EP 15 Pt 2: Packy McCormick and Ben Thompson Talk About Their Own Start, Finding Your Audience and The Creative Process

(00:00:00) Intro (00:02:28) Packy & Ben’s Businesses (00:23:08) Finding Your Audience (00:36:01) VC Hindsight (00:46:18) Creative Process (00:57:52) Web3 (01:05:57) Advice for Content Creators (01:14:59) All-In and Twitter (01:23:54) One Last Thing Follow the show: https://twitter.com/3cartoonavatars https://www.instagram.com/3cartoonavatars/ https://www.tiktok.com/@3cartoonavatars Follow the hosts: https://twitter.com/loganbartlett Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson Not Boring - The Great Online Game - https://www.notboring.co/p/the-great-online-game?s=r Not Boring – Schumpeter’s Gale - https://www.notboring.co/p/schumpeters-gale?s=r Not Boring – Ramping Up - https://www.notboring.co/p/ramping-up?s=r Not Boring – Ramp’s Double Unicorn - https://www.notboring.co/p/ramps-double-unicorn-rounds-behind?s=r Stratechery – What Clayton Christensen Got Wrong - https://stratechery.com/2013/clayton-christensen-got-wrong/ Stratechery – Bubble Talk Revisited - https://stratechery.com/2020/bubble-talk-revisited-it-wasnt-1999-the-big-tech-basket/ Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

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

• 0:04Logan Bartlett?

  This is about to be part two of the 15th episode of Three Cartoon Avatars. It's a conversation that I recorded with Ben Thompson and Packy McCormick, where we talk about a bunch of stuff that's related to them launching newsletters and how they think about their business model, how they, the inspiration each of them has taken from the other and all of that stuff. So excited for you to hear that now. All right, well, I am joined today by Ben Thompson and Packy McCormick. For those that don't know, Ben is the founder of Sturteckery, which is a blog slash website and newsletter that has existed since 2013, 2014, covering the strategy that exists within technology broadly defined. Packy McCormick has been on the podcast before. He's the founder of Not Boring, a longtime friend.

• 0:47Logan Bartlett?

  Not Boring is also a blog and website, as well as a newsletter that started at the beginning of 2020 to cover technology and strategy as well. So I've given the context of my relationship with Packy before, but quick rehashing of that, we were friends in New York when we were 22 years old. And here we are a dozen years later and we've both ended up in tech and doing some content related stuff. Ben and I have, I've just been a longtime reader of his. Ben, I went back and looked, I've been reading since November 2015. So not the earliest days, but definitely the early days. And your writing has shaped a lot of how I think about the tech industry at large. And so I wanted to pull the two of you together because somehow both of you have not spoken, although, Packy, I know you've taken a lot of inspiration from Ben.

• 1:28Logan Bartlett?

  And yeah, so I'm happy to be able to facilitate this and excited for where we're going to head.

• 1:35Speaker 01

  Awesome. Well, it's nice to, it's nice to meet both of you virtually, if not in person. And I'm feeling good. I'm feeling good. The Bucks just won. I might be feeling good because I was, I was up very late enjoying the victory. But we'll roll the dice and see how it goes.

• 1:49Logan Bartlett?

  Yeah, totally. I was going to say that we, Packy and I are, right now it's 10:00 PM Eastern time. And so if we were operating, otherwise we'd be exactly as quick as Ben and just as smart as him.

• 2:00Speaker 01

  No, no, I slowed myself down to your level. Don't worry. We're all on the same page here. Yeah, you should be listening to this on 1.5 to 1.8x to make us sound smarter.

• 2:08Logan Bartlett?

  That's right. There's going to be some heavy audio engineering we're going to do on our side to make us sound far smarter than we are.

• 2:13Speaker 01

  No, no, no, don't worry. We're all in a depressive state right now for various reasons.

• 2:18Logan Bartlett?

  Yeah, exactly, exactly. Well, good. Well, uh, so just to start off, uh, we'll have you guys say something nice about the other one. Um, no, uh, so, so totally kidding. Uh, so I guess we'll ostensibly.

• 2:28Speaker 01

  No, no, I'm happy to do that. I, I, I'm actually, I, I, I'm, no, it's cool. We're talking about content and talking to Packy because I think one of the thing that has been really, uh, interesting to me is on one hand, obviously I'm, it's super great to see people doing the model broadly that I'm doing. But it's actually cool because Packy's model is different than mine. And I know, Packy, you, you kind of did some subscriptions at the beginning and then you kind of went all free or I don't know if you ever turned on the subscription or not, but, but to do like the sponsored approach, which I thought was very clever for a lot of reasons. Um, one, it's good because you can just reach way more people, um, which is always a good thing. You know, that, that makes me jealous in a way. But two, I think it gives you a much better approach to covering things like startups because like, um, there's a, you know, you,

• 3:10Speaker 01

  the problem with covering startups and new companies, it is a problem that I've always had with Chitkery is you, there's no public data. And if there's no public data, it's hard to know what to do or believe. And so you can kind of go the opposite direction and say, hey, look, there's no public data. I'm looking to invest. Here's my investment thesis. I think it makes a ton of sense. You get a really strong alignment between what you write, your business model and all that sort of stuff. And so I find what you do really impressive, not just because the writing is good, but also I love when businesses are kind of like fully aligned. And you didn't just like mimic what I was doing, but actually sort of figured out a different way. So I, from my perspective, it's super cool. I would have to sort of railroad or jump ahead in the conversation, but, um, it's, I've really admired what you've done for that reason alone.

• 3:51Speaker 02

  I mean, that means a ton. So I, as we, we were kind of talking about a little bit before this, I mean, the, you know, Chitkery is, is the inspiration certainly for, for not boring. I think the first piece I wrote when I wrote, I took this writing course and you had to write something about somebody who's working like they wrote the best of Ben and it was about how your work had impacted the stuff that I was doing at Breather for better or worse, I guess, because the company ended up selling for $3 million. So thanks a lot. Um, but, uh, no, I mean, it was, it was certainly an inspiration as I got in, I think in the beginning I called the newsletter kind of Ben Thompson and Bill Simmons had a baby. You get not boring. But to your point, I, I think I realized really hard, I was actually, you know, I've always been fascinated in tech and strategy and all of that. And I've avoided it for a really long time because I was like,

• 4:34Speaker 02

  shit, Ben has this covered. There's nothing else to do here. And so when I decided to finally do it after kind of, you know, writing around the edges for a year. There was a very intentional choice, not on the business model necessarily, but to say like, look, this guy is way smarter than me and this is his corner. I have to go full in on the memes and like all kind of this, you know, more humorous and lighter approach. And I think a bunch of things kind of evolved just from that needing to counter position because there was no way that I can compete directly.

• 5:03Speaker 01

  Well, I think you're being a little generous here. I probably said that was fortunate to be early, but um, but yeah, no, I think that gets to a broader point too, which is this space is very large, right? And one of the things that I realized very early on, and because a lot of people were very skeptical. I mean, because when I, when I watched the pay version of Stratechery, you know, this model didn't really exist. I mean, there'd been like, there'd been newsletters on Wall Street and stuff like that. Like they literally, they literally like printed them out and bailed them to you. And you paid like, like they still, they're still around. You pay like $25,000 or $30,000 a year for these. And this idea of sort of doing high volume, taking advantage of services like Stripe to sort of like serve a broad audience. It really rests on this idea that the internet is way bigger than you think it is.

• 5:45Speaker 01

  And you go back to 2013 and like, there was widespread dismissal of, or 2014, I should say, of when I went, of when I started offering for pay from Intech and a lot of people like, hey, well, that you're trying this, but man, I just, you know, I want you to really think about this, da, da, da, da. You should do whatever. And that, I just wanted a thousand subscribers, right? And so it's, it's, it's, it's interesting how, you know, of course that was wildly pessimistic. But I think it's pessimistic. I think you were also wildly pessimistic in that there's, there's not, I don't have it covered, right? Like there's, there's plenty of room for lots of people doing that. And now we see a bunch of people writing about this sort of stuff and it's great. It's awesome. I love to see it.

• 6:28Speaker 01

  And every time that anyone sort of puts a limit on a business based on the size of the internet, they're basically always wrong. And, and I think that that is sort of a broad takeaway from this sort of stuff.

• 6:42Speaker 02

  What's the, the line there? The internet's bigger than you think it is, even when you think that the internet's bigger than you think it is or something along those lines?

• 6:48Speaker 01

  I know, absolutely. I, I, I was, I was way more optimistic, obviously than lots of people. But when I started Stratechery, I had a five-year plan, right? I'm going to, you know, my goal in five years is that this is going to be my business. And it became my business in a year and in part because things like social media are so unbelievably powerful. And the, you know, the, the reason why social media is so beneficial to writers and a lot of writers don't get this, they like, they spend too much time on Twitter, uh, frankly. The reason why social media is so powerful is if you have a word of mouth business, then your readers getting a platform is the best thing possible. And so that's the power, the power of social media is what it enables your readers to do as far as sharing your stuff.

• 7:30Speaker 01

  It's not about you being on Twitter, like if you, if you have great stuff, save for the newsletter, right? Like, uh, you know, and let your readers take care of your marketing for you. And I, that was the one where I didn't fully appreciate how powerful that was like, like, uh, you know, Streakery sort of took off and got a large audience in a way faster time than I realized. And, and that was the biggest reason why.

• 7:51Speaker 02

  Was that a ground swell of a lot of smaller people? Was that some bigger people started tweeting about it early on where, where they're like, kind of big inflection points, or was it just repeated people saying, oh, this is really smart?

• 8:01Speaker 01

  There's been one inflection point in Streakery's history, which was, so I started out, one of my, one of my big inspirations for Streakery was John Gruber and Daring Fireball. You know, the, the sort of the, the Apple blogger and, but he had started, um, he actually doesn't get, uh, enough credit, I think, for some of his stuff that he did, where he sort of invented the in-feed advertisement. And it was funny because he had this, you know, he had this situation where he was charging for an SFE, so he was actually doing this subscription thing too. And then Google Reader came along and Googled in support authentication in RSS feeds. So he's like, well, I'll put ads in my RSS feed and people are reading through, because he had all these little articles, right? So people read, read, read, read, read, read. One of them is an ad and it's a, it's an engaging ad that you're reading, just like, you know,

• 8:46Speaker 01

  obviously feed advertising became a huge thing, but this was back in like, you know, the, the, the 2000s. And so, um, I knew that wasn't going to work for me. Number one, I write long pieces and I write a bunch of short pieces. I, I experimented with that, not that good at it. Um, but number two, the advertising market was not in the place it was in the 2000s, right? And so just the, uh, that, that wasn't going to be an opportunity. And so I had to do, uh, so I had to, I planned to do this subscription thing. But anyhow, that's long and short. He was the inspiration. So I started Streakery and I'd been going at it about a month or, or six weeks. Or so and I purposely did not reach out to him because I wanted there to be a lot of content on the site and you know said just said like one article I'm sure he gets a million sort of pitches or whatever.

