Not Boring (with Packy McCormick) - Extended Cut

1. 0:00 – 3:07

   Mission: Get Packy to 100K — why Not Boring is an Acquired-worthy “one-person company”

   1. DRDavid Rosenthal0:00

      Okay, we gotta get you over 100K. This episode is a failure if we don't get you over 100K subscribers.

   2. PMPacky McCormick0:04

      Right, so let me, let me timestamp where we are right now, just so we know what we need to do. [chuckles] So we are at eighty-eight thousand four hundred and sixty.

   3. DRDavid Rosenthal0:12

      Oh, we can so do that.

   4. BGBen Gilbert0:13

      Oh, we'll juice this. [laughing]

   5. PMPacky McCormick0:16

      [laughing]

   6. SPSpeaker0:16

      Who got the truth? Is it you, is it you, is it you? Who got the truth now? Is it you, is it you, is it you? Sit me down, say it straight. Another story on the way. Who got the truth?

   7. BGBen Gilbert0:33

      Welcome to season nine, episode six of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I am the co-founder and managing director of Seattle-based Pioneer Square Labs, and our venture fund, PSL Ventures.

   8. DRDavid Rosenthal0:48

      And I'm David Rosenthal, and I am an angel investor based in San Francisco, and I am back, sort of, from paternity leave. [chuckles]

   9. BGBen Gilbert0:59

      An, a, an abbreviated, partial, ongoing paternity leave.

   10. DRDavid Rosenthal1:02

       Yeah, you know, we're, we're making it work, but-

   11. BGBen Gilbert1:05

       And we are your hosts. [chuckles] Well, today we have a first for Acquired. We are covering a business that is only one person, Not Boring, the newsletter-gone-media-and-investment empire run by Packy McCormick. I did some research last night. Not Boring is the number one Substack newsletter on business. If Packy decided to switch to the technology category, from everything I can tell, he would be number one there, too. In fact, even in the crypto category, there are only two newsletters with more reach, and they've existed much longer. Not Boring is only a year and a half old. The Not Boring story isn't just impressive because of its explosive growth. Packy is reinventing the media business model, and simultaneously, the startup investing business model. He's done all this with a very distinct personal flair, writing in a unique, whimsical voice that makes us all just wanna have fun and play the great online game. And we're very lucky that he is a part of our liquid super team here at Acquired, so he could join us today, live, to help tell the story. Welcome, Packy.

   12. PMPacky McCormick2:13

       That was amazing. Thank you, Ben and David. Great to be here.

   13. BGBen Gilbert2:18

       I was doing my best, uh, my best Packy impression, trying to write, you know, whimsically in the unique style you've cultivated.

   14. PMPacky McCormick2:24

       It was beautiful. [chuckles]

   15. DRDavid Rosenthal2:26

       Got some good buzzword bingo in there with Not Boring piece titles over the y- I wanna say years, but it hasn't been years. It feels like years.

   16. BGBen Gilbert2:33

       I had two-

   17. DRDavid Rosenthal2:33

       Feels like you've always been here.

   18. BGBen Gilbert2:34

       I had two more. I cut them. It, it, it turned into just, like, a long series of Not Boring titles. Anyway, Packy, uh, we do have to let you know, this is not gonna be all softballs. We're gonna, like, actually do the, the full Acquired deep dive here, if that's okay with you.

   19. PMPacky McCormick2:48

       I mean, Acquired is... I think, particularly for the first year when I wrote about SoftBank, when I wrote about Tencent, when I wrote about all these companies, like, getting deep, the work that you did to, to go deep on those companies was hugely instrumental in being able to write those pieces. So I would expect nothing less than the full Acquired treatment.

2. 3:07 – 7:09

   Housekeeping: Acquired LP Show feed + sponsor setup (Pilot)

   1. BGBen Gilbert3:07

      All right, let's do this. Well, listeners, we have a huge announcement, a gigantic, exciting piece of n- news, uh, to share with all of you today. For the 98% of you out there who have not joined the Acquired LP community, we are opening up every single episode of the LP Show back catalog to you today. We have created a new public podcast feed in Apple, Spotify, or wherever you get your podcasts, called the Acquired LP Show. Very creative. That is right, that includes our series on VC fundamentals and our startup deep dives on pricing, marketplaces, SaaS investing with top investors and founders. And in fact, we are about to drop an episode that, right there in that feed, where I interview 15-year president of Blue Origin, Rob Meyerson, on how he sees the space landscape today. Now, of course, members of the paid LP community still get great benefits, like exclusive access to new episode for two weeks before we drop it in the public feed, the ability to join LP calls, Zoom, book club, you know, all this stuff. But if you aren't an LP and you really wanna start getting these episodes, you can click the link in the show notes or go search Acquired LP Show wherever you get your podcasts, and subscribe.

   2. DRDavid Rosenthal4:19

      Thank you to all of our LPs for being on this journey with us, and, um, we are very excited to now share all this content more broadly. There's some good stuff. Man, uh, Ben, you interviewed Joseph Gordon-Levitt the other day [chuckles] on the LP show.

   3. BGBen Gilbert4:32

      Super fun, yeah. [chuckles]

   4. DRDavid Rosenthal4:34

      So fun. [chuckles]

   5. PMPacky McCormick4:35

      You guys kind of look alike.

   6. BGBen Gilbert4:36

      Uh, we've gotten that a few times.

   7. DRDavid Rosenthal4:38

      [laughing]

   8. BGBen Gilbert4:38

      I, uh, uh, since Joe is a professional Hollywood actor, I take that as a great, unbelievable compliment, so thank you, Packy.

   9. DRDavid Rosenthal4:46

      Ben, you've g- you've got a future in, uh, in video.

   10. BGBen Gilbert4:48

       [chuckles]

   11. DRDavid Rosenthal4:49

       [chuckles] All right.

   12. BGBen Gilbert4:50

       Well, David, uh, take us into Pilot.

   13. DRDavid Rosenthal4:52

       Yeah, all right. Before we dive in with Packy, I'd like to welcome our presenting sponsor for all of Season 9, Pilot.com. Pilot is the backbone of the modern financial stack for startups, and they are backed themselves, as you know, by all-star investors like Sequoia, Index, Bezos Expeditions, and Stripe. They are truly the gold standard in startup bookkeeping, including maybe solo corporations that we'll have to dive into here on this episode. Uh, now over to our conversation with Pilot co-founders Waseem Daher and Jessica McKellar. So for this episode, let's talk about how Pilot actually works. You have both software and a large team of human accountants and finance professionals. What does the software look like, and how do the humans and the software interact together to help your customers?

   14. SPSpeaker5:46

       Our interface to you is that you have this really delightful and useful way of understanding your finances, and you have a person who understands you and your business, and engages with you on questions that we have for you, questions that you have for us, insights about your business.... under the hood, we're using software to ensure an exceptionally correct experience and consistent experience, and then we're also able to use software to surface key observations, insights, concerns about your finances so that you can engage on those in a really accessible way, and also with a person, if you want to.

   15. DRDavid Rosenthal6:29

       I love that answer, Jessica. You know, one thing I've heard Waseem say in the past about Pilot is that it's like an Iron Man suit for your finance professionals that you have working at Pilot, and I just love that. Pilot is the Tony Stark of accountants for your customers. Thanks, Waseem and Jessica. You can learn more about Pilot and whether they can help your company, solo or otherwise, eliminate the pain of tax prep and bookkeeping by going to Pilot.com/Acquired. And all Acquired listeners, if you use that link, you will get twenty percent off your first six months of service. Thank you, as always, for being with us this season, and go check them out.

3. 7:09 – 8:37

   Who is Packy McCormick? The identity problem of a modern creator-founder

   1. BGBen Gilbert7:09

      Thank you, David. Well, before we dive into history and facts, we should say this show is not investment advice, though David and I are both investors in multiple Not Boring entities. So not only are we conflicted, we want to be extremely open about that. Uh, we definitely have investments that we are discussing today. This show is for informational and entertainment purposes only, and I promise you it will be both of those.

   2. DRDavid Rosenthal7:31

      All right, so to kick this off, we gotta, you know... Look, we're gonna do the whole Acquired treatment on you, Packy, but, um, [chuckles] I gotta start. The first place I went when I was like, "All right, I'm gonna start researching, build the script here for the Not Boring story," I went to your LinkedIn. You know, I know that's kind of a boomer thing to do, but, uh, I did, and, um, it, uh, it lists-- You are listed there as the, quote-unquote, "founder of Not Boring." How on earth did you decide on what to put there? [chuckles]

   3. PMPacky McCormick8:03

      It's a really tough question for me. Still, when I get asked to do... You know, if I'm going on a panel or joining, you know, a podcast or something, I get asked to send over a short bio, and sometimes-

   4. BGBen Gilbert8:12

      Or CNBC.

   5. PMPacky McCormick8:13

      Or, you know, if I'm on CNBC, or I get asked for a short bio, uh, bio, and, and sometimes it's writer, sometimes it's author, sometimes it's founder. I don't know really what I do or how to describe what I do, and then if you m- mix that in with Not Boring cap, like, the whole thing gets very confusing. Founder feels like a catch-all, like I did definitely start this thing, uh, and so anything else beyond that I think is subject to change.

4. 8:37 – 16:49

   Origins: childhood ‘newspapers,’ humor as a weapon, and the work-ethic engine

   1. DRDavid Rosenthal8:37

      Love it. You are definitely the founder of the Not Boring empire. [chuckles] All right, so let's tell the story. We will start back in... I actually couldn't find this. This is something I couldn't find. Uh, I'm assuming you were born in either 1986 or 1987.

   2. PMPacky McCormick8:53

      1987.

   3. DRDavid Rosenthal8:55

      1987.

   4. PMPacky McCormick8:56

      January 26, the same birthday as-

   5. DRDavid Rosenthal8:59

      Ooh

   6. PMPacky McCormick8:59

      ... Wayne Gretzky, Vince Carter, you know, a lot of the great athletes.

   7. DRDavid Rosenthal9:03

      Okay, so January 26, 1987, in Bryn Mawr, Pennsylvania, just outside Philadelphia, there's the birth of a baby boy named Patrick?

   8. PMPacky McCormick9:15

      Patrick.

   9. DRDavid Rosenthal9:16

      Also known as Packy McCormick. So Urban Dictionary tells me that Packy is a very common diminutive form of the name Patrick that is especially popular amongst residents of County Cork, Ireland. Is that where your family is originally from?

   10. PMPacky McCormick9:32

       I believe so. My dad has done kind of the Ancestry.com deep dives. I think we're, you know, on his side of the family, I think we're probably fourth generation over here, uh, and so we think it's County Cork, but not one hundred percent positive.

   11. DRDavid Rosenthal9:44

       Nice. All in the Philadelphia area?

   12. PMPacky McCormick9:47

       All in kind of the Lehigh Valley. Allentown is where my dad grew up. We have a bunch of family in Scranton, so the Joe Biden country.

   13. DRDavid Rosenthal9:55

       Yeah, totally. Uh, Billy Joel, Allentown, growing up in Allentown. Um, so what were you like as a kid? Like, uh, you know, i- is there anything, like, ooh, any, any little glimmers of the future Not Boring empire that were popping up, uh, when you were growing up?

   14. PMPacky McCormick10:14

       Yeah. So I, I think probably there, there are a bunch of glimpses. I used to make these little books or newspapers on Post-it notes. So one of my dad's-- My dad was a consultant, uh, at Arthur Andersen, uh, and, but luckily got out before Enron, thank God. Um, but one of his early clients was the Miami Herald, and so when I was, like, you know, six years old, I would make these little Post-it note versions of the Miami Herald. I also have this one, which is creepy, and maybe we cut this part, but, uh, it was called Golden Memories of a Young Boy's Life. And so I had all these au pairs, and they would take me in, like, you know, the women's locker room at the pool or something like that, and I was, like, a five-year-old kid, and I would come home and draw stick figures of boobs, [chuckles] uh, on, in this little book called Golden Memories of a Young Boy's Life.

   15. DRDavid Rosenthal10:57

       [chuckles]

   16. PMPacky McCormick10:57

       So that was probably the earliest version of, of Not Boring.

   17. BGBen Gilbert11:01

       Wow, you, you could have taken a very different career direction after that.

   18. DRDavid Rosenthal11:04

       Yeah. [chuckles]

   19. PMPacky McCormick11:04

       I could have. I wasn't a particularly good artist, you know, I don't-

   20. BGBen Gilbert11:07

       [chuckles]

   21. PMPacky McCormick11:07

       ... don't know if anybody would've, uh, would have signed up-

   22. BGBen Gilbert11:10

       Which actually has carried through perfectly. [chuckles]

   23. DRDavid Rosenthal11:12

       Perfectly to today. [chuckles]

   24. PMPacky McCormick11:14

       I'm still not a good artist. I think it's part of the charm.

