PackyMcCormick

LubaThank you so much for coming on the show.Link

PackyThanks for having me. This is so cool.Link

LubaThe weather here is so nice today — let's get out in the sun. Do you guys go on a lot of walks?Link

PackyIt's a good question. We don't go on as many walks. I think we both go on walks separately during the day, walk the kids a couple places, but long walks with the family, not as much — because our daughter just gets tired.Link

LubaWalks in the city have been my recent revelation. Every morning I take a walk to the West Side Highway and I leave my phone at home, and I take a book and sit and read a few pages and then meditate. I've been so obsessed with the walks — phoneless walks specifically. That's been really nice.Link

PackyThat's really nice. I run, so I'll run on the West Side Highway a bunch, or the equivalent would be Brooklyn Bridge Park. We walk with the kids, but walking around the city is the greatest. Since you're newish, it's the greatest way to get to know this place.Link

LubaThe city is really conducive to walking, and there's so many things happening. What I've noticed is that oftentimes the thing is not immediately available on Google Maps — you search up restaurants, and then you walk and discover some hole in the wall, or maybe it's actually a really nice place, and you're like, I would never have found this if I'd just searched OpenTable or Resy.Link

PackyExactly. When I was getting ready to leave investment banking — I'd moved up here and did that for a few years, so I didn't really experience the city, because you're mostly in the office the whole time — but I got jury duty right at the end, after I'd told them I was quitting. So I went from working eight to whenever, to working jury duty nine to four.Link

LubaHow many days was jury duty?Link

PackyI did it for like two weeks. You get out earlier some days, and I just wouldn't go back into the office. It was so leisurely. I was in the Union Square area, downtown where all the courthouses are, and I walked a different way down there every day. It was the first time, a few years in, that I really felt like I knew the city. It was amazing.Link

LubaDid you get to explore Brooklyn as much as Union Square in Manhattan?Link

PackyI'd explore Brooklyn more probably running, through a bunch of different spots. But for a while, my wife and I, before we had kids, lived in downtown Brooklyn, and I worked in Soho then, so I'd walk over the bridge and back.Link

LubaHow long did that take?Link

PackyAbout 40 minutes. The subway would've been 20-something, so it wasn't a big delta, and it just made me so happy to be able to walk in every day. My kids go to school literally in the building right next to where we live, so I'll walk them in sometimes.Link

LubaWhy would you choose walking versus, say, biking? Was city biking not as much of a thing back then?Link

PackyNow I bought a bike in Colombia — the country. We have a portfolio company down there and were at a startup event, and one of the other companies was a guy from America who was making electric bikes for delivery people. I'd had a couple of drinks and I was like, "Yeah, I'll buy one of those if you can get it to America." And then he called me and was like, "All right, got your bike." We brought it up in pieces to avoid tariffs, and now we have this bike that I have not used once. My wife is starting to use it now.Link

LubaThat's a very random guy — a bike guy. I love both. I only really like biking that's electric powered.Link

So when you left your job at Breather and were figuring out what startup you wanted to build, one thing that stood out to me is that you were making weekly coaching calls with your mom. Can you tell me more about that period of your life?Link

PackyOh man, dark period — it was amazing. I was at this company called Breather for six years after finance. Way too long. Amazing experience, great people. By the end I got sick of it, left at the end of 2019, and was thinking about what to do. I started thinking about kind of a Soho House for nerds — I was going to call it the Not Boring Club. I'd been doing a debate club as a test run, we'd done some dinners, and I was looking at spaces to sign a lease. Thankfully I didn't do that. I was talking to some investors to invest. Thankfully I didn't do that.Link

LubaSorry to interrupt — why were you thinking about a debate club specifically? Why was that the thing pulling you?Link

PackyThere was a conversation I had with my mom and her business partner.Link

LubaWhat does your mom do?Link

PackyShe's a consultant — organizational development type stuff — and she has her own consulting practice. They were up here for meetings and we got a drink, and my mom's partner was like, "What do you do for fun? What do you do outside of work?" And I was like, "Actually, nothing really." In college and high school I ran cross country, I was in the debate club, I was social chair — I did a lot more stuff, and then I realized I'd become very one-dimensional. And I thought, a lot of people feel like this. Thank God COVID happened and saved me from actually doing the business, because I think it was a bad idea — it wasn't a good fit for me, because I don't want to be out every night hosting a place like that. That takes a certain type of person...Link

Luba...Totally, and not the type of person who'd then be happy writing for six years.Link

PackyRight. So I went a very different route. But everybody has these ideas that are some version of the Peter Pan, extend-my-college-experience thing. That was very much one of those.Link

LubaWhy do you think you became one-dimensional during finance and then Breather?Link

PackyDuring finance you don't even have a choice, really. You just work all the time.Link

LubaYou just work all the time.Link

PackyAnd there's something liberating about it, versus working for myself now. When you're in control, you want to work really hard, but you don't have somebody to blame. Back then I just turned off the idea that I could do anything, and if I was free for a weekend it was a nice surprise. That mind shift was actually great — for a little while here, I'm just going to be working all the time, and that's totally fine.Link

LubaWhat was your goal with work then? If you remember Packy at that period of time, you were working to do what?Link

PackyGreat question. I was interested in finance vaguely as a concept, and the idea of doing something that made a bunch of money when I was young. I went to Duke, and most people went into finance from Duke, so I did that. It was just to be good at it and to move up in it. I didn't have "I want to run a private equity fund, so I need to do X, Y, Z." One of many reasons I ended up quitting: I was fine, but I wasn't going to be world class. I had some friends who still work in finance who were way better at it than I am, and loved it — in their free time they'd read the Financial Times; that's what they studied and loved talking about and researching. That certainly wasn't the case for me. For me, I was interested in startups. There was one startup at Duke when I was there, and I was an intern there for a little while. They're actually still around — it was called Shoeboxed.com. Shout out Shoeboxed. You could take a picture of a receipt and scan it, super early. Ramp does that for free as part of the product now. But back then OCR — optical character recognition — was new, and all of a sudden you could take this messy process where you put receipts in your shoebox and digitize them. This was 2007 or so. This guy I worked with there, Evan Beard, now runs Standard Bots in New York, recently valued at a billion dollars — the most deployed American robotics company. An idiot should have — always invest in your friends.Link

