Not Boring (with Packy McCormick)

0:00 Okay, we gotta get you over a hundred K. This episode is a failure if we don't get you over a hundred K subscribers. All right, so let me time stamp where we are right now, just so we No, we need to do. So we are at eighty eight thousand four hundred and sixty.

0:13 Oh, we can so do that. Oh, we'll juice this. Who got the truth? Is it you, is it you, is it you who we got No. Is it you, is it you, is it you

0:29 Me down Say it straight. Another story on the Welcome to Season 9, Episode 6 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.

0:50 And I'm David Rosenthal, and I am an angel investor. Based. In San Francisco, and I am Back. Sort of.

0:58 From paternity leave. An abbreviated partial ongoing paternity leave. Yeah, we're making it work. And we Are your hosts. Well today we have a first for acquired. We are covering a business that is only one person.

1:11 Not boring. The newsletter gone Media and Investment Empire run by Packie McCormick. I did some research last night. Not boring is the number one substack newsletter on business.

1:23 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.

1:45 Paki 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 want to have fun and play the great online game.

2:01 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, Packie. That was amazing. Thank you, Ben and David. Great to be here. I was doing my best packing pressure and trying to write, you know, whimsically in the

2:19 unique style you've cultivated. It was beautiful. It's some good buzzword bingo in there with not boring piece titles over the I wanna say years, but it hasn't been. It feels like yours. Feels like you've always been here. I had two more, I cut'em, it turned into just like a long series of not boring titles. Anyway.

2:36 Packie, we do have to let you know this is not gonna be all softballs. We're gonna like actually do the full acquired deep dive here, if that's okay with you. 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. Getting deep the work that you did 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. All right, let's do this.

3:03 Well, listeners, we have a huge announcement, a gigantic exciting piece of news 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 podcast called The Acquired L P Show very creative.

3:28 That is right, it 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 right there in that feed where I interview Fifteen year president of Blue Origin, Rob Myerson. On how he sees

3:47 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 want to 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.

4:12 Thank you to all of our LPs for Being on this journey with us. We are very excited to now share all this content. More broadly. There's some good stuff. Ben, you interviewed Joseph Gordon Levit the other day on the L P show. Super fun. Yeah. So fun. You guys kinda look alike.

4:28 We've gotten that a few times uh since Joe is a professional Hollywood actor, I take that as a great Unbelievable compliment. So thank you Packy. All right listeners. Now is a great time to talk about a new partner of ours here on Acquired, Lagora.

4:44 The agentic operating system that is redefining how the world's best legal teams work. Yep. It's sort of obvious that AI is gonna completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Ligora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry? So the founders did exactly what great founders do. operate with obsessive customer focus. They embedded inside a massive law firm.

5:16 For months. They sat with the lawyers just watching how the work really gets done. And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Lagora's Bet Here is interesting, since it lets each lawyer handle more complexity, any given person can increase the quality of their work. and do higher value work. And this means that the pie can grow even as each individual task takes less time. And they recently launched Lagora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

6:04 And Ligora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Ligora numbers essentially speak for themselves. When they have a head to head pilot with their top competitor, they win seventy percent of the time. Legora now has over a hundred thousand lawyers on the platform from twelve hundred legal teams in fifty countries. And crazily, they went from one million to a hundred million in ARR. In about.

6:32 Eighteen months. truly insane numbers. And that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reach for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at Lagora.com/slash acquired.

6:55 And just tell'em that Ben and David sent you. 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. 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.

7:19 All right. Look, we're gonna do the whole acquired treatment on you, Paki. But 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 I did. You are listed there as the quote unquote founder.

7:36 Of not boring. How on earth did you decide on what to put there? 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. Or C N B C Or you know, if I'm on C N B C or

7:54 I can ask for a short bio 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 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.

8:12 Uh, and so anything else beyond that I think is subject to change. Love it. You are definitely the founder of the not boring empire. All right. So let's tell the story.

8:22 I'm assuming You were born in either nineteen eighty six or nineteen eighty seven. Nineteen eighty seven. January twenty sixth, the same birthday as Wayne Gretzky, Vince Carter, you know, a lot of the great athletes.

8:37 Okay. So January twenty sixth, nineteen eighty seven, in Brynmarr, Pennsylvania, just outside Philadelphia. There is the birth of a baby boy named Patrick. Patrick. Also known as Paki.

8:51 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? I believe so. My dad has done kind of the Ancestry.com deep dives on his side of the family, I think we're probably

9:11 fourth generation over here. And so we think it's County Cork, but not a hundred percent positive. Nice. All in the Philadelphia area? All in kind of the Lehigh Valley. Allentown is where my dad grew up. We have a bunch of family in Scranton, so Joe Biden country. Yeah. Billy Joel.

9:29 Growing up in Owntown. What were you like as a kid? Any little glimmers of the future not boring empire that were popping up, uh when you were growing up? Yeah. I used to make these little books or newspapers on post-it notes. So one of my dad's my dad was a consultant at Arthur Anderson.

9:45 But luckily got out before Enron, thank God. 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.

9:58 Uh that 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. Uh in this little book called Golden Memories of a Young Boy's Life. So that was probably the earliest version of not boring. You could have taken a very different career direction after that. I could have. I wasn't a particularly good artist. Which actually has carried through perfectly. Perfectly to today. I'm still not a good artist. I think it's part of the charm.

10:28 But you know, it even in high school or middle school We had an eighth grade teacher, Mr. Algio, who would make you write a composition or an essay if you got in trouble. So for me, I would actually sometimes try to get in trouble. Cause for most kids that's punishment. For me, like if I have to write As much as you rate, I couldn't do it. There's no way. I mean, I did cross country and track in high school, and that was kind of a similar vibe where for most people that's punishment making them run many miles, and I love that.

10:52 But Mr. Algio, 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 very well done and well researched and all that, but Funny. So that, you know, even my most serious teachers would have to laugh and give me a good grade despite the fact that I turned them into a joke. So I think kind of always combination of

11:16 class clown with the backing of kind of serious research. It's pretty rare to find those two combinations to Somebody who is Both the class clown. And has a work ethic.

11:28 And I think that comes through and not boring. All of us who read Every or close to every one of your Posts I think that's The charm.

11:37 That is the style is that You're diligent. You've written many times about how the process works and how you go into your basement and 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. If there are people who've read every or close to every not boring.

11:59 Thank you. I think it takes a work ethic to read all of the not boring because it's been probably close to a million words in a year and a half at this point. To get people to read that much, it has to be both kind of informative and entertaining. I think I'm using your phrase here when I say that the reason it works is because you don't put on your serious business pants. I don't even own serious business fans. So

12:22 Where does the work ethic come from? That is certainly from both of my parents. My dad, as I said, was a consultant at Arthur Anderson and literally fly to Germany for a day and come home or fly down to Miami to go to Miami Herald and then make it home by four o'clock that night to take us to the fair and then fly back out the next morning. So it was working all of the time. My mom was getting her PhD and working and raising two kids. And so like both entrepreneurial, they both ended up starting their own kind of consulting practices. Both incredible work ethic.

12:50 And then there was just a way that they parented my absolute favorite story growing up was When I was I think in fifth grade, I had told my parents everything was going really, really well. I was probably gonna get straight A's, maybe like a B plus, but Probably not. And then I got my report card and I remember my dad was coming home from a business trip and you know, he was a fancy consultant, so he had a cell phone way back in the day in his car.

13:12 We got our report card and my mom made me call my dad and tell him the grades that I got and so I was like science, a English, a French C plus. Blah blah blah.

13:22 And he's like, All right, Packie. I'm gonna be home. In an hour. By the time that I get home, I want all of your certificates, all of your trophies. Anything that would suggest that you might be a winner, I want them in a box in the attic.

13:37 We're calling that box the loser box because you're a loser. What and my mom said that my dad went to like the Mo Market Affe School parenting for this. I actually think it was awesome because what he was mad about wasn't that I got a C plus, like that wasn't the big deal. It was that I lied all semester and said that I was doing really well in the class. Uh And so I thought that was, you know, the best parenting lesson. that I could have ever received because it was a really good lesson both in honesty and in work ethic. Because after that I actually started trying in French and I ended up taking it all the way through college and got pretty good at it. I can't really speak it anymore, but

14:07 It was a really good lesson that If you're not gonna do well, at least be honest about the fact that you're not gonna do well. And so now I think, you know, when I get things wrong and not boring, I Blair it from the rooftops and probably comes back to that moment. Yeah, you feel like an intense need to own the mistake. There's a tweet that you had at around the crypto winter where you said them's the rules, you gotta play fair and I think you were owning the fact that a lot of things that you thought were gonna go up did not go up.

14:30 I mean our ideas dinner podcast, I think, is a testament to the fact that I get things wrong all the time. Oh, we all do. So okay. So you go to Duke. You were on the debate team at Duke, right?

14:41 I was. Shocking. We were able to unearth some pretty awesome photos from that time. Maybe we'll link to it in the show notes. I was incredibly cool. I was, you know, in the debate club. I was in an a cappella group. You know, there are a couple of big all male acapella groups, I wasn't the cool one.

14:56 On the debate team, 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 all of those things, but that was certainly my kind of college vibe was just getting involved in a lot of different things. So okay. You graduated in two thousand nine, which I mean, I remember I graduated in oh seven.

15:16 I sailed through. I was a French literature major. I get the investment banking job. I'm like, Oh, this is great. And then of course I got my butt kicked when I actually got to Wall Street, but You got an investment banking job in two thousand nine. Like nobody got investment banking jobs in two thousand nine. This was the middle of the recession. Also, just to drive David's point home here. Even French lit majors could get investment banking jobs in two thousand and seven, and by the time the door slammed in oh nine It took something special packy for you to get there.

15:43 Yeah, so I I was To be fully fair. kind of an investment banking light in public finance, but it started the summer before in two thousand eight, 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 X Enron people.

16:04 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 that, which will take delivery if they need to of barrels of oil or whatever else. Like those are the kind of serious tests. And then they're more just pure financial deaths like we had at Bank of America.

16:27 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 an intern on Wall Street. My desk wouldn't let me go to any of those things. 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. Right. You're not licensed. You don't have the series seven and series sixty three. Is that the other one you need? Exactly right. So I asked them dumb questions throughout the day while they were trying to focus on these multi-million 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. The summer before my internship.

17:04 They didn't like the intern and so they took him out drinking until like four AM 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 the environment that I was coming into. This is like Liar's Poker. 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. Merged, quote unquote. Merged, quote unquote. So we bought them, but There were higher quality interns, quite frankly, at Merrill Lynch.

17:30 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 Meryl got hired into specific desks. So all the Meryl Kids for both of those reasons they're

17:47 probably smarter than I was, 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 training 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 bonds that were backed by their tax obligations or the Pennsylvania Turnpike when they wanted to build news and issue debt to do that. Wow. That sounds kind of uh boring.

18:12 It was a little bit boring. Hopefully that's the first of hundreds of buttons throughout this podcast. But yeah, 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 very early on, because I had friends who were I remember a New York Times article came out. About the fact that really top quality investment analysts were getting their PE offers way, way earlier. And I think they quoted.

18:35 Two of my friends in that article. So like I had friends who just love this stuff. And I just was not one of those people, so I knew that I'd want to get out of finance at some point. And so I was really just playing to be as uh in the top of my class and Go to business school.

18:50 So You apply to business school. And trollers of your LinkedIn profile will note that you do not have an MBA. Walk us through that and what happens. One other thing to add was while I was in finance, I started

19:03 A company called Throgo, which was a terrible name. I bought the site for something else, and then I applied it to building this company that essentially Took people from New York down to the Jersey Shore and to the Hamptons every weekend. So it's the party bus ride. It was So much fun, paid for my summers.

19:21 I took it way too seriously and thought that this was gonna be my ticket to a great business school, applied to Stanford, got summarily rejected from GSP. 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 April or May. And I also found a company called Breather on Angelist and had just started a conversation with the founder of Breather 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 deposits already in. If it were Harvard or Stanford, they would have let me defer, but you know, they know that people might try to say they want to defer so they can go to Harvard or Stanford.

19:59 So they wouldn't let me defer. And so I just said, All right, cool, not going to business school. Had already quit my job. And so really spent kind of the next four months, I think, in this weird kind of winding interview just with Breather.

20:13 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 twenty nine dollars and sold it. I bought Facebook at nineteen dollars, sold that. plowed a bunch of like Apple options into earnings, which you know is just like not what you're doing. You're admitting your mistakes here. I bought Bitcoin at a hundred, sold it at one fifty. So like You know, really had a fun a fun summer where I've got some nice little returns here. Some nice pops. Pretty good.

20:39 So, you know, had this kind of summer 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. I will say it's hard to buy and hold when you're in that position in life where like the cash is useful and a material amount of your net worth and you don't have a job. Acquired wasn't around back then, but you could listen to us have All these people on over the years saying how great it is to let compounding do its thing, or the Berkshire episodes, or even if you're a deep student of all this on your own and you know this. You kind of can't at that point in your life when you're looking to A learn or B potentially use the cache in a pretty short period of time.

21:19 I mean the bitcoin sale was a result of going to Oktoberfest with my friends while I was unemployed and they all had jobs in finance still. And so they went out to the club and I was like, Yeah, of course I can Do that. You know, I just got my bonus. And then I woke up the next morning in the hotel And I was like, you know what? That was stupid. I shouldn't have done that. I should have conserved my cash. Let me sell these stupid Bitcoin so that I like just kind of refill the coffers with USD.

21:42 And so that was why I sold all thirty eight of my Bitcoin at one hundred and fifty. Whoa, whoa. Okay, wait we can let you gloss over a couple of things here. We gotta rewind. Am I hearing you right? That you wrote your Business school application.

21:57 about starting a quote unquote company. T Bus. drunk people from Manhattan to the Jersey Shore and the Hamptons. I mean it wasn't about busting drunk people from New York to the Jersey Shore and the Hamptons. It was about community and bringing people together. I mean people who had never met somebody going to the beach town that they were going to.

22:15 made friends, people got married who met on the party bus. It was about community. But yeah, no, seriously, that is how I tried to spin my business school essays. The hard part about being a great writer Is that you can convince people that a really bad idea is a really great idea. And you just did that to me.

22:36 That is another one of those formative experiences where obviously it wasn't a startup. It was startup light. It was stupid and it was fun and it paid for my summers and all of that. When I was applying to Breather though, I mean like I had done marketing, I had done operations, I had to deal with a bunch of shitty situations and so like That company in particular, the CEO is kind of an iconoclast. He runs a company now called Practice, Julian, great guy. But he didn't care at all about the finance background, other than it proved that I could work hard and like maybe I could help with some business stuff.

23:07 But he really cared that I like got my hands dirty and like had to deal with all of the junk in just being kind of a one person running this company. So It was Definitely a silly experience, but I think it also kind of helped with the next chapter. What was the name of the party best company? Throgo.