   25. DRDavid Rosenthal11:16

       [chuckles]

   26. PMPacky McCormick11:16

       Uh, but, you know, even in, in high school or middle school... In middle school, we had an eighth-grade teacher, Mr. Algeo, who, uh, would make you write a composition or an essay if you got in trouble, and so for me, I would actually sometimes try to get in trouble-

   27. DRDavid Rosenthal11:29

       'Cause for most kids, that's punishment. Like, for me, like, if I have to write as much as you write, like, I, I, I couldn't do it. There's no way. [chuckles]

   28. PMPacky McCormick11:36

       I mean, I did cross country and track in high school, too, and that was kind of a similar vibe, where for most people, that's punishment, making them run many miles, and I love that. But Mr. Algeo, you know, you'd have to write a composition, and I would love to do it because I would try to write a composition that was so funny that Mr. Algeo would let me read it in front of the class. Or, you know, in high school, I would try to write essays that were a combination of, like, very well done and well-researched and all that, but funny, uh, so that, you know, even my most serious teachers would have to laugh and give me a good grade, despite the fact that I, that I turned them into a joke. So I think kind of always combination of-... class clown with the backing of kind of serious research. [chuckles]

   29. DRDavid Rosenthal12:11

       That's exactly what I was gonna say. Like, you know, most, uh- it's pretty rare to find those two combinations together in one person, right? Like, somebody who is both the class clown and has a work ethic. [chuckles]

   30. BGBen Gilbert12:24

       Well, and, and, and I think that comes through in Not Boring. Like, I think, uh, that, uh, all of us who read every or close to every one of your posts, I think that's the charm. Like, that is the style, is that you're diligent. You've written many times about how, like, the process works, and how you go into your basement and, you know, like, spend the time and do the research and start writing and tear it down and write something... I mean, there's real diligence there, and for sure, you are the class clown of serious business newsletter writers. [chuckles]
5. 16:49 – 29:26

   Duke to Wall Street (in the recession): Enron vibes, public finance, and the MBA that never happened

   1. DRDavid Rosenthal16:49

      So I maybe... I, I may be reaching for threads here, but, like, it's funny, that story, uh, kinda- I mean, that's kind of what you happened in Not Boring, right? Like, you got it wrong. [chuckles] You- the whole thing was like... I mean, we're gonna get into it in a sec, but it was an in-person social club, right? [chuckles] And, uh, and here we are. Uh, so okay, before we get there, so you go to Duke. Uh, you were on the debate team at Duke, right? [chuckles]

   2. PMPacky McCormick17:15

      I was.

   3. BGBen Gilbert17:16

      Shocking.

   4. DRDavid Rosenthal17:17

      We, we were able to unearth some, uh, [chuckles] some pretty awesome photos from, uh, from that time, that maybe we'll link to in the show notes, but...

   5. PMPacky McCormick17:24

      I mean, I was, I was incredibly cool. I was, uh, you know-

   6. DRDavid Rosenthal17:27

      [laughing]

   7. PMPacky McCormick17:27

      ... in the debate club. I was, uh, in an a cappella group. Uh, I... You know, there were a couple of big all-male a cappella groups. I was in the cool one. On the debate team, we were the, you know, me and my partner, who was my best friend from high school also, we were, like, the cool team. So I was, like, in all the nerdy things and tried to be cooler than I was probably in, in all of those things, but that was certainly my, my kind of college vibe, was just getting involved in, in a lot of different things.

   8. DRDavid Rosenthal17:51

      So, okay, you graduated in 2009, which also, naturally, was the year that my wife, Jenny, graduated from college. And, uh, I mean, I remember I graduated in '07. I sailed through. I was a French literature major. I get the investment banking job. I'm like: "Oh, this is good." Then, of course, I got my butt kicked on, on- when I actually got to Wall Street. But, um, so-... you got an investment banking job in 2009. Like, nobody got investment banking jobs in 2009. This was the middle of the recession. How, you know, like, how did this happen? Was this something that you, like, worked all through college to get? Like, what-

   9. BGBen Gilbert18:26

      Also, just to drive David's point home here, even French lit majors could get investment banking jobs in 2007, and by the time the door slammed in '09, it took something special, Packy, for you to, to get there.

   10. PMPacky McCormick18:39

       Yeah, so I, I was, to be fully fair, uh, kind of an investment banking lite in public finance, but it started the summer before in 2008. When I got my internship, things were actually still pretty good. So I got an internship at Bank of America on the energy trading desk. That was a wild experience in itself because Bank of America's energy trading desk was all ex-Enron people. Uh, and so they were not psyched to not be at Enron anymore and not psyched to be on a desk that didn't take physical delivery. So there are two types of kind of energy trading desks. Some, like, you know, the bigger banks, Morgan Stanley, all of that, which will take delivery if they need to, of barrels of oil or whatever else. Like, those are the kind of serious desks, and then there are more just pure financial desks like we had, uh, at Bank of America. Worked my butt off that summer. Like, you know, there's the intern programs, and there's drinks, and there's speeches, and there's all these things that you do when you're, uh, an intern on Wall Street. My desk wouldn't let me go to any of those things. Like, I, I had to sit there, and you don't do anything when you're a trading intern. Like, you literally sit on these people's shoulders. You're not allowed to trade. You're not licensed to trade, so you sit on their shoulders-

   11. DRDavid Rosenthal19:44

       Wait, you're not licensed? You don't have the Series 7, Series 63, is that the other one you need?

   12. PMPacky McCormick19:48

       Exactly right. So I, I, you know, I, I asked them dumb questions throughout the day while they were trying to focus on these multimillion-dollar trades. It was, like, the worst experience. They didn't like me being on the desk, but they also didn't want me to have any fun, so they wouldn't let me go to any of the other things. Uh, the summer before my internship, uh, they, they didn't like the intern, and so they took him out drinking until, like, 4:00 a.m., and then when he came in a little bit late the next morning, they marched him to the HR team's office and got him fired, and so that was kind of the... That was the environment that I was coming into.

   13. DRDavid Rosenthal20:16

       This is like liar's poker.

   14. PMPacky McCormick20:17

       Totally. But, you know, there's definitely the, the work ethic there, where I just didn't let it bother me, and so got an offer to come back. Bank of America merged with Merrill Lynch. I, I don't know what the league tables look like now, but certainly Merrill Lynch was-

   15. DRDavid Rosenthal20:29

       Merged, quote, unquote

   16. PMPacky McCormick20:30

       ... higher quality. Merged, quote, unquote. So we bought them, uh, but there were higher-quality interns, quite frankly, uh, at Merrill Lynch. Uh, and so when we merged, I guess the other problem was we all got put at, on the Bank of America side in a rotational program. So you got your offer from a specific desk, but you came back and had to rotate around different desks, whereas Merrill got hired into specific desks. So all the Merrill kids, for both of those reasons, they were probably smarter than I was, and, uh, and they already had their desk kind of placement locked in. They got their desk. We rotated around, and about half the people in the trading program ended up getting spit into public finance, which, for those listening at home, is municipal bonds. So I worked, you know, on the State of New Jersey's [chuckles] uh, the State of New Jersey's bonds that were backed by their tax obligations or the Pennsylvania Turnpike when they wanted to build new roads and issued debt to do that.

   17. DRDavid Rosenthal21:19

       Wow, that sounds kind of, uh, boring.

   18. PMPacky McCormick21:23

       [sighs] It was a little bit boring.

   19. DRDavid Rosenthal21:24

       [chuckles]

   20. PMPacky McCormick21:24

       I think hopefully, hopefully, that's the first of hundreds of funs, uh, throughout this, this podcast. But yeah, it was, it was boring, but I actually... You know, I, I liked it. I was number one in my class, kind of each of the years that I was there, and I realized, like, very early on, 'cause I had friends who were... I remember a New York Times article came out about the fact that really top-quality investment bank analysts were getting their PE offers way, way earlier, and I think they quoted two of my friends, uh, in that article. So, like, I had friends who just loved this stuff, and I just was not one of those people, so I knew that I'd, you know, want to get out of finance at some point, and so I was really just playing to get, you know, to be as, uh, in the top of my class and go to business school.

   21. DRDavid Rosenthal22:05

       So you apply to business school, right? And astute readers of Not Boring will know, or, and, and trawlers of your LinkedIn profile will note that you do not have an MBA. [chuckles] Uh, walk us through that and what happens.

   22. PMPacky McCormick22:20

       One other thing to add was, while I was in finance, I started a company called Throgo, which was a terrible name. I had bought the site for something else, and then I applied it to, uh, building this company that essentially took people from New York down to the Jersey Shore and to the Hamptons every weekend. Uh, [chuckles] so it was a party bus ride. It was so much fun, paid for my summers. I took it, you know, way too seriously and, and thought that this was gonna be my ticket to a great business school. Applied to Stanford, got summarily rejected, uh, from, from GSB. Um, ended up getting into Chicago, had my deposit down, was going to go, and then, one, I kind of visited, and it was snowing, and it was, like, May or something, you know, April or May, and I also found a company called Breather on AngelList and had just started a conversation with the founder of Breather, uh, where there was no guarantee of even an interview or anything, but I asked Chicago if I could defer. They told me, "No, I couldn't defer. Your deposit's already in." If it were Harvard or Stanford, they would've let me defer, but Chicago wants to... You know, they know that people might try to say they want to defer, so they can go to Harvard or Stanford, so they wouldn't let me defer. And so I just said, "All right, cool, not going to business school." Uh, had already quit my job, and so really spent, uh, kind of the next four months, I think, in this weird, kind of winding interview process just with Breather. Um, you know, traded pretty actively, made some of the dumbest trades in the history of the world. I think I bought Tesla during that summer at, like, 19 or $29 and sold it. I bought Facebook at $19-

   23. DRDavid Rosenthal23:51

       [chuckles]

   24. PMPacky McCormick23:52

       ... sold that. Plowed a bunch into, like, Apple options-

   25. DRDavid Rosenthal23:55

       [chuckles] God

   26. PMPacky McCormick23:55

       ... into e- into earnings, which, you know, is just not-

   27. DRDavid Rosenthal23:57

       You're admitting your mistakes here.

   28. PMPacky McCormick23:59

       Oh, I admit, admit all of it. So it was a t- uh, I bought Bitcoin at 100, sold it at 150, so, like, you know, really had a fun, a fun summer where I was-

   29. BGBen Gilbert24:06

       You got some nice little returns here, some nice pops. [chuckles]

   30. PMPacky McCormick24:08

       Yeah, a few percent pop, pretty good. Um-... So, you know, had this, had this kind of summer, uh, where I had no job. I didn't have a future job lined up, but I was interviewing and trading and making a bunch of dumb decisions that I think would kind of make me a better investor later on, but-
6. 29:26 – 39:53

   Breather: first U.S. hire, on-the-ground hustle, and learning ‘strategy actually matters’

   1. BGBen Gilbert29:26

      Yeah, so let's, let's jump to Breather.

   2. PMPacky McCormick29:28

      So yeah, so that summer, I had, you know, thrown away my money in business school as well. That deposit was gone. Terrible summer from a financial perspective, but the way that I was thinking about it was like: I'm either gonna spend the next two years not making a single dollar and paying for business school and racking up debt doing that, or I can go somewhere, anywhere really, that will pay me more than negative dollars and, you know, learn on the job and get that experience. And so that opened the door. I mean, I think when I ended up... You know, so my interview process at, at Breather was doing a bunch of really random things. I don't think they knew what they were doing from a hiring perspective. I wrote the JD for the job that I ended up getting, which was New York City general manager.

   3. DRDavid Rosenthal30:08

      How big was the company at that point?

   4. PMPacky McCormick30:10

      It was six people in Montreal, so I was gonna be our first US employee. One of my jobs was, Julian said, "There's a guy at Uber who does a job similar to the one that you want to do.... go track him down, and then get him to interview you, and then he'll tell me what he thinks. And so that ended up being Josh Moore, who was the New York City general manager at Uber. So I met him. He's, you know, remained a friend. That was a lot of fun.

   5. BGBen Gilbert30:34

      I think he works at Levels now.

   6. PMPacky McCormick30:36

      He- yeah, exactly. He's at, he's at, ah, Supersapiens' competitor, Levels, now. Um, and so [chuckles] that was one. Another was, you know, our other co-founder, Katarina, was a designer by background, and so she was like, "Go to a Marriott business lobby, and go to the Ace Hotel lobby, and then make a presentation on why they're different." And they're obviously very different, but I'm not a designer, ah, as everybody who reads Not Boring knows, and so I, like, had this whole thing about, you know, the vibe of both of the spaces, and it wasn't particularly good, but the fact that, that I did it is probably what they wanted to see. I learned later that it came down to me and somebody who ended up working for the company later, who's way more talented and smarter than I am, and they went... Julian and Katarina went point by point on both of us, in the lobby, actually, of the Ace Hotel, the night before they made their decision, and I won by one point and got the job, or else I would've had, you know, four months down the drain and absolutely nothing. [laughing] So I ended getting the job, and the job for the first year at Breather was, we needed to... So what, what Breather did was it rented out meeting and workspace, in the beginning, these very small meeting rooms for as little as half an hour at a time. So my job was twofold. My job was, first, convince landlords to rent spaces to this random Canadian company that wants random people to come in and out of the building for half an hour at a time throughout the day. So that was challenge number one, and I literally, like, got on my knees, and, in one case, this is actually like, I mean, literally, got on my knees and begged to one of the landlords to give us the space, and they ended up giving us the space-

   7. BGBen Gilbert32:01

      Oh, my God!

