Packy McCormick - Making Newsletters Fun (Podcast)

[01:35] Paul: Today I'm talking with Packy McCormick, who is the creator of the Not Boring newsletter. I will dive into some of his story, which is him leaving his job in 2019 and planning to start an in-person community, including buying a clubhouse. Luckily, he didn't take too much action on that before the pandemic hit, and he decided to shift his to writing, and he's built a pretty impressive following writing about startups and businesses and strategy and having a ton of fun with it. I think that's what really resonates with me, and it's exciting to see somebody doing something they're enjoying. We'll also talk about a piece he wrote last week on the future of work and why he thinks the employee will decide the future. So today I'm talking with Packy McCormick, who is a a solopreneur, I would say, and left his job last year, uh, to start an in-person community company.

So not pandemic-friendly, but we're going to dive into that shift, uh, what he's working on now, and we're going to dive into a piece I resonated with that you wrote last week about the future of work. Uh, so welcome to Reimagine Work, Packy.

[02:56] Packy McCormick: Good to be here. I'm a huge fan of your writing as well and you're living this, so I'm excited to talk about it.

[03:02] Paul: I stumbled across your writing early, I think mid-2019, after you started publishing online. And I think the thing that jumped out at me is you seem to be having fun with it. I find a lot of people aren't. They either feel like they have to do writing online or they're trying to like surface things that they want to be excited about, but like yours just jumps out from the pack early, and I think you're still doing it, which is awesome. Where does that come from?

[03:32] Packy McCormick: Yes, I mean, I had no, you know, no reason to write really other than I was at a company called Breather for 6 years, so it's a long time, and wanted to kind of like, you know, start using my brain in a different way. And so took this writing course, and, you know, it wasn't a mandatory thing, it wasn't homework. I love reading obviously on my own. I didn't love reading when it was homework, work, et cetera. I think that's a common theme. But this was just a fun thing that I got to do on the side and a good way to kind of explore things that I was interested in and kind of organize my thoughts on paper.

And I do think that some essays I'd wrote in the beginning were fun and I had fun with, and some were, like, I think me trying to sound smarter than I actually am or put on airs or find a topic that maybe I could try to become— you know, all the stuff that I think people do when they start writing. And I think I got to a certain point, particularly over the past, call it 8 months since I've started writing full-time, where, you know, like my only differentiation really, if I'm writing about business strategy and finance, is that I'm gonna be having more fun than people and I'm gonna be taking it less seriously. Like I'm not smarter than Ben Thompson. There's plenty of people who have spent the past, you know, multiple decades in finance who are better there.

But I think if you can kind of infuse the fun and approachability to the topics and explore the things that I'm passionate about, then hopefully that comes through.

[04:51] Paul: Well, there's a certain aspect too of writing in which you step into that unknown and you force yourself to level up and get smarter. I think for me, what I realize when I write is, "Oh crap, I don't actually know anything about this topic. Now I'm going to spend 5 to 10 hours actually going deep on that." And that's also one of the challenges of writing too.

[05:13] Packy McCormick: It's challenge and opportunity there. I've always been obsessed with, and I think that we can talk about the in-person community, but continued learning and why learning has to stay and why you have to kind of find one track where you're in a job and then you learn more and more and more and more specific things within that job or that industry. And I hated that. And so I think for me, like learning writing is every week, I get to write about something that like very often I'm a noob on and I have to be able to like, you know, within the course of 3 or 4 days, by the time I hit send on Monday, have to be able to write at a level that's both like, I understand it well enough to explain to people who've never heard about it, and also not embarrass myself to people who are in the industry. And so like, it just forces you to go deep and kind of learn and figure out what people are saying.

[06:00] Paul: Yeah, how do you handle that? I think I've been a bit afraid of growing too fast with my newsletter. I've been writing pretty consistently in it in 2 years, and as the numbers get bigger, I get a little more nervous. I write about things that I am not fully an expert in. And I try to push, do that to push myself and grow and stay curious and stay energized. But at the same time, you could, you have this sense that, oh, do I really know what I'm saying?