23:22 I actually don't think I've actually technically shut down that L C so I'm one of those too. Yeah. It's funny, you know, actually doing that gritty stuff of like Dealing with Tor bus operators. You gotta do that when you're an entrepreneur and so many people that go to business school think

23:40 Oh, I'm gonna get all this glory and start some internet company and it's like Yeah, you gotta be willing to Shovel your fair share of manure here. I mean that's like the Kresaka quote about you know he won't hire or work with anybody who hasn't had

23:54 just a shitty job growing up. So you know, I'd washed dishes. I I had my fair share of Kind of those types of jobs. And I think that all helps because I mean, we'll get to very there, but that was my first year's experience was doing that exact same thing. Yeah, so let's jump to Breather. So that summer

24:09 I had 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.

24:22 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 learn on the job and get that experience. My interview process at Breather was

24:36 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 ended up getting, which was New York City general manager. How big was the company at that point? 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 uh at Uber. So I met him, he's

25:07 You know, remained a friend. That was a lot of fun. I think he works at levels now. Yeah, exactly. He's at Super Sapiens competitor levels now. And so that was one. Another was, you know, our other co founder, Katerina, was a designer by background. And so she was like Go to a Marriott. Business lobby.

25:25 And go to the aceotel lobby and then make a presentation on why they're different. And they're obviously very different, but I'm not a designer, 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 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 than I am. And Julian and Katerina 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 have had four months down the drain and absolutely nothing.

25:58 Yeah. So ended getting the job. So what Breather did was it run it out. meeting in workspace and 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

26:12 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.

26:26 Got on my knees and begged. to one of the landlords to give us the space and they ended up giving us the space. Oh my god. Cause Julian told me I was gonna get fired if I couldn't get three spaces by X State. And you're probably competing against We Work for a lot of these leases, right? Ours were really tiny in the beginning. So ultimately we ended up competing with We Work. In the beginning, we were looking for like the hundred and fifty square foot, really quirky space somewhere in the building where someone could come take a nap or like maybe get

26:53 The idea was that your phone should be able to unlock all these spaces that are underused throughout the city. Turns out one of the challenges with that thesis is in Manhattan there's really no underused space 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 a 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're like, by the way,

27:24 We don't want to 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 and 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.

27:42 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. We never had that outside New York, I don't think. It was a New York test that there might have gotten to a couple of other markets, but really kind of a a New York test where

28:03 The idea was if you want to deliver documents from one place in the city to another, which is super common in New York. It was super common. From you know, our banking days we know, Oh, you're always couriering documents around. Exactly. And I think part of that is probably what became Uber Eats ultimately is these people kind of 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.

28:32 And to be fair, these people opted in. So we had our own view where it's all only people who opted in and they made a little bit more by doing that. But I'll 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, six A. M. to Eleven PM pretty much when we closed.

28:53 I was just on my phone texting messengers who were gonna go clean Breathers. So talking about startups not being glamorous, like there was absolutely nothing glamorous about this. The fun part 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 Uber. And so it's all on me. And 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.

29:17 And so that was a really fun experience. And then, you know, hired a team, signed a bunch of leases. got promoted a couple of times, ultimately ended up kind of like running our operations and real estate and design, which doesn't make any sense, but managed a really talented design team. And a bunch of stuff that our COO didn't want to do. I did all of that. Kind of globally for us. So Incredible experience of breather, but none of it was particularly easy.

29:38 And how big was your team and the company by the time you left? So in New York, my team grew to about twenty five people and we were about half the revenue uh in the company, which was ten markets. And then when I got promoted to V P of Experience, which is a fancy title for a bunch of Junk jobs. Not junk jobs, but like Not jobs that would normally go together. It's a catch all.

29:59 Yeah, it was a catch all. That sounded way fancier than it was. But that was about a hundred and fifty person team, including our operations associates, who were full time employees of Breather and clean to maintain the spaces. All the way to our team of designers, our customer care team, our real estate team, operations team, and all that. Alright, so I'm assembling sort of the cornucopia or the puzzle pieces that would become

30:22 not boring eventually. I mean you started 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.

30:38 Then of course you have one of the most operational jobs one could possibly imagine. And of course you have the entrepreneurial moment before that of starting your own company. Now you have leadership. So you have that piece of the puzzle too of understanding like it turns out actually the hardest thing that any of these companies is the people. 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 was working with. I'd say the last turning point and the last kind of thing that contributed to not boring was We

31:07 Deeply. over expanded 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.

31:23 Which we did. The catch was there was actually demand for Uber. There was demand for Uber and Uber 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. In twenty sixteen, twenty seventeen, for about a year there, every day we were launching a new space.

31:45 And so we're deeply oversupplied. Our Gross margins were awful negative, I think negative twenty five percent. And then me and Ben Rollard, who now runs a company called Composer, which just launched. Congrats, Ben. who was 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.

32:07 But we like just went Deep into the con 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 can actually turn the company around by adding monthly space and competing kind of more at the margins with companies like we work in No Tell. And then we send it out to the company. We got back. We got the blessing of the exact team. We send it out to the company.

32:32 Did it have Gifs and Taylor Swift references in it? I actually don't think it had just intelligent. We took this very seriously. You put on your serious business pants for this. We put on our serious business pants for once, and the company was on the really on the line. Like It was gonna be really hard fundraising or doing anything when we had negative gross margins 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

33:05 If somebody wants to rent a space for one month and then we want to put it on 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 designed between the two types of spaces.

33:21 Absolute nightmare. But everybody bought in and we turned the thing and we went from negative twenty five percent margins to positive twenty five percent 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

33:38 Fits within the market, like All of that actually, like, it's not just BS, like it's a real meaningful Thing. And so I think that was probably also part of why I ended up writing a newsletter that was about strategy. to foreshadow, I think at one point early on you described not boring as if Bill Simmons and Ben Thompson had a baby. And so that clearly this is where the sort of Ben Thompson side comes from.

33:57 A hundred percent. Newsletter Post. Which is not called not boring. It's about this course that you're taking, this writing course.

34:06 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. It was. The spiritual godfather. Spiritual godfather. Yeah. The fun thing about that course was 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.

34:27 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. And so that was David Pearl's Right of Passage course, right?

34:49 Exactly right. And you also did on deck at the same time? I did on deck at the same time 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 tried to quit a few times in twenty nineteen. I took a sabbatical, went to Japan.

35:05 And while I was there, I called our general counsel and was like, Get me out of here, please. Whoa you quit from Japan? 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 want to come back. And while I was there, I just realized that I did not want to stay there. And so I quit from Japan by calling our general counsel.

35:25 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. For sure. I think it's also valuable to give like the team I had a hundred and fifty person team that I think I got along really well with. And so I think the sabbatical is also useful in being like look.

35:44 Packies. 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. Yeah, it's a good point. Okay, so When you did leave

35:55 You didn't start Not boring as we know it today right away. Am I right that you started two things concurrently? With the not boring club, this social in person experiment.

36:08 but also a different email newsletter. I had had per my last email going and that was really like kind of a link. round up where it was an assignment from the rite of passage course. To start a newsletter and to get twenty people to sign up. And so while I was a breather, I was I was writing that and I realized I like writing and occasionally I would do an essay.

36:26 But for the most part it was like here are the five things that I read and listened to this week that I really liked. And they're all Still on the not boring sub stack, you can go Read them. But if you go to per my last email dot substack.com, the day that I took it down. Somebody else.

36:41 took the site over and I think it's maybe like advertising shampoo or something. It's some scam that uh is now on per my last email.substack.com. Everything turns into a link farm eventually. Exactly. So I had that going. And then I use 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,

37:03 When I was a 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 they're all as dumb as me, so why not, you know, start something myself?

37:24 And so I use writing as a way to kind of think through and 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 kinda combines Soho House and college extracurricular, so I was 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, twenty friends to come and debate.

37:44 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 going to be a huge business because twenty people like debate club. This was the NYC debate club, right? Which you can go read about in the Pur My Last Email archive. Yes, you can. 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 notborn comes from, which is

38:05 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 like 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 because in college, like that was all I did. I spent a lot more time doing other things than I did actually probably studying.

38:28 And so I think that kind of just like put a bug in my head that I wanted to figure out how to 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 it's like oh cool, like that plus Soho House, that sounds like the coolest thing in the world. Let me go start that.

38:56 And of course, you're coming from a physical real estate company that you just spent six years at. Well, that was part of the thing, too, is like 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 this. I can go like here's the model, all the numbers work. 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 have worked. I don't know. I mean today what not Boring Club would have been is really a Dow probably with physical

39:29 locations. I think actually that model works really well for what I was trying to do. At the time it was a real stretch. Did you pitch any VCs or investors about investing in not boring club as it was coming together at the end of twenty nineteen.

39:42 Yeah, so I had a few early conversations with friendly VCs that I knew 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 we'll back you, you'll figure it out. Oh my God, if any of these people had actually invested in not boring, like wow. I know. I might have shut that one down and started fresh, but Yeah, 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 bunch of advice from a bunch of other people who were like Don't raise money and

40:12 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.

40:31 got the community up and running. We were doing like some book clubs, we did the debate club. There are 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 twenty twenty. Late February, we had I think our first four ten 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.

40:57 And somebody's like, you know what? I'm not feeling particularly good. I'm gonna just bow out tonight and other people are 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 covet thing. And so you know, we put it on pause.

41:13 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 two weeks here. Do we remember that? We're we're all gonna be back in two weeks, right? We're all gonna be back in two weeks. As soon as this blows over We'll be back. I'm gonna put a pin in here. I was trying to figure out listeners how to do the thing that I did during the Uber episode where I

41:36 bring in the share price at every moment throughout history. And I I don't have Pack's internal number, so I don't have the newsletter count, but what I do have is his personal Twitter following as of every month along the way. So here we are Today where Packy has a hundred and five thousand, hundred and ten thousand, something like that followers. Here in February of twenty twenty.

41:57 Taking us back to the story. Nine hundred and fifty six followers. And that was good. That was like a triple from earlier in the year from before I started writing per my last email. And we could talk about this. 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. Oh. Such a good growth hack.

42:19 And it wasn't even meant to be a growth act. 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.

42:37 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 journey. It's so funny you had that impression of us because 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 point to be fair, there was a front page Seattle Times article about you before uh you started acquired. One day, one moment in time Yeah, but Packy, like I know that exact feeling, and it's so funny how like at some point

43:11 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 side what? It's Crazy. And like, you know, I I try to be the same idiot that I was and it it is as you know like

43:29 I'd still tweet dumb stuff and maybe that's good. 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. Not in any like, you know. Fame hasn't changed me, but really and just like I don't want to care that like

43:43 I'm gonna get responses from a bunch of trolls now if I say something. I really think this breaks when I let that change me and I like 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 and 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 kind of remaining the same idiot that I was in the beginning. I think it's super important. This is the not boring episode, not the acquired episode, but I've had a few conversations recently with people who have

44:10 Grown a personal brand very quickly online. And I think a lot of people make a lot of tradeoff to do that. Where they play a part. on the internet and play a character rather than being themselves.

44:21 And 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 think

44:35 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 character on the internet so that I could quickly grow. It's Easy to make that

44:49 trade off. And I probably did a little bit of that, frankly, early on, like where I would do more threads and different things. So 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 kinda 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.

45:23 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've realized really early on that I just needed to like kinda be as close to myself as humanly possible, or else it was just gonna be too much work. 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 sub segment of the internet who can discover me, then shoot. I'll take my ball and go home. But if it works, it's actually

45:48 Remarkably scalable for a one person operation. Exactly. So We can debate when you cross this valley, but certainly at this point in time you have not. What are you feeling now in March twenty twenty?

46:02 You're unemployed again. But you're older, you're married. Your wife is Pregnant at this point, right? Correct.

46:09 You are working on a I won't say hairbrained, but maybe a start up idea in a physical real estate space with maybe some issues with the business model. Not particularly venture backable business. Not particularly venture backable. What are your emotions like right now? Are you just I'm happy go lucky it's all gonna work out or are you like Kind of tearing your hair out.

46:30 I'm To a fault and like I you know, everybody has their double edged sword and mine is optimism. Never once was there a time when I was like My life is Absolutely. over you know, like when I joined Breather and took a lower salary and it was a risky thing.

46:44 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.

46:57 There's 100% ego piece of this because I have a bunch of friends who are doing really, really great things. And I was, you know, when I try to bring not boring club online. I was sitting there, I had trivial nights. That I like spent all day writing trivi questions and making slides. And seven people showed up. And I was like, this is with my Duke education, my expensive high school education, all my experience, like this is incredibly embarrassing.

47:19 And so I I decided to kind of just let not boring club the digital version. Fall by the way side. In February, early February. And I learned that we were pregnant. COVID kinda hit and

47:32 I remember this probably April when I decided like really go all in. It was like a bunch of soul searching conversations with Pooja with my mom, talking to my mom and being like, 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 the not pouring thing. So that was my mom's idea to port the name over. Nice. Wow. Thanks, Mom. Thanks, Mom. We should all thank our mothers more. Thank you, Mom. Totally. Thank you, Mom. And even my dad who's always been kind of like don't close off doors and like just serious about me making sure that I did the best that I possibly could. was super supportive of 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 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. So I went to the beach with my brother for a week and was just like, all right, like what if I just start writing this newsletter and what if I start writing essays and

48:24 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 bullsh jobs and were gonna be freed up to go do the things that they actually wanted to do. Which is ironically also the subject of your most recent piece. A little bit.

48:50 It's a different twist on it for sure. It's more about the sort of community and societal impacts of that, but of the same impetus. Totally. There are definitely some through lines through a lot of the pieces. I wrote about Amazon had a fashion show and I tried to examine Amazon strategy through the lens of this fashion show and

49:07 Did a bunch of those like direct pop culture ex 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 direct thing, but Yeah, I mean I it just like I asked Pooja if I could have three months 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 Getting ready to leave. help me out on the growth side of things and

49:39 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 Something very small, like A thousand subscribers to two thousand subscribers. So that was a huge leap. And I remember sitting with Poja 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. This is amazing. Seven people at Trivia Night.

50:00 No, you have two thousand people on the internet. Maybe this internet thing is a good idea. That's a V C term, so Yeah, so I mean things like kinda 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

50:22 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 Pusha where she was like Are we gonna do like a revenue thing here. And mind you, now we're living at at my in law's house in New Jersey during Covid and I was writing with her parents. With her parents and I was writing from a basement. So like none of this is glamorous. She's like, Are we gonna like

50:42 Yeah, at some point we'll need like health insurance and blah blah blah. Like you're gonna turn on revenue and I was like, No, no, trust me, if we can keep 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. Subscriptions work as a business model if you're architect the right way. There's nothing wrong with it. And obviously our friend Mario Gabriele is doing great with it at the generalist, but Oh, that's such a fallacy, that way of thinking of Oh, if I only get X percent to convert Oh, I'm so glad.