   8. PMPacky McCormick32:01

      ... 'cause Julian told me I was gonna get fired if I couldn't get three spaces by X date.

   9. BGBen Gilbert32:05

      And you're probably competing against WeWork for a lot of these leases, right?

   10. PMPacky McCormick32:09

       Ours were, like, really tiny in the beginning. So ultimately, we ended up competing with WeWork. In the beginning, we were looking for, like, the 150-square-foot, really quirky space somewhere in the building, where someone could come take a nap or, like, maybe get a little bit of work done. But the idea was that you should... Like, your phone should be able to unlock all these spaces that are underused throughout the city. Turns out, one of the challenges of that thesis is, in Manhattan, there's really no underused space [chuckles] in the city, and so we ended up just having to compete with whichever firm wanted to rent that space. Ended up, I think, kind of figuring out how to make that pitch, and so that was one side of it. Once we made it, we had to design and furnish and all these things, these spaces, and then we had to get people to clean them. So we worked with one cleaning company that ended up getting acquired by a company that got acquired by Google, and the day after they got acquired, they were like, "By the way, we don't wanna do these terrible five-minute jobs that we have to run all over the city for anymore. You're on your own." So some of that was me going and literally just cleaning Breather spaces. I would leave dinners with friends and whatever, kind of after hours. The other was, because I had met Josh during this process, I called Josh and was like: Hey, you have that Uber Rush thing. Is there any chance that we could get Uber Rush messengers to clean Breather spaces, since they're moving around the city anyway? And so we actually- I was the largest consumer of Uber Rush messengers in the world for a while.

   11. BGBen Gilbert33:26

       We never had that outside New York, I don't think.

   12. PMPacky McCormick33:28

       It was a New York test, that might have gotten to a couple of other markets, but really kind of a, a New York test, where the idea was, if you wanna deliver documents from one place in the city to another, or-

   13. BGBen Gilbert33:37

       Which is super common in New York.

   14. PMPacky McCormick33:39

       It was super common.

   15. BGBen Gilbert33:40

       From, you know, our banking days, we know, oh, you're always couriering documents around, and-

   16. PMPacky McCormick33:44

       Exactly, and I think part of that is probably what became Uber Eats, ultimately, is these people kind of, ah, moving around the city on, on their bikes. But we had a slider in the Uber app where I would call. Hopefully, there was somebody nearby. I would hit the button. I would drop the pin on the space, hit the button, and then have to text with that person and be like: "Hey, by the way, like, this isn't a delivery job. You're cleaning a space."

   17. BGBen Gilbert34:03

       [laughing]

   18. PMPacky McCormick34:03

       And if you go... And, and, and to be fair, these people opted in, so we had our own view, where it's only people who opted in, and they made a little bit more by doing that. But I'd be like: "All right, so this particular space, you go into the room. There's a set of cleaning supplies under the couch. There's instructions there. If you have any questions, just text me. This is my number." And so seven days a week, 6:00 AM to 11:00 PM, pretty much when we closed, I was just on my phone, texting messengers who were gonna go clean Breather. So there, there was like, you know, talking about startups not being glamorous, like, there was absolutely nothing glamorous about this. The fun part, on the, on the flip side of that, was, you know, I had equity in the company. I was our only US employee. I designed the system myself. I chose to work with, with Uber, and so it's all on, it's all on me, and the, the fun thing about startups is, it's all on you. All the crappy stuff is, you know, a product of the way that you designed the system. Uh, and so that was a really fun experience, and then, you know, hired a team, signed a bunch of leases, ah, got promoted a couple of times, and ultimately ended up kind of like running our operations and real estate and design [chuckles] which doesn't make any sense, but managed a really talented design team, uh, and a bunch of stuff that our COO didn't wanna do. I did all of that, ah, kind of globally for us, so incredible experience at Breather, but none of it was particularly easy.

   19. BGBen Gilbert35:16

       And how big was your, your team and the company by the time you left?

   20. PMPacky McCormick35:20

       So in New York, my team grew to about 25 people, and we were about half the revenue, ah, in the company, which was 10 markets. Um, and then, ah, when I got promoted to VP of Experience, which is a fancy title for a bunch of junk jobs, not junk jobs, but like n- not jobs that would normally go together.

   21. BGBen Gilbert35:38

       It's a catch-all, yeah.

   22. PMPacky McCormick35:40

       It was a catch-all, um, that, that sounded probably fancier, way fancier than it was. Um, but that was about 150-person team, including kind of our operations associates, who were full-time employees at Breather and, and cleaned and maintained the spaces, all the way to our team of designers, our customer care team, our real estate team, operations team, and all of that.

   23. BGBen Gilbert36:00

       All right, so I'm assembling sort of the, the, the cornucopia or the puzzle pieces that, that would become Not Boring eventually. I mean, you started w- pure finance, pure analysis, pure spreadsheet jockey, so disconnected from what actually happens at any of the companies or even in the physical trading of the commodities that you're looking at. Ah, then, of course, you have one of the most operational jobs one could possibly imagine, and of course, you have the entrepreneurial, um, the entrepreneurial moment before that, of, of starting your own company. Ah, now you have leadership, so you have that piece of the puzzle, too, of understanding, like, ooh, the... It turns out, actually, the hardest thing at any of these companies is the people.

   24. PMPacky McCormick36:42

       ... And that was the most amazing thing, too. I probably stayed at Breather for two years longer than I should have because I really loved the team of people that I, that I was working with. I'd say the last kind of turning point, uh, and the last kind of thing that contributed to Not Boring was we deeply over-expanded, uh, our supply because we had been given advice by people on the board and others who said, "You're pretty much like Uber. The job for Uber is to get as much supply on the map as humanly possible. You should also get as much supply on the map as humanly possible," which we did.

   25. DRDavid Rosenthal37:15

       The catch was there was actually demand for Uber. [laughing]

   26. PMPacky McCormick37:18

       There was demand for Uber, and Uber's supply could come and go, and Uber didn't have to pay them anything. We signed five-year leases and did construction, and so it was just a very different situation. So we added a space per day, uh, in 2016, 2017. For about a year there, every day, we were launching a new space. And so we were deeply oversupplied. Our gross margins were awful, negative, I think negative 25%. And then me and Ben Rolert, who now runs a company called Composer, which just launched, congrats, Ben, who was, uh, kind of our head of data science at the time, decided to spend a Christmas break just figuring out how we could fix this thing. And we had always had this thing where we only did short-term rentals, we only did meetings, whatever, but we, like, just went deep into the com- we read, like, a bunch of Ben Thompson, and we read Good Strategy, Bad Strategy, and we're like: We're gonna turn this company around using strategy. And so we wrote this, like, detailed memo full of his data science and my crazy ideas on how we could actually turn the company around by adding monthly space and competing kind of more at the margins with companies like WeWork and Knotel, and then we sent it out to the company. When we got back, we got the blessing of the exec team. We sent it out to the company.

   27. DRDavid Rosenthal38:24

       Did it have GIFs and, and, like, Taylor Swift references in it?

   28. PMPacky McCormick38:28

       I actually don't think it had GIFs and Taylor- we took this very seriously.

   29. BGBen Gilbert38:31

       You put on your serious business pants for this.

   30. PMPacky McCormick38:32

       We put on our serious business pants for once, and the company was on the li- uh, really on the line. Like, it was gonna be really hard fundraising or doing anything when we had negative gross margins and, and too much supply. And the craziest thing that happened was, one, everybody bought in and got really excited by this vision, even though it was a ton of work. Like, we had to flip spaces. Part of the thesis was, we have this crazy thing that nobody else has, which is that we can rent spaces out for as little as an hour, and we have this data science team that can price spaces for as little as an hour. So if somebody wants to rent a space for one month, and then we wanna put it on- uh, back online for hourly bookings in three days, we'll flip it back and forth, depending on what the market is telling us, which meant that for the ops team, it was an absolute nightmare. For the design team, having to design between the two types of spaces, absolute nightmare. But everybody bought in, and we turned the thing around, and we went from negative 25% margins to positive 25% margins, and, like, things were going really, really well. And so I think Ben and I were both like: Wow, strategy, like, actually kind of matters here. Like, having a plan and getting people to buy into it and having something that makes sense and fits within the market, like, all of that actually, like, it's not just BS. Like, it's a real, meaningful thing. Um, and so I think that was probably also part of why I ended up writing a newsletter that was, that was about strategy.
7. 39:53 – 42:01

   Rite of Passage & quitting from Japan: writing as therapy becomes a serious craft

   1. DRDavid Rosenthal39:53

      There's a quote from your first, uh, your first newsletter post, [chuckles] which was not called Not Boring, uh, that says, uh, uh, it's about this course that you're taking, this writing course, and it says, "The first piece I wrote for the course was an introduction to Ben Thompson, and if you check it out, I would love your feedback." [chuckles]

   2. PMPacky McCormick40:13

      It was, so- I mean-

   3. DRDavid Rosenthal40:14

      The spiritual godfather.

   4. PMPacky McCormick40:16

      Spiritual godfather, yeah. The fun thing about that course was, you know, it got me, it got me writing. I took the course because then we brought in a professional management team, and strategy was less valued, and my brain was dying, and so I decided to take a writing course, and I wrote about Ben Thompson because they're like, "You know what? Instead of starting from scratch," and I think this actually just showed up in my last piece, kind of like, "Go remix other people who you respect. Go remix their ideas, and, like, kind of just get a sense for what it feels like to write about and to write like the people that you respect." And so that's how this whole thing kicked off, by writing about Ben Thompson.

   5. DRDavid Rosenthal40:48

      And so that was David Perell's Rite of Passage course, right?

   6. PMPacky McCormick40:51

      Exactly right.

   7. DRDavid Rosenthal40:53

      And you also did On Deck at the same time?

   8. PMPacky McCormick40:56

      I did On Deck at the same time because I... after I left Breather, so, you know, it was a little bit later that I did On Deck. But after I finally left Breather, I, I had tried to quit a few times. In 2019, I took a sabbatical, went to Japan, and while I was there, I called our general counsel and was like: "Get me out of here, please." Uh, and so at that point, I decided to, to go, uh-

   9. BGBen Gilbert41:15

      Whoa, you quit from Japan?

   10. PMPacky McCormick41:18

       It was... You know, it was, the, the sabbatical was, like, the last-ditch effort to get me to stay. It was kind of like: "All right, go take a month off and see if there's any way that you'd wanna come back." And while I was there, I just realized that I did not want to, did not wanna stay there, uh, and so I quit from Japan by, by calling our general counsel.

   11. BGBen Gilbert41:34

       Does that ever work? It feels like when people get to disconnect and they're already sort of emotionally disconnected, all it does is make them more sure that they're ready to be done.

   12. PMPacky McCormick41:43

       For sure. I think it's also valuable to give, like, the team... I had a 150-person team that I think I, I got along really well with, and so I think the sabbatical is also useful in being like: "Look, Packy's away in Japan right now, and the company hasn't fallen apart, and your life is not miserable, so everything will be fine when he leaves."

8. 42:01 – 52:39

   Not Boring Club (the original plan): community-first, then COVID hits

   1. BGBen Gilbert42:01

      Yeah, that's a good point. Okay, so when you did leave, uh, and, uh, I think many people, uh, know some of your history here, you didn't start Not Boring as we know it today right away. Uh, am I right that you started two things concurrently with the Not Boring Club, this social in-person experiment, but also a different email newsletter?

   2. PMPacky McCormick42:27

      Yes. I'd, I'd had Per My Last Email going, and that was really, like, kind of a link roundup, where it was an assignment from the Rite of Passage course to start a newsletter and to get 20 people to sign up. And so while I was at Breather, I was, I was writing that, and I realized I like writing, and occasionally, I would do an essay. Um, but for the most part, it was like: Here are the five things that I've read and listened to this week that I, that I really liked.

   3. DRDavid Rosenthal42:48

      And they're all still on the Not Boring Substack. You can go read them.

   4. PMPacky McCormick42:53

      ... But if you go to permylastemail.substack.com, this, like, the day that I took it down, somebody else took the site over, and I think it's maybe-

   5. BGBen Gilbert43:01

      Ah

   6. PMPacky McCormick43:01

      ... advertising shampoo or something. It's, like, some scam that, uh, is now on permylastemail.substack.com.

