Not Boring's Packy McCormick: Content Excellence to Venture Success

Hey, good to be here, Grace.

This should be the one that you're least nervous for.

Zero worries. And everybody could use smoother fund operations, so...

It's a good place to start. I mean, I guess the primary one, right, was that I was in investment banking, I was about to go to business school, and realized that I kind of wanted to do a startup instead. And so I just kind of quit and interviewed for months, kind of unemployed right after I left investment banking. With Breather, I kind of quit before I had something lined up. I was thinking about starting a company, and then COVID hit, but had a bunch of time to just kind of write. And you know, really that was COVID — we were stuck inside, I had plenty of time to write. And so in both cases, kind of looking back, burn the boats and just kind of go for it. Luckily I had some savings and all of that, but not a ton. And we were pregnant with our first kid when I started Not Boring and all of that. So, burn the boats and just give yourself no choice but to go do something is maybe one piece of risky advice.

For the rest of it, you know, I haven't done a ton on thinking about growth and growth hacking things. It's really just been focus on writing the things that I'm most interested in, and focus on writing as well as I possibly can about those things. And so for me, particularly with creation becoming so much easier, the focus on quality I think matters more and more.

Yeah. The content diet is pretty broad. So, you know, I'm generally just — if you could see my desk right now, I have like a ton of books on my desk that I'm reading a part of, and my Kindle which comes with me everywhere. I'm reading a book on Ibn Saud right now. Try to read fairly widely, and use reading almost just like an idea — my brain is not very structured, and so I just try to dump as much stuff into my brain as I possibly can. And then when I decide on a topic that I'm writing about, then I'll just go super deep. So I'll read relevant books, I'll read everything kind of written, I'll listen to all the different kind of podcasts, I'll talk to smart people. I think that's something that you can just get so much more from, talking to people directly than reading often. And then I'll just sit down and write, and I'll realize that I don't understand a certain thing, and so I'll go to ChatGPT or Claude and ask for explanations, or I'll try to explain something and then throw it back in and see if it makes sense what I've written.

And then I'll just kind of continue to look for sources as I come up with specific questions, because a lot of my pieces are about a company but then also about the industry that that company operates in. And so as I'm trying to explain something about the company, I'll realize that I have a shortcoming in my understanding of a particular way that an industry works. So I wrote about a company called Earth AI a while back that's in mining, and I kind of had to learn about the mining industry to have — one, on the investment side, to invest in them, but then two, on the writing side, to write about them. And so as I'm getting through and kind of being like, well, here's their business equation and here's what they're doing differently, I realized I had to go back and learn more about the business model of the mining industry kind of more broadly. And so it's a lot of that kind of iterative process of like getting the high level, kind of figuring out what I want to say, and then going back and forth to find more specifics as I go.

It's so interesting, right? Like in the first fund, and so I increasingly view the fund and the newsletter as the same thing, and I'm writing about companies that are in the fund kind of more and more often. And you know, that's because they're the companies that I think are going to be the most impactful and biggest and all of that anyway. And so those, I think, fit together really well. But you mentioned Ramp and Scale AI. Both of them were — in the first fund, I didn't have a valuation cap. I would do growth stage stuff as well out of the same small fund. And both of those were very expensive when I invested, and both of those are worth much, much more now than they were at the time that I invested. So I'm probably less, you know, even now that I've focused kind of earlier stage, I'm probably less entry valuation sensitive than a lot of people, just because I think that the biggest companies are going to get so much bigger, and if you find the great ones, they'll continue to compound. And so a lot of my job is like, can I find the companies that I think will be great ones as early as possible, which I think is the venture job generally, but like I'm even more focused on, can I find a small group that I think will be really, really valuable versus constructing my portfolio in such a way that, you know, even a mediocre outcome will drive good fund returns. Like that's a different game than I'm playing.

Yeah, so I didn't think about the flywheel originally. I was just writing, no plan to raise a fund, didn't even think that was within the realm of possibility. Then some companies started reaching out, wanting me to write about them, offering for me to be able to invest. The first fund was like almost accidental, and so to your point, it was very much high net worth individuals that were the LPs. And all the, you know, you hear horror stories about fundraising, and I was like, first of all, it was 2021 and 2022, but I was like, wow, this is way nicer than I would have expected, because I write all this stuff on the internet. Either people just like don't think I'll be good at it, and so they don't even take the call, or they already read my stuff, and so there's a lot of background that we have going into the conversation. Certainly now that I'm raising more institutional funds, that's a totally different thing. Some of them will read it sometimes, but plenty of them are like, wait, you write a newsletter? Like what the hell are you doing running a venture fund? A question I get often is how you split your time between the venture fund and the newsletter. And to me, they're very much the same thing, and so I don't even know really how to answer that question.

But the way that I think about the flywheel now — I think some people do explicitly use their content on the LP side, and I think I'm jealous of those people. They do a really good job. Like Harry Stebbings, I think, does a very good job of bringing LPs into the universe and building those relationships. And some others do as well. But for me, you know, I think about the flywheel in terms of, can I find and write about and add value to the very best companies that I possibly can, and earn the right to invest in those companies because of it? And then the LP side is almost, to me, an output of that flywheel, because if I'm able to get into and invest in companies that end up doing really well, that's what LPs are ultimately looking for.

