In Conversation with Ryan Holiday: Optimism, Stoicism and Building Companies that Last

If you were looking for insights on how to push your product or company to stratospheric heights, you may not think to look to the Stoic Marcus Aurelius.

And that’s a mistake.

You might also think that talking about a Roman philosopher at a conference dedicated to the notion of Optimism and technology is a little misplaced.

Wrong again.

Aurelius, Emperor of Rome from 161 AD until 180 AD, was the inspiration that drove author and media strategist Ryan Holiday to write several books including The Obstacle is the Way, and come up with compelling marketing ideas that put brands like American Apparel on the map. Aurelius is one of the most important of the “Stoic” school of philosophers; an inventor, if you will, of the attitude that is surprisingly well-adapted to the chaotic business world.

“I call it a quake book, The Meditations by Marcus Aurelius is a book that shook me to my core,” said Holiday in an interview after the publication of his first book, Trust Me, I’m Lying – Confessions of a Media Manipulator.

I will be talking to Holiday at the Rakuten Optimism conference in September, to dig into the kind of thinking that has made him a key advisor to clients like Google, TASER, and Complex, as well as many prominent bestselling authors, including Neil Strauss, Tony Robbins and Tim Ferriss.

As a book retailer and a serious booklover, I know exactly what he means by a “quake” book – that book that upends your thinking. Books have the power to do that. Holiday’s own books have changed the course for many – Growth Hacker Marketing rocked the startup world, and is a great precis on how the world of marketing has shifted from creating expensive TV ads to finding and persuading people at the right moment, in an instant, anywhere they happen to be. It explains how companies like Airbnb managed to grow so fast and so huge without spending a dime doing what marketers have always done.

At the inaugural Rakuten Optimism Conference, I’ll be talking to Holiday about that, and what’s next. Trust Me, I’m Lying was the first book to blow the lid off the speed and force at which rumors travel online—and get “traded up” the media ecosystem until they become real headlines and generate real responses in the real world. It also talks about how to use those systems to your benefit, if you need to, because it’s not enough to simply make great products – you also have to make sure people know about them.

Holiday says one common trap is having too much of a focus on what’s popular right this second, and we will discuss the fundamentals of marketing longevity, which include developing a dedicated audience that spreads your work by word of mouth.

Holiday also writes about Stoicism, with books including The Obstacle is the Way and Ego is the Enemy. I’ll be talking to him about that, too.

So, what do really good PR stunts and Stoicism have in common? Discipline, and the ability to see forest for the trees. Recognizing you can’t control what is happening but you can control what you do about it. And when you regard what looks like hardship or difficulty as an opportunity, great things can happen.

That’s straight out of Stoicism and is the core of what makes a human being, and companies, great. It’s what Ryan Holiday has been talking about all along. I’m looking forward to learning more.

About the author

Michael Tamblyn is President and CEO of Rakuten Kobo, one of the world’s most innovative eReading services offering more than 6 million eBooks and audiobooks to millions of customers in 190 countries. Rakuten recently announced the launch of Walmart eBooks by Rakuten Kobo, which offers a comprehensive eBook, audiobook and eReader solution to Walmart customers in the U.S.

At Rakuten Optimism 2018, he will speak with Ryan Holiday about on how disruptive, counter-intuitive and ultimately human ideas are the engine of success in our fast, distracted and technology-driven world.

About Rakuten Optimism 2018

Rakuten Optimism is a new retail and marketing conference that will provoke discussions and inspire by sharing the latest trends and insights from industry leaders, and bring together senior-level marketers, entrepreneurs, influencers, tech and industry experts from around the world. The inaugural edition of the event will be held in San Francisco, California, on September 7, 2018.

This fast-paced, one-day event will include speakers from some of the world’s most beloved brands and an exclusive evening of entertainment with a private concert from Shakira, global pop icon and one of the most successful Latin recording artists of all-time.

For more information about Rakuten Optimism 2018, visit here.