Why Packy McCormick Went All-In on a Newsletter With Only 400 Subscribers

Packy McCormick is the best story in media and venture capital.

While unemployed with a kid on the way, Packy chose to write a free newsletter for 400 subscribers over finding a job with benefits and a salary. Three years later, Packy's newsletter 'Not Boring' is the #1 Business newsletter on Substack with 187,000 subscribers. And his success doesn't end there.

Packy was able to start a venture capital firm, Not Boring Capital, solely based on the audience he generated from his newsletter. Packy started the firm as an angel syndicate to invest in companies with stories to tell, and when he announced his firm was raising its first $8 million venture fund, 900 subscribers showed $50 million in interest.

Less than two years later, Packy's firm is raising its third fund to help tell the stories of early-stage companies in biotech, energy, education, and web3. So far, the firm has invested $40 million across 200 companies.

I sat down with Packy to talk about his biggest decision of the past ten years: going all-in on writing the Not Boring newsletter.

You can read our full conversation below or watch it on our YouTube channel.

Enjoy.

What was the biggest decision you've made in the last ten years?

The biggest decision I made in the last ten years was to go full time on 'Not Boring,' which was a free newsletter I was writing at the time that had 400 subscribers. I did that instead of getting a full time job.

That’s wild. What was the context around the decision?

Yeah, so I quit my job at the end of 2019. I was at a company called Breather for six years, and was riding out my severance. I did some exploration – looked at starting my own thing and considered doing some consulting – as I was basically freed after having a job for six years. But then COVID hit.

So the thing that I was thinking about starting called Not Boring Club – a physical space –was immediately out in the COVID world. Consulting didn't make much sense because my wife had just gotten pregnant with our first kid, and I didn't want to be going out into the COVID world in person consulting with people. So that was also out.

But I had this newsletter that I'd been writing on the side – just to keep my brain going –while I was at Breather. And I was like, well I really like doing this. What if I just give myself three months to do this? 

And that was a big thing–both to convince myself, who's definitely more risk seeking, and my wife, who is more risk averse. Despite COVID, the fact that I had no income, and that we were having our first kid, I decided to give myself three months to see if I could grow this thing.

What was the worst thing that could have happened? And the best thing?

The worst thing that could have happened was us ending up without health insurance. My wife was pregnant at the time and she worked in operations, so her company required her to come in every day. She didn't want to be going in because it was still super early COVID, and we had no idea what it would mean for the baby if she ended up getting COVID. So she wanted to not do that anymore.

And another worst case scenario was that nobody would read this thing. It had grown from zero to 400 people in the past year, so odds were that it was going to grow from 400 to 500 in the next few months. And then we'd be stuck without health insurance with a kid on the way, and I'd be this 33 year old dude in the middle of my career, totally unemployed, with the economy shut down, who has no idea what he could possibly be doing.

The best case scenario that I saw was–and I think I wrote this down in an early post around the time I decided to go full time on the newsletter – maybe I'll be able to at least cover rent with this thing. And by putting my thoughts out in the world, I'll find some job that is the perfect thing or some opportunity that's the perfect thing. So cover the expenses while creating optionality was kind of my best case scenario at the time.

What made you go for it?

The alternatives weren't great either at the time. I was married to the idea of starting my own thing. I'd worked for other people, run the company a little while, and then went back and worked for somebody again all while at Breather. I realized that I really liked being in charge, and I didn't love working for somebody else. I didn't really want to go work for somebody else.

And I really liked writing. My dream always was, when I retire, to write, invest, and talk to smart people all day. And so I was like, well, this could be a shot at at least writing. I had no idea the investing side was going to come as part of this. But, I thought hey, maybe this is a good chance at mini retirement when the world has given us this very weird opportunity.

Was there a moment that you committed to it and you made a decision?

Yeah, I went to the beach with my brother. It was wild –it was during the period of time when you could drive out of New York City when there was no traffic on the road. I remember driving down and I remember shaving my head. We talked about what I might do to grow this thing.

By the end of the weekend, I was kind of convinced I could do it. I asked my wife if I could do this, and she said yeah, sure. I think it was just having the confidence that yeah, there are enough things that I could try to keep busy for three months.

The other big point was – I changed the name of it from Per My Last Email to Not Boring. I went from doing a link roundup with the occasional essay to writing an essay every week that combined some topic from economics or strategy with something from pop culture.

Once I shifted the content of the newsletter, it just started growing and people liked it. And even my most cynical friends were giving me really good feedback. So there were enough signals, even though I wasn't making money and had no clear path to making money, that it was something that was worth continuing to pursue.

So it sounds like you made a few choices to help mitigate the risk?

Probably to make myself feel better, but certainly the idea of writing every week and being consistent about that. I couldn't just say, I'm going to write a full-time newsletter on the side. I said, if I'm going to do this, I'm going to treat it like a job, and I'm going to spend as much time on this as I would spend on a job. That made it feel a little bit more real.

Looking back, how did it turn out?

Turned out better than the best case scenario. I mean, I'm doing what I would have wanted to do in retirement. I get to write this newsletter. We have 155,000 subscribers now (in Sep '22). The business side of it is doing well, and a nice offshoot of it is that I've been able to meet and invest in a lot of companies, like Almanac, through writing the newsletter.

That has been this really pleasant surprise–lots of founders and other investors ended up reading this thing. I was at a failed startup myself a few years ago. It's just very cool that it's opened up this world to me that I didn't even think was an option.

If you could go back and talk to yourself when you were at that beach in Long Island, what advice would you give yourself?

I actually think I handled it pretty well. I'm dumb, and I don't say this in a self deprecating way, but I just don't plan particularly well. I see the upside way better than I see the downside. I don't get nervous about things like that, so I wasn't particularly nervous at the time. It was more about convincing other people that I hadn't completely lost my mind wanting to go do this.

I guess I'd go back and tell myself it'll all work out, but I actually even think saying that–like the butterfly effect–might have changed things if I were a little bit more comfortable and not working as hard in the beginning. So I probably would just not say anything to myself.