Not Boring: How Packy McCormick Built a $1M Newsletter Business From His Mother-in-Law’s Basement
Chapter 1: The begining of a journey
After working for 6 years at a venture-backed startup Breather, Packy McCormick was looking to get out.
Reason?
He didn’t agree with the way things were being run by the new leadership.
But he was managing a team of 150 people and didn’t just want to up and leave. Also, he didn’t know what he’d do after leaving.
In March 2019, while he was thinking of what to do (basically procrastinating on Twitter) - he came across a tweet by David Perell (love this guy) who was launching his new writing course - ‘Write of Passage’.
And Packy had his fair share of experience with writing - writing funny analytical essays in school and also extensive writing strategy documents at Breather.
This piqued his interest and he used his $2,000 learning and development budget at Breather to sign up for the course.
As a part of the course - he had to start a substack newsletter and get 20 people to sign up.
After sending a tweet asking his 400-odd Twitter followers to sign up (he also pleaded with his mom and his in-laws). All of this helped and he managed to get 28 subscribers in the next 2 days.
His newsletter was called ‘Per My Last Email’ - where he was curating links to essays, books, podcasts and videos that he enjoyed.
At this point, Packy thought of it only as a hobby. He didn't know it yet - but it was the start of a journey.
Chapter 2: Packy has a (bad) startup idea
In October 2019, Packy finally decided to quit his job to explore his own startup idea - Not Boring Club.
Here’s the pitch for his ‘Not Boring Club’:
Before he could start hosting offline events - COVID had entered the scene.
But Packy didn’t give up just yet. He tried to bring the community online and keep it engaged through trivia nights.
Keeping an online community engaged is a tough job and Packy hated every bit of it. And to rub it in his face - there weren’t a lot of people showing up for these events either.
Packy had to finally give up on his startup idea.
Chapter 3: Packy has no job, no startup and is about to become a father
“In February (2020), Puja (his wife) and I found out we were having a baby, and I had zero income. The pressure was on.”
Packy was in a tough spot.
They had moved to his mother-in-law’s place (where he’d work out of their basement) to save some money.
So what did Packy do?
Let him tell you:
“My brilliant plan? To turn the newsletter into something that could at least pay rent at some point in the future while I tried to figure out what I wanted to do next. Maybe it would even help me find a new job.”
Writing that little newsletter which started as a part of his writing course was the only thing he was enjoying and it was now his only hope.
By March 2020 - he had written 44 editions of his newsletter and grown it to 473 subscribers over the last 11 months.
But it was time to shake things up.
Chapter 4: Packy’s life becomes Not Boring
At the suggestion of his mother - he changed the name of his newsletter from ‘Per My Last Email’ to ‘Not Boring’ (after his failed startup).
In April 2020, Not Boring as we know it was born.
But it wasn’t just the name that had changed - Packy also changed the way he was writing the newsletter.
Until now - it was just a hobby and his writing was all over the place.
Now, he decided to write more seriously about everything that he wanted to write about - tech and business strategy.
Oh, and his newsletter got long - like REALLY LONG.
He doubled down on it and essentially made Not Boring his life - writing two essays every week (Monday and Thursday).
Chapter 5: How to make ‘Not Boring’ - not boring
Personal Monopoly
When Packy started writing Not Boring - he was really conscious.
He wanted to write about exactly the same things one of his idols Ben Thompson was writing about - tech and business strategy. But he never thought he could write it better than him.
So, instead of being better or writing about something else - he decided to be different and focused on building his personal monopoly.
What is a personal monopoly?
‘Personal Monopoly’ is a concept popularized by David Perell.
Here’s how he defines it:
“It’s your unique intersection of skills, interests, and personality traits where you can be known as the best thinker on a topic and open yourself up to the serendipity that makes writing online so special.”
What was Not Boring/Packy’s personal monopoly?
Not Boring: Tech + Pop Culture + Fun
Technically, combining strategy, finance, and pop culture isn’t a new business model, nor is it better, but it’s still a moat.
Not Boring had developed a unique style of its own.
Just look at this breakdown of one of Packy’s essays by Aakash Gupta - in his newsletter Product Growth:
Packy’s Optimism
But there was one more thing that separated Packy’s Not Boring from everyone else.
It was Packy’s optimism.
In a world where everyone is talking about the doom and gloom of tech and startups, Packy’s Not Boring provides a breath of fresh air with its optimistic take on technology.
I’m far more interested in answering the question, “What does the world look like if this goes right?” than in analyzing all of the reasons something might not work. It’s how I’m wired.
In fact, he even went on to write an entire piece on optimism.
Chapter 6: Growth, Growth, Growth
The most insane thing about Not Boring is the fact that all of its growth has been organic - mostly through word of mouth.
“I’m not a growth hack person. The most important growth levers over the past year ended up being really simple: quality and consistency. Show up enough for good things to happen every once in a while.”
But there were two things that did help push Not Boring in its initial days - giving it a little boost to get the growth ball rolling.
Product Hunt Launch
On 11th June 2020, when Not Boring had reached 1,885 subscribers, Packy decided to launch his newsletter on Product Hunt.
Unlike doing what ‘growth hackers’ do - Packy simply announced his Product Hunt launch to all his subscribers and by the end of the day - Not Boring ended up becoming the #2 Product of the day.
This almost doubled his subscribers within two days from 1,885 to 3,850.
That’s the power of building a community that cares.
Leveraging Passionate Builders
One of the growth hacks that Packy almost picked up accidentally was - if you write about companies whose founders and employees are passionate and vocal on social media - they are most likely to sign up for the newsletter.