51:13 You went a different direction. There's also the dirty secret, which it seems like you kind of intrinsically knew, which is even ten Percent. is gonna be a pretty big stretch. Creators

51:23 Can At best two to three percent. to a paid offering unless they're significantly handicapping. the main content where you'd say like sorry, every other main post is behind the paywall or something big like that. But even then, I think it's like ten, fifteen percent if you bring out your big stick.

51:42 And that Prevents growth. And so like it's hard to model out exactly how that's going to play out, but My big thing was like I was just like dicted because I had locked myself into this thing where I was telling people how many I grew every week like. I was kind of addicted to that number continuing to go up. And so I just

51:58 kept pushing off, kinda turning on subscriptions. So then that number would keep going up and Mario did it well. Lenny Rachky obviously Did it really well and and has a great business. So there are ways to do it. I think a huge difference between like someone like a Lenny and and someone like me is that Lenny's audience is so specific and like you know exactly who you are and who should be paying for that, which is

52:19 people who do product or people who do growth. And not only do they know that they should be reading that and that they need to pay for it, their companies are gonna be willing to pay for it for them. Whereas I could not imagine a company that'd be willing to pay. So somebody could read about the Mickey Mouse Club. And so that was the other kind of thing that kept me from going to the subscription model is like I just don't know if companies will be able to pay for not boring. Well, I mean that was the secret when I was at the Wall Street Journal. And this was in the days of like paid content was such a thing and it was everybody thought, Oh, the Wall Street Journal, they did it so right, the New York Times was wrong. And it's like Yeah, this is the dirty secret. Most people who pay for the journal, it's their companies that are paying for the journal.

52:54 And it's hyper specific. It's, you know, business, finance. It's the most reputable of that. Yeah, if you're gonna go the paid subscription route, it's great, but you need to architect your whole business and content strategy around that. And obviously you had taken

53:09 A different path. Packy's just gonna be Packy on the internet. Yeah, I was I was too lazy to do the subscription thing too and think about which should go behind the paywall and which shouldn't. And like could I possibly double the amount of content that I was doing so that I could still grow. And have some things behind the paywall and keep the quality. And so I just frankly couldn't figure all of that out. And so that was one of the reasons that I decided not to go that route, too.

53:31 Okay, so what month was your baby born? Our baby was born on October fourth. 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.

53:46 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. Devin, who is the absolute best. Shout out to Dev if you're listening to this in the future. Okay. Well I asked for our tracker here. So you were talking about 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 thirty five hundred Twitter followers when you get that question.

54:13 Then we fast forward to, you know, your Devin is born, spig moment in your life, you're already up to twelve thousand Twitter followers. So you're starting to feel like Jeez. I'm assuming that this maps similarly to newsletter subscribers. You're kinda looking at this like Well

54:29 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 pitching yourself in going This can't continue, right? In the summer, kind of late summer.

54:43 Somebody was nice enough to reach out, Chris at Marketer 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. 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, twenty-five to thirty-four.

55:03 high income households, leadership positions of companies, well educated. Owning big budgets, decision makers. Exactly. This deck is amazing, by the way. It's still on the internet. We'll link to it in the show notes. It's still on the internet, which haunts me actually, because people reach out and they're like, great, I'd love to do a sponsorship at a thousand dollars 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, market hire came in, a few other sponsors came in from that.

55:34 But that filled up. Pretty much through the end of twenty twenty all of my sponsorship slots, which was great. And I was like, Oh wow. So then I remember having a conversation With pushware is like I don't if things go really well. I I think maybe there's a chance that in the future we could do three or four hundred thousand dollars on this newsletter on sponsorships.

55:52 You're an optimist. Yeah, I optimist and I kept relying on the math. Like I like had some sophisticated formula here. I was like, it's like it's purely math. It's just a CPM thing. And so as long as we have enough reader, 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 twenty four year old in investment banking again. 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

56:19 One day when we get to a certain point, we're gonna flip to subscription. 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 like the growth too much and I realized that I like the fact that I was gonna be spending All of this time like

56:34 you know, 40, 50 hours to write an essay. I didn't want a thousand 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 slow growth and the people wouldn't like me doing ads. Uh, and so I was trying to hold off on that for a little while too. But yeah, a few

56:54 companies kind of pushed me in that direction and proved that I could actually make A dollar doing that, which is great. There is another moment where I wasn't allowed to buy an iPad until I actually made money from not boring and so finally I made like ten thousand dollars and push will let me buy an iPad. So like a bunch of little wins late twenty twenty.

57:10 How proud were you at that moment? It's quaint now looking back on it, but like these are the things along the way that I'm sure you remember. Totally. And it is a glorified Kindle for me. I read books on it and occasionally I'll draw something and throw in the essay like this last week's title image I actually drew myself. It's horrendous. I was like, you know, I'm gonna be Ben Thompson. It's all all I need is an iPad. Like, Pooh, 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. Like you cannot buy yourself an iPad that you don't need. You have a computer, you're fine. Okay, so two questions for you. One.

57:40 Did you experience the thing where The period of time Where Hey, this isn't gonna cover our lifestyle. Is long.

57:49 And then hey, the period of time where whoa, this is gonna more than cover our lifestyle. Yes. Long. But the period of Hey, this is great. 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 a like a longer period of the journey.

58:08 One hundred percent. 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. We had a baby and so that was a real meaningful thing, but When you have a baby.

58:22 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 don't really start incurring expenses on the kid for a bunch of months 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 Hoogie every once in a while. Yes, wawa hoagies. Yes, the best. You guys need to do an acquired on on Wawa at some point. Oh, we totally should. Wait, so okay, let me get to question number two then. And I asked question one because

58:51 As I've talked with other creators who experience that moment, there's this really weird thing where you feel like because phase one was so long and you've been looking forward to phase two, the break even phase. I mean in it's great to be in phase three, but it's like weirdly unsatisfying how fast you blow through phase two because you've been looking forward to it for so long. I guess it's the optimist thing again, like we're Because I set the first three months up as an experiment and knew that I could go

59:16 You know, find another job somewhere and that hopefully maybe the newsletter would have introduced me to somebody who might be willing to hire me because they like what I wrote. So that wasn't like a revenue Desirous period. And then there were those months in between that kind of after that where it was growing and I was like, this is gonna happen. So probably everybody around me was relieved that it happened, but for me it was kind of like no no no again, it's math here. And so like

59:37 This will happen and as long as it keeps growing, then it'll become like a number that is really exciting. I didn't think it was gonna go as well as it did, but There was no point where I was like, I really hope that I'm like, you know. able to eat and that I can scrape things together. Again, probably because we were living in my in law's basement. But I think that probably would have made it a little more satisfying if I was like every month dreading the rent check. But fortunately.

1:00:00 That was not an issue for us. Yeah. Okay, so then that leads me to question number two, which is you have pioneered a pretty unique sponsorship format. Like we thought we pioneered a unique sponsorship format in the presenting sponsorship where you we like really throw our lot in with the presenting sponsor for three months. Shout out to Pilate, albumar, website, everything. Interview on the top of the show.

1:00:22 And then Here comes Packie McCormick. And says you know what? Every week. One of the two posts that I do.

1:00:29 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 freak out. And I'm just gonna own that. How did you come to this and what were your fears around it? How did it come to be? All that.

1:00:48 So I'm gonna get the origin story. Somewhat wrong. I'd started talking to Nick Avazid at at 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, you could write those on startups and I bet people would be willing to pay. And he had just come over from Shrug Capital to run marketing at Main Street and he's like,

1:01:12 We'll be the first ones who do this. And I was like all right. Cool. Let's Try it. Like I'm the 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

1:01:26 My audience is a 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 some Main Street will get you kinda your tax credits back in in an easy way. By the way, what month was this that you're having this conversation ish? This was actually pretty early in the sponsorship journey. So this was probably also in like the August, September. Range. Okay. So still a ten thousand ish Twitter followers. Still at ten thousand ish Twitter followers.

1:01:53 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, in a normal journalistic institution that has integrity, there's a wall between the people who write 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

1:02:18 Name, but I was like, all right, so if I do this. 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 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.

1:02:35 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? Please let me know if you hated this. 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.

1:02:49 But the vast majority. Either don't Care. Although the open rates are actually like fairly consistent, maybe a little bit higher on the Mondays. 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 love that.

1:03:02 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. 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. Yeah, even Ben Thompson on his podcast, I think it was back in February.

1:03:32 without calling me by name was like There's 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

1:03:43 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 talk about what I think Isn't great if there are things and I will talk about competitors. In a positive light and I will never say just like

1:04:05 You know, do a hatchet job on competitors in the piece unless competitors like a straw man like You know, I talked a lot of shit on passwords when I wrote about Stitch and that's fine because nobody loves passwords. But you know, as long as I keep that bar high and I'm like very honest, I say up front 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.

1:04:24 People end up liking. The post and so What I was saying was Founders end up liking those because 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.

1:04:44 I wanna pause for a second, uh In the action movie story of the not boring story. I think this is a good point to talk about a few things kinda just going on in the world. Around you doing this.

1:04:57 And one Obviously. what you're doing wouldn't be possible without All the platforms and infrastructure. Substack, Twitter, all of the things that

1:05:07 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 be doing what you do. Even when Ben Thompson did it, he had to roll his own for so much of this. You are operating a venture fund with no other employees. Angelist makes that possible. But

1:05:26 It's interesting, right? Like you said a traditional media organization would have journalistic integrity and would never do this, right? Well, what is journalistic integrity, right? And like, you know, post twenty sixteen and Donald Trump and everything, like, you know, this is kinda one of those second third order effects of the last five years in the world in this country of like Well maybe Mainstream journalism still has a great place, but maybe it's okay to also

1:05:53 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 kinda looked at this like ghetto of sponsored content. And it truly was a ghetto.

1:06:06 Was it a ghetto because it didn't have integrity or because Nobody put the work in to make it great, you know? You made it great. Yeah, there's a lot to first of all the platforms like You know, I'm all in on web three now, certainly rely on web two platforms in a really big way. The most beautiful Substack is because they've taken such a strong stand

1:06:26 for subscriptions and against advertising. No one on their team has ever even reached out to me. And so I paid zero dollars for my main platform because they want to pretend like ads don't exist. And I hope they don't hear this and start charging. They've never reached out to you? Never reached out. Oh my God. Yeah. So that is just like kind of this happy accident where my main platform ends up being free. And so people Will pitch me kind of new newsletter platforms all the time and they're like, Bet you're pretty bummed that you're paying ten percent of your revenue to substack, right? And I'm like, I actually haven't paid anything to substack. Twitter

1:06:58 is free and I've written about this before, but actually I pay for Twitter Blue now just out of like a thank you. It's a garbage product so far, but just as a out of a thank you for all that Twitter has done. I I pay two ninety nine a month for that now. So that's a cost, but You know, these platforms have been Hugely helpful in making that boring what it is and and our low cost. On the other side, the the point that you're talking about journalistic

1:07:19 integrity. We're catching me at a time where I'm like kind of in this mini Self-proclaimed, nobody cares, but like kind of war against all the cynicism that's happening out there. I think everybody has incentives and motives. And at least if I'm saying I am sponsored and this company is paying me right now to write about this. It is just very out in the open what I'm trying to do. Or if I say I invested in this company or whatever else, like

1:07:42 Everybody can go into the piece kind of knowing that that is The table stakes. I don't know what the incentives are for traditional tech journalists and they're not certainly all this bad, but I think a lot of the reason that not boring works is because there's so much snark about tech out there for all of these companies that are one just groups of People not making a ton of money and like now maybe salaries are a little bit better and all that, but

1:08:04 For the past decade. People at these small companies not making a ton of money and like actually trying to change the world. And that's like a corny phrase, but like that is how you can recruit people to come work somewhere and not make a lot of money. trying these new things, like taking different pieces off the shelf, going and trying to build something, and then there's like Snarky fifty year old men sitting back and being like, Oh no, I've seen something like this before. This is really stupid.

1:08:27 Or you know, like X, Y, and Z. And This is not well thought out enough even for me to like be saying this publicly. But it feels like a lot of journalism is like left over from an era where journalism was like really needed because not everything was out in the open and like you needed journalism to expose corruption and like

1:08:45 Take down Tammany Hall and like All this stuff. And then you apply all of that. To like these little tech companies that have raised like five million dollars, and you like try to dig through the garbage. There was an article in Business Insider on Spring Health about their work culture the other day. that was like trying to be a hatchet job, but there was nothing bad in there. It was that the like people worked hard at the company

1:09:04 A marketing guy said his team was working too hard and so they want he wanted to lower the goals, and the CEO said, No, we're not lowering the goals, but I'll hire more people for you. Like That is a tale as old as time in startups that You know, there's a battle between the CEO and the marketing team about what the goal should be, and the CEO sets an overly aggressive goal. And the fact that somebody think it's worth investigating for four months the story about this company, or like the hit job that they just did on Row, which was like Also, total BS. Like you can always find someone who's unhappy in a company when you're not making that much money and when you're working a lot. And then to use these people who have gotten fired as sources for these hit pieces that are poorly done and nobody believes.

1:09:39 That is Just abysmal. I think when the the market turns and when we enter a bit of a bear market in tech and web three, like It will be really easy to throw stones at me. Like I am unabashedly optimistic about all of this and like Things are gonna turn, I'm gonna like, you know, the tide's gonna go out and my pants are gonna be down.

1:09:56 I'm also totally fine with that. Because I do think that like the overall tone of tech journalism is like What's wrong with these companies? Like they're making too much money. And so if somebody has to be on the other side saying like no, this is awesome.

1:10:09 I'm happy to be that guy. It's exactly what you said. It's incentives and it's audiences, right? You planted your flag from the very beginning that you are going to be an optimist And your audience Is founders. And people who are also optimists about this whole industry.

1:10:26 There's a viable audience of people who are pessimists out there and who don't like it. And that's what the other media outlets can rate four and two. But it's like Nobody was doing what you're doing. The other piece of it too is like

1:10:38 Yeah, I want to be optimistic because that's like naturally what I am and it goes back to doing the thing that you actually are and there's a reason I worked at a startup and even though that startup didn't do well, I'm still optimist about this because I think like a lot of really great stuff has come out of this. I also want to be realistic. So like I'm not gonna just be like this is always the greatest thing in the whole entire world. My favorite kind of audience are the people who come in and they're like I was frankly really skeptical about crypto or about web three or about tech in general until I read this piece and it explained it really well.

1:11:06 In ways that make sense. So I still try to tie this stuff back to like business principles. I mean we're both huge seven powers fans. So try to actually tie back to like what is the competitive advantage of this protocol or of this company. And so I don't want it to just be like pie in the sky optimism. So if I can convert people who were like either pessimistic or skeptical.

