Not Boring (with Packy McCormick) - Extended Cut

When does a creator become a company? Who says that media companies — or venture firms — have to be organizations? How high is the ceiling on one person + the internet? Acquired has the answers and they are... Not Boring. 🙂 *Links:* - Not Boring: https://www.notboring.co/ - Proto-Not Boring: https://www.packym.com/blog/nyc-debate-club - Not Boring's first sponsor deck: https://projector.com/story/2cb6296d-e229-4774-839c-efbf86d7f69f?scene=7127c7a0 - Jake Singer's Not Boring Flywheel: https://theflywheel.substack.com/p/not-boring-packy-m - Proof Ben was famous even before Acquired: https://web.archive.org/web/20150814041757/https://www.seattletimes.com/business/high-octane-leader-drives-microsoftrsquos-innovation-garage/ *Carve Outs:* - Velcro swaddles (dad life...): https://www.amazon.com/s?k=velcro+swaddle - An Engineer's Hype-Free Observations on Web3: https://www.psl.com/feed-posts/web3-engineer-take - Rabbits: https://www.amazon.com/Rabbits-Novel-Terry-Miles-ebook/dp/B08HY29VM2 *More Acquired:* - Get email updates https://www.acquired.fm/email and vote on future episodes! - Join the Slack http://acquired.fm/slack - Check out the latest swag in the ACQ Merch Store https://www.acquired.fm/store! _Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions._

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Rosenthal?

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

• 0:05Speaker 01

  All right, so let me timestamp where we are right now, just so we know what we need to do. So we are at 88,460.

• 0:13David Rosenthal?

  Oh, we can so do that.

• 0:15Speaker 01

  Oh, we'll juice this.

• 0:35Ben Gilbert?

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

• 0:50David Rosenthal?

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

• 1:00Ben Gilbert?

  An abbreviated, partial, ongoing paternity leave.

• 1:02David Rosenthal?

  Yeah, we're making it work.

• 1:04Ben Gilbert?

  And we are your hosts. Well, today we have a first for Acquired. We are covering a business that is only one person, Not Boring, the newsletter gone media and investment empire run by Packy McCormick. I did some research last night. Not Boring is the number one Substack newsletter on business. If Packy decided to switch to the technology category, from everything I can tell, he would be number one there, too. In fact, even in the crypto category, there are only two newsletters with more reach, and they've existed much longer. Not Boring is only a year and a half old. The Not Boring story isn't just impressive because of its explosive growth.

• 1:45Ben Gilbert?

  Packy is reinventing the media business model and simultaneously, the startup investing business model. He's done all this with a very distinct personal flair, writing in a unique, whimsical voice that makes us all just want to have fun and play the great online game. And we're very lucky that he is a part of our liquid super team here at Acquired, so he could join us today, live, to help tell the story. Welcome, Packy.

• 2:11Speaker 01

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

• 2:15Ben Gilbert?

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

• 2:21Speaker 01

  It was beautiful.

• 2:22David Rosenthal?

  You had some good buzzword bingo in there with not boring piece titles over the, I want to say years, but it hasn't been, it feels like years. It feels like you've always been here.

• 2:30Ben Gilbert?

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

• 2:43Speaker 01

  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. I would expect nothing less than the full acquired treatment.

• 3:02Ben Gilbert?

  All right, let's do this. 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 podcasts called the Acquired LP Show. Very creative. That is right. That includes our series on VC fundamentals and our startup deep dives on pricing, marketplaces, SaaS investing with top investors and founders. And in fact, we are about to drop an episode right there in that feed where I interview

• 3:42Ben Gilbert?

  15-year president of Blue Origin, Rob Meyerson, on how he sees the space landscape today. Now, of course, members of the paid LP community still get great benefits like exclusive access to new episode for two weeks before we drop it in the public feed, the ability to join LP calls, Zoom, book club, 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.

• 4:12David Rosenthal?

  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-Levitt the other day on the LP Show.

• 4:24Ben Gilbert?

  Super fun. Yeah.

• 4:25David Rosenthal?

  So fun.

• 4:26Speaker 01

  You guys kind of look alike.

• 4:28Ben Gilbert?

  We've gotten that a few times. 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 tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture. It used to be that you proved that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 4:55David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature, or someone writes in a new model without telling IT, and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this quote-unquote "shadow AI" running with no security review at all.

• 5:16Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's Governance, Risk and Compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes, and cuts the time that you'd spend on vendor assessments in half.

• 5:38David Rosenthal?

  In half! Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor, and Snowflake all stay audit-ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 5:56Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance, and the work to earn and prove trust. We're huge fans of Vanta over here, and literally hundreds of Acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V-A-N-T-A dot com slash acquired for $1,000 off, and just tell them 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

• 6:41Ben Gilbert?

  only, and I promise you, it will be both of those.

• 6:44David Rosenthal?

  All right. Look, we're gonna do the whole acquired treatment on you, Packy. But the first place I went, when I was like, all right, I will 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 of not boring. How on earth did you decide on what to put there?

• 7:07Speaker 01

  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, podcasts or something, I get asked to send over a short bio. Or CNBC. Or, you know, if I'm on CNBC, or I get asked 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 capital, like the whole thing gets very confusing. Founder feels like a catchall. Like I did definitely start this thing. And so anything else beyond that, I think is subject to change.

• 7:40David Rosenthal?

  Love it. You are definitely the founder of the not boring empire. All right. So let's tell the story. I'm assuming you were born in either 1986 or 1987.

• 7:52Speaker 01

  1987.

• 7:53David Rosenthal?

  1987.

• 7:55Speaker 01

  January 26th, the same birthday as Wayne Gretzky, Vince Carter, you know, a lot of the great athletes.

• 8:02David Rosenthal?

  Okay. So January 26th, 1987, in Bryn Mawr, Pennsylvania, just outside Philadelphia. There is the birth of a baby boy named Patrick.

• 8:13Speaker 01

  Patrick.

• 8:14David Rosenthal?

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

• 8:30Speaker 01

  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 fourth generation over here. And so we think it's County Cork, but not 100% positive.

• 8:42David Rosenthal?

  Nice. All in the Philadelphia area?

• 8:45Speaker 01

  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.

• 8:52David Rosenthal?

  Yeah. Billy Joel, growing up in Allentown. What were you like as a kid? Any little glimmers of the future not boring empire that were popping up when you were growing up?

• 9:02Speaker 01

  Yeah. I used to make these little books or newspapers on Post-it notes. So one of my dads, my dad was a consultant at Arthur Andersen, 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 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 in this little book called Golden Memories of a Young Boy's Life. So that was probably the earliest version of Not Boring.

• 9:41Ben Gilbert?

  You could have taken a very different career direction after that.

• 9:44Speaker 01

  I could have. I wasn't a particularly good artist.

• 9:47Ben Gilbert?

  Which actually has carried through perfectly.

• 9:50David Rosenthal?

  Perfectly to today.

• 9:51Speaker 01

  I'm still not a good artist. I think it's part of the charm. But you know, even in high school or middle school, we had an eighth grade teacher, Mr. Algejo, 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.

• 10:04David Rosenthal?

  Because for most kids, that's punishment. For me, like if I have to write as much as you write, I couldn't do it. There's no way.

• 10:10Speaker 01

  I mean, I did cross country and track in high school too. And that was kind of a similar vibe where for most people, that's punishment, making them run many miles. And I love that. But Mr. Algejo, 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. Algejo 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 of 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 class clown with a backing of kind of serious research.

• 10:44David Rosenthal?

  It's pretty rare to find those two combinations together in one person, right? Somebody who is both the class clown and has a work ethic.

• 10:53Ben Gilbert?

  And I think that comes through in Not Boring. All of us who read every or close to every one of your posts, I think that's the charm. 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.

• 11:12Speaker 01

  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, thank you. I think it takes a work ethic to read all of the not boring. 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 pants.

• 11:46Speaker 01

  So 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 Andersen and would 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. 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 going to 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

• 12:31Speaker 01

  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. 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+, blah, blah, blah, A. And he was like, all right, Packy, I'm going to 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. We're calling that box the loser box because you're a loser.

• 13:05David Rosenthal?

  What?

• 13:06Speaker 01

  And my mom said that my dad went to like the Mo Market Offy School of 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. 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. Cause 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 at it anymore, but it was a really good lesson that if you're not going to do well, at least be honest about the fact that you're not going to do well. And so now I think, you know, when I get things wrong and not boring, I blare it from the rooftops and probably comes back to that moment.

• 13:42Ben Gilbert?

  Yeah. You feel like an intense need to own the mistake. There's a tweet that you had around the crypto winter where you said them's the rules. You got to play fair. And I think you were owning the fact that a lot of things that you thought were going to go up did not go up.

• 13:55Speaker 01

  I mean, our ideas dinner podcast, I think is a testament to the fact that I get things wrong all the time.

• 14:00David Rosenthal?

  Oh, we all do. So, okay. So you go to Duke, you were on the debate team at Duke, right?

• 14:06Speaker 01

  I was. Shocking.

• 14:07David Rosenthal?

  We were able to unearth some pretty awesome photos from that time. Then maybe we'll link to it in the show notes.

• 14:12Speaker 01

  I was incredibly cool. I was, you know, in the debate club. I was in an a cappella group. You know, there were a couple of big all male a cappella groups. I was the cool one 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.

• 14:36David Rosenthal?

  So, okay. You graduated in 2009, which, I mean, I remember I graduated in 07. I sailed through. I was a French literature major. I get the investment banking job. I'm like, oh, this is great. Then of course I got my butt kicked when I actually got to Wall Street. But you got an investment banking job in 2009. Like, nobody got investment banking jobs in 2009. This was the middle of the recession.

• 14:56Ben Gilbert?

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

• 15:08Speaker 01

  Yeah. So I was. To be fully fair, kind of an investment banking light in public finance, but it started the summer before in 2008. When I got my internship, things were actually still pretty good. So I got an internship at Bank of America on the energy trading desk. That was a wild experience in itself because Bank of America's energy trading desk was all ex-Nron people. And so they were not psyched to not be at Enron anymore and not psyched to be on a desk that didn't take physical delivery. So there are two types of kind of energy trading desks. Some, like, you know, the bigger banks, Morgan Stanley, all of that, which will take delivery if they need to of barrels of oil or whatever else. Like, those are the kind of serious desks. And then there are more just pure financial

• 15:50Speaker 01

  desks like we had at Bank of America. Worked my butt off that summer. Like, you know, there's the intern programs and there's drinks and there's speeches and there's all these things that you do when you're 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.

• 16:11David Rosenthal?

  Right. You're not licensed. You don't have the Series 7, Series 63. Is that the other one you need?

• 16:15Speaker 01

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

• 16:39David Rosenthal?

  This is like liar's poker.

• 16:40Speaker 01

  Totally. But, you know, there's definitely 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.

• 16:48David Rosenthal?

  Merged, quote unquote.

• 16:49Speaker 01

  Merged, quote unquote. So we bought them, but there were higher quality interns, quite frankly, at Merrill Lynch. And so when we merged, I guess the other problem was we all got put on the Bank of America side in a rotational program. So you got your offer from a specific desk, but you came back and had to rotate around different desks. Whereas Merrill got hired into specific desks. So all the Merrill kids, for both of those reasons, they were probably smarter than I was, and they already had their desk kind of placement locked in. They got their desk. We rotated around and about half the people in the trading program ended up getting spit into public finance, which for those listening at home is municipal bonds. 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 new roads and issue debt to do that.