   7. BGBen Gilbert43:07

      Everything turns into a link farm eventually.

   8. PMPacky McCormick43:09

      Exactly. So I had that going, and then I used that to, like, kind of just think through and write about different ideas that I had for a company that I wanted to start. I mean, like, even while I was at Bank of America, when I was in college, when I was at Breather, I always knew that I wanted to start what I thought, you know, would be a real big startup. I had just managed a big team, and I thought I'd-- I was actually interim CEO for a little while at Breather and thought that I did a fine job there, and so I was like, "Oh, I can do this." Like, every level that you go up in a company, I thought that there were, like, these godlike people above you who had all the answers, and realized that, like, they're all as dumb as me, so why not, you know, start something myself? [chuckles] And so I used writing as a way to kind of think through in public a bunch of these different ideas, and somehow, despite that tool, the best idea that I came up with was a social club that kind of combined Soho House and college extracurriculars. So I was a, a debater in high school and college, and one of the tests that I ran was starting a debate club in New York and got, you know, 20 friends to come and debate, and people loved it. I had a blast. People really enjoyed it, and so I was like, "That's a really good signal. This is gonna be a huge business because 20 people like debate club."

   9. BGBen Gilbert44:10

      This was the NYC Debate Club, right? Which you can go read about in the Per My Last Email archive. [chuckles]

   10. PMPacky McCormick44:16

       Yes, you can. Uh, but it was... I mean, like, all of this stuff is a blast, and I think it all comes from the same spot as, you know, the name Not Boring comes from, which is I had dinner with my mom and her business partner one night in New York while I was still at Breather, and her business partner asked me what I liked to do outside of work, and I, like, just did not have an answer. Like, you know, other than I like traveling and I like hanging out with my friends. Like, I had no passions, which is crazy, 'cause in college, like, that was all I did. I spent a lot more time doing other things than, than I did actually probably studying. Uh, and so, you know, I think that kind of just, like, put a, put a bug in my head that I wanted to figure out how to, like, get some of that back. And then I talked to a bunch of other people, and they realized that they had kind of the same thing going on, that once you kind of got out of school, it was work, and then it was your tight group of friends and whoever became your significant other, and then your family, but you didn't have those, like, kind of small groups that were bonded around a particular kind of passion or hobby. So I was like: Oh, cool, like that plus Soho House, that sounds like the coolest thing in the world. Let me go start that.

   11. BGBen Gilbert45:18

       And, of course, you're coming from a physical real estate company that you just spent six years at.

   12. PMPacky McCormick45:22

       Well, that was part of the thing, too, is, like, I, I just thought that, you know, if I tried to build a software business, I'd have a lot less credibility, even with investors, than if I said: Look, you know, I know how to do all of this. I can go... Like, here's the model. All the numbers work. Like, I wrote a bunch, and you can see these essays, too, trying to justify, like, how this could be a venture scale thing if you added a bunch of stuff on top and started community first. And, like, maybe that would've worked. I don't know. I mean, today, what Not Boring Club would've been is really a DAO, probably with physical locations. I think actually that model works really well for what I was trying to do. At the time, it was a real stretch.

   13. BGBen Gilbert45:58

       So did you, did you pitch any VCs or investors about investing in Not Boring Club as it was coming together at the end of 2019?

   14. PMPacky McCormick46:07

       Yeah, so I had a, a few early conversations with friendly VCs that I knew from, uh, from Not Boring, and some people actually were like: "Cool, when you actually start raising, like, let us know. This is actually pretty interesting, and, like, you'll, you'll figure it out. Like, we'll, we'll back you. You'll figure it out."

   15. BGBen Gilbert46:20

       Oh, my God, if any of these people had actually invested in Not Boring, like, wow. [chuckles]

   16. PMPacky McCormick46:25

       I know. I, I might have shut that one, shut that one down and, and started fresh, but, y- you know, it was more of a, I think, we'll back you, this idea, like maybe you can do something with it that gets interesting at some point, but we'll back you. But I got a, a bunch of advice from a bunch of other people who were like: "Don't raise money, and don't sign a lease. Please, for the love of God, don't sign a lease before you actually try to build a community, because it sounds like the other stuff is hard, but what's really hard is actually building a community around this kind of stuff." So I started a Slack group. I used the newsletter that had, you know, 400 people at the time to try to get the early applicants. Got the community up and running. We were doing, like, some, you know, book clubs. We did debate club. There were about 150 of the first people, and before we had a club to welcome people in, I was like: Great, we're gonna do a bunch of small group dinners starting in February of 2020. Uh, late February, we had, I think, our first four 10-person group dinners. They were a lot of fun. People were really enjoying getting to know each other, and then I think it was March 10th, we had these, like, separate Slack groups for each one of the dinner groups, and somebody was like: "You know what? I'm not feeling particularly good. I'm gonna just... I'm gonna bow out tonight." And other people were like, "Uh, you know what? I'm gonna bow out tonight, too, because I'm hearing a lot about this Covid thing." And so, you know, I was trying to start Not Boring Club in the middle of this Covid thing, and, [chuckles] uh, so, so, you know, we put it, we put it on pause, uh, canceled that dinner, out of an abundance of caution, canceled the next night's dinner and the next night's, and I was like: Guys, we'll be back in, you know, two weeks here.

   17. BGBen Gilbert47:55

       [chuckles] Do you remember that? We're, we're all gonna be back in two weeks, right? [chuckles]

   18. PMPacky McCormick47:58

       We're all gonna be back in two weeks. As soon as this blows over, we'll be back.

   19. BGBen Gilbert48:03

       I'm gonna put a pin in here. Uh, I was trying to figure out, listeners, how to do the thing that I did during the Uber episode, where I bring in the share price at every moment throughout history, and I, I don't have Packy's internal numbers, so I don't have the newsletter count, but what I do have is, uh, his personal Twitter following as of every month along the way. So here we are, uh, today, where Packy has 105,000, 110,000, something like that, followers. Here in, uh, February of 2020, taking us back to the story, 956 followers.

   20. PMPacky McCormick48:35

       And that was good. That was like a triple from earlier in the year before- [chuckles] ... I started writing Per My Last Email, and we can talk about this, but one of the things that I wanted to do, I, from, like, very, very early on, I would say, like: Welcome to the new X subscribers. Now there are Y of us here.

   21. BGBen Gilbert48:51

       Ah, such a good growth hack.

   22. PMPacky McCormick48:53

       ... and it wasn't even meant to be a growth hack. It was really kind of like, just in case this works out and becomes a big thing, like, there are all these people with a big Twitter following or a big audience, like, certainly you were in that conversation, where I was like, there's all these people that seem, again, like, kind of godlike and like it was just, like, preordained that they were gonna be successful. In case this newsletter becomes anything, I just kinda wanna show, like, that I was just a random, unemployed idiot who started writing this thing, and so we can kind of like track the whole progression of number of subscribers and all of that throughout the, throughout the journey.

   23. BGBen Gilbert49:24

       It's so funny you had that impression of us because, uh, I had, like, zero credibility before starting Acquired. I mean, I felt exactly like you did. Like, I had these startup experiences, and I've worked at this-

   24. PMPacky McCormick49:34

       Well, to be fair, there was a front-page Seattle Times article [chuckles] about you before, uh, you started Acquired, but-

   25. BGBen Gilbert49:41

       One day, one moment in time. Yeah, but, but Packy, like, I know that exact feeling, and it's so funny how, like, at some point, i- and, and there's no, like, clear moment in time when it changes, but at some point, then people look at you like you're on the other side of that valley, and you're like: "Wait, how did I get to the other si- What?"

   26. PMPacky McCormick50:00

       It's crazy, and like, you know, I, I try to be the same idiot that I was then. It, it is... You know, as you know, like, I, I still tweet dumb stuff, and maybe that's good, and maybe, like, the SEC is gonna knock down my door at some point. But I'm, like, really trying to just be the same person that I've been the whole time. Uh, not in any, like, you know, fame hasn't changed me, but really just, like, I don't, I, I don't want to care that, like, a respon- uh, I'm gonna get responses from a bunch of trolls now if I say something. I really... Like, I think this breaks when I let that change me, and I, like, I get a little bit safer in what I write about because, or what I tweet about or anything, because there are more trolls out there, more people who are paying attention to what I'm writing and, and all of that. And so that's been important to me the whole time, is, is kind of remaining the same idiot that I was in the beginning.

   27. BGBen Gilbert50:45

       I think it's super important. I, I... This is the Not Boring episode, not the Acquired episode, but I, I've had a few conversations recently with people who have grown, um, a brand, a personal brand, very quickly online, and I think a lot of people make a lot of trade-offs to do that, where they play a part on the internet and play a character rather than being themselves. And y- you sort of have this magical thing, at least my perception, knowing you personally and following your work, is that they're pretty much the same person. But you've managed to, like, grow very quickly by being yourself, which is remarkable, 'cause I, I, I think in three conversations that I can think of recently, people have told me, like: "I really wish I could be more myself, but I played a, a character on the internet so that I could quickly grow."

   28. PMPacky McCormick51:33

       It's easy to make that trade-off, and I probably did a little bit of that, frankly, early on, like, where I would do more threads and different things to, like, try to boost engagement and all of that. But I still- it was, like, so small that nobody was paying attention. By the time that I had anybody kind of following, I've just decided to be myself because I'm spending so much time doing this, both writing and tweeting and meeting people and all of that, that if you're not yourself... It's not like a be true to yourself kind of thing. It's like, you're gonna have a miserable experience because all of your interactions are gonna be other people wanting to interact with this persona, or if I were writing from a different voice, everyone would expect me to write from that, and it would just make it twice as hard to both figure out the content and the voice every week. And so I realized really early on that I just needed to, like, kind of be as close to myself as humanly possible, or else it was just gonna be too much work.

   29. BGBen Gilbert52:22

       And once you admit that, you're kinda like: "Okay, well, if it works, it works, and if I don't have product market fit with some subsegment of the internet who can discover me, then, shoot, I'll take my ball and go home." But if it works, it's actually remarkably scalable for a one-person operation.

   30. PMPacky McCormick52:37

       Exactly.

9. 52:39 – 1:01:12

   Not Boring becomes the newsletter: three-month bet, Product Hunt growth, and refusing subscriptions

   1. DRDavid Rosenthal52:39

      So we can debate when you crossed this valley [chuckles] , but certainly at this point in time, you have not. [chuckles] Um, what are you feeling now in March 2020? Like, you're, you're unemployed again, but you're older, you're married. Your wife is pregnant at this point, right?

   2. PMPacky McCormick52:56

      Correct.

   3. DRDavid Rosenthal52:58

      You are [chuckles] working on a, mmm, I won't say harebrained, but, uh, [chuckles] maybe a, a, a startup idea in a physical real estate space with maybe some p- some issues with the business model.

   4. PMPacky McCormick53:10

      Not particularly venture backable business.

   5. DRDavid Rosenthal53:12

      Not particularly venture backable. What are your emotions like right now? Are you just like: "I'm happy-go-lucky, it's all gonna work out," or are you, like, kind of tearing your hair out?

   6. PMPacky McCormick53:22

      I'm, to a fault, and, like, uh, you know, everybody has their double-edged sword, and mine is optimism. Um, and so, you know, like, never, never once was there a time when I was like, uh, my life is absolutely over. You know, like, when I joined Breather and took a lower salary, and it was a risky thing, my mindset was like: "You know, my absolute worst-case scenario here is that I move back to my parents' house, and I can still eat meals, and I can still sleep in a bed, and there's a roof over my head," so, like, the floor is not that low. Certainly, this time around, you know, there's s- there's 100% an ego piece of this 'cause I have a bunch of friends who are doing really, really great things, and I was... You know, when I tried to bring Not Boring Club online, I was sitting there. I had trivia nights that I, like, spent all day writing trivia questions and making slides, and seven people showed up, and I was like: "This is with my Duke education, my expensive high school education, m- all my experience. Like, this is what I'm doing with my... This is incredibly embarrassing." And so, you know, I, I decided to kind of just let Not Boring Club, the digital version, uh, fall by the wayside. In, uh, you know, February, early February, Pooja and I decided, or learned that we were, uh, learned that we were pregnant, um, and then really, you know, COVID, COVID kind of hit, and I remember, uh, this was probably April when I decided to, like, really go all in. It was, like, a bunch of soul-searching conversations with, like, Pooja, with my mom, just, like, really, you know, pathetic, pathetic stuff here. Like, I'm, like, you know, just-... talking to my mom and being like, "I don't, you know, I don't, I don't know what to do here." And she's like, "Well, I like the name Not Boring Club. Like, maybe you should just, like, apply that to the newsletter and just go all in on, on the Not Boring thing." So that was my mom's idea to port the name over.

   7. BGBen Gilbert54:56

      Nice!

   8. DRDavid Rosenthal54:57

      Wow. Thanks, Mom.

   9. PMPacky McCormick54:59

      Thanks, Mom.

