Tim O'Reilly
Appearances
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
was like you might be running on a digital machine. You might be running it on a data general machine. You might be running on a prime machine. You might be running it on a Burroughs B20. So you had to have source code. And so the source code culture grew up around Unix.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Yeah, yeah. But anyway, so the point was I kept thinking about all this and it kept taking me further and further down the path into thinking about networks as the center. And so then after the dot-com bust, I started noticing, I ran a conference in 2001 where called building the internet operating system, which is again, a kind of pattern recognition.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I said, increasingly the internet is becoming the platform.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I think of it more in this image of one image I've used in trying to explain it to people. It's like you're doing a jigsaw puzzle, which is a pattern recognition exercise again. but all the pieces aren't on the table. And then somebody dumps another 100 pieces on the table, and you sort them through, and then suddenly you can see a piece of the pattern you couldn't see before.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
In the case of Web 2.0, I had been going down this path of trying to talk about the internet as the platform. And then Dale was the one who came up with this notion of Web 2.0. I had run this series of conferences. I had started with really this notion that in my building the internet operating system, there were three things that had landed on me at the same time. And one was,
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
distributed computation, which was through applications like SETI at home. You may remember that, whereas people were using, they would basically put a piece of software on your PC, so you'd have distributed computation running across thousands or tens of thousands of PCs.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
It was the era of Napster, where basically, instead of having all the songs in one place, everybody would be serving them up to each other. So that was the whole peer-to-peer movement. And then there was the very beginnings of web services. Basically, these were all the same thing.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
They were all people who were starting to see the internet itself as the platform and it break out of the paradigm that software just lived on a device. And then the piece that clicked it into Web 2.0 was Dale had tried to put together a conference with another company that used to run Comdex and they wanted to do something with us and we wanted to learn
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
from somebody else who had been doing the business longer than we had. So we said, oh, let's do a joint venture and launch a conference together. And Dale's the one who came up with calling it Web 2.0. If you read the What is Web 2.0 paper, it's basically this one table in the beginning, which was where Dale was saying, here was Web 1.0. You're going to be a portal. You're going to aggregate.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Web 2.0 is syndication. It was a bunch of things that we did a set of comparisons. And then I kind of, brought in all of my ideas about the internet as operating system and fleshed that out to tell a story about what was really going on.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
We were in an expansive period and that was before, but it was again, a pattern recognition exercise. It was really triggered by the fact that I had become friends with a guy named Andrew Shulman. Again, you just hear these people just drop a piece on the table. And it was in the early days of a Microsoft technology called ActiveX.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And Andrew had written a book called Undocumented DOS and Unauthorized Windows 95. He was an author for a different publisher, but he eventually came to work for me because I decided to try to do some Windows-based books. And he told me about this national advertising campaign by Microsoft about ActiveX. We're activating the internet.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And he said, actually, everything in that commercial, except the little animated taxicab that was going across the screen, was done with Perl. And I was outraged because Pearl, of course, was our best-selling book. And I kind of got outraged. And it was also right after Sun had introduced the Java 1 conference, this massive Java conference. And I go, wait, there's no conference for Pearl.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So I decided to throw a party for them. And it was really kind of this idea of it would be, in some sense, a kind of subsidized marketing. I didn't really think of it as a business. It was really like, oh, Sun is marketing Java. We could do something for these people who've given so much to us.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And then I realized, oh, wait, all of our bestselling books are about, which is what led me up to the Open Source Summit the next year. And maybe it gave you another piece of how reading and literature and the kinds of things that shape your personal philosophy. There's two books I'm going to mention. One is a book from the 1930s called The Meaning of Culture by a guy named John Cooper Powers.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
He was a Welsh author and lecturer. And The meaning of culture is about the difference between what he calls culture and education. And he said, culture is the education that you put to use in your own life, your personal culture. That became a lens for me.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And the other thing I was going to tell you about as a piece of personal culture is this fabulous scene in the Canadian television production of Anne of Green Gables, which I watched with my daughter when she was 10. and came to love those books. The story of Anne of Green Gables is an orphan who is adopted by this elderly brother and sister.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