• 17:33David Rosenthal?

  Wow. That sounds kind of boring.

• 17:37Speaker 01

  It was a little bit boring. Hopefully that's the first of hundreds of puns throughout this podcast. But yeah, it was boring, but I actually, you know, 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 bank analysts were getting their PE offers way, way earlier. And I think they quoted two of my friends in that article. So like, I had friends who just loved this stuff and I just was not one of those people. So I knew that I'd want to get out of finance at some point. And so I was really just playing to be in the top of my class and go to business school.

• 18:15David Rosenthal?

  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.

• 18:25Speaker 01

  One other thing to add was while I was in finance, I started 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 the party bus ride, it was so much fun, paid for my summers. I took it way too seriously and thought that this was going to 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.

• 19:04Speaker 01

  And I also found a company called Breather on Angel List 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 deposit's 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. So they wouldn't let me defer. And so I just said, all right, cool. Not going to business school. I had already quit my job and so really spent kind of the next four months, I think, in this weird kind of winding interview process, just with Breather. 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 $29 and sold it. I bought Facebook at $19,

• 19:49Speaker 01

  sold that, plowed a bunch into like Apple options into earnings, which, you know, it's just like not what

• 19:54David Rosenthal?

  You're admitting your mistakes here.

• 19:55Speaker 01

  I bought Bitcoin at 100, sold it at 150. So like, you know, really had a fun, a fun summer where I was

• 20:00Ben Gilbert?

  You got some nice little returns here. Some nice pops.

• 20:03Speaker 01

  A few percent pop, pretty good. 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.

• 20:15Ben Gilbert?

  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.

• 20:22David Rosenthal?

  And you don't have a job.

• 20:23Ben Gilbert?

  The 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 cash in a pretty short period of time.

• 20:44Speaker 01

  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 Bitcoins so that I like just kind of refill the coffers with USD. And so that was why I sold all 38 of my Bitcoin at 150.

• 21:10David Rosenthal?

  Whoa, whoa. Okay. Wait, we can't let you gloss over a couple of things here. We got to rewind. Am I hearing you right that you wrote your business school application about starting a quote unquote company to bus drunk people from Manhattan to the Jersey Shore and the Hamptons?

• 21:29Speaker 01

  I mean, it wasn't about buffing 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 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.

• 21:47Ben Gilbert?

  Wait, wait, wait. So to quote a writer named Packy McCormick, 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.

• 22:01Speaker 01

  That is another one of those formative experiences where obviously it wasn't a startup. It was startup lite. 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 of them. It proved that I could work hard and like, maybe I could help with some business stuff, 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.

• 22:45David Rosenthal?

  What was the name of the party best company?

• 22:46Speaker 01

  Throgo. I actually don't think I've actually technically shut down that LLC. So. I have one of those too.

• 22:54David Rosenthal?

  It's funny, you know, actually doing that gritty stuff of like dealing with tour bus operators. You gotta do that when you're an entrepreneur and so many people that go to business school think, oh, I'm going to get all this glory. It starts some internet company. And it's like, you gotta be willing to shovel your fair share of manure here.

• 23:13Speaker 01

  I mean, that's like the Chris Saka quote about, you know, he won't hire or work with anybody who hasn't had just a shitty job growing up. So, you know, I'd wash dishes. 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 Breather, but that was my first year's experience was doing that exact same thing. Yeah. So let's jump to Breather. So that summer 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 going to spend the next two years not making a single dollar and paying for business school and racking up debt doing that. Or I can go somewhere, anywhere really, that will pay me more than negative dollars and learn on the job and get that experience.

• 23:59Speaker 01

  My interview process at Breather was doing a bunch of really random things. I don't think they knew what they were doing from a hiring perspective. I wrote the JD for the job that I ended up getting, which was New York City General Manager. How big was the company at that point? It was six people in Montreal, so I was going to be our first US employee. One of my jobs was Julian said, there's a guy at Uber who does a job similar to the one that you want to do. Go track him down and then get him to interview you and then he'll tell me what he thinks. And so that ended up being Josh Moore, who was the New York City General Manager at Uber. So I met him, he's 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 that was one.

• 24:42Speaker 01

  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 and go to the Ace Hotel lobby and then make a presentation on why they're different. And they're obviously very different, but I'm not a designer, 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 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. So I ended up getting the job.

• 25:25Speaker 01

  So what Breather did was it rented out, meeting and 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 rent spaces to this random Canadian company that wants random people to come in and out of the building for half an hour at a time throughout the day. So that was challenge number one. And I literally like got on my knees and in one case, this is actually like I mean literally, got on my knees and begged to one of the landlords to give us the space. And they ended up giving us the space. Oh, my God. Cause Julian told me I was going to get fired if I couldn't get three spaces by X date.

• 26:01David Rosenthal?

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

• 26:04Speaker 01

  Ours were really tiny in the beginning. So ultimately, we ended up competing with WeWork. In the beginning, we were looking for like the 150 square foot, really quirky space somewhere in the building where someone could come take a nap or like maybe get a little bit of work done. But the idea was that your phone should be able to unlock all these spaces that are underused throughout the city. Turns out, one of the challenges of that thesis is in Manhattan, there's really no underused space 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

• 26:47Speaker 01

  the day after they got acquired, they're like, by the way, 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. I would leave dinners with friends and whatever kind of after hours. The other was because I had met Josh during this process, I called Josh and was like, hey, you have that Uber Rush thing. Is there any chance that we could get Uber Rush messengers to clean breather spaces since they're moving around the city anyway? And so we actually, I was the largest consumer of Uber Rush messengers in the world for a while. We never had that outside New York, I don't think. It was a New York test that might have gotten to a couple of other markets, but really kind of a New York test where the idea was if you want to deliver documents from one place in the city to another.

• 27:31David Rosenthal?

  Which is super common in New York.

• 27:33Speaker 01

  It was super common.

• 27:33David Rosenthal?

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

• 27:38Speaker 01

  Exactly. And I think part of that is probably what became Uber Eats ultimately, is these people kind of moving around the city 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 to be like, hey, by the way, like, this isn't a delivery job, you're cleaning a space. And to be fair, these people opted in. So we had our own view where it's only people who opted in and they made a little bit more by doing that. But I'd be like, all right, so this particular space, you go into the room, there is a set of cleaning supplies under the couch. There's instructions there. If you have any questions, just text me. This is my number. And so seven days a week, 6:00 AM to 11:00 PM, pretty much when we closed, I was just on my phone texting messengers who were going to go clean breather.

• 28:23Speaker 01

  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. 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 in 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 at Breather, but none of it was particularly easy.

• 29:03Ben Gilbert?

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

• 29:06Speaker 01

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

• 29:24Ben Gilbert?

  It's a catchall.

• 29:24Speaker 01

  Yeah, it was a catchall. That sounded way fancier than it was, but that was about 150 person team, including our operations associates who were full-time employees at 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 of that.

• 29:42Ben Gilbert?

  All right, so I'm assembling sort of the cornucopia or the puzzle pieces that would become 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. 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 at any of these companies is the people.

• 30:19Speaker 01

  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 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, which we did.

• 30:49David Rosenthal?

  The catch was there was actually demand for Uber.

• 30:52Speaker 01

  There was demand for Uber and Uber's supply could come and go and Uber didn't have to pay them anything. We signed five year leases and did construction. And so it was just a very different situation. So we added a space per day in 2016, 2017 for about a year there. Every day we were launching a new space. And so we were deeply over supplied. Our gross margins were awful, negative, I think negative 25%. 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. But we like just went deep into the company. We read like a bunch

• 31:35Speaker 01

  of Ben Thompson and we read good strategy, bad strategy. And we're like, we're going to turn this company around using strategy. And so we wrote this like detailed memo full of his data science and my crazy ideas on how we could actually turn the company around by adding monthly space and competing kind of more at the margins with companies like WeWork and Notel. And then we sent it out to the company. We got back, we got the blessing of the exec team. We sent it out to the company.

• 31:57David Rosenthal?

  Did it have GIFs and Taylor Swift references in it?

• 32:00Speaker 01

  I actually don't think it had just in Taylor. 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 going to be really hard fundraising or doing anything. 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 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

• 32:43Speaker 01

  design team, having to design between the two types of spaces, absolute nightmare. But everybody bought in and we turned the thing around and we went from negative 25% margins to positive 25% margins. And like, things were going really, really well. And so I think Ben and I were both like, wow, it's strategy that actually kind of matters here, like having a plan and getting people to buy into it and having something that makes sense and fits within the market. Like, all of that, actually, like, it's not just BS. Like, it's a real, meaningful thing. And so I think that was probably also part of why I ended up writing a newsletter that was about strategy.

• 33:13Ben Gilbert?

  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 clearly, this is where the sort of Ben Thompson side comes from.

• 33:22Speaker 01

  100%.

• 33:23David Rosenthal?

  Here's a quote from your first newsletter post, which was not called Not Boring. It was about this course that you're taking, this writing course. 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."

• 33:38Speaker 01

  It was.

• 33:39David Rosenthal?

  The spiritual godfather.

• 33:40Speaker 01

  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. 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.

• 34:11David Rosenthal?

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

• 34:14Speaker 01

  Exactly right.

• 34:15David Rosenthal?

  And you also did On Deck at the same time?

• 34:18Speaker 01

  I did On Deck at the same time, after I left Breather. So, you know, it was a little bit later than I did On Deck. But after I finally left Breather, I tried to quit a few times in 2019. I took a sabbatical, went to Japan. And while I was there, I called our general counsel and was like, get me out of here, please.

• 34:34Ben Gilbert?

  Whoa, you quit from Japan?

• 34:37Speaker 01

  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.

• 34:50Ben Gilbert?

  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.

• 34:59Speaker 01

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

• 35:16Ben Gilbert?

  Yeah, it's a good point. Okay, so when you did leave, 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, but also a different email newsletter?

• 35:35Speaker 01

  I had had Per My Last Email going, and that was really like kind of a link roundup, where it was an assignment from the Right of Passage course to start a newsletter and to get 20 people to sign up. And so while I was at Breather, I was, I was writing that. And I realized I like writing and occasionally I would do an essay. 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.

• 35:55Ben Gilbert?

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

• 36:00Speaker 01

  But if you go to permylastemail.substack.com, the day that I took it down, somebody else took the site over. And I think it's maybe like advertising shampoo or some scam that is now on permylastemail.substack.com.

• 36:13Ben Gilbert?

  Everything turns into a link farm eventually.

• 36:16Speaker 01

  Exactly. So I had that going. And then I used that to like, kind of just think through and write about different ideas that I had for a company that I wanted to start. I mean, like even while I was at Bank of America, when I was in college, when I was at Breather, I always knew that I wanted to start what I thought, you know, would be a real big startup. I had just managed a big team and I thought I'd, I was actually interim CEO for a little while at Breather and thought that I did a fine job there. And so I was like, oh, I can do this. Like every level that you go up in a company, I thought that there were like these godlike people above you who had all the answers and realized that they're all as dumb as me. So why not, you know, start something myself? And so I use writing as a way to kind of think through in public a bunch of these different ideas. And somehow, despite that tool, the best idea that I came up with was a social club that kind of combined Soho House and college extracurriculars.