• 9:25Speaker 01

  And I was actually in the hospital getting my appendix taken out. I can remember it very clearly. I was I was thinking I just got into a CAT scan or whatever or or and I was ready to go in. And um, and I just like I had nothing to do and I was listening to a podcast of him with someone else. And he was talking about all he'd been like an editor at the school newspaper and his background etc, etc. And I'm like, hey, I had a similar background. Always wanted, you know, wish I would have done it more out of college, but I'm doing it now. Here's my new site. You can check it out, da, da, da, da. Uh, heard nothing back from him. And so then uh, it was a few weeks later. And I got an email from him out of the blue saying like, hey, you misuse this word. I think it was like jibe, jive and. Like there's three words that are very similar. And he's like, I screw this up all the time.

• 10:08Speaker 01

  He's like, I actually had, I actually have like a text expander shortcut that fixes it for me. But he's like, this is the etymology of the words. If you, if you've ever read Gruber, that's very on brand for him, right? And that's all the email said. And so like, oh, well, I think I'm gonna get a link soon. And so Gruber has long articles, then he has all these short links. I'm like, I'm gonna get a short link. He's gonna link to an article. It's gonna be great. So I was sitting on, on, on Google. Uh, on the analytics, you know, waiting, waiting for the hit to come.

• 10:32Speaker 01

  He drops a piece. It's not a short link. It's actually an article. And he goes out, he's like, this is the best news site I've read in years. And he's like, you should read this, this article, this article, this article. And it's like 200 words of just like, you know, of kissing my ren. And then he gets to the end of it. He's like, but for the first time I disagree with Thompson. And then he spends like a thousand words saying like, I was wrong about something. Um, but that I had at the time I had 500 Twitter followers. And in 24 hours, it went five to 1500, which I mean today's doesn't sound like anything, but. Relatively speaking, it was a 300% increase. And that was the uh, that got a, that's, that was sort of the, that opened me up to a bunch more people.

• 11:14Speaker 01

  Um, cause you know, a lot of people in tech is, is, you know, re, re Gruber. And that was in the center of like when the iPhone was everything. And so he was like ground zero. And that was the one sort of. Leap that I had and since then it's just been sort of linear growth. I mean, I'm 200 some thousand followers for now, but there was no, there was no moment like that. That was sort of the big one that that got me off the ground. So I, I walked on the story because I, he gets all the credit in the world. I now do a paid podcast with him called Dithering and uh, yeah, it made a big difference for sure.

• 11:45Logan Bartlett?

  And Ben, you were pretty purposeful in the early days, right? Of, of this was going to be subscription and this is how you're going to monetize. And that, that was like a very intentional thing that you thought this could be a scalable business and you would be able to build around subscriptions and paid?

• 11:58Speaker 01

  Yeah, that was the, that was very much the plan. I mean, Stripe had just come, I mean, when, when did their product launch? 2011, I think. Um, yeah. And so, uh, this, I felt like there was an opportunity here to do this description model. I mean, you just do the math in your head, the whole like 1,000 true, true fans. Um, that was, that was sort of my, my, my goal and my thinking. And so it, it took a, a couple, the first couple of weeks of Shakeria, I was sort of figuring out the model of like content, but that'd be very clear. One, I'm definitely best at these long form pieces. Two, I'm not going to do too many. I want to do at most two a week.

• 12:32Speaker 01

  And because I had seen, I think around that time, Andrew Sullivan gets a lot of credit because he did, um, he did a subscription, uh, offering and it worked very well. The problem was his blog was like a, just a, like someone on Adderall, like, and an average, it was like the combination of Adderall and advertising producing like, he's putting out like 25 things a day, right? And he burned out. Um, but also that was a model that worked well with advertising, right? You just put out a ton of content. People are always going there. You know, Gruber, the Gruber model would have made sense, I think for, for, for Andrew in that, in that regard. And so then he put up a paywall and then the paywall is like, you're punishing your best customers. And if you, it, it was too, it was a lack, it wasn't stringent enough for your, for his casual customers. It was too stringent for his best customers and just kind of left a bad taste in your mouth.

• 13:19Speaker 01

  He still grossed like a million dollars a year, his first year. Like it was, it like, people pointed to it as a failure. It was a massive success. He just burned out. Um, and so when I started and I saw that, I'm like, well, I want to be very intentional about my content where when I watched the, the. Subscription product, I want it to be, uh, people are excited about it where there's like you get more. So I really wanted to have that sense of getting more instead of me cutting you off. And so that was the idea. And then the, the metric that I was looking at was number of visitors to the homepage on days I didn't post. Cause to me that was people, they're typing in stratechery into their browser, they're clicking a bookmark, hoping that I wrote that day.

• 13:59Speaker 01

  And they were, and so they were disappointed, but in this case it was a disappointment that I could alleviate. I could give them something in the future. So they were, they were disappointed ahead of time as opposed to like, I drop a paywall. They're like disappointed after the fact. And so, uh, once this number got pretty large, that was sort of my goal. And then I would give them more. The way I gave them more was kind of a mess. I built this whole complicated website where I was going to do like, uh, Gruber style, like lots of links and short commentary. That was a disaster. Like the actual implementation was very poor and I knew it. And so I tore it all out over a weekend. And then said, no, I'm just going to email you, uh, if you want more. So I, I had the subscription model in mind, but I absolutely sort of backed into the email thing.

• 14:42Speaker 01

  Uh, delivering it via email. And it's so funny that people came along and be like, oh, Ben invented email or paid email newsletters. I'm like, well, I invented the paid part, but I got very lucky on the newsletter part because it was, it was, uh, it was sort of backing into it. And so, uh, and so, yeah, that, that was, but it was very intentional. And I think that being intentional upfront helps a lot. It particularly, you know, getting the, again, I'm a big fan of sort of getting that alignment and, um, then I, Packy, I think you, you actually, you understate your decision-making. Cause what I was observing not boring, I think it was a similar thing, right? You, you, you, you, you spent that year, that little bit before you've been at your job, sort of figuring out what worked for you, what the content was good for you. And then once you figure out the subject matter, then the business model that made sense.

• 15:26Speaker 01

  And again, that's where magic happens. Like when you have all the sort of pieces that make sense and they're all aligned. And, uh, and so, yeah, the, the, that's, that's the, uh, that is a long answer to a short question.

• 15:36Logan Bartlett?

  Yeah, no, no, it's super helpful. Packy, maybe, maybe take us through that, that what Ben was just alluding to of how this came to be for, for people. I know you've told. The story before, but maybe give a quick primer for people on like how you thought about this initially. I know both your wives are pretty inspirational in encouraging you to pursue this path.

• 15:54Speaker 01

  Well, no, she wasn't very, she wasn't very excited when I, when I quit my job. I'll, I'll tell you that much, but from my perspective, I did want to live in Taiwan. And so that, that was a, that was a reason to find a non-traditional job. But sorry, not to jump in.

• 16:08Speaker 02

  No, no, I mean, yeah, for, for me, that's when I ended up finally putting advertising on was, was many, many months in. And she was like, are you ever going to make money off of this thing? But before that, we were, you know, in her parents basement. It was a kid on the way. It's super fun. But before that, to your point, you know, I'd, I'd started exploring. I did a year while I was still working where I was just doing kind of the links and occasional essays and all of that. Went full time at the beginning of COVID, started writing some essays and the things that took off were like comparing, you know, Schumpeter's Gale and Creative Destruction to the Mickey Mouse Club or a Hey Arnold episode to like the oversupply of virtual events that people were throwing and why like if there's a oversupply in both virtual events and oil, people don't want it and, and price falls and the whole thing falls apart.

• 16:54Speaker 02

  And as I was writing those, I was starting to get a good reaction from people. But I couldn't picture anywhere in the world, somebody going to their boss and saying, "Hey, I'm reading this newsletter called Not Boring. There's all these cartoons and memes and everything in it, and I need to put this on my corporate card and expense this. Uh, and so, you know, now I can afford to pay $8 a month, $10 a month, whatever it ends up being because my company is paying for it. And because of that, and the original plan was to do subscription, but then I just kind of kept writing and kept pushing it off and got a little bit addicted just to continuing to grow. And then finally, I, I think it was probably six months into going full time through a sponsor deck out on the internet

• 17:34Speaker 02

  after I had done a little survey of the audience and was able to fill up kind of the next, uh, three months, kind of through the end of the year with advertisements, just regular advertisements for the newsletter. One thing led to another. I did a sponsor deep dive on, I think, uh, on Main Street and then Ramp and then Pipe. Uh, and then just that started snowballing. The first time I did one of the sponsor deep dives, I thought I was going to get a bunch of hate mail from people saying, I can't believe you're such a sellout. And I think the thing that worked is, one, to your point, it's a peek behind the curtain that people don't often get into these companies. But two, it's not like I had been this like deep cynic and I was ripping companies apart.

• 18:13Speaker 02

  Five days a week and then the two days that they're paying me, I'm like, actually, you know what? Like this is a really wonderful business that they're running over here. And so I think my kind of dumb optimism just kind of fits the, the angle and fits that model pretty well.

• 18:26Speaker 01

  What do they do? I actually think from your perspective, opening the fund and doing investments, actually, I think it's, it's affirmative of what you're doing. Because it's like, it's super clear. Like, obviously I'm rooting for this company. Obviously I think it's a good thing. And it almost would be odd if you weren't investing, whereas like, like with my model, I don't invest in it. I, I, I mean index funds, I do no startup investing. And that's kind of aligned with, look, you're going to pay me money because I'm giving you my best thought on it. And I have like, this is just, you know, sort of objective. And so I, I think that's a thing where it's not just that you're taking advantage of it, but me as a reader, I like the fact you're invested in these companies.

• 19:09Speaker 01

  Because it's not like I'm expecting you to be, you know, it's a startup, you're, you're, you don't have the details. I'm not expecting objectivity anyway. And so again, that's, that's, that's part that gets at what I love about, about your model in particular, it's, and the fact you're not subscription. Again, I love what, I love the subscription business. I'm so proud of the model. Like when I die someday, I'll be proud of your tech career, but I'll be equally proud. That this model exists and so many people make a living off of it. But I admire what you've done in large part because it's not the model. And also because, again, I just keep going back to it. Like if you can get that alignment between your business model and your audience expectations and what you're good at. Like that, that's, that's where magic happens for sure.

• 19:49Speaker 02

  I appreciate it. I mean, I think, yeah, the, the burden kind of shifts further up to what I choose to invest in and write about. And I'd actually say. The writing about filter is even higher than the investing filter because it has to pass, pass both.

• 20:02Speaker 01

  Yeah. Cause then other people see it. Yeah.

• 20:04Speaker 02

  Exactly. If other people see it, it's a company both that I think is a good business, but also that like people are going to want to read. There's plenty of businesses that Logan might invest in that like just wouldn't make particularly compelling newsletter topics. And so, you know, I think it does shape a little bit of it, but I'm making that decision kind of upfront. And then from there, it's like, hey, I'm all in for this company. I'll point out where I think there's some challenges. Obviously, I don't want to just say that this is going to save the world, even though sometimes I do. But yeah, hopefully I've done a lot of the screening and vetting ahead of time. So that once I dive in and write, I'm really saying like, this is why I got so excited about this business.

