Packy McCormick’s Not Boring parlay: Angel S6 E3 + Producer Rachel visits Miami Hack Week | E1372



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.

about this episode

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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
11:41 Using a parallel fund structure
15:33 How media-first investors can optimize their fund structure
20:50 LinkedIn Jobs – Go to 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
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

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