LubaThat's a common thread I've been hearing from everyone who has a regret about not investing in their friends. Not even because those friends ended up building amazing companies, but because it's a good rule — if you can support your friend, who knows, maybe they'll do something amazing next time, even if it didn't work out this time around.Link

PackyTotally. We'd been close during school and lost touch a little while I was in finance and doing startup stuff. Now we've reconnected — I probably texted him yesterday, and we wrote a piece together — but I didn't know him at the earliest stages; by the time I knew him the company was already worth a bunch. It still has a lot of room to go, so I should probably just bite the bullet and invest. All to say, the thing I really cared about — in a dumb way — you see kids now who are in college or high school or 12 years old who are interested in startups, and they're really interested, actually building really meaningful things. My side thing when I was in finance: in the summertime we'd go to this town, Avalon, New Jersey — I'm from outside Philadelphia originally, and Irish Catholic people from outside Philadelphia go to Avalon. It was impossible to get to. There was a train to Atlantic City for one summer called the Aces Train, and then it shut down. One weekend a bunch of friends coming back had to take a limousine, because it was the only way we could all get back, and we were like, this is way better than whatever we were doing before — what if we did this every weekend? So we did. We told people about it, they told more people, and eventually we were taking a party bus, or two party buses, down with like 50 people every weekend, there and back. It was the most fun thing in the world. So I taught myself how to build a website for it.Link

LubaThat's amazing. It sounds like Uber Black before Uber.Link

PackyIt wasn't a business — I didn't have insurance. I got very lucky that nothing happened. But it was a little thing in my free time. What I wanted to do was teach myself — not coding exactly, but how to build a website and how the internet worked — and make $10,000. It was more that than trying to get better at finance. Ultimately I knew I was going to leave, go to business school — and then I stumbled on this company Breather.Link

LubaDo you remember why you were so interested in being a self-starter when you were young? Was it because of your mom and her having a business?Link

PackyMy parents both have their own consulting practices, so there's definitely that. My brother now has his own company — it's called Create, it makes creatine gummies. Shout out Create — I was smart enough to invest in that one. And my sister has a company; she lives in South Africa now, but founded it in Ghana, a fintech in Africa. So there's something in the water. Both my parents were entrepreneurial, we grew up upper middle class, so there's room above, but you have the comfort to take risks without going hungry — a perfect socioeconomic spot. Good schools and all that, so I feel very fortunate. That combination, that stew, clearly produced something in us.Link

LubaLet's jump back to the debate club. COVID happens, and you were like, this debate club idea, maybe it'll be a great business, I need to become less one-dimensional, bring my hobbies back. And during that time you have your weekly calls with your mom.Link

PackyYeah. I was on garden leave — the non-compete period — for about four months, still getting paid by Breather. This was October to February, and I was planning this club. My mom does business coaching as part of her practice — it's not her main thing, but if she's working with somebody she'll do the one-on-one stuff. She was like, "We should just do this to keep you accountable, because for the first time you're not working with anybody." I'd had a coach at Breather that the company paid for, and I really enjoyed that experience.Link

LubaDid you have any reservations about having coaching by your mom?Link

PackyNo, because it's super different — it's on the business side. What I found with the business coach, and maybe this was the coach and maybe it was me, is that the really valuable thing is you kind of just talk at them and they ask hard questions until you talk yourself into the right answer.Link

LubaSo it's on you to figure it out, but it's a methodology to process your own thinking.Link

PackyExactly. She's actually the one who told me, once I started the newsletter, to change the name and go full time. The newsletter was called "Per My Last Email" when it was just a side thing; she said I should rename it "Not Boring" — the same as the club — and that was her idea. So that was wonderful.Link

LubaSo I saw that you really started your writing with Write of Passage. I remember that time, 2019, 2020, when David Perell started coming up on what used to be Twitter, now X, and there was a lot of hype about Write of Passage. At the time I was a big fan of Ali Abdaal, the productivity and business YouTuber, and he took Write of Passage, and I was like, maybe this is something I should do. But I guess I'm like you — I was not that into writing; I always tell myself it's something I want to learn at some point. Write of Passage felt like a huge commitment for someone who really cares about writing. I'm kind of bummed they closed the cohort — I didn't take it, but you did. Tell me more about that decision — why you decided to do it, and were you writing before Write of Passage?Link

PackyIn college I was an econ major and a philosophy minor, so I had to write a bunch for the philosophy minor. I always enjoyed writing — in high school I enjoyed writing for class, but I'd never been on the newspaper. I wasn't a writer-writer.Link

LubaWhat about writing did you like?Link

PackyGreat question. I like the idea of being able to put together — maybe the same reason I like debate — an argument in words. One-on-one, in conversation, I'm fine, but I'm not going to knock anybody's socks off. But if I have time, I can sit there and grind it out and come up with a good argument, and put something clever and creative down on paper. Some of it was, in middle school, if you got in trouble in Latin class he'd make you write an essay, and most people were like, "Ah, this sucks," and I'd be like, "All right, cool." You had to read the essay in front of the class as part of the punishment — most people hated that, and I was like, I'm going to take this opportunity to make fun of the whole thing and be funny. I did the same in high school, and that carried over — it certainly influenced the early Not Boring writing, when it was a little more jokey and less serious.Link