• 20:39Speaker 01

  Yeah. And I don't Logan, you can answer this question because I don't know Packy personally, really before this podcast, but I get the impression as a reader that the other bit of alignment here is that writing in this sort of positive affirmative way matches sort of his personality, right? And I get a lot of personality of his pieces coming out, which again, I think is another sort of great fit there.

• 21:02Logan Bartlett?

  Totally. Yeah, I think it would be, it would be weird to do anything but what he's doing, right? If it was, I mean, I think.

• 21:08Speaker 01

  This is super dry, like, like, like, I'm like, I'm like, racked with doubt, right? Like, I, like, I want to, like, well, maybe it's, I want to, like, make sure I've still manned my argument. You consider this. If I write, if I write a strong opinion, the next day is always, here's why the strong opinion is wrong, right? So like, yeah, they're like, they're just a, that's a better match for me. And so I'm not surprised to hear that.

• 21:32Logan Bartlett?

  No, and it's 100%. I think what's so interesting about what you guys are doing is like, honestly, on almost every vector, you sort of exist at outer ends of the spectrum, right? And so business model, subscription versus advertising, like explicitly biased versus objective and unbiased, right? It's sort of outside in versus inside out. It's news oriented versus interest oriented. And so I just think the, the fact that both, I mean, everything in the internet ultimately barbells, right? In some way, shape or form. And so you guys are honestly like pioneering. I mean, Ben, you have and Packy, you are these two different approaches. And so I think.

• 22:07Speaker 01

  Just, just the other thing, the sort of, sort of double down on this is I mentioned before about how large the internet is. And the mistake that anyone who is used to the analog world makes is they're they're they're used to there sort of being a depth of opportunity. And so like, for example, if you wanted to be a sports columnist, well, there was a lot of sports columnist jobs. You can be a sports columnist in in New York, be a sports columnist in Boston, you be a sports columnist in Madison, Wisconsin, right? You're not going to make as much money or give as many readers, but hey, it's a job. Uh, you mentioned the Bill Simmons point, like once Bill Simmons came along, there was one Bill Simmons, right? And everyone read him. But the the change in opportunity was there's a lot of people that tried to imitate Simmons, right?

• 22:48Speaker 01

  It could be the sort of the fan point of view and I'm gonna do news and I'm gonna do an email bag and stuff like that. And and they were like painful to read because they weren't as good as Simmons. They're also so transparently trying to be Simmons. And it's like, why would I want to read a facsimile when I can, when the real thing is literally a click away? Well, the opportunity of the internet, the opportunity there is a horizontal one. The the key success on the internet is not competing with the big fish. It's that you have the opportunity to create a pond anywhere you want to. And you can create that pond that's perfectly suited to your capabilities, right? And so like, again, I think it's great for you to have me and Pacquiao on here or Pacquiao and I on here at the same time. Because it's a perfect example. We're nominally covering the same thing.

• 23:29Speaker 01

  And yet no one in the world is ever gonna like, does anyone think of us as being competitors? Like, and and why? Because Pacquiao writes a a a Pacquiao, Pacquiao dominates the Pacquiao pond. I dominate the Ben pond. And lots of other people dominate their ponds and that's and you see that not just on writing, but the internet generally is the opportunity is a horizontal one. If the internet provides an incredible amount of breadth where you can build a niche, again, because that audience is so large. And and people that think that see the limitations, the opportunity. It's because they see, well, yeah, everyone, everyone's could be with Bill Simmons. How can you be Bill Simmons? Well, you can be Bill Simmons by Zach Lowe comes along and he does all these video breakdowns. And it's like, oh, my God, this is incredible. Like, I understand basketball to a degree that I never did previously.

• 24:13Speaker 01

  And and now you have lots of, you know, well, imitators, but there's people, but now the thing about the low model is, well, you can have that on a per team basis, right? What team does not want the guy who's breaking down videos about their specific team? And so that's Further defined pond, that's a new sort of approach to content that takes the internet. It's a combination of text and video, but it's it's defined by, you know, it's a narrow, narrow, narrow niche. And sorry, that's just a long, but this, this, this thing about the depth versus breadth is an important thing.

• 24:39Logan Bartlett?

  One of the things that I talk about with venture firms in general is, and I use this controversial analogy just because it gets people leaning forward in the conversation, but it used to be, I compare like the pre 2008 days to broadcast television, where you were trying to broadly appeal in a very thin way. I love Lucy gets made and happy old market or happy, uh, happy days get made. And all of those shows get made because you want to appeal to as broad a group as possible.

• 25:06Speaker 01

  The lowest common denominator that reaches as wide as possible. Sorry, this is one of my favorite things. Well, like the whole economy aligned to snap to broadcast TV. You had P and G making brands that appealed to the lowest common denominator or the broadest common denominator. You had big box retailers that then sold self space that would align with the P and G advertising on TV. You had people driving cars to the big box retailers and, and all those industries, the car industry, the big box retailers, the CPG industry, they ran ads on TV. It was, it was this perfectly aligned model that entire segments of the society were predicated on there being three broadcast channels and the, the, the degree to which that is the case is still underappreciated.

• 25:48Speaker 01

  People like, why is TV still going on? Like who watches TV anymore? It's because we have all these massive companies that are so locked into this model. The model actually persists. If you were starting from scratch, would you have P and G, would you have these companies? No, you would have a completely different approach, but they're so big and have so much sort of, uh, what's the word for it? Uh, momentum, what's that for momentum? Would you just keep going, uh, inertia that it actually leaves the structure in place for far longer. People have been predicting the death of TV for 25 years, still hasn't happened. And, uh, and it's because you have all this sort of inertia behind it.

• 26:28Logan Bartlett?

  No, and that's the analogy I'll draw to the venture industry as well is the broadcast television days were the days of, you know, where you could just be broadly appealing to a narrow subset. And the analogy I use now in the venture world is like, you don't, we don't live in a ranked choice, uh, primary process, right? Jeb Bush loses, Donald Trump wins. It's better to be deeply appealing to a narrow subset than it is broadly appealing, but kind of milquetoast in that way. And so I think we're sort of seeing it in the venture industry as well. And it's true of, you know, we're seeing these healthcare specific early stage funds getting started, or we're seeing PACs start with not boring and have all the distribution, right? Or we're seeing fintech only late-stage funds that all their LPs

• 27:11Logan Bartlett?

  are, are banks, right? And so if you're not going to be thought of for something, you're going to be thought of for nothing. And something that I think venture firms in general is sort of existentially thinking about of like, where we exist in this whole spectrum, right? And so it's, it's true of broadcast television. I mean, it's true of CPG. I think everything's sort of going through this in some way, shape or form, enabled by the internet.

• 27:31Speaker 01

  And yet, at the same time, if you're still Sequoia, you, you have so much, like, it's like, Sequoia is like the P and G, right? Everyone knows who you are and you still have, and so you can, you can coexist, but if you're a new venture fund, you shouldn't say, I'm going to be the next Sequoia. Like, you're 50 years too late for that.

• 27:50Logan Bartlett?

  A hundred percent.

• 27:51Speaker 02

  And coming full, full circle, so that first piece that I wrote on, on some of your pieces, I had this big block quote, uh, and I believe it was from the Clayton Christensen got wrong piece. And the quote was, differentiation based on design, which while it can't be measured, can certainly be felt by consumers who are both buyers and users. It's time for the theory to change. And I think like, I don't know, obviously aggregation theory is what you're best known for, but on the internet, I think it's kind of aggregation theory, number one. And then the point that you're making now around kind of differentiation, number two. And if you're not differentiated, like, I almost think you want differentiation at all costs, even if it means you're going to be worse, but maybe even across the board. It's almost like a comparative advantage in, in economics that even if you're worse across the board, as long as you're different, there's something better to that than just

• 28:36Speaker 02

  trying to be the same thing. Even if you think you might be able to outcompete.

• 28:40Speaker 01

  You you need to be willing to forego stuff, right? Like, um, the I I realized at some point that even though I was getting like, well, the startup, the startups is a great example, right? People, you know, I just didn't cover startups basically at all unless they were late stage, or there was like some clear, interesting strategic implication where you didn't necessarily need to know the financials. But then something like Uber came along where there was a lot of interesting stuff there. And honestly, uh, it would have been nice to have known the financials to a greater degree than I did, right? Especially because, you know, in retrospect, a lot of the stuff that Uber put out publicly ended up being, uh, wrong is a generous way, I think, way to put it. And so, and so that was sort of a lesson where, look, I like, people get, they're like, oh, you know, I wish, Ben, can you write about startups? Can you not write about XYZ?

• 29:26Speaker 01

  And it's like, I understand that you're bored about me writing these companies. And to an extent, like, writing about, like, you met, you know, right, like, Washington and politics, I got sick of that, too, right? But there's an extent where, at the end of the day, like,

• 29:41Speaker 01

  there's a, like, someone has to write about Facebook, and someone has to write about ATT and app tracking transparency. And that's kind of my thing. And if you're sick of hearing about it, go repack it. Like, and that's okay. You have to be okay with that, right? Like, like, you know, look, I'm, that's my niche. I'm going to cover the hell out of it. And, and I have to be okay that that means that some people are getting tired of it or bored of it or whatever. And, and that, you know, uh, you go to not boring if you're bored. So that it all works out.

• 30:10Speaker 02

  I mean, I think, you know, and I think of like my model, the risk on on mine is, you know, had I been writing when Uber was in its heyday, there would have been a lot of glowing articles about Uber. And the the test that I always put myself through, and I fail every time I run this through my head, is if Elizabeth, sorry, is if Elizabeth Holmes had reached out to me, there's no way I wouldn't have writ- written a glowing article on Theranos. Like, that's just so cool. Full blood test in a prick of blood? Like, that's, that's amazing. That's revolutionary. And so that's a downside to my model. And, you know, I think I'm going to get wrecked at some point here in a downturn or whatever. Else, there will be one or two companies that I've written glowingly about that end up not working out. At the very best and maybe even worse at the very worst. And so that's just something that I need to be kind of comfortable with, I think, going into it.

• 30:55Speaker 01

  Yeah, I, I, I, I've very fortunately avoided the Theranos trap. But I think what you have to do, but, but I felt the same way when it blew up, like, oh, thank God. Like, I, I didn't get it that one. But, um, I think what works is, and this is a, an amazing message that like the mainstream media has gone the opposite direction, which is when you screw up, you have to go over the top in owning it. Be like, what, and so whenever I get even the slightest thing wrong, not only do I always correct it, but I will walk, I'll spend a whole segment saying, this was my thought process. This is how I ended up saying this sort of thing. And sometimes I just, I, I rarely, I, it was a factual thing and I feel terrible with those.

• 31:40Speaker 01

  Cause I'm like, I, I just, I, how did I do that? Usually it's like some sort of cognitive bias where it's like, look, you know, and obviously, you know, if you have a model of the world, which is, you know, the, the foundation of what you write, you're always susceptible to confirmation bias where it's like, oh, look, here's an example that perfectly fits my model. Right. And, and then you sort of, you miss something on the other side. Sometimes you're just unlucky, like, um, what probably one of my worst things was WeWork. You know, I was very optimistic on them. And I actually still, like, I think that it was, I think it was right. They just, they just went too far. And if they had come along, I mean, they're still, I, I think they're still, they're actually doing decently now.