• 37:01Speaker 01

  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, 20 friends to come and debate. And people loved it. I had a blast. People really enjoyed it. And so I was like, that's a really good signal. This is going to be a huge business because 20 people like debate club.

• 37:17Ben Gilbert?

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

• 37:23Speaker 01

  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 Not Boring comes from, which is I had dinner with my mom and her business partner one night in New York while I was still a 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. 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,

• 38:06Speaker 01

  it was work and then it was your tight group of friends and whoever became your significant other and then your family, but you didn't have those like kind of small groups that were bonded around a particular kind of passion or hobby. So I was like, oh, cool. Like that plus Soho House. That sounds like the coolest thing in the world. Let me go start that.

• 38:21David Rosenthal?

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

• 38:25Speaker 01

  Well, that was part of the thing too. It was 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 of 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, then like, maybe that would have worked. I don't know. I mean, today, what not boring club would have been is really a DAO, probably with physical locations. I think actually that model works really well for what I was trying to do. At the time, it was a real stretch.

• 39:00David Rosenthal?

  Did you pitch any VCs or investors about investing in not boring club as it was coming together at the end of 2019?

• 39:07Speaker 01

  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.

• 39:18David Rosenthal?

  Oh my God. If any of these people had actually invested in not boring, like, wow.

• 39:22Speaker 01

  I know. I might've shut that one down and started fresh, but you know, it was more of a, I think we'll back you this idea. Like maybe you can do something with it. It 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 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 a time to try to get the early applicants. Got the community up and running. We were doing like some book clubs. We did debate club. They're about 150 of the first people. And before we had a club to welcome people in,

• 40:03Speaker 01

  I was like, great, we're gonna do a bunch of small group dinners, starting in February of 2020, late February, we had, I think, our first four 10-person group dinners. They were a lot of fun. People were really enjoying getting to know each other. And then I think it was March 10. We had these like, separate Slack groups for each one of the dinner groups. And somebody was like, you know what, I'm not feeling particularly good. I'm gonna just bow out tonight. And other people were like, 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 the boring club in the middle of this COVID thing. And so, you know, we put it on pause, 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.

• 40:46Speaker 01

  Remember that? 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.

• 40:54Ben Gilbert?

  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 bring in the share price at every moment throughout history. And I don't have Packy'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 105,000, 110,000, something like that, followers, here in February of 2020, taking us back to the story, 956 followers.

• 41:26Speaker 01

  And that was good. That was like, a triple from earlier in the year, before I started writing per my last email. And we could talk about this. One of the things that I wanted to do, from like, very, very early on, I would say, like, welcome to the new X subscribers. Now there are Y of us here. Ah, such a good growth hack. And it wasn't even meant to be a growth hack. It was really kind of like, just in case this works out and becomes a big thing, like, there are all these people with a big Twitter following, or a big audience, like, certainly, you were in that conversation, where I was like, there's all these people that seem, again, like, kind of godlike, and like, it was just like, preordained that they were gonna be successful. In case this newsletter becomes anything, I just kind of want to show that I was just a random unemployed idiot who started writing this thing. And so, we can kind of like, track the whole progression

• 42:10Speaker 01

  of number of subscribers and all of that throughout the journey.

• 42:13Ben Gilbert?

  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.

• 42:23David Rosenthal?

  Well, to be fair, there was a front page Seattle Times article about you before you started acquired.

• 42:29Ben Gilbert?

  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, 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?

• 42:47Speaker 01

  It's crazy. And like, you know, I try to be the same idiot that I was. And it is as, you know, like I still tweet dumb stuff and maybe that's good. And maybe like the SEC is going to 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 just like, I don't want to care that like, I'm going to 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, more people who are paying attention to what I'm writing 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.

• 43:28Ben Gilbert?

  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 grown a personal brand very quickly online. And I think a lot of people make a lot of trade offs to do that, where they play a part on the internet and play a character rather than being themselves. And 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 because I think in three conversations that I can think of recently, people have told me like, I really wish I could be more myself, but I played a character on the internet so that I could quickly grow.

• 44:12Speaker 01

  It's easy to make that trade off. And I probably did a little bit of that frankly, early on, like where I would do more threads and different things. 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 kind of following, I've just decided to be myself because. I'm spending so much time doing this, both writing and tweeting and meeting people and all of that, that if you're not yourself, it's not like a be true to yourself kind of thing. It's like you're gonna have a miserable experience because all of your interactions are gonna be other people wanting to interact with this persona, or if I were writing from a different voice, everyone would expect me to write from that and it would just make it twice as hard to both figure out the content and the voice every week. And so I realized really early

• 44:56Speaker 01

  on that I just needed to like, kind of be as close to myself as humanly possible, or else it was just gonna be too much work.

• 45:01Ben Gilbert?

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

• 45:16Speaker 01

  Exactly.

• 45:17David Rosenthal?

  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 2020? You're unemployed again, but you're older, you're married, your wife is pregnant at this point, right?

• 45:33Speaker 01

  Correct.

• 45:34David Rosenthal?

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

• 45:44Speaker 01

  Not particularly venture backable business.

• 45:46David Rosenthal?

  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?

• 45:55Speaker 01

  I'm to a fault and like, 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, my mindset was like, you know, my absolute worst-case scenario here is that I moved 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, 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 tried to bring Not Boring Club online, I was sitting there, I had trivia nights that I like, spent all day writing trivia questions and making slides, and seven people showed up. And I was like, this is with my Duke education,

• 46:40Speaker 01

  my expensive high school education, all my experience, like this is incredibly embarrassing. And so I decided to kind of just let Not Boring Club, the digital version, fall by the wayside. In February, early February, Pooja and I had learned that we were pregnant, COVID kind of hit and... I remember just 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 Pouring Club. Like, maybe you should just like, apply that to the newsletter and just go all in on, on the not pouring thing. So that was my mom's idea to port the name over.

• 47:14Ben Gilbert?

  Nice.

• 47:15David Rosenthal?

  Wow. Thanks, Mom.

• 47:17Speaker 01

  Thanks, Mom.

• 47:17David Rosenthal?

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

• 47:19Speaker 01

  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 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,

• 48:03Speaker 01

  because it meant that people were no longer going to be stuck in bullshit jobs and were going to be freed up to go do the things that they actually wanted to do.

• 48:10Ben Gilbert?

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

• 48:14Speaker 01

  A little bit.

• 48:15Ben Gilbert?

  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.

• 48:22Speaker 01

  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's strategy through the lens of this fashion show and 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 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. A friend of mine, Tommy Gamba, who was at Airbnb and getting ready to leave, helped me out on the growth side of things. And I had this brilliant

• 49:05Speaker 01

  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 1,000 subscribers to 2,000 subscribers. So that was a huge leap. And I remember sitting with Pooja at dinner and being like, oh, my God, I could actually like this newsletter could be a full time thing. I have 2,000 subscribers now. This is amazing.

• 49:23David Rosenthal?

  Seven people at trivia night. Now you have 2,000 people on the internet. Maybe this internet thing is a good idea.

• 49:30Speaker 01

  We like to say we're talking orders of magnitude difference here. It's a VC term. So yeah, so I mean, things like kind of started looking up from that point and wasn't making any revenue for a long time. And I still remember having conversations like deeper into the pregnancy where it was like clearly going to be a thing. And I had planned to turn on subscriptions and decided to keep holding off on that because I really liked the growth. And I had conversations with Pooja where she was like, are we gonna do a revenue thing here? And mind you, now we're living at my in-laws' house in New Jersey during COVID and I was writing-

• 50:02David Rosenthal?

  With her parents.

• 50:02Speaker 01

  With her parents. And I was writing from a basement. So like, none of this is glamorous. But she's like, are we like, you know, 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 10% of the audience at $5 a month, then like, we could be making a couple thousand dollars a month.

• 50:23David Rosenthal?

  Subscriptions work as a business model. If you architect the right way, there's nothing wrong with it. And obviously, our friend Mario Gabrielli 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% to convert. Oh, I'm so glad you went a different direction.

• 50:40Ben Gilbert?

  There's also the dirty secret, which it seems like you kind of intrinsically knew, which is even 10% is going to be a pretty big stretch. Creators can typically convert, at best, 2% to 3% 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 10, 15% if you bring out your big stick.

• 51:07Speaker 01

  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 addicted 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 kept pushing off, kind of turning on subscriptions so that that number would keep going up. And then Mario did it well. Lenny Rochitsky, obviously, did it really well and has a great business. So there are ways to do it. I think a huge difference between like, someone like a Lenny and then 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 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 going to be willing to pay for it for

• 51:51Speaker 01

  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.

• 52:04David Rosenthal?

  Well, I think 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. It was like, yeah, this is the dirty secret. Most people who pay for the Journal, it's their companies that are paying for the Journal.

• 52:19Ben Gilbert?

  And it's hyper-specific. It's, you know, business, finance. It's the most reputable of that.

• 52:26David Rosenthal?

  Yeah. If you're going to 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 a different path.

• 52:36Ben Gilbert?

  Packy's just gonna be Packy on the internet.

• 52:38Speaker 01

  Yeah. So 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.

• 52:55Ben Gilbert?

  Hmm. Okay. So what month was your baby born?

• 52:59Speaker 01

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

• 53:24Ben Gilbert?

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

• 54:06Speaker 01

  In the summer, kind of late summer, 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, 25 to 34, high income households, leadership positions, the companies, well educated.

• 54:31Ben Gilbert?

  Owning big budgets, decision makers.

• 54:33Speaker 01

  Exactly.

• 54:34David Rosenthal?

  This deck is amazing, by the way. It's still on the internet. We'll link to it in the show notes.

• 54:38Speaker 01

  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 $1,000 or whatever price I put in the deck at that point. But after I made that deck, I was like, you know, this internet thing has been pretty amazing and Twitter's been pretty great. I'm just going to tweet the deck out. And so that filled up and, you know, public came in, Marketer Hire came in, a few other sponsors came in from that. But that filled up pretty much through the end of 2020, all of my sponsorship slots, which was great. And I was like, oh, wow. So then I remember having a conversation with Pooja, I was like, I don't know. Things go really well. I think maybe there's a chance that in the future, we could do $300,000 or $400,000 on this newsletter on sponsorships.

• 55:17David Rosenthal?

  You're an optimist.

• 55:18Speaker 01

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

• 55:34David Rosenthal?

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

• 55:47Speaker 01

  No, I mean, I think the other thing about me is I have an addictive personality. And so, you know, I think we had probably crossed a point where I just realized that I liked the growth too much. And I realized that I liked the fact that, you know, if I was going to be spending all of this time, like, 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 going to 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. And so I was trying to hold off on that for a little while, too. But yeah, a few 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

• 56:29Speaker 01

  Not Boring. And so finally I had made like $10,000 and Pooja let me buy an iPad. So like a bunch of little wins late 2020.

• 56:35David Rosenthal?

  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.

• 56:41Speaker 01

  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 going to be Ben Thompson. All I need is an iPad. Like, Pooja, can I please like dip into savings here and get an iPad? And she's like, no, you don't make any money on this newsletter. Like, you cannot buy yourself an iPad that you don't need. You have a computer, you're fine.

• 57:02Ben Gilbert?

