Money in a business is like gas in your car. You need to pay attention so you don’t end up on the side of the road. But your trip is not a tour of gas stations

TIM O’REILLY is the founder and CEO of O’Reilly Media. His original business plan was simply “interesting work for interesting people,” and it seems to have worked out well. O’Reilly Media delivers online learning, publishes books, runs conferences, urges companies to create more value than they capture, and tries to change the world by spreading and amplifying the knowledge of innovators. He has been dubbed the “Trend Spotter” by Wired magazine. Tim has now turned his attention to implications of AI, the on- demand economy, and other technologies that are transforming the nature of work and the future shape of the business world. This is the subject of his new book, WTF?: What’s the Future and Why It’s Up to Us.

What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?

It is very hard to limit this list to three books, because books and the ideas I’ve taken from them are such a large part of my mental toolbox.

I have to start with The Meaning of Culture by John Cowper Powys, because it explains something about my relationship to literature (and the other arts). Powys makes the point that the difference between education and culture is that culture is the incorporation of music, art, literature, and philosophy not just into your library or your CV but into who you are. He talks about the interplay of culture and life, the way that what we read can enrich what we experience, and what we experience can enrich what we read.

The Way of Life According to Lao Tzu, the Tao Te Ching as translated by Witter Bynner. This book is close to the heart of my personal religious and moral philosophy, stressing the rightness of what is, if only we can accept it. Most people who know me have heard me quote from this book. “Seeing as how nothing is outside the vast, wide-meshed net of heaven, who is there to say just how it is cast?” “I find good people good, and I find bad people good, if I am good enough.”

Rissa Kerguelen by F. M. Busby. I read this now largely forgotten science fiction book at about the time I was starting my company, and it influenced me deeply. One key idea is the role of entrepreneurship as a “subversive force.” In a world dominated by large companies, it is the smaller companies that keep freedom alive, with economics at least one of the battlegrounds. This book gave me the courage to submerge myself in the details of a fundamentally trivial business (technical writing and publishing) and to let go of my earlier hopes of writing deep books that would change the world. Those hopes came back around later.

The other wonderful idea in this book is “the long view.” Well before the Long Now Foundation popularized the idea, Busby hinged his plot on the science fiction trope that in a world of near-light-speed travel, time passes more slowly for those at near-relativistic speed than for those left behind. The characters must set events in motion and travel to meet up with them decades hence. That was also a useful framing as I set out to build a business that would allow me to affect the world of the future in ways that I couldn’t yet as a young entrepreneur.

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
I do actually have gigantic billboards of this sort. They are just online rather than by the side of the road. A number of things I’ve said have been turned into Internet memes, complete with a stunning variety of imagery (and sometimes a butchery of the text). Three of the most popular are:

“Work on stuff that matters.”
“Create more value than you capture.”

“Money in a business is like gas in your car. You need to pay attention so you don’t end up on the side of the road. But your trip is not a tour of gas stations.”

If I had to pick just one, it would probably be “Create more value than you capture,” because so much of what’s wrong with our economy comes from a failure to do that. In a rich society, or a rich, complex ecosystem . . . Brian Erwin, at the time my VP of marketing, came up with this line at a company executive retreat in about 2000, when I remarked wryly that more than one Internet billionaire had told me that he’d started his business with what he’d learned from an O’Reilly book. Brian suggested we embrace that principle, and I’ve never looked back.

I once tried to explain to Eric Schmidt why I thought this would be a better guiding light for Google than “Don’t be evil!” It’s measurable—you can actually compare what you get out of an activity to what others do. Google actually does do some of that measurement in its annual economic impact report, but I don’t think they’d be heading into antitrust trouble right now if they had spent more time thinking about the health of their ecosystem as they develop new services. It isn’t enough just to think about yourself and your users or customers. You have to think of your company as part of a web of life, just like an organism in an ecosystem. If you become too dominant, you suck all the life out of the ecosystem. It gets out of balance, and everyone suffers, eventually even the creatures that think themselves safe at the top of the pile.

What is an unusual habit or an absurd thing that you love?

Every morning, on my run, I try to take a picture of a flower and share it on Instagram. I was inspired to do this by a passage I read many years ago in a book by C. S. Lewis (I think it was The Great Divorce), in which a character, after death, only sees the flowers as blobs of color, and his spirit guide tells him, “That’s because you never really looked at them when you were alive.” As the line from Hamilton says, “Look around. Look around. How lucky we are to be alive right now!”