1:11:23 over to at least being thoughtful about it. Like that's all I'm going for is be thoughtful about it. And I think if you're thoughtful about this industry, you're gonna come away at least being like, wow Done a lot in the past few decades. Well, and you seem to operate under the same primary principle that we do, and David and I text ourselves this phrase all the time, or text each other this phrase when one of us is straying from it. But rule number one at acquired is assume the audience is smart. And

1:11:46 If you assume that The cool thing is long term, it means you'll get a whole bunch of smart people, as long as you keep doing your thing and you stay true to that. That'll pay attention. It comes with these interesting trade offs where you can never allow yourself to hide the ball. Or else you're compromising that long term goal.

1:12:03 And so you always to the extent that you are assuming your audience is smart. You have to write well reasoned stuff, or else you are just going to take an enormous amount of shit for what you put out in the world. It's not like you can say, Hey, here are my incentives, this thing is sponsored, and then write a total fluff thing with zero serious analysis in there, because everyone's just gonna look at it and go, Well, Yeah, you told me that

1:12:26 your independence was compromised and then it wasn't useful then it wasn't something that I enjoyed thinking about. You can't waste people's time, certainly. One of the tests that I always run for myself, and I probably actually would have failed this test. Is If Theranos had come to me on a sponsored post

1:12:43 You know, however many years ago. Chances are, frankly, I would have written something positive on therapist because I assume the best and I'm not technical and so I'm not digging into that machine and being like

1:12:54 Actually, do you know the the science doesn't make any sense? Impossible. With that small of a blood sample, how could you possibly And that's where investigative journalism has a very valid role. A hundred percent. They're goods to both and they're bad things to my approach and and I don't know which company Probably none of them, but Maybe there's a company that I've written about that ends up being a total house of cards, you know, in five years and I look like an idiot for writing that piece.

1:13:16 I probably would have written it about Theranos and that's you know, that's an okay trade as long as I'm like Nobody's expecting me to analyze the science behind Theranos if I could analyze like the business side of the business at least and do the work and maybe somebody learn something that is, you know, not just about Theranos, but about some other concept that I'm using to analyze the company, then that's okay. So I guess that's the risk. Well that gets back to this, you know, frankly. I don't know if it was intentional or not, but this

1:13:42 Brilliant. You know, so did Jiu Jitsu, you did. With Sponsored content that was a ghetto and sucked because nobody actually gave a damn, put any effort in to make it great. You've done that, but you do have to put the effort in to make it great.

1:13:57 A hundred percent. Yeah. The worst thing that could possibly happen is if I did one of those and wasted people's Time because People would unsubscribe, people wouldn't read the next sponsored post. So if the whole thing falls apart, if I lose my integrity throughout this process. The lucky thing is that I've been A pretty like open optimist the whole time. So no one's like, That's so weird. You rip apart tech on Monday and then on Thursday when people pay you, you're like really generous to this whole industry. So it it's all consistent, at least.

1:14:23 So I told you at the beginning this wasn't gonna be all softballs. I don't wanna pretend that Every Thursday piece is exactly as interesting as every Monday piece. Because And again, I think this is okay. But

1:14:33 There are a lot of Thursday pieces that the headline doesn't sound interesting to me. And I end up either not reading it or just like skimming it to make sure I like didn't miss some huge piece of information where I'm like, it would be good for me to know this. However, when the Monday pieces come out I'm like Ooh, this could be the next great online game.

1:14:50 This could be the next cooperation economy. And It's rare that I think that a Thursday piece is going to be that. Actually ba except for like Solana Summer, that kinda was that. But I I do think that

1:15:03 that's probably in line with your sponsors' expectations is that it's gonna appeal to a group of people that they particularly want to appeal to who wants to know about their company and happens to be a subset of your audience, but it's probably not going to be like Hey, let's all close our eyes and pray and do kumbaya that this is exactly the same thing as the non sponsored content. That's totally fair. I try to make it as good as I possibly can. I'm often writing though about Either

1:15:28 a specific company, which is just like a smaller design space than something like a great online game would be. And I'm also writing I guess about a you know, a company that has less of a history and like less complexity to it, maybe, than some of the the larger public companies that are right about. So My goal is to write the best thing that's been

1:15:46 written on that company every time I do a sponsored deep dive. And Chances are in a lot of cases it's a two year old company, like the best thing that's ever been written on that company. Isn't going to be as interesting as breaking down Tencent over 20,000 words because Tencent is a sprawling business that has this like crazy innovative business model. And so

1:16:05 While I want it to be as close to the Monday as humanly possible, like my real bar for myself is can this be the best thing that's ever been written on this particular company? Plus, is this a company that I would invest in and all of that? And so if the open rate is thirty seven percent instead of forty five percent on Thursdays. I'm totally fine with that. And you know, everybody's come away very happy from the sponsored deep dives on the company side. Yeah. To my mind the right question to ask.

1:16:27 isn't necessarily is every Thursday piece gonna be as good as every Monday. It's If I'm the company, if I'm your customer Is this Blatantly obviously the very best thing that I can do.

1:16:42 To get something written. And a great deep analysis done about my company. And that is so obviously, yes. What are their alternatives, you know? I'm sure there'll be more people like you who pop up and that's great. It's not a zero sum game, but If I'm a two year old. Company.

1:16:58 And I'm the founders of that company and I want to I think I've got something great, but I need to cross the chasm to have people Know about it. It's not like you're gonna write a Monday piece about it otherwise.

1:17:10 Necessarily. The other fun thing too is like Companies can almost choose how interesting they want it to be. I think the best example of a sponsored deep dive that I've done was And this was

1:17:21 You know, this was kind of early on, but was ramp. And like they're kind of double unicorn round when they raised at a one point one billion dollar valuation and a one point six billion dollar valuation in the same transaction. And the reason that that one worked so well was because Eric. The CEO there was like

1:17:36 Dude, completely open kimono. Ask us anything. I will give you the timeline of how this round game came together. I will give you exactly how we think about cap table construction. You tell me what you need to make this the most interesting piece possible, and I will give that to you. And a lot of companies make the trade on the other side, which is also totally fair, that they want to keep some information private that they think there's an advantage to keeping private. And so that's the trade that that I think you make there, but There's a reason like I think people refer to that piece often when you know they're reaching out to me about sponsored posts. And then a lot of companies make that trade off when I'm like, Cool, the reason that one works so well is because they told me everything. And they're like, Cool, do that, but like, you know, with maybe ninety percent of the information.

1:18:13 Before we move on, I wanna cover one final topic of journalistic integrity. Cause David, I think like Your take may come across when we go back and listen to this as a little bit too like And this is when the downfall of democracy started. We can point to this moment where David Rosenthal said that journalistic integrity is not important. I don't mean it that way. A I don't think that's like really the right takeaway, but it could be heard that way. I think there's like two

1:18:37 pieces when you really unpack it. of like why is journalistic integrity important. The first one. is that the reader is fully disclosed on the incentives and knows what they're getting. And we've covered that topic. Like Packy, you wave your arms around all over the place and everyone knows what they signed up for.

1:18:54 So that's almost like the microeconomic or like the micro to your business. But then there's a macro one too. Where It could be a bad thing for the state of the republic.

1:19:05 If every journalist looks over Uh what you're doing, Packy, and says Uh I could do that. And you have the very best writers from the New York Times or Forbes or the the Wall Street Journal that are just like I could go make five to ten times as much and have a much more independent

1:19:24 lifestyle with control over my life. Okay, by opening this up, this independent journalism, quote unquote journalism, I think it's important to not call it journalism independent content creation, that is Entertaining to read. and fulclosed incentivized. Do we chisel away at the third estate?

1:19:44 So one of the things that I think has been really interesting is that people have jumped over the fence from working for a publication to going independent and then now have started to jump Back? And like I couldn't do what they do. And this is not like you know, a lack of respect for those people. Like my brain wouldn't work if someone hired me to be like, you have to go be an investigative journalist.

1:20:04 It wouldn't work. Right. And so That's one part. I I do have respect for that, particularly where it's applied the right way. My problem is when it's applied to like A one year old startup that maybe like overwork their

1:20:14 quote unquote overworks their employees a little bit, as startups occasionally do, and as a lot of companies occasionally do. Like when you apply the same rigor to that as like Watergate? Like that's when I I kind of have a bit of an issue with it. So going back to the the piece on kind of people jumping over and back, there's a lot that goes into that. And I think it's really hard to do that kind of journalism. independently because you need lawyers who have your back and you need

1:20:40 editors to make sure that you get everything right and you need like All this stuff to protect you when you're doing this really brave work. That I think is tougher to do on the on the independent side. So I a hundred percent think that there's a place for that kind of journalism. It's just like Don't apply that to like a startup that makes hot dogs and like

1:20:57 came in over budget one quarter and like that shows how stupid startups are. Like that kind of article is what what really gets me. Well, I think it also works the other way too, which is that It's hard to do what you're doing. The goal of this episode has been to tell your story. And I think

1:21:14 What are the takeaways that I'm not surprised by is like Your whole life and career led to this. So if you were an investigative journalist at XYZ publication. Doing very much not this. And then you're like, Oh, I'm just gonna jump over and do what Packy does. You wouldn't be equipped in the same way that you are. You know, you worked for six years at a startup from employee six through hundreds of people.

1:21:36 And through failure, which helps. Through failure, yeah, exactly. I think that's right. There's there's definitely an empathy there too. And like I go into this Knowing full well that it's Wild that's I

1:21:48 Was an employee, not a founder. at a startup that sold for three million dollars after raising hundred twenty million dollars. So like It unless the content stands for itself, like nobody should be listening to me because there are many more successful people to listen to out there. So all of that has let in, I think, gives me a great empathy for what founders are doing, but the content has to stand for itself. Okay, so taking us back to the story, uh, you mentioned February is when

1:22:11 Ben Thompson mentioned you as some guy who writes a newsletter whose name I can't remember or something like that. And of course The funny thing about compounding, you went from zero Ben Thompson mentions your whole life to like now it feels like every few uh newsletters I read from him, I'm like, Oh, there's Packie again. But that first no name, name, mention. I think was in February when you had twenty two thousand Twitter followers. You also sent out a tweet in February that you wanted not Boring to make one million dollars this year, which as David has in the notes, sounds effing crazy.

1:22:42 And I'm curious. What happened in your brain as you formulated that tweet? Was it that the sponsored posts had been going well? Were you already contemplating not boring capital? What was that moment like? Yeah, so I'd been thinking a little bit about not boring capital. And so that was there, but really was talking about just purely making a million dollars off of the newsletter.

1:23:05 A couple of things that happened around that time, like Me and Ben from Composer wrote this piece on Excel. that got picked up, I think, by two separate New York Times articles and got to the top of Hacker News and all of that kind of stuff. So I was like, whoa, that was my first taste of like this thing really going kind of mainstream. I had written a sponsored post I think probably, you know, either that week or was in the middle of writing the post. And the company was really happy with it.

1:23:29 And I was in Miami and the weather was nice and I could have been in New York in the middle of February and I probably wouldn't have tweeted the same thing, but I woke up and the sun was shining and I was like, you know what? Life is pretty good. Like I'm probably making at this point. Call it Ten or fifteen thousand dollars a month or something like that. So like Not close, maybe twenty. I I don't know. But I just woke up feeling like really

1:23:48 Good and I was like, you know, I'm just gonna say this. And like people will probably think I'm an asshole, but I've struggled on zero dollars for the past X number of Months and I'm just gonna say it and then As I think happens often with those tweets, like the support was actually Huge from them. Like nobody reads that as a

1:24:03 cocky signal'cause first I didn't say like guess what I just did. It was more like I hope that'd be wild if this happens. But also people like Wanna see other people take risks and succeed at them, I think. It's like if Packie's making it, maybe I'm kinda making it in a way. The other thing is I guess there is like a tiny buffer between just like Me saying like I'm gonna make a million dollar salary this year and saying like not boring will make a million dollars, cause it's still a business and for a business, a million dollars a year is like Fine. You could probably raise.

1:24:29 A seed and maybe a series A in this market on that. And certainly not in a media company. So You know, it's not like anything crazy from a business perspective, but Yeah, that was that was where that came from. Alright, so give us the update.

1:24:40 We're now in uh it'll be December. By the time this comes out. How we trending? I think Wag Me. We were talking about pilot, and I certainly probably need the help of bookkeepers. I just pulled my Mercury account. That you know, I I do all of my banking in and

1:24:57 And I think that probably has about seven hundred and fifty thousand in revenue. There's a bunch of invoices outstanding. Some people send checks, some goes to my like personal banking. Like this is not a well run business by any stretch of the imagination. And I have a few pieces kind of coming up. And so I think chances are we're gonna just kind of cross uh a million dollars in twenty twenty one. Wow. So great.

1:25:20 What would you have put the percentage chance at when you sent that tweet. I would have put the percentage chance that we got to a million dollar run rate. Pretty high. I thought probably given that I kind of like knew what my sponsorship calendar was for the next couple months at that point.

1:25:34 And it wasn't. the right run rate to get me there, I probably would have put it at like twenty percent that I actually hit a million this year. It is the power of compounding kind of happening where like The numbers just keep getting bigger to the point where it's like, you know, what would have Taking me ten sponsor deep dives, I can now do in one sponsor deep dive. And so that just kind of all

1:25:51 grows and compounds, I guess, but Still. Absolutely. Crazy. I mean, speaking of compounding, so you had gone from

1:25:58 A few hundred followers. to twenty thousand followers or twenty two thousand followers by that February when you sent that tweet. You'd already doubled that then by June. to forty two thousand. It's crazy that you're now over a hundred thousand. You definitely have this thing where

1:26:13 You're growing somewhere from twenty to forty percent per month, it kinda bumps up and down. But At this point it's probably for you more of a market saturation question of like when does that top of the S curve start to hit, or when does this thing linear out a little bit? There's a little bit of a bummer in those Twitter numbers, which is a point of pride for a while was that I had more subscribers than I had Twitter followers. And now I have more Twitter followers than I have subscribers. I'm at like you know, a hundred and five or something on Twitter and eighty eight.

1:26:43 in the newsletter. Uh and so like let's change that. That probably means that I should spend a little less time tweeting. Everybody, we need to help Packy out here. Go subscribe if you haven't already. In some ways it would shock me actually if Well, I know numbers wise, there are people who listen to Acquired who aren't Subscribe to not boring, but In my head I'm like, who are those people?

1:27:02 Like we're a little bit less And this is something I wanted to talk to you about, like Ethereal, theoretical, abstract. And frankly, like a little bit less future looking. Like one question I have for you is at what point did you skeptically walk up to the web three cliff and then just jump off it without a parachute? Cause you did way more of that than we've done here at Acquire. So I can imagine maybe that's a difference in audience, but let me bring it back to If you're not subscribed and not boring, oh my God, go subscribe.

1:27:28 Thank you. Not boring.co. Yeah, so the web three point I I think the web three was a turning point. And so, you know, I wrote about for a lot of twenty twenty A lot of companies that are

1:27:38 super fascinating and that I've always wanted to just like dig really deep into and frankly that 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. Thank you. Not true. Different approaches.