  Okay, so two questions for you. One, did you experience the thing where the period of time where, hey, this isn't going to cover our lifestyle is long. And then, hey, the period of time where, whoa, this is going to more than cover our lifestyle is 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 like a longer period of the journey.

• 57:33Speaker 01

  100%. Yeah, that that happened really quickly. And again, to be fair, covering our lifestyle was like not particularly difficult when we were living in my in-laws basement. We had a baby, and so that was a real meaningful thing. But when you have a baby, David, you know this, people send you probably like the first at least six months worth of clothes and diapers and all of that kind of stuff. So you 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 hoagie every once in a while. Yes, Wawa hoagies. Yes. It's the best. You guys need to do an acquired on on Wawa at some point. Oh, we totally should.

• 58:12Ben Gilbert?

  Wait, so, okay, let me get to question number two then. And I asked question one, because as I've talked with other creators who experienced 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, 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.

• 58:33Speaker 01

  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, 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, again, it's math here. And so like, 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 going to 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.

• 59:16Speaker 01

  Again, probably because we were living in my in-laws 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, that was not an issue for us.

• 59:27Ben Gilbert?

  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 and the presenting sponsorship where you'd be like, really throw our lot in with the presenting sponsor for three months. Shout out to Pilot, Albemarle, website, everything, interview on the top of the show. And then here comes Packy McCormick and says, you know what? Every week. One of the two posts that I do is going to be pure, unadulterated. I'm getting paid by the subject to write this. I am doing the thing that is going to make classically trained journalists freak out. And I'm just going to own that. How did you come to this? And what were your fears around it? How did it come to be? All that.

• 1:00:13Speaker 01

  So I'm going to get the origin story somewhat wrong. I'd started talking to Nick Abazid 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 can write those on startups. And I bet people would be willing to pay. And he had just come over from Shred Capital to run marketing at Main Street. And he's like, we'll be the first ones who do this. And I was like, all right, cool. Let's try it. Like, I'm going to caveat the hell out of it and tell everybody right up front that it's sponsored. But like, I think Main Street is really cool. So I would actually love to write about Main Street and explain. And like, my audience is a bunch of entrepreneurs and founders. And I bet my entrepreneur and founder audience would love to make money back from the government

• 1:00:58Speaker 01

  that otherwise they might not have. And so Main Street will get you kind of your tax credits back in an easy way.

• 1:01:03Ben Gilbert?

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

• 1:01:06Speaker 01

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

• 1:01:13Ben Gilbert?

  Okay. So still at 10,000 ish Twitter followers.

• 1:01:16Speaker 01

  Still at 10,000 ish Twitter followers. 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, the 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. Sponsored content like does not have a particularly great 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 going to 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. And so that was kind of

• 1:02:01Speaker 01

  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. But the vast majority either don't care, although the open rates are actually like fairly consistent, maybe a little bit higher on the Monday pieces, 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. 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.

• 1:02:46Ben Gilbert?

  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.

• 1:02:53Speaker 01

  Even Ben Thompson on his podcast, I think it was back in February, without calling me by name was like, there's somebody who writes a newsletter who does this thing where the startups actually pay him to write about them. But it's actually kind of good because he gets more information for these companies that aren't publicly available. He was, he was kind of saying that he doesn't write about private companies as much because he doesn't have as much material to analyze, but that if I actually work with the company, I have a bunch of stuff to analyze. And I'm very honest with them that like, I 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, 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

• 1:03:37Speaker 01

  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 upfront every time, this is a sponsored post, this is how it works. Here's a link to a doc that I wrote about how I choose them. People end up liking the posts. 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.

• 1:04:09David Rosenthal?

  I want to pause for a second, the, in the action movie story of the not boring story. I think this is a good point to talk about a few things, kind of just going on in the world around you doing this. And one, obviously, what you're doing wouldn't be possible without all the platforms and infrastructure, Substack, Twitter, all of the things that we take for granted now, but 10 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.

• 1:04:44Speaker 01

  You are operating a venture fund with no other employees. Angelus makes that possible.

• 1:04:50David Rosenthal?

  But 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 2016 and Donald Trump and everything, like, you know, this is kind of one of those second, third order effects of the last five years in the world in this country of like, well, maybe mainstream journalism still has a great place, but maybe it's okay to also do things differently. And maybe they don't have all the truth. And maybe, maybe you can think differently about what journalistic integrity means. And then you kind of looked at this like ghetto of sponsored content, and it truly was a ghetto. Was it a ghetto because it didn't have integrity? Or because

• 1:05:35David Rosenthal?

  nobody put the work in to make it great, you know? You made it great.

• 1:05:39Speaker 01

  Yeah, there's a lot to unpack. So 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 part about Substack is because they've taken such a strong stand for subscriptions and against advertising. No one on their team has ever even reached out to me. And so I paid $0 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.

• 1:06:04David Rosenthal?

  They've never reached out to you?

• 1:06:06Speaker 01

  Never reached out.

• 1:06:06David Rosenthal?

  Oh, my God.

• 1:06:07Speaker 01

  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. 10% of your revenue to Substack, right? And I'm like, I actually haven't paid anything to Substack. Twitter 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 out of a thank you for all that Twitter has done. I paid $2.99 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 a little cost. On the other side, the point you're talking about journalistic integrity.

• 1:06:46Speaker 01

  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 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 of that.

• 1:07:28Speaker 01

  But 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 50 year old men sitting back and being like, oh no, I've seen something like this before. This is really stupid 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 take down Tammany Hall and like all this stuff.

• 1:08:13Speaker 01

  And then you apply all of that to like these little tech companies that have raised like $5 million 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 like people worked hard at the company. 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, this story about this company, or like the hit job that they just did on Ro, 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

• 1:08:57Speaker 01

  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, that is just abysmal. I think when the market turns and when we enter a bit of a bear market in tech in 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 going to turn on. I'm going to like, you know, the tide's going to go out and my pants are going to be down. 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. I'm happy to be that guy.

• 1:09:35David Rosenthal?

  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. 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 for and to, but it's like, nobody was doing what you're doing.

• 1:10:02Speaker 01

  The other piece of it too is like, you know, 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 optimistic 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 going to 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 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 I'll 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

• 1:10:46Speaker 01

  who were like either pessimistic or skeptical 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 going to come away at least being like, wow, they've done a lot in the past few decades.

• 1:10:58Ben Gilbert?

  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 Acquire it is assume the audience is smart. And 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. 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

• 1:11:42Ben Gilbert?

  sponsored, and then write a total fluff thing with zero serious analysis in there. Because everyone's just going to look at it and go, well, yeah, you told me that your independence was compromised, and then it wasn't useful. Then it wasn't something that I enjoyed thinking about.

• 1:11:57Speaker 01

  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, you know, however many years ago, chances are, frankly, I would have written something positive on Theranos, because I assume the best, and I'm not technical. And so I'm not digging into that machine and being like, actually, you know, the science doesn't make any sense.

• 1:12:22Ben Gilbert?

  That's impossible. With that small of a blood sample, how could you possibly?

• 1:12:26David Rosenthal?

  And that's where investigative journalism has a very valid role.

• 1:12:29Speaker 01

  A hundred percent. There are goods to both and there are bad things to my approach. And I don't know which company and 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. 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 learns 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.

• 1:13:02David Rosenthal?

  Well, that gets back to this, you know, frankly, I don't know if it was intentional or not, but this brilliant, you know, sort of jujitsu 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.

• 1:13:22Speaker 01

  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 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's all consistent at least.

• 1:13:48Ben Gilbert?

  So I told you at the beginning, this wasn't going to be all softballs. I don't want to pretend that every Thursday piece is exactly as interesting as every Monday piece. Because, and again, I think this is okay, but 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, whoo, this could be the next great online game. This could be the next cooperation economy. And it's rare that I think that a Thursday piece is going to be that. Actually, except for like Solana summer, that kind of was that. But I do think that that's probably in line with your sponsors' expectations

• 1:14:31Ben Gilbert?

  is that it's going to 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.

• 1:14:47Speaker 01

  That's totally fair. I try to make it as good as I possibly can. I'm often writing, though, about either 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, you know, a company that has less of a history and like less complexity to it, maybe than some of the larger public companies that are it about. So my goal is to write the best thing that's been 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

• 1:15:29Speaker 01

  model. And so 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 37% instead of 45% 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.

• 1:15:49David Rosenthal?

  Yeah. To my mind, the right question to ask isn't necessarily, is every Thursday piece going to be as good as every Monday piece? It's, if I'm the company, if I'm your customer, is this blatantly, obviously, the very best thing that I can do 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, 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

• 1:16:33David Rosenthal?

  write a Monday piece about it otherwise, necessarily.

• 1:16:36Speaker 01

  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, you know, this was kind of early on, but it was Ramp. And like, their kind of double unicorn round when they raised at a $1.1 billion valuation and a $1.6 billion valuation in the same transaction. And the reason that that one worked so well was because Eric, the CEO there, was like, 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.

• 1:17:22Speaker 01

  And so that's the trade 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 aren't willing to make that trade off. When I'm like, cool, the reason that one worked so well is because they told me everything. And they're like, cool, do that, but like, you know, maybe 90% of the information.

• 1:17:38Ben Gilbert?

  Before we move on, I want to cover one final topic of journalistic integrity. Because 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.

• 1:17:56David Rosenthal?

  I don't mean it that way.

• 1:17:57Ben Gilbert?

  Hey, I don't think that's like, really the right takeaway, but it could be heard that way. I think there's like, two 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, wave your arms around all over the place, and everyone knows what they signed up for. So that's almost like the micro economic, 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 if every journalist looks over at what you're doing, Packy, and says, "Uh, I could do that."

• 1:18:38Ben Gilbert?

  And you have the very best writers from the New York Times, or Forbes, or the Wall Street Journal, that are just like, "I could go make five to 10 times as much and have a much more independent 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 fully disclosed incentivized, do we chisel away at the third estate?

• 1:19:09Speaker 01

  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. It wouldn't work. Right? And so that's one part. 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 overworks their 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,

• 1:19:50Speaker 01

  that's when I kind of have a bit of an issue with it. So going back to 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 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 independent side. So I 100% 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 hotdogs and like, came in over budget one quarter and like, that shows how stupid startups are. Like, that kind of article is what really gets me.

• 1:20:29David Rosenthal?

  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, one of 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.

• 1:21:01Speaker 01

  And through failure, which helps.

• 1:21:03David Rosenthal?

  Through failure, yeah, exactly.

• 1:21:05Speaker 01

  I think that's right. There's definitely an empathy there, too. And like, I go into this knowing full well that it's wild that I was an employee, not a founder, at a startup that sold for $3 million after raising $120 million. So like, 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, and I think gives me a great empathy for what founders are doing, but the content has to stand for itself.

• 1:21:32Ben Gilbert?

  Okay, so taking us back to the story, you mentioned February is when 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 newsletters I read from him, I'm like, oh, there's Packy again. But that first no-name-name mention, I think, was in February, when you had 22,000 Twitter followers. You also sent out a tweet in February that you wanted Not Boring to make $1 million this year, which, as David has in the notes, sounds effing crazy. And I'm curious, what happened in your brain as you formulated that tweet? Was it that the sponsored posts had been going well?

• 1:22:16Ben Gilbert?

  Were you already contemplating Not Boring Capital? What was that moment like?