• 32:22Speaker 01

  Right. Cause COVID comes along, you have this whole sort of work from home. It's like the thesis was right, but the timing was wrong. It's like a startup, right? That could be the case with an article where you have, like, your thesis was actually right. The timing or circumstances were wrong. You're going to be right eventually, but in the meantime, it's very painful. Cause like, like at the end, this is a packing newsletter, it's a Ben newsletter. So I have to own it if I, and that's the most important thing for a reputation is like, look, I, I, I own it. I'm sorry. I screwed up.

• 32:51Speaker 02

  I mean, WeWork would have gotten, it'd gotten away with it too, if it weren't for that damn S1. Like they were so close. I mean, and the public markets would have crushed them and all of that, but they were so close to pulling off that IPO.

• 33:01Logan Bartlett?

  I don't know, without the self dealing and all that, it seems like that's where they really soured was on all the little bullshit around the edges. And I think the public markets actually would have been receptive.

• 33:10Speaker 01

  Well, the funny thing about about my super positive article is in there, I said, I would not invest in this company because of all this bullshit. And so it's funny, it's really funny because that article actually was, was, I think it was, it was mostly right. I was right in the model being really interesting. I was right in the long term, like trends favoring it. I was right to say, don't invest in this company because there's all this bullshit going on. It was a weird thing where I screwed up in the tone, like it was just, it was, and part of it was, and this is always a danger. Everyone was so down on it and like, like the temptation to be contrary and like get it right. And, and it's annoying because they, it failed for the exact reasons that I said, but I have to admit.

• 33:53Speaker 01

  I, you know, I stuck those in to be clear and I, I wasn't like, you know, the tone was wrong. Like that was, is a weird one where I was wrong because the tone and, and I was wrong. I accept it, but the, accepting it is important. So.

• 34:07Logan Bartlett?

  But this is where I think Packy benefits from being an optimist in some ways is like when.

• 34:11Speaker 01

  Yeah, he gets more of a pass on it.

• 34:13Logan Bartlett?

  Well, if, if, if we're investing in a company and it has a 20% chance of success, you better have five or six of those. Because you're going to look, even if your mental model is right on it, right? And you're saying, hey, 20% chance this is going to be Stripe, 80% of the time you're going to look stupid. And so internalizing when there's only one outcome, internalizing probabilities of things like that, like you gave all the caveats on the WeWork thing. And so it just cynicism always looks better in hindsight than the optimistic outcomes look. And so the ball goes further when you're right than zero is when you're wrong.

• 34:45Speaker 01

  Absolutely. Yeah. No, and from an investor perspective, no, I think that's spot on. And I think that's a really great point to make. And this is, I think, Packy, you don't need to worry about something blowing up. Because I think anyone who reads you understands you're dealing with venture capital dynamics, which is most of these companies are, should fail, right? And so, but if one hits it big, it makes up for all them. And I think this is just an issue where I was a little out of my box because I mostly do public companies. And at that point, they've already succeeded, right? And so whenever, whenever I'm a little outside that, that's where it gets riskier. And I think that was, that was probably an example there. But then again, we had the S1, so, um, whatever. It is, it is what it is. I didn't, I didn't expect to get out here talking about WeWork, but I guess I brought it on myself, so.

• 35:26Speaker 02

  That, that emotion that you feel, I mean, I, I don't know how you guys are feeling about this, but seeing just Twitter and seeing VCs and public market investors and everybody right now talking about like, how obvious it was that things were going to crash and how they've luckily been responsible, but most of the other investors have not been responsible. And like this whole thing that's going on right now where everybody is just so unbelievably bearish and like kind of smug almost, it makes you want to just write the opposite piece over and over and over again.

• 35:54Logan Bartlett?

  To be clear, this isn't about Twitter specifically. This is on Twitter, VCs saying the market's gone down and all that, yeah.

• 36:01Speaker 01

  Everyone is always sort of right in hindsight, for sure. I mean, I think this is, you know, the reality is, is, you know, when it comes to you and I, like, our stuff's out there, so you can go back, you can go back and look at it and read it. And, you know, I wrote a piece in 2015, basically saying this, anyone who says this is a bubble is stupid. And like, and going through all these sorts of things. And so you could be a guy on Twitter and you could go pull that piece here and say, look, you moron, you know, there's a bubble. I'm like, what happened between 2015 and 2022, right? Like, that was, like, actually, that was completely right. I had someone do that to me the other day. They pulled up a 2013 piece on Facebook where I said, Facebook needs to be an app. They need to abandon this, these platform ambitions.

• 36:45Speaker 01

  And they're like, oh yeah, look what Apple did to them. I'm like, yeah, look what Apple did to them in 2021, after they made eight years of astronomical profits. I'm not, I was completely right, right?

• 36:55Speaker 02

  It is funny too, like, that must annoy you still. And like, that shocked me, I think, to the extent to which like a random troll on Twitter can annoy me. I don't know if you still feel that, kind of eight years into this journey, but like even that, like, person with one follower could really just like, put a dent in your day.

• 37:12Speaker 01

  It's one of the hardest things you have to learn to adjust to is, and it's a cliche, but it's definitely true and you feel it a ton if you're a public figure, which is. The people who rip on you or are down you, you hear and feel it a million times more than all the compliments in the world. And it's, and so you, you do have to learn to, there's a couple of things. Number one, I, I did learn pretty early on. I noticed that, and this is where I think the subscription model is great and you don't get this benefit package, but, but it's so helpful and useful to have a feedback mechanism that is independent from Twitter, that's independent from, from whatever it might be. Because I noticed that there'd be these people on Twitter that would come back at every article and I'd be arguing with these people. I'm like,

• 37:56Speaker 01

  I'm arguing with the same like 30 people. And meanwhile, my subscriber numbers are up and to the right. There's clearly this, this Twitter is not representative of my user base. And that was a super important lesson to learn, which is don't index on Twitter. And I think this is a massive problem with the media generally. It's funny, like you hear like, um, they go, oh, our readers don't see any metrics, right? And they say this like it's a good thing because the, the problem is you're going to search for feedback. And so what happens is the writers go to Twitter for feedback and they, they, they're, they're, this is how you get this harmonization effect on Twitter where everyone on Twitter believes the same thing. All the journalists are

• 38:37Speaker 01

  sitting on Twitter. All of their feedback comes from other journalists and, and then their editors are brave. We don't show them the numbers. It's like, yeah, that's part of the problem, right? They, they might not be resonating with an audience at all. And with subscription is even more so because they're pulling out a credit card to pay. That's a much bigger commitment than just clicking on a link. And also, if they have the money to pay for a subscription, they're probably busy doing work. They're not sitting on Twitter all day, right? And so-

• 39:02Logan Bartlett?

  Unless they're a VC, in which case that's, that's their job. But yeah, VCs can do it, but otherwise-

• 39:07Speaker 01

  The VCs are great because, uh, you know, I had some early readers in VC land and, you know, I think they like, oh, they could bring up, you know, and steal my insights. That's what VCs do. Um, but then it crossed the line where if you didn't subscribe to TechCrunch, then you like, you look like a moron. And, uh, that's maybe less fulfilling as a writer, but it's much better financially. It's just a cost of doing business. So, hey, I'm not going to complain.

• 39:32Logan Bartlett?

  Hey, one of the questions I had, Ben, how did you, Pacquiao, you obviously, you've had to figure out what the sponsor post and costs are of all that. But Ben, you know, there's probably, we talked about, I forget if this, this was before we started recording, that these newsletters, once upon a time, 25, 35K, that were actually printed out and mailed in the financial institutions that went out. Like, how did you land on the price point that you did? And how do you think about the trade offs of being at that price point versus some much higher one versus some much lower one?

• 40:02Speaker 01

  Yeah, it's super hard. And I don't know that I'm, I'm for sure not optimal as far as revenue goes. You know, I raised prices once, and I think my subscribers accelerated, so I should probably raise price more. Basically, when I started, I actually, I was, this is another thing I sort of had to figure out. People don't forget, but I have a pretty convoluted model. There was like $5. That was just like, basically, you get access to the forums, which, I'm not good at forum management, but it's still there. But 10, 100, you got everything. And then 30, 300, I did like a subscriber, like, call, like, once a month, like that. In retrospect, I real,

• 40:43Speaker 01

  all the people that subscribed to that 30, 300, a lot of them did it because they want to support me. And I, and it made a huge difference. When I actually went independent, I thought I had this consulting thing lined up. So I was going to do like, because we're in automatic at the time. And automatic, then, to be fully distributed was very unique, right? And so that's why I could live in Taiwan. But they had a very strict no monetization side of work policy, which, you know, made sense, because, I mean, you see, there was that tweet going around the other day about someone working for Twitter and, or for Facebook and Microsoft or whatever, right? And so, and so I had to quit the job, but I thought there's something lined up. That fell through. All I had was just checkery. And I had, and I had to quit early because I had to build the whole payment side, right? Because Substack didn't exist. I had to like, actually, like,

• 41:27Speaker 01

  put the stuff together myself. And so, and so this fell through, and I was, it was, I mean, it was, it was, it was rough. Like, I stopped paying all my credit cards, because in Taiwan, especially back then, was much more cash heavy. So I needed to like maximize cash flow. I was like not sleeping. I was not telling my wife, because I, she knew I'd quit, but I didn't, like, I had a one day goal, one week goal, one month goal. I failed to reach all of them. And based on that number of how many people were visiting the homepage. And so it was, it was very, it was very difficult and there was a lot of people, or not a lot, obviously. There were some number of people that I know came in and bought those $300 plans. Uh, just because they wanted me to succeed. There was also a lot of people that didn't sign up.

• 42:10Speaker 01

  What happened was, um, was I think it was six or seven months later, I got a thousand subscribers and I put a little post up saying, hey, got a thousand subscribers and that was my one year goal. I actually got the one year goal early. I'm like, the model works. And then as the next day I got 250 new subscribers. That was the biggest percentage jump by far. What it was, was all the people that I was counting on subscribing at the beginning. They all wanted to subscribe, but they all assumed I was going to fail and go out of business and they were worried about losing their money. And so, once it was clear that I was successful, then they all signed up. Uh, and but, so there, there, uh, I appreciate they've been there all along, but my, my true fondness is for those people that like, had no expectation of succeed. They just like, hey, I'm going to buy the most expensive plan, even though you didn't really get anything for it.

• 42:53Speaker 01

  Um, what I also did was when I announced that, I simplified it to 10 100. There's one plan. That's what you subscribe to. There's no, there's no higher level thing. I'm not going to do this extra stuff. It didn't scale, obviously at all. And one thing I've been super disciplined on is checkery is I only do stuff that scales. Uh, I, I, like, uh, I did do a little bit of consulting at the beginning. Um, but that was just to pay the bills. The moment I didn't need that, um, I haven't done really much of that. I rarely do speaking anymore. Um, just I want, everything that I do, I want to be, because the front end is not scalable at all. I still write every day, like it's a ton of work. And so I want the backend, my audience side to be perfectly scalable. So that I get sort of the maximum leverage off of, off of all that work.

