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.
Gary Vaynerchuk is a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients. Gary rose to prominence in the late ’90s after establishing one of the first e-commerce wine sites, Wine Library, which helped his father grow the family business from $4 million to $60 million in annual sales. He is a venture capitalist, four-time New York Times best-selling author, and an early investor in companies such as Twitter, Tumblr, Venmo, and Uber. Gary has been named to both Crain‘s and Fortune‘s “40 Under 40” lists. Gary is currently the subject of DailyVee, an online documentary series highlighting what it’s like to be a CEO and public figure in today’s digital world.
What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)?
My random assortment of 1980s wrestling T-shirts.
How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
I believe that being a small guy, being an immigrant, peeing my bed until I was 12, all of these things really set me up for macro success. I was a terrible student and I sucked shit at school.
I think the extremities of my educational life set me up for the extreme winnings that I’m having in real life, because the market—a.k.a. my friends, parents, and the teachers who always razzed on me, and put me down, and anticipated losses from me—forced me to become better.
Burnout is not the price you have to pay for success.
Arianna Huffington has been named to Time magazine’s list of the world’s 100 most influential people and Forbes‘ “Most Powerful Women” list. Originally from Greece, she moved to England when she was 16 and graduated from Cambridge University with an MA in economics. In May 2005, she launched The Huffington Post, a news and blog site that quickly became one of the most widely read, linked-to, and frequently cited media brands on the Internet, and in 2012 won a Pulitzer Prize for national reporting. In August 2016, she launched Thrive Global with the mission of ending the stress and burnout epidemic by offering companies and individuals sustainable, science-based solutions to well-being. Arianna serves on numerous boards, including Uber and The Center for Public Integrity, and she is the author of 15 books, including her most recent, Thrive: The Third Metric to Redefining Success and Creating a Life of Well-Being, Wisdom, and Wonder, and The Sleep Revolution: Transforming Your Life, One Night at a Time.
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?
One of my favorite books that I often give is Meditations by Marcus Aurelius. He spent 19 years as the emperor of Rome facing nearly constant war, a horrific plague, an attempt at the throne by one of his closest allies, and an incompetent and greedy stepbrother as co-emperor, and he still had the presence of mind to write one of my favorite quotes, “People look for retreats for themselves, in the country, by the coast, or in the hills. There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind … So constantly give yourself this retreat, and renew yourself.” And stoicism, as we can see from the almost daily articles about its revival, has never been more relevant. I find the book so inspirational and instructive, it lies on my nightstand.
The fairest rules are those to which everyone would agree if they did not know how much power they would have. —John Rawls
Jason Fried is the co-founder and CEO of Basecamp (previously 37signals), a Chicago-based software firm. The company’s flagship product, Basecamp, is a project management and team communication application trusted by millions. He is the co-author of Getting Real: The Smarter, Faster, Easier, Way to Build a Successful Web Application, which is available for free at gettingreal.37signals.com. He is also the co-author of the New York Times bestseller Rework and Remote: Office Not Required. Jason writes a regular column for Inc. magazine and is a frequent contributor to Basecamp’s popular blog, Signal v. Noise, which offers “strong opinions and shared thoughts on design, business, and tech.”
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?
I think this one’s out of print, but I always tell people to find it and read it: Seeking Wisdom: From Darwin to Munger by Peter Bevelin. I think any book that reviews Charlie Munger‘s ideas is worth reading, and this one in particular weaves in wisdom from some of history’s greatest minds. It’s a bit meandering and loose, but that’s fine with me.
How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
Way back in the ’90s, when I was getting started as a web designer, I sent my work into an awards site called HighFive.com. At the time, it was the shit. If you were awarded a High Five award, you were recognized.
This may come as strange advice from someone who majored in electrical engineering and got a PhD in math modeling of computer security, but I tell students I encounter to spend the remainder of their time in college filling their minds with the best of the humanities their school has to offer.
Ann Miura-Ko is a partner at Floodgate, a venture capital firm specializing in micro-cap investments in startups. She has been called “the most powerful woman in startups” by Forbes and is a lecturer in entrepreneurship at Standford. The child of a rocket scientist at NASA, Ann is a Palo Alto native and has been steeped in technology startups since she was a teenager. Prior to co-founding Floodgate, she worked at Charles River Ventures and McKinsey and Company. Some of Ann’s investments include Lyft, Ayasdi, Xamarin, Refinery29, Chloe and Isabel, Maker Media, Wanelo, TaskRabbit, and Modcloth.
