Not Boring (with Packy McCormick)
Acquired
Ben Gilbert and David Rosenthal
4.7 • 5.2K Ratings
🗓️ 3 December 2021
⏱️ 166 minutes
🧾️ Download transcript
Summary
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. 🙂
Sponsors:
- Anthropic: https://bit.ly/acquiredclaude25
- Sentry: https://bit.ly/acquiredsentry
- WorkOS: https://acquired.fm/unplugged
- Playing Cards: https://bit.ly/workOSshop (Code: ACQDECK)
- Statsig: https://bit.ly/acquiredstatsig26
More Acquired!
- Get email updates with hints on next episode and follow-ups from recent episodes
- Join the Slack
- Subscribe to ACQ2
- Merch Store!
© Copyright 2015-2026 ACQ, LLC
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.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Okay, we got to get you over a hundred K. This episode is a failure if we don't get you over a hundred K subscribers |
| 0:05.2 | All right, so let me time stamp where we are right now just so we know we need to do |
| 0:10.1 | So we are at 88,460. Oh, we can so do that. Oh, we'll juice this |
| 0:30.4 | Straight another story on the way |
| 0:35.4 | Welcome to season nine episode six of acquired the podcast about great technology companies and the stories and playbooks behind them |
| 0:43.2 | I'm Ben Gilbert and I am the co-founder and managing director of Seattle based pioneer square labs and our venture fund |
| 0:48.8 | PSL ventures and I'm David Rosenthal and I am an angel investor based in San Francisco and I am |
| 0:56.6 | Back sort of from paternity leave |
| 1:00.0 | an abbreviated partial ongoing paternity leave. Yeah, we're making it work and we are your hosts |
| 1:06.4 | Well, today we have a first for acquired. We are covering a business that is only one person |
| 1:11.8 | Not boring the newsletter gone media and investment empire run by packy McCormick |
| 1:18.0 | I did some research last night |
| 1:19.7 | Not boring is the number one sub stack newsletter on business |
| 1:23.7 | If packy decided to switch to the technology category from everything |
| 1:27.6 | I can tell he would be number one there too in fact even in the crypto category |
| 1:32.4 | There are only two newsletters with more reach and they've existed much longer |
| 1:37.1 | Not boring is only a year and a half old |
| 1:40.5 | The not boring story isn't just impressive because of its explosive growth |
| 1:44.8 | packy is reinventing the media business model and simultaneously the startup investing business model |
| 1:51.0 | He's done all this with a very distinct personal flair writing in a unique whimsical voice that |
| 1:57.6 | Makes us all just want to have fun and play the great online game |
| 2:01.3 | And we're very lucky that he is a part of our liquid super team here at acquired |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Ben Gilbert and David Rosenthal, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Ben Gilbert and David Rosenthal and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

