Not Boring (with Packy McCormick) - Extended Cut
David Rosenthal (host), Packy McCormick (guest), Ben Gilbert (host), Ben Gilbert (host)
In this episode of Acquired, featuring David Rosenthal and Packy McCormick, Not Boring (with Packy McCormick) - Extended Cut explores packy McCormick builds Not Boring into media-investing solo empire fast Acquired profiles Not Boring as a rare “one-person company” that became Substack’s top business newsletter in ~18 months, combining deep strategy research with a playful voice.
Packy McCormick builds Not Boring into media-investing solo empire fast
Acquired profiles Not Boring as a rare “one-person company” that became Substack’s top business newsletter in ~18 months, combining deep strategy research with a playful voice.
Packy’s path runs from finance to ultra-ops-heavy startup life at Breather, then to writing (via David Perell’s course) and a COVID-era pivot from an in-person club to the Not Boring newsletter.
He pioneered a distinctive model: high-quality sponsored deep dives where startups pay to be analyzed—fully disclosed—turning “sponsored content” into a credible, useful product.
Not Boring later expanded into Not Boring Capital (AngelList-powered), leveraging audience + content to source deals, while Packy remains a solo operator balancing scale, integrity, and personal bandwidth.
Key Takeaways
A ‘failed’ idea can be the brand seed for the winning one.
Not Boring began as an in-person social club concept; COVID killed the format, but the name and mission migrated to the newsletter—an example of salvaging brand equity even when the initial product dies.
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Packy’s edge is the uncommon mix of rigor + entertainment.
He repeatedly describes himself as “class clown with serious research,” which becomes a differentiated content moat: people will read unusually long strategy pieces because they’re fun.
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Operational scars became strategic credibility.
Breather taught him unglamorous reality (leasing, cleaning logistics, negative margins) and later the power of strategy when a memo-led turnaround moved margins from ~-25% to ~+25%.
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Growth came from shipping consistently, staying free, and narrating progress.
He delayed subscriptions to avoid slowing growth, used Product Hunt via a landing page, and publicly tracked subscriber counts—turning the audience into participants in the journey.
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He redefined sponsored content by making it ‘best on the internet.’
The model works because he discloses sponsorship upfront, keeps the analytical bar high, and uses privileged access to produce deeper, more useful breakdowns than independent coverage often can for young startups.
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Platform unbundling enables ‘solo corporations.’
Substack, Twitter, Mercury, and especially AngelList let one person run media + a venture vehicle without a traditional staff, turning specialization-of-labor into leverage for individuals.
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The main constraint is Packy himself (and that’s both moat and risk).
His “process power” is hard to replicate or delegate, but it also makes the business fragile (vacations, burnout, “hit by a bus” risk) and caps expansion into products without diluting the core.
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Notable Quotes
“This episode is a failure if we don't get you over 100K subscribers.”
— David Rosenthal
“The earliest version of Not Boring... was called Golden Memories of a Young Boy's Life.”
— Packy McCormick
“By the time that I get home, I want all of your certificates... in a box in the attic. We're calling that box the loser box because you're a loser.”
— Packy McCormick (recounting his dad)
“Seven days a week, 6:00 AM to 11:00 PM... I was just on my phone, texting messengers who were gonna go clean Breather.”
— Packy McCormick
“At least if I'm saying, 'I am sponsored'... it is just very out in the open what I'm trying to do.”
— Packy McCormick
Questions Answered in This Episode
How exactly did the Breather strategy memo get adopted—what data, incentives, and internal selling made the turnaround stick?
Acquired profiles Not Boring as a rare “one-person company” that became Substack’s top business newsletter in ~18 months, combining deep strategy research with a playful voice.
Get the full analysis with uListen AI
What are the concrete criteria Packy uses to accept or reject a sponsored deep dive (and how often does he say ‘no’)?
Packy’s path runs from finance to ultra-ops-heavy startup life at Breather, then to writing (via David Perell’s course) and a COVID-era pivot from an in-person club to the Not Boring newsletter.
Get the full analysis with uListen AI
Where is the line between ‘optimism’ and ‘insufficient skepticism’—what would Packy do differently today to avoid being the Theranos-style mark he worries about?
He pioneered a distinctive model: high-quality sponsored deep dives where startups pay to be analyzed—fully disclosed—turning “sponsored content” into a credible, useful product.
Get the full analysis with uListen AI
What’s the measurable impact of a sponsored deep dive (pipeline, hiring, investor interest), and which metrics do sponsors value most?
Not Boring later expanded into Not Boring Capital (AngelList-powered), leveraging audience + content to source deals, while Packy remains a solo operator balancing scale, integrity, and personal bandwidth.
Get the full analysis with uListen AI
How does Not Boring Capital’s lightweight diligence model perform in a downturn—what changes if the market stops rewarding momentum?
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Transcript Preview
Okay, we gotta get you over 100K. This episode is a failure if we don't get you over 100K subscribers.
Right, so let me, let me timestamp where we are right now, just so we know what we need to do. [chuckles] So we are at eighty-eight thousand four hundred and sixty.
Oh, we can so do that.
Oh, we'll juice this. [laughing]
[laughing]
Who got the truth? Is it you, is it you, is it you? Who got the truth now? Is it you, is it you, is it you? Sit me down, say it straight. Another story on the way. Who got the truth?
Welcome to season nine, episode six of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I am the co-founder and managing director of Seattle-based Pioneer Square Labs, and our venture fund, PSL Ventures.
And I'm David Rosenthal, and I am an angel investor based in San Francisco, and I am back, sort of, from paternity leave. [chuckles]
An, a, an abbreviated, partial, ongoing paternity leave.
Yeah, you know, we're, we're making it work, but-
And we are your hosts. [chuckles] Well, today we have a first for Acquired. We are covering a business that is only one person, Not Boring, the newsletter-gone-media-and-investment empire run by Packy McCormick. I did some research last night. Not Boring is the number one Substack newsletter on business. If Packy decided to switch to the technology category, from everything I can tell, he would be number one there, too. In fact, even in the crypto category, there are only two newsletters with more reach, and they've existed much longer. Not Boring is only a year and a half old. The Not Boring story isn't just impressive because of its explosive growth. Packy is reinventing the media business model, and simultaneously, the startup investing business model. He's done all this with a very distinct personal flair, writing in a unique, whimsical voice that makes us all just wanna have fun and play the great online game. And we're very lucky that he is a part of our liquid super team here at Acquired, so he could join us today, live, to help tell the story. Welcome, Packy.
That was amazing. Thank you, Ben and David. Great to be here.
I was doing my best, uh, my best Packy impression, trying to write, you know, whimsically in the unique style you've cultivated.
It was beautiful. [chuckles]
Got some good buzzword bingo in there with Not Boring piece titles over the y- I wanna say years, but it hasn't been years. It feels like years.
I had two-
Feels like you've always been here.
I had two more. I cut them. It, it, it turned into just, like, a long series of Not Boring titles. Anyway, Packy, uh, we do have to let you know, this is not gonna be all softballs. We're gonna, like, actually do the, the full Acquired deep dive here, if that's okay with you.
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