Like, it must be pretty scary. I think yours has grown pretty fast over the last 6 months. How do you deal with that?

[06:37] Packy McCormick: To me, honestly, it was scarier at 20 people, you know, scary at 20 people, scary at 100 people. Doing the first few posts where I was like, guys, like, take, take a couple of hours, you know, take, take half an hour and read what I have to say on this topic. And, you know, then it was scarier because I knew each one of the faces of the people who were reading the newsletter. Whereas now I think, you know, like, the, the audience is bigger, and it's just been enough weeks of forcing myself to get over the fear and hit send that it's just become kind of, you know, a habit a little bit, and something that's less scary. Every week still, I'm scared that like I'm exploring a new industry and people who are actually in the industry are going to be like, this is either, you know, an amateur hour or wrong or, you know, totally missing the main point or whatever.

But I think just doing it enough times and realizing that even when it's not perfect, nobody really cares has been, has been helpful for me.

[07:32] Paul: I think people see you doing it in good faith too. And the thing a lot of people don't see when you publish and create online is 98% of the feedback I get back is like, wow, this was so cool. This made me think. It's the emails you receive on the other side that aren't as legible to people that don't create online. That's really the feedback cycle that kept me going. And I definitely resonate with it being a lot weirder to send to 100 people and crickets, right?

It's like, oh shit.

[08:02] Packy McCormick: Totally. Yeah, it's like, what am I doing here? So yeah, I mean, I think that's, that's definitely a part of it. I think because I've been public about growing it and the process and whatever, from the time that I started writing it, it builds, it's building fast, but it builds slowly enough that like everyone can still see that I'm like that idiot who was just trying to figure something out 8 months ago. And so like, there's no expectations that this is going to be a perfect thing, uh, because I think it's just been like such an open process the whole time.

[08:34] Paul: Last February, I was looking back at my emails. I exchanged a few emails with you. This was early February, and this looks so ridiculous now. You were outlining your plans to build an in-person community by a clubhouse. This is like February 14th.

[08:51] Packy McCormick: Yep.

[08:53] Paul: Not a great year for in-person community. So how did— how was like February and March for you? That must have been pretty wild time.

[09:03] Packy McCormick: Yeah, so I, I guess, rewind a little bit. Uh, you know, for the past kind of— for most of 2019, I knew that I wanted to leave Breather. I knew that I wanted to start my own thing. I was trying to figure out what that was, and I really used a lot of like the writing to explore what that was. And I wrote a 4-part series on, uh, in-person communities and clubs and like this kind of burgeoning SoHo for— SoHo House for X movement that was happening. And, you know, it kind of resonated with this thing that I've always wanted, which is this kind of like continued college atmosphere.

And so what I tried to build was a combination of, you know, Soho House and college extracurriculars. So I was doing a debate club on the side, or we had drinks, like drinks and philosophy papers, or like just like different, like kind of nerdy small group things. And it was a really, really fun idea, and I loved like kind of nerding out on it. But I also think that I like talked myself into it being a good business. And so I think you can tell when there is like that natural kind of like pull and when you have to push it. And it really felt like, you know, I launched the community, thankfully launched the community first before going out and raising money or signing a lease on a space.

And that was not how I had been thinking about it, but I talked to enough community people who said, please like start building the community first. And I'd done all of that, and it felt like, you know, particularly after COVID hit, I tried to bring it online a little bit. And I know you, like, you helped out with an event. And I realized that because what I was trying to build was so broad in terms of the type of people and wasn't very niche, it's like the exact wrong thing that you want to build online. I still think you maybe could have pulled it off in person, but online it's just not the way to build a community by going super, super broad.

Um, and so when COVID— when it became clear that like COVID wasn't going away anytime soon, and that I didn't want to become an online community manager, it actually was a bit of a relief where I was like, you know, I would have been bullheaded about this. I told enough people, I had written publicly about the fact that I was doing this, that I would have just like banged my head against the wall, you know, tried to find little reasons to convince myself that I was doing it right. But frankly, looking back on it, wasn't a great idea. I think it'd be a really fun thing to do now with an audience as a side thing, or in the future if I'm able to make, you know, enough money off of Not Boring the newsletter and all the surrounding things there. But as a startup, I think it would have been a ton of effort for pretty low payoff.