I was at Breather at the same time, with one other guy, Ben Roller. I'd spent Christmas break writing this strategy memo about how we could turn the business around — we had terrible gross margins, negative 25%, and these long-term leases. We wrote it down, gave it to the exec team, and they were like, "Yep, great idea, go do it." We gave it to the rest of the company who had to execute the plan, and they got excited about it. I was like, that's cool — you can just write your way into decision making.Link

LubaExactly.Link

PackyYou can write your way into decision making and get people to rally around it. That was a little signal. And frankly, the exec team we'd hired the last year at Breather just wasn't super cerebral. So I saw a tweet from David Perell talking about Write of Passage — I probably had 200 Twitter followers at the time, and I viewed him as this celebrity on Twitter because he'd get like 100 likes.Link

LubaAnd he's so articulate.Link

PackyHe's so articulate, so good at it. There was a particular exec team meeting where I said the word "enumerate" — in context; we were talking about how people in the company didn't know our numbers well enough. I said "enumerate" and they looked at me like I had seven heads. Then I saw David Perell's tweet about this writing course and I was like, I'm just going to do that, or else I'm going to lose any last mental anything that I have. So I took the course, and it ended up being great — maybe for the same reason as coaching. There were some interesting tricks. There's "find your personal monopoly" — I'm never going to be the best at writing about business, but if you pick, in the early days, business and Philadelphia sports and pop culture, you find an overlap where, because you've overlapped it so much, you have to be the best in the world at that very specific thing. I thought that was a really interesting idea. But a lot of it was just that every week you had to show up with a new essay and join a small group, and you couldn't be the asshole who hadn't done the assignment. A lot of it was getting in the practice.Link

LubaWere there a lot of people who dropped out of the groups during the cohort?Link

PackyI don't think so, actually.Link

LubaThat's very impressive, because most live courses have high attrition.Link

PackyI guess by the end it was COVID-y and people were bored — actually, no, it wasn't even a COVID thing. It was just a very well done course: good people, small group, and he kept it super compelling.Link

LubaIf you were to bring it down to three things outside of accountability and showing up every week, what else really helped you kick off your writing?Link

PackyHonestly, it was really just getting into the routine of doing it. The personal monopoly thing — figuring out what you want to write about that's interesting to you. A lot of people who get started in content creation, whether writing or YouTubing, are like, "What would the market want out of me? Where's a hole?" And you get so tired — you tell me your experience — but if you're pretending to be someone you're not...Link

Luba100%.Link

Packy...you can't sustain it. So really finding the thing you want to write about, that you'd be happy spending hours and hours writing about.Link

LubaI definitely fell into creator burnout with my YouTube channel a few years ago. At the beginning I really started building a community around getting a job as a software engineer, life in Silicon Valley, career advice from the lens of a software engineer, and those videos started doing really well. I was like, okay, this is what people want from me. Then in my own life and career I was transitioning out of engineering to product and chief-of-staff roles, and I didn't bring my audience along, because I thought, this is what they want from me. And I had such burnout, because it felt so one-dimensional and frustrating. I didn't catch it early enough to think about that trifecta — the things I really care about that I want to combine. So that's awesome that the course gave you that.Link

PackyThe audience-capture thing still happens to everybody. I've really tried to avoid it — there've been spots where I've fallen into it more than others — and now I feel totally liberated. I'll still write deep dives on companies because I really enjoy it, and it's what people expect — but people expect it because I've done it a bunch because I enjoy it. Then I'll also — my most popular piece this year so far was about the meaning of life. I really try to just follow my curiosity, and I love it. If I were on an island by myself, I'd be happy writing 10 hours a day, every day, no problem.Link

LubaWhat made you feel so liberated to write whatever you care about and not fall into audience capture?Link

PackyPart of it was just having to write an essay every week. Some weeks I couldn't come up with something particularly on theme, so I'd write more of a think-piece or a more personal thing because they're easier to write, and those ended up doing well. Part of it too was that I was on this meteoric rise for a small business newsletter in '21, '22, and then the market crashed. I got absolutely crushed in this one Twitter interaction. A few things happened where it felt like my stock had flatlined — not even dipped tremendously, but stopped growing meteorically. That was difficult for a bit. And then it was a real "nobody gives a shit" moment.Link

LubaDo you remember that moment? What happened?Link

PackyNot even a moment — it was a period of time where it's like, I don't care, I'm going to do exactly what I want. I feel super lucky that my job is I get to invest in the companies I'm most excited about, spend time with these people who are some of the most extraordinary in the world, learn from them, and then write about what I learn, or whatever I'm curious about. I could spend a whole day in the office reading philosophy if I wanted, and that would be a productive day for my job. So as long as I can pay the bills doing this, why not play whatever I want on that side? Part of it too is I've gotten more into the investing side and learned I really love that, and that frees me up to not put so much pressure on the writing, because there's this whole career on that side that I'm super excited about.Link

LubaWe're going to come back to writing and investing, but for someone who hasn't read your most popular piece from this year — what is the meaning of life?Link

PackyThe piece was called "Riding the Leopard." It's from a Joseph Campbell reader — somebody who'd worked with him put together different talks he'd given over time.Link

LubaIs that the hero's journey?Link

PackyIt's not the hero's journey. I'm going to take a whole different direction, because I'm not going to remember the quote exactly. A few years ago I listened to The Telepathy Tapes. Did you listen to it?Link

LubaI've heard about it but didn't listen. I think I started the first episode — lots of my friends were obsessed with it.Link

PackyThere are debunkers out there — could the experiments have been run better? For sure. But the thing that got me was you'd hear from some of these nonverbal autistic kids who seem to have telepathic abilities. Debunkers say the parents influence how their hand moves, but to me it pretty clearly seemed like some sort of telepathic ability, or at least an unbelievably sensitive appreciation for their parents' touch directing them to have these complex thoughts. There was a telepathy piece, but also some of them would know languages they couldn't have known — nobody in their family knew or spoke those languages, and they just knew them.Link

LubaIt's almost like — do you know the book Many Lives, Many Masters, about past lives?Link