   10. DRDavid Rosenthal55:00

       We should all thank our mothers more. Thank you, Mom. [chuckles]

   11. PMPacky McCormick55:02

       Totally. Thank you, Mom. Uh, and, like, even, you know, my dad, who's always been kind of like, "Don't close off doors," and like, you know, very like, just serious about me, me making sure that, you know, I did the best that I possibly could, was super supportive of this, this whole thing. Maybe just because they saw that there was, like, nothing else on the table. I- to be fair, I could have gotten a job somewhere, but, you know, there were... I, I just didn't want to get a job yet. I didn't want to quit on the idea of being an entrepreneur and doing my own thing. Um, and so I went to the beach with my brother for a week, and it was just like, all right, like, my... What if I just start writing this, this newsletter, and what if I start writing essays? And it needs to be different than Ben Thompson. So I came up with this idea to do kind of a mix between business strategy and pop culture, and so my earliest essays were like, "Creative Destruction" and "The Mickey Mouse Club" to explain why COVID was actually a really good thing because it meant that people were no longer gonna be stuck in bullshit jobs and were gonna be freed up to go do the things that they actually wanted to do, which, you know, I think is kind of borne out and, and-

   12. BGBen Gilbert56:00

       Which is ironically also the subject of your most recent piece.

   13. PMPacky McCormick56:04

       A little bit.

   14. BGBen Gilbert56:05

       It's a different twist on it, for sure. It's, it's more about the, the sort of community and societal impacts of that, but of the same impetus.

   15. PMPacky McCormick56:12

       Totally. Yeah, I mean, I- the there are definitely some through lines through, through a lot of, a lot of the pieces. I wrote about Amazon had a fashion show, and I tried to examine Amazon's strategy through the lens of this fashion show and, you know, like, did a bunch of those like, direct pop culture X business strategy type essays. That also, like pretending to be a character, became too much, where I'd have to both think of, like, the business side of it and then also figure out what movie that business was like, and that became too much. So I kept the tone, and I dropped that, that direct thing. But, uh, yeah, I mean, I just like... I asked Puja if I could have three months to, to grow the newsletter and see if there was anything there, and, like, maybe one day I'd start making money. But for now, let me just see if I can grow this. Uh, a friend of mine, Tommy Gamba, who was at Airbnb and, uh, and getting ready to leave, helped me out on the growth side of things, and, uh, you know, just had, had this brilliant idea to launch a landing page so that we could launch on Product Hunt, and that alone, I think, took us from, uh, you know, something very small, like a thousand subscribers to two thousand subscribers, so that was a huge leap. And I remember sitting with Puja at dinner and being like: "Oh, my God, I could actually... Like, this newsletter could be a full-time thing. I have two thousand subscribers now. [chuckles] This is amazing!"

   16. DRDavid Rosenthal57:20

       You had seven people at trivia night. Now you have two thousand people on the internet. Maybe this internet thing is a good idea. [chuckles]

   17. PMPacky McCormick57:27

       The internet thing is a good... As, as we like to say, we're talking orders of magnitude difference here. That's a VC term. So-

   18. DRDavid Rosenthal57:33

       [chuckles]

   19. PMPacky McCormick57:33

       ... Um, yeah, so, I mean, things, like, kind of started looking up from that point and wasn't making any revenue for a long time, and I still remember having conversations, like, deeper into the pregnancy, where it was, like, clearly going to be a thing, and I had planned to turn on subscriptions and decided to keep holding off on that because I really liked the growth. And I had conversations with Puja, where she was like: "Are we gonna do, like, a revenue thing here?"

   20. DRDavid Rosenthal57:56

       [laughing]

   21. PMPacky McCormick57:56

       And mind you, now we're living at, at my, at my in-laws' house in New Jersey during COVID, and I was writing from-

   22. DRDavid Rosenthal58:01

       With her parents.

   23. PMPacky McCormick58:02

       With her parents, and I was writing from a basement.

   24. DRDavid Rosenthal58:04

       [chuckles]

   25. PMPacky McCormick58:04

       So, like, none of this is glamorous. But she's like: "Are we gonna, like... You know, at some point, we'll need, like, health insurance and blah, blah, blah.

   26. DRDavid Rosenthal58:10

       [chuckles]

   27. PMPacky McCormick58:10

       Like, are you gonna turn on revenue?" And I was like: "No, no, trust me. If we can, like, get-

   28. DRDavid Rosenthal58:14

       [chuckles]

   29. PMPacky McCormick58:14

       ... If we can keep not having, [chuckles] not having subscriptions turned on for a while, then we can grow to a point where, like, I'll be able to turn on subscriptions, and if I convert ten percent of the audience at five dollars a month, then, like, we could be making a couple thousand dollars a month." [chuckles] Yeah, so like, that was-

   30. DRDavid Rosenthal58:26

       Which is such a fal- not that, like, subscriptions work as a business model if you architect the right way. There, there's nothing wrong with it, and ob- obviously, our friend Mario Gabriele is doing great with it, The Generalist. But, oh, that's such a fallacy, that, like, way of thinking of the like: "Oh, if I only get X percent, uh, to convert," uh, like it's... Oh, it's just... Oh, I'm so glad you went a different direction.
10. 1:01:12 – 1:09:39

    Monetization breakthrough: ad deck, early sponsors, and the ‘buy an iPad’ milestone

    1. PMPacky McCormick1:01:12

       Our baby was born on October 4th. I remember I had my laptop in the hospital. Like, he was supposed to be born, like, a day later, and so I was gonna be able to finish a piece I was writing about Reliance, and so I was, like, almost done that piece, sitting in the hospital while we were waiting for him to be born, and I just couldn't get it finished. So he was born, uh, Devin, who is the absolute best. Shout out to Dev, if you're listening to this in the future. Um, but, you know, he, he was born on October 4th, uh, uh, that year.

    2. BGBen Gilbert1:01:41

       Okay, well, I asked for our tracker here. So you were talking about sort of, like, later into the pregnancy when Pooja was asking you, like, "Hey, are we gonna do this revenue thing?" I'm gonna assume somewhere end of the second trimester, beginning of the third trimester, you're at 3,500 Twitter followers when you get that question. Then we fast-forward to, you know, Devin is born. It's a big moment in your life. You're already up to 12,000 Twitter followers, so you're starting to feel like, geez, I, I'm assuming that this maps similarly to newsletter subscribers. You're kind of looking at this like, well, if it's gonna keep growing like this, and it's actually gonna grow geometrically, not linearly, we could be in good shape pretty soon. But I imagine you're probably also pinching yourself and going, "This can't continue, right?"

    3. PMPacky McCormick1:02:24

       I remember having a conversation with Pooja, and, and this is, I think, after... So I- in the summer, kind of late summer, somebody was nice enough to reach out. Chris at Market or Hire was nice enough to reach out and be like: "Hey, I like your newsletter. Are you thinking about taking advertisers?" And I was like: "Yeah, I'd love to have you advertise." And he's like: "Great, send me your deck," and I didn't have a deck. And so I surveyed the audience, and I asked them for their characteristics, and they all came back, like, exactly like you'd want, 25 to 34, uh, high-income households, leadership positions at companies, well-educated. Like, I was- I was-

    4. BGBen Gilbert1:02:57

       Owning big budgets-

    5. PMPacky McCormick1:02:58

       Yeah

    6. BGBen Gilbert1:02:58

       ... decision-makers.

    7. PMPacky McCormick1:03:00

       Exactly.

    8. DRDavid Rosenthal1:03:00

       Well, the this deck is amazing, by the way. Well, uh, it's still on the internet. We'll link to it in the show notes. [chuckles]

    9. PMPacky McCormick1:03:05

       It's still, it's still on the internet, which haunts me, actually, 'cause people reach out, and they're like: "Great-

    10. DRDavid Rosenthal1:03:09

        [laughing]

    11. PMPacky McCormick1:03:09

        ... I'd love to do a sponsorship at $1,000"

    12. DRDavid Rosenthal1:03:11

        [laughing]

    13. PMPacky McCormick1:03:11

        ... or whatever price I put in, in the deck at that point. But after I made that deck, I was like: You know what? This internet thing has been pretty amazing, and Twitter's been pretty great. I'm just gonna tweet the deck out. And so that filled up, and, you know, Public came in, and Market to Hire came in. A few other, uh, sponsors came in from that, but that filled up pretty much through the end of 2020, all of, all of my sponsorship slots, which was great. And I was like: Oh, wow! So then I remember having a conversation with Pooja, and I was like: I don't- if things go really well, I, I think maybe there's a chance that, like, in the future, we could do, like, $300,000 or $400,000 on this newsletter on sponsorships. And, like, I, I, you know... She thought it was crazy. I thought it was a little bit crazy, but I kept-

    14. DRDavid Rosenthal1:03:49

        You're an optimist

    15. PMPacky McCormick1:03:50

        ... relying on, like, yeah, optimist, and I kept relying on the math. Like, I, like, had some sophisticated formula here. I was like: Pooja, it's like, it's purely math. Like, it's just a CPM thing, and so as long as we have enough readers, and then, like, you know, the rates will grow, and this will be something that, you know, at least I can make what I was making when I was a 24-year-old in investment banking again.

    16. DRDavid Rosenthal1:04:09

        So before Chris at Market or Hire reached out to you about sponsorship, had you been thinking about advertising, or were you totally focused on one day, when we get to a certain point, we're gonna flip to subscription?

    17. PMPacky McCormick1:04:21

        No, I mean, I think the other thing about me is I have an addictive personality, and so, you know, I, I think we had probably crossed a point where I just realized that I liked the growth too much, and I realized that I liked the fact that, you know, if I was gonna be spending all of this time, like, you know, 40, 50 hours to write an essay, I didn't want 1,000 people to read that essay, and I wanted people tweeting about it and talking about it and all of that. And so at some point, I realized it was probably gonna go ads. I just, like, hadn't made the leap because I thought even ads would, would slow growth and that people wouldn't like me doing ads. Uh, and so I was trying to hold off on that for a little while, too. Uh, but yeah, so, th- you know, a, a few companies kind of pushed me, pushed me in that direction and proved that I could actually make a dollar doing that, which was great. There is another moment where I wasn't allowed to buy an iPad until, uh, I actually made money from Not Boring. Uh, and so finally, I had made, like, $10,000, and Pooja let me buy an iPad, so, like, a bunch of, a bunch of little wins, late 2020.

    18. DRDavid Rosenthal1:05:13

        How proud were you at that moment? Like, it's so- it's quaint now, looking back on it, but, like, these are the things along the way that I'm sure you remember.

    19. PMPacky McCormick1:05:19

        Totally, and it is a glorified Kindle for me. I read books on it, and, like, occasionally, I'll draw something and, and throw in the essay. Like, this last week's, uh, title image, I actually drew myself. It's, it's horrendous. Uh, but I, I, I was like, "You know, I'm gonna be Ben Thompson. As... All, all I need is an iPad."

    20. DRDavid Rosenthal1:05:35

        [laughing]

    21. PMPacky McCormick1:05:35

        "Like, Pooja, can I please, like, dip into savings here and get an iPad?" And she's like: "No, you don't make any money on this newsletter.

    22. DRDavid Rosenthal1:05:39

        [laughing]

    23. PMPacky McCormick1:05:39

        Like, you cannot buy yourself an iPad that you don't need. You have a computer. You're fine."

    24. BGBen Gilbert1:05:43

        Okay, so two questions for you. One, did you experience the thing where the period of time where, "Hey, this isn't gonna cover our lifestyle," is long, and then, "Hey," the period of time where, "Whoa, this is gonna more than cover our lifestyle," is long, but the period of, like, "Hey, this is great, we're, we're, like, right at break even, sustainable," is, like, remarkably short, so you sort of, like, blow by it, and then you're like: "Whoa, holy crap! I expected that to be, like, a longer period of the journey?"

    25. PMPacky McCormick1:06:17

        100%. Yeah, that, that happened really quickly, and again, to be fair, covering our lifestyle was, like, not particularly difficult when we were living in my in-laws' basement. Um, obviously, you know, like, we had a baby, and so that was a real meaningful thing. But when you have a baby, David, you know this, people send you probably, like, the first at least six months' worth of clothes and diapers and all of that kind of stuff. So you, you don't really start incurring expenses on the kid for a bunch of months, uh, and we were living in a basement, and my mother-in-law is a phenomenal cook, and so, like, you know, I was maybe paying for, like, a Wawa hoagie every once in a while.

    26. DRDavid Rosenthal1:06:51

        Yes, Wawa hoagies! Yes.

    27. PMPacky McCormick1:06:53

        It's the best. Uh, and you guys, you guys need to do an Acquired on, on Wawa at some point.