[11:28] Paul: Yeah, that's— it's kind of interesting how the pandemic merged with the idea you're dealing with too, because you were able to test out a lot of things virtually. And I think a lot of the thinking around community now is kind of, okay, test it and try to build it online and then go offline, which is probably going to be pretty exciting for many types of communities post-COVID in terms of how people are experimenting in new ways of living. I mean, this is essentially how I travel, is connect with people online and find places to live and then go there. And you wrote a pretty detailed piece, Senius. How do you, how do you say that?

[12:17] Packy McCormick: That's right, seniors.

[12:18] Paul: Seniors. Um, about this idea of all these communities converging, uh, in different parts of history, and you say you're pretty passionate about community building and happiness. So how are you thinking about that thread?

[12:35] Packy McCormick: Community is super important. I think when I started this journey, I didn't have an online community necessarily. Like, I had my friends, I had my family, I had all this, And I wasn't very deep in Twitter. Twitter actually really kind of scratches a lot of the itch for me in terms of having this community of people that, you know, some you have really, really light interactions with, some you're constantly engaging with. I'm sure that's how you found a lot of people that you kind of meet up with when you travel. And so I think part of it was just like kind of not realizing the power of the community that I like already had the software for.

And now, you know, by putting— by broadcasting, you're able to just attract a bunch of people who also, you know, are interested in the same things. And so I think Twitter has filled that, that void for me in a pretty big, uh, pretty big way. I think like the really interesting question around seniors, like if this trend continues and if people do stay remote and connect online and better and better tools are built, kind of my entry point into that exploration was the question of like, great, we're all online now. All of these senior, like, you know, the Renaissance or the Scottish Enlightenment or whatever, were these like very geographical things where For whatever reason, there was this magic that happened in certain times and places where there was an explosion of creativity and new ideas that other people in the future would build off of, and people interacting.

Can you recreate that magic online? And I think so far, we've seen like early signs that absolutely, I think you can, when everybody's forced online and you take away the geographic constraint and you can find the 5 people in the world who are the most interested in that particular thing that you're interested with. And all like kind of the tangential pieces around it that make a scene kind of magical. But I think it'll be really interesting to see over time, like how that sustains and how you can kind of, once you're allowed to go back to the real world and sometimes go to the office and whatever, like if that kind of takes some of the energy back away from the internet or if the internet kind of takes over from there. So I think nobody knows and we'll see what what that ends up looking like.

But I think for this, like, kind of year in time, it's been like the internet has been just this, like, magical community kind of almost in and of itself.

[14:46] Paul: Yeah, it's been pretty amazing. I think, I mean, even someone like you— you, me and you lived in New York. I lived there from 2015 to 2017. We never met. We probably should have met, right?

[14:58] Packy McCormick: Yeah, um, totally.

[15:01] Paul: But And now it's so easy to find other people. I didn't know I needed people that like— like the kind of people I want to connect with are essentially people that think it makes sense to spend 40 hours diving deep into a topic and then writing about it.

[15:21] Packy McCormick: Yeah.

[15:22] Paul: Which when I think about the overlap with my friends in real life, it's not very many people. So it's really been a nice place to meet these basically uber nerds who want to go super deep on different topics.

[15:39] Packy McCormick: Twitter has, what, 300 million monthly active users or something like that? And your friend group, if you're super, super popular and define it loosely, is like 100 people. So the odds of you finding those people are just so much higher in that space. And so I think it'll be really interesting, again, to see how digital and physical continue to to blur, because I do still think there's a ton of magic in the in-person interactions. But to your point earlier, finding like— using the internet as the top of funnel and then in person is kind of bottom of funnel is a really interesting way of thinking about it.

[16:12] Paul: So let's talk about the newsletter and then dive into some of the future of work. So you're writing a different newsletter than you were, uh, 6 months ago. You were writing to— your first thing was kind of per my last email, it was more of like life updates, and now you're going like super deep Deep across a wide range of topics to probably, I don't know, 20 times the audience you were 6 months ago.

