Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
Thu, 29 May 2025
Tim O'Reilly’s entrepreneurial journey began with odd jobs like being a janitor, cemetery caretaker, and dishwasher. With just $500, he founded O'Reilly Media, initially focusing on publishing tech manuals. After a major setback during the dot-com bust, which saw revenue drop by $20 million, Tim continued building his business and creating a huge impact in the tech world. His work with Web 2.0 and open-source technologies like Linux and Perl helped position O'Reilly Media as a key player in the internet’s evolution. In this episode, Tim shares how he built O'Reilly Media from the ground up, navigated industry shifts, and why focusing on value is essential for long-term business success. Tim O'Reilly is an entrepreneur, author, and the founder of O'Reilly Media, a leading tech publishing company known for its groundbreaking books, conferences, and online learning platforms. In this episode, Ilana and Tim will discuss: (00:00) Introduction (02:29) Growing Up with Poor Vision and a Love for Books (03:53) Building O'Reilly Media with Just $500 (07:07) Leadership Lessons from the Dot-Com Crash (11:32) How Web 2.0 and Open Source Transformed the Web (19:27) The Problem with Silicon Valley’s Business Model (26:15) Scaling a Business with Limited Resources (31:11) AI and the Future of Programming (35:11) Tim’s Key Lessons in Entrepreneurship (37:47) Why Every Business Should Prioritize Value Tim O'Reilly is an entrepreneur, author, and the founder of O'Reilly Media, a leading tech publishing company known for its groundbreaking books, conferences, and online learning platforms. A key figure in the evolution of the internet, Tim played a major role in popularizing tech concepts such as open-source software and Web 2.0. He has been a strong advocate for ethical technology and continues to explore the future of AI, programming, and innovation. Connect with Tim: Tim’s Website: oreilly.com Tim’s LinkedIn: linkedin.com/in/timo3 Resources Mentioned: The Whole Internet User's Guide & Catalog by Ed Krol: https://www.amazon.com/Whole-Internet-Users-Guide-Catalog/dp/1565920635 Sailing Alone Around the World by Joshua Slocum: https://www.amazon.com/Sailing-Alone-Around-Joshua-Slocum/dp/0486203263 Dune Mass Market by Frank Herbert: https://www.amazon.com/Dune-Frank-Herbert/dp/0441172717 The Golden Warrior, the Story of Harold and William, a Novel of the Norman Conquest by Hope Muntz: https://www.amazon.com/Golden-Warrior-Harold-William-Conquest/dp/B001DA6IKC Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: How did Tim O'Reilly start O'Reilly Media with just $500?
Tim O'Reilly is a true pioneer in the tech world. As the founder of O'Reilly Media, he played such a crucial role in evangelizing the World Wide Web, the Perl programming language, Linux, open source, so many others.
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.
For thousands of years, people have started businesses with whatever they can scrape together, and they basically grow bigger.
Chapter 2: What leadership lessons did Tim learn from the dot-com crash?
How do you keep growing in terms of expanding to the conferences and to venture capital and investment?
Three things. One was...
Today I have a really fun episode. It's extra fun for me. It's gonna be amazing for you. And I want you to listen because when I got into Intel, the very first job I ever had, I was put in front of this big pile of books And apparently they were all Tim O'Reilly here and just so excited to have him on the show with us.
So Tim O'Reilly is a true pioneer in the tech world, is someone that didn't just ride the wave of innovation, but helped define it. And to me, it's just so interesting because as the founder of O'Reilly Media, he played such a crucial role. in evangelizing the World Wide Web, the Perl programming language, Linux, open source, so many others that we're going to talk about.
Chapter 3: How did Web 2.0 and open source transform the web?
But O'Reilly Media is expanded into online publishing and conferences and magazines and early stage ventures, investing, et cetera. And I'm just so excited for you to hear this incredible, incredible journey. So Tim, thank you for being with me.
Oh, thank you for having me. And I'm glad that the books didn't put you off and that you kept going.
Chapter 4: What is the problem with Silicon Valley's business model?
I became the master of pearl here. It was all thanks to you. So I want to take you back in time for a second, Tim, because the way you grew up somehow sparked that love for books, for writing, for what do you think shaped you to the person that you are today?
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.
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.
And I realized, my gosh, that was the stupidest advice from my brother ever.
How did you see the whiteboard? Didn't you like what's in there?
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.
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Chapter 5: How to scale a business with limited resources?
So how did you move from there to starting to write manuals?
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.
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.
Chapter 6: What are Tim's key lessons in entrepreneurship?
That started everything. Were there moments where you're like, oh my God, this is hard. I don't even know if it's going to pay the bills. Let me go back to work. Or was there any like- Well, because I've never had any- Decent work.
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.
Chapter 7: Why should every business prioritize value?
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.
So we produced a few of these things and they caught on and the rest is history, as they say.
Chapter 8: How does Tim envision the future of AI and programming?
So you notice even when it was hard, you're basically adapting, finding another thing that maybe will work out. Eventually, we'll talk about venture capital versus non-venture backed, because I think when your back is a little bit against the wall, you have to find other ways.
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.
Same as Leap Academy, right?
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.
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.
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.
But tell me about those moments when they're really, really hard. And I think the reason why I'm asking, and I'm sure there were more, because as you grow, there's just a risk is just bigger.
Yeah, dot-com bust. I lost a lot of my hair then.
I will go there because I was assuming that that was a hard one. I mean, it was hard for everybody in tech. But let's take one of those hard moments because I think as a leader, especially if there's no million spare sitting there as cushion, that can get really, really, really hairy.
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