Welcome in, everyone. It is great to have you
here with us for another deep dive. Yeah, really
glad to be here today. We always say that you,
the listener, are the crucial third person in
this conversation. And today, we have a topic
that is going to spark some serious recognition,
especially if you spend any time staring at a
computer screen trying to learn a new skill.
Oh, absolutely. I want you to picture a bookshelf.
Specifically, a bookshelf belonging to... Anyone
who has ever dabbled in programming or web design
or, you know, IT in general. I think I know exactly
what shelf you're talking about. Right. If you
look closely, you are guaranteed to see at least
one of these highly distinctive books. You know
the ones that usually have this stark white background.
And dead center on the cover, there is an incredibly
intricate black and white woodcut illustration
of an animal. Right, like a camel or maybe a
lemur. Yeah, or some obscure bird you can't quite
identify. It is a brilliant piece of visual branding,
honestly. You see the animal and you instantly
know the publisher. Exactly. So today's deep
dive is all about the fascinating evolution of
the company behind those covers, O 'Reilly Media
Inc. They are a company that has... quietly shaped
the entire tech landscape over the last few decades.
Yeah, and our mission for this deep dive is to
trace that specific evolution. We're going to
look at how O 'Reilly started as just a small
technical writing consulting firm way back in
1978. That's a consulting firm. Exactly. And
we'll explore how they transformed into a real
kingmaker in the tech world, how they navigated
the dot -com bust, pioneered the very concept
of web advertising, and eventually executed a
radical shift in their business model just to
start. survive in the digital age. It really
is a story of constant reinvention. And just
to set the stage here, O 'Reilly is headquartered
in Sebastopol, California. Right. But while they
operate out of Sonoma County, their influence
is totally global. They've acted as the quiet
architects behind exactly how we learn about
technology today. They don't just report on what
is happening in tech. They often define it. Totally.
And to understand how they reached that position
of influence, we really have to establish a chronological
baseline. We need to go back to 1978 in the Cambridge,
Massachusetts area. At that time, Tim O 'Reilly
started this company, but it was not a publishing
house. It was originally a private consulting
firm focused strictly on technical writing. Okay,
let's unpack this because the leap from private
consulting to global publishing empire is not
a straight line. line. No, not at all. The shift
really started happening in 1984. O 'Reilly began
retaining the publishing rights for the vendor
annuals they were actually creating for Unix
systems. They started producing these little
70 -page guides that they called nutshell handbooks.
And they were well -received, but consulting
was still paying the bills. Right. It was a side
project, basically. Exactly. The actual turning
point was in 1988. They took some preliminary
manuals for something called Exlib to a conference.
Oh, wow. Exlib. Yeah. Now, XLib was essentially
the foundational code for building graphical
user interfaces on Unix systems. And the attention
those specific manuals received at that conference
was unprecedented. I can imagine. It was the
catalyst that made them realize they needed to
seriously ramp up their book production. It was
a classic example of finding a distinct need
in a niche market and just scaling up to meet
it. But as they scaled their book production,
they needed a visual identity that would make
them stand out. on a shelf. And the story behind
those famous covers is surprisingly practical.
You might think there was some intensive corporate
branding study done to choose these specific
animals. Right. Some big agency involved. Exactly.
Yeah. But designer E .D. Friedman created the
original animal cover art for a very simple reason.
She was looking at all these strange, obscure
Unix program names, and she thought they literally
sounded like weird animals. That is so funny.
So she just started putting weird animals on
the covers. Functional design becoming iconic
by total accident. And that animal theme became
so deeply ingrained in the company's DNA that
it became their face to the world. Think about
the cover of their book on the Vi editor. Oh,
man, that notoriously complex text editor. The
one every programmer has to fight with at least
once. Yeah. The animal on that cover is a tarsier.
And that exact tarsier illustration was eventually
incorporated right into the official O 'Reilly
logo itself. It moved from being just a cover
aesthetic to the corporate identity. A weird
eunuch's name leads to a picture of a Tarsier,
which leads to a global brand logo. That is wild.