• 43:36Speaker 01

  So yeah, I know 10 100. I love the simplicity of it. Again, I remember I was the first one to go, right? There's no one else doing it. And so to charge 20, 25, 50, a hundred dollars out the gate would have been a no go. Like, like people, again, I had a whole bunch of people that wanted to subscribe that didn't subscribe for $10 because they thought I'd go out of business. And so it had to start at an approachable price point. I think the the thing that I think about is I do still want to have reach. I do still want to have an impact. I uh I want so I want the price to be approachable and as long as the audience is still growing, then I'm okay with not harvesting sort of the audience that exists. I also love

• 44:15Speaker 01

  the fact that uh people get upset and I'm like bye like no what no reader has any sort of leverage over me at all. And so like last week, like there's people like in that I was, you know, or just happens all the time. Like I just don't worry about it. Right. And um, and so that's that's a uh uh that's a very sorry, I'm kind of rambling here.

• 44:39Logan Bartlett?

  No, no, no, it's helpful to think about. I mean, it sounds like the answer is the price point was one, you just established it early on. And then two, you still care about the the reach and the influence side of things, which Packy, I know in in, you know, when you did the ramp piece, right? I still think that's one of like the single biggest drivers for them. Every time someone comes in and interviews with ramp, like the fact that it's it's out there and you were one of the first to do it and you have all this reach. I think that influence thing, I mean, you've talked about in the past, but was definitely addictive, right? Of like, oh, these numbers are going up.

• 45:11Speaker 02

  I mean, I think to Ben's point, too, the the like almost anti fragility of having thousands of people who support your business is really, really nice. I think it lets you be a little bit kind of braver in what you go out there and and say, because there is no one person that if they pull out because they didn't like what you said, you're in trouble. And I kind of view mine the same way, even though I advertisers coming in and paying big chunks, at least for now, and we'll see when the market turns. But at least for now, there's enough demand there that like really the the base that I care absolutely the most about is keeping kind of the trust of of the readers. And there, I can really have to, I think, do some damage to like, lose enough of them that the momentum slows and that I couldn't make it up in kind of a week's worth of of growth. So I

• 45:54Speaker 02

  think there is something really nice about having that broader base, even if you're not kind of like maximizing uh revenue or maximizing profit under the under the curve.

• 46:02Speaker 01

  I'm jealous. The best part of an advertising model is is reach, right? And and and Like, I don't think it makes sense for me. I think my distribution model makes sense. But that's one of the things I look at you like, that must be nice. So there's definitely huge, huge advantages to that.

• 46:18Speaker 02

  Ben, I wanted to, to ask, I mean, something that I've always been curious on. You and Bern Hobart are the two people who just completely blow my mind with the output and that there can be something smart that you write every day. Like, what does that process look like? And, and for me, like, I do not have a good memory. And so I'm doing research, like, very often, kind of fresh every time I write a piece. How much of it do you know what you're gonna write going in and you kind of have in your head? And how much of it is a good system? And how much is it just like grunt work every day?

• 46:48Speaker 01

  Yeah, well, I mean, I feel lazy because when I started, because I remember I was doing two free pieces a week. So when I went pay, I was doing two free pieces and I added on five, five emails. And I was doing a podcast. So that was, that was not very, I remember the, uh, uh, we were on vacation with my wife and I was in the bathroom, like typing like a daily update. Um, so the, right after I started, so the, uh, I, I like to think that even though I didn't start some billion dollar business, I, I have at least a taste of what the grind is at the beginning. Um, so now I just do a luxurious, uh, for a week, uh, which is, which is, which is much better. But I think this actually goes back to, remember I made the point about confirmation bias before? I have a model of the world, the way the world works.

• 47:31Speaker 01

  And, uh, you know, I think a lot of people at this point have a pretty good handle of model of the world is. When I started, it was very contrarian. Like, when I started, it was all this idea that the internet is a decentralizing force, all these sort of things. And mine was the exact opposite. No, actually, the internet is a centralizing force. And that has massive implications for all kinds of businesses. And, um, and so when you have a model of the world, uh, at least from my perspective, so I read extremely quickly. I write very quickly and I have an insane memory. So, uh, when I get facts wrong, it's because I'm memorizing. It's, I bring up some fact like six years ago and I'm pretty sure I know it. And I, so I do need to be more disciplined and always checking like numbers on those, on those hands. But it, that is definitely sort of a superpower as far as writing goes.

• 48:14Speaker 01

  And so I have this model of the world. It passed through the model and pretty for daily update. A lot of stuff, it's very easy to explain. I can just turn out 800 words on it because it's pretty straightforward what's happening. There's a lot of stuff where there's a missing piece and this is actually where you can get predictions. It's like there's, there's, there's something else going on here. There's something, you know, it's, there's X, Y, Z. I would look for this to happen, whatever it might be. Uh, and then the third one is I'm wrong or, or there's something I didn't think about. And that's sort of the genesis of the longer articles, like, like the big pieces, which is, oh, I'm now enhancing and extending my worldview and, and, uh, let me explain this and how I got to this. And it's funny, if you read strictly super closely,

• 48:56Speaker 01

  uh, you can always see a big article coming because I'll be working on different bits and pieces of it. For a while, sort of, sort of, sort of coming up to it. And then it's sort of, you know, that, that piece is sort of putting it all together. And, um, and so the danger there, so one that lets me produce a lot of content because anything that happens, I have a point of view on it. Almost certainly, um, a lot, so a lot of my day is doing all the supporting research around it to make sure I have all the numbers right. I have X, Y, Z. Uh, you know, maybe there's some sort of historical linkage and make sure I, I read up on that, but I usually have the take, um, pretty early. Uh, and then the, the danger though is this confirmation bias because like I'm basically leaning into the fact I have a model of the world. So the temptation is always to

• 49:41Speaker 01

  find data that supports your view. And so I try to be super disciplined about, you know, looking for disconfirming information that, that, that, that shows why what I believe might be wrong. And I think I do a pretty good job of that. And there's sometimes where I've changed views because I, I actually went through that process. But for sure, when I make mistakes, that's what happens, right? Like I blew the clubhouse thing, um, a couple of years ago. Cause I, I, I had this insight and it's, oh, this very, this very neat model and I fell in love with the model and I wrote this very optimistic sort of take on it. That obviously completely missed the boat and I, and that was one where I had to do, that was a big follow-up, right? It was like an all-day follow-up. Like, look, this is, this is what I was thinking. This is the mistake that I made. Like I totally fell into this trap of doing X, Y, Z.

• 50:23Speaker 01

  Here's someone else that wrote a piece where they got it totally right and, and I got it wrong. And, um, and so that, that's for sure the risk, but that is also what sort of enables the, the level of output.

• 50:34Logan Bartlett?

  So Ben, it sounds like your process is you have this existing framework. We have a great memory and you remember all these facts and you have a bunch of existing frameworks in place of how you think about things. And so you're able to pass any news as it comes through or any strategic decision that happens through those frameworks and able to operate pretty quickly. And you ruminate on a bunch of different ideas and build on top to come to things like aggregation theory as you sort of are noodling them. Is that a fair characterization?

• 51:02Speaker 01

  Yeah, I think so. And I think the other thing that's advantage, one of the advantage I had from being early is there was so much uncovered ground that I could be half right. And get a lot of credit and a lot of credibility. I think ads is a good example of this. When I first started writing about ads, I came from business school. I came from Kellogg that was very heavy on brand marketing, like they're the kings of of marketing. And so that helped me because I really understood CPG and I understood the ad market broadly. But a lot of my early analysis of ads on the internet was wrong. I was way too anchored on brand advertising. I didn't really understand direct response and and and to the degree that it worked. But there was no one writing about ads. So me writing about ads and being half right and half wrong.

• 51:44Speaker 01

  I was miles ahead of anybody else. And now today, and so I look back at some of those pieces, I'm like, eh, you know, like I wrote a piece about like, you know, Google and how they're going to have problems because of the brand advertising, it was totally wrong, like just and um and. But at the same time, because I was early, I didn't have a packy on the side coming in saying like, oh, no, Ben didn't totally doesn't understand how this works. Here's the issue. I could, I had time to sort of self, self uh improve and sort of like, see, well, I got that. And this is where they're being disciplined about saying we got stuff wrong. And I wasn't quite wrong, so I adjusted. And now I feel like, you know, it is funny, like I spent my whole life preparing for ATT, right?

• 52:21Speaker 01

  Which is like the the most boringest pitch ever, but you know, to, you know, I just felt like when I write about like that and the implication of what Apple's doing and how this will play out. I feel so much farther ahead than almost anybody else. Um, you know, there's a good guy called Eric Suford, who's very, very good on this stuff, but he's coming from the ad perspective. But as far as like some of the the strategic stuff, I'm just like, you know, I'm so locked in on this, but that was the good. Fortune of I've been figuring out ads for for eight or nine years. It had H T T come along in 2014. I would have written stupid shit about it, right? And so um, uh, so I'm sort of fortunate in that regard.

• 52:57Logan Bartlett?

  Similarly, it's how I feel about memes and VCs. Now that other people are getting into it, I'm like, you know, I've been out, I've been way out in front of this and doing all the different stuff. What is your?

• 53:05Speaker 02

  Which is true, which is true.

• 53:07Logan Bartlett?

  Kind of is, but uh, Packy, what is your process that you go through?

• 53:11Speaker 02

  Through through media pioneers here. Um, yeah, my process is is again, I think this is another area where it's completely the exact opposite. I'm almost like a golden retriever coming in fresh to each new thing. Almost no memory, like there's some things that I try to run things through, but my process is really, you know, if I know what I'm writing about, then that's an advantage and I'll just read and listen to and, you know, dig in as much as I possibly can. If I don't know what I'm writing about, then I'd sit there and kind of panic for a little while, but let's assume that I figure out what I'm writing about. It's dumping as much information in my head as possible, which is both a good thing and a bad thing.

• 53:51Speaker 02

  Because I'm learning about totally new industries. I need to kind of learn what the overall kind of thoughts that people have on the industry are and on that particular company might be. Soak all of that in and then I sit and look at a blank page for like a very long time where I will really like, try to get the intro right for like a day and that will just.

• 54:11Speaker 01

  I can relate to that. A lot of this is totally different, but it getting, that's the hardest part by far. Once you get that, you're off, but that takes hours.

