The not boring trajectory of Not Boring to 145k+ newsletter subscribers
Packy McCormick started a newsletter in 2019, it now has over 145k+ subscribers (plus 200 companies invested) and is #1 business newsletter on Substack.
How it all started;
Major milestones along the journey and how it led to 140k+ subscribers in less than 3 and a half years;
From newsletter to building an investment fund;
Not Boring audience as the center;
Takeaways from its trajectory;
How Not Boring started
Per My Last Email
Before starting the newsletter, Packy was working as a VP with a team of 150 people at a Canadian company called Breather, but he wanted to start something that would excite him.
So he bought David Perell's Write of Passage course and because one of the assignments was creating a Substack newsletter, Not Boring was born (started as Per My Last Email).
In May 2019, when he had a few hundred followers on Twitter and he sent out this tweet:
He got 28 subscribers in two days and started from there.
At first, it was a curation of books, podcasts, and essays that he found interesting with his comments.
He had no intention of going full-time (or probably didn't know this could be a thing) and no monetization strategy in mind.
Not Boring Club
In October 2019, he decided to quit his position at Breather to start Not Boring Club.
It was a social club where people would gather to “learn, build and grow together".
But product-market fit was never achieved and with the pandemic, it was paused indefinitely.
His wife Puja was pregnant and he didn't have a full-time job (or any income source).
Now he had this newsletter that grew to 473 subscribers, almost 1k Twitter followers and he wanted to try new things on it to at least help cover rent in the near future (Packy and his wife were living in his in-laws house and he was writing in the basement).
Per My Last Email → Not Boring
After pausing Not Boring Club, he took it more seriously by doing it full-time.
Via his mom's advice, he changed the name from Per My Last Email to Not Boring. Listen to your mom, everyone.
Packy also shifted the strategy of curating things from the web with some commentary to writing essays. But it had to be different than Ben Thompson from Stratechery, one of the creators he look up to.
Since his category was already crowded with a lot of established people talking about tech, strategy, finance, and economics he was afraid that no one would want another newsletter exactly about this.
So he went for business strategy + pop culture.
Readers liked that. So they started sharing more.
The Financial Times too.
By end of April (what he thought would be the end of quarantine) his goal was to reach 1k subscribers.
Paid or free content?
A clear way to monetize a newsletter is to put a paywall and ask people for money for full access.
The Substack team used to say that you can convert ~10% of your free subscribers to paid.
A lot of newsletter creators are (very) successfully monetizing it this way making 7-figures a year.
In 2020, one of his goals was to launch a paid version of the newsletter, but he decided to not go this route because of a few things you lose once you go paid:
Is it really a 10% conversion to paid?
Packy talked with other creators with paid newsletters and none of them managed the 10% conversion to paid subscribers.
So he did the math considering 5% conversion.
By then, he had 5k subscribers with a 5% conversion it would be 250 paid subscribers.
By charging $10/month it would generate $2,500 a month minus the 10% cut from Substack (assuming he would continue using the platform going paid) plus Stripe fees.
In the end, it would result in ~$2k a month for him, before taxes.
Your best posts are behind a paywall
It would make it harder for new people to discover your best content and make the decision to pay.
People wouldn't be able to share with friends that aren't subscribed, slowing down a big (if not his biggest) growth strategy.
Freedom to write
He likes to keep his content general, so he believes that it doesn't fit quite well the paid route where subscribers usually expect specific kinds of posts.
Being the only writer, he would have to find more time for paid content because he wanted to keep publishing free stuff so readers would continue to talk about Not Boring posts.
Can I expense it?
Checking other niched newsletters going paid at the time like Lenny's newsletter about product management and growth, there was a clear incentive for companies to pay for their product people to learn.
Business expense is one of the main sources of revenue for paid newsletters.
But he couldn't see people expensing Not Boring subscriptions at their companies, what would be the business return?
So he kept pushing back going paid.