1:27:52 Continue. You were first. I I can tell you for a fact that without Again, we'll go to the ten cent episode, but without the ten cent episode on Unacquired. There wouldn't probably be that not boring two parter on Tencent.

1:28:05 And so 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 a kind of that clean a choice to say like,

1:28:24 You know what, instead of public companies I'm gonna do this web three thing, but when I Started writing about Web Three. I remember there was one essay that I wrote, The Value Chain of the Open Metaverse, back in January where I was really apologetic almost even in the intro to that piece that I was writing about crypto in the metaverse and I was like Everybody, this is really weird. My audience had become like fairly fin twit and finance heavy and I That's this year. That's Packie McCormick writing in twenty twenty one apologetically that I I'm sorry, I'm talking about crypto. Right? I mean it shows how much

1:28:52 The world has changed since then. This was before Beeples sixty nine million dollar sale and a bunch of stuff, but I talked about kind of some of the early early Beeples. Before you tried to buy the US Constitution. But you know, that piece ended up being, I think, really well received because it was a Again, optimistic. take I guess on crypto? It was like a non dismissive take, at least on what was going on.

1:29:15 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 middlemen and we're gonna Blah blah blah. And I was like, no, no, all right, so just taking a step back.

1:29:33 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.

1:29:53 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 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 don't understand it still, but I understand it a little bit better, and I understand that maybe it's worth looking into. And

1:30:11 I even set myself a rule that I would just do kind of like maybe one web three, I probably called it crypto back in the day before it was even called web three. one crypto piece a month and then Something else interesting happened. And so then it was two. And then other ideas that I was thinking about, like if you know, I wrote this piece called Power to the Person. Which wasn't ostensibly about

1:30:29 Crypto but it Certainly it was partially about the things that Crypto lets a solo creator, solopreneur do and then there were 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 that we discussed on a previous acquired episode about Ethereum and then dove into Solana.

1:30:49 And I think Hopefully what I can do and I actually need to keep myself honest because 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.

1:31:04 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

1:31:21 Here's maybe one way you'd think about valuing the blockchain and And go from there. But 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. I like that.

1:31:36 That is a thing that doesn't exist. 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 that divide. Is

1:31:49 really around business fundamentals and structure fundamentals because a lot of people are like Oh, well with Dows, we throw everything out. So no one even like has a manager. 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

1:32:16 If our goal is to ship a product, we do have to figure out some structure to ship a product. 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 I've spent too much time in tech and V C 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 Dallas, I think are really great. in certain situations. I think Eight out of ten Dows 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.

1:32:49 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 to Dallas 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 Dows outright because Sometimes they can be a little bit chaotic or whatever else. I mean, like I got involved in The constitution dial, which was trying to

1:33:15 by 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 fifty million dollars to go fight to win the constitution and bring it back to the people. And then it's also like very hard to make Huge decisions in a seven day time frame and to organize a twenty thousand person discord, all of whom has been told that they're a part of a Dow and has a voice and

1:33:38 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 seed 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

1:34:04 Here's something that might kind of work and oh let's go try it. The worst thing you could do is just dismiss something. Do you get blowback from people who were really into what you used to write about and are now like you gotta like spin something off or like I just can't I'm not buying it. Before I I had and I still have it on, but I I just

1:34:21 Don't read them. I had my unsubs Turned on and and would literally go through every time someone unsubscribe and be like Oh Ah. Someone unsubscribed. Now I don't care as much. I think this is kinda to your point earlier about kind of like

1:34:34 getting the audience that you deserve. Maybe there's 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 you're the actual quote It does make sense. The actual code is not you get the shareholders you do, you get the shareholders you ask for. In the long run. You get the audience you ask for. Exactly. And I hope like I what I don't want to do is alienate everybody who has like some sense of that fundamentals have value. Like those are people that I really want to read not bore, and I want to keep me accountable. But if people are just like, Hey

1:35:12 You're writing about web three 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 Then I'm out, like that's when I'll know that I have an issue. There was one There's 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. And then of course Solana like three and a half in the next two months. I just gave you a truckload of alpha. But like that stuff still hurts. Like I don't want to not

1:35:43 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 each week what I want to write about based on what I think it the most interesting thing happening is. But You know, I do want to follow whatever I think is is the most interesting thing going on.

1:36:02 And look, that has attracted an audience that includes CEOs of fang companies. I mean, that are active subscribers to your newsletter. So unless they've unsubscribed. Uh seems like it's working. Did Jeff Bezos send you that email? Yeah, Jeff and I so the thing about Jeff You're not giving him the alpha anymore. Jeff Azus and I have never spoken. He doesn't subscribe. Someone I think signed up with Satchin Adela's email address, but it certainly wasn't him and that email address has never opened an email. So I think that was a prank. But like you know, I do know that you know CEOs of big companies and all of that. It's actually Puta that no

1:36:35 That would be messed up. I was so excited. Alright, so Speaking of web three. You wrote in your

1:36:43 Power to the person. Peace. Another crazy sounding prognostication that you predicted that within a decade or two there would be multiple trillion dollar market cap

1:36:55 organizations that were run, quote unquote, by just one person. That you called solo corporations. And your point was, hey, it already exists. It's called Bitcoin. Nobody works for Bitcoin and it's a trillion dollar market cap. Back to

1:37:10 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

1:37:26 Packy is the head of the distribution in the creator economy and one of the few people that have really broken out You're gonna be like an MBA 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.

1:37:45 And 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. How do you think about that?

1:37:55 This is like a s One of the hypocritical things about not boring maybe is that you know I analyze everybody else's strategy and Plans and all these things and they're really Isn't one for not boring. Like would I love not boring to be

1:38:09 a big and lasting thing that builds actual Products and Does you know things that kind of outlive me A hundred percent. I would love that. I'm right now worried about

1:38:20 what I'm gonna write about on Monday. And so that's like Both a blessing and a curse, I think so far. I think maybe the good thing about not boring Has been that you know I'm fully focused on the content and making sure that's as good as possible. The downside is

1:38:34 That I'm not planning ahead. By like any stretch I'm like one of the worst planners you've ever met. Clearly, if you've been listening to this story. So There isn't right now a long term plan for something like that. I think the really fun thing About

1:38:49 kind of like, you know, the exponential growth of this is that new opportunities kind of pop up. I do think I need to put, you know, a bit of a structure in place, whether that's formal or informal. around not boring so that I can have some time. To Focus on

1:39:03 other opportunities, you know, either as they arrive or God forbid, proactively. But For right now. I mean I think one of the things that I can And this is maybe why media businesses are hard and have a hard time transitioning into into something a lot lot bigger.

1:39:17 is that if I say Yeah, you know what, I really want to like go start building apps and I'm gonna build like I'm gonna launch Packy Coin and I'm gonna build a bunch of apps and make like try to make like a billion. And I don't focus on the content, the whole thing probably falls apart. And if I bring in people to like help on the research and to ghost write for me and all of that. Then it loses the thing that's

1:39:38 One that I like doing and two is at the core of it and on which everything else Relies. I think there's a really interesting kind of web three angle here, where like how do I figure out how to build? you know, whether it's a Dow or some like kind of loose structure around this where other people can go off and like kind of tap into the not boring

1:39:56 Audience and network and all of those things to build things on top that are aligned with with what we're doing. Obviously not boring capital. You know, you can kind of scale the outcomes with, I guess, both a combination of AUM and actual kind of ability to invest in the right companies. But there's not a lot of plans. Beyond that, like if this becomes a thing that is A couple million dollars a year. Like you'll never hear a complaint. From me

1:40:18 About that. But like certainly I think when I'm eighty would would I want to look back and say like that I built something that the second I stop writing doesn't fall apart? Like a hundred percent. Yes. I think it's worth spending a little bit of time on not boring capital. Which is obviously not web three.

1:40:33 Other than You are. Able to invest in web three projects via it, but It is this really interesting thing, like And maybe it's unique to

1:40:42 Sort of R collective corner of the creator economy. But it is a real business. And it is a real step towards going from just being a Yeah, I'm thinking about like the Oprah episode that we did a year and a half ago, whatever it was. Where

1:40:58 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 you like you can Make a few million dollars a year, you'll have a great life, right?

1:41:07 Or you can own the production, you know? And then then you can become Oprah. It does feel like w 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. Yeah, I mean I think certainly not bringing capital is a step in that

1:41:24 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

1:41:45 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 Sevings falls into this camp and a bunch of other people do as well, Lenny and Turner. I'll 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

1:42:06 I actually don't want to do this without having skin in the game. And I don't want to do this without kind of like digging in and getting involved in the companies that I'm writing about and like trying to help shape their trajectories. And like I love picking up the phone talking to a founder about like, Not just like Here's this idea that I came up with and wrote about kind of abstractly, but like Here's this problem that we're having right now. How should we think about solving this problem?

1:42:29 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 because it does scale a lot better to run a venture fund than to show up every week and get a sponsor and then Write an essay? But like Again, like this wasn't even

1:42:50 Plan. Like that's not where it came. It really came from like one time where I 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 memos every time that I wanted to do a deal and founders didn't want to wait three weeks to see how much money I might be able to give them. Wait, you're telling me As an L P in your fund one and fund two, you don't write investment memos for every single one of your Packy!

1:43:17 I I write them up here. Yeah, no, so I did uh fun one I did ninety one investments and not all of them have investment memos, but in All seriousness, 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 that, like really helped me show up kind of prepared and thinking about what to look for in these different businesses. And a lot of your investments you've written about. A lot of my investments I've written about a lot of investments frankly come in because you know, I start writing about web three and I write something

1:43:46 Yeah, 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.

1:44:10 It probably won't be planned and it'll probably be because it makes sense with what I'm doing, but 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 be honest when I get stuff wrong like Bill.com, my worst call of all time being short Bill.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

1:44:32 to be able to run a veteran 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 in how Well, fun one, fun two, fun 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. Well, it does seem like you're publishing pretty much like I think on Saturday you send out

1:44:53 the email to LPs and then come Monday you send out a public version and It's pretty much the same. Obviously there's some things that the companies don't want you sharing, but other than that It's a remarkably transparent way of going about venture investing. And it's also super different.

1:45:07 than classic venture capital. Like Did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those ninety one investments? Never. And that's all part of the strategy. Like I mean, we all love talking about strategy 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

1:45:27 Even like 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

1:45:39 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. Mm. At least as I'm currently constructed, doesn't work.

1:45:52 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 you know make fun of that that that pun, but put on your khakis and ask the question. Yeah. Yeah, but there's a bunch of things that, you know, you make trade offs throughout. And I wrote in the both the public and private memo. I'm doing

1:46:12 Probably less diligence on a specific company. Then 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 up, but it's a fact of the business that like

1:46:25 There's just no way in the world that by myself here, while I have another job and I'm investing in ninety one companies. I'm going as deep looking for the flaws in a company and like calling references to look at what this person did wrong managerially. Like I trust that If a good fund is leading the round or somebody that I trust 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 this will either blow up totally in my face or run this crazy bull market and I should have been a lot more conservative and like gone for like V C value investing.

1:46:57 Or it'll work, but the whole thing is transparent. Which is a thing that's never worked, by the way. Even Ho and Altus would probably agree with that. I would argue. I mean I'm sort of doing Very similar things with kindergarten adventures with Net is what you're doing with Not Born Capital.

1:47:13 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. It it's not like you cooked it all up on a whiteboard. But It's kinda like the sponsored Post right.

1:47:28 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. And

1:47:41 Obviously that wouldn't work for what you're doing, you know. You you've got a big big business writing a newsletter. But there's aspects. of what you're doing that work way better than that one specific way of thinking, right? And You know, you've already scaled

1:47:57 capital under management doing this, you could probably keep scaling even a lot further with this strategy. But what you're bringing to the table and how you're doing it is just this kinda new way of thinking, right? Yeah, and there's A group of people who I think are doing this and I mean you're certainly involved in this and it's maybe a liquid super team to quote myself, which is always fun. But that's coming together and like sharing deals with each other and like trading thought and advice and here's where I think you were maybe wrong on that investment. The kind of things that maybe before you would have gotten out of a partnership at a firm and certainly the

1:48:29 right now you get out of a partnership with a firm. And it's not as formal and I will still make more mistakes than probably a firm will make, at least on like saying yes to things that maybe I shouldn't say yes to. But venture capital's never about the mistakes. The only thing that matters in venture capital are the ones you get right. And that's kinda the point, all right? There may even be one founder committing fraud that you've invested in and it Kind of doesn't matter. To the best of my knowledge, none of my founders are committing fraud and they're all amazing, but

1:48:55 I mean I you hope that doesn't happen, right? Like 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 putting trust in the overall kind of ecosystem and system. that other people are doing their jobs but which again could

1:49:12 totally blow up in my face or not, but that's just a trade off. Well, the way you're constructing your portfolio with ninety one companies is you know, of course, look Absolutely. We don't want any fraud to happen. Like that's not the goal, but You've kinda shifted the mindset from like playing defense of like we're going to make sure fraud doesn't happen.

1:49:31 But in venture capital, the zeros are meaningless. The most you can lose is your money. The most you can make is a thousand times your money. And so you want to 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.

1:49:54 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 byproduct. I think that part is totally true. I mean 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 are right off. And at some point you just kind of stop caring about that particular company and you move on to the next one.

1:50:21 I really don't want to take That attitude towards it. 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 This is why I'm totally cool with founders.

1:50:36 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 a thousand employees or a hundred employees or even twenty employees, you have people who rely 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 more. All right, so we're talking about portfolio construction.

1:51:05 You invested in ninety one companies. You're on your second fund. First fund was Nine point nine nine million dollars. Nine point nine nine. Your second fund's twenty five million? You couldn't get it to ten? Oh you're not allowed to get it to ten. Oh I see. I was gonna see you could call me up. I'd give you an extra hundred bucks. And Fun two, were it to exist, would potentially be in the twenty five to thirty million dollar range. In that range. Okay.

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1:53:22 I think before we move on from not pouring capital is sort of this next phase, maybe it's the final additional phase of not boring. Maybe there's more phases to come in the future. We talked about Sub Stack. Twitter, et cetera, you know the platforms enabling, not boring the media company. Angel list.

1:53:39 Enables. Not pouring capital enables kindergarten capital, like I've spent. Eleven, twelve years in venture now. Nine or ten of those as a traditional professional venture capitalist.

1:53:50 This would not have been possible. You are one person. You did ninety one deals in fund one. Who knows how many you'll do in future funds. now having the equivalent of Substack for a venture firm It's game changing. This was not possible before. It's more than I'd say the equivalent

1:54:07 Um sub stack for a venture firm because Substack, I still have to Right. everything and edit everything and make all of my own graphics and all of that. I work with Jen on the Angeles team. I will give Jen a shout out.