    28. DRDavid Rosenthal1:06:58

        Oh, we totally should.... total digression. My, one of my proudest moments in business school was I was in this super boring class that was, um, I forget, the title was, it was something like, you know, board management or something. And I was like: "Oh, I'm a VC, this will be really helpful." It turned out it was about, like, public company board, like, like compliance, [chuckles] and it was so boring. And so I just, like, zoned out the whole semester or the whole quarter. And then one day, I was just completely zoned out, and I hear Wawa, and I'm like: "Oh, I know all about this." And the professor was like: [laughing] "I don't know why it's called Wawa." My hand goes right up in the air, [laughing] and I'm like: "I can tell you exactly why it's called Wawa." [laughing]

    29. PMPacky McCormick1:07:41

        When I was a freshman at Duke, during freshman orientation, they did the thing where, like, they had improv comedy or something, and all the freshmen went to it, and they would call a couple people up on stage, and they'd ask you questions like: "What do you miss most about your hometown?" And I was like, "Wawa!" And, like, the six people from Pennsylvania and New Jersey cheered, and everybody else was like: "What is this guy talking about?" So that was the beginning of my, my college career.

    30. BGBen Gilbert1:08:01

        For us Ohioans, that is, uh, Swensen's.
11. 1:09:39 – 1:39:28

    The ‘Thursday sponsored deep dive’ model: reinventing sponsored content and redefining integrity

    1. BGBen Gilbert1:09:39

       Yeah. Okay, so then that leads me to question number two, which is, y- you have pioneered a pretty unique sponsorship format. Like, we thought we pioneered a unique sponsorship format in, in the, the presenting sponsorship, where you'd- we, like, really throw our lot in with, with the presenting sponsor for, for three months. Shout-out to Pilot.com, Albemarle, website, you know, uh, everything, interview on the, the top of the show. And then here comes Packy McCormick and says: "You know what? Like, every week, one of the two posts that I do is gonna be pure, unadulterated, I'm getting paid by the subject to write this. I am doing the thing that is gonna make classically trained journalists, like, freak out, and I'm just gonna own that." How did you come to this, and, and how did you... What were your fears around it? How did it come to be, all that?

    2. PMPacky McCormick1:10:29

       Totally. So I'm gonna get the origin story somewhat wrong. I'd started talking to Nick Abate at, that Main Street, and if you use Twitter, you've probably gotten a sponsored tweet from him about using Main Street. Also happens to be a phenomenal guy. Love, Nick. Thank you. And he was like: "By the way, like, these posts that you write on companies, like, you could write those on startups, and I bet people would be willing to pay." And he had just come over from Shrunk Capital to run marketing at Main Street, and he's like: "You know, we'll be the first ones who, who do this." And I was like: "All right, cool. Let's try it. Like, I'm gonna caveat the hell out of it and tell everybody right up front that it's sponsored, but, like, I think Main Street is really cool, so I would actually love to write about Main Street and explain, and, like, my audience is a bunch, bunch of entrepreneurs and founders, and I bet my entrepreneur and founder audience would love to make money back from the government that otherwise they might not have. And so Main Street will get you kind of your tax credits back in, in an easy way."

    3. BGBen Gilbert1:11:21

       By the way, what, what month was this, that you're having this conversation-ish?

    4. PMPacky McCormick1:11:24

       This was also... This was actually pretty early in the sponsorship journey, so this was probably also in, like, the August, September range.

    5. BGBen Gilbert1:11:31

       Okay, so still at ten thousand-ish Twitter followers?

    6. PMPacky McCormick1:11:35

       Still at ten thousand, ten thousand-ish Twitter followers. And it ended up... You know, so my fears were, obviously, like, this is not what you're supposed to do. You're not supposed to use a newsletter to shill. Sponsored content is a sturdy word because, you know, at a normal, you know, journalistic institution that has integrity, there's a wall between the people who write, you know, the, the actual journalists and the people who write sponsored content, and it's this thing that is, like, optimized for SEO and, like, kind of, like, clickbaity and, like, all that kind of stuff. So sponsored content, like, does not have a particularly great name. But I was like: All right, so if I do this, like, really, my kind of bar for myself has to be as high as it would be writing a normal piece, and I'm only gonna write about things that I'm actually bullish on and, you know, companies that I would actually invest in myself. And this is before there was a fund or anything, but, you know, that I'd put my personal money into. Uh, and so that was kind of the bar that I set for myself, and I was like: You know what? I'm gonna, like, ask the audience even, like: Did you hate this? Like, please let me know if you hated this. And I- probably one, you know, one or two people every time I write a sponsored post is like, "You're shilling. This is sponsored. No sponsored content, please." But the vast majority either don't care, although the open rates are actually, like, fairly consistent, maybe a little bit higher on the Monday pieces, uh, or they get something out of it. So, you know, Main Street, a bunch of people went and got a bunch of money back, so they loved that. It's interesting because I serve a bunch of different audiences. When I talk to founders for Not Boring Capital now-... A lot of their favorite pieces actually end up being some of the sponsored posts because I get behind-the-scenes access into some of these really fast-growing, successful startups and get to write something more detailed on them than anybody else has written before.

    7. BGBen Gilbert1:13:11

       Oh, yeah. I am an investor in Modern Treasury, and I learned a lot about the company from your recent sponsored post on Modern Treasury. [chuckles]

    8. PMPacky McCormick1:13:18

       Yeah, even Ben Thompson, on his podcast, I think it was back in February, without calling me by name, was like:

    9. BGBen Gilbert1:13:24

       [chuckles]

    10. PMPacky McCormick1:13:24

        "You know, there is, there is somebody who writes a newsletter who does this thing where the, the startups actually pay him to write about them, but it's actually kind of good because he gets more information for these companies that aren't publicly available." He was, he was kind of saying that he doesn't write about private companies as much because he doesn't have as much material to analyze, but that if I actually work with the company, I have a bunch of stuff to analyze. And I'm very honest with them that, like, I'll- I will, you know, talk about what I think isn't great if, if there are things, and I will talk about competitors in a positive light, and I will never say, just, like, you know, do a hatchet job on competitors in the piece unless the competitor is, like, a straw man. Like, you know, I talked a lot of shit on passwords when I wrote about Stitch, and that's fine 'cause nobody loves passwords. Um, but, you know, as long as I keep that bar high, and I'm, like, very honest, I say upfront every time, "This is a sponsored post. This is how it works. Here's a link to a doc that I wrote about how I choose them," people end up, uh, people end up liking the posts. And so what I was saying was, founders end up liking those because it is, like, oftentimes, they're either at the same spot in their journey, or they're a little bit behind where those companies are, and so they're learning kind of like practical, on-the-ground things that those companies are doing and can take lessons from that. So those actually feed, in a lot of different ways, really well into the fund.

    11. DRDavid Rosenthal1:14:38

        I wanna pause for a second in the, [chuckles] in the, the sort of like action movie story of the Not Boring story. And I think this is a good point to talk about a few things kind of just, like, going on in the world around you doing this. Like, um... And one, you know, o- obviously, what you're doing wouldn't be possible without all the platforms and infrastructure, you know, to Substack, Twitter, you know, what have you, all of, all of the things that we take for granted now but ten years ago didn't exist. Like, it just wouldn't be possible to have a solo corporation like Not Boring to do- be doing what you do. Even when Ben Thompson did it, he had to roll his own for so much of this.

    12. BGBen Gilbert1:15:22

        I mean, you, you are, you are operating a venture fund with no other employees. Like, uh, AngelList makes that possible.

    13. DRDavid Rosenthal1:15:29

        But it's interesting, right? Like, you said something that, uh... Uh, oh, what was the word you used when you were talking about, uh, uh... Oh, the, uh, traditional media organization would have journalistic integrity and would never do this, right? Well, what is journalistic integrity, right? And, like, I think, like, you know, post-2016 and Donald Trump and everything, like, you know, this is kind of one of those second, third-order effects of the last five years in the world and this country of like... Well, maybe, like, you know, mainstream journalism still has a great place, but maybe it's okay to also do things differently, and maybe they don't have all the truth, and maybe, maybe you can think differently about what journalistic integrity means. And then you kind of looked at this, like, ghetto [chuckles] of sponsored content, and it truly was a ghetto. Was it a ghetto because it wasn't, didn't have integrity, or because it just nobody tried, like, put the work in to make it great, you know? [chuckles] Like, you made it great.

    14. PMPacky McCormick1:16:29

        Yeah, there's, there's a lot to, a lot to unpack. So first of all, the platforms, like, you know, I'm all in on Web3 now, certainly rely on Web2 platforms in a really big way. The most beautiful part about Substack is because they've taken such a strong stand for subscriptions and against advertising, no one on their team has ever even reached out to me. Uh-

    15. DRDavid Rosenthal1:16:48

        Whoa!

    16. PMPacky McCormick1:16:48

        ... and so I've paid zero dollars for my main platform-

    17. DRDavid Rosenthal1:16:51

        Oh

    18. PMPacky McCormick1:16:51

        ... because they wanna pretend like ads don't exist, and I hope they don't hear this and-

    19. DRDavid Rosenthal1:16:54

        That is-

    20. PMPacky McCormick1:16:54

        ... and start charging me.

    21. DRDavid Rosenthal1:16:55

        They've never reached out to you?

    22. PMPacky McCormick1:16:57

        Never reached out. Uh-

    23. DRDavid Rosenthal1:16:57

        Oh, my God. [chuckles]

    24. PMPacky McCormick1:16:58

        Yeah, so, you know, uh, that, that is just, like, kind of this happy accident where my main platform ends up being free. And so people will pitch me-

    25. DRDavid Rosenthal1:17:07

        [chuckles]

    26. PMPacky McCormick1:17:07

        ... kind of new newsletter platforms all the time, and they're like: "Bet you're pretty bummed that you're paying 10% of your revenue to Substack, right?" I'm like: I actually haven't paid anything to Substack.

    27. DRDavid Rosenthal1:17:15

        [chuckles]

    28. PMPacky McCormick1:17:15

        Twitter is free, and I've written about this before but it's, like, you know, the least... Actually, I pay for Twitter Blue now just out of, like, a thank you. It's a garbage product so far but, like, just as a, out of a thank you for a- all that Twitter has done, I, I pay $2.99 a month-

    29. DRDavid Rosenthal1:17:29

        [chuckles]

    30. PMPacky McCormick1:17:29

        ... for that now, so that's a cost. But, you know, these-
12. 1:39:28 – 1:53:55

    Web3 shift: from apologizing for crypto to writing the playbook (and surviving the backlash)

    1. BGBen Gilbert1:39:28

       In some ways, it would shock me, actually, if the, if... Well, I know numbers-wise, there are people who listen to Acquired who aren't, um, subscribed to Not Boring, but I don't-- in my head, I'm like: Who are those people? 'Cause I, like, I want... Like, we're a little bit less, I think, and this is something I wanted to talk to you about, like, ethereal, theoretical, abstract, uh, and frankly, like, a little bit less future-looking. Like, one question I have for you is like: At what point did you skeptically walk up to the web3 cliff and then just jump off it without a parachute? 'Cause, like, you did way more of that than we've done here at Acquired. So I can imagine maybe that's a difference in audience, but let me bring it back to, if you're not subscribed to Not Boring, oh, my God, go, go, go subscribe.

    2. PMPacky McCormick1:40:10

       Thank you. notboring.co. Um, yeah, so the web3 point, I, I think did, I think the web3 was a turning point, and so, you know, I wrote about, for a lot of twenty twenty, a lot of the... A lot of companies that are super fascinating and that I, I've always wanted to just, like, dig really deep into, and frankly, that, you know, you all have done way better work on than I have and was able to kind of build on the back of, of what you'd done there.

    3. BGBen Gilbert1:40:34

       Thank you. Not true. Different approaches. Continue.

    4. PMPacky McCormick1:40:37

       You were first, and so, like, I, I can tell you for a fact that without, you know, again, we'll go to the Tencent episode, but without the Tencent episode on, uh, uh, on Acquired, there wouldn't probably be that Not Boring two-parter on Tencent. Um, and so, you know, uh, either way, like, that is just foundational stuff, and I realized, I think, probably something that I realized when I was in finance in the first place, is that there are people who are just so much better at digging into public companies than I am and analyzing public companies than I am. And so it wasn't really kind of that clean a choice to say, like: You know what? Instead of public companies, I'm gonna do this web3 thing. But when I started writing about web3, I remember there was one, uh, one essay that I wrote, The Value Chain of the Open Metaverse, back in January, where I was really apologetic, almost [chuckles] even in the intro to that piece, that I was writing about crypto and the metaverse, and I was like: Everybody, this is really weird. My audience had become, like, fairly fin-twit and finance-heavy, and I thought-

    5. BGBen Gilbert1:41:32

       That's this year. That's Packy McCormick writing in twenty twenty-one, apologetically, that, "I, I'm sorry, I'm talking about crypto."

    6. PMPacky McCormick1:41:39

       Right? I mean, it shows how much the world has changed since then. This was before Beeple's sixty-nine million dollar sale and a bunch of stuff, but I talked about kind of some of the early, early Beeples.