It really is. But as we move into the 90s, O
'Reilly didn't just stick to printing physical
books. Here's where it gets really interesting.
Today... We take a heavily monetized ad -driven
web as a given. Oh, absolutely. But back in 1993,
someone actually had to be the first to pull
that trigger. And ironically, it was O 'Reilly.
They created one of the very first web portals
called Global Network Navigator, or GNN. We really
need to pause and look at the historical significance
of GNN. Based on our sources, GNN was the very
first site on the World Wide Web to feature paid
advertising. That is a profound contradiction
when you think about it. How so? The company
that championed open source ideals and free information
is the exact same company that created the ad
-supported monetization model of the modern Internet.
Yeah, that's a wild juxtaposition. But they didn't
hold onto it for long, right? Right. By 1995,
they sold GNN to AOL. Why get out so early when
the internet was just starting to take off? Well,
it was likely a matter of recognizing their core
competencies versus where the web was heading.
The sale to AOL in 1995 occurred right during
the early swell of the dot -com bubble. It was
one of the first really large transactions of
that era. They capitalized on their early foresight
and secured funding that would allow them to
focus heavily on their broader ambitions in publishing
and community building. Of course, the dot -com
bubble eventually burst and the whole industry
History took a massive hit. Yeah, it was brutal.
Fast forward to 2003, and the landscape was pretty
grim. People were writing off the internet as
a failed experiment. This is where Tim O 'Reilly
and Dale Daugherty stepped in with a very specific
goal. They wanted to reignite enthusiasm in the
computer industry. They needed a way to signal
that the Internet wasn't dead, it was just evolving.
Right. To do this, they popularized a term you
have definitely heard, Web 2 .0. Oh, yeah. Now,
to be precise, the term was originally coined
back in January 1999 by a writer named Darcy
DiNucci. Right. We should give credit where it's
due. Exactly. But O 'Reilly and Daugherty took
that term and used it as the banner for a major
summit they were co -producing with TechWeb,
which was formerly known as CMP Media. Web 2
.0 became the ultimate buzzword. It was everywhere.
But what did it actually mean in practice? If
we connect this to the bigger picture, Web 2
.0 was a crucial framing device. It was used
to distinguish the companies that survived the
dot -com bust from the ones that disappeared.
Makes sense. More importantly, it identified
the key drivers of future success. It put a name
to concepts that are foundational today. Things
like cloud computing, big data, and new approaches
to iterative, data -driven software development.
It was effectively a roadmap out of the bust.
But whenever you create a highly visible buzzword,
the lawyers eventually get involved. Naturally.
There was some serious drama surrounding the
term Web 2 .0 in May of 2006. CMP Media, who
co -produced that Web 2 .0 summit with O 'Reilly,
had actually registered Web 2 .0 as a service
mark. Right. Just to clarify for everyone, a
service mark is essentially a trademark, but
it specifically protects services like live events
and conferences rather than physical products.
Good distinction. Well, an Irish nonprofit decided
to run a small Web 2 .0 half -day conference.
Just a little half -day event. Exactly. And CPU
Media caught wind of this and sent them a full
-blown cease and desist letter. It was a very
heavy -handed corporate move against a nonprofit.
And it generated immediate backlash online. It
clashed directly with the open, collaborative
ethos that O 'Reilly was known for championing.
O 'Reilly had to step in to do damage control.
They apologized publicly. for the aggressive
early involvement of attorneys, noting that someone
should have just picked up the phone and called
the organizers instead. Which is how you'd hope
things would work. Ultimately, they allow the
nonprofit to use the service mark for that single
event. That incident is a great lesson in community
management. You have to protect your intellectual
property, but you absolutely cannot alienate
the very developers who make up your core audience.
And O 'Reilly wasn't just defending Web 2 .0
in the courtroom. They were literally building
the rooms where these developers gathered. Which
brings us to their leap into live events. Yes.