1:54:19 anywhere that I possibly can because it is like having more than just a teammate, like a whole team of people working with me like I will come up with a crazy idea and be like, Hey, we need this Crazy idea. Done kind of like tomorrow, is that okay? I'm so sorry. And she's like, Yeah, 100%. I went and talked to our legal team and we can make it work if we do X, Y, and Z thing.

1:54:41 And so having both the platform itself, which is great and makes it really easy to raise money from LPs and for LPs to get visibility into kind of how the portfolio is performing, although data is a little bit delayed, LPs, so it's actually performing better than it looks on there. But really like Having a teammate over there who is like fully responsible for making sure that things go smoothly. Let's

1:55:01 all of this happen if there was no Janet Angelists. Not boring capital would not. A hundred percent would not be a thing. It's a total reorganization of the value chain by dismantling the vertical integration of venture firms.

1:55:14 And it's so interesting. That Going into this episode I thought Oh I see. And this is a crude oversimplification, but for not boring capital, Packie doesn't need to have associates that are pounding the pavement out in the community meeting with entrepreneurs because he has a digital way to do that called not boring the newsletter. And that way he gets deal flow from that. But it's so much more fundamental than that. Like you look at a venture firm that has 50 employees that has several funds and has been around for a while.

1:55:39 It's not just that There's a massive back office that you now don't need to have to. I mean, traditionally adventure firms, you have an IT person. Like I imagine you don't have an IT person. So not only does your media company not have a vertically integrated staff associated with it. But your venture capital firm

1:55:55 also doesn't have a staff associated with it. And so you actually can leverage all this new value chain that is completely reorganized for both the media and the venture capital business to stay a one person corporation. I mean none of this is possible. 10 years ago. I'm not nearly technical enough to make any of this happen on my own. I'm not organized enough to build the systems to even make it happen, even if I couldn't build software. having these software tools is the only reason that not boring exist. I mean this is kind of the point of the power to the person piece.

1:56:25 was that there are just all of these things that you can snap off of a shelf. And so instead of having to deal with all of the organizational headache of managing and organizing A firm It's very easy then to just snap one piece in at a time. When you need it.

1:56:41 Now it's great, you know, substack it's not an as needed thing. It's every week I'm sending on that angel list is like Snapping a whole huge sophisticated back office into place. It's not even like Substack for a Venture Firm. It's like AWS for a venture firm. It's like AWS for Venture Firm with a little bit of like Also the person doing, you know, like let's say I'm not technical, like also the person doing

1:57:02 the integration when setting up AWS in the first place, because that has been the big thing for me is not just that the fact that there's the software there that makes it really easy, but even when I don't know what to do. There's somebody that I can ask about, like, hey, is this a thing? Like we ask about You know, nine point nine nine nine million dollars for fund one. That was You know, through a conversation with Jen, where she's like, by the way, like I looked into it, this fund actually has this many beneficiary owners.

1:57:28 But if they're less than 10% of this, then you can do X, Y, and Z thing. And so it's even better than normal software until AI gets a lot better. Because like All the things that I'm too stupid to know that I Don't know. They can kind of anticipate and show you the ropes and so this is not an angelist ad, but it is maybe a gen ad, gen subest. Nicole is also great. She's our person. There you go. Thank you, Nicole.

1:57:48 It is Amazing that it's not just software and like there are like when you think about the future and tech and like AI stealing everyone's job. Maybe that happens at some point in the future, but I think the really great thing is that it's just people kind of like pulling resources in the right place and then you can go access them at the time that makes sense. So Angelus model would never work if I only paid them twenty five thousand dollars a year to do what they're doing for not boring. I'm getting hundreds of thousands of dollars worth of advice and service and all of that from Angelists, but they also have thousands of other clients. And so it works and

1:58:18 the more there are places that get really, really good at one specific thing, The easier it is for one person to start a business that draws from all of that. You're championing specialization of labor. It's like Hey, pie growth happens when everybody gets really good at one thing and we have a super, super liquid way of stitching all those together. Exactly.

1:58:36 Okay, so we're sitting here evaluating in all the most positive ways and sunshine and butterflies around this one person corporation thing. What are the trade offs? You're a strategy person, where's it get hard? So the trade offs Right now are I don't have any outside investors. I mean I have LPs for the fund, but

1:58:55 If I get hit by a bus, not boring is Just Done. And that's like the extreme example and the example that everybody uses when they talk about one personal things, but

1:59:04 That means 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 that perspective. Like you'll hear zero complaints out of me, but It's really hard to take A week off?

1:59:19 Because I'm worried every time that the momentum will slow and there's not, you know, somebody else in the team who's just gonna like go write something else and keep the momentum going that particular week. So I think that is the obvious one and 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 Napborry 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 this thing.

1:59:48 So that's one big downside. The other I guess like there's the whole churning group thesis, right? That if you have a big audience that is loyal and dedicated to kind of this like one particular thing. then you should be able to build businesses all around that person.

2:00:04 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

2:00:15 Sponsorship if I could be using that same kind of microphone to sell my own products. That probably is actually better and higher upside and like more equity value and all of those things. And I don't have either the capabilities or the time to build out those types of things. I guess here's another downside with the one person model.

2:00:32 So the more I do of that stuff, the more it dilutes the core thing. And the more it makes it seem like kind of a shell factory, like Advertising is just kind of part of the model. But if I were like, hey, you guys should also buy Packy branded hats.

2:00:44 Alright, like maybe I'll buy a hat. Can we get some sneakers? I'd definitely pimp some not boring sneakers. Alright, we'll we'll do some not boring sneakers. That we can do. There are certain things where like I could plug in also to kind of these off the shelf companies that let you launch your own brands and all of that, but like At some point people are like, Dude, we like you because we like to read your stuff every once in a while. Like chill out with building these other businesses on the side. And so I do think it's limited in that. Whereas

2:01:07 Other companies are set up expressly for the purpose of like building their core product and then expanding on top of it and you know exactly what you can expect. I think it's all about expectations. And the expectation with not boring is that it's mainly about the content. And then other things that like plug in very cleanly to that content. And the more I do things that like seem like a stretch. The more people are like, you know what, never mind, we're gonna go read this other person who just does the content.

2:01:28 It's funny, it flies in the face of the most common advice I give Seed and Series A founders, which is Until now. Until product market fit. You were the only reason that the business could exist. you uniquely figured out the product that people wanted and willed it into existence and needed to do everything.

2:01:47 And now The only thing holding the business back is you because you still are doing all that stuff and you need to stop and pull yourself out and hire and You know, that sort of thing. That is like exactly not true here. You will always be in that first phase, and David and I will too.

2:02:03 because we're not willing to organization build around sort of pulling ourselves out of the core product because you are the product. A hundred percent. And for better or worse, right? Like That has other benefits for you, I'm sure, as well and for me as well that You are the product. You're probably more visible than CEOs of a lot of companies whose products you love. And that gives you all sorts of other personal opportunities, but for the business itself, It means that it is harder to kind of scale it out in a

2:02:29 predictable way. Maybe we could both figure out how to scale these things out. I mean, like, you know, I like business breakdowns a lot from the and best like the best crew and so like. Patrick's kind of figuring out how to scale out the business. It looks like Harry with 20 B C and some of the data stuff that they're doing is figuring out how to scale out the business in different ways. But it's really hard and it requires like At least for me, it would require a big pause and a step back where I was like, All right, I can't do as much content for the next three months.

2:02:54 because I need to build out a team and I know how hard it is to hire, I know how hard it is to manage. I know how hard it is to manage on an ongoing basis. And so it would be a real risky move to even hire people in and take that kind of step back. that you need to build the structure to build an organization on top. It's to kind of go that morning brew route where you're like, actually there is a brand voice and a format here. And if we can hire correctly for people that can do the not boring thing.

2:03:21 kinda like they did for the I mean it's a what is it a hundred person team now or something doing Morning Brew and I don't think Austin uh uh or Alex are actually writing the letter anymore, but it still feels like a pretty similar letter to what I was reading five years ago or four years ago, so That worked. It's a totally different way to go about it, though. And you guys could probably do it better than I could, right? Like I think the great thing about that business is they had

2:03:43 Both Alex and Austin. And so you know, if one person could focus on the content then one person could focus on kind of building the organization and take turns and all that. Again, a little bit different with acquired because you're both the personalities and you're both kind of on on the podcast, but It is nice, I think, for them that they've had this partnership where you know, I'm sitting in a room alone here. But you have robots on the wall. I have robots on the wall. I have my brother who edits the vast majority of my pieces and help me think helps me think through the business side. Pooja is a saint and like

2:04:12 In addition to kind of like working a full time job and managing our growing boy. Also we'll you know, when she's dead tired on Sunday, read drafts like I'm not solely alone here, but I also can't be like

2:04:25 All right, Dan and Pusha, you write the next not boring while I think about building this organization. You know, Ben and I talk about this. It is interesting. been thinking for a long time now, and you know, certainly this is the path we've taken and acquired of like

2:04:39 What is the ceiling to the core thing? Like if the core thing Is great. And continues to be. Do you need all the other stuff? Do you need more shows? Do you need more content or On the Internet, can it just get Big. And then when you add the capital piece too, then that is very scalable and directly related to the content as well. So

2:05:00 So just him. I think it can scale with this one thing pretty well and like everything also kind of continues to feed off each other where If I have a bigger portfolio of companies, but each time I mention a company in a newsletter, it has a bigger impact because the audience has gotten bigger. It all kind of scales.

2:05:15 With each other. Which I think is really nice. And yeah, I don't know. I mean if this ends up being a thing where I do, you know, one sponsored post a month instead of two and get a little bit more time to like

2:05:27 Yeah, take a weekend off every once in a while, like That'd be great. But you know, there's a path to this being a million person newsletter at some point in the next five years. I'd be very psyched about that. From the graph I'm looking at, if it keeps this shape, it would be in the next two years. So that's the question is how long can it continue on this

2:05:45 twenty percent month over month growth. What do you think the saturation point of your audience is? I mean Yeah, it doesn't feel As

2:05:55 Exponential The chart where like It still grows a thousand to two thousand people a week, the newsletter. But a thousand to two thousand people a week is a lot different when you're at forty thousand versus eighty thousand. And so like maybe it does go a little bit more linear than exponential at some point. Maybe we are hitting the

2:06:12 S part of the S curve. I certainly hope that's not the case. I think probably the reason that that would happen. is if I get really lazy on it, frankly, and I'm like, look, I have a big audience, things are great. Making money. This is awesome. I'm just gonna kinda keep doing what I'm doing and

2:06:26 Don't want to mess it up on the content side specifically. But I think if I kind of keep pushing on the content side and keep attracting new readers who are interested and want to learn while also kind of keeping a tether to the audience that's there already. Then I think it can kind of continue to grow. And that's why like

2:06:42 on the content side, other than just being kind of obsessed with the idea of constitution dial, why I was like Right, I could either write a normal map waring piece or I could like kinda go gonzo on this and like actually join it and write about what's happening and like take part in this whole thing. And so like I I think where this ends up Losing its team is if people don't think that they can get a glimpse into the near future from reading not boring and a glimpse into the near future that's explained in an approachable and not crazy sounding way.

2:07:08 Like if I go And I'm just making stuff up, then that's bad. But if I'm just like, hey, here's what happened last week. Here's your kind of like tech round up.

2:07:18 Then that's not good. I think like What I will hopefully continue to do well at is looking into like the very near future, never being the earliest person on something, but like kind of being the person who can say, like, all right, this is actually probably worth taking a look at now. And here's actually like why it's not as wild as it seems, or why it is as wild as it seems, but it just might work. That's I think where I can hopefully

2:07:38 kind of continue to grow is the future will continue to get crazier and crazier and crazier. And so if I can just like kind of help keep translating what's going on and make people feel a little bit more comfortable with it, then I think I'll be able to kinda continue to grow. I feel like you live three to six months in the

2:07:53 possible future and we live one month into the probably future. I don't know if you think about it that way at all, but that's like whenever I'm reading your pieces I'm like oh I'm not there yet. But I bet.

2:08:04 This will help me get there by reading it. The fun thing. for me has been that I'm writing this like very Tech. Optimistic newsletter in

2:08:13 the greatest bull run ever that somehow instead of getting You know, like hitting its own S curve point. Like keeps getting wilder. If that keeps happening then I'm in really good shape. But you know, it could also slow down and like not boring is still I think You know, even if there's a two year bear market.

2:08:30 We come out the other side and reload and continue to grow and things continue to get better and all of that. But like those two years are gonna be a really interesting time in not boring where I'm like, All right, everybody just like Uh, here's another piece talking about why we should hang on and not lose hope. Like that will get old pretty quickly. And so that's probably actually the biggest risk to the business in the short term, both on the venture side and the newsletter side, is that people are like Enough of this optimism. Like things are kinda tough right now.

2:08:55 Okay, so just to highlight before we finish history and facts here and move into power is the insane last month. Speaking of compounding, like all this somehow happened in one month. And I'm just again looking at your Twitter. You went from seventy eight thousand followers to a hundred and six thousand five hundred followers. You made your first and then second appearance on CNBC. You with Chris Dixon wrote a piece that was published in The Economist and proved to the world that you can write in the economist voice, not just in the

2:09:25 Unique Packy voice that I love that brings me three to six months of the future today. And and it is a very different voice. I mean you read that economist piece and you're like wow, this is written by the economist, not by Packie and Chris.

2:09:38 And Of course, speaking of Chris Stickson. You're working with entries and Horowitz now. The whole world Including Paki.

2:09:47 They've hired. So I wanna point out all the results of this crazy compounding that unbelievably happened to you in mid October to mid November of twenty twenty one. And A, what does that feel like? And B, what are you doing with A sixteen Z? Yeah, so I think actually the biggest

2:10:02 Growth driver. Potentially was that Maria and I wrote. That's piece on Discord and then Discord CEO in the replies to my tweet about the piece. announced that they were adding web three integrations and then announced that they were not adding web three integrations. And so that brought out

2:10:18 The deepest, darkest, worst parts of Twitter. The replies to that were Fast and furious and crazy. But it also added, you know, I think a bunch of followers and that happened that yeah, the same week that the Economist piece came out and announced the uh advisory at Andreessen Off the back of that, so just a bunch of things happen at the same time, so that makes the Twitter graph look a little bit. Uh wild, but I think that was an underappreciated one.

