could help him throughout the next phase of his career.

As an assignment for the Write of Passage course, Packy started a newsletter called “Per My Last Email,” which he used primarily to share links of articles he read each week — and laid the groundwork for what would be an incredible year to come.

Packy’s experimentation continued well into 2019. He pursued his startup dreams by prototyping a “product that helped curate, synthesize, and package all of the content online… into courses.” He released one course on Sam Hinkie’s famous management of the Sixers basketball team and another “learning playlist” on Safi Bahcall’s book “Loonshots”.

And, all the time, he was building up his IRL (“In Real Life”) Social Club idea. In September 2019, Packy wrote a piece explaining the startup opportunity he intended to address:

We have shifted too quickly from doing everything offline to doing most things online, creating disconnection and unhappiness, but the rise of IRL Member Communities is one step towards a state of online-offline equilibrium in which we take advantage of the convenience and capabilities the internet enables to reconnect in real life.

By October, he officially left his day job to pursue his idea full time; in January 2020, Packy officially released his idea — again, a startup built on in-person interaction — to the world.

Of course, he had no idea that a once-in-a-century pandemic was coming. But there’s also a second lesson here:

💡 How you respond to bad luck is just as important as how you capitalize on good luck.

On March 2, 2020, Packy referenced coronavirus for the first time in his newsletter, and on March 10, he pivoted. As he explained in his next newsletter:

“I started Not Boring to help people build connection and learn new things, IRL, supported by technology. Due to the circumstances, we are postponing all IRL events, and moving everything online. It’s a setback, but it’s also a huge opportunity to get creative and provide connection and learning to people when they need it most.”

After a brief attempt to do what we all did in the first weeks of the pandemic — create skeuomorphic online experiences that were just lame versions of in-person events — Packy realized that he would have to find a new path. And his answer, as crazy as it must have seemed to his wife and friends at the time, was to throw his energy into his newsletter.

On March 23, 2020, Packy officially rebranded his newsletter from Per My Last Email to Not Boring. At the time of the rebrand, Packy had 473 subscribers, a number he hoped to grow to 1,000 by the end of the year. With the shift in focus, however, he accelerated that goal to grow to 1,000 “by the end of quarantine or the end of April, whichever comes first.” 😂

Packy McCormick @packyM

Last Per My Last E-Mail ever is out 🗣 ✨ Shiny rebrand as the Not Boring Newsletter 🔜 📈 Setting myself a goal of 1k subscribers by end of quarantine or end of April, whichever comes first 🙏🏻 Help me get there by subscribing and sharing packym.substack.com/p/the-last-per…

March 23rd 2020

16 Likes

And then his hard work began. One year after his transition, Packy wrote a great “year in review” that included this passage explaining what it took for him to grow from 500 to 42,000 subscribers in a single year:

I’m writing this on Easter Sunday. I’ve been up since 7am after sleeping six restless, post-COVID-vaccine hours. I’m physically and mentally exhausted. But I’ve been at the computer for eight hours today. I was at the computer eight hours yesterday. I don’t think I’m smarter than anyone, but I do think I can outwork everyone. I haven’t taken a day off this year other than the two days I had COVID, the four days after Dev was born, and a week around Christmas, including weekends. Seven days a week, 352 of the past 365 days. 

The lesson is clear:

💡 Having a great idea isn’t enough: there’s no substitute for working incredibly hard.

Even people who make their work look effortless — because they’re having fun, because they’re successful so quickly, etc. — can’t achieve superlative results without superlative effort. One of the things that I love about the culture of Silicon Valley (and Very Online People more generally) is that everyone wants to work as hard as I do.

I’m not saying that working ridiculously hard, never taking a weekend off, and generally sacrificing personal things for work things is the right decision for everyone (or, much less, cool). Packy is also quick to caveat his hard work:

That’s not a brag. I wish I could take time off. It seemed particularly silly when I was making no money on this newsletter and had to turn down socially distanced hangs with friends or dinners with family to write it.