Roughly two decades into their existence, they
expanded heavily into event production, running
conferences from 1997 all the way up to 2020.
It started in 1997 with the Perl Conference.
Initially, it was just a smart way to cross -promote
their books on the Perl programming language.
But then, in 1998, they did something truly visionary.
They invited leaders from various software projects
to a single meeting. They originally called it
the Freeware Summit, but it soon became known
as the Legendary Open Source Summit. They were
bringing together rival factions of the open
source world and just getting them to talk to
each other. Exactly. They became famous for their
flagship events. You had OSCON, the O 'Reilly
Open Source Convention. You had the Strata Conference,
which was laser focused on big data. They ran
the Velocity Conference for web performance and
the highly exclusive FOO Camp. This raises an
important question about how O 'Reilly viewed
their role in the industry. They eventually stated
that they didn't view their business as just
publishing or just running conferences. Right.
Their stated goal was changing the world by spreading
the knowledge of innovators. They viewed themselves
as the central nervous system for tech knowledge.
And they didn't just limit this philosophy to
software either. They took a fascinating detour
into the world of hardware and DIY culture with
the maker movement. That was a huge shift. In
January 2005, O 'Reilly launched Make Magazine.
And the very next year, in 2006, they launched
the Maker Faire. The scale of these events was
staggering. It really was. The flagship Maker
Faire in San Mateo, California, drew over 130
,000 attendees. It was a massive celebration
of physical invention, craft, and engineering.
They tried to expand that DIY ethos into other
areas as well. In the fall of 2006, they launched
a second magazine called Craft with the tagline
Transforming Traditional Crafts. However, that
publication folded by 2009. But the core maker
brand was successful enough that in 2012, O 'Reilly
Media spun out the make properties into a completely
separate venture -backed company called Maker
Media. Right. It was headed up by Dale Dougherty,
the former O 'Reilly executive who actually helped
coin Web 2 .0. The Maker Media story has a difficult
ending, unfortunately. Despite the massive cultural
impact and millions of people attending fairs
globally, the financial model eventually collapsed.
Yeah, that was tough. In the summer of 2019,
Maker Media laid off its staff and ceased operations.
It is worth noting, though, that Make Magazine
itself survived and is currently published by
a different entity, Make Community LLC. It was
a heavy blow to that community. And it was somewhat
of a harbinger for... O 'Reilly's own live event
business. Because in March 2020, an earthquake
hit their business model. O 'Reilly announced
they were permanently closing the entire live
conference's arm of their business. Decades of
legendary tech summits came to an abrupt end.
It was a monumental shift. But O 'Reilly survived
that sudden loss of their event empire because
they had spent the previous two decades quietly
building a robust digital infrastructure. So
what does this all mean? Think about how you
consume information right now. You stream it.
You subscribe to it. O 'Reilly saw this coming
way back in 2001. That is the year they launched
Safari Books Online. It was a subscription -based
service providing access to e -books and videos,
and it originally started as a joint venture
with the Pearson Technology Group. They were
so far ahead of the curve on the subscription
model for technical education, and as the years
went on, they strategically doubled down on it.
In 2014, O 'Reilly acquired Pearson's entire
stake in Safari Books Online, making it a wholly
owned subsidiary. They redesigned the site and
heavily expanded their focus outward. They pushed
hard into the B2B enterprise market, basically
getting corporations to buy subscriptions for
their entire engineering teams. And then in 2017,
they made a business decision that seems incredibly
risky on paper. They completely stopped selling
single books online. including e -books. Completely
cut it off. Taking away the ability to just buy
a single book online seems like corporate suicide
for a publisher. How did they justify cutting
off a proven revenue stream like that? It comes
down to the sheer economics of the subscription
model. Direct single unit sales are unpredictable.