PackyI just read Many Lives, Many Masters — oh my God.Link

LubaI just reread it. It was really good. Why did you read it?Link

PackyI've been very into all of this stuff — this is kind of what the piece is about — the weird parapsychology.Link

LubaDo you believe in it? Reincarnation?Link

PackyTotally. I think so, yeah. I'll go back to the piece and explain why. Some of these kids who society, or the people around them, would say are "just totally lost, they can't speak, they're autistic" — when they figured out how to unlock their communication would be talking about something equivalent to the Akashic records, this collective shared memory. They talked about the reincarnation of some of their friends — one friend who'd passed away, and they all separately told their parents they saw his spirit there. Even if you don't buy the telepathy thing — how in the world are these kids tapping into what all the religions have said forever, but at a deeper, experiential level? Some of what they said rhymed with Christianity, Buddhist texts, Daoism — all of it. Aldous Huxley wrote The Perennial Philosophy — the idea that the mystics and experiencers across all these religions and spiritual traditions basically say the same thing: you're a small part of the universe knowing itself. Atman is Brahman, all of that. Everybody says that, and then these random kids were also saying the same thing, and it sent me down a rabbit hole. So the piece was a little about that, and a little about the idea that the purpose of technology is to expand the potential for new experiences — but our job is to go have those experiences. The better AI gets — if it takes your job, well then you weren't that job; that's not the most human thing you could be doing. It'll do that while you go figure out something else. There's always something else to go experience. You're a unique person whose job is to go live out this life that only you possibly could. Somebody recommended Many Lives, Many Masters, and I just think it's fascinating that there's so much evidence. The University of Virginia has thousands and thousands of records of kids around the world who have a scar and a memory of where they'd have gotten it, or memories of past lives with dates and names they go check, and those dates and names are real. There's so much smoke, and the fact that it all points to the same thing — it would be the greatest coincidence ever if all these people across space and time said the same thing that was made up. That feels impossible to me.Link

LubaI have so many bookmarks and questions. First — why do you think our role is to go and experience things?Link

PackyThis guy Chris Bache was a professor at Youngstown State University. On the side of his religious studies role he did 73 high-dose LSD trips, and came back saying the same thing: you're the universe experiencing itself. People throughout history and all the spiritual traditions say the universe, or God, or whatever, is perfect — so the reason we're here is sharding that thing, putting it in physical form where it can suffer and not know the future, so it can actually have experience. A perfect, all-knowing, omniscient thing can't have experience, because it already knows everything. So it's this creative process of having people come down to Earth and experience all these things on behalf of the universe, so it can grow and expand and know itself. If that's the case, then your job, as one of these little shards of the universe, is to come down and have experience in only the way that you can.Link

LubaIt's almost the same thought as the purpose of everything being to create entropy. So we're experiencing all these things to create entropy, and with entropy, something new is going to come out — innovations, progress, different processes.Link

PackyTotally. On the tech and innovation side — it actually changed my mind on engineering our bodies and longevity. Like, one day do we give ourselves wings? Before, it would've been "you shouldn't play God — maybe you're taking it too far." As I was writing this piece — it was actually for a talk I gave — it struck me as ridiculous that God, if there is this all-knowing thing, would be like, "Everything you've done so far — glasses, medicine, bombs — totally fine. But making yourself, giving your body, touching any of that — is way too far." That feels not correct. If I had wings and nobody else did, that's an experience no human has ever had. If you think the point is experience-maxing, then getting out there and flying around, certainly you should go do that. So there are technologies that expand the potential for experience — that's the best thing tech can do. And there are some, like the downside of AI potentially, where you all talk to this thing and it gives you the same answer, and you turn off your brain and stop critically thinking. That can be bad. There's some centralizing or homogenizing tech you need to be careful of. It can be powerful if you use it for expansion, and damaging if you use it for contraction.Link

LubaIs this a recent interest, or have you always been interested in life beyond the life we have on Earth, why we're here, expansion and experiences?Link

PackyWhen I was five or six, my mom and dad still make fun of me for this — the thing I'd go into their room in the middle of the night scared by was infinity. Just the concept of infinity. I'd sit there like, "It just never ends. What about 10,000 years? And it just never ends." So that was always there. I went to Catholic school; I would not say I was religious at all growing up.Link

LubaAre you religious now?Link

PackySpiritual, but... I don't know. I believe they're all saying something very similar, and I love it. So yes, I guess, but I couldn't tell you which religion.Link

LubaOne thing I've heard someone say that really resonated with me is that there's faith, and then there's religion. Faith is believing in something otherworldly, and religion is a certain vertical of rules and guides and stories you're told you need to believe and rules you need to abide by. That resonated because I'm really open-minded and curious about similar topics, but I don't think I'll ever live my life by a certain rulebook that someone put together.Link

PackyPart of it too — I went to Catholic school for middle school, and there was a girl in my class who was the nicest girl, and her mom was super nice but was divorced, and I remember one of our teachers being like, "Oh, your mom's going to hell because she was divorced." That's not nice — I don't necessarily want to be a part of that. I'm reading the Tao Te Ching now — I don't know how I hadn't before.Link

LubaWhat are you reading?Link

PackyThe Tao Te Ching. There are 81 little lessons — little poems, almost. Part of Taoism's thing is that it's not a religion — one of them says something like, the more religion there is in the world, the worse. I'll get the words wrong, but the ideas are very similar across all of them. Do you put all those extra rules on it or not? I think there's value in it — it depends. We met through Ali, and Ali and I met through crypto, and there's almost this underlying protocol that is all of this stuff, and then on top there are all these apps that speak to different end users — that's kind of what religions are. For some people, if it's the way you can get into these ideas, amazing.Link

LubaI want to go back to the piece about the meaning of life, and this idea of experiences and expansion. What stood out is that it's very optimistic, and you're seen as this optimistic guy. Where does your optimism come from?Link