The brother is sent to get this orphan, and he accidentally brings home a girl instead of a boy. And his sister says to him, a girl? What use could she be to us? Richard Farnsworth is the actor. And Richard Farnsworth sang in this slow, kind of thoughtful way. He said, well... I was thinking maybe we could be of some use to her. It's just such a beautiful line. And it went right in.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So why did I do the Pearl Conference? I thought we could be of some use to this community. And this kind of goes to entrepreneurship. We've perverted the idea of entrepreneurship, I think, in Silicon Valley. It's become about this is this way to get rich. And there's always been a thread of it. But there's also this essential thread that we forget at our peril, which is- Right.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And it's this thing. Oh, wait, there's this opportunity to be of some use. So the opportunity to serve is also the opportunity to profit, because if you serve customers and they pay you for what you do. that becomes a business.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
But this whole idea that now the whole game is, it reminds me a lot more of the mortgage business before the big crash of 2007 than it ought to, where the idea is what we're really trying to do is create a financial instrument that we can sell to other investors. And yeah, and it's so driven by growth and so on and the whole blitzscaling idea of
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
If we can tell a story that gives us a higher and higher valuation, we can eventually walk home with a ton of money, even if the business isn't sustainable. You look at WeWork as an example of that.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I think it's a sickness in our entire economy that you can make so much more money by financializing a business than by delivering value to customers. So again, there are absolutely cases where you need to raise a ton of money. Think about Tesla building out the supercharger network, or thinking about Amazon building out its warehouse and delivery infrastructure.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
But it's really interesting because Jeff Bezos actually understood that because he was actually delivering value to customers, he was getting their money up front. He didn't actually raise that much money. He borrowed a ton of money. Amazon was funded with debt. And I had that once. Our version of venture capital tended to be joint ventures.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I built my international business in joint ventures with a company called International Thompson. And then I bought them out at some point. When we started the first web portal called the Global Network Navigator, we sold to AOL and we had a joint venture with them on the first content side of the web, something called Songline Studios, a content studio. We eventually bought them out.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And in a similar way, we started this, what we called Safari Books Online with our biggest competitor starting in 2000. And then in 2014, we bought them out. Essentially, because I had a conversation, I thought, oh, well, we'll have to take some venture capital. And I talked to an old friend of mine who was a private equity guy.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And he said, I'd love to invest in your business, but why wouldn't you do this with debt? We had cash flow from the business, positive cash flow. So we ended up buying it with a loan. So I think there's a bigger palette of financing opportunities if you're not thinking your goal is to exit, but to actually build and run a business.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
But so much of Silicon Valley, it's like you start the company with the idea that you are going to sell it, sell it as fast as possible for as much as possible. And occasionally, people are really clear, I want to build this as a business, but not often enough.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Because I was always self-financed, the business was always, does this make more money than it costs to do it? And eventually you get some scale that allows you to place some bets. But in a lot of ways, the book publishing business is you're continually investing. You're spending a chunk of money to develop a book. You buy a bunch of inventory, and it might not sell. But on average, they do.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
A conference, if you do it right, you put out a bunch of money up front, but you get it back not long after. And so we've tended to be in those kinds of businesses. Now, we did, for example, build GNN back in when we started it. We launched the whole Internet Users Guide in 1992, and then we launched GNN, which is the first web portal in 1993.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And for two years, we put every penny of company profits. We spent a third of our revenue on this thing that had no profits, that we didn't know what it was, but we thought it was really important. And eventually I sold it. And the reason I sold it was actually because it was, again, it was pattern recognition. I had read a book by Ron Davido called Marketing High Technology.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Oh, thank you for having me. And I'm glad that the books didn't put you off and that you kept going.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And he had an appendix in which he talked about what he called the math of market domination. And he said, in order to dominate a market, you have to be at least half the market and growing faster than the market as a whole. And I thought, oh, there's no way we can do that without taking in massive amounts of capital. And I don't want to do that.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And the reason I didn't want to do that was because of my experience a decade earlier as a consultant. working with, I mean, it was more than 15 years earlier, working with all these startups that turned out to be very boring and unpleasant companies, you know, that were idealistic and whatever. And then they became just like everybody else. I didn't want to be like everybody else.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Let's just stop in my experience. Yes, it's true. But this notion that it's always you're taking your big investment, big risk, big swing, win big or go home is just part of the myth of Silicon Valley. For thousands of years, people have started businesses with whatever they can scrape together. They scrape by, and some of them are good at it, and they basically grow bigger.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Our first books that we published My first print run of my first book was 100 copies, and they cost us a dollar, and we sold them for $5 each. And we went, oh, that worked. Let's print some more. It does not have to be a big swing, and you just bit by bit. You know, it's a little bit like Annie Lamont's wonderful book about writing. It's called Bird by Bird.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
It is. Actually, most of them are a lot of small swings. I mean, yes, there are big things that we invest in. But relative to the scale of the company, they're not big. They're not betting the company big. Now, again, in one sense, you're always betting the company because the collection of all the things you do, even if they're small, add up to the company that you become. Right.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And you have to pay attention to it. One of the things I wrote once is probably the thing of mine that's been probably repeated as much as anything on the internet. I said, money in a business is like gas in a car. You have to pay attention to filling the tank, but you are not making a tour of gas stations when you go on a road trip.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
In business, you should have a purpose that's bigger than money. And if you do, then you're just trying to find a way to finance that purpose. It's a very different approach than if you think your job is to make as much money as possible. If you think your job is to do something, you find ways to make it happen.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I've been semi-retired for the last 10 years and AI has got me back in founder mode for two reasons. One, it's an existential threat to our business. You know, I do think that there's a lot of new capabilities and basically the AI companies have basically been pretty ruthless in stealing everybody's content and basically making
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
products that effectively compete with the people whose content they trained on. That means we have to think about, well, what's our value beyond replacement? And we have a lot of ideas about that and we're doing some great new products, but it's also calls for kind of some of the things that I've always been It's been a big part of what I do in the past, which is storytelling.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Certainly reading. I was a total nerd. I basically, I lived very close to my school, less than a block away. We had an hour for lunch and I ran home and spent the entire time reading books. So I was not terribly well socialized. I was fairly blind and my older brother had this idea that if we wore our glasses, we'd become dependent on them.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So one of the things that's been a threat to our business is there's been a whole narrative out there that we're not going to need programmers anymore. O'Reilly is primarily an enterprise learning service that we sell to corporations. I mean, we do still sell books and so on, but the biggest part of our business is a subscription.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So these corporate learning buyers are like, hey, everybody's telling us we're not going to need developers anymore. And so I go, well, A, it's wrong. And B, I want to tell you why. I just organized a four-hour virtual conference. We had something like 22,000 people sign up.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And we told the story of why AI actually still requires programmers to change their job, which, of course, for our business is a good thing because they actually have to learn new skills or double down on skills that we're undervaluing. Chelsea Troy, for example, is one of our computer science professor and one of our experts who does stuff for us on the platform, gave this fabulous talk.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And he said, look, we have this incredible mismatch between the idea of what a programmer does and what they actually do and how we teach them. We try to teach people to write code from scratch. And then once they get out in the real world, most of their work is actually fixing code that was written by someone else. And now, you know, with AI, maybe it's gone from 80% to 96%, you know.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
But it's not as big a gap as you think. And we've always had to teach people the skills of how do you actually think through a problem? How do you actually figure out whether the code is doing what you thought it should do? Again, one wonderful quote from a friend in the past, a guy named Andrew Singer, told me this wonderful line once. I was working on a manual.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
It was the first C compiler for the Mac, ThinkC. It was called LightspeedC originally. And Andrew... Drop this line, which I've treasured. He said, the skill of debugging is figuring out what you really told your program to do instead of what you thought you told it to do. When you think about that, what did you really tell your LLM to do? It's still true. You've got to figure out.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
We've got this wonderful piece recently by Philip Carter at Honeycomb who wrote about LLMs are weird computers. We now have two computers really, two full computers that have to be brought together. One of them can write a sonnet but can't do math. And the other one can do math, but couldn't write a song no matter what you did to it.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Programming is now getting the best out of these two systems, not just one. So it's like this amazing time to be helping to figure out what does programming look like today? What can we do with these machines? And I'm super excited about it, and we're figuring it out and teaching it. Yeah.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I wrote a piece on LinkedIn many years ago called How I Failed. And there were a set of things that I put in there that I learned too late. One of them was that as an entrepreneur, you need to value the financial people. I know a lot of entrepreneurs who fail because they don't pay attention to their numbers.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Yeah, yeah. And, you know, I tell some stories about things that because I didn't, that do that well enough. You know, I had to make suboptimal choices because I had not given myself the optionality. So get a great CFO until actually she's no longer my CFO, but when I hired in 2000, I was always the best financial person in the company.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
You know, my CFOs, I was, I would go, Hey, there's something wrong with that number. And they go, why? And I go, well, because I had developed my own kind of financial reporting system. And a lot of it was like what percentage, every expense, what percentage was it of total sales? And so I could see, again, it was a pattern matching kind of thing for me.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So I did not wear, even though without my glasses, I was the equivalent of legally blind. And I didn't wear them until I was in high school. I basically wore them when I suddenly, you know, you're in high school and you start having friends and people would say, hi, Tim. And I was like, who was that? And I would turn around and try to figure out who it was who just said hi.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So I go, wait, so I go, there's something wrong with that number. And they would say, well, how do you know? And I'd say, well, because it's normally it's 0.35% of sales and suddenly it's 2% of sales. So you either have an error or something happened. You need to tell me what it is. Finally, I got somebody who was better than I was. And I went, great. I don't have to do that anymore.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I used to literally carry with me at all times, this set of financial reports, because I was always, I was the one who had to really be monitoring the health of the business. So hire people who compliment you. So that's probably one of those big pieces of advice. And the other thing, and this is probably more relevant for me as an entrepreneur at my age,
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
You have to understand that at some point you're going to have to let go one way or the other. So you have to think about succession. You have to think about who takes up the reins from you and how to teach people to do what you do and all those kinds of things.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I wouldn't call it an empire. I would call it a small island nation.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Well, that's, again, one of our things that we always say, create more value than you capture. That came to us back around 2000. I was telling a story at a management meeting and I won't name the names. There were a couple of early internet billionaires who told me that they started their company with an O'Reilly book. Thank me for it.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I was telling the story and I laughed and I said, yeah, we got 35 bucks. That's pretty awesome. Yeah, and I think it was Brian Irwin, the guy I mentioned earlier, he said, we create more value than we capture. And we immediately said, oh, that's a great slogan. It should be our goal. It should be the goal of every business to create more value than you capture.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And if you follow Cory Doctorow's work on enshitification, you understand that companies lose the plot on that. They stop saying we have to create more value than we capture. The market slows down and suddenly they're going, actually, we have to take out more than we put in because we have to keep growing. And that's just wrong.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
We actually have to keep reinventing ourselves so that we keep creating more value than we capture so that the system itself can continue.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I feel like kind of an old fart kind of telling stories of 20, 30 years ago, but... We could have thought probably more about interesting parts of the AI future, but we'll figure it out. We just have to remember that we should be using AI to solve new problems and not just to put people out of work.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And I realized, my gosh, that was the stupidest advice from my brother ever.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Yeah, well, I would keep them in my pocket and I would put them on when I needed to see the blackboard. But it definitely... Hurt my sports career. I didn't really take up sports until I was in my 30s. That's when I learned to play basketball and soccer.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
My only jobs before I started my own company, I had been a janitor at a home for the mentally retarded. Ha! I had been a cemetery caretaker at Arlington National Cemetery, mowing lawns. And I'd been a dishwasher in a deli that we referred to as the greasy spoon. Those are my three jobs, right? And then I had a student job at Harvard and a student job being a janitor. But I never had any other job.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I came out of college and I basically did this work on George Simon's notebooks. And then I got this Frank Herbert book to write. And then because I have this connection with this friend who got asked to write a manual, I just said, I'll help you out.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I've never had a job. And of course, the original business became a consulting business. So work was very precarious anyway. The book business, as we know today, actually started in 1985. When there was a big downturn in our consulting business, and I had maybe 12 employees at that point, but we were all contractors. I was the only employee.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I just basically had work for people when I had work for them. But because I didn't want to just turn them out on the street, I said, well, while between jobs, let's write some manuals of our own. So we started looking around and we go, oh, there's no manual for this. There's no manual for that. People will buy it.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Money in a business is like gas in a car. You have to pay attention to filling the tank. In business, you should have a purpose that's bigger than money. And if you do, then you're just trying to find a way to finance that purpose.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So we produced a few of these things and they caught on and the rest is history, as they say.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I think that's super interesting. And it really eventually shaped what my partner, Bryce Roberts, did at Alpha Tech Ventures with Indie VC, was to look for businesses where the funding comes from customers. We got our funding from customers. That's what I'm asking.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Bryce told a fabulous story about the founders of RX Bars, those fitness bars. And it was two friends and both of their parents were immigrants in the restaurant business. And they came home one day with their business plan. They were going to grab venture capital for this fitness bar.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And the father, who was this very different generation of entrepreneur, starting a restaurant or whatever, he says, forget about that. Go out and sell some bars. Yeah. And they did. And they formulated themselves. They lucked into this. They figured out they could piggyback on CrossFit. And they ended up building a business which they sold for $800 million with no VC.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I started my company with $500. And everything else came from customers. There was one exception, which is in that period when we nearly went out of business. My mother gave me a $10,000 loan. And then a few years later, she said, hey, do you still need that money? I'd like to give it to your brother so he can buy a house. It was an interest-free loan.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Yeah, dot-com bust. I lost a lot of my hair then.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
The toughest time for us was with the dot-com bust. We had just moved into a new building, new complex of buildings. We had tried to leave space for growth, so it was too big for us already. We tried to move in about two-thirds full, and suddenly our revenues dropped, I think, in one year from $70 million to $50 million. It was pretty brutal, and we had to do layoffs.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I had always run a very paternalistic company, and I still remember it. I was sitting there poring over the lists of people who were trying to figure out who to lay off. And I have a binder with all the names. And we were probably 300 or 400 people at the time. I had to let go of 100 people. And I suddenly, I go, why is there all this hair on my binder? Wow.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I mean, literally, my hair was falling out. I was so stressed. Not only that, I then didn't get paid myself for a couple of years. because we had some debt that I had to basically sign a personal guarantee on all the business debt. So it was pretty, pretty rough.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
I didn't think about it as having to motivate myself to get through it. I remember once reading Sir Joshua Slocum's book about sailing around the world solo. He's in a big storm and he's lashed himself to the wheel. It goes on for like several days. It's like, if I fall asleep, if I let go, I will die. And at first he said, I can make it through another hour, another day or whatever.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And then it's like, I can make it through another hour. And then ultimately I can make it through another minute. And I was just like, okay. It just never occurred to me that there was an alternative to to going forward. I don't know, partly because I felt enormous responsibility to all the people who worked for me.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And I guess that's something also that just, there were two books that I read when I was a teenager that really shaped my view of leadership. One was Dune, which of course I had read it when I was 13 or 14. I later got to meet Frank and write a book about him and his work. But there's a scene early in Dune where
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Paul's father goes down to, you probably remember if you saw the movies recently, he goes down to rescue the men in the stranded in the spice crawler. And the people are all amazed to see that he risks his own life for his people. And it's just in the book, it's just super clear. That's the compact of leadership. And I probably had gotten that even, I don't remember which one I read first.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
My only jobs before I started my own company, I had been a janitor at a home for the mentally retarded. I had been a cemetery caretaker at Arlington National Cemetery, you know, mowing lawns. I started my company with $500. Win big or go home is just part of the myth of Silicon Valley.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
It was a wonderful historical novel called The Golden Warrior by Hope Muntz about Harold, the last of the Saxon kings. And if you don't know the history, he had had a huge battle up in the north of England with the Vikings who'd invaded with his half-brother, Tostig, and he fought them off. And then William invades in the south. And everybody's saying, you've got to regroup, you've got to regroup.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And at least as told in this novel, he was like, that's not the deal. These people follow me and I protect them, that is the deal. And so he basically went south to his death, right? And it's a beautiful story. And it just totally shaped my idea of what it meant. So these people are choosing to follow me and I owe them a duty of loyalty.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And I kind of had this idea of a company as a pact of mutual loyalty. Of course, not at all how people think of it these days, but that was sort of my root version of entrepreneurship and leadership. It was probably very tribal in a sense. You kind of go, I've got to bring down the mammoth, you know, because we're starving. And so we just tried different things.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Two years after the dot-com bust, we were still hurting. But our strategic goal for that year was how do we reignite enthusiasm in the computer industry? Because everybody was like, it's over. And that's when I basically told the story of Web 2.0. Why did some companies survive the dot-com bust? Why Google? Why Amazon? Why did they flourish when so many other companies died?