By forcing users to either sign up for their
Safari subscription or buy the physical book
from an external retailer like Amazon, they were
heavily incentivizing recurring revenue. It was
a calculated risk to sacrifice the single sale
margin for the long term stability of enterprise
subscriptions. And it clearly paid off. By 2018,
they officially rebranded Safari to simply O
'Reilly Online Learning. It became an all encompassing
modern platform. It houses books, videos. live
online training and the archives of their conference
videos. They also made some strategic acquisitions
to build out that platform. In 2014, they bought
Infinite Skills, a Canadian publisher that made
online and DVD video courses. Then in 2019, they
acquired a company called Katakoda. Katakoda
is a critical piece of this puzzle. Oh, absolutely.
It allowed users to experiment with code directly
inside the web browser while they were reading
or watching a tutorial. Exactly. The shift from
static reading to interactive browser -based
learning is a massive paradigm shift. If you
are learning a new programming language, setting
up a local development environment on your own
computer is notoriously frustrating. It's the
worst part. Katakota removed that friction completely.
It allowed O 'Reilly to offer a hands -on learning
environment, which was necessary for a tech education
company to stay relevant against thousands of
free coding tutorials on YouTube. And this entire
digital transformation happened alongside a significant
shift in corporate leadership. Yeah. We are currently
in the post -Tim O 'Reilly era regarding the
day -to -day business. Right. Back in 2011, Tim
O 'Reilly stepped down from his daily duties
as CEO to focus on the Gov 2 .0 movement. The
company is now run by CEO Laura Baldwin. Interestingly,
she didn't come from a hardcore programming background.
She brought a background in finance and consulting.
Her background maps perfectly onto the timeline
of their aggressive shift toward a highly structured
B2B subscription model. The financial discipline
required to pivot a legacy publisher entirely
toward enterprise subscriptions is immense. But
while the business model has modernized under
her leadership, O 'Reilly still maintains one
very specific philosophical quirk regarding how
they handle the actual information they publish.
Yeah, the way they handle their publishing rights
is quite different from a traditional publisher.
What's fascinating here is their approach to
licensing. O 'Reilly uses the Creative Commons
founder's copyright. Let's explain what that
actually means. When an author signs a contract
to write a book for O 'Reilly, This founder's
copyright grants the company exclusive use of
that author's produced content for exactly 28
years. Think of it like this. Traditional copyright
law locks intellectual property away for roughly
a century, usually the life of the author, plus
another 70 years. Right. On the other end of
the spectrum, open source licenses allow you
to share and remix content immediately today.
O 'Reilly planted their flag right in the middle.
They say, we own this exclusively. for exactly
28 years and then it belongs to the world. It
is a compromise between ruthless business protection
and their open source ideals. It perfectly encapsulates
who they are. They champion open source, but
they are also a sharp business protecting their
assets. Let's wrap this all up because what a
journey we've just tracked. Yeah, quite a history.
We started looking at an entity that began by
doing private consulting in 1978. They accidentally
created iconic, weird, animal -themed tech manuals.
They were the first to pioneer paid web ads.
They defined the era of Web 2 .0. They hosted
global summits for decades. And ultimately, under
the leadership of Laura Baldwin, they transformed
themselves into a subscription -based digital
learning empire. They've constantly anticipated
where the technology industry is moving and positioned
themselves right at the center of it. But before
we go, I want to leave you with a final thought
to mull over, specifically regarding that founder's
copyright we just discussed. Let's hear it. Consider
this. If a tech publisher claims exclusive rights
to cutting -edge software knowledge for exactly
28 years, what happens to the relevance of that
heavily protected information in an industry
where the technology itself completely reinvents
itself every five years? It is a fascinating
tension between legal protection and the rapid
decay of technical relevance. That is a great
point to leave off on, a 28 -year lock on a technology
that might be completely obsolete in 36 months.
we love giving you something to chew on after
the deep jive is over thank you so much for joining
us for this exploration today keep exploring
keep questioning the world around you and we
will catch you on the next one