• 1:22:20Speaker 01

  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. 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. 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,

• 1:23:04Speaker 01

  call it $10,000 or $15,000 a month, or something like that. So like, not close, maybe 20, I don't know. But I just woke up feeling like, really 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 $0 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 cocky signal, because first, I didn't say, like, guess what I just did? It was more like, I hope it'd be wild if this happens. But also, people like... Want to see other people take risks and succeed at them, I think.

• 1:23:38Ben Gilbert?

  It's like if Packy's making it, maybe I'm kind of making it in a way.

• 1:23:41Speaker 01

  And the other thing is, I guess there is like a tiny buffer between just like me saying like, I'm going to make a million dollar salary this year and saying like, not boring will make a million dollars because it's still a business. And for a business, a million dollars a year is like, fine, you could probably raise 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 you know, that was, that was where that came from.

• 1:24:04David Rosenthal?

  All right. So give us the update. We're now in, uh, it'll be December by the time this comes out. How we trending?

• 1:24:11Speaker 01

  I think wag me.

• 1:24:14Speaker 01

  We're talking about pilot and I certainly probably need the help of bookkeepers. I just pulled my Mercury account that, you know, I do all of my banking in and, and I think that probably has about 750,000 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 going to just kind of cross a million dollars in 2021.

• 1:24:43David Rosenthal?

  Wow. So great.

• 1:24:45Ben Gilbert?

  What would you have put the percentage chance at when you sent that tweet?

• 1:24:49Speaker 01

  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 of months at that point, and that wasn't the right run rate to get me there. I probably would have put it at like 20% 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 taken me 10 sponsor deep dives, I can now do in one sponsor deep dive. And so that just kind of all grows and compounds, I guess, but still absolutely crazy.

• 1:25:20Ben Gilbert?

  I mean, speaking of compounding, so you had gone from a few hundred followers to 20,000 followers or 22,000 followers by that February, when you sent that tweet, you'd already doubled that then by June to 42,000. It's crazy that you're now over 100,000. You definitely have this thing where you're growing somewhere from 20 to 40% per month. It kind of 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?

• 1:25:54Speaker 01

  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 on like, you know, 105 or something on Twitter and 88 in the newsletter.

• 1:26:10Ben Gilbert?

  And so like, let's change that.

• 1:26:11Speaker 01

  That probably means that I should spend a little less time tweeting.

• 1:26:14David Rosenthal?

  Everybody, we need to help Packy out here. Go subscribe if you haven't already.

• 1:26:18Ben Gilbert?

  In some ways, it would shock me, actually, if, well, I know numbers wise, there are people who listen to Acquired who aren't subscribed to Not Boring, but in my head, I'm like, who are those people? 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 3 cliff and then just jump off it without a parachute? Because you did way more of that than we've done here at Acquired. So I can imagine, maybe that's a difference in audience. But let me bring it back to, if you're not subscribed to Not Boring, oh, my God, go subscribe.

• 1:26:53Speaker 01

  Thank you. NotBoring.co. Yeah, so the Web 3 point, I think the Web 3 was a turning point. And so, you know, I wrote about for a lot of 2020, a lot of companies that are 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.

• 1:27:14Ben Gilbert?

  Thank you. Not true. Different approaches. Continue.

• 1:27:18Speaker 01

  You were first. And so like, I can tell you for a fact that without, again, we'll go to the Tencent episode, but without the Tencent episode on, on Acquired, there wouldn't probably be that Not Boring two-parter on Tencent. 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 kind of that clean a choice to say, like, you know what, instead of public companies, I'm going to do this Web 3 thing. But when I started writing about Web 3, 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

• 1:28:01Speaker 01

  to that piece, that I was writing about crypto and the metaverse. And I was like, everybody, this is really weird. My audience had become like fairly FinTwit and finance-heavy and I thought-

• 1:28:09Ben Gilbert?

  That's this year. That's Packy McCormick writing in 2021 apologetically that I'm sorry, I'm talking about crypto.

• 1:28:15Speaker 01

  Right? I mean, it shows how much the world has changed since then. This was before Beeple's $69 million sale and a bunch of stuff. But I talked about kind of some of the early, early Beeple's.

• 1:28:24David Rosenthal?

  Before you tried to buy the US Constitution.

• 1:28:27Speaker 01

  Before I tried to buy the US Constitution with a bunch of friends. 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. 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 going to take down the institutions and we're going to remove the middleman and we're going to blah, blah, blah. And I was like, no, no, all right. So just taking a step back, if you take out somebody from the transaction and you let the consumer and the creator interact directly, more value accrues to the consumer and the creator. And everybody out there reading is more likely to be a consumer

• 1:29:12Speaker 01

  or a creator than you are likely to be Facebook or Twitter. So like, this is actually probably a pretty good thing for most of us, that, you know, there's just more value that can accrue to both sides of this equation. And so that was kind of, I think, my 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 I even set myself a rule that I would just do kind of like, maybe one web three, I'd probably call 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, you know, I wrote this piece called Power to the Person, which wasn't ostensibly about crypto,

• 1:29:55Speaker 01

  but it certainly 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. And then, you know, wrote a piece that we discussed on a previous acquired episode about Ethereum and then dove into Solana. And I think, hopefully, what I can do, and I actually need to keep myself honest, because I'm getting so excited that I might like actually lose some of this, but really want to give the like, somewhere between this is a scam and this is like going to save the world and take down the institutions. I want to 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

• 1:30:38Speaker 01

  needs to attract developers to build on top of the platform. And those developers need to attract users. And if that happens, then Solana will probably be in a pretty good shape. And like, here's maybe one way you 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.

• 1:31:00Ben Gilbert?

  I like that. 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 really around business fundamentals and structure fundamentals, because a lot of people are like, oh, well, with DAOs, we throw everything out. So no one even like has a manager. 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, if our goal is to ship a product, we do have to figure out some structure to ship a product.

• 1:31:45Speaker 01

  Yeah, I mean, nothing is a panacea. I think this is a really amazing new toolkit to have. And it opens up, again, I'm just probably have spent too much time in tech and VC, and so I say design space now too often, but it opens up this like new design space where you just have a new set of tools that you can build with. And so DAOs, I think, are really great in certain situations. I think eight out of 10 DAOs might totally fail because they, they have like, kind of that leadership issue, or like, who is the final decision maker issue. But I think those other two are going to 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 going to be some emergent properties to DAOs that are really interesting and probably previously would not have been possible. And so that's

• 1:32:30Speaker 01

  a really good thing. And so I don't want people to just dismiss DAOs outright, because sometimes they can be a little bit chaotic, or whatever else. I mean, like, I got involved in the Constitution DAO, which was trying to buy the Constitution this week, and it shows both the amazing things, which is you can rally a group of people around this shared mission and raise almost $50 million 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 timeframe and to organize a 20,000 person discord, all of whom has been told that they're a part of a DAO and has a voice. And so like, what's the right balance there? Then you go into the idea of like progressive decentralization, which I think makes a lot of sense, which is start out kind of like a company. And then over time, particularly if you're building

• 1:33:13Speaker 01

  a protocol or something that is not as like consumer facing, maybe then over time, you can kind of progressively give up control and cede more control to the users and the owners. So I guess, yeah, again, there, the whole, the whole approach is like, here's where it's good. Here's where there's issues and like, here's something that might kind of work and I don't know, let's go try it. The worst thing you could do is just dismiss something.

• 1:33:34Ben Gilbert?

  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?

• 1:33:43Speaker 01

  Before I had, and I still have it on, but I just don't read them. I had my unsubscribes turned on and would literally go through every time someone unsubscribed and be like, oh, someone unsubscribed. Now I don't care as much. I think this is kind of to your point earlier about kind of like getting the audience that you deserve. Maybe there's a little, 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

• 1:34:16David Rosenthal?

  Well, I think the actual quote, it does make sense. The actual quote is not, you get shareholders, you just, you get the shareholders you ask for. In the long run, you get the audience you ask for.

• 1:34:24Speaker 01

  Exactly. And I hope like, what I don't want to do is alienate everybody who has like some sense of the fundamentals of that. Like, those are people that I really want to read, not boring. And I want to keep me accountable. But if people are just like, hey, 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 X in the next two months.

• 1:35:02David Rosenthal?

  I just gave you a truckload of alpha.

• 1:35:05Speaker 01

  But like that stuff still hurts. Like I don't want to not 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 going to 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 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.

• 1:35:27Ben Gilbert?

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

• 1:35:37David Rosenthal?

  Did Jeff Bezos send you that email?

• 1:35:39Speaker 01

  Yeah, Jeff and I, so the thing about-

• 1:35:41David Rosenthal?

  You're not giving him the alpha anymore?

• 1:35:43Speaker 01

  No, I'm kidding. Jeff Bezos and I have never spoken. He doesn't subscribe. Someone, I think, signed up with Satya Nadella'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 CEOs of big companies and all of that-

• 1:35:57David Rosenthal?

  It's actually Putin.

• 1:36:00Speaker 01

  That would be messed up. I was so excited.

• 1:36:03David Rosenthal?

  All right. So, speaking of Web 3, you wrote in your Power to the Person piece, another sort of crazy sounding prognostication that you predicted that within a decade or two, there would be multiple trillion dollar market cap 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 Not Boring itself. It's so awesome. It's like incredible. And like, Ben and I are 100% in the camp that are cheering for you, that you made it to your

• 1:36:45David Rosenthal?

  goal of making a billion dollars in revenue this year. A kind of old school way of thinking about that would be like, Packy is the head of the distribution in the creator economy and one of the few people that have really broken out. You're going to be like an NBA player, you know, level in the, a professional player in the creator economy. Another way to think about where this could go though, is no, you're building a solo corporation. And it's not just that you're going to make a few million dollars a year writing a newsletter. Not boring can be something a lot more. How do you think about that?

• 1:37:20Speaker 01

  This is, I guess, one of the hypocritical things about Not Boring, maybe, is that I analyze everybody else's strategy and plans and all these things, and there really isn't one for Not Boring. Like, would I love Not Boring to be a big and lasting thing that builds actual products and does, you know, things that kind of outlive me 100%. I would love that. I'm, right now, worried about 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 that I'm not planning ahead by like, any stretch. I'm like, one of the worst planners you've ever met.

• 1:38:05Speaker 01

  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, 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 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, is that if I say, you know what, I really wanna like, go start building apps, and I'm gonna build, like, I'm

• 1:38:48Speaker 01

  gonna launch PackEcon, and I'm gonna build a bunch of apps and make, like, try to make, like, a billion dollars, 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 ghostwrite for me and all of that, then it loses the thing that's, 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, like, how do I figure out how to build, you know, whether it's a DAO or some like kind of loose structure around this where other people can go off and like, kind of tap into the not boring 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,

• 1:39:31Speaker 01

  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 about that. But it's like, certainly, I think when I'm 80, 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.

• 1:39:53David Rosenthal?

  I think it's worth spending a little bit of time on not boring capital, which is obviously not web three, 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 sort of our collective corner of the creator economy. But it is a real business and it is a real step towards going from just being a, you know, I'm thinking about like the Oprah episode that we did a year and a half ago, whatever it was, where 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're like, you can make a few million dollars a year, you'll have a great life, right? Or you can own the production, you know, and then you can become Oprah.

• 1:40:37David Rosenthal?

