Hello friends,

For our second episode of Rough Draft, we’re thrilled to welcome Packy McCormick of Not Boring.

We discuss Packy's unique writing style, his rather frenetic approach to writing 10,000+ word essays each week, the business behind Not Boring, and why Packy focuses on great writing over any intentional growth efforts.

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.

I love talking to Packy because I always learn something, but also because of his infectious optimism and enthusiasm. Whether you're an aspiring or experienced writer, you'll enjoy this conversation with Packy.

Check out the full episode on Apple Podcasts, Spotify, and YouTube.

Let's dive into a few highlights from our conversation.

Monopoly of you

A pivotal moment in the origin story of Not Boring came when Packy signed up for David Perell’s Write of Passage course. The key idea Packy learned during the course was nailing the “monopoly of you”.

The idea is to bring together a few things that make you unique — your distinctive passions, areas of expertise, or personality quirks — and then write at the center of those things.

For Packy, he wanted to write about a business strategy. The problem was Ben Thompson’s Stratechery was already one of the best newsletters on the internet.

Packy felt there was an opportunity to write about tech and business strategy but in a fun, less serious way. He drew inspiration from being a fan of Bill Simmons, who mixed sports journalism with pop culture references in a novel way. Packy’s optimism and enthusiasm would also become distinctive characteristics of Not Boring.

Worldconnectors & the new mainstream — “If Ben Thompson and Bill Simmons had a baby, it would look like Not Boring.”

Most importantly, none of this was manufactured — this is who Packy is: optimistic, enthusiastic, and humorous with a deep appreciation and interest in tech, building the future, and business strategy. Packy talks about how hard it would be to “fake it” because he’s always online, writing the newsletter, tweeting, and talking to founders. It would be exhausting if he were playing a character.

It’s really hard to do this every single week if you’re not being yourself.

If you’re early in your journey, or maybe even experienced but in a reflective state, think about what makes you unique and how to form your own monopoly of you.

Growth

In the early days of Not Boring, Packy had a list of 100 ideas for how to grow the newsletter. One early experiment was posting to a Kardashian subreddit about a relevant post, after which he was effectively shadow-banned.

Any time that I would be spending on growth, I really want to spend on writing.

There were other experiments, but ultimately Packy ended up focusing all his energy on writing great posts, and then hoping readers would share it. There may be a cost to this approach: Packy mentioned falling behind other writers who are more intentional about growth, especially writers with backgrounds in product, engineering, or marketing that think about growth systematically.

But Packy didn’t seem to care as much about growing his email list these days, echoing a similar theme from our discussion with Doomberg — no doubt, a luxury for writers that already have a large, owned audience.

While Twitter was massively helpful in building Not Boring, it doesn't drive much value anymore, and Packy expressed little interest in developing a presence on TikTok or Instagram. He seems to care more about delivering value to a small group of readers he respects than, say, reaching a million subscribers.

I would much rather write something that in group chats, smart people in a particular category are sharing with each other because it helps them think about something in a different way.

We discussed how writers starting from scratch today can’t follow the same playbook as Packy and other writers with large audiences. Platforms like Twitter and Instagram were once powerful tools for building an audience, but changes like limited external linking, in-feed link throttling, whimsical moderation, and other restrictions have turned these platforms into more closed-off, siloed environments.

For new writers, rather than spend a ton of time on general audience growth, Packy suggested focusing on developing your personal monopoly and getting a small group of the right people to read in a narrow niche. Looking forward, Packy suggested more opportunities to build reliable income around smaller, niche publications (i.e., < 25k deeply engaged readers vs. >1M subscribers).

The sponsored deep dive

In the early days, despite nearly all his peers launching paid newsletters, Packy kept Not Boring free. He did this in part to focus on growing his reach and readership, choosing to avoid paywalling any of his writing, and kicking the can down the road on how to generate income.

Eventually, Packy would start to dabble with sponsorships and would come to redefine the sponsored post. Before Packy’s spin on it, “sponsored content” mostly meant brands paying Buzzfeed for listicles. Packy flipped that on its head, writing 15,000-word deep dives on startups that he found fascinating.

Like other aspects of Not Boring, the sponsored deep dives came about organically without super sophisticated thinking. One example: pricing. The cost of the sponsored deep dives came about naturally by having conversations with readers who wanted Packy to write about their company. From there, Packy set a minimum price in his mind for a 15,000-word deep dive, and then normal supply/demand mechanics helped shape the pricing over time.

Packy has had incredible success with the sponsored deep dive model. Today, for every 1 sponsored post, 20 more companies are asking Packy to do one of them. This allows Packy to choose the companies he's most excited about and to ensure he’s threading the needle in delivering value to his readers and sponsors.

A huge thank you to Packy for joining.

We hope you enjoy the conversation — let us know what you think!

We’ll be back with you next Thursday. :)

As always, thank you for your support,
Reid