2:10:42 It's weird. I have to pinch myself every week that this stuff is happening or else it's like Oh yeah, I don't know. That was last week. Like what are we doing this week? You're like picky in the brain. Yeah, take over the world. But I don't think it's compounding the same way that interest would, where like Next week. Even cooler things will happen and then next week even cooler things will happen. Like

2:11:01 There will certainly be ebbs and flows. We're gonna go into the holiday season here where everything like I'm gonna get panicked because my graph looks a lot flatter than it would have otherwise. actually taking some time off, so maybe this whole thing falls apart and We regret having this conversation in the first place. But you know, hopefully the ebbs and flow just kind of average higher over time. In terms of the A six C and Z advisory

2:11:22 That's a really you know, a really fun one, I think, where we're just kind of mission and values aligned. And I think Chris said it that there's A lot of complex stuff happening and the overall kind of like Arc is really good and really positive, but If you can't translate. what's happening and why this is gonna be actually good for people and like

2:11:40 Actually what's happening beneath the surface here. Everybody's kind of just gonna miss out and dismiss this whole thing. And so I think really it's kind of the the advisory there is like you know, working with some of the companies in their portfolio to think about how they tell their story, writing pieces like I wrote with Chris in The Economist. they'll introduce me to companies, you know, that they've invested and are excited about. Not in like you know, there's no

2:12:01 guarantee that I have to write about them or anything like that, but Maybe I invest in them, maybe I, you know, write about them, but I think you know, the the main thrust of the partnership is That we're both out there just trying to like explain what is going on and why this can be You know, potentially

2:12:17 Good thing and where it can go wrong and why it's not as scary as it seems. And so I think it's really all about kind of that. We're both This is gonna sound way cornier than I wanted to, but Both kind of just like working in service of this thing that's happening. And one of the things that I think really impressed me, like I

2:12:32 Signed on, obviously, as you alluded to, in the middle of them hiring all of these people. And so I was like So excited to announce it and then I was like, Oh man. Everybody's not. Like I don't know about that. And so I was like gonna do a like a snarky tweet. Not snarky, but you know, like I was gonna do a tweet that was kind of like I'm joining A sixteen Z two

2:12:50 And then I went out to the offset the team did out out in California. And it was so clear that like this big team of people was there because Andrees was just kind of throwing its resources. behind making sure that this nascent movement kind of had the resources it needed to grow. And so there's, you know, a bunch of people working on the regulatory side there. There's a bunch of people working on the technical side there. They have Genius engineers who like other web through protocols and companies we're trying to hire who are just in house there working on behalf of portfolio companies.

2:13:17 And I know that I'm like romanticizing the services model of Venture Capital right now, and there's obviously a reason that they're doing that. We did a two part series on it. Exactly. I mean the It's Good for them if the industry and their particular companies do really well. But it really feels like a group of people that just like actually believes in this thing and wants to put the management fees to work in service of it actually happening and not getting kind of

2:13:40 choked at the beginning by overregulation and by people's lack of understanding. And so I came out of that feeling a lot more optimistic and just even like more excited about working with them after kinda getting to meet more of the team. Cool. Well, thanks for cluing us in. I mean, it's fascinating to me that Yeah, then it's not like you joined the firm and you are still investing completely separately out of a separate pool of capital. You have your own newsletter that's staying totally separate, but that there's

2:14:04 I think it's a smart evolution of the venture model to say, Hey, actually Crypto Advisor. I don't know exactly what your title is, but it's smart. Yeah. I mean I've had that other conversation with funds too, where it's like, Hey, you wanna come

2:14:18 work and, you know, be a full time partner at this fund. And no, like we've talked for the past couple of hours about how much fun I'm having doing this particular thing, so that would never be an attractive model. Stealing the thunder on our big idea for grading. Yeah, listeners, we're gonna talk about this in grading,'cause I I I'm curious to dig into that note, so hold that thought for now. Let's do powers. You've got this concept of the not boring flywheel.

2:14:40 Which I wanna say it's kinda like you can make an Excel spreadsheet say anything. You can put a flywheel diagram down on paper and it will always look good, but no one has Amazon's flywheel. And so before actually naming the powers You've got the not boring flywheel here that has audience at the core.

2:14:58 that feeds out into founders, their sponsors, we'll link to this in the show notes, and they're sort of the Monday pieces that really feed it all and go back in and grow the audience. That was from Great interview you did with Jake Singer. Like a year plus ago? That We're big resource here. Actually right around February.

2:15:14 Oh wow, so it needs to be updated. It probably actually was a result of the million dollar tweet. I think that's when he was like, All right, we should talk. I'm curious how you would describe the most powerful aspect. of the flywheel. Like what is the thing Where you are like, Oh, these mutually reinforcing aspects

2:15:30 are strongly tied. I think as we talked about a little bit before. Audience at the center of the flywheels maybe not Exactly. the thing like if I had a million person audience of people who didn't care about startups or

2:15:42 Whatever, like it wouldn't be kind of as powerful. I think it's really just kind of the alignment between The content. The Particular.

2:15:51 People who are in the audience and then The investing and like those three just I think really work well. Together. because they all kind of feed each other. So that's a cop out answer where I think I pretty much just named the whole flywheel, but I I don't think there's any one particularly strong link. I really think that it is that the content has attracted a certain type of audience member who's both more valuable to companies and who also include people who are starting companies and running companies and all of that.

2:16:17 And it all just kind of feeds back into each other. But I think maybe the core part is that the content itself is so aligned with the venture business. I think that's the magic. With what types of companies or founders do you have strong product market fit on the investment side versus weak? Where has it happened where someone's been like uh Sorry, there's not really space in this round for this reason.

2:16:39 Or you're talking to somebody about sponsoring and then they're like, Eh, actually no. On the sponsor side. Really it comes down to Price, frankly. And I think if this were a

2:16:50 business, I'd probably be more relaxed on pricing sometimes, but because it's me at the center of it and I'm Equally happy. Not writing a sponsored Deep dive and like giving myself an extra week off. As long as I like the company.

2:17:02 I'd like to write about them, but I'm gonna stand pretty firm on price. And so that's where that falls apart. It's not necessarily a particular type of company. What's really interesting is like There are actually companies that I'll say no to that I think that I would invest in that I think are great businesses. And then I think they're like. have something interesting strategically that like

2:17:20 Just maybe. Isn't Interesting enough to the audience where like actually It would still perform and I've done stuff like this a little bit in the past and have learned from that where It still does well because maybe they're a high A C V product and

2:17:35 If they get fifty people to sign up coming out of the newsletter. Like that is a huge win. The ROI is fantastic and all of that, but Maybe those fifty people are the only fifty people who actually cared about that s particular Story. So I try to do a little bit less of that.

2:17:49 On the founder side, I don't think it's a particular type of industry as much as it really comes down to like Nobody gives a shit that I write not boring, and so that's why I'm like I kinda bristle at the audience like size being the thing. Because if somebody comes in and they're introduced cold to me and someone's like, This is Packie from not boring and the eighty eight thousand person audience, they're like Oh, cool. You read a newsletter? Uh, I think like the divide is did the person actually read not boring before and like really get value out of something that I've written or not? And I think that's actually where where the divide is. Such a good point. Cause otherwise it's transactional. And they're like, so are you gonna write about me for free? Why do I care that you have a newsletter? A hundred percent. And like you know, I'll get that sometimes from founders but that's kind of the introduction path where like

2:18:33 I had found a recently Email me and ask. You know, after I said, you know, I I committed and said, Here's what I'd you know I'd love to do on the allocation side. He was like, Great, and can you give me the open rates on your last five posts and like your audience size and I was like

2:18:47 This feels more transactional than I Want it. This will be good for both of us if this works out. Yeah, I'd really don't like

2:18:56 when I'm on a pitch being like here's how the newsletter will like this will change your company's trajectory like I think it can be really, really helpful for companies and I don't want it to be this transactional thing where it's like All right, we'll give you seventy five thousand dollars in allocation because you have a forty five percent open rate and eighty eight thousand subscribers and I've done the math. That doesn't feel right. It's more like am I aligned with this founder and want it excited about the story. Put another way, the size of the audience is not important because that is reach.

2:19:22 that a founder or company will have access to after you invest. It's because the larger the audience size is of the right types of people the more likely it is that someone has read something you've written and that introduction is warm and appreciated rather than who are you? And that mental leap is like automatic. If you're already a not boring fan.

2:19:43 Then you're like, Oh yeah, I get it, right? Like people like me read not boring. I wanna get in front of more people in my orbit. This makes sense. The other way to describe that is

2:19:54 I don't think it's gotten Any easier convincing founders to give me allocation. Uh fifty thousand readers or eighty eight thousand readers, like if they're a reader, then they kinda get it. And if they're not, then You know, they don't on the sponsorship side it's different. Like there's more of a

2:20:10 an equation there and people are willing to pay more with the bigger audience, which makes total sense. But I do think on the founder side. That's really the binary is do you read not boring or not? Yeah, it makes sense. Makes total sense.

2:20:21 Okay, powers. Seven powers for Not boring? Yes. This is gonna be fun. I'm going out on a limb here.

2:20:28 I think it's not gonna be scale economies. No. For folks, I don't know how this could possibly be your first exposure to seven powers, because you either have listened to Acquired or Red Not Boring coming into this, but briefly The real question is what thing enables this business to achieve persistent differential returns, sort of more profitable than their closest competitor on a sustainable basis for years and years and years in the future. So It's kind of interesting. The first thing that I was thinking about when I was

2:20:58 Prepping for this episode is Hamilton Helmer makes the point that Actually public company shareholders are not short term oriented. They're long term oriented. And that's why when you change your guidance for the next Corner. the valuation can change by billions and billions and billions of dollars because people are

2:21:16 Accounting for the next twenty nine and three quarters years after next quarter. in the way that they think about the trajectory of the business. And so It's interesting thinking about the future value of not boring because it's actually much more near term.

2:21:31 than you would forecast in a public company with a durable organization and product market fit, because it's so packy dependent. And I know that's not naming a power and I think we should do that too, but it's an interesting observation and Probably why you know, media companies and small organizations and family run businesses get lower multiples. I think that's right. I don't want to raise money because then I'd have

2:21:54 Bosses and I don't think I'd get a valuation that I'd be happy to sell part of myself for. Yeah. Well, David, where do you think the strongest one is? I hadn't thought about this before going through the whole episode, but I think there's a strong element of counter positioning here with what you're doing.

2:22:09 At least relative to traditional media companies. Yeah, certainly on the journalism side. Actually and on the venture side. Totally on the venture side. I think there may be some element of network economies here, kinda like what you were just talking about with the flywheel and you know being a read like the more People in your target audiences who are Readers. The more

2:22:28 Powerful. Taking an investment from not boring capital. Or Sponsoring, not boring. Or frankly, just Continuing to read not boring.

2:22:38 becomes as more people In your circle are reading it. I think that's Probably right, but I don't want to give myself

2:22:45 Too much credit on it and I know like Yeah, there's definitely a difference between network economies and like some sort of kind of benefits to scale. And I wouldn't call it scale economies either, where Hopefully it gets better.

2:22:57 I think this is like data network effects or something where like Maybe it's there and like kinda sometimes, like maybe people have it, but probably like you say that there's data network effects just to like pretend like there are network effects. And I d I actually don't know if I If I have them. Like if it means that I'm able to write about more interesting

2:23:15 Companies because there are more readers and some more different types of companies want me to tell their story. And all of that, or you know, the audiences getting bigger and I have more interesting conversations with people. So I have more interesting ideas. Like then maybe that is there, but it's certainly not. Facebook level network academies where it's very clear that one extra person coming on is really good for the people who know that person, et cetera. Well, there's a factor of strength of network effects and like no, you're not Facebook strength network, but I do think it's there. Like it is valuable to me that Ben Reid's not boring.

2:23:42 We talk about not boring. Yeah. It's weak, though. Like you notably don't have a Community. There's a pseudo community that exists in your Twitter replies, but like you haven't organized the community in a way that Actually has network value.

2:23:58 I'd say that's an opportunity. Now maybe one that doesn't meet the bar, but an opportunity. I think that's a hundred percent right. I'm Definitely, I think probably because of not boring club, shied away from trying to like Be a community manager again.

2:24:11 But I I do think Twitter is kind of where that exists now, but I think they're absolutely opportunities and maybe that's where, you know, a Dow or something comes in, or even, you know, where a not boring token at some point down the line. comes into play where then, you know, you get all the network effects that come built in with crypto. But for now I don't think that it's particularly strong. I agree, it's pretty weak.

2:24:31 There's one that I wanna bring up where Hamilton would probably yell at me for calling it the cornered resource of Packy. So I guess it's probably more process power, but You could not write a document. such that you could hand it to someone else and they could do your job. Like that, they could create the product that you create. And I think that's definitionally process power that you can't actually write down the process of creating the product that you create. And I've heard you try to explain it a few times and it's always a little bit different and you can never

2:24:58 Really articulate the consistent way that lightning strikes you. Such that you have a great idea. And it seems like you go into your basement, you surf the internet and magic happens and you might have to start that process a few times, but I don't think even you can really articulate the process by which the product comes out. That's an incredibly good point. I've tried to explain this many times. It's one of the first questions that I get from people if I go talk to a group of people.

2:25:23 And I never have a good answer for it because there isn't. A good answer for it. Totally. It's funny. We get it a lot too. Like what's your process? Like, Well I can tell you mechanically, but it's not gonna sound like Well Ben opens up text edit and he has a document that has a zillion fonts in it because it's been cloned from Two hundred and fifty episodes and that text edit document plus David's notion has almost nothing to do with what our actual process is to create an episode.

2:25:47 I mean that's the beauty, right? I think for acquired, for not boring, for like Good content businesses. This is why I don't wanna scale it and have to write like Um brand guideline or the style guide or even the economist has their guide. Where you should be able to kind of plug into that thing and kind of sound like

2:26:02 The brand voice. I don't want to do that. Okay, so What was that process like writing for The Economist? Like What was the transition from you wrote a draft to final piece?

2:26:13 It was pretty close. Like it goes to their editors, but the interesting thing is that they send you their guide Up front. On ten of the things to avoid until like one of those things is to not use the word increasingly, which I then realized that I do. all of the time in my writing. But they give you those things up front so that you come in kind of aware and so it's as much of what you've written as there can possibly be. And then obviously I think just normally like

2:26:34 An editor that they go for it, but I definitely tried to kind of You know, catch the economist style in the thing that we wrote. Alright, done with powers. Yeah, I'm with the I think it's process power. It's look at the end of the day, it's creative business. For sure.

2:26:47 All right listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team, and deploying them is uh no longer the hard part. Yeah. The hard part is knowing what permissions they have, what employees are using them for, or what decisions AI is making. AI security for an enterprise at scale is not a small concern. Like the risks

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2:28:31 Go check out service now.com slash acquired and tell'em that Ben and David sent you. All right. So Packie. I was thinking about this. Should you go work at a venture firm? And

2:28:42 Without naming a venture firm because then it gets harder to talk about. Let's say you were to go work at a big, big venture capital firm where a fund is like a billion dollars plus. And let's say to reflect the very quick audience that you sort of built this relationship and community you've cultivated and

2:29:00 You know, the way that you're seeing into a very important future in web three you would become a general partner. And the offer would be for like a big, let's call it, I don't know what Carry is a big firm, but call a double digit percentage of Carrie in a brand new multi-billion dollar fund. Or at least billion dollar fund. So you're getting like

2:29:18 serious economics. But the returns are probably like seven and plus years out in the future. And you make a pretty good salary. Like you probably make, I don't know, half of what not Warring is making just in salary. So you have this sort of interesting question of like Do you want to delay most of your upside?