[16:39] Packy McCormick: 40 or 50 at this point. Yeah, it's crazy.

[16:42] Paul: Talk to me about that transition and how you've kind of thought of yourself as what you're working on and your path and how you define as a writer and thinking about all of that.

[16:54] Packy McCormick: I think I'll start with the second question first in terms of like how I think about it and The fun of this is that I'm not really, um, and I'm really just like every week, so kind of like up to my eyeballs and trying to figure out a new topic and just get something that I feel happy with out the door, that there actually has not been nearly as much kind of long-term thinking or planning as I've ever done. It's less than I've ever done in my entire life. Um, but kind of rewinding. So yeah, when the club shut down, I realized I had this newsletter on the side You know, this per my last email that had about 500 people. I was sending links and listens and maybe sometimes would write a deeper essay. And then I had more time during a pandemic when I realized, like, look, I'm probably shutting this thing down.

And at the very least, if I'm not shutting this thing down, it will certainly benefit from having a wider audience on the newsletter. So let me just focus on the newsletter. And around that time is when I realized, like, you know, the thing that I really love digging into is tech, business strategy, finance, like these things that I thought were way too well covered. And so I spent the first year of writing trying to avoid them and find a unique angle. But I think like it's super, super important if I'm going to be writing, you know, 60 hours a week to find things that I'm actually super passionate about. Writing does attract a bunch of people to you, right?

Like just putting your thoughts out there, writing videos, podcasts, whatever. Attract people to you who are interested in the things that you're writing about. And so like, you wanna— what you write about defines who you're gonna be spending a lot of time interacting with and talking to. So like, it better be something that you're really interested in, or those conversations are gonna be painful. Um, and so finally just realized, like, what if I infused pop culture into all of that stuff? And like, you know, talk about the Gartner hype cycle through the lens of the movie She's All That, or, uh, creative destruction through the lens of the Mickey Mouse Club.

And so like, I really like force myself— every one of the essays that I wrote early after I changed the name to Not Boring, to blend kind of some concept in economics or finance or strategy with some very just on-the-nose pop culture thing. And then I think over time, as it's grown and as I realized I was spending half as much time thinking about what movie this topic might make sense for, I've dropped the exact direct pop culture reference, but tried to keep the spirit of what I'm writing about. And so that ends up being these like really, really big fascinating companies or trends on Mondays, and then really small kind of like early stage stuff, uh, either companies that we're investing in. We can talk about the, the syndicate because I think that's a fun kind of community type thing that we're doing. Or, you know, even sponsored posts.

And I think I've been like fairly nakedly commercial and open about the fact that like this is what I'm doing, so I need to make money on this. And so that's given me a lot of freedom, I think, to try new formats that are me making money writing about things that I'm really excited about writing about anyway.

[19:50] Paul: Yeah, how have you thought about that? And it seems like you're really going out there on your own, like getting advertisers, or I don't know if people are reaching out to you, but a lot of people think, okay, how can I actually monetize this? How have you tried to approach that, putting on like a business hat?

[20:08] Packy McCormick: So my plan was grow from, you know, the 500 people that I was at in, in April to hopefully 1,000 by the end of the year. Then I updated it to like 5,000 people by the end of the year. And I was like, when that happens, I'll think about monetization then. And by monetization, like, I drank the Substack Kool-Aid, and I was like, I'm definitely doing paid subscriptions. And so hopefully if 10% of my 5,000-person audience converts at $8, I'll be making $4,000 a month. And at least that covers rent, and then I can have that going on the side, and I can figure out what I want to do with my life.

It grew faster than I expected, and I realized that I loved the growth, not just because like it's fun, but it also, I think, creates more opportunities and more surface area on the writing. And I do spend so many hours that I like to kind of amortize that over a bigger audience. So realized that I didn't want to close that off by going paid. So advertising is kind of the next model there. I had put it out there that I was maybe like to a couple people thinking about doing it. Somebody asked me for my ad deck or my sponsor deck.