In the last five years, what new belief, behavior, or habit has most improved your life?
When I roll out of bed, I do the plank for two minutes right off, followed by downward dog for the same, then a series of stretches. It gets my metabolism going, and makes me much more likely to start with a more vigorous bout of exercise. I used to start the day by getting on my computer, getting sucked in, then looking up and realizing it was too late to get out before the day started in earnest.

In the last five years, what have you become better at saying no to?

I have profited greatly from Esther Dyson’s advice about accepting speaking engagements: “Would I say yes if it were on Tuesday?” Because the day will come when it is on Tuesday, and you’ll be saying, “Damn, why did I say yes to that?” Forethought is a virtue; remember that one day, that distant future will be now, and the choices you make today will have shaped the choices you are able to make then. This obviously has wide applications to social and environmental issues (ahem, climate change or income inequality) as well.

What are bad recommendations you hear in your profession or area of expertise?
“Disrupt!” When Clayton Christensen introduced the term “disruptive technology” in his 1997 business classic, The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail, he was asking a very different question than “How can I get funded by convincing VCs that there’s a huge market I can blow up?” He wanted to know why existing companies fail to take advantage of new opportunities. He discovered that breakthrough technologies that are not yet mature first succeed by finding radically new markets, and only later disrupt existing markets.

The point of a disruptive technology is not the market or the competitors that it destroys. It is the new markets and the new possibilities that it creates. Just like transistor radios or the early World Wide Web, these new markets are often too small for established companies to consider them worth pursuing. By the time they wake up, an upstart has taken a leadership position in the emerging segment.

But more important, the idea that we should focus on disruption rather than the new value that we can create is at the heart of the current economic malaise, income inequality, and political upheaval. The secret to building a better future is to use technology to do things that were previously impossible. That was true in the first industrial revolution, and it is true now. It isn’t technology that eliminates jobs, it is the shortsighted business decisions that use technology simply to cut costs and fatten corporate profits. The point of technology isn’t to make money. It’s to solve problems!

This is the master design pattern for applying technology: Do more. Do things that were previously unimaginable.

For all its talk of disruption, Silicon Valley too is often in thrall to the financial system. The ultimate fitness function for too many entrepreneurs is not the change they want to make in the world, but “the exit,” the sale or IPO that will make them and the venture capitalists who funded them a giant pile of money. It’s easy to point fingers at “Wall Street” without realizing our own complicity in the problem or in finding a way to bring it under control.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? “Let life ripen and then fall. Will is not the way at all.”—Lao Tzu, from The Way of Life According to Lao Tzu

We equate being smart and being driven as the ways to get ahead. But sometimes, an attitude of alert watchfulness is far wiser and more effective. Learning to follow your nose, pulling on threads of curiosity or interest, may take you places that being driven will never lead you to.

My own life has been shaped by happy coincidences. When I was barely out of college, a friend asked if I’d write a book about science fiction writer Frank Herbert. I’d never written a book, but Dick Riley, the editor of a new series about science fiction authors, knew I loved science fiction and was a good writer. I remember talking to my thesis adviser at Harvard, Zeph Stewart, who was still a friend, about whether it would take me “off course.” He laughed, and said, “You’re only 21. If you don’t know what you’re doing by the time you’re 30, that might be something to worry about.”

Because I said yes, I came to think of myself as a writer. And because I thought of myself as a writer, a few years later, I agreed to help a programmer friend write a computer manual (even though I knew nothing about computers). That lucky break led me to start what was to become O’Reilly Media.

And even later in my career, there were moments when waiting for the right moment led to the perfect outcome. Take “the freeware summit” that I organized in April 1998. I’d been thinking about bringing together people from the Linux community, the Perl community, and the Internet all through the fall of 1997, but something kept me from pulling the trigger. Then Netscape announced that they were going to release their browser as free software, and when I organized the meeting in April of 1998, the timing was perfect. The term “open source” software had been coined by Christine Peterson only a few weeks earlier. If I’d held my meeting in the fall of the previous year, I wouldn’t have had the chance to persuade the assembled leaders to agree to the new name and to showcase it to the assembled press.

Listen to your inner voice, which tells you what to choose. Socrates called it his “daimon.” Lao Tzu said of the wise man that “He has his no, and he has his yes.” It is this ability to wait quietly for the right moment, rather than rushing about aimlessly, that can lead even an ambitious success-hunter to capture the biggest game.

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