  It does feel like there's kind of this opportunity for creators now to go from just being like an indie version of the talent in front of the camera to a lot more.

• 1:40:46Speaker 01

  Yeah. I mean, I think certainly not more capital is a step in that direction. I think the three of us are very lucky that the type of content that we make is also really well aligned with doing venture capital. Obviously there's a lot of creators who are starting to invest in startups. I'm less dismissive of that, you know, you can probably tell at this point than most people are, because I think, you know, they probably have really deep insights into certain spaces that other people who haven't been creators and haven't built that kind of business wouldn't understand. But I think for us in particular, we're really lucky and, you know, Harry Sevings falls into this camp and a bunch of other people do as well. Lenny and Turner all fall into this camp where. We're living and breathing this stuff every day. And this probably goes back to our conversation on journalistic integrity.

• 1:41:31Speaker 01

  We're like, 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 and 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? 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 planned. Like, that's not where it came.

• 1:42:16Speaker 01

  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.

• 1:42:35Ben Gilbert?

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

• 1:42:42Speaker 01

  I write them up here. Yeah. And so I found when I did 91 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 of 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, you know, like the cooperation economy that unlocks like how somebody thinks about something and then they want to start. 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.

• 1:43:24Speaker 01

  And so like, that kind of helps, you know, on the sourcing and, and winning deal side. But this wasn't planned either. And so I think the next iteration of not boring, whatever, like we kind of add on top here. It probably won't be planned and it'll probably be because it makes sense with 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 like being honest when I get something wrong. Like bill.com, my worst call of all time, being short bill.com only really, the only time I've ever gone kind of pessimistic. I like being called out when I'm wrong on stuff. And I think to be able to run a venture fund that says like, cool, here are the ideas. But then also like, I'm putting money behind it and you'll see the results in how well Fund One, Fund Two, Fund Three did.

• 1:44:06Speaker 01

  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 in the results of how these funds do.

• 1:44:14Ben Gilbert?

  Well, it does seem like you're publishing pretty much like, I think on Saturday you send out 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 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 91 investments?

• 1:44:41Speaker 01

  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 taking advantage of those things. And so 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 it is a house of cards already where you move one thing and like the whole thing breaks. And so if I'm doing kind of the more deeply time consuming parts of a venture, it at least as I'm currently constructed, doesn't work. But it really works very well when, you know, I can talk to a founder and we have the specific area,

• 1:45:21Speaker 01

  either kind of internally or externally where I can be helpful, not to, you know, make fun of that, that venture pun, but.

• 1:45:27Ben Gilbert?

  Put on your khakis and ask a question. Yeah.

• 1:45:29Speaker 01

  Yeah, but there's a bunch of things that, you know, you make trade offs throughout. And I wrote in both the public and private memo that I'm doing probably less diligence on a specific company than most people who are investing in a company will. And that's like an embarrassing thing to say publicly when LPs are reading that or when like the world is reading it. But it's a fact of the business that like. There's just no way in the world that by myself here, while I have another job and I'm investing in 91 companies, I'm going as deep looking for the flaws in a company and like calling references to look 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

• 1:46:12Speaker 01

  go really, really right here. And so this will either blow up totally in my face, or we're in this crazy bull market, and I should have been a lot more conservative and like gone for like VC value investing, or it'll work, but the whole thing is transparent. Which is a thing that's never worked, by the way.

• 1:46:27David Rosenthal?

  Even Ho and Altus would probably agree with that. I would argue, I mean, I'm sort of doing very similar things with kindergarten ventures with Nat is what you're doing with Not Boring Capital. 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's not like you cooked it all up on a whiteboard, but it's kind of like the sponsored posts, right? 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 obviously that wouldn't work for what you're doing. You know, you've got a big business writing

• 1:47:11David Rosenthal?

  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 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 kind of new way of thinking, right?

• 1:47:33Speaker 01

  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 thoughts 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 that. Right now, you get out of a partnership at a firm and it's not as formal and I will still make more mistakes than probably a firm will make, at least on the like saying yes to things that maybe I shouldn't say yes to.

• 1:48:04David Rosenthal?

  But venture capital is never about the mistakes. The only thing that matters in venture capital are the ones you get right. And that's kind of the point, right?

• 1:48:11Ben Gilbert?

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

• 1:48:16Speaker 01

  To the best of my knowledge, none of my founders are committing fraud and they're all amazing, but I mean, 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 don't really care. But I'm putting trust in the overall kind of ecosystem and system that other people are doing their jobs, which again, could totally blow up in my face or not, but that's just a trade off.

• 1:48:41David Rosenthal?

  Well, the way you're constructing your portfolio with 91 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 kind of shifted the mindset from like playing defense of like, we're going to make sure fraud doesn't happen. But in venture capital, the zeros are meaningless. 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 effort and work to build it. We're going to take board seats. We're going to give you great advice. We're going to do all this stuff. For you, it's a byproduct.

• 1:49:27Speaker 01

  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. 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 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 20 employees, you have people who are relying on you.

• 1:50:12Speaker 01

  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.

• 1:50:28Ben Gilbert?

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

• 1:50:36Speaker 01

  Nine point nine nine million dollars.

• 1:50:38Ben Gilbert?

  Nine point nine nine. Your second fund's 25 million.

• 1:50:41David Rosenthal?

  You couldn't get it to 10? Oh.

• 1:50:43Speaker 01

  You're not allowed to get it to 10.

• 1:50:44David Rosenthal?

  Oh, I see. I was gonna say, you could have called me up. I'd give you an extra 100 bucks.

• 1:50:50Speaker 01

  And fund two, were it to exist, would potentially be in the 25 to 30 million dollar range.

• 1:50:56Ben Gilbert?

  In that range. Okay. 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 no longer the hard part.

• 1:51:12David Rosenthal?

  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 are real.

• 1:51:26Ben Gilbert?

  Exactly. And the challenge with AI is governing it, securing it, measuring it, and making sure that it actually delivers value. That is why ServiceNow built the AI Control Tower.

• 1:51:36David Rosenthal?

  Yep. AI Control Tower gives enterprises a single place to see, manage, govern, and optimize AI across the entire business. And it works with any AI, not just theirs. Every device on your network, every permission across every system, every AI agent, visible and secure in one place.

• 1:51:53Ben Gilbert?

  And ServiceNow can do this because they've spent more than 20 years building the operational backbone of the enterprise. The workflows, governance, approvals, security controls, and institutional knowledge that power how work actually gets done across IT, HR, customer service, finance, and security.

• 1:52:09David Rosenthal?

  ServiceNow already runs more than 100 billion workflows annually and trillions of transactions for more than 85% of the Fortune 500. So when companies need a place to govern AI at enterprise scale, they're building on a platform at the center of how their business already operates.

• 1:52:26Ben Gilbert?

  And in a future that isn't going to be one AI, it's going to be thousands of AI agents working across every function of the company. But the question is, who's managing them all?

• 1:52:35David Rosenthal?

  So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely, at scale, go check out servicenow.com/acquired and tell them that Ben and David sent you. Okay, so I think before we move on from not boring capital, it's 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 Substack, Twitter, et cetera. You know, the platforms enabling not boring the media company. Angel List enables not boring capital, enables kindergarten capital. Like, I've spent 11, 12 years in venture now, nine or 10 of those as a traditional professional venture capitalist. This would not have been possible. You are one person. You did 91 deals in Fund One.

• 1:53:20David Rosenthal?

  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.

• 1:53:30Speaker 01

  It's more than, I'd say, the equivalent of Substack for a venture firm because Substack, I still have to write everything and edit everything and make all of my own graphics and all of that. I work with Jen on the Angel List team. I will give Jen a shout out 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. And so having both the platform itself, which is great and makes it really easy to raise money from LPs

• 1:54:12Speaker 01

  and for LPs to get visibility into kind of how the portfolio is performing. All the 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, lets all of this happen. If there was no Janet Angel List, not boring capital would not, 100% would not be a thing.

• 1:54:33Ben Gilbert?

  It's a total reorganization of the value chain by dismantling the vertical integration of venture firms. 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, Packy 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. 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. It's not just that there's a massive back office that you now don't need to have too. I mean, traditionally, a venture firms, you have an IT person. Like I mentioned, you don't have an IT person.

• 1:55:13Ben Gilbert?

  So not only does your media company not have a vertically integrated staff associated with it, but your venture capital firm 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.

• 1:55:34Speaker 01

  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 bringing this. I mean, this is kind of the point of the power to the person piece, 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. Now, it's great, you know, Substack is 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.

• 1:56:18Speaker 01

  It's like AWS for a venture firm. It's like AWS for a 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 the integration and 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, $9.999 million 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. 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.

• 1:57:00Speaker 01

  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 said, this is not an Angelus ad, but it is maybe a Gen ad. Gen's the best. Nicole is also great. She's our person there. There you go. Thank you, Nicole. 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 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 $25,000 a year to do what they're doing for not boring. Like I've getting hundreds of thousands of dollars worth of advice and service and all of that from Angelus, but they also have thousands of other clients. And so it works. And the more there are places that get really, really

• 1:57:45Speaker 01

  good at one specific thing, the easier it is for one person to start a business that draws from all of that.

• 1:57:50Ben Gilbert?

  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.

• 1:58:01Speaker 01

  Exactly.

• 1:58:02Ben Gilbert?

  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?

• 1:58:14Speaker 01

  So the trade offs right now are, I don't have any outside investors. I mean, I have LPs for the fund, but 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 person things, but that means that 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 because I'm worried every time that the momentum will slow and there's not, you know, somebody else on the team who's just going to 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

• 1:58:57Speaker 01

  side, that if I have other people writing, maybe people don't want to come to not boring to read X, Y, and Z other person. That's not the point. I don't want to be an editor and make sure that we all have the same tone. And so like, I'm kind of limited, I think, to whatever I can do as kind of one, at least kind of front person on this thing. 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. 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.

• 1:59:40Speaker 01

  But 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. 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 tacky branded hats. They'd be like, all right, like, maybe I'll buy a hat. Can we get some sneakers? I'd definitely pimp some Not Boring sneakers. All right, well, we'll do some Not Boring sneakers. That we can do. But 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.

• 2:00:24Speaker 01

  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 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 going to go read this other person who just does the content.

• 2:00:54Ben Gilbert?

  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. 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, because we're not willing to organization build around sort of pulling ourselves out of the core product because you are the product.

• 2:01:35Speaker 01

  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 predictable way. Maybe we could both figure out how to scale these things out. I've been like, you know, I like business breakdowns a lot from the invest 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 VC 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

• 2:02:19Speaker 01

  months 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.

• 2:02:36Ben Gilbert?

  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, kind of like they did for the, I mean, that's a, what is it a hundred person team now or something doing morning brew? And I don't think Austin 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.

• 2:03:05Speaker 01

  And you guys could probably do it better than I could, right? Like, I think the great thing about that business is they had 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.

• 2:03:29David Rosenthal?

  But you have robots on the walls.

• 2:03:30Speaker 01

  Robots on the wall. I have my brother who edits the vast majority of my pieces and helps me things, helps me think through the business side. Pooja is a saint and like in addition to kind of like working a full-time job and managing our growing boy also will, 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, all right, Dan and Pooja, you write the next not boring while I think about building this organization.

• 2:03:56David Rosenthal?