    7. DRDavid Rosenthal1:41:48

       Before you tried to buy the US Constitution. [chuckles]

    8. PMPacky McCormick1:41:50

       Before I tried to buy the US Constitution with a bunch of friends. Um, but, you know, that piece ended up being, I think, really well-received because it was a, you know, again, optimistic take, I guess, on crypto. It was, like, a non-dismissive take, at least on, on what was going on, but it was really back to, like, the basics of like: All right, take a value chain. What happens when you take the middleman out? Like, I didn't like the language that was used around crypto at the time, and I think it had scared me away, where it was like: We're gonna take down the institutions, and we're gonna remove the middleman, and we're gonna blah, blah, blah. And I was like, "No, no, all right," so just taking a step back, if you take out somebody from the transaction, and you let the consumer and the creator interact directly, more value accrues to the consumer and the creator, and everybody out there reading is more likely to be a consumer or a creator than you are likely to be Facebook or Twitter. So, like, this is actually probably a pretty good thing for most of us that, you know, there's just more value that can accrue to both sides of this equation. And so that was kind of, I think, my, my jumping-off point into it when people were like: Oh, this is actually really interesting, and I didn't understand this stuff at all before, and now I really, like, I don't understand it still, but I understand it a little bit better, and I understand that maybe it's worth looking into. And I even set myself a rule that I would just do kind of, like, maybe one web3, I'd probably call it crypto back in the day before it was even called web3, one crypto piece, uh, a month, and then something else interesting happened, and so then it was two. And then other ideas that I was thinking about, like, you know, I wrote this piece called Power to the Person, which wasn't ostensibly about crypto, but it certainly was partially about the things that crypto lets a, a solo creator or solopreneur-... do, and then there are a few more articles like that where I wanted to write about something else, and crypto just kind of kept creeping back into it. Uh, and then, you know, wrote a piece, uh, that we discussed on a previous Acquired episode about Ethereum, and then dove into Solana. And I think hopefully what I can do, and I actually need to keep myself honest 'cause I'm getting so excited that I might, like, actually lose some of this, but really wanna give the, like, somewhere between this is a scam and this is, like, going to save the world and take down the institutions. I wanna be able to give that take in the middle that is like, "Here's where it's good." So I think the thing about the Solana piece maybe that worked is that it's like, here's what this thing is. Like, it's a blockchain, and that's crazy. It's a platform, and it needs to attract developers to build on top of the platform, and those developers need to attract users, and if that happens, then Solana will probably be in a pretty good shape. And, like, here's maybe one way you'd think about valuing the blockchain and, and go from there. But it- it's really that's kind of the approach that I'm trying to take to all of this, is like, "This is amazing, and let's tie it back to some sort of, like, business concept that you're familiar with."

    9. BGBen Gilbert1:44:28

       I like that. I mean, I think it is totally... That, that is a thing that doesn't exist. There, there's a clear divide between the "let's look at regular companies' world and invest in regular companies' world" and the people who have, for lack of a better phrase, gone down the rabbit hole. And, and that divide is really around business fundamentals and structure fundamentals. Because a lot of people are like, "Oh, well, with DAOs, we throw everything out, so no one even, like, has a manager. Uh, uh, and, like, of course, there's no board, and of course, there's no shares, and of course, there's no contracts, and of course, there's no employment agreements, but, like, yeah, this way, everyone gets to do what they want." And I liked your point when you were writing about the cooperation economy, where you're sort of like, "Well, at the end of the day, humans are still humans and do need to organize in ways that... Like, if our goal is to ship a product, like, we do have to figure out some [chuckles] structure to ship a product."

    10. PMPacky McCormick1:45:17

        Yeah, I mean, nothing is a panacea. I think this is a really amazing new toolkit to have, and it opens up... Again, I'm just probably have spent too much time in tech and VC, and so I say design space now too often, but it opens up this, like, new design space where you just have a new set of tools that you can build with. And so DAOs, I think, are really great in certain situations. I think eight out of 10 DAOs might totally fail because they, they have, like, kind of that leadership issue, or, like, who is the final decision-maker issue. But I think those other two are gonna do things that, like, you might not have ever thought to do with a traditional corporation, and they'll spin up faster, and they'll be more responsive. And so I think, like, nothing is all good and bad, but I think there are gonna be some emergent properties, uh, to DAOs that are really interesting and probably previously would not have been possible. And so that's a really good thing, and so I don't want people to just dismiss DAOs outright because sometimes they can be a little bit chaotic or whatever else. I mean, like, I got involved in the Constitution DAO, which was trying to buy the Constitution this week, and it shows both the amazing things, which is that you can rally a group of people around this shared mission and raise almost $50 million to go fight to win the Constitution and, and bring it back to the people. And then it's also, like, very hard to make huge decisions in a seven-day timeframe and to organize a 20,000-person Discord, all of whom has been told that they're a part of a DAO and has a voice, and so, like, what's the right balance there? Then you go into the idea of, like, progressive decentralization, which I think makes a lot of sense, which is start out kind of like a company, and then over time, particularly if you're building a protocol or something that is not as, like, consumer-facing maybe, then over time, you can kind of progressively give up control and, and cede more control to the users and the owners. So I guess, yeah, again, there the whole, the whole approach is like, here's where it's good, here's where there's issues, and, like, here's something that might kind of work, and, I don't know, let's go try it. Like, the, the worst thing you could do is just dismiss something.

    11. BGBen Gilbert1:47:07

        Yeah. Do you get blowback from people who were really into what you used to write about and are now like, "You, you gotta, like, spin something off," or like, "I, I just can't... I'm, I'm not into... I'm not buying it?"

    12. PMPacky McCormick1:47:20

        Before, I, I had, and I still have it on, but I, I just don't read them. I had my unsubscribes turned on and, and would literally go through every time someone unsubscribed and be like, "Oh, [sighs] someone unsubscribed." Now I don't care as much. I think this is kind of to your point earlier about kind of, like, getting the audience that you deserve. Maybe there's a little, a little... I'm not comparing myself to Jeff Bezos here, but, like, a little bit of the Amazon shareholder thing, right? Where, like, he had to work his ass off to get the shareholders that would actually appreciate what Amazon was doing, but then when he did, that puts you in a really great spot as a company when you have shareholders who are bought into the fact that-

    13. BGBen Gilbert1:47:52

        Well, I think the actual quote, it does make sense. The actual quote is not, "You get the shareholders you deserve," "You get the shareholders you ask for." In the long run, you get the, you get the audience you ask for. [chuckles]

    14. PMPacky McCormick1:48:01

        Exactly. And I hope, like, I- what I don't wanna do is alienate everybody who has, like, some sense of, you know, uh, that, that fundamentals have va- Like, I- those are people that I really want to read Not Boring, and I want to keep me accountable. Um, but if people are just like, "Hey, you're writing about web3, and I think it's stupid," and they leave, then that's totally fine. It's really, like, the people who are like, "Hey, you're actually, like, losing all sense of fundamentals here," like, uh, "then I'm, then I'm out," like, that's when I'll know that I have an issue. There was one- there was somebody who DM'd me after I wrote the piece on Solana, actually, that was like, "Man, I miss the old Packy when you would give us alpha, and you'd be early on things like Snap or whatever."

    15. BGBen Gilbert1:48:38

        [chuckles]

    16. PMPacky McCormick1:48:38

        And then, of course, Solana, like-

    17. BGBen Gilbert1:48:40

        Yeah, [laughing]

    18. PMPacky McCormick1:48:40

        ... three and a half X'd in the next two months.

    19. BGBen Gilbert1:48:42

        You're like, "Here, I just gave you a truckload of alpha." [laughing]

    20. PMPacky McCormick1:48:45

        [chuckles] But, like, that stuff still hurts. Like, I don't wanna, I don't wanna, like, not, you know, do the thing that I'm promising to people, but I also have been... You know, I've never had a very specific focus, and I've always been honest that I'm gonna follow whatever I think is the most interesting. It makes my schedule miserable because I pick, like, each week what I wanna write about based on what I think is the most interesting thing happening is. But, you know, I do wanna follow whatever I think is, is the most interesting thing going on.

    21. BGBen Gilbert1:49:09

        And look, like, that has attracted an audience that includes CEOs of FAANG companies, I mean, that, that are, that are active subscribers to your newsletter. So I, uh, unless they've subscribed, unsubscribed, uh, seems like it's working.

    22. PMPacky McCormick1:49:20

        [chuckles] Is that... Did Jeff Bezos send you that email?

    23. BGBen Gilbert1:49:24

        Yeah, Jeff and I... So the thing about-

    24. PMPacky McCormick1:49:25

        You're not giving him the alpha anymore?

    25. BGBen Gilbert1:49:28

        [laughing] I'm kidding. Jeff, Jeff Bezos and I have never spoken. He doesn't subscribe. Someone, I think, signed up with Satya Nadella's email address, but, like, it certainly wasn't him, and that email address has never opened an email.

    26. PMPacky McCormick1:49:36

        [laughing]

    27. BGBen Gilbert1:49:36

        So I think that was a prank. Um... [laughing] But, like, you know, I do know that, that, uh, that, you know, CEOs of big companies and all that-

    28. PMPacky McCormick1:49:42

        It's actually Pujat, that, [chuckles] no.

    29. BGBen Gilbert1:49:45

        [chuckles] That would be messed up. I was so excited.

    30. DRDavid Rosenthal1:49:48

        ... All right, so speaking of web3, uh, you wrote in your Power to the Person piece another sort of, um, crazy-sounding, uh, prognostication, that you predicted that within ten years, within a decade or two, there would be multiple trillion-dollar market cap organizations that were run, quote, unquote, "by just one person," that were, that you called solo corporations. And your point was, hey, it already exists. It's called Bitcoin. [chuckles] Nobody works for Bitcoin, and it's a trillion-dollar market cap. Um, back to Not Boring itself, it's so awesome. It's, like, incredible, and, like, Ben and I are a hundred percent in the camp that are cheering for you, that you made it to your goal of making a billion dollars in revenue this year. A kinda old-school way of thinking about that would be like, Packy is the head of the distribution in the creator economy, and one of the few people that have really broken out and are ... You know, you're gonna make a great- you're gonna be, like, an NBA player, you know, level in the- a professional player in the creator economy. Another way to think about where this could go, though, is, no, you're building a solo corporation. [chuckles] And, you know, it's not just that you're gonna make a few million dollars a year writing a newsletter. Not Boring can be something a lot more. [chuckles] Uh, how do you think about that?
13. 1:53:55 – 2:14:23

    Not Boring Capital: from syndicates to funds, transparency as strategy, and AngelList as ‘AWS for VC’

    1. DRDavid Rosenthal1:53:55

       I think it's worth spending a little bit of time on Not Boring Capital, um, which is obviously not wh- other, other... It's not web3, other than you are able to invest in web3 projects via it. But, um, it is this really interesting thing, like, and maybe it's unique to sort of our collective corner of the creator economy, but it is a real business, and it is a real step towards going from just being a... You know, I'm thinking about, like, the Oprah episode that we did, uh, uh, two years ago? A year and a half ago, whatever it was, um, where it was, was it her first agent, if I'm remembering right, who said, like: "Look, you can be the talent in front of the camera, and, like, you can make a few million dollars a year. You'll have a great life, right? Like, or you can own the production," [chuckles] you know, "and then you, and then then you can become Oprah." Right? And, um, it does feel like there's kind of this opportunity for creators now to go from just being, like, an indie version of the talent in front of the camera to a lot more.

    2. PMPacky McCormick1:54:58

       Yeah, I mean, I think certainly Not Boring Capital is a step in, in that direction. I think the three of us are very lucky that the type of content that we make is also really well aligned with doing venture capital. Obviously, there's a lot of creators who are starting to invest in startups. I'm less dismissive of that, you know, as you can probably tell at this point, than most people are because I think, you know, they probably have really deep insights into certain spaces that other people who haven't been creators and haven't built that kind of business wouldn't understand. But I think for us, in particular, we're really lucky, and, you know, Harry Stebbings falls into this camp, and a bunch of other people do as well. Lenny and Turner, uh, all fall into this camp where we're living and breathing this stuff every day. And this probably goes back to our conversation on journalistic integrity, where like, I actually don't want to do this without having skin in the game, and I don't wanna do this without kind of like-... digging in and getting involved, uh, in the companies that I'm writing about and, like, trying to help shape their trajectories. And, like, I love picking up the phone and talking to a founder about, like, not just like, "Here's this idea that I came up with and wrote about," like, kind of ab- abstractly, but like, "Here's this problem that we're having right now. How should we think about solving this problem?" And so I think, like, that is really, like, a huge benefit of being able to have both Not Boring Capital and Not Boring the newsletter, and there's all sorts of ways that they work together. And from a business perspective, it's phenomenal 'cause it does scale a lot better to run a venture fund than to show up every week and get a sponsor and then write, write an essay. But like, again, like, this wasn't even planned. Like, that's not where it ca- it really came from, like, one time where I, you know, wrote an essay to help a friend who was trying to explain how his company worked, and then he raised a syndicate with somebody else, and then that turned into my own syndicate, which turned into a fund because it was too much of a pain in the ass to write, uh, memos every time that I wanted to do a deal, and founders didn't wanna wait three weeks to see how much money I might be able to give them, and so that turned into a fund.