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And I tried to tell a story about that. And then, of course, everybody went, oh, now we understand. The principles of this new era are collective intelligence, big data, what I called at the time, we now call it cloud computing. I called it software above the level of a single device. When I wrote that, what is Web 2.0 paper, it just catalyzed the industry.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
No, my colleague Dale Doherty, who was one of the first people that I hired at O'Reilly, coined it. I had been writing, and this again goes to this notion of how maps and terms and language emerges. So when I convened in 1998, which is six years earlier, the meeting that came to be called the Open Source Summit, because that's where a group of free software leaders agreed to use this new term.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
For thousands of years, people have started businesses with whatever they can scrape together, and they basically grow bigger.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
My first piece was this pattern recognition thing. I'd been concerned about this notion that the free software narrative that was being told by Richard Stallman and the Free Software Foundation was just wrong because I go, wait, wait, how can you be talking about free software and not talk about the World Wide Web, which was put into the public domain?
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
But anyway, so the point was I told this new story that the internet, not the Free Software Foundation and Linux should be the heart of this story. And it really changed the arc of that narrative. I'd also learned early on this great trick from this guy, Brian Irwin. What he really taught me was advocacy as marketing. Tell a big story.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
When we published the book, you know, he said, we're going to go on tour. And he said, but people don't care about the book. They care about the internet. We use the book to market the internet. We didn't try to market the book.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So then five years after that, here I am at the open source meeting. And I organized, you know, I got a lot of press attention. contacts through this period of being an advocate for the commercialization of the internet. And so I invite them in and I have a set of people. I go, well, what's the most mission critical program on the internet? And they're scratching their head.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
They've not heard this story before. And I say, I'd memorized the IP address for the New York Times and the Wall Street Journal and whatever. And I said, yeah, why do you get to call yourself newyorktimes.com instead of whatever their IP address was. And it goes, this guy over here, he wrote and has been maintaining for the last 15 years, this software called the domain name system, right?
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
and this program called Bind, the Berkeley Internet Name Demon. Okay, you send email. It's this guy here. He wrote this. I went down the list, and I kind of finally, about number five, I got to the line of store walls, you know, talking about Linux. And I said, you're able to do all these things because of this software that was created and given away by these long-term developers.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Yeah. A month later, Linus was on the cover of Forbes. There was a spread of all these guys' full-page photos inside and changed the narrative. But here's the thing. The narrative was still wrong. Most people don't really remember this ancient history, but... Everybody still was focused so much on that open source was about licenses.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
And my pattern recognition sense was like, that's just wrong because I lived the open source story through the early part of my life with Unix, which was basically this community had grown up under the proprietary license from AT&T. And you had Berkeley Unix, the Berkeley version, I was a Berkeley Unix guy more than a Linux guy. And it was this community that was happening.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
So I went, oh, this is really about recentering on the internet. It was really about internet-enabled software development was really at the heart of this. And it was also about something that I called the architecture of participation. It was something about the design of Unix itself that made open source possible.
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Three things. One was...
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
and so it was even going back to my first experience with the documentation problem you actually had to give source code there was a big freeware community on say back when i first got my first computer which was a personal computer which was an osborne there was this the bog live osborne user group library you know where you got all this fabulous free software it was all binary but unix it was all source code because the underlying architectures