• 54:19Speaker 02

  Once you get that, you're you're golden, but it's really like, you know, what is like, what is the hook? And like, what am I trying to say here? That's not just like, this company is very cool. Like, what is this company like? And what's something that's kind of approachable that people might be able to relate to? Uh, that that will help them understand this company or like what goes right in the world if this company gets it right? And that takes forever. Like literally last weekend, I was writing about Cello, this blockchain that I was super excited about and like kind of knew all the different facts and all the different things that I wanted to say. And I just could not get that angle right for days. It was two full days of deleting and starting over and deleting and then like taking a section and moving it later in the piece and just like tricking myself to get out of the way. And then to Ben's point, like, once I get that part right, then it's a matter of just kind

• 55:04Speaker 02

  of it flows and, you know, normally be a panicked kind of Sunday of just writing the rest of the piece. Then I have my brother Dan edit it. And then we, you know, make all the graphics and make the title image and get it sent out to kind of come hell or high water 8:55 AM on Monday. But it is a lot of kind of just knowledge ingestion and then panic until I figure out what's right. The other tough part is, I think, because I am pulling so much information in that's fresh, there's like a little bit of just like sadness whenever there's a piece of information that I know exists out there that other people might like, I'm like, oh, man, they're gonna know that I didn't cite this like old study that said blah, blah, blah, that like fits perfectly here. Whereas

• 55:49Speaker 02

  obviously, nobody cares or knows that that thing exists or would have related it. But everything that I leave on the cutting room floor is definitely like, oh, killing a baby in my head a little bit.

• 55:58Speaker 01

  I can relate to a lot of that. On the other hand, I think this is a great example of where we have alignment with our models, right? Where, especially when it comes like the startup stuff or the web three stuff, like, people want to learn. And so we get to like go along with Packy's learning process, right? The whole idea of a new space is we don't want the old models. We like, we want sort of like a freshness and view. And, and so I think it's great hearing you talk through that, your process and how you're thinking is, is different than mine, because it actually sort of makes the broader point, which is you want all this stuff to sort of work in a similar, you know, to be aligned.

• 56:40Speaker 02

  I mean, there's also, it's very funny. I mean, I think the great bifurcation is one of the best things that I've read on, on web three. And I think that the thing that you do where like you are completely kind of objective and you are analyzing and you are being cynical like on some things, when you make a point that is not like completely anti web three, there's some like real kind of gravitas to that. Whereas, you know, for me, I'm investing in things, I'm writing out things, I've kind of like put a stake in the ground that I'm into this. And then you come out and kind of say like, look, we have this online life and this physical life. And of course you want new kind of models for this digital life where you have your whole kind of digital person and your digital things and all and like,

• 57:22Speaker 02

  of course you want that. I thought that was like a very good succinct way of describing that. And so I think, I don't know, this is why differentiation and having, I think, a lot of voices in this system works well, because I think there's, I can come in and kind of like say great things about Web3 all the time, but then that one piece from you, I think, not too cheerleading, just like, hey, there is an actual kind of reason that the stuff might be useful, I think is also, you know, an incredibly important thing to have in the conversation. Yeah, I mean, the internet's big. There's lots of niches.

• 57:53Logan Bartlett?

  Well, I think Web3 is actually the most interesting sort of like forum for both of these worldviews to some extent, where it is, if you're, if you're so optimistic about the way the world could be, Packy, to your, to your model in all of this, like, Web3 is just like, you know, kid in a candy store walking around, right? Yeah, it's like catnip. It's like, everything here could be so exciting and so disruptive to the old way of, of, of doing things, right? But, you know, you're risking all the, the downside and the soft underbelly of all these things.

• 58:24Speaker 02

  Totally. I also think like, I don't know, I've probably, maybe like, there's been a couple of cases, like when Scott Galloway wrote something anti-Web3 and I had to like, jump down his throat on, on Web3's side, just because I thought he made like a bunch of like moderately dishonest points in there, like, you know, just kind of stretched backs a little bit to, to make his, his point and to kind of rile up his, his base. And so like, I probably cheerleading too much for Web3 in that case. And a lot of other ones, like, really, my take is that this is a new set of tools that people have. I don't think that it completely replaces every other business and that we're going to see a Web3 Facebook and a Web3 Twitter and a Web3 LinkedIn and Web3, I don't actually think we'll probably

• 59:09Speaker 02

  see squamorphic versions of any of those. And I think like, whatever the next kind of like, Web three social network might be well a hell of a lot different than any of the social networks that we have today, kind of subscribe to the Eugene way, status of service theory there. And so a lot of the work that I've tried to do particularly early on in the web three stuff is saying like, hey, I know that we all think this is kind of weird, but look like there's something called a value chain. And what happens when you take out the middle man and like, how might you coordinate those things? I mean, I think Ben's point that aggregation theory still applies. I mean, it's the internet and demand is a really, really important thing. And whoever controls demand controls the universe, like, all that stuff still applies. It's just, does this new toolkit

• 59:51Speaker 02

  give you areas to enhance those things in certain places? But I really don't love anti the old thing positioning as much as I love, you know, this is the other thing that this new thing might enable positioning.

• 1:00:04Speaker 01

  Yeah, I think that's a really good point. I think where a lot of the web three advocates and you see, because you see, this isn't a web three thing. This is a every new thing that comes along is there. And I think people, you go back to the very early days of tech and people are stuck in this mind frame from like the 80s and 90s, where we were just figuring this stuff out. And so companies like would come along and would disappear because a better version of that company came along, right? And you had to have a shakeout to see who's going to win PCs if you're who's going to win XYZ. And, and people think that tech's still like that. And it's not. What happens is you're we're, we keep moving up the stack and all this stuff that's foundational is not changing, right? Like,

• 1:00:47Speaker 01

  Microsoft still dominates PCs. Microsoft in phone, like phones are something that came in addition to PCs. Now they, it was a bit of disruption that phones became the most important device in your life and the PC became a satellite, but PCs didn't go away. And you see this all over the place where everything that's there is going to keep being there. And there's going to be stuff on top. And whenever you're talking about replacement, you're almost always wrong. And, and I think this happens a lot in web three where, where people talk about like, oh, you're going to replace stuff. Because it's not just that you're, you have the inertia stuff and all that. It's that whatever came along is perfectly suited to that moment in time, right? P and G was perfectly suited to a big box retail world.

• 1:01:32Speaker 01

  And you're not going to disrupt that. If you're going to beat it, it's because you have something new that's suited to the new world. And you're, and you're going to succeed at that, right? I think advertising is one of my favorite examples where when, when web, when, when web advertising came along, they just put ads next to the content because that's what you did in newspapers, right? And, and then they only talk about, oh, the web monetizes so terribly. It's like, and so what happened was the, the, the transformation was having feed advertising, where you had an endless supply of content and then you put in ads in the middle of that content. And just as you're choosing the best content for the person, you're also choosing the best ad for that person. And that was something you could not do in the analog world.

• 1:02:14Speaker 01

  That was uniquely enabled by digital and by the internet. And that's always going to be the quality of something that succeeds. Any web three project that is just doing a web two job, but with a blockchain is going to fail. Without question, because all this web two stuff is optimized for years to be really good, right? Like, like it's hard to get database performance for like, like, like we, whether I did this thing for Striker, I believe this like new backend. We went silent for like six months. We had to completely rework our database because like the, the, and this is for a relatively small audience, right? Like you're, if I'm on a blockchain, like, no, there's no worry.

• 1:02:55Speaker 01

  And so you have to think through what is actually only possible with this technology. That's where the opportunity is. Replacement, there's no opportunity there. It, it, you're fighting inertia and you have worse tech. You need to find something that's, that's actually better. And that's where, that's where there's going to be opportunity.

• 1:03:12Speaker 02

  We have one, I have one coming out tomorrow morning that I covered with Alex Stanko on what Shopify is doing in the space. And I thought the answer was going to be Shopify is making it really easy to sell NFTs because that's what you do on Shopify. You sell stuff. And of course, that's not the answer. Alex and Toby and all of them are smarter than what I think about for 30 seconds a day. And the big push that they're making is trying to make Shopify and kind of everything that builds on top of Shopify wallet aware. And so they're calling it token gated commerce, but you know, what shows up and what you have access to and how collabs work and all that stuff. When you can show up to a site with your whole inventory of things that represent you and that you care about. And so I think like that kind of stuff is, is really interesting and how Shopify does there, I think will, will set a tone.

• 1:03:55Speaker 02

  And that's a web two company, but I think, you know, their, their impact here will be really big in terms of just putting resources and scale behind. What can happen when people show up with an inventory of all their things to every website they go to?

• 1:04:08Speaker 01

  Yeah. And I'm, I'm very optimistic on things that are, and this is an example of it, that are 99.99% web two. With this one specific layer that's only possible with sort of web three. I think that Shopify, that's actually a perfect example. I, I did, ran an interview with Adam Mosser a couple of weeks ago about what, how Instagram's thinking about this. And it was great because that was actually a pitch for like the way I'm thinking about it, uh, which is from a creator perspective, you like, I have this audience and I want this audience to, to get access to things around, you know, around the internet. And, and traditionally you would do a business development deal, right? But we just talked about on this podcast that the opportunity on the internet is broad.

• 1:04:51Speaker 01

  It's not deep and you can't do business development deals with every possible opportunity on the internet. So wouldn't it be great if there, they had an identity that they could carry around that shows they're a Shetland subscriber? Boy, who's, what, what's out there that could, that is not doing computation is not, all it is, is just a ledger of do they have access to this or not? Boy, it'd be great if someone invented that, right? And, uh, and, and, and, and suddenly, oh, wait, that's exactly, only a blockchain can solve that, only. Blockchain can be accessible to every single possible service on the internet without a business development deal.

• 1:05:29Speaker 01

  And can be accessible and it's like, and once you see that, it's like, of course, there's something here, right? Is that replacing Facebook? Is that replacing Twitter? No, it's not. It's something that can only be done by this and it enables, could it enable sign into Twitter? Sure, absolutely. Now we're talking, there's something interesting there, but it's not a Twitter replacement. It's that bit of the stack that that actually could use something like this.

• 1:05:57Logan Bartlett?

  You know, there's gonna be a lot of people that that look to both of you in terms of what you're doing and your process and all this stuff. Is there advice for people? I mean, I guess myself included to some extent, but do you all have advice for people that want to create? And do look at you guys, Packy, have you come up with anything of just advice for people to? Build on some of the things you guys have done to date and ways to stand out?

• 1:06:22Speaker 02

  I mean, I think it's a lot of the things that we've talked about today. Frankly, it's find the thing that you're uniquely. Either qualified to talk about, which I might not have been, or at least passionate enough to kind of continue to show up and do the research and do the work and all of that until you can get good. Probably find your own kind of voice and maybe medium, maybe business model. I'd say experiment a whole hell of a lot in the beginning while nobody is watching, which I was lucky enough to be able to do because. Practically nobody subscribed to the newsletter for over a year. And then like, if you know, if you can stick with it for over a year without making any money on the thing and you still show up every week and do it and you love doing it that much.

• 1:07:00Speaker 02

  I think there's probably something there, but I don't know. I would say there's not a shortcut and you have to do a just an absolute shitload of work to be able to make it happen. But have as much fun as possible, kind of on the way and experiment with different things and. And to kind of what Ben and I have been saying the whole time and what Ben's kind of called out. Just like find that alignment in the whole thing that you do, the topics that you write about your own voice. Because if you talk in somebody else's voice, it gets even harder to show up and write every day or every week or whatever. Uh, and then make sure that kind of the whole, the whole stack of what you're doing, uh, aligns with, with things that you believe in and, and are interested in.

• 1:07:39Speaker 01

  I, I agree with all those points. I think the most important bit is, is the bit about making your own pond. Like, like you, you, that's the opportunity. Like I think, for example, there should be a daily newsletter about every single major tech company. Like there should be a daily Amazon newsletter. There is a daily Apple one. Uh, there should be one about Google. Like there, like there's little stuff that happens that is actually pretty impactful. And I have, I have, you know, I have, I have a, an outline where I just put links in and stuff that happens. I have tons of stuff that I, that, and I try to pull it all in. Once I, I'm writing about Facebook, let me pull in a bunch of stuff that I've, that has been building up or Amazon or whatever it might be. Um, so, and what's, I think in some respects, Chitakiri is a bad example for everyone.

• 1:08:24Speaker 01

  Because I have kind of the dream gig, right? I sit at home and I write about the most popular tech companies that everybody knows about, right? And everyone's like, oh, would that be great? But it's, it's like, I'm like the most competitive market on earth. Everyone has an opinion on the big tech companies, right? Everyone, and, and so

• 1:08:45Speaker 01

  I was lucky that I was early and so there was no one else doing what I did. But part of that is what you can do too. I identified an opportunity in the market, which was you had all these sites that wrote about products. You had Wall Street that wrote about results and there was this big gap in the middle that no one talked about. And so that was like sort of the, the market opportunity that I saw, but just because I'm in that market doesn't mean there's not lots of other markets available, right? And so, um, Where if you want to write about the same thing everyone's writing about, you're competing on your ability to generate differentiation on your own. And that's exceptionally difficult, right? And even today, like I now have the benefit of inertia and you have been around and have lots of readers.

• 1:09:28Speaker 01

  And people give me feedback, which is like its own sort of like, like, uh, superpower. And so if you're just starting out, say, I want to, I want to write a checker 2.0, like good luck. Like if you want to succeed writing the same stuff I do, your content is going to be so unbelievably exceptional. And even then you, it's going to be, it's going to be tough, right? And so, cause I'll just link to you and say, hey, look at this great thing that I wrote. And I'm going to add a couple of things to it. Um, and so, so, uh, so that, but you don't, you can define, like you, you get to define your market. It's, this isn't the old newspaper model where I'm the sports columnist in New York and you're trying to take my job. Right? Go be a sports columnist in Boston. Go be a sports columnist in LA, right? Like there's, there's, there's lots of opportunities there. That's number one.

• 1:10:12Speaker 01

  But then, so it's really define your market. Number two, uh, and this is a life advice in general. You always want to double down on what you're good at. People spend too much time trying to, uh, to, to humiliate their, or like, take care of their weaknesses or address where it is. I think, Packer, you've kind of like you're, you lean, you're the best golden retriever on the internet, right? Like you lean into that, right? And, um, I would be terrible at that if I was trying to do that. And you know, this goes back to almost like why I charge less money. Like everything about my life and business is all about, as long as I write four pieces a week that are decent, then everything else works out, right? And I just said, if I keep up on that and I try to, everything else in my life,

• 1:10:57Speaker 01

  that I'm not good at, or I'm bad at, or whatever, like, like I try to, to, to outsource to someone else to do, like all those sorts of things. And, and obviously when you start out, you're doing everything, right? So you have to, you, you have to humiliate your weaknesses, but you want to find an opportunity and a career and a job that is doubling down on what we're good. And so in my case, just go back to, I read fast, I write fast and I have a good memory, right? So writing four days a week works well for me, right? If you don't have those three things, it's going to be tough to write four days, like write every day. I, I, and so, but you might have something else that makes sense that works. Um, and so, uh, don't get too hung up on. I think number three is we talked a lot about alignment and that's why Packy and I are doing very well.

• 1:11:42Speaker 01

  I think you don't want to get too hung up on that early. You want to have a direction that you're going. But the biggest danger in life is having like a five year goal, which I say is I started to strike the five year goal, but uh but because what's gonna happen is you're gonna succeed and you're gonna get there and you're gonna look around and say crap, I'm totally in the wrong place. I've been so head down. I'm trying to get to this place and meanwhile, the world went in a different direction or there's different sort of opportunities. Uh, you know, with the five year goal, actually, I didn't have a five year plan. I had, I want this to be my job in five years. And then we just talked about, there's a lot of adjustments and changes I made along the way. Uh, even, you know, like I said, the way ripping out a weekend, completely changing the format with the daily update, update is, that's the approach you want to have and um, and honestly,

• 1:12:28Speaker 01

  people look at what Packy and I do and this is a challenge because we're both visible figures on the internet. And so it's like, well, people are jealous, like, oh, that, that looks so great. That looks so fun. Um, and it is fun. Like, I feel very fortunate that this gets to be my job. It's not so fun when it's Wednesday night at nine PM and my out update is supposed to be out two hours ago. And I, I'm stuck and I just don't know what to write about and I'm just like by sheer force of will. I'm churning out 1800 words about something and I, and not only does it suck. And I feel terrible, but I know I'm gonna be absolutely miserable for the next 24 hours because when I write something that I don't feel great about, I feel sick.

• 1:13:12Speaker 01

  And I, I like, and I just feel, I feel horrible and like, that's not, that's not, that's not very fun, right? There's, not everything is fun and you know, if now it's balanced out by all the good stuff for sure to be, I'm not, I'm not trying to beg poor here. But I think just observing friends and people in, in tack or people in, in the world. Real joy comes from being good at something and.

• 1:13:39Speaker 01

  This whole follow your passion business is nonsense. You, what, what you are passionate about is what you're good at. And, and you talk to a 20 year old, oh, follow your passion. They have no idea what they're passionate about because they have no idea what they're good at. And so your goal in life in general should be figuring out what it is you're uniquely capable of doing. Because if you can do what you're uniquely capable of doing, if you focus on your weaknesses, you double down, you don't waste time, you humiliate your weaknesses, or sorry, you double down on your strengths, excuse me, you double down on your strengths, you humiliate your weaknesses. You're going to end up being the best in the world and being the best, like, I don't know, like, say you're an accountant for fintech startups, but you're the best accountant for fintech startups in the world.

• 1:14:23Speaker 01

  Whoever that person is, maybe you know who it is, Logan, I bet they're absolutely, they love life, right? And, and they're, they're, they don't have to be a writer on the internet, which honestly, you know, being a plug figure kind of sucks. Uh, no one knows who they are and they're probably making a ton of money and they love life. Like, like that's, that's the dream. The dream is being awesome at something. And with the internet, there's so many things that you can be awesome at because the market's so big and it's so broad that I think the opportunity to have joyous existences is much higher than ever before. And you don't have to do that by writing a subscription newsletter. Like, there's lots of things you could do.

• 1:14:59Logan Bartlett?

  That's great. Yeah, I, I, I'll just add, and I probably won't even add this bit, but it is just for your guys own benefit. I saw what the all in guys, uh, were doing and I was like, you know, they're wearing, they're talking about their cashmere sweaters and their private planes and that they're all billionaires. And I'm like, that's just, it's great and they're killing it, but like, that's just not relatable to the masses. And some people want to hear that stuff, but for the most part, people like, that's going to be off putting in some way and they keep talking about the war in the Ukraine. And like, that's just pretty somber to be talking about all the time and like, If if I can bring on and involve people with just like a little bit different fun tone, that's not so hef like people, I think the way the politics got covered in the 50 or sorry,

• 1:15:44Logan Bartlett?

  Hollywood got covered in the 50s and 60s and sports got covered in the 80s and 90s and politics in the 90s and 2000s, we're clearly entering that world for tech now. And there's this palace intrigue that exists about what's going on in general, right? And if you can help people bridge the gap and help them see around the corner a little bit and they get to feel like they're on the inside or just a little bit smarter, I just think that's an exponentially growing market right now. And so if anyone, if you just stake out a corner of that.

• 1:16:13Speaker 01

  Well, the two is the cost structure is incredible, right? You don't need very many people. And I mean, and just to go back to the all in point, I think is the interesting point. Ah, if that podcast would be so much worse if they were pretending to be the common man, right? Like that, that's an example where guess what? They are billionaires. So like lead into it, right? You know what I mean? So it kind of makes your point in a different way.

• 1:16:36Speaker 02

  Well, and you've been playing this character on Twitter for the past, for a very long time that I think makes you the right person to host the kind of thing that you're talking about. So.

• 1:16:46Logan Bartlett?

  I think, I mean, you know, what's interesting is, is, is you, uh, one of the reasons I wanted to do this is because, you know, the character you are, Twitter is a interesting form factor because, you know, Ben has to have not tech Ben and he has Ben Thompson, the tech account.

• 1:17:00Speaker 01

  Which I need to go back and review some of my tweets from last night. Cause like I said, the implication of me not being with it this morning is, is, uh, if I ever get canceled, it's for sure because of some NBA playoffs being on at three in the morning my time and, uh, be doing something regretful.

• 1:17:16Logan Bartlett?

  Mine will be for paying college football players to go to the University of Tennessee. But yeah, no, it's one of these things that like you, you, you're not enabled, uh, Twitter's uh, as a medium, you're force feeding people, uh, all of your posts, right? And so the ways to grow in general are to stay narrow and have people show up and know what they're showing up for, right? And at the end of the day, you don't get to be a three dimensional person if you want to refine the interest graph.

• 1:17:43Logan Bartlett?

  And because people are tied to followers and not interests are tied to followers, you're force-feeding people your entirety of the personality. And so I would need to almost fork my Tennessee football stuff from my tech stuff in the way that Ben did it. And one of the things I felt was I was becoming too much of a character, right? And I've had to sort of evolve from it a little bit because I felt myself falling victim to the trap where I have enough followers, right? I have almost 50,000 followers. That's enough, right? And I'm sure it's great to have Packy 116 and Ben.

• 1:18:15Speaker 02

  Yeah, I was gonna say, I don't know if it, I thought the same thing at 50, but.

• 1:18:19Logan Bartlett?

  Yeah, exactly. It's a myopic viewpoint.

• 1:18:21Speaker 01

  No, I, well, I'll go the opposite direction. I have 200,000 some and it sucks.

• 1:18:25Speaker 02

  No, I'm kidding. I, it was so much more fun at 50.

• 1:18:28Logan Bartlett?

  Yeah, totally. I actually had the most fun at like eight, right? The climb, and it's one of these things, Ben, I'm sure you appreciate this with the Milwaukee Bucks. Like the climb is so much more fun than like the, the defending the title, right? And I'm sure defending the title and having it as the consummate like fun. But I'm seeing this with Tennessee football right now where like, I just really hope we're finally on level playing field. And like, we're getting back to where we were in the nineties, right? But like this whole momentum and the process of it, and this sort of goes to, you know, you can't look at, I'm sure at some point you guys recognize that you were at the end and everyone admires you for where you've gotten, right? But like, it's not like you feel as a different person now that you got there.

• 1:19:07Logan Bartlett?

  You've succeeded and you're the same person. You have all the same insecurities and successes and whatever, relationships with people and all that stuff. And so if you're not appreciating the inputs on the journey, you're going to be miserable when you think you get to where you're going ultimately, right?