PackyA similar-ish place. I've been very lucky to have a really good life, and knock on wood, nothing terrible has happened. There've been plenty of times where — I don't want to oversell this — I wouldn't be elected to student government, and then I'd go back and become the president of it the next time. That's been a theme enough times: the first time it doesn't happen, and the second time I come back and it does. And part of it is, if you just look at the numbers — the GDP per capita graph, any of this — things do get better over time. It weirds me out that you'd see all this miraculous stuff happening around you and focus on the thing that could go really wrong. It's good that there are people thinking about what could go wrong — not everybody can be optimistic, and I have the privilege of being optimistic because there are plenty of naturally pessimistic people thinking about the downsides. Even the Anthropic way of being is a little pessimistic to me.Link

LubaYou were like, why not be optimistic?Link

PackyWhy not be optimistic? But I also think it's self-fulfilling. If you think everything's going to be bad, why do anything? If you think you can't make a contribution or solve something, you're not going to start. So the more people who are optimistic, the more it's a self-fulfilling prophecy.Link

LubaDo you think optimism is a choice, then?Link

PackyI think people are more or less optimistic naturally, and then based on how they've been raised and their experiences. But there are plenty of people I talk to — because we write this Weekly Dose of Optimism every week — who say, "Thank you for doing this, because before, I'd read the same story and be like, this is terrible, I can't believe data centers are using so much water." There's always a way to look at it that's positive. Just having that in their inboxes, I've seen enough people change their stance. It can certainly be taught, or practiced.Link

LubaWould you say your mission is to spread optimism and positivity and a desire for people to make progress?Link

PackyI've said the mission of Not Boring is to make the world more optimistic, and that's probably true. But I wrote that in 2022, 2023, when everything felt so pessimistic. Fortunately the world has gotten more optimistic and more progress-pilled recently, so that mission is well underway, and I don't need that to be my mission anymore.Link

LubaWhat do you think is your mission now?Link

PackyI honestly don't know. I feel lucky that I get to write things like the Riding the Leopard piece that people will read. Maybe it's being this translator between normal and weird — that could be a really complex business and the esoteric topics, or esoteric topics and a general audience. Hopefully over the past six years I've built up enough trust that, one, I'm going to be wrong plenty of times, so use your own brain and don't just follow whatever I say; and two, I'm going to follow my curiosity and try to find things I think are interesting and important, and then — because I'm the right level of dumb, where none of it just naturally occurs and I need to figure it out myself — I'll translate it and explain it to people. That could be businesses, esoteric ideas, whatever. Taking things that are complex but important and communicating them in a way people resonate with.Link

LubaI sometimes grapple with this idea — do you need to always have a 100% articulated mission, or do you just do the things that are interesting to you and have fun? When I embarked on this journey, I spent some time being like, I have to manufacture a very specific mission, because you build a tribe of like-minded people if they're clear about why they're listening to you and what mission you're on — people want to come with you on a mission. But then I was like, finding a mission can also be a pursuit in and of itself, and you can just focus on the things that are fun, like getting to write and meet interesting people. I get to talk and meet interesting people and ask questions. It's been so over-talked-about that everyone needs to have a grand mission.Link

PackyIt's a cool way to live life if you think you have something, but it's most important to follow your own. If you know what you want to do, you can direct a lot of resources to it and attract people to it — there's something really magic there. We were talking about Lenny earlier, and how he was one of the first people you spoke to when you entered the YouTube world. He got lucky — well, "lucky" is the wrong word —Link

LubaThe free newsletter at Airbnb, right?Link

PackyYeah, the free newsletter at Airbnb. It feels like he found this perfect spot where he's super clear about what his thing is, and it's also something he's excellent at and seems to love, and all those things come together. If you can find that, amazing. My shit is too all over the place to really have a super clear mission an audience would come for, so I've had to learn to accept that. He's probably grown — we were neck and neck for a while, and he's grown five times faster than I have, and that's totally fine. Part of it is just not forcing a mission to hit some metric or find an audience — that'll lock you into something you might not want to do.Link

LubaI want to bring it back to your story and how you had the courage to go be a self-starter. One of the things I heard you say is that you felt like you wouldn't be a good enough founder of a startup, so you decided to take a step back and write and found a business in that. But in a way, that is taking a bet on yourself and becoming very much a founder. Take me to that time and your decision-making process.Link

PackyA lot of this stuff — there's a clear story in hindsight, and then in the moment... I'd wanted to be a founder, then COVID hit and that wasn't going to work, but I liked this newsletter I was writing, and I thought maybe I could start writing some longer-form essays and at least see what happened for three months, until I found a real job and the world opened back up.Link

LubaThat was the real story.Link

PackyThat was the real story. And then it just kind of started taking off — nothing crazy. I didn't make any money off it for a while.Link

LubaHow long was the while?Link

PackyFrom April to September. Then I started making money, but it'd be like $1,000 for an ad spot every once in a while. Not big money, but clearly on the right trajectory.Link

LubaTell me more about the conversation at home, because at that point your wife Pooja was already pregnant, right? Was she like, "What the heck are you doing?" or very supportive?Link

PackySuper supportive. She'd also left a stable job. She was at a company called Nuts.com — shout out Nuts.com, now it's doing really well. It's a third-generation family business — a nut and candy store in Newark; the third generation bought the web domain nuts.com back when domains didn't cost billions of dollars, and turned it into this massive business: super high-quality nuts, but also any powder restaurants use in bulk, a bunch of ingredients. A monster business. She did supply chain there, then went to a startup doing supply chain, which didn't have great health insurance. And I was giving up my job, so I wasn't going to get health insurance. She was very supportive. Our lease expired in June of 2020, so we moved in with my in-laws, and I wrote from their basement for a while. I had money saved up — not a ton, but some.Link