2:29:37 another five, seven plus years. And do you wanna like cut down on something that is sort of at an inflection point right now. Or do you want to stay the course and hope that what you're building now has way more risk, but what you're building can

2:29:53 eclipse even what the greatest upside would be from becoming a general partner at a big firm. Am I thinking about that sort of right in the set of trade offs? I think that you're thinking about it right in the set of trade offs. I think the Tricky part is That

2:30:10 And Schrodinger's cat is not right here. But maybe you'll understand the right version of what I'm saying is Then as soon as I go in house somewhere. I lose half of my value.

2:30:19 or X percent of my value as soon as I go in house somewhere. And that is kind of one, even though you know I do do sponsored posts and all that, there is like this independent voice that I have that obviously goes away. Everything that I write would go through

2:30:35 a legal team and a compliance team and all of those types of things. probably wouldn't be able to even do it at the cadence or you know, even the schedule that I do now where it's like I'm making my last kind of edit or writing my last sentence. thirty minutes before the piece goes out, or even a minute before the piece goes out. So I think it would lose a little bit of that flavor.

2:30:54 And so I think probably You know, you need to add like a time dimension on this, which is When does it make sense to do this? And there's probably like When I'm deeply in that S curve, if I've like gotten big enough that like somehow just because I'm backing before make people like now think that I'm smart where like now I kind of need to prove that.

2:31:12 the I can add value every week. Like maybe at some point in the future when there's half a million subscribers. People will just assume that I know what I'm talking about, even though I don't and I'm just making it up every week. then maybe the trade makes sense both for me because there's not that exponential upside and for the fun because I don't lose all of my value. As soon as I set foot in the door of that fund. But I think for the time being

2:31:34 It would be upside limiting for me and option limiting for me, and it would be you know, the fund would not, I don't think, get what it paid for. It's funny. I'm thinking as you're saying that You

2:31:46 Doing this, joining a venture firm would To my mind be Almost exactly like Amazon buying Kiva systems. Kiva Systems Robotic Warehouse Company. They had lots of clients. I think like maybe Target was a client, Walmart, like lots of clients, including Amazon. Lots of value.

2:32:03 And then at a certain point Amazon was like, Okay, it's worth more to us. To buy you. And it's worth more to you to sell to us at Amazon. Then Continue. Yeah, and we're gonna shut down ninety percent of your business.

2:32:18 But the ultimate value's gonna be higher. I think that's probably right. So maybe, you know, where it would make sense right now is like if there is It's more than just, you know, kind of like having a GP. It's their strategic value in another firm not. Hiring me or in

2:32:34 maybe you don't have a web three practice, but like you need to play catch up. I still think they're better people. frankly, who are like way more technical. I it'd have to be me and some technical people who are like kind of deeper in the space than me, but like maybe it helps you get a quicker leg up into an an area where you feel that you're Behind But I think you're absolutely right that like Amazon was not just making that decision based on Kiva's revenue and client roster because that all goes away.

2:32:59 They're making it to keep that away from other people and to do something themselves. There's this funny like uh game theory thing happening here where It seems like you're willing to be reasonably public about the idea that like it's not that attractive and it doesn't make sense to go join Which then

2:33:15 makes me with my professional venture capitalist hat on going, Well, I guess I don't need to do a takeout acquisition here because he's not gonna go join anywhere else either. Or makes me more like Shoot if I'm gonna game theory this all the way out. If Faggy's gonna do it at some point then Do I actually need to make the over the top offer now to make sure that he doesn't go anywhere else in the future? Well, I've been public about kind of everything in in not boring's path, so if this

2:33:42 does happen if people start making big offers, I'll come back on and and let you know what those offers look like. Okay. So to be though, I think the wild card sits where, you know, It's our show. We get to grade you. You can chime in if you had to. I still think, you know, look, I'm I feel like I'm the I'm packy on this episode. I'm the optimist. The question to me, if you had that offer on the table, it'd be really hard to turn down, right? Like that's a lot of economics and Ben's probably underselling the amount of salary you'd make every year from like the management fees on multi billion dollars. It's a lot of money.

2:34:11 Yeah, I was trying to create this straw man that wasn't just like Well, if you want lifestyle, you do not boring and if you want a whole bunch of cash now and a whole bunch of cash in the future, then you go join the firm. It's actually not lifestyle. I'm sorry, let me restate that. Lifestyle would be better actually in that one. It's control. Yeah. If you want control now or you want lifestyle And cash now, and cash in the future. Go trying to bet it for him. But here's my question.

2:34:37 Can you also manage Billions of capital. In not boring capital. That's the question. Some day. It's such an interesting question.

2:34:45 'Cause I I keep telling myself, no, right? And like we've actually had this conversation over text and voice. with this group of people before. Right now, the answer is Clearly no. Like if I built out infrastructure and not worrying keeps getting bigger and I was able to hire like a really phenomenal team of people who are much smarter than me.

2:35:04 Around me. Would not boring be a platform. From which you could launch a billion dollar fund potentially. It changes the strategy. Completely though. You can't

2:35:13 deploy a billion in follow checks. You can't just slide in a little yeah Yeah, exactly. You'd have to be able to invest in like every Even at all reasonable company.

2:35:23 It it just wouldn't work. And so I'd have to change the strategy totally where it's not friendly and you'd have to go head to head with these big reputable established firms with teams full of smart people. And so that I think is also a limiting factor. That said, you know.

2:35:35 Josh and Locky and like that group of people has turned kind of a solo capitalist thing into a bigger fund and they're competing and winning deals. And so it's doable. It is just a very different strategy that I don't know if I'd be good at or not. Well hell Andreason itself, the Andreason story was that, right? Like Mark and Ben were super angels. They played nice with everybody. They had everybody in the except maybe Benchmark after the Loud Cloud experience.

2:35:57 And then they were like, Well, I think we can turn this into a firm and they did. They're a little smarter than I am. Well, it's a different thing than being a super angel, but it doesn't mean it's not possible. Listeners, stay tuned to find out. As the I don't know if you're the primary or the sole shareholder of not boring, you also kinda just get to pick. You're like, Well, if this will make my life worse

2:36:16 And I don't need to make more money, why would I do it? There's I mean, I think a lot of this is Don't get greedy. Like that I think getting greedy and that is hiring more people, that is lowering the bar on who I write sponsored posts on or even who the advertisers are on a normal piece like This works if I don't get greedy and this stops working if I get greedy. And so it's like a pretty actually clear binary there.

2:36:40 And maybe that means I'm being too risk averse on some things, but I'm very happy with kind of the way things are going now and I know that I can mess it up by getting too greedy. Fair answer. We'll accept it. Uh you guys want to do carve outs? Yeah.

2:36:55 Let's do it. Alright, David, you first. Okay. My car out fitting for My status is.

2:37:02 New dad. This might be pretending a lot of Parenting car about to come. But some people had told us this before we went to the hospital. Um I didn't pay attention and I wish I had.

2:37:15 So If you're a parent, you know what I'm talking about. If you're not This may happen to you someday. Baby comes out and then like babies need to be swaddled, right? And the nurse is in the hospital. They just like a regular blanket and they take it.

2:37:28 And they put the baby in the blanket and they do some folds and it and like this is how you do it. It's so easy like Oh yeah, that's so easy. I can do that. That's just like folding a you know sheet of paper, no problem. And then the nurses leave the room. And then you're like, the baby comes out of the swaddle, you gotta reswaddle the baby. Like I got it's just like Whoa. How did they do that? That was magic. You can't do it.

2:37:51 New parents, do not try and swaddle your baby in a regular blanket. Get some dedicated baby blanket swaddles with velcro and zippers. It will save you so much heartache and bring them to the hospital for God's sakes. Uh that's my carb out. Seconded. Boy, David's carvats have really changed. Totally.

2:38:13 It's great advice though. I I'll take a note. So it's funny, in prepping for carve outs for this, normally I have like five or six I can choose from that I'm reading that are off the wall stuff or different things I'm watching. I'm watching succession, but I've already curved that out. Everything that I'm reading or listening to right now is either prep for this episode or our next two episodes, which I won't spoil. So

2:38:33 I'm gonna do something that is way too much talking in my own book, but I think it's a Awesome. thing to read and we were uh top few posts on Hacker News yesterday, so Clearly there's other sort of heat around it. There's a Pioneer Square Labs piece by Dave Peck, who's a veteran engineer on our team called An Engineers Hype Free Observations on Web Three.

2:38:53 And its possibilities. And I helped a little bit in this and our goal was really to like take all the spelunking that our engineering team has done in the studio. And this is people who have worked their whole careers not in crypto and explore what actually are the technical merits of these technologies, what should be built.

2:39:10 Is there a lot of discussion around building, but doesn't actually make a lot of sense to us why you would build that distributed? Uh, and try and write like a balanced, honest take on like Here's what the tech can do, here's what the tech can't do, and you know, we're gonna try and ignore some of the cultural elements of web three and just do it a little bit more analytically. And of course you can't help but throw in some cultural elements'cause it's a cultural movement. But I'm really proud of how it came out. I welcome all feedback and we'll put a link in the show notes. So I'm gonna keep it.

2:39:39 In Seattle for mine. I think the last time that we talked, maybe I I recommended a sci fi book I've been reading. a lot of sci-fi. I think it's just if I'm spending so much time in real stuff when I'm writing, it's nice to turn my brain off. The other day I finished a book and I Googled Best Sci Fi twenty twenty one. And this one book came up.

2:39:57 And it was described as Haruki Mirakami meets ready player one. And Hiroki Murakami is my favorite author. Ready Player One, maybe not the best written book of all time, but it certainly inspired a lot of the things that people are talking about right now. So this book is called Rabbits.

2:40:13 It's this Thriller. about this kind of global game that takes place to save the world and You play it by following a bunch of these coincidences that seem like coincidences, but maybe they aren't. And

2:40:27 Ultimately. Playing and winning rabbits is how you kind of like reset balance. In the universe? It's You know, again, maybe not the best written book that I've ever read. I've heard the ending isn't great. I haven't gotten there yet.

2:40:39 But it's been a really entertaining I can't put it down kind of read. And it has Murakami ish vibes, if it's not quite as good as Murakami. Oh, I'm gonna have to check this out. And I'm learning a lot about Seattle, which is making me feel closer to Ben. You're welcome any time, my friend. Oh, Seattle's such a great sci fi. Tenuous Seattle. Connection but also sci fi and sci fi books. I am so hype.

2:40:59 November thirtieth, which will be probably after this comes out, but before as we're recording it. The last book of the expanse is finally coming out. Oh wow. Oh I'm so hyped. Someone recommended the expanse to me today. I've never read any of them, so I just I bought book one. Oh my God. You gotta read it. It's the Best. It's so good. Have you watched the show?

2:41:19 No. I've been told to read the books first and then watch the show. I could see having not read any of the books, at least the first two, maybe three seasons of the show were excellent. Like some of the best sci-fi TV I've ever watched. I'm rereading to get ready for the final book. Uh so there's

2:41:33 Gonna be nine books total. Eight have already come out, the ninth is coming out. The first two Amazing. So great. And then I would say three through Uh three is pretty good too.

2:41:45 Four, five, six, and seven are like they're still really good. Like read'em through the first time. I reread one and two, and then I'm rereading eight, and then I'm gonna go right into nine. Have you read Red Rising? The Red Rising trilogy? No, I need to. So just what you said reminded me like normally because again, like I'm a happy go lucky optimist kind of guy. When people say that, where they're like I liked one and two. I didn't like three. I loved four. I hated five. I don't have that kind of nuance in my brain.

2:42:12 But Red Rising, it feels like it was written by like not only a different person, but A different species almost after book three, like Books one, two, and three were so good, and book four was an abomination, and it's one of the few books that I've stopped in the past few years. Wow. Yeah. How many books total are in the series? I couldn't tell you. You just stopped. Stopped. Wow.

2:42:34 Interesting. Okay, I'll have to check it out. One through three though, you should definitely read once the expanse is over. Great. Well the expanse is um If you only watch the TV show, you might not know it.

2:42:44 There's two authors. So James SA Corey is a pen name. Of the two authors who collaborate. They are George R Martin's assistants. No way So the expanse is Game of Thrones in space. Oh, I never realized that.

2:42:57 Yeah. It's really good. Alright, well now I have to go read the books. Me too. Wild. All right listeners.

2:43:05 Now is a great time to talk about one of our favorite companies, Statsig. Yes, there is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI powered experiences at scale. Yeah. In the crazy speed of today's AI world. Shipping fast is just table stakes now.

2:43:27 It's basically trivial to build and deploy your app constantly. The real advantage is how quickly you learn what changes actually created value for customers. And how fast you can use that signal to guide what you ship next. This is where StatsIG comes in. It brings experimentation, feature flags, and product analytics into one unified system so teams can ship safely, test rigorously, and directly link what they changed to how users actually behaved. So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com slash acquired to get started. Well, Packie, we can't thank you enough for being here.

2:44:08 Thank you for I mean, this was a dream come true. This is so much fun. It's a very unique acquired episode for us. Notably not a special. We want to be very intentional that like this is profiling the history and strategy of a company the way that we would the New York Times or Standard oil or Amazon. And

2:44:25 The company just happens to be It's surreal. I also as we drift toward our closing notes here.

2:44:35 Yeah, I was gonna Tell folks seriously you should go subscribe to the public acquired LP show wherever you get your podcast now. But it's worth pointing out. The strategy to shift to make episodes and the whole back catalog public to listeners on a new feed.

2:44:51 After two weeks of being just for the paid subscribers is totally inspired by you, Packy. I mean I think the realization that with such a smart, valuable audience that attention is the scarce resource. I think that Part of

2:45:06 Us realizing oh we should change the way that the limited partner program works and really make it just the limited partner community with some early exclusive access to this content. And actually in crypto, I guess two weeks is forever. So that two weeks is valuable. Especially as we do more crypto stuff. But yeah, that was really largely inspired by you. So thanks for that too. If my biggest contribution to the world is making more great content free on the internet, I am very psych with that legacy.

2:45:33 Awesome. Well, Packie Where Can listeners find you or not boring on the internet? So not boring is it not boring dot co? I have a poorly produced podcast that you can find by searching Not Boring Podcast wherever you listen to podcasts. We're gonna get you upgraded. We're gonna get me upgraded. Next time we do this, you're not gonna be saying poorly produced. It's not that poor like that is how I read not boring is listening. That's true. Yeah, I mean none of it is overly produced, which I think is good. Uh or Twitter is at Packy M P A C K Y M.

2:46:02 Awesome. And listeners. We'll catch you next time. See you next time. Bye. Who got the truth?

2:46:11 Is it you, is it you, is it you Who got the truth now

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