I didn't have one. So I did a survey of the audience. Like the results were perfect, kind of like the exact the exact type of people that, you know, a SaaS or finance company would want to target, put together an ad deck to send to this one person who had asked for it. And then I was like, yeah, I already have this thing, like, let me just put it on Twitter. And so I did a Twitter thread, and literally the first 2 months of sponsors all came from that, that thread. And then it's come from either referrals or readers reaching out and asking if they can advertise since then.

[21:38] Paul: And are you doing affiliate fees, or do you pay a set amount per subscriber?

[21:44] Packy McCormick: Yeah, so it's somewhere— I've done both, frankly. Like, so I've done mostly for just like a top-level sponsorship, it's just been, here's my rate for this month based on the number of subscribers. I frankly pulled the first rate out of thin air. Um, you know, I realized that I'm doing something like a little bit different that I think people are used to on the newsletter. Like, I'm doing these in-depth analyses that people really like want to— need to want to like invest time in to get through. And so it's very different than if I had like a 100,000-person audience of people who were like not at all, uh, committed.

So I would lose if I tried to do kind of CPMs. And so I just picked a number and then was like, well, you know, I grew 40% this month, so my rate's 40% higher now. I don't know. And it's worked so far. Um, and then sometimes I'll do CPA. So a couple times I've done company deep dives, uh, on two that I've done CPA on are Main Street, which finds tax credits for companies and then gives them free money.

So like, that was a no-brainer CPA deal because I was like, I don't know who in my audience wouldn't sign up for this. Like, they literally just send you a check of money that the government gives you. Um, and then another one is a company called Pipe, and they can turn your recurring revenue into an upfront payment and you can raise better capital for your business and all that. And so if it like really, really, uh, I think aligns into something that feels like my audience is like absolutely going to go for, and the math works out, I'm happy to take a risk on that. Typically though, you know, just because I have a kid and a wife and like want to make money, typically I just charge a set rate for the sponsorship.

[23:15] Paul: I wanted to ask you about that too. You had a kid during the pandemic. Uh, I think our generation, the millennials, have kind of woken up and been like, oh, maybe it's time to start our lives and buy houses and move out of these cramped apartments and have children. It's pretty amazing how many of my friends have, uh, taken some pretty major life shifts in the last 12 months, but how has that impacted how you're thinking about your work, how you spend your time, just like everything you write about and talk about?

[23:52] Packy McCormick: Yeah, I don't know. It's been like the absolute best thing in the whole world. I know everybody says that, but like, just could not be happier being a dad and getting to spend time with him. Like, certainly way more distracting because, like, after this call, normally I just, like, put on a song and keep writing, and I want to go hang out with him if he's awake. And so, like, my schedule is choppier, and I'm, like, squeezing it in in different places, and my sleep is horrible. And so, like, I need to caffeinate myself more than usual in the morning to get going and all of that.

But it's just, like, absolutely the greatest thing in the world. I think one of the things that it made me realize is that, like, humans have been around for a very, very, very long time. We've lived in small apartments and cities away from our families for a very short, like maybe couple century if you're being generous, window. And, you know, now we're living for a couple months in my in-laws' house, in their basement right now. And you can see, like, it's just so nice to be able to be with and near family. Like, my parents are an hour away.

They come often. We were with them for Thanksgiving. And just being able to kind of, like, raise the kid collectively. It makes it seem like almost barbaric that like, that you would go back to work within a week or that you wouldn't be near your family or any of those things. So I think it's kind of opened my eyes to like why it's like a little bit of like a family unit Lindy effect where like, if that type existed for thousands and thousands and thousands of years, like there's a good reason for it. Um, beyond just like we didn't have the option to move to cities before.

So I don't know, that's like a broader thing, but generally it's, it's been about finding like ways to squeeze it in, but totally, totally worth it.

[25:31] Paul: Yeah. And that, I mean, that connects to the future of work. And I've, I've written a lot about this. People don't realize how much this has shifted. Essentially, we have a bifurcated economy where we've increased low-wage jobs and increased high-wage jobs. The high-wage jobs are awesome.