LubaWere you surprised by how supportive she was, or was that a given?Link

PackyBoth her and her family — we moved in with her parents, and her mom made us food every day and let us crash. Then we had our son Devon, and we spent the first few months with them. The whole thing was lovely. There are a lot of good things about COVID — one was we got to spend all this time with her family. None of this happens without that period and them being like, "Yeah, of course, come here." All of them being as supportive as they were was super important.Link

LubaAny tips for someone listening on how to find a supportive partner?Link

PackyThere's probably some consistency. She knew what she was signing up for when we met — we met doing finance, so obviously a totally different path from that. But I probably worked the most hours of anybody we worked with, and had this weird side hustle. She knew I was weird and loved working, so she knew at least I wouldn't just become a lazy bum. We had a couple of conversations where I had to be like, "Look, I know it's been a while, and this person's getting these CPMs, so even if I turn on monetization now, even a bad number, at least we could pay rent." Then the money started coming in, even in drips, and it felt better from there.Link

LubaIn one of the profiles someone did on you — I think it was Mercury, around 2022 — you were talking about how you have to work really hard on every single newsletter and essay because you were scared that one moment it could all go away. Do you still have that fear?Link

PackyNo, which is good and bad. There's something really healthy about having the fear that drives you to be good. There was this period in early 2025 where I changed my sponsorship situation — instead of having a sponsor on a particular date, a sponsor buys five or ten spots, and then whenever I write, they go in — which lets me give myself all the time in the world to read and think, and then I'll just write. And you end up being worse. I ended up not writing as well, because there's something to the forcing function of having to put something out, which means some things you put out are going to be bad.Link

LubaJust to clarify — there was a period where you were like, "I'm not going to be on a set schedule, I'll write when I write, but these sponsor spots will support me." But that accountability of having to put out an article is different.Link

PackyAccountability, and — I was talking to somebody about this the other day, and they brought up the clay pot experiment, where the teacher tells one group they have to make one perfect pot...Link

LubaOh yes — and this group has to make a bunch of pots.Link

Packy...and then you compare, and it's always the one that made a bunch that's best. So I'd rather have the opportunity for something really good. No one is going to be like, "I'm never reading Packy again because that piece was eh." But they'll come in and get re-excited by a really great piece. So I'd rather optimize for great than for avoiding anything not-great. I say that, and I still give myself probably more pressure than I should about any given one — I send 50-something pieces a year; if any one is not great, it's not the end of the world. But I still put as much as I possibly can into it. I just don't think, as much as I did before, that it all falls apart.Link

LubaWhen you say 50 pieces a year, does the Weekly Dose of Optimism count?Link

PackyThat would be closer — let's call it 30 essays a year.Link

LubaWhen you say a piece is great or mediocre, are you the judge of that before you send it, or in retrospect based on how the audience responds?Link

PackyBoth, and they're not always the same. But at least it has to be good enough to stand out.Link

LubaWhat's the delta between good enough and great?Link

PackyI don't know if I hit that all the time. There's a lot more editing I could do that I actually don't, and maybe I should, but that would slow the kick, so there are trade-offs — editing down would probably be the biggest one. But I always want to make sure I've done as much research as I possibly can on a subject, and then explain it as clearly as I can. Or if I'm writing about a company, capturing the essence of what they're doing, and bottling up this moment in time for the company as well as I can. There's no clear metric — just a bunch of things I feel about the inputs.Link

LubaTheir whole vibe is that you take responsibility for everything — everything is an opportunity to expand and learn. It's a very growth-oriented philosophy.Link

PackyWhat's the place to start? I'm trying to find other books.Link

LubaThe Power of Kabbalah is a really good book. I actually go to classes every week at the Kabbalah Centre — I've really gotten on the train of learning. They believe in reincarnation too: your life is a quest to become better, and if you don't fulfill the quest and don't work on all your soul corrections, you reincarnate again to give it another shot. Before I stumbled on it, that was kind of my belief about life, and I was like, "Damn, this articulates it well."Link

PackyIt's funny how many people say that. There has to be something there.Link

LubaEven if nothing is like that, it's cool to be open-minded about it, because I think there are useful ways of living life, and then there are right ways — proven ones. Just to go day to day, why not pick a useful, optimistic, positive quest?Link

PackyI feel the exact same way. If you look at everything this general philosophy would tell you to do — working on yourself, imagining there are things you need to work through, taking everything as healthy — even to say, "Oh, that terrible thing happened, I must have had to learn something through it." What's the opportunity to learn? It's a way better way to live.Link

Luba100% agree. So, what does a day in the life of Packy McCormick look like?Link

PackyGood question. This morning I woke up, and my daughter woke up a little after me — call it 6:30. Every morning we make creatine; she loves cutting the thing and pouring the glass.Link

LubaShe drinks creatine too?Link

PackyNo — she likes making it. Shout out Create. Then I make her breakfast — she had toast this morning. I wake up early, at like five or six, no matter what. Last week a couple of nights I went to bed before nine, and every time I do that I'm like, this is the greatest thing in the whole entire world.Link

LubaThe key is going to bed on time.Link

PackyThe key is going to bed on time, for sure. Normally, say six on average, I wake up. The kids wake up around 6:30 — we do creatine, breakfast, coffee, dishes. During the school year I'll drop them off, but otherwise I come into work around eight, and try to keep the mornings as open as possible to read and write. Today I'm working on this deep dive — I got in at eight, sat at my desk for four hours, and just wrote all the way through. We're doing this now, then I'll go back this afternoon and write until seven or so, maybe later, because my wife and daughter went to her parents' house for the night — until the piece is done, because it goes out Monday. A normal day would have at least one or two meetings, with a founder I'm talking to or a founder in the portfolio. In the beginning I tried to talk to as many companies as possible; now I've gotten a better sense of the companies I like and can add value to, so that top of funnel is smaller. And I've come to appreciate that the way I can be most helpful to a company is being good at writing and having an audience that trusts me — finding the very best companies I can and telling their stories as well as I can. So a lot of my effort has to go into the writing side, so that when it's time to pull out that arrow for a particular company, the arrow shoots straight.Link

