Today’s guest is Packy McCormick of Not Boring, for Episode 3 of Season 6 of Angel. Packy turned his massive newsletter into a Not Boring Fund I in 2021, and has since invested $10M into startups. In this episode you will learn:

1. How Packy raised his first fund from his readers.

2. What regulations he needed to navigate to comply with the SEC.

3. Which sectors he invested his first $10M into (in just 6 months) and some of his breakout startups.

4. Why IRR can be hilariously large in the early stages of a small fund.

5. How he manages a syndicate and a venture fund while still doing right by LPs.

As Packy signs off we check in with Producer Rachel who went down to Miami Hack Week and spoke to one of the organizers of Tap House for an "OK Boomer" segment.

(00:00) Molly introduces the show
(01:43) Jason and Molly chat with Packy McCormick
(04:40) Packy's editorial philosophy
(08:06) How Packy used the 506c designation
(10:38) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/angel
(11:41) Using a parallel fund structure
(15:33) How media-first investors can optimize their fund structure
(20:50) LinkedIn Jobs - Go to https://linkedin.com/angel and post your first job for free.
(21:57) Not Boring Fund II goals
(24:42) How responsibilities change as check size increases
(27:45) Managing Venture LPs and a Syndicate simultaneously
(29:08) Embroker - Get an extra 10% off insurance for your business at https://Embroker.com/twist
(30:25) Does it matter what time you enter the market as a VC?
(37:04) IRR (internal rate of return) versus and multiple on cash
(46:25) Packy's weekly cadence for investing and writing
(51:39) OK Boomer - Rachel Reporting from Miami Hack Week

Check out Not Boring: https://www.notboring.co

FOLLOW Packy: https://twitter.com/packym

FOLLOW Rachel: https://twitter.com/_@rachelbraun

FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood