WEBVTT

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Welcome in, everyone. It is great to have you

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here with us for another deep dive. Yeah, really

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glad to be here today. We always say that you,

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the listener, are the crucial third person in

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this conversation. And today, we have a topic

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that is going to spark some serious recognition,

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especially if you spend any time staring at a

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computer screen trying to learn a new skill.

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Oh, absolutely. I want you to picture a bookshelf.

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Specifically, a bookshelf belonging to... Anyone

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who has ever dabbled in programming or web design

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or, you know, IT in general. I think I know exactly

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what shelf you're talking about. Right. If you

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look closely, you are guaranteed to see at least

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one of these highly distinctive books. You know

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the ones that usually have this stark white background.

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And dead center on the cover, there is an incredibly

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intricate black and white woodcut illustration

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of an animal. Right, like a camel or maybe a

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lemur. Yeah, or some obscure bird you can't quite

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identify. It is a brilliant piece of visual branding,

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honestly. You see the animal and you instantly

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know the publisher. Exactly. So today's deep

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dive is all about the fascinating evolution of

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the company behind those covers, O 'Reilly Media

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Inc. They are a company that has... quietly shaped

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the entire tech landscape over the last few decades.

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Yeah, and our mission for this deep dive is to

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trace that specific evolution. We're going to

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look at how O 'Reilly started as just a small

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technical writing consulting firm way back in

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1978. That's a consulting firm. Exactly. And

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we'll explore how they transformed into a real

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kingmaker in the tech world, how they navigated

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the dot -com bust, pioneered the very concept

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of web advertising, and eventually executed a

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radical shift in their business model just to

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start. survive in the digital age. It really

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is a story of constant reinvention. And just

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to set the stage here, O 'Reilly is headquartered

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in Sebastopol, California. Right. But while they

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operate out of Sonoma County, their influence

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is totally global. They've acted as the quiet

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architects behind exactly how we learn about

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technology today. They don't just report on what

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is happening in tech. They often define it. Totally.

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And to understand how they reached that position

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of influence, we really have to establish a chronological

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baseline. We need to go back to 1978 in the Cambridge,

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Massachusetts area. At that time, Tim O 'Reilly

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started this company, but it was not a publishing

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house. It was originally a private consulting

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firm focused strictly on technical writing. Okay,

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let's unpack this because the leap from private

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consulting to global publishing empire is not

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a straight line. line. No, not at all. The shift

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really started happening in 1984. O 'Reilly began

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retaining the publishing rights for the vendor

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annuals they were actually creating for Unix

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systems. They started producing these little

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70 -page guides that they called nutshell handbooks.

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And they were well -received, but consulting

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was still paying the bills. Right. It was a side

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project, basically. Exactly. The actual turning

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point was in 1988. They took some preliminary

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manuals for something called Exlib to a conference.

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Oh, wow. Exlib. Yeah. Now, XLib was essentially

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the foundational code for building graphical

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user interfaces on Unix systems. And the attention

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those specific manuals received at that conference

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was unprecedented. I can imagine. It was the

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catalyst that made them realize they needed to

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seriously ramp up their book production. It was

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a classic example of finding a distinct need

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in a niche market and just scaling up to meet

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it. But as they scaled their book production,

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they needed a visual identity that would make

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them stand out. on a shelf. And the story behind

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those famous covers is surprisingly practical.

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You might think there was some intensive corporate

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branding study done to choose these specific

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animals. Right. Some big agency involved. Exactly.

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Yeah. But designer E .D. Friedman created the

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original animal cover art for a very simple reason.

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She was looking at all these strange, obscure

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Unix program names, and she thought they literally

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sounded like weird animals. That is so funny.

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So she just started putting weird animals on

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the covers. Functional design becoming iconic

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by total accident. And that animal theme became

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so deeply ingrained in the company's DNA that

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it became their face to the world. Think about

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the cover of their book on the Vi editor. Oh,

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man, that notoriously complex text editor. The

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one every programmer has to fight with at least

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once. Yeah. The animal on that cover is a tarsier.

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And that exact tarsier illustration was eventually

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incorporated right into the official O 'Reilly

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logo itself. It moved from being just a cover

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aesthetic to the corporate identity. A weird

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eunuch's name leads to a picture of a Tarsier,

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which leads to a global brand logo. That is wild.

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It really is. But as we move into the 90s, O

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'Reilly didn't just stick to printing physical

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books. Here's where it gets really interesting.

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Today... We take a heavily monetized ad -driven

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web as a given. Oh, absolutely. But back in 1993,

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someone actually had to be the first to pull

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that trigger. And ironically, it was O 'Reilly.

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They created one of the very first web portals

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called Global Network Navigator, or GNN. We really

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need to pause and look at the historical significance

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of GNN. Based on our sources, GNN was the very

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first site on the World Wide Web to feature paid

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advertising. That is a profound contradiction

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when you think about it. How so? The company

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that championed open source ideals and free information

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is the exact same company that created the ad

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-supported monetization model of the modern Internet.

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Yeah, that's a wild juxtaposition. But they didn't

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hold onto it for long, right? Right. By 1995,

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they sold GNN to AOL. Why get out so early when

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the internet was just starting to take off? Well,

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it was likely a matter of recognizing their core

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competencies versus where the web was heading.

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The sale to AOL in 1995 occurred right during

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the early swell of the dot -com bubble. It was

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one of the first really large transactions of

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that era. They capitalized on their early foresight

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and secured funding that would allow them to

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focus heavily on their broader ambitions in publishing

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and community building. Of course, the dot -com

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bubble eventually burst and the whole industry

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History took a massive hit. Yeah, it was brutal.

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Fast forward to 2003, and the landscape was pretty

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grim. People were writing off the internet as

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a failed experiment. This is where Tim O 'Reilly

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and Dale Daugherty stepped in with a very specific

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goal. They wanted to reignite enthusiasm in the

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computer industry. They needed a way to signal

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that the Internet wasn't dead, it was just evolving.

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Right. To do this, they popularized a term you

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have definitely heard, Web 2 .0. Oh, yeah. Now,

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to be precise, the term was originally coined

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back in January 1999 by a writer named Darcy

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DiNucci. Right. We should give credit where it's

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due. Exactly. But O 'Reilly and Daugherty took

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that term and used it as the banner for a major

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summit they were co -producing with TechWeb,

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which was formerly known as CMP Media. Web 2

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.0 became the ultimate buzzword. It was everywhere.

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But what did it actually mean in practice? If

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we connect this to the bigger picture, Web 2

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.0 was a crucial framing device. It was used

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to distinguish the companies that survived the

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dot -com bust from the ones that disappeared.

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Makes sense. More importantly, it identified

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the key drivers of future success. It put a name

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to concepts that are foundational today. Things

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like cloud computing, big data, and new approaches

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to iterative, data -driven software development.

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It was effectively a roadmap out of the bust.

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But whenever you create a highly visible buzzword,

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the lawyers eventually get involved. Naturally.

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There was some serious drama surrounding the

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term Web 2 .0 in May of 2006. CMP Media, who

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co -produced that Web 2 .0 summit with O 'Reilly,

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had actually registered Web 2 .0 as a service

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mark. Right. Just to clarify for everyone, a

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service mark is essentially a trademark, but

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it specifically protects services like live events

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and conferences rather than physical products.

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Good distinction. Well, an Irish nonprofit decided

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to run a small Web 2 .0 half -day conference.

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Just a little half -day event. Exactly. And CPU

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Media caught wind of this and sent them a full

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-blown cease and desist letter. It was a very

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heavy -handed corporate move against a nonprofit.

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And it generated immediate backlash online. It

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clashed directly with the open, collaborative

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ethos that O 'Reilly was known for championing.

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O 'Reilly had to step in to do damage control.

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They apologized publicly. for the aggressive

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early involvement of attorneys, noting that someone

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should have just picked up the phone and called

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the organizers instead. Which is how you'd hope

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things would work. Ultimately, they allow the

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nonprofit to use the service mark for that single

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event. That incident is a great lesson in community

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management. You have to protect your intellectual

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property, but you absolutely cannot alienate

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the very developers who make up your core audience.

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And O 'Reilly wasn't just defending Web 2 .0

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in the courtroom. They were literally building

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the rooms where these developers gathered. Which

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brings us to their leap into live events. Yes.

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Roughly two decades into their existence, they

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expanded heavily into event production, running

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conferences from 1997 all the way up to 2020.

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It started in 1997 with the Perl Conference.

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Initially, it was just a smart way to cross -promote

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their books on the Perl programming language.

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But then, in 1998, they did something truly visionary.

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They invited leaders from various software projects

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to a single meeting. They originally called it

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the Freeware Summit, but it soon became known

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as the Legendary Open Source Summit. They were

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bringing together rival factions of the open

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source world and just getting them to talk to

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each other. Exactly. They became famous for their

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flagship events. You had OSCON, the O 'Reilly

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Open Source Convention. You had the Strata Conference,

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which was laser focused on big data. They ran

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the Velocity Conference for web performance and

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the highly exclusive FOO Camp. This raises an

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important question about how O 'Reilly viewed

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their role in the industry. They eventually stated

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that they didn't view their business as just

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publishing or just running conferences. Right.

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Their stated goal was changing the world by spreading

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the knowledge of innovators. They viewed themselves

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as the central nervous system for tech knowledge.

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And they didn't just limit this philosophy to

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software either. They took a fascinating detour

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into the world of hardware and DIY culture with

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the maker movement. That was a huge shift. In

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January 2005, O 'Reilly launched Make Magazine.

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And the very next year, in 2006, they launched

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the Maker Faire. The scale of these events was

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staggering. It really was. The flagship Maker

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Faire in San Mateo, California, drew over 130

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,000 attendees. It was a massive celebration

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of physical invention, craft, and engineering.

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They tried to expand that DIY ethos into other

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areas as well. In the fall of 2006, they launched

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a second magazine called Craft with the tagline

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Transforming Traditional Crafts. However, that

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publication folded by 2009. But the core maker

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brand was successful enough that in 2012, O 'Reilly

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Media spun out the make properties into a completely

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separate venture -backed company called Maker

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Media. Right. It was headed up by Dale Dougherty,

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the former O 'Reilly executive who actually helped

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coin Web 2 .0. The Maker Media story has a difficult

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ending, unfortunately. Despite the massive cultural

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impact and millions of people attending fairs

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globally, the financial model eventually collapsed.

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Yeah, that was tough. In the summer of 2019,

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Maker Media laid off its staff and ceased operations.

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It is worth noting, though, that Make Magazine

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itself survived and is currently published by

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a different entity, Make Community LLC. It was

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a heavy blow to that community. And it was somewhat

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of a harbinger for... O 'Reilly's own live event

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business. Because in March 2020, an earthquake

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hit their business model. O 'Reilly announced

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they were permanently closing the entire live

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conference's arm of their business. Decades of

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legendary tech summits came to an abrupt end.

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It was a monumental shift. But O 'Reilly survived

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that sudden loss of their event empire because

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they had spent the previous two decades quietly

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building a robust digital infrastructure. So

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what does this all mean? Think about how you

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consume information right now. You stream it.

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You subscribe to it. O 'Reilly saw this coming

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way back in 2001. That is the year they launched

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Safari Books Online. It was a subscription -based

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service providing access to e -books and videos,

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and it originally started as a joint venture

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with the Pearson Technology Group. They were

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so far ahead of the curve on the subscription

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model for technical education, and as the years

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went on, they strategically doubled down on it.

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In 2014, O 'Reilly acquired Pearson's entire

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stake in Safari Books Online, making it a wholly

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owned subsidiary. They redesigned the site and

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heavily expanded their focus outward. They pushed

00:12:30.149 --> 00:12:33.129
hard into the B2B enterprise market, basically

00:12:33.129 --> 00:12:35.129
getting corporations to buy subscriptions for

00:12:35.129 --> 00:12:37.690
their entire engineering teams. And then in 2017,

00:12:37.870 --> 00:12:39.970
they made a business decision that seems incredibly

00:12:39.970 --> 00:12:43.049
risky on paper. They completely stopped selling

00:12:43.049 --> 00:12:45.700
single books online. including e -books. Completely

00:12:45.700 --> 00:12:48.100
cut it off. Taking away the ability to just buy

00:12:48.100 --> 00:12:50.320
a single book online seems like corporate suicide

00:12:50.320 --> 00:12:53.500
for a publisher. How did they justify cutting

00:12:53.500 --> 00:12:56.080
off a proven revenue stream like that? It comes

00:12:56.080 --> 00:12:58.399
down to the sheer economics of the subscription

00:12:58.399 --> 00:13:01.600
model. Direct single unit sales are unpredictable.

00:13:02.220 --> 00:13:04.879
By forcing users to either sign up for their

00:13:04.879 --> 00:13:07.299
Safari subscription or buy the physical book

00:13:07.299 --> 00:13:09.919
from an external retailer like Amazon, they were

00:13:09.919 --> 00:13:12.460
heavily incentivizing recurring revenue. It was

00:13:12.460 --> 00:13:15.299
a calculated risk to sacrifice the single sale

00:13:15.299 --> 00:13:17.659
margin for the long term stability of enterprise

00:13:17.659 --> 00:13:20.940
subscriptions. And it clearly paid off. By 2018,

00:13:21.379 --> 00:13:24.960
they officially rebranded Safari to simply O

00:13:24.960 --> 00:13:28.200
'Reilly Online Learning. It became an all encompassing

00:13:28.200 --> 00:13:32.019
modern platform. It houses books, videos. live

00:13:32.019 --> 00:13:34.860
online training and the archives of their conference

00:13:34.860 --> 00:13:37.740
videos. They also made some strategic acquisitions

00:13:37.740 --> 00:13:41.299
to build out that platform. In 2014, they bought

00:13:41.299 --> 00:13:43.879
Infinite Skills, a Canadian publisher that made

00:13:43.879 --> 00:13:48.399
online and DVD video courses. Then in 2019, they

00:13:48.399 --> 00:13:50.799
acquired a company called Katakoda. Katakoda

00:13:50.799 --> 00:13:52.940
is a critical piece of this puzzle. Oh, absolutely.

00:13:53.279 --> 00:13:55.919
It allowed users to experiment with code directly

00:13:55.919 --> 00:13:57.879
inside the web browser while they were reading

00:13:57.879 --> 00:14:00.639
or watching a tutorial. Exactly. The shift from

00:14:00.639 --> 00:14:02.799
static reading to interactive browser -based

00:14:02.799 --> 00:14:05.539
learning is a massive paradigm shift. If you

00:14:05.539 --> 00:14:07.539
are learning a new programming language, setting

00:14:07.539 --> 00:14:09.440
up a local development environment on your own

00:14:09.440 --> 00:14:11.740
computer is notoriously frustrating. It's the

00:14:11.740 --> 00:14:14.259
worst part. Katakota removed that friction completely.

00:14:14.539 --> 00:14:17.200
It allowed O 'Reilly to offer a hands -on learning

00:14:17.200 --> 00:14:19.639
environment, which was necessary for a tech education

00:14:19.639 --> 00:14:22.779
company to stay relevant against thousands of

00:14:22.779 --> 00:14:25.700
free coding tutorials on YouTube. And this entire

00:14:25.700 --> 00:14:28.879
digital transformation happened alongside a significant

00:14:28.879 --> 00:14:31.860
shift in corporate leadership. Yeah. We are currently

00:14:31.860 --> 00:14:34.179
in the post -Tim O 'Reilly era regarding the

00:14:34.179 --> 00:14:37.460
day -to -day business. Right. Back in 2011, Tim

00:14:37.460 --> 00:14:39.340
O 'Reilly stepped down from his daily duties

00:14:39.340 --> 00:14:43.700
as CEO to focus on the Gov 2 .0 movement. The

00:14:43.700 --> 00:14:47.019
company is now run by CEO Laura Baldwin. Interestingly,

00:14:47.259 --> 00:14:49.639
she didn't come from a hardcore programming background.

00:14:49.879 --> 00:14:52.080
She brought a background in finance and consulting.

00:14:52.700 --> 00:14:55.080
Her background maps perfectly onto the timeline

00:14:55.080 --> 00:14:57.620
of their aggressive shift toward a highly structured

00:14:57.620 --> 00:15:00.720
B2B subscription model. The financial discipline

00:15:00.720 --> 00:15:02.919
required to pivot a legacy publisher entirely

00:15:02.919 --> 00:15:06.139
toward enterprise subscriptions is immense. But

00:15:06.139 --> 00:15:08.419
while the business model has modernized under

00:15:08.419 --> 00:15:10.879
her leadership, O 'Reilly still maintains one

00:15:10.879 --> 00:15:13.539
very specific philosophical quirk regarding how

00:15:13.539 --> 00:15:15.500
they handle the actual information they publish.

00:15:15.720 --> 00:15:17.940
Yeah, the way they handle their publishing rights

00:15:17.940 --> 00:15:20.139
is quite different from a traditional publisher.