But my experience aligns with Packy’s: if you really want to pursue startups, content creation, or any other career without guardrails, you’ll need to work really, really hard to succeed.

Importantly, however, going hard for Packy didn’t mean going it alone.

It’s tempting to conclude from the “work hard” advice above that the way to be successful is to cast off your social obligations, lock yourself in a cave, and emerge with a perfectly-formed diamond of a product once it’s complete. That’s certainly what I thought I needed to do when I tried to start my own company — I spent way too much time by myself and way too little time building a universe of support around me. Packy didn’t make the same mistake.

From the very beginning, Not Boring has been a communal effort. In March 2020, Packy sat down with his brother and brainstormed 1,000 ways to scale his newsletter without being spammy. In May, he brought on Ali Montag to write the first guest piece. In June, he took the advice of his friend Tommy Gamba to release his newsletter on Product Hunt, nearly doubling his readership overnight. And, as anyone who follows Not Boring can attest, Packy found help at every step of the way by his wife/editor Puja and his editor/editor Dan, both of whom read every one of the hundreds of thousands of words he produced.

What I really love about the growth of Not Boring is that, although it may seem like a huge pivot from Packy’s original hope to build an IRL Member Community, it’s closer to home that meets the eye.

💡 Packy’s success has been his community’s success.

In May 2020 — back when it was “Per My Last Email,” and before his subscriber chart went vertical — Packy wrote a piece about Scenius: groups that together push the world forward.

Throughout the piece, Packy describes how communities can collectively approximate genius even in the absence of a traditional heroic central figure — why some communities, like modern-day Silicon Valley or Renaissance Italy, can be “so astonishingly more productive than the rest.”

One answer, he writes, is crisis that “reshuffles the deck and spurs creativity”:

Silicon Valley is responsible for much of the world’s progress over the last half-century, and it would not exist without World War II. Since Shockley Semiconductor’s use of silicon in semiconductors in Mountain View in 1956, one relatively small corner of the world with a current population of four million people has produced an unprecedented amount of innovation. The Silicon Valley scenius is responsible for commercial radio, radar, videotape, random access memory, lasers, microprocessors, personal computers, satellites, 3-D computing, Google, the iPhone, and myriad other inventions. Without catastrophe, there would be no Silicon Valley. 

Of course, the crisis that made Packy’s Scenius possible was coronavirus. He tapped into the world of the Very Online writers, entrepreneurs, and investors in a magical way, and may never have done so if the world didn’t shut down just as he was building a startup focused on IRL communities.

Some of this was due to his participation in David Perell’s course, some due to connecting into the “Type House” with Li Jin and Nathan Baschez, and much of it due to Packy’s great Twitter presence, which he parlayed into connecting with other Very Online People like Mario Gabriele, Ramp Capital, Ndamukong Suh (yes, that Ndamukong Suh), Turner Novak, Jack Butcher, the Acquired guys, Sahil Bloom, and whoever writes Party Round’s tweets.

Party Round @PartyRound

alright I just bought a bunch of fortune cookies 🥠 🥠 🥠 tag your startup and we’ll tell you its fortune

October 21st 2021

6 Retweets214 Likes

It’s been an absolute joy to watch Packy discover, harness, and expand the power of his community over the past two years, and given its continued acceleration, it’s exciting to imagine what the Not Boring universe might look like two years from today.

I’m not sure where Packy hopes to take his newsletter and his community, but to use his words, I’m bullish. This guy is clearly going places, and he’s doing so with an ever-growing community at his side.

This, of course, is only part of Packy’s story! If you want to dive even deeper, join us on Thursday at the Chief of Staff Summit. And if you learned something by reading Packy’s story, consider sharing this newsletter.

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Thanks for reading Silicon Valley Outsider! I’m Christian, the Chief of Staff of Astranis, and I write this newsletter for folks who are interested in startups and live outside of the SF Bay Area. Here are a few past editions that you might like if you enjoyed this one:

• 🧠 An Outsider’s Search for Meaning

• ✍ Three lessons from a year of weekly writing

• 🤠 An Outsider’s take on Silicon Valley culture