So, I've always taken the newsletter very seriously, and then I've always experimented on the podcast side. So I had something, Not Boring Founders, for a while, and that was interviewing just a bunch of founders, and some of them were in the portfolio, some of them weren't. Certainly part of the reason for that was we have a bunch of portfolio founders, and I don't have time to write a deep dive on every company. And so this is a way to kind of get them out there. Right now I started doing something again, which is kind of more portfolio companies, but will be broader than that, where I'm just doing follow-ups on the deep dives that I wrote, kind of with a shorter deep dive and a podcast conversation with the founder to say like, what did we get right and what did we get wrong when I wrote this thing? And it's been interesting. I'm working on my second one now. The first one I did on a company called Primer, and Primer's doing really, really well, but their model is like completely different than when I — like there were hints of what they were going to do when I first wrote about it, but they've gone from kind of pure software for education to actually building their own micro schools and like really freaking vertically integrating. And that's, you know, the vertical integration thing is a big part of my thesis. So I was like, look, not only is this company great, but they're also doing the thing that I say companies should do.

And now I'm writing the second one, and it's like the exact opposite. They went from being very vertically integrated to actually going more asset light. And now I have to kind of eat crow on that one, where the last piece was really like — and they're also doing really, really well, but the last piece was really like, look how vertically integrated this is, amazing. And now it's like, actually, all of that piece of it didn't matter as much as I thought. So it's a fun way to keep myself honest, to kind of go back and see what I was thinking then, see what's happening at the company now. And I think what you realize doing this, you know, talking to founders over time, whether they're portfolio or not, is that it's true what people say — even like, you know, not at the pre-seed stage — that the end vision is probably going to be there most of the time, but how people get there ends up changing an awful lot. And so like you really do... maybe one of the biggest realizations from this whole thing is I think of it as like the midwit curve, where in the beginning you're like, I just need to find great founders. And then in the middle you're like, no, no, no, all this other stuff, business model and blah blah blah. And then at the end you realize it all comes down to finding really great founders. And I think that's both cliche and true.

Yeah. It's a good one. I would say on the last part, it's almost about not making the content to sell your product, because that's almost going to come off as — people can tell. And so I would say probably the better thing to do is figure out the root reason why you wanted to build that product in the first place, and why you think that's the most important thing that you can be doing with your time, and then create content around that. So there's this really big problem, or the solution, or this opportunity that you see, or this market that's broken or something like that, and that is what got you into this thing in the first place. And so I'd focus the content on that. At the same time, it's really — we talked about this on the Out of Office panel where we met. It is hard to stand out. Like, you know, sometimes the best thing to do is like, you're building a SaaS for a particular vertical, like don't try to build a big content engine, and like get out and do the on-the-ground kind of sales work. I think figure out what's right for you. If you think you have something really interesting to say, it can be a huge lever and something that kind of just gives you a lot more reach for the same amount of time. But it's also like, if you're just creating content in order to sell, I think it's tough.

Yeah. I think getting any algo to pick up on you every time is almost impossible. I do think though that, you know, if you're in an industry that is absolutely fascinating to you, that you think people don't understand, but you have a really good perspective on, I think you can do a lot of different content consistently around that. Otherwise, a lot of the stuff I end up reading is the best piece that somebody could possibly write, and it's like their one-time thing. We have a company in our portfolio where the founder wrote a piece on why drugs are so expensive. And he doesn't write a lot, and he wrote this one piece that was so big that it got him on Invest Like the Best with Patrick O'Shaughnessy. Apparently it filled their pipeline for months with potential customers, and it was just one really, really, really good piece. So I think that that can work really well too, if you're known as just like — you just, you know, precision hit, nailed it, one-of-one kind of piece. If you put all of the interesting stuff you have to say in one kind of magnum opus, I think that can be a calling card as well.

I don't know how many he had. Certainly not a very large following. Like I don't know if they have — certainly more than 20, but not a very big following. I'm sure... and like this happens a few times. I interviewed somebody called Parakeet, who's pseudonymous, on Hyper Leisure, which is the podcast we've been doing. And her piece, the people that were sharing it were just not people that I would ever expect to be reading her Substack. I didn't read her Substack, but somebody found it and then they shared it, and because of their recommendation, somebody else found it and liked it and shared it, and that just kind of went. I think the most valuable thing that can happen is that like, whether you have a million followers or two, somebody — and it's actually often easier with a smaller following for people to feel like they're discovering something, as opposed to like if I write something, it's like, oh, Packy wrote something again, great. But with a smaller following, finding people who are like, holy crap, this is really, really good, look what I just discovered — I think can do an awful lot for you.

Amazing.

When I said that I didn't focus on growth, like I don't think about any of this type of stuff. And I didn't in the beginning, I don't think about it now. Like I viewed it as, what is the thing that I think is most interesting? There was a little bit of it less from the audience perspective, but more like the David Perell personal monopoly, where it's like the intersection of these different things, and I did pop culture and tech and business together. And so I wanted that to be a thing, but it was more like, is the product new and good, versus like I'm writing to John in Indiana who, you know, is a 23-year-old aspiring software engineer. For me it was more just focus on the product itself and see who likes it. Because I wasn't, you know, in the beginning I wasn't planning on making this my full-time thing forever. So it's not like I approached it like a business. It was just kind of like, I'm writing the things that I'm interested in.

About what?

Yeah.

Something about swarms. Yeah.