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

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 29 January 2022

⏱️ 62 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

Click on a timestamp to play from that location

0:00.0	Welcome to Angel. This is episode three of our sixth season of Angel. And today's guest is
0:05.6	Packie McCormick of Not Boring. That's what it's called. He runs and you already know this,
0:11.0	by the way, because you probably subscribe to his newsletter. It is one of the largest newsletters
0:15.6	in startups. Packie just invested his first 10 million dollar fund over the last six months,
0:21.2	and he is now raising fund too. So we're going to talk about his fund structure, the fact that it
0:26.5	includes some of his most dedicated readers as LPs, how he uses his syndicates, and a lot more
0:33.1	it's fascinating. And then after that, we check in with producer Rachel, who went down to Miami,
0:37.7	yes, in person for half a week and spoke to one of the organizers of Tap House, yes, in person.
0:44.8	Gonna be an amazing episode. Stick with us.
0:49.2	Season six of Angel is brought to you by our crowd. Our crowd helps you invest early
0:56.2	in pre-IPO companies alongside professional VCs. If you're interested in investing,
1:02.5	you can join our crowd for free at OURCROWD.com slash angel.
1:10.3	Linked in jobs. A business is only as strong as its people and every higher matters.
1:16.4	host your first job for free at linkedin.com slash angel.
1:22.1	And the Embroker Startup Insurance Program helps start up secure the most important
1:27.8	types of insurance at a lower cost than with less hassle. Save up to 20% off traditional
1:33.6	insurance today at embroker.com slash twist. While you're there, get an extra 10% off using
1:40.7	offer code twist. Alright everybody, welcome to episode three of the sixth season of Angel.
1:47.1	This is a podcast we started when I wrote my book, Angel. And it's kind of like a sister podcast
1:51.3	of this week and stars week. Candidly post it to two different feeds or see Angel feed if you
1:55.2	want to go look for that and just geek out to those pods and download them all in your player.
1:59.6	Or you just listen to this week and start ups. And we started thinking of seasons
	...

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