LubaHow do you meet companies these days?Link

PackyAll over the place. If I write about a certain category I'm interested in, a lot of inbound comes in, through other investors or founders I know. I've been doing this a little over five years, so the network is growing. If I can be as clear as possible about the type of company I'm excited about, I get to see more of that. A lot of it is talking to people and keeping the feelers out; a lot of it's Twitter — if I see something interesting I can reach out directly. The good thing about the newsletter is that even if people don't read it, they've at least heard about it, or I can find somebody who can get me in touch with almost anybody. When LPs ask about sourcing, it's one of the questions I'm worst at answering, because a bigger firm would have a really tight sourcing funnel — mine is like, each of my best companies came in through a totally different channel.Link

LubaThere's something to be said about attraction too, because people who resonate with you get attracted to you naturally and reach out, or you stumble upon them.Link

PackyI completely agree. It's harder to explain, but that's half the point of the newsletter with the fund — it probably repels people who aren't interested, but hopefully attracts the ones who are, in a way that's unique and isn't just cold outreach all the time.Link

LubaYou mentioned that twice a day — today you're sitting there for four or five hours writing. Have you intentionally developed this muscle of deep focus, or are you just a focused guy?Link

PackyBack to our earlier conversation — I had this deadline Monday. Not always. I'd say my focus is probably not as good as it has been or could be. The internet generally contributes to that. I think AI is super pernicious in this respect — you think you're doing something productive by talking to it, asking questions, building stuff, and most of the time you're not. I can trick myself: "What if I go ask it a couple questions on this topic, or have it make me a report" — and then I don't read the report, but it feels productive. Or the report's fairly milquetoast. There's a million ways to get distracted. The thing that fixes it for me is having a deadline. Today's a special day in that I just have to get this thing done, so I'll write eight hours if I need to.Link

LubaNow that you've been writing for so long, is there a more quantitative process to research — like, I'm going to talk to X people about this company, read three articles about it?Link

PackyNothing quantitative. If I'm writing about a company, it's a different process than a general idea. A general idea normally starts with, I've been reading stuff and talking to people, and I've noticed this thing happening over and over, so I'll talk to more people once I've formed the basis of the idea and ask, "Have you seen this? What are some examples?" I'll research case studies and then write it. With a company, a lot of it is talking to the people in the company, realizing where I have questions or gaps, and then talking to people or reading something, or doing research with ChatGPT.Link

LubaSo the underlying thread is curiosity — you're driven by your own curiosity, and then you pull the string.Link

PackyYeah, I think that's right.Link

LubaI thought it was interesting that you started writing because you're very forgetful — you had a bad memory. Is that still the case?Link

PackyOn the detail side, 100%. I'll run into people I know and just...Link

LubaYou're like, who's this person? I know that I know you.Link

PackyIt's weirder now because I know a lot more people, but I also have more of a one-to-many relationship with the newsletter.Link

LubaPeople are like, "Oh my god, I know you, I know where you went on vacation last month," and you're like, I have no idea who you are.Link

PackyBecause my memory's so bad, I'll be like, "Oh, hey," and they're like, "We've never met." But if you ask me to riff on some of my favorite companies now that I've spent so much time writing about them, I can recall more. So it's probably made my brain stronger than it was before.Link

LubaIs it just that your memory is selective, and because you're writing there's constant recollection, so it precipitated in your brain — and if you did that with faces it would be the same?Link

PackyMaybe. That's definitely possible.Link

LubaThere are certain things where I feel like my memory's not great, and I'm trying to figure out ways to commemorate my own life. I remember things in abstract facts — like, this is how I felt — but details are sometimes harder to come by. And then there are other things, like conversations, where I remember very specific details most people forget. So I'm trying to figure out whether I have to give up and double down on things I'm naturally strong at, and write down the things I'm not good at — or is there some mechanism to practice better recall and improve your memory overall?Link

PackyI have not found anything. Even the stuff I'm good at recalling — I wouldn't say I'm above average; mine is just below average across the board, and I haven't found a way to train it. Maybe I could, but it doesn't feel like the best use of my time. To that question generally — do you strengthen the thing you're good at, or fill in the weak spots? — I'm a double-down-on-the-strengths guy. You'll get a lot more out of doubling down on your strengths, unless your weakness is so glaring it's really holding you back in life — like you can't start work in the morning without seven drinks. Then you should fix that. But otherwise, I like doubling down on the strengths.Link

LubaI notice that in some of your pieces you do a more elaborate intro, sharing personal details — if you're traveling somewhere, or something's happening — and you have the reflections on the year where you share more of your life. Have you intentionally thought about how much of your personal life to share versus focusing on the serious writing?Link

PackyI try not to have it be too serious. I want all kinds to blend. I want to be able to do this forever, and I don't want it to be the "me" show, because who cares in a lot of cases — but I also don't want it to be a faceless thing writing very serious content. If anything, I've made it too serious maybe, and I need to bring some levity back.Link

LubaDo you feel like it's too serious and heavy?Link

PackyNot heavy, but — it very much was almost cartoonish in the beginning, and it's not that anymore, which is fine; I've figured out the voice and gotten better at the core thing, so you don't need as much of the stuff around it. But I don't want it to just be one of 50 business or tech analysis things. And this is dumb, but in the age of AI, the more personality you inject, the less an AI can do that, so there's value to that.Link

LubaIs there someone's writing you recently saw and were like, "Damn, I wish I wrote that"?Link

PackyIn my world, Jeremy Stern and Dom Cooke at Colossus have both been writing excellent stuff. Dom Cooke's recent profile on Sarah Guo was really good. Jeremy Stern's profile on Josh Kushner was amazing. Mario Gabriele just continues to write.Link