    3. BGBen Gilbert1:56:50

       Wait, you're telling me, as an LP in your fund one and fund two, you don't write investment memos for every single one of your packy?

    4. PMPacky McCormick1:56:58

       I, I write them up here. Yeah, no, [laughing] so I-

    5. BGBen Gilbert1:56:59

       [laughing]

    6. PMPacky McCormick1:57:01

       ... fund one I did, uh, fund one I did 91, uh, 91 investments, and not all of them have investment memos. Uh, but in, I mean, like, i- in, in all seriousness, like, I do think that all of the time that I've spent writing about all of these different kind of industries and companies and all of that, like, really helped me show up kind of prepared and thinking about what to look for in these different businesses.

    7. DRDavid Rosenthal1:57:20

       And a lot of your investments you've written about.

    8. PMPacky McCormick1:57:23

       A lot of my investments I've written about. A lot of investments, frankly, come in because, you know, I start writing about Web3, and I write something, you know, like the cooperation economy that unlocks, like, how somebody thinks about something, and then they want to start a... I've, I've had that conversation with founders a few times where they're like, "This is actually like... We make all of our employees read this because this is what we're trying to do." And so, like, that kind of helps, you know, on the sourcing and, and winning deal side. But this wasn't planned either, and so I think the next iteration of Not Boring, whatever, like, we kind of add on top here, it probably won't be planned, and it'll probably be because it makes sense with, with what I'm doing. But yeah, I, I think I could not do this, and I didn't plan it this way. I couldn't do this if I didn't have some sort of skin in the game with what's going on here and some sort of like... I, I like being honest when I get stuff wrong. Like Pilot.com, my worst call of all time, being short Pilot.com, only really the only time I've ever gotten kind of pessimistic. I like being called out when I'm wrong on stuff, and I think, you know, to be able to, to run a venture fund that says like, "Cool, here are the ideas," but then also, like, I'm putting money behind it, and you'll see the results and how well fund one, fund two, fund three did, and whether I'm just, like, fully talking out of my ass or only partially talking out of my ass and got lucky a little bit, uh, in the results of, of how these funds do.

    9. BGBen Gilbert1:58:35

       Well, it does seem like you're publishing pretty much... Like, I think on Saturday you send out the e- email to LPs, and then come Monday, you send out a public version, and it's pretty much the same. I mean, you are- obviously, there's some things you're, you're, that the companies don't want you sharing, but other than that, it's a pretty- it's a remarkably transparent way of going about venture investing. And it's also super different than, you know, classic venture capital. Like, uh, uh, did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those 91 investments?

    10. PMPacky McCormick1:59:07

        Never, and that's, that's all part of the strategy, right? Like, I mean, we all love talking about strategy, and, and strategy isn't doing everything well, it's picking what things you want to do well and, and taking advantage of those things. And so even like, you know, figuring out how to price the round and figuring out what should go into the term sheet and spending time negotiating that and then being on a board, God forbid, like, it actually just doesn't work with my strategy because, like, it is a house of cards already, where you move one thing, and, like, the whole thing breaks. And so if I'm doing kind of the more deeply time-consuming parts of a venture, it, at least as I'm currently constructed, doesn't work. But it really works very well when, you know, I can talk to a founder, and we have the specific area, either kind of internally or externally, where I can be helpful. Not to [chuckles] kind of-

    11. DRDavid Rosenthal1:59:53

        [laughing]

    12. PMPacky McCormick1:59:53

        ... you know, make fun of that, that, that venture pun, but-

    13. BGBen Gilbert1:59:55

        Put on your khakis and ask the question, yeah.

    14. PMPacky McCormick1:59:57

        Yeah, but, uh, you know, like, there, there's a bunch of things that, you know, you make trade-offs throughout, and I wrote in both the public and private memo that, like, I'm doing probably less diligence than most people on a specific company, than most people who are investing in a company will. And that's, like, an embarrassing thing to say publicly when LPs are reading that or when, like, the world is reading it. But it's a, it's a fact of the business that, like, there's just no way in the world that by myself here, while I have another job and I'm investing in 91 companies, I'm going as deep looking for the flaws in a company and, like, calling references to look up, like, what this person did wrong managerially. Like, I trust that if a good fund is leading the round or somebody that I trust is, is leading the round, that they've done that stuff, and my job is, you know, as it is with Not Boring, to look for like what can go really, really right here. And so, you know, this will either blow up totally in my face, or we're in this crazy bull market, and, you know, I should have been a lot more conservative and, like, gone for, like, VC value investing, or it'll work. But, you know, the, the whole thing is transparent.

    15. BGBen Gilbert2:00:57

        Which is a thing that's never worked, by the way.

    16. PMPacky McCormick2:00:59

        Which is a thing that's never worked. I mean, I'm, I, I do base everything on... Like, it sounds footloose and fancy-free. I do base everything on-

    17. DRDavid Rosenthal2:01:05

        Even Ho and Altus would probably agree with that. [chuckles]

    18. PMPacky McCormick2:01:08

        [chuckles] Uh, on, like, the analysis and, and the numbers and-

    19. DRDavid Rosenthal2:01:10

        Well, I think you're, um... I, I would argue, I mean, I'm sort of doing very similar things with, with Kindergarten Ventures, with, with Nat, as, as what you're doing with Not Boring Capital. But, um, so I'm arguing my own book here to a certain extent, but I would argue you're selling yourself short with Not Boring Capital, and I love how... You know, everything you've done is, like, emergent, you know? [chuckles] It, it's not, uh, uh, it's not like you cooked it all up in a, on a whiteboard. Um, but it's kinda like the content, uh, like the, like the sponsored posts, right? Like, people used to think about venture capital in a box and only one way.... you did a lot of diligence, you wrote the term sheet, you came to evaluation, you negotiated, you joined the board, you did all these things, right? [chuckles] And obviously, that wouldn't work for what you're doing. [chuckles] You know, you're writing a- y- you've got a big, big business writing a newsletter. But there's aspects that work, of what you're doing, that work way better [chuckles] than that old way of thinking. Old- not old, old, it's still valid, but than that one specific way of thinking, right? Uh, and you're able... You know, you've already scaled capital under management doing this. You could probably keep scaling even a lot further with this strategy. Um, and but what you're bringing to the table and how you're doing it is, is just this kind of new way of thinking, right?

    20. PMPacky McCormick2:02:38

        Yeah, and there's a group of people who I think are doing this, and, uh, I mean, you're certainly involved in this, and, and it's great that we kind of like... It's maybe a liquid super team, to quote myself, which is always fun. Um, but, you know, that, that's coming together and, like, sharing deals with each other and, like, trading, you know, thoughts and advice and, you know, "Here's where I think you were maybe wrong on that investment," the kind of things that maybe before you would've gotten out of a partnership at a firm, and certainly that right now you get out of a partnership at a firm. And it's not as formal, and I will still make more mistakes than probably a firm will make, at least on the, like, saying yes to things that maybe I shouldn't say yes to.

    21. DRDavid Rosenthal2:03:12

        Ah, but venture capital's never about the mistakes. [chuckles] The only thing that matters in venture capital are the ones you get right. [chuckles] And that's kind of the point, right?

    22. BGBen Gilbert2:03:19

        There may even be one founder committing fraud that you've invested in, and it kind of doesn't matter.

    23. PMPacky McCormick2:03:24

        To the best of my knowledge, [chuckles] none of my founders are committing fraud, and they're, they're all amazing. But, I mean, I- you hope that doesn't happen, right? Like, that, that's, that's... I, I don't want to, like, leave room for people to commit fraud and for me to just kind of look the other way and make a quick decision and be like, "I, I don't really care." But I'm- I am probably putting too much... Or, or, you know, I'm putting trust in the overall kind of ecosystem and, and system, um, that other people are doing their jobs well, which, again, could totally blow up in my face, or not, but that's just the trade-off.

    24. DRDavid Rosenthal2:03:55

        Well, the way you're constructing your portfolio with 91 companies is... You know, of course, look, absolutely, we don't want [chuckles] any fraud to happen. Like, that's not the goal. But y- you've kind of shifted the mindset from, like, playing defense of, like, "We're going to make sure fraud doesn't happen," but in venture capital, the zeros are meaningless. [chuckles] You know, the most you can lose is your money. [chuckles] The most you can make is 1,000 times your money. Uh, and so you wanna maximize the winners. And the thing is, because of what you're doing with Not Boring, you're getting access to these great investment opportunities that otherwise, if you were a traditional venture investor, you would have to do all of that effort and work to build it. "We're gonna take board seats. We're gonna give you great advice. We're gonna do all this stuff." For you, it's a by-product.

    25. PMPacky McCormick2:04:42

        I think that part is totally true. I mean, the, the portfolio construction thing is super interesting, too, because I spent way longer than you should spend inside of even a successful startup, at a startup that ended up failing. And so I saw, you know, the other side of that, where there are investors who, you know, were a write-off, and at some point, you just kind of stop caring about that particular company, and you move on to the next one. You really, like, I, I really don't want to take that attitude towards it. Like, if there are companies that are not doing well, I want to answer their call as quickly as the companies who are doing really, really well, 'cause, like, I know how it feels to be on the other side of that. But at the same time, like, uh, this is why I'm totally cool with founders being investors as well, and all that. Like, you should diversify and not put all of your eggs in one basket. Obviously, if you're a founder and you have 1,000 employees, or 100 employees, or even 20 employees, you have people who are relying on you. You should be giving a vast majority of your time to make sure that those people who are definitely putting all of their eggs in one basket get the best possible outcome and as much care as they need from a leader. But I do think there's obviously value to constructing a portfolio, and having been on the other side of that, I appreciate that, I think, even, even more.

    26. BGBen Gilbert2:05:46

        All right, so we're talking about portfolio construction. You invested in 91 companies. You're on your second fund. First fund was how many?

    27. PMPacky McCormick2:05:54

        $9.99 million.

    28. BGBen Gilbert2:05:56

        9.99. Second fund's-

    29. DRDavid Rosenthal2:05:57

        You couldn't get it to 10? Oh.

    30. BGBen Gilbert2:05:59

        25 million.
14. 2:14:23 – 2:38:40

    Scale limits and future optionality: solo-corp trade-offs, potential S-curve, and a16z advisory role

    1. BGBen Gilbert2:14:23

       Okay, so we're, we're sitting here evaluating, like, in all the most positive ways, and sunshine, and butterflies around this one-person corporation thing. What are the trade-offs? Like, you're a strategy person, where does it get hard?

    2. PMPacky McCormick2:14:35

       So the trade-offs right now are, like, I don't have any outside investors, right? Like, I mean, I have LPs for the fund, but if I get hit by a bus, like, Not Boring is just done. And that's, like, the extreme example and the example that everybody uses when they talk about one-person things, but that means that, like, every week, if I don't show up and write something, the momentum slows a little bit. And so it's, like, very, very, very hard, I think, from, from that perspective. Like, you'll hear zero complaints out of me, but it's really hard to take a week off because I'm worried every time that the momentum will slow, and there's not, you know, somebody else on the team who's just gonna, like, go write something else and keep the momentum going that particular week. So I think that is, like, the obvious one and the, the, the one that, you know, I don't have a solution to because I've said on the other side that if I have other people writing, maybe people don't want to come to Not Boring to read X, Y, and Z other person. That's not the point. I don't want to be an editor and make sure that we all have the same tone, and so, like, I'm kind of limited, I think, to whatever I can do as kind of one, at least, kind of front person on, on this thing. Uh, so that's one big downside. The other... I mean, like, like I said before, this is a... I guess, like, there's the whole churning group thesis, right? That if you have a big audience that is loyal and, and dedicated to kind of this, like, one particular thing, then you should be able to build businesses all around that person. Uh, and like I said, like, I have zero time to think about building other businesses around Not Boring, and so the sponsorship model is, like, phenomenal, and, you know, it works really, really well. But, you know, like, sponsorship, i- if I could be using that same kind of microphone to sell my own products, like, that probably is actually better and higher upside and, like, more equity value and all of those things. Uh, and I don't have either the capabilities or the time to, to build out those types of things, nor do I think, like... I guess here's another downside with the one-person model, that the more I do of that stuff, the more it dilutes the core thing, uh, and the more it makes it seem like kind of a shill factory. Like, advertising is just kind of part of the model, but if I were like, "Hey, you guys should also buy Packy-branded, you know, hats," they'd be like, "All right, like, maybe I'll buy a hat."

Episode duration: 3:05:50