• 1:19:21Speaker 01

  No, absolutely. And like the, I mean, one of the things I'm working on now is like, I might actually be launching a new podcast soon. And part of that is like, if you're, I don't want to get stuck just doing the same thing, right? Like you, you want to. Stratechery succeeded beyond my wildest dreams and imaginations. And there's also the fact that aggregation theory was totally right and it all came true. And I wrote an article, I think a couple of weeks after I wrote Aggregation Theory originally, saying like, look, the long-term outcome of this is a bunch of antitrust cases. And then the antitrust cases showed up. It was like, and then I was writing about like, you know, this sucks. I don't actually want to write it.

• 1:19:59Logan Bartlett?

  And so from a materiality standpoint, anything you write about ATT and antitrust is so much more important than talking to startup CEOs and interviewing them from a pure materiality on the world standpoint, but it fucking sucks. It's boring. Like it just, it's mind numbing.

• 1:20:14Speaker 01

  But to that point, like, I'm like, you know, I stepped back from it. I'm like, look, if big stuff happens, I'm going to cover it, but like, I can't do this every day. And that's where I was like, well, I want to think about, you know, this, this new podcast. I'm building this service for Stratechery and, you know, and, and I think to your point,

• 1:20:34Speaker 01

  yeah, you, you like the journey, like I wasn't enjoying, like I wanted to get on a new journey, right? Because I don't know, I agree with you completely. You gotta embrace the journey.

• 1:20:44Logan Bartlett?

  No, and it's one of these things that now I got to the Twitter, like I've had some level of Twitter success, but ultimately, it's always like, I'll try this, right? And you know what? It's fucking hard. It really, like, do you guys know this? It's a grind, right? And people say mean shit and they like, I was able to hide behind a little avatar and be snarky and never serious, right? And now I'm totally exposed and people say mean stuff and I'm like, where the fuck? Where is that coming from? Right? Like my favorite, cause we had, we had not spoken for maybe like a couple of years, uh, kind of before I got back into this, into this world. Before you were going to benefit me in some way? Before I was going to benefit you in some way and I, I will spit out my drink.

• 1:21:27Logan Bartlett?

  So I started, you know, I started writing and Logan was reading it. And so then like, I guess I like broke, maybe I like said something funny. So I broke into the inner circle and Logan would like a couple of times send me like drafts of tweets that he was going to send and be like, what do you think here? Like, can I get feedbacks? And I was like, holy shit. Like it seems like just pure shit posting, but he's like working over here. So there is that whole thing behind the curtain. Oh, totally. Yeah. I have the whole ghostwriters writing for me too. I have the whole staff, you know, the writer's room.

• 1:21:53Speaker 01

  No, I, I think this is a point that, that we've all made implicitly, but.

• 1:22:00Speaker 01

  There's a, there's a component of just hard work and grind, right? I mean, like, like I, I mentioned in passing, like being on vacation when I launched and literally waking up at like, we're in Europe, waking up at like six in the morning, we're in Paris, sitting in a bathroom and writing a daily update. Because I, like, I just started, I had a couple hundred subscribers, like, and I, I probably had like 150 subscribers, maybe? And, and like that, you just had to do it. And like, I've been writing, you know, I, I joke about doing four a day now, but I've been doing four a day for nine years or, or eight years.

• 1:22:39Logan Bartlett?

  Four a week.

• 1:22:39Speaker 01

  Yeah, four a week, I should say, yeah, that'd be tough.

• 1:22:42Logan Bartlett?

  That's back to the Adderall, the guy taking Adderall and just like burning out, right?

• 1:22:46Speaker 01

  Which, yeah, I, I, uh, is not, not my thing. And I think that, um, there's just an aspect of grind and discipline. And a challenge is you can grind to nowhere. So you definitely want to have feedback loops, so you're going in the right direction. But there's a point, particularly if you want to be in the content game, like you're gonna produce a lot, like a lot of content with very few readers. And, uh, and, and that's gonna, that's gonna wash a lot of people out.

• 1:23:14Speaker 02

  I did the math at one point early in that like period where I had like 300 subscribers and how much time I was spending. And I was like, damn, the amount of time I'm spending for per free reader is just like a pathetic amount of time. I'm like spending eight minutes or something for every one of the free readers on my news. Not just that, but I swear I used up all my, all my best content. I don't want to generate new insights now? What's up with that?

• 1:23:37Logan Bartlett?

  It's like, I always think about Nas, like spending his entire life writing his first album. And then like, you know, one year later, he has to come up with another one. It's like, shit, I, that was, that was 19 years of my life. And now I have to, you know, come up with another album.

• 1:23:50Speaker 01

  Yeah, Jay, Jay, Jay-Z told me about that.

• 1:23:53Logan Bartlett?

  Yeah, exactly, exactly. So, uh, wait, then one last thing, I guess, before we hop. I, you had said something about like, uh, the John Gruber thing you had said earlier about making sure you actually had a breadth of content before you started publishing a little bit. How do you, how do you think about as someone's getting going on this, like the perfection? I, I tried three test episodes before I actually did a podcast and to some extent I wish I had done 10.

• 1:24:17Speaker 01

  No, because you want to get it out there, right? You're fine, do this work. But I mean, like, just to give an example for Dithering, I think we did 30, uh, before we launched. And, uh, a big thing on the internet is The, the most important article people will read is the second article on your site. Because like, anyone can, lots of people come up with one great article, right? But then you read that article, you click around, you're like, oh wow, that was also really good. Or, in one day, I was like, Strickery had started, I was, I thought a lot about branding. People, I joke about the name, but it's, it's a memorable name. And it has the orange, and I had a custom font, which was, which was rare back then, I had those hand drawn images. And the reason was because I wanted people to show up and say, wow, that was a good article.

• 1:25:02Speaker 01

  Then they would show up weeks or months later, and there'd be a sense of familiarity, I've been here before. And, because, because that's, it's that second article where it's like, bam. Like, you don't see that often, where you get sort of the, the second article, that, that's really good. And so, I think just, um, and, and this speaks to the, you know,

• 1:25:24Speaker 01

  you don't have to be, I don't, I think frequency is over, it's both overrated and underrated. I think particularly when you're starting, it's very overrated. No, like, your 100 subscribers are not, who cares if they show up every day, right? Especially with the email, or even Twitter, you have a way to connect with them. And so, you should really take the time, it's, I don't know, and I'm kind of disagreeing with myself. I want you need to iterate, you need, you need to be regular, because you need to figure it out. You need to figure out what your voice is, what your topic is, et cetera. At the same time, you don't need to copy my four days a week sort of schedule, right? Like, I have a lot of subscribers now that are, that are paying for that. And so, I have to live up to that. But when you start, you, I think, Packy just said that, you can sort of, you can sort of figure that out, and you should, and you should take advantage of that.

• 1:26:07Speaker 01

  Now, I do think, once you're established, people, I think the regularity is extremely underrated. It's a huge Strickery, uh, point of differentiation, is people, people will tell you, this is where I think revealed preference and stated preference is different. They'll say, oh, I don't, don't worry about doing every day, I just want you to do a good job. And I think, actually, no, like, people are, they have a habit, they read it the same day every time, it's always there. They don't think about it, like, 75% of our subscribers are annual subscribers instead of monthly. So like, I just have this base where I am a habitual part of their life. And from a business perspective, that's exactly where you want to be. Like, you're not earning an audience with sort of every, everything you write. But, I'm nine years in, like, you don't need to be doing that at the beginning. You, like, you, like, and so, you, you have a-

• 1:26:52Speaker 01

  You have a, you know, what is it? One chance to make a first impression on the internet is not quite right. You have a, you have one chance to make a second impression. And that's the part that is actually really important. Yeah. Packy, what do you say about that?

• 1:27:04Speaker 02

  Yeah, I mean, I, I think, I think I agree there. I was consistent, kind of the whole time. I would just do kind of like a weekly something, but it could have been a bunch of links. And like, you know, there was a period in my life where I went to the gym every day for, you know, X. When I was in much, much better shape when I was younger, but some days it would be, I'd run to the gym. I do a pull up and I would leave and it was just to kind of like, make sure that I didn't break that streak. And I think it probably is a personality thing. So for me, like, I just don't miss Mondays. Like I took one off when, uh, when Devin was, our son was born and then I was back the next week. I take holidays off and that's it. And then, you know, I'm writing Monday, I'm writing Thursday. It's not like Ben's output, but, um, I think that consistency is important.

• 1:27:50Speaker 02

  But I did give myself that space in the beginning to just like throw some links out there. While I was working on like a bigger essay in the backend, as long as I can kind of keep that consistency up just almost for myself more than the audience in the beginning. Cause nobody cares. I think that's like the other big secret here. It's tougher for you to start a podcast because you have a following. It's tougher for Ben to start a new podcast or for me to try something else because we have followings. In the beginning, there's something really liberating about the fact that like, nobody gives a shit about what you're doing. If it's really good, people might find it and that's great. If it's really bad, nobody cares and they're just not going to waste their time thinking about it at all. And so there is something liberating, I think, about that in the beginning. And so just take advantage, experiment, but like impose some discipline on yourself so that you don't just let it slip and let it slip and let it slip.

• 1:28:33Speaker 01

  Yeah, the, the discipline thing is, is huge. I mean, like people think I'm this unbelievably productive and prolific writer. And the reality is, is like, I have four daily deadlines and so I have four, uh, instigators of panic a week.

• 1:28:48Speaker 02

  Yep.

• 1:28:48Speaker 01

  And if like, I'm terrified of like writing a book. On one hand, I think the, you know, my model is much more lucrative. Uh, on the other hand, I just, I would. I wrote, I wrote a, my thesis paper when I was like a senior in college. I wrote the whole thing in like a 48 hour span, like the middle of finals week. Well, I mean, I'd done all the research. I had all the pieces and I had it all in my head. But like, I just not the sort of person that's gonna like, oh, I'm gonna sit down and do, do work, do 10 pages of my book today. Um, so there's little hacks you can do for sure. Uh, but I think just to emphasize, as Packer's point, it doesn't, again, this has to be four days a week. But there is some value in if you can get some sort of deadline on yourself, even if it's an artificial one.

• 1:29:30Speaker 01

  And just because it, the other advantage that I have is I've, I've just, I've been doing this. I, I know how to write a daily update, right? Like I, I could sit down and there's some days I'm busy. I have stuff going on and I can churn something out. Is it my best possible piece? No, but it's pretty good. And, uh, and that's just a competitive advantage, but that only comes with sort of time.

• 1:29:53Logan Bartlett?

  Yeah, got it. Well, that's great. Well, thank you guys both for doing this. This is a, this is a lot of fun.

• 1:29:58Speaker 01

  It was, it was great, great fun to chat and thanks for, thanks for having me on.

• 1:30:01Logan Bartlett?

  Likewise, this was awesome.

• 1:30:07Logan Bartlett?

  And that concludes part two of, uh, episode 15, Three Cartoon Avatars. Obviously a ton of content this week. Thanks everyone for, for listening. If you made it through everything and excited for, uh, for next week of, uh, of episode 16 of Three Cartoon Avatars or episode two of Cartoon Avatars, however you want to score it. Uh, we have a really, uh, exciting guest coming on to co-host with me. Someone that I've admired for a long time and taken a lot of inspiration from. And so, uh, excited for you to hear next week as well.