And there's actually been more people making more money than ever before. And the downside of that is it's basically required people to move to high-cost cities. And for the first time ever, those people are moving to high-cost cities and not leaving. And we'll see what the pandemic does to that shift. But essentially, that's broken the connection. To family and starting families and buying houses and this traditional, um, narrative that's existed.

[26:24] Packy McCormick: Totally. Um, and by the way, like, I love cities and I think, you know, in a few months we're probably moving back to New York, but we're doing it kind of with the choice of, you know, do we live in New York or somewhere else? And do I have to get on the subway 5 days a week, twice a day, and do that whole thing? Like, not gonna do that again. So it's That's an interesting thing that even with choice, you might make the same choice again, but just having that choice is a really nice thing.

[26:49] Paul: Yeah, and that was part of your hypothesis with the future of work piece you wrote. You said people will move more often, and one of the ways you saw that was through companies like Nextdoor, which lower the transaction costs and friction to moving and selling a house, right? I think remote work, I've seen a lot of people with full-time jobs experiment with living in different places. How do you see that playing out?

[27:16] Packy McCormick: Yeah, I mean, I think that's going to be a massive one. There's like the anecdotal stuff about everybody and their brother moving to Austin or moving to different places in the country. There's that idea that I think everybody has wanted to live on a commune with their friends forever, and it's just never been feasible before. So I would imagine like you'll start to see things like that happen more often. A lot is going to stay the same. People have friend networks in cities, and they have, you know, they've chosen cities because maybe it's close to their family.

Like We'd love to try out Austin, but both of our families are on the East Coast, so we're going to stay on the East Coast. So there's going to be plenty that stays very much the same. But I think the big kind of, I think, thesis of the piece that I wrote was that one, employees will just have more choice now. And so employers think the decision to go back to work or not is up to them. And maybe in the very, very, very short term it is, although I think people will drop off the day that that happens. And I've talked to plenty of friends for whom that's the case.

But I think over time, like, it just makes the labor market more of an actual market than it has been in the past. And, you know, the best— I wrote something that like some people maybe thought was like a little bit too much, which is the best employees will never want to go back to a 5-day work week in an office again. And I think that's true in a lot of cases, but it's more that like a company is never going to be able to attract all of the top employees again if they're 5 days a week in an office. And so like that talent density over time will just like kind of slowly and slowly and slowly decrease. So it, it's incumbent upon companies to really figure out how to get good at remote work because I think as we talked about the first time we talked on a Zoom call, you know, in the beginning of the pandemic, like you can do remote work really shitty.

Like right now the way that a lot of people do remote work isn't good, but I think the companies that are able to figure out how to do it well and how to mix the in-person stuff and the remote stuff, like, those companies are going to be at such a massive advantage because they're going to be able to pull talent from anywhere, and they'll be able to attract people with the, you know, the offer of flexibility with some structure that people do crave still.

[29:21] Paul: Yeah, I was calling this the basically free strategic option, uh, that companies were taking in April. I, I was basically saying that I thought it was a no-brainer in like April or May to go fully remote indefinitely, because if you're looking at strategy, strategy is basically probability. And I was looking at, you can have a certain outcome of going fully remote, or you can have an uncertain outcome of not knowing what the future looks like and muddling through. Um, now the certain outcome of shifting to remote may actually be costly and you may be able to quantify that, but it's actually going to set you up for future competitiveness in all these things.

[30:08] Packy McCormick: Totally. And it doesn't mean that you can't go back to the office, right? Like, it means that you're telling your employees that they can work remotely forever if they'd like to. And you can also change that at some point in the future. But I think it's like, you know, I wrote about the fact that Stripe, you know, they didn't say everyone's remote for the— till the end of time. They said We have 5 hubs that are of equal importance to each other, one of which is remote, and it's just like kind of signals a dedication to making that experience on par or better than, you know, or at least kind of different, uh, and equal to the in-person experience.