This worked extremely well for Packy - since his optimistic outlook meant that he was always going to write something good. And companies’ founders and employees were more than happy to share that with their own audience. Creating almost a growth loop for Not Boring to tap a new audience with every post.
And getting a shoutout from others is much more valuable than shouting about your own newsletter.
Shoutouts from people other people trust go 1000x further than me saying things about Not Boring ever could.
Packy managed to get a lot of those.
Chapter 7: Show me the money
By August 2020, Not Boring’s subscriber count had crossed 12,000 subscribers. Packy had been writing consistently for 16 months now (Per My Last Email - 11 months, Not Boring - 5 months) and had earned a grand total of $0.
With Packy being a soon-to-be father - he needed the money.
Initially, he had thought about turning Not Boring into a paid subscriber-only newsletter at some point. But the more he thought about it, the less sense it made.
Instead, he decided to keep his newsletter free for his subscribers by opting for the sponsorship model.
Why?
One thing that stands out throughout Packy’s journey has been his transparency with his audience. It’s this transparency that has allowed Packy to do things most newsletter writers or content creators can’t without losing trust (sponsored posts - more on this later).
His transparent decision-making has helped him build trust with his subscribers.
He even unpacked his reasoning to opt for the sponsorship model in one of his posts for his subscribers.
Here are the three main reasons for his opting for the sponsorship model:
Not niche enough: Not Boring was a little all over the place. A less clear focus means that it’s harder for people to justify expensing Not Boring.
Slow growth: Not Boring grows mainly through word of mouth. Putting the best content behind a paywall means that people can’t share the best stuff. I want as many people as possible to read and share what I write.
Money matters: I did some rough math when I was making the decision, and realized that I could probably make a lot more money over time with sponsorships assuming that keeping the newsletter free meant growing faster.
Once he decided on the sponsorship model - he quickly created a sponsor deck and shared it through a tweet. And it worked like magic.
He managed to book all the sponsored slots for the entire year. Not Boring ended 2020 with $50,000 in revenue.
Packy’s little newsletter was now officially a business with actual revenue.
Chapter 8: Thinking bigger - like $1 Million
In 2021, Packy tweeted that he wanted his free newsletter to make $1 million in revenue.
And guess what? He actually did it.
But that’s not even the crazy part.
He was just a one-man army at the time (his wife Puja and brother Dan were the ones who helped him edit his VERY LONG posts each week).
And the legend has it - Puja and Dan never got paid a cent for their hard work.
Not bad for a single-person newsletter.
Since then, he has onboarded a few more people including his brother Dan (finally he’s getting his due) to help him run his newsletter empire.
Let’s look at the unique sponsorship model that made him $1 million in revenue:
Monday ad slot: $5,000
Thursday ad slot: $3,000
Thursday deep dives: $20,000
Now, the Monday and Thursday ad slots are pretty straightforward. Companies pay Packy to include a short shoutout about them.
But it’s the Thursday deep dives that are interesting. This is where companies pay up to $20,000 to break down their business and share it with his audience.
If it was anyone else - people would blame the writer for being biased as they are getting paid to write about the company. But remember Packy’s optimistic take and transparent approach? That’s a big factor here.
He made sure he only wrote about the companies he would have written about regardless - so charging them and making it clear to his audience only helped his case.
He even went ahead and shared an entire document with his audience - explaining how he picked these companies.
This was a far cry from creators and media companies who try very hard to hide their sponsored content.
Oh, and these numbers are old (2021) - when Not Boring had around 30,000 subscribers. They now have over 185,000 subscribers. Expect Packy’s rates to be much higher now.
Chapter 9: The Investment Syndicate
Packy and Not Boring was building quite a reputation in the tech and startup circles by now. Everyone was talking about his newsletter and everyone wanted to be featured - to access his amazing audience.
One of Packy’s old friends who was now building his own startup Apt - had reached out to him for a sponsored deep dive. But Packy did them something better.
Since he loved the company - he even invested in it. Making it his first angel investment. This happened in 2020. One thing led to another and before you knew it - Packy had made a bunch of investments throughout the year.
By 2021, Packy had launched his own venture fund - the Not Boring Capital - where he’d invest in companies with stories to tell, and helps tell them.
And he invited his subscribers to take part in these investments as well - creating a Not Boring Investment Syndicate.
To date, Not Boring Capital has made investments worth over $38M (through two funds and they are now raising a third one) in more than 200 companies.
Chapter 10: The Not Boring Flywheel
Jake Singer, the writer of The Flywheel newsletter, wrote an interesting piece on the Not Boring Flywheel - on how “Packy is a better investor because of his writing, and he’s a better writer because of his investing.”
Here’s Jake’s illustration of the Not Boring Flywheel:
Here’s the breakdown:
Step 1 - Monday Piece:
Packy writes his Monday piece - which has high virality potential and fuels subscriber growth. Jake calls it - the crown jewel of Packy’s empire.
Step 2 - Growth:
These hit Monday pieces bring in loads of subscribers - week after week.
Step 3 - Everyone wants to be a sponsor:
As the audience grows - more and more founders and startups want to sponsor Not Boring - hoping Packy tells their story.
Step 4 - Sponsored Thursday deep dives:
These deep dives help Packy get an inside view of how these startups work and better understand the micro and macroeconomics and tailwinds behind the guiding trends.
Step 5 - Back to Step 1 with insightful Monday pieces:
All these valuable insights help him create even better Monday pieces. Completing the Not Boring Flywheel.
And that’s how you build a $1 million newsletter business - out of your mother-in-law’s basement (I hope Packy has moved out of there by now).
That’s a wrap.
Thanks for reading.