Then around the summer of 2020, a company reached out to see if they could advertise in the newsletter. Packy liked the idea but when the company asked for the deck, he didn't have one.
Because of that, he surveyed the subscribers and got what anyone wanting to advertise seeks. High-income, working at great companies, leadership positions with big budgets.
He had almost 14k subscribers by now.
So he sent out a deck on his Twitter in Sep/2020 to get companies interested.
Let's look at his growth trajectory for a moment.
He had around:
300 followers in May 2019;
before the pandemic had 350 subscribers;
42 weekly posts;
By Sep/2020 (6 months after going full-time) he had:
10k followers on Twitter;
almost 14k subscribers to his newsletter;
84 weekly posts (plus the audio versions);
With this launch, he filled up his slots for the rest of the year.
By early 2021, he made more with the newsletter than when he was a startup executive.
How did he grow so much in such a short period?
People talking about it and sharing;
He tweeted about it.
That looks simple, right? Well, this may happen when you have a rock-solid foundation (great content).
Let's learn more about strategies that he used to grow his subscriber base.
Building in public
Since the beginning, Packy shared (and still does!) his numbers, failures, successes, and insights with his readers, this likely created a feeling of we're together on this.
The details and nuances (especially the numbers) in this article wouldn't be here otherwise.
Not only that, he's still active on his Twitter to this date.
He tries to reply to reader's feedback, not feed the trolls, and share what's going on in his life and newsletter.
Product Hunt launch
In June 2020, when he had around 1,8k subs, his friend Tommy suggested building a landing page for Not Boring and just launching it on Product Hunt.
He liked the idea to try out a PH launch as a growth strategy and it worked.
It went from 1,8k → 3,2k subscribers in just two days.
How he monetizes now
Not Boring Capital
In interviews, he mentions that he wouldn't be able to get into some deals if it weren't for Not Boring.
This idea started because a friend of Packy had a company that was trying to raise money from investors.
Packy sent out an investment memo and it ended up working.
After doing it successfully for other companies he saw an opportunity and Not Boring Syndicate was born.
After a while, it became a fund called Not Boring Capital.
To this date, over $30M was invested in ~200 companies.
Packy picks the companies that will be sponsoring Not Boring emails based on what he believes the readers would be interested to learn more about.
It's important for both the company paying for the sponsor (the more connected to the reader's interest the bigger the ROI) and the readers (keep them engaged even with sponsors).
Back when he started monetizing on Sep/20, he had ~14k subscribers, and the rates were:
Monday's email: $2k;
Thursday's email: $1.4k;
Deep dives’ email: $5k;
For Q1/21 when he had 30k subscribers his rates were:
Deep dives: $20k;
The Mondays placements are more expensive because they tend to be shared more compared to Thursdays'.
Recently, he created a Friday email called Weekly Dose of Optimism.
Sponsored deep dives are where Packy writes about a company (that he believes in already and would likely write about for free), but they pay for him to write about it.
After Not Boring Capital, he also uses this space to write about companies he invested in.
This idea came up when his friend and reader Nick told him that if he did paid pieces on startups similar to the free ones, he would happily pay for that.
For this type of post, he meets people from their team and really deep dives to get a good sense of the company.
That could be tricky because some people could say:
“He's now a sellout, writing about random companies just for the money”, said the trolls.
But no one gets to more than 140k subscribers without earning trust from readers.
Packy can do that because before launching the sponsored deep dives he delivered high-quality, consistent content for years and clearly states that it's sponsored content and if he has any relation with the company.
He even created a public doc on his process for deep dives, if you're curious.
His first sponsored deep dive was before creating the deck and the readers liked it.
It's now one of the most popular kinds of posts because it covers high-growth private startups and Packy shares a lot of how things work from the inside.
Those posts ended up having an unexpected effect: he created relationships with founders of those exciting startups that opened investment opportunities for Not Boring Capital.
Podcast and Talent Collective
This year, Packy relaunched Not Boring's podcast and he also has a talent platform formed by pre-approved job profiles of readers interested in joining other companies.