[30:43] Paul: Yeah, I think you're generally right about, um, talented employees. Uh, I've seen this trickling out over the past few years. The kind of people that normally, maybe 10, 15 years ago, would be climbing the ladder and staying within a company are opting out in increasing rates. And I've seen this go earlier and earlier. I've talked to a lot of Gen Z people who are like not even taking that first entry-level job. Me and you both started in consulting and investment banking.

And we did, you did 10 years. I think I did 10 years in the corporate world and bounced out. People are bouncing out now in 5 years, people are bouncing out in 2 years. Uh, and these are people who would traditionally be very successful in organizations. And I feel this on my end too. Like companies try to hire me and I'm just not interested.

There's really good, I could make a lot more money through freelancing, but Last year they were trying to hire me 5 days on site for 3 months. Not interested.

[31:52] Packy McCormick: I can't imagine going back to a job where I have to, one, work for somebody, and two, go to an office every day. Like, it just seems like once you've had a taste of the other side, it seems like a crazy, just like constriction of optionality. That, that, that's been the biggest thing because I've talked to companies during this process about maybe joining full-time, and each time, like Man, I have all of this optionality and then it just goes like this. So I think we probably will also see these like more liquid implement options that are somewhere between being a full-time employee that feel a little more permanent, but they're not like totally optionality limiting. But yeah, to me, I can't, like, it just seems like infinite upside kind of just constricted by going in-house somewhere.

[32:42] Paul: And do you have explicit conversations with your wife about, okay, I'm actually willing to give up, uh, I'm actually willing to dramatically lower my cost of living or the amount I could potentially make for this freedom. Do you guys talk about that? Because I talk about this a lot with my wife in terms of like what actually makes our life awesome and how do we keep some of this freedom that we really love?

[33:07] Packy McCormick: 100%. I mean, she's been— I can't— I'm so incredibly lucky that she's been down with this whole thing, right? Like, from wanting to start the company to then being like, ah, you know what, I'm not gonna do the company, I'm gonna write this free newsletter, then to like having months of building it and like there are clear signs of progress, but that ultimately resulted in $0. And so she's been amazing there. And I think like the, the goal was I was always like, look, this is a math problem. Like, you get to a certain size and then you can monetize in a certain way.

So like, please just trust me here. But I'm finding now that I don't think I'm going to have to give up— it was a year to get here of like no money, but I don't think I'm going to have to really make a sacrifice in terms of the income level. It'll be less predictable and all of that, and I'm going to be a terrible candidate to like go out and get a mortgage somewhere. But otherwise, I mean, I think like the upside potential is actually even better here. So she's been really comfortable with the risk, understanding that like the payoff could be greater too. And like most importantly, if she has to go back to the office or go back to work, like I'll be here to get to hang out with our son all the time.

So, you know, it's a really nice kind of set of trade-offs.

[34:21] Paul: I've kind of taken the route to work less and purposefully keep my income lower, but it also gives me space to create all these random bets that I'm actually working less, enjoying life more. I feel like I'm becoming a better person because just working full-time was just edging out— it was, it had this like base level of anxiety and frustration I had. Plus I'm working on these things I'm actually excited about that might pay off in a dramatic way. It kind of feels like I'm on cheat mode and Totally. I talk to a lot of people about taking the leap and they look at, well, it, I won't be able to make a lot, but they're looking at it the wrong way. Uh, they're not seeing that the hardest part is actually just the psychological shift of saying, oh, I'm making less, but I'm not a worse person.

Uh, but I'm learning all these kind of like life mode skills that will pay off plus there's all this potential upside.

[35:27] Packy McCormick: Yeah, that part's the hard part to appreciate, and it was for me as well. I was like, look, I'm gonna try something that probably means I'm gonna be making a lot less money for a very long time. And then it got to a spot where I think I'll be like kind of at parity, or kind of like, you know, certain weeks am at parity, way more quickly than I expected. And now I can't, like, I can't imagine like the annual salary review conversation as like my chance to start making more money. Whereas like this week, every time somebody subscribes, there's like a little bit more earning potential. So it's just a very, like, it is a totally uncomfortable shift to make, but once you're in it, like, it also looks silly the other way too, where you're like, I don't know, I hope like my boss likes me this year.