  You know, Ben and I talk about this. It is interesting. Like I've been thinking for a long time now and you know, certainly this is the path we've taken and acquired of like, 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 it's interesting.

• 2:04:26Speaker 01

  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 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, you know, take a weekend off every once in a while, like that would 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.

• 2:05:02Ben Gilbert?

  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 20% month over month growth? What do you think the saturation point of your audience is?

• 2:05:17Speaker 01

  I mean, you know, it doesn't feel. As exponential, the chart where like it still grows 1,000 to 2,000 people a week, the newsletter, but 1,000 to 2,000 people a week is a lot different when you're at 40,000 versus 80,000. And so like, maybe it does go a little bit more linear than exponential at some point. Maybe we are hitting the 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 going to kind of keep doing what I'm doing and 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,

• 2:06:00Speaker 01

  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 I like on the content side, other than just being kind of obsessed with the idea of Constitution Dow, why I was like, all right, I could either write a normal, not boring piece, or I could like kind of 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 think where this ends up losing its steam 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. Like if I go too far into the future 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

• 2:06:42Speaker 01

  your kind of like tech roundup, 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 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 more comfortable with it, then I think I'll be able to kind of continue to grow.

• 2:07:15Ben Gilbert?

  I feel like you live three to six months in the 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 this will help me get there by reading it.

• 2:07:32Speaker 01

  The fun thing for me has been that I'm writing this like very tech optimistic newsletter in the greatest bull run ever that somehow instead of getting, you know, like hitting its own S curve point, like keeps getting wilder. And so, you know, 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, 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 going to be a really interesting time in not boring, where I'm like, all right, everybody just like, 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

• 2:08:14Speaker 01

  the venture side and the newsletter side, is that people are like, enough with this optimism. Like, things are kind of tough right now.

• 2:08:20Ben Gilbert?

  Okay. So just to highlight before we finish history and facts here and move into powers, 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 78,000 followers to 106,500 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's voice, not just in the unique Packy voice that I love, that brings me three to six months of the future today. And it is a very different voice. I mean, you read that Economist piece and you're like, wow, this is written

• 2:09:00Ben Gilbert?

  by The Economist, not by Packy and Chris. And of course, speaking of Chris Dixon, you're working with Andreessen Horowitz now. The whole world, including Packy, they've hired. So I want to point out all the results of this crazy compounding that unbelievably happened to you in mid-October to mid-November of 2021. And A, what does that feel like? And B, what are you doing with A16Z?

• 2:09:25Speaker 01

  Yeah, so I think actually the biggest growth driver potentially was that Mario and I wrote this piece on Discord.

• 2:09:32David Rosenthal?

  Oh, yeah.

• 2:09:33Speaker 01

  And then Discord CEO, in the replies to my tweet about the piece, announced that they were adding Web3 integrations and then announced that they were not adding Web3 integrations. And so that brought out 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, you know, the same week that the Economist piece came out and announced the advisory at Andreessen off the back of that. So just a bunch of things happened at the same time. So that makes the Twitter graph look a little bit wild, but I think that was an underappreciated one. 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?

• 2:10:15David Rosenthal?

  You're like picky in the brain.

• 2:10:17Speaker 01

  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, there will certainly be ebbs and flows. We're going to go into the holiday season here where everything, like, I'm going to 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 flows just kind of average higher over time. In terms of the A60Z advisory, 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.

• 2:11:01Speaker 01

  But if you can't translate what's happening and why this is going to be actually good for people and like actually what's happening beneath the surface here, everybody's kind of just going to miss out and dismiss this whole thing. And so I think really kind of 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 in or are excited about. And not like, you know, there's no 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 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, a potentially

• 2:11:43Speaker 01

  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 going to 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 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 I was like, oh, man, everybody's out like, I don't know about that. And so I was like, gonna do a snarky tweet, not snarky, but you know, like, I was gonna do a tweet that was kind of like, I'm joining A16Z2. And then I went out to the offsite that the team did out in California. And it was so clear that like, this big team of people was there because Andreessen was just kind of throwing its

• 2:12:24Speaker 01

  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. 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, 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 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 choked at the beginning by overregulation and by people's lack of

• 2:13:09Speaker 01

  understanding. And so I came out of that feeling a lot more optimistic and just even like more excited about working with them after kind of getting to meet more of the team.

• 2:13:17Ben Gilbert?

  Cool. Well, thanks for cluing us in. I mean, it's fascinating to me that, yeah, that 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, 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.

• 2:13:38Speaker 01

  Yeah. I mean, I've had that other conversation with funds too, where it's like, hey, you want to come work and 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.

• 2:13:55Ben Gilbert?

  Yeah, listeners, we're going to talk about this in grading because I'm curious to dig into that. No. So hold that thought for now. Let's do powers. You've got this concept of the not boring flywheel, which I want to say it's kind of 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 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.

• 2:14:31David Rosenthal?

  And that was from a great interview you did with Jake Singer like a year plus ago that we use as a big resource here.

• 2:14:38Speaker 01

  Actually, right around February.

• 2:14:40Ben Gilbert?

  Oh, wow. So it needs to be updated.

• 2:14:41Speaker 01

  It probably actually was a result of the million dollar tweet. I think that's when he was like, all right, we should talk.

• 2:14:46Ben Gilbert?

  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 are strongly tied?

• 2:14:57Speaker 01

  I think as we talked about a little bit before, audience at the center of the flywheel is maybe not exactly the thing. Like, if I had a million person audience of people who didn't care about startups or 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 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 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

• 2:15:39Speaker 01

  and who also include people who are starting companies and running companies and all of that. 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.

• 2:15:52Ben Gilbert?

  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, ah, sorry, there's not really space in this round for this reason?

• 2:16:04David Rosenthal?

  Or you're talking to somebody about sponsoring and then they're like, eh, actually, no.

• 2:16:08Speaker 01

  On the sponsor side? Really, it comes down to price, frankly. And I think if this were a 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, I'd like to write about them, but I'm going to 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 are like, have something interesting strategically that like, just maybe isn't interesting enough to the audience where like, actually, it would

• 2:16:51Speaker 01

  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 ACV product. And if they get 50 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 50 people are the only 50 people who actually cared about that particular story. So I try to do a little bit less of that. On the founder's 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 kind of 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 Packy from Not Boring and it's an 88,000 person audience. They're like, oh, cool. You read

• 2:17:35Speaker 01

  a newsletter? 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.

• 2:17:46Ben Gilbert?

  Such a good point. Because otherwise, it's transactional. And they're like, so are you going to write about me for free? Why do I care that you have a newsletter?

• 2:17:53Speaker 01

  A hundred percent. And like, you know, I'll get that sometimes from founders when that's kind of the introduction path where like, I had a founder recently email me and ask, you know, after I said, you know, I committed and said, here's what 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, this feels more transactional than I want it to feel like. This will be good for both of us if this works out. Yeah, I really don't like 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 $75,000 in allocation because you have a 45% open rate and 88,000 subscribers and I've done the math. That doesn't feel right.

• 2:18:38Speaker 01

  It's more like, am I aligned with this founder and want it excited about the story?

• 2:18:42Ben Gilbert?

  Put another way, the size of the audience is not important because that is reach 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?

• 2:19:05David Rosenthal?

  And that mental leap is like automatic. If you're already a Not Boring fan, then you're like, oh, I get it, right? Like, people like me read Not Boring. I want to get in front of more people in my orbit. This makes sense.

• 2:19:18Speaker 01

  The other way to describe that is I don't think it's gotten any easier convincing founders to give me allocation at 50,000 readers or 88,000 readers. Like, if they're a reader, then they kind of 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, 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's side, that's really the binary is do you read Not Boring or not?

• 2:19:44Ben Gilbert?

  Yeah, makes sense.

• 2:19:45David Rosenthal?

  Makes total sense.

• 2:19:47Ben Gilbert?

  Okay, powers.

• 2:19:48David Rosenthal?

  Seven powers for Not Boring?

• 2:19:51Ben Gilbert?

  Yes.

• 2:19:51David Rosenthal?

  This is gonna be fun. I'm going out on a limb here. I think it's not gonna be scale economies.

• 2:19:57Ben Gilbert?

  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 read 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 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 quarter, The valuation can change by billions and billions and billions of dollars because

• 2:20:41Ben Gilbert?

  people are accounting for the next 29 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 than you would forecast in a public company with a durable organization and product market fit, because it's so PACY 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.

• 2:21:16Speaker 01

  That's right. I don't want to raise money, because then I'd have bosses, and I don't think I'd get a valuation that I'd be happy to sell part of myself for.

• 2:21:25Ben Gilbert?

  Yeah. Well, David, where do you think the strongest one is?

• 2:21:29David Rosenthal?

  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, at least relative to traditional media companies.

• 2:21:37Ben Gilbert?

  Yeah, certainly on the journalism side, actually, and on the venture side.

• 2:21:40David Rosenthal?

  Totally on the venture side. I think there may be some element of network economies here, kind of like what you were just talking about with the flywheel and being a reader. Like, the more people in your target audiences who are readers, the more powerful taking an investment from not boring capital, or sponsoring not boring, or frankly, just continuing to read not boring, becomes as more people in your circle are reading it.

• 2:22:07Speaker 01

  I think that's probably right, but I don't want to give myself too much credit on it. And I know, like, you know, 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. I think this is like, data network effects, or something where like, maybe it's there. And like, kind of sometimes, like, maybe people have it, but probably, like you say, there's data network effects, just to like, pretend like there are network effects. And I actually don't know if I If I have them, like if it means that I'm able to write about more interesting 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 audience is getting bigger and I have more interesting conversations with people.

• 2:22:49Speaker 01

  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.

• 2:23:00David Rosenthal?

  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 Reed's not boring. We talk about not boring.

• 2:23:09Ben Gilbert?

  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. I'd say that's an opportunity. Now, maybe one that doesn't meet the bar, but an opportunity.

• 2:23:29Speaker 01

  I think that's 100% right. I definitely, I think probably because of Not Boring Club, shied away from trying to like be a community manager again. But I do think Twitter is kind of where that exists now, but I think there are absolutely opportunities and maybe that's where you know, 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.

• 2:23:56Ben Gilbert?

  There's one that I want to 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 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.

• 2:24:41Speaker 01

  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 and I never have a good answer for it because there isn't a good answer for it.

• 2:24:52David Rosenthal?

  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 going to sound like.

• 2:24:59Ben Gilbert?

  Well, Ben opens up text edit and he has a document that has a zillion fonts in it because it's been cloned from 250 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.

• 2:25:12Speaker 01

  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 want to scale it and have to write like a 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 the brand voice. I don't want to do that.

• 2:25:31David Rosenthal?

  Okay. So what was that process like writing for The Economist? Like, what was the transition from you wrote a draft to final piece?

• 2:25:38Speaker 01

  It was pretty close. Like, yeah, it goes to their editors, but the interesting thing is that they send you their guide upfront on kind of the things to avoid. And so 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 upfront 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 an editor, they go for it. But I definitely tried to kind of, you know, catch The Economist's style in the thing that we wrote.

• 2:26:06Ben Gilbert?

  All right. Done with powers?

• 2:26:08David Rosenthal?

  Yeah, I'm with that. I think it's process power. It's like, at the end of the day, it's creative business.

• 2:26:12Ben Gilbert?

  For sure. All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Logora, the agentic operating system that is redefining how the world's best legal teams work.