00:15:20.539 --> 00:15:22.440
What's fascinating here is their approach to

00:15:22.440 --> 00:15:25.480
licensing. O 'Reilly uses the Creative Commons

00:15:25.480 --> 00:15:28.460
founder's copyright. Let's explain what that

00:15:28.460 --> 00:15:31.240
actually means. When an author signs a contract

00:15:31.240 --> 00:15:34.100
to write a book for O 'Reilly, This founder's

00:15:34.100 --> 00:15:37.100
copyright grants the company exclusive use of

00:15:37.100 --> 00:15:40.059
that author's produced content for exactly 28

00:15:40.059 --> 00:15:43.299
years. Think of it like this. Traditional copyright

00:15:43.299 --> 00:15:46.539
law locks intellectual property away for roughly

00:15:46.539 --> 00:15:49.500
a century, usually the life of the author, plus

00:15:49.500 --> 00:15:52.320
another 70 years. Right. On the other end of

00:15:52.320 --> 00:15:54.679
the spectrum, open source licenses allow you

00:15:54.679 --> 00:15:57.539
to share and remix content immediately today.

00:15:57.779 --> 00:16:00.059
O 'Reilly planted their flag right in the middle.

00:16:00.120 --> 00:16:02.850
They say, we own this exclusively. for exactly

00:16:02.850 --> 00:16:05.909
28 years and then it belongs to the world. It

00:16:05.909 --> 00:16:08.289
is a compromise between ruthless business protection

00:16:08.289 --> 00:16:11.649
and their open source ideals. It perfectly encapsulates

00:16:11.649 --> 00:16:14.350
who they are. They champion open source, but

00:16:14.350 --> 00:16:16.529
they are also a sharp business protecting their

00:16:16.529 --> 00:16:19.429
assets. Let's wrap this all up because what a

00:16:19.429 --> 00:16:21.590
journey we've just tracked. Yeah, quite a history.

00:16:21.750 --> 00:16:24.250
We started looking at an entity that began by

00:16:24.250 --> 00:16:27.620
doing private consulting in 1978. They accidentally

00:16:27.620 --> 00:16:31.480
created iconic, weird, animal -themed tech manuals.

00:16:31.480 --> 00:16:33.980
They were the first to pioneer paid web ads.

00:16:34.200 --> 00:16:37.279
They defined the era of Web 2 .0. They hosted

00:16:37.279 --> 00:16:40.200
global summits for decades. And ultimately, under

00:16:40.200 --> 00:16:42.500
the leadership of Laura Baldwin, they transformed

00:16:42.500 --> 00:16:45.320
themselves into a subscription -based digital

00:16:45.320 --> 00:16:47.460
learning empire. They've constantly anticipated

00:16:47.460 --> 00:16:50.019
where the technology industry is moving and positioned

00:16:50.019 --> 00:16:52.120
themselves right at the center of it. But before

00:16:52.120 --> 00:16:54.519
we go, I want to leave you with a final thought

00:16:54.519 --> 00:16:57.240
to mull over, specifically regarding that founder's

00:16:57.240 --> 00:16:59.419
copyright we just discussed. Let's hear it. Consider

00:16:59.419 --> 00:17:02.440
this. If a tech publisher claims exclusive rights

00:17:02.440 --> 00:17:04.579
to cutting -edge software knowledge for exactly

00:17:04.579 --> 00:17:09.099
28 years, what happens to the relevance of that

00:17:09.099 --> 00:17:11.279
heavily protected information in an industry

00:17:11.279 --> 00:17:14.579
where the technology itself completely reinvents

00:17:14.579 --> 00:17:17.440
itself every five years? It is a fascinating

00:17:17.440 --> 00:17:20.200
tension between legal protection and the rapid

00:17:20.200 --> 00:17:22.819
decay of technical relevance. That is a great

00:17:22.819 --> 00:17:25.500
point to leave off on, a 28 -year lock on a technology

00:17:25.500 --> 00:17:28.279
that might be completely obsolete in 36 months.

00:17:28.799 --> 00:17:31.099
we love giving you something to chew on after

00:17:31.099 --> 00:17:33.599
the deep jive is over thank you so much for joining

00:17:33.599 --> 00:17:35.779
us for this exploration today keep exploring

00:17:35.779 --> 00:17:38.460
keep questioning the world around you and we

00:17:38.460 --> 00:17:39.400
will catch you on the next one