By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
AcquiredNot Boring (with Packy McCormick) - Extended Cut
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
At a glance
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 ideasA ‘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 quotesThis 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
High quality AI-generated summary created from speaker-labeled transcript.