LubaThe research in those Colossus pieces was incredible — and how long they were researching it.Link

PackyThey're in bed with them; it's really cool. It's cool to see that whole Colossus flywheel work — he's gotten incredible writers together, he himself has amazing access, so it's combining the ability to get to anybody with really amazing writers. A lot of them end up coming out with his podcast, and I think he's one of the best question-askers out there. There's also the obvious stuff — going back and reading anything David Foster Wallace wrote. I was talking to a friend the other day who was like, "I wanted to be a writer in college until I read" — I forget which David Foster Wallace piece, maybe A Supposedly Fun Thing I'll Never Do Again — "and I just stopped writing then, because I saw I was never going to be that good, so what's the point?"Link

LubaHis writing is insane, because you're literally embedded in the brain of the person he's writing from the perspective of.Link

PackyIt's so good. I don't get it. I love reading him and then writing right afterward — you get some style transference. I'm not going to start writing like David Foster Wallace, but I start doing more run-ons, and it's a fun mindset to get into. His profile on David Lynch — "David Lynch Keeps His Head" — is so, so good. And there's "Something to Do with Paying Attention."Link

LubaOh yeah, I read that maybe six months ago. It was so good.Link

PackyIt's still number one — I was in McNally Jackson yesterday, and it's still their number one edition.Link

LubaWow.Link

PackyJust the way he can describe certain emotions or feelings so succinctly — I'd never be able to put the words to them, but you read it and you're like, I get exactly what you're talking about. There was a scene at the pool where he was watching people get out of the pool, and it was so precise. And the other thing he does — "Something to Do with Paying Attention," it's about paying attention, and then he leaves these little Easter eggs throughout, so that if you are paying attention, it really rewards paying attention. It clearly drove him crazy that he has a brain like this, but it's beautiful.Link

LubaNow I'll have to go back and see if I was paying attention.Link

PackyYou should 100% go back and read that one. It's so good.Link

LubaDo you spend a lot of time focusing on improving your own writing, writing as a discipline?Link

PackyThere are times when I'm like, I want to become a better writer, so I'll read more profiles and more David Foster Wallace, and maybe even type out some of the stuff they wrote, and then hope it happens through osmosis. There's nothing specific — when I sit down to write a piece, I'm not like, "I'm going to pull in this trick I learned recently." Everything I do is dump a bunch of stuff in, hopefully it sticks, and it comes out the other end, with no real clear process.Link

LubaI want to go back to optimism. What are some people or things that recently made you more optimistic about the world?Link

PackyGreat question. To go back to David Foster Wallace — he has the "This Is Water" speech, where the young fish are swimming and someone asks, "How's the water?" and they're like, "What's water?" — because you're swimming in it. That's kind of what it feels like right now. There's so much stuff. Two or three years ago, Julia DeWahl, who's a co-founder at Antares — they just raised $470 million making microreactors. Shout out Antares — if you're a branch of the military and you need a nuclear reactor, call Antares. We did this podcast where the whole first half of the season was, "How do we come up with nuclear energy — we don't have it everywhere." And now, before the Fourth of July, four companies went critical. A couple others decided to go straight for producing power. So we're going to have a number of advanced reactor startups putting power in the grid — this thing that was stagnant for the past 40-plus years is coming back. What's happening in bio and health — we now have a pill or a shot where you can lose weight, and it has all these other incredible side effects; each week there's a new GLP-1 side effect that's really good. There's a company called Alef — Alef Neuro — using an ultrasound on a chip to image the brain from outside the skull at higher resolution than ever before. People who decided at 15 that they wanted to figure out how to read our brains and use that as the next interface, and they're out there actually doing it. And where I spend a lot of my time now — these companies that are a couple of years old, whose express goal is to topple monster incumbents in the biggest industries in the world. There was a period where software was the main thing, and that's great — we didn't really do software forever, and then we softwared everything in 40 to 50 years — but now they're actually going after it, saying, "I don't just want to help this industry, I want to go win energy," or in Anduril's case, "we're going to become the biggest defense company," or SpaceX in launch. Because of those companies, that's happening to every industry. Maybe not as crazy-sexy as "we're going to read your brain from the outside," but in terms of everyday impact — if you can replace every big, stale, sclerotic company with a younger, cheaper, better, faster version, everyone's day-to-day life improves and gets more affordable.Link

LubaMore expansions and experiences.Link

PackyTotally, more expansions and experiences. There's the supersonic flight company I wrote about in that piece — when that happens, you'll be able to see more of the world. It expands what we can do, and part of that is taking away stuff we don't have to worry about anymore. It's hard for me to look at all this and not be optimistic.Link

LubaWhat do you think we have to do as a society to instill more of this optimism and pursue big ideas? What's our individual contribution?Link

PackyThe individual one is — you find yourself in conversation with people all the time where you're like, "Oh, this thing is so terrible," and you get used to it and accept it. Even just pushing back on those things — "the world is so terrible, the government's out to get us" — even on a local level, that's the kind of thing.Link

LubaAnd maybe on a local level, if you hear someone being very negative, pausing and trying to prove them wrong, or instilling more positivity into the frame of their arguments.Link

PackyYeah — not necessarily trying to... There's a reason people feel a certain way. I'd never go to somebody and be like, "No, no, you should be way more — the world is great," and they're like, "Dude, I wasn't able to afford dinner last night." It's not that. But if you can infuse positivity — if there are two ways to look at a situation that isn't their lived experience, something they read about, and their natural inclination is "that's obviously terribly evil" —Link

LubaYeah, that's what I'm talking about — exactly those conversations.Link

PackyExactly.Link

LubaAnd Packy, just to wrap it up — what's something that brought you joy this week?Link

PackyOh man — going to bed before 9 o'clock. Amazing. Game changer.Link

LubaAmazing. Thank you so much for your time.Link

PackyThank you. This was so much fun.Link

LubaThank you.Link

PackyGreat stuff.Link