Angel Investors, Ventri Capitalists, and the Deal Flow

Packy McCormick writes the popular newsletter Not Boring, which is all about strategy and investing, from big companies to small. Packy was the VP of experience at a company called Breather, but when he left that role to start another startup he ended up creating a blockbuster newsletter instead! Not Boring has grown to over 30,000 subscribers.

Packy’s newsletter is generating fantastic revenue, and his business model is a little different from the paid subscriptions that are popular right now. He dives into all the specifics. If you’re curious just how much you can make from a 30,000-subscriber mailing list, don’t miss this episode!

In additional to business models and why he chose his, Packy also talks about the tactics that worked to rapidly grow his newsletter past 30,000 subscribers, the difference between being a writer and being an investor, and more.

Links & Resources

• Prof. Scott Galloway: Overhauling Twitter
• Breather - Unique Meeting Rooms, Hourly Offices & Workspaces
• David Perell - Write of Passage
• Roam Research – A note taking tool for networked thought.
• Benedict Evans
• Clubhouse: Drop-in audio chat

Packy McCormick’s Links

• Not Boring by Packy McCormick
• Home page: packy - Beacons mobile website
• Twitter: @packyM

Episode Transcript

Packy: [00:00:00]
It is about sitting at your computer for hours and hours and hours every week. And making sure that you’re getting it right. And then you’re finding the right angle. Find something that you actually care about if you’re not interested by the things that you’re writing in. So you could probably bake it for a little while, but I think it really comes through when the writer is really interested in the things that they’re writing about.

Nathan: [00:00:25]
In today’s episode, I talked to Packy McCormick who writes a really popular newsletter, Not Boring. Packy was the VP of experience at a company called Breather. And then he left that role to start another startup and then decided to start a newsletter instead. And Not Boring has grown to over 30,000 subscribers.

He’s got some pretty fantastic revenue. He dives into the specifics. So if you’re curious how much you can make off of a 30,000-subscriber mailing list, we talked about that. One of my favorite things is we get into business models. Paid subscription, is that best, or selling products or sponsorships?

And so we dive in Packy shares why he chose the model that he did and why he thinks that’s the best for his audience. So it’s a really fun, wide ranging conversation. I think you’re going to enjoy it. Packy, welcome to the show. 

Packy: [00:01:12]
Great to be here. 

Nathan: [00:01:13]
Thanks for having me. So I want to just dive in and hear a little bit about what are your, some of your favorite things to write about?

Packy: [00:01:19]
Yeah. So my favorite things to write about, and I actually, it took me a while to kind of get back to my favorite things to write about. I was writing about community and sleep and like just kind of all over, just doing the, I think the normal early newsletter thing of like thinking that you’re a fantastic curator of the internet.

And what I really loved writing about recently is as business strategy companies, big companies, small, and mixing that with finance, that’s taken a couple of years, but I think I’ve kind of hit this sweet spot where it’s a more fun approach to these topics that are kind of. Not super fun normally, which is business analysis and finance and the stock market.

So I’m just trying to, you know, make it approachable, fun, and enjoyable while you’re learning something. Yeah. 

Nathan: [00:02:01]
So what’s an example of one of those, of like a business strategy for a particular company that you’ve, you’ve enjoyed. 

Packy: [00:02:06]
So I, this past week I wrote about Twitter, and, and wrote about, you know, how Twitter is this company that has been, you know, that I think a lot of us use and are on all the time, but it’s done.

An absolutely horrendous job of monetizing. So talked about it through the lens of professor Scott Galloway wrote a piece. And so what was wrong with that piece? And then what I thought that Twitter should do and why I think that Twitter is actually undervalued and this idea of like, you know, once things start kind of changing for Twitter, there’s so much love for the company that I think people are just gonna pile into the stock.

A lot of this is about being lucky. I wrote this on Monday, they reported earnings on Tuesday and it’s up like 27% since I wrote about it. So just got super lucky on timing there, but there’s a lot of that like kind of combining how they should think about business strategy and then how that parlays into the market.

So it’s less really quantitative and more like, here’s kind of what everybody’s saying about this company. Here’s what they’re doing. Here’s what maybe they should be doing. And if they do that, here’s what it might look like today. For example, I wrote about, Y angel at early stage valuations are not as crazy as they seem based on the fact that Amazon and Apple and Facebook and all these huge companies have grown actually way faster than the average startup valuation has round by round by round.

And so just kind of walking through that, but then weaving in. The movie up as an analogy and, you know, the four minute mile. And so just try to like, make it super fun and approachable. 

Nathan: [00:03:31]
Yeah. I like that one. And I have to say, I, on Monday, last week, I read your Twitter post, especially as you know, you’re diving into the creator economy and all this stuff that.

It’s just so much fun. and then I was like, this is a compelling case and I’ve owned, you know, Twitter stock for years, but not very much. I bought more, after that article, so you’re already making me money. 

Packy: [00:03:52]
That’s, that’s amazing to hear that scares the hell out of me. So I wrote about Slack a couple of weeks before they, before they got acquired and, had this, like really this, this case of like, I love this company.

They’re just being mistreated by the market, all these things and, and made a, I think a fairly compelling bull case. And then they popped for totally different reasons. Something that I did not write about, but people came out of the woodwork and were like, Oh, thank you so much. I bought Slack because you said to buy Slack and bill.

And I got a little bit scared, frankly, because I was like, I’m not a professional, I’m not a registered advisor. I’m not like. Amazing. If you like, then go do your own due diligence, I love that you’re investing, but it’s scary now that the audience is big enough that people are actually putting money behind the things that I’m writing, which is why.

Nathan: [00:04:33]
Yeah...