• 2:26:26David Rosenthal?

  Yep. It's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Logora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 2:26:43Ben Gilbert?

  So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done.

• 2:26:58David Rosenthal?

  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. Legora'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.

• 2:27:22Ben Gilbert?

  And they recently launched Legora 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.

• 2:27:41David Rosenthal?

  And Legora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Legora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Legora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months.

• 2:28:11Ben Gilbert?

  Truly insane numbers. And that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reaches 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 legora.com/acquired and just tell them that Ben and David sent you. All right. So, Packy, I was thinking about this. Should you go work at a venture firm? And 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.

• 2:28:52Ben Gilbert?

  And let's say to reflect the very quick audience that you've sort of built this relationship and community you've cultivated and, you know, the way that you're seeing into a very important future in Web 3. 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 it double-digit percentage of carry in a brand-new, multi-billion-dollar fund, or at least billion-dollar fund. So you're getting like, serious economics, but the returns are probably like, seven-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 baking, just in salary. So you have this sort of interesting

• 2:29:33Ben Gilbert?

  question of like, do you want to delay most of your upside another five, seven-plus years? And do you want to 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 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?

• 2:30:03Speaker 01

  I think that you're thinking about it right in the set of trade-offs. I think the tricky part is that, and Schrödinger's cat is not right here, but maybe you'll understand the right version of what I'm saying, is that as soon as I go in-house somewhere, I lose half of my value, 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 of that, there is like this independent voice that I have that obviously goes away. Everything that I write would go through 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

• 2:30:46Speaker 01

  my last sentence 30 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. 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 McCormick, people like now think that I'm smart where like now I kind of need to prove that that 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 fund, because I don't lose all of my value as soon as I set foot in the door of that fund.

• 2:31:31Speaker 01

  But I think for the time being, 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.

• 2:31:42David Rosenthal?

  It's funny, I'm thinking as you're saying that you 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. 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 than continue. And we're going to shut down 90% of your business, but the ultimate value is going to be higher.

• 2:32:21Speaker 01

  I think that's probably right. And 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 maybe you don't have a web three practice, but like you need to play catch up. I still think there are better people, frankly, who are like way more technical. 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 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. They're making it to keep that away from other people and to do something themselves.

• 2:33:03Ben Gilbert?

  There's this funny like 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 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 going to go join anywhere else either.

• 2:33:24David Rosenthal?

  Or it makes me more like, shoot, if I'm gonna game theory this all the way out, if Packy'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?

• 2:33:38Speaker 01

  Well, I've been public about kind of everything in Not Boring's path. So if this does happen, if people start making big offers, I'll come back on and let you know what those offers look like.

• 2:33:47David Rosenthal?

  Okay, so to me, though, I think the wild crisis is where, you know, it's our show. We get to grade you. You can chime in at the end, too. 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.

• 2:34:11Ben Gilbert?

  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.

• 2:34:21Ben Gilbert?

  It's actually not lifestyle. I'm sorry, I'm really restate that.

• 2:34:24Speaker 01

  Lifestyle would be better, actually, in that one, too.

• 2:34:26Ben Gilbert?

  It's control.

• 2:34:28David Rosenthal?

  Yeah. If you want control now, or you want lifestyle and cash now and cash in the future, go join a venture firm. But here's my question. Can you also manage billions of capital in not boring capital? That's the question someday.

• 2:34:44Speaker 01

  It's such an interesting question because 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 boring keeps getting bigger and I was able to hire like a really phenomenal team of people who are much smarter than me 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 deploy a billion dollars in follow checks.

• 2:35:16Ben Gilbert?

  You can't just slide in a little. Yeah.

• 2:35:17Speaker 01

  Yeah, exactly. You'd have to be able to invest in like every, even at all reasonable company. 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, Josh and Lucky and like that group of people has turned kind of a sole 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.

• 2:35:47David Rosenthal?

  Well, hell, Andreessen itself, the Andreessen story was that, right? Like Mark and Ben were super angels. They played nice with everybody. They had everybody in the valley, except maybe Benchmark after the LoudCloud experience. And then they were like, well, I think we can turn this into a firm and they did.

• 2:36:01Speaker 01

  They're a little smarter than I am.

• 2:36:02David Rosenthal?

  Well, it's a different thing than being a super angel, but it doesn't mean it's not possible.

• 2:36:06Speaker 01

  Listeners, stay tuned to find out.

• 2:36:08Ben Gilbert?

  As the, I don't know if you're the primary or the sole shareholder of not boring, you also kind of just get to pick. You're like, well, if this will make my life worse and I don't need to make more money, why would I do it?

• 2:36:20Speaker 01

  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. 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.

• 2:36:49David Rosenthal?

  Fair answer. We'll accept it.

• 2:36:53Ben Gilbert?

  You guys want to do carve outs?

• 2:36:55David Rosenthal?

  Yeah, let's do it.

• 2:36:56Ben Gilbert?

  All right, David, you first.

• 2:36:57David Rosenthal?

  Okay. My carve out fitting for my status as new dad. This might be portending a lot of parenting carve outs to come, but some people had told us this before we went to the hospital to give right there. And I didn't pay attention and I wish I had. 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 nurses in the hospital, they just like a regular blanket and they take it and they put the baby in the blanket and they do some folds and they're 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

• 2:37:42David Rosenthal?

  baby comes out of the swaddle, you got to re-swaddle the baby. Like I got it's just like, whoa.

• 2:37:47David Rosenthal?

  How did they do that? That was magic. You can't do it. 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. That's my carve out. Seconded.

• 2:38:08Ben Gilbert?

  Boy, David's carve outs have really changed.

• 2:38:10David Rosenthal?

  Totally.

• 2:38:13Ben Gilbert?

  It's great advice, though. 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 carved 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 I'm going to do something that is way too much talk in my own book, but I think it's an awesome thing to read. And we were 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 Engineer's Hype-Free Observations on Web3 and Its Possibilities."

• 2:38:54Ben Gilbert?

  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? 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? 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 going to try and ignore some of the cultural elements of Web3 and just do it a little bit more analytically. And of course, you can't help but throw in some cultural elements because 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.

• 2:39:37Speaker 01

  So I'm gonna keep it in Seattle for mine. I think the last time that we talked, maybe 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 2021. And this one book came up and it was described as Haruki Murakami meets Ready Player One. And Haruki Murakami is my favorite author. Ready Player One, maybe not the best written book of all time, but it's certainly inspired a lot of the things that people are talking about right now. So this book is called Rabbits. It's this thriller about this kind of global game that takes place to save the world.

• 2:40:20Speaker 01

  And you play it by following a bunch of these coincidences that seem like coincidences, but maybe they aren't. And 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, 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.

• 2:40:47David Rosenthal?

  Oh, I'm gonna have to check this out.

• 2:40:49Speaker 01

  And I'm learning a lot about Seattle, which is making me feel closer to Ben.

• 2:40:52Ben Gilbert?

  You're welcome anytime, my friend.

• 2:40:53David Rosenthal?

  Oh, Seattle's such a great sci fi. Tenuous Seattle connection, but also sci fi and sci fi books. I am so hype November 30th, 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.

• 2:41:08Ben Gilbert?

  Oh, wow.

• 2:41:09David Rosenthal?

  Oh, I'm so hyped.

• 2:41:10Speaker 01

  Someone recommended The Expanse to me today. I've never read any of them, so I just, I bought book one.

• 2:41:14David Rosenthal?

  Oh, my God, you gotta read it. It's the best. It's so good.

• 2:41:17Ben Gilbert?

  Have you watched the show?

• 2:41:19Speaker 01

  No, I've been told to read the books first and then watch the show.

• 2:41:22Ben Gilbert?

  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.

• 2:41:30David Rosenthal?

  I'm rereading to get ready for the final book. Uh, so there's 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. Four, five, six, and seven are like, they're still really good. Like read them through the first time. I reread one and two, and then I'm rereading eight, and then I'm going to go right into nine.

• 2:41:55Speaker 01

  Have you read Red Rising, the Red Rising trilogy?

• 2:41:58David Rosenthal?

  No, I need to.

• 2:42:00Speaker 01

  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, 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.

• 2:42:27David Rosenthal?

  Wow.

• 2:42:28Speaker 01

  Yeah.

• 2:42:28David Rosenthal?

  How many books total are in the series?

• 2:42:30Speaker 01

  I couldn't tell you.

• 2:42:31David Rosenthal?

  You just stopped.

• 2:42:31Speaker 01

  Stopped.

• 2:42:32David Rosenthal?

  Wow. Interesting. Okay. I'll have to check it out.

• 2:42:36Speaker 01

  One through three, though, you should definitely read once the expanse is over.

• 2:42:39David Rosenthal?

  Great. Well, the expanses, um, if you only watch the TV show, you might not know it. There's two authors. So James S. A. Corey is a pen name of the two authors who collaborate. They are George R. R. Martin's assistants.

• 2:42:51Speaker 01

  No way.

• 2:42:52David Rosenthal?

  So the expanse is Game of Thrones in space.

• 2:42:55Speaker 01

  Oh, I never realized that.

• 2:42:57David Rosenthal?

  Yeah, it's really good.

• 2:42:59Speaker 01

  All right. Well, now I have to go read the books.

• 2:43:01David Rosenthal?

  Me too.

• 2:43:02Speaker 01

  Wild.

• 2:43:04David Rosenthal?

  All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig.

• 2:43:10Ben Gilbert?

  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.

• 2:43:21David Rosenthal?

  Yep. In the crazy speed of today's AI world, shipping fast is just table stakes now. 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.

• 2:43:41Ben Gilbert?

  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.

• 2:43:53David Rosenthal?

  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/acquired to get started.

• 2:44:04Ben Gilbert?

  Well, Packy, we can't thank you enough for being here.

• 2:44:08Speaker 01

  Thank you for having me. This was a dream come true. This is so much fun.

• 2:44:12Ben Gilbert?

  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

• 2:44:25Speaker 01

  The company just happens to be

• 2:44:27Ben Gilbert?

  Paki. One person at 18 months old.

• 2:44:31Speaker 01

  It's surreal.

• 2:44:31Ben Gilbert?

  I also, as we drift toward our closing notes here, I was going to tell folks, seriously, you should go subscribe to the public acquired LP show, wherever you get your podcasts 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 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 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

• 2:45:14Ben Gilbert?

  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.

• 2:45:26Speaker 01

  If my biggest contribution to the world is making more great content free on the internet, I am very psyched with that legacy.

• 2:45:33Ben Gilbert?

  Awesome. Well, Packy, where can listeners find you or Not Boring on the internet?

• 2:45:38Speaker 01

  So Not Boring is at notboring.co. I have a poorly produced podcast that you can find by searching Not Boring Podcast wherever you listen to podcasts. We're going to get you upgraded. We're going to get me upgraded. Next time we do this, you're not going to be saying poorly produced.

• 2:45:51Ben Gilbert?

  It's not that poor. Like, that is how I read Not Boring is listening.

• 2:45:54Speaker 01

  That's true. Yeah. I mean, none of it is overly produced, which I think is good. Or Twitter is at Packy M. P A C K Y M.

• 2:46:02Ben Gilbert?

  Awesome. And listeners, we'll catch you next time.

• 2:46:05Speaker 01

  See you next time. Bye.