How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
As a 12-year-old, I stood on a stage next to my brother, who confidently pointed to me and announced, “This is Ann Miura. She will be playing a Chopin Nocturne in C sharp minor.” I stood next to him, mute, and then strode over to the piano and started to play. Even though I could play a piano recital in front of many people, [my brother spoke for me because] I was absolutely terrified of speaking in public. Compounding that fear was the fact that I spoke Japanese at home and, while I was very confident of my abilities in other subjects, English was never particularly a strong suit.
Josh Waitzkin was the basis for the book and movie Searching for Bobby Fischer. Considered a chess prodigy, he has perfected learning strategies that can be applied to anything, including his other loves of Brazilian jujitsu (he’s a black belt under phenom Marcelo Garcia) and tai chi push hands (he’s a world champion). These days, he spends his time coaching the world’s top athletes and investors, working to revolutionize education, and tackling his new passion of paddle surfing, often nearly killing me (Tim) in the process. I first met Josh many years ago after reading his book, The Art of Learning.
What is the book (or books) you’ve given most as a gift, and why? Or what are books that have greatly influenced your life?
On the Road by Jack Kerouac: Opened up the ecstatic beauty of life’s little moments to me as a teenager.
Tao Te Ching, Gia-Fu Feng and Jane English translation: Inspired my study of softness and receptivity as a counterpoint to my mad passions.
Zen and the Art of Motorcycle Maintenance by Robert Pirsig: Inspired my cultivation of dynamic quality as a way of life.
Ernest Hemingway on Writing: The most potent little book of wisdom on the creative process that I have run into.
The “problem” with meditation—I thought—was that it wasn’t “practical.” … But I eventually reframed meditation as a way to relinquish control of my conscious mind so that my more powerful unconscious mind could take over.
Adam Robinson has made a lifelong study of outflanking and outsmarting the competition. He is a rated chess master and has been awarded a Life Master title by the United States Chess Federation. As a teenager, he was personally mentored by Bobby Fischer in the 18 months leading up to his winning the world championship. Then, in his first career, Adam developed a revolutionary approach to taking standardized tests as one of the two original co-founders of The Princeton Review. His paradigm-breaking—or “category killing,” as they say in publishing—test-prep book, Cracking the System: The SAT, is the only test-prep book to have ever become a New York Times bestseller. After selling his interest in The Princeton Review, Adam turned his attention in the early ’90s to the then-emerging field of artificial intelligence, developing a program that could analyze text and provide human-like commentary. He was later invited to join a well-known quant fund to develop statistical trading models, and since, he has established himself as an independent global macro advisor to the chief investment officers of a select group of the world’s most successful hedge funds and ultra-high-net-worth family offices.
What is the book (books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?
Our unconscious mind is working all the time, processing orders of magnitude more information, and with astoundingly greater facility, than is our conscious mind. Of course our entire education system, and indeed much of Western philosophy—is devoted to improving our conscious thinking and capacities rather than our unconscious ones.
What makes a river so restful to people is that it doesn’t have any doubt—it is sure to get where it is going, and it doesn’t want to go anywhere else.—Hal Boyle
Maria Sharapova is the winner of five Grand Slam titles and is an Olympic silver medalist in tennis. Maria was born in Nyagan, Russia, and turned professional at the age of 14. She is one of only a handful of players to hold all four Grand Slam titles—Wimbledon (2004), US Open (2006), Australian Open (2008), and the French Open (2012, 2014). She has held the world #1 ranking for 21 weeks and has won 35 singles titles in her career. Forbes named her the highest paid female athlete of all time in 2005, and she held that title for a record 11 years. She is the author of Unstoppable: My Life So Far.
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?
I like to gift The Beggar King and the Secret of Happiness: A True Story by Joel ben Izzy. Some of today’s books come as manuals, step-by-step guides, and although that’s practical, it is not how life always turns out. You might have to take the tenth step before you take the second. I enjoyed this book because it doesn’t give you answers; it makes you wonder what answers you might give yourself.
How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
In my profession, losses are often seen as failures. Not being the person who wins the last point, walking off the court first. All those visible things. But internally, losing sets you up for winning. Losing makes you think in ways victories can’t. You begin asking questions instead of feeling like you have the answers. Questions open up the doors to so many possibilities. If a loss sets me up for those tough questions I might have to ask, then I will get the answers that will ultimately turn those losses into victories.