He uses a platform called Pallet (which he invests in).
It's free for both candidates and companies that are part of his investment portfolio (because hiring is hard).
But for other companies to gain access to the profiles, they pay a monthly subscription fee.
Other newsletter creators use Pallet as another source of income:
$1M a year with a solo newsletter
In Feb/2021, Packy tweeted this:
As you can see if you click it, the replies were really supportive.
Not Boring was making around $20k/month at this point.
It actually made more than $1M in 2021.
Not Boring uses Substack as an email platform and since they only charge when you start charging for your newsletter, so basically he pays $0 for delivering at least 1.5M emails a month.
If you ever used an email marketing platform you know how expensive it can get after creating a big audience of subscribers.
Twitter is free, but he pays $299 for Twitter Blue out of gratitude for what the platform did and continues to deliver to him.
I'm not sure how much it costs for him to run his podcast, so I won't comment on that.
The business' biggest bottleneck is time.
There are not enough hours for Packy to write about all the things he finds interesting. He could try to scale that by hiring other writers, but he's hesitant to bring someone in.
It makes sense to have that fear that people won't like someone else to write essays because Not Boring is Packy at the end of the day.
For now, he doesn't want to go for the Morning Brew route where they defined a voice and style that is scalable and reproduced across dozens of writers.
Packy already mentioned working at least 60h/week and has taken a few weeks off over the years and now has 2 kids to take care of (congrats!).
Downsides of being one-person writing it all
Packy said in multiple interviews that he works a lot. He's very successful but if he's away for a month, who would write Not Boring?
He also doesn't like the idea of having a content calendar where he could produce essays weeks or even months in advance.
Part of his current process is that pressure of “I have to finish by Sunday!" or as he admittedly mentioned that he edits out some pieces a minute before going out.
Not solo anymore
For more than 2 years, Packy was a one-person fully dedicated team (with the help of his family reading his drafts), but now his brother Dan is officially part of the company as Chief of Staff taking over the business side.
At the time of this writing, he's also hiring two analysts for Not Boring Capital and one EA.
Takeaways from Not Boring's trajectory
The compound effect
At first, it took its time to grow, then after consistently delivering value, more and more people took notice.
His approach to writing is what I believe any content creator in any medium should work towards:
Keep the audience's trust;
Keep them engaged;
Put your best stuff out there;
It's pretty crazy to go back to his first post as Not Boring when it had 544 subscribers, with 70 new in one week just almost 2 years and a half ago.
The most recent post mentions 1,582 new subscribers with 145,467 in total.
Most important in Packy's/Not Boring journey so far is being consistent and delivering the best content he can write every week.
But being consistent is not enough. Delivering real value, and keeping readers' trust and respect is what made Not Boring and will keep it a thriving business.
Not Boring's flywheel
It started out as a newsletter. But his audience, Not Boring's greatest asset, is the engine that allows Packy to not only charge a premium fee for his deep dives and sponsorship placements but also:
Gain access to founders (a lot of them may be readers or listeners already) of exciting private startups in the field of his interest → opening up opportunities for investing (Not Boring Capital);
Use his reach to help startups he's invested in through sponsored Deep Dives and podcast interviews.
With this great asset of access to those exciting startups:
Readers keep the engagement up because they get to learn about the backstage of high-growth private companies with exciting products and trajectories;
Keep his content fresh and unique, since there isn't a lot of information out there if the startup is not a high-profile one probably already covered by mainstream media (differentiator);
His readers are incentivized to share the newsletter with their friends to make them look smart (btw, if you're interested in what makes people share stuff, go read Contagious: Why things catch on);
Staying up-to-date with the market's trends and strategies promising companies are using, which Packy absorbs to ultimately apply in his current and future investments.
Hopefully, this post helped share light on Not Boring's trajectory which was a one-person operation until very recently.
If you haven't yet, check out the Not Boring newsletter here.
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