Not Boring (with Packy McCormick) - Extended Cut

When does a creator become a company? Who says that media companies — or venture firms — have to be organizations? How high is the ceiling on one person + the internet? Acquired has the answers and they are... Not Boring. 🙂 Big news!! All back catalog LP Show episodes are now free and available to anyone!! You can follow our new public LP Show feed in the podcast player of your choice. It's already chock-full of 60+ great episodes like our VC Fundamentals series, interviews with founders of top early-stage startups, and master classes on pricing, marketplaces, SaaS investing and many more topics. Happy listening and happy holidays to everyone!! http://pod.link/acquiredlp Sponsors: - Thank you to our presenting sponsor for all of Season 9, Pilot.com! Pilot takes care of startups' bookkeeping, tax and CFO services so busy founders can focus on what matters. To paraphrase Jeff Bezos's AWS analogy: bookkeeping and tax don't make your product any better — so you should let Pilot handle them for you. Pilot is in fact backed by Bezos himself, along with other all-star investors including Sequoia, Index, and Stripe. They are truly the gold standard for startup bookkeeping, and many of the companies we work with run on them. You can get in touch with Pilot here: https://bit.ly/acquiredfmpilot , and Acquired listeners get 20% off their first 6 months! (use the link above) - Thank you as well to PitchBook and to Nord Security. You can learn more about them at: - https://bit.ly/acquiredpitchbook - https://bit.ly/acquirednord Links: - Not Boring: https://www.notboring.co/ - Proto-Not Boring: https://www.packym.com/blog/nyc-debate-club - Not Boring's first sponsor deck: https://projector.com/story/2cb6296d-e229-4774-839c-efbf86d7f69f?scene=7127c7a0 - Jake Singer's Not Boring Flywheel: https://theflywheel.substack.com/p/not-boring-packy-m - Proof Ben was famous even before Acquired: https://web.archive.org/web/20150814041757/https://www.seattletimes.com/business/high-octane-leader-drives-microsoftrsquos-innovation-garage/ Carve Outs: - Velcro swaddles (dad life...): https://www.amazon.com/s?k=velcro+swaddle - An Engineer's Hype-Free Observations on Web3: https://www.psl.com/feed-posts/web3-engineer-take - Rabbits: https://www.amazon.com/Rabbits-Novel-Terry-Miles-ebook/dp/B08HY29VM2 *Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

David RosenthalhostPacky McCormickguestBen Gilberthost

Dec 2, 20213h 5mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

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.

IDEAS WORTH REMEMBERING

5 ideas

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.

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.

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%.

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.

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.

WORDS WORTH SAVING

5 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

Origins: childhood writing + humor + researchBreather: operational grind, strategy turnaroundNot Boring Club failure and COVID pivotNewsletter growth mechanics and voiceSponsored deep dives as a new ad productWeb3/crypto pivot and translation roleNot Boring Capital and AngelList as ‘AWS for VC’

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