Uh, and I'm able to get that 5% raise that I'm, that I'm due.

[36:10] Paul: What, what were some of those kind of like inner, because a lot of people just don't understand the inner game challenges of of making this shift? I mean, I had many, I still have many moments when I'm like, well, I'm an idiot. All these people are making more money in my former profession. Am I just a fool doing this? What were some of those conversations you had with yourself in the first year?

[36:38] Packy McCormick: Yeah, it goes back further than that, right? Like when I was, I remember being like 8 years old and being in the backseat of the car and telling my parents that my goal was to be the richest person in the world. And then like, yeah, I spent a lot of time towards that and like went into finance and all that. And then I realized while I was in finance that I didn't like it nearly as much as the other people who were in it. And I wasn't willing to like sacrifice nearly as much. And by the way, they were actually just like naturally better at it than I was too.

So I was like, man, I could make a lot of money and like get increasingly comfortable doing it this way, but I'm not going to win this game. So like, why not go try something that I think I can win? And so like joined a startup because that, you know, requires a more generalist skill set, which I think I possess. And so did that whole thing, and I was like, you know what, I want to start something and that's going to be lower risk and higher upside. Chances are I'm not going to be the richest person in the world by doing, you know, particularly that in-person social club idea. But, um, and then going to this and being like, I don't know, this is just like what I've told my wife for a while, that if I had infinite time and money, I just want to get paid to or just not even get paid to, just read and write.

And so like, if I can do this and figure out how to build a business off of it, like, that would be amazing. And we're in this weird time where like, we're living with my in-laws and not paying rent. So like, if you can't figure out, like, if I can't figure out how to do this now, and if this isn't the perfect opportunity for this, like, it's just never happening. So let me, let me give this a shot. And then like, now I've come weirdly come back to like this world of finance and I'm writing about, you know, companies and investing and all of that kind of stuff from this like totally different route that does make me feel super silly compared to the people who are actually like in finance every day. And I'm coming in like doing memes and stuff.

But it is funny that like it's taken me this long to get back to that like original kind of passion for it, but from a different angle.

[38:28] Paul: I, I think within the next 5 years we'll see some like JP Morgan or Goldman report with memes in it. They'll probably be using your charts.

[38:37] Packy McCormick: 100%.

[38:38] Paul: I loved your Future of Work piece because the takeaway for me, the headline was like, the worker decides. I think that's right. I, I think it may be— I think the biggest hurdle with that is people realizing they have that power, right? And I think a lot of people have woken up to the fact that they do have this power. And it sounds like Packy is not for hire.

[39:02] Packy McCormick: Packy is— yeah, I was talking to my wife about this yesterday. I think if Stripe was like, you can do whatever job you want for us and make your own role, or like, you know, some dream role that like Patio11 has, like maybe I would do that. I think that's the only job I can think of that I would actually go do.

[39:22] Paul: Uh, yeah, I mean, Stripe— Stripe is a company that just like blows my mind. It's like, oh my God, this this company is basically going to be the operating system for the world.

[39:32] Packy McCormick: It'd be cool to be a part of that and get to see from the inside of what that looks like, because I think it'll be that transformational. But otherwise, yeah, not for hire.

[39:42] Paul: What are you thinking about for 2021?

[39:46] Packy McCormick: Every January 1st, and I used to have free access to Breather Spaces, I no longer do, so I'll need to find a new space for it. But I would lock myself in a Breather Space for 5 or 6 hours, reflect on kind of the past year, and then set goals for the next year. Right now I feel really good not having goals. And there's been enough serendipitous things happening that I'm comfortable without setting those goals. And I've also given myself kind of like till my son is sleeping through the night to like really put brainpower towards— if that happens by January 1st, then hopefully I'll spend that day and like really think about what I want this to become in the next year. I'd love to have more people involved in a loose kind of association type of way, not formal structure, most likely for a little while.

I'd love to kind of go deeper on the investing side. I have this angel investing syndicate that I think we can do a whole lot more with. But otherwise, like, I don't know, I'm having such a fun time just exploring and seeing where